N-(2-Nitro­benzyl­idene)aniline

In the title compound, C₃₄H₁₀N₂O₂, the dihedral angle between the two six-membered aromatic rings is 60.49 (9)°. The mol­ecule adopts an E configuration with respect to the imine C=N bond.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.051
• wR factor = 0.172
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON.

N-(2-Nitrobenzylidene)aniline

Crystal data

C13H10N2O2	F(000) = 472
Mr = 226.23	Dx = 1.321 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3583 reflections
a = 11.178 (13) Å	θ = 3.1–25.0°
b = 7.718 (5) Å	µ = 0.09 mm^−1
c = 13.217 (16) Å	T = 295 K
β = 94.064 (3)°	Block, pale yellow
V = 1137 (2) Å^3	0.25 × 0.23 × 0.22 mm
Z = 4

Data collection

MacScience DIPLabo 32001 diffractometer	1555 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 25.0°, θmin = 3.1°
Detector resolution: 10.0 pixels mm^-1	h = −13→13
ω scans	k = −8→8
3583 measured reflections	l = −15→15
1923 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.172	w = 1/[σ^2(Fo^2) + (0.1279P)^2 + 0.0772P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
1923 reflections	Δρmax = 0.27 e Å^−3
155 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.081 (12)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2, conventional R-factors R are based on F, with F set to zero for negative F^2. The observed criterion of F^2 > σ(F^2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2 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
O8	0.00571 (14)	0.1380 (3)	0.09731 (14)	0.0931 (7)
O9	0.16962 (13)	−0.0031 (2)	0.09510 (13)	0.0771 (6)
N7	0.10594 (15)	0.1188 (2)	0.06905 (12)	0.0619 (6)
N11	0.47063 (13)	0.23753 (19)	0.06941 (11)	0.0519 (5)
C1	0.2230 (2)	0.4690 (3)	−0.14600 (16)	0.0670 (7)
C2	0.30484 (18)	0.4046 (2)	−0.07250 (14)	0.0580 (7)
C3	0.27086 (15)	0.2895 (2)	0.00127 (13)	0.0496 (6)
C4	0.14966 (16)	0.2461 (2)	−0.00221 (14)	0.0521 (6)
C5	0.06591 (18)	0.3115 (3)	−0.07450 (16)	0.0634 (7)
C6	0.1037 (2)	0.4228 (3)	−0.14711 (17)	0.0693 (8)
C10	0.35996 (15)	0.2297 (2)	0.08162 (13)	0.0499 (6)
C12	0.55308 (15)	0.1916 (2)	0.15159 (13)	0.0476 (5)
C13	0.65628 (16)	0.1045 (2)	0.12956 (14)	0.0549 (6)
C14	0.74091 (17)	0.0600 (3)	0.20630 (17)	0.0627 (7)
C15	0.72453 (18)	0.1057 (3)	0.30544 (16)	0.0630 (7)
C16	0.62333 (18)	0.1939 (3)	0.32780 (15)	0.0633 (7)
C17	0.53740 (16)	0.2378 (2)	0.25167 (14)	0.0555 (6)
H1	0.24840	0.54410	−0.19520	0.0800*
H2	0.38460	0.43890	−0.07220	0.0700*
H5	−0.01450	0.28070	−0.07400	0.0760*
H6	0.04890	0.46680	−0.19680	0.0830*
H10	0.33410	0.18580	0.14190	0.0600*
H13	0.66870	0.07580	0.06280	0.0660*
H14	0.80920	−0.00090	0.19120	0.0750*
H15	0.78210	0.07670	0.35690	0.0760*
H16	0.61240	0.22450	0.39460	0.0760*
H17	0.46910	0.29810	0.26730	0.0670*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O8	0.0592 (10)	0.1275 (15)	0.0953 (13)	−0.0015 (9)	0.0242 (9)	0.0218 (10)
O9	0.0669 (9)	0.0745 (9)	0.0888 (11)	−0.0078 (7)	−0.0028 (8)	0.0227 (8)
N7	0.0491 (10)	0.0767 (11)	0.0595 (10)	−0.0090 (8)	0.0016 (7)	0.0053 (8)
N11	0.0466 (9)	0.0608 (9)	0.0483 (9)	−0.0007 (6)	0.0039 (6)	−0.0015 (6)
C1	0.0759 (14)	0.0638 (12)	0.0603 (12)	−0.0059 (9)	−0.0026 (10)	0.0104 (9)
C2	0.0583 (12)	0.0603 (11)	0.0552 (11)	−0.0094 (8)	0.0023 (9)	0.0019 (8)
C3	0.0490 (10)	0.0537 (9)	0.0459 (10)	−0.0028 (7)	0.0010 (7)	−0.0050 (7)
C4	0.0491 (10)	0.0559 (10)	0.0512 (10)	−0.0015 (7)	0.0034 (8)	−0.0012 (7)
C5	0.0478 (11)	0.0713 (13)	0.0698 (13)	0.0012 (8)	−0.0044 (9)	0.0037 (10)
C6	0.0676 (14)	0.0717 (13)	0.0663 (13)	0.0022 (10)	−0.0110 (10)	0.0085 (10)
C10	0.0483 (10)	0.0550 (10)	0.0462 (10)	−0.0057 (7)	0.0028 (7)	−0.0013 (7)
C12	0.0428 (9)	0.0520 (9)	0.0483 (10)	−0.0068 (7)	0.0050 (7)	0.0003 (7)
C13	0.0509 (11)	0.0620 (11)	0.0526 (11)	0.0004 (7)	0.0093 (8)	−0.0027 (8)
C14	0.0482 (11)	0.0643 (11)	0.0759 (14)	0.0042 (8)	0.0055 (9)	0.0040 (9)
C15	0.0518 (12)	0.0698 (13)	0.0659 (13)	−0.0104 (8)	−0.0066 (9)	0.0135 (9)
C16	0.0621 (12)	0.0806 (13)	0.0469 (11)	−0.0122 (10)	0.0023 (9)	−0.0030 (9)
C17	0.0477 (10)	0.0669 (11)	0.0524 (11)	−0.0025 (8)	0.0068 (8)	−0.0071 (8)

