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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1824–o1825.
Published online 2010 June 26. doi:  10.1107/S1600536810023639
PMCID: PMC3006730

Ethyl 1-(2-hy­droxy­eth­yl)-2-phenyl-1H-benzimidazole-5-carboxyl­ate

Abstract

There are two mol­ecules in the asymmetric unit of the title compound, C18H18N2O3. In each one, the benzimidazole ring system is essentially planar, with maximum deviations of 0.027 (1) and 0.032 (1)Å, and makes dihedral angles of 38.64 (6) and 41.48 (6)°, respectively, with the attached benzene rings. An intra­molecular C—H(...)O hydrogen bond is observed in each mol­ecule. The two independent mol­ecules are connected into a dimer by two inter­molecular O—H(...)N hydrogen bonds. In the crystal, mol­ecules form a two-dimensional layers parallel to (012) via weak inter­molecular C—H(...)O hydrogen bonds. In addition, weak π-π stacking inter­actions are observed with centroid–centroid distances of 3.5244 (12) and 3.6189 (12) Å.

Related literature

For the applications of benzimidazole and its derivatives in the pharmaceutical and biological fields, see: Horton et al. (2003 [triangle]). These heterocycles can serve as mol­ecular scaffolds with versatile binding properties via modifications of their functional groups, see: DeSimone et al. (2004 [triangle]). For the biological activity of benzimidazole derivatives, see: Gowda et al. (2009 [triangle]); Tunçbilek et al. (2009 [triangle]); Achar et al. (2010 [triangle]). For related structures, see: Arumugam et al. (2010 [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1824-scheme1.jpg

Experimental

Crystal data

  • C18H18N2O3
  • M r = 310.34
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1824-efi1.jpg
  • a = 8.997 (2) Å
  • b = 12.988 (3) Å
  • c = 15.030 (3) Å
  • α = 103.764 (6)°
  • β = 107.202 (6)°
  • γ = 102.929 (6)°
  • V = 1545.5 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.34 × 0.20 × 0.11 mm

Data collection

  • Bruker APEXII DUO CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.970, T max = 0.990
  • 34907 measured reflections
  • 9838 independent reflections
  • 6952 reflections with I > 2σ(I)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.167
  • S = 1.04
  • 9838 reflections
  • 425 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.40 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 datablocks global, I. DOI: 10.1107/S1600536810023639/lh5069sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023639/lh5069Isup2.hkl

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

Acknowledgments

NH, SAH and ASAR gratefully acknowledge the Inter­national Islamic University Malaysia (IIUM) for an FRGS Grant (FRGS0510-119), USM Research Grant (1001/PFARMASI/815016) and MOSTI (304/PFARMASI/650512/I121) for funding the synthetic chemistry work. FHK and MMR thank Universiti Sains Malaysia for the Research University Golden Goose grant (No. 1001/PFIZIK/811012).

supplementary crystallographic information

Comment

Benzimidazole and its derivatives are compounds which are well known in the pharmaceutical and biological fields (Horton et al., 2003). These heterocycles can serve as molecular scaffolds with versatile binding properties via modifications of their functional groups (DeSimone et al., 2004). Suitably substituted benzimidazole derivatives have been reported to show anti-tumor (Gowda et al., 2009), antimicrobial (Tunçbilek et al., 2009) and anti-inflammatory (Achar et al., 2010) activities. On this basis, we report the structure of the title compound.

The asymmetric unit of (I) contains two molecules (Fig. 1) [A and B] with all geometrical parameters within normal ranges. For both molecules, the benzimidazole ring system (N1/N2/C1–C7) is essentially planar with a maximum deviation of 0.027 (1) and 0.032 (1)Å respectively for atom C7A and N1B. The dihedral angle between the benzimidazole ring system (N1/N2/C1–C7) and the attached benzene ring (C8–C13) is 38.64 (6) and 41.48 (6)° respectively for molecules A and B.

