Torsional vibration and central bond length of N-benzylideneanilines

The crystal structures of N-benzylideneaniline (1), N-benzyl­idene-4-carboxyaniline (2), N-(4-methylbenzylidene)-4-nitroaniline (3), N-(4-nitrobenzylidene)-4-methoxyaniline (4), N-(4-nitrobenzylidene)-4-methylaniline (5), N-(4-methoxybenzylidene)aniline (6) and N-(4-methoxybenzylidene)-4-methylaniline (7) were determined by X-ray diffraction analyses at various temperatures. In the crystal structures of all the compounds, an apparent shortening of the central C=N bond was observed at room temperature. As the temperature was lowered, the observed bond lengths increased to approximately 1.28 Å at 90 K, irrespective of substituents in the molecules. The shortening and the temperature dependence of the C=N bond length are interpreted in terms of an artifact caused by the torsional vibration of the C-Ph and N-Ph bonds in the crystals. In the crystal structures of (1) and (7), a static disorder around the C=N bond was observed, which is also responsible for the apparent shortening of the C=N bond.

Computing details

For all compounds, data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures

(1_rt) N-benzylideneaniline

Crystal data

C13H11N	Dx = 1.185 Mg m^−3
Mr = 181.23	Melting point: 49.9 C K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.9503 (19) Å	Cell parameters from 2949 reflections
b = 7.9347 (13) Å	θ = 3.2–23.8°
c = 12.1664 (19) Å	µ = 0.07 mm^−1
β = 118.321 (3)°	T = 300 K
V = 1015.6 (3) Å^3	Block, colourless
Z = 4	0.36 × 0.30 × 0.01 mm
F(000) = 384

Data collection

Bruker SMART 1000 CCD diffractometer	2966 independent reflections
Radiation source: fine-focus sealed tube	1781 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.192 pixels mm^-1	θmax = 30.1°, θmin = 1.9°
ω scan	h = −16→16
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −11→11
Tmin = 0.976, Tmax = 0.999	l = −17→17
15417 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.0552P)^2 + 0.1448P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
2966 reflections	Δρmax = 0.18 e Å^−3
175 parameters	Δρmin = −0.16 e Å^−3
0 restraints

Special details

Experimental. ? The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different ϕ angle (0, 90, 180 and 270°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −32°. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections.

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	Occ. (<1)
N1A	0.42571 (12)	0.73672 (15)	0.41079 (12)	0.0557 (3)	0.96
C7A	0.45547 (13)	0.75772 (17)	0.32577 (13)	0.0515 (3)	0.96
H7A	0.3972	0.8084	0.2516	0.062*	0.96
N1B	0.499 (3)	0.755 (4)	0.413 (3)	0.055 (6)*	0.04
C7B	0.382 (4)	0.714 (5)	0.334 (4)	0.059 (8)*	0.04
H7B	0.3527	0.6529	0.2601	0.071*	0.04
C1	0.57904 (11)	0.70499 (16)	0.33957 (11)	0.0494 (3)
C2	0.61401 (14)	0.75402 (19)	0.25049 (14)	0.0614 (4)
C3	0.73115 (15)	0.7083 (2)	0.26343 (15)	0.0684 (4)
C4	0.81314 (15)	0.6135 (2)	0.36327 (16)	0.0661 (4)
C5	0.77889 (14)	0.56098 (19)	0.45110 (15)	0.0624 (4)
C6	0.66255 (12)	0.60632 (17)	0.43976 (12)	0.0540 (3)
C8	0.30384 (12)	0.78967 (16)	0.39113 (12)	0.0522 (3)
C9	0.29931 (14)	0.89441 (18)	0.47976 (14)	0.0610 (4)
C10	0.18440 (16)	0.9449 (2)	0.46887 (18)	0.0713 (4)
C11	0.07288 (15)	0.8890 (2)	0.37090 (18)	0.0747 (5)
C12	0.07606 (15)	0.7839 (2)	0.28247 (19)	0.0750 (5)
C13	0.19166 (14)	0.7345 (2)	0.29232 (16)	0.0650 (4)
H2	0.5533 (15)	0.822 (2)	0.1769 (15)	0.079 (5)*
H3	0.7543 (15)	0.745 (2)	0.2028 (16)	0.081 (5)*
H4	0.8952 (16)	0.582 (2)	0.3722 (14)	0.081 (5)*
H5	0.8340 (15)	0.495 (2)	0.5196 (15)	0.076 (5)*
H6	0.6370 (13)	0.5676 (19)	0.5010 (13)	0.065 (4)*
H9	0.3807 (16)	0.933 (2)	0.5504 (16)	0.078 (5)*
H10	0.1839 (16)	1.024 (3)	0.5319 (16)	0.092 (5)*
H11	−0.0082 (17)	0.922 (2)	0.3632 (15)	0.088 (5)*
H12	0.0002 (19)	0.741 (2)	0.2151 (18)	0.092 (6)*
H13	0.1950 (15)	0.665 (2)	0.2315 (15)	0.077 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0488 (7)	0.0631 (7)	0.0560 (8)	0.0047 (5)	0.0255 (6)	0.0039 (6)
C7A	0.0472 (7)	0.0536 (8)	0.0495 (8)	0.0008 (6)	0.0196 (6)	0.0036 (6)
C1	0.0478 (7)	0.0477 (6)	0.0524 (7)	−0.0039 (5)	0.0235 (6)	−0.0051 (5)
C2	0.0605 (8)	0.0680 (9)	0.0549 (8)	−0.0026 (7)	0.0268 (7)	0.0036 (7)
C3	0.0711 (9)	0.0812 (10)	0.0676 (9)	−0.0067 (8)	0.0448 (8)	−0.0042 (8)
C4	0.0578 (8)	0.0642 (9)	0.0855 (10)	0.0004 (7)	0.0414 (8)	−0.0086 (8)
C5	0.0555 (8)	0.0584 (8)	0.0695 (9)	0.0066 (6)	0.0266 (7)	0.0040 (7)
C6	0.0577 (8)	0.0513 (7)	0.0560 (7)	0.0000 (6)	0.0295 (6)	0.0011 (6)
C8	0.0500 (7)	0.0486 (7)	0.0616 (8)	0.0029 (5)	0.0295 (6)	0.0086 (6)
C9	0.0595 (8)	0.0569 (8)	0.0673 (9)	0.0008 (6)	0.0306 (7)	−0.0005 (7)
C10	0.0786 (11)	0.0591 (9)	0.0912 (11)	0.0076 (8)	0.0524 (9)	0.0006 (8)
C11	0.0601 (9)	0.0603 (9)	0.1150 (14)	0.0097 (7)	0.0508 (10)	0.0138 (9)
C12	0.0515 (8)	0.0697 (10)	0.0921 (12)	−0.0065 (7)	0.0244 (8)	0.0031 (9)
C13	0.0606 (9)	0.0628 (9)	0.0714 (9)	−0.0047 (7)	0.0311 (7)	−0.0066 (7)

Geometric parameters (Å, º)

N1A—C7A	1.2543 (19)	C4—H4	0.967 (17)
N1A—C8	1.4227 (17)	C5—C6	1.3783 (19)
C7A—C1	1.4658 (18)	C5—H5	0.941 (17)
C7A—H7A	0.9300	C6—H6	0.979 (15)
N1B—C7B	1.31 (5)	C8—C13	1.380 (2)
N1B—C1	1.64 (3)	C8—C9	1.383 (2)
C7B—C8	1.53 (4)	C9—C10	1.375 (2)
C7B—H7B	0.9300	C9—H9	0.993 (17)
C1—C2	1.3894 (19)	C10—C11	1.373 (2)
C1—C6	1.3930 (18)	C10—H10	0.996 (19)
C2—C3	1.381 (2)	C11—C12	1.376 (3)
C2—H2	1.000 (17)	C11—H11	0.964 (18)
C3—C4	1.368 (2)	C12—C13	1.385 (2)
C3—H3	0.948 (18)	C12—H12	0.95 (2)
C4—C5	1.378 (2)	C13—H13	0.940 (17)
C7A—N1A—C8	119.36 (13)	C6—C5—H5	119.0 (10)
N1A—C7A—C1	122.14 (13)	C5—C6—C1	120.28 (13)
N1A—C7A—H7A	118.9	C5—C6—H6	120.4 (8)
C1—C7A—H7A	118.9	C1—C6—H6	119.3 (8)
C7B—N1B—C1	104 (3)	C13—C8—C9	119.25 (13)
N1B—C7B—C8	104 (3)	C13—C8—N1A	123.14 (13)
N1B—C7B—H7B	128.1	C9—C8—N1A	117.52 (12)
C8—C7B—H7B	128.1	C13—C8—C7B	91.6 (16)
C2—C1—C6	118.96 (12)	C9—C8—C7B	148.3 (16)
C2—C1—C7A	119.36 (12)	N1A—C8—C7B	33.2 (16)
C6—C1—C7A	121.68 (12)	C10—C9—C8	120.44 (15)
C2—C1—N1B	145.8 (10)	C10—C9—H9	121.1 (9)
C6—C1—N1B	91.3 (11)	C8—C9—H9	118.5 (9)
C7A—C1—N1B	34.4 (11)	C11—C10—C9	120.21 (17)
C3—C2—C1	120.09 (14)	C11—C10—H10	121.0 (10)
C3—C2—H2	120.6 (9)	C9—C10—H10	118.8 (10)
C1—C2—H2	119.3 (9)	C10—C11—C12	119.93 (15)
C4—C3—C2	120.39 (15)	C10—C11—H11	120.9 (10)
C4—C3—H3	120.5 (10)	C12—C11—H11	119.1 (10)
C2—C3—H3	119.1 (10)	C11—C12—C13	120.00 (16)
C3—C4—C5	120.24 (14)	C11—C12—H12	121.5 (11)
C3—C4—H4	120.1 (10)	C13—C12—H12	118.5 (11)
C5—C4—H4	119.7 (10)	C8—C13—C12	120.17 (16)
C4—C5—C6	120.02 (15)	C8—C13—H13	119.0 (10)
C4—C5—H5	121.0 (10)	C12—C13—H13	120.8 (10)
C8—N1A—C7A—C1	−179.55 (12)	N1B—C1—C6—C5	−162.0 (10)
C1—N1B—C7B—C8	−170.0 (18)	C7A—N1A—C8—C13	56.2 (2)
N1A—C7A—C1—C2	−170.36 (14)	C7A—N1A—C8—C9	−127.28 (15)
N1A—C7A—C1—C6	9.8 (2)	C7A—N1A—C8—C7B	36 (3)
N1A—C7A—C1—N1B	−21.3 (18)	N1B—C7B—C8—C13	178 (2)
C7B—N1B—C1—C2	81 (3)	N1B—C7B—C8—C9	11 (5)
C7B—N1B—C1—C6	−126 (2)	N1B—C7B—C8—N1A	−18.7 (16)
C7B—N1B—C1—C7A	28.0 (18)	C13—C8—C9—C10	−0.8 (2)
C6—C1—C2—C3	−1.5 (2)	N1A—C8—C9—C10	−177.46 (13)
C7A—C1—C2—C3	178.68 (13)	C7B—C8—C9—C10	165 (3)
N1B—C1—C2—C3	147.6 (19)	C8—C9—C10—C11	1.2 (2)
C1—C2—C3—C4	0.5 (2)	C9—C10—C11—C12	−0.8 (3)
C2—C3—C4—C5	0.8 (2)	C10—C11—C12—C13	0.0 (3)
C3—C4—C5—C6	−1.1 (2)	C9—C8—C13—C12	0.0 (2)
C4—C5—C6—C1	0.1 (2)	N1A—C8—C13—C12	176.45 (14)
C2—C1—C6—C5	1.2 (2)	C7B—C8—C13—C12	−172.5 (14)
C7A—C1—C6—C5	−179.01 (13)	C11—C12—C13—C8	0.4 (2)

(1_90K) N-benzylideneaniline

Crystal data

C13H11N	Dx = 1.234 Mg m^−3
Mr = 181.23	Melting point: 49.9 C K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.8429 (9) Å	Cell parameters from 6138 reflections
b = 7.7182 (5) Å	θ = 3.3–30.0°
c = 12.1211 (9) Å	µ = 0.07 mm^−1
β = 118.341 (1)°	T = 90 K
V = 975.14 (12) Å^3	Block, colourless
Z = 4	0.36 × 0.30 × 0.01 mm
F(000) = 384

Data collection

Bruker SMART 1000 CCD diffractometer	2834 independent reflections
Radiation source: fine-focus sealed tube	2406 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 8.192 pixels mm^-1	θmax = 30.0°, θmin = 2.0°
ω scan	h = −16→16
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −10→10
Tmin = 0.975, Tmax = 0.999	l = −17→16
14636 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0577P)^2 + 0.1821P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2834 reflections	Δρmax = 0.36 e Å^−3
159 parameters	Δρmin = −0.19 e Å^−3
0 restraints

Special details

Experimental. The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different ϕ angle (0, 90, 180 and 270°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −32°. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections.

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	Occ. (<1)
N1A	0.42735 (7)	0.73867 (9)	0.41382 (7)	0.01921 (16)	0.95
C1A	0.57865 (7)	0.70215 (11)	0.33740 (9)	0.01613 (16)	0.95
C2A	0.61321 (9)	0.75104 (11)	0.24623 (8)	0.01949 (17)	0.95
H2A	0.5551	0.8158	0.1752	0.023*	0.95
C3A	0.73295 (10)	0.70470 (12)	0.25976 (8)	0.02155 (18)	0.95
H3A	0.7565	0.7386	0.1981	0.026*	0.95
C4A	0.81794 (8)	0.60897 (12)	0.36329 (10)	0.02077 (18)	0.95
H4A	0.8998	0.5788	0.3727	0.025*	0.95
C5A	0.78319 (8)	0.55706 (11)	0.45348 (8)	0.01937 (17)	0.95
H5A	0.8409	0.4901	0.5234	0.023*	0.95
C6A	0.66419 (9)	0.60347 (11)	0.44080 (8)	0.01728 (17)	0.95
H6A	0.6407	0.5683	0.5022	0.021*	0.95
C7A	0.45365 (8)	0.75612 (10)	0.32381 (8)	0.01793 (16)	0.95
H7A	0.3914	0.8048	0.2468	0.022*	0.95
C8A	0.30498 (8)	0.79195 (10)	0.39550 (9)	0.01663 (16)	0.95
C9A	0.30083 (8)	0.89847 (11)	0.48667 (8)	0.01825 (17)	0.95
H9A	0.3784	0.9354	0.5564	0.022*	0.95
C10A	0.18354 (10)	0.95058 (11)	0.47572 (9)	0.02071 (18)	0.95
H10A	0.1812	1.0254	0.5368	0.025*	0.95
C11A	0.06928 (9)	0.89323 (12)	0.37520 (11)	0.02167 (19)	0.95
H11A	−0.0108	0.9272	0.3686	0.026*	0.95
C12A	0.07298 (8)	0.78602 (12)	0.28465 (9)	0.02193 (18)	0.95
H12A	−0.0048	0.7472	0.2160	0.026*	0.95
C13A	0.19053 (9)	0.73530 (11)	0.29422 (8)	0.02000 (17)	0.95
H13A	0.1927	0.6625	0.2321	0.024*	0.95
N1B	0.4977 (18)	0.749 (2)	0.4113 (16)	0.036 (3)*	0.05
C1B	0.2601 (16)	0.7729 (18)	0.3368 (16)	0.027 (3)*	0.05
C2B	0.1275 (17)	0.7631 (19)	0.2652 (11)	0.038 (4)*	0.05
H2B	0.0903	0.7048	0.1868	0.045*	0.05
C3B	0.0493 (11)	0.839 (2)	0.3084 (16)	0.046 (6)*	0.05
H3B	−0.0414	0.8320	0.2595	0.055*	0.05
C4B	0.1037 (17)	0.924 (2)	0.4231 (17)	0.043 (6)*	0.05
H4B	0.0503	0.9757	0.4526	0.052*	0.05
C5B	0.2364 (18)	0.934 (2)	0.4947 (12)	0.041 (6)*	0.05
H5B	0.2736	0.9922	0.5731	0.049*	0.05
C6B	0.3146 (11)	0.858 (2)	0.4515 (15)	0.033 (4)*	0.05
H6B	0.4052	0.8650	0.5004	0.039*	0.05
C7B	0.3834 (19)	0.738 (2)	0.3319 (19)	0.033 (4)*	0.05
H7B	0.3704	0.6996	0.2522	0.040*	0.05
C8B	0.6064 (13)	0.675 (2)	0.3938 (14)	0.032 (4)*	0.05
C9B	0.7188 (16)	0.583 (2)	0.4664 (11)	0.041 (5)*	0.05
H9B	0.7335	0.5341	0.5440	0.049*	0.05
C10B	0.8098 (12)	0.5640 (19)	0.4257 (14)	0.035 (5)*	0.05
H10B	0.8866	0.5016	0.4754	0.042*	0.05
C11B	0.7884 (13)	0.636 (2)	0.3123 (15)	0.030 (4)*	0.05
H11B	0.8506	0.6229	0.2844	0.036*	0.05
C12B	0.6760 (16)	0.7275 (17)	0.2396 (10)	0.029 (4)*	0.05
H12B	0.6613	0.7767	0.1621	0.035*	0.05
C13B	0.5850 (11)	0.7468 (16)	0.2804 (13)	0.025 (3)*	0.05
H13B	0.5082	0.8093	0.2307	0.030*	0.05

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0157 (3)	0.0213 (3)	0.0203 (3)	0.0006 (2)	0.0083 (3)	−0.0009 (3)
C1A	0.0154 (3)	0.0162 (3)	0.0170 (4)	−0.0007 (3)	0.0079 (3)	−0.0006 (3)
C2A	0.0183 (4)	0.0232 (4)	0.0176 (4)	−0.0007 (3)	0.0090 (3)	0.0005 (3)
C3A	0.0212 (4)	0.0251 (4)	0.0219 (4)	−0.0013 (3)	0.0132 (3)	−0.0018 (3)
C4A	0.0187 (4)	0.0206 (4)	0.0258 (5)	0.0001 (3)	0.0127 (4)	−0.0020 (3)
C5A	0.0168 (4)	0.0188 (4)	0.0222 (4)	0.0015 (3)	0.0091 (3)	0.0009 (3)
C6A	0.0173 (4)	0.0165 (4)	0.0188 (4)	0.0009 (3)	0.0092 (3)	0.0006 (3)
C7A	0.0156 (3)	0.0191 (4)	0.0180 (4)	0.0001 (3)	0.0071 (3)	0.0012 (3)
C8A	0.0164 (4)	0.0161 (4)	0.0186 (4)	0.0003 (3)	0.0093 (3)	0.0008 (3)
C9A	0.0179 (4)	0.0175 (4)	0.0205 (4)	0.0009 (3)	0.0101 (3)	−0.0008 (3)
C10A	0.0213 (5)	0.0182 (4)	0.0266 (4)	0.0024 (3)	0.0146 (3)	0.0003 (3)
C11A	0.0177 (4)	0.0189 (4)	0.0304 (5)	0.0026 (3)	0.0130 (4)	0.0032 (4)
C12A	0.0166 (4)	0.0220 (4)	0.0257 (4)	−0.0011 (3)	0.0088 (3)	0.0009 (3)
C13A	0.0174 (4)	0.0209 (4)	0.0218 (4)	−0.0020 (3)	0.0094 (3)	−0.0021 (3)

Geometric parameters (Å, º)

N1A—C7A	1.2760 (11)	N1B—C7B	1.24 (3)
N1A—C8A	1.4188 (10)	N1B—C8B	1.51 (2)
C1A—C2A	1.4002 (11)	C1B—C2B	1.3900
C1A—C6A	1.4042 (11)	C1B—C6B	1.3900
C1A—C7A	1.4699 (11)	C1B—C7B	1.51 (2)
C2A—C3A	1.3947 (12)	C2B—C3B	1.3900
C3A—C4A	1.3909 (13)	C3B—C4B	1.3900
C4A—C5A	1.3972 (12)	C4B—C5B	1.3900
C5A—C6A	1.3902 (11)	C5B—C6B	1.3900
C8A—C9A	1.3968 (11)	C8B—C9B	1.3900
C8A—C13A	1.3984 (11)	C8B—C13B	1.3900
C9A—C10A	1.3907 (11)	C9B—C10B	1.3900
C10A—C11A	1.3950 (13)	C10B—C11B	1.3900
C11A—C12A	1.3917 (14)	C11B—C12B	1.3900
C12A—C13A	1.3970 (12)	C12B—C13B	1.3900
C7A—N1A—C8A	118.78 (7)	C7B—N1B—C8B	123.7 (17)
C2A—C1A—C6A	119.56 (7)	C2B—C1B—C6B	120.0
C2A—C1A—C7A	119.43 (8)	C2B—C1B—C7B	142.3 (14)
C6A—C1A—C7A	121.01 (8)	C6B—C1B—C7B	97.2 (14)
C3A—C2A—C1A	120.00 (8)	C3B—C2B—C1B	120.0
C4A—C3A—C2A	120.15 (8)	C2B—C3B—C4B	120.0
C3A—C4A—C5A	120.17 (8)	C5B—C4B—C3B	120.0
C6A—C5A—C4A	119.95 (8)	C4B—C5B—C6B	120.0
C5A—C6A—C1A	120.16 (7)	C5B—C6B—C1B	120.0
N1A—C7A—C1A	121.06 (8)	N1B—C7B—C1B	133 (2)
C9A—C8A—C13A	119.67 (7)	C9B—C8B—C13B	120.0
C9A—C8A—N1A	117.63 (8)	C9B—C8B—N1B	136.5 (13)
C13A—C8A—N1A	122.63 (8)	C13B—C8B—N1B	102.6 (13)
C10A—C9A—C8A	120.23 (8)	C8B—C9B—C10B	120.0
C9A—C10A—C11A	120.15 (8)	C11B—C10B—C9B	120.0
C12A—C11A—C10A	119.79 (8)	C12B—C11B—C10B	120.0
C11A—C12A—C13A	120.28 (8)	C11B—C12B—C13B	120.0
C12A—C13A—C8A	119.85 (8)	C12B—C13B—C8B	120.0
C6A—C1A—C2A—C3A	−1.29 (12)	C6B—C1B—C2B—C3B	0.0
C7A—C1A—C2A—C3A	178.25 (7)	C7B—C1B—C2B—C3B	−170 (2)
C1A—C2A—C3A—C4A	0.42 (13)	C1B—C2B—C3B—C4B	0.0
C2A—C3A—C4A—C5A	0.74 (13)	C2B—C3B—C4B—C5B	0.0
C3A—C4A—C5A—C6A	−1.01 (13)	C3B—C4B—C5B—C6B	0.0
C4A—C5A—C6A—C1A	0.13 (12)	C4B—C5B—C6B—C1B	0.0
C2A—C1A—C6A—C5A	1.02 (12)	C2B—C1B—C6B—C5B	0.0
C7A—C1A—C6A—C5A	−178.52 (7)	C7B—C1B—C6B—C5B	174.0 (12)
C8A—N1A—C7A—C1A	−179.64 (7)	C8B—N1B—C7B—C1B	167.8 (17)
C2A—C1A—C7A—N1A	−168.55 (8)	C2B—C1B—C7B—N1B	−176.3 (18)
C6A—C1A—C7A—N1A	10.99 (12)	C6B—C1B—C7B—N1B	12 (2)
C7A—N1A—C8A—C9A	−130.63 (8)	C7B—N1B—C8B—C9B	−137.3 (17)
C7A—N1A—C8A—C13A	52.56 (11)	C7B—N1B—C8B—C13B	54 (2)
C13A—C8A—C9A—C10A	−1.15 (12)	C13B—C8B—C9B—C10B	0.0
N1A—C8A—C9A—C10A	−178.06 (7)	N1B—C8B—C9B—C10B	−167.7 (17)
C8A—C9A—C10A—C11A	1.60 (13)	C8B—C9B—C10B—C11B	0.0
C9A—C10A—C11A—C12A	−1.10 (13)	C9B—C10B—C11B—C12B	0.0
C10A—C11A—C12A—C13A	0.18 (13)	C10B—C11B—C12B—C13B	0.0
C11A—C12A—C13A—C8A	0.26 (13)	C11B—C12B—C13B—C8B	0.0
C9A—C8A—C13A—C12A	0.23 (12)	C9B—C8B—C13B—C12B	0.0
N1A—C8A—C13A—C12A	176.98 (8)	N1B—C8B—C13B—C12B	171.3 (12)

