





Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810040687/pv2329sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810040687/pv2329Isup2.hkl |
CCDC reference: 799669
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.058
- wR factor = 0.155
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.05 PLAT334_ALERT_2_C Small Average Benzene C-C Dist. C1 -C6 1.37 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 5
Alert level G PLAT154_ALERT_1_G The su's on the Cell Angles are Equal (x 10000) 3000 Deg. 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 4 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
4-Chloro-3-nitrobenzamide (4.0 g, 0.02 mol) was heated in 4-fluorobenzenamine (10 ml) for 18 h at 403 K. On completion of the reaction (TLC control) was added ethanol (50 ml), at room temperature. The red precipitate thus formed was filtered, washed with cold ethanol (2 × 15 ml), dried over sodium sulfate to provide 5.8 g (79%) of (I) (Schelz & Inst, 1978). The compound (I) was purified by crystallizing from methanol. The crystals of (I) suitable for X-ray diffraction were obstained by slow evaporation of a methanol solution.
H atoms were positioned geometrically, with N—H = 0.86 and C—H = 0.93 Å, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C/N).
The crystal structure of the title compound, (I), is presented in this article. In the title molecule (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The phenylaminobenzamide moiety (C1–C13/N1/O1) is essentially planar with maximum deviation of any atom being 0.036 (3) Å for C11 with F2 lying 0.109 (4) Å out of its plane, nitro group (N3/O2/O3) titlted at an angle 9.6 (5)° from its plane and the phenyl ring (C14–C19) inclined at 62.20 (8)° with its plane. In the crystal structure, weak intermolecular C—H···O, N—H···O and C—H···F hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in stabilizing the structure.
For comparison of bond lengths, see: Allen et al. (1987). For the synthetic procedure, see: Schelz & Inst (1978).
Data collection: CAD-4 Software (Enraf–Nonius, 1994); cell refinement: CAD-4 Software (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
C19H13F2N3O3 | Z = 2 |
Mr = 369.32 | F(000) = 380 |
Triclinic, P1 | Dx = 1.499 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8510 (16) Å | Cell parameters from 25 reflections |
b = 8.2720 (17) Å | θ = 9–12° |
c = 13.835 (3) Å | µ = 0.12 mm−1 |
α = 74.75 (3)° | T = 293 K |
β = 85.67 (3)° | Block, colourless |
γ = 70.76 (3)° | 0.30 × 0.20 × 0.10 mm |
V = 818.4 (3) Å3 |
Enraf–Nonius CAD-4 diffractometer | 1559 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 25.3°, θmin = 1.5° |
ω and 2θ scans | h = 0→9 |
Absorption correction: ψ scan (North et al., 1968) | k = −9→9 |
Tmin = 0.965, Tmax = 0.988 | l = −16→16 |
3198 measured reflections | 3 standard reflections every 200 reflections |
