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The title compound, C
19H
13N
3O
6, 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
CCDC reference: 636847
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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
C19H13N3O6 | Dx = 1.501 Mg m−3 |
Mr = 379.32 | Melting point: 218 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 19637 reflections |
a = 5.0815 (2) Å | θ = 2.3–27.9° |
b = 13.5782 (8) Å | µ = 0.11 mm−1 |
c = 24.3279 (12) Å | T = 173 K |
V = 1678.57 (14) Å3 | Rod, light brown |
Z = 4 | 0.38 × 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 tube | Rint = 0.055 |
Graphite monochromator | θmax = 27.5°, θmin = 2.2° |
ω scans | h = −6→6 |
19554 measured reflections | k = −17→17 |
2264 independent reflections | l = −31→31 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H 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 = 1.06 | Δρmax = 0.20 e Å−3 |
2264 reflections | Δρmin = −0.14 e Å−3 |
258 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.047 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), Friedel pair number ? |
Secondary atom site location: difference Fourier map | Absolute 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 | x | y | z | Uiso*/Ueq | |
N1 | 0.5383 (3) | 0.50065 (11) | 0.32605 (5) | 0.0382 (3) | |
O11 | 0.3305 (3) | 0.54604 (14) | 0.32297 (6) | 0.0634 (5) | |
O12 | 0.6715 (4) | 0.47690 (10) | 0.28625 (4) | 0.0510 (4) | |
C1 | 0.8533 (3) | 0.36481 (10) | 0.53873 (6) | 0.0249 (3) | |
O1 | 1.0812 (2) | 0.33727 (9) | 0.54683 (4) | 0.0336 (3) | |
N2 | 0.6592 (3) | 0.36170 (10) | 0.57693 (5) | 0.0268 (3) | |
H2 | 0.507 (5) | 0.3762 (17) | 0.5662 (9) | 0.046 (6)* | |
O2 | 0.7498 (3) | 0.28587 (10) | 0.80199 (4) | 0.0391 (3) | |
N3 | −0.0228 (3) | 0.10357 (9) | 0.92925 (5) | 0.0321 (3) | |
O31 | −0.1695 (3) | 0.04335 (9) | 0.90759 (5) | 0.0447 (3) | |
O32 | −0.0415 (3) | 0.12776 (10) | 0.97780 (5) | 0.0455 (3) | |
C11 | 0.6300 (3) | 0.47200 (11) | 0.38129 (6) | 0.0292 (3) | |
C12 | 0.8459 (3) | 0.41023 (11) | 0.38582 (5) | 0.0303 (3) | |
H12 | 0.9429 | 0.3909 | 0.3542 | 0.036* | |
C13 | 0.9163 (3) | 0.37747 (10) | 0.43768 (6) | 0.0281 (3) | |
H13 | 1.0645 | 0.3355 | 0.4420 | 0.034* | |
C14 | 0.7707 (3) | 0.40576 (10) | 0.48373 (5) | 0.0242 (3) | |
C15 | 0.5611 (3) | 0.47130 (11) | 0.47812 (6) | 0.0283 (3) | |
H15 | 0.4677 | 0.4931 | 0.5097 | 0.034* | |
C16 | 0.4890 (3) | 0.50474 (11) | 0.42628 (6) | 0.0311 (3) | |
H16 | 0.3460 | 0.5491 | 0.4219 | 0.037* | |
C21 | 0.6845 (3) | 0.33624 (10) | 0.63336 (5) | 0.0247 (3) | |
C22 | 0.8846 (3) | 0.27623 (12) | 0.65337 (6) | 0.0327 (3) | |
H22 | 1.0108 | 0.2489 | 0.6289 | 0.039* | |
