2,2'-Dimethyl-1,1'-[2,2-bis-(bromo-methyl)propane-1,3-di-yl]dibenzimidazole hemihydrate.

The title compound, C(21)H(22)Br(2)N(4)·0.5H(2)O, contains two benzimidazole groups which may provide two potential coordination nodes for the construction of metal-organic frameworks. The mean planes of the two imidazole groups are almost perpendicular, with a dihedral angle of 83.05 (2)°, and adjacent mol-ecules are linked into a one-dimensional chain by π-π stacking inter-actions between imidazole groups of different mol-ecules [centroid-to-centroid distances of 3.834 (2) and 3.522 (2) Å].

Related literature

For preparation of the N-donor compound, see: Bai et al. (2010 ▶). For a related structure, see: Wei et al. (2011 ▶). For constructions and applications of metal–organic frameworks, see: Kuppler et al. (2009 ▶); Wang et al. (2011 ▶).

Experimental

Crystal data

C21H22Br2N4·0.5H2O

M = 499.26

Monoclinic,

a = 12.647 (3) Å

b = 8.1065 (16) Å

c = 20.580 (4) Å

β = 107.42 (3)°

V = 2013.1 (7) Å3

Z = 4

Mo Kα radiation

μ = 4.04 mm−1

T = 153 K

0.15 × 0.11 × 0.10 mm

Data collection

Rigaku Saturn 724+ CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T min = 0.582, T max = 0.688

9078 measured reflections

3662 independent reflections

2786 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.159

S = 1.13

3662 reflections

253 parameters

H-atom parameters constrained

Δρmax = 1.00 e Å−3

Δρmin = −0.71 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalClear and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812007751/bg2435sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007751/bg2435Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007751/bg2435Isup3.cml

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

C21H22Br2N4·0.5H2O	F(000) = 1004
Mr = 499.26	Dx = 1.647 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6583 reflections
a = 12.647 (3) Å	θ = 2.5–29.1°
b = 8.1065 (16) Å	µ = 4.04 mm−1
c = 20.580 (4) Å	T = 153 K
β = 107.42 (3)°	Prism, colourless
V = 2013.1 (7) Å3	0.15 × 0.11 × 0.10 mm
Z = 4

Rigaku Saturn 724+ CCD diffractometer	3662 independent reflections
Radiation source: fine-focus sealed tube	2786 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
Detector resolution: 28.5714 pixels mm-1	θmax = 25.4°, θmin = 3.0°
ω scans	h = −14→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −9→9
Tmin = 0.582, Tmax = 0.688	l = −20→24
9078 measured reflections

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.053P)2 + 5.0634P] where P = (Fo2 + 2Fc2)/3
3662 reflections	(Δ/σ)max = 0.001
253 parameters	Δρmax = 1.00 e Å−3
0 restraints	Δρmin = −0.71 e Å−3

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	Occ. (<1)
C1	0.6424 (6)	0.2016 (8)	0.9301 (3)	0.0256 (16)
H1A	0.7009	0.1863	0.9726	0.031*
H1B	0.6036	0.3025	0.9342	0.031*
C2	0.4530 (6)	0.0612 (8)	0.8838 (3)	0.0242 (15)
C3	0.3807 (6)	0.1770 (9)	0.8446 (3)	0.0297 (17)
H3	0.4043	0.2829	0.8386	0.036*
C4	0.2721 (6)	0.1286 (10)	0.8149 (4)	0.0364 (18)
H4	0.2216	0.2040	0.7888	0.044*
C5	0.2365 (7)	−0.0308 (10)	0.8233 (4)	0.042 (2)
H5	0.1634	−0.0600	0.8014	0.051*
C6	0.3062 (7)	−0.1452 (10)	0.8627 (4)	0.039 (2)
H6	0.2813	−0.2502	0.8690	0.047*
C7	0.4159 (6)	−0.0989 (9)	0.8933 (3)	0.0308 (17)
C8	0.5876 (6)	−0.0897 (9)	0.9525 (4)	0.0308 (17)
C9	0.6978 (6)	−0.1342 (10)	0.9993 (4)	0.0386 (19)
H9A	0.7479	−0.0432	1.0028	0.058*
H9B	0.7259	−0.2289	0.9818	0.058*
H9C	0.6911	−0.1592	1.0434	0.058*
C10	0.8018 (5)	0.3379 (8)	0.8972 (3)	0.0286 (16)
H10A	0.8364	0.3435	0.8611	0.034*
H10B	0.7769	0.4483	0.9034	0.034*
C11	1.0146 (6)	0.1356 (10)	0.9069 (4)	0.0401 (19)
H11A	0.9545	0.1503	0.8658	0.060*
H11B	1.0283	0.0200	0.9153	0.060*
H11C	1.0800	0.1877	0.9020	0.060*
C12	0.9851 (6)	0.2113 (9)	0.9649 (4)	0.0354 (18)
C13	0.9953 (6)	0.3007 (9)	1.0651 (4)	0.0327 (17)
C14	1.0284 (6)	0.3408 (10)	1.1335 (4)	0.0362 (18)
H14	1.0959	0.3042	1.1623	0.043*
C15	0.9585 (7)	0.4364 (10)	1.1578 (4)	0.044 (2)
H15	0.9791	0.4651	1.2037	0.052*
C16	0.8556 (7)	0.4915 (9)	1.1138 (4)	0.0390 (19)
H16	0.8099	0.5572	1.1310	0.047*
C17	0.8226 (6)	0.4492 (8)	1.0462 (4)	0.0300 (17)
H17	0.7551	0.4853	1.0172	0.036*
C20	0.8938 (6)	0.3495 (8)	1.0220 (3)	0.0258 (16)
C21	0.7252 (6)	0.0544 (9)	0.8506 (4)	0.0324 (18)
H21A	0.6603	−0.0156	0.8428	0.039*
H21B	0.7833	0.0069	0.8880	0.039*
C22	0.6175 (6)	0.3104 (9)	0.8090 (3)	0.0302 (17)
H22A	0.5539	0.2397	0.7899	0.036*
H22B	0.6553	0.3245	0.7747	0.036*
C23	0.6969 (5)	0.2250 (8)	0.8721 (3)	0.0225 (15)
N1	0.5029 (5)	−0.1870 (7)	0.9376 (3)	0.0305 (14)
N2	0.5642 (5)	0.0633 (7)	0.9216 (3)	0.0250 (13)
N3	0.8870 (5)	0.2914 (7)	0.9599 (3)	0.0296 (14)
N4	1.0516 (5)	0.2108 (8)	1.0281 (3)	0.0378 (16)
O1W	0.5525 (10)	−0.4843 (13)	1.0222 (6)	0.055 (3)	0.50
Br1	0.56570 (7)	0.52696 (9)	0.83015 (4)	0.0391 (3)
Br2	0.77367 (7)	0.05147 (10)	0.76915 (4)	0.0389 (3)

	U11	U22	U33	U12	U13	U23
C1	0.029 (4)	0.022 (3)	0.026 (4)	−0.006 (3)	0.009 (3)	0.005 (3)
C2	0.032 (4)	0.021 (4)	0.021 (4)	−0.003 (3)	0.011 (3)	−0.005 (3)
C3	0.031 (4)	0.037 (4)	0.023 (4)	−0.002 (3)	0.010 (3)	0.000 (3)
C4	0.029 (4)	0.050 (5)	0.028 (4)	−0.001 (4)	0.005 (3)	0.003 (4)
C5	0.041 (5)	0.051 (5)	0.031 (4)	−0.015 (4)	0.005 (4)	−0.010 (4)
C6	0.045 (5)	0.039 (5)	0.036 (5)	−0.020 (4)	0.016 (4)	−0.014 (4)
C7	0.044 (5)	0.024 (4)	0.026 (4)	−0.003 (3)	0.013 (4)	−0.008 (3)
C8	0.036 (4)	0.032 (4)	0.033 (4)	0.004 (3)	0.023 (4)	0.004 (3)
C9	0.038 (5)	0.041 (5)	0.035 (4)	0.008 (4)	0.009 (4)	0.003 (4)
C10	0.026 (4)	0.029 (4)	0.028 (4)	−0.006 (3)	0.004 (3)	0.006 (3)
C11	0.038 (5)	0.049 (5)	0.036 (5)	0.002 (4)	0.015 (4)	−0.001 (4)
C12	0.033 (4)	0.039 (4)	0.037 (5)	−0.003 (4)	0.014 (4)	−0.001 (4)
C13	0.032 (4)	0.036 (4)	0.029 (4)	−0.007 (3)	0.008 (4)	−0.002 (3)
C14	0.029 (4)	0.044 (5)	0.034 (4)	−0.004 (4)	0.007 (4)	0.001 (4)
C15	0.046 (5)	0.052 (5)	0.034 (5)	−0.020 (4)	0.013 (4)	0.002 (4)
C16	0.044 (5)	0.035 (4)	0.041 (5)	−0.013 (4)	0.017 (4)	−0.008 (4)
C17	0.031 (4)	0.020 (4)	0.039 (4)	−0.005 (3)	0.011 (4)	0.000 (3)
C20	0.024 (4)	0.032 (4)	0.018 (4)	−0.012 (3)	0.002 (3)	0.005 (3)
C21	0.043 (5)	0.031 (4)	0.031 (4)	−0.006 (3)	0.024 (4)	−0.004 (3)
C22	0.024 (4)	0.043 (4)	0.021 (4)	0.004 (3)	0.004 (3)	0.000 (3)
C23	0.026 (4)	0.020 (3)	0.023 (4)	−0.003 (3)	0.009 (3)	0.000 (3)
N1	0.047 (4)	0.021 (3)	0.028 (3)	0.000 (3)	0.017 (3)	−0.003 (3)
N2	0.030 (3)	0.028 (3)	0.019 (3)	−0.002 (3)	0.010 (3)	0.001 (2)
N3	0.025 (3)	0.027 (3)	0.035 (4)	−0.003 (3)	0.006 (3)	0.002 (3)
N4	0.037 (4)	0.041 (4)	0.035 (4)	0.006 (3)	0.010 (3)	0.002 (3)
O1W	0.062 (8)	0.031 (6)	0.066 (9)	−0.007 (6)	0.012 (7)	0.014 (6)
Br1	0.0404 (5)	0.0328 (5)	0.0436 (5)	0.0076 (3)	0.0121 (4)	0.0086 (3)
Br2	0.0469 (5)	0.0441 (5)	0.0302 (4)	0.0022 (4)	0.0184 (4)	−0.0040 (3)

C1—N2	1.470 (8)	C11—H11A	0.9600
C1—C23	1.559 (9)	C11—H11B	0.9600
C1—H1A	0.9700	C11—H11C	0.9600
C1—H1B	0.9700	C12—N4	1.321 (9)
C2—C3	1.388 (9)	C12—N3	1.377 (9)
C2—N2	1.389 (9)	C13—C20	1.381 (10)
C2—C7	1.413 (9)	C13—C14	1.383 (10)
C3—C4	1.382 (10)	C13—N4	1.393 (9)
C3—H3	0.9300	C14—C15	1.377 (11)
C4—C5	1.396 (11)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.417 (11)
C5—C6	1.367 (11)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.372 (10)
C6—C7	1.392 (10)	C16—H16	0.9300
C6—H6	0.9300	C17—C20	1.408 (10)
C7—N1	1.397 (9)	C17—H17	0.9300
C8—N1	1.291 (9)	C20—N3	1.341 (8)
C8—N2	1.386 (9)	C21—C23	1.526 (9)
C8—C9	1.481 (10)	C21—Br2	1.951 (7)
C9—H9A	0.9600	C21—H21A	0.9700
C9—H9B	0.9600	C21—H21B	0.9700
C9—H9C	0.9600	C22—C23	1.547 (9)
C10—N3	1.460 (8)	C22—Br1	1.968 (7)
C10—C23	1.567 (9)	C22—H22A	0.9700
C10—H10A	0.9700	C22—H22B	0.9700
C10—H10B	0.9700	O1W—O1Wi	1.39 (2)
C11—C12	1.486 (10)
N2—C1—C23	115.9 (5)	N4—C12—C11	123.5 (7)
N2—C1—H1A	108.3	N3—C12—C11	124.9 (7)
C23—C1—H1A	108.3	C20—C13—C14	121.8 (7)
N2—C1—H1B	108.3	C20—C13—N4	109.2 (6)
C23—C1—H1B	108.3	C14—C13—N4	129.1 (7)
H1A—C1—H1B	107.4	C15—C14—C13	118.1 (7)
C3—C2—N2	134.2 (6)	C15—C14—H14	121.0
C3—C2—C7	120.9 (7)	C13—C14—H14	121.0
N2—C2—C7	104.9 (6)	C14—C15—C16	120.8 (8)
C4—C3—C2	117.3 (7)	C14—C15—H15	119.6
C4—C3—H3	121.3	C16—C15—H15	119.6
C2—C3—H3	121.3	C17—C16—C15	120.8 (8)
C3—C4—C5	121.5 (7)	C17—C16—H16	119.6
C3—C4—H4	119.2	C15—C16—H16	119.6
C5—C4—H4	119.2	C16—C17—C20	118.0 (7)
C6—C5—C4	121.8 (7)	C16—C17—H17	121.0
C6—C5—H5	119.1	C20—C17—H17	121.0
C4—C5—H5	119.1	N3—C20—C13	107.1 (6)
C5—C6—C7	117.6 (7)	N3—C20—C17	132.4 (7)
C5—C6—H6	121.2	C13—C20—C17	120.5 (6)
C7—C6—H6	121.2	C23—C21—Br2	114.9 (5)
C6—C7—N1	129.8 (7)	C23—C21—H21A	108.5
C6—C7—C2	120.8 (7)	Br2—C21—H21A	108.5
N1—C7—C2	109.3 (6)	C23—C21—H21B	108.5
N1—C8—N2	112.9 (6)	Br2—C21—H21B	108.5
N1—C8—C9	123.9 (7)	H21A—C21—H21B	107.5
N2—C8—C9	123.1 (7)	C23—C22—Br1	112.9 (4)
C8—C9—H9A	109.5	C23—C22—H22A	109.0
C8—C9—H9B	109.5	Br1—C22—H22A	109.0
H9A—C9—H9B	109.5	C23—C22—H22B	109.0
C8—C9—H9C	109.5	Br1—C22—H22B	109.0
H9A—C9—H9C	109.5	H22A—C22—H22B	107.8
H9B—C9—H9C	109.5	C21—C23—C22	108.2 (6)
N3—C10—C23	118.0 (5)	C21—C23—C1	107.9 (5)
N3—C10—H10A	107.8	C22—C23—C1	111.9 (5)
C23—C10—H10A	107.8	C21—C23—C10	112.1 (6)
N3—C10—H10B	107.8	C22—C23—C10	106.8 (5)
C23—C10—H10B	107.8	C1—C23—C10	110.0 (5)
H10A—C10—H10B	107.1	C8—N1—C7	106.2 (6)
C12—C11—H11A	109.5	C8—N2—C2	106.7 (5)
C12—C11—H11B	109.5	C8—N2—C1	125.7 (6)
H11A—C11—H11B	109.5	C2—N2—C1	127.5 (6)
C12—C11—H11C	109.5	C20—N3—C12	107.1 (6)
H11A—C11—H11C	109.5	C20—N3—C10	124.8 (6)
H11B—C11—H11C	109.5	C12—N3—C10	126.8 (6)
N4—C12—N3	111.7 (6)	C12—N4—C13	104.9 (6)
N2—C2—C3—C4	−178.8 (7)	N3—C10—C23—C21	−66.2 (8)
C7—C2—C3—C4	−0.7 (10)	N3—C10—C23—C22	175.5 (6)
C2—C3—C4—C5	−0.7 (10)	N3—C10—C23—C1	53.8 (8)
C3—C4—C5—C6	2.0 (12)	N2—C8—N1—C7	0.7 (8)
C4—C5—C6—C7	−1.7 (12)	C9—C8—N1—C7	179.1 (6)
C5—C6—C7—N1	177.4 (7)	C6—C7—N1—C8	−179.0 (7)
C5—C6—C7—C2	0.3 (11)	C2—C7—N1—C8	−1.6 (8)
C3—C2—C7—C6	1.0 (10)	N1—C8—N2—C2	0.5 (8)
N2—C2—C7—C6	179.5 (6)	C9—C8—N2—C2	−178.0 (6)
C3—C2—C7—N1	−176.7 (6)	N1—C8—N2—C1	178.2 (6)
N2—C2—C7—N1	1.9 (7)	C9—C8—N2—C1	−0.2 (10)
C20—C13—C14—C15	−2.1 (11)	C3—C2—N2—C8	176.8 (7)
N4—C13—C14—C15	178.0 (7)	C7—C2—N2—C8	−1.4 (7)
C13—C14—C15—C16	0.2 (11)	C3—C2—N2—C1	−0.8 (12)
C14—C15—C16—C17	0.8 (11)	C7—C2—N2—C1	−179.1 (6)
C15—C16—C17—C20	0.1 (10)	C23—C1—N2—C8	99.7 (7)
C14—C13—C20—N3	−179.9 (7)	C23—C1—N2—C2	−83.0 (8)
N4—C13—C20—N3	0.1 (8)	C13—C20—N3—C12	−1.5 (7)
C14—C13—C20—C17	3.0 (10)	C17—C20—N3—C12	175.1 (7)
N4—C13—C20—C17	−177.0 (6)	C13—C20—N3—C10	−169.2 (6)
C16—C17—C20—N3	−178.2 (7)	C17—C20—N3—C10	7.4 (11)
C16—C17—C20—C13	−1.9 (10)	N4—C12—N3—C20	2.6 (8)
Br2—C21—C23—C22	49.9 (7)	C11—C12—N3—C20	−176.8 (7)
Br2—C21—C23—C1	171.1 (5)	N4—C12—N3—C10	169.9 (6)
Br2—C21—C23—C10	−67.6 (7)	C11—C12—N3—C10	−9.5 (11)
Br1—C22—C23—C21	176.2 (4)	C23—C10—N3—C20	−94.6 (8)
Br1—C22—C23—C1	57.5 (6)	C23—C10—N3—C12	100.1 (8)
Br1—C22—C23—C10	−62.9 (6)	N3—C12—N4—C13	−2.4 (8)
N2—C1—C23—C21	−40.4 (8)	C11—C12—N4—C13	177.0 (7)
N2—C1—C23—C22	78.5 (7)	C20—C13—N4—C12	1.5 (8)
N2—C1—C23—C10	−162.9 (5)	C14—C13—N4—C12	−178.6 (8)