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Acta Crystallogr Sect E Struct Rep Online. 2012 January 1; 68(Pt 1): o87–o88.
Published online 2011 December 10. doi:  10.1107/S1600536811052391
PMCID: PMC3254439

Ethyl 2-(4-hy­droxy-3-meth­oxy­phen­yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate monohydrate

Abstract

In the title compound, C24H27N3O5·H2O, the essentially planar benzimidazole ring system [maximum deviation = 0.020 (1) Å] forms dihedral angles of 54.10 (11) and 67.79 (6)°, respectively, with the mean plane of pyrrolidin-2-one ring and the benzene ring. The pyrrolidin-2-one ring adopts an envelope conformation with one of the methylene C atoms at the flap. An intra­molecular C—H(...)π inter­action is observed. In the crystal, O—H(...)O and O—H(...)N hydrogen bonds link the two components into a double-tape structure along the a axis. The crystal packing is further stabilized by weak π–π stacking [centroid–centroid distance = 3.6632 (9) Å] and C—H(...)O inter­actions.

Related literature

For the biological activity of benzimidazole derivatives, see: Rao et al. (2002 [triangle]); Thakurdesai et al. (2007 [triangle]); Dubey & Sanyal (2010 [triangle]). For related structures, see: Yoon et al. (2011 [triangle]). For the ring conformation, see: Cremer & Pople (1975) [triangle].

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Object name is e-68-00o87-scheme1.jpg

Experimental

Crystal data

  • C24H27N3O5·H2O
  • M r = 455.50
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-00o87-efi1.jpg
  • a = 9.7460 (8) Å
  • b = 10.0436 (8) Å
  • c = 12.6072 (10) Å
  • α = 85.737 (1)°
  • β = 89.684 (2)°
  • γ = 70.238 (1)°
  • V = 1157.91 (16) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 296 K
  • 0.43 × 0.32 × 0.16 mm

Data collection

  • Bruker APEXII DUO CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.960, T max = 0.985
  • 18195 measured reflections
  • 6686 independent reflections
  • 4485 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.185
  • S = 1.07
  • 6686 reflections
  • 312 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.26 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/S1600536811052391/is5022sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052391/is5022Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052391/is5022Isup3.cml

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

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant Nos. 1001/PFIZIK/811151 and 1001/PSK/8620012. The authors also wish to express their thanks to the Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Mol­ecular Medicine, Universiti of Sains Malaysia.

supplementary crystallographic information

Comment

Benzimidazole derivatives are of wide interest because of their diverse biological activities and various clinical applications. This ring system is present in numerous anti-HIV (Rao et al., 2002), anti-inflammatory (Thakurdesai et al., 2007) and anthelmintics (Dubey and Sanyal, 2010) drugs. As part of our ongoing structural studies of benzimidazole derivatives (Yoon et al., 2011), we now report the structure of the title compound.

In the title compound, Fig. 1, the benzimidazole (N1/N2/C1–C7) ring system is essentially planar with a maximum deviation of 0.020 (1) Å for atom N2. Dihedral angles of benzimidazole, (N1/N2/C1–C7) ring with the mean plane of pyrrolidin-2-one ring (N3/C20–C23) and the 2-methoxyphenol (C8–C13) ring are 54.10 (11) and 67.79 (6)°, respectively. The pyrrolidin-2-one ring adopts an envelope conformation with puckering parameters of Q = 0.148 (3) Å and [var phi] = 78.5 (10)° (Cremer & Pople, 1975) with atom C21 at the flap, deviating by 0.095 (3) Å. In the crystal packing (Fig. 2), intermolecular O1W—H2W1···O2, O4—H1O4···O1W and O1W—H1W1···N1 hydrogen bonds link the molecules into a double-tape structure running along the a axis. There is a π–π stacking interaction between the benzene (C1–C6; centroid Cg3) rings with a Cg3···Cg3iv distance of 3.6632 (9) Å [symmetry code: (iv) -x, -y, -z + 1]. The crystal packing is further stabilized by a C16—H16A···O5 hydrogen bond and a weak C20—H20B···Cg4 interaction (Table 1), where Cg4 is the centroid of the benzene (C8–C13) ring.

