Ethyl 2-(4-bromophenyl)-1-[3-(1H-imidazol-1-yl)prop-yl]-1H-benzimidazole-5-carboxyl-ate monohydrate.

In the title compound, C(22)H(21)BrN(4)O(2)·H(2)O, the two pyrazole rings are essentially planar [maximum deviations 0.002 (1) and 0.002 (1) Å], and form a dihedral angle of 73.46 (9)°. The dihedral angle between the benzene rings is 29.33 (7)°. In the crystal, mol-ecules are connected via C-H⋯O and O-H⋯N hydrogen bonds, forming layers in the ab plane.

Related literature

For applications of benzimidazole derivatives, see: Garuti et al. (2000 ▶); Rao et al. (2002 ▶); Thakurdesai et al. (2007 ▶); Yoon et al. (2011 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C22H21BrN4O2·H2O

M = 471.35

Monoclinic,

a = 9.1854 (1) Å

b = 16.7389 (2) Å

c = 13.7379 (2) Å

β = 98.283 (1)°

V = 2090.22 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.00 mm−1

T = 100 K

0.47 × 0.42 × 0.41 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.452, T max = 0.494

28847 measured reflections

7482 independent reflections

5514 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.085

S = 1.03

7482 reflections

280 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.63 e Å−3

Δρmin = −0.34 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681104342X/tk5002sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104342X/tk5002Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104342X/tk5002Isup3.cml

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

C22H21BrN4O2·H2O	F(000) = 968
Mr = 471.35	Dx = 1.498 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9939 reflections
a = 9.1854 (1) Å	θ = 2.5–31.3°
b = 16.7389 (2) Å	µ = 2.00 mm−1
c = 13.7379 (2) Å	T = 100 K
β = 98.283 (1)°	Block, yellow
V = 2090.22 (5) Å3	0.47 × 0.42 × 0.41 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	7482 independent reflections
Radiation source: fine-focus sealed tube	5514 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 32.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.452, Tmax = 0.494	k = −25→17
28847 measured reflections	l = −20→19

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0386P)2 + 0.518P] where P = (Fo2 + 2Fc2)/3
7482 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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 s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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
Br1	0.123446 (18)	0.050021 (9)	0.931417 (13)	0.02720 (6)
O1	0.40323 (12)	0.80153 (6)	0.87745 (9)	0.0247 (2)
O2	0.17930 (13)	0.76409 (7)	0.90802 (9)	0.0260 (2)
N1	0.23105 (14)	0.45313 (7)	0.89922 (10)	0.0199 (3)
N2	0.46106 (14)	0.42561 (7)	0.87069 (9)	0.0174 (2)
N3	0.71289 (14)	0.23427 (8)	0.76584 (10)	0.0216 (3)
N4	0.61875 (16)	0.11193 (8)	0.75103 (11)	0.0265 (3)
C1	0.18138 (17)	0.29413 (9)	0.95735 (11)	0.0207 (3)
H1A	0.1411	0.3363	0.9913	0.025*
C2	0.13384 (17)	0.21676 (9)	0.96832 (12)	0.0209 (3)
H2A	0.0622	0.2056	1.0099	0.025*
C3	0.19242 (17)	0.15558 (9)	0.91768 (11)	0.0197 (3)
C4	0.29838 (17)	0.17037 (9)	0.85769 (12)	0.0212 (3)
H4A	0.3385	0.1279	0.8242	0.025*
C5	0.34509 (17)	0.24861 (9)	0.84737 (11)	0.0201 (3)
H5A	0.4170	0.2595	0.8059	0.024*
C6	0.28788 (16)	0.31134 (8)	0.89703 (11)	0.0174 (3)
C7	0.32652 (16)	0.39632 (9)	0.88789 (11)	0.0181 (3)
C8	0.44933 (16)	0.50829 (8)	0.87200 (11)	0.0175 (3)
C9	0.54989 (17)	0.56882 (9)	0.86054 (12)	0.0207 (3)
H9A	0.6473	0.5574	0.8490	0.025*
C10	0.50014 (17)	0.64649 (9)	0.86687 (11)	0.0204 (3)
H10A	0.5648	0.6895	0.8589	0.025*
C11	0.35573 (17)	0.66335 (8)	0.88480 (11)	0.0188 (3)
C12	0.25683 (17)	0.60237 (9)	0.89609 (11)	0.0201 (3)
H12A	0.1595	0.6137	0.9078	0.024*
C13	0.30541 (16)	0.52409 (9)	0.88960 (11)	0.0186 (3)
C14	0.30222 (17)	0.74678 (9)	0.89169 (11)	0.0209 (3)
C15	0.35706 (19)	0.88442 (9)	0.88439 (14)	0.0271 (4)
H15A	0.3201	0.8936	0.9477	0.033*
H15B	0.2771	0.8970	0.8302	0.033*
C16	0.4876 (2)	0.93640 (10)	0.87762 (16)	0.0345 (4)
H16A	0.4609	0.9924	0.8859	0.052*
H16B	0.5196	0.9293	0.8131	0.052*
H16C	0.5679	0.9215	0.9294	0.052*
C17	0.59623 (16)	0.38267 (9)	0.85909 (11)	0.0186 (3)
H17A	0.5934	0.3290	0.8891	0.022*
H17B	0.6814	0.4118	0.8948	0.022*
C18	0.61756 (17)	0.37351 (9)	0.75149 (12)	0.0209 (3)
H18A	0.5262	0.3523	0.7132	0.025*
H18B	0.6376	0.4265	0.7242	0.025*
C19	0.74492 (18)	0.31714 (9)	0.74141 (13)	0.0241 (3)
H19A	0.7669	0.3193	0.6730	0.029*
H19B	0.8335	0.3354	0.7854	0.029*
C20	0.62362 (17)	0.18286 (9)	0.70936 (12)	0.0223 (3)
H20A	0.5706	0.1962	0.6469	0.027*
C21	0.7101 (2)	0.11857 (11)	0.83933 (14)	0.0318 (4)
H21A	0.7297	0.0769	0.8864	0.038*
C22	0.76797 (19)	0.19311 (11)	0.84941 (13)	0.0310 (4)
H22A	0.8338	0.2130	0.9037	0.037*
O1W	0.41413 (16)	0.03202 (9)	0.36883 (13)	0.0409 (4)
H2W1	0.406 (4)	−0.015 (2)	0.334 (2)	0.092 (10)*
H1W1	0.496 (3)	0.0391 (14)	0.3976 (19)	0.052 (8)*

	U11	U22	U33	U12	U13	U23
Br1	0.02447 (9)	0.01647 (7)	0.04180 (11)	−0.00321 (6)	0.00871 (7)	0.00484 (6)
O1	0.0236 (6)	0.0141 (5)	0.0369 (7)	−0.0002 (4)	0.0064 (5)	0.0000 (4)
O2	0.0224 (6)	0.0207 (5)	0.0355 (7)	0.0011 (4)	0.0059 (5)	−0.0032 (5)
N1	0.0168 (6)	0.0168 (6)	0.0267 (7)	−0.0011 (5)	0.0054 (5)	0.0010 (5)
N2	0.0152 (6)	0.0147 (5)	0.0232 (6)	−0.0008 (4)	0.0056 (5)	0.0004 (5)
N3	0.0179 (6)	0.0207 (6)	0.0270 (7)	0.0007 (5)	0.0065 (5)	−0.0022 (5)
N4	0.0254 (7)	0.0227 (7)	0.0324 (8)	0.0012 (5)	0.0077 (6)	0.0011 (6)
C1	0.0190 (7)	0.0200 (7)	0.0239 (8)	−0.0014 (6)	0.0056 (6)	−0.0009 (6)
C2	0.0179 (7)	0.0215 (7)	0.0239 (8)	−0.0016 (6)	0.0054 (6)	0.0029 (6)
C3	0.0187 (7)	0.0157 (6)	0.0245 (8)	−0.0022 (5)	0.0025 (6)	0.0041 (6)
C4	0.0213 (8)	0.0178 (7)	0.0250 (8)	0.0001 (6)	0.0051 (6)	0.0002 (6)
C5	0.0190 (7)	0.0193 (7)	0.0232 (8)	−0.0012 (5)	0.0070 (6)	0.0010 (6)
C6	0.0158 (7)	0.0170 (6)	0.0197 (7)	−0.0021 (5)	0.0032 (5)	0.0013 (5)
C7	0.0178 (7)	0.0172 (6)	0.0198 (7)	−0.0014 (5)	0.0039 (5)	0.0003 (5)
C8	0.0180 (7)	0.0149 (6)	0.0199 (7)	−0.0001 (5)	0.0039 (5)	−0.0004 (5)
C9	0.0176 (7)	0.0197 (7)	0.0255 (8)	−0.0019 (5)	0.0056 (6)	0.0000 (6)
C10	0.0205 (7)	0.0174 (6)	0.0237 (8)	−0.0035 (6)	0.0042 (6)	0.0011 (6)
C11	0.0199 (7)	0.0164 (6)	0.0199 (7)	−0.0001 (5)	0.0023 (6)	−0.0006 (5)
C12	0.0169 (7)	0.0196 (7)	0.0238 (8)	0.0003 (5)	0.0031 (6)	0.0003 (6)
C13	0.0166 (7)	0.0172 (6)	0.0221 (7)	−0.0019 (5)	0.0035 (6)	0.0008 (5)
C14	0.0214 (8)	0.0186 (7)	0.0221 (8)	−0.0010 (6)	0.0007 (6)	−0.0014 (6)
C15	0.0292 (9)	0.0142 (7)	0.0384 (10)	0.0025 (6)	0.0062 (7)	−0.0004 (6)
C16	0.0313 (10)	0.0184 (8)	0.0557 (12)	−0.0001 (6)	0.0127 (9)	−0.0008 (7)
C17	0.0162 (7)	0.0175 (6)	0.0229 (7)	0.0004 (5)	0.0055 (6)	0.0002 (5)
C18	0.0208 (7)	0.0183 (7)	0.0250 (8)	−0.0012 (6)	0.0079 (6)	−0.0007 (6)
C19	0.0208 (8)	0.0213 (7)	0.0325 (9)	−0.0039 (6)	0.0113 (6)	−0.0039 (6)
C20	0.0211 (8)	0.0215 (7)	0.0250 (8)	−0.0002 (6)	0.0063 (6)	−0.0018 (6)
C21	0.0301 (9)	0.0293 (9)	0.0351 (10)	0.0053 (7)	0.0013 (8)	0.0065 (7)
C22	0.0259 (9)	0.0338 (9)	0.0313 (9)	0.0032 (7)	−0.0027 (7)	0.0001 (7)
O1W	0.0218 (7)	0.0354 (8)	0.0648 (10)	0.0047 (6)	0.0035 (7)	−0.0090 (7)

Br1—C3	1.8957 (14)	C9—H9A	0.9500
O1—C14	1.3384 (19)	C10—C11	1.412 (2)
O1—C15	1.4579 (18)	C10—H10A	0.9500
O2—C14	1.2174 (19)	C11—C12	1.390 (2)
N1—C7	1.3179 (19)	C11—C14	1.488 (2)
N1—C13	1.3860 (18)	C12—C13	1.391 (2)
N2—C7	1.3811 (19)	C12—H12A	0.9500
N2—C8	1.3884 (18)	C15—C16	1.495 (2)
N2—C17	1.4630 (19)	C15—H15A	0.9900
N3—C20	1.353 (2)	C15—H15B	0.9900
N3—C22	1.372 (2)	C16—H16A	0.9800
N3—C19	1.4668 (19)	C16—H16B	0.9800
N4—C20	1.322 (2)	C16—H16C	0.9800
N4—C21	1.376 (2)	C17—C18	1.527 (2)
C1—C2	1.382 (2)	C17—H17A	0.9900
C1—C6	1.400 (2)	C17—H17B	0.9900
C1—H1A	0.9500	C18—C19	1.525 (2)
C2—C3	1.389 (2)	C18—H18A	0.9900
C2—H2A	0.9500	C18—H18B	0.9900
C3—C4	1.385 (2)	C19—H19A	0.9900
C4—C5	1.392 (2)	C19—H19B	0.9900
C4—H4A	0.9500	C20—H20A	0.9500
C5—C6	1.396 (2)	C21—C22	1.355 (3)
C5—H5A	0.9500	C21—H21A	0.9500
C6—C7	1.476 (2)	C22—H22A	0.9500
C8—C9	1.395 (2)	O1W—H2W1	0.92 (3)
C8—C13	1.403 (2)	O1W—H1W1	0.80 (3)
C9—C10	1.385 (2)
C14—O1—C15	115.33 (12)	N1—C13—C8	110.14 (13)
C7—N1—C13	105.17 (13)	C12—C13—C8	120.50 (14)
C7—N2—C8	106.18 (12)	O2—C14—O1	123.01 (14)
C7—N2—C17	129.68 (12)	O2—C14—C11	123.97 (14)
C8—N2—C17	124.04 (12)	O1—C14—C11	113.02 (13)
C20—N3—C22	106.29 (14)	O1—C15—C16	107.83 (14)
C20—N3—C19	126.52 (14)	O1—C15—H15A	110.1
C22—N3—C19	127.19 (14)	C16—C15—H15A	110.1
C20—N4—C21	104.76 (14)	O1—C15—H15B	110.1
C2—C1—C6	121.07 (15)	C16—C15—H15B	110.1
C2—C1—H1A	119.5	H15A—C15—H15B	108.5
C6—C1—H1A	119.5	C15—C16—H16A	109.5
C1—C2—C3	119.01 (15)	C15—C16—H16B	109.5
C1—C2—H2A	120.5	H16A—C16—H16B	109.5
C3—C2—H2A	120.5	C15—C16—H16C	109.5
C4—C3—C2	121.48 (14)	H16A—C16—H16C	109.5
C4—C3—Br1	119.95 (12)	H16B—C16—H16C	109.5
C2—C3—Br1	118.56 (12)	N2—C17—C18	112.59 (12)
C3—C4—C5	118.83 (14)	N2—C17—H17A	109.1
C3—C4—H4A	120.6	C18—C17—H17A	109.1
C5—C4—H4A	120.6	N2—C17—H17B	109.1
C4—C5—C6	120.99 (14)	C18—C17—H17B	109.1
C4—C5—H5A	119.5	H17A—C17—H17B	107.8
C6—C5—H5A	119.5	C19—C18—C17	110.93 (13)
C5—C6—C1	118.62 (13)	C19—C18—H18A	109.5
C5—C6—C7	124.85 (14)	C17—C18—H18A	109.5
C1—C6—C7	116.47 (13)	C19—C18—H18B	109.5
N1—C7—N2	113.02 (13)	C17—C18—H18B	109.5
N1—C7—C6	120.87 (13)	H18A—C18—H18B	108.0
N2—C7—C6	126.07 (13)	N3—C19—C18	112.50 (13)
N2—C8—C9	131.96 (14)	N3—C19—H19A	109.1
N2—C8—C13	105.48 (12)	C18—C19—H19A	109.1
C9—C8—C13	122.55 (13)	N3—C19—H19B	109.1
C10—C9—C8	116.42 (14)	C18—C19—H19B	109.1
C10—C9—H9A	121.8	H19A—C19—H19B	107.8
C8—C9—H9A	121.8	N4—C20—N3	112.23 (15)
C9—C10—C11	121.69 (14)	N4—C20—H20A	123.9
C9—C10—H10A	119.2	N3—C20—H20A	123.9
C11—C10—H10A	119.2	C22—C21—N4	110.16 (15)
C12—C11—C10	121.21 (14)	C22—C21—H21A	124.9
C12—C11—C14	117.06 (14)	N4—C21—H21A	124.9
C10—C11—C14	121.73 (13)	C21—C22—N3	106.55 (15)
C11—C12—C13	117.63 (14)	C21—C22—H22A	126.7
C11—C12—H12A	121.2	N3—C22—H22A	126.7
C13—C12—H12A	121.2	H2W1—O1W—H1W1	113 (3)
N1—C13—C12	129.35 (14)
C6—C1—C2—C3	−0.6 (2)	C14—C11—C12—C13	179.87 (13)
C1—C2—C3—C4	0.8 (2)	C7—N1—C13—C12	−179.26 (15)
C1—C2—C3—Br1	−178.80 (11)	C7—N1—C13—C8	0.03 (17)
C2—C3—C4—C5	−0.9 (2)	C11—C12—C13—N1	179.06 (15)
Br1—C3—C4—C5	178.77 (11)	C11—C12—C13—C8	−0.2 (2)
C3—C4—C5—C6	0.6 (2)	N2—C8—C13—N1	0.23 (16)
C4—C5—C6—C1	−0.4 (2)	C9—C8—C13—N1	−179.16 (14)
C4—C5—C6—C7	−177.66 (14)	N2—C8—C13—C12	179.59 (13)
C2—C1—C6—C5	0.3 (2)	C9—C8—C13—C12	0.2 (2)
C2—C1—C6—C7	177.85 (13)	C15—O1—C14—O2	1.0 (2)
C13—N1—C7—N2	−0.29 (17)	C15—O1—C14—C11	−179.41 (13)
C13—N1—C7—C6	177.75 (13)	C12—C11—C14—O2	1.2 (2)
C8—N2—C7—N1	0.43 (17)	C10—C11—C14—O2	−179.21 (15)
C17—N2—C7—N1	176.78 (14)	C12—C11—C14—O1	−178.39 (13)
C8—N2—C7—C6	−177.48 (14)	C10—C11—C14—O1	1.2 (2)
C17—N2—C7—C6	−1.1 (2)	C14—O1—C15—C16	173.90 (14)
C5—C6—C7—N1	150.20 (15)	C7—N2—C17—C18	100.34 (17)
C1—C6—C7—N1	−27.1 (2)	C8—N2—C17—C18	−83.90 (17)
C5—C6—C7—N2	−32.0 (2)	N2—C17—C18—C19	−170.67 (12)
C1—C6—C7—N2	150.63 (15)	C20—N3—C19—C18	75.0 (2)
C7—N2—C8—C9	178.93 (16)	C22—N3—C19—C18	−105.67 (18)
C17—N2—C8—C9	2.3 (2)	C17—C18—C19—N3	68.15 (17)
C7—N2—C8—C13	−0.38 (15)	C21—N4—C20—N3	0.10 (19)
C17—N2—C8—C13	−176.99 (13)	C22—N3—C20—N4	−0.28 (19)
N2—C8—C9—C10	−179.58 (15)	C19—N3—C20—N4	179.12 (14)
C13—C8—C9—C10	−0.4 (2)	C20—N4—C21—C22	0.1 (2)
C8—C9—C10—C11	0.5 (2)	N4—C21—C22—N3	−0.3 (2)
C9—C10—C11—C12	−0.5 (2)	C20—N3—C22—C21	0.35 (19)
C9—C10—C11—C14	179.95 (14)	C19—N3—C22—C21	−179.05 (15)
C10—C11—C12—C13	0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W1···N4i	0.92 (3)	1.99 (3)	2.910 (2)	175 (3)
O1W—H1W1···N1ii	0.81 (3)	2.16 (3)	2.891 (2)	151 (2)
C17—H17B···O1Wiii	0.99	2.41	3.236 (2)	141.
C19—H19B···O1Wiii	0.99	2.56	3.327 (2)	135.
C20—H20A···O2iv	0.95	2.58	3.301 (2)	133.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W1⋯N4i	0.92 (3)	1.99 (3)	2.910 (2)	175 (3)
O1W—H1W1⋯N1ii	0.81 (3)	2.16 (3)	2.891 (2)	151 (2)
C17—H17B⋯O1Wiii	0.99	2.41	3.236 (2)	141
C19—H19B⋯O1Wiii	0.99	2.56	3.327 (2)	135
C20—H20A⋯O2iv	0.95	2.58	3.301 (2)	133

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .