PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2012 October 1; 68(Pt 10): o2967–o2968.
Published online 2012 September 22. doi:  10.1107/S1600536812039268
PMCID: PMC3470336

Ethyl 2-[4-(morpholin-4-yl)phen­yl]-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-1,3-benzimidazole-5-carboxyl­ate monohydrate

Abstract

The asymmetric unit of the title compound, C27H32N4O4·H2O, contains two independent benzimidazole-5-carboxyl­ate mol­ecules and two water mol­ecules. In both main mol­ecules, the pyrrolidine rings are in an envelope conformation with a methyl­ene C atom as the flap. The morpholine rings adopt chair conformations. Both benzimidazole rings are essentially planar, with maximum deviations of 0.008 (1) Å, and form dihedral angles of 37.65 (6) and 45.44 (6)° with the benzene rings. In one mol­ecule, an intra­molecular C—H(...)O hydrogen bond forms an S(7) ring motif. In the crystal, O—H(...)O and O—H(...)N hydrogen bonds connect pairs of main mol­ecules and pairs of water mol­ecules into two independent centrosymmetric four-compoment aggregates. These aggregates are connect by C—H(...)O hydrogen bonds leading to the formation of a three-dimensional network, which is stabilized by C—H(...)π interactions.

Related literature  

For the biological activity of benzimidazoles, see: Townsend & Revankar (1970 [triangle]); Dubey & Sanyal (2010 [triangle]). For related structures, see: Yoon, Ali, Wei et al. (2011 [triangle]); Yoon et al. (2012 [triangle]); Yoon, Ali, Choon et al. (2011 [triangle]). For ring conformations, see: Cremer & Pople (1975 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-68-o2967-scheme1.jpg

Experimental  

Crystal data  

  • C27H32N4O4·H2O
  • M r = 494.58
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-o2967-efi1.jpg
  • a = 12.2602 (3) Å
  • b = 13.7267 (4) Å
  • c = 15.3163 (4) Å
  • α = 99.357 (1)°
  • β = 93.700 (1)°
  • γ = 94.003 (1)°
  • V = 2529.56 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.67 × 0.40 × 0.11 mm

Data collection  

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.942, T max = 0.991
  • 61724 measured reflections
  • 14611 independent reflections
  • 10995 reflections with I > 2σ(I)
  • R int = 0.042

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.152
  • S = 1.03
  • 14611 reflections
  • 667 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.58 e Å−3
  • Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039268/lh5526sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039268/lh5526Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039268/lh5526Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research University grants (Nos. 1001/PFIZIK/811151 and 1001/PSK/8620012) and HiCoE research grant (No. 311.CIPPM.4401005). They also wish to express their thanks to the Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Mol­ecular Medicine, Universiti Sains Malaysia for supporting this work. SA thanks the Malaysian Government and USM for an Academic Staff Training Scheme (ASTS) fellowship.

supplementary crystallographic information

Comment

Benzimidazoles belong to one of the well known and most extensively studied class of compounds due to their biological activities such as anti-cancer (Townsend & Revankar, 1970) and anthelmintics (Dubey & Sanyal, 2010). As part of our ongoing structural studies of benzimidazole derivatives (Yoon, Ali, Wei et al. 2011), we report herein the crystal structure of the title compound.

The asymmetric unit of the title compound, (Fig. 1), consists of two crystallographically independent (A and B) Ethyl 2-(4-morpholinophenyl)-1-(3-oxopyrolidin-1-yl) propyl)-1H-benzo [d]imidazole-5-carboxylate and two water molecules. In both molecules, the pyrrolidine rings (N3A/C20A–C23A & N3B/C20B–C23B) are in envelope conformations (Cremer & Pople, 1975) with puckering parameters, Q= 0.2575 (19) Å and [var phi]= 69.4 (4)° in which C21A is the flap and Q= 0.2563 (17) Å and [var phi]= 71.7 (4)° in which C21B is the flap. The morpholine rings, O4A/N4A/C24A–C27A [puckering paramaters; Q = 0.4341 (18) Å, Θ= 1.1 (3)° and [var phi]= 256 (10)°] and O4B/N4B/C24B–C27B [puckering paramaters; Q = 0.5605 (16) Å, Θ= 176.18 (16)° and [var phi]= 153 (3)°] adopt chair conformations. The benzimidazole rings (N1A/N2A/C1A–C7A and N1B/N2B/C1B–C7B) are essentially planar with maximum deviation of 0.008 (1) Å at atom N2A, C6B and C7B. In molecule A, the benzimidazole ring, N1A/N2A/C1A–C7A, forms a dihedral of 37.65 (6)° with the benzene (C8A–C13A) ring. The corresponding dihedral angle in molecule B is 45.44 (6)°. In molecule B, an intramolecular C17A—H17B···O3A hydrogen bond (Table 1) forms S(7) ring motif (Bernstein et al., 1995). The bond lengths and angles are within normal ranges and comparable to the related structures (Yoon, Ali, Wei et al., 2011; Yoon et al., 2012; Yoon, Ali, Choon et al., 2011).

In the crystal packing (Fig. 2), intermolecular O—H···O, C—H···N and C—H···O hydrogen bonds (Table 1) link the molecules into a three-dimensional network. The intermolecular C13B—H13B···Cg1iii, C21B—H21D···Cg2, C24A—H24B···Cg3iii and C24B—H24D···Cg4vii (Table 1) interactions further stabilize the crystal structure (Cg1, Cg2, Cg3 and Cg4 are the centroids of N1A/N2A/C1A/C6A/C7A, C21B–C26B, C21A–C26A and C21B–C26B rings, respectively).

Experimental

Ethyl 3-amino-4-(3(2-oxopyrrolidin-1yl)propylamino)benzoate (0.84 mmol) and sodium metabisulfite adduct of 4-morpholino benzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was reflux at 403K for 2 h. After completion, the reaction mixture was diluted in ethyl acetate (20 ml) and washed with water (20 ml). The organic layer was collected, dried over Na2SO4 and the evaporated in vacuo to yield the product. The product was recrystallized from ethyl acetate. The crystals were then removed and washed twice gently with cold ethyl acetate.

Refinement

H atoms of the water molecules were located in a difference Fourier map and refined freely [O–H = 0.84 (3)–0.91 (3) Å]. All other H atoms were positioned geometrically [C–H = 0.95 and 0.99 Å] and refined using a riding model with Uiso(H) = 1.2 and 1.5 Ueq(C). A rotating group model was applied to the methyl groups. Two outliner reflections (0 0 1 and -9 - 2 12) were omitted in the final refinement.

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids. The dashed line indicates a hydrogen bond.
Fig. 2.
The crystal packing of the title compound. The H atoms not involved in the hydrogen bonds (dashed lines) have been omitted for clarity.

