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Acta Crystallogr Sect E Struct Rep Online. Sep 1, 2011; 67(Pt 9): o2405.
Published online Aug 27, 2011. doi:  10.1107/S1600536811033654
PMCID: PMC3200625
Ethyl 1-[3-(1H-imidazol-1-yl)prop­yl]-2-(4-chloro­phen­yl)-1H-benzo[d]imidazole-5-carboxyl­ate dihydrate
Yeong Keng Yoon,a Mohamed Ashraf Ali,a Ang Chee Wei,a Ching Kheng Quah,b and Hoong-Kun Funb*§
aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun/at/usm.my
Thomson Reuters ResearcherID: A-5525-2009.
§Thomson Reuters ResearcherID: A-3561-2009.
Received August 16, 2011; Accepted August 18, 2011.
In the title compound, C22H21ClN4O2·2H2O, the almost-planar benzimidazole ring system [maximum deviation 0.014 (1) Å] is inclined at angles of 36.32 (5) and 74.75 (7)° with respect to the phenyl and imidazole rings, respectively. In the crystal structure, the water mol­ecules are linked to the organic mol­ecules to form a three-dimensional network via O—H(...)N and O—H(...)O hydrogen bonds. The packing is further consolidated by a pair of bifurcated C—H(...)O bonds, generating R 1 2(6) loops. C—H(...)π inter­actions are also observed.
Related literature
For related structures and background to benzimidazoles, see: Eltayeb et al. (2009 [triangle], 2011 [triangle]). For standard bond-length data, see: Allen et al. (1987 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).
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Object name is e-67-o2405-scheme1.jpg Object name is e-67-o2405-scheme1.jpg
Crystal data
  • C22H21ClN4O2·2H2O
  • M r = 444.91
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-67-o2405-efi1.jpg
  • a = 9.0611 (1) Å
  • b = 13.8393 (2) Å
  • c = 18.0470 (3) Å
  • β = 92.386 (1)°
  • V = 2261.12 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 100 K
  • 0.40 × 0.30 × 0.27 mm
Data collection
  • Bruker SMART APEX II CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.922, T max = 0.947
  • 31604 measured reflections
  • 8235 independent reflections
  • 6221 reflections with I > 2σ(I)
  • R int = 0.030
Refinement
  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.136
  • S = 1.05
  • 8235 reflections
  • 296 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.54 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
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033654/hb6369sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033654/hb6369Isup2.hkl
Supplementary material file. DOI: 10.1107/S1600536811033654/hb6369Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank Universiti Sains Malaysia (USM), Penang, Malaysia, for providing research facilities. HKF and CKQ also thank USM for a Research University Grant (No. 1001/PFIZIK/811160).
supplementary crystallographic information
Comment
As part of our ongoing structural studies of benzimidazole derivatives (Eltayeb et al., 2011), we now report the structure of the title compound, (I), which crystallised as a dihydrate.
In the title molecule, Fig. 1, the benzimidazole ring system (N1/N2/C1–C7, maximum deviation of 0.014 (1) Å at atom C4) is inclined at angles of 36.32 (5) and 74.75 (7)° with respect to the phenyl (C8–C13) and imidazole (N3/N4/C20–C22 ) rings. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those in related structures (Eltayeb et al., 2009, 2011).
In the crystal, water molecules are linked to main molecules to form a three-dimensional network (Fig. 2) by O1W—H1W1···N1, O1W—H2W1···O2W, O2W—H1W2···N4 and O2W—H2W2···O2 hydrogen bonds (Table 1). The crystal packing is further consolidated by bifurcated C17—H17B···O1W and C19—H19B···O1W acceptor bonds, generating R12(6) ring motifs (Bernstein et al., 1995). The crystal structure is also stabilized by C10—H10A···Cg1 (Table 1) interactions, where Cg1 is the centroid of the C1–C6 phenyl ring.
Experimental
Ethyl 4-(3-(1H-imidazol-1-yl)propylamino)-3-aminobenzoate (0.84 mmol) and sodium metabisulfite adduct of chlorobenzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was refluxed at 403 K 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 then evaporated in vacuo to yield the product. The product was recrystallised from ethyl acetate to yield bronze blocks of (I).
Refinement
O-bound H atoms were located from the difference Fourier map and refined freely [O—H = 0.85 (2)–0.94 (3) Å]. The remaining H atoms were positioned geometrically and refined using a riding model with C—H = 0.95-0.99 Å and Uiso(H) = 1.2 Ueq(C). A rotating-group model was applied for the methyl group.
