Benzimidazolium hydrogen phenyl­malonate

In the title compound, C₇H₇N₂⁺·C₉H₇O₄⁻, hydrogen phenyl­malonate anions are connected by O—H...O hydrogen bonds to form zigzag chains. The chains are connected to each other by N—H...O hydro­gen bonds through benzimidazolium cations, forming a layer.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.059
• wR factor = 0.214
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.67 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT432_ALERT_2_C Short Inter X...Y Contact  O3     ..  C10     ..       2.97 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O4     ..  C10     ..       2.93 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O4     ..  C3      ..       2.97 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15    ..  CG      ..       2.92 Ang.

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

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

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1990); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows.

(I)

Crystal data

C7H7N2^+·C9H7O4^−	Z = 2
Mr = 298.30	F(000) = 312
Triclinic, P1	Dx = 1.430 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.1003 (13) Å	Cell parameters from 25 reflections
b = 9.244 (3) Å	θ = 10.5–12.4°
c = 15.274 (4) Å	µ = 0.11 mm^−1
α = 102.2 (5)°	T = 298 K
β = 90.64 (2)°	Prism, colorless
γ = 99.87 (2)°	0.50 × 0.30 × 0.25 mm
V = 692.6 (14) Å^3

Data collection

Rigaku AFC-5R diffractometer	2059 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.042
Graphite monochromator	θmax = 29.0°, θmin = 2.3°
ω–2θ scans	h = −6→6
Absorption correction: ψ scan (North et al., 1968)	k = −1→12
Tmin = 0.95, Tmax = 0.97	l = −20→20
4300 measured reflections	3 standard reflections every 97 reflections
3657 independent reflections	intensity decay: 0.2%