Crystal data

C27H32N4O4·H2OZ = 4
Mr = 494.58F(000) = 1056
Triclinic, P1Dx = 1.299 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.2602 (3) ÅCell parameters from 9908 reflections
b = 13.7267 (4) Åθ = 2.5–33.5°
c = 15.3163 (4) ŵ = 0.09 mm1
α = 99.357 (1)°T = 100 K
β = 93.700 (1)°Plate, colourless
γ = 94.003 (1)°0.67 × 0.40 × 0.11 mm
V = 2529.56 (12) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer14611 independent reflections
Radiation source: fine-focus sealed tube10995 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
[var phi] and ω scansθmax = 30.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −17→17
Tmin = 0.942, Tmax = 0.991k = −19→19
61724 measured reflectionsl = −21→21

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0734P)2 + 1.0729P] where P = (Fo2 + 2Fc2)/3
14611 reflections(Δ/σ)max = 0.001
667 parametersΔρmax = 0.58 e Å3
0 restraintsΔρmin = −0.37 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O1A0.66537 (9)0.88724 (8)0.48359 (7)0.0207 (2)
O2A0.80726 (9)0.79642 (8)0.44866 (7)0.0229 (2)
O3A0.25226 (9)0.68922 (8)−0.13551 (8)0.0235 (2)
O4A0.64255 (10)0.32281 (11)−0.46338 (9)0.0396 (4)
N1A0.68276 (10)0.65123 (9)0.11445 (8)0.0147 (2)
N2A0.52634 (9)0.71947 (9)0.08170 (8)0.0150 (2)
N3A0.38761 (10)0.80132 (9)−0.16261 (8)0.0184 (2)
N4A0.63208 (11)0.45033 (11)−0.29891 (8)0.0240 (3)
C1A0.65487 (11)0.71291 (10)0.18925 (9)0.0138 (3)
C2A0.70794 (11)0.73504 (10)0.27435 (9)0.0152 (3)
H2AA0.77330.70580.28870.018*
C3A0.66221 (11)0.80115 (10)0.33738 (9)0.0157 (3)
C4A0.56478 (12)0.84465 (11)0.31643 (10)0.0178 (3)
H4AA0.53550.88960.36110.021*
C5A0.51084 (12)0.82345 (11)0.23243 (10)0.0182 (3)
H5AA0.44550.85280.21820.022*
C6A0.55780 (11)0.75645 (10)0.16971 (9)0.0152 (3)
C7A0.60465 (11)0.65698 (10)0.05185 (9)0.0142 (3)
C8A0.60534 (11)0.60341 (10)−0.03932 (9)0.0141 (3)
C9A0.51195 (12)0.55865 (10)−0.09139 (9)0.0165 (3)
H9AA0.44210.5637−0.06830.020*
C10A0.51939 (12)0.50689 (11)−0.17616 (9)0.0172 (3)
H10A0.45460.4772−0.21030.021*
C11A0.62128 (12)0.49775 (11)−0.21216 (9)0.0161 (3)
C12A0.71504 (12)0.54133 (11)−0.15894 (9)0.0173 (3)
H12A0.78520.5356−0.18140.021*
C13A0.70707 (11)0.59237 (10)−0.07463 (9)0.0163 (3)
H13A0.77190.6206−0.03980.020*
C14A0.72009 (12)0.82628 (11)0.42737 (9)0.0169 (3)
C15A0.71598 (14)0.91412 (12)0.57342 (10)0.0256 (3)
H15A0.78530.95590.57410.031*
H15B0.73230.85400.59820.031*
C16A0.63542 (16)0.97026 (15)0.62659 (12)0.0353 (4)
H16A0.66390.98590.68900.053*
H16B0.56550.92980.62180.053*
H16C0.62401.03180.60390.053*
C17A0.43840 (11)0.75615 (11)0.02944 (9)0.0160 (3)
H17A0.37890.77480.06800.019*
H17B0.40770.7024−0.01880.019*
C18A0.47845 (12)0.84531 (11)−0.01077 (10)0.0187 (3)
H18A0.54680.8313−0.03980.022*
H18B0.49520.90340.03690.022*
C19A0.39221 (13)0.86937 (11)−0.07883 (10)0.0204 (3)
H19A0.31940.8663−0.05450.025*
H19B0.40930.9378−0.08960.025*
C20A0.45280 (15)0.82253 (13)−0.23446 (11)0.0293 (4)
H20A0.53030.8422−0.21270.035*
H20B0.42320.8759−0.26300.035*
C21A0.44200 (16)0.72360 (14)−0.29895 (12)0.0328 (4)
H21A0.43930.7345−0.36130.039*
H21B0.50400.6835−0.28800.039*
C22A0.33378 (14)0.67318 (13)−0.27850 (11)0.0270 (3)
H22A0.27270.6857−0.31960.032*
H22B0.33810.6008−0.28330.032*
C23A0.31818 (12)0.71960 (11)−0.18452 (10)0.0185 (3)
C24A0.53510 (13)0.41985 (14)−0.35701 (11)0.0285 (4)
H24A0.48810.4759−0.35470.034*
H24B0.49350.3650−0.33570.034*
C25A0.55943 (15)0.38658 (17)−0.45059 (11)0.0380 (5)
H25A0.49140.3532−0.48380.046*
H25B0.57930.4460−0.47700.046*
C26A0.73703 (15)0.35354 (15)−0.40709 (11)0.0340 (4)
H26A0.77600.4099−0.42810.041*
H26B0.78580.2987−0.41200.041*
C27A0.71833 (14)0.38407 (13)−0.31218 (11)0.0283 (4)
H27A0.69920.3242−0.28620.034*
H27B0.78720.4172−0.28020.034*
O1B0.17128 (9)0.40808 (8)0.45880 (7)0.0202 (2)
O2B0.32510 (9)0.33404 (8)0.42527 (7)0.0232 (2)
O3B−0.23642 (9)0.17337 (8)−0.16601 (8)0.0231 (2)
O4B0.12139 (10)−0.16714 (9)−0.48934 (7)0.0254 (2)
N1B0.20016 (10)0.15817 (9)0.09803 (8)0.0146 (2)
N2B0.04049 (9)0.21890 (9)0.06163 (8)0.0143 (2)
N3B−0.09212 (10)0.28326 (9)−0.18049 (8)0.0173 (2)
N4B0.13616 (10)−0.08559 (9)−0.30449 (8)0.0177 (2)
C1B0.17154 (11)0.22424 (10)0.16978 (9)0.0134 (3)
C2B0.22552 (11)0.25486 (10)0.25383 (9)0.0151 (3)
H2BA0.29300.22980.26980.018*
C3B0.17737 (11)0.32329 (10)0.31350 (9)0.0157 (3)
C4B0.07777 (12)0.36160 (11)0.28975 (9)0.0175 (3)
H4BA0.04730.40860.33200.021*
C5B0.02341 (12)0.33243 (11)0.20668 (9)0.0176 (3)
H5BA−0.04340.35840.19050.021*
C6B0.07180 (11)0.26286 (10)0.14780 (9)0.0145 (3)
C7B0.12087 (11)0.15719 (10)0.03483 (9)0.0138 (3)
C8B0.11987 (11)0.09680 (10)−0.05387 (9)0.0141 (3)
C9B0.02794 (12)0.03843 (10)−0.09653 (9)0.0156 (3)
H9BA−0.03930.0395−0.06900.019*
C10B0.03271 (12)−0.02111 (11)−0.17829 (9)0.0166 (3)
H10B−0.0311−0.0607−0.20510.020*
C11B0.12970 (12)−0.02411 (10)−0.22224 (9)0.0153 (3)
C12B0.22229 (12)0.03535 (11)−0.17892 (9)0.0175 (3)
H12B0.28940.0354−0.20670.021*
C13B0.21727 (11)0.09352 (10)−0.09678 (9)0.0163 (3)
H13B0.28130.1320−0.06890.020*
C14B0.23436 (12)0.35468 (11)0.40338 (9)0.0172 (3)
C15B0.21555 (13)0.43897 (12)0.55009 (10)0.0223 (3)
H15C0.27020.49650.55470.027*
H15D0.25160.38430.57190.027*
C16B0.12101 (16)0.46633 (18)0.60303 (12)0.0411 (5)
H16D0.14710.48700.66560.062*
H16E0.06720.40900.59720.062*
H16F0.08670.52100.58110.062*
C17B−0.05096 (11)0.24722 (11)0.00739 (9)0.0158 (3)
H17C−0.11560.25380.04280.019*
H17D−0.07060.1942−0.04440.019*
C18B−0.02321 (13)0.34433 (11)−0.02516 (10)0.0195 (3)
H18C0.05220.3455−0.04480.023*
H18D−0.02590.40030.02410.023*
C19B−0.10395 (13)0.35643 (11)−0.10218 (10)0.0206 (3)
H19C−0.17980.3491−0.08420.025*
H19D−0.09100.4238−0.11670.025*
C20B−0.00713 (13)0.29695 (12)−0.24108 (11)0.0254 (3)
H20C0.06480.3189−0.20800.030*
H20D−0.02620.3462−0.27900.030*
C21B−0.00526 (13)0.19367 (13)−0.29671 (11)0.0256 (3)
H21C0.00880.1982−0.35890.031*
H21D0.05160.1561−0.27160.031*
C22B−0.11994 (13)0.14519 (12)−0.29112 (10)0.0217 (3)
H22C−0.16930.1531−0.34280.026*
H22D−0.11750.0737−0.28890.026*
C23B−0.15789 (11)0.19944 (11)−0.20610 (9)0.0171 (3)
C24B0.03344 (13)−0.13261 (12)−0.35087 (10)0.0226 (3)
H24C−0.0104−0.0815−0.37120.027*
H24D−0.0095−0.1652−0.30950.027*
C25B0.05476 (14)−0.20895 (12)−0.43018 (11)0.0254 (3)
H25C0.0915−0.2637−0.40910.030*
H25D−0.0161−0.2369−0.46220.030*
C26B0.22365 (14)−0.12744 (12)−0.44363 (10)0.0247 (3)
H26C0.2709−0.0998−0.48520.030*
H26D0.2613−0.1810−0.42120.030*
C27B0.20697 (14)−0.04717 (12)−0.36697 (10)0.0236 (3)
H27C0.2789−0.0211−0.33580.028*
H27D0.17310.0081−0.38980.028*
O1WA0.34451 (10)1.00467 (10)0.12704 (10)0.0318 (3)
O1WB0.83897 (11)0.50664 (10)0.14244 (12)0.0425 (4)
H1WA0.303 (2)0.955 (2)0.1401 (16)0.052 (7)*
H2WA0.295 (2)1.048 (2)0.1147 (17)0.061 (8)*
H1WB0.790 (2)0.5461 (19)0.1295 (16)0.052 (7)*
H2WB0.808 (2)0.450 (2)0.1384 (17)0.054 (7)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0249 (5)0.0226 (5)0.0130 (5)0.0054 (4)0.0001 (4)−0.0023 (4)
O2A0.0218 (5)0.0278 (6)0.0175 (5)0.0051 (4)−0.0023 (4)−0.0006 (4)
O3A0.0185 (5)0.0212 (5)0.0304 (6)−0.0006 (4)0.0018 (4)0.0040 (5)
O4A0.0298 (7)0.0514 (8)0.0284 (7)0.0123 (6)−0.0044 (5)−0.0222 (6)
N1A0.0156 (5)0.0144 (5)0.0133 (5)0.0020 (4)0.0000 (4)0.0005 (4)
N2A0.0155 (5)0.0162 (5)0.0127 (5)0.0034 (4)−0.0012 (4)0.0005 (4)
N3A0.0197 (6)0.0190 (6)0.0154 (6)−0.0020 (5)−0.0026 (5)0.0025 (5)
N4A0.0200 (6)0.0367 (8)0.0131 (6)0.0121 (6)−0.0037 (5)−0.0044 (5)
C1A0.0136 (6)0.0132 (6)0.0140 (6)0.0018 (5)0.0004 (5)0.0006 (5)
C2A0.0134 (6)0.0169 (6)0.0151 (7)0.0018 (5)−0.0004 (5)0.0021 (5)
C3A0.0157 (6)0.0166 (6)0.0136 (6)−0.0002 (5)0.0000 (5)0.0004 (5)
C4A0.0180 (7)0.0186 (7)0.0160 (7)0.0039 (5)0.0018 (5)−0.0010 (5)
C5A0.0154 (6)0.0200 (7)0.0184 (7)0.0056 (5)−0.0007 (5)0.0001 (5)
C6A0.0142 (6)0.0153 (6)0.0156 (7)0.0010 (5)−0.0004 (5)0.0018 (5)