C23 | 0.8987 (3) | 0.25635 (12) | 0.70980 (6) | 0.0350 (3) | |
H23 | 1.0347 | 0.2155 | 0.7239 | 0.042* | |
C24 | 0.7140 (3) | 0.29648 (12) | 0.74487 (6) | 0.0306 (3) | |
C25 | 0.5098 (3) | 0.35383 (12) | 0.72519 (6) | 0.0341 (3) | |
H25 | 0.3810 | 0.3794 | 0.7496 | 0.041* | |
C26 | 0.4950 (3) | 0.37369 (11) | 0.66923 (6) | 0.0315 (3) | |
H26 | 0.3553 | 0.4129 | 0.6553 | 0.038* | |
C31 | 0.5567 (3) | 0.23850 (11) | 0.83140 (5) | 0.0296 (3) | |
C32 | 0.5257 (4) | 0.26777 (12) | 0.88616 (6) | 0.0346 (3) | |
H32 | 0.6331 | 0.3185 | 0.9010 | 0.042* | |
C33 | 0.3384 (4) | 0.22261 (11) | 0.91845 (6) | 0.0331 (3) | |
H33 | 0.3151 | 0.2417 | 0.9557 | 0.040* | |
C34 | 0.1841 (3) | 0.14874 (10) | 0.89559 (5) | 0.0282 (3) | |
C35 | 0.2166 (3) | 0.11743 (11) | 0.84176 (6) | 0.0302 (3) | |
H35 | 0.1104 | 0.0661 | 0.8272 | 0.036* | |
C36 | 0.4075 (3) | 0.16259 (11) | 0.80950 (5) | 0.0305 (3) | |
H36 | 0.4354 | 0.1416 | 0.7727 | 0.037* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0453 (8) | 0.0412 (7) | 0.0282 (6) | −0.0084 (7) | −0.0041 (6) | 0.0075 (5) |
O11 | 0.0520 (9) | 0.0952 (12) | 0.0430 (7) | 0.0135 (9) | −0.0078 (7) | 0.0254 (8) |
O12 | 0.0792 (11) | 0.0501 (7) | 0.0238 (5) | −0.0022 (8) | 0.0027 (6) | −0.0005 (5) |
C1 | 0.0224 (6) | 0.0273 (6) | 0.0252 (6) | −0.0012 (5) | −0.0006 (5) | −0.0009 (5) |
O1 | 0.0224 (5) | 0.0467 (6) | 0.0316 (5) | 0.0049 (5) | 0.0012 (4) | 0.0048 (5) |
N2 | 0.0207 (6) | 0.0364 (6) | 0.0233 (5) | 0.0020 (5) | −0.0008 (5) | 0.0029 (5) |
O2 | 0.0360 (6) | 0.0559 (7) | 0.0255 (5) | −0.0127 (6) | −0.0052 (4) | 0.0092 (5) |
N3 | 0.0368 (7) | 0.0306 (6) | 0.0288 (5) | 0.0019 (6) | 0.0028 (5) | 0.0048 (5) |
O31 | 0.0509 (8) | 0.0404 (6) | 0.0426 (6) | −0.0148 (6) | 0.0060 (6) | −0.0009 (5) |
O32 | 0.0544 (8) | 0.0536 (7) | 0.0285 (5) | −0.0042 (7) | 0.0110 (6) | −0.0013 (5) |
C11 | 0.0336 (8) | 0.0301 (6) | 0.0240 (6) | −0.0066 (6) | −0.0026 (6) | 0.0035 (5) |
C12 | 0.0332 (7) | 0.0330 (7) | 0.0247 (6) | −0.0036 (7) | 0.0052 (6) | −0.0029 (5) |
C13 | 0.0269 (7) | 0.0294 (6) | 0.0282 (6) | 0.0001 (6) | 0.0031 (6) | −0.0019 (5) |
C14 | 0.0230 (6) | 0.0260 (6) | 0.0236 (6) | −0.0023 (6) | 0.0003 (5) | −0.0007 (5) |
C15 | 0.0275 (7) | 0.0308 (6) | 0.0265 (6) | 0.0033 (6) | 0.0041 (6) | 0.0008 (5) |
C16 | 0.0290 (7) | 0.0327 (7) | 0.0317 (7) | 0.0022 (6) | 0.0001 (6) | 0.0048 (6) |
C21 | 0.0231 (6) | 0.0282 (6) | 0.0228 (6) | −0.0015 (6) | 0.0002 (5) | 0.0017 (5) |
C22 | 0.0286 (7) | 0.0379 (7) | 0.0314 (7) | 0.0075 (6) | 0.0018 (6) | 0.0029 (6) |
C23 | 0.0298 (8) | 0.0423 (8) | 0.0329 (7) | 0.0048 (7) | −0.0033 (6) | 0.0109 (6) |
C24 | 0.0301 (7) | 0.0373 (7) | 0.0246 (6) | −0.0064 (6) | −0.0026 (6) | 0.0052 (6) |