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.214	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 0.25P] where P = (Fo^2 + 2Fc^2)/3
3657 reflections	(Δ/σ)max = 0.001
215 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3
0 constraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.4227 (4)	0.6051 (2)	0.97296 (14)	0.0388 (5)
O2	0.6577 (6)	0.5463 (3)	0.85367 (17)	0.0623 (8)
O3	0.8513 (4)	0.8869 (2)	0.95494 (14)	0.0337 (5)
O4	0.5963 (4)	1.0311 (2)	0.90810 (14)	0.0347 (5)
N1	0.9205 (5)	0.3204 (3)	0.84192 (17)	0.0370 (6)
N2	1.2051 (5)	0.1756 (3)	0.85451 (18)	0.0370 (6)
C1	0.5186 (6)	0.6264 (3)	0.89867 (18)	0.0298 (6)
C2	0.4531 (5)	0.7637 (3)	0.86797 (17)	0.0254 (5)
C3	0.6443 (5)	0.9069 (3)	0.91438 (17)	0.0262 (5)
C4	0.4578 (5)	0.7420 (3)	0.76660 (18)	0.0289 (6)
C5	0.6727 (7)	0.8041 (4)	0.7244 (2)	0.0442 (8)
C6	0.6740 (8)	0.7778 (5)	0.6307 (2)	0.0561 (10)
C7	0.4620 (8)	0.6878 (4)	0.5801 (2)	0.0558 (10)
C8	0.2490 (9)	0.6266 (5)	0.6201 (3)	0.0642 (11)
C9	0.2423 (7)	0.6540 (4)	0.7141 (2)	0.0493 (9)
C10	1.0529 (6)	0.2654 (3)	0.8978 (2)	0.0369 (7)
C11	0.9869 (6)	0.2630 (3)	0.7558 (2)	0.0330 (6)
C12	0.9059 (7)	0.2825 (4)	0.6724 (2)	0.0455 (8)
C13	1.0139 (8)	0.2064 (5)	0.5985 (2)	0.0561 (9)
C14	1.1989 (8)	0.1139 (5)	0.6065 (3)	0.0602 (10)
C15	1.2792 (7)	0.0922 (4)	0.6887 (2)	0.0490 (8)
C16	1.1702 (6)	0.1697 (3)	0.7638 (2)	0.0339 (6)
H1	0.471 (15)	0.544 (7)	0.998 (5)	0.037 (19)*	0.50
H1N	0.818 (8)	0.390 (5)	0.855 (3)	0.073 (13)*
H2	0.272	0.775	0.8854	0.030*
H2N	1.311 (8)	0.131 (4)	0.880 (3)	0.057 (11)*
H3	0.958 (13)	0.963 (6)	0.987 (4)	0.021 (16)*	0.50
H5	0.819	0.864	0.759	0.053*
H6	0.819	0.822	0.603	0.067*
H7	0.464	0.669	0.518	0.067*
H8	0.105	0.566	0.585	0.077*
H9	0.093	0.613	0.741	0.059*
H10	1.040	0.287	0.960	0.044*
H12	0.784	0.345	0.667	0.055*
H13	0.963	0.217	0.542	0.067*
H14	1.270	0.065	0.555	0.072*
H15	1.400	0.029	0.694	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0519 (13)	0.0352 (12)	0.0372 (12)	0.0153 (10)	0.0096 (10)	0.0188 (9)
O2	0.101 (2)	0.0543 (15)	0.0552 (15)	0.0549 (15)	0.0311 (14)	0.0289 (12)
O3	0.0342 (11)	0.0272 (10)	0.0410 (12)	0.0088 (9)	−0.0083 (9)	0.0083 (9)
O4	0.0399 (11)	0.0236 (10)	0.0435 (12)	0.0119 (8)	−0.0035 (9)	0.0089 (8)
N1	0.0438 (15)	0.0302 (13)	0.0405 (14)	0.0138 (11)	−0.0009 (11)	0.0101 (11)
N2	0.0358 (13)	0.0377 (14)	0.0437 (15)	0.0132 (11)	−0.0014 (11)	0.0176 (11)
C1	0.0375 (15)	0.0250 (13)	0.0292 (14)	0.0091 (11)	0.0018 (11)	0.0079 (11)
C2	0.0278 (13)	0.0235 (12)	0.0277 (13)	0.0087 (10)	0.0035 (10)	0.0088 (10)
C3	0.0325 (13)	0.0264 (13)	0.0232 (12)	0.0109 (11)	0.0031 (10)	0.0083 (10)
C4	0.0357 (14)	0.0251 (13)	0.0284 (14)	0.0097 (11)	−0.0010 (11)	0.0081 (10)
C5	0.0422 (17)	0.0494 (19)	0.0387 (17)	0.0022 (15)	0.0039 (14)	0.0088 (15)
C6	0.065 (2)	0.069 (3)	0.0368 (18)	0.013 (2)	0.0189 (17)	0.0162 (17)
C7	0.083 (3)	0.056 (2)	0.0302 (17)	0.019 (2)	0.0007 (17)	0.0076 (16)
C8	0.079 (3)	0.063 (2)	0.041 (2)	−0.004 (2)	−0.0182 (19)	0.0049 (18)
C9	0.051 (2)	0.048 (2)	0.0445 (19)	−0.0068 (16)	−0.0056 (15)	0.0117 (15)
C10	0.0422 (16)	0.0369 (16)	0.0329 (15)	0.0076 (13)	−0.0004 (12)	0.0100 (12)
C11	0.0318 (14)	0.0281 (14)	0.0407 (16)	0.0046 (11)	−0.0003 (12)	0.0119 (12)
C12	0.0484 (18)	0.0415 (18)	0.050 (2)	0.0071 (15)	−0.0093 (15)	0.0186 (15)
C13	0.065 (2)	0.062 (2)	0.0413 (19)	0.0054 (19)	−0.0024 (17)	0.0155 (17)
C14	0.069 (3)	0.059 (2)	0.049 (2)	0.008 (2)	0.0201 (19)	0.0042 (18)
C15	0.0442 (18)	0.0449 (19)	0.060 (2)	0.0131 (15)	0.0112 (16)	0.0109 (16)
C16	0.0314 (14)	0.0297 (14)	0.0423 (17)	0.0045 (11)	0.0002 (12)	0.0125 (12)

Geometric parameters (Å, º)

O1—C1	1.280 (4)	C5—H5	0.93
O1—H1	0.82 (6)	C6—C7	1.364 (7)
O2—C1	1.225 (5)	C6—H6	0.93
O3—C3	1.278 (3)	C7—C8	1.350 (6)
O3—H3	0.87 (5)	C7—H7	0.93
O4—C3	1.237 (3)	C8—C9	1.406 (5)
N1—C10	1.316 (5)	C8—H8	0.93
N1—C11	1.379 (6)	C9—H9	0.93
N1—H1N	0.89 (4)	C10—H10	0.93
N2—C10	1.316 (5)	C11—C12	1.392 (4)
N2—C16	1.383 (4)	C11—C16	1.397 (4)
N2—H2N	0.87 (4)	C12—C13	1.372 (7)
C1—C2	1.528 (5)	C12—H12	0.93
C2—C4	1.520 (4)	C13—C14	1.399 (6)
C2—C3	1.533 (6)	C13—H13	0.93
C2—H2	0.98	C14—C15	1.381 (6)
C4—C5	1.379 (5)	C14—H14	0.93
C4—C9	1.383 (6)	C15—C16	1.393 (7)
C5—C6	1.400 (5)	C15—H15	0.93
O1···C10^i	3.206 (4)	O4···C10^v	2.926 (4)
O1···C1^ii	3.239 (4)	O4···C3^iii	2.974 (3)
O3···N2^i	3.092 (4)	C3···C3^iii	3.321 (4)
O3···O4^iii	3.191 (3)	C5···C9^vi	3.417 (5)
O3···C3^iv	3.292 (3)	C12···C15^vii	3.413 (5)
C1—O1—H1	121 (5)	C8—C7—H7	119.9
C3—O3—H3	120 (4)	C6—C7—H7	119.9
C10—N1—C11	108.4 (3)	C7—C8—C9	120.8 (4)
C10—N1—H1N	128 (3)	C7—C8—H8	119.6
C11—N1—H1N	124 (3)	C9—C8—H8	119.6
C10—N2—C16	108.1 (4)	C4—C9—C8	120.0 (4)
C10—N2—H2N	124 (3)	C4—C9—H9	120.0
C16—N2—H2N	128 (3)	C8—C9—H9	120.0
O2—C1—O1	124.3 (3)	N2—C10—N1	111.0 (3)
O2—C1—C2	120.1 (3)	N2—C10—H10	124.5
O1—C1—C2	115.6 (4)	N1—C10—H10	124.5
C4—C2—C1	111.1 (4)	N1—C11—C12	132.5 (3)
C4—C2—C3	110.9 (4)	N1—C11—C16	106.2 (3)
C1—C2—C3	110.9 (5)	C12—C11—C16	121.3 (4)
C4—C2—H2	107.9	C13—C12—C11	117.2 (3)
C1—C2—H2	107.9	C13—C12—H12	121.4
C3—C2—H2	107.9	C11—C12—H12	121.4
O4—C3—O3	124.6 (3)	C12—C13—C14	121.5 (4)
O4—C3—C2	119.5 (3)	C12—C13—H13	119.3
O3—C3—C2	115.9 (6)	C14—C13—H13	119.3
C5—C4—C9	118.3 (3)	C15—C14—C13	122.0 (4)
C5—C4—C2	122.4 (3)	C15—C14—H14	119.0
C9—C4—C2	119.2 (3)	C13—C14—H14	119.0
C4—C5—C6	121.0 (4)	C14—C15—C16	116.6 (3)
C4—C5—H5	119.5	C14—C15—H15	121.7
C6—C5—H5	119.5	C16—C15—H15	121.7
C7—C6—C5	119.8 (4)	N2—C16—C15	132.3 (3)
C7—C6—H6	120.1	N2—C16—C11	106.3 (4)
C5—C6—H6	120.1	C15—C16—C11	121.4 (3)
C8—C7—C6	120.2 (3)
O2—C1—C2—C4	27.3 (4)	C7—C8—C9—C4	−1.3 (6)
O1—C1—C2—C4	−153.7 (6)	C16—N2—C10—N1	−0.5 (4)
O2—C1—C2—C3	−96.5 (4)	C11—N1—C10—N2	0.5 (4)
O1—C1—C2—C3	82.5 (4)	C10—N1—C11—C12	179.5 (3)
C4—C2—C3—O4	67.0 (4)	C10—N1—C11—C16	−0.3 (3)
C1—C2—C3—O4	−169.1 (6)	N1—C11—C12—C13	−179.9 (3)
C4—C2—C3—O3	−110.6 (3)	C16—C11—C12—C13	−0.1 (5)
C1—C2—C3—O3	13.4 (3)	C11—C12—C13—C14	−0.4 (6)
C1—C2—C4—C5	−99.9 (3)	C12—C13—C14—C15	1.1 (6)
C3—C2—C4—C5	23.9 (4)	C13—C14—C15—C16	−1.2 (6)
C1—C2—C4—C9	78.5 (3)	C10—N2—C16—C15	−179.5 (3)
C3—C2—C4—C9	−157.7 (3)	C10—N2—C16—C11	0.3 (3)
C9—C4—C5—C6	−0.5 (5)	C14—C15—C16—N2	−179.6 (3)
C2—C4—C5—C6	177.9 (3)	C14—C15—C16—C11	0.7 (5)
C4—C5—C6—C7	−1.0 (6)	N1—C11—C16—N2	0.0 (3)
C5—C6—C7—C8	1.3 (6)	C12—C11—C16—N2	−179.8 (3)
C6—C7—C8—C9	−0.2 (6)	N1—C11—C16—C15	179.8 (3)
C5—C4—C9—C8	1.7 (5)	C12—C11—C16—C15	−0.1 (5)
C2—C4—C9—C8	−176.8 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.89 (4)	1.78 (4)	2.645 (4)	163 (4)
N2—H2N···O4^viii	0.87 (4)	1.94 (4)	2.788 (3)	165 (4)
O1—H1···O1^ii	0.82 (6)	1.70 (7)	2.504 (3)	167 (8)
O3—H3···O3^iv	0.87 (6)	1.63 (6)	2.494 (3)	177 (8)
C10—H10···O3^i	0.93	2.40	2.972 (4)	119
C15—H15···Cg^viii	0.93	2.92	3.713 (4)	144

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y+1, −z+2; (iv) −x+2, −y+2, −z+2; (viii) x+1, y−1, z.