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The title compound, C19H13N3O6, is a precursor for the synthesis of polymers. The mol­ecule is not planar and the terminal benzene rings are almost perpendicular to each other, at an angle of 85.19 (7)°. In the crystal structure, the mol­ecules are linked by C—H...O and N—H...O inter­molecular hydrogen bonds to form a one-dimensional network parallel to the bc face.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680605344X/ym2044sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680605344X/ym2044Isup2.hkl
Contains datablock I

CCDC reference: 636847

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.029
  • wR factor = 0.079
  • Data-to-parameter ratio = 8.8

checkCIF/PLATON results

No syntax errors found



Alert level C STRVA01_ALERT_2_C Chirality of atom sites is inverted? From the CIF: _refine_ls_abs_structure_Flack 1.400 From the CIF: _refine_ls_abs_structure_Flack_su 0.900 PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 0.90 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 1.40
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 2264 Count of symmetry unique reflns 2270 Completeness (_total/calc) 99.74% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

4-Nitro-N-[4-(4-nitrophenoxy)phenyl]benzamide top
Crystal data top
C19H13N3O6Dx = 1.501 Mg m3
Mr = 379.32Melting point: 218 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 19637 reflections
a = 5.0815 (2) Åθ = 2.3–27.9°
b = 13.5782 (8) ŵ = 0.11 mm1
c = 24.3279 (12) ÅT = 173 K
V = 1678.57 (14) Å3Rod, light brown
Z = 40.38 × 0.18 × 0.14 mm
F(000) = 784
Data collection top
Stoe IPDSII two-circle
diffractometer
2180 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.055
Graphite monochromatorθmax = 27.5°, θmin = 2.2°
ω scansh = 66
19554 measured reflectionsk = 1717
2264 independent reflectionsl = 3131
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.029 w = 1/[σ2(Fo2) + (0.0528P)2 + 0.1513P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.079(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.20 e Å3
2264 reflectionsΔρmin = 0.14 e Å3
258 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.047 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), Friedel pair number ?
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 1.4 (9)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.5383 (3)0.50065 (11)0.32605 (5)0.0382 (3)
O110.3305 (3)0.54604 (14)0.32297 (6)0.0634 (5)
O120.6715 (4)0.47690 (10)0.28625 (4)0.0510 (4)
C10.8533 (3)0.36481 (10)0.53873 (6)0.0249 (3)
O11.0812 (2)0.33727 (9)0.54683 (4)0.0336 (3)
N20.6592 (3)0.36170 (10)0.57693 (5)0.0268 (3)
H20.507 (5)0.3762 (17)0.5662 (9)0.046 (6)*
O20.7498 (3)0.28587 (10)0.80199 (4)0.0391 (3)
N30.0228 (3)0.10357 (9)0.92925 (5)0.0321 (3)
O310.1695 (3)0.04335 (9)0.90759 (5)0.0447 (3)
O320.0415 (3)0.12776 (10)0.97780 (5)0.0455 (3)
C110.6300 (3)0.47200 (11)0.38129 (6)0.0292 (3)
C120.8459 (3)0.41023 (11)0.38582 (5)0.0303 (3)
H120.94290.39090.35420.036*
C130.9163 (3)0.37747 (10)0.43768 (6)0.0281 (3)
H131.06450.33550.44200.034*
C140.7707 (3)0.40576 (10)0.48373 (5)0.0242 (3)
C150.5611 (3)0.47130 (11)0.47812 (6)0.0283 (3)
H150.46770.49310.50970.034*
