In the title compound, C
8H
6N
2O
5, 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
CCDC reference: 610904
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C8H6N2O5 | F(000) = 432 |
Mr = 210.15 | Dx = 1.693 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1556 reflections |
a = 9.6080 (12) Å | θ = 2.6–25.9° |
b = 6.8998 (9) Å | µ = 0.14 mm−1 |
c = 15.3291 (14) Å | T = 293 K |
β = 125.755 (5)° | Plate, yellow |
V = 824.68 (17) Å3 | 0.25 × 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 tube | 1368 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.0°, θmin = 2.6° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −8→6 |
Tmin = 0.965, Tmax = 0.991 | l = −18→18 |
4196 measured reflections | |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H-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 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.62 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 | Uiso*/Ueq | |
O1 | 0.7912 (3) | −0.4418 (3) | −0.20664 (16) | 0.0468 (5) | |
O2 | 0.9127 (3) | −0.1740 (3) | −0.12679 (17) | 0.0496 (6) | |
O3 | 0.4840 (2) | −0.6242 (3) | −0.24030 (14) | 0.0377 (5) | |
O4 | 0.5396 (3) | −0.8626 (3) | −0.06282 (17) | 0.0545 (6) | |
O5 | 0.6242 (3) | −0.7928 (3) | 0.10274 (18) | 0.0645 (7) | |
H5A | 0.5766 | −0.8959 | 0.0963 | 0.097* | |
N1 | 0.8385 (3) | −0.3243 (3) | −0.13537 (17) | 0.0316 (5) | |
N2 | 0.7157 (2) | −0.8134 (2) | −0.15392 (15) | 0.0244 (4) | |
H2A | 0.6724 | −0.8962 | −0.2055 | 0.029* | |
H2B | 0.8173 | −0.8308 | −0.0963 | 0.029* | |
C1 | 0.8077 (3) | −0.3678 (3) | −0.05371 (19) | 0.0291 (5) | |
C2 | 0.8749 (3) | −0.2417 (4) | 0.0314 (2) | 0.0379 (6) | |
H2C | 0.9316 | −0.1299 | 0.0344 | 0.045* | |
C3 | 0.8568 (4) | −0.2838 (4) | 0.1126 (2) | 0.0450 (7) | |
H3A | 0.8993 | −0.1988 | 0.1700 | 0.054* | |
C4 | 0.7751 (3) | −0.4529 (4) | 0.1081 (2) | 0.0419 (7) | |
H4A | 0.7666 | −0.4832 | 0.1640 | 0.050* | |
C5 | 0.7058 (3) | −0.5779 (4) | 0.0209 (2) | 0.0331 (6) | |
C6 | 0.7186 (3) | −0.5351 (3) | −0.06341 (19) | 0.0282 (5) | |
C7 | 0.6269 (3) | −0.6612 (3) | −0.16310 (19) | 0.0292 (5) | |
C8 | 0.6153 (3) | −0.7591 (4) | 0.0158 (2) | 0.0383 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0664 (13) | 0.0386 (11) | 0.0481 (11) | −0.0116 (9) | 0.0407 (10) | −0.0080 (9) |
O2 | 0.0612 (13) | 0.0357 (11) | 0.0624 (13) | −0.0165 (9) | 0.0420 (11) | −0.0018 (9) |
O3 | 0.0354 (9) | 0.0279 (9) | 0.0356 (10) | −0.0005 (7) | 0.0128 (8) | 0.0014 (7) |
O4 | 0.0755 (15) | 0.0456 (12) | 0.0499 (12) | −0.0262 (11) | 0.0408 (12) | −0.0071 (10) |
O5 | 0.0981 (18) | 0.0553 (14) | 0.0497 (13) | −0.0297 (13) | 0.0485 (13) | −0.0031 (10) |
N1 | 0.0328 (10) | 0.0253 (10) | 0.0377 (11) | −0.0004 (8) | 0.0211 (9) | 0.0016 (9) |
N2 | 0.0245 (9) | 0.0141 (8) | 0.0282 (10) | 0.0011 (7) | 0.0117 (8) | −0.0047 (7) |