2962 independent reflections | intensity decay: 1% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.155 | w = 1/[σ2(Fo2) + (0.065P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
2962 reflections | Δρmax = 0.16 e Å−3 |
245 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.021 (4) |
C19H13F2N3O3 | γ = 70.76 (3)° |
Mr = 369.32 | V = 818.4 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.8510 (16) Å | Mo Kα radiation |
b = 8.2720 (17) Å | µ = 0.12 mm−1 |
c = 13.835 (3) Å | T = 293 K |
α = 74.75 (3)° | 0.30 × 0.20 × 0.10 mm |
β = 85.67 (3)° |
Enraf–Nonius CAD-4 diffractometer | 1559 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.026 |
Tmin = 0.965, Tmax = 0.988 | 3 standard reflections every 200 reflections |
3198 measured reflections | intensity decay: 1% |
2962 independent reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.16 e Å−3 |
2962 reflections | Δρmin = −0.18 e Å−3 |
245 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
F1 | 0.7511 (3) | 0.0655 (3) | −0.12706 (14) | 0.0823 (8) | |
N1 | 0.1978 (4) | −0.2157 (3) | 0.58538 (17) | 0.0468 (7) | |
H1A | 0.2383 | −0.2652 | 0.5372 | 0.056* | |
F2 | −0.0468 (3) | −0.6359 (3) | 0.90592 (15) | 0.0839 (8) | |
C1 | 0.0848 (6) | −0.5958 (5) | 0.7467 (3) | 0.0687 (12) | |
H1C | 0.0888 | −0.7083 | 0.7443 | 0.082* | |
N2 | 0.4401 (4) | 0.3033 (3) | 0.20096 (18) | 0.0511 (8) | |
H2A | 0.4232 | 0.4141 | 0.1934 | 0.061* | |
O1 | 0.1462 (4) | 0.0382 (3) | 0.63333 (16) | 0.0645 (8) | |
C2 | 0.1458 (5) | −0.4877 (4) | 0.6679 (3) | 0.0618 (11) | |
H2B | 0.1932 | −0.5290 | 0.6120 | 0.074* | |
O2 | 0.3708 (4) | 0.5620 (3) | 0.29073 (19) | 0.0787 (9) | |
C3 | 0.1378 (4) | −0.3197 (4) | 0.6703 (2) | 0.0424 (8) | |
N3 | 0.3373 (4) | 0.4670 (4) | 0.3685 (2) | 0.0579 (9) | |
C4 | 0.0683 (5) | −0.2610 (5) | 0.7541 (2) | 0.0515 (9) | |
H4A | 0.0612 | −0.1478 | 0.7569 | 0.062* | |
O3 | 0.3066 (5) | 0.5176 (4) | 0.4448 (2) | 0.1081 (13) | |
C5 | 0.0093 (5) | −0.3689 (5) | 0.8339 (2) | 0.0573 (10) | |
H5A | −0.0360 | −0.3301 | 0.8909 | 0.069* | |
C6 | 0.0189 (5) | −0.5329 (5) | 0.8276 (3) | 0.0577 (10) | |
C7 | 0.1996 (4) | −0.0465 (4) | 0.5702 (2) | 0.0413 (8) | |
C8 | 0.2697 (4) | 0.0325 (4) | 0.4724 (2) | 0.0367 (7) | |
C9 | 0.3296 (4) | −0.0471 (4) | 0.3930 (2) | 0.0458 (9) | |
H9A | 0.3288 | −0.1616 | 0.3996 | 0.055* | |
C10 | 0.3893 (4) | 0.0400 (4) | 0.3058 (2) | 0.0463 (9) | |
H10A | 0.4292 | −0.0178 | 0.2550 | 0.056* | |
C11 | 0.3924 (4) | 0.2150 (4) | 0.2904 (2) | 0.0408 (8) | |
C12 | 0.3347 (4) | 0.2909 (4) | 0.3723 (2) | 0.0411 (8) | |
C13 | 0.2751 (4) | 0.2014 (4) | 0.4597 (2) | 0.0417 (8) | |
H13A | 0.2376 | 0.2568 | 0.5116 | 0.050* | |
C14 | 0.5150 (5) | 0.2322 (4) | 0.1184 (2) | 0.0422 (8) | |
C15 | 0.6711 (5) | 0.0901 (5) | 0.1283 (2) | 0.0518 (9) | |
H15A | 0.7234 | 0.0318 | 0.1914 | 0.062* | |
C16 | 0.7504 (5) | 0.0333 (5) | 0.0459 (3) | 0.0574 (10) | |