Figures
Fig. 1.
Fig. 1.
The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms.
Fig. 2.
Fig. 2.
The crystal structure of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.
Crystal data
C22H21ClN4O2·2H2OF(000) = 936
Mr = 444.91Dx = 1.307 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9994 reflections
a = 9.0611 (1) Åθ = 2.3–32.3°
b = 13.8393 (2) ŵ = 0.20 mm1
c = 18.0470 (3) ÅT = 100 K
β = 92.386 (1)°Block, bronze
V = 2261.12 (6) Å30.40 × 0.30 × 0.27 mm
Z = 4
Data collection
Bruker SMART APEX II CCD diffractometer8235 independent reflections
Radiation source: fine-focus sealed tube6221 reflections with I > 2σ(I)
graphiteRint = 0.030
[var phi] and ω scansθmax = 32.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −13→12
Tmin = 0.922, Tmax = 0.947k = −15→20
31604 measured reflectionsl = −27→27
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.067P)2 + 0.584P] where P = (Fo2 + 2Fc2)/3
8235 reflections(Δ/σ)max = 0.001
296 parametersΔρmax = 0.54 e Å3
0 restraintsΔρmin = −0.40 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 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
Cl10.00707 (4)1.20793 (2)1.108564 (19)0.03204 (9)
O10.79039 (11)0.47315 (7)0.97069 (5)0.0284 (2)
O20.71434 (12)0.49126 (7)1.08701 (6)0.0345 (2)
N10.39801 (11)0.80622 (7)1.05570 (5)0.02072 (19)
N20.39541 (11)0.84567 (7)0.93472 (5)0.01967 (19)
N30.31059 (13)1.05497 (9)0.76026 (6)0.0275 (2)
N40.07811 (15)1.10407 (11)0.74881 (7)0.0405 (3)
C10.47996 (13)0.73886 (9)1.01809 (6)0.0201 (2)
C20.55633 (14)0.65815 (9)1.04496 (6)0.0223 (2)
H2A0.55630.64081.09590.027*
C30.63268 (14)0.60382 (9)0.99427 (7)0.0228 (2)
C40.63171 (14)0.62896 (9)0.91822 (7)0.0246 (2)
H4A0.68590.59050.88520.030*
C50.55404 (14)0.70792 (9)0.89077 (6)0.0237 (2)
H5A0.55160.72410.83960.028*
C60.47921 (13)0.76287 (9)0.94225 (6)0.0201 (2)
C70.34981 (13)0.86860 (9)1.00442 (6)0.0194 (2)
C80.25981 (13)0.95260 (8)1.02341 (6)0.0192 (2)
C90.27664 (13)1.04393 (9)0.99159 (6)0.0214 (2)
H9A0.34211.05210.95230.026*
C100.19832 (14)1.12307 (9)1.01704 (7)0.0228 (2)
H10A0.20981.18500.99530.027*
C110.10321 (14)1.11010 (9)1.07454 (7)0.0235 (2)
C120.08425 (14)1.01997 (9)1.10666 (7)0.0253 (2)
H12A0.01831.01211.14580.030*
C130.16240 (14)0.94177 (9)1.08108 (6)0.0229 (2)
H13A0.14980.88001.10290.027*
C140.71494 (14)0.51778 (9)1.02296 (7)0.0255 (2)
C150.87442 (16)0.38867 (10)0.99498 (8)0.0303 (3)
H15A0.80830.33981.01600.036*
H15B0.95030.40681.03350.036*
C160.94627 (18)0.34885 (11)0.92785 (9)0.0379 (3)
H16A1.00400.29140.94190.057*
H16B1.01160.39790.90770.057*
