organic compounds
Ethyl 1-[3-(1H-imidazol-1-yl)propyl]-2-(4-chlorophenyl)-1H-benzo[d]imidazole-5-carboxylate dihydrate
aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my
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 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 R12(6) loops. C—H⋯π interactions are also observed.
Related literature
For related structures and background to benzimidazoles, see: Eltayeb et al. (2009, 2011). For standard bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).
Experimental
Crystal data
|
Refinement
|
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536811033654/hb6369sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811033654/hb6369Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811033654/hb6369Isup3.cml
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).
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.
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms. | |
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. |
C22H21ClN4O2·2H2O | F(000) = 936 |
Mr = 444.91 | Dx = 1.307 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9994 reflections |
a = 9.0611 (1) Å | θ = 2.3–32.3° |
b = 13.8393 (2) Å | µ = 0.20 mm−1 |
c = 18.0470 (3) Å | T = 100 K |
β = 92.386 (1)° | Block, bronze |
V = 2261.12 (6) Å3 | 0.40 × 0.30 × 0.27 mm |
Z = 4 |
Bruker SMART APEX II CCD diffractometer | 8235 independent reflections |
Radiation source: fine-focus sealed tube | 6221 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ϕ and ω scans | θmax = 32.7°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −13→12 |
Tmin = 0.922, Tmax = 0.947 | k = −15→20 |
31604 measured reflections | l = −27→27 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.067P)2 + 0.584P] where P = (Fo2 + 2Fc2)/3 |
8235 reflections | (Δ/σ)max = 0.001 |
296 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
C22H21ClN4O2·2H2O | V = 2261.12 (6) Å3 |
Mr = 444.91 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.0611 (1) Å | µ = 0.20 mm−1 |
b = 13.8393 (2) Å | T = 100 K |
c = 18.0470 (3) Å | 0.40 × 0.30 × 0.27 mm |
β = 92.386 (1)° |
Bruker SMART APEX II CCD diffractometer | 8235 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 6221 reflections with I > 2σ(I) |
Tmin = 0.922, Tmax = 0.947 | Rint = 0.030 |
31604 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.54 e Å−3 |
8235 reflections | Δρmin = −0.40 e Å−3 |
296 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.00707 (4) | 1.20793 (2) | 1.108564 (19) | 0.03204 (9) | |
O1 | 0.79039 (11) | 0.47315 (7) | 0.97069 (5) | 0.0284 (2) | |
O2 | 0.71434 (12) | 0.49126 (7) | 1.08701 (6) | 0.0345 (2) | |