H16A | 0.8563 | −0.0623 | 0.0524 | 0.069* | |
C17 | 0.6702 (6) | 0.1204 (5) | −0.0458 (3) | 0.0554 (10) | |
C18 | 0.5142 (5) | 0.2600 (5) | −0.0589 (2) | 0.0566 (10) | |
H18A | 0.4617 | 0.3155 | −0.1221 | 0.068* | |
C19 | 0.4358 (5) | 0.3171 (4) | 0.0244 (2) | 0.0495 (9) | |
H19A | 0.3298 | 0.4126 | 0.0173 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.114 (2) | 0.0861 (17) | 0.0570 (13) | −0.0353 (15) | 0.0258 (13) | −0.0374 (12) |
N1 | 0.065 (2) | 0.0442 (16) | 0.0382 (15) | −0.0275 (15) | 0.0133 (13) | −0.0135 (12) |
F2 | 0.108 (2) | 0.0535 (14) | 0.0715 (14) | −0.0251 (13) | 0.0345 (13) | 0.0043 (11) |
C1 | 0.094 (3) | 0.038 (2) | 0.068 (3) | −0.020 (2) | 0.017 (2) | −0.0092 (19) |
N2 | 0.078 (2) | 0.0423 (16) | 0.0389 (16) | −0.0291 (16) | 0.0172 (15) | −0.0130 (13) |
O1 | 0.104 (2) | 0.0492 (15) | 0.0487 (14) | −0.0345 (15) | 0.0227 (14) | −0.0192 (12) |
C2 | 0.090 (3) | 0.044 (2) | 0.050 (2) | −0.024 (2) | 0.020 (2) | −0.0121 (17) |
O2 | 0.136 (3) | 0.0554 (16) | 0.0587 (16) | −0.0535 (17) | 0.0343 (16) | −0.0184 (13) |
C3 | 0.052 (2) | 0.042 (2) | 0.0342 (18) | −0.0201 (17) | 0.0066 (16) | −0.0069 (15) |
N3 | 0.089 (3) | 0.0494 (18) | 0.0465 (18) | −0.0370 (18) | 0.0176 (17) | −0.0165 (16) |
C4 | 0.063 (3) | 0.055 (2) | 0.044 (2) | −0.031 (2) | 0.0094 (18) | −0.0129 (17) |
O3 | 0.225 (4) | 0.072 (2) | 0.0626 (18) | −0.087 (2) | 0.050 (2) | −0.0403 (16) |
C5 | 0.068 (3) | 0.064 (3) | 0.043 (2) | −0.028 (2) | 0.0144 (18) | −0.0145 (18) |
C6 | 0.062 (3) | 0.046 (2) | 0.049 (2) | −0.0125 (19) | 0.0141 (18) | 0.0043 (17) |
C7 | 0.045 (2) | 0.0400 (19) | 0.0396 (18) | −0.0162 (17) | 0.0017 (16) | −0.0091 (16) |
C8 | 0.040 (2) | 0.0355 (18) | 0.0351 (17) | −0.0139 (15) | −0.0003 (14) | −0.0072 (14) |
C9 | 0.061 (2) | 0.043 (2) | 0.0426 (19) | −0.0269 (18) | 0.0063 (17) | −0.0134 (15) |
C10 | 0.060 (2) | 0.046 (2) | 0.0427 (19) | −0.0260 (18) | 0.0105 (17) | −0.0201 (16) |
C11 | 0.044 (2) | 0.0385 (19) | 0.0412 (19) | −0.0149 (16) | 0.0005 (15) | −0.0106 (15) |
C12 | 0.053 (2) | 0.0365 (18) | 0.0384 (18) | −0.0195 (17) | 0.0029 (16) | −0.0110 (15) |
C13 | 0.053 (2) | 0.0418 (19) | 0.0339 (17) | −0.0186 (17) | 0.0030 (15) | −0.0116 (14) |
C14 | 0.060 (2) | 0.0416 (19) | 0.0353 (18) | −0.0296 (19) | 0.0097 (16) | −0.0125 (15) |
C15 | 0.062 (3) | 0.050 (2) | 0.043 (2) | −0.020 (2) | 0.0041 (18) | −0.0094 (16) |
C16 | 0.064 (3) | 0.049 (2) | 0.060 (2) | −0.0173 (19) | 0.014 (2) | −0.0197 (19) |
C17 | 0.082 (3) | 0.060 (2) | 0.041 (2) | −0.040 (2) | 0.022 (2) | −0.0237 (18) |
C18 | 0.073 (3) | 0.065 (3) | 0.039 (2) | −0.036 (2) | 0.0023 (19) | −0.0083 (18) |
C19 | 0.050 (2) | 0.046 (2) | 0.049 (2) | −0.0173 (18) | 0.0048 (18) | −0.0066 (17) |
F1—C17 | 1.358 (3) | C5—H5A | 0.9300 |
N1—C7 | 1.365 (4) | C7—C8 | 1.490 (4) |
N1—C3 | 1.413 (3) | C8—C13 | 1.376 (4) |
N1—H1A | 0.8600 | C8—C9 | 1.400 (4) |
F2—C6 | 1.373 (4) | C9—C10 | 1.369 (4) |
