In the title compound, C
14H
12N
2O
3, the dihedral angle between the two aromatic rings is 86.13 (15)°. Intermolecular N—H
O hydrogen bonds [N
O = 2.886 (3) Å and N—H
O = 174 (3)°] between the NH
2 and C=O groups link the molecules into a one-dimensional ribbon augmented by secondary N—H
O interactions [N
O = 3.105 (4) Å and N—H
O = 154 (3)°] involving NH
2 and NO
2 groups. Adjacent chains are linked
via π–π interactions.
Supporting information
CCDC reference: 640332
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.004 Å
- R factor = 0.041
- wR factor = 0.098
- Data-to-parameter ratio = 11.2
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
| Author Response: we consider that this coverage is sufficient for the purposes
of this study (elucidation of H bonds). Very good precision on the
derived geometrical parameters has been obtained.
|
Alert level B
PLAT024_ALERT_4_B Merging of Friedel Pairs is STRONGLY Indicated . !
| Author Response: The Friedel equivalents were merged prior to the final
refinements.
|
Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
From the CIF: _diffrn_reflns_theta_max 27.00
From the CIF: _reflns_number_total 2036
From the CIF: _diffrn_reflns_limit_ max hkl 13. 10. 16.
From the CIF: _diffrn_reflns_limit_ min hkl -7. -8. -13.
TEST1: Expected hkl limits for theta max
Calculated maximum hkl 13. 10. 18.
Calculated minimum hkl -13. -10. -18.
REFLT03_ALERT_4_G ALERT: MoKa measured Friedel data cannot be used to
determine absolute structure in a light-atom
study EXCEPT under VERY special conditions.
It is preferred that Friedel data is merged in such cases.
From the CIF: _diffrn_reflns_theta_max 27.00
From the CIF: _reflns_number_total 2036
Count of symmetry unique reflns 1374
Completeness (_total/calc) 148.18%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 662
Fraction of Friedel pairs measured 0.482
Are heavy atom types Z>Si present no
1 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Siemens, 1994); cell refinement: SMART; data reduction: SAINT (Siemens, 1994); 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.
1-(4-aminophenyl)-2-(4-nitrophenyl)ethanone
top
Crystal data top
C14H12N2O3 | F(000) = 536 |
Mr = 256.26 | Dx = 1.402 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 3710 reflections |
a = 10.1889 (16) Å | θ = 2.7–27.0° |
b = 8.0102 (11) Å | µ = 0.10 mm−1 |
c = 14.8722 (17) Å | T = 150 K |
V = 1213.8 (3) Å3 | Plate, yellow |
Z = 4 | 0.28 × 0.18 × 0.08 mm |
Data collection top
Siemens SMART CCD 1000 diffractometer | 1475 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.050 |
Graphite monochromator | θmax = 27.0°, θmin = 2.7° |
φ and ω scans | h = −7→13 |
3710 measured reflections | k = −8→10 |
2036 independent reflections | l = −13→16 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.91 | w = 1/[σ2(Fo2) + (0.0458P)2] where P = (Fo2 + 2Fc2)/3 |
2036 reflections | (Δ/σ)max < 0.001 |
181 parameters | Δρmax = 0.18 e Å−3 |
1 restraint | Δρmin = −0.29 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 | |
N1 | 0.0756 (3) | 0.3352 (3) | −0.42269 (19) | 0.0217 (6) | |
N2 | 0.1920 (3) | 0.1364 (4) | 0.37986 (16) | 0.0234 (7) | |
