Benzyl­ammonium 3,5-di­nitro­benzoate

In the title compound, C₇H₁₀N⁺·C₇H₃N₂O₆^-, the ammonium group of the cation and the carboxyl­ate group of the anion are connected via hydrogen bonds, forming columns along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.040
• wR factor = 0.106
• Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N9
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors  for        C10

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.51
           From the CIF: _reflns_number_total               1900
           Count of symmetry unique reflns         1902
           Completeness (_total/calc)             99.89%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

(I)

Crystal data

C7H10N^+·C7H3N2O6^−	F(000) = 332
Mr = 319.27	Dx = 1.398 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 11.602 (3) Å	Cell parameters from 25 reflections
b = 6.2657 (12) Å	θ = 10.1–12.6°
c = 10.898 (2) Å	µ = 0.11 mm^−1
β = 106.85 (2)°	T = 298 K
V = 758.2 (3) Å^3	Plate, colorless
Z = 2	0.6 × 0.5 × 0.2 mm

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.014
ω–2θ scans	θmax = 27.5°
Absorption correction: integration (ABSCOR; Higashi, 1999)	h = −5→15
Tmin = 0.948, Tmax = 0.978	k = −8→3
2172 measured reflections	l = −14→14
1900 independent reflections	3 standard reflections every 150 reflections
1568 reflections with I > 2σ(I)	intensity decay: 0.5%

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.0591P)^2 + 0.0545P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.106	(Δ/σ)max = 0.003
S = 1.08	Δρmax = 0.23 e Å^−3
1900 reflections	Δρmin = −0.32 e Å^−3
208 parameters