(2_rt) N-benzylidene-4-carboxyaniline

Crystal data

C14H11NO2	Dx = 1.319 Mg m^−3
Mr = 225.24	Melting point: 189.7 C K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.6639 (7) Å	Cell parameters from 8458 reflections
b = 30.878 (3) Å	θ = 2.6–30.0°
c = 7.6091 (9) Å	µ = 0.09 mm^−1
β = 133.576 (2)°	T = 300 K
V = 1134.3 (2) Å^3	Block, pale yellow
Z = 4	0.70 × 0.66 × 0.16 mm
F(000) = 472

Data collection

Bruker SMART 1000 CCD diffractometer	3305 independent reflections
Radiation source: fine-focus sealed tube	2783 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 8.192 pixels mm^-1	θmax = 30.0°, θmin = 1.3°
ω scan	h = −9→9
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −43→43
Tmin = 0.940, Tmax = 0.986	l = −10→10
17030 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.160	w = 1/[σ^2(Fo^2) + (0.0516P)^2 + 0.6951P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
3305 reflections	Δρmax = 0.23 e Å^−3
202 parameters	Δρmin = −0.22 e Å^−3
0 restraints

Special details

Experimental. The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different ϕ angle (0, 90, 180 and 270°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −32°. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections.

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	Occ. (<1)
N1	0.8293 (3)	0.12608 (5)	0.3235 (3)	0.0409 (3)
O1	0.2834 (3)	0.03495 (5)	0.6644 (3)	0.0500 (4)
O2	0.0043 (3)	0.01118 (5)	0.2837 (3)	0.0548 (4)
C1	0.8208 (4)	0.17062 (5)	0.0577 (3)	0.0360 (3)
C2	0.6514 (4)	0.19632 (7)	−0.1494 (4)	0.0478 (4)
C3	0.7650 (5)	0.22198 (8)	−0.2113 (4)	0.0568 (5)
C4	1.0464 (5)	0.22155 (7)	−0.0702 (5)	0.0548 (5)
C5	1.2164 (5)	0.19561 (7)	0.1346 (4)	0.0501 (5)
C6	1.1050 (4)	0.17024 (6)	0.1998 (4)	0.0411 (4)
C7	0.6920 (4)	0.14453 (6)	0.1199 (3)	0.0394 (4)
C8	0.6778 (4)	0.10145 (6)	0.3568 (3)	0.0360 (3)
C9	0.7526 (4)	0.10412 (6)	0.5786 (3)	0.0405 (4)
C10	0.6025 (4)	0.08167 (6)	0.6138 (3)	0.0385 (4)
C11	0.3780 (3)	0.05610 (5)	0.4287 (3)	0.0333 (3)
C12	0.3110 (4)	0.05219 (6)	0.2112 (3)	0.0413 (4)
C13	0.4609 (4)	0.07448 (6)	0.1758 (3)	0.0435 (4)
C14	0.2124 (4)	0.03264 (5)	0.4618 (3)	0.0361 (3)
H2	0.448 (5)	0.1970 (8)	−0.253 (4)	0.055 (7)*
H3	0.647 (6)	0.2397 (9)	−0.358 (5)	0.066 (7)*
H4	1.122 (6)	0.2394 (10)	−0.121 (5)	0.084 (9)*
H5	1.417 (6)	0.1959 (9)	0.237 (5)	0.073 (8)*
H6	1.222 (5)	0.1523 (7)	0.339 (4)	0.043 (5)*
H7	0.481 (5)	0.1432 (7)	−0.012 (4)	0.050 (6)*
H9	0.916 (5)	0.1224 (8)	0.711 (5)	0.057 (7)*
H10	0.653 (4)	0.0848 (7)	0.777 (4)	0.044 (6)*
H12	0.155 (5)	0.0336 (7)	0.082 (4)	0.044 (6)*
H13	0.426 (5)	0.0702 (7)	0.031 (4)	0.051 (6)*
H14	0.173 (10)	0.0209 (18)	0.678 (8)	0.050 (10)*	0.52 (4)
H14'	−0.098 (12)	0.000 (2)	0.298 (9)	0.050 (10)*	0.48 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0418 (8)	0.0427 (8)	0.0446 (8)	−0.0033 (6)	0.0322 (7)	0.0009 (6)
O1	0.0598 (9)	0.0583 (9)	0.0462 (8)	−0.0165 (7)	0.0420 (7)	−0.0091 (6)
O2	0.0587 (9)	0.0664 (10)	0.0507 (8)	−0.0285 (8)	0.0421 (8)	−0.0195 (7)
C1	0.0414 (9)	0.0348 (8)	0.0380 (8)	−0.0012 (6)	0.0298 (8)	−0.0017 (6)
C2	0.0461 (10)	0.0542 (11)	0.0432 (10)	0.0021 (9)	0.0308 (9)	0.0054 (8)
C3	0.0680 (14)	0.0536 (12)	0.0522 (12)	0.0036 (10)	0.0428 (12)	0.0135 (10)
C4	0.0730 (15)	0.0475 (11)	0.0660 (14)	−0.0105 (10)	0.0563 (13)	−0.0010 (10)
C5	0.0483 (11)	0.0505 (11)	0.0622 (13)	−0.0068 (9)	0.0422 (11)	−0.0050 (9)
C6	0.0428 (9)	0.0374 (9)	0.0459 (10)	0.0018 (7)	0.0317 (8)	0.0025 (7)
C7	0.0392 (9)	0.0421 (9)	0.0421 (9)	−0.0018 (7)	0.0300 (8)	−0.0005 (7)
C8	0.0367 (8)	0.0362 (8)	0.0403 (8)	−0.0001 (6)	0.0285 (7)	0.0018 (6)
C9	0.0362 (8)	0.0456 (9)	0.0345 (8)	−0.0063 (7)	0.0224 (7)	−0.0018 (7)
C10	0.0406 (9)	0.0428 (9)	0.0321 (8)	−0.0043 (7)	0.0251 (7)	−0.0020 (7)
C11	0.0379 (8)	0.0315 (7)	0.0348 (8)	−0.0014 (6)	0.0267 (7)	−0.0008 (6)
C12	0.0500 (10)	0.0401 (9)	0.0389 (9)	−0.0123 (8)	0.0326 (8)	−0.0095 (7)
C13	0.0576 (11)	0.0440 (9)	0.0419 (9)	−0.0101 (8)	0.0392 (9)	−0.0072 (7)
C14	0.0413 (9)	0.0343 (8)	0.0391 (8)	−0.0035 (7)	0.0302 (8)	−0.0033 (6)

Geometric parameters (Å, º)

N1—C7	1.268 (2)	C5—C6	1.385 (3)
N1—C8	1.420 (2)	C5—H5	0.98 (3)
O1—C14	1.265 (2)	C6—H6	0.95 (2)
O1—H14	0.92 (6)	C7—H7	1.02 (2)
O2—C14	1.268 (2)	C8—C13	1.391 (3)
O2—H14'	0.84 (7)	C8—C9	1.394 (2)
C1—C6	1.390 (3)	C9—C10	1.386 (2)
C1—C2	1.391 (3)	C9—H9	1.00 (3)
C1—C7	1.473 (2)	C10—C11	1.393 (2)
C2—C3	1.383 (3)	C10—H10	1.04 (2)
C2—H2	0.99 (2)	C11—C12	1.390 (2)
C3—C4	1.376 (4)	C11—C14	1.480 (2)
C3—H3	0.98 (3)	C12—C13	1.384 (3)
C4—C5	1.385 (3)	C12—H12	0.98 (2)
C4—H4	0.99 (3)	C13—H13	0.96 (2)
C7—N1—C8	117.12 (16)	C1—C7—H7	114.9 (13)
C14—O1—H14	117 (3)	C13—C8—C9	119.64 (16)
C14—O2—H14'	118 (4)	C13—C8—N1	121.70 (16)
C6—C1—C2	119.50 (17)	C9—C8—N1	118.65 (16)
C6—C1—C7	121.91 (16)	C10—C9—C8	120.04 (16)
C2—C1—C7	118.59 (17)	C10—C9—H9	120.9 (14)
C3—C2—C1	120.4 (2)	C8—C9—H9	119.1 (14)
C3—C2—H2	118.9 (14)	C9—C10—C11	120.20 (16)
C1—C2—H2	120.7 (14)	C9—C10—H10	119.9 (12)
C4—C3—C2	120.0 (2)	C11—C10—H10	119.8 (12)
C4—C3—H3	119.0 (16)	C12—C11—C10	119.51 (15)
C2—C3—H3	120.9 (16)	C12—C11—C14	119.67 (15)
C3—C4—C5	120.08 (19)	C10—C11—C14	120.82 (15)
C3—C4—H4	118.6 (18)	C13—C12—C11	120.38 (16)
C5—C4—H4	121.3 (18)	C13—C12—H12	120.0 (13)
C4—C5—C6	120.3 (2)	C11—C12—H12	119.6 (13)
C4—C5—H5	119.9 (17)	C12—C13—C8	120.12 (16)
C6—C5—H5	119.8 (17)	C12—C13—H13	120.9 (14)
C5—C6—C1	119.72 (18)	C8—C13—H13	118.8 (14)
C5—C6—H6	119.8 (13)	O1—C14—O2	123.14 (16)
C1—C6—H6	120.5 (13)	O1—C14—C11	118.95 (15)
N1—C7—C1	123.28 (17)	O2—C14—C11	117.91 (15)
N1—C7—H7	121.8 (13)
C6—C1—C2—C3	−1.3 (3)	N1—C8—C9—C10	177.69 (17)
C7—C1—C2—C3	178.68 (19)	C8—C9—C10—C11	0.6 (3)
C1—C2—C3—C4	1.2 (3)	C9—C10—C11—C12	2.0 (3)
C2—C3—C4—C5	−0.3 (4)	C9—C10—C11—C14	−178.79 (17)
C3—C4—C5—C6	−0.5 (3)	C10—C11—C12—C13	−1.8 (3)
C4—C5—C6—C1	0.5 (3)	C14—C11—C12—C13	178.93 (17)
C2—C1—C6—C5	0.4 (3)	C11—C12—C13—C8	−0.9 (3)
C7—C1—C6—C5	−179.53 (17)	C9—C8—C13—C12	3.4 (3)
C8—N1—C7—C1	−179.12 (16)	N1—C8—C13—C12	−177.56 (18)
C6—C1—C7—N1	12.5 (3)	C12—C11—C14—O1	176.87 (17)
C2—C1—C7—N1	−167.46 (19)	C10—C11—C14—O1	−2.4 (3)
C7—N1—C8—C13	42.0 (3)	C12—C11—C14—O2	−3.3 (3)
C7—N1—C8—C9	−138.93 (19)	C10—C11—C14—O2	177.42 (17)
C13—C8—C9—C10	−3.2 (3)

(2_90K) N-benzylidene-4-carboxyaniline

Crystal data

C14H11NO2	Dx = 1.369 Mg m^−3
Mr = 225.24	Melting point: 189.7 C K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.6193 (5) Å	Cell parameters from 11149 reflections
b = 30.381 (2) Å	θ = 3.2–30.0°
c = 7.5764 (6) Å	µ = 0.09 mm^−1
β = 134.151 (1)°	T = 90 K
V = 1093.21 (14) Å^3	Block, pale yellow
Z = 4	0.70 × 0.66 × 0.16 mm
F(000) = 472

Data collection

Bruker SMART 1000 CCD diffractometer	3193 independent reflections
Radiation source: fine-focus sealed tube	3046 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 8.192 pixels mm^-1	θmax = 30.0°, θmin = 1.3°
ω scan	h = −9→9
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −42→42
Tmin = 0.938, Tmax = 0.985	l = −10→10
16650 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0447P)^2 + 0.6769P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
3193 reflections	Δρmax = 0.48 e Å^−3
202 parameters	Δρmin = −0.21 e Å^−3
0 restraints

Special details

Experimental. The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different ϕ angle (0, 90, 180 and 270°) for the crystal and each exposure of 5 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −32°. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections.

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	Occ. (<1)
N1	0.8541 (2)	0.12646 (3)	0.33984 (18)	0.01509 (19)
O1	0.29184 (19)	0.03516 (3)	0.67316 (16)	0.01824 (18)
O2	0.00442 (19)	0.01147 (3)	0.28363 (17)	0.02062 (19)
C1	0.8380 (2)	0.17080 (3)	0.0644 (2)	0.0133 (2)
C2	0.6619 (2)	0.19682 (4)	−0.1475 (2)	0.0164 (2)
C3	0.7742 (3)	0.22270 (4)	−0.2132 (2)	0.0186 (2)
C4	1.0629 (3)	0.22237 (4)	−0.0693 (2)	0.0179 (2)
C5	1.2394 (2)	0.19602 (4)	0.1412 (2)	0.0169 (2)
C6	1.1284 (2)	0.17038 (4)	0.2085 (2)	0.0147 (2)
C7	0.7106 (2)	0.14476 (4)	0.1296 (2)	0.0145 (2)
C8	0.6996 (2)	0.10171 (4)	0.3717 (2)	0.0134 (2)
C9	0.7758 (2)	0.10450 (4)	0.5963 (2)	0.0144 (2)
C10	0.6210 (2)	0.08193 (4)	0.6287 (2)	0.0139 (2)
C11	0.3904 (2)	0.05615 (3)	0.4381 (2)	0.0124 (2)
C12	0.3221 (2)	0.05187 (4)	0.2180 (2)	0.0147 (2)
C13	0.4770 (2)	0.07426 (4)	0.1853 (2)	0.0154 (2)
C14	0.2183 (2)	0.03279 (3)	0.4670 (2)	0.0131 (2)
H2	0.458 (4)	0.1966 (6)	−0.251 (3)	0.028 (5)*
H3	0.649 (4)	0.2411 (6)	−0.362 (3)	0.023 (4)*
H4	1.142 (4)	0.2404 (6)	−0.117 (4)	0.032 (5)*
H5	1.443 (4)	0.1957 (5)	0.242 (3)	0.020 (4)*
H6	1.251 (3)	0.1524 (5)	0.355 (3)	0.018 (4)*
H7	0.505 (3)	0.1427 (5)	0.003 (3)	0.018 (4)*
H9	0.933 (4)	0.1232 (6)	0.727 (3)	0.020 (4)*
H10	0.674 (3)	0.0842 (5)	0.788 (3)	0.020 (4)*
H12	0.167 (4)	0.0332 (6)	0.088 (3)	0.020 (4)*
H13	0.430 (4)	0.0701 (6)	0.034 (3)	0.020 (4)*
H14	0.184 (8)	0.0190 (12)	0.676 (6)	0.026 (7)*	0.55 (3)
H14'	−0.102 (9)	−0.0018 (15)	0.296 (8)	0.026 (7)*	0.45 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0166 (4)	0.0147 (4)	0.0176 (4)	−0.0007 (3)	0.0132 (4)	0.0002 (3)
O1	0.0227 (4)	0.0206 (4)	0.0178 (4)	−0.0026 (3)	0.0165 (4)	−0.0009 (3)
O2	0.0200 (4)	0.0240 (4)	0.0212 (4)	−0.0094 (3)	0.0155 (4)	−0.0078 (3)
C1	0.0160 (5)	0.0122 (4)	0.0149 (5)	−0.0008 (4)	0.0119 (4)	−0.0011 (4)
C2	0.0156 (5)	0.0178 (5)	0.0155 (5)	0.0004 (4)	0.0107 (4)	0.0007 (4)
C3	0.0215 (6)	0.0181 (5)	0.0174 (5)	0.0013 (4)	0.0140 (5)	0.0032 (4)
C4	0.0227 (6)	0.0159 (5)	0.0213 (5)	−0.0030 (4)	0.0176 (5)	−0.0010 (4)
C5	0.0165 (5)	0.0173 (5)	0.0199 (5)	−0.0017 (4)	0.0138 (5)	−0.0018 (4)
C6	0.0158 (5)	0.0130 (5)	0.0160 (5)	0.0007 (4)	0.0114 (4)	0.0005 (4)
C7	0.0148 (5)	0.0146 (5)	0.0166 (5)	−0.0003 (4)	0.0118 (4)	−0.0003 (4)
C8	0.0137 (5)	0.0133 (5)	0.0154 (5)	0.0013 (4)	0.0110 (4)	0.0018 (4)
C9	0.0131 (5)	0.0154 (5)	0.0127 (5)	−0.0010 (4)	0.0083 (4)	0.0002 (4)
C10	0.0149 (5)	0.0148 (5)	0.0122 (4)	−0.0001 (4)	0.0095 (4)	0.0001 (4)
C11	0.0139 (5)	0.0115 (4)	0.0140 (5)	0.0007 (3)	0.0105 (4)	0.0008 (3)
C12	0.0170 (5)	0.0139 (5)	0.0144 (5)	−0.0028 (4)	0.0113 (4)	−0.0025 (4)
C13	0.0190 (5)	0.0157 (5)	0.0152 (5)	−0.0019 (4)	0.0133 (4)	−0.0015 (4)
C14	0.0146 (5)	0.0120 (4)	0.0144 (5)	0.0004 (4)	0.0107 (4)	0.0001 (4)

Geometric parameters (Å, º)

N1—C7	1.2811 (15)	C5—C6	1.3894 (15)
N1—C8	1.4193 (14)	C5—H5	0.984 (17)
O1—C14	1.2741 (13)	C6—H6	0.967 (17)
O1—H14	0.88 (4)	C7—H7	0.980 (16)
O2—C14	1.2704 (14)	C8—C9	1.4004 (15)
O2—H14'	0.87 (5)	C8—C13	1.4006 (15)
C1—C2	1.3980 (15)	C9—C10	1.3897 (15)
C1—C6	1.4009 (15)	C9—H9	0.974 (17)
C1—C7	1.4699 (15)	C10—C11	1.3993 (15)
C2—C3	1.3905 (16)	C10—H10	0.995 (17)
C2—H2	0.982 (19)	C11—C12	1.3967 (15)
C3—C4	1.3923 (17)	C11—C14	1.4821 (15)
C3—H3	0.985 (18)	C12—C13	1.3893 (15)
C4—C5	1.3977 (17)	C12—H12	0.968 (17)
C4—H4	0.98 (2)	C13—H13	0.964 (17)
C7—N1—C8	116.33 (10)	C1—C7—H7	115.8 (10)
C14—O1—H14	112 (2)	C9—C8—C13	119.80 (10)
C14—O2—H14'	119 (3)	C9—C8—N1	118.83 (10)
C2—C1—C6	119.62 (10)	C13—C8—N1	121.37 (10)
C2—C1—C7	118.39 (10)	C10—C9—C8	119.94 (10)
C6—C1—C7	121.98 (10)	C10—C9—H9	120.5 (10)
C3—C2—C1	120.30 (11)	C8—C9—H9	119.6 (10)
C3—C2—H2	119.8 (11)	C9—C10—C11	120.14 (10)
C1—C2—H2	119.9 (11)	C9—C10—H10	119.8 (10)
C2—C3—C4	120.02 (11)	C11—C10—H10	120.0 (10)
C2—C3—H3	119.8 (10)	C12—C11—C10	119.85 (10)
C4—C3—H3	120.1 (10)	C12—C11—C14	119.25 (10)
C3—C4—C5	119.87 (11)	C10—C11—C14	120.90 (10)
C3—C4—H4	119.9 (11)	C13—C12—C11	120.12 (10)
C5—C4—H4	120.3 (11)	C13—C12—H12	119.9 (10)
C6—C5—C4	120.31 (11)	C11—C12—H12	120.0 (10)
C6—C5—H5	120.0 (10)	C12—C13—C8	120.02 (10)
C4—C5—H5	119.7 (10)	C12—C13—H13	118.8 (10)
C5—C6—C1	119.87 (10)	C8—C13—H13	121.2 (10)
C5—C6—H6	120.2 (10)	O2—C14—O1	123.53 (10)
C1—C6—H6	119.9 (10)	O2—C14—C11	117.94 (10)
N1—C7—C1	123.33 (10)	O1—C14—C11	118.53 (10)
N1—C7—H7	120.9 (10)
C6—C1—C2—C3	−1.03 (17)	N1—C8—C9—C10	177.51 (10)
C7—C1—C2—C3	178.62 (10)	C8—C9—C10—C11	0.49 (17)
C1—C2—C3—C4	0.83 (18)	C9—C10—C11—C12	2.28 (16)
C2—C3—C4—C5	−0.10 (18)	C9—C10—C11—C14	−178.38 (10)
C3—C4—C5—C6	−0.43 (18)	C10—C11—C12—C13	−2.03 (17)
C4—C5—C6—C1	0.23 (17)	C14—C11—C12—C13	178.61 (10)
C2—C1—C6—C5	0.50 (16)	C11—C12—C13—C8	−0.98 (17)
C7—C1—C6—C5	−179.13 (10)	C9—C8—C13—C12	3.73 (17)
C8—N1—C7—C1	−178.77 (10)	N1—C8—C13—C12	−177.29 (10)
C2—C1—C7—N1	−166.65 (11)	C12—C11—C14—O2	−3.67 (16)
C6—C1—C7—N1	12.98 (17)	C10—C11—C14—O2	176.98 (10)
C7—N1—C8—C9	−139.64 (11)	C12—C11—C14—O1	176.44 (10)
C7—N1—C8—C13	41.36 (15)	C10—C11—C14—O1	−2.91 (16)
C13—C8—C9—C10	−3.48 (17)

(3_rt) N-(4-methylbenzylidene)-4-nitroaniline

Crystal data

C14H12N2O2	Dx = 1.324 Mg m^−3
Mr = 240.26	Melting point: 135.7 C K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.5033 (12) Å	Cell parameters from 4693 reflections
b = 7.2979 (5) Å	θ = 2.8–27.3°
c = 12.7983 (8) Å	µ = 0.09 mm^−1
β = 123.625 (1)°	T = 300 K
V = 1205.74 (15) Å^3	Plate, pale yellow
Z = 4	0.60 × 0.56 × 0.04 mm
F(000) = 504

Data collection

Bruker SMART 1000 CCD diffractometer	3506 independent reflections
Radiation source: fine-focus sealed tube	2359 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.192 pixels mm^-1	θmax = 30.0°, θmin = 3.2°
ω scan	h = −21→21
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −10→10
Tmin = 0.948, Tmax = 0.996	l = −18→18
16372 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0475P)^2 + 0.2849P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
3506 reflections	Δρmax = 0.20 e Å^−3
219 parameters	Δρmin = −0.16 e Å^−3
0 restraints

Special details

Experimental. The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different ϕ angle (0, 90, 180 and 270°) for the crystal and each exposure of 20 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −32°. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections.

