Ethyl 1-[3-(1H-imidazol-1-yl)prop­yl]-2-(4-chloro­phen­yl)-1H-benzo[d]imidazole-5-carboxyl­ate dihydrate

Yoon, Y.K.; Ali, M.A.; Wei, A.C.; Quah, C.K.; Fun, H.-K.

doi:10.1107/S1600536811033654

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2405

doi:10.1107/S1600536811033654

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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 Fun ^b ^*§

^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

(Received 16 August 2011; accepted 18 August 2011; online 27 August 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 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

C₂₂H₂₁ClN₄O₂·2H₂O
M_r = 444.91
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.136
S = 1.05
8235 reflections
296 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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⋯O1W^iv	0.99	2.49	3.3785 (16)	149
C19—H19B⋯O1W^iv	0.99	2.51	3.3799 (19)	147
C10—H10A⋯Cg1^v	0.95	2.86	3.4875 (14)	125
Symmetry codes: (i) x, y, z-1; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (v) -x+1, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2009); cell refinement: 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811033654/hb6369sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033654/hb6369Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811033654/hb6369Isup3.cml

checkCIF report

Comment top

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.

Related literature top

For related sturctures 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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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).

Figures top

	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.

Ethyl 1-[3-(1H-imidazol-1-yl)propyl]-2-(4-chlorophenyl)-1H- benzo[d]imidazole-5-carboxylate dihydrate top

Crystal data top

C₂₂H₂₁ClN₄O₂·2H₂O	F(000) = 936
M_r = 444.91	D_x = 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

Data collection top

Bruker SMART APEX II CCD diffractometer	8235 independent reflections
Radiation source: fine-focus sealed tube	6221 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 32.7°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→12
T_min = 0.922, T_max = 0.947	k = −15→20
31604 measured reflections	l = −27→27

Refinement top

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(F_o²) + (0.067P)² + 0.584P] where P = (F_o² + 2F_c²)/3
8235 reflections	(Δ/σ)_max = 0.001
296 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₂₂H₂₁ClN₄O₂·2H₂O	V = 2261.12 (6) Å³
M_r = 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)°

Data collection top

Bruker SMART APEX II CCD diffractometer	8235 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6221 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.947	R_int = 0.030
31604 measured reflections

Refinement top

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	Δρ_max = 0.54 e Å⁻³
8235 reflections	Δρ_min = −0.40 e Å⁻³
296 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O1W^iv	0.99	2.49	3.3785 (16)	149
C19—H19B···O1W^iv	0.99	2.51	3.3799 (19)	147
C10—H10A···Cg1^v	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
M_r	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)
T_min, T_max	0.922, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	31604, 8235, 6221
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.40

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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···O1W^iv	0.99	2.49	3.3785 (16)	149
C19—H19B···O1W^iv	0.99	2.51	3.3799 (19)	147
C10—H10A···Cg1^v	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.

Footnotes

‡Thomson Reuters ResearcherID: A-5525-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

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

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 1-[3-(1H-imidazol-1-yl)prop­yl]-2-(4-chloro­phen­yl)-1H-benzo[d]imidazole-5-carboxyl­ate dihydrate

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Experimental

Crystal data

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organic compounds

Ethyl 1-[3-(1H-imidazol-1-yl)propyl]-2-(4-chlorophenyl)-1H-benzo[d]imidazole-5-carboxylate dihydrate