C7A0.0145 (6)0.0124 (6)0.0153 (6)0.0006 (5)−0.0001 (5)0.0017 (5)
C8A0.0166 (6)0.0124 (6)0.0131 (6)0.0019 (5)0.0000 (5)0.0020 (5)
C9A0.0158 (6)0.0184 (7)0.0150 (7)0.0002 (5)0.0010 (5)0.0027 (5)
C10A0.0163 (6)0.0196 (7)0.0147 (7)0.0000 (5)−0.0019 (5)0.0011 (5)
C11A0.0184 (6)0.0185 (7)0.0119 (6)0.0048 (5)−0.0003 (5)0.0034 (5)
C12A0.0152 (6)0.0213 (7)0.0159 (7)0.0040 (5)0.0018 (5)0.0035 (5)
C13A0.0141 (6)0.0177 (6)0.0169 (7)0.0023 (5)−0.0006 (5)0.0023 (5)
C14A0.0184 (6)0.0167 (6)0.0146 (7)0.0002 (5)0.0016 (5)0.0005 (5)
C15A0.0358 (9)0.0258 (8)0.0131 (7)0.0072 (7)−0.0028 (6)−0.0033 (6)
C16A0.0399 (10)0.0419 (11)0.0213 (8)0.0027 (8)0.0081 (7)−0.0047 (7)
C17A0.0135 (6)0.0189 (7)0.0152 (7)0.0038 (5)−0.0027 (5)0.0024 (5)
C18A0.0201 (7)0.0163 (6)0.0181 (7)−0.0003 (5)−0.0049 (5)0.0013 (5)
C19A0.0254 (7)0.0141 (6)0.0203 (7)0.0020 (6)−0.0060 (6)0.0012 (5)
C20A0.0312 (9)0.0318 (9)0.0245 (8)−0.0057 (7)0.0041 (7)0.0061 (7)
C21A0.0381 (10)0.0381 (10)0.0214 (8)0.0013 (8)0.0082 (7)0.0010 (7)
C22A0.0326 (9)0.0273 (8)0.0178 (7)−0.0010 (7)−0.0050 (6)−0.0015 (6)
C23A0.0162 (6)0.0180 (7)0.0204 (7)0.0008 (5)−0.0052 (5)0.0036 (5)
C24A0.0185 (7)0.0396 (10)0.0218 (8)0.0042 (7)−0.0040 (6)−0.0094 (7)
C25A0.0316 (9)0.0608 (13)0.0186 (8)0.0215 (9)−0.0048 (7)−0.0074 (8)
C26A0.0340 (9)0.0451 (11)0.0210 (8)0.0200 (8)−0.0024 (7)−0.0054 (7)
C27A0.0281 (8)0.0307 (9)0.0233 (8)0.0136 (7)−0.0038 (6)−0.0065 (7)
O1B0.0226 (5)0.0223 (5)0.0136 (5)0.0063 (4)−0.0013 (4)−0.0044 (4)
O2B0.0198 (5)0.0301 (6)0.0170 (5)0.0051 (4)−0.0046 (4)−0.0032 (4)
O3B0.0177 (5)0.0255 (6)0.0272 (6)−0.0001 (4)0.0021 (4)0.0081 (5)
O4B0.0312 (6)0.0290 (6)0.0141 (5)0.0029 (5)0.0024 (4)−0.0023 (4)
N1B0.0174 (5)0.0146 (5)0.0112 (5)0.0029 (4)−0.0010 (4)−0.0001 (4)
N2B0.0140 (5)0.0163 (5)0.0117 (5)0.0021 (4)−0.0019 (4)−0.0001 (4)
N3B0.0165 (6)0.0202 (6)0.0149 (6)0.0002 (5)−0.0010 (4)0.0037 (5)
N4B0.0205 (6)0.0201 (6)0.0107 (5)−0.0014 (5)0.0011 (4)−0.0017 (4)
C1B0.0144 (6)0.0131 (6)0.0117 (6)0.0016 (5)−0.0003 (5)−0.0003 (5)
C2B0.0148 (6)0.0165 (6)0.0131 (6)0.0027 (5)−0.0016 (5)0.0007 (5)
C3B0.0158 (6)0.0174 (6)0.0128 (6)0.0018 (5)−0.0008 (5)−0.0001 (5)
C4B0.0167 (6)0.0199 (7)0.0147 (7)0.0051 (5)0.0008 (5)−0.0018 (5)
C5B0.0152 (6)0.0210 (7)0.0160 (7)0.0055 (5)−0.0004 (5)0.0003 (5)
C6B0.0143 (6)0.0160 (6)0.0124 (6)0.0010 (5)−0.0018 (5)0.0008 (5)
C7B0.0153 (6)0.0122 (6)0.0133 (6)0.0001 (5)−0.0006 (5)0.0014 (5)
C8B0.0172 (6)0.0134 (6)0.0109 (6)0.0015 (5)−0.0011 (5)0.0009 (5)
C9B0.0178 (6)0.0168 (6)0.0119 (6)−0.0010 (5)0.0016 (5)0.0024 (5)
C10B0.0184 (6)0.0172 (6)0.0128 (6)−0.0026 (5)−0.0009 (5)0.0009 (5)
C11B0.0206 (7)0.0153 (6)0.0096 (6)0.0016 (5)−0.0013 (5)0.0015 (5)
C12B0.0158 (6)0.0211 (7)0.0148 (7)0.0018 (5)0.0008 (5)0.0008 (5)
C13B0.0153 (6)0.0170 (6)0.0155 (7)0.0002 (5)−0.0014 (5)0.0008 (5)
C14B0.0189 (7)0.0176 (6)0.0136 (6)0.0017 (5)0.0001 (5)−0.0017 (5)
C15B0.0289 (8)0.0231 (7)0.0121 (7)0.0029 (6)−0.0027 (6)−0.0045 (5)
C16B0.0360 (10)0.0642 (14)0.0193 (9)0.0046 (9)0.0058 (7)−0.0061 (8)
C17B0.0132 (6)0.0197 (7)0.0142 (6)0.0026 (5)−0.0032 (5)0.0031 (5)
C18B0.0235 (7)0.0165 (7)0.0173 (7)0.0023 (5)−0.0059 (6)0.0014 (5)
C19B0.0247 (7)0.0190 (7)0.0178 (7)0.0058 (6)−0.0039 (6)0.0025 (5)
C20B0.0234 (8)0.0283 (8)0.0242 (8)−0.0039 (6)0.0050 (6)0.0051 (6)
C21B0.0246 (8)0.0320 (9)0.0200 (8)0.0021 (7)0.0062 (6)0.0021 (6)
C22B0.0247 (7)0.0249 (8)0.0147 (7)0.0007 (6)−0.0020 (6)0.0026 (6)
C23B0.0148 (6)0.0209 (7)0.0160 (7)0.0016 (5)−0.0042 (5)0.0062 (5)
C24B0.0218 (7)0.0264 (8)0.0164 (7)−0.0013 (6)−0.0006 (6)−0.0039 (6)
C25B0.0272 (8)0.0260 (8)0.0196 (8)−0.0015 (6)0.0000 (6)−0.0044 (6)
C26B0.0288 (8)0.0247 (8)0.0188 (7)0.0007 (6)0.0060 (6)−0.0023 (6)
C27B0.0296 (8)0.0220 (7)0.0176 (7)−0.0023 (6)0.0070 (6)−0.0012 (6)
O1WA0.0230 (6)0.0226 (6)0.0512 (8)0.0041 (5)−0.0005 (6)0.0104 (6)
O1WB0.0237 (6)0.0195 (6)0.0827 (12)0.0014 (5)−0.0133 (7)0.0104 (7)