The two independent molecules are connected into a dimer by two intermolecular O—H···N hydrogen bonds (Table 1). In the crystal structure, molecules are connected by weak intermolecular C—H···O interactions (Table 1). These interactions form two-dimensional layers parallel to (0 1 2). In addition there are weak π···π stacking interactions within the asymmetric unit with distances of Cg1···Cg3 = 3.5244 (12) Å and Cg2···Cg4 = 3.6189 (12) Å; Cg1, Cg2, Cg3 and Cg4 and are the centroids of N1A/N2A/C1A/C6A–C7A, C1A–C6A, N1B/N2B/C1B/C6B–C7B and C1B–C6B rings, respectively.

Experimental

The title compound was synthesised by the addition of sodium sulfite adduct of benzaldehyde (562 mg, 2.67 mmol) to a mixture of ethyl 3-amino-4-(2-hydroxylethylamino) benzoate (300 mg, 1.33 mmol) in 0.5 mL of DMF. Subsequently, the mixture was irradiated at 403K in a microwave reactor for 2 min. After the reaction, the mixture was diluted with 30 mL of EtOAc and washed with 20 mL of H2O. The organic layer was collected, dried over Na2SO4 and the solvent was evaporated under pressure to afford the crude product. The product was recrystallised with hot EtOAc which was slowly evaporated to give a single block of clear crystal.

Refinement

The H atoms attached to O1A and O1B were located in a difference map and refined isotropically. The remaining H atoms were positioned geometrically [C-H = 0.93, 0.96 or 0.97 Å] and were refined using a riding model, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and 1.2 for all other H atoms. A rotating group model was used for the methyl groups.

Figures

Fig. 1.
The molecular structure, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius.
Fig. 2.
The crystal packing of (I) viewed along the a axis. Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.

Crystal data

C18H18N2O3Z = 4
Mr = 310.34F(000) = 656
Triclinic, P1Dx = 1.334 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.997 (2) ÅCell parameters from 6508 reflections
b = 12.988 (3) Åθ = 2.6–31.1°
c = 15.030 (3) ŵ = 0.09 mm1
α = 103.764 (6)°T = 100 K
β = 107.202 (6)°Block, colourless
γ = 102.929 (6)°0.34 × 0.20 × 0.11 mm
V = 1545.5 (6) Å3