H16C0.87000.33140.89010.057*
C170.35549 (14)0.89102 (9)0.86335 (6)0.0219 (2)
H17A0.26970.93420.86940.026*
H17B0.32560.84020.82710.026*
C180.48274 (14)0.94958 (10)0.83277 (6)0.0260 (2)
H18A0.50951.00270.86750.031*
H18B0.57030.90740.82860.031*
C190.43969 (16)0.99175 (11)0.75674 (7)0.0293 (3)
H19A0.52381.02900.73820.035*
H19B0.41750.93850.72140.035*
C200.17101 (17)1.03385 (12)0.73574 (7)0.0339 (3)
H20A0.14350.97500.71180.041*
C210.16200 (19)1.17397 (13)0.78406 (9)0.0414 (4)
H21A0.12521.23410.80070.050*
C220.30538 (18)1.14512 (11)0.79179 (8)0.0349 (3)
H22A0.38541.18020.81440.042*
O1W0.35783 (15)0.73706 (9)0.20403 (6)0.0449 (3)
O2W0.78478 (15)0.35533 (11)0.20142 (7)0.0478 (3)
H1W10.354 (3)0.7653 (18)0.1566 (14)0.067 (7)*
H2W10.307 (2)0.7811 (16)0.2306 (12)0.052 (6)*
H1W20.870 (2)0.3758 (15)0.2149 (12)0.045 (5)*
H2W20.757 (3)0.3993 (16)0.1690 (14)0.057 (6)*
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
Cl10.03324 (18)0.02542 (16)0.03796 (17)0.00757 (13)0.00755 (13)−0.00212 (12)
O10.0276 (5)0.0222 (4)0.0355 (5)0.0066 (4)0.0011 (4)0.0004 (4)
O20.0391 (6)0.0306 (5)0.0336 (5)0.0089 (4)0.0012 (4)0.0078 (4)
N10.0233 (5)0.0215 (5)0.0175 (4)0.0019 (4)0.0022 (3)0.0011 (3)
N20.0222 (5)0.0213 (4)0.0156 (4)0.0017 (4)0.0010 (3)0.0011 (3)
N30.0310 (6)0.0312 (6)0.0202 (4)−0.0011 (5)−0.0003 (4)0.0056 (4)
N40.0324 (6)0.0539 (8)0.0351 (6)0.0007 (6)0.0024 (5)0.0165 (6)
C10.0211 (5)0.0217 (5)0.0174 (4)−0.0001 (4)0.0020 (4)0.0005 (4)
C20.0239 (6)0.0225 (5)0.0204 (5)0.0009 (4)0.0013 (4)0.0020 (4)
C30.0232 (6)0.0201 (5)0.0250 (5)0.0017 (4)0.0003 (4)0.0001 (4)
C40.0264 (6)0.0249 (6)0.0227 (5)0.0037 (5)0.0025 (4)−0.0032 (4)
C50.0270 (6)0.0261 (6)0.0180 (5)0.0023 (5)0.0019 (4)−0.0015 (4)
C60.0209 (5)0.0217 (5)0.0176 (4)0.0010 (4)0.0006 (4)0.0003 (4)
C70.0201 (5)0.0213 (5)0.0168 (4)−0.0007 (4)0.0017 (4)0.0002 (4)
C80.0199 (5)0.0205 (5)0.0173 (4)0.0003 (4)0.0000 (4)−0.0003 (4)
C90.0209 (5)0.0237 (5)0.0196 (4)−0.0008 (4)0.0004 (4)0.0021 (4)
C100.0231 (5)0.0200 (5)0.0251 (5)0.0004 (4)−0.0009 (4)0.0026 (4)
C110.0217 (5)0.0232 (5)0.0255 (5)0.0028 (4)0.0000 (4)−0.0020 (4)
C120.0256 (6)0.0259 (6)0.0246 (5)0.0012 (5)0.0055 (4)−0.0002 (4)
C130.0246 (6)0.0219 (5)0.0225 (5)0.0005 (4)0.0041 (4)0.0017 (4)
C140.0237 (6)0.0209 (5)0.0317 (6)0.0011 (5)−0.0005 (4)0.0008 (4)
C150.0276 (6)0.0217 (6)0.0413 (7)0.0049 (5)−0.0009 (5)0.0011 (5)
C160.0360 (8)0.0301 (7)0.0473 (8)0.0094 (6)0.0010 (6)−0.0014 (6)
C170.0240 (5)0.0268 (6)0.0149 (4)0.0021 (5)−0.0005 (4)0.0023 (4)
C180.0244 (6)0.0324 (6)0.0212 (5)0.0008 (5)0.0021 (4)0.0051 (5)
