3,4-Di­hydroxy­benzyl­ammonium 3,5-di­nitro­benzoate monohydrate

In the title compound, C₇H₁₀NO₂⁺·C₇H₃N₂O₆⁻·H₂O, the aromatic rings of the cation and anion are stacked alternately along the a axis. The ammonium group of the cation, the carboxyl­ate moiety of the anion and a water mol­ecule of crystallization are connected via N—H...O and O—H...O hydrogen bonds, forming hydro­philic columns along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.033
• wR factor = 0.090
• Data-to-parameter ratio = 7.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.50
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   C20     ..       5.11 su
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              H2 O

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           27.49
           From the CIF: _reflns_number_total               1883
           Count of symmetry unique reflns         1884
           Completeness (_total/calc)             99.95%
           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

   0 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
   1 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

C7H10NO2^+·C7H3N2O6^−·H2O	Dx = 1.615 Mg m^−3
Mr = 369.29	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 25 reflections
a = 14.546 (3) Å	θ = 10.9–13.6°
b = 15.065 (4) Å	µ = 0.14 mm^−1
c = 6.930 (2) Å	T = 298 K
V = 1518.6 (7) Å^3	Plate, yellow
Z = 4	0.5 × 0.4 × 0.2 mm
F(000) = 768

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.017
ω–2θ scans	θmax = 27.5°
Absorption correction: integration (ABSCOR; Higashi, 1999)	h = −7→18
Tmin = 0.950, Tmax = 0.974	k = 0→19
2296 measured reflections	l = −3→9
1883 independent reflections	3 standard reflections every 150 reflections
1654 reflections with I > 2σ(I)	intensity decay: 0.2%

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.033	w = 1/[σ^2(Fo^2) + (0.0564P)^2 + 0.1249P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.090	(Δ/σ)max = 0.002
S = 1.06	Δρmax = 0.18 e Å^−3
1883 reflections	Δρmin = −0.27 e Å^−3
251 parameters	Absolute structure: see text

