A 2:1 complex of 2-nitro­aniline and picric acid

Saminathan, K.; Sivakumar, K.

doi:10.1107/S1600536806053785

A 2:1 complex of 2-nitroaniline and picric acid

In the title molecular complex, 2C₆H₆N₂O₂·C₆H₃N₃O₇, an undissociated picric acid molecule is sandwiched between two crystallographically independent nitroaniline molecules. The molecules stack in columns down the a axis, with the packing stabilized by N—H

O and C—H

O hydrogen bonds and π–π stacking interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053785/sj2197sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053785/sj2197Isup2.hkl Contains datablock I

CCDC reference: 634058

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.009 Å
R factor = 0.056
wR factor = 0.179
Data-to-parameter ratio = 5.9

checkCIF/PLATON results

No syntax errors found



Alert level B
REFNR01_ALERT_3_B  Ratio of reflections to parameters is < 6 for a
            non-centrosymmetric structure, where ZMAX < 18
            sine(theta)/lambda                0.6012
            Proportion of unique data used    0.9450
            Ratio reflections to parameters   5.8988
PLAT024_ALERT_4_B Merging of Friedel Pairs is STRONGLY Indicated .          !
PLAT089_ALERT_3_B Poor Data / Parameter Ratio (Zmax .LT. 18) .....       5.90
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for       C10B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C7B

Alert level C
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.67 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O9B    -   N4B     ..       6.40 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10B   -   C11B    ..       6.27 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C12B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N4A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N4B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C8B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C11B
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3     ..  O9B     ..       2.62 Ang.

Alert level G
REFLT03_ALERT_4_G  WARNING: CuKa measured Friedel data can be used to
                     determine absolute structure in a light-atom
                     study only if the Friedel fraction is large.
           From the CIF: _diffrn_reflns_theta_max           67.96
           From the CIF: _reflns_number_total               2035
           Count of symmetry unique reflns         1922
           Completeness (_total/calc)            105.88%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       113
           Fraction of Friedel pairs measured     0.059
           Are heavy atom types Z>Si present         no
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
   5 ALERT level B = Potentially serious problem
  15 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

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

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

2-nitroaniline–picric acid (2/1) top

Crystal data top

2C₆H₆N₂O₂·C₆H₃N₃O₇	F(000) = 1040
M_r = 505.37	D_x = 1.586 Mg m⁻³
Monoclinic, Cc	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: C -2yc	Cell parameters from 25 reflections
a = 10.3644 (17) Å	θ = 15–35°
b = 15.1394 (19) Å	µ = 1.17 mm⁻¹
c = 14.1042 (15) Å	T = 293 K
β = 106.943 (11)°	Prism, red
V = 2117.0 (5) Å³	0.40 × 0.26 × 0.15 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1654 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 68.0°, θ_min = 5.3°
ω/2θ scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = 0→18
T_min = 0.755, T_max = 0.871	l = −16→16
2035 measured reflections	2 standard reflections every 100 reflections
2035 independent reflections	intensity decay: none

