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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o20–o21.
Published online 2008 December 3. doi:  10.1107/S1600536808038002
PMCID: PMC2967940

6,6′-Dimeth­oxy-2,2′-[2,2-dimethyl­propane-1,3-diylbis(nitrilo­methyl­idyne)]diphenol

Abstract

The title Schiff base compound, C21H26N2O4, exhibits two crystallographically independent mol­ecules in the asymmetric unit with similar conformations. The imino groups are coplanar with the benzene rings; the maximum deviations of the N atoms from the planes comprising the benzene rings and the imino groups are −0.037 (4), 0.013 (4), −0.021 (5), and 0.008 (5) Å. The dihedral angles between the benzene rings in the two mol­ecules are 53.64 (17) and 51.93 (17)°. Strong intra­molecular O—H(...)N hydrogen bonds generate S(6) ring motifs. The N atoms are also in close proximity to the H atoms of the dimethyl­propane groups, with H(...)N distances between 2.54 and 2.75 Å. The crystal structure is further stabilized by weak inter­molecular C—H(...)O hydrogen bonds, weak inter­molecular C—H(...)π inter­actions and π–π contacts involving the imine C atom and two C atoms from the adjacent benzene rings.

Related literature

For reference bond lengths, see Allen et al. (1987 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For information on Schiff base ligands and complexes and their applications, see: Calligaris & Randaccio (1987 [triangle]). For related structures, see: Li et al. (2005 [triangle]); Bomfim et al. (2005 [triangle]); Glidewell et al. (2006 [triangle]); Sun et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-00o20-scheme1.jpg

Experimental

Crystal data

  • C21H26N2O4
  • M r = 370.44
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-00o20-efi1.jpg
  • a = 6.8859 (3) Å
  • b = 30.8090 (14) Å
  • c = 18.8611 (9) Å
  • β = 96.102 (3)°
  • V = 3978.7 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100.0 (1) K
  • 0.45 × 0.38 × 0.26 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.962, T max = 0.978
  • 55368 measured reflections
  • 7045 independent reflections
  • 6422 reflections with I > 2σ(I)
  • R int = 0.050

Refinement

  • R[F 2 > 2σ(F 2)] = 0.070
  • wR(F 2) = 0.202
  • S = 1.07
  • 7045 reflections
  • 495 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.45 e Å−3
  • Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 [triangle]); 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, 2003 [triangle]).

Table 1
Selected geometric parameters (Å) associated with π–π stacking interactions between the planar sections of C1A–C6A–C7A–N1A and C5B–C6B–C7B–N1B
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038002/zl2157sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038002/zl2157Isup2.hkl

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

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia for an RU research grant (No. 101/PKIMIA/815002) and facilities. HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for a Science Fund grant (No. 305/PFIZIK/613312). RK thanks Universiti Sains Malaysia for a postdoctoral research fellowship. HK thanks PNU for partial financial support.

supplementary crystallographic information

Comment

Schiff bases are one of the most prevalent mixed-donor ligands in the field of coordination chemistry. They play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism, and supramolecular architectures (Calligaris & Randaccio, 1987). Structures of Schiff bases derived from substituted benzaldehydes and closely related to the title compound have been reported earlier (Li et al., 2005; Bomfim et al., 2005; Glidewell et al., 2006; Sun et al., 2004).

The molecule of the title compound (Fig. 1), consists of two crystallographically independent molecules, A and B, with similar conformations. The bond lengths (Allen et al., 1987) and angles are within the normal ranges. The imino groups in both molecules are coplanar with the benzene rings they are attached to, and the dihedral angles between the benzene rings in molecules A and B are 53.64 (17) and 51.93 (17)°, respectively. Strong intramolecular O—H···N hydrogen bonds generate S(6) ring motifs (Bernstein et al., 1995). The nitrogen atoms are also in close proximity to the hydrogen atoms of the dimethylpropane groups with H···N distances between 2.54 and 2.75 Å (Table 2). There is also a significant π-stacking interaction between the planar sections associated with C1A–C6A–C7A–N1A and C5B–C6B–C7B–N1B (Table 1), and the crystal structure is further stabilized by weak intermolecular C—H···O hydrogen bonds and weak intermolecular C—H···π interactions (Cg1 and Cg2 are the centroids of the C12B–C17B and C12A–C17A benzene rings) (Table 2).

Experimental

In a 50 ml round-bottomed flask, 3-methoxy salicylaldehyde (2 mmol, 304 mg) was added into a 30 ml ethanolic solution of 2,2-dimethyl-1,3-propane diamine (1 mmol, 102 mg) and then the mixture was next refluxed for 1 h. The resulting yellow solid was filtered and washed with cold ethanol. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution at room temperature.