O1 | 0.0466 (2) | 0.3696 (3) | 0.00411 (16) | 0.0264 (5) | |
O2 | 0.2625 (2) | 0.2349 (3) | 0.42155 (15) | 0.0338 (6) | |
O3 | 0.1210 (2) | 0.0341 (3) | 0.41780 (15) | 0.0312 (6) | |
C1 | 0.0882 (3) | 0.3255 (3) | −0.33199 (19) | 0.0154 (7) | |
C2 | 0.0141 (3) | 0.4293 (4) | −0.27441 (18) | 0.0190 (7) | |
H2A | −0.0424 | 0.5085 | −0.2988 | 0.023* | |
C3 | 0.0248 (3) | 0.4145 (3) | −0.1834 (2) | 0.0168 (7) | |
H3A | −0.0246 | 0.4847 | −0.1468 | 0.020* | |
C4 | 0.1078 (3) | 0.2970 (4) | −0.14350 (19) | 0.0151 (7) | |
C5 | 0.1828 (3) | 0.1966 (3) | −0.20056 (19) | 0.0163 (7) | |
H5A | 0.2403 | 0.1190 | −0.1758 | 0.020* | |
C6 | 0.1733 (3) | 0.2099 (4) | −0.2926 (2) | 0.0177 (7) | |
H6A | 0.2242 | 0.1412 | −0.3289 | 0.021* | |
C7 | 0.1129 (3) | 0.2811 (4) | −0.0444 (2) | 0.0160 (7) | |
C8 | 0.2037 (3) | 0.1504 (4) | −0.0042 (2) | 0.0194 (7) | |
H8A | 0.1789 | 0.0412 | −0.0267 | 0.023* | |
H8B | 0.2929 | 0.1726 | −0.0236 | 0.023* | |
C9 | 0.1995 (3) | 0.1483 (4) | 0.09631 (19) | 0.0152 (7) | |
C10 | 0.1173 (3) | 0.0388 (4) | 0.14149 (19) | 0.0183 (7) | |
H10A | 0.0632 | −0.0322 | 0.1087 | 0.022* | |
C11 | 0.1143 (3) | 0.0332 (4) | 0.2345 (2) | 0.0194 (7) | |
H11A | 0.0601 | −0.0418 | 0.2644 | 0.023* | |
C12 | 0.1940 (3) | 0.1421 (4) | 0.2816 (2) | 0.0169 (7) | |
C13 | 0.2772 (3) | 0.2536 (4) | 0.2391 (2) | 0.0194 (7) | |
H13A | 0.3302 | 0.3256 | 0.2721 | 0.023* | |
C14 | 0.2793 (3) | 0.2547 (4) | 0.14641 (19) | 0.0200 (7) | |
H14A | 0.3352 | 0.3281 | 0.1167 | 0.024* | |
H1 | 0.031 (3) | 0.428 (4) | −0.449 (2) | 0.028 (10)* | |
H2 | 0.125 (3) | 0.279 (4) | −0.455 (2) | 0.028 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0255 (15) | 0.0232 (15) | 0.0164 (17) | 0.0036 (13) | 0.0010 (13) | 0.0002 (13) |
N2 | 0.0312 (16) | 0.0252 (17) | 0.0136 (16) | 0.0050 (14) | 0.0028 (11) | −0.0022 (12) |
O1 | 0.0302 (12) | 0.0338 (12) | 0.0153 (12) | 0.0172 (10) | 0.0031 (11) | −0.0014 (12) |
O2 | 0.0436 (13) | 0.0411 (14) | 0.0168 (13) | −0.0091 (12) | 0.0004 (11) | −0.0112 (12) |
O3 | 0.0394 (13) | 0.0379 (13) | 0.0163 (13) | −0.0050 (11) | 0.0078 (11) | 0.0023 (12) |
C1 | 0.0172 (15) | 0.0186 (15) | 0.0102 (19) | −0.0052 (12) | 0.0001 (12) | 0.0015 (12) |
C2 | 0.0123 (14) | 0.0191 (15) | 0.026 (2) | 0.0008 (13) | −0.0035 (12) | 0.0003 (14) |
C3 | 0.0164 (14) | 0.0159 (14) | 0.0179 (19) | −0.0002 (11) | 0.0023 (12) | −0.0004 (13) |
C4 | 0.0138 (16) | 0.0152 (15) | 0.0163 (18) | 0.0007 (12) | −0.0020 (12) | 0.0002 (12) |
C5 | 0.0136 (14) | 0.0182 (16) | 0.017 (2) | 0.0000 (11) | 0.0004 (12) | 0.0012 (13) |
C6 | 0.0178 (15) | 0.0185 (15) | 0.0168 (19) | 0.0013 (12) | 0.0027 (12) | −0.0004 (13) |
C7 | 0.0190 (15) | 0.0171 (16) | 0.0118 (16) | −0.0008 (12) | −0.0012 (12) | −0.0003 (13) |
C8 | 0.0216 (15) | 0.0215 (16) | 0.0153 (18) | 0.0047 (13) | −0.0001 (14) | 0.0018 (15) |
C9 | 0.0178 (15) | 0.0186 (15) | 0.0092 (17) | 0.0068 (13) | 0.0011 (12) | −0.0009 (13) |
C10 | 0.0182 (15) | 0.0194 (15) | 0.017 (2) | −0.0005 (12) | −0.0026 (12) | −0.0003 (14) |
C11 | 0.0215 (16) | 0.0209 (16) | 0.0157 (19) | −0.0003 (13) | 0.0025 (12) | 0.0018 (14) |