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)] = 0.056	Hydrogen site location: difference Fourier map
wR(F²) = 0.179	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.1298P)² + 0.4588P] where P = (F_o² + 2F_c²)/3
1923 reflections	(Δ/σ)_max < 0.001
326 parameters	Δρ_max = 0.41 e Å⁻³
10 restraints	Δρ_min = −0.26 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
O1	0.5712 (4)	0.5211 (3)	0.8386 (3)	0.0715 (9)
H1	0.5646	0.4681	0.8265	0.107*
C1	0.5545 (4)	0.5656 (3)	0.7555 (4)	0.0542 (9)
C2	0.5251 (5)	0.5283 (3)	0.6599 (4)	0.0564 (10)
C3	0.5066 (5)	0.5771 (4)	0.5756 (4)	0.0620 (12)
H3	0.4877	0.5501	0.5138	0.074*
C4	0.5168 (5)	0.6689 (4)	0.5849 (4)	0.0620 (11)
C5	0.5429 (6)	0.7096 (4)	0.6757 (4)	0.0694 (13)
H5	0.5474	0.7708	0.6809	0.083*
C6	0.5619 (5)	0.6579 (3)	0.7582 (4)	0.0614 (11)
N1	0.5135 (6)	0.4329 (3)	0.6484 (4)	0.0769 (13)
O2	0.5327 (7)	0.3880 (3)	0.7234 (4)	0.1091 (18)
O3	0.4862 (7)	0.4022 (4)	0.5669 (4)	0.1161 (19)
N2	0.4993 (6)	0.7230 (4)	0.4958 (4)	0.0834 (14)
O4	0.4930 (7)	0.6849 (4)	0.4184 (4)	0.1066 (16)
O5	0.4966 (8)	0.8030 (4)	0.5042 (5)	0.119 (2)
N3	0.5957 (6)	0.7027 (3)	0.8548 (4)	0.0788 (13)
O6	0.5280 (7)	0.7672 (3)	0.8604 (5)	0.1132 (18)
O7	0.6889 (6)	0.6751 (4)	0.9204 (4)	0.1117 (19)
C7A	0.8376 (4)	0.5874 (3)	0.6048 (3)	0.0498 (9)
C8A	0.8704 (4)	0.6175 (3)	0.7033 (3)	0.0520 (10)
C9A	0.8913 (5)	0.5507 (4)	0.7757 (4)	0.0692 (13)
H9A	0.9138	0.5664	0.8423	0.083*
C10A	0.8791 (6)	0.4630 (4)	0.7503 (6)	0.087 (2)
H10A	0.8933	0.4205	0.8000	0.104*
C11A	0.8466 (6)	0.4367 (4)	0.6534 (6)	0.0832 (18)
H11A	0.8383	0.3769	0.6376	0.100*
C12A	0.8264 (5)	0.4979 (3)	0.5807 (4)	0.0665 (12)
H12A	0.8051	0.4803	0.5148	0.080*
N4A	0.8125 (5)	0.6482 (3)	0.5233 (3)	0.0708 (11)
O8A	0.7895 (7)	0.6210 (4)	0.4383 (4)	0.1121 (18)
O9A	0.8110 (6)	0.7275 (3)	0.5390 (4)	0.0986 (15)
N5A	0.8799 (6)	0.7019 (3)	0.7302 (4)	0.0800 (13)
H5A	0.8656	0.7426	0.6858	0.096*
H5B	0.9005	0.7158	0.7919	0.096*
C7B	0.2104 (4)	0.5352 (3)	0.7276 (3)	0.0640 (12)
C8B	0.2222 (6)	0.6189 (3)	0.7726 (4)	0.0814 (16)
C9B	0.1988 (7)	0.6936 (5)	0.7105 (8)	0.134 (4)
H9B	0.2047	0.7504	0.7366	0.161*
C10B	0.1671 (11)	0.6799 (9)	0.6102 (8)	0.173 (7)
H10B	0.1527	0.7301	0.5705	0.207*
C11B	0.1542 (9)	0.6004 (9)	0.5624 (6)	0.132 (4)
H11B	0.1316	0.5950	0.4938	0.158*
C12B	0.1776 (6)	0.5305 (7)	0.6247 (5)	0.123 (4)
H12B	0.1714	0.4745	0.5965	0.147*
N4B	0.2305 (6)	0.4559 (3)	0.7860 (6)	0.106 (2)
N5B	0.2518 (8)	0.6345 (6)	0.8693 (4)	0.126 (3)
H5C	0.2657	0.5912	0.9104	0.152*
H5D	0.2570	0.6880	0.8907	0.152*
O8B	0.2215 (9)	0.3857 (4)	0.7437 (8)	0.171 (4)
O9B	0.2553 (8)	0.4606 (5)	0.8769 (6)	0.136 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.092 (2)	0.068 (2)	0.0565 (19)	0.0094 (18)	0.0247 (18)	0.0182 (16)
C1	0.046 (2)	0.065 (3)	0.051 (2)	0.006 (2)	0.0118 (16)	0.005 (2)
C2	0.049 (2)	0.065 (3)	0.052 (2)	−0.0069 (18)	0.0099 (17)	0.0026 (19)
C3	0.050 (2)	0.084 (3)	0.048 (2)	−0.006 (2)	0.0078 (18)	0.004 (2)
C4	0.057 (2)	0.078 (3)	0.051 (2)	0.014 (2)	0.0150 (18)	0.017 (2)
C5	0.077 (3)	0.067 (3)	0.065 (3)	0.023 (2)	0.021 (2)	0.015 (2)
C6	0.067 (3)	0.062 (3)	0.053 (2)	0.022 (2)	0.0139 (19)	0.008 (2)
N1	0.090 (3)	0.070 (3)	0.068 (3)	−0.036 (2)	0.020 (2)	−0.010 (2)
O2	0.166 (5)	0.075 (3)	0.090 (3)	−0.037 (3)	0.042 (3)	0.011 (2)
O3	0.162 (5)	0.088 (3)	0.085 (3)	−0.047 (3)	0.014 (3)	−0.020 (3)
N2	0.083 (3)	0.103 (4)	0.062 (3)	0.024 (3)	0.018 (2)	0.030 (3)
O4	0.131 (4)	0.130 (4)	0.055 (2)	0.006 (3)	0.022 (2)	0.018 (2)
O5	0.169 (5)	0.095 (3)	0.101 (3)	0.057 (4)	0.054 (3)	0.049 (3)
N3	0.108 (3)	0.067 (3)	0.060 (3)	0.021 (2)	0.022 (2)	0.001 (2)
O6	0.154 (5)	0.090 (3)	0.093 (3)	0.047 (3)	0.033 (3)	−0.012 (3)
O7	0.144 (5)	0.108 (3)	0.060 (2)	0.043 (3)	−0.006 (3)	−0.007 (2)
C7A	0.047 (2)	0.049 (2)	0.054 (2)	−0.0033 (16)	0.0159 (17)	−0.0045 (17)
C8A	0.0454 (19)	0.055 (2)	0.056 (2)	−0.0074 (17)	0.0144 (17)	−0.0098 (18)
C9A	0.061 (3)	0.092 (4)	0.055 (3)	0.003 (2)	0.019 (2)	0.011 (2)
C10A	0.069 (3)	0.078 (4)	0.119 (6)	0.015 (3)	0.035 (3)	0.044 (4)
C11A	0.080 (3)	0.047 (3)	0.129 (6)	0.000 (2)	0.040 (4)	−0.005 (3)
C12A	0.062 (3)	0.059 (3)	0.080 (3)	−0.006 (2)	0.022 (2)	−0.023 (2)
N4A	0.063 (2)	0.085 (3)	0.060 (2)	−0.010 (2)	0.0102 (18)	0.008 (2)
O8A	0.132 (4)	0.145 (5)	0.056 (2)	−0.023 (3)	0.023 (2)	−0.003 (2)
O9A	0.121 (4)	0.071 (3)	0.091 (3)	−0.012 (2)	0.013 (3)	0.022 (2)
N5A	0.093 (3)	0.062 (2)	0.082 (3)	−0.010 (2)	0.021 (3)	−0.025 (2)
C7B	0.048 (2)	0.071 (3)	0.072 (3)	0.002 (2)	0.016 (2)	−0.004 (2)
C8B	0.066 (3)	0.079 (4)	0.096 (4)	−0.004 (3)	0.018 (3)	0.002 (3)
C9B	0.078 (4)	0.081 (5)	0.233 (13)	−0.017 (4)	0.027 (6)	0.043 (6)
C10B	0.091 (6)	0.27 (2)	0.147 (11)	−0.036 (9)	0.028 (7)	0.096 (13)
C11B	0.066 (4)	0.250 (14)	0.078 (5)	−0.001 (6)	0.021 (4)	0.030 (7)
C12B	0.058 (4)	0.206 (11)	0.106 (6)	0.010 (5)	0.026 (4)	−0.025 (7)
N4B	0.080 (3)	0.070 (3)	0.154 (7)	0.009 (3)	0.014 (4)	0.015 (4)
N5B	0.125 (5)	0.114 (5)	0.115 (5)	0.012 (4)	−0.004 (4)	−0.041 (4)
O8B	0.173 (7)	0.066 (3)	0.224 (9)	0.026 (4)	−0.019 (6)	−0.030 (4)
O9B	0.146 (5)	0.142 (6)	0.109 (5)	0.009 (4)	0.022 (4)	0.046 (4)

Geometric parameters (Å, º) top

O1—C1	1.319 (6)	C10A—C11A	1.368 (10)
O1—H1	0.8200	C10A—H10A	0.9300
C1—C6	1.399 (7)	C11A—C12A	1.352 (8)
C1—C2	1.410 (7)	C11A—H11A	0.9300
C2—C3	1.366 (7)	C12A—H12A	0.9300
C2—N1	1.456 (7)	N4A—O9A	1.222 (7)
C3—C4	1.396 (8)	N4A—O8A	1.224 (7)
C3—H3	0.9300	N5A—H5A	0.8600
C4—C5	1.375 (8)	N5A—H5B	0.8600
C4—N2	1.467 (6)	C7B—C12B	1.393 (6)
C5—C6	1.369 (7)	C7B—C8B	1.407 (5)
C5—H5	0.9300	C7B—N4B	1.436 (5)
C6—N3	1.469 (7)	C8B—N5B	1.328 (5)
N1—O3	1.194 (7)	C8B—C9B	1.408 (6)
N1—O2	1.224 (7)	C9B—C10B	1.371 (9)
N2—O4	1.219 (8)	C9B—H9B	0.9300
N2—O5	1.219 (8)	C10B—C11B	1.368 (10)
N3—O7	1.202 (7)	C10B—H10B	0.9300
N3—O6	1.219 (6)	C11B—C12B	1.352 (8)
C7A—C12A	1.393 (6)	C11B—H11B	0.9300
C7A—C8A	1.407 (5)	C12B—H12B	0.9300
C7A—N4A	1.436 (5)	N4B—O8B	1.210 (9)
C8A—N5A	1.329 (5)	N4B—O9B	1.234 (10)
C8A—C9A	1.408 (6)	N5B—H5C	0.8600
C9A—C10A	1.371 (9)	N5B—H5D	0.8600
C9A—H9A	0.9300

C1—O1—H1	109.5	C11A—C10A—H10A	119.3
O1—C1—C6	119.5 (4)	C9A—C10A—H10A	119.3
O1—C1—C2	125.6 (4)	C12A—C11A—C10A	119.8 (5)
C6—C1—C2	114.9 (4)	C12A—C11A—H11A	120.1
C3—C2—C1	123.5 (5)	C10A—C11A—H11A	120.1
C3—C2—N1	117.0 (5)	C11A—C12A—C7A	119.9 (5)
C1—C2—N1	119.5 (4)	C11A—C12A—H12A	120.1
C2—C3—C4	117.9 (4)	C7A—C12A—H12A	120.1
C2—C3—H3	121.0	O9A—N4A—O8A	119.9 (5)
C4—C3—H3	121.0	O9A—N4A—C7A	119.6 (4)
C5—C4—C3	121.5 (4)	O8A—N4A—C7A	120.5 (5)
C5—C4—N2	119.3 (5)	C8A—N5A—H5A	120.0
C3—C4—N2	119.2 (5)	C8A—N5A—H5B	120.0
C6—C5—C4	118.4 (5)	H5A—N5A—H5B	120.0
C6—C5—H5	120.8	C12B—C7B—C8B	118.7 (6)
C4—C5—H5	120.8	C12B—C7B—N4B	120.3 (7)
C5—C6—C1	123.7 (5)	C8B—C7B—N4B	121.0 (5)
C5—C6—N3	117.4 (5)	N5B—C8B—C7B	126.0 (6)
C1—C6—N3	118.9 (4)	N5B—C8B—C9B	116.2 (8)
O3—N1—O2	123.3 (5)	C7B—C8B—C9B	117.8 (6)
O3—N1—C2	118.8 (5)	C10B—C9B—C8B	117.8 (9)
O2—N1—C2	117.8 (5)	C10B—C9B—H9B	121.1
O4—N2—O5	124.1 (5)	C8B—C9B—H9B	121.1
O4—N2—C4	117.6 (5)	C11B—C10B—C9B	127.0 (11)
O5—N2—C4	118.2 (5)	C11B—C10B—H10B	116.5
O7—N3—O6	125.2 (5)	C9B—C10B—H10B	116.5
O7—N3—C6	118.3 (4)	C12B—C11B—C10B	113.3 (10)
O6—N3—C6	116.4 (5)	C12B—C11B—H11B	123.4
C12A—C7A—C8A	122.3 (4)	C10B—C11B—H11B	123.4
C12A—C7A—N4A	116.5 (4)	C11B—C12B—C7B	125.5 (9)
C8A—C7A—N4A	121.2 (4)	C11B—C12B—H12B	117.3
N5A—C8A—C7A	124.7 (4)	C7B—C12B—H12B	117.3
N5A—C8A—C9A	120.1 (5)	O8B—N4B—O9B	121.7 (7)
C7A—C8A—C9A	115.2 (4)	O8B—N4B—C7B	118.4 (8)
C10A—C9A—C8A	121.6 (5)	O9B—N4B—C7B	119.9 (7)
C10A—C9A—H9A	119.2	C8B—N5B—H5C	120.0
C8A—C9A—H9A	119.2	C8B—N5B—H5D	120.0
C11A—C10A—C9A	121.3 (5)	H5C—N5B—H5D	120.0