N1 | 0.39801 (11) | 0.80622 (7) | 1.05570 (5) | 0.02072 (19) | |
N2 | 0.39541 (11) | 0.84567 (7) | 0.93472 (5) | 0.01967 (19) | |
N3 | 0.31059 (13) | 1.05497 (9) | 0.76026 (6) | 0.0275 (2) | |
N4 | 0.07811 (15) | 1.10407 (11) | 0.74881 (7) | 0.0405 (3) | |
C1 | 0.47996 (13) | 0.73886 (9) | 1.01809 (6) | 0.0201 (2) | |
C2 | 0.55633 (14) | 0.65815 (9) | 1.04496 (6) | 0.0223 (2) | |
H2A | 0.5563 | 0.6408 | 1.0959 | 0.027* | |
C3 | 0.63268 (14) | 0.60382 (9) | 0.99427 (7) | 0.0228 (2) | |
C4 | 0.63171 (14) | 0.62896 (9) | 0.91822 (7) | 0.0246 (2) | |
H4A | 0.6859 | 0.5905 | 0.8852 | 0.030* | |
C5 | 0.55404 (14) | 0.70792 (9) | 0.89077 (6) | 0.0237 (2) | |
H5A | 0.5516 | 0.7241 | 0.8396 | 0.028* | |
C6 | 0.47921 (13) | 0.76287 (9) | 0.94225 (6) | 0.0201 (2) | |
C7 | 0.34981 (13) | 0.86860 (9) | 1.00442 (6) | 0.0194 (2) | |
C8 | 0.25981 (13) | 0.95260 (8) | 1.02341 (6) | 0.0192 (2) | |
C9 | 0.27664 (13) | 1.04393 (9) | 0.99159 (6) | 0.0214 (2) | |
H9A | 0.3421 | 1.0521 | 0.9523 | 0.026* | |
C10 | 0.19832 (14) | 1.12307 (9) | 1.01704 (7) | 0.0228 (2) | |
H10A | 0.2098 | 1.1850 | 0.9953 | 0.027* | |
C11 | 0.10321 (14) | 1.11010 (9) | 1.07454 (7) | 0.0235 (2) | |
C12 | 0.08425 (14) | 1.01997 (9) | 1.10666 (7) | 0.0253 (2) | |
H12A | 0.0183 | 1.0121 | 1.1458 | 0.030* | |
C13 | 0.16240 (14) | 0.94177 (9) | 1.08108 (6) | 0.0229 (2) | |
H13A | 0.1498 | 0.8800 | 1.1029 | 0.027* | |
C14 | 0.71494 (14) | 0.51778 (9) | 1.02296 (7) | 0.0255 (2) | |
C15 | 0.87442 (16) | 0.38867 (10) | 0.99498 (8) | 0.0303 (3) | |
H15A | 0.8083 | 0.3398 | 1.0160 | 0.036* | |
H15B | 0.9503 | 0.4068 | 1.0335 | 0.036* | |
C16 | 0.94627 (18) | 0.34885 (11) | 0.92785 (9) | 0.0379 (3) | |
H16A | 1.0040 | 0.2914 | 0.9419 | 0.057* | |
H16B | 1.0116 | 0.3979 | 0.9077 | 0.057* | |
H16C | 0.8700 | 0.3314 | 0.8901 | 0.057* | |
C17 | 0.35549 (14) | 0.89102 (9) | 0.86335 (6) | 0.0219 (2) | |
H17A | 0.2697 | 0.9342 | 0.8694 | 0.026* | |
H17B | 0.3256 | 0.8402 | 0.8271 | 0.026* | |
C18 | 0.48274 (14) | 0.94958 (10) | 0.83277 (6) | 0.0260 (2) | |
H18A | 0.5095 | 1.0027 | 0.8675 | 0.031* | |
H18B | 0.5703 | 0.9074 | 0.8286 | 0.031* | |
C19 | 0.43969 (16) | 0.99175 (11) | 0.75674 (7) | 0.0293 (3) | |
H19A | 0.5238 | 1.0290 | 0.7382 | 0.035* | |
H19B | 0.4175 | 0.9385 | 0.7214 | 0.035* | |
C20 | 0.17101 (17) | 1.03385 (12) | 0.73574 (7) | 0.0339 (3) | |
H20A | 0.1435 | 0.9750 | 0.7118 | 0.041* | |
C21 | 0.16200 (19) | 1.17397 (13) | 0.78406 (9) | 0.0414 (4) | |
H21A | 0.1252 | 1.2341 | 0.8007 | 0.050* | |
C22 | 0.30538 (18) | 1.14512 (11) | 0.79179 (8) | 0.0349 (3) | |
H22A | 0.3854 | 1.1802 | 0.8144 | 0.042* | |