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	Occ. (<1)
N1	0.43342 (9)	0.24058 (16)	0.88783 (11)	0.0503 (3)
N2	0.05236 (11)	0.3426 (2)	0.83441 (14)	0.0651 (4)
O1	0.05555 (10)	0.4133 (2)	0.92320 (13)	0.0873 (4)
O2	−0.02727 (10)	0.2868 (3)	0.74129 (15)	0.1024 (5)
C1	0.55407 (10)	0.21476 (16)	0.82877 (11)	0.0404 (3)
C2	0.57844 (11)	0.25652 (19)	0.74200 (13)	0.0481 (3)
C3	0.67707 (12)	0.2248 (2)	0.76983 (14)	0.0517 (3)
C4	0.75418 (10)	0.15237 (18)	0.88445 (13)	0.0481 (3)
C5	0.72885 (11)	0.1067 (2)	0.96974 (13)	0.0490 (3)
C6	0.63068 (10)	0.13629 (19)	0.94288 (12)	0.0445 (3)
C7	0.45132 (10)	0.25514 (17)	0.80310 (12)	0.0433 (3)
C8	0.33450 (10)	0.27414 (17)	0.86332 (12)	0.0441 (3)
C9	0.32908 (12)	0.3862 (2)	0.94789 (14)	0.0519 (3)
C10	0.23660 (12)	0.4112 (2)	0.93680 (14)	0.0523 (3)
C11	0.14952 (10)	0.32348 (19)	0.84136 (13)	0.0488 (3)
C12	0.15137 (11)	0.2148 (2)	0.75415 (14)	0.0523 (3)
C13	0.24491 (11)	0.1908 (2)	0.76581 (13)	0.0487 (3)
C14	0.86278 (15)	0.1250 (3)	0.9170 (2)	0.0712 (5)
H2	0.5254 (12)	0.312 (2)	0.6624 (15)	0.059 (4)*
H3	0.6917 (13)	0.257 (2)	0.7086 (16)	0.068 (5)*
H5	0.7814 (12)	0.055 (2)	1.0504 (15)	0.064 (4)*
H6	0.6164 (11)	0.103 (2)	1.0032 (14)	0.059 (4)*
H7	0.4000 (11)	0.300 (2)	0.7196 (14)	0.051 (4)*
H9	0.2484 (12)	0.113 (2)	0.7061 (14)	0.061 (4)*
H10	0.0886 (13)	0.155 (2)	0.6870 (15)	0.064 (5)*
H12	0.2355 (11)	0.487 (2)	0.9969 (14)	0.057 (4)*
H13	0.3925 (12)	0.443 (2)	1.0160 (15)	0.061 (4)*
H141	0.862 (2)	0.144 (5)	0.837 (3)	0.068 (4)*	0.60 (2)
H142	0.908 (3)	0.207 (5)	0.975 (3)	0.068 (4)*	0.60 (2)
H143	0.890 (2)	−0.010 (5)	0.953 (3)	0.068 (4)*	0.60 (2)
H144	0.888 (4)	0.253 (7)	0.913 (5)	0.068 (4)*	0.40 (2)
H145	0.918 (4)	0.090 (8)	1.014 (5)	0.068 (4)*	0.40 (2)
H146	0.866 (4)	0.052 (7)	0.866 (5)	0.068 (4)*	0.40 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0461 (6)	0.0550 (7)	0.0490 (6)	0.0067 (5)	0.0258 (5)	0.0014 (5)
N2	0.0571 (8)	0.0780 (9)	0.0702 (9)	0.0127 (7)	0.0415 (7)	0.0144 (7)
O1	0.0845 (9)	0.1118 (11)	0.0943 (9)	0.0134 (8)	0.0675 (8)	−0.0002 (8)
O2	0.0529 (7)	0.1616 (16)	0.0914 (10)	0.0022 (9)	0.0391 (8)	−0.0107 (10)
C1	0.0435 (6)	0.0356 (6)	0.0399 (6)	−0.0018 (5)	0.0217 (5)	−0.0028 (5)
C2	0.0555 (8)	0.0458 (7)	0.0415 (7)	0.0003 (6)	0.0259 (6)	0.0034 (6)
C3	0.0637 (9)	0.0505 (8)	0.0530 (8)	−0.0073 (6)	0.0400 (7)	−0.0039 (6)
C4	0.0495 (7)	0.0431 (7)	0.0564 (8)	−0.0053 (6)	0.0323 (6)	−0.0111 (6)
C5	0.0463 (7)	0.0518 (8)	0.0435 (7)	0.0039 (6)	0.0214 (6)	0.0007 (6)
C6	0.0480 (7)	0.0466 (7)	0.0407 (6)	0.0010 (5)	0.0258 (6)	0.0008 (5)
C7	0.0437 (7)	0.0393 (6)	0.0415 (6)	0.0018 (5)	0.0202 (6)	0.0003 (5)
C8	0.0456 (7)	0.0422 (6)	0.0454 (7)	0.0059 (5)	0.0257 (6)	0.0055 (5)
C9	0.0523 (8)	0.0503 (8)	0.0510 (8)	−0.0001 (6)	0.0272 (7)	−0.0058 (6)
C10	0.0618 (9)	0.0481 (8)	0.0535 (8)	0.0072 (6)	0.0359 (7)	−0.0005 (6)
C11	0.0488 (7)	0.0502 (7)	0.0533 (7)	0.0101 (6)	0.0321 (6)	0.0123 (6)
C12	0.0480 (8)	0.0569 (8)	0.0500 (8)	−0.0013 (6)	0.0260 (7)	0.0012 (6)
C13	0.0522 (8)	0.0497 (7)	0.0465 (7)	0.0017 (6)	0.0289 (6)	−0.0033 (6)
C14	0.0557 (10)	0.0844 (14)	0.0834 (14)	−0.0071 (9)	0.0448 (10)	−0.0204 (12)

Geometric parameters (Å, º)

N1—C7	1.2638 (17)	C7—H7	0.970 (15)
N1—C8	1.4063 (16)	C8—C13	1.3917 (19)
N2—O2	1.217 (2)	C8—C9	1.3957 (18)
N2—O1	1.2239 (18)	C9—C10	1.373 (2)
N2—C11	1.4657 (18)	C9—H13	0.975 (16)
C1—C2	1.3904 (17)	C10—C11	1.378 (2)
C1—C6	1.3965 (18)	C10—H12	0.953 (15)
C1—C7	1.4673 (18)	C11—C12	1.382 (2)
C2—C3	1.384 (2)	C12—C13	1.384 (2)
C2—H2	0.973 (16)	C12—H10	0.974 (16)
C3—C4	1.385 (2)	C13—H9	0.978 (16)
C3—H3	0.958 (18)	C14—H141	1.03 (3)
C4—C5	1.3898 (19)	C14—H142	0.91 (4)
C4—C14	1.507 (2)	C14—H143	1.07 (3)
C5—C6	1.3790 (19)	C14—H144	1.03 (5)
C5—H5	0.970 (16)	C14—H145	1.08 (5)
C6—H6	0.946 (15)	C14—H146	0.86 (5)
C7—N1—C8	121.63 (12)	C9—C10—H12	118.5 (9)
O2—N2—O1	123.23 (14)	C11—C10—H12	122.5 (9)
O2—N2—C11	118.60 (14)	C10—C11—C12	122.30 (13)
O1—N2—C11	118.17 (14)	C10—C11—N2	118.62 (13)
C2—C1—C6	118.37 (12)	C12—C11—N2	119.06 (14)
C2—C1—C7	121.24 (12)	C11—C12—C13	118.32 (14)
C6—C1—C7	120.37 (11)	C11—C12—H10	120.7 (10)
C3—C2—C1	120.52 (13)	C13—C12—H10	121.0 (9)
C3—C2—H2	120.7 (9)	C12—C13—C8	120.47 (13)
C1—C2—H2	118.8 (9)	C12—C13—H9	119.8 (9)
C2—C3—C4	121.27 (13)	C8—C13—H9	119.7 (9)
C2—C3—H3	118.4 (10)	C4—C14—H141	108.3 (17)
C4—C3—H3	120.3 (10)	C4—C14—H142	112 (2)
C3—C4—C5	118.03 (12)	H141—C14—H142	108 (3)
C3—C4—C14	121.34 (15)	C4—C14—H143	110.8 (16)
C5—C4—C14	120.63 (15)	H141—C14—H143	110 (2)
C6—C5—C4	121.30 (13)	H142—C14—H143	108 (3)
C6—C5—H5	119.1 (9)	C4—C14—H144	105 (3)
C4—C5—H5	119.6 (9)	H141—C14—H144	68 (3)
C5—C6—C1	120.46 (12)	H142—C14—H144	46 (3)
C5—C6—H6	118.7 (9)	H143—C14—H144	142 (3)
C1—C6—H6	120.8 (9)	C4—C14—H145	114 (2)
N1—C7—C1	121.20 (12)	H141—C14—H145	138 (3)
N1—C7—H7	122.5 (9)	H142—C14—H145	57 (3)
C1—C7—H7	116.2 (9)	H143—C14—H145	54 (3)
C13—C8—C9	119.52 (12)	H144—C14—H145	101 (4)
C13—C8—N1	123.19 (12)	C4—C14—H146	113 (3)
C9—C8—N1	117.10 (12)	H141—C14—H146	46 (3)
C10—C9—C8	120.38 (14)	H142—C14—H146	133 (4)
C10—C9—H13	120.9 (9)	H143—C14—H146	66 (3)
C8—C9—H13	118.7 (9)	H144—C14—H146	110 (4)
C9—C10—C11	118.97 (13)	H145—C14—H146	113 (4)
C6—C1—C2—C3	−1.5 (2)	C13—C8—C9—C10	1.4 (2)
C7—C1—C2—C3	177.22 (12)	N1—C8—C9—C10	−173.87 (13)
C1—C2—C3—C4	−0.5 (2)	C8—C9—C10—C11	0.3 (2)
C2—C3—C4—C5	2.0 (2)	C9—C10—C11—C12	−1.7 (2)
C2—C3—C4—C14	−177.44 (16)	C9—C10—C11—N2	176.61 (13)
C3—C4—C5—C6	−1.5 (2)	O2—N2—C11—C10	170.06 (16)
C14—C4—C5—C6	177.95 (15)	O1—N2—C11—C10	−10.3 (2)
C4—C5—C6—C1	−0.5 (2)	O2—N2—C11—C12	−11.5 (2)
C2—C1—C6—C5	2.0 (2)	O1—N2—C11—C12	168.10 (15)
C7—C1—C6—C5	−176.73 (12)	C10—C11—C12—C13	1.5 (2)
C8—N1—C7—C1	−178.24 (11)	N2—C11—C12—C13	−176.82 (13)
C2—C1—C7—N1	−170.26 (13)	C11—C12—C13—C8	0.2 (2)
C6—C1—C7—N1	8.44 (19)	C9—C8—C13—C12	−1.6 (2)
C7—N1—C8—C13	52.32 (19)	N1—C8—C13—C12	173.36 (13)
C7—N1—C8—C9	−132.62 (14)

(3_90K) N-(4-methylbenzylidene)-4-nitroaniline

Crystal data

C14H12N2O2	Dx = 1.376 Mg m^−3
Mr = 240.26	Melting point: 135.7 C K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.4449 (13) Å	Cell parameters from 6799 reflections
b = 7.1070 (5) Å	θ = 3.2–30.0°
c = 12.6557 (9) Å	µ = 0.09 mm^−1
β = 123.370 (1)°	T = 90 K
V = 1160.15 (15) Å^3	Plate, pale yellow
Z = 4	0.60 × 0.56 × 0.04 mm
F(000) = 504

Data collection

Bruker SMART 1000 CCD diffractometer	3365 independent reflections
Radiation source: fine-focus sealed tube	2780 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 8.192 pixels mm^-1	θmax = 30.0°, θmin = 3.2°
ω scan	h = −21→21
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −9→9
Tmin = 0.946, Tmax = 0.996	l = −17→17
15616 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0626P)^2 + 0.3251P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3365 reflections	Δρmax = 0.45 e Å^−3
219 parameters	Δρmin = −0.17 e Å^−3
0 restraints

Special details

Experimental. The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different ϕ angle (0, 90, 180 and 270°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −32°. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections.

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	Occ. (<1)
N1	0.43165 (6)	0.24014 (12)	0.88694 (8)	0.01574 (17)
N2	0.04824 (7)	0.34159 (13)	0.83231 (8)	0.01911 (19)
O1	0.05160 (6)	0.41052 (12)	0.92406 (8)	0.02522 (19)
O2	−0.03237 (6)	0.28578 (15)	0.73658 (8)	0.0303 (2)
C1	0.55256 (7)	0.21083 (13)	0.82635 (9)	0.01300 (18)
C2	0.57748 (8)	0.25264 (14)	0.73791 (9)	0.01505 (19)
C3	0.67749 (8)	0.22028 (14)	0.76737 (9)	0.01587 (19)
C4	0.75481 (8)	0.14732 (13)	0.88467 (9)	0.01485 (19)
C5	0.72849 (8)	0.10173 (14)	0.97171 (9)	0.01505 (19)
C6	0.62912 (7)	0.13204 (13)	0.94302 (9)	0.01414 (18)
C7	0.44919 (7)	0.25284 (13)	0.79937 (9)	0.01407 (18)
C8	0.33242 (7)	0.27458 (13)	0.86192 (9)	0.01430 (19)
C9	0.32663 (8)	0.38844 (14)	0.94862 (9)	0.01639 (19)
C10	0.23299 (8)	0.41402 (14)	0.93717 (9)	0.0166 (2)
C11	0.14557 (8)	0.32393 (14)	0.83904 (9)	0.01565 (19)
C12	0.14787 (8)	0.21436 (14)	0.74954 (9)	0.01624 (19)
C13	0.24241 (8)	0.18994 (14)	0.76173 (9)	0.01532 (19)
C14	0.86434 (8)	0.12176 (17)	0.91930 (11)	0.0211 (2)
H2	0.5259 (11)	0.306 (2)	0.6553 (13)	0.023 (3)*
H3	0.6944 (11)	0.248 (2)	0.7040 (14)	0.025 (3)*
H5	0.7805 (11)	0.047 (2)	1.0535 (13)	0.021 (3)*
H6	0.6110 (10)	0.0966 (19)	1.0030 (12)	0.016 (3)*
H7	0.3952 (11)	0.297 (2)	0.7134 (14)	0.025 (4)*
H9	0.2458 (11)	0.109 (2)	0.7016 (13)	0.024 (3)*
H10	0.0855 (11)	0.154 (2)	0.6831 (14)	0.025 (3)*
H12	0.2291 (10)	0.495 (2)	0.9959 (13)	0.024 (3)*
H13	0.3882 (10)	0.448 (2)	1.0138 (13)	0.019 (3)*
H141	0.870 (2)	0.148 (6)	0.847 (3)	0.020 (3)*	0.58 (6)
H142	0.911 (2)	0.206 (5)	0.989 (3)	0.020 (3)*	0.58 (6)
H143	0.887 (3)	−0.004 (4)	0.947 (4)	0.020 (3)*	0.58 (6)
H144	0.904 (3)	0.243 (6)	0.952 (5)	0.020 (3)*	0.42 (6)
H145	0.907 (3)	0.015 (6)	0.993 (5)	0.020 (3)*	0.42 (6)
H146	0.864 (3)	0.083 (8)	0.842 (4)	0.020 (3)*	0.42 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0150 (4)	0.0170 (4)	0.0158 (4)	0.0016 (3)	0.0088 (3)	−0.0002 (3)
N2	0.0183 (4)	0.0221 (4)	0.0203 (4)	0.0044 (3)	0.0127 (4)	0.0046 (3)
O1	0.0269 (4)	0.0314 (4)	0.0262 (4)	0.0045 (3)	0.0202 (4)	0.0008 (3)
O2	0.0165 (4)	0.0480 (6)	0.0251 (4)	0.0007 (4)	0.0106 (3)	−0.0022 (4)
C1	0.0142 (4)	0.0118 (4)	0.0130 (4)	−0.0006 (3)	0.0074 (3)	−0.0011 (3)
C2	0.0174 (4)	0.0145 (4)	0.0128 (4)	−0.0001 (3)	0.0080 (4)	0.0007 (3)
C3	0.0200 (5)	0.0153 (4)	0.0159 (4)	−0.0020 (3)	0.0121 (4)	−0.0014 (3)
C4	0.0155 (4)	0.0135 (4)	0.0170 (4)	−0.0017 (3)	0.0099 (4)	−0.0034 (3)
C5	0.0151 (4)	0.0151 (4)	0.0130 (4)	0.0004 (3)	0.0065 (4)	0.0000 (3)
C6	0.0163 (4)	0.0143 (4)	0.0132 (4)	0.0000 (3)	0.0090 (4)	0.0001 (3)
C7	0.0145 (4)	0.0127 (4)	0.0136 (4)	0.0003 (3)	0.0068 (3)	0.0000 (3)
C8	0.0152 (4)	0.0141 (4)	0.0149 (4)	0.0021 (3)	0.0090 (4)	0.0027 (3)
C9	0.0178 (4)	0.0155 (4)	0.0154 (4)	0.0000 (3)	0.0088 (4)	−0.0010 (3)
C10	0.0209 (5)	0.0148 (4)	0.0174 (4)	0.0023 (3)	0.0126 (4)	0.0005 (3)
C11	0.0161 (4)	0.0165 (4)	0.0174 (4)	0.0036 (3)	0.0111 (4)	0.0042 (3)
C12	0.0154 (4)	0.0179 (4)	0.0147 (4)	0.0001 (3)	0.0078 (4)	0.0011 (3)
C13	0.0173 (4)	0.0155 (4)	0.0145 (4)	0.0006 (3)	0.0096 (4)	−0.0005 (3)
C14	0.0163 (5)	0.0260 (5)	0.0235 (5)	−0.0017 (4)	0.0125 (4)	−0.0044 (4)

Geometric parameters (Å, º)