Data collection

Bruker APEXII DUO CCD area-detector diffractometer9838 independent reflections
Radiation source: fine-focus sealed tube6952 reflections with I > 2σ(I)
graphiteRint = 0.051
[var phi] and ω scansθmax = 31.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −13→13
Tmin = 0.970, Tmax = 0.990k = −18→18
34907 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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0944P)2 + 0.2365P] where P = (Fo2 + 2Fc2)/3
9838 reflections(Δ/σ)max = 0.001
425 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = −0.40 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
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
O1A1.15213 (13)0.95597 (9)0.66787 (8)0.0189 (2)
O2A0.54072 (14)1.15419 (10)0.96176 (9)0.0311 (3)
O3A0.78042 (13)1.28774 (9)1.05882 (8)0.0235 (2)
N1A1.02010 (14)0.92733 (10)0.82790 (8)0.0147 (2)
N2A0.74895 (14)0.84883 (10)0.78666 (9)0.0155 (2)
C1A0.96687 (16)1.00752 (11)0.87590 (10)0.0148 (2)
C2A1.05169 (17)1.11622 (12)0.94178 (10)0.0171 (3)
H2AA1.16411.14800.95960.020*
C3A0.95920 (17)1.17389 (12)0.97904 (10)0.0171 (3)
H3AA1.01101.24621.02330.021*
C4A0.78835 (17)1.12585 (12)0.95159 (10)0.0160 (3)
C5A0.70664 (17)1.01725 (12)0.88665 (10)0.0161 (3)
H5AA0.59430.98530.86890.019*
C6A0.79750 (16)0.95790 (12)0.84909 (10)0.0150 (3)
C7A0.88525 (16)0.83316 (11)0.77649 (10)0.0149 (3)
C8A0.88701 (16)0.72261 (11)0.72397 (10)0.0161 (3)
C9A0.78407 (17)0.62979 (12)0.73233 (11)0.0192 (3)
H9AA0.71780.64040.76860.023*
C10A0.78010 (19)0.52256 (13)0.68722 (12)0.0219 (3)
H10A0.71130.46160.69310.026*
C11A0.87878 (19)0.50601 (13)0.63319 (12)0.0234 (3)
H11A0.87850.43420.60430.028*
C12A0.97797 (19)0.59712 (13)0.62236 (12)0.0235 (3)
H12A1.04250.58580.58500.028*
C13A0.98171 (18)0.70472 (12)0.66663 (11)0.0195 (3)
H13A1.04740.76510.65820.023*
C14A1.19033 (16)0.94750 (12)0.83426 (10)0.0170 (3)
H14A1.20890.87630.81380.020*
H14B1.26330.98680.90230.020*
C15A1.23125 (17)1.01573 (12)0.77022 (10)0.0178 (3)
H15A1.19931.08240.78500.021*
H15B1.34901.03920.78670.021*
C16A0.68862 (19)1.18841 (12)0.98976 (11)0.0195 (3)
C17A0.6900 (2)1.35453 (14)1.09824 (13)0.0270 (3)
H17A0.60011.35591.04410.032*
H17B0.76221.43071.13340.032*
C18A0.6227 (2)1.30985 (16)1.16688 (13)0.0309 (4)
H18A0.57061.35911.19440.046*
H18B0.71051.30511.21900.046*
H18C0.54381.23691.13100.046*
O1B0.44589 (13)0.70587 (9)0.63176 (8)0.0198 (2)