C190.0338 (7)0.0342 (7)0.0203 (5)0.0022 (5)0.0054 (5)0.0052 (5)
C200.0344 (7)0.0438 (8)0.0232 (5)−0.0083 (6)−0.0025 (5)0.0084 (5)
C210.0451 (9)0.0374 (8)0.0421 (8)0.0076 (7)0.0070 (7)0.0098 (6)
C220.0406 (8)0.0317 (7)0.0323 (6)−0.0015 (6)0.0010 (6)0.0033 (5)
O1W0.0663 (8)0.0436 (6)0.0255 (5)0.0184 (6)0.0094 (5)0.0097 (5)
O2W0.0364 (6)0.0639 (8)0.0424 (6)−0.0085 (6)−0.0064 (5)0.0247 (6)
Geometric parameters (Å, °)
Cl1—C111.7358 (13)C10—C111.3880 (17)
O1—C141.3387 (16)C10—H10A0.9500
O1—C151.4529 (16)C11—C121.3892 (18)
O2—C141.2131 (16)C12—C131.3831 (17)
N1—C71.3261 (15)C12—H12A0.9500
N1—C11.3868 (15)C13—H13A0.9500
N2—C71.3773 (14)C15—C161.504 (2)
N2—C61.3782 (15)C15—H15A0.9900
N2—C171.4646 (14)C15—H15B0.9900
N3—C201.3544 (18)C16—H16A0.9800
N3—C221.3729 (19)C16—H16B0.9800
N3—C191.4642 (18)C16—H16C0.9800
N4—C201.313 (2)C17—C181.5310 (18)
N4—C211.370 (2)C17—H17A0.9900
C1—C21.3906 (17)C17—H17B0.9900
C1—C61.4081 (15)C18—C191.5268 (17)
C2—C31.3906 (17)C18—H18A0.9900
C2—H2A0.9500C18—H18B0.9900
C3—C41.4154 (17)C19—H19A0.9900
C3—C141.4864 (17)C19—H19B0.9900
C4—C51.3805 (17)C20—H20A0.9500
C4—H4A0.9500C21—C221.361 (2)
C5—C61.3979 (16)C21—H21A0.9500
C5—H5A0.9500C22—H22A0.9500
C7—C81.4687 (16)O1W—H1W10.94 (3)
C8—C91.3993 (16)O1W—H2W10.91 (2)
C8—C131.4004 (16)O2W—H1W20.85 (2)
C9—C101.3933 (17)O2W—H2W20.87 (2)
C9—H9A0.9500
C14—O1—C15115.80 (10)C12—C13—H13A119.6
C7—N1—C1105.28 (9)C8—C13—H13A119.6
C7—N2—C6106.64 (9)O2—C14—O1123.67 (12)
C7—N2—C17129.20 (10)O2—C14—C3123.52 (12)
C6—N2—C17123.91 (9)O1—C14—C3112.80 (11)
C20—N3—C22106.48 (13)O1—C15—C16106.91 (11)
C20—N3—C19126.43 (13)O1—C15—H15A110.3
C22—N3—C19127.03 (12)C16—C15—H15A110.3
C20—N4—C21104.98 (13)O1—C15—H15B110.3
N1—C1—C2129.64 (10)C16—C15—H15B110.3
N1—C1—C6109.64 (10)H15A—C15—H15B108.6
C2—C1—C6120.72 (10)C15—C16—H16A109.5
C1—C2—C3117.31 (10)C15—C16—H16B109.5
C1—C2—H2A121.3H16A—C16—H16B109.5
C3—C2—H2A121.3C15—C16—H16C109.5
C2—C3—C4121.46 (11)H16A—C16—H16C109.5
C2—C3—C14117.39 (11)H16B—C16—H16C109.5
C4—C3—C14121.16 (11)N2—C17—C18112.44 (10)
C5—C4—C3121.67 (11)N2—C17—H17A109.1
C5—C4—H4A119.2C18—C17—H17A109.1
C3—C4—H4A119.2N2—C17—H17B109.1
C4—C5—C6116.50 (11)C18—C17—H17B109.1
C4—C5—H5A121.7H17A—C17—H17B107.8
C6—C5—H5A121.7C19—C18—C17110.99 (10)
N2—C6—C5131.86 (10)C19—C18—H18A109.4
N2—C6—C1105.81 (10)C17—C18—H18A109.4
C5—C6—C1122.33 (11)C19—C18—H18B109.4
N1—C7—N2112.63 (10)C17—C18—H18B109.4
N1—C7—C8121.49 (10)H18A—C18—H18B108.0
N2—C7—C8125.88 (10)N3—C19—C18111.35 (10)
C9—C8—C13118.98 (11)N3—C19—H19A109.4
C9—C8—C7123.24 (10)C18—C19—H19A109.4
C13—C8—C7117.52 (10)N3—C19—H19B109.4