Geometric parameters (Å, º)

O1A—C14A1.3455 (17)O2B—C14B1.2070 (17)
O1A—C15A1.4515 (18)O3B—C23B1.2377 (18)
O2A—C14A1.2149 (18)O4B—C25B1.420 (2)
O3A—C23A1.2344 (19)O4B—C26B1.4235 (19)
O4A—C25A1.392 (2)N1B—C7B1.3247 (17)
O4A—C26A1.396 (2)N1B—C1B1.3869 (17)
N1A—C7A1.3264 (17)N2B—C6B1.3773 (17)
N1A—C1A1.3864 (17)N2B—C7B1.3830 (18)
N2A—C6A1.3808 (17)N2B—C17B1.4642 (17)
N2A—C7A1.3824 (17)N3B—C23B1.3456 (18)
N2A—C17A1.4669 (17)N3B—C19B1.4558 (19)
N3A—C23A1.3427 (18)N3B—C20B1.462 (2)
N3A—C19A1.4546 (19)N4B—C11B1.4080 (17)
N3A—C20A1.456 (2)N4B—C24B1.4591 (18)
N4A—C11A1.4001 (18)N4B—C27B1.468 (2)
N4A—C24A1.4330 (19)C1B—C2B1.3953 (18)
N4A—C27A1.445 (2)C1B—C6B1.4089 (18)
C1A—C2A1.3959 (18)C2B—C3B1.3906 (19)
C1A—C6A1.4053 (18)C2B—H2BA0.9500
C2A—C3A1.3877 (19)C3B—C4B1.4124 (19)
C2A—H2AA0.9500C3B—C14B1.4865 (19)
C3A—C4A1.4138 (19)C4B—C5B1.3824 (19)
C3A—C14A1.4857 (19)C4B—H4BA0.9500
C4A—C5A1.3852 (19)C5B—C6B1.3947 (19)
C4A—H4AA0.9500C5B—H5BA0.9500
C5A—C6A1.3993 (19)C7B—C8B1.4707 (18)
C5A—H5AA0.9500C8B—C9B1.3957 (18)
C7A—C8A1.4694 (19)C8B—C13B1.400 (2)
C8A—C9A1.3961 (18)C9B—C10B1.3867 (19)
C8A—C13A1.3992 (19)C9B—H9BA0.9500
C9A—C10A1.387 (2)C10B—C11B1.404 (2)
C9A—H9AA0.9500C10B—H10B0.9500
C10A—C11A1.403 (2)C11B—C12B1.4115 (19)
C10A—H10A0.9500C12B—C13B1.3835 (19)
C11A—C12A1.4029 (19)C12B—H12B0.9500
C12A—C13A1.378 (2)C13B—H13B0.9500
C12A—H12A0.9500C15B—C16B1.492 (2)
C13A—H13A0.9500C15B—H15C0.9900
C15A—C16A1.496 (2)C15B—H15D0.9900
C15A—H15A0.9900C16B—H16D0.9800
C15A—H15B0.9900C16B—H16E0.9800
C16A—H16A0.9800C16B—H16F0.9800
C16A—H16B0.9800C17B—C18B1.522 (2)
C16A—H16C0.9800C17B—H17C0.9900
C17A—C18A1.523 (2)C17B—H17D0.9900
C17A—H17A0.9900C18B—C19B1.5281 (19)
C17A—H17B0.9900C18B—H18C0.9900
C18A—C19A1.5271 (19)C18B—H18D0.9900
C18A—H18A0.9900C19B—H19C0.9900
C18A—H18B0.9900C19B—H19D0.9900
C19A—H19A0.9900C20B—C21B1.533 (2)
C19A—H19B0.9900C20B—H20C0.9900
C20A—C21A1.536 (2)C20B—H20D0.9900
C20A—H20A0.9900C21B—C22B1.527 (2)
C20A—H20B0.9900C21B—H21C0.9900
C21A—C22A1.528 (3)C21B—H21D0.9900
C21A—H21A0.9900C22B—C23B1.509 (2)
C21A—H21B0.9900C22B—H22C0.9900
C22A—C23A1.506 (2)C22B—H22D0.9900
C22A—H22A0.9900C24B—C25B1.519 (2)
C22A—H22B0.9900C24B—H24C0.9900
C24A—C25A1.488 (2)C24B—H24D0.9900
C24A—H24A0.9900C25B—H25C0.9900
C24A—H24B0.9900C25B—H25D0.9900
C25A—H25A0.9900C26B—C27B1.509 (2)
C25A—H25B0.9900C26B—H26C0.9900
C26A—C27A1.483 (2)C26B—H26D0.9900
C26A—H26A0.9900C27B—H27C0.9900
C26A—H26B0.9900C27B—H27D0.9900
C27A—H27A0.9900O1WA—H1WA0.88 (3)
C27A—H27B0.9900O1WA—H2WA0.91 (3)
O1B—C14B1.3482 (17)O1WB—H1WB0.87 (3)
O1B—C15B1.4514 (17)O1WB—H2WB0.84 (3)
C14A—O1A—C15A115.63 (12)C25B—O4B—C26B109.43 (12)
C25A—O4A—C26A113.58 (13)C7B—N1B—C1B105.19 (11)
C7A—N1A—C1A105.09 (11)C6B—N2B—C7B106.63 (11)
C6A—N2A—C7A106.39 (11)C6B—N2B—C17B124.46 (11)
C6A—N2A—C17A124.43 (11)C7B—N2B—C17B128.17 (11)
C7A—N2A—C17A128.26 (12)C23B—N3B—C19B124.77 (13)
C23A—N3A—C19A124.63 (13)C23B—N3B—C20B113.41 (12)
C23A—N3A—C20A113.69 (13)C19B—N3B—C20B121.79 (12)
C19A—N3A—C20A121.42 (13)C11B—N4B—C24B117.25 (12)
C11A—N4A—C24A118.85 (13)C11B—N4B—C27B116.73 (12)
C11A—N4A—C27A117.46 (12)C24B—N4B—C27B110.38 (12)
C24A—N4A—C27A113.95 (13)N1B—C1B—C2B130.21 (12)
N1A—C1A—C2A129.91 (12)N1B—C1B—C6B109.88 (11)
N1A—C1A—C6A109.98 (12)C2B—C1B—C6B119.91 (12)
C2A—C1A—C6A120.11 (12)C3B—C2B—C1B117.82 (12)
C3A—C2A—C1A117.90 (12)C3B—C2B—H2BA121.1
C3A—C2A—H2AA121.0C1B—C2B—H2BA121.1
C1A—C2A—H2AA121.0C2B—C3B—C4B121.27 (12)
C2A—C3A—C4A121.23 (13)C2B—C3B—C14B117.65 (12)
C2A—C3A—C14A117.83 (12)C4B—C3B—C14B121.07 (12)
C4A—C3A—C14A120.93 (12)C5B—C4B—C3B121.69 (13)
C5A—C4A—C3A121.70 (13)C5B—C4B—H4BA119.2
C5A—C4A—H4AA119.1C3B—C4B—H4BA119.2
C3A—C4A—H4AA119.1C4B—C5B—C6B116.50 (13)
C4A—C5A—C6A116.38 (13)C4B—C5B—H5BA121.8
C4A—C5A—H5AA121.8C6B—C5B—H5BA121.8
C6A—C5A—H5AA121.8N2B—C6B—C5B131.51 (13)
N2A—C6A—C5A131.51 (13)N2B—C6B—C1B105.69 (12)
N2A—C6A—C1A105.81 (12)C5B—C6B—C1B122.80 (12)
C5A—C6A—C1A122.68 (13)N1B—C7B—N2B112.61 (12)
N1A—C7A—N2A112.72 (12)N1B—C7B—C8B123.05 (12)
N1A—C7A—C8A122.28 (12)N2B—C7B—C8B124.34 (12)
N2A—C7A—C8A124.98 (12)C9B—C8B—C13B117.60 (12)
