The molecule of the title compound, C
14H
10N
4O
6, lies on a crystallographically imposed center of symmetry at the mid-point of the C—C bond of the oxamide unit. Molecules are linked into zigzag chains by N—H
O hydrogen bonds. The packing is further stabilized by van der Waals forces.
Supporting information
CCDC reference: 621486
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.048
- wR factor = 0.120
- Data-to-parameter ratio = 12.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C7 - C7_a ... 1.54 Ang.
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
3 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
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
N,
N'-Bis(4-nitrophenyl)oxalamide
top
Crystal data top
C14H10N4O6 | F(000) = 340 |
Mr = 330.26 | Dx = 1.579 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 3.7185 (8) Å | Cell parameters from 794 reflections |
b = 13.942 (3) Å | θ = 2.9–24.7° |
c = 13.571 (3) Å | µ = 0.13 mm−1 |
β = 99.059 (6)° | T = 293 K |
V = 694.8 (3) Å3 | Needle, colourless |
Z = 2 | 0.50 × 0.08 × 0.06 mm |
Data collection top
Siemens SMART 1000 CCD area-detector diffractometer | 1370 independent reflections |
Radiation source: fine-focus sealed tube | 1001 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.0°, θmin = 2.1° |
ω scans | h = −4→4 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −12→17 |
Tmin = 0.939, Tmax = 0.992 | l = −16→16 |
3825 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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0562P)2 + 0.0313P] where P = (Fo2 + 2Fc2)/3 |
1370 reflections | (Δ/σ)max < 0.001 |
114 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.19 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 | −0.3471 (4) | −0.12462 (12) | −0.55005 (11) | 0.0538 (5) | |
O2 | −0.0265 (4) | −0.25422 (12) | −0.53195 (11) | 0.0507 (5) | |
O3 | 0.2323 (5) | 0.07470 (12) | −0.08431 (11) | 0.0606 (5) | |
N1 | −0.1298 (5) | −0.17827 (13) | −0.49971 (12) | 0.0372 (5) | |
N2 | 0.4290 (5) | −0.07814 (12) | −0.10492 (12) | 0.0354 (5) | |
H2A | 0.5556 | −0.1229 | −0.0726 | 0.050 (7)* | |
C1 | 0.3343 (5) | −0.19258 (14) | −0.23766 (15) | 0.0334 (5) | |
H1A | 0.4597 | −0.2372 | −0.1942 | 0.039 (6)* | |
C2 | 0.2030 (5) | −0.21848 (15) | −0.33440 (14) | 0.0337 (5) | |
H2B | 0.2405 | −0.2800 | −0.3573 | 0.041 (6)* | |
C3 | 0.0135 (5) | −0.15098 (14) | −0.39701 (14) | 0.0300 (5) | |
C4 | −0.0466 (5) | −0.05960 (15) | −0.36570 (14) | 0.0336 (5) | |
H4A | −0.1770 | −0.0159 | −0.4093 | 0.036 (6)* | |
C5 | 0.0890 (5) | −0.03310 (15) | −0.26888 (14) | 0.0349 (5) | |
H5A | 0.0531 | 0.0288 | −0.2469 | 0.052 (7)* | |
C6 | 0.2800 (5) | −0.09995 (14) | −0.20447 (14) | 0.0303 (5) | |
C7 | 0.3987 (6) | 0.00299 (15) | −0.05385 (15) | 0.0363 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0636 (11) | 0.0567 (11) | 0.0341 (9) | 0.0016 (9) | −0.0137 (8) | 0.0030 (8) |
O2 | 0.0693 (12) | 0.0446 (10) | 0.0362 (9) | −0.0031 (8) | 0.0022 (8) | −0.0117 (7) |
O3 | 0.0902 (13) | 0.0473 (10) | 0.0365 (9) | 0.0273 (9) | −0.0141 (8) | −0.0099 (8) |
N1 | 0.0441 (11) | 0.0386 (11) | 0.0278 (10) | −0.0094 (9) | 0.0026 (8) | 0.0000 (8) |
N2 | 0.0466 (11) | 0.0320 (10) | 0.0250 (9) | 0.0049 (8) | −0.0027 (8) | −0.0012 (8) |
C1 | 0.0393 (12) | 0.0323 (12) | 0.0271 (11) | 0.0027 (9) | 0.0007 (8) | 0.0018 (9) |
C2 | 0.0410 (12) | 0.0288 (11) | 0.0310 (11) | −0.0026 (9) | 0.0044 (9) | −0.0042 (9) |
C3 | 0.0324 (11) | 0.0356 (12) | 0.0214 (10) | −0.0071 (9) | 0.0022 (8) | −0.0018 (9) |
C4 | 0.0374 (12) | 0.0353 (12) | 0.0267 (11) | 0.0013 (9) | 0.0007 (9) | 0.0054 (9) |
C5 | 0.0416 (12) | 0.0324 (12) | 0.0293 (12) | 0.0013 (9) | 0.0015 (9) | −0.0006 (9) |
C6 | 0.0321 (11) | 0.0335 (12) | 0.0249 (10) | −0.0029 (8) | 0.0031 (8) | −0.0014 (9) |
C7 | 0.0436 (13) | 0.0352 (13) | 0.0287 (12) | 0.0033 (9) | 0.0011 (9) | −0.0028 (9) |
Geometric parameters (Å, º) top
O1—N1 | 1.227 (2) | C1—H1A | 0.9300 |
O2—N1 | 1.230 (2) | C2—C3 | 1.384 (3) |
O3—C7 | 1.214 (2) | C2—H2B | 0.9300 |
N1—C3 | 1.462 (2) | C3—C4 | 1.372 (3) |
N2—C7 | 1.341 (3) | C4—C5 | 1.381 (3) |
N2—C6 | 1.410 (2) | C4—H4A | 0.9299 |
N2—H2A | 0.8600 | C5—C6 | 1.393 (3) |
C1—C2 | 1.375 (3) | C5—H5A | 0.9300 |
C1—C6 | 1.393 (3) | C7—C7i | 1.538 (4) |
| | | |
O1—N1—O2 | 122.81 (17) | C2—C3—N1 | 118.83 (18) |
O1—N1—C3 | 118.78 (18) | C3—C4—C5 | 119.33 (19) |
O2—N1—C3 | 118.41 (17) | C3—C4—H4A | 120.3 |
C7—N2—C6 | 128.68 (18) | C5—C4—H4A | 120.4 |
C7—N2—H2A | 115.6 | C4—C5—C6 | 119.4 (2) |
C6—N2—H2A | 115.7 | C4—C5—H5A | 120.3 |
C2—C1—C6 | 120.29 (19) | C6—C5—H5A | 120.3 |
C2—C1—H1A | 119.8 | C1—C6—C5 | 120.19 (18) |
C6—C1—H1A | 119.9 | C1—C6—N2 | 117.04 (17) |
C1—C2—C3 | 118.5 (2) | C5—C6—N2 | 122.77 (18) |
C1—C2—H2B | 120.8 | O3—C7—N2 | 126.79 (19) |
C3—C2—H2B | 120.7 | O3—C7—C7i | 121.0 (2) |
C4—C3—C2 | 122.22 (18) | N2—C7—C7i | 112.2 (2) |
C4—C3—N1 | 118.95 (17) | | |
| | | |
C6—C1—C2—C3 | −0.7 (3) | C3—C4—C5—C6 | −0.9 (3) |
C1—C2—C3—C4 | 0.0 (3) | C2—C1—C6—C5 | 0.6 (3) |
C1—C2—C3—N1 | −179.45 (17) | C2—C1—C6—N2 | −178.74 (17) |
O1—N1—C3—C4 | −11.5 (3) | C4—C5—C6—C1 | 0.2 (3) |
O2—N1—C3—C4 | 168.48 (18) | C4—C5—C6—N2 | 179.50 (17) |
O1—N1—C3—C2 | 168.04 (19) | C7—N2—C6—C1 | −176.0 (2) |
O2—N1—C3—C2 | −12.0 (3) | C7—N2—C6—C5 | 4.6 (3) |
C2—C3—C4—C5 | 0.8 (3) | C6—N2—C7—O3 | 0.2 (4) |
N1—C3—C4—C5 | −179.76 (17) | C6—N2—C7—C7i | 179.5 (2) |
Symmetry code: (i) −x+1, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O3i | 0.86 | 2.25 | 2.677 (2) | 110 |
N2—H2A···O2ii | 0.86 | 2.32 | 3.148 (2) | 161 |
C5—H5A···O3 | 0.93 | 2.29 | 2.898 (3) | 122 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, −y−1/2, z+1/2. |