C10—C9—C8120.61 (11)C18—C19—H19B109.4
C10—C9—H9A119.7H19A—C19—H19B108.0
C8—C9—H9A119.7N4—C20—N3112.24 (14)
C11—C10—C9119.04 (11)N4—C20—H20A123.9
C11—C10—H10A120.5N3—C20—H20A123.9
C9—C10—H10A120.5C22—C21—N4110.43 (15)
C10—C11—C12121.30 (11)C22—C21—H21A124.8
C10—C11—Cl1120.00 (10)N4—C21—H21A124.8
C12—C11—Cl1118.70 (9)C21—C22—N3105.87 (14)
C13—C12—C11119.30 (11)C21—C22—H22A127.1
C13—C12—H12A120.3N3—C22—H22A127.1
C11—C12—H12A120.3H1W1—O1W—H2W1101.6 (19)
C12—C13—C8120.77 (11)H1W2—O2W—H2W2101 (2)
C7—N1—C1—C2179.48 (12)C7—C8—C9—C10−173.62 (11)
C7—N1—C1—C6−0.08 (13)C8—C9—C10—C110.05 (17)
N1—C1—C2—C3−178.60 (12)C9—C10—C11—C12−0.39 (18)
C6—C1—C2—C30.91 (18)C9—C10—C11—Cl1178.71 (9)
C1—C2—C3—C4−0.60 (18)C10—C11—C12—C130.39 (19)
C1—C2—C3—C14179.73 (11)Cl1—C11—C12—C13−178.73 (10)
C2—C3—C4—C5−0.6 (2)C11—C12—C13—C8−0.04 (19)
C14—C3—C4—C5179.08 (12)C9—C8—C13—C12−0.30 (18)
C3—C4—C5—C61.37 (19)C7—C8—C13—C12173.96 (11)
C7—N2—C6—C5−179.35 (13)C15—O1—C14—O2−0.03 (19)
C17—N2—C6—C55.9 (2)C15—O1—C14—C3179.57 (10)
C7—N2—C6—C10.18 (13)C2—C3—C14—O22.6 (2)
C17—N2—C6—C1−174.58 (11)C4—C3—C14—O2−177.04 (13)
C4—C5—C6—N2178.41 (12)C2—C3—C14—O1−176.97 (11)
C4—C5—C6—C1−1.06 (19)C4—C3—C14—O13.36 (17)
N1—C1—C6—N2−0.07 (13)C14—O1—C15—C16178.52 (12)
C2—C1—C6—N2−179.67 (11)C7—N2—C17—C18108.32 (14)
N1—C1—C6—C5179.52 (11)C6—N2—C17—C18−78.16 (14)
C2—C1—C6—C5−0.08 (19)N2—C17—C18—C19177.29 (10)
C1—N1—C7—N20.20 (14)C20—N3—C19—C18−105.09 (14)
C1—N1—C7—C8−178.91 (10)C22—N3—C19—C1871.78 (17)
C6—N2—C7—N1−0.24 (14)C17—C18—C19—N359.23 (15)
C17—N2—C7—N1174.15 (11)C21—N4—C20—N3−0.39 (16)
C6—N2—C7—C8178.82 (11)C22—N3—C20—N40.51 (15)
C17—N2—C7—C8−6.79 (19)C19—N3—C20—N4177.91 (11)
N1—C7—C8—C9140.42 (12)C20—N4—C21—C220.12 (17)
N2—C7—C8—C9−38.57 (18)N4—C21—C22—N30.19 (17)
N1—C7—C8—C13−33.57 (16)C20—N3—C22—C21−0.41 (15)
N2—C7—C8—C13147.44 (12)C19—N3—C22—C21−177.78 (12)
C13—C8—C9—C100.29 (17)
Hydrogen-bond geometry (Å, °)
Cg1 is the centroid of the C1–C6 phenyl ring.
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···N1i0.94 (3)1.96 (3)2.8802 (14)164 (2)
O1W—H2W1···O2Wii0.91 (2)1.83 (2)2.7284 (18)169 (2)
O2W—H1W2···N4iii0.849 (19)1.978 (19)2.8147 (19)169 (2)
O2W—H2W2···O2i0.87 (2)1.98 (2)2.8460 (17)172 (2)
C17—H17B···O1Wiv0.992.493.3785 (16)149
C19—H19B···O1Wiv0.992.513.3799 (19)147
C10—H10A···Cg1v0.952.863.4875 (14)125
Symmetry codes: (i) x, y, z−1; (ii) −x+1, y+1/2, −z+1/2; (iii) x+1, −y+3/2, z−1/2; (iv) x, −y+3/2, z+1/2; (v) −x+1, −y+2, −z+2.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6369).
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