3-Nitroanilinium perchlorate crystallizes with a molecule of 3-nitroaniline to give the title compound, C6H7N2O2+·ClO4-·C6H6N2O2; all atoms except one O atom of the perchlorate ion and two H atoms bonded to nitrogen lie on a mirror plane. Hydrogen bonds link the cation, anion and neutral molecule into a chain that runs along the c axis of the orthorhombic unit cell.
Supporting information
CCDC reference: 620701
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.008 Å
- R factor = 0.065
- wR factor = 0.196
- Data-to-parameter ratio = 9.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.51
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cl1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety N1
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra
N1 -H1N1 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra
N3 -H3N1 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra
N1 -H1# 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra
N3 -H3# 1.555 1.555
PLAT736_ALERT_1_C H...A Calc 1.91(3), Rep 1.910(10) ...... 3.00 su-Ra
H1# -O2 1.555 6.556
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
12 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
7 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
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.
3-nitrophenylanilinium perchlorate–3-nitroaniline (1/1)
top
Crystal data top
C6H7N2O2+·ClO4−·C6H6N2O2 | F(000) = 776 |
Mr = 376.71 | Dx = 1.603 Mg m−3 |
Orthorhombic, Pbcm | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2c 2b | Cell parameters from 5700 reflections |
a = 7.9181 (3) Å | θ = 2.5–28.2° |
b = 30.848 (2) Å | µ = 0.30 mm−1 |
c = 6.3894 (4) Å | T = 292 K |
V = 1560.7 (1) Å3 | Block, colorless |
Z = 4 | 0.20 × 0.10 × 0.10 mm |
Data collection top
Bruker APEX area-detector diffractometer | 1402 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 25.0°, θmin = 2.6° |
φ and ω scans | h = −9→9 |
14008 measured reflections | k = −36→36 |
1512 independent reflections | l = −7→7 |
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.196 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.1029P)2 + 3.8634P] where P = (Fo2 + 2Fc2)/3 |
1512 reflections | (Δ/σ)max = 0.001 |
159 parameters | Δρmax = 0.34 e Å−3 |
3 restraints | Δρmin = −0.80 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.7147 (2) | 0.49220 (4) | 0.7500 | 0.0347 (4) | |
O1 | 0.7120 (5) | 0.5391 (1) | 0.7500 | 0.064 (1) | |
O2 | 0.8088 (4) | 0.4771 (1) | 0.5645 (5) | 0.062 (1) | |
O3 | 0.5439 (5) | 0.4751 (1) | 0.7500 | 0.055 (1) | |
O4 | 1.1274 (5) | 0.3408 (2) | 0.2500 | 0.068 (1) | |
O5 | 1.0313 (7) | 0.2767 (2) | 0.2500 | 0.098 (2) | |
O6 | 0.3735 (5) | 0.6486 (1) | 0.2500 | 0.056 (1) | |
O7 | 0.4824 (6) | 0.7121 (1) | 0.2500 | 0.069 (1) | |
N1 | 0.6238 (6) | 0.4383 (1) | 0.2500 | 0.034 (1) | |
N2 | 1.0133 (6) | 0.3155 (2) | 0.2500 | 0.053 (1) | |
N3 | 0.8579 (6) | 0.5451 (1) | 0.2500 | 0.043 (1) | |