O1W | 0.35783 (15) | 0.73706 (9) | 0.20403 (6) | 0.0449 (3) | |
O2W | 0.78478 (15) | 0.35533 (11) | 0.20142 (7) | 0.0478 (3) | |
H1W1 | 0.354 (3) | 0.7653 (18) | 0.1566 (14) | 0.067 (7)* | |
H2W1 | 0.307 (2) | 0.7811 (16) | 0.2306 (12) | 0.052 (6)* | |
H1W2 | 0.870 (2) | 0.3758 (15) | 0.2149 (12) | 0.045 (5)* | |
H2W2 | 0.757 (3) | 0.3993 (16) | 0.1690 (14) | 0.057 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.03324 (18) | 0.02542 (16) | 0.03796 (17) | 0.00757 (13) | 0.00755 (13) | −0.00212 (12) |
O1 | 0.0276 (5) | 0.0222 (4) | 0.0355 (5) | 0.0066 (4) | 0.0011 (4) | 0.0004 (4) |
O2 | 0.0391 (6) | 0.0306 (5) | 0.0336 (5) | 0.0089 (4) | 0.0012 (4) | 0.0078 (4) |
N1 | 0.0233 (5) | 0.0215 (5) | 0.0175 (4) | 0.0019 (4) | 0.0022 (3) | 0.0011 (3) |
N2 | 0.0222 (5) | 0.0213 (4) | 0.0156 (4) | 0.0017 (4) | 0.0010 (3) | 0.0011 (3) |
N3 | 0.0310 (6) | 0.0312 (6) | 0.0202 (4) | −0.0011 (5) | −0.0003 (4) | 0.0056 (4) |
N4 | 0.0324 (6) | 0.0539 (8) | 0.0351 (6) | 0.0007 (6) | 0.0024 (5) | 0.0165 (6) |
C1 | 0.0211 (5) | 0.0217 (5) | 0.0174 (4) | −0.0001 (4) | 0.0020 (4) | 0.0005 (4) |
C2 | 0.0239 (6) | 0.0225 (5) | 0.0204 (5) | 0.0009 (4) | 0.0013 (4) | 0.0020 (4) |
C3 | 0.0232 (6) | 0.0201 (5) | 0.0250 (5) | 0.0017 (4) | 0.0003 (4) | 0.0001 (4) |
C4 | 0.0264 (6) | 0.0249 (6) | 0.0227 (5) | 0.0037 (5) | 0.0025 (4) | −0.0032 (4) |
C5 | 0.0270 (6) | 0.0261 (6) | 0.0180 (5) | 0.0023 (5) | 0.0019 (4) | −0.0015 (4) |
C6 | 0.0209 (5) | 0.0217 (5) | 0.0176 (4) | 0.0010 (4) | 0.0006 (4) | 0.0003 (4) |
C7 | 0.0201 (5) | 0.0213 (5) | 0.0168 (4) | −0.0007 (4) | 0.0017 (4) | 0.0002 (4) |
C8 | 0.0199 (5) | 0.0205 (5) | 0.0173 (4) | 0.0003 (4) | 0.0000 (4) | −0.0003 (4) |
C9 | 0.0209 (5) | 0.0237 (5) | 0.0196 (4) | −0.0008 (4) | 0.0004 (4) | 0.0021 (4) |
C10 | 0.0231 (5) | 0.0200 (5) | 0.0251 (5) | 0.0004 (4) | −0.0009 (4) | 0.0026 (4) |
C11 | 0.0217 (5) | 0.0232 (5) | 0.0255 (5) | 0.0028 (4) | 0.0000 (4) | −0.0020 (4) |
C12 | 0.0256 (6) | 0.0259 (6) | 0.0246 (5) | 0.0012 (5) | 0.0055 (4) | −0.0002 (4) |
C13 | 0.0246 (6) | 0.0219 (5) | 0.0225 (5) | 0.0005 (4) | 0.0041 (4) | 0.0017 (4) |
C14 | 0.0237 (6) | 0.0209 (5) | 0.0317 (6) | 0.0011 (5) | −0.0005 (4) | 0.0008 (4) |
C15 | 0.0276 (6) | 0.0217 (6) | 0.0413 (7) | 0.0049 (5) | −0.0009 (5) | 0.0011 (5) |
C16 | 0.0360 (8) | 0.0301 (7) | 0.0473 (8) | 0.0094 (6) | 0.0010 (6) | −0.0014 (6) |
C17 | 0.0240 (5) | 0.0268 (6) | 0.0149 (4) | 0.0021 (5) | −0.0005 (4) | 0.0023 (4) |
C18 | 0.0244 (6) | 0.0324 (6) | 0.0212 (5) | 0.0008 (5) | 0.0021 (4) | 0.0051 (5) |
C19 | 0.0338 (7) | 0.0342 (7) | 0.0203 (5) | 0.0022 (5) | 0.0054 (5) | 0.0052 (5) |