C9A—C8A—C13A117.83 (12)C9B—C8B—C7B123.58 (13)
C9A—C8A—C7A124.42 (13)C13B—C8B—C7B118.75 (12)
C13A—C8A—C7A117.68 (12)C10B—C9B—C8B121.37 (13)
C10A—C9A—C8A121.15 (13)C10B—C9B—H9BA119.3
C10A—C9A—H9AA119.4C8B—C9B—H9BA119.3
C8A—C9A—H9AA119.4C9B—C10B—C11B121.43 (13)
C9A—C10A—C11A120.90 (13)C9B—C10B—H10B119.3
C9A—C10A—H10A119.5C11B—C10B—H10B119.3
C11A—C10A—H10A119.5C10B—C11B—N4B121.98 (12)
N4A—C11A—C12A119.47 (13)C10B—C11B—C12B116.94 (12)
N4A—C11A—C10A122.80 (13)N4B—C11B—C12B121.06 (13)
C12A—C11A—C10A117.70 (13)C13B—C12B—C11B121.28 (13)
C13A—C12A—C11A121.08 (13)C13B—C12B—H12B119.4
C13A—C12A—H12A119.5C11B—C12B—H12B119.4
C11A—C12A—H12A119.5C12B—C13B—C8B121.37 (13)
C12A—C13A—C8A121.31 (13)C12B—C13B—H13B119.3
C12A—C13A—H13A119.3C8B—C13B—H13B119.3
C8A—C13A—H13A119.3O2B—C14B—O1B123.61 (13)
O2A—C14A—O1A123.10 (13)O2B—C14B—C3B124.76 (13)
O2A—C14A—C3A124.59 (13)O1B—C14B—C3B111.62 (12)
O1A—C14A—C3A112.30 (12)O1B—C15B—C16B106.61 (13)
O1A—C15A—C16A106.53 (14)O1B—C15B—H15C110.4
O1A—C15A—H15A110.4C16B—C15B—H15C110.4
C16A—C15A—H15A110.4O1B—C15B—H15D110.4
O1A—C15A—H15B110.4C16B—C15B—H15D110.4
C16A—C15A—H15B110.4H15C—C15B—H15D108.6
H15A—C15A—H15B108.6C15B—C16B—H16D109.5
C15A—C16A—H16A109.5C15B—C16B—H16E109.5
C15A—C16A—H16B109.5H16D—C16B—H16E109.5
H16A—C16A—H16B109.5C15B—C16B—H16F109.5
C15A—C16A—H16C109.5H16D—C16B—H16F109.5
H16A—C16A—H16C109.5H16E—C16B—H16F109.5
H16B—C16A—H16C109.5N2B—C17B—C18B112.14 (11)
N2A—C17A—C18A112.28 (11)N2B—C17B—H17C109.2
N2A—C17A—H17A109.1C18B—C17B—H17C109.2
C18A—C17A—H17A109.1N2B—C17B—H17D109.2
N2A—C17A—H17B109.1C18B—C17B—H17D109.2
C18A—C17A—H17B109.1H17C—C17B—H17D107.9
H17A—C17A—H17B107.9C17B—C18B—C19B110.76 (12)
C17A—C18A—C19A111.11 (12)C17B—C18B—H18C109.5
C17A—C18A—H18A109.4C19B—C18B—H18C109.5
C19A—C18A—H18A109.4C17B—C18B—H18D109.5
C17A—C18A—H18B109.4C19B—C18B—H18D109.5
C19A—C18A—H18B109.4H18C—C18B—H18D108.1
H18A—C18A—H18B108.0N3B—C19B—C18B111.28 (12)
N3A—C19A—C18A112.24 (12)N3B—C19B—H19C109.4
N3A—C19A—H19A109.2C18B—C19B—H19C109.4
C18A—C19A—H19A109.2N3B—C19B—H19D109.4
N3A—C19A—H19B109.2C18B—C19B—H19D109.4
C18A—C19A—H19B109.2H19C—C19B—H19D108.0
H19A—C19A—H19B107.9N3B—C20B—C21B103.47 (13)
N3A—C20A—C21A103.17 (13)N3B—C20B—H20C111.1
N3A—C20A—H20A111.1C21B—C20B—H20C111.1
C21A—C20A—H20A111.1N3B—C20B—H20D111.1
N3A—C20A—H20B111.1C21B—C20B—H20D111.1
C21A—C20A—H20B111.1H20C—C20B—H20D109.0
H20A—C20A—H20B109.1C22B—C21B—C20B103.60 (13)
C22A—C21A—C20A103.56 (14)C22B—C21B—H21C111.0
C22A—C21A—H21A111.0C20B—C21B—H21C111.0
C20A—C21A—H21A111.0C22B—C21B—H21D111.0
C22A—C21A—H21B111.0C20B—C21B—H21D111.0
C20A—C21A—H21B111.0H21C—C21B—H21D109.0
H21A—C21A—H21B109.0C23B—C22B—C21B104.39 (12)
C23A—C22A—C21A104.34 (12)C23B—C22B—H22C110.9
C23A—C22A—H22A110.9C21B—C22B—H22C110.9
C21A—C22A—H22A110.9C23B—C22B—H22D110.9
C23A—C22A—H22B110.9C21B—C22B—H22D110.9
C21A—C22A—H22B110.9H22C—C22B—H22D108.9
H22A—C22A—H22B108.9O3B—C23B—N3B124.75 (14)
O3A—C23A—N3A125.12 (14)O3B—C23B—C22B126.85 (13)
O3A—C23A—C22A126.42 (13)N3B—C23B—C22B108.40 (13)
N3A—C23A—C22A108.45 (13)N4B—C24B—C25B111.00 (13)
N4A—C24A—C25A112.80 (14)N4B—C24B—H24C109.4
N4A—C24A—H24A109.0C25B—C24B—H24C109.4
C25A—C24A—H24A109.0N4B—C24B—H24D109.4
N4A—C24A—H24B109.0C25B—C24B—H24D109.4
C25A—C24A—H24B109.0H24C—C24B—H24D108.0
H24A—C24A—H24B107.8O4B—C25B—C24B111.78 (13)
O4A—C25A—C24A116.21 (15)O4B—C25B—H25C109.3
O4A—C25A—H25A108.2C24B—C25B—H25C109.3
C24A—C25A—H25A108.2O4B—C25B—H25D109.3
O4A—C25A—H25B108.2C24B—C25B—H25D109.3
C24A—C25A—H25B108.2H25C—C25B—H25D107.9
H25A—C25A—H25B107.4O4B—C26B—C27B110.79 (13)
O4A—C26A—C27A115.26 (15)O4B—C26B—H26C109.5
O4A—C26A—H26A108.5C27B—C26B—H26C109.5
C27A—C26A—H26A108.5O4B—C26B—H26D109.5
O4A—C26A—H26B108.5C27B—C26B—H26D109.5
C27A—C26A—H26B108.5H26C—C26B—H26D108.1
H26A—C26A—H26B107.5N4B—C27B—C26B110.81 (13)
N4A—C27A—C26A113.01 (14)N4B—C27B—H27C109.5
N4A—C27A—H27A109.0C26B—C27B—H27C109.5
C26A—C27A—H27A109.0N4B—C27B—H27D109.5
N4A—C27A—H27B109.0C26B—C27B—H27D109.5
C26A—C27A—H27B109.0H27C—C27B—H27D108.1
H27A—C27A—H27B107.8H1WA—O1WA—H2WA103 (2)
C14B—O1B—C15B116.99 (11)H1WB—O1WB—H2WB108 (2)