Geometric parameters (Å, º)

O8—N7	1.215 (2)	C13—C14	1.380 (3)
O9—N7	1.215 (2)	C14—C15	1.382 (3)
N7—C4	1.468 (2)	C15—C16	1.370 (3)
N11—C10	1.260 (2)	C16—C17	1.383 (3)
N11—C12	1.419 (2)	C1—H1	0.9304
C1—C2	1.379 (3)	C2—H2	0.9298
C1—C6	1.379 (3)	C5—H5	0.9302
C2—C3	1.392 (2)	C6—H6	0.9300
C3—C4	1.393 (2)	C10—H10	0.9305
C3—C10	1.477 (2)	C13—H13	0.9297
C4—C5	1.385 (3)	C14—H14	0.9301
C5—C6	1.377 (3)	C15—H15	0.9299
C12—C13	1.384 (2)	C16—H16	0.9303
C12—C17	1.393 (3)	C17—H17	0.9298
O8···N7^i	3.151 (3)	C14···H1^vii	3.0618
O9···C16^ii	3.396 (3)	C15···H1^vii	3.0955
O9···C10	2.800 (2)	C16···H1^vii	3.0939
O8···H5	2.5136	C17···H10	2.6387
O8···H14^iii	2.8108	C17···H1^vii	3.0621
O8···H6^iv	2.8472	H1···C12^vii	3.0391
O9···H10	2.3932	H1···C13^vii	3.0187
O9···H5^i	2.7579	H1···C14^vii	3.0618
O9···H13^v	2.9105	H1···C15^vii	3.0955
O9···H1^iv	2.8656	H1···C16^vii	3.0939
N7···O8^i	3.151 (3)	H1···C17^vii	3.0621
N7···H10	2.7112	H1···O9^vi	2.8656
N11···H2	2.5668	H2···N11	2.5668
N11···H16^vi	2.9076	H5···O8	2.5136
C1···C13^vii	3.558 (3)	H5···O9^i	2.7579
C3···C15^viii	3.531 (3)	H6···O8^vi	2.8472
C10···C15^viii	3.427 (3)	H10···O9	2.3932
C10···O9	2.800 (2)	H10···N7	2.7112
C13···C1^vii	3.558 (3)	H10···C17	2.6387
C15···C3^ii	3.531 (3)	H10···H17	2.3283
C15···C10^ii	3.427 (3)	H13···O9^v	2.9105
C16···O9^viii	3.396 (3)	H13···C3^v	3.0337
C3···H13^v	3.0337	H13···C10^v	3.0363
C3···H15^viii	2.9892	H14···O8^ix	2.8108
C10···H13^v	3.0363	H15···C3^ii	2.9892
C10···H17	2.7139	H16···N11^iv	2.9076
C12···H1^vii	3.0391	H17···C10	2.7139
C13···H1^vii	3.0187	H17···H10	2.3283
O8—N7—O9	122.82 (18)	C12—C17—C16	120.03 (17)
O8—N7—C4	118.14 (17)	C2—C1—H1	119.79