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	0.9333 (1)	0.0604 (1)	0.4546 (3)	0.0349 (4)
O2	0.8719 (1)	0.1622 (1)	0.6458 (3)	0.0358 (4)
O3	0.8645 (2)	0.4724 (1)	0.3919 (4)	0.0681 (7)
O4	0.9559 (2)	0.5077 (1)	0.1578 (5)	0.0749 (8)
O5	1.0530 (1)	0.2750 (1)	−0.2709 (3)	0.0473 (5)
O6	1.0573 (1)	0.1394 (1)	−0.1693 (3)	0.0404 (4)
O7	0.7707 (1)	0.2857 (1)	−0.1585 (3)	0.0329 (4)
O8	0.7171 (1)	0.3985 (1)	0.1117 (3)	0.0348 (4)
O9	1.1134 (1)	0.0024 (1)	0.3687 (3)	0.0327 (3)
N10	0.7929 (1)	−0.0200 (1)	0.2363 (3)	0.0302 (4)
N11	0.9192 (2)	0.4536 (2)	0.2644 (4)	0.0460 (6)
N12	1.0388 (1)	0.2183 (1)	−0.1488 (3)	0.0296 (4)
C13	0.7070 (2)	0.0308 (2)	0.2801 (4)	0.0318 (5)
C14	0.7130 (1)	0.1282 (1)	0.2332 (3)	0.0258 (4)
C15	0.7410 (2)	0.1597 (1)	0.0520 (3)	0.0259 (4)
C16	0.7434 (1)	0.2504 (1)	0.0151 (3)	0.0246 (4)
C17	0.7148 (1)	0.3102 (1)	0.1573 (3)	0.0250 (4)
C18	0.6862 (2)	0.2787 (1)	0.3350 (4)	0.0287 (4)
C19	0.6863 (2)	0.1884 (1)	0.3733 (3)	0.0285 (4)
C20	0.9110 (1)	0.1393 (1)	0.4942 (3)	0.0269 (4)
C21	0.9341 (1)	0.2089 (1)	0.3437 (4)	0.0254 (4)
C22	0.9163 (2)	0.2981 (2)	0.3755 (4)	0.0292 (4)
C23	0.9394 (2)	0.3589 (1)	0.2332 (4)	0.0314 (5)
C24	0.9805 (2)	0.3356 (1)	0.0604 (4)	0.0303 (5)
C25	0.9960 (1)	0.2459 (1)	0.0335 (3)	0.0253 (4)
C26	0.9738 (1)	0.1827 (1)	0.1693 (3)	0.0248 (4)
H7	0.789 (2)	0.244 (2)	−0.220 (5)	0.0405 (1)*
H8	0.676 (2)	0.426 (2)	0.187 (7)	0.0649 (1)*
H9A	1.054 (3)	0.020 (2)	0.402 (7)	0.0717 (1)*
H9B	1.108 (2)	−0.045 (2)	0.295 (5)	0.0394 (1)*
H10A	0.8421	0.0027	0.3117	0.0362*
H10B	0.8073	−0.0140	0.1033	0.0362*
H10C	0.7838	−0.0809	0.2662	0.0362*
H13A	0.6581	0.0058	0.2073	0.0382*
H13B	0.6940	0.0248	0.4139	0.0382*
H15	0.7584	0.1190	−0.0459	0.0311*
H18	0.6664	0.3193	0.4314	0.0344*
H19	0.6679	0.1676	0.4969	0.0342*
H22	0.8888	0.3173	0.4927	0.0350*
H24	0.9972	0.3786	−0.0337	0.0363*
H26	0.9854	0.1217	0.1445	0.0298*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0447 (9)	0.0278 (8)	0.0322 (9)	0.0014 (7)	0.0043 (8)	0.0039 (7)
O2	0.0368 (9)	0.0453 (10)	0.0255 (8)	0.0034 (7)	0.0057 (7)	0.0008 (7)
O3	0.097 (2)	0.045 (1)	0.062 (2)	0.026 (1)	0.003 (1)	−0.019 (1)
O4	0.110 (2)	0.0236 (9)	0.091 (2)	−0.001 (1)	0.007 (2)	0.007 (1)
O5	0.060 (1)	0.052 (1)	0.030 (1)	−0.0088 (9)	0.0099 (9)	0.0099 (9)
O6	0.0439 (9)	0.0435 (10)	0.0339 (9)	0.0118 (7)	0.0035 (8)	−0.0059 (8)
O7	0.0453 (9)	0.0290 (8)	0.0243 (8)	0.0058 (7)	0.0097 (8)	0.0047 (8)
O8	0.0507 (10)	0.0234 (7)	0.0301 (9)	0.0046 (7)	0.0059 (8)	0.0005 (7)
O9	0.0385 (8)	0.0273 (7)	0.0322 (9)	−0.0027 (6)	−0.0018 (8)	−0.0049 (7)
N10	0.041 (1)	0.0224 (8)	0.0270 (10)	0.0042 (7)	0.0009 (8)	0.0019 (8)
N11	0.060 (1)	0.0275 (10)	0.050 (1)	0.0087 (10)	−0.012 (1)	−0.008 (1)
N12	0.0258 (8)	0.040 (1)	0.0234 (9)	−0.0018 (7)	0.0004 (8)	0.0000 (9)
C13	0.033 (1)	0.030 (1)	0.033 (1)	−0.0002 (9)	0.0014 (9)	0.0064 (10)
C14	0.0264 (9)	0.0270 (10)	0.024 (1)	0.0036 (8)	−0.0004 (8)	0.0035 (9)
C15	0.029 (1)	0.0261 (10)	0.023 (1)	0.0053 (8)	0.0014 (8)	0.0006 (8)
C16	0.0254 (9)	0.0281 (10)	0.020 (1)	0.0050 (8)	0.0001 (8)	0.0016 (9)
C17	0.0272 (10)	0.0241 (10)	0.024 (1)	0.0039 (8)	−0.0013 (9)	0.0021 (8)
C18	0.0325 (10)	0.031 (1)	0.023 (1)	0.0058 (8)	0.0022 (9)	−0.0025 (9)
C19	0.0289 (9)	0.034 (1)	0.0220 (10)	0.0040 (8)	0.0023 (9)	0.0040 (10)
C20	0.0237 (9)	0.035 (1)	0.022 (1)	−0.0018 (8)	−0.0020 (8)	0.0036 (9)
C21	0.0238 (9)	0.0274 (9)	0.025 (1)	0.0004 (7)	−0.0017 (9)	0.0005 (9)
C22	0.031 (1)	0.032 (1)	0.025 (1)	0.0037 (8)	−0.0024 (9)	−0.0034 (9)
C23	0.035 (1)	0.0221 (10)	0.037 (1)	0.0026 (8)	−0.006 (1)	−0.0037 (9)
C24	0.035 (1)	0.0247 (10)	0.031 (1)	−0.0016 (8)	−0.0036 (9)	0.0046 (9)
C25	0.0240 (9)	0.030 (1)	0.022 (1)	−0.0003 (8)	−0.0012 (8)	0.0001 (8)
C26	0.0272 (9)	0.0246 (9)	0.0226 (9)	0.0009 (8)	−0.0009 (9)	−0.0006 (8)