C1—C6 | 1.354 (5) | C9—H9A | 0.9300 |
C1—C2 | 1.382 (4) | C10—C11 | 1.415 (4) |
C1—H1C | 0.9300 | C10—H10A | 0.9300 |
N2—C11 | 1.357 (4) | C11—C12 | 1.412 (4) |
N2—C14 | 1.421 (4) | C12—C13 | 1.378 (4) |
N2—H2A | 0.8600 | C13—H13A | 0.9300 |
O1—C7 | 1.225 (3) | C14—C15 | 1.376 (4) |
C2—C3 | 1.379 (4) | C14—C19 | 1.388 (4) |
C2—H2B | 0.9300 | C15—C16 | 1.375 (4) |
O2—N3 | 1.222 (3) | C15—H15A | 0.9300 |
C3—C4 | 1.380 (4) | C16—C17 | 1.366 (5) |
N3—O3 | 1.214 (3) | C16—H16A | 0.9300 |
N3—C12 | 1.451 (4) | C17—C18 | 1.363 (5) |
C4—C5 | 1.381 (4) | C18—C19 | 1.384 (4) |
C4—H4A | 0.9300 | C18—H18A | 0.9300 |
C5—C6 | 1.360 (5) | C19—H19A | 0.9300 |
C7—N1—C3 | 128.1 (3) | C10—C9—C8 | 121.5 (3) |
C7—N1—H1A | 115.9 | C10—C9—H9A | 119.3 |
C3—N1—H1A | 115.9 | C8—C9—H9A | 119.3 |
C6—C1—C2 | 117.9 (4) | C9—C10—C11 | 122.1 (3) |
C6—C1—H1C | 121.0 | C9—C10—H10A | 118.9 |
C2—C1—H1C | 121.0 | C11—C10—H10A | 118.9 |
C11—N2—C14 | 126.9 (3) | N2—C11—C12 | 123.5 (3) |
C11—N2—H2A | 116.6 | N2—C11—C10 | 121.2 (3) |
C14—N2—H2A | 116.6 | C12—C11—C10 | 115.2 (3) |
C3—C2—C1 | 121.4 (3) | C13—C12—C11 | 121.9 (3) |
C3—C2—H2B | 119.3 | C13—C12—N3 | 116.8 (3) |
C1—C2—H2B | 119.3 | C11—C12—N3 | 121.2 (3) |
C2—C3—C4 | 118.6 (3) | C8—C13—C12 | 121.9 (3) |
C2—C3—N1 | 117.8 (3) | C8—C13—H13A | 119.0 |
C4—C3—N1 | 123.6 (3) | C12—C13—H13A | 119.0 |
O3—N3—O2 | 120.7 (3) | C15—C14—C19 | 119.5 (3) |
O3—N3—C12 | 118.4 (3) | C15—C14—N2 | 121.5 (3) |
O2—N3—C12 | 120.9 (3) | C19—C14—N2 | 118.8 (3) |
C3—C4—C5 | 120.5 (3) | C16—C15—C14 | 120.6 (3) |
C3—C4—H4A | 119.7 | C16—C15—H15A | 119.7 |
C5—C4—H4A | 119.7 | C14—C15—H15A | 119.7 |
C6—C5—C4 | 118.7 (3) | C17—C16—C15 | 118.5 (4) |
C6—C5—H5A | 120.7 | C17—C16—H16A | 120.7 |
C4—C5—H5A | 120.7 | C15—C16—H16A | 120.7 |
C1—C6—C5 | 122.9 (3) | F1—C17—C18 | 119.1 (3) |
C1—C6—F2 | 119.1 (3) | F1—C17—C16 | 118.1 (4) |
C5—C6—F2 | 117.9 (3) | C18—C17—C16 | 122.8 (3) |
O1—C7—N1 | 122.2 (3) | C17—C18—C19 | 118.3 (3) |
O1—C7—C8 | 120.9 (3) | C17—C18—H18A | 120.8 |
N1—C7—C8 | 116.9 (3) | C19—C18—H18A | 120.8 |
C13—C8—C9 | 117.3 (3) | C18—C19—C14 | 120.2 (3) |
C13—C8—C7 | 115.9 (3) | C18—C19—H19A | 119.9 |
C9—C8—C7 | 126.8 (3) | C14—C19—H19A | 119.9 |
C6—C1—C2—C3 | −0.9 (6) | N2—C11—C12—C13 | 175.3 (3) |
C1—C2—C3—C4 | 0.5 (6) | C10—C11—C12—C13 | −1.7 (5) |
C1—C2—C3—N1 | −178.1 (3) | N2—C11—C12—N3 | −5.3 (5) |
C7—N1—C3—C2 | 178.7 (3) | C10—C11—C12—N3 | 177.6 (3) |
C7—N1—C3—C4 | 0.2 (5) | O3—N3—C12—C13 | 7.8 (5) |
C2—C3—C4—C5 | 0.4 (5) | O2—N3—C12—C13 | −172.6 (3) |
N1—C3—C4—C5 | 178.9 (3) | O3—N3—C12—C11 | −171.5 (4) |
C3—C4—C5—C6 | −0.9 (5) | O2—N3—C12—C11 | 8.1 (5) |
C2—C1—C6—C5 | 0.5 (6) | C9—C8—C13—C12 | 0.8 (5) |
C2—C1—C6—F2 | 178.4 (3) | C7—C8—C13—C12 | −179.1 (3) |
C4—C5—C6—C1 | 0.4 (6) | C11—C12—C13—C8 | 0.4 (5) |
C4—C5—C6—F2 | −177.5 (3) | N3—C12—C13—C8 | −178.9 (3) |
C3—N1—C7—O1 | 0.3 (5) | C11—N2—C14—C15 | −56.2 (5) |
C3—N1—C7—C8 | −179.6 (3) | C11—N2—C14—C19 | 128.7 (3) |