C160.4890 (3)0.50474 (11)0.42628 (6)0.0311 (3)
H160.34600.54910.42190.037*
C210.6845 (3)0.33624 (10)0.63336 (5)0.0247 (3)
C220.8846 (3)0.27623 (12)0.65337 (6)0.0327 (3)
H221.01080.24890.62890.039*
C230.8987 (3)0.25635 (12)0.70980 (6)0.0350 (3)
H231.03470.21550.72390.042*
C240.7140 (3)0.29648 (12)0.74487 (6)0.0306 (3)
C250.5098 (3)0.35383 (12)0.72519 (6)0.0341 (3)
H250.38100.37940.74960.041*
C260.4950 (3)0.37369 (11)0.66923 (6)0.0315 (3)
H260.35530.41290.65530.038*
C310.5567 (3)0.23850 (11)0.83140 (5)0.0296 (3)
C320.5257 (4)0.26777 (12)0.88616 (6)0.0346 (3)
H320.63310.31850.90100.042*
C330.3384 (4)0.22261 (11)0.91845 (6)0.0331 (3)
H330.31510.24170.95570.040*
C340.1841 (3)0.14874 (10)0.89559 (5)0.0282 (3)
C350.2166 (3)0.11743 (11)0.84176 (6)0.0302 (3)
H350.11040.06610.82720.036*
C360.4075 (3)0.16259 (11)0.80950 (5)0.0305 (3)
H360.43540.14160.77270.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0453 (8)0.0412 (7)0.0282 (6)0.0084 (7)0.0041 (6)0.0075 (5)
O110.0520 (9)0.0952 (12)0.0430 (7)0.0135 (9)0.0078 (7)0.0254 (8)
O120.0792 (11)0.0501 (7)0.0238 (5)0.0022 (8)0.0027 (6)0.0005 (5)
C10.0224 (6)0.0273 (6)0.0252 (6)0.0012 (5)0.0006 (5)0.0009 (5)
O10.0224 (5)0.0467 (6)0.0316 (5)0.0049 (5)0.0012 (4)0.0048 (5)
N20.0207 (6)0.0364 (6)0.0233 (5)0.0020 (5)0.0008 (5)0.0029 (5)
O20.0360 (6)0.0559 (7)0.0255 (5)0.0127 (6)0.0052 (4)0.0092 (5)
N30.0368 (7)0.0306 (6)0.0288 (5)0.0019 (6)0.0028 (5)0.0048 (5)
O310.0509 (8)0.0404 (6)0.0426 (6)0.0148 (6)0.0060 (6)0.0009 (5)
O320.0544 (8)0.0536 (7)0.0285 (5)0.0042 (7)0.0110 (6)0.0013 (5)
C110.0336 (8)0.0301 (6)0.0240 (6)0.0066 (6)0.0026 (6)0.0035 (5)
C120.0332 (7)0.0330 (7)0.0247 (6)0.0036 (7)0.0052 (6)0.0029 (5)
C130.0269 (7)0.0294 (6)0.0282 (6)0.0001 (6)0.0031 (6)0.0019 (5)
C140.0230 (6)0.0260 (6)0.0236 (6)0.0023 (6)0.0003 (5)0.0007 (5)
C150.0275 (7)0.0308 (6)0.0265 (6)0.0033 (6)0.0041 (6)0.0008 (5)
C160.0290 (7)0.0327 (7)0.0317 (7)0.0022 (6)0.0001 (6)0.0048 (6)
C210.0231 (6)0.0282 (6)0.0228 (6)0.0015 (6)0.0002 (5)0.0017 (5)
C220.0286 (7)0.0379 (7)0.0314 (7)0.0075 (6)0.0018 (6)0.0029 (6)
C230.0298 (8)0.0423 (8)0.0329 (7)0.0048 (7)0.0033 (6)0.0109 (6)
C240.0301 (7)0.0373 (7)0.0246 (6)0.0064 (6)0.0026 (6)0.0052 (6)
C250.0332 (8)0.0428 (8)0.0262 (6)0.0038 (7)0.0050 (6)0.0007 (6)
C260.0289 (7)0.0377 (7)0.0279 (6)0.0063 (6)0.0011 (6)0.0038 (5)
C310.0301 (7)0.0341 (7)0.0246 (6)0.0005 (6)0.0025 (6)0.0070 (5)
C320.0414 (9)0.0337 (7)0.0288 (6)0.0068 (7)0.0061 (7)0.0008 (6)
C330.0424 (9)0.0332 (7)0.0237 (6)0.0009 (7)0.0009 (6)0.0011 (5)
C340.0318 (7)0.0282 (6)0.0246 (6)0.0013 (6)0.0006 (6)0.0033 (5)
C350.0350 (8)0.0301 (6)0.0256 (6)0.0013 (6)0.0030 (6)0.0003 (5)
C360.0347 (8)0.0357 (7)0.0211 (5)0.0006 (7)0.0019 (6)0.0012 (5)
Geometric parameters (Å, º) top
N1—O111.225 (2)C16—H160.9500
N1—O121.225 (2)C21—C221.391 (2)
N1—C111.4747 (18)C21—C261.395 (2)
C1—O11.2332 (18)C22—C231.4010 (19)
C1—N21.3557 (19)C22—H220.9500
C1—C141.5085 (18)C23—C241.381 (2)
N2—C211.4216 (16)C23—H230.9500
N2—H20.84 (3)C24—C251.383 (2)
O2—C311.3741 (19)C25—C261.3898 (19)
O2—C241.4089 (16)C25—H250.9500
N3—O311.2257 (19)C26—H260.9500
N3—O321.2297 (16)C31—C361.386 (2)
N3—C341.467 (2)C31—C321.3992 (19)
C11—C161.382 (2)C32—C331.378 (2)