Experimental

Ethyl 3-amino-4-(3(2-oxopyrrolidin-1yl)propylamino)benzoate (0.84 mmol) and sodium metabisulfite adduct of 4-hydroxy-3-metoxybenzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was reflux at 130 °C for 2 hrs. 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.

Refinement

The O-bound H atom was located in a difference Fourier map and refined freely [O—H = 0.88 (3), 0.85 (3) and 0.95 (3) Å]. The remaining H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 Å. The Uiso(H) values were constrained to be 1.5Ueq (methyl-H atom) and 1.2Ueq (other H atoms). The rotating model group was applied for the methyl group.

Figures

Fig. 1.
The structure of the title compound, showing 50% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.
Fig. 2.
The crystal packing, viewed along the a-axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C24H27N3O5·H2OZ = 2
Mr = 455.50F(000) = 484
Triclinic, P1Dx = 1.306 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.7460 (8) ÅCell parameters from 4470 reflections
b = 10.0436 (8) Åθ = 2.5–29.5°
c = 12.6072 (10) ŵ = 0.10 mm1
α = 85.737 (1)°T = 296 K
β = 89.684 (2)°Block, brown
γ = 70.238 (1)°0.43 × 0.32 × 0.16 mm
V = 1157.91 (16) Å3

Data collection

Bruker APEXII DUO CCD area-detector diffractometer6686 independent reflections
Radiation source: fine-focus sealed tube4485 reflections with I > 2σ(I)
graphiteRint = 0.029
[var phi] and ω scansθmax = 30.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −13→13
Tmin = 0.960, Tmax = 0.985k = −14→14
18195 measured reflectionsl = −17→17

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) = 0.185H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.0974P)2 + 0.1068P] where P = (Fo2 + 2Fc2)/3
6686 reflections(Δ/σ)max < 0.001
312 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = −0.26 e Å3