Refinement

H atoms of the hydroxy groups were positioned by a freely rotating O—H bond and constrained with a fixed distance of 0.84 Å. The rest of the hydrogen atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.97 Å and Uiso(H) = 1.2 or 1.5Ueq(C). A rotating-group model was applied for the methyl hydrogen atoms of the methoxy groups. In the absence of sufficient anomalous scattering effects the Friedel pairs were merged prior to refinement.

Figures

Fig. 1.
The molecular structure of the title compound with atom labels and 50% probability ellipsoids for non-H atoms. Dashed lines indicate intramolecular O—H···N hydrogen bonds.
Fig. 2.
The crystal structure of the title compound, viewed down the a axis.

Crystal data

C21H26N2O4F(000) = 1584
Mr = 370.44Dx = 1.237 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 9913 reflections
a = 6.8859 (3) Åθ = 2.5–31.8°
b = 30.8090 (14) ŵ = 0.09 mm1
c = 18.8611 (9) ÅT = 100 K
β = 96.102 (3)°Block, yellow
V = 3978.7 (3) Å30.45 × 0.38 × 0.26 mm
Z = 8

Data collection

Bruker SMART APEXII CCD area-detector diffractometer7045 independent reflections
Radiation source: fine-focus sealed tube6422 reflections with I > 2σ(I)
graphiteRint = 0.050
[var phi] and ω scansθmax = 32.3°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −10→10
Tmin = 0.962, Tmax = 0.978k = −46→46
55368 measured reflectionsl = −28→28

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)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.202H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.1051P)2 + 8.0789P] where P = (Fo2 + 2Fc2)/3
7045 reflections(Δ/σ)max = 0.002
495 parametersΔρmax = 0.45 e Å3
2 restraintsΔρmin = −0.37 e Å3

