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The occurrence of N—H...O and C—H...O hydrogen bonds in the title compound, C6H6N2O2, results in the formation of two-dimensional sheets parallel to the (101) plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040608/dn2073sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040608/dn2073Isup2.hkl
Contains datablock I

CCDC reference: 627491

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.033
  • wR factor = 0.095
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - N1 .. 6.95 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C1 .. 6.75 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.

4-nitroaniline top
Crystal data top
C6H6N2O2F(000) = 288
Mr = 138.13Dx = 1.430 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1869 reflections
a = 8.601 (1) Åθ = 2.7–28.1°
b = 6.043 (1) ŵ = 0.11 mm1
c = 12.352 (2) ÅT = 298 K
β = 91.43 (3)°Block, colorless
V = 641.81 (17) Å30.30 × 0.23 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
1334 independent reflections
Radiation source: fine-focus sealed tube1010 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω scansθmax = 26.5°, θmin = 2.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.968, Tmax = 0.980k = 77
4953 measured reflectionsl = 1514
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.041P)2 + 0.0481P]
where P = (Fo2 + 2Fc2)/3
1334 reflections(Δ/σ)max = 0.001
91 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.12 e Å3
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
xyzUiso*/Ueq
O10.13518 (12)0.12030 (18)1.07067 (8)0.0798 (3)
O20.27899 (12)0.40842 (16)1.05394 (8)0.0771 (4)
N10.24026 (11)0.21968 (18)1.02619 (8)0.0546 (3)
N20.54929 (14)0.1791 (2)0.68754 (9)0.0763 (4)
H2A0.52220.30850.66500.092*
H2B0.62390.11000.65710.092*
C10.32067 (12)0.11439 (18)0.93955 (9)0.0442 (3)
C20.27604 (14)0.09554 (18)0.90513 (10)0.0497 (3)
H20.19500.16900.93830.060*
C30.35252 (13)0.19298 (19)0.82193 (10)0.0524 (3)
H30.32310.33370.79890.063*
C40.47456 (13)0.0844 (2)0.77078 (10)0.0512 (3)
C50.51814 (14)0.1269 (2)0.80791 (10)0.0521 (3)
H50.59950.20110.77540.062*
C60.44237 (13)0.22455 (19)0.89115 (9)0.0477 (3)
H60.47220.36440.91540.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0764 (6)0.0864 (7)0.0780 (7)0.0224 (5)0.0336 (5)0.0069 (5)
O20.0841 (7)0.0619 (6)0.0864 (7)0.0141 (5)0.0241 (5)0.0223 (5)
N10.0529 (6)0.0585 (7)0.0527 (6)0.0050 (5)0.0062 (5)0.0015 (5)
N20.0780 (8)0.0774 (8)0.0744 (8)0.0006 (6)0.0196 (6)0.0184 (6)
C10.0439 (6)0.0453 (6)0.0434 (6)0.0013 (5)0.0004 (5)0.0035 (5)
C20.0491 (6)0.0469 (6)0.0530 (7)0.0087 (5)0.0001 (5)0.0083 (5)
C30.0586 (7)0.0411 (6)0.0573 (7)0.0031 (5)0.0049 (6)0.0003 (5)
C40.0490 (7)0.0543 (7)0.0501 (7)0.0059 (5)0.0020 (5)0.0003 (5)
C50.0455 (6)0.0576 (7)0.0533 (7)0.0073 (5)0.0052 (5)0.0044 (5)
C60.0489 (6)0.0438 (6)0.0502 (7)0.0075 (5)0.0016 (5)0.0025 (5)
Geometric parameters (Å, º) top
O1—N11.2265 (13)C2—C31.3672 (17)
O2—N11.2343 (13)C2—H20.9300
N1—C11.4371 (15)C3—C41.4017 (17)
N2—C41.3531 (16)C3—H30.9300
N2—H2A0.8600C4—C51.4047 (17)
N2—H2B0.8600C5—C61.3651 (17)
C1—C61.3884 (16)C5—H50.9300
C1—C21.3890 (16)C6—H60.9300
O1—N1—O2121.65 (11)C2—C3—C4121.13 (11)
O1—N1—C1119.37 (11)C2—C3—H3119.4
O2—N1—C1118.97 (10)C4—C3—H3119.4
C4—N2—H2A120.0N2—C4—C3121.32 (12)
C4—N2—H2B120.0N2—C4—C5120.31 (12)
H2A—N2—H2B120.0C3—C4—C5118.37 (11)
C6—C1—C2120.78 (11)C6—C5—C4120.69 (11)
C6—C1—N1119.36 (10)C6—C5—H5119.7
C2—C1—N1119.86 (10)C4—C5—H5119.7
C3—C2—C1119.27 (11)C5—C6—C1119.76 (11)
C3—C2—H2120.4C5—C6—H6120.1
C1—C2—H2120.4C1—C6—H6120.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.862.433.1290 (17)139
N2—H2B···O2ii0.862.233.0765 (17)168
C6—H6···O2iii0.932.563.3229 (17)139
C3—H3···Cg1iv0.932.813.5103 (15)133
Symmetry codes: (i) x+1/2, y1/2, z1/2; (ii) x+1/2, y+1/2, z1/2; (iii) x+1, y+1, z+2; (iv) x+1/2, y1/2, z+3/2.
 

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