Special details

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
O1−0.17090 (17)0.13373 (19)0.18216 (12)0.0762 (4)
O2−0.35072 (14)0.11827 (17)0.28604 (13)0.0702 (4)
O30.1298 (3)0.2186 (2)1.00505 (19)0.1183 (8)
O40.64165 (13)0.40228 (14)0.73582 (10)0.0538 (3)
O50.64019 (13)0.14280 (12)0.76404 (10)0.0552 (3)
N10.17611 (13)0.25473 (14)0.43596 (10)0.0416 (3)
N20.09463 (13)0.23337 (13)0.60105 (10)0.0401 (3)
N30.12756 (16)0.41105 (17)0.89776 (11)0.0529 (4)
C10.04959 (15)0.21973 (15)0.43129 (12)0.0379 (3)
C2−0.02368 (16)0.19669 (16)0.34357 (13)0.0412 (3)
H2A0.01000.20350.27490.049*
C3−0.14954 (15)0.16306 (15)0.36302 (13)0.0421 (3)
C4−0.20115 (16)0.15385 (17)0.46613 (14)0.0456 (4)
H4A−0.28630.13250.47590.055*
C5−0.12959 (16)0.17542 (17)0.55325 (13)0.0443 (3)
H5A−0.16360.16860.62180.053*
C6−0.00288 (15)0.20810 (15)0.53349 (12)0.0378 (3)
C70.19826 (15)0.26220 (15)0.53799 (12)0.0386 (3)
C80.31855 (15)0.29914 (16)0.58469 (12)0.0391 (3)
C90.42362 (16)0.19835 (15)0.65042 (12)0.0419 (3)
H9A0.42060.10680.66160.050*
C100.53227 (15)0.23334 (15)0.69912 (12)0.0397 (3)
C110.53539 (16)0.37285 (16)0.68324 (12)0.0399 (3)
C120.43197 (17)0.47134 (16)0.61670 (13)0.0436 (3)
H12A0.43460.56300.60510.052*
C130.32404 (17)0.43507 (16)0.56685 (13)0.0437 (3)
H13A0.25570.50190.52160.052*
C14−0.23434 (18)0.13642 (17)0.27471 (15)0.0492 (4)
C15−0.2499 (4)0.1148 (4)0.0897 (2)0.1125 (11)
H15A−0.24170.01590.08930.135*
H15B−0.35240.17070.09420.135*
C16−0.1953 (5)0.1561 (5)−0.0036 (3)0.1330 (14)
H16A−0.24530.1380−0.06330.199*
H16B−0.09300.1034−0.00680.199*
H16C−0.20950.2556−0.00550.199*
C170.07375 (17)0.25520 (17)0.71444 (12)0.0440 (3)
H17A0.16790.22340.75100.053*
H17B0.01740.19900.74470.053*
C18−0.00473 (18)0.41025 (18)0.73095 (13)0.0489 (4)
H18A−0.10240.43880.70030.059*
H18B0.04620.46690.69360.059*
C19−0.01470 (19)0.4404 (2)0.84774 (15)0.0574 (4)
H19A−0.07250.53930.85370.069*
H19B−0.06440.38280.88530.069*
C200.2172 (3)0.4956 (3)0.86944 (19)0.0786 (7)
H20A0.16550.59510.87830.094*
H20B0.24850.48510.79640.094*
C210.3479 (3)0.4349 (4)0.9482 (2)0.0957 (9)
H21A0.43900.41910.91130.115*
H21B0.34200.49961.00280.115*
C220.3385 (3)0.2990 (3)0.9957 (2)0.0910 (8)
H22A0.35410.29091.07210.109*
H22B0.41120.21940.96590.109*
C230.1884 (3)0.3012 (2)0.96930 (17)0.0675 (5)
C240.6452 (2)−0.0001 (2)0.7783 (2)0.0696 (6)
H24A0.7301−0.05500.82040.104*
H24B0.6497−0.03810.71020.104*
H24C0.5593−0.00410.81410.104*