N1—C7	1.2806 (12)	C7—H7	0.989 (15)
N1—C8	1.4054 (12)	C8—C13	1.4012 (14)
N2—O2	1.2312 (13)	C8—C9	1.4052 (13)
N2—O1	1.2347 (11)	C9—C10	1.3840 (14)
N2—C11	1.4636 (12)	C9—H13	0.948 (14)
C1—C2	1.4011 (13)	C10—C11	1.3895 (14)
C1—C6	1.4040 (13)	C10—H12	0.967 (14)
C1—C7	1.4681 (13)	C11—C12	1.3909 (13)
C2—C3	1.3944 (13)	C12—C13	1.3922 (13)
C2—H2	0.976 (14)	C12—H10	0.964 (15)
C3—C4	1.3959 (14)	C13—H9	0.979 (14)
C3—H3	0.991 (15)	C14—H141	0.99 (3)
C4—C5	1.4057 (13)	C14—H142	0.98 (3)
C4—C14	1.5072 (14)	C14—H143	0.95 (3)
C5—C6	1.3859 (13)	C14—H144	1.00 (4)
C5—H5	0.976 (14)	C14—H145	1.10 (4)
C6—H6	0.975 (13)	C14—H146	1.01 (4)
C7—N1—C8	121.08 (8)	C9—C10—H12	120.1 (8)
O2—N2—O1	123.36 (9)	C11—C10—H12	121.3 (8)
O2—N2—C11	118.68 (9)	C10—C11—C12	122.57 (9)
O1—N2—C11	117.96 (9)	C10—C11—N2	118.32 (9)
C2—C1—C6	118.83 (9)	C12—C11—N2	119.09 (9)
C2—C1—C7	120.83 (8)	C11—C12—C13	118.33 (9)
C6—C1—C7	120.31 (8)	C11—C12—H10	119.9 (8)
C3—C2—C1	120.13 (9)	C13—C12—H10	121.7 (8)
C3—C2—H2	118.7 (8)	C12—C13—C8	120.32 (9)
C1—C2—H2	121.1 (8)	C12—C13—H9	119.3 (8)
C2—C3—C4	121.30 (9)	C8—C13—H9	120.4 (8)
C2—C3—H3	119.9 (8)	C4—C14—H141	111.6 (17)
C4—C3—H3	118.8 (8)	C4—C14—H142	110.3 (16)
C3—C4—C5	118.17 (9)	H141—C14—H142	109 (2)
C3—C4—C14	121.38 (9)	C4—C14—H143	110.2 (17)
C5—C4—C14	120.43 (9)	H141—C14—H143	109 (2)
C6—C5—C4	120.98 (9)	H142—C14—H143	107 (2)
C6—C5—H5	119.1 (8)	C4—C14—H144	110 (2)
C4—C5—H5	120.0 (8)	H141—C14—H144	83 (3)
C5—C6—C1	120.54 (8)	H142—C14—H144	29 (2)
C5—C6—H6	120.4 (8)	H143—C14—H144	129 (3)
C1—C6—H6	119.0 (8)	C4—C14—H145	112.8 (19)
N1—C7—C1	120.34 (8)	H141—C14—H145	127 (3)
N1—C7—H7	121.5 (8)	H142—C14—H145	81 (2)
C1—C7—H7	118.1 (8)	H143—C14—H145	27 (2)
C13—C8—C9	119.75 (9)	H144—C14—H145	107 (3)
C13—C8—N1	123.05 (8)	C4—C14—H146	110 (2)
C9—C8—N1	117.02 (9)	H141—C14—H146	27 (2)
C10—C9—C8	120.37 (9)	H142—C14—H146	130 (3)
C10—C9—H13	121.6 (8)	H143—C14—H146	85 (3)
C8—C9—H13	118.1 (8)	H144—C14—H146	108 (3)
C9—C10—C11	118.61 (9)	H145—C14—H146	108 (3)
C6—C1—C2—C3	−1.54 (14)	C13—C8—C9—C10	1.42 (14)
C7—C1—C2—C3	176.90 (9)	N1—C8—C9—C10	−173.80 (9)
C1—C2—C3—C4	−0.40 (15)	C8—C9—C10—C11	0.43 (14)
C2—C3—C4—C5	1.84 (14)	C9—C10—C11—C12	−2.22 (15)
C2—C3—C4—C14	−176.75 (9)	C9—C10—C11—N2	176.08 (9)
C3—C4—C5—C6	−1.35 (14)	O2—N2—C11—C10	169.68 (10)
C14—C4—C5—C6	177.25 (9)	O1—N2—C11—C10	−10.97 (14)
C4—C5—C6—C1	−0.58 (15)	O2—N2—C11—C12	−11.96 (14)
C2—C1—C6—C5	2.02 (14)	O1—N2—C11—C12	167.38 (9)
C7—C1—C6—C5	−176.42 (9)	C10—C11—C12—C13	2.05 (15)
C8—N1—C7—C1	−178.16 (8)	N2—C11—C12—C13	−176.23 (9)
C2—C1—C7—N1	−169.73 (9)	C11—C12—C13—C8	−0.11 (14)
C6—C1—C7—N1	8.69 (14)	C9—C8—C13—C12	−1.59 (14)
C7—N1—C8—C13	50.40 (14)	N1—C8—C13—C12	173.33 (9)
C7—N1—C8—C9	−134.55 (10)

(4_rt) N-(4-nitrobenzylidene)-4-methoxyaniline

Crystal data

C14H12N2O3	Dx = 1.359 Mg m^−3
Mr = 256.26	Melting point: 130.8 C K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.8889 (8) Å	Cell parameters from 5863 reflections
b = 7.1007 (4) Å	θ = 2.9–29.3°
c = 14.0304 (8) Å	µ = 0.10 mm^−1
β = 102.815 (1)°	T = 300 K
V = 1252.08 (13) Å^3	Prism, yellow
Z = 4	0.58 × 0.48 × 0.18 mm
F(000) = 536

Data collection

Bruker SMART 1000 CCD diffractometer	3649 independent reflections
Radiation source: fine-focus sealed tube	2515 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 8.192 pixels mm^-1	θmax = 30.0°, θmin = 1.6°
ω scan	h = −18→18
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −9→9
Tmin = 0.946, Tmax = 0.983	l = −19→19
18959 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	All H-atom parameters refined
wR(F^2) = 0.141	w = 1/[σ^2(Fo^2) + (0.0613P)^2 + 0.2307P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
3649 reflections	Δρmax = 0.16 e Å^−3
220 parameters	Δρmin = −0.24 e Å^−3
0 restraints

Special details

Experimental. The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different ϕ angle (0, 90, 180 and 270°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −32°. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections.

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	0.51289 (8)	0.24483 (16)	0.90773 (7)	0.0515 (3)
N2	0.92174 (10)	0.2176 (2)	1.27013 (9)	0.0685 (4)
O1	0.90046 (10)	0.1285 (2)	1.33712 (8)	0.0910 (4)
O2	1.00781 (11)	0.2921 (3)	1.27551 (10)	0.1131 (6)
O3	0.23167 (8)	0.32935 (17)	0.54688 (7)	0.0700 (3)
C1	0.68902 (9)	0.26982 (18)	1.00889 (9)	0.0479 (3)
C2	0.78473 (10)	0.3664 (2)	1.02095 (10)	0.0549 (3)
C3	0.86143 (11)	0.3506 (2)	1.10623 (10)	0.0584 (3)
C4	0.84103 (10)	0.2350 (2)	1.17868 (9)	0.0529 (3)
C5	0.74722 (11)	0.1358 (2)	1.16906 (10)	0.0559 (3)
C6	0.67116 (11)	0.1527 (2)	1.08331 (10)	0.0538 (3)
C7	0.60922 (10)	0.29332 (19)	0.91721 (9)	0.0506 (3)
C8	0.44267 (9)	0.26902 (17)	0.81522 (9)	0.0472 (3)
C9	0.33783 (11)	0.3170 (2)	0.81278 (10)	0.0553 (3)
C10	0.26534 (11)	0.3412 (2)	0.72466 (11)	0.0568 (3)
C11	0.29688 (11)	0.31503 (18)	0.63778 (9)	0.0529 (3)
C12	0.40158 (11)	0.2653 (2)	0.63930 (10)	0.0567 (3)
C13	0.47340 (10)	0.24217 (19)	0.72713 (9)	0.0520 (3)
C14	0.12379 (16)	0.3763 (4)	0.53988 (16)	0.0865 (6)
H2	0.7976 (11)	0.446 (2)	0.9704 (11)	0.066 (4)*
H3	0.9276 (13)	0.422 (2)	1.1155 (11)	0.071 (4)*
H5	0.7358 (12)	0.052 (2)	1.2194 (11)	0.066 (4)*
H6	0.6060 (12)	0.078 (2)	1.0734 (10)	0.062 (4)*
H7	0.6352 (11)	0.357 (2)	0.8665 (10)	0.057 (4)*
H9	0.3157 (13)	0.331 (2)	0.8752 (12)	0.073 (5)*
H10	0.1939 (13)	0.371 (2)	0.7269 (11)	0.073 (5)*
H12	0.4220 (12)	0.246 (2)	0.5799 (12)	0.072 (5)*
H13	0.5451 (11)	0.200 (2)	0.7274 (10)	0.054 (4)*
H141	0.1150 (17)	0.501 (4)	0.5704 (16)	0.113 (8)*
H142	0.0939 (17)	0.380 (3)	0.4691 (17)	0.104 (6)*
H143	0.0902 (15)	0.282 (3)	0.5738 (15)	0.093 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0509 (6)	0.0551 (6)	0.0484 (5)	0.0007 (5)	0.0107 (4)	0.0024 (4)
N2	0.0588 (7)	0.0877 (9)	0.0560 (7)	0.0083 (7)	0.0060 (5)	−0.0019 (6)
O1	0.0806 (8)	0.1357 (12)	0.0542 (6)	0.0106 (8)	0.0099 (5)	0.0149 (7)
O2	0.0692 (8)	0.1644 (16)	0.0901 (9)	−0.0281 (9)	−0.0156 (7)	0.0235 (10)
O3	0.0667 (6)	0.0798 (7)	0.0562 (6)	−0.0002 (5)	−0.0023 (5)	0.0042 (5)
C1	0.0478 (6)	0.0487 (6)	0.0479 (6)	0.0015 (5)	0.0124 (5)	−0.0018 (5)
C2	0.0531 (7)	0.0586 (8)	0.0545 (7)	−0.0041 (6)	0.0147 (6)	0.0041 (6)
C3	0.0473 (7)	0.0670 (9)	0.0613 (8)	−0.0060 (6)	0.0128 (6)	−0.0029 (6)
C4	0.0501 (6)	0.0600 (8)	0.0477 (6)	0.0076 (6)	0.0087 (5)	−0.0048 (5)
C5	0.0588 (7)	0.0590 (8)	0.0509 (7)	0.0018 (6)	0.0140 (6)	0.0059 (6)
C6	0.0507 (7)	0.0556 (7)	0.0555 (7)	−0.0047 (6)	0.0123 (6)	0.0023 (6)
C7	0.0536 (7)	0.0499 (7)	0.0483 (6)	−0.0016 (5)	0.0117 (5)	0.0025 (5)
C8	0.0488 (6)	0.0437 (6)	0.0484 (6)	−0.0022 (5)	0.0097 (5)	0.0015 (5)
C9	0.0538 (7)	0.0609 (8)	0.0532 (7)	0.0020 (6)	0.0159 (6)	−0.0004 (6)
C10	0.0484 (7)	0.0575 (8)	0.0635 (8)	0.0047 (6)	0.0106 (6)	0.0008 (6)
C11	0.0578 (7)	0.0440 (6)	0.0531 (7)	−0.0040 (5)	0.0042 (5)	0.0021 (5)
C12	0.0602 (8)	0.0609 (8)	0.0500 (7)	−0.0065 (6)	0.0145 (6)	−0.0046 (6)
C13	0.0482 (6)	0.0536 (7)	0.0555 (7)	−0.0020 (5)	0.0140 (5)	−0.0042 (5)
C14	0.0676 (10)	0.1026 (16)	0.0770 (12)	0.0093 (10)	−0.0104 (9)	0.0063 (11)

Geometric parameters (Å, º)

N1—C7	1.2667 (16)	C5—H5	0.961 (16)
N1—C8	1.4185 (15)	C6—H6	0.976 (16)
N2—O1	1.2142 (18)	C7—H7	0.962 (15)
N2—O2	1.2161 (18)	C8—C9	1.3867 (18)
N2—C4	1.4668 (17)	C8—C13	1.3921 (17)
O3—C11	1.3666 (15)	C9—C10	1.3853 (19)
O3—C14	1.412 (2)	C9—H9	0.984 (16)
C1—C2	1.3888 (18)	C10—C11	1.3804 (19)
C1—C6	1.3934 (18)	C10—H10	0.952 (16)
C1—C7	1.4674 (17)	C11—C12	1.391 (2)
C2—C3	1.3772 (19)	C12—C13	1.3771 (18)
C2—H2	0.950 (16)	C12—H12	0.939 (16)
C3—C4	1.377 (2)	C13—H13	0.970 (14)
C3—H3	0.974 (16)	C14—H141	1.00 (3)
C4—C5	1.3795 (19)	C14—H142	0.98 (2)
C5—C6	1.3783 (19)	C14—H143	0.98 (2)
C7—N1—C8	118.34 (11)	C1—C7—H7	114.2 (8)
O1—N2—O2	122.58 (13)	C9—C8—C13	118.65 (11)
O1—N2—C4	118.86 (13)	C9—C8—N1	118.22 (11)
O2—N2—C4	118.56 (14)	C13—C8—N1	123.12 (11)
C11—O3—C14	118.35 (14)	C10—C9—C8	120.88 (12)
C2—C1—C6	119.57 (12)	C10—C9—H9	120.7 (9)
C2—C1—C7	118.79 (11)	C8—C9—H9	118.4 (9)
C6—C1—C7	121.64 (11)	C11—C10—C9	119.93 (13)
C3—C2—C1	120.85 (13)	C11—C10—H10	122.3 (10)
C3—C2—H2	119.1 (9)	C9—C10—H10	117.7 (10)
C1—C2—H2	120.0 (9)	O3—C11—C10	124.99 (13)
C4—C3—C2	118.17 (13)	O3—C11—C12	115.28 (12)
C4—C3—H3	121.0 (9)	C10—C11—C12	119.71 (12)
C2—C3—H3	120.8 (9)	C13—C12—C11	120.10 (13)
C3—C4—C5	122.61 (12)	C13—C12—H12	120.8 (10)
C3—C4—N2	118.76 (13)	C11—C12—H12	119.1 (10)
C5—C4—N2	118.62 (13)	C12—C13—C8	120.73 (12)
C6—C5—C4	118.64 (13)	C12—C13—H13	119.4 (8)
C6—C5—H5	120.0 (9)	C8—C13—H13	119.8 (8)
C4—C5—H5	121.3 (9)	O3—C14—H141	112.5 (13)
C5—C6—C1	120.15 (12)	O3—C14—H142	103.7 (12)
C5—C6—H6	120.0 (9)	H141—C14—H142	110.5 (18)
C1—C6—H6	119.8 (9)	O3—C14—H143	109.9 (12)
N1—C7—C1	122.77 (12)	H141—C14—H143	107.1 (17)
N1—C7—H7	122.9 (8)	H142—C14—H143	113.3 (17)
C6—C1—C2—C3	−1.2 (2)	C6—C1—C7—N1	15.9 (2)
C7—C1—C2—C3	179.16 (12)	C7—N1—C8—C9	−145.42 (13)
C1—C2—C3—C4	0.7 (2)	C7—N1—C8—C13	36.29 (18)
C2—C3—C4—C5	−0.2 (2)	C13—C8—C9—C10	−1.2 (2)
C2—C3—C4—N2	−179.64 (12)	N1—C8—C9—C10	−179.55 (12)
O1—N2—C4—C3	173.90 (15)	C8—C9—C10—C11	0.9 (2)
O2—N2—C4—C3	−6.7 (2)	C14—O3—C11—C10	0.7 (2)
O1—N2—C4—C5	−5.5 (2)	C14—O3—C11—C12	178.93 (16)
O2—N2—C4—C5	173.87 (16)	C9—C10—C11—O3	177.88 (13)
C3—C4—C5—C6	0.3 (2)	C9—C10—C11—C12	−0.3 (2)
N2—C4—C5—C6	179.72 (12)	O3—C11—C12—C13	−178.34 (12)
C4—C5—C6—C1	−0.8 (2)	C10—C11—C12—C13	0.0 (2)
C2—C1—C6—C5	1.3 (2)	C11—C12—C13—C8	−0.3 (2)
C7—C1—C6—C5	−179.10 (12)	C9—C8—C13—C12	0.9 (2)
C8—N1—C7—C1	−178.37 (11)	N1—C8—C13—C12	179.16 (12)
C2—C1—C7—N1	−164.45 (13)

(4_90K) N-(4-nitrobenzylidene)-4-methoxyaniline

Crystal data

C14H12N2O3	Dx = 1.407 Mg m^−3
Mr = 256.26	Melting point: 130.8 C K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.7478 (7) Å	Cell parameters from 10589 reflections
b = 6.9429 (4) Å	θ = 2.9–30.0°
c = 13.9980 (8) Å	µ = 0.10 mm^−1
β = 102.446 (1)°	T = 90 K
V = 1209.80 (12) Å^3	Prism, yellow
Z = 4	0.58 × 0.48 × 0.18 mm
F(000) = 536

Data collection

Bruker SMART 1000 CCD diffractometer	3530 independent reflections
Radiation source: fine-focus sealed tube	3163 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 8.192 pixels mm^-1	θmax = 30.0°, θmin = 1.6°
ω scan	h = −17→17
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −9→9
Tmin = 0.944, Tmax = 0.982	l = −19→19
18152 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	All H-atom parameters refined
wR(F^2) = 0.111	w = 1/[σ^2(Fo^2) + (0.0659P)^2 + 0.2901P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3530 reflections	Δρmax = 0.40 e Å^−3
220 parameters	Δρmin = −0.26 e Å^−3
0 restraints

Special details

Experimental. The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different ϕ angle (0, 90, 180 and 270°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −32°. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections.

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	0.51219 (6)	0.24560 (10)	0.90779 (5)	0.01753 (15)
N2	0.92524 (6)	0.22464 (12)	1.27071 (5)	0.02133 (16)
O1	0.90206 (5)	0.13703 (11)	1.33961 (5)	0.02754 (17)
O2	1.01351 (6)	0.30118 (13)	1.27513 (5)	0.03452 (19)
O3	0.23258 (5)	0.33417 (10)	0.54427 (4)	0.02205 (15)
C1	0.69059 (6)	0.27218 (12)	1.00863 (6)	0.01645 (16)
C2	0.78750 (6)	0.37299 (12)	1.01990 (6)	0.01803 (16)
C3	0.86562 (7)	0.35853 (13)	1.10568 (6)	0.01904 (17)
C4	0.84426 (6)	0.24017 (12)	1.17914 (6)	0.01772 (16)
C5	0.74920 (7)	0.13655 (12)	1.17029 (6)	0.01869 (17)
C6	0.67226 (6)	0.15237 (12)	1.08408 (6)	0.01808 (16)
C7	0.61051 (6)	0.29571 (12)	0.91669 (6)	0.01722 (16)
C8	0.44244 (6)	0.27035 (11)	0.81487 (6)	0.01621 (16)
C9	0.33554 (7)	0.31836 (12)	0.81207 (6)	0.01835 (17)
C10	0.26274 (7)	0.34419 (12)	0.72291 (6)	0.01870 (17)
C11	0.29707 (7)	0.31884 (11)	0.63567 (6)	0.01744 (16)
C12	0.40380 (7)	0.26828 (12)	0.63758 (6)	0.01872 (17)
C13	0.47548 (6)	0.24366 (12)	0.72629 (6)	0.01759 (16)
C14	0.12250 (7)	0.38198 (15)	0.53751 (7)	0.0273 (2)
H2	0.8000 (9)	0.4564 (18)	0.9671 (8)	0.022 (3)*
H3	0.9327 (10)	0.435 (2)	1.1149 (9)	0.029 (3)*
H5	0.7388 (9)	0.0521 (18)	1.2225 (8)	0.024 (3)*
H6	0.6053 (10)	0.0757 (19)	1.0743 (9)	0.024 (3)*
H7	0.6366 (10)	0.3595 (18)	0.8634 (8)	0.022 (3)*
H9	0.3112 (10)	0.3317 (19)	0.8738 (9)	0.028 (3)*
H10	0.1872 (11)	0.376 (2)	0.7246 (9)	0.032 (3)*
H12	0.4251 (10)	0.2468 (19)	0.5761 (9)	0.027 (3)*
H13	0.5475 (9)	0.2009 (18)	0.7268 (8)	0.019 (3)*
H141	0.1132 (10)	0.509 (2)	0.5655 (9)	0.031 (3)*
H142	0.0904 (11)	0.383 (2)	0.4673 (10)	0.037 (4)*
H143	0.0882 (11)	0.283 (2)	0.5706 (10)	0.033 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0183 (3)	0.0177 (3)	0.0162 (3)	0.0006 (2)	0.0029 (2)	0.0001 (2)
N2	0.0189 (3)	0.0256 (4)	0.0188 (3)	0.0025 (3)	0.0026 (3)	−0.0010 (3)
O1	0.0259 (3)	0.0393 (4)	0.0175 (3)	0.0036 (3)	0.0048 (2)	0.0039 (3)
O2	0.0218 (3)	0.0484 (5)	0.0295 (4)	−0.0086 (3)	−0.0030 (3)	0.0062 (3)
O3	0.0208 (3)	0.0255 (3)	0.0178 (3)	0.0004 (2)	−0.0004 (2)	0.0008 (2)
C1	0.0169 (3)	0.0161 (3)	0.0166 (3)	0.0009 (3)	0.0042 (3)	−0.0012 (3)
C2	0.0182 (4)	0.0181 (4)	0.0183 (4)	−0.0004 (3)	0.0052 (3)	0.0005 (3)
C3	0.0163 (3)	0.0209 (4)	0.0201 (4)	−0.0008 (3)	0.0046 (3)	−0.0017 (3)
C4	0.0170 (3)	0.0199 (4)	0.0158 (3)	0.0027 (3)	0.0025 (3)	−0.0018 (3)
C5	0.0201 (4)	0.0187 (4)	0.0175 (4)	0.0008 (3)	0.0045 (3)	0.0012 (3)
C6	0.0175 (3)	0.0182 (4)	0.0185 (4)	−0.0008 (3)	0.0036 (3)	0.0001 (3)
C7	0.0191 (4)	0.0157 (3)	0.0169 (3)	−0.0001 (3)	0.0039 (3)	0.0001 (3)
C8	0.0173 (3)	0.0144 (3)	0.0166 (3)	−0.0010 (3)	0.0031 (3)	0.0004 (3)
C9	0.0184 (4)	0.0189 (4)	0.0183 (4)	0.0001 (3)	0.0052 (3)	−0.0002 (3)
C10	0.0167 (3)	0.0179 (4)	0.0212 (4)	0.0012 (3)	0.0036 (3)	0.0003 (3)
C11	0.0196 (4)	0.0141 (3)	0.0173 (4)	−0.0013 (3)	0.0012 (3)	0.0009 (3)
C12	0.0203 (4)	0.0189 (4)	0.0173 (4)	−0.0017 (3)	0.0048 (3)	−0.0016 (3)
C13	0.0171 (3)	0.0167 (4)	0.0192 (4)	−0.0007 (3)	0.0044 (3)	−0.0014 (3)
C14	0.0210 (4)	0.0314 (5)	0.0260 (4)	0.0029 (3)	−0.0026 (3)	0.0012 (4)

Geometric parameters (Å, º)