Special details

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1A0.6602 (3)0.61681 (8)0.79393 (15)0.0220 (5)
H1A0.65140.64330.78370.033*
O2A0.1871 (4)0.81687 (9)0.62720 (15)0.0262 (5)
H2A0.25520.81260.66620.039*
O3A0.7407 (4)0.53607 (8)0.82872 (15)0.0231 (5)
O4A−0.0011 (4)0.84221 (9)0.50566 (15)0.0256 (5)
N1A0.7730 (4)0.69245 (9)0.75795 (16)0.0200 (5)
N2A0.5033 (4)0.82012 (9)0.71799 (16)0.0209 (5)
C1A0.8478 (4)0.60400 (10)0.79486 (17)0.0162 (5)
C2A0.8952 (5)0.56063 (10)0.81212 (17)0.0187 (6)
C3A1.0852 (5)0.54614 (11)0.81211 (19)0.0223 (6)
H3AA1.11630.51690.82430.027*
C4A1.2326 (5)0.57441 (12)0.7942 (2)0.0228 (6)
H4AA1.36230.56410.79330.027*
C5A1.1880 (5)0.61752 (11)0.7780 (2)0.0205 (6)
H5AA1.28790.63680.76660.025*
C6A0.9952 (5)0.63275 (10)0.77833 (17)0.0175 (5)
C7A0.9487 (5)0.67788 (10)0.76016 (18)0.0183 (5)
H7AA1.05040.69690.74970.022*
C8A0.7357 (5)0.73797 (10)0.74149 (19)0.0210 (6)
H8AA0.65480.74040.69500.025*
H8AB0.86100.75300.73750.025*
C9A0.6290 (5)0.76003 (10)0.79997 (18)0.0202 (6)
C10A0.6207 (5)0.80896 (10)0.78462 (19)0.0213 (6)
H10A0.56590.82390.82450.026*
H10B0.75530.81990.78270.026*
C11A0.5777 (5)0.84575 (10)0.67483 (18)0.0198 (6)
H11A0.70690.85610.68700.024*
C12A0.4712 (5)0.85970 (11)0.60758 (18)0.0198 (6)
C13A0.5596 (5)0.88882 (14)0.5638 (2)0.0267 (7)
H13A0.68660.89980.57830.032*
C14A0.4617 (6)0.90153 (14)0.4996 (2)0.0285 (7)
H14A0.52250.92100.46980.034*
C15A0.2746 (6)0.88615 (13)0.4779 (2)0.0253 (7)
H15A0.20950.89490.43330.030*
C16A0.1831 (5)0.85812 (11)0.52116 (19)0.0206 (6)
C17A0.2814 (5)0.84420 (10)0.58698 (18)0.0184 (5)
C18A0.7447 (7)0.75372 (13)0.8731 (2)0.0300 (8)
H18A0.67570.76780.90970.045*
H18B0.87470.76670.87290.045*
H18C0.75800.72260.88350.045*
C19A0.4231 (6)0.74167 (13)0.7997 (2)0.0289 (8)
H19A0.35120.74590.75250.043*
H19B0.35520.75670.83570.043*
H19C0.43060.71060.81080.043*
C20A−0.1043 (6)0.85672 (13)0.4401 (2)0.0272 (7)
H20A−0.23550.84400.43460.041*
H20B−0.03350.84770.40020.041*
H20C−0.11460.88840.44060.041*
C21A0.7845 (7)0.49164 (11)0.8457 (2)0.0291 (7)
H21A0.66510.47670.85600.044*
H21B0.88160.49020.88750.044*
H21C0.83680.47760.80510.044*
O1B0.5634 (3)0.64558 (8)0.58470 (15)0.0216 (5)
H1B0.56390.62100.60410.032*
O2B0.2253 (4)0.44378 (9)0.76179 (15)0.0255 (5)
H2B0.27860.45070.72540.038*
O3B0.6121 (4)0.72611 (9)0.54496 (16)0.0260 (5)
O4B0.1066 (4)0.41813 (9)0.88280 (15)0.0270 (5)
N1B0.7096 (4)0.57124 (9)0.62454 (16)0.0204 (5)
N2B0.4884 (4)0.44138 (9)0.67216 (16)0.0206 (5)
C1B0.7484 (4)0.65956 (10)0.58381 (18)0.0170 (5)
C2B0.7791 (5)0.70283 (11)0.56300 (18)0.0202 (6)
C3B0.9687 (5)0.71851 (11)0.5621 (2)0.0228 (6)
H3BA0.98950.74760.54790.027*
C4B1.1290 (5)0.69138 (12)0.5821 (2)0.0249 (7)
H4BA1.25780.70240.58210.030*