O1W0.63716 (17)0.67068 (15)0.71300 (12)0.0565 (3)
H2W10.556 (3)0.736 (3)0.7004 (18)0.073 (7)*
H1W10.703 (3)0.695 (2)0.6663 (19)0.076 (7)*
H1O40.630 (3)0.493 (3)0.7238 (18)0.075 (7)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0729 (9)0.1176 (13)0.0612 (9)−0.0609 (9)−0.0102 (7)−0.0141 (8)
O20.0485 (7)0.0835 (10)0.0904 (10)−0.0369 (7)−0.0121 (7)−0.0103 (8)
O30.1466 (19)0.0967 (14)0.1279 (17)−0.0717 (14)−0.0518 (14)0.0407 (12)
O40.0477 (6)0.0476 (7)0.0739 (8)−0.0271 (5)−0.0160 (6)−0.0001 (6)
O50.0519 (6)0.0420 (6)0.0730 (8)−0.0197 (5)−0.0242 (6)0.0066 (5)
N10.0363 (6)0.0502 (7)0.0435 (7)−0.0221 (5)−0.0036 (5)−0.0006 (5)
N20.0382 (6)0.0431 (7)0.0430 (7)−0.0192 (5)−0.0022 (5)−0.0026 (5)
N30.0548 (8)0.0617 (9)0.0458 (8)−0.0234 (7)−0.0013 (6)−0.0086 (6)
C10.0316 (6)0.0379 (7)0.0462 (8)−0.0151 (6)−0.0041 (5)0.0001 (6)
C20.0367 (7)0.0432 (8)0.0460 (8)−0.0171 (6)−0.0052 (6)−0.0011 (6)
C30.0338 (7)0.0362 (7)0.0577 (9)−0.0139 (6)−0.0086 (6)−0.0017 (6)
C40.0337 (7)0.0423 (8)0.0641 (10)−0.0177 (6)−0.0005 (7)−0.0005 (7)
C50.0383 (7)0.0458 (8)0.0514 (9)−0.0186 (6)0.0033 (6)−0.0004 (6)
C60.0337 (6)0.0348 (7)0.0457 (8)−0.0131 (5)−0.0038 (5)0.0002 (5)
C70.0346 (7)0.0388 (7)0.0443 (8)−0.0155 (6)−0.0037 (6)−0.0003 (6)
C80.0364 (7)0.0419 (7)0.0423 (8)−0.0180 (6)−0.0025 (6)−0.0020 (6)
C90.0419 (7)0.0351 (7)0.0528 (9)−0.0189 (6)−0.0077 (6)−0.0008 (6)
C100.0365 (7)0.0366 (7)0.0473 (8)−0.0145 (6)−0.0073 (6)0.0006 (6)
C110.0360 (7)0.0406 (7)0.0478 (8)−0.0191 (6)0.0000 (6)−0.0047 (6)
C120.0432 (8)0.0378 (7)0.0545 (9)−0.0208 (6)−0.0018 (6)0.0015 (6)
C130.0417 (7)0.0418 (8)0.0491 (8)−0.0176 (6)−0.0066 (6)0.0039 (6)
C140.0426 (8)0.0444 (8)0.0645 (11)−0.0203 (7)−0.0120 (7)−0.0002 (7)
C150.124 (2)0.192 (3)0.0685 (16)−0.112 (3)−0.0155 (15)−0.0232 (18)
C160.184 (4)0.162 (3)0.088 (2)−0.108 (3)−0.050 (2)0.003 (2)
C170.0454 (8)0.0480 (8)0.0404 (8)−0.0189 (7)−0.0021 (6)−0.0004 (6)
C180.0408 (8)0.0543 (9)0.0485 (9)−0.0118 (7)−0.0045 (6)−0.0056 (7)
C190.0480 (9)0.0665 (11)0.0564 (10)−0.0157 (8)0.0059 (8)−0.0154 (8)
C200.0812 (14)0.1101 (19)0.0640 (12)−0.0598 (14)−0.0060 (11)0.0033 (12)
C210.0717 (15)0.157 (3)0.0758 (15)−0.0603 (18)−0.0095 (12)−0.0113 (16)
C220.0764 (15)0.103 (2)0.0856 (17)−0.0190 (15)−0.0253 (13)−0.0107 (14)
C230.0776 (13)0.0626 (12)0.0628 (12)−0.0239 (11)−0.0135 (10)−0.0052 (9)
C240.0683 (12)0.0404 (9)0.0982 (16)−0.0193 (9)−0.0323 (11)0.0140 (9)
O1W0.0552 (7)0.0477 (7)0.0723 (9)−0.0254 (6)0.0088 (6)−0.0028 (6)