O1—C1—C2—C3	179.0 (4)	N4A—C7A—C8A—N5A	0.7 (7)
C6—C1—C2—C3	0.8 (7)	C12A—C7A—C8A—C9A	0.1 (6)
O1—C1—C2—N1	−1.2 (7)	N4A—C7A—C8A—C9A	179.5 (4)
C6—C1—C2—N1	−179.3 (4)	N5A—C8A—C9A—C10A	178.5 (5)
C1—C2—C3—C4	−0.4 (7)	C7A—C8A—C9A—C10A	−0.4 (7)
N1—C2—C3—C4	179.8 (4)	C8A—C9A—C10A—C11A	0.2 (8)
C2—C3—C4—C5	−0.8 (7)	C9A—C10A—C11A—C12A	0.3 (9)
C2—C3—C4—N2	179.1 (4)	C10A—C11A—C12A—C7A	−0.6 (8)
C3—C4—C5—C6	1.5 (8)	C8A—C7A—C12A—C11A	0.4 (7)
N2—C4—C5—C6	−178.5 (5)	N4A—C7A—C12A—C11A	−179.0 (5)
C4—C5—C6—C1	−1.0 (8)	C12A—C7A—N4A—O9A	174.6 (5)
C4—C5—C6—N3	177.3 (5)	C8A—C7A—N4A—O9A	−4.8 (7)
O1—C1—C6—C5	−178.4 (5)	C12A—C7A—N4A—O8A	−3.6 (7)
C2—C1—C6—C5	−0.2 (7)	C8A—C7A—N4A—O8A	177.0 (5)
O1—C1—C6—N3	3.4 (7)	C12B—C7B—C8B—N5B	179.6 (7)
C2—C1—C6—N3	−178.4 (4)	N4B—C7B—C8B—N5B	0.1 (9)
C3—C2—N1—O3	−1.5 (8)	C12B—C7B—C8B—C9B	0.6 (8)
C1—C2—N1—O3	178.7 (6)	N4B—C7B—C8B—C9B	−178.9 (6)
C3—C2—N1—O2	178.5 (5)	N5B—C8B—C9B—C10B	−179.6 (8)
C1—C2—N1—O2	−1.3 (8)	C7B—C8B—C9B—C10B	−0.5 (10)
C5—C4—N2—O4	171.1 (6)	C8B—C9B—C10B—C11B	0.5 (16)
C3—C4—N2—O4	−8.9 (8)	C9B—C10B—C11B—C12B	−0.6 (16)
C5—C4—N2—O5	−6.4 (8)	C10B—C11B—C12B—C7B	0.7 (12)
C3—C4—N2—O5	173.6 (6)	C8B—C7B—C12B—C11B	−0.7 (10)
C5—C6—N3—O7	−131.8 (6)	N4B—C7B—C12B—C11B	178.8 (7)
C1—C6—N3—O7	46.6 (8)	C12B—C7B—N4B—O8B	1.8 (10)
C5—C6—N3—O6	46.2 (8)	C8B—C7B—N4B—O8B	−178.7 (7)
C1—C6—N3—O6	−135.5 (6)	C12B—C7B—N4B—O9B	−177.7 (7)
C12A—C7A—C8A—N5A	−178.7 (5)	C8B—C7B—N4B—O9B	1.8 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.85	2.547 (6)	142
N5A—H5A···O9A	0.86	2.00	2.610 (7)	128
N5B—H5C···O9B	0.86	2.03	2.635 (12)	127
N5A—H5B···O4ⁱ	0.86	2.32	3.090 (7)	150
N5B—H5D···O9Aⁱⁱ	0.86	2.38	3.100 (8)	142
C5—H5···O8Bⁱⁱⁱ	0.93	2.48	3.228 (10)	138
C10A—H10A···O8A^iv	0.93	2.57	3.308 (9)	137
C11B—H11B···O9B^v	0.93	2.51	3.224 (13)	134
C3—H3···O9B^v	0.93	2.62	3.272 (9)	128

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

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A 2:1 complex of 2-nitro­aniline and picric acid

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A 2:1 complex of 2-nitroaniline and picric acid