O2B0.98042 (13)1.37266 (9)0.85047 (9)0.0261 (2)
O3B0.72718 (13)1.37041 (9)0.84618 (8)0.0218 (2)
N1B0.56260 (14)0.88812 (10)0.55835 (8)0.0146 (2)
N2B0.83526 (14)0.96642 (10)0.60695 (9)0.0159 (2)
C1B0.60025 (16)0.99572 (11)0.61970 (10)0.0144 (2)
C2B0.50052 (16)1.05442 (12)0.64814 (10)0.0163 (3)
H2BA0.38731.02240.62550.020*
C3B0.57926 (17)1.16295 (12)0.71190 (10)0.0170 (3)
H3BA0.51741.20550.73200.020*
C4B0.75098 (17)1.21029 (11)0.74702 (10)0.0158 (3)
C5B0.84839 (16)1.15126 (11)0.71697 (10)0.0155 (3)
H5BA0.96181.18300.74040.019*
C6B0.77088 (16)1.04313 (11)0.65068 (10)0.0146 (2)
C7B0.70751 (16)0.87512 (11)0.55223 (10)0.0150 (3)
C8B0.72348 (17)0.77623 (12)0.48846 (10)0.0169 (3)
C9B0.83211 (19)0.79407 (13)0.43951 (12)0.0235 (3)
H9BA0.88940.86660.44670.028*
C10B0.8546 (2)0.70370 (15)0.38006 (13)0.0299 (4)
H10B0.92840.71600.34860.036*
C11B0.7677 (2)0.59535 (14)0.36748 (13)0.0270 (3)
H11B0.78130.53520.32640.032*
C12B0.66018 (19)0.57676 (13)0.41618 (12)0.0224 (3)
H12B0.60270.50400.40820.027*
C13B0.63813 (17)0.66645 (12)0.47681 (11)0.0187 (3)
H13B0.56660.65360.50970.022*
C14B0.39725 (16)0.80879 (12)0.51552 (10)0.0166 (3)
H14C0.39170.74540.46360.020*
H14D0.32040.84420.48640.020*
C15B0.34895 (17)0.76807 (12)0.59306 (11)0.0187 (3)
H15C0.35990.83200.64630.022*
H15D0.23470.72200.56390.022*
C16B0.83472 (18)1.32504 (12)0.81937 (10)0.0179 (3)
C17B0.7947 (2)1.48136 (13)0.91805 (12)0.0243 (3)
H17C0.87081.53010.90000.029*
H17D0.85271.47870.98270.029*
C18B0.6526 (2)1.52376 (16)0.91910 (15)0.0354 (4)
H18D0.69241.59770.96590.053*
H18E0.57861.47500.93740.053*
H18F0.59601.52560.85470.053*
H1OA1.061 (3)0.9613 (18)0.6519 (16)0.033 (6)*
H1OB0.551 (3)0.753 (2)0.6837 (18)0.048 (7)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0133 (5)0.0260 (5)0.0181 (5)0.0069 (4)0.0064 (4)0.0070 (4)
O2A0.0197 (5)0.0316 (6)0.0346 (7)0.0082 (5)0.0096 (5)−0.0017 (5)
O3A0.0230 (5)0.0193 (5)0.0255 (6)0.0058 (4)0.0114 (4)0.0006 (4)
N1A0.0137 (5)0.0153 (5)0.0152 (5)0.0043 (4)0.0061 (4)0.0048 (4)
N2A0.0133 (5)0.0161 (5)0.0162 (5)0.0036 (4)0.0058 (4)0.0045 (4)
C1A0.0155 (6)0.0160 (6)0.0139 (6)0.0049 (5)0.0064 (5)0.0055 (5)
C2A0.0146 (6)0.0178 (6)0.0168 (6)0.0031 (5)0.0047 (5)0.0056 (5)
C3A0.0178 (6)0.0164 (6)0.0152 (6)0.0036 (5)0.0055 (5)0.0042 (5)
C4A0.0169 (6)0.0176 (6)0.0142 (6)0.0058 (5)0.0059 (5)0.0056 (5)
C5A0.0140 (6)0.0183 (6)0.0158 (6)0.0046 (5)0.0053 (5)0.0059 (5)
