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The molecule of the title compound, C14H12N2O2, lies on a crystallographically imposed center of symmetry at the mid-point of the C—C bond of the oxalamide unit. Mol­ecules are linked into ribbons along the a axis by N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015972/sj2052sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015972/sj2052Isup2.hkl
Contains datablock I

CCDC reference: 610891

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.037
  • wR factor = 0.103
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C7 - C7_a ... 1.54 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C14 H12 N2 O2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 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

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).

N,N'-Diphenyloxalamide top
Crystal data top
C14H12N2O2F(000) = 252
Mr = 240.26Dx = 1.388 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1766 reflections
a = 5.3207 (7) Åθ = 3.9–26.0°
b = 5.3723 (7) ŵ = 0.10 mm1
c = 20.5227 (19) ÅT = 293 K
β = 101.437 (3)°Block, colorless
V = 574.98 (12) Å30.43 × 0.21 × 0.20 mm
Z = 2
Data collection top
Siemens SMART 1000 CCD area detector
diffractometer
1133 independent reflections
Radiation source: fine-focus sealed tube1039 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 2.0°
ω scansh = 66
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 66
Tmin = 0.960, Tmax = 0.981l = 1825
3076 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0546P)2 + 0.089P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
1133 reflectionsΔρmax = 0.18 e Å3
83 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.203 (17)
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
O11.22647 (16)0.88346 (19)0.04334 (5)0.0579 (3)
N10.8048 (2)0.77849 (19)0.05075 (5)0.0440 (3)
H1B0.67350.81340.03390.053*
C10.5715 (2)0.4231 (2)0.10229 (7)0.0477 (4)
H1A0.46730.43340.07100.057*
C20.5288 (3)0.2394 (2)0.15016 (7)0.0525 (4)
H2A0.39680.12550.15070.063*
C30.6809 (3)0.2236 (2)0.19729 (7)0.0517 (4)
H3A0.65200.09970.22960.062*
C40.8756 (3)0.3932 (3)0.19598 (7)0.0519 (4)
H4A0.97790.38300.22770.062*
C50.9222 (2)0.5787 (2)0.14827 (6)0.0469 (3)
H5A1.05400.69260.14800.056*
C60.7696 (2)0.5925 (2)0.10077 (6)0.0392 (3)
C71.0193 (2)0.9056 (2)0.02690 (6)0.0419 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0402 (5)0.0772 (7)0.0590 (6)0.0050 (4)0.0161 (4)0.0228 (5)
N10.0392 (5)0.0509 (6)0.0436 (6)0.0008 (4)0.0125 (4)0.0069 (4)
C10.0426 (7)0.0510 (7)0.0515 (7)0.0016 (5)0.0145 (5)0.0016 (6)
C20.0463 (7)0.0448 (7)0.0651 (8)0.0065 (5)0.0080 (6)0.0025 (6)
C30.0486 (7)0.0468 (7)0.0572 (8)0.0041 (5)0.0044 (6)0.0109 (6)
C40.0480 (7)0.0618 (8)0.0477 (7)0.0003 (6)0.0138 (6)0.0100 (6)
C50.0437 (7)0.0518 (7)0.0465 (7)0.0069 (5)0.0125 (5)0.0045 (5)
C60.0368 (6)0.0411 (6)0.0389 (6)0.0029 (4)0.0054 (4)0.0002 (5)
C70.0396 (7)0.0477 (7)0.0388 (6)0.0014 (5)0.0089 (5)0.0019 (5)
Geometric parameters (Å, º) top
O1—C71.2209 (14)C2—H2A0.9300
N1—C71.3366 (16)C3—C41.3757 (19)
N1—C61.4182 (15)C3—H3A0.9300
N1—H1B0.8600C4—C51.3847 (18)
C1—C21.3789 (19)C4—H4A0.9300
C1—C61.3887 (17)C5—C61.3886 (17)
C1—H1A0.9300C5—H5A0.9300
C2—C31.381 (2)C7—C7i1.543 (2)
C7—N1—C6127.27 (10)C3—C4—C5121.26 (12)
C7—N1—H1B116.4C3—C4—H4A119.4
C6—N1—H1B116.4C5—C4—H4A119.4
C2—C1—C6120.13 (12)C4—C5—C6119.16 (12)
C2—C1—H1A119.9C4—C5—H5A120.4
C6—C1—H1A119.9C6—C5—H5A120.4
C1—C2—C3120.43 (12)C5—C6—C1119.74 (11)
C1—C2—H2A119.8C5—C6—N1122.29 (11)
C3—C2—H2A119.8C1—C6—N1117.95 (11)
C4—C3—C2119.27 (12)O1—C7—N1126.95 (11)
C4—C3—H3A120.4O1—C7—C7i121.16 (13)
C2—C3—H3A120.4N1—C7—C7i111.89 (12)
C6—C1—C2—C30.6 (2)C2—C1—C6—C50.99 (19)
C1—C2—C3—C40.0 (2)C2—C1—C6—N1179.71 (11)
C2—C3—C4—C50.2 (2)C7—N1—C6—C523.99 (19)
C3—C4—C5—C60.3 (2)C7—N1—C6—C1157.32 (12)
C4—C5—C6—C10.83 (19)C6—N1—C7—O10.8 (2)
C4—C5—C6—N1179.50 (12)C6—N1—C7—C7i179.45 (12)
Symmetry code: (i) x+2, y2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O1ii0.862.383.161 (1)152
N1—H1B···O1i0.862.262.680 (1)110
C5—H5A···O10.932.392.925 (2)116
Symmetry codes: (i) x+2, y2, z; (ii) x1, y, z.
 

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