C5B1.1014 (5)0.64898 (11)0.6016 (2)0.0215 (6)
H5BA1.21110.63080.61440.026*
C6B0.9113 (5)0.63246 (11)0.60275 (17)0.0173 (5)
C7B0.8806 (5)0.58763 (10)0.62376 (18)0.0187 (5)
H7BA0.99130.56990.63740.022*
C8B0.6908 (5)0.52569 (11)0.64410 (19)0.0212 (6)
H8BA0.63930.52380.69110.025*
H8BB0.82110.51180.64830.025*
C9B0.5533 (5)0.50155 (10)0.58819 (18)0.0194 (6)
C10B0.5641 (5)0.45275 (10)0.60503 (19)0.0203 (6)
H10C0.48890.43670.56570.024*
H10D0.70190.44320.60710.024*
C11B0.5880 (5)0.41536 (10)0.71459 (19)0.0208 (6)
H11B0.70980.40500.70210.025*
C12B0.5202 (5)0.40099 (11)0.78172 (18)0.0193 (6)
C13B0.6361 (5)0.37212 (13)0.8259 (2)0.0264 (7)
H13B0.75580.36170.81160.032*
C14B0.5756 (6)0.35898 (14)0.8901 (2)0.0290 (7)
H14B0.65320.33930.91970.035*
C15B0.4011 (6)0.37457 (12)0.91147 (19)0.0245 (7)
H15B0.36240.36580.95620.029*
C16B0.2833 (5)0.40253 (11)0.86886 (18)0.0210 (6)
C17B0.3442 (5)0.41619 (10)0.80270 (18)0.0191 (6)
C18B0.6217 (7)0.50736 (13)0.5136 (2)0.0317 (8)
H18D0.53230.49190.47830.048*
H18E0.75370.49550.51340.048*
H18F0.62240.53830.50160.048*
C19B0.3445 (6)0.51819 (13)0.5896 (3)0.0302 (8)
H19D0.30410.51420.63740.045*
H19E0.25640.50190.55500.045*
H19F0.33910.54910.57730.045*
C20B0.0398 (6)0.40411 (14)0.9482 (2)0.0291 (7)
H20D−0.08610.41780.95380.044*
H20E0.13530.41240.98810.044*
H20F0.02450.37250.94740.044*
C21B0.6384 (6)0.76900 (12)0.5185 (3)0.0313 (8)
H21D0.51140.78350.51030.047*
H21E0.69750.76730.47350.047*
H21F0.72420.78550.55350.047*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0150 (10)0.0177 (10)0.0338 (13)0.0015 (8)0.0053 (9)0.0003 (9)
O2A0.0263 (13)0.0208 (11)0.0296 (13)−0.0085 (10)−0.0051 (10)0.0080 (10)
O3A0.0230 (11)0.0157 (10)0.0314 (13)−0.0021 (9)0.0057 (9)0.0016 (9)
O4A0.0227 (12)0.0256 (12)0.0266 (12)−0.0056 (9)−0.0064 (9)0.0038 (10)
N1A0.0208 (12)0.0137 (11)0.0250 (13)0.0031 (9)−0.0003 (10)−0.0006 (10)
N2A0.0233 (13)0.0137 (11)0.0244 (13)0.0026 (10)−0.0036 (10)0.0004 (9)
C1A0.0147 (12)0.0152 (12)0.0184 (13)0.0005 (10)−0.0007 (10)−0.0028 (10)
C2A0.0205 (14)0.0159 (13)0.0191 (13)−0.0015 (10)0.0001 (10)−0.0013 (10)
C3A0.0237 (15)0.0164 (13)0.0258 (15)0.0036 (11)−0.0020 (12)−0.0026 (11)
C4A0.0178 (13)0.0207 (14)0.0294 (16)0.0031 (11)−0.0002 (12)−0.0036 (12)
C5A0.0141 (12)0.0186 (13)0.0285 (16)0.0013 (10)0.0013 (11)−0.0037 (11)
C6A0.0151 (12)0.0170 (13)0.0200 (13)−0.0003 (10)−0.0007 (10)−0.0027 (10)
C7A0.0170 (13)0.0156 (12)0.0221 (14)−0.0008 (10)0.0010 (10)−0.0008 (10)
C8A0.0238 (14)0.0124 (12)0.0271 (15)0.0032 (11)0.0032 (12)0.0015 (11)
C9A0.0232 (14)0.0154 (12)0.0212 (14)0.0015 (11)−0.0005 (11)−0.0012 (10)
C10A0.0235 (15)0.0128 (12)0.0260 (15)0.0014 (11)−0.0055 (12)−0.0003 (11)