C6A0.0148 (6)0.0162 (6)0.0135 (6)0.0041 (5)0.0048 (5)0.0051 (5)
C7A0.0143 (6)0.0164 (6)0.0144 (6)0.0038 (5)0.0056 (5)0.0061 (5)
C8A0.0141 (6)0.0163 (6)0.0166 (6)0.0051 (5)0.0038 (5)0.0052 (5)
C9A0.0179 (6)0.0194 (7)0.0204 (7)0.0046 (5)0.0077 (5)0.0073 (5)
C10A0.0207 (7)0.0168 (7)0.0262 (7)0.0038 (5)0.0072 (6)0.0076 (6)
C11A0.0223 (7)0.0171 (7)0.0274 (8)0.0052 (6)0.0080 (6)0.0035 (6)
C12A0.0230 (7)0.0211 (7)0.0277 (8)0.0072 (6)0.0137 (6)0.0044 (6)
C13A0.0190 (6)0.0180 (7)0.0215 (7)0.0046 (5)0.0091 (6)0.0054 (5)
C14A0.0131 (6)0.0204 (7)0.0187 (6)0.0060 (5)0.0068 (5)0.0068 (5)
C15A0.0131 (6)0.0211 (7)0.0196 (7)0.0040 (5)0.0071 (5)0.0071 (5)
C16A0.0227 (7)0.0199 (7)0.0163 (6)0.0079 (5)0.0077 (5)0.0049 (5)
C17A0.0333 (8)0.0218 (7)0.0321 (8)0.0130 (6)0.0202 (7)0.0055 (6)
C18A0.0329 (9)0.0348 (9)0.0279 (8)0.0157 (7)0.0129 (7)0.0084 (7)
O1B0.0212 (5)0.0172 (5)0.0204 (5)0.0043 (4)0.0072 (4)0.0073 (4)
O2B0.0185 (5)0.0217 (6)0.0302 (6)0.0023 (4)0.0064 (5)0.0019 (5)
O3B0.0196 (5)0.0198 (5)0.0242 (5)0.0064 (4)0.0088 (4)0.0032 (4)
N1B0.0121 (5)0.0158 (5)0.0157 (5)0.0033 (4)0.0054 (4)0.0057 (4)
N2B0.0138 (5)0.0166 (6)0.0178 (6)0.0048 (4)0.0059 (4)0.0067 (4)
C1B0.0130 (6)0.0158 (6)0.0145 (6)0.0033 (5)0.0046 (5)0.0066 (5)
C2B0.0127 (6)0.0202 (7)0.0169 (6)0.0051 (5)0.0060 (5)0.0072 (5)
C3B0.0160 (6)0.0194 (7)0.0177 (6)0.0065 (5)0.0077 (5)0.0071 (5)
C4B0.0168 (6)0.0156 (6)0.0148 (6)0.0038 (5)0.0060 (5)0.0053 (5)
C5B0.0131 (6)0.0171 (6)0.0163 (6)0.0036 (5)0.0046 (5)0.0073 (5)
C6B0.0127 (6)0.0167 (6)0.0161 (6)0.0049 (5)0.0057 (5)0.0078 (5)
C7B0.0133 (6)0.0172 (6)0.0163 (6)0.0051 (5)0.0055 (5)0.0080 (5)
C8B0.0154 (6)0.0186 (7)0.0173 (6)0.0054 (5)0.0064 (5)0.0063 (5)
C9B0.0247 (7)0.0223 (7)0.0304 (8)0.0085 (6)0.0165 (6)0.0118 (6)
C10B0.0358 (9)0.0295 (8)0.0367 (9)0.0138 (7)0.0267 (8)0.0123 (7)
C11B0.0291 (8)0.0244 (8)0.0288 (8)0.0112 (6)0.0143 (7)0.0038 (6)
C12B0.0209 (7)0.0178 (7)0.0270 (8)0.0052 (5)0.0089 (6)0.0053 (6)
C13B0.0170 (6)0.0190 (7)0.0212 (7)0.0055 (5)0.0081 (5)0.0073 (5)
C14B0.0117 (6)0.0183 (6)0.0177 (6)0.0026 (5)0.0043 (5)0.0054 (5)
C15B0.0160 (6)0.0189 (7)0.0224 (7)0.0032 (5)0.0099 (5)0.0074 (5)
C16B0.0191 (6)0.0175 (6)0.0177 (6)0.0058 (5)0.0069 (5)0.0070 (5)
C17B0.0266 (8)0.0190 (7)0.0251 (8)0.0071 (6)0.0107 (6)0.0022 (6)
C18B0.0384 (10)0.0310 (9)0.0467 (11)0.0165 (8)0.0253 (9)0.0126 (8)