Geometric parameters (Å, °)

O1—C141.315 (2)C11—C121.382 (2)
O1—C151.460 (2)C12—C131.391 (2)
O2—C141.214 (2)C12—H12A0.9300
O3—C231.216 (3)C13—H13A0.9300
O4—C111.3575 (17)C15—C161.382 (5)
O4—H1O40.88 (3)C15—H15A0.9700
O5—C101.3621 (18)C15—H15B0.9700
O5—C241.418 (2)C16—H16A0.9600
N1—C71.317 (2)C16—H16B0.9600
N1—C11.3944 (17)C16—H16C0.9600
N2—C71.3750 (19)C17—C181.515 (2)
N2—C61.3774 (18)C17—H17A0.9700
N2—C171.465 (2)C17—H17B0.9700
N3—C231.341 (3)C18—C191.521 (2)
N3—C201.437 (3)C18—H18A0.9700
N3—C191.453 (2)C18—H18B0.9700
C1—C21.395 (2)C19—H19A0.9700
C1—C61.395 (2)C19—H19B0.9700
C2—C31.394 (2)C20—C211.542 (3)
C2—H2A0.9300C20—H20A0.9700
C3—C41.399 (2)C20—H20B0.9700
C3—C141.483 (2)C21—C221.481 (4)
C4—C51.373 (2)C21—H21A0.9700
C4—H4A0.9300C21—H21B0.9700
C5—C61.398 (2)C22—C231.494 (3)
C5—H5A0.9300C22—H22A0.9700
C7—C81.4808 (19)C22—H22B0.9700
C8—C131.386 (2)C24—H24A0.9600
C8—C91.394 (2)C24—H24B0.9600
C9—C101.3830 (19)C24—H24C0.9600
C9—H9A0.9300O1W—H2W10.85 (3)
C10—C111.411 (2)O1W—H1W10.95 (3)
C14—O1—C15117.16 (17)C16—C15—H15B109.4
C11—O4—H1O4109.2 (16)O1—C15—H15B109.4
C10—O5—C24117.13 (13)H15A—C15—H15B108.0
C7—N1—C1104.76 (12)C15—C16—H16A109.5
C7—N2—C6106.56 (12)C15—C16—H16B109.5
C7—N2—C17126.45 (12)H16A—C16—H16B109.5
C6—N2—C17125.80 (13)C15—C16—H16C109.5
C23—N3—C20114.78 (18)H16A—C16—H16C109.5
C23—N3—C19123.57 (18)H16B—C16—H16C109.5
C20—N3—C19121.59 (17)N2—C17—C18110.95 (13)
N1—C1—C2129.84 (14)N2—C17—H17A109.4
N1—C1—C6109.94 (12)C18—C17—H17A109.4
C2—C1—C6120.21 (13)N2—C17—H17B109.4
C3—C2—C1117.26 (15)C18—C17—H17B109.4
C3—C2—H2A121.4H17A—C17—H17B108.0
C1—C2—H2A121.4C17—C18—C19112.78 (15)
C2—C3—C4121.49 (14)C17—C18—H18A109.0
C2—C3—C14121.05 (15)C19—C18—H18A109.0
C4—C3—C14117.46 (14)C17—C18—H18B109.0
C5—C4—C3121.84 (14)C19—C18—H18B109.0
C5—C4—H4A119.1H18A—C18—H18B107.8
C3—C4—H4A119.1N3—C19—C18112.58 (14)
C4—C5—C6116.48 (15)N3—C19—H19A109.1
C4—C5—H5A121.8C18—C19—H19A109.1
C6—C5—H5A121.8N3—C19—H19B109.1
N2—C6—C1105.75 (12)C18—C19—H19B109.1
N2—C6—C5131.54 (14)H19A—C19—H19B107.8
C1—C6—C5122.71 (13)N3—C20—C21103.2 (2)
N1—C7—N2112.96 (12)N3—C20—H20A111.1
N1—C7—C8125.86 (13)C21—C20—H20A111.1
N2—C7—C8121.17 (13)N3—C20—H20B111.1
C13—C8—C9119.76 (13)C21—C20—H20B111.1
C13—C8—C7120.35 (13)H20A—C20—H20B109.1
C9—C8—C7119.84 (13)C22—C21—C20105.7 (2)
C10—C9—C8120.56 (13)C22—C21—H21A110.6
C10—C9—H9A119.7C20—C21—H21A110.6
C8—C9—H9A119.7C22—C21—H21B110.6
O5—C10—C9125.15 (13)C20—C21—H21B110.6
O5—C10—C11115.23 (12)H21A—C21—H21B108.7
C9—C10—C11119.62 (13)C21—C22—C23106.0 (2)