C1 | 0.0293 (11) | 0.0230 (11) | 0.0344 (13) | 0.0004 (9) | 0.0182 (10) | 0.0011 (9) |
C2 | 0.0386 (13) | 0.0303 (13) | 0.0441 (14) | −0.0079 (10) | 0.0237 (12) | −0.0059 (11) |
C3 | 0.0502 (15) | 0.0432 (16) | 0.0422 (15) | −0.0098 (12) | 0.0272 (13) | −0.0157 (12) |
C4 | 0.0463 (14) | 0.0455 (16) | 0.0383 (14) | −0.0044 (12) | 0.0272 (12) | −0.0020 (12) |
C5 | 0.0340 (12) | 0.0313 (13) | 0.0339 (13) | 0.0006 (10) | 0.0197 (11) | 0.0025 (10) |
C6 | 0.0267 (11) | 0.0233 (11) | 0.0315 (12) | 0.0020 (9) | 0.0152 (10) | 0.0015 (9) |
C7 | 0.0337 (12) | 0.0224 (11) | 0.0321 (12) | −0.0041 (9) | 0.0195 (11) | 0.0006 (9) |
C8 | 0.0457 (14) | 0.0336 (14) | 0.0401 (14) | −0.0005 (11) | 0.0277 (12) | 0.0073 (11) |
Geometric parameters (Å, º) top
O1—N1 | 1.215 (3) | C1—C6 | 1.393 (3) |
O2—N1 | 1.221 (3) | C2—C3 | 1.385 (4) |
O3—C7 | 1.205 (3) | C2—H2C | 0.9300 |
O4—C8 | 1.212 (3) | C3—C4 | 1.385 (4) |
O5—C8 | 1.305 (3) | C3—H3A | 0.9300 |
O5—H5A | 0.8200 | C4—C5 | 1.391 (4) |
N1—C1 | 1.476 (3) | C4—H4A | 0.9300 |
N2—C7 | 1.308 (3) | C5—C6 | 1.399 (4) |
N2—H2A | 0.8600 | C5—C8 | 1.499 (3) |
N2—H2B | 0.8600 | C6—C7 | 1.515 (3) |
C1—C2 | 1.375 (4) | | |
| | | |
C8—O5—H5A | 109.5 | C3—C4—C5 | 120.6 (3) |
O1—N1—O2 | 123.5 (2) | C3—C4—H4A | 119.7 |
O1—N1—C1 | 118.16 (19) | C5—C4—H4A | 119.7 |
O2—N1—C1 | 118.3 (2) | C4—C5—C6 | 120.4 (2) |
C7—N2—H2A | 120.0 | C4—C5—C8 | 120.3 (2) |
C7—N2—H2B | 120.0 | C6—C5—C8 | 119.3 (2) |
H2A—N2—H2B | 120.0 | C1—C6—C5 | 117.2 (2) |
C2—C1—C6 | 123.0 (2) | C1—C6—C7 | 122.9 (2) |
C2—C1—N1 | 117.4 (2) | C5—C6—C7 | 119.8 (2) |
C6—C1—N1 | 119.6 (2) | O3—C7—N2 | 125.0 (2) |
C1—C2—C3 | 119.0 (2) | O3—C7—C6 | 121.7 (2) |
C1—C2—H2C | 120.5 | N2—C7—C6 | 113.24 (19) |
C3—C2—H2C | 120.5 | O4—C8—O5 | 123.6 (2) |
C2—C3—C4 | 119.8 (3) | O4—C8—C5 | 122.4 (2) |
C2—C3—H3A | 120.1 | O5—C8—C5 | 114.0 (2) |
C4—C3—H3A | 120.1 | | |
| | | |
O1—N1—C1—C2 | 174.6 (2) | N1—C1—C6—C7 | −9.7 (3) |
O2—N1—C1—C2 | −4.3 (3) | C4—C5—C6—C1 | 2.1 (3) |
O1—N1—C1—C6 | −3.2 (3) | C8—C5—C6—C1 | −178.4 (2) |
O2—N1—C1—C6 | 178.0 (2) | C4—C5—C6—C7 | −173.7 (2) |
C6—C1—C2—C3 | 1.3 (4) | C8—C5—C6—C7 | 5.8 (3) |
N1—C1—C2—C3 | −176.4 (2) | C1—C6—C7—O3 | −83.6 (3) |
C1—C2—C3—C4 | 1.4 (4) | C5—C6—C7—O3 | 92.0 (3) |
C2—C3—C4—C5 | −2.2 (4) | C1—C6—C7—N2 | 98.9 (3) |
C3—C4—C5—C6 | 0.4 (4) | C5—C6—C7—N2 | −85.6 (3) |
C3—C4—C5—C8 | −179.1 (2) | C4—C5—C8—O4 | 173.1 (3) |
C2—C1—C6—C5 | −3.0 (3) | C6—C5—C8—O4 | −6.4 (4) |
N1—C1—C6—C5 | 174.6 (2) | C4—C5—C8—O5 | −6.2 (4) |
C2—C1—C6—C7 | 172.6 (2) | C6—C5—C8—O5 | 174.3 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O3i | 0.86 | 1.99 | 2.697 (3) | 138 |
O5—H5A···O4ii | 0.82 | 1.90 | 2.716 (3) | 172 |
C2—H2C···O2iii | 0.93 | 2.48 | 3.323 (4) | 150 |
C4—H4A···O5 | 0.93 | 2.41 | 2.733 (4) | 100 |
Symmetry codes: (i) −x+1, y−1/2, −z−1/2; (ii) −x+1, −y−2, −z; (iii) −x+2, −y, −z. |