Geometric parameters (Å, °)

O1A—C15A1.4186 (18)O1B—C15B1.4109 (18)
O1A—H1OA0.81 (2)O1B—H1OB0.98 (3)
O2A—C16A1.2085 (19)O2B—C16B1.2069 (18)
O3A—C16A1.3427 (18)O3B—C16B1.3484 (18)
O3A—C17A1.4564 (18)O3B—C17B1.4463 (19)
N1A—C7A1.3772 (18)N1B—C7B1.3779 (17)
N1A—C1A1.3801 (17)N1B—C1B1.3815 (18)
N1A—C14A1.4647 (18)N1B—C14B1.4563 (17)
N2A—C7A1.3328 (18)N2B—C7B1.3306 (18)
N2A—C6A1.3879 (18)N2B—C6B1.3900 (18)
C1A—C2A1.4007 (19)C1B—C2B1.3953 (19)
C1A—C6A1.4048 (19)C1B—C6B1.4037 (18)
C2A—C3A1.386 (2)C2B—C3B1.384 (2)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.413 (2)C3B—C4B1.408 (2)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.393 (2)C4B—C5B1.3892 (19)
C4A—C16A1.484 (2)C4B—C16B1.488 (2)
C5A—C6A1.3889 (19)C5B—C6B1.3915 (19)
C5A—H5AA0.9300C5B—H5BA0.9300
C7A—C8A1.471 (2)C7B—C8B1.472 (2)
C8A—C13A1.396 (2)C8B—C9B1.398 (2)
C8A—C9A1.4030 (19)C8B—C13B1.402 (2)
C9A—C10A1.384 (2)C9B—C10B1.390 (2)
C9A—H9AA0.9300C9B—H9BA0.9300
C10A—C11A1.387 (2)C10B—C11B1.386 (2)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.389 (2)C11B—C12B1.388 (2)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.386 (2)C12B—C13B1.390 (2)
C12A—H12A0.9300C12B—H12B0.9300
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.522 (2)C14B—C15B1.5221 (19)
C14A—H14A0.9700C14B—H14C0.9700
C14A—H14B0.9700C14B—H14D0.9700
C15A—H15A0.9700C15B—H15C0.9700
C15A—H15B0.9700C15B—H15D0.9700
C17A—C18A1.505 (2)C17B—C18B1.504 (2)
C17A—H17A0.9700C17B—H17C0.9700
C17A—H17B0.9700C17B—H17D0.9700
C18A—H18A0.9600C18B—H18D0.9600
C18A—H18B0.9600C18B—H18E0.9600
C18A—H18C0.9600C18B—H18F0.9600
C15A—O1A—H1OA106.6 (15)C15B—O1B—H1OB112.7 (14)
C16A—O3A—C17A115.62 (13)C16B—O3B—C17B116.69 (12)
C7A—N1A—C1A106.75 (11)C7B—N1B—C1B106.88 (11)
C7A—N1A—C14A130.19 (12)C7B—N1B—C14B130.48 (12)
C1A—N1A—C14A123.05 (12)C1B—N1B—C14B122.60 (11)
C7A—N2A—C6A105.31 (11)C7B—N2B—C6B105.39 (11)
N1A—C1A—C2A131.57 (13)N1B—C1B—C2B131.25 (12)
N1A—C1A—C6A105.94 (12)N1B—C1B—C6B105.80 (12)
C2A—C1A—C6A122.46 (13)C2B—C1B—C6B122.93 (13)
C3A—C2A—C1A116.44 (13)C3B—C2B—C1B116.39 (13)
C3A—C2A—H2AA121.8C3B—C2B—H2BA121.8
C1A—C2A—H2AA121.8C1B—C2B—H2BA121.8
C2A—C3A—C4A121.80 (13)C2B—C3B—C4B121.44 (13)
C2A—C3A—H3AA119.1C2B—C3B—H3BA119.3
C4A—C3A—H3AA119.1C4B—C3B—H3BA119.3
C5A—C4A—C3A120.83 (13)C5B—C4B—C3B121.46 (13)
C5A—C4A—C16A117.33 (13)C5B—C4B—C16B117.66 (12)
C3A—C4A—C16A121.83 (13)C3B—C4B—C16B120.88 (13)
C6A—C5A—C4A118.18 (13)C4B—C5B—C6B117.88 (12)
C6A—C5A—H5AA120.9C4B—C5B—H5BA121.1
C4A—C5A—H5AA120.9C6B—C5B—H5BA121.1
N2A—C6A—C5A130.04 (13)N2B—C6B—C5B130.50 (12)