C11A0.0179 (13)0.0173 (13)0.0232 (14)0.0011 (10)−0.0022 (11)0.0001 (11)
C12A0.0175 (13)0.0181 (13)0.0234 (14)−0.0004 (11)0.0006 (11)0.0006 (11)
C13A0.0193 (15)0.0313 (18)0.0291 (17)−0.0024 (13)0.0010 (13)0.0038 (14)
C14A0.0268 (17)0.0337 (19)0.0258 (16)−0.0005 (14)0.0059 (13)0.0058 (14)
C15A0.0261 (16)0.0268 (16)0.0224 (15)0.0063 (13)−0.0002 (12)0.0006 (12)
C16A0.0214 (14)0.0178 (13)0.0217 (14)0.0028 (11)−0.0021 (11)−0.0015 (11)
C17A0.0180 (13)0.0148 (12)0.0221 (14)0.0000 (10)0.0002 (10)−0.0007 (10)
C18A0.043 (2)0.0221 (15)0.0228 (16)0.0059 (15)−0.0043 (15)0.0005 (12)
C19A0.0213 (15)0.0220 (16)0.043 (2)−0.0010 (12)0.0033 (14)0.0057 (14)
C20A0.0284 (17)0.0277 (16)0.0234 (16)0.0010 (14)−0.0066 (13)0.0023 (13)
C21A0.038 (2)0.0159 (14)0.0341 (19)−0.0042 (14)0.0081 (15)−0.0020 (13)
O1B0.0135 (10)0.0181 (10)0.0328 (13)−0.0021 (8)0.0010 (9)0.0017 (9)
O2B0.0310 (13)0.0203 (11)0.0270 (12)0.0112 (10)0.0106 (10)0.0082 (9)
O3B0.0221 (12)0.0186 (11)0.0368 (14)0.0028 (9)0.0014 (10)0.0038 (10)
O4B0.0273 (13)0.0280 (13)0.0277 (13)0.0048 (10)0.0125 (10)0.0056 (10)
N1B0.0221 (13)0.0171 (12)0.0216 (12)−0.0021 (10)0.0011 (10)0.0012 (10)
N2B0.0238 (13)0.0144 (11)0.0246 (13)−0.0010 (10)0.0077 (10)0.0003 (10)
C1B0.0144 (12)0.0161 (12)0.0205 (13)−0.0006 (10)0.0026 (10)−0.0011 (10)
C2B0.0201 (14)0.0181 (13)0.0222 (14)−0.0006 (11)0.0024 (11)−0.0010 (11)
C3B0.0218 (15)0.0167 (13)0.0302 (16)−0.0024 (11)0.0042 (12)−0.0008 (12)
C4B0.0211 (15)0.0215 (15)0.0326 (17)−0.0014 (12)0.0056 (13)−0.0022 (13)
C5B0.0164 (13)0.0204 (14)0.0278 (16)−0.0022 (11)0.0028 (11)−0.0018 (12)
C6B0.0168 (12)0.0187 (13)0.0164 (12)−0.0002 (10)0.0011 (10)−0.0018 (10)
C7B0.0185 (13)0.0158 (12)0.0217 (14)0.0000 (10)0.0013 (10)−0.0013 (10)
C8B0.0238 (15)0.0142 (12)0.0249 (15)−0.0005 (11)−0.0006 (12)0.0030 (11)
C9B0.0216 (14)0.0154 (12)0.0209 (14)−0.0012 (10)0.0016 (11)0.0021 (10)
C10B0.0244 (15)0.0152 (12)0.0226 (14)−0.0020 (11)0.0082 (12)0.0005 (11)
C11B0.0215 (14)0.0156 (13)0.0264 (15)−0.0030 (11)0.0075 (12)−0.0014 (11)
C12B0.0196 (14)0.0163 (13)0.0220 (14)−0.0040 (10)0.0017 (11)0.0008 (10)
C13B0.0188 (15)0.0271 (16)0.0328 (18)0.0033 (12)0.0009 (13)0.0065 (14)
C14B0.0232 (16)0.0313 (18)0.0315 (18)−0.0018 (14)−0.0026 (14)0.0079 (14)
C15B0.0260 (16)0.0242 (15)0.0226 (15)−0.0061 (13)−0.0005 (12)0.0027 (12)
C16B0.0244 (15)0.0179 (13)0.0209 (14)−0.0020 (11)0.0034 (11)−0.0026 (11)
C17B0.0234 (14)0.0118 (11)0.0223 (14)−0.0022 (10)0.0038 (11)0.0011 (10)
C18B0.047 (2)0.0244 (17)0.0244 (16)−0.0090 (16)0.0100 (16)0.0029 (13)
C19B0.0211 (16)0.0275 (17)0.041 (2)−0.0001 (13)−0.0013 (14)0.0073 (15)
C20B0.0352 (19)0.0304 (18)0.0233 (16)−0.0035 (15)0.0110 (14)−0.0004 (13)
C21B0.0323 (19)0.0149 (14)0.046 (2)0.0030 (13)0.0013 (17)0.0026 (14)