N1—C7	1.2807 (11)	C5—H5	0.968 (12)
N1—C8	1.4190 (10)	C6—H6	0.990 (13)
N2—O1	1.2289 (10)	C7—H7	0.985 (12)
N2—O2	1.2338 (10)	C8—C9	1.3952 (11)
N2—C4	1.4662 (10)	C8—C13	1.4051 (11)
O3—C11	1.3677 (9)	C9—C10	1.3970 (11)
O3—C14	1.4251 (11)	C9—H9	0.983 (13)
C1—C2	1.3989 (11)	C10—C11	1.3943 (11)
C1—C6	1.4031 (11)	C10—H10	0.993 (13)
C1—C7	1.4693 (11)	C11—C12	1.3999 (12)
C2—C3	1.3886 (11)	C12—C13	1.3846 (11)
C2—H2	0.978 (12)	C12—H12	0.968 (12)
C3—C4	1.3883 (12)	C13—H13	0.963 (12)
C3—H3	0.991 (13)	C14—H141	0.984 (14)
C4—C5	1.3917 (12)	C14—H142	0.980 (14)
C5—C6	1.3856 (11)	C14—H143	0.985 (15)
C7—N1—C8	117.58 (7)	C1—C7—H7	115.4 (7)
O1—N2—O2	123.01 (8)	C9—C8—C13	118.91 (7)
O1—N2—C4	118.64 (7)	C9—C8—N1	118.03 (7)
O2—N2—C4	118.35 (7)	C13—C8—N1	123.04 (7)
C11—O3—C14	117.71 (7)	C8—C9—C10	120.83 (7)
C2—C1—C6	119.87 (7)	C8—C9—H9	119.3 (7)
C2—C1—C7	118.24 (7)	C10—C9—H9	119.9 (7)
C6—C1—C7	121.89 (7)	C11—C10—C9	119.52 (7)
C3—C2—C1	120.84 (7)	C11—C10—H10	122.5 (8)
C3—C2—H2	119.5 (7)	C9—C10—H10	117.9 (7)
C1—C2—H2	119.6 (7)	O3—C11—C10	124.80 (7)
C4—C3—C2	117.69 (7)	O3—C11—C12	115.03 (7)
C4—C3—H3	121.5 (7)	C10—C11—C12	120.14 (7)
C2—C3—H3	120.8 (7)	C13—C12—C11	119.93 (7)
C3—C4—C5	123.09 (8)	C13—C12—H12	121.4 (7)
C3—C4—N2	118.52 (7)	C11—C12—H12	118.7 (7)
C5—C4—N2	118.38 (7)	C12—C13—C8	120.65 (7)
C6—C5—C4	118.42 (7)	C12—C13—H13	119.2 (7)
C6—C5—H5	121.3 (7)	C8—C13—H13	120.0 (7)
C4—C5—H5	120.2 (7)	O3—C14—H141	112.6 (8)
C5—C6—C1	120.07 (7)	O3—C14—H142	105.2 (8)
C5—C6—H6	120.3 (7)	H141—C14—H142	109.5 (11)
C1—C6—H6	119.5 (7)	O3—C14—H143	109.7 (8)
N1—C7—C1	122.39 (7)	H141—C14—H143	109.7 (11)
N1—C7—H7	122.1 (7)	H142—C14—H143	110.1 (12)
C6—C1—C2—C3	−0.99 (12)	C6—C1—C7—N1	16.02 (12)
C7—C1—C2—C3	179.11 (7)	C7—N1—C8—C9	−146.14 (8)
C1—C2—C3—C4	0.34 (12)	C7—N1—C8—C13	35.63 (11)
C2—C3—C4—C5	0.17 (12)	C13—C8—C9—C10	−1.51 (13)
C2—C3—C4—N2	−179.34 (7)	N1—C8—C9—C10	−179.82 (7)
O1—N2—C4—C3	172.23 (8)	C8—C9—C10—C11	0.95 (13)
O2—N2—C4—C3	−7.41 (12)	C14—O3—C11—C10	0.85 (12)
O1—N2—C4—C5	−7.30 (12)	C14—O3—C11—C12	178.93 (8)
O2—N2—C4—C5	173.06 (8)	C9—C10—C11—O3	177.85 (7)
C3—C4—C5—C6	−0.02 (13)	C9—C10—C11—C12	−0.14 (13)
N2—C4—C5—C6	179.49 (7)	O3—C11—C12—C13	−178.27 (7)
C4—C5—C6—C1	−0.63 (12)	C10—C11—C12—C13	−0.09 (13)
C2—C1—C6—C5	1.13 (12)	C11—C12—C13—C8	−0.48 (13)
C7—C1—C6—C5	−178.97 (7)	C9—C8—C13—C12	1.27 (12)
C8—N1—C7—C1	−178.41 (7)	N1—C8—C13—C12	179.49 (7)
C2—C1—C7—N1	−164.08 (8)

(5_rt) N-(4-nitrobenzylidene)-4-methylaniline

Crystal data

C14H12N2O2	F(000) = 504
Mr = 240.26	Dx = 1.310 Mg m^−3
Triclinic, P1	Melting point: 121.8 C K
a = 7.1098 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.5649 (9) Å	Cell parameters from 5945 reflections
c = 14.3814 (10) Å	θ = 2.6–29.8°
α = 72.617 (1)°	µ = 0.09 mm^−1
β = 83.926 (1)°	T = 300 K
γ = 86.144 (1)°	Block, yellow
V = 1218.33 (15) Å^3	0.50 × 0.36 × 0.18 mm
Z = 4

Data collection

Bruker SMART 1000 CCD diffractometer	7068 independent reflections
Radiation source: fine-focus sealed tube	4658 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.192 pixels mm^-1	θmax = 30.0°, θmin = 1.5°
ω scan	h = −10→9
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −17→17
Tmin = 0.957, Tmax = 0.984	l = −20→20
18799 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.0637P)^2 + 0.1715P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.150	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.19 e Å^−3
7068 reflections	Δρmin = −0.25 e Å^−3
438 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.029 (3)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different ϕ angle (0, 90, 180 and 270°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −32°. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections.

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	Occ. (<1)
N1A	0.74334 (18)	0.48207 (10)	0.11926 (8)	0.0529 (3)
N2A	0.7310 (2)	0.90881 (11)	−0.26706 (9)	0.0640 (3)
O1A	0.6565 (2)	0.88399 (11)	−0.32966 (8)	0.0853 (4)
O2A	0.7977 (3)	0.99906 (11)	−0.27939 (10)	0.0995 (5)
C1A	0.77029 (19)	0.66512 (11)	0.00561 (9)	0.0487 (3)
C2A	0.8413 (2)	0.76994 (12)	−0.01147 (10)	0.0552 (3)
C3A	0.8277 (2)	0.85106 (12)	−0.10027 (10)	0.0554 (3)
C4A	0.7420 (2)	0.82415 (11)	−0.17123 (9)	0.0497 (3)
C5A	0.6680 (2)	0.72159 (12)	−0.15658 (11)	0.0549 (3)
C6A	0.6821 (2)	0.64141 (12)	−0.06772 (10)	0.0534 (3)
C7A	0.7922 (2)	0.58088 (12)	0.10032 (10)	0.0540 (3)
C8A	0.77232 (19)	0.40525 (11)	0.21225 (10)	0.0472 (3)
C9A	0.7974 (2)	0.29368 (12)	0.21729 (12)	0.0582 (4)
C10A	0.8293 (2)	0.21410 (12)	0.30495 (12)	0.0591 (4)
C11A	0.83659 (19)	0.24271 (11)	0.39011 (10)	0.0518 (3)
C12A	0.8068 (2)	0.35414 (13)	0.38507 (11)	0.0584 (4)
C13A	0.7746 (2)	0.43507 (12)	0.29812 (10)	0.0554 (3)
C14A	0.8710 (3)	0.15485 (16)	0.48477 (15)	0.0694 (5)
H2A	0.902 (2)	0.7874 (13)	0.0385 (12)	0.063 (4)*
H3A	0.879 (2)	0.9237 (14)	−0.1122 (12)	0.069 (5)*
H5A	0.609 (2)	0.7053 (13)	−0.2073 (12)	0.068 (5)*
H6A	0.627 (2)	0.5718 (14)	−0.0565 (12)	0.067 (5)*
H7A	0.858 (2)	0.6066 (14)	0.1434 (12)	0.072 (5)*
H9A	0.798 (2)	0.2711 (13)	0.1597 (13)	0.069 (5)*
H10A	0.850 (2)	0.1365 (15)	0.3027 (12)	0.073 (5)*
H12A	0.807 (2)	0.3768 (14)	0.4427 (13)	0.072 (5)*
H13A	0.749 (2)	0.5121 (15)	0.2985 (12)	0.074 (5)*
H141	0.772 (6)	0.099 (3)	0.503 (3)	0.074 (5)*	0.57 (3)
H142	0.894 (6)	0.190 (3)	0.542 (3)	0.074 (5)*	0.57 (3)
H143	0.992 (6)	0.107 (3)	0.474 (3)	0.074 (5)*	0.57 (3)
H144	1.000 (8)	0.150 (4)	0.499 (3)	0.074 (5)*	0.43 (3)
H145	0.864 (9)	0.086 (4)	0.470 (4)	0.074 (5)*	0.43 (3)
H146	0.777 (7)	0.158 (4)	0.542 (3)	0.074 (5)*	0.43 (3)
N1B	0.26330 (17)	0.49977 (9)	0.40250 (8)	0.0502 (3)
N2B	0.21164 (19)	0.06914 (10)	0.78303 (8)	0.0548 (3)
O1B	0.1070 (2)	0.09144 (10)	0.84828 (8)	0.0777 (4)
O2B	0.2986 (2)	−0.01962 (10)	0.79355 (9)	0.0897 (4)
C1B	0.27808 (18)	0.31267 (10)	0.50873 (9)	0.0442 (3)
C2B	0.3639 (2)	0.20752 (11)	0.52188 (10)	0.0479 (3)
C3B	0.3434 (2)	0.12661 (11)	0.61175 (10)	0.0487 (3)
C4B	0.23200 (19)	0.15358 (10)	0.68703 (9)	0.0441 (3)
C5B	0.1413 (2)	0.25630 (11)	0.67581 (10)	0.0494 (3)
C6B	0.1649 (2)	0.33665 (11)	0.58616 (9)	0.0493 (3)
C7B	0.30801 (19)	0.39831 (11)	0.41318 (9)	0.0477 (3)
C8B	0.29046 (18)	0.57933 (11)	0.30897 (9)	0.0457 (3)
C9B	0.3478 (2)	0.68409 (12)	0.30423 (11)	0.0571 (4)
C10B	0.3663 (2)	0.76715 (13)	0.21579 (12)	0.0595 (4)
C11B	0.32712 (19)	0.74863 (12)	0.12968 (10)	0.0523 (3)
C12B	0.2707 (2)	0.64356 (12)	0.13475 (10)	0.0555 (3)
C13B	0.2522 (2)	0.55891 (11)	0.22287 (10)	0.0506 (3)
C14B	0.3374 (3)	0.84166 (17)	0.03469 (14)	0.0713 (5)
H2B	0.443 (2)	0.1909 (12)	0.4705 (11)	0.055 (4)*
H3B	0.406 (2)	0.0551 (13)	0.6221 (11)	0.062 (4)*
H5B	0.059 (2)	0.2729 (12)	0.7291 (11)	0.060 (4)*
H6B	0.100 (2)	0.4081 (13)	0.5773 (11)	0.060 (4)*
H7B	0.371 (2)	0.3709 (12)	0.3598 (11)	0.060 (4)*
H9B	0.375 (3)	0.6971 (15)	0.3630 (14)	0.078 (5)*
H10B	0.403 (3)	0.8409 (15)	0.2182 (13)	0.077 (5)*
H12B	0.241 (2)	0.6292 (13)	0.0749 (13)	0.067 (5)*
H13B	0.203 (2)	0.4858 (13)	0.2243 (11)	0.058 (4)*
H147	0.366 (5)	0.812 (3)	−0.020 (2)	0.072 (4)*	0.64 (2)
H148	0.450 (5)	0.885 (3)	0.035 (2)	0.072 (4)*	0.64 (2)
H149	0.216 (5)	0.888 (2)	0.031 (2)	0.072 (4)*	0.64 (2)
H150	0.341 (9)	0.919 (5)	0.046 (4)	0.072 (4)*	0.36 (2)
H151	0.243 (8)	0.834 (4)	−0.020 (4)	0.072 (4)*	0.36 (2)
H152	0.455 (9)	0.847 (5)	−0.007 (4)	0.072 (4)*	0.36 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0587 (7)	0.0486 (6)	0.0474 (6)	−0.0029 (5)	−0.0083 (5)	−0.0064 (5)
N2A	0.0828 (9)	0.0557 (7)	0.0461 (7)	0.0100 (6)	−0.0054 (6)	−0.0067 (6)
O1A	0.1191 (11)	0.0842 (9)	0.0494 (6)	0.0076 (8)	−0.0229 (7)	−0.0118 (6)
O2A	0.1601 (15)	0.0550 (7)	0.0700 (8)	−0.0148 (8)	−0.0195 (9)	0.0074 (6)
C1A	0.0529 (7)	0.0470 (7)	0.0438 (7)	−0.0054 (6)	−0.0060 (5)	−0.0082 (5)
C2A	0.0671 (9)	0.0538 (8)	0.0453 (7)	−0.0144 (7)	−0.0104 (6)	−0.0110 (6)
C3A	0.0694 (9)	0.0446 (7)	0.0502 (7)	−0.0111 (6)	−0.0028 (6)	−0.0100 (6)
C4A	0.0592 (8)	0.0451 (7)	0.0405 (6)	0.0043 (6)	−0.0033 (6)	−0.0075 (5)
C5A	0.0645 (9)	0.0554 (8)	0.0477 (7)	−0.0002 (6)	−0.0147 (6)	−0.0169 (6)
C6A	0.0638 (9)	0.0451 (7)	0.0520 (7)	−0.0083 (6)	−0.0095 (6)	−0.0125 (6)
C7A	0.0584 (8)	0.0534 (8)	0.0469 (7)	−0.0110 (6)	−0.0109 (6)	−0.0057 (6)
C8A	0.0450 (7)	0.0450 (7)	0.0470 (7)	−0.0047 (5)	−0.0046 (5)	−0.0057 (5)
C9A	0.0685 (9)	0.0511 (8)	0.0559 (8)	0.0010 (7)	−0.0092 (7)	−0.0164 (7)
C10A	0.0621 (9)	0.0417 (7)	0.0693 (9)	0.0045 (6)	−0.0086 (7)	−0.0105 (7)
C11A	0.0423 (7)	0.0495 (7)	0.0549 (8)	−0.0049 (5)	−0.0039 (6)	−0.0018 (6)
C12A	0.0719 (10)	0.0551 (8)	0.0454 (7)	−0.0098 (7)	−0.0053 (7)	−0.0091 (6)
C13A	0.0693 (9)	0.0434 (7)	0.0504 (7)	−0.0070 (6)	−0.0037 (6)	−0.0086 (6)
C14A	0.0700 (11)	0.0578 (10)	0.0661 (10)	−0.0036 (9)	−0.0144 (9)	0.0065 (8)
N1B	0.0571 (7)	0.0473 (6)	0.0411 (5)	−0.0004 (5)	−0.0038 (5)	−0.0056 (5)
N2B	0.0738 (8)	0.0454 (6)	0.0417 (6)	−0.0100 (5)	−0.0067 (5)	−0.0055 (5)
O1B	0.1108 (10)	0.0693 (7)	0.0449 (6)	−0.0084 (7)	0.0114 (6)	−0.0096 (5)
O2B	0.1360 (12)	0.0550 (7)	0.0584 (7)	0.0173 (7)	0.0004 (7)	0.0055 (5)
C1B	0.0476 (7)	0.0442 (6)	0.0384 (6)	−0.0009 (5)	−0.0070 (5)	−0.0077 (5)
C2B	0.0520 (7)	0.0492 (7)	0.0409 (6)	0.0031 (6)	−0.0033 (5)	−0.0124 (5)
C3B	0.0569 (8)	0.0412 (7)	0.0464 (7)	0.0031 (6)	−0.0084 (6)	−0.0103 (5)
C4B	0.0515 (7)	0.0412 (6)	0.0373 (6)	−0.0074 (5)	−0.0075 (5)	−0.0057 (5)
C5B	0.0552 (8)	0.0504 (7)	0.0411 (6)	−0.0003 (6)	−0.0011 (6)	−0.0125 (6)
C6B	0.0556 (8)	0.0439 (7)	0.0443 (7)	0.0047 (6)	−0.0029 (6)	−0.0087 (5)
C7B	0.0509 (7)	0.0492 (7)	0.0387 (6)	0.0005 (6)	−0.0034 (5)	−0.0073 (5)
C8B	0.0455 (7)	0.0449 (7)	0.0414 (6)	0.0010 (5)	−0.0033 (5)	−0.0054 (5)
C9B	0.0658 (9)	0.0533 (8)	0.0522 (8)	−0.0077 (7)	−0.0123 (7)	−0.0120 (6)
C10B	0.0596 (9)	0.0471 (8)	0.0666 (9)	−0.0104 (6)	−0.0084 (7)	−0.0062 (7)
C11B	0.0452 (7)	0.0508 (7)	0.0496 (7)	0.0029 (5)	0.0011 (5)	−0.0004 (6)
C12B	0.0648 (9)	0.0543 (8)	0.0433 (7)	0.0052 (6)	−0.0071 (6)	−0.0091 (6)
C13B	0.0595 (8)	0.0430 (7)	0.0469 (7)	0.0005 (6)	−0.0065 (6)	−0.0095 (5)
C14B	0.0727 (12)	0.0608 (10)	0.0594 (10)	0.0011 (9)	0.0042 (9)	0.0099 (8)

Geometric parameters (Å, º)

