Benzimidazolium 2-carb­oxy-4-hydroxy­benzene­sulfonate trihydrate

Wang, Z.-L.; Wei, L.-H.

doi:10.1107/S1600536807008173

Benzimidazolium 2-carboxy-4-hydroxybenzenesulfonate trihydrate

The ions and water molecules of the title compound, C₇H₇N₂⁺·C₇H₅O₆S⁻·3H₂O, are organized into an infinite two-dimensional network via N—H

O and O—H

O hydrogen bonds parallel to the (100) plane.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807008173/hb2301sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807008173/hb2301Isup2.hkl Contains datablock I

CCDC reference: 640350

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Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.042
wR factor = 0.107
Data-to-parameter ratio = 12.0

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Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

benzimidazolium 2-carboxy-4-hydroxybenzenesulfonate trihydrate top

Crystal data top

C₇H₇N₂⁺·C₇H₅O₆S⁻·3H₂O	F(000) = 816
M_r = 390.36	D_x = 1.535 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4489 reflections
a = 13.8416 (12) Å	θ = 0.0–0.0°
b = 7.4582 (6) Å	µ = 0.25 mm⁻¹
c = 16.9000 (14) Å	T = 298 K
β = 104.481 (1)°	Block, colorless
V = 1689.2 (2) Å³	0.23 × 0.16 × 0.12 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3296 independent reflections
Radiation source: fine-focus sealed tube	2727 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
ω scans	θ_max = 26.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −17→17
T_min = 0.946, T_max = 0.971	k = −9→9
13335 measured reflections	l = −20→20

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0653P)²] where P = (F_o² + 2F_c²)/3
3296 reflections	(Δ/σ)_max = 0.001
275 parameters	Δρ_max = 0.35 e Å⁻³
12 restraints	Δρ_min = −0.33 e Å⁻³

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
S1	0.67492 (3)	0.71136 (6)	0.22883 (2)	0.02882 (15)
N1	0.90573 (12)	0.3668 (2)	0.55418 (10)	0.0415 (4)
H1A	0.9020 (14)	0.411 (3)	0.6004 (8)	0.051 (6)*
N2	0.86461 (12)	0.2822 (2)	0.42761 (10)	0.0406 (4)
H2A	0.8308 (15)	0.264 (3)	0.3790 (8)	0.054 (7)*
O1	0.61554 (10)	0.87910 (19)	−0.08164 (7)	0.0410 (3)
H1'	0.6172 (17)	0.888 (3)	−0.1300 (7)	0.067 (7)*
O2	0.45883 (10)	0.81364 (19)	−0.14648 (7)	0.0470 (4)
O3	0.33700 (10)	0.6996 (2)	−0.06283 (9)	0.0503 (4)
H3	0.352 (2)	0.731 (3)	−0.1073 (18)	0.079 (9)*
O4	0.76666 (9)	0.70079 (19)	0.20260 (8)	0.0456 (4)
O5	0.66498 (10)	0.87575 (17)	0.27086 (7)	0.0441 (3)
O6	0.66119 (9)	0.55558 (16)	0.27752 (6)	0.0352 (3)
O7	0.09486 (12)	0.5998 (3)	0.77426 (12)	0.0641 (4)
H7A	0.1401 (14)	0.523 (2)	0.7795 (16)	0.088 (10)*
H7B	0.1186 (18)	0.6994 (17)	0.7668 (19)	0.094 (11)*
O8	0.90228 (12)	0.5036 (2)	0.70370 (9)	0.0501 (4)
H8A	0.9597 (8)	0.551 (3)	0.7227 (13)	0.083 (9)*
H8B	0.8624 (11)	0.585 (2)	0.7093 (14)	0.068 (8)*
O9	0.74307 (10)	0.21700 (19)	0.27721 (9)	0.0434 (3)
H9A	0.7133 (14)	0.1190 (15)	0.2691 (14)	0.076 (8)*
H9B	0.6979 (13)	0.2970 (19)	0.2700 (16)	0.075 (9)*
C1	0.83305 (15)	0.3577 (3)	0.48670 (12)	0.0441 (5)
H1	0.7684	0.3990	0.4817	0.053*
C2	0.99085 (14)	0.2927 (2)	0.53838 (11)	0.0340 (4)
C3	1.08643 (15)	0.2672 (3)	0.58706 (12)	0.0418 (5)
H3A	1.1040	0.3024	0.6416	0.050*
C4	1.15403 (15)	0.1874 (3)	0.55111 (13)	0.0442 (5)
H4	1.2189	0.1681	0.5819	0.053*
C5	1.12745 (15)	0.1345 (3)	0.46895 (12)	0.0443 (5)
H5	1.1755	0.0820	0.4465	0.053*
C6	1.03264 (15)	0.1579 (2)	0.42061 (11)	0.0398 (4)
H6	1.0150	0.1213	0.3663	0.048*
C7	0.96471 (14)	0.2388 (2)	0.45681 (11)	0.0333 (4)
C8	0.51114 (13)	0.7632 (2)	−0.00370 (10)	0.0285 (4)
C9	0.41716 (13)	0.7014 (2)	0.00188 (11)	0.0339 (4)
C10	0.40501 (13)	0.6399 (3)	0.07630 (11)	0.0381 (4)
H10	0.3431	0.5969	0.0797	0.046*
C11	0.48277 (13)	0.6416 (2)	0.14483 (10)	0.0344 (4)
H11	0.4734	0.6013	0.1945	0.041*
C12	0.57609 (12)	0.7040 (2)	0.13971 (10)	0.0278 (4)
C13	0.59021 (13)	0.7631 (2)	0.06609 (10)	0.0284 (4)
H13	0.6528	0.8030	0.0630	0.034*
C14	0.52503 (14)	0.8206 (2)	−0.08382 (10)	0.0322 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0300 (3)	0.0334 (3)	0.0227 (2)	0.00011 (17)	0.00588 (17)	0.00185 (16)
N1	0.0416 (10)	0.0461 (10)	0.0396 (9)	−0.0049 (7)	0.0153 (8)	−0.0028 (8)
N2	0.0368 (9)	0.0417 (10)	0.0387 (9)	−0.0051 (7)	0.0009 (8)	−0.0006 (7)
O1	0.0417 (8)	0.0600 (9)	0.0231 (6)	−0.0044 (6)	0.0114 (6)	0.0022 (6)
O2	0.0439 (8)	0.0658 (10)	0.0271 (7)	0.0044 (7)	0.0012 (6)	0.0038 (6)
O3	0.0308 (8)	0.0787 (11)	0.0368 (8)	−0.0013 (7)	−0.0002 (6)	−0.0013 (7)
O4	0.0296 (7)	0.0710 (10)	0.0359 (7)	−0.0010 (6)	0.0080 (6)	0.0066 (6)
O5	0.0562 (9)	0.0333 (7)	0.0378 (7)	0.0000 (6)	0.0025 (6)	−0.0049 (6)
O6	0.0461 (7)	0.0331 (7)	0.0276 (6)	0.0042 (5)	0.0115 (5)	0.0042 (5)
O7	0.0465 (9)	0.0598 (11)	0.0884 (12)	−0.0067 (9)	0.0212 (9)	0.0105 (10)
O8	0.0472 (9)	0.0534 (9)	0.0533 (8)	0.0019 (8)	0.0190 (8)	−0.0055 (7)
O9	0.0382 (8)	0.0364 (8)	0.0516 (9)	0.0005 (7)	0.0038 (7)	−0.0030 (6)
C1	0.0355 (11)	0.0437 (11)	0.0543 (12)	−0.0026 (9)	0.0135 (9)	0.0005 (9)
C2	0.0368 (10)	0.0333 (10)	0.0321 (9)	−0.0052 (8)	0.0088 (8)	0.0003 (7)
C3	0.0450 (12)	0.0435 (11)	0.0325 (9)	−0.0080 (9)	0.0016 (9)	0.0000 (8)
C4	0.0339 (10)	0.0453 (12)	0.0495 (12)	−0.0012 (8)	0.0030 (9)	0.0043 (9)
C5	0.0436 (11)	0.0395 (11)	0.0528 (12)	0.0013 (9)	0.0176 (10)	0.0005 (9)
C6	0.0503 (12)	0.0364 (10)	0.0332 (9)	−0.0034 (9)	0.0116 (9)	−0.0024 (8)
C7	0.0364 (10)	0.0289 (9)	0.0323 (9)	−0.0062 (7)	0.0041 (8)	0.0021 (7)
C8	0.0298 (9)	0.0304 (9)	0.0252 (8)	0.0044 (7)	0.0066 (7)	−0.0014 (7)
C9	0.0291 (9)	0.0384 (10)	0.0325 (9)	0.0044 (7)	0.0044 (7)	−0.0031 (7)
C10	0.0278 (9)	0.0471 (11)	0.0415 (10)	−0.0031 (8)	0.0125 (8)	−0.0008 (9)
C11	0.0336 (10)	0.0405 (10)	0.0315 (9)	−0.0009 (8)	0.0126 (8)	0.0033 (8)
C12	0.0290 (9)	0.0294 (9)	0.0253 (8)	0.0014 (7)	0.0074 (7)	−0.0003 (7)
C13	0.0285 (9)	0.0308 (9)	0.0268 (8)	0.0006 (7)	0.0084 (7)	−0.0018 (7)
C14	0.0363 (10)	0.0342 (10)	0.0257 (9)	0.0070 (8)	0.0072 (8)	−0.0012 (7)

Geometric parameters (Å, º) top

S1—O5	1.4407 (13)	C1—H1	0.9300
S1—O4	1.4480 (13)	C2—C3	1.385 (3)
S1—O6	1.4633 (12)	C2—C7	1.394 (3)
S1—C12	1.7642 (17)	C3—C4	1.372 (3)
N1—C1	1.320 (2)	C3—H3A	0.9300
N1—C2	1.386 (2)	C4—C5	1.401 (3)
N1—H1A	0.860 (9)	C4—H4	0.9300
N2—C1	1.313 (3)	C5—C6	1.373 (3)
N2—C7	1.388 (2)	C5—H5	0.9300
N2—H2A	0.848 (10)	C6—C7	1.382 (3)
O1—C14	1.318 (2)	C6—H6	0.9300
O1—H1'	0.825 (9)	C8—C13	1.394 (2)
O2—C14	1.216 (2)	C8—C9	1.405 (2)
O3—C9	1.349 (2)	C8—C14	1.478 (2)
O3—H3	0.86 (3)	C9—C10	1.388 (2)
O7—H7A	0.835 (9)	C10—C11	1.370 (2)
O7—H7B	0.835 (10)	C10—H10	0.9300
O8—H8A	0.856 (10)	C11—C12	1.396 (2)
O8—H8B	0.842 (9)	C11—H11	0.9300
O9—H9A	0.834 (9)	C12—C13	1.379 (2)
O9—H9B	0.850 (9)	C13—H13	0.9300

O5—S1—O4	113.36 (8)	C6—C5—H5	119.0
O5—S1—O6	110.89 (7)	C4—C5—H5	119.0
O4—S1—O6	112.09 (7)	C5—C6—C7	116.56 (17)
O5—S1—C12	107.35 (7)	C5—C6—H6	121.7
O4—S1—C12	106.81 (8)	C7—C6—H6	121.7
O6—S1—C12	105.86 (7)	C6—C7—N2	132.35 (17)
C1—N1—C2	108.28 (16)	C6—C7—C2	121.78 (18)
C1—N1—H1A	126.8 (13)	N2—C7—C2	105.87 (17)
C2—N1—H1A	125.0 (13)	C13—C8—C9	119.14 (15)
C1—N2—C7	108.79 (16)	C13—C8—C14	121.40 (16)
C1—N2—H2A	126.7 (16)	C9—C8—C14	119.42 (16)
C7—N2—H2A	124.5 (16)	O3—C9—C10	118.03 (16)
C14—O1—H1'	105.1 (16)	O3—C9—C8	122.43 (16)
C9—O3—H3	112.1 (19)	C10—C9—C8	119.55 (16)
H7A—O7—H7B	108.2 (15)	C11—C10—C9	121.04 (16)
H8A—O8—H8B	103.6 (14)	C11—C10—H10	119.5
H9A—O9—H9B	106.0 (14)	C9—C10—H10	119.5
N2—C1—N1	110.64 (17)	C10—C11—C12	119.62 (16)
N2—C1—H1	124.7	C10—C11—H11	120.2
N1—C1—H1	124.7	C12—C11—H11	120.2
C3—C2—N1	132.21 (17)	C13—C12—C11	120.29 (16)
C3—C2—C7	121.38 (18)	C13—C12—S1	120.38 (13)
N1—C2—C7	106.41 (16)	C11—C12—S1	119.31 (12)
C4—C3—C2	116.90 (18)	C12—C13—C8	120.34 (16)
C4—C3—H3A	121.5	C12—C13—H13	119.8
C2—C3—H3A	121.5	C8—C13—H13	119.8
C3—C4—C5	121.44 (19)	O2—C14—O1	122.84 (15)
C3—C4—H4	119.3	O2—C14—C8	122.91 (17)
C5—C4—H4	119.3	O1—C14—C8	114.25 (15)
C6—C5—C4	121.94 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9A···O5ⁱ	0.83 (1)	1.94 (1)	2.7567 (19)	168 (2)
O8—H8A···O7ⁱⁱ	0.86 (1)	1.89 (1)	2.730 (2)	166 (2)
O8—H8B···O4ⁱⁱⁱ	0.84 (1)	2.06 (1)	2.893 (2)	170 (2)
O9—H9B···O6	0.85 (1)	2.01 (1)	2.7684 (18)	149 (2)
O7—H7A···O4^iv	0.84 (1)	2.09 (1)	2.912 (2)	169 (2)
O7—H7B···O9^iv	0.84 (1)	2.31 (2)	2.938 (2)	133 (2)
O7—H7B···O8^v	0.84 (1)	2.36 (2)	3.033 (3)	139 (2)
O1—H1′···O6^vi	0.83 (1)	1.86 (1)	2.6559 (16)	161 (2)
N1—H1A···O8	0.86 (1)	1.88 (1)	2.736 (2)	177 (2)
N2—H2A···O9	0.85 (1)	1.87 (1)	2.718 (2)	173 (2)
O3—H3···O2	0.86 (3)	1.87 (3)	2.600 (2)	142 (3)

Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z; (iii) x, −y+3/2, z+1/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, y+1/2, −z+3/2; (vi) x, −y+3/2, z−1/2.

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Benzimidazolium 2-carb­oxy-4-hydroxy­benzene­sulfonate trihydrate

Supporting information

Key indicators

checkCIF/PLATON results

Benzimidazolium 2-carboxy-4-hydroxybenzenesulfonate trihydrate