Geometric parameters (Å, °)

O1A—C1A1.349 (4)O1B—C1B1.347 (4)
O1A—H1A0.8400O1B—H1B0.8400
O2A—C17A1.346 (4)O2B—C17B1.362 (4)
O2A—H2A0.8400O2B—H2B0.8400
O3A—C2A1.369 (4)O3B—C2B1.367 (4)
O3A—C21A1.430 (4)O3B—C21B1.431 (5)
O4A—C16A1.362 (4)O4B—C16B1.360 (4)
O4A—C20A1.431 (4)O4B—C20B1.427 (5)
N1A—C7A1.287 (4)N1B—C7B1.283 (4)
N1A—C8A1.454 (4)N1B—C8B1.460 (4)
N2A—C11A1.280 (5)N2B—C11B1.279 (4)
N2A—C10A1.461 (4)N2B—C10B1.462 (4)
C1A—C2A1.406 (4)C1B—C2B1.412 (4)
C1A—C6A1.407 (5)C1B—C6B1.413 (4)
C2A—C3A1.382 (5)C2B—C3B1.394 (5)
C3A—C4A1.406 (5)C3B—C4B1.404 (5)
C3A—H3AA0.9500C3B—H3BA0.9500
C4A—C5A1.390 (5)C4B—C5B1.376 (5)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.409 (4)C5B—C6B1.407 (5)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—C7A1.460 (4)C6B—C7B1.458 (5)
C7A—H7AA0.9500C7B—H7BA0.9500
C8A—C9A1.546 (5)C8B—C9B1.533 (5)
C8A—H8AA0.9900C8B—H8BA0.9900
C8A—H8AB0.9900C8B—H8BB0.9900
C9A—C19A1.526 (5)C9B—C19B1.530 (5)
C9A—C18A1.530 (5)C9B—C10B1.537 (4)
C9A—C10A1.535 (4)C9B—C18B1.540 (5)
C10A—H10A0.9900C10B—H10C0.9900
C10A—H10B0.9900C10B—H10D0.9900
C11A—C12A1.461 (4)C11B—C12B1.464 (5)
C11A—H11A0.9500C11B—H11B0.9500
C12A—C13A1.401 (5)C12B—C17B1.395 (5)
C12A—C17A1.406 (5)C12B—C13B1.407 (5)
C13A—C14A1.378 (5)C13B—C14B1.382 (6)
C13A—H13A0.9500C13B—H13B0.9500
C14A—C15A1.392 (6)C14B—C15B1.393 (6)
C14A—H14A0.9500C14B—H14B0.9500
C15A—C16A1.385 (5)C15B—C16B1.381 (5)
C15A—H15A0.9500C15B—H15B0.9500
C16A—C17A1.416 (4)C16B—C17B1.422 (5)
C18A—H18A0.9800C18B—H18D0.9800
C18A—H18B0.9800C18B—H18E0.9800
C18A—H18C0.9800C18B—H18F0.9800
C19A—H19A0.9800C19B—H19D0.9800
C19A—H19B0.9800C19B—H19E0.9800
C19A—H19C0.9800C19B—H19F0.9800
C20A—H20A0.9800C20B—H20D0.9800
C20A—H20B0.9800C20B—H20E0.9800
C20A—H20C0.9800C20B—H20F0.9800
C21A—H21A0.9800C21B—H21D0.9800
C21A—H21B0.9800C21B—H21E0.9800
C21A—H21C0.9800C21B—H21F0.9800
C1A···C7B3.298 (5)C7A···C5B3.393 (5)
C6A···C6B3.300 (5)C7A···C6B3.267 (5)
C6A···C7B3.250 (3)
C1A—O1A—H1A109.5C1B—O1B—H1B109.5
C17A—O2A—H2A109.5C17B—O2B—H2B109.5
C2A—O3A—C21A115.4 (3)C2B—O3B—C21B115.9 (3)
C16A—O4A—C20A116.0 (3)C16B—O4B—C20B115.9 (3)
C7A—N1A—C8A119.2 (3)C7B—N1B—C8B119.2 (3)
C11A—N2A—C10A118.0 (3)C11B—N2B—C10B118.4 (3)
O1A—C1A—C2A118.7 (3)O1B—C1B—C2B118.3 (3)
O1A—C1A—C6A121.7 (3)O1B—C1B—C6B122.3 (3)
C2A—C1A—C6A119.6 (3)C2B—C1B—C6B119.4 (3)
O3A—C2A—C3A125.5 (3)O3B—C2B—C3B125.4 (3)
O3A—C2A—C1A114.3 (3)O3B—C2B—C1B114.7 (3)
C3A—C2A—C1A120.2 (3)C3B—C2B—C1B119.9 (3)
C2A—C3A—C4A120.5 (3)C2B—C3B—C4B120.1 (3)
C2A—C3A—H3AA119.7C2B—C3B—H3BA120.0
C4A—C3A—H3AA119.7C4B—C3B—H3BA120.0
C5A—C4A—C3A119.8 (3)C5B—C4B—C3B120.7 (3)
C5A—C4A—H4AA120.1C5B—C4B—H4BA119.7
C3A—C4A—H4AA120.1C3B—C4B—H4BA119.7
C4A—C5A—C6A120.2 (3)C4B—C5B—C6B120.2 (3)
C4A—C5A—H5AA119.9C4B—C5B—H5BA119.9
C6A—C5A—H5AA119.9C6B—C5B—H5BA119.9
C1A—C6A—C5A119.6 (3)C5B—C6B—C1B119.8 (3)
C1A—C6A—C7A120.4 (3)C5B—C6B—C7B120.6 (3)
C5A—C6A—C7A120.0 (3)C1B—C6B—C7B119.6 (3)
N1A—C7A—C6A121.5 (3)N1B—C7B—C6B122.4 (3)
N1A—C7A—H7AA119.3N1B—C7B—H7BA118.8