C20 | 0.0344 (7) | 0.0438 (8) | 0.0232 (5) | −0.0083 (6) | −0.0025 (5) | 0.0084 (5) |
C21 | 0.0451 (9) | 0.0374 (8) | 0.0421 (8) | 0.0076 (7) | 0.0070 (7) | 0.0098 (6) |
C22 | 0.0406 (8) | 0.0317 (7) | 0.0323 (6) | −0.0015 (6) | 0.0010 (6) | 0.0033 (5) |
O1W | 0.0663 (8) | 0.0436 (6) | 0.0255 (5) | 0.0184 (6) | 0.0094 (5) | 0.0097 (5) |
O2W | 0.0364 (6) | 0.0639 (8) | 0.0424 (6) | −0.0085 (6) | −0.0064 (5) | 0.0247 (6) |
Cl1—C11 | 1.7358 (13) | C10—C11 | 1.3880 (17) |
O1—C14 | 1.3387 (16) | C10—H10A | 0.9500 |
O1—C15 | 1.4529 (16) | C11—C12 | 1.3892 (18) |
O2—C14 | 1.2131 (16) | C12—C13 | 1.3831 (17) |
N1—C7 | 1.3261 (15) | C12—H12A | 0.9500 |
N1—C1 | 1.3868 (15) | C13—H13A | 0.9500 |
N2—C7 | 1.3773 (14) | C15—C16 | 1.504 (2) |
N2—C6 | 1.3782 (15) | C15—H15A | 0.9900 |
N2—C17 | 1.4646 (14) | C15—H15B | 0.9900 |
N3—C20 | 1.3544 (18) | C16—H16A | 0.9800 |
N3—C22 | 1.3729 (19) | C16—H16B | 0.9800 |
N3—C19 | 1.4642 (18) | C16—H16C | 0.9800 |
N4—C20 | 1.313 (2) | C17—C18 | 1.5310 (18) |
N4—C21 | 1.370 (2) | C17—H17A | 0.9900 |
C1—C2 | 1.3906 (17) | C17—H17B | 0.9900 |
C1—C6 | 1.4081 (15) | C18—C19 | 1.5268 (17) |
C2—C3 | 1.3906 (17) | C18—H18A | 0.9900 |
C2—H2A | 0.9500 | C18—H18B | 0.9900 |
C3—C4 | 1.4154 (17) | C19—H19A | 0.9900 |
C3—C14 | 1.4864 (17) | C19—H19B | 0.9900 |
C4—C5 | 1.3805 (17) | C20—H20A | 0.9500 |
C4—H4A | 0.9500 | C21—C22 | 1.361 (2) |
C5—C6 | 1.3979 (16) | C21—H21A | 0.9500 |
C5—H5A | 0.9500 | C22—H22A | 0.9500 |
C7—C8 | 1.4687 (16) | O1W—H1W1 | 0.94 (3) |
C8—C9 | 1.3993 (16) | O1W—H2W1 | 0.91 (2) |
C8—C13 | 1.4004 (16) | O2W—H1W2 | 0.85 (2) |
C9—C10 | 1.3933 (17) | O2W—H2W2 | 0.87 (2) |
C9—H9A | 0.9500 | ||
C14—O1—C15 | 115.80 (10) | C12—C13—H13A | 119.6 |
C7—N1—C1 | 105.28 (9) | C8—C13—H13A | 119.6 |
C7—N2—C6 | 106.64 (9) | O2—C14—O1 | 123.67 (12) |
C7—N2—C17 | 129.20 (10) | O2—C14—C3 | 123.52 (12) |
C6—N2—C17 | 123.91 (9) | O1—C14—C3 | 112.80 (11) |
C20—N3—C22 | 106.48 (13) | O1—C15—C16 | 106.91 (11) |
C20—N3—C19 | 126.43 (13) | O1—C15—H15A | 110.3 |
C22—N3—C19 | 127.03 (12) | C16—C15—H15A | 110.3 |
C20—N4—C21 | 104.98 (13) | O1—C15—H15B | 110.3 |
N1—C1—C2 | 129.64 (10) | C16—C15—H15B | 110.3 |
N1—C1—C6 | 109.64 (10) | H15A—C15—H15B | 108.6 |
C2—C1—C6 | 120.72 (10) | C15—C16—H16A | 109.5 |
C1—C2—C3 | 117.31 (10) | C15—C16—H16B | 109.5 |
C1—C2—H2A | 121.3 | H16A—C16—H16B | 109.5 |
C3—C2—H2A | 121.3 | C15—C16—H16C | 109.5 |
C2—C3—C4 | 121.46 (11) | H16A—C16—H16C | 109.5 |
C2—C3—C14 | 117.39 (11) | H16B—C16—H16C | 109.5 |
C4—C3—C14 | 121.16 (11) | N2—C17—C18 | 112.44 (10) |
C5—C4—C3 | 121.67 (11) | N2—C17—H17A | 109.1 |
C5—C4—H4A | 119.2 | C18—C17—H17A | 109.1 |
C3—C4—H4A | 119.2 | N2—C17—H17B | 109.1 |
C4—C5—C6 | 116.50 (11) | C18—C17—H17B | 109.1 |
C4—C5—H5A | 121.7 | H17A—C17—H17B | 107.8 |
C6—C5—H5A | 121.7 | C19—C18—C17 | 110.99 (10) |
N2—C6—C5 | 131.86 (10) | C19—C18—H18A | 109.4 |
N2—C6—C1 | 105.81 (10) | C17—C18—H18A | 109.4 |
C5—C6—C1 | 122.33 (11) | C19—C18—H18B | 109.4 |
N1—C7—N2 | 112.63 (10) | C17—C18—H18B | 109.4 |
N1—C7—C8 | 121.49 (10) | H18A—C18—H18B | 108.0 |
N2—C7—C8 | 125.88 (10) | N3—C19—C18 | 111.35 (10) |
C9—C8—C13 | 118.98 (11) | N3—C19—H19A | 109.4 |
C9—C8—C7 | 123.24 (10) | C18—C19—H19A | 109.4 |
C13—C8—C7 | 117.52 (10) | N3—C19—H19B | 109.4 |
C10—C9—C8 | 120.61 (11) | C18—C19—H19B | 109.4 |
C10—C9—H9A | 119.7 | H19A—C19—H19B | 108.0 |
C8—C9—H9A | 119.7 | N4—C20—N3 | 112.24 (14) |
C11—C10—C9 | 119.04 (11) | N4—C20—H20A | 123.9 |
C11—C10—H10A | 120.5 | N3—C20—H20A | 123.9 |
C9—C10—H10A | 120.5 | C22—C21—N4 | 110.43 (15) |
C10—C11—C12 | 121.30 (11) | C22—C21—H21A | 124.8 |
C10—C11—Cl1 | 120.00 (10) | N4—C21—H21A | 124.8 |
C12—C11—Cl1 | 118.70 (9) | C21—C22—N3 | 105.87 (14) |
C13—C12—C11 | 119.30 (11) | C21—C22—H22A | 127.1 |
C13—C12—H12A | 120.3 | N3—C22—H22A | 127.1 |
C11—C12—H12A | 120.3 | H1W1—O1W—H2W1 | 101.6 (19) |
C12—C13—C8 | 120.77 (11) | H1W2—O2W—H2W2 | 101 (2) |
C7—N1—C1—C2 | 179.48 (12) | C7—C8—C9—C10 | −173.62 (11) |
C7—N1—C1—C6 | −0.08 (13) | C8—C9—C10—C11 | 0.05 (17) |
N1—C1—C2—C3 | −178.60 (12) | C9—C10—C11—C12 | −0.39 (18) |
C6—C1—C2—C3 | 0.91 (18) | C9—C10—C11—Cl1 | 178.71 (9) |
C1—C2—C3—C4 | −0.60 (18) | C10—C11—C12—C13 | 0.39 (19) |
C1—C2—C3—C14 | 179.73 (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—C5 | 179.08 (12) | C9—C8—C13—C12 | −0.30 (18) |
C3—C4—C5—C6 | 1.37 (19) | C7—C8—C13—C12 | 173.96 (11) |
C7—N2—C6—C5 | −179.35 (13) | C15—O1—C14—O2 | −0.03 (19) |
C17—N2—C6—C5 | 5.9 (2) | C15—O1—C14—C3 | 179.57 (10) |
C7—N2—C6—C1 | 0.18 (13) | C2—C3—C14—O2 | 2.6 (2) |
C17—N2—C6—C1 | −174.58 (11) | C4—C3—C14—O2 | −177.04 (13) |
C4—C5—C6—N2 | 178.41 (12) | C2—C3—C14—O1 | −176.97 (11) |
C4—C5—C6—C1 | −1.06 (19) | C4—C3—C14—O1 | 3.36 (17) |
N1—C1—C6—N2 | −0.07 (13) | C14—O1—C15—C16 | 178.52 (12) |
C2—C1—C6—N2 | −179.67 (11) | C7—N2—C17—C18 | 108.32 (14) |
N1—C1—C6—C5 | 179.52 (11) | C6—N2—C17—C18 | −78.16 (14) |
C2—C1—C6—C5 | −0.08 (19) | N2—C17—C18—C19 | 177.29 (10) |
C1—N1—C7—N2 | 0.20 (14) | C20—N3—C19—C18 | −105.09 (14) |
C1—N1—C7—C8 | −178.91 (10) | C22—N3—C19—C18 | 71.78 (17) |
C6—N2—C7—N1 | −0.24 (14) | C17—C18—C19—N3 | 59.23 (15) |
C17—N2—C7—N1 | 174.15 (11) | C21—N4—C20—N3 | −0.39 (16) |
C6—N2—C7—C8 | 178.82 (11) | C22—N3—C20—N4 | 0.51 (15) |
C17—N2—C7—C8 | −6.79 (19) | C19—N3—C20—N4 | 177.91 (11) |