C7A—N1A—C1A—C2A179.95 (15)C7B—N1B—C1B—C2B−179.34 (15)
C7A—N1A—C1A—C6A−0.31 (15)C7B—N1B—C1B—C6B0.25 (16)
N1A—C1A—C2A—C3A179.21 (14)N1B—C1B—C2B—C3B179.76 (14)
C6A—C1A—C2A—C3A−0.5 (2)C6B—C1B—C2B—C3B0.2 (2)
C1A—C2A—C3A—C4A0.2 (2)C1B—C2B—C3B—C4B−0.7 (2)
C1A—C2A—C3A—C14A−178.72 (13)C1B—C2B—C3B—C14B179.18 (13)
C2A—C3A—C4A—C5A−0.1 (2)C2B—C3B—C4B—C5B0.5 (2)
C14A—C3A—C4A—C5A178.81 (14)C14B—C3B—C4B—C5B−179.44 (14)
C3A—C4A—C5A—C6A0.2 (2)C3B—C4B—C5B—C6B0.3 (2)
C7A—N2A—C6A—C5A179.00 (15)C7B—N2B—C6B—C5B178.63 (15)
C17A—N2A—C6A—C5A9.2 (2)C17B—N2B—C6B—C5B7.7 (2)
C7A—N2A—C6A—C1A−0.55 (15)C7B—N2B—C6B—C1B−0.42 (15)
C17A—N2A—C6A—C1A−170.37 (13)C17B—N2B—C6B—C1B−171.32 (12)
C4A—C5A—C6A—N2A179.96 (15)C4B—C5B—C6B—N2B−179.76 (15)
C4A—C5A—C6A—C1A−0.6 (2)C4B—C5B—C6B—C1B−0.9 (2)
N1A—C1A—C6A—N2A0.54 (16)N1B—C1B—C6B—N2B0.12 (16)
C2A—C1A—C6A—N2A−179.68 (13)C2B—C1B—C6B—N2B179.75 (13)
N1A—C1A—C6A—C5A−179.05 (13)N1B—C1B—C6B—C5B−179.03 (13)
C2A—C1A—C6A—C5A0.7 (2)C2B—C1B—C6B—C5B0.6 (2)
C1A—N1A—C7A—N2A−0.05 (16)C1B—N1B—C7B—N2B−0.53 (16)
C1A—N1A—C7A—C8A178.61 (12)C1B—N1B—C7B—C8B179.32 (13)
C6A—N2A—C7A—N1A0.39 (16)C6B—N2B—C7B—N1B0.62 (16)
C17A—N2A—C7A—N1A169.69 (13)C17B—N2B—C7B—N1B171.07 (13)
C6A—N2A—C7A—C8A−178.23 (13)C6B—N2B—C7B—C8B−179.23 (13)
C17A—N2A—C7A—C8A−8.9 (2)C17B—N2B—C7B—C8B−8.8 (2)
N1A—C7A—C8A—C9A141.68 (15)N1B—C7B—C8B—C9B133.39 (15)
N2A—C7A—C8A—C9A−39.8 (2)N2B—C7B—C8B—C9B−46.8 (2)
N1A—C7A—C8A—C13A−35.0 (2)N1B—C7B—C8B—C13B−43.5 (2)
N2A—C7A—C8A—C13A143.50 (14)N2B—C7B—C8B—C13B136.29 (14)
C13A—C8A—C9A—C10A−1.5 (2)C13B—C8B—C9B—C10B0.3 (2)
C7A—C8A—C9A—C10A−178.16 (13)C7B—C8B—C9B—C10B−176.69 (13)
C8A—C9A—C10A—C11A0.1 (2)C8B—C9B—C10B—C11B−1.0 (2)
C24A—N4A—C11A—C12A−170.35 (15)C9B—C10B—C11B—N4B178.81 (13)
C27A—N4A—C11A—C12A45.7 (2)C9B—C10B—C11B—C12B0.7 (2)
C24A—N4A—C11A—C10A7.4 (2)C24B—N4B—C11B—C10B11.1 (2)
C27A—N4A—C11A—C10A−136.52 (16)C27B—N4B—C11B—C10B145.42 (14)
C9A—C10A—C11A—N4A−176.83 (14)C24B—N4B—C11B—C12B−170.82 (14)
C9A—C10A—C11A—C12A1.0 (2)C27B—N4B—C11B—C12B−36.54 (19)
N4A—C11A—C12A—C13A177.14 (14)C10B—C11B—C12B—C13B0.2 (2)
C10A—C11A—C12A—C13A−0.8 (2)N4B—C11B—C12B—C13B−177.93 (13)
C11A—C12A—C13A—C8A−0.6 (2)C11B—C12B—C13B—C8B−0.9 (2)
C9A—C8A—C13A—C12A1.7 (2)C9B—C8B—C13B—C12B0.6 (2)
C7A—C8A—C13A—C12A178.62 (13)C7B—C8B—C13B—C12B177.74 (13)
C15A—O1A—C14A—O2A−1.4 (2)C15B—O1B—C14B—O2B−1.9 (2)
C15A—O1A—C14A—C3A179.14 (13)C15B—O1B—C14B—C3B176.96 (12)
C2A—C3A—C14A—O2A3.4 (2)C2B—C3B—C14B—O2B8.8 (2)
C4A—C3A—C14A—O2A−175.51 (15)C4B—C3B—C14B—O2B−171.27 (15)
C2A—C3A—C14A—O1A−177.09 (12)C2B—C3B—C14B—O1B−170.03 (13)
C4A—C3A—C14A—O1A4.0 (2)C4B—C3B—C14B—O1B9.9 (2)
C14A—O1A—C15A—C16A−172.75 (14)C14B—O1B—C15B—C16B−162.12 (15)
C6A—N2A—C17A—C18A85.14 (17)C6B—N2B—C17B—C18B74.78 (17)
C7A—N2A—C17A—C18A−82.40 (17)C7B—N2B—C17B—C18B−94.10 (17)
N2A—C17A—C18A—C19A168.93 (12)N2B—C17B—C18B—C19B163.07 (12)
C23A—N3A—C19A—C18A94.52 (17)C23B—N3B—C19B—C18B100.16 (16)
C20A—N3A—C19A—C18A−91.63 (17)C20B—N3B—C19B—C18B−81.86 (17)
C17A—C18A—C19A—N3A−76.53 (16)C17B—C18B—C19B—N3B−66.92 (17)
C23A—N3A—C20A—C21A−17.48 (18)C23B—N3B—C20B—C21B−16.40 (17)
C19A—N3A—C20A—C21A168.04 (14)C19B—N3B—C20B—C21B165.41 (13)
N3A—C20A—C21A—C22A24.94 (18)N3B—C20B—C21B—C22B24.60 (16)
C20A—C21A—C22A—C23A−24.16 (18)C20B—C21B—C22B—C23B−24.49 (16)
C19A—N3A—C23A—O3A−3.0 (2)C19B—N3B—C23B—O3B−0.6 (2)
C20A—N3A—C23A—O3A−177.29 (15)C20B—N3B—C23B—O3B−178.71 (14)
C19A—N3A—C23A—C22A176.23 (13)C19B—N3B—C23B—C22B178.76 (12)
C20A—N3A—C23A—C22A1.95 (18)C20B—N3B—C23B—C22B0.63 (17)
C21A—C22A—C23A—O3A−166.17 (15)C21B—C22B—C23B—O3B−165.12 (14)
C21A—C22A—C23A—N3A14.59 (17)C21B—C22B—C23B—N3B15.55 (16)
C11A—N4A—C24A—C25A170.14 (16)C11B—N4B—C24B—C25B−170.75 (13)
C27A—N4A—C24A—C25A−44.7 (2)C27B—N4B—C24B—C25B52.27 (17)
C26A—O4A—C25A—C24A−46.8 (3)C26B—O4B—C25B—C24B59.34 (17)
N4A—C24A—C25A—O4A45.7 (3)N4B—C24B—C25B—O4B−55.84 (18)
C25A—O4A—C26A—C27A47.3 (2)C25B—O4B—C26B—C27B−60.60 (17)
C11A—N4A—C27A—C26A−168.58 (15)C11B—N4B—C27B—C26B168.84 (13)
C24A—N4A—C27A—C26A45.7 (2)C24B—N4B—C27B—C26B−53.93 (17)
O4A—C26A—C27A—N4A−47.1 (2)O4B—C26B—C27B—N4B58.54 (18)