C6A—C7A—H7AA119.3C6B—C7B—H7BA118.8
N1A—C8A—C9A111.0 (3)N1B—C8B—C9B110.9 (3)
N1A—C8A—H8AA109.4N1B—C8B—H8BA109.5
C9A—C8A—H8AA109.4C9B—C8B—H8BA109.5
N1A—C8A—H8AB109.4N1B—C8B—H8BB109.5
C9A—C8A—H8AB109.4C9B—C8B—H8BB109.5
H8AA—C8A—H8AB108.0H8BA—C8B—H8BB108.0
C19A—C9A—C18A110.5 (3)C19B—C9B—C8B109.8 (3)
C19A—C9A—C10A110.3 (3)C19B—C9B—C10B110.4 (3)
C18A—C9A—C10A107.5 (3)C8B—C9B—C10B108.7 (3)
C19A—C9A—C8A110.3 (3)C19B—C9B—C18B110.8 (3)
C18A—C9A—C8A110.2 (3)C8B—C9B—C18B110.2 (3)
C10A—C9A—C8A108.0 (3)C10B—C9B—C18B106.8 (3)
N2A—C10A—C9A113.5 (3)N2B—C10B—C9B113.6 (3)
N2A—C10A—H10A108.9N2B—C10B—H10C108.9
C9A—C10A—H10A108.9C9B—C10B—H10C108.9
N2A—C10A—H10B108.9N2B—C10B—H10D108.9
C9A—C10A—H10B108.9C9B—C10B—H10D108.9
H10A—C10A—H10B107.7H10C—C10B—H10D107.7
N2A—C11A—C12A122.4 (3)N2B—C11B—C12B122.1 (3)
N2A—C11A—H11A118.8N2B—C11B—H11B118.9
C12A—C11A—H11A118.8C12B—C11B—H11B118.9
C13A—C12A—C17A120.2 (3)C17B—C12B—C13B119.9 (3)
C13A—C12A—C11A119.4 (3)C17B—C12B—C11B120.7 (3)
C17A—C12A—C11A120.4 (3)C13B—C12B—C11B119.4 (3)
C14A—C13A—C12A119.8 (3)C14B—C13B—C12B119.9 (4)
C14A—C13A—H13A120.1C14B—C13B—H13B120.0
C12A—C13A—H13A120.1C12B—C13B—H13B120.0
C13A—C14A—C15A120.8 (4)C13B—C14B—C15B120.1 (4)
C13A—C14A—H14A119.6C13B—C14B—H14B119.9
C15A—C14A—H14A119.6C15B—C14B—H14B119.9
C16A—C15A—C14A120.3 (3)C16B—C15B—C14B121.2 (3)
C16A—C15A—H15A119.9C16B—C15B—H15B119.4
C14A—C15A—H15A119.9C14B—C15B—H15B119.4
O4A—C16A—C15A124.7 (3)O4B—C16B—C15B126.2 (3)
O4A—C16A—C17A115.3 (3)O4B—C16B—C17B114.7 (3)
C15A—C16A—C17A120.0 (3)C15B—C16B—C17B119.1 (3)
O2A—C17A—C12A123.1 (3)O2B—C17B—C12B122.5 (3)
O2A—C17A—C16A118.0 (3)O2B—C17B—C16B117.8 (3)
C12A—C17A—C16A118.9 (3)C12B—C17B—C16B119.7 (3)
C9A—C18A—H18A109.5C9B—C18B—H18D109.5
C9A—C18A—H18B109.5C9B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C9A—C18A—H18C109.5C9B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
C9A—C19A—H19A109.5C9B—C19B—H19D109.5
C9A—C19A—H19B109.5C9B—C19B—H19E109.5
H19A—C19A—H19B109.5H19D—C19B—H19E109.5
C9A—C19A—H19C109.5C9B—C19B—H19F109.5
H19A—C19A—H19C109.5H19D—C19B—H19F109.5
H19B—C19A—H19C109.5H19E—C19B—H19F109.5
O4A—C20A—H20A109.5O4B—C20B—H20D109.5
O4A—C20A—H20B109.5O4B—C20B—H20E109.5
H20A—C20A—H20B109.5H20D—C20B—H20E109.5
O4A—C20A—H20C109.5O4B—C20B—H20F109.5
H20A—C20A—H20C109.5H20D—C20B—H20F109.5
H20B—C20A—H20C109.5H20E—C20B—H20F109.5
O3A—C21A—H21A109.5O3B—C21B—H21D109.5
O3A—C21A—H21B109.5O3B—C21B—H21E109.5
H21A—C21A—H21B109.5H21D—C21B—H21E109.5
O3A—C21A—H21C109.5O3B—C21B—H21F109.5
H21A—C21A—H21C109.5H21D—C21B—H21F109.5
H21B—C21A—H21C109.5H21E—C21B—H21F109.5
C21A—O3A—C2A—C3A−1.4 (5)C21B—O3B—C2B—C3B4.6 (5)
C21A—O3A—C2A—C1A179.3 (3)C21B—O3B—C2B—C1B−175.4 (3)
O1A—C1A—C2A—O3A−2.0 (4)O1B—C1B—C2B—O3B−0.6 (4)
C6A—C1A—C2A—O3A178.6 (3)C6B—C1B—C2B—O3B179.3 (3)
O1A—C1A—C2A—C3A178.6 (3)O1B—C1B—C2B—C3B179.4 (3)
C6A—C1A—C2A—C3A−0.7 (5)C6B—C1B—C2B—C3B−0.7 (5)
O3A—C2A—C3A—C4A−179.9 (3)O3B—C2B—C3B—C4B179.8 (3)
C1A—C2A—C3A—C4A−0.6 (5)C1B—C2B—C3B—C4B−0.2 (5)