Special details

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
O1	0.1527 (1)	0.2556 (3)	0.0355 (2)	0.0550 (4)
O2	0.2343 (2)	0.5448 (3)	0.1444 (2)	0.0665 (5)
O3	0.4323 (2)	−0.3256 (4)	0.0223 (2)	0.0758 (6)
O4	0.5980 (2)	−0.3573 (5)	0.1726 (3)	0.1063 (10)
O5	0.7031 (2)	0.1570 (7)	0.5143 (2)	0.120 (1)
O6	0.6083 (3)	0.4582 (7)	0.4897 (3)	0.126 (1)
N7	0.0744 (2)	−0.1284 (3)	0.1096 (2)	0.0471 (4)
N8	0.5041 (2)	−0.2654 (4)	0.1202 (2)	0.0605 (5)
N9	0.6221 (2)	0.2741 (6)	0.4580 (2)	0.0806 (9)
C10	0.0814 (3)	−0.1016 (6)	0.2466 (3)	0.0720 (8)
C11	0.0139 (2)	0.0887 (5)	0.2728 (2)	0.0549 (6)
C12	−0.1092 (3)	0.1157 (6)	0.2137 (3)	0.0640 (7)
C13	−0.1694 (3)	0.2900 (7)	0.2430 (3)	0.0741 (9)
C14	−0.1082 (3)	0.4338 (6)	0.3344 (3)	0.0762 (8)
C15	0.0125 (3)	0.4086 (6)	0.3943 (3)	0.0738 (8)
C16	0.0734 (2)	0.2384 (6)	0.3623 (2)	0.0633 (7)
C17	0.2354 (2)	0.3563 (4)	0.1143 (2)	0.0431 (5)
C18	0.3494 (2)	0.2303 (4)	0.1763 (2)	0.0388 (4)
C19	0.3722 (2)	0.0401 (4)	0.1236 (2)	0.0400 (4)
C20	0.4777 (2)	−0.0677 (4)	0.1815 (2)	0.0453 (5)
C21	0.5605 (2)	0.0039 (5)	0.2912 (2)	0.0531 (6)
C22	0.5344 (2)	0.1932 (5)	0.3408 (2)	0.0530 (6)
C23	0.4318 (2)	0.3101 (4)	0.2856 (2)	0.0478 (5)
H7A	0.1066	−0.0055	0.0804	0.0566*
H7B	0.1194	−0.2506	0.0998	0.0566*
H7C	−0.0073	−0.1462	0.0607	0.0566*
H10A	0.0492	−0.2257	0.2743	0.0864*
H10B	0.1637	−0.0866	0.2943	0.0864*
H12	−0.1519	0.0135	0.1530	0.0768*
H13	−0.2526	0.3106	0.2003	0.0889*
H14	−0.1500	0.5516	0.3561	0.0916*
H15	0.0539	0.5079	0.4577	0.0885*
H16	0.1575	0.2237	0.4022	0.0761*
H19	0.3162	−0.0155	0.0487	0.0480*
H21	0.6321	−0.0735	0.3306	0.0637*
H23	0.4179	0.4423	0.3215	0.0573*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0370 (7)	0.0494 (10)	0.0687 (10)	0.0036 (7)	−0.0006 (6)	0.0131 (9)
O2	0.060 (1)	0.041 (1)	0.092 (1)	0.0161 (9)	0.0127 (9)	0.0005 (10)
O3	0.081 (1)	0.065 (1)	0.088 (1)	0.006 (1)	0.036 (1)	−0.021 (1)
O4	0.092 (2)	0.096 (2)	0.126 (2)	0.063 (2)	0.024 (1)	−0.003 (2)
O5	0.078 (1)	0.163 (3)	0.082 (1)	0.017 (2)	−0.034 (1)	−0.009 (2)
O6	0.084 (2)	0.159 (3)	0.110 (2)	0.005 (2)	−0.010 (1)	−0.075 (2)
N7	0.0338 (8)	0.0356 (9)	0.064 (1)	0.0037 (8)	0.0019 (7)	−0.0011 (9)
N8	0.061 (1)	0.051 (1)	0.078 (1)	0.019 (1)	0.034 (1)	0.005 (1)
N9	0.052 (1)	0.121 (3)	0.058 (1)	0.003 (2)	−0.0013 (10)	−0.019 (2)
C10	0.084 (2)	0.065 (2)	0.061 (1)	0.027 (2)	0.012 (1)	0.017 (1)
C11	0.060 (1)	0.056 (1)	0.047 (1)	0.009 (1)	0.014 (1)	0.010 (1)
C12	0.059 (1)	0.070 (2)	0.059 (1)	0.005 (1)	0.010 (1)	−0.010 (1)
C13	0.060 (1)	0.089 (2)	0.072 (2)	0.016 (2)	0.018 (1)	−0.006 (2)
C14	0.090 (2)	0.069 (2)	0.077 (2)	0.013 (2)	0.037 (2)	−0.002 (2)
C15	0.087 (2)	0.069 (2)	0.066 (2)	−0.013 (2)	0.023 (1)	−0.008 (2)
C16	0.058 (1)	0.072 (2)	0.055 (1)	−0.006 (1)	0.009 (1)	0.010 (1)
C17	0.0360 (9)	0.037 (1)	0.055 (1)	0.0088 (9)	0.0123 (8)	0.0088 (10)
C18	0.0322 (8)	0.038 (1)	0.0453 (10)	0.0039 (9)	0.0100 (7)	0.0066 (9)
C19	0.0351 (9)	0.040 (1)	0.045 (1)	0.0022 (9)	0.0121 (8)	0.0029 (9)
C20	0.045 (1)	0.044 (1)	0.051 (1)	0.0110 (10)	0.0205 (9)	0.007 (1)
C21	0.039 (1)	0.067 (2)	0.051 (1)	0.017 (1)	0.0103 (9)	0.013 (1)
C22	0.038 (1)	0.073 (2)	0.043 (1)	−0.002 (1)	0.0042 (8)	−0.001 (1)
C23	0.043 (1)	0.049 (1)	0.051 (1)	0.0007 (10)	0.0128 (9)	−0.006 (1)

Geometric parameters (Å, º)

O1—C17	1.256 (3)	C12—H12	0.950
O2—C17	1.227 (3)	C13—C14	1.377 (5)
O3—N8	1.208 (3)	C13—H13	0.950
O4—N8	1.218 (3)	C14—C15	1.372 (5)
O5—N9	1.209 (4)	C14—H14	0.950
O6—N9	1.228 (6)	C15—C16	1.379 (5)
N7—C10	1.481 (4)	C15—H15	0.950
N7—H7A	0.950	C16—H16	0.950
N7—H7B	0.950	C17—C18	1.520 (3)
N7—H7C	0.950	C18—C19	1.381 (3)
N8—C20	1.481 (4)	C18—C23	1.387 (3)
N9—C22	1.473 (3)	C19—C20	1.380 (3)
C10—C11	1.499 (5)	C19—H19	0.950
C10—H10A	0.950	C20—C21	1.374 (3)
C10—H10B	0.951	C21—C22	1.373 (4)
C11—C12	1.396 (4)	C21—H21	0.950
C11—C16	1.385 (4)	C22—C23	1.379 (3)
C12—C13	1.383 (5)	C23—H23	0.950
C10—N7—H7A	109.5	C15—C14—H14	119.7
C10—N7—H7B	109.5	C14—C15—C16	119.7 (3)
C10—N7—H7C	109.5	C14—C15—H15	120.1
H7A—N7—H7B	109.5	C16—C15—H15	120.1
H7A—N7—H7C	109.5	C11—C16—C15	120.9 (2)
H7B—N7—H7C	109.5	C11—C16—H16	119.5
O3—N8—O4	124.1 (3)	C15—C16—H16	119.5
O3—N8—C20	118.6 (2)	O1—C17—O2	127.0 (2)
O4—N8—C20	117.2 (2)	O1—C17—C18	115.9 (2)
O5—N9—O6	124.9 (3)	O2—C17—C18	117.2 (2)
O5—N9—C22	118.1 (3)	C17—C18—C19	120.7 (2)
O6—N9—C22	117.0 (3)	C17—C18—C23	119.3 (2)
N7—C10—C11	113.8 (2)	C19—C18—C23	120.0 (2)
N7—C10—H10A	108.4	C18—C19—C20	118.9 (2)
N7—C10—H10B	108.4	C18—C19—H19	120.5
C11—C10—H10A	108.4	C20—C19—H19	120.5
C11—C10—H10B	108.4	N8—C20—C19	118.4 (2)
H10A—C10—H10B	109.4	N8—C20—C21	118.8 (2)
C10—C11—C12	122.0 (3)	C19—C20—C21	122.8 (2)
C10—C11—C16	119.5 (2)	C20—C21—C22	116.5 (2)
C12—C11—C16	118.5 (3)	C20—C21—H21	121.7
C11—C12—C13	120.5 (3)	C22—C21—H21	121.8
C11—C12—H12	119.8	N9—C22—C21	117.6 (2)
C13—C12—H12	119.8	N9—C22—C23	119.2 (3)
C12—C13—C14	119.6 (3)	C21—C22—C23	123.2 (2)
C12—C13—H13	120.2	C18—C23—C22	118.5 (2)
C14—C13—H13	120.2	C18—C23—H23	120.7
C13—C14—C15	120.7 (4)	C22—C23—H23	120.8
C13—C14—H14	119.7
O1—C17—C18—C19	17.1 (3)	C10—C11—C12—C13	178.0 (3)
O1—C17—C18—C23	−164.1 (2)	C10—C11—C16—C15	−176.1 (3)
O2—C17—C18—C19	−161.8 (2)	C11—C12—C13—C14	−2.3 (5)
O2—C17—C18—C23	17.1 (4)	C11—C16—C15—C14	−1.8 (5)
O3—N8—C20—C19	−0.4 (4)	C12—C11—C16—C15	1.1 (5)
O3—N8—C20—C21	−178.5 (3)	C12—C13—C14—C15	1.6 (6)
O4—N8—C20—C19	179.6 (3)	C13—C12—C11—C16	1.0 (5)
O4—N8—C20—C21	1.5 (4)	C13—C14—C15—C16	0.4 (6)
O5—N9—C22—C21	−10.2 (4)	C17—C18—C19—C20	178.9 (2)
O5—N9—C22—C23	170.5 (3)	C17—C18—C23—C22	179.7 (2)
O6—N9—C22—C21	168.4 (3)	C18—C19—C20—C21	1.2 (4)
O6—N9—C22—C23	−10.9 (4)	C18—C23—C22—C21	1.6 (4)
N7—C10—C11—C12	57.8 (4)	C19—C18—C23—C22	−1.4 (4)
N7—C10—C11—C16	−125.2 (3)	C19—C20—C21—C22	−1.0 (4)
N8—C20—C19—C18	−176.8 (2)	C20—C19—C18—C23	0.1 (4)
N8—C20—C21—C22	177.0 (2)	C20—C21—C22—C23	−0.4 (4)
N9—C22—C21—C20	−179.7 (3)	C20—C21—C22—C23	−0.4 (4)
N9—C22—C23—C18	−179.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7A···O1	0.95	1.83	2.774 (3)	171
N7—H7B···O2^i	0.95	1.81	2.715 (3)	158
N7—H7C···O1^ii	0.95	1.82	2.748 (2)	167

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