O4—C11—C12123.67 (13)C21—C22—H22A110.5
O4—C11—C10117.02 (13)C23—C22—H22A110.5
C12—C11—C10119.31 (13)C21—C22—H22B110.5
C11—C12—C13120.81 (13)C23—C22—H22B110.5
C11—C12—H12A119.6H22A—C22—H22B108.7
C13—C12—H12A119.6O3—C23—N3125.0 (2)
C8—C13—C12119.90 (14)O3—C23—C22126.9 (2)
C8—C13—H13A120.1N3—C23—C22108.1 (2)
C12—C13—H13A120.1O5—C24—H24A109.5
O2—C14—O1122.90 (16)O5—C24—H24B109.5
O2—C14—C3123.72 (18)H24A—C24—H24B109.5
O1—C14—C3113.38 (14)O5—C24—H24C109.5
C16—C15—O1111.0 (2)H24A—C24—H24C109.5
C16—C15—H15A109.4H24B—C24—H24C109.5
O1—C15—H15A109.4H2W1—O1W—H1W1105 (2)
C7—N1—C1—C2−179.26 (15)C8—C9—C10—C110.9 (2)
C7—N1—C1—C60.55 (16)O5—C10—C11—O4−1.7 (2)
N1—C1—C2—C3−179.84 (15)C9—C10—C11—O4177.88 (14)
C6—C1—C2—C30.4 (2)O5—C10—C11—C12178.61 (14)
C1—C2—C3—C40.5 (2)C9—C10—C11—C12−1.8 (2)
C1—C2—C3—C14−179.84 (13)O4—C11—C12—C13−178.67 (15)
C2—C3—C4—C5−0.9 (2)C10—C11—C12—C131.0 (2)
C14—C3—C4—C5179.39 (14)C9—C8—C13—C12−1.7 (2)
C3—C4—C5—C60.4 (2)C7—C8—C13—C12175.77 (14)
C7—N2—C6—C11.43 (15)C11—C12—C13—C80.7 (2)
C17—N2—C6—C1169.57 (13)C15—O1—C14—O23.1 (3)
C7—N2—C6—C5−179.21 (16)C15—O1—C14—C3−177.2 (2)
C17—N2—C6—C5−11.1 (3)C2—C3—C14—O2−173.74 (17)
N1—C1—C6—N2−1.25 (16)C4—C3—C14—O25.9 (2)
C2—C1—C6—N2178.58 (13)C2—C3—C14—O16.5 (2)
N1—C1—C6—C5179.31 (14)C4—C3—C14—O1−173.82 (15)
C2—C1—C6—C5−0.9 (2)C14—O1—C15—C16161.8 (3)
C4—C5—C6—N2−178.83 (15)C7—N2—C17—C1877.86 (19)
C4—C5—C6—C10.4 (2)C6—N2—C17—C18−87.97 (18)
C1—N1—C7—N20.40 (17)N2—C17—C18—C19−173.95 (13)
C1—N1—C7—C8−178.76 (14)C23—N3—C19—C18−108.7 (2)
C6—N2—C7—N1−1.19 (17)C20—N3—C19—C1868.2 (2)
C17—N2—C7—N1−169.23 (14)C17—C18—C19—N363.3 (2)
C6—N2—C7—C8178.01 (13)C23—N3—C20—C21−7.6 (3)
C17—N2—C7—C810.0 (2)C19—N3—C20—C21175.20 (18)
N1—C7—C8—C1367.7 (2)N3—C20—C21—C2213.8 (3)
N2—C7—C8—C13−111.44 (17)C20—C21—C22—C23−15.0 (3)
N1—C7—C8—C9−114.92 (18)C20—N3—C23—O3178.6 (3)
N2—C7—C8—C965.99 (19)C19—N3—C23—O3−4.3 (3)
C13—C8—C9—C100.8 (2)C20—N3—C23—C22−1.7 (3)
C7—C8—C9—C10−176.60 (14)C19—N3—C23—C22175.38 (18)
C24—O5—C10—C93.3 (3)C21—C22—C23—O3−169.5 (3)
C24—O5—C10—C11−177.18 (17)C21—C22—C23—N310.8 (3)
C8—C9—C10—O5−179.58 (15)

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C8–C13 benzene ring.
D—H···AD—HH···AD···AD—H···A
O1W—H2W1···O2i0.85 (3)2.06 (3)2.879 (2)164 (2)
O1W—H1W1···N1ii0.95 (3)1.90 (3)2.8416 (19)176 (2)
O4—H1O4···O1W0.88 (3)1.80 (3)2.675 (2)169 (3)
C16—H16A···O5iii0.962.443.380 (3)166.
C20—H20B···Cg40.972.863.750 (3)153

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5022).

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