C25 | 0.0332 (8) | 0.0428 (8) | 0.0262 (6) | 0.0038 (7) | 0.0050 (6) | 0.0007 (6) |
C26 | 0.0289 (7) | 0.0377 (7) | 0.0279 (6) | 0.0063 (6) | 0.0011 (6) | 0.0038 (5) |
C31 | 0.0301 (7) | 0.0341 (7) | 0.0246 (6) | −0.0005 (6) | −0.0025 (6) | 0.0070 (5) |
C32 | 0.0414 (9) | 0.0337 (7) | 0.0288 (6) | −0.0068 (7) | −0.0061 (7) | 0.0008 (6) |
C33 | 0.0424 (9) | 0.0332 (7) | 0.0237 (6) | −0.0009 (7) | −0.0009 (6) | −0.0011 (5) |
C34 | 0.0318 (7) | 0.0282 (6) | 0.0246 (6) | 0.0013 (6) | 0.0006 (6) | 0.0033 (5) |
C35 | 0.0350 (8) | 0.0301 (6) | 0.0256 (6) | −0.0013 (6) | −0.0030 (6) | −0.0003 (5) |
C36 | 0.0347 (8) | 0.0357 (7) | 0.0211 (5) | 0.0006 (7) | −0.0019 (6) | 0.0012 (5) |
Geometric parameters (Å, º) top
N1—O11 | 1.225 (2) | C16—H16 | 0.9500 |
N1—O12 | 1.225 (2) | C21—C22 | 1.391 (2) |
N1—C11 | 1.4747 (18) | C21—C26 | 1.395 (2) |
C1—O1 | 1.2332 (18) | C22—C23 | 1.4010 (19) |
C1—N2 | 1.3557 (19) | C22—H22 | 0.9500 |
C1—C14 | 1.5085 (18) | C23—C24 | 1.381 (2) |
N2—C21 | 1.4216 (16) | C23—H23 | 0.9500 |
N2—H2 | 0.84 (3) | C24—C25 | 1.383 (2) |
O2—C31 | 1.3741 (19) | C25—C26 | 1.3898 (19) |
O2—C24 | 1.4089 (16) | C25—H25 | 0.9500 |
N3—O31 | 1.2257 (19) | C26—H26 | 0.9500 |
N3—O32 | 1.2297 (16) | C31—C36 | 1.386 (2) |
N3—C34 | 1.467 (2) | C31—C32 | 1.3992 (19) |
C11—C16 | 1.382 (2) | C32—C33 | 1.378 (2) |
C11—C12 | 1.386 (2) | C32—H32 | 0.9500 |
C12—C13 | 1.385 (2) | C33—C34 | 1.389 (2) |
C12—H12 | 0.9500 | C33—H33 | 0.9500 |
C13—C14 | 1.3966 (19) | C34—C35 | 1.3867 (19) |
C13—H13 | 0.9500 | C35—C36 | 1.390 (2) |
C14—C15 | 1.395 (2) | C35—H35 | 0.9500 |
C15—C16 | 1.3895 (19) | C36—H36 | 0.9500 |
C15—H15 | 0.9500 | | |
| | | |
O11—N1—O12 | 124.11 (15) | C21—C22—C23 | 119.55 (14) |
O11—N1—C11 | 117.44 (15) | C21—C22—H22 | 120.2 |
O12—N1—C11 | 118.45 (16) | C23—C22—H22 | 120.2 |
O1—C1—N2 | 124.36 (13) | C24—C23—C22 | 119.65 (15) |
O1—C1—C14 | 120.98 (13) | C24—C23—H23 | 120.2 |
N2—C1—C14 | 114.66 (13) | C22—C23—H23 | 120.2 |
C1—N2—C21 | 127.14 (13) | C23—C24—C25 | 121.23 (13) |
C1—N2—H2 | 116.7 (15) | C23—C24—O2 | 118.77 (14) |
C21—N2—H2 | 116.2 (15) | C25—C24—O2 | 119.75 (14) |
C31—O2—C24 | 117.97 (12) | C24—C25—C26 | 119.27 (14) |
O31—N3—O32 | 122.96 (15) | C24—C25—H25 | 120.4 |
O31—N3—C34 | 118.36 (12) | C26—C25—H25 | 120.4 |
O32—N3—C34 | 118.68 (14) | C25—C26—C21 | 120.30 (14) |
C16—C11—C12 | 122.85 (13) | C25—C26—H26 | 119.9 |
C16—C11—N1 | 118.25 (15) | C21—C26—H26 | 119.9 |
C12—C11—N1 | 118.84 (13) | O2—C31—C36 | 122.59 (13) |
C13—C12—C11 | 118.13 (13) | O2—C31—C32 | 116.31 (14) |
C13—C12—H12 | 120.9 | C36—C31—C32 | 121.03 (14) |
C11—C12—H12 | 120.9 | C33—C32—C31 | 119.62 (14) |
C12—C13—C14 | 120.38 (14) | C33—C32—H32 | 120.2 |