N4 | 0.4933 (6) | 0.6727 (2) | 0.2500 | 0.042 (1) | |
C1 | 0.6528 (6) | 0.3917 (2) | 0.2500 | 0.030 (1) | |
C2 | 0.8164 (6) | 0.3767 (2) | 0.2500 | 0.034 (1) | |
C3 | 0.8394 (6) | 0.3323 (2) | 0.2500 | 0.036 (1) | |
C4 | 0.7056 (7) | 0.3035 (2) | 0.2500 | 0.046 (1) | |
C5 | 0.5436 (7) | 0.3198 (2) | 0.2500 | 0.045 (1) | |
C6 | 0.5178 (6) | 0.3641 (2) | 0.2500 | 0.036 (1) | |
C7 | 0.8378 (6) | 0.5920 (1) | 0.2500 | 0.027 (1) | |
C8 | 0.6769 (5) | 0.6093 (2) | 0.2500 | 0.029 (1) | |
C9 | 0.6644 (6) | 0.6537 (2) | 0.2500 | 0.032 (1) | |
C10 | 0.8013 (6) | 0.6810 (2) | 0.2500 | 0.041 (1) | |
C11 | 0.9606 (6) | 0.6625 (2) | 0.2500 | 0.042 (1) | |
C12 | 0.9798 (6) | 0.6181 (2) | 0.2500 | 0.0334 (11) | |
H1n1 | 0.675 (4) | 0.450 (1) | 0.148 (4) | 0.05 (1)* | |
H1n2 | 0.519 (2) | 0.444 (2) | 0.2500 | 0.05 (2)* | |
H3n1 | 0.820 (5) | 0.535 (1) | 0.364 (4) | 0.05 (1)* | |
H2 | 0.9077 | 0.3957 | 0.2500 | 0.040* | |
H4 | 0.7246 | 0.2737 | 0.2500 | 0.055* | |
H5 | 0.4518 | 0.3010 | 0.2500 | 0.054* | |
H6 | 0.4084 | 0.3751 | 0.2500 | 0.043* | |
H8 | 0.5815 | 0.5917 | 0.2500 | 0.035* | |
H10 | 0.7875 | 0.7109 | 0.2500 | 0.049* | |
H11 | 1.0556 | 0.6802 | 0.2500 | 0.050* | |
H12 | 1.0871 | 0.6059 | 0.2500 | 0.040* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0365 (7) | 0.0310 (7) | 0.0367 (7) | 0.0023 (5) | 0.000 | 0.000 |
O1 | 0.043 (2) | 0.029 (2) | 0.119 (4) | −0.001 (2) | 0.000 | 0.000 |
O2 | 0.049 (2) | 0.090 (2) | 0.047 (2) | 0.012 (2) | 0.004 (1) | −0.021 (2) |
O3 | 0.039 (2) | 0.038 (2) | 0.087 (3) | −0.006 (2) | 0.000 | 0.000 |
O4 | 0.028 (2) | 0.094 (4) | 0.082 (4) | 0.010 (2) | 0.000 | 0.000 |
O5 | 0.071 (3) | 0.052 (3) | 0.170 (7) | 0.036 (3) | 0.000 | 0.000 |
O6 | 0.027 (2) | 0.069 (3) | 0.073 (3) | 0.005 (2) | 0.000 | 0.000 |
O7 | 0.058 (3) | 0.043 (2) | 0.105 (4) | 0.027 (2) | 0.000 | 0.000 |
N1 | 0.038 (2) | 0.031 (2) | 0.034 (2) | 0.004 (2) | 0.000 | 0.000 |
N2 | 0.037 (3) | 0.062 (3) | 0.061 (3) | 0.019 (2) | 0.000 | 0.000 |
N3 | 0.046 (3) | 0.026 (2) | 0.059 (3) | 0.002 (2) | 0.000 | 0.000 |
N4 | 0.030 (2) | 0.050 (3) | 0.045 (3) | 0.012 (2) | 0.000 | 0.000 |
C1 | 0.036 (3) | 0.028 (2) | 0.026 (2) | 0.001 (2) | 0.000 | 0.000 |
C2 | 0.030 (2) | 0.033 (2) | 0.037 (3) | −0.002 (2) | 0.000 | 0.000 |
C3 | 0.029 (2) | 0.041 (3) | 0.038 (3) | 0.009 (2) | 0.000 | 0.000 |
C4 | 0.050 (3) | 0.031 (3) | 0.056 (3) | 0.002 (2) | 0.000 | 0.000 |
C5 | 0.037 (3) | 0.038 (3) | 0.058 (4) | −0.008 (2) | 0.000 | 0.000 |
C6 | 0.031 (2) | 0.041 (3) | 0.035 (3) | −0.001 (2) | 0.000 | 0.000 |
C7 | 0.028 (2) | 0.027 (2) | 0.026 (2) | 0.002 (2) | 0.000 | 0.000 |
C8 | 0.022 (2) | 0.031 (2) | 0.036 (2) | −0.005 (2) | 0.000 | 0.000 |
C9 | 0.025 (2) | 0.035 (3) | 0.035 (3) | 0.007 (2) | 0.000 | 0.000 |
C10 | 0.037 (3) | 0.027 (2) | 0.059 (3) | −0.001 (2) | 0.000 | 0.000 |
C11 | 0.028 (3) | 0.039 (3) | 0.059 (4) | −0.007 (2) | 0.000 | 0.000 |