Geometric parameters (Å, º)

O1—C20	1.263 (3)	C13—H13B	0.950
O2—C20	1.244 (3)	C14—C15	1.403 (3)
O3—N11	1.222 (4)	C14—C19	1.384 (3)
O4—N11	1.223 (4)	C15—C16	1.390 (3)
O5—N12	1.220 (3)	C15—H15	0.950
O6—N12	1.227 (3)	C16—C17	1.398 (3)
O7—C16	1.374 (3)	C17—C18	1.384 (3)
O7—H7	0.80 (3)	C18—C19	1.387 (3)
O8—C17	1.368 (3)	C18—H18	0.950
O8—H8	0.89 (4)	C19—H19	0.950
O9—H9A	0.93 (4)	C20—C21	1.517 (3)
O9—H9B	0.88 (3)	C21—C22	1.386 (3)
N10—C13	1.496 (3)	C21—C26	1.396 (3)
N10—H10A	0.950	C22—C23	1.387 (3)
N10—H10B	0.950	C22—H22	0.950
N10—H10C	0.950	C23—C24	1.384 (4)
N11—C23	1.472 (3)	C24—C25	1.383 (3)
N12—C25	1.468 (3)	C24—H24	0.950
C13—C14	1.506 (3)	C25—C26	1.377 (3)
C13—H13A	0.950	C26—H26	0.950
C16—O7—H7	105 (2)	O8—C17—C16	117.2 (2)
C17—O8—H8	107 (2)	O8—C17—C18	123.1 (2)
H9A—O9—H9B	107 (3)	C16—C17—C18	119.7 (2)
C13—N10—H10A	109.5	C17—C18—C19	120.4 (2)
C13—N10—H10B	109.5	C17—C18—H18	119.8
C13—N10—H10C	109.5	C19—C18—H18	119.8
H10A—N10—H10B	109.5	C14—C19—C18	120.6 (2)
H10A—N10—H10C	109.5	C14—C19—H19	119.7
H10B—N10—H10C	109.5	C18—C19—H19	119.7
O3—N11—O4	124.5 (2)	O1—C20—O2	124.2 (2)
O3—N11—C23	117.4 (2)	O1—C20—C21	116.3 (2)
O4—N11—C23	118.0 (3)	O2—C20—C21	119.4 (2)
O5—N12—O6	124.1 (2)	C20—C21—C22	121.3 (2)
O5—N12—C25	118.1 (2)	C20—C21—C26	119.5 (2)
O6—N12—C25	117.8 (2)	C22—C21—C26	119.3 (2)
N10—C13—C14	113.9 (2)	C21—C22—C23	118.8 (2)
N10—C13—H13A	108.4	C21—C22—H22	120.6
N10—C13—H13B	108.4	C23—C22—H22	120.6
C14—C13—H13A	108.4	N11—C23—C22	119.2 (2)
C14—C13—H13B	108.3	N11—C23—C24	117.3 (2)
H13A—C13—H13B	109.5	C22—C23—C24	123.5 (2)
C13—C14—C15	122.7 (2)	C23—C24—C25	115.7 (2)
C13—C14—C19	118.0 (2)	C23—C24—H24	122.1
C15—C14—C19	119.2 (2)	C25—C24—H24	122.1
C14—C15—C16	120.3 (2)	N12—C25—C24	117.5 (2)
C14—C15—H15	119.8	N12—C25—C26	119.5 (2)
C16—C15—H15	119.8	C24—C25—C26	123.1 (2)
O7—C16—C15	123.3 (2)	C21—C26—C25	119.5 (2)
O7—C16—C17	117.0 (2)	C21—C26—H26	120.2
C15—C16—C17	119.7 (2)	C25—C26—H26	120.2
O1—C20—C21—C22	−177.2 (2)	N11—C23—C24—C25	−178.1 (2)
O1—C20—C21—C26	3.1 (3)	N12—C25—C24—C23	179.4 (2)
O2—C20—C21—C22	2.9 (3)	N12—C25—C26—C21	179.2 (2)
O2—C20—C21—C26	−176.8 (2)	C13—C14—C15—C16	178.6 (2)
O3—N11—C23—C22	−16.7 (4)	C13—C14—C19—C18	−176.9 (2)
O3—N11—C23—C24	163.1 (3)	C14—C15—C16—C17	−2.1 (3)
O4—N11—C23—C22	165.5 (3)	C14—C19—C18—C17	−1.5 (3)
O4—N11—C23—C24	−14.7 (4)	C15—C14—C19—C18	0.7 (3)
O5—N12—C25—C24	−4.5 (3)	C15—C16—C17—C18	1.3 (3)
O5—N12—C25—C26	176.0 (2)	C16—C15—C14—C19	1.1 (3)
O6—N12—C25—C24	176.1 (2)	C16—C17—C18—C19	0.5 (3)
O6—N12—C25—C26	−3.4 (3)	C20—C21—C22—C23	179.7 (2)
O7—C16—C15—C14	179.5 (2)	C20—C21—C26—C25	−179.2 (2)
O7—C16—C17—O8	−0.4 (3)	C21—C22—C23—C24	−0.8 (4)
O7—C16—C17—C18	179.8 (2)	C21—C26—C25—C24	−0.2 (3)
O8—C17—C16—C15	−178.9 (2)	C22—C21—C26—C25	1.1 (3)
O8—C17—C18—C19	−179.3 (2)	C22—C23—C24—C25	1.6 (4)
N10—C13—C14—C15	52.3 (3)	C23—C22—C21—C26	−0.6 (3)
N10—C13—C14—C19	−130.2 (2)	C23—C24—C25—C26	−1.1 (3)
N11—C23—C22—C21	179.0 (2)	C23—C24—C25—C26	−1.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O2^i	0.80 (3)	1.96 (3)	2.733 (2)	161 (3)
O8—H8···O9^ii	0.89 (4)	1.89 (4)	2.770 (3)	167 (4)
O9—H9A···O1	0.93 (4)	1.90 (4)	2.825 (3)	176 (4)
O9—H9B···O2^iii	0.88 (3)	2.07 (3)	2.930 (3)	166 (3)
N10—H10A···O1	0.95	1.87	2.816 (3)	173
N10—H10B···O9^iii	0.95	2.00	2.901 (3)	158
N10—H10C···O7^iv	0.95	2.22	3.155 (2)	167
N10—H10C···O8^iv	0.95	2.41	2.880 (3)	110

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