C12 | 0.0195 (15) | 0.0207 (16) | 0.0106 (16) | 0.0047 (13) | 0.0027 (13) | −0.0010 (13) |
C13 | 0.0239 (16) | 0.0187 (15) | 0.0156 (17) | 0.0021 (13) | −0.0040 (13) | −0.0028 (14) |
C14 | 0.0196 (16) | 0.0195 (16) | 0.0208 (19) | 0.0001 (12) | 0.0018 (13) | 0.0021 (14) |
Geometric parameters (Å, º) top
N1—C1 | 1.357 (4) | C5—H5A | 0.9300 |
N1—H1 | 0.96 (3) | C6—H6A | 0.9300 |
N1—H2 | 0.83 (3) | C7—C8 | 1.520 (4) |
N2—O3 | 1.230 (3) | C8—C9 | 1.495 (4) |
N2—O2 | 1.234 (3) | C8—H8A | 0.9700 |
N2—C12 | 1.462 (4) | C8—H8B | 0.9700 |
O1—C7 | 1.217 (4) | C9—C10 | 1.387 (4) |
C1—C6 | 1.398 (4) | C9—C14 | 1.394 (4) |
C1—C2 | 1.412 (4) | C10—C11 | 1.384 (4) |
C2—C3 | 1.363 (4) | C10—H10A | 0.9300 |
C2—H2A | 0.9300 | C11—C12 | 1.383 (4) |
C3—C4 | 1.398 (4) | C11—H11A | 0.9300 |
C3—H3A | 0.9300 | C12—C13 | 1.384 (4) |
C4—C5 | 1.396 (4) | C13—C14 | 1.378 (4) |
C4—C7 | 1.480 (4) | C13—H13A | 0.9300 |
C5—C6 | 1.376 (4) | C14—H14A | 0.9300 |
| | | |
C1—N1—H1 | 119.8 (19) | C4—C7—C8 | 118.2 (3) |
C1—N1—H2 | 119 (2) | C9—C8—C7 | 112.6 (2) |
H1—N1—H2 | 118 (3) | C9—C8—H8A | 109.1 |
O3—N2—O2 | 122.5 (3) | C7—C8—H8A | 109.1 |
O3—N2—C12 | 119.2 (3) | C9—C8—H8B | 109.1 |
O2—N2—C12 | 118.3 (3) | C7—C8—H8B | 109.1 |
N1—C1—C6 | 120.9 (3) | H8A—C8—H8B | 107.8 |
N1—C1—C2 | 121.2 (3) | C10—C9—C14 | 118.7 (3) |
C6—C1—C2 | 117.9 (3) | C10—C9—C8 | 120.6 (3) |
C3—C2—C1 | 120.6 (3) | C14—C9—C8 | 120.7 (3) |
C3—C2—H2A | 119.7 | C11—C10—C9 | 121.2 (3) |
C1—C2—H2A | 119.7 | C11—C10—H10A | 119.4 |
C2—C3—C4 | 121.9 (3) | C9—C10—H10A | 119.4 |
C2—C3—H3A | 119.1 | C12—C11—C10 | 118.3 (3) |
C4—C3—H3A | 119.1 | C12—C11—H11A | 120.9 |
C5—C4—C3 | 117.4 (2) | C10—C11—H11A | 120.9 |
C5—C4—C7 | 122.4 (3) | C11—C12—C13 | 122.3 (3) |
C3—C4—C7 | 120.1 (3) | C11—C12—N2 | 118.6 (3) |
C6—C5—C4 | 121.4 (3) | C13—C12—N2 | 119.1 (3) |
C6—C5—H5A | 119.3 | C14—C13—C12 | 118.1 (3) |
C4—C5—H5A | 119.3 | C14—C13—H13A | 121.0 |
C5—C6—C1 | 120.8 (3) | C12—C13—H13A | 121.0 |
C5—C6—H6A | 119.6 | C13—C14—C9 | 121.4 (3) |
C1—C6—H6A | 119.6 | C13—C14—H14A | 119.3 |
O1—C7—C4 | 121.4 (3) | C9—C14—H14A | 119.3 |
O1—C7—C8 | 120.4 (3) | | |
| | | |
N1—C1—C2—C3 | 177.9 (3) | C7—C8—C9—C10 | 94.6 (3) |
C6—C1—C2—C3 | −0.9 (4) | C7—C8—C9—C14 | −86.3 (3) |
C1—C2—C3—C4 | −0.3 (4) | C14—C9—C10—C11 | −0.5 (4) |
C2—C3—C4—C5 | 1.5 (4) | C8—C9—C10—C11 | 178.7 (3) |
C2—C3—C4—C7 | −177.8 (3) | C9—C10—C11—C12 | 1.1 (4) |
C3—C4—C5—C6 | −1.4 (4) | C10—C11—C12—C13 | −0.9 (4) |
C7—C4—C5—C6 | 177.9 (3) | C10—C11—C12—N2 | −179.7 (3) |
C4—C5—C6—C1 | 0.2 (4) | O3—N2—C12—C11 | 0.8 (4) |
N1—C1—C6—C5 | −177.9 (3) | O2—N2—C12—C11 | −179.3 (3) |
C2—C1—C6—C5 | 1.0 (4) | O3—N2—C12—C13 | −177.9 (2) |
C5—C4—C7—O1 | −179.9 (3) | O2—N2—C12—C13 | 1.9 (4) |
C3—C4—C7—O1 | −0.6 (5) | C11—C12—C13—C14 | 0.1 (4) |
C5—C4—C7—C8 | 0.1 (4) | N2—C12—C13—C14 | 178.8 (3) |
C3—C4—C7—C8 | 179.4 (2) | C12—C13—C14—C9 | 0.6 (4) |
O1—C7—C8—C9 | −0.2 (4) | C10—C9—C14—C13 | −0.4 (4) |
C4—C7—C8—C9 | 179.8 (3) | C8—C9—C14—C13 | −179.6 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.96 (3) | 1.93 (3) | 2.886 (3) | 174 (3) |
N1—H2···O2ii | 0.83 (3) | 2.34 (3) | 3.105 (4) | 154 (3) |
Symmetry codes: (i) −x, −y+1, z−1/2; (ii) x, y, z−1. |