C12 | 0.021 (2) | 0.042 (3) | 0.036 (3) | 0.002 (2) | 0.000 | 0.000 |
Geometric parameters (Å, º) top
Cl1—O1 | 1.447 (4) | C7—C8 | 1.381 (6) |
Cl1—O3 | 1.451 (4) | C7—C12 | 1.384 (7) |
Cl1—O2i | 1.475 (3) | C8—C9 | 1.373 (6) |
Cl1—O2 | 1.475 (3) | C9—C10 | 1.372 (7) |
O4—N2 | 1.195 (7) | C10—C11 | 1.385 (7) |
O5—N2 | 1.205 (6) | C11—C12 | 1.376 (7) |
O6—N4 | 1.205 (6) | N1—H1n1 | 0.85 (1) |
O7—N4 | 1.217 (6) | N1—H1n2 | 0.85 (1) |
N1—C1 | 1.457 (6) | N3—H3n1 | 0.85 (1) |
N2—C3 | 1.472 (7) | C2—H2 | 0.93 |
N3—C7 | 1.457 (6) | C4—H4 | 0.93 |
N4—C9 | 1.476 (6) | C5—H5 | 0.93 |
C1—C6 | 1.368 (7) | C6—H6 | 0.93 |
C1—C2 | 1.376 (7) | C8—H8 | 0.93 |
C2—C3 | 1.381 (7) | C10—H10 | 0.93 |
C3—C4 | 1.384 (8) | C11—H11 | 0.93 |
C4—C5 | 1.378 (8) | C12—H12 | 0.93 |
C5—C6 | 1.382 (7) | | |
| | | |
O1—Cl1—O3 | 110.4 (2) | C10—C9—C8 | 123.7 (4) |
O1—Cl1—O2i | 108.8 (2) | C10—C9—N4 | 118.8 (4) |
O3—Cl1—O2i | 110.9 (2) | C8—C9—N4 | 117.5 (4) |
O1—Cl1—O2 | 108.8 (2) | C9—C10—C11 | 117.9 (5) |
O3—Cl1—O2 | 110.9 (2) | C12—C11—C10 | 120.7 (5) |
O2i—Cl1—O2 | 106.9 (3) | C11—C12—C7 | 119.3 (4) |
O4—N2—O5 | 124.1 (5) | C1—N1—H1n1 | 111 (3) |
O4—N2—C3 | 118.4 (5) | C1—N1—H1n2 | 111 (4) |
O5—N2—C3 | 117.5 (5) | H1n1—N1—H1n2 | 112 (3) |
O6—N4—O7 | 124.0 (4) | C7—N3—H3n1 | 109 (3) |
O6—N4—C9 | 118.5 (4) | C1—C2—H2 | 121.4 |
O7—N4—C9 | 117.5 (4) | C3—C2—H2 | 121.4 |
C6—C1—C2 | 121.8 (4) | C5—C4—H4 | 120.7 |
C6—C1—N1 | 119.5 (4) | C3—C4—H4 | 120.7 |
C2—C1—N1 | 118.7 (4) | C4—C5—H5 | 120.0 |
C1—C2—C3 | 117.2 (4) | C6—C5—H5 | 120.0 |
C2—C3—C4 | 122.5 (5) | C1—C6—H6 | 120.0 |
C2—C3—N2 | 118.3 (5) | C5—C6—H6 | 120.0 |
C4—C3—N2 | 119.3 (5) | C9—C8—H8 | 121.6 |
C5—C4—C3 | 118.6 (5) | C7—C8—H8 | 121.6 |
C4—C5—C6 | 119.9 (5) | C9—C10—H10 | 121.1 |
C1—C6—C5 | 120.1 (5) | C11—C10—H10 | 121.1 |
C8—C7—C12 | 121.6 (4) | C12—C11—H11 | 119.7 |
C8—C7—N3 | 119.0 (4) | C10—C11—H11 | 119.7 |
C12—C7—N3 | 119.3 (4) | C11—C12—H12 | 120.4 |
C9—C8—C7 | 116.9 (4) | C7—C12—H12 | 120.4 |
| | | |
C6—C1—C2—C3 | 0.0 | C12—C7—C8—C9 | 0.0 |
N1—C1—C2—C3 | 180.0 | N3—C7—C8—C9 | 180.0 |
C1—C2—C3—C4 | 0.0 | C7—C8—C9—C10 | 0.0 |
C1—C2—C3—N2 | 180.0 | C7—C8—C9—N4 | 180.0 |
O4—N2—C3—C2 | 0.0 | O6—N4—C9—C10 | 180.0 |
O5—N2—C3—C2 | 180.0 | O7—N4—C9—C10 | 0.0 |
O4—N2—C3—C4 | 180.0 | O6—N4—C9—C8 | 0.0 |
O5—N2—C3—C4 | 0.0 | O7—N4—C9—C8 | 180.0 |
C2—C3—C4—C5 | 0.0 | C8—C9—C10—C11 | 0.0 |
N2—C3—C4—C5 | 180.0 | N4—C9—C10—C11 | 180.0 |
C3—C4—C5—C6 | 0.0 | C9—C10—C11—C12 | 0.0 |
C2—C1—C6—C5 | 0.0 | C10—C11—C12—C7 | 0.0 |
N1—C1—C6—C5 | 180.0 | C8—C7—C12—C11 | 0.0 |
C4—C5—C6—C1 | 0.0 | N3—C7—C12—C11 | 180.0 |
Symmetry code: (i) x, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n2···O1ii | 0.85 (1) | 1.90 (1) | 2.748 (6) | 177 (6) |
N1—H1n1···O2iii | 0.85 (1) | 1.91 (1) | 2.760 (4) | 174 (4) |
N3—H3n1···O2 | 0.85 (1) | 2.20 (2) | 2.929 (5) | 144 (4) |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) x, y, −z+1/2. |