N2A—C6A—C1A109.67 (12)N2B—C6B—C1B109.69 (12)
C5A—C6A—C1A120.28 (13)C5B—C6B—C1B119.80 (12)
N2A—C7A—N1A112.31 (12)N2B—C7B—N1B112.22 (12)
N2A—C7A—C8A121.48 (12)N2B—C7B—C8B122.11 (12)
N1A—C7A—C8A125.92 (12)N1B—C7B—C8B125.54 (12)
C13A—C8A—C9A118.79 (13)C9B—C8B—C13B119.22 (13)
C13A—C8A—C7A124.62 (13)C9B—C8B—C7B117.73 (13)
C9A—C8A—C7A116.59 (12)C13B—C8B—C7B123.04 (12)
C10A—C9A—C8A120.72 (14)C10B—C9B—C8B120.14 (14)
C10A—C9A—H9AA119.6C10B—C9B—H9BA119.9
C8A—C9A—H9AA119.6C8B—C9B—H9BA119.9
C9A—C10A—C11A119.98 (14)C11B—C10B—C9B120.35 (15)
C9A—C10A—H10A120.0C11B—C10B—H10B119.8
C11A—C10A—H10A120.0C9B—C10B—H10B119.8
C10A—C11A—C12A119.75 (14)C10B—C11B—C12B119.94 (15)
C10A—C11A—H11A120.1C10B—C11B—H11B120.0
C12A—C11A—H11A120.1C12B—C11B—H11B120.0
C13A—C12A—C11A120.63 (14)C11B—C12B—C13B120.24 (14)
C13A—C12A—H12A119.7C11B—C12B—H12B119.9
C11A—C12A—H12A119.7C13B—C12B—H12B119.9
C12A—C13A—C8A120.08 (13)C12B—C13B—C8B120.10 (13)
C12A—C13A—H13A120.0C12B—C13B—H13B120.0
C8A—C13A—H13A120.0C8B—C13B—H13B120.0
N1A—C14A—C15A112.25 (11)N1B—C14B—C15B111.15 (11)
N1A—C14A—H14A109.2N1B—C14B—H14C109.4
C15A—C14A—H14A109.2C15B—C14B—H14C109.4
N1A—C14A—H14B109.2N1B—C14B—H14D109.4
C15A—C14A—H14B109.2C15B—C14B—H14D109.4
H14A—C14A—H14B107.9H14C—C14B—H14D108.0
O1A—C15A—C14A113.10 (12)O1B—C15B—C14B112.51 (11)
O1A—C15A—H15A109.0O1B—C15B—H15C109.1
C14A—C15A—H15A109.0C14B—C15B—H15C109.1
O1A—C15A—H15B109.0O1B—C15B—H15D109.1
C14A—C15A—H15B109.0C14B—C15B—H15D109.1
H15A—C15A—H15B107.8H15C—C15B—H15D107.8
O2A—C16A—O3A123.39 (14)O2B—C16B—O3B123.64 (14)
O2A—C16A—C4A123.88 (14)O2B—C16B—C4B124.81 (14)
O3A—C16A—C4A112.73 (13)O3B—C16B—C4B111.55 (12)
O3A—C17A—C18A112.42 (14)O3B—C17B—C18B106.85 (14)
O3A—C17A—H17A109.1O3B—C17B—H17C110.4
C18A—C17A—H17A109.1C18B—C17B—H17C110.4
O3A—C17A—H17B109.1O3B—C17B—H17D110.4
C18A—C17A—H17B109.1C18B—C17B—H17D110.4
H17A—C17A—H17B107.9H17C—C17B—H17D108.6
C17A—C18A—H18A109.5C17B—C18B—H18D109.5
C17A—C18A—H18B109.5C17B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C17A—C18A—H18C109.5C17B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
C7A—N1A—C1A—C2A176.50 (14)C7B—N1B—C1B—C2B177.03 (14)
C14A—N1A—C1A—C2A−4.2 (2)C14B—N1B—C1B—C2B−5.3 (2)
C7A—N1A—C1A—C6A−1.25 (14)C7B—N1B—C1B—C6B−1.51 (14)
C14A—N1A—C1A—C6A178.06 (12)C14B—N1B—C1B—C6B176.20 (11)
N1A—C1A—C2A—C3A−178.13 (13)N1B—C1B—C2B—C3B179.89 (13)
C6A—C1A—C2A—C3A−0.7 (2)C6B—C1B—C2B—C3B−1.8 (2)
C1A—C2A—C3A—C4A−0.4 (2)C1B—C2B—C3B—C4B−1.0 (2)
C2A—C3A—C4A—C5A1.0 (2)C2B—C3B—C4B—C5B1.9 (2)
C2A—C3A—C4A—C16A−178.65 (13)C2B—C3B—C4B—C16B−176.95 (13)
C3A—C4A—C5A—C6A−0.5 (2)C3B—C4B—C5B—C6B0.0 (2)