C11—C121.386 (2)C32—H320.9500
C12—C131.385 (2)C33—C341.389 (2)
C12—H120.9500C33—H330.9500
C13—C141.3966 (19)C34—C351.3867 (19)
C13—H130.9500C35—C361.390 (2)
C14—C151.395 (2)C35—H350.9500
C15—C161.3895 (19)C36—H360.9500
C15—H150.9500
O11—N1—O12124.11 (15)C21—C22—C23119.55 (14)
O11—N1—C11117.44 (15)C21—C22—H22120.2
O12—N1—C11118.45 (16)C23—C22—H22120.2
O1—C1—N2124.36 (13)C24—C23—C22119.65 (15)
O1—C1—C14120.98 (13)C24—C23—H23120.2
N2—C1—C14114.66 (13)C22—C23—H23120.2
C1—N2—C21127.14 (13)C23—C24—C25121.23 (13)
C1—N2—H2116.7 (15)C23—C24—O2118.77 (14)
C21—N2—H2116.2 (15)C25—C24—O2119.75 (14)
C31—O2—C24117.97 (12)C24—C25—C26119.27 (14)
O31—N3—O32122.96 (15)C24—C25—H25120.4
O31—N3—C34118.36 (12)C26—C25—H25120.4
O32—N3—C34118.68 (14)C25—C26—C21120.30 (14)
C16—C11—C12122.85 (13)C25—C26—H26119.9
C16—C11—N1118.25 (15)C21—C26—H26119.9
C12—C11—N1118.84 (13)O2—C31—C36122.59 (13)
C13—C12—C11118.13 (13)O2—C31—C32116.31 (14)
C13—C12—H12120.9C36—C31—C32121.03 (14)
C11—C12—H12120.9C33—C32—C31119.62 (14)
C12—C13—C14120.38 (14)C33—C32—H32120.2
C12—C13—H13119.8C31—C32—H32120.2
C14—C13—H13119.8C32—C33—C34118.87 (13)
C15—C14—C13120.11 (13)C32—C33—H33120.6
C15—C14—C1122.30 (12)C34—C33—H33120.6
C13—C14—C1117.57 (13)C35—C34—C33122.17 (14)
C16—C15—C14119.92 (13)C35—C34—N3118.96 (14)
C16—C15—H15120.0C33—C34—N3118.87 (13)
C14—C15—H15120.0C34—C35—C36118.74 (14)
C11—C16—C15118.50 (14)C34—C35—H35120.6
C11—C16—H16120.7C36—C35—H35120.6
C15—C16—H16120.7C31—C36—C35119.52 (13)
C22—C21—C26119.95 (13)C31—C36—H36120.2
C22—C21—N2123.13 (13)C35—C36—H36120.2
C26—C21—N2116.92 (12)
O1—C1—N2—C216.5 (2)C22—C23—C24—C251.9 (3)
C14—C1—N2—C21173.31 (13)C22—C23—C24—O2172.20 (15)
O11—N1—C11—C165.2 (2)C31—O2—C24—C23120.83 (17)
O12—N1—C11—C16175.59 (16)C31—O2—C24—C2565.0 (2)
O11—N1—C11—C12172.02 (16)C23—C24—C25—C261.9 (3)
O12—N1—C11—C127.2 (2)O2—C24—C25—C26172.18 (15)
C16—C11—C12—C132.4 (2)C24—C25—C26—C210.1 (2)
N1—C11—C12—C13174.76 (14)C22—C21—C26—C252.0 (2)
C11—C12—C13—C140.5 (2)N2—C21—C26—C25178.58 (14)
C12—C13—C14—C153.3 (2)C24—O2—C31—C3632.7 (2)
C12—C13—C14—C1178.12 (14)C24—O2—C31—C32150.29 (15)
O1—C1—C14—C15154.03 (15)O2—C31—C32—C33179.11 (15)
N2—C1—C14—C1525.8 (2)C36—C31—C32—C332.0 (2)
O1—C1—C14—C1324.6 (2)C31—C32—C33—C340.0 (2)
N2—C1—C14—C13155.60 (13)C32—C33—C34—C351.5 (2)
C13—C14—C15—C163.1 (2)C32—C33—C34—N3177.44 (14)
C1—C14—C15—C16178.30 (14)O31—N3—C34—C353.9 (2)
C12—C11—C16—C152.5 (2)O32—N3—C34—C35176.11 (14)
N1—C11—C16—C15174.67 (14)O31—N3—C34—C33175.06 (15)
C14—C15—C16—C110.3 (2)O32—N3—C34—C334.9 (2)
C1—N2—C21—C2225.3 (2)C33—C34—C35—C360.9 (2)
C1—N2—C21—C26155.33 (15)N3—C34—C35—C36178.03 (13)
C26—C21—C22—C232.0 (2)O2—C31—C36—C35179.52 (14)
N2—C21—C22—C23178.67 (15)C32—C31—C36—C352.6 (2)
C21—C22—C23—C240.0 (3)C34—C35—C36—C311.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···O10.952.362.8988 (18)116
N2—H2···O1i0.84 (3)2.28 (3)3.0449 (17)152 (2)
C25—H25···O11ii0.952.323.240 (2)164
C26—H26···O31iii0.952.523.396 (2)153
C33—H33···O32iv0.952.513.297 (2)141
C36—H36···O12v0.952.543.2329 (19)130
Symmetry codes: (i) x1, y, z; (ii) x+1/2, y+1, z+1/2; (iii) x, y+1/2, z+3/2; (iv) x+1/2, y+1/2, z+2; (v) x1/2, y+1/2, z+1.
 

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