O9—N7—C4	119.01 (16)	C6—C1—H1	119.75
C10—N11—C12	118.70 (15)	C1—C2—H2	119.24
C2—C1—C6	120.5 (2)	C3—C2—H2	119.21
C1—C2—C3	121.55 (18)	C4—C5—H5	120.55
C2—C3—C4	116.32 (16)	C6—C5—H5	120.59
C2—C3—C10	119.97 (16)	C1—C6—H6	120.07
C4—C3—C10	123.58 (15)	C5—C6—H6	120.06
N7—C4—C3	120.45 (15)	N11—C10—H10	119.63
N7—C4—C5	116.55 (16)	C3—C10—H10	119.65
C3—C4—C5	122.92 (17)	C12—C13—H13	119.88
C4—C5—C6	118.86 (19)	C14—C13—H13	119.83
C1—C6—C5	119.9 (2)	C13—C14—H14	119.88
N11—C10—C3	120.72 (15)	C15—C14—H14	119.90
N11—C12—C13	117.79 (15)	C14—C15—H15	120.06
N11—C12—C17	122.98 (15)	C16—C15—H15	120.06
C13—C12—C17	119.14 (16)	C15—C16—H16	119.78
C12—C13—C14	120.29 (17)	C17—C16—H16	119.81
C13—C14—C15	120.22 (19)	C12—C17—H17	119.98
C14—C15—C16	119.89 (19)	C16—C17—H17	119.99
C15—C16—C17	120.41 (18)
O8—N7—C4—C3	146.97 (18)	C2—C3—C4—C5	0.2 (3)
O9—N7—C4—C3	−35.0 (2)	C2—C3—C4—N7	176.84 (15)
O8—N7—C4—C5	−36.2 (2)	C10—C3—C4—C5	175.99 (17)
O9—N7—C4—C5	141.83 (19)	C3—C4—C5—C6	0.8 (3)
C10—N11—C12—C13	143.06 (16)	N7—C4—C5—C6	−175.91 (18)
C12—N11—C10—C3	175.05 (14)	C4—C5—C6—C1	−0.9 (3)
C10—N11—C12—C17	−40.3 (2)	N11—C12—C13—C14	178.56 (16)
C2—C1—C6—C5	−0.1 (3)	N11—C12—C17—C16	−177.79 (17)
C6—C1—C2—C3	1.2 (3)	C13—C12—C17—C16	−1.2 (2)
C1—C2—C3—C10	−177.14 (17)	C17—C12—C13—C14	1.7 (3)
C1—C2—C3—C4	−1.2 (3)	C12—C13—C14—C15	−1.5 (3)
C4—C3—C10—N11	163.25 (16)	C13—C14—C15—C16	0.7 (3)
C10—C3—C4—N7	−7.4 (2)	C14—C15—C16—C17	−0.1 (3)
C2—C3—C10—N11	−21.2 (2)	C15—C16—C17—C12	0.3 (3)

Symmetry codes: (i) −x, −y, −z; (ii) −x+1, y−1/2, −z+1/2; (iii) x−1, y, z; (iv) x, −y+1/2, z+1/2; (v) −x+1, −y, −z; (vi) x, −y+1/2, z−1/2; (vii) −x+1, −y+1, −z; (viii) −x+1, y+1/2, −z+1/2; (ix) x+1, y, z.