C16A—C4A—C5A—C6A179.14 (12)C16B—C4B—C5B—C6B178.85 (12)
C7A—N2A—C6A—C5A−178.09 (14)C7B—N2B—C6B—C5B178.20 (14)
C7A—N2A—C6A—C1A0.21 (15)C7B—N2B—C6B—C1B−0.70 (15)
C4A—C5A—C6A—N2A177.63 (13)C4B—C5B—C6B—N2B178.57 (13)
C4A—C5A—C6A—C1A−0.5 (2)C4B—C5B—C6B—C1B−2.63 (19)
N1A—C1A—C6A—N2A0.67 (15)N1B—C1B—C6B—N2B1.40 (14)
C2A—C1A—C6A—N2A−177.34 (12)C2B—C1B—C6B—N2B−177.30 (12)
N1A—C1A—C6A—C5A179.17 (12)N1B—C1B—C6B—C5B−177.64 (12)
C2A—C1A—C6A—C5A1.2 (2)C2B—C1B—C6B—C5B3.7 (2)
C6A—N2A—C7A—N1A−1.05 (15)C6B—N2B—C7B—N1B−0.29 (15)
C6A—N2A—C7A—C8A173.07 (12)C6B—N2B—C7B—C8B175.92 (12)
C1A—N1A—C7A—N2A1.49 (15)C1B—N1B—C7B—N2B1.17 (15)
C14A—N1A—C7A—N2A−177.76 (12)C14B—N1B—C7B—N2B−176.30 (12)
C1A—N1A—C7A—C8A−172.31 (12)C1B—N1B—C7B—C8B−174.89 (12)
C14A—N1A—C7A—C8A8.4 (2)C14B—N1B—C7B—C8B7.6 (2)
N2A—C7A—C8A—C13A145.39 (14)N2B—C7B—C8B—C9B−37.4 (2)
N1A—C7A—C8A—C13A−41.3 (2)N1B—C7B—C8B—C9B138.34 (15)
N2A—C7A—C8A—C9A−33.94 (19)N2B—C7B—C8B—C13B141.16 (14)
N1A—C7A—C8A—C9A139.34 (14)N1B—C7B—C8B—C13B−43.1 (2)
C13A—C8A—C9A—C10A2.0 (2)C13B—C8B—C9B—C10B0.0 (2)
C7A—C8A—C9A—C10A−178.61 (13)C7B—C8B—C9B—C10B178.61 (15)
C8A—C9A—C10A—C11A0.1 (2)C8B—C9B—C10B—C11B1.1 (3)
C9A—C10A—C11A—C12A−1.8 (2)C9B—C10B—C11B—C12B−1.4 (3)
C10A—C11A—C12A—C13A1.3 (2)C10B—C11B—C12B—C13B0.6 (3)
C11A—C12A—C13A—C8A0.9 (2)C11B—C12B—C13B—C8B0.5 (2)
C9A—C8A—C13A—C12A−2.5 (2)C9B—C8B—C13B—C12B−0.8 (2)
C7A—C8A—C13A—C12A178.16 (14)C7B—C8B—C13B—C12B−179.33 (13)
C7A—N1A—C14A—C15A102.15 (16)C7B—N1B—C14B—C15B104.85 (16)
C1A—N1A—C14A—C15A−76.99 (16)C1B—N1B—C14B—C15B−72.28 (16)
N1A—C14A—C15A—O1A−69.79 (15)N1B—C14B—C15B—O1B−64.92 (15)
C17A—O3A—C16A—O2A−0.9 (2)C17B—O3B—C16B—O2B−1.5 (2)
C17A—O3A—C16A—C4A178.92 (12)C17B—O3B—C16B—C4B178.76 (12)
C5A—C4A—C16A—O2A−6.3 (2)C5B—C4B—C16B—O2B3.6 (2)
C3A—C4A—C16A—O2A173.36 (14)C3B—C4B—C16B—O2B−177.50 (14)
C5A—C4A—C16A—O3A173.93 (12)C5B—C4B—C16B—O3B−176.65 (12)
C3A—C4A—C16A—O3A−6.43 (19)C3B—C4B—C16B—O3B2.24 (19)
C16A—O3A—C17A—C18A73.83 (18)C16B—O3B—C17B—C18B167.61 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1A—H1OA···N2B0.81 (3)1.96 (3)2.7700 (19)177 (3)
O1B—H1OB···N2A0.98 (3)1.89 (3)2.8680 (18)177 (2)
C2B—H2BA···O1Ai0.932.423.238 (2)146
C12B—H12B···O1Bii0.932.553.416 (2)155
C13A—H13A···O1A0.932.403.273 (2)157
C13B—H13B···O1B0.932.433.300 (2)155
C15A—H15B···O2Aiii0.972.533.135 (2)120
C17B—H17D···O2Biv0.972.543.282 (2)133

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+2, −y+3, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5069).

References

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