1-(4-Amino­phen­yl)-2-(4-nitro­phen­yl)ethanone

In the title compound, C₁₄H₁₂N₂O₃, 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 NH₂ 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 NH₂ and NO₂ groups. Adjacent chains are linked via π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](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

---

Computing details

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

Crystal data

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) Å^3	Plate, yellow
Z = 4	0.28 × 0.18 × 0.08 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0458P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.96 (3)	1.93 (3)	2.886 (3)	174 (3)
N1—H2···O2^ii	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.