N1—C7—C8—C9 | 140.42 (12) | C20—N4—C21—C22 | 0.12 (17) |
N2—C7—C8—C9 | −38.57 (18) | N4—C21—C22—N3 | 0.19 (17) |
N1—C7—C8—C13 | −33.57 (16) | C20—N3—C22—C21 | −0.41 (15) |
N2—C7—C8—C13 | 147.44 (12) | C19—N3—C22—C21 | −177.78 (12) |
C13—C8—C9—C10 | 0.29 (17) |
Cg1 is the centroid of the C1–C6 phenyl ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···N1i | 0.94 (3) | 1.96 (3) | 2.8802 (14) | 164 (2) |
O1W—H2W1···O2Wii | 0.91 (2) | 1.83 (2) | 2.7284 (18) | 169 (2) |
O2W—H1W2···N4iii | 0.849 (19) | 1.978 (19) | 2.8147 (19) | 169 (2) |
O2W—H2W2···O2i | 0.87 (2) | 1.98 (2) | 2.8460 (17) | 172 (2) |
C17—H17B···O1Wiv | 0.99 | 2.49 | 3.3785 (16) | 149 |
C19—H19B···O1Wiv | 0.99 | 2.51 | 3.3799 (19) | 147 |
C10—H10A···Cg1v | 0.95 | 2.86 | 3.4875 (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. |
Experimental details
Crystal data | |
Chemical formula | C22H21ClN4O2·2H2O |
Mr | 444.91 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 9.0611 (1), 13.8393 (2), 18.0470 (3) |
β (°) | 92.386 (1) |
V (Å3) | 2261.12 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.40 × 0.30 × 0.27 |
Data collection | |
Diffractometer | Bruker SMART APEX II CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.922, 0.947 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 31604, 8235, 6221 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.759 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.136, 1.05 |
No. of reflections | 8235 |
No. of parameters | 296 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.54, −0.40 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg1 is the centroid of the C1–C6 phenyl ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···N1i | 0.94 (3) | 1.96 (3) | 2.8802 (14) | 164 (2) |
O1W—H2W1···O2Wii | 0.91 (2) | 1.83 (2) | 2.7284 (18) | 169 (2) |
O2W—H1W2···N4iii | 0.849 (19) | 1.978 (19) | 2.8147 (19) | 169 (2) |
O2W—H2W2···O2i | 0.87 (2) | 1.98 (2) | 2.8460 (17) | 172 (2) |
C17—H17B···O1Wiv | 0.99 | 2.49 | 3.3785 (16) | 149 |
C19—H19B···O1Wiv | 0.99 | 2.51 | 3.3799 (19) | 147 |
C10—H10A···Cg1v | 0.95 | 2.86 | 3.4875 (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. |
Acknowledgements
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).
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, S1–S19. CrossRef Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Eltayeb, N. E., Teoh, S. G., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o2243–o2244. CrossRef IUCr Journals Google Scholar
Eltayeb, N. E., Teoh, S. G., Quah, C. K., Fun, H.-K. & Adnan, R. (2009). Acta Cryst. E65, o1613–o1614. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.