C12—C13—H13 | 119.8 | C31—C32—H32 | 120.2 |
C14—C13—H13 | 119.8 | C32—C33—C34 | 118.87 (13) |
C15—C14—C13 | 120.11 (13) | C32—C33—H33 | 120.6 |
C15—C14—C1 | 122.30 (12) | C34—C33—H33 | 120.6 |
C13—C14—C1 | 117.57 (13) | C35—C34—C33 | 122.17 (14) |
C16—C15—C14 | 119.92 (13) | C35—C34—N3 | 118.96 (14) |
C16—C15—H15 | 120.0 | C33—C34—N3 | 118.87 (13) |
C14—C15—H15 | 120.0 | C34—C35—C36 | 118.74 (14) |
C11—C16—C15 | 118.50 (14) | C34—C35—H35 | 120.6 |
C11—C16—H16 | 120.7 | C36—C35—H35 | 120.6 |
C15—C16—H16 | 120.7 | C31—C36—C35 | 119.52 (13) |
C22—C21—C26 | 119.95 (13) | C31—C36—H36 | 120.2 |
C22—C21—N2 | 123.13 (13) | C35—C36—H36 | 120.2 |
C26—C21—N2 | 116.92 (12) | | |
| | | |
O1—C1—N2—C21 | 6.5 (2) | C22—C23—C24—C25 | 1.9 (3) |
C14—C1—N2—C21 | −173.31 (13) | C22—C23—C24—O2 | −172.20 (15) |
O11—N1—C11—C16 | −5.2 (2) | C31—O2—C24—C23 | −120.83 (17) |
O12—N1—C11—C16 | 175.59 (16) | C31—O2—C24—C25 | 65.0 (2) |
O11—N1—C11—C12 | 172.02 (16) | C23—C24—C25—C26 | −1.9 (3) |
O12—N1—C11—C12 | −7.2 (2) | O2—C24—C25—C26 | 172.18 (15) |
C16—C11—C12—C13 | 2.4 (2) | C24—C25—C26—C21 | −0.1 (2) |
N1—C11—C12—C13 | −174.76 (14) | C22—C21—C26—C25 | 2.0 (2) |
C11—C12—C13—C14 | 0.5 (2) | N2—C21—C26—C25 | −178.58 (14) |
C12—C13—C14—C15 | −3.3 (2) | C24—O2—C31—C36 | 32.7 (2) |
C12—C13—C14—C1 | 178.12 (14) | C24—O2—C31—C32 | −150.29 (15) |
O1—C1—C14—C15 | −154.03 (15) | O2—C31—C32—C33 | −179.11 (15) |
N2—C1—C14—C15 | 25.8 (2) | C36—C31—C32—C33 | −2.0 (2) |
O1—C1—C14—C13 | 24.6 (2) | C31—C32—C33—C34 | 0.0 (2) |
N2—C1—C14—C13 | −155.60 (13) | C32—C33—C34—C35 | 1.5 (2) |
C13—C14—C15—C16 | 3.1 (2) | C32—C33—C34—N3 | −177.44 (14) |
C1—C14—C15—C16 | −178.30 (14) | O31—N3—C34—C35 | −3.9 (2) |
C12—C11—C16—C15 | −2.5 (2) | O32—N3—C34—C35 | 176.11 (14) |
N1—C11—C16—C15 | 174.67 (14) | O31—N3—C34—C33 | 175.06 (15) |
C14—C15—C16—C11 | −0.3 (2) | O32—N3—C34—C33 | −4.9 (2) |
C1—N2—C21—C22 | −25.3 (2) | C33—C34—C35—C36 | −0.9 (2) |
C1—N2—C21—C26 | 155.33 (15) | N3—C34—C35—C36 | 178.03 (13) |
C26—C21—C22—C23 | −2.0 (2) | O2—C31—C36—C35 | 179.52 (14) |
N2—C21—C22—C23 | 178.67 (15) | C32—C31—C36—C35 | 2.6 (2) |
C21—C22—C23—C24 | 0.0 (3) | C34—C35—C36—C31 | −1.1 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22···O1 | 0.95 | 2.36 | 2.8988 (18) | 116 |
N2—H2···O1i | 0.84 (3) | 2.28 (3) | 3.0449 (17) | 152 (2) |
C25—H25···O11ii | 0.95 | 2.32 | 3.240 (2) | 164 |
C26—H26···O31iii | 0.95 | 2.52 | 3.396 (2) | 153 |
C33—H33···O32iv | 0.95 | 2.51 | 3.297 (2) | 141 |
C36—H36···O12v | 0.95 | 2.54 | 3.2329 (19) | 130 |
Symmetry codes: (i) x−1, 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) x−1/2, −y+1/2, −z+1. |
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