O1—C7—C8—C13 | 1.9 (5) | C19—C14—C15—C16 | 1.0 (5) |
N1—C7—C8—C13 | −178.2 (3) | N2—C14—C15—C16 | −174.0 (3) |
O1—C7—C8—C9 | −178.0 (3) | C14—C15—C16—C17 | −0.4 (5) |
N1—C7—C8—C9 | 1.9 (5) | C15—C16—C17—F1 | 178.9 (3) |
C13—C8—C9—C10 | −0.7 (5) | C15—C16—C17—C18 | −0.6 (5) |
C7—C8—C9—C10 | 179.2 (3) | F1—C17—C18—C19 | −178.4 (3) |
C8—C9—C10—C11 | −0.6 (5) | C16—C17—C18—C19 | 1.0 (5) |
C14—N2—C11—C12 | 173.7 (3) | C17—C18—C19—C14 | −0.4 (5) |
C14—N2—C11—C10 | −9.4 (5) | C15—C14—C19—C18 | −0.5 (5) |
C9—C10—C11—N2 | −175.3 (3) | N2—C14—C19—C18 | 174.6 (3) |
C9—C10—C11—C12 | 1.8 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O3i | 0.86 | 2.37 | 3.185 (4) | 158 |
N2—H2A···O2 | 0.86 | 1.98 | 2.636 (4) | 132 |
N2—H2A···N3 | 0.86 | 2.58 | 2.917 (4) | 105 |
C2—H2B···O3i | 0.93 | 2.40 | 3.240 (5) | 151 |
C4—H4A···O1 | 0.93 | 2.20 | 2.821 (4) | 123 |
C10—H10A···F1ii | 0.93 | 2.53 | 3.205 (4) | 130 |
C13—H13A···O1 | 0.93 | 2.39 | 2.728 (4) | 102 |
C13—H13A···O3 | 0.93 | 2.33 | 2.661 (5) | 100 |
C15—H15A···O1iii | 0.93 | 2.55 | 3.454 (4) | 164 |
C16—H16A···F2iv | 0.93 | 2.39 | 3.272 (5) | 158 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y, −z; (iii) −x+1, −y, −z+1; (iv) −x+1, −y−1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C19H13F2N3O3 |
Mr | 369.32 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.8510 (16), 8.2720 (17), 13.835 (3) |
α, β, γ (°) | 74.75 (3), 85.67 (3), 70.76 (3) |
V (Å3) | 818.4 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.965, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3198, 2962, 1559 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.601 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.155, 1.00 |
No. of reflections | 2962 |
No. of parameters | 245 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.18 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O3i | 0.86 | 2.37 | 3.185 (4) | 158 |
N2—H2A···O2 | 0.86 | 1.98 | 2.636 (4) | 132 |
C2—H2B···O3i | 0.93 | 2.40 | 3.240 (5) | 151 |
C10—H10A···F1ii | 0.93 | 2.53 | 3.205 (4) | 130 |
C15—H15A···O1iii | 0.93 | 2.55 | 3.454 (4) | 164 |
C16—H16A···F2iv | 0.93 | 2.39 | 3.272 (5) | 158 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y, −z; (iii) −x+1, −y, −z+1; (iv) −x+1, −y−1, −z+1. |
The crystal structure of the title compound, (I), is presented in this article. In the title molecule (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The phenylaminobenzamide moiety (C1–C13/N1/O1) is essentially planar with maximum deviation of any atom being 0.036 (3) Å for C11 with F2 lying 0.109 (4) Å out of its plane, nitro group (N3/O2/O3) titlted at an angle 9.6 (5)° from its plane and the phenyl ring (C14–C19) inclined at 62.20 (8)° with its plane. In the crystal structure, weak intermolecular C—H···O, N—H···O and C—H···F hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in stabilizing the structure.