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In the title compound, C8H6N2O5, mol­ecules are linked into ribbons along the b axis by N—H...O hydrogen bonds. The ribbons are inter­linked into a three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018836/sj2072sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018836/sj2072Isup2.hkl
Contains datablock I

CCDC reference: 610904

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.057
  • wR factor = 0.170
  • Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N2 - C7 .. 10.51 su PLAT415_ALERT_2_B Short Inter D-H..H-X H2B .. H2C .. 2.03 Ang. PLAT430_ALERT_2_B Short Inter D...A Contact O3 .. N1 .. 2.87 Ang.
Alert level C DIFMN02_ALERT_2_C The minimum difference density is < -0.1*ZMAX*0.75 _refine_diff_density_min given = -0.620 Test value = -0.600 DIFMN03_ALERT_1_C The minimum difference density is < -0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT098_ALERT_2_C Minimum (Negative) Residual Density ............ -0.62 e/A   3 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.35 Ratio PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2B ... ? PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C8 H6 N2 O5
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

2-Carbamoyl-3-nitrobenzoic acid top
Crystal data top
C8H6N2O5F(000) = 432
Mr = 210.15Dx = 1.693 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1556 reflections
a = 9.6080 (12) Åθ = 2.6–25.9°
b = 6.8998 (9) ŵ = 0.14 mm1
c = 15.3291 (14) ÅT = 293 K
β = 125.755 (5)°Plate, yellow
V = 824.68 (17) Å30.25 × 0.20 × 0.06 mm
Z = 4
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
1606 independent reflections
Radiation source: fine-focus sealed tube1368 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 2.6°
ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 86
Tmin = 0.965, Tmax = 0.991l = 1818
4196 measured reflections
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0923P)2 + 0.663P]
where P = (Fo2 + 2Fc2)/3
1606 reflections(Δ/σ)max < 0.001
136 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = 0.62 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
O10.7912 (3)0.4418 (3)0.20664 (16)0.0468 (5)
O20.9127 (3)0.1740 (3)0.12679 (17)0.0496 (6)
O30.4840 (2)0.6242 (3)0.24030 (14)0.0377 (5)
O40.5396 (3)0.8626 (3)0.06282 (17)0.0545 (6)
O50.6242 (3)0.7928 (3)0.10274 (18)0.0645 (7)
H5A0.57660.89590.09630.097*
N10.8385 (3)0.3243 (3)0.13537 (17)0.0316 (5)
N20.7157 (2)0.8134 (2)0.15392 (15)0.0244 (4)
H2A0.67240.89620.20550.029*
H2B0.81730.83080.09630.029*
C10.8077 (3)0.3678 (3)0.05371 (19)0.0291 (5)
C20.8749 (3)0.2417 (4)0.0314 (2)0.0379 (6)
H2C0.93160.12990.03440.045*
C30.8568 (4)0.2838 (4)0.1126 (2)0.0450 (7)
H3A0.89930.19880.17000.054*
C40.7751 (3)0.4529 (4)0.1081 (2)0.0419 (7)
H4A0.76660.48320.16400.050*
C50.7058 (3)0.5779 (4)0.0209 (2)0.0331 (6)