C2A—C3A—C4A—C5A1.4 (5)C2B—C3B—C4B—C5B1.0 (6)
C3A—C4A—C5A—C6A−1.0 (5)C3B—C4B—C5B—C6B−0.9 (6)
O1A—C1A—C6A—C5A−178.1 (3)C4B—C5B—C6B—C1B−0.1 (5)
C2A—C1A—C6A—C5A1.2 (5)C4B—C5B—C6B—C7B−179.7 (3)
O1A—C1A—C6A—C7A0.6 (5)O1B—C1B—C6B—C5B−179.3 (3)
C2A—C1A—C6A—C7A179.9 (3)C2B—C1B—C6B—C5B0.9 (5)
C4A—C5A—C6A—C1A−0.3 (5)O1B—C1B—C6B—C7B0.3 (5)
C4A—C5A—C6A—C7A−179.1 (3)C2B—C1B—C6B—C7B−179.5 (3)
C8A—N1A—C7A—C6A178.3 (3)C8B—N1B—C7B—C6B178.1 (3)
C1A—C6A—C7A—N1A−0.8 (5)C5B—C6B—C7B—N1B−179.1 (3)
C5A—C6A—C7A—N1A177.9 (3)C1B—C6B—C7B—N1B1.3 (5)
C7A—N1A—C8A—C9A−125.4 (3)C7B—N1B—C8B—C9B−128.7 (3)
N1A—C8A—C9A—C19A−67.3 (4)N1B—C8B—C9B—C19B−67.9 (4)
N1A—C8A—C9A—C18A55.0 (4)N1B—C8B—C9B—C10B171.2 (3)
N1A—C8A—C9A—C10A172.1 (3)N1B—C8B—C9B—C18B54.4 (4)
C11A—N2A—C10A—C9A−130.8 (3)C11B—N2B—C10B—C9B−134.3 (3)
C19A—C9A—C10A—N2A−55.8 (4)C19B—C9B—C10B—N2B−54.7 (4)
C18A—C9A—C10A—N2A−176.4 (3)C8B—C9B—C10B—N2B65.8 (4)
C8A—C9A—C10A—N2A64.8 (4)C18B—C9B—C10B—N2B−175.3 (3)
C10A—N2A—C11A—C12A−178.6 (3)C10B—N2B—C11B—C12B−177.8 (3)
N2A—C11A—C12A—C13A178.2 (3)N2B—C11B—C12B—C17B−1.5 (5)
N2A—C11A—C12A—C17A−1.6 (5)N2B—C11B—C12B—C13B179.7 (3)
C17A—C12A—C13A—C14A−1.4 (6)C17B—C12B—C13B—C14B−0.2 (6)
C11A—C12A—C13A—C14A178.8 (4)C11B—C12B—C13B—C14B178.7 (3)
C12A—C13A—C14A—C15A0.7 (6)C12B—C13B—C14B—C15B−0.6 (6)
C13A—C14A—C15A—C16A0.7 (6)C13B—C14B—C15B—C16B1.4 (6)
C20A—O4A—C16A—C15A−1.0 (5)C20B—O4B—C16B—C15B0.4 (5)
C20A—O4A—C16A—C17A178.6 (3)C20B—O4B—C16B—C17B178.6 (3)
C14A—C15A—C16A—O4A178.2 (4)C14B—C15B—C16B—O4B176.8 (4)
C14A—C15A—C16A—C17A−1.4 (5)C14B—C15B—C16B—C17B−1.3 (5)
C13A—C12A—C17A—O2A−178.7 (3)C13B—C12B—C17B—O2B−179.3 (3)
C11A—C12A—C17A—O2A1.1 (5)C11B—C12B—C17B—O2B1.8 (5)
C13A—C12A—C17A—C16A0.7 (5)C13B—C12B—C17B—C16B0.2 (5)
C11A—C12A—C17A—C16A−179.5 (3)C11B—C12B—C17B—C16B−178.6 (3)
O4A—C16A—C17A—O2A0.5 (5)O4B—C16B—C17B—O2B1.7 (4)
C15A—C16A—C17A—O2A−179.8 (3)C15B—C16B—C17B—O2B−180.0 (3)
O4A—C16A—C17A—C12A−179.0 (3)O4B—C16B—C17B—C12B−177.8 (3)
C15A—C16A—C17A—C12A0.7 (5)C15B—C16B—C17B—C12B0.5 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1A—H1A···N1A0.841.822.570 (4)148
O1B—H1B···N1B0.841.852.581 (4)144
O2A—H2A···N2A0.841.892.625 (4)145
O2B—H2B···N2B0.841.872.607 (4)146
C5B—H5BA···O1Bi0.952.593.233 (4)125
C18A—H18C···N1A0.982.562.900 (5)100
C18B—H18F···N1B0.982.542.889 (5)101
C18A—H18C···N1A0.982.562.900 (5)101
C19A—H19C···N1A0.982.713.021 (5)99
C19A—H19A···N2A0.982.632.950 (5)100
C19B—H19F···N1B0.982.703.012 (5)99
C19B—H19D···N2B0.982.632.946 (5)99
C8B—H8BA···N2B0.992.753.021 (5)96
C10A—H10B···Cg1ii0.992.733.481 (4)133
C10B—H10D···Cg2iii0.992.793.524 (4)131

Symmetry codes: (i) x+1, y, z; (ii) x+1/2, y+1/2, z; (iii) x+1/2, y−1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2157).

References

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  • Calligaris, M. & Randaccio, L. (1987). Comprehensive Coordination Chemistry, Vol. 2, edited by G. Wilkinson, pp. 715–738. London: Pergamon.
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