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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033873/bt2172sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033873/bt2172Isup2.hkl
Contains datablock I

CCDC reference: 620701

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](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

Computing details top

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·C6H6N2O2F(000) = 776
Mr = 376.71Dx = 1.603 Mg m3
Orthorhombic, PbcmMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2c 2bCell parameters from 5700 reflections
a = 7.9181 (3) Åθ = 2.5–28.2°
b = 30.848 (2) ŵ = 0.30 mm1
c = 6.3894 (4) ÅT = 292 K
V = 1560.7 (1) Å3Block, colorless
Z = 40.20 × 0.10 × 0.10 mm
Data collection top
Bruker APEX area-detector
diffractometer
1402 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
φ and ω scansh = 99
14008 measured reflectionsk = 3636
1512 independent reflectionsl = 77
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196H 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 parametersΔρmax = 0.34 e Å3
3 restraintsΔρmin = 0.80 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.7147 (2)0.49220 (4)0.75000.0347 (4)
O10.7120 (5)0.5391 (1)0.75000.064 (1)
O20.8088 (4)0.4771 (1)0.5645 (5)0.062 (1)
O30.5439 (5)0.4751 (1)0.75000.055 (1)
O41.1274 (5)0.3408 (2)0.25000.068 (1)
O51.0313 (7)0.2767 (2)0.25000.098 (2)
O60.3735 (5)0.6486 (1)0.25000.056 (1)
O70.4824 (6)0.7121 (1)0.25000.069 (1)
N10.6238 (6)0.4383 (1)0.25000.034 (1)
N21.0133 (6)0.3155 (2)0.25000.053 (1)
N30.8579 (6)0.5451 (1)0.25000.043 (1)
N40.4933 (6)0.6727 (2)0.25000.042 (1)
C10.6528 (6)0.3917 (2)0.25000.030 (1)
C20.8164 (6)0.3767 (2)0.25000.034 (1)
C30.8394 (6)0.3323 (2)0.25000.036 (1)
C40.7056 (7)0.3035 (2)0.25000.046 (1)
C50.5436 (7)0.3198 (2)0.25000.045 (1)
C60.5178 (6)0.3641 (2)0.25000.036 (1)
C70.8378 (6)0.5920 (1)0.25000.027 (1)
C80.6769 (5)0.6093 (2)0.25000.029 (1)
C90.6644 (6)0.6537 (2)0.25000.032 (1)
C100.8013 (6)0.6810 (2)0.25000.041 (1)
C110.9606 (6)0.6625 (2)0.25000.042 (1)
C120.9798 (6)0.6181 (2)0.25000.0334 (11)
H1n10.675 (4)0.450 (1)0.148 (4)0.05 (1)*
H1n20.519 (2)0.444 (2)0.25000.05 (2)*
H3n10.820 (5)0.535 (1)0.364 (4)0.05 (1)*
H20.90770.39570.25000.040*
H40.72460.27370.25000.055*
H50.45180.30100.25000.054*
H60.40840.37510.25000.043*
H80.58150.59170.25000.035*
H100.78750.71090.25000.049*
H111.05560.68020.25000.050*
H121.08710.60590.25000.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0365 (7)0.0310 (7)0.0367 (7)0.0023 (5)0.0000.000
O10.043 (2)0.029 (2)0.119 (4)0.001 (2)0.0000.000
O20.049 (2)0.090 (2)0.047 (2)0.012 (2)0.004 (1)0.021 (2)
O30.039 (2)0.038 (2)0.087 (3)0.006 (2)0.0000.000
O40.028 (2)0.094 (4)0.082 (4)0.010 (2)0.0000.000
O50.071 (3)0.052 (3)0.170 (7)0.036 (3)0.0000.000
O60.027 (2)0.069 (3)0.073 (3)0.005 (2)0.0000.000
O70.058 (3)0.043 (2)0.105 (4)0.027 (2)0.0000.000
N10.038 (2)0.031 (2)0.034 (2)0.004 (2)0.0000.000
N20.037 (3)0.062 (3)0.061 (3)0.019 (2)0.0000.000
N30.046 (3)0.026 (2)0.059 (3)0.002 (2)0.0000.000
N40.030 (2)0.050 (3)0.045 (3)0.012 (2)0.0000.000
C10.036 (3)0.028 (2)0.026 (2)0.001 (2)0.0000.000
C20.030 (2)0.033 (2)0.037 (3)0.002 (2)0.0000.000
C30.029 (2)0.041 (3)0.038 (3)0.009 (2)0.0000.000
C40.050 (3)0.031 (3)0.056 (3)0.002 (2)0.0000.000
C50.037 (3)0.038 (3)0.058 (4)0.008 (2)0.0000.000
C60.031 (2)0.041 (3)0.035 (3)0.001 (2)0.0000.000
C70.028 (2)0.027 (2)0.026 (2)0.002 (2)0.0000.000
C80.022 (2)0.031 (2)0.036 (2)0.005 (2)0.0000.000
C90.025 (2)0.035 (3)0.035 (3)0.007 (2)0.0000.000
C100.037 (3)0.027 (2)0.059 (3)0.001 (2)0.0000.000
C110.028 (3)0.039 (3)0.059 (4)0.007 (2)0.0000.000
C120.021 (2)0.042 (3)0.036 (3)0.002 (2)0.0000.000
Geometric parameters (Å, º) top
Cl1—O11.447 (4)C7—C81.381 (6)
Cl1—O31.451 (4)C7—C121.384 (7)
Cl1—O2i1.475 (3)C8—C91.373 (6)
Cl1—O21.475 (3)C9—C101.372 (7)
O4—N21.195 (7)C10—C111.385 (7)
O5—N21.205 (6)C11—C121.376 (7)
O6—N41.205 (6)N1—H1n10.85 (1)
O7—N41.217 (6)N1—H1n20.85 (1)
N1—C11.457 (6)N3—H3n10.85 (1)
N2—C31.472 (7)C2—H20.93
N3—C71.457 (6)C4—H40.93
N4—C91.476 (6)C5—H50.93
C1—C61.368 (7)C6—H60.93
C1—C21.376 (7)C8—H80.93
C2—C31.381 (7)C10—H100.93
C3—C41.384 (8)C11—H110.93
C4—C51.378 (8)C12—H120.93
C5—C61.382 (7)
O1—Cl1—O3110.4 (2)C10—C9—C8123.7 (4)
O1—Cl1—O2i108.8 (2)C10—C9—N4118.8 (4)
O3—Cl1—O2i110.9 (2)C8—C9—N4117.5 (4)
O1—Cl1—O2108.8 (2)C9—C10—C11117.9 (5)
O3—Cl1—O2110.9 (2)C12—C11—C10120.7 (5)
O2i—Cl1—O2106.9 (3)C11—C12—C7119.3 (4)
O4—N2—O5124.1 (5)C1—N1—H1n1111 (3)
O4—N2—C3118.4 (5)C1—N1—H1n2111 (4)
O5—N2—C3117.5 (5)H1n1—N1—H1n2112 (3)
O6—N4—O7124.0 (4)C7—N3—H3n1109 (3)
O6—N4—C9118.5 (4)C1—C2—H2121.4
O7—N4—C9117.5 (4)C3—C2—H2121.4
C6—C1—C2121.8 (4)C5—C4—H4120.7
C6—C1—N1119.5 (4)C3—C4—H4120.7
C2—C1—N1118.7 (4)C4—C5—H5120.0
C1—C2—C3117.2 (4)C6—C5—H5120.0
C2—C3—C4122.5 (5)C1—C6—H6120.0
C2—C3—N2118.3 (5)C5—C6—H6120.0
C4—C3—N2119.3 (5)C9—C8—H8121.6
C5—C4—C3118.6 (5)C7—C8—H8121.6
C4—C5—C6119.9 (5)C9—C10—H10121.1
C1—C6—C5120.1 (5)C11—C10—H10121.1
C8—C7—C12121.6 (4)C12—C11—H11119.7
C8—C7—N3119.0 (4)C10—C11—H11119.7
C12—C7—N3119.3 (4)C11—C12—H12120.4
C9—C8—C7116.9 (4)C7—C12—H12120.4
C6—C1—C2—C30.0C12—C7—C8—C90.0
N1—C1—C2—C3180.0N3—C7—C8—C9180.0
C1—C2—C3—C40.0C7—C8—C9—C100.0
C1—C2—C3—N2180.0C7—C8—C9—N4180.0
O4—N2—C3—C20.0O6—N4—C9—C10180.0
O5—N2—C3—C2180.0O7—N4—C9—C100.0
O4—N2—C3—C4180.0O6—N4—C9—C80.0
O5—N2—C3—C40.0O7—N4—C9—C8180.0
C2—C3—C4—C50.0C8—C9—C10—C110.0
N2—C3—C4—C5180.0N4—C9—C10—C11180.0
C3—C4—C5—C60.0C9—C10—C11—C120.0
C2—C1—C6—C50.0C10—C11—C12—C70.0
N1—C1—C6—C5180.0C8—C7—C12—C110.0
C4—C5—C6—C10.0N3—C7—C12—C11180.0
Symmetry code: (i) x, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n2···O1ii0.85 (1)1.90 (1)2.748 (6)177 (6)
N1—H1n1···O2iii0.85 (1)1.91 (1)2.760 (4)174 (4)
N3—H3n1···O20.85 (1)2.20 (2)2.929 (5)144 (4)
Symmetry codes: (ii) x+1, y+1, z+1; (iii) x, y, z+1/2.
 

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