C60.7186 (3)0.5351 (3)0.06341 (19)0.0282 (5)
C70.6269 (3)0.6612 (3)0.16310 (19)0.0292 (5)
C80.6153 (3)0.7591 (4)0.0158 (2)0.0383 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0664 (13)0.0386 (11)0.0481 (11)0.0116 (9)0.0407 (10)0.0080 (9)
O20.0612 (13)0.0357 (11)0.0624 (13)0.0165 (9)0.0420 (11)0.0018 (9)
O30.0354 (9)0.0279 (9)0.0356 (10)0.0005 (7)0.0128 (8)0.0014 (7)
O40.0755 (15)0.0456 (12)0.0499 (12)0.0262 (11)0.0408 (12)0.0071 (10)
O50.0981 (18)0.0553 (14)0.0497 (13)0.0297 (13)0.0485 (13)0.0031 (10)
N10.0328 (10)0.0253 (10)0.0377 (11)0.0004 (8)0.0211 (9)0.0016 (9)
N20.0245 (9)0.0141 (8)0.0282 (10)0.0011 (7)0.0117 (8)0.0047 (7)
C10.0293 (11)0.0230 (11)0.0344 (13)0.0004 (9)0.0182 (10)0.0011 (9)
C20.0386 (13)0.0303 (13)0.0441 (14)0.0079 (10)0.0237 (12)0.0059 (11)
C30.0502 (15)0.0432 (16)0.0422 (15)0.0098 (12)0.0272 (13)0.0157 (12)
C40.0463 (14)0.0455 (16)0.0383 (14)0.0044 (12)0.0272 (12)0.0020 (12)
C50.0340 (12)0.0313 (13)0.0339 (13)0.0006 (10)0.0197 (11)0.0025 (10)
C60.0267 (11)0.0233 (11)0.0315 (12)0.0020 (9)0.0152 (10)0.0015 (9)
C70.0337 (12)0.0224 (11)0.0321 (12)0.0041 (9)0.0195 (11)0.0006 (9)
C80.0457 (14)0.0336 (14)0.0401 (14)0.0005 (11)0.0277 (12)0.0073 (11)
Geometric parameters (Å, º) top
O1—N11.215 (3)C1—C61.393 (3)
O2—N11.221 (3)C2—C31.385 (4)
O3—C71.205 (3)C2—H2C0.9300
O4—C81.212 (3)C3—C41.385 (4)
O5—C81.305 (3)C3—H3A0.9300
O5—H5A0.8200C4—C51.391 (4)
N1—C11.476 (3)C4—H4A0.9300
N2—C71.308 (3)C5—C61.399 (4)
N2—H2A0.8600C5—C81.499 (3)
N2—H2B0.8600C6—C71.515 (3)
C1—C21.375 (4)
C8—O5—H5A109.5C3—C4—C5120.6 (3)
O1—N1—O2123.5 (2)C3—C4—H4A119.7
O1—N1—C1118.16 (19)C5—C4—H4A119.7
O2—N1—C1118.3 (2)C4—C5—C6120.4 (2)
C7—N2—H2A120.0C4—C5—C8120.3 (2)
C7—N2—H2B120.0C6—C5—C8119.3 (2)
H2A—N2—H2B120.0C1—C6—C5117.2 (2)
C2—C1—C6123.0 (2)C1—C6—C7122.9 (2)
C2—C1—N1117.4 (2)C5—C6—C7119.8 (2)
C6—C1—N1119.6 (2)O3—C7—N2125.0 (2)
C1—C2—C3119.0 (2)O3—C7—C6121.7 (2)
C1—C2—H2C120.5N2—C7—C6113.24 (19)
C3—C2—H2C120.5O4—C8—O5123.6 (2)
C2—C3—C4119.8 (3)O4—C8—C5122.4 (2)
C2—C3—H3A120.1O5—C8—C5114.0 (2)
C4—C3—H3A120.1
O1—N1—C1—C2174.6 (2)N1—C1—C6—C79.7 (3)
O2—N1—C1—C24.3 (3)C4—C5—C6—C12.1 (3)
O1—N1—C1—C63.2 (3)C8—C5—C6—C1178.4 (2)
O2—N1—C1—C6178.0 (2)C4—C5—C6—C7173.7 (2)
C6—C1—C2—C31.3 (4)C8—C5—C6—C75.8 (3)
N1—C1—C2—C3176.4 (2)C1—C6—C7—O383.6 (3)
C1—C2—C3—C41.4 (4)C5—C6—C7—O392.0 (3)
C2—C3—C4—C52.2 (4)C1—C6—C7—N298.9 (3)
C3—C4—C5—C60.4 (4)C5—C6—C7—N285.6 (3)
C3—C4—C5—C8179.1 (2)C4—C5—C8—O4173.1 (3)
C2—C1—C6—C53.0 (3)C6—C5—C8—O46.4 (4)
N1—C1—C6—C5174.6 (2)C4—C5—C8—O56.2 (4)
C2—C1—C6—C7172.6 (2)C6—C5—C8—O5174.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O3i0.861.992.697 (3)138
O5—H5A···O4ii0.821.902.716 (3)172
C2—H2C···O2iii0.932.483.323 (4)150
C4—H4A···O50.932.412.733 (4)100
Symmetry codes: (i) x+1, y1/2, z1/2; (ii) x+1, y2, z; (iii) x+2, y, z.
 

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