Hydrogen-bond geometry (Å, º)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1A/N2A/C1A/C6A/C7A, C21B–C26B, C21A–C26A and C21B–C26B rings, respectively.

D—H···AD—HH···AD···AD—H···A
C17A—H17B···O3A0.992.503.2624 (18)133
O1WA—H1WA···O3Bi0.88 (3)2.00 (3)2.8652 (18)168 (2)
O1WA—H2WA···N1Bii0.91 (3)2.01 (3)2.9142 (18)172 (2)
O1WB—H1WB···N1A0.87 (3)2.05 (3)2.9142 (19)172 (2)
O1WB—H2WB···O3Aiii0.83 (3)1.99 (3)2.8218 (18)174 (2)
C15A—H15B···O2Biv0.992.593.412 (2)141
C15B—H15D···O2Aiv0.992.503.227 (2)130
C17A—H17A···O3Bi0.992.443.4334 (18)178
C17B—H17C···O3Ai0.992.363.3274 (18)166
C25A—H25A···O2Bv0.992.373.309 (2)159
C26A—H26B···O4Bvi0.992.543.425 (2)148
C13B—H13B···Cg1iii0.952.873.5419 (15)129
C21B—H21D···Cg20.992.963.8494 (18)150
C24A—H24B···Cg3iii0.992.793.7712 (19)172
C24B—H24D···Cg4vii0.992.673.6357 (17)165

Symmetry codes: (i) −x, −y+1, −z; (ii) x, y+1, z; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+1, −z+1; (v) x, y, z−1; (vi) −x+1, −y, −z−1; (vii) −x, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5526).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.
  • Bruker (2009). SADABS, APEX2 and SAINTBruker AXS Inc., Madison, Wisconsin, USA.
  • Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.
  • Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.
  • Dubey, A. K. & Sanyal, P. K. (2010). Vet. Scan. 5, 63.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Townsend, L. B. & Revankar, G. R. (1970). Chem. Rev. 70, 389–438. [PubMed]
  • Yoon, Y. K., Ali, M. A., Choon, T. S., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o3060. [PMC free article] [PubMed]
  • Yoon, Y. K., Ali, M. A., Wei, A. C., Asik, S. I. J. & Razak, I. A. (2012). Acta Cryst. E68, o471–o472. [PMC free article] [PubMed]
  • Yoon, Y. K., Ali, M. A., Wei, A. C., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o2405. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography