1-(Carboxy­meth­yl)-1,3-benzimidazol-3-ium-3-acetate

The title compound, C₁₁H₁₀N₂O₄, was synthesized from benzimidazole and chloro­acetic acid. In the crystal structure, O—H...O hydrogen bonds lead to the formation of extended one-dimensional chains along the [101] direction.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.038
• wR factor = 0.104
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   3 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

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

1-(Carboxymethyl)-1,3-benzimidazol-3-ium-3-acetate

Crystal data

C11H10N2O4	F(000) = 976
Mr = 234.21	Dx = 1.519 Mg m^−3
Monoclinic, C2/c	Melting point = 573.4–573.5 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 14.9168 (17) Å	Cell parameters from 2512 reflections
b = 9.8014 (11) Å	θ = 2.5–28.3°
c = 14.3344 (16) Å	µ = 0.12 mm^−1
β = 102.283 (1)°	T = 293 K
V = 2047.8 (4) Å^3	Block, colorless
Z = 8	0.39 × 0.28 × 0.15 mm

Data collection

Siemens SMART CCD area-detector diffractometer	2512 independent reflections
Radiation source: fine-focus sealed tube	1991 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
ω and φ scans	θmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.961, Tmax = 0.982	k = −13→12
8976 measured reflections	l = −18→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.051P)^2 + 0.7851P] where P = (Fo^2 + 2Fc^2)/3
2512 reflections	(Δ/σ)max = 0.001
194 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Experimental. IR (KBr, cm^-1): ν_max 3141.8, 3085.9, 1741.6, 1678.0, 1564.2, 1487.0, 1363.6, 1201.6, 1139.9, 877.6, 819.7, 761.8. ¹H NMR (200 MHz, D₂O-d₆): δ 9.21 (1H, s), 7.02–7.22 (4H, m), 4.64 (4H, s).

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.34245 (7)	0.57941 (10)	0.29096 (7)	0.0434 (3)
O2	0.25165 (7)	0.76108 (10)	0.29187 (7)	0.0428 (3)
O3	−0.15054 (7)	1.04349 (11)	0.00920 (8)	0.0496 (3)
O4	−0.08041 (7)	0.86736 (10)	−0.04436 (7)	0.0481 (3)
N1	−0.00180 (7)	0.77652 (10)	0.12957 (7)	0.0319 (2)
N2	0.11894 (7)	0.64458 (10)	0.14693 (7)	0.0301 (2)
C1	0.08969 (9)	0.77319 (13)	0.14479 (9)	0.0328 (3)
H1	0.1279 (10)	0.8532 (16)	0.1538 (11)	0.039 (4)*
H3	−0.1754 (11)	0.6490 (16)	0.0872 (12)	0.045 (4)*
H4	−0.1909 (13)	0.4082 (17)	0.0789 (12)	0.054 (5)*
H5	−0.0628 (13)	0.264 (2)	0.1023 (13)	0.063 (5)*
H6	0.0886 (12)	0.3592 (16)	0.1351 (12)	0.048 (4)*
H8A	0.2144 (11)	0.4993 (18)	0.1674 (12)	0.049 (4)*
H8B	0.2418 (12)	0.6274 (17)	0.1110 (13)	0.053 (5)*
H10A	−0.1074 (12)	0.8852 (16)	0.1542 (12)	0.047 (4)*
H10B	−0.0163 (11)	0.9762 (17)	0.1507 (11)	0.044 (4)*
H11	−0.1184 (16)	0.892 (2)	−0.1196 (18)	0.098 (8)*
C2	−0.03439 (8)	0.64281 (13)	0.11931 (8)	0.0306 (3)
C3	−0.12306 (9)	0.59001 (15)	0.09940 (10)	0.0388 (3)
C4	−0.13054 (10)	0.44945 (17)	0.09524 (11)	0.0447 (3)
C5	−0.05310 (10)	0.36453 (16)	0.10885 (11)	0.0442 (3)
C6	0.03488 (10)	0.41730 (14)	0.12684 (10)	0.0374 (3)
C7	0.04236 (8)	0.55855 (13)	0.13173 (8)	0.0293 (3)
C8	0.21464 (9)	0.59868 (15)	0.16436 (10)	0.0353 (3)
C9	0.27245 (8)	0.65448 (12)	0.25710 (9)	0.0304 (3)
C10	−0.05789 (10)	0.90007 (14)	0.12270 (10)	0.0377 (3)
C11	−0.10142 (8)	0.94271 (13)	0.02086 (9)	0.0333 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0405 (5)	0.0427 (6)	0.0390 (5)	0.0097 (4)	−0.0094 (4)	−0.0039 (4)
O2	0.0403 (5)	0.0342 (5)	0.0487 (6)	0.0018 (4)	−0.0020 (4)	−0.0088 (4)
O3	0.0478 (6)	0.0478 (6)	0.0516 (6)	0.0223 (5)	0.0071 (5)	0.0089 (5)
O4	0.0548 (6)	0.0455 (6)	0.0360 (5)	0.0173 (5)	−0.0079 (4)	−0.0067 (4)
N1	0.0310 (5)	0.0301 (5)	0.0316 (5)	0.0060 (4)	0.0001 (4)	0.0002 (4)
N2	0.0265 (5)	0.0295 (5)	0.0314 (5)	0.0030 (4)	−0.0006 (4)	−0.0017 (4)
C1	0.0324 (6)	0.0311 (6)	0.0316 (6)	0.0021 (5)	−0.0003 (5)	0.0011 (5)
C2	0.0306 (6)	0.0321 (6)	0.0275 (6)	0.0030 (5)	0.0028 (5)	−0.0004 (5)
C3	0.0287 (6)	0.0486 (8)	0.0377 (7)	0.0037 (6)	0.0039 (5)	−0.0003 (6)
C4	0.0328 (7)	0.0517 (9)	0.0479 (8)	−0.0099 (6)	0.0046 (6)	−0.0027 (7)
C5	0.0442 (8)	0.0366 (8)	0.0488 (8)	−0.0064 (6)	0.0033 (6)	−0.0029 (6)
C6	0.0366 (7)	0.0318 (7)	0.0408 (7)	0.0019 (5)	0.0016 (6)	−0.0031 (5)
C7	0.0272 (6)	0.0313 (6)	0.0271 (6)	0.0013 (4)	0.0011 (5)	−0.0014 (5)
C8	0.0254 (6)	0.0415 (7)	0.0362 (7)	0.0052 (5)	0.0003 (5)	−0.0058 (6)
C9	0.0280 (6)	0.0313 (6)	0.0306 (6)	−0.0022 (5)	0.0033 (5)	0.0021 (5)
C10	0.0394 (7)	0.0336 (7)	0.0377 (7)	0.0124 (6)	0.0028 (6)	−0.0017 (6)
C11	0.0248 (6)	0.0331 (6)	0.0393 (7)	0.0024 (5)	0.0008 (5)	0.0006 (5)

Geometric parameters (Å, º)

O1—C9	1.2853 (15)	C3—C4	1.382 (2)
O2—C9	1.2256 (15)	C3—H3	0.958 (16)
O3—C11	1.2200 (15)	C4—C5	1.403 (2)
O4—C11	1.2816 (16)	C4—H4	0.969 (18)
O4—H11	1.13 (2)	C5—C6	1.383 (2)
N1—C1	1.3358 (17)	C5—H5	0.997 (19)
N1—C2	1.3947 (16)	C6—C7	1.3895 (18)
N1—C10	1.4632 (16)	C6—H6	0.970 (17)
N2—C1	1.3322 (16)	C8—C9	1.5239 (18)
N2—C7	1.3990 (15)	C8—H8A	0.975 (18)
N2—C8	1.4667 (16)	C8—H8B	0.979 (18)
C1—H1	0.962 (16)	C10—C11	1.5244 (19)
C2—C7	1.3920 (16)	C10—H10A	0.955 (17)
C2—C3	1.3922 (18)	C10—H10B	0.998 (17)
C11—O4—H11	114.9 (12)	C5—C6—H6	122.0 (10)
C1—N1—C2	108.38 (10)	C7—C6—H6	121.6 (10)
C1—N1—C10	125.51 (11)	C6—C7—C2	121.97 (12)
C2—N1—C10	126.10 (11)	C6—C7—N2	131.50 (12)
C1—N2—C7	108.31 (10)	C2—C7—N2	106.52 (11)
C1—N2—C8	126.61 (11)	N2—C8—C9	112.84 (11)
C7—N2—C8	125.07 (11)	N2—C8—H8A	107.5 (10)
N2—C1—N1	110.19 (11)	C9—C8—H8A	109.0 (10)
N2—C1—H1	125.9 (9)	N2—C8—H8B	109.1 (10)
N1—C1—H1	123.9 (9)	C9—C8—H8B	109.1 (10)
C7—C2—C3	121.69 (12)	H8A—C8—H8B	109.2 (14)
C7—C2—N1	106.58 (11)	O2—C9—O1	126.16 (12)
C3—C2—N1	131.72 (12)	O2—C9—C8	121.03 (11)
C4—C3—C2	116.34 (13)	O1—C9—C8	112.80 (11)
C4—C3—H3	122.6 (10)	N1—C10—C11	114.35 (11)
C2—C3—H3	121.0 (10)	N1—C10—H10A	109.3 (10)
C3—C4—C5	121.91 (13)	C11—C10—H10A	106.2 (10)
C3—C4—H4	119.2 (10)	N1—C10—H10B	107.1 (9)
C5—C4—H4	118.8 (10)	C11—C10—H10B	106.4 (9)
C6—C5—C4	121.64 (14)	H10A—C10—H10B	113.6 (13)
C6—C5—H5	120.0 (11)	O3—C11—O4	126.84 (12)
C4—C5—H5	118.3 (11)	O3—C11—C10	118.31 (12)
C5—C6—C7	116.42 (13)	O4—C11—C10	114.84 (11)
C1—N1—C2—C7	1.58 (14)	C1—N2—C7—C2	0.65 (13)
C10—N1—C2—C7	−179.73 (11)	C8—N2—C7—C2	179.34 (11)
C1—N1—C2—C3	−177.52 (13)	C1—N2—C8—C9	54.54 (18)
C10—N1—C2—C3	1.2 (2)	C7—N2—C8—C9	−123.91 (13)
C7—N2—C1—N1	0.34 (14)	O2—C9—C8—N2	−25.34 (18)
C8—N2—C1—N1	−178.32 (11)	O1—C9—C8—N2	155.44 (11)
C2—N1—C1—N2	−1.20 (15)	C7—C2—C3—C4	1.70 (19)
C10—N1—C1—N2	−179.90 (11)	N1—C2—C3—C4	−179.32 (13)
C5—C6—C7—C2	0.04 (19)	C7—C6—C5—C4	0.7 (2)
C5—C6—C7—N2	−178.87 (12)	C1—N1—C10—C11	100.56 (15)
C3—C2—C7—C6	−1.29 (19)	C2—N1—C10—C11	−77.91 (17)
N1—C2—C7—C6	179.50 (12)	O3—C11—C10—N1	178.75 (12)
C3—C2—C7—N2	177.87 (11)	O4—C11—C10—N1	−2.24 (18)
N1—C2—C7—N2	−1.34 (12)	C2—C3—C4—C5	−1.0 (2)
C1—N2—C7—C6	179.69 (14)	C6—C5—C4—C3	−0.2 (2)
C8—N2—C7—C6	−1.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H11···O1^i	1.13 (2)	1.32 (2)	2.4521 (13)	176 (2)
O4—H11···O2^i	1.13 (2)	2.56 (2)	3.2968 (14)	121.2 (15)

Symmetry code: (i) x−1/2, −y+3/2, z−1/2.