N1A—C7A	1.2539 (18)	N1B—C7B	1.2605 (17)
N1A—C8A	1.4223 (17)	N1B—C8B	1.4190 (16)
N2A—O2A	1.2153 (18)	N2B—O2B	1.2147 (16)
N2A—O1A	1.2162 (18)	N2B—O1B	1.2223 (16)
N2A—C4A	1.4740 (17)	N2B—C4B	1.4682 (15)
C1A—C2A	1.3856 (19)	C1B—C2B	1.3858 (18)
C1A—C6A	1.3953 (19)	C1B—C6B	1.3987 (18)
C1A—C7A	1.4701 (18)	C1B—C7B	1.4754 (17)
C2A—C3A	1.3836 (19)	C2B—C3B	1.3858 (18)
C2A—H2A	0.963 (17)	C2B—H2B	0.944 (15)
C3A—C4A	1.376 (2)	C3B—C4B	1.3840 (18)
C3A—H3A	0.964 (17)	C3B—H3B	0.951 (16)
C4A—C5A	1.374 (2)	C4B—C5B	1.3758 (18)
C5A—C6A	1.3792 (19)	C5B—C6B	1.3817 (18)
C5A—H5A	0.956 (17)	C5B—H5B	0.979 (15)
C6A—H6A	0.944 (17)	C6B—H6B	0.961 (16)
C7A—H7A	0.953 (18)	C7B—H7B	0.986 (16)
C8A—C9A	1.3823 (19)	C8B—C9B	1.384 (2)
C8A—C13A	1.395 (2)	C8B—C13B	1.3939 (19)
C9A—C10A	1.385 (2)	C9B—C10B	1.384 (2)
C9A—H9A	0.951 (17)	C9B—H9B	0.948 (18)
C10A—C11A	1.382 (2)	C10B—C11B	1.385 (2)
C10A—H10A	0.987 (17)	C10B—H10B	0.990 (18)
C11A—C12A	1.383 (2)	C11B—C12B	1.384 (2)
C11A—C14A	1.506 (2)	C11B—C14B	1.508 (2)
C12A—C13A	1.385 (2)	C12B—C13B	1.3902 (19)
C12A—H12A	0.953 (17)	C12B—H12B	0.977 (17)
C13A—H13A	0.975 (17)	C13B—H13B	0.998 (15)
C14A—H141	0.99 (4)	C14B—H147	0.97 (3)
C14A—H142	1.07 (4)	C14B—H148	1.00 (3)
C14A—H143	1.04 (4)	C14B—H149	1.00 (3)
C14A—H144	0.96 (5)	C14B—H150	1.03 (6)
C14A—H145	0.96 (5)	C14B—H151	1.12 (6)
C14A—H146	1.01 (5)	C14B—H152	0.97 (6)
C7A—N1A—C8A	119.51 (12)	C7B—N1B—C8B	120.17 (11)
O2A—N2A—O1A	123.67 (14)	O2B—N2B—O1B	123.23 (12)
O2A—N2A—C4A	118.34 (14)	O2B—N2B—C4B	118.45 (12)
O1A—N2A—C4A	117.98 (13)	O1B—N2B—C4B	118.32 (12)
C2A—C1A—C6A	119.39 (12)	C2B—C1B—C6B	119.74 (12)
C2A—C1A—C7A	119.07 (12)	C2B—C1B—C7B	119.52 (11)
C6A—C1A—C7A	121.53 (12)	C6B—C1B—C7B	120.74 (11)
C3A—C2A—C1A	121.10 (13)	C3B—C2B—C1B	120.77 (12)
C3A—C2A—H2A	118.7 (9)	C3B—C2B—H2B	118.7 (9)
C1A—C2A—H2A	120.2 (9)	C1B—C2B—H2B	120.5 (9)
C4A—C3A—C2A	117.85 (13)	C4B—C3B—C2B	117.93 (12)
C4A—C3A—H3A	121.2 (10)	C4B—C3B—H3B	120.7 (9)
C2A—C3A—H3A	120.9 (10)	C2B—C3B—H3B	121.4 (9)
C5A—C4A—C3A	122.70 (13)	C5B—C4B—C3B	122.76 (12)
C5A—C4A—N2A	118.88 (13)	C5B—C4B—N2B	118.81 (11)
C3A—C4A—N2A	118.41 (12)	C3B—C4B—N2B	118.42 (11)
C4A—C5A—C6A	118.94 (13)	C4B—C5B—C6B	118.71 (12)
C4A—C5A—H5A	120.8 (10)	C4B—C5B—H5B	121.7 (9)
C6A—C5A—H5A	120.2 (10)	C6B—C5B—H5B	119.6 (9)
C5A—C6A—C1A	120.01 (13)	C5B—C6B—C1B	120.07 (12)
C5A—C6A—H6A	119.2 (10)	C5B—C6B—H6B	119.2 (9)
C1A—C6A—H6A	120.7 (10)	C1B—C6B—H6B	120.7 (9)
N1A—C7A—C1A	123.07 (13)	N1B—C7B—C1B	121.81 (12)
N1A—C7A—H7A	123.2 (10)	N1B—C7B—H7B	122.9 (9)
C1A—C7A—H7A	113.5 (10)	C1B—C7B—H7B	115.2 (9)
C9A—C8A—C13A	118.33 (12)	C9B—C8B—C13B	118.76 (12)
C9A—C8A—N1A	117.30 (12)	C9B—C8B—N1B	117.99 (12)
C13A—C8A—N1A	124.36 (12)	C13B—C8B—N1B	123.15 (12)
C8A—C9A—C10A	120.66 (14)	C10B—C9B—C8B	120.67 (14)
C8A—C9A—H9A	120.1 (10)	C10B—C9B—H9B	121.1 (11)
C10A—C9A—H9A	119.2 (10)	C8B—C9B—H9B	118.2 (11)
C11A—C10A—C9A	121.64 (14)	C9B—C10B—C11B	121.33 (14)
C11A—C10A—H10A	122.1 (10)	C9B—C10B—H10B	116.4 (10)
C9A—C10A—H10A	116.3 (10)	C11B—C10B—H10B	122.2 (10)
C10A—C11A—C12A	117.40 (13)	C12B—C11B—C10B	117.76 (13)
C10A—C11A—C14A	120.82 (15)	C12B—C11B—C14B	121.38 (15)
C12A—C11A—C14A	121.76 (15)	C10B—C11B—C14B	120.80 (16)
C11A—C12A—C13A	121.86 (14)	C11B—C12B—C13B	121.71 (14)
C11A—C12A—H12A	119.8 (10)	C11B—C12B—H12B	118.9 (10)
C13A—C12A—H12A	118.3 (10)	C13B—C12B—H12B	119.4 (10)
C12A—C13A—C8A	120.06 (14)	C12B—C13B—C8B	119.76 (13)
C12A—C13A—H13A	119.1 (10)	C12B—C13B—H13B	119.4 (9)
C8A—C13A—H13A	120.8 (10)	C8B—C13B—H13B	120.7 (9)
C11A—C14A—H141	111 (2)	C11B—C14B—H147	110.4 (18)
C11A—C14A—H142	112.7 (17)	C11B—C14B—H148	105.9 (17)
H141—C14A—H142	114 (3)	H147—C14B—H148	106 (2)
C11A—C14A—H143	109.2 (19)	C11B—C14B—H149	108.7 (16)
H141—C14A—H143	102 (3)	H147—C14B—H149	113 (3)
H142—C14A—H143	107 (3)	H148—C14B—H149	113 (2)
C11A—C14A—H144	113 (3)	C11B—C14B—H150	112 (3)
H141—C14A—H144	132 (3)	H147—C14B—H150	136 (3)
H142—C14A—H144	66 (3)	H148—C14B—H150	51 (3)
H143—C14A—H144	44 (3)	H149—C14B—H150	62 (3)
C11A—C14A—H145	104 (3)	C11B—C14B—H151	115 (3)
H141—C14A—H145	49 (3)	H147—C14B—H151	50 (3)
H142—C14A—H145	144 (3)	H148—C14B—H151	137 (3)
H143—C14A—H145	59 (3)	H149—C14B—H151	65 (3)
H144—C14A—H145	100 (4)	H150—C14B—H151	117 (4)
C11A—C14A—H146	115 (2)	C11B—C14B—H152	117 (3)
H141—C14A—H146	64 (3)	H147—C14B—H152	53 (3)
H142—C14A—H146	54 (3)	H148—C14B—H152	53 (3)
H143—C14A—H146	136 (3)	H149—C14B—H152	134 (3)
H144—C14A—H146	114 (4)	H150—C14B—H152	97 (4)
H145—C14A—H146	111 (4)	H151—C14B—H152	96 (4)
C6A—C1A—C2A—C3A	−0.6 (2)	C6B—C1B—C2B—C3B	−1.9 (2)
C7A—C1A—C2A—C3A	178.55 (14)	C7B—C1B—C2B—C3B	177.86 (12)
C1A—C2A—C3A—C4A	−0.2 (2)	C1B—C2B—C3B—C4B	1.2 (2)
C2A—C3A—C4A—C5A	1.0 (2)	C2B—C3B—C4B—C5B	0.3 (2)
C2A—C3A—C4A—N2A	−178.42 (13)	C2B—C3B—C4B—N2B	−179.04 (12)
O2A—N2A—C4A—C5A	−179.66 (16)	O2B—N2B—C4B—C5B	−176.86 (14)
O1A—N2A—C4A—C5A	−0.1 (2)	O1B—N2B—C4B—C5B	3.58 (19)
O2A—N2A—C4A—C3A	−0.2 (2)	O2B—N2B—C4B—C3B	2.6 (2)
O1A—N2A—C4A—C3A	179.36 (15)	O1B—N2B—C4B—C3B	−177.01 (13)
C3A—C4A—C5A—C6A	−0.9 (2)	C3B—C4B—C5B—C6B	−1.1 (2)
N2A—C4A—C5A—C6A	178.49 (13)	N2B—C4B—C5B—C6B	178.25 (12)
C4A—C5A—C6A—C1A	0.1 (2)	C4B—C5B—C6B—C1B	0.4 (2)
C2A—C1A—C6A—C5A	0.6 (2)	C2B—C1B—C6B—C5B	1.0 (2)
C7A—C1A—C6A—C5A	−178.46 (14)	C7B—C1B—C6B—C5B	−178.67 (13)
C8A—N1A—C7A—C1A	178.97 (13)	C8B—N1B—C7B—C1B	−178.62 (11)
C2A—C1A—C7A—N1A	−175.13 (15)	C2B—C1B—C7B—N1B	−166.65 (13)
C6A—C1A—C7A—N1A	4.0 (2)	C6B—C1B—C7B—N1B	13.1 (2)
C7A—N1A—C8A—C9A	−152.23 (15)	C7B—N1B—C8B—C9B	−142.97 (14)
C7A—N1A—C8A—C13A	28.6 (2)	C7B—N1B—C8B—C13B	40.65 (19)
C13A—C8A—C9A—C10A	−1.8 (2)	C13B—C8B—C9B—C10B	0.2 (2)
N1A—C8A—C9A—C10A	179.01 (13)	N1B—C8B—C9B—C10B	−176.31 (13)
C8A—C9A—C10A—C11A	0.2 (2)	C8B—C9B—C10B—C11B	0.4 (2)
C9A—C10A—C11A—C12A	1.3 (2)	C9B—C10B—C11B—C12B	−0.7 (2)
C9A—C10A—C11A—C14A	179.88 (16)	C9B—C10B—C11B—C14B	176.60 (15)
C10A—C11A—C12A—C13A	−1.3 (2)	C10B—C11B—C12B—C13B	0.4 (2)
C14A—C11A—C12A—C13A	−179.84 (16)	C14B—C11B—C12B—C13B	−176.89 (15)
C11A—C12A—C13A—C8A	−0.3 (2)	C11B—C12B—C13B—C8B	0.2 (2)
C9A—C8A—C13A—C12A	1.8 (2)	C9B—C8B—C13B—C12B	−0.5 (2)
N1A—C8A—C13A—C12A	−179.04 (14)	N1B—C8B—C13B—C12B	175.82 (12)

(5_90K) N-(4-nitrobenzylidene)-4-methylaniline

Crystal data

C14H12N2O2	F(000) = 504
Mr = 240.26	Dx = 1.366 Mg m^−3
Triclinic, P1	Melting point: 121.8 C K
a = 6.9610 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.3496 (7) Å	Cell parameters from 11270 reflections
c = 14.3296 (8) Å	θ = 3.0–30.0°
α = 73.168 (1)°	µ = 0.09 mm^−1
β = 82.719 (1)°	T = 90 K
γ = 85.061 (1)°	Block, yellow
V = 1167.99 (11) Å^3	0.50 × 0.36 × 0.18 mm
Z = 4

Data collection

Bruker SMART 1000 CCD diffractometer	6782 independent reflections
Radiation source: fine-focus sealed tube	6118 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Detector resolution: 8.192 pixels mm^-1	θmax = 30.0°, θmin = 1.5°
ω scan	h = −9→9
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −17→17
Tmin = 0.955, Tmax = 0.983	l = −20→20
18035 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.038	w = 1/[σ^2(Fo^2) + (0.0698P)^2 + 0.2469P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.111	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.44 e Å^−3
6782 reflections	Δρmin = −0.32 e Å^−3
438 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.021 (2)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different ϕ angle (0, 90, 180 and 270°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −32°. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections.

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	Occ. (<1)
N1A	0.74038 (10)	0.47775 (6)	0.12434 (5)	0.01732 (14)
N2A	0.73545 (11)	0.90625 (6)	−0.26485 (5)	0.01915 (15)
O1A	0.66506 (10)	0.87894 (6)	−0.32876 (5)	0.02448 (15)
O2A	0.79990 (12)	0.99966 (6)	−0.27727 (5)	0.02895 (16)
C1A	0.77132 (11)	0.66258 (7)	0.00916 (6)	0.01582 (15)
C2A	0.84431 (12)	0.76964 (7)	−0.00837 (6)	0.01756 (16)
C3A	0.83149 (12)	0.85102 (7)	−0.09786 (6)	0.01766 (16)
C4A	0.74456 (12)	0.82265 (7)	−0.16874 (6)	0.01562 (15)
C5A	0.66826 (12)	0.71771 (7)	−0.15352 (6)	0.01714 (15)
C6A	0.68178 (12)	0.63755 (7)	−0.06382 (6)	0.01688 (15)
C7A	0.79348 (12)	0.57920 (7)	0.10429 (6)	0.01737 (15)
C8A	0.77108 (11)	0.40218 (7)	0.21743 (6)	0.01539 (15)
C9A	0.79349 (12)	0.28681 (7)	0.22343 (6)	0.01773 (16)
C10A	0.82835 (12)	0.20756 (7)	0.31144 (6)	0.01771 (16)
C11A	0.84048 (11)	0.23997 (7)	0.39610 (6)	0.01645 (15)
C12A	0.81178 (12)	0.35515 (7)	0.39036 (6)	0.01751 (16)
C13A	0.77670 (12)	0.43555 (7)	0.30269 (6)	0.01695 (15)
C14A	0.87991 (14)	0.15217 (7)	0.49019 (6)	0.02081 (17)
H141	0.801 (2)	0.0869 (14)	0.5036 (12)	0.027 (3)*	0.834 (19)
H142	0.862 (2)	0.1831 (14)	0.5476 (12)	0.027 (3)*	0.834 (19)
H143	1.009 (3)	0.1258 (15)	0.4847 (14)	0.027 (3)*	0.834 (19)
H144	1.006 (12)	0.156 (7)	0.526 (6)	0.027 (3)*	0.166 (19)
H145	1.000 (13)	0.085 (7)	0.478 (7)	0.027 (3)*	0.166 (19)
H146	0.783 (13)	0.132 (7)	0.540 (6)	0.027 (3)*	0.166 (19)
H2A	0.9095 (19)	0.7879 (11)	0.0419 (9)	0.026 (3)*
H3A	0.8855 (18)	0.9242 (10)	−0.1108 (9)	0.024 (3)*
H5A	0.6027 (19)	0.7019 (11)	−0.2036 (10)	0.029 (3)*
H6A	0.6256 (18)	0.5663 (11)	−0.0522 (9)	0.024 (3)*
H7A	0.8591 (19)	0.6055 (11)	0.1495 (9)	0.028 (3)*
H9A	0.7872 (18)	0.2649 (10)	0.1646 (9)	0.024 (3)*
H10A	0.846 (2)	0.1284 (11)	0.3135 (10)	0.031 (3)*
H12A	0.8140 (18)	0.3785 (11)	0.4492 (9)	0.025 (3)*
H13A	0.7481 (18)	0.5136 (10)	0.3025 (9)	0.023 (3)*
N1B	0.26840 (10)	0.49861 (6)	0.40339 (5)	0.01578 (14)
N2B	0.21277 (10)	0.06419 (6)	0.78443 (5)	0.01619 (14)
O1B	0.10169 (10)	0.08815 (5)	0.85014 (4)	0.02239 (14)
O2B	0.30724 (11)	−0.02657 (5)	0.79516 (5)	0.02611 (15)
C1B	0.28130 (11)	0.30849 (6)	0.50853 (6)	0.01430 (14)
C2B	0.37400 (11)	0.20091 (7)	0.52165 (6)	0.01488 (15)
C3B	0.35296 (11)	0.11978 (7)	0.61229 (6)	0.01517 (15)
C4B	0.23431 (11)	0.14843 (6)	0.68796 (5)	0.01404 (14)
C5B	0.13588 (12)	0.25358 (7)	0.67684 (6)	0.01551 (15)
C6B	0.16121 (12)	0.33402 (7)	0.58639 (6)	0.01590 (15)
C7B	0.31321 (11)	0.39383 (7)	0.41277 (6)	0.01528 (15)
C8B	0.29582 (11)	0.57777 (7)	0.30964 (6)	0.01460 (15)
C9B	0.35779 (12)	0.68429 (7)	0.30448 (6)	0.01736 (16)
C10B	0.37564 (12)	0.76791 (7)	0.21541 (6)	0.01828 (16)
C11B	0.33020 (11)	0.74902 (7)	0.12928 (6)	0.01672 (15)
C12B	0.27002 (12)	0.64187 (7)	0.13502 (6)	0.01704 (15)
C13B	0.25213 (12)	0.55693 (7)	0.22389 (6)	0.01588 (15)
C14B	0.33917 (14)	0.84247 (8)	0.03454 (7)	0.02208 (17)
H147	0.371 (3)	0.8101 (16)	−0.0211 (14)	0.029 (3)*	0.76 (3)
H148	0.441 (3)	0.8955 (17)	0.0348 (15)	0.029 (3)*	0.76 (3)
H149	0.206 (3)	0.8861 (18)	0.0296 (16)	0.029 (3)*	0.76 (3)
H150	0.249 (10)	0.906 (6)	0.042 (5)	0.029 (3)*	0.24 (3)
H151	0.277 (10)	0.828 (5)	−0.029 (4)	0.029 (3)*	0.24 (3)
H152	0.465 (9)	0.861 (5)	0.005 (5)	0.029 (3)*	0.24 (3)
H2B	0.4571 (17)	0.1836 (10)	0.4678 (8)	0.018 (3)*
H3B	0.4203 (18)	0.0466 (10)	0.6225 (9)	0.024 (3)*
H5B	0.0499 (18)	0.2700 (10)	0.7298 (9)	0.024 (3)*
H6B	0.0910 (18)	0.4065 (10)	0.5770 (9)	0.023 (3)*
H7B	0.3774 (18)	0.3653 (10)	0.3592 (9)	0.026 (3)*
H9B	0.3871 (19)	0.6987 (11)	0.3649 (9)	0.026 (3)*
H10B	0.4165 (18)	0.8424 (10)	0.2142 (9)	0.024 (3)*
H12B	0.2394 (18)	0.6283 (10)	0.0759 (9)	0.023 (3)*
H13B	0.2010 (18)	0.4835 (10)	0.2257 (9)	0.023 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0188 (3)	0.0162 (3)	0.0153 (3)	−0.0003 (2)	−0.0026 (2)	−0.0016 (2)
N2A	0.0237 (3)	0.0172 (3)	0.0145 (3)	0.0030 (3)	−0.0017 (3)	−0.0026 (2)
O1A	0.0320 (3)	0.0259 (3)	0.0154 (3)	0.0027 (3)	−0.0065 (2)	−0.0051 (2)
O2A	0.0460 (4)	0.0162 (3)	0.0216 (3)	−0.0044 (3)	−0.0044 (3)	0.0006 (2)
C1A	0.0162 (3)	0.0159 (3)	0.0146 (3)	−0.0012 (3)	−0.0018 (3)	−0.0029 (3)
C2A	0.0204 (4)	0.0177 (4)	0.0148 (3)	−0.0040 (3)	−0.0032 (3)	−0.0036 (3)
C3A	0.0210 (4)	0.0153 (3)	0.0164 (3)	−0.0034 (3)	−0.0011 (3)	−0.0037 (3)
C4A	0.0179 (3)	0.0148 (3)	0.0124 (3)	0.0015 (3)	−0.0014 (3)	−0.0019 (3)
C5A	0.0190 (4)	0.0178 (4)	0.0155 (3)	0.0000 (3)	−0.0040 (3)	−0.0055 (3)
C6A	0.0194 (4)	0.0146 (3)	0.0169 (4)	−0.0021 (3)	−0.0031 (3)	−0.0039 (3)
C7A	0.0177 (4)	0.0186 (4)	0.0149 (3)	−0.0029 (3)	−0.0035 (3)	−0.0020 (3)
C8A	0.0143 (3)	0.0156 (3)	0.0149 (3)	−0.0014 (3)	−0.0020 (3)	−0.0019 (3)
C9A	0.0192 (4)	0.0169 (4)	0.0174 (4)	−0.0006 (3)	−0.0026 (3)	−0.0051 (3)
C10A	0.0180 (4)	0.0140 (3)	0.0201 (4)	0.0003 (3)	−0.0025 (3)	−0.0034 (3)
C11A	0.0137 (3)	0.0161 (3)	0.0173 (3)	−0.0015 (3)	−0.0020 (3)	−0.0008 (3)
C12A	0.0198 (4)	0.0170 (4)	0.0149 (3)	−0.0025 (3)	−0.0021 (3)	−0.0028 (3)
C13A	0.0192 (4)	0.0144 (3)	0.0165 (4)	−0.0015 (3)	−0.0017 (3)	−0.0030 (3)
C14A	0.0224 (4)	0.0177 (4)	0.0190 (4)	−0.0007 (3)	−0.0053 (3)	0.0012 (3)
N1B	0.0168 (3)	0.0154 (3)	0.0133 (3)	−0.0006 (2)	−0.0017 (2)	−0.0011 (2)
N2B	0.0202 (3)	0.0146 (3)	0.0132 (3)	−0.0028 (2)	−0.0025 (2)	−0.0023 (2)
O1B	0.0292 (3)	0.0216 (3)	0.0146 (3)	−0.0029 (2)	0.0035 (2)	−0.0043 (2)
O2B	0.0375 (4)	0.0167 (3)	0.0192 (3)	0.0058 (3)	−0.0014 (3)	−0.0001 (2)
C1B	0.0149 (3)	0.0143 (3)	0.0130 (3)	−0.0008 (3)	−0.0026 (3)	−0.0023 (3)
C2B	0.0155 (3)	0.0156 (3)	0.0131 (3)	−0.0001 (3)	−0.0013 (3)	−0.0037 (3)
C3B	0.0169 (3)	0.0137 (3)	0.0145 (3)	0.0003 (3)	−0.0028 (3)	−0.0032 (3)
C4B	0.0157 (3)	0.0136 (3)	0.0120 (3)	−0.0022 (3)	−0.0022 (3)	−0.0015 (3)
C5B	0.0163 (3)	0.0163 (3)	0.0135 (3)	−0.0003 (3)	−0.0008 (3)	−0.0040 (3)
C6B	0.0171 (3)	0.0142 (3)	0.0152 (3)	0.0010 (3)	−0.0015 (3)	−0.0028 (3)
C7B	0.0155 (3)	0.0163 (3)	0.0128 (3)	−0.0002 (3)	−0.0017 (3)	−0.0023 (3)
C8B	0.0145 (3)	0.0143 (3)	0.0130 (3)	0.0008 (3)	−0.0011 (2)	−0.0013 (3)
C9B	0.0190 (4)	0.0164 (3)	0.0168 (4)	−0.0014 (3)	−0.0037 (3)	−0.0038 (3)
C10B	0.0179 (4)	0.0147 (3)	0.0204 (4)	−0.0025 (3)	−0.0026 (3)	−0.0014 (3)
C11B	0.0146 (3)	0.0166 (3)	0.0155 (3)	0.0008 (3)	0.0004 (3)	−0.0003 (3)
C12B	0.0188 (4)	0.0170 (3)	0.0140 (3)	0.0012 (3)	−0.0021 (3)	−0.0029 (3)
C13B	0.0177 (3)	0.0138 (3)	0.0152 (3)	0.0002 (3)	−0.0022 (3)	−0.0026 (3)
C14B	0.0228 (4)	0.0188 (4)	0.0182 (4)	0.0009 (3)	0.0013 (3)	0.0029 (3)

Geometric parameters (Å, º)

N1A—C7A	1.2779 (11)	N1B—C7B	1.2768 (10)
N1A—C8A	1.4188 (10)	N1B—C8B	1.4154 (10)
N2A—O2A	1.2303 (10)	N2B—O1B	1.2286 (9)
N2A—O1A	1.2303 (10)	N2B—O2B	1.2294 (9)
N2A—C4A	1.4676 (10)	N2B—C4B	1.4687 (10)
C1A—C2A	1.4000 (11)	C1B—C2B	1.3984 (10)
C1A—C6A	1.4012 (11)	C1B—C6B	1.4018 (11)
C1A—C7A	1.4681 (11)	C1B—C7B	1.4726 (10)
C2A—C3A	1.3892 (11)	C2B—C3B	1.3913 (10)
C2A—H2A	0.985 (13)	C2B—H2B	0.968 (11)
C3A—C4A	1.3853 (11)	C3B—C4B	1.3886 (11)
C3A—H3A	0.968 (13)	C3B—H3B	0.962 (12)
C4A—C5A	1.3909 (11)	C4B—C5B	1.3912 (11)
C5A—C6A	1.3852 (11)	C5B—C6B	1.3873 (11)
C5A—H5A	0.970 (13)	C5B—H5B	0.964 (12)
C6A—H6A	0.956 (12)	C6B—H6B	0.964 (12)
C7A—H7A	0.978 (13)	C7B—H7B	0.977 (12)
C8A—C9A	1.3986 (11)	C8B—C9B	1.3983 (11)
C8A—C13A	1.4036 (11)	C8B—C13B	1.4001 (11)
C9A—C10A	1.3889 (11)	C9B—C10B	1.3891 (11)
C9A—H9A	0.965 (12)	C9B—H9B	0.981 (13)
C10A—C11A	1.3970 (12)	C10B—C11B	1.3986 (12)
C10A—H10A	0.967 (13)	C10B—H10B	0.981 (12)
C11A—C12A	1.3992 (11)	C11B—C12B	1.3989 (11)
C11A—C14A	1.5050 (11)	C11B—C14B	1.5041 (11)
C12A—C13A	1.3919 (11)	C12B—C13B	1.3950 (10)
C12A—H12A	0.969 (13)	C12B—H12B	0.962 (12)
C13A—H13A	0.966 (12)	C13B—H13B	0.995 (12)
C14A—H141	0.975 (17)	C14B—H147	0.984 (19)
C14A—H142	0.993 (17)	C14B—H148	1.01 (2)
C14A—H143	0.931 (19)	C14B—H149	1.03 (2)
C14A—H144	1.08 (9)	C14B—H150	0.98 (7)
C14A—H145	1.16 (9)	C14B—H151	1.12 (6)
C14A—H146	0.91 (9)	C14B—H152	0.94 (6)
C7A—N1A—C8A	118.45 (7)	C7B—N1B—C8B	119.49 (7)
O2A—N2A—O1A	123.57 (7)	O1B—N2B—O2B	123.47 (7)
O2A—N2A—C4A	118.13 (7)	O1B—N2B—C4B	118.34 (7)
O1A—N2A—C4A	118.30 (7)	O2B—N2B—C4B	118.19 (7)
C2A—C1A—C6A	119.72 (7)	C2B—C1B—C6B	119.87 (7)
C2A—C1A—C7A	118.27 (7)	C2B—C1B—C7B	119.16 (7)
C6A—C1A—C7A	122.01 (7)	C6B—C1B—C7B	120.97 (7)
C3A—C2A—C1A	120.79 (7)	C3B—C2B—C1B	120.60 (7)
C3A—C2A—H2A	118.6 (7)	C3B—C2B—H2B	119.7 (7)
C1A—C2A—H2A	120.5 (7)	C1B—C2B—H2B	119.7 (7)
C4A—C3A—C2A	117.85 (7)	C4B—C3B—C2B	117.91 (7)
C4A—C3A—H3A	121.3 (7)	C4B—C3B—H3B	121.1 (7)
C2A—C3A—H3A	120.9 (7)	C2B—C3B—H3B	121.0 (7)
C3A—C4A—C5A	122.95 (7)	C3B—C4B—C5B	123.04 (7)
C3A—C4A—N2A	118.60 (7)	C3B—C4B—N2B	118.52 (7)
C5A—C4A—N2A	118.44 (7)	C5B—C4B—N2B	118.44 (7)
C6A—C5A—C4A	118.50 (7)	C6B—C5B—C4B	118.22 (7)
C6A—C5A—H5A	120.7 (8)	C6B—C5B—H5B	120.5 (7)
C4A—C5A—H5A	120.8 (8)	C4B—C5B—H5B	121.2 (7)
C5A—C6A—C1A	120.17 (7)	C5B—C6B—C1B	120.33 (7)
C5A—C6A—H6A	118.8 (7)	C5B—C6B—H6B	119.2 (7)
C1A—C6A—H6A	121.0 (7)	C1B—C6B—H6B	120.4 (7)
N1A—C7A—C1A	122.30 (7)	N1B—C7B—C1B	121.08 (7)
N1A—C7A—H7A	122.4 (8)	N1B—C7B—H7B	123.3 (7)
C1A—C7A—H7A	115.2 (8)	C1B—C7B—H7B	115.6 (7)
C9A—C8A—C13A	118.76 (7)	C9B—C8B—C13B	119.02 (7)
C9A—C8A—N1A	116.78 (7)	C9B—C8B—N1B	117.63 (7)
C13A—C8A—N1A	124.45 (7)	C13B—C8B—N1B	123.22 (7)
C10A—C9A—C8A	120.32 (7)	C10B—C9B—C8B	120.29 (7)
C10A—C9A—H9A	121.7 (7)	C10B—C9B—H9B	121.0 (7)
C8A—C9A—H9A	117.9 (7)	C8B—C9B—H9B	118.7 (7)
C9A—C10A—C11A	121.48 (7)	C9B—C10B—C11B	121.44 (7)
C9A—C10A—H10A	118.9 (8)	C9B—C10B—H10B	118.5 (7)
C11A—C10A—H10A	119.6 (8)	C11B—C10B—H10B	120.0 (7)
C10A—C11A—C12A	117.90 (7)	C10B—C11B—C12B	117.84 (7)
C10A—C11A—C14A	120.23 (7)	C10B—C11B—C14B	120.82 (7)
C12A—C11A—C14A	121.86 (7)	C12B—C11B—C14B	121.31 (8)
C13A—C12A—C11A	121.26 (7)	C13B—C12B—C11B	121.35 (7)
C13A—C12A—H12A	119.9 (7)	C13B—C12B—H12B	120.5 (7)
C11A—C12A—H12A	118.8 (7)	C11B—C12B—H12B	118.2 (7)
C12A—C13A—C8A	120.22 (7)	C12B—C13B—C8B	120.05 (7)
C12A—C13A—H13A	119.0 (7)	C12B—C13B—H13B	118.9 (7)
C8A—C13A—H13A	120.7 (7)	C8B—C13B—H13B	121.0 (7)
C11A—C14A—H141	112.1 (9)	C11B—C14B—H147	109.8 (11)
C11A—C14A—H142	112.8 (9)	C11B—C14B—H148	108.9 (11)
H141—C14A—H142	109.3 (13)	H147—C14B—H148	110.3 (15)
C11A—C14A—H143	108.7 (12)	C11B—C14B—H149	108.6 (12)
H141—C14A—H143	107.2 (14)	H147—C14B—H149	109.9 (16)
H142—C14A—H143	106.5 (14)	H148—C14B—H149	109.4 (15)
C11A—C14A—H144	121 (4)	C11B—C14B—H150	110 (4)
H141—C14A—H144	126 (4)	H147—C14B—H150	130 (4)
H142—C14A—H144	62 (5)	H148—C14B—H150	84 (4)
H143—C14A—H144	45 (4)	H149—C14B—H150	28 (4)
C11A—C14A—H145	113 (4)	C11B—C14B—H151	118 (3)
H141—C14A—H145	81 (4)	H147—C14B—H151	37 (3)
H142—C14A—H145	125 (4)	H148—C14B—H151	129 (3)
H143—C14A—H145	28 (4)	H149—C14B—H151	73 (3)
H144—C14A—H145	69 (6)	H150—C14B—H151	97 (5)
C11A—C14A—H146	120 (5)	C11B—C14B—H152	115 (4)
H141—C14A—H146	55 (5)	H147—C14B—H152	71 (4)
H142—C14A—H146	56 (5)	H148—C14B—H152	40 (4)
H143—C14A—H146	131 (5)	H149—C14B—H152	133 (4)
H144—C14A—H146	104 (7)	H150—C14B—H152	116 (5)
H145—C14A—H146	119 (7)	H151—C14B—H152	100 (5)
C6A—C1A—C2A—C3A	−0.90 (12)	C6B—C1B—C2B—C3B	−1.97 (12)
C7A—C1A—C2A—C3A	178.50 (7)	C7B—C1B—C2B—C3B	177.49 (7)
C1A—C2A—C3A—C4A	−0.04 (12)	C1B—C2B—C3B—C4B	1.36 (11)
C2A—C3A—C4A—C5A	0.88 (13)	C2B—C3B—C4B—C5B	0.34 (12)
C2A—C3A—C4A—N2A	−178.02 (7)	C2B—C3B—C4B—N2B	−179.19 (7)
O2A—N2A—C4A—C3A	−2.38 (11)	O1B—N2B—C4B—C3B	−177.15 (7)
O1A—N2A—C4A—C3A	177.14 (8)	O2B—N2B—C4B—C3B	2.98 (11)
O2A—N2A—C4A—C5A	178.67 (8)	O1B—N2B—C4B—C5B	3.30 (11)
O1A—N2A—C4A—C5A	−1.81 (11)	O2B—N2B—C4B—C5B	−176.58 (7)
C3A—C4A—C5A—C6A	−0.74 (12)	C3B—C4B—C5B—C6B	−1.40 (12)
N2A—C4A—C5A—C6A	178.16 (7)	N2B—C4B—C5B—C6B	178.13 (7)
C4A—C5A—C6A—C1A	−0.24 (12)	C4B—C5B—C6B—C1B	0.77 (12)
C2A—C1A—C6A—C5A	1.04 (12)	C2B—C1B—C6B—C5B	0.88 (12)
C7A—C1A—C6A—C5A	−178.34 (7)	C7B—C1B—C6B—C5B	−178.57 (7)
C8A—N1A—C7A—C1A	178.69 (7)	C8B—N1B—C7B—C1B	−178.13 (7)
C2A—C1A—C7A—N1A	−176.20 (8)	C2B—C1B—C7B—N1B	−164.28 (8)
C6A—C1A—C7A—N1A	3.18 (13)	C6B—C1B—C7B—N1B	15.17 (12)
C7A—N1A—C8A—C9A	−152.90 (8)	C7B—N1B—C8B—C9B	−142.99 (8)
C7A—N1A—C8A—C13A	28.29 (12)	C7B—N1B—C8B—C13B	41.25 (11)
C13A—C8A—C9A—C10A	−2.54 (12)	C13B—C8B—C9B—C10B	−0.04 (12)
N1A—C8A—C9A—C10A	178.58 (7)	N1B—C8B—C9B—C10B	−175.98 (7)
C8A—C9A—C10A—C11A	0.53 (13)	C8B—C9B—C10B—C11B	0.88 (13)
C9A—C10A—C11A—C12A	1.48 (12)	C9B—C10B—C11B—C12B	−1.43 (12)
C9A—C10A—C11A—C14A	−179.54 (8)	C9B—C10B—C11B—C14B	176.43 (7)
C10A—C11A—C12A—C13A	−1.47 (12)	C10B—C11B—C12B—C13B	1.18 (12)
C14A—C11A—C12A—C13A	179.57 (8)	C14B—C11B—C12B—C13B	−176.67 (7)
C11A—C12A—C13A—C8A	−0.54 (13)	C11B—C12B—C13B—C8B	−0.38 (12)
C9A—C8A—C13A—C12A	2.55 (12)	C9B—C8B—C13B—C12B	−0.21 (12)
N1A—C8A—C13A—C12A	−178.66 (7)	N1B—C8B—C13B—C12B	175.49 (7)

(6_rt) N-(4-methoxybenzylidene)aniline

Crystal data

C14H13NO	Dx = 1.196 Mg m^−3
Mr = 211.25	Melting point: 61.3 C K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.2529 (6) Å	Cell parameters from 7226 reflections
b = 12.6440 (7) Å	θ = 2.2–25.3°
c = 18.2037 (10) Å	µ = 0.08 mm^−1
β = 95.998 (1)°	T = 300 K
V = 2347.0 (2) Å^3	Block, colourless
Z = 8	0.46 × 0.40 × 0.20 mm
F(000) = 896

Data collection

Bruker SMART 1000 CCD diffractometer	6867 independent reflections
Radiation source: fine-focus sealed tube	3566 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 8.192 pixels mm^-1	θmax = 30.1°, θmin = 2.0°
ω scan	h = −14→14
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −17→17
Tmin = 0.966, Tmax = 0.985	l = −25→25
35497 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	All H-atom parameters refined
wR(F^2) = 0.147	w = 1/[σ^2(Fo^2) + (0.0208P)^2 + 0.8084P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
6867 reflections	Δρmax = 0.16 e Å^−3
393 parameters	Δρmin = −0.20 e Å^−3
0 restraints

Special details

Experimental. The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different ϕ angle (0, 90, 180 and 270°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −32°. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections.

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
N1A	0.38099 (14)	0.91681 (12)	0.15455 (9)	0.0631 (4)
O1A	0.52869 (18)	0.58915 (12)	−0.09114 (8)	0.0959 (5)
C1A	0.43032 (16)	0.83813 (14)	0.04057 (9)	0.0558 (4)
C2A	0.42241 (19)	0.85055 (16)	−0.03514 (11)	0.0658 (5)
C3A	0.4531 (2)	0.76970 (16)	−0.08118 (11)	0.0687 (5)
C4A	0.49464 (19)	0.67410 (15)	−0.05105 (10)	0.0666 (5)
C5A	0.5040 (2)	0.66036 (17)	0.02498 (11)	0.0752 (6)
C6A	0.47206 (19)	0.74060 (16)	0.06988 (11)	0.0655 (5)
C7A	0.39159 (17)	0.92481 (15)	0.08640 (11)	0.0613 (4)
C8A	0.33845 (16)	1.00390 (14)	0.19477 (11)	0.0610 (4)
C9A	0.3559 (2)	0.99644 (19)	0.27058 (12)	0.0772 (6)
C10A	0.3202 (3)	1.0781 (2)	0.31405 (16)	0.0977 (8)
C11A	0.2627 (3)	1.1676 (2)	0.28274 (18)	0.0957 (8)
C12A	0.2416 (2)	1.1743 (2)	0.20756 (18)	0.0930 (7)
C13A	0.2778 (2)	1.09372 (18)	0.16335 (14)	0.0817 (6)
C14A	0.5069 (4)	0.5934 (3)	−0.16959 (15)	0.1053 (9)
H2A	0.391 (2)	0.9191 (16)	−0.0560 (11)	0.082 (6)*
H3A	0.4467 (18)	0.7806 (15)	−0.1336 (11)	0.078 (6)*
H5A	0.534 (2)	0.5936 (17)	0.0441 (11)	0.090 (7)*
H6A	0.4772 (17)	0.7318 (14)	0.1225 (10)	0.068 (5)*
H7A	0.376 (2)	0.9910 (16)	0.0595 (11)	0.086 (6)*
H9A	0.400 (2)	0.9326 (19)	0.2909 (12)	0.099 (8)*
H10A	0.337 (2)	1.0696 (18)	0.3672 (14)	0.103 (8)*
H11A	0.232 (2)	1.223 (2)	0.3107 (14)	0.114 (9)*
H12A	0.199 (2)	1.236 (2)	0.1842 (13)	0.108 (8)*
H13A	0.262 (2)	1.1001 (17)	0.1112 (13)	0.092 (7)*
H14A	0.531 (3)	0.528 (2)	−0.1864 (15)	0.118 (9)*
H15A	0.412 (3)	0.608 (2)	−0.1848 (17)	0.143 (12)*
H16A	0.562 (3)	0.649 (3)	−0.1872 (19)	0.165 (15)*
N1B	0.80662 (14)	0.97512 (11)	0.13195 (8)	0.0590 (4)
O1B	1.00362 (16)	0.60192 (12)	−0.06645 (8)	0.0916 (5)
C1B	0.93794 (17)	0.85753 (14)	0.06682 (10)	0.0593 (4)
C2B	1.0641 (2)	0.82856 (19)	0.05550 (14)	0.0843 (7)
C3B	1.0907 (2)	0.74486 (19)	0.01120 (13)	0.0801 (6)
C4B	0.9886 (2)	0.68691 (15)	−0.02225 (9)	0.0645 (5)
C5B	0.8609 (2)	0.71454 (17)	−0.01210 (11)	0.0708 (5)
C6B	0.83572 (19)	0.79821 (16)	0.03171 (10)	0.0628 (5)
C7B	0.91726 (19)	0.94515 (15)	0.11619 (11)	0.0645 (5)
C8B	0.79809 (17)	1.06201 (13)	0.18054 (9)	0.0555 (4)
C9B	0.6977 (2)	1.06192 (16)	0.22563 (11)	0.0670 (5)
C10B	0.6832 (2)	1.14477 (18)	0.27353 (12)	0.0758 (6)
C11B	0.7679 (2)	1.22903 (18)	0.27665 (12)	0.0773 (6)
C12B	0.8665 (2)	1.23029 (17)	0.23146 (13)	0.0797 (6)
C13B	0.8821 (2)	1.14803 (16)	0.18323 (12)	0.0692 (5)
C14B	1.1323 (4)	0.5650 (3)	−0.0723 (2)	0.1047 (9)
H2B	1.135 (2)	0.8695 (19)	0.0792 (13)	0.104 (7)*
H3B	1.180 (2)	0.7245 (16)	0.0056 (11)	0.087 (6)*
H5B	0.791 (2)	0.6736 (17)	−0.0351 (12)	0.091 (7)*
H6B	0.7463 (19)	0.8174 (14)	0.0399 (10)	0.069 (5)*
H7B	0.998 (2)	0.9792 (16)	0.1393 (11)	0.087 (6)*
H9B	0.6375 (19)	1.0033 (16)	0.2218 (10)	0.076 (6)*
H10B	0.609 (2)	1.1417 (17)	0.3051 (12)	0.098 (7)*
H11B	0.758 (2)	1.2879 (17)	0.3108 (12)	0.092 (7)*
H12B	0.931 (2)	1.2875 (18)	0.2327 (11)	0.093 (7)*
H13B	0.947 (2)	1.1510 (16)	0.1496 (11)	0.085 (6)*
H14B	1.186 (3)	0.617 (2)	−0.0948 (16)	0.132 (11)*
H15B	1.122 (3)	0.506 (2)	−0.1007 (17)	0.131 (10)*
H16B	1.176 (3)	0.546 (2)	−0.0242 (17)	0.128 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0613 (9)	0.0605 (9)	0.0668 (10)	−0.0016 (7)	0.0027 (7)	0.0004 (7)
O1A	0.1354 (14)	0.0759 (10)	0.0743 (10)	0.0147 (9)	0.0018 (9)	−0.0098 (8)
C1A	0.0476 (8)	0.0575 (10)	0.0609 (10)	−0.0098 (8)	−0.0003 (7)	0.0032 (8)
C2A	0.0703 (12)	0.0604 (11)	0.0656 (12)	−0.0007 (9)	0.0017 (9)	0.0091 (9)
C3A	0.0752 (12)	0.0728 (13)	0.0567 (11)	−0.0036 (10)	−0.0001 (9)	0.0065 (10)
C4A	0.0737 (12)	0.0615 (11)	0.0630 (11)	−0.0035 (9)	0.0000 (9)	−0.0039 (9)
C5A	0.0957 (15)	0.0612 (12)	0.0662 (12)	0.0076 (11)	−0.0038 (11)	0.0072 (10)
C6A	0.0724 (12)	0.0678 (12)	0.0545 (11)	−0.0025 (9)	−0.0017 (9)	0.0052 (9)
C7A	0.0548 (10)	0.0563 (11)	0.0724 (12)	−0.0053 (8)	0.0049 (8)	0.0065 (9)
C8A	0.0484 (9)	0.0605 (11)	0.0746 (12)	−0.0054 (8)	0.0091 (8)	−0.0022 (9)
C9A	0.0860 (15)	0.0748 (14)	0.0733 (13)	0.0035 (12)	0.0196 (11)	−0.0003 (11)
C10A	0.112 (2)	0.103 (2)	0.0818 (17)	0.0081 (16)	0.0281 (15)	−0.0110 (15)
C11A	0.0872 (16)	0.0873 (18)	0.117 (2)	0.0060 (14)	0.0333 (15)	−0.0240 (17)
C12A	0.0845 (16)	0.0735 (15)	0.122 (2)	0.0174 (13)	0.0159 (14)	−0.0015 (15)
C13A	0.0797 (14)	0.0781 (15)	0.0865 (16)	0.0150 (11)	0.0047 (12)	0.0007 (13)
C14A	0.137 (3)	0.103 (2)	0.0741 (16)	0.012 (2)	0.0047 (17)	−0.0231 (16)
N1B	0.0606 (9)	0.0541 (8)	0.0621 (9)	−0.0051 (7)	0.0057 (7)	0.0016 (7)
O1B	0.0973 (11)	0.0919 (11)	0.0867 (10)	−0.0031 (9)	0.0144 (8)	−0.0329 (9)
C1B	0.0551 (10)	0.0616 (10)	0.0607 (10)	−0.0064 (8)	0.0038 (8)	−0.0030 (8)
C2B	0.0568 (11)	0.0901 (16)	0.1058 (17)	−0.0139 (11)	0.0074 (11)	−0.0345 (13)
C3B	0.0589 (12)	0.0880 (15)	0.0950 (15)	−0.0062 (11)	0.0154 (11)	−0.0238 (12)
C4B	0.0768 (12)	0.0646 (11)	0.0522 (10)	−0.0055 (10)	0.0078 (9)	−0.0051 (9)
C5B	0.0627 (11)	0.0763 (13)	0.0709 (12)	−0.0110 (10)	−0.0048 (9)	−0.0116 (10)
C6B	0.0544 (10)	0.0689 (12)	0.0641 (11)	−0.0025 (9)	0.0015 (8)	−0.0026 (9)
C7B	0.0577 (11)	0.0648 (11)	0.0699 (12)	−0.0083 (9)	0.0014 (9)	−0.0077 (9)
C8B	0.0596 (10)	0.0518 (9)	0.0540 (9)	−0.0004 (8)	0.0011 (8)	0.0059 (8)
C9B	0.0694 (12)	0.0603 (11)	0.0727 (12)	−0.0030 (10)	0.0132 (10)	0.0093 (10)
C10B	0.0877 (15)	0.0750 (14)	0.0673 (12)	0.0100 (12)	0.0201 (11)	0.0101 (11)
C11B	0.0984 (16)	0.0696 (13)	0.0625 (12)	0.0096 (12)	0.0025 (11)	−0.0056 (10)
C12B	0.0874 (15)	0.0644 (13)	0.0864 (15)	−0.0153 (11)	0.0044 (12)	−0.0106 (11)
C13B	0.0716 (12)	0.0665 (12)	0.0705 (12)	−0.0120 (10)	0.0130 (10)	−0.0025 (10)
C14B	0.121 (2)	0.097 (2)	0.099 (2)	0.0112 (19)	0.0290 (19)	−0.0270 (18)

Geometric parameters (Å, º)

N1A—C7A	1.261 (2)	N1B—C7B	1.257 (2)
N1A—C8A	1.416 (2)	N1B—C8B	1.419 (2)
O1A—C4A	1.364 (2)	O1B—C4B	1.361 (2)
O1A—C14A	1.423 (3)	O1B—C14B	1.414 (3)
C1A—C2A	1.381 (2)	C1B—C2B	1.380 (3)
C1A—C6A	1.393 (2)	C1B—C6B	1.389 (2)
C1A—C7A	1.457 (3)	C1B—C7B	1.456 (2)
C2A—C3A	1.379 (3)	C2B—C3B	1.375 (3)
C2A—H2A	0.99 (2)	C2B—H2B	0.95 (2)
C3A—C4A	1.377 (3)	C3B—C4B	1.367 (3)
C3A—H3A	0.959 (19)	C3B—H3B	0.97 (2)
C4A—C5A	1.388 (3)	C4B—C5B	1.386 (3)
C5A—C6A	1.364 (3)	C5B—C6B	1.366 (3)
C5A—H5A	0.95 (2)	C5B—H5B	0.94 (2)
C6A—H6A	0.961 (18)	C6B—H6B	0.974 (18)
C7A—H7A	0.97 (2)	C7B—H7B	0.99 (2)
C8A—C9A	1.376 (3)	C8B—C9B	1.382 (3)
C8A—C13A	1.389 (3)	C8B—C13B	1.385 (2)
C9A—C10A	1.374 (3)	C9B—C10B	1.381 (3)
C9A—H9A	0.98 (2)	C9B—H9B	0.96 (2)
C10A—C11A	1.372 (4)	C10B—C11B	1.372 (3)
C10A—H10A	0.97 (2)	C10B—H10B	1.00 (2)
C11A—C12A	1.366 (4)	C11B—C12B	1.368 (3)
C11A—H11A	0.94 (3)	C11B—H11B	0.98 (2)
C12A—C13A	1.373 (3)	C12B—C13B	1.381 (3)
C12A—H12A	0.97 (2)	C12B—H12B	0.98 (2)
C13A—H13A	0.95 (2)	C13B—H13B	0.95 (2)
C14A—H14A	0.93 (3)	C14B—H14B	0.98 (3)
C14A—H15A	1.00 (3)	C14B—H15B	0.91 (3)
C14A—H16A	0.97 (3)	C14B—H16B	0.97 (3)
C7A—N1A—C8A	120.61 (16)	C7B—N1B—C8B	119.44 (15)
C4A—O1A—C14A	119.0 (2)	C4B—O1B—C14B	118.0 (2)
C2A—C1A—C6A	117.81 (18)	C2B—C1B—C6B	117.50 (18)
C2A—C1A—C7A	119.65 (17)	C2B—C1B—C7B	119.55 (17)
C6A—C1A—C7A	122.52 (17)	C6B—C1B—C7B	122.91 (17)
C3A—C2A—C1A	121.93 (19)	C3B—C2B—C1B	122.6 (2)
C3A—C2A—H2A	120.2 (11)	C3B—C2B—H2B	119.7 (14)
C1A—C2A—H2A	117.8 (11)	C1B—C2B—H2B	117.8 (14)
C4A—C3A—C2A	119.32 (18)	C4B—C3B—C2B	119.0 (2)
C4A—C3A—H3A	120.5 (12)	C4B—C3B—H3B	119.9 (12)
C2A—C3A—H3A	120.1 (12)	C2B—C3B—H3B	121.0 (12)
O1A—C4A—C3A	124.34 (18)	O1B—C4B—C3B	123.94 (19)
O1A—C4A—C5A	116.10 (18)	O1B—C4B—C5B	116.38 (17)
C3A—C4A—C5A	119.57 (19)	C3B—C4B—C5B	119.68 (19)
C6A—C5A—C4A	120.55 (19)	C6B—C5B—C4B	120.79 (18)
C6A—C5A—H5A	121.9 (13)	C6B—C5B—H5B	120.2 (13)
C4A—C5A—H5A	117.5 (13)	C4B—C5B—H5B	119.0 (13)
C5A—C6A—C1A	120.82 (18)	C5B—C6B—C1B	120.49 (18)
C5A—C6A—H6A	121.3 (11)	C5B—C6B—H6B	121.3 (11)
C1A—C6A—H6A	117.9 (11)	C1B—C6B—H6B	118.2 (11)
N1A—C7A—C1A	124.03 (18)	N1B—C7B—C1B	124.28 (17)
N1A—C7A—H7A	122.5 (12)	N1B—C7B—H7B	120.5 (12)
C1A—C7A—H7A	113.5 (12)	C1B—C7B—H7B	115.1 (12)
C9A—C8A—C13A	118.3 (2)	C9B—C8B—C13B	118.61 (18)
C9A—C8A—N1A	116.75 (18)	C9B—C8B—N1B	117.90 (16)
C13A—C8A—N1A	124.87 (18)	C13B—C8B—N1B	123.46 (17)
C10A—C9A—C8A	120.8 (2)	C10B—C9B—C8B	120.7 (2)
C10A—C9A—H9A	122.9 (13)	C10B—C9B—H9B	121.3 (12)
C8A—C9A—H9A	116.2 (13)	C8B—C9B—H9B	118.0 (12)
C11A—C10A—C9A	120.6 (3)	C11B—C10B—C9B	120.4 (2)
C11A—C10A—H10A	122.0 (14)	C11B—C10B—H10B	121.5 (13)
C9A—C10A—H10A	117.4 (15)	C9B—C10B—H10B	118.2 (13)
C12A—C11A—C10A	118.9 (3)	C12B—C11B—C10B	119.2 (2)
C12A—C11A—H11A	118.1 (16)	C12B—C11B—H11B	120.4 (13)
C10A—C11A—H11A	122.9 (16)	C10B—C11B—H11B	120.4 (13)
C11A—C12A—C13A	121.1 (3)	C11B—C12B—C13B	121.0 (2)
C11A—C12A—H12A	120.3 (14)	C11B—C12B—H12B	122.2 (13)
C13A—C12A—H12A	118.6 (15)	C13B—C12B—H12B	116.8 (13)
C12A—C13A—C8A	120.1 (2)	C12B—C13B—C8B	120.0 (2)
C12A—C13A—H13A	119.6 (14)	C12B—C13B—H13B	121.0 (13)
C8A—C13A—H13A	120.3 (14)	C8B—C13B—H13B	118.8 (13)
O1A—C14A—H14A	106.1 (17)	O1B—C14B—H14B	112.4 (17)
O1A—C14A—H15A	109.3 (18)	O1B—C14B—H15B	105.4 (19)
H14A—C14A—H15A	111 (2)	H14B—C14B—H15B	111 (2)
O1A—C14A—H16A	109 (2)	O1B—C14B—H16B	110.9 (17)
H14A—C14A—H16A	111 (3)	H14B—C14B—H16B	108 (2)
H15A—C14A—H16A	111 (3)	H15B—C14B—H16B	109 (3)
C6A—C1A—C2A—C3A	0.7 (3)	C6B—C1B—C2B—C3B	0.3 (3)
C7A—C1A—C2A—C3A	−177.47 (17)	C7B—C1B—C2B—C3B	178.2 (2)
C1A—C2A—C3A—C4A	−1.0 (3)	C1B—C2B—C3B—C4B	−0.9 (4)
C14A—O1A—C4A—C3A	−7.4 (4)	C14B—O1B—C4B—C3B	6.5 (3)
C14A—O1A—C4A—C5A	172.7 (3)	C14B—O1B—C4B—C5B	−173.9 (2)
C2A—C3A—C4A—O1A	−179.35 (19)	C2B—C3B—C4B—O1B	−179.2 (2)
C2A—C3A—C4A—C5A	0.5 (3)	C2B—C3B—C4B—C5B	1.2 (3)
O1A—C4A—C5A—C6A	−179.9 (2)	O1B—C4B—C5B—C6B	179.53 (18)
C3A—C4A—C5A—C6A	0.2 (3)	C3B—C4B—C5B—C6B	−0.8 (3)
C4A—C5A—C6A—C1A	−0.5 (3)	C4B—C5B—C6B—C1B	0.2 (3)
C2A—C1A—C6A—C5A	0.1 (3)	C2B—C1B—C6B—C5B	0.1 (3)
C7A—C1A—C6A—C5A	178.15 (18)	C7B—C1B—C6B—C5B	−177.77 (18)
C8A—N1A—C7A—C1A	−177.83 (15)	C8B—N1B—C7B—C1B	−179.68 (16)
C2A—C1A—C7A—N1A	171.44 (17)	C2B—C1B—C7B—N1B	−177.5 (2)
C6A—C1A—C7A—N1A	−6.6 (3)	C6B—C1B—C7B—N1B	0.3 (3)
C7A—N1A—C8A—C9A	−166.58 (18)	C7B—N1B—C8B—C9B	−147.77 (18)
C7A—N1A—C8A—C13A	15.3 (3)	C7B—N1B—C8B—C13B	34.5 (3)
C13A—C8A—C9A—C10A	−3.2 (3)	C13B—C8B—C9B—C10B	−1.4 (3)
N1A—C8A—C9A—C10A	178.6 (2)	N1B—C8B—C9B—C10B	−179.25 (17)
C8A—C9A—C10A—C11A	1.9 (4)	C8B—C9B—C10B—C11B	0.5 (3)
C9A—C10A—C11A—C12A	−0.1 (4)	C9B—C10B—C11B—C12B	0.4 (3)
C10A—C11A—C12A—C13A	−0.5 (4)	C10B—C11B—C12B—C13B	−0.3 (3)
C11A—C12A—C13A—C8A	−0.8 (4)	C11B—C12B—C13B—C8B	−0.6 (3)
C9A—C8A—C13A—C12A	2.6 (3)	C9B—C8B—C13B—C12B	1.4 (3)
N1A—C8A—C13A—C12A	−179.3 (2)	N1B—C8B—C13B—C12B	179.18 (18)

(6_90K) N-(4-methoxybenzylidene)aniline

Crystal data

C14H13NO	Dx = 1.249 Mg m^−3
Mr = 211.25	Melting point: 61.3 C K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.0666 (13) Å	Cell parameters from 11566 reflections
b = 12.6374 (17) Å	θ = 2.3–30.0°
c = 17.732 (2) Å	µ = 0.08 mm^−1
β = 95.226 (3)°	T = 90 K
V = 2246.4 (5) Å^3	Block, colourless
Z = 8	0.46 × 0.40 × 0.20 mm
F(000) = 896

Data collection

Bruker SMART 1000 CCD diffractometer	6556 independent reflections
Radiation source: fine-focus sealed tube	5379 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 8.192 pixels mm^-1	θmax = 30.0°, θmin = 2.0°
ω scan	h = −14→14
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −17→17
Tmin = 0.965, Tmax = 0.984	l = −24→24
33475 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	All H-atom parameters refined
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0608P)^2 + 0.6548P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
6556 reflections	Δρmax = 0.35 e Å^−3
393 parameters	Δρmin = −0.25 e Å^−3
0 restraints

Special details

Experimental. The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different ϕ angle (0, 90, 180 and 270°) for the crystal and each exposure of 5 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −32°. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections.

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
N1A	0.38298 (9)	0.91441 (7)	0.15582 (5)	0.02108 (17)
O1A	0.53658 (9)	0.58368 (6)	−0.09568 (4)	0.02944 (18)
C1A	0.43631 (9)	0.83502 (8)	0.03890 (6)	0.01923 (19)
C2A	0.42892 (10)	0.84770 (8)	−0.03943 (6)	0.0214 (2)
C3A	0.46030 (10)	0.76572 (8)	−0.08695 (6)	0.0223 (2)
C4A	0.50165 (10)	0.66935 (8)	−0.05516 (6)	0.0218 (2)
C5A	0.50998 (11)	0.65521 (8)	0.02357 (6)	0.0235 (2)
C6A	0.47725 (10)	0.73673 (8)	0.06982 (6)	0.0215 (2)
C7A	0.39675 (10)	0.92304 (8)	0.08507 (6)	0.02039 (19)
C8A	0.33855 (10)	1.00261 (8)	0.19609 (6)	0.02023 (19)
C9A	0.36089 (11)	0.99829 (9)	0.27481 (6)	0.0241 (2)
C10A	0.32438 (12)	1.08174 (10)	0.31923 (7)	0.0293 (2)
C11A	0.26235 (11)	1.17053 (9)	0.28586 (7)	0.0294 (2)
C12A	0.23609 (11)	1.17382 (9)	0.20761 (7)	0.0286 (2)
C13A	0.27289 (11)	1.09089 (9)	0.16278 (7)	0.0256 (2)
C14A	0.51639 (14)	0.58948 (10)	−0.17657 (7)	0.0313 (2)
H2A	0.3978 (14)	0.9158 (11)	−0.0612 (8)	0.029 (4)*
H3A	0.4519 (14)	0.7759 (11)	−0.1411 (8)	0.025 (3)*
H5A	0.5370 (14)	0.5865 (11)	0.0439 (8)	0.031 (4)*
H6A	0.4827 (13)	0.7267 (10)	0.1253 (8)	0.025 (3)*
H7A	0.3809 (15)	0.9909 (12)	0.0576 (8)	0.033 (4)*
H9A	0.4048 (14)	0.9363 (11)	0.2973 (8)	0.026 (3)*
H10A	0.3424 (15)	1.0769 (12)	0.3745 (9)	0.036 (4)*
H11A	0.2348 (16)	1.2316 (13)	0.3165 (9)	0.041 (4)*
H12A	0.1901 (16)	1.2355 (12)	0.1848 (9)	0.037 (4)*
H13A	0.2522 (15)	1.0951 (12)	0.1069 (9)	0.037 (4)*
H14A	0.5407 (16)	0.5208 (13)	−0.1951 (9)	0.040 (4)*
H15A	0.4217 (16)	0.6016 (12)	−0.1926 (9)	0.037 (4)*
H16A	0.5736 (16)	0.6452 (13)	−0.1968 (9)	0.038 (4)*
N1B	0.80278 (9)	0.97763 (7)	0.13085 (5)	0.01969 (17)
O1B	1.00972 (8)	0.59501 (6)	−0.06576 (5)	0.02847 (18)
C1B	0.93871 (10)	0.85776 (8)	0.06521 (5)	0.01935 (19)
C2B	1.06899 (10)	0.82916 (9)	0.05444 (6)	0.0251 (2)
C3B	1.09804 (11)	0.74246 (9)	0.01088 (6)	0.0242 (2)
C4B	0.99325 (10)	0.68236 (8)	−0.02265 (5)	0.02079 (19)
C5B	0.86139 (10)	0.71039 (8)	−0.01342 (6)	0.0225 (2)
C6B	0.83410 (10)	0.79694 (8)	0.03010 (6)	0.02051 (19)
C7B	0.91751 (10)	0.94739 (8)	0.11469 (6)	0.02057 (19)
C8B	0.79563 (10)	1.06590 (8)	0.17975 (5)	0.01847 (18)
C9B	0.69426 (10)	1.06643 (8)	0.22839 (6)	0.0217 (2)
C10B	0.68101 (11)	1.15139 (9)	0.27698 (6)	0.0240 (2)
C11B	0.76808 (11)	1.23662 (9)	0.27740 (6)	0.0244 (2)
C12B	0.86771 (11)	1.23676 (8)	0.22806 (6)	0.0250 (2)
C13B	0.88148 (10)	1.15269 (8)	0.17920 (6)	0.0217 (2)
C14B	1.14310 (13)	0.55886 (10)	−0.07089 (7)	0.0312 (2)
H2B	1.1407 (14)	0.8714 (12)	0.0782 (8)	0.031 (4)*
H3B	1.1884 (14)	0.7240 (11)	0.0043 (8)	0.029 (3)*
H5B	0.7930 (15)	0.6683 (12)	−0.0361 (8)	0.031 (4)*
H6B	0.7423 (14)	0.8154 (11)	0.0382 (8)	0.026 (3)*
H7B	0.9983 (15)	0.9823 (11)	0.1360 (8)	0.031 (4)*
H9B	0.6317 (14)	1.0069 (11)	0.2277 (8)	0.029 (3)*
H10B	0.6091 (13)	1.1525 (11)	0.3110 (8)	0.024 (3)*
H11B	0.7582 (14)	1.2958 (11)	0.3111 (8)	0.029 (3)*
H12B	0.9304 (14)	1.2962 (12)	0.2286 (8)	0.031 (4)*
H13B	0.9501 (14)	1.1550 (11)	0.1430 (8)	0.027 (3)*
H14B	1.1963 (16)	0.6104 (12)	−0.0967 (9)	0.036 (4)*
H15B	1.1337 (16)	0.4933 (13)	−0.0994 (9)	0.042 (4)*
H16B	1.1873 (15)	0.5449 (12)	−0.0201 (9)	0.035 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0194 (4)	0.0206 (4)	0.0229 (4)	−0.0004 (3)	0.0002 (3)	−0.0009 (3)
O1A	0.0426 (5)	0.0228 (4)	0.0225 (4)	0.0031 (3)	0.0007 (3)	−0.0017 (3)
C1A	0.0157 (4)	0.0205 (4)	0.0212 (4)	−0.0027 (3)	−0.0001 (3)	0.0005 (3)
C2A	0.0208 (5)	0.0207 (5)	0.0221 (5)	−0.0016 (4)	−0.0006 (4)	0.0031 (4)
C3A	0.0242 (5)	0.0233 (5)	0.0189 (4)	−0.0023 (4)	−0.0008 (4)	0.0024 (4)
C4A	0.0226 (5)	0.0202 (5)	0.0221 (5)	−0.0022 (4)	−0.0004 (4)	−0.0011 (4)
C5A	0.0274 (5)	0.0198 (5)	0.0226 (5)	0.0008 (4)	−0.0013 (4)	0.0033 (4)
C6A	0.0217 (5)	0.0226 (5)	0.0197 (4)	−0.0023 (4)	−0.0008 (3)	0.0024 (4)
C7A	0.0175 (4)	0.0199 (5)	0.0236 (5)	−0.0025 (3)	0.0008 (3)	0.0016 (4)
C8A	0.0158 (4)	0.0196 (4)	0.0253 (5)	−0.0025 (3)	0.0020 (3)	−0.0004 (4)
C9A	0.0237 (5)	0.0239 (5)	0.0251 (5)	0.0005 (4)	0.0043 (4)	0.0009 (4)
C10A	0.0309 (6)	0.0313 (6)	0.0266 (5)	−0.0001 (4)	0.0075 (4)	−0.0030 (4)
C11A	0.0250 (5)	0.0256 (5)	0.0387 (6)	0.0001 (4)	0.0094 (4)	−0.0065 (5)
C12A	0.0231 (5)	0.0233 (5)	0.0394 (6)	0.0039 (4)	0.0035 (4)	0.0010 (4)
C13A	0.0220 (5)	0.0256 (5)	0.0288 (5)	0.0028 (4)	0.0003 (4)	0.0015 (4)
C14A	0.0396 (7)	0.0310 (6)	0.0228 (5)	0.0017 (5)	0.0003 (5)	−0.0044 (4)
N1B	0.0223 (4)	0.0163 (4)	0.0204 (4)	−0.0012 (3)	0.0016 (3)	0.0006 (3)
O1B	0.0306 (4)	0.0282 (4)	0.0267 (4)	−0.0015 (3)	0.0030 (3)	−0.0111 (3)
C1B	0.0205 (4)	0.0188 (4)	0.0185 (4)	−0.0012 (3)	0.0006 (3)	−0.0002 (3)
C2B	0.0196 (5)	0.0255 (5)	0.0299 (5)	−0.0034 (4)	0.0005 (4)	−0.0076 (4)
C3B	0.0197 (5)	0.0261 (5)	0.0268 (5)	−0.0010 (4)	0.0029 (4)	−0.0048 (4)
C4B	0.0265 (5)	0.0202 (4)	0.0156 (4)	−0.0014 (4)	0.0015 (3)	−0.0008 (3)
C5B	0.0225 (5)	0.0229 (5)	0.0212 (4)	−0.0047 (4)	−0.0023 (4)	−0.0024 (4)
C6B	0.0184 (4)	0.0219 (5)	0.0209 (4)	−0.0011 (4)	−0.0001 (3)	0.0010 (4)
C7B	0.0207 (5)	0.0191 (4)	0.0214 (4)	−0.0021 (3)	−0.0004 (4)	−0.0008 (4)
C8B	0.0203 (4)	0.0170 (4)	0.0176 (4)	0.0004 (3)	−0.0010 (3)	0.0020 (3)
C9B	0.0229 (5)	0.0191 (4)	0.0232 (5)	−0.0002 (4)	0.0029 (4)	0.0040 (4)
C10B	0.0266 (5)	0.0249 (5)	0.0211 (5)	0.0046 (4)	0.0048 (4)	0.0037 (4)
C11B	0.0309 (5)	0.0215 (5)	0.0202 (4)	0.0040 (4)	−0.0014 (4)	−0.0012 (4)
C12B	0.0270 (5)	0.0199 (5)	0.0276 (5)	−0.0037 (4)	0.0000 (4)	−0.0015 (4)
C13B	0.0223 (5)	0.0202 (5)	0.0228 (5)	−0.0027 (4)	0.0028 (4)	0.0007 (4)
C14B	0.0346 (6)	0.0302 (6)	0.0294 (6)	0.0035 (5)	0.0067 (5)	−0.0085 (5)

Geometric parameters (Å, º)

N1A—C7A	1.2794 (14)	N1B—C7B	1.2737 (13)
N1A—C8A	1.4179 (13)	N1B—C8B	1.4187 (12)
O1A—C4A	1.3631 (13)	O1B—C4B	1.3614 (12)
O1A—C14A	1.4322 (14)	O1B—C14B	1.4290 (15)
C1A—C2A	1.3933 (14)	C1B—C2B	1.3902 (14)
C1A—C6A	1.4044 (14)	C1B—C6B	1.4028 (14)
C1A—C7A	1.4579 (14)	C1B—C7B	1.4603 (14)
C2A—C3A	1.3899 (15)	C2B—C3B	1.3869 (15)
C2A—H2A	0.983 (14)	C2B—H2B	0.963 (15)
C3A—C4A	1.3898 (14)	C3B—C4B	1.3888 (14)
C3A—H3A	0.964 (14)	C3B—H3B	0.957 (14)
C4A—C5A	1.4023 (14)	C4B—C5B	1.3978 (15)
C5A—C6A	1.3754 (15)	C5B—C6B	1.3805 (14)
C5A—H5A	0.969 (15)	C5B—H5B	0.932 (15)
C6A—H6A	0.989 (13)	C6B—H6B	0.976 (14)
C7A—H7A	0.992 (15)	C7B—H7B	0.971 (15)
C8A—C9A	1.3945 (15)	C8B—C9B	1.3948 (14)
C8A—C13A	1.3998 (15)	C8B—C13B	1.3970 (14)
C9A—C10A	1.3859 (15)	C9B—C10B	1.3906 (15)
C9A—H9A	0.968 (14)	C9B—H9B	0.981 (14)
C10A—C11A	1.3899 (17)	C10B—C11B	1.3883 (16)
C10A—H10A	0.981 (16)	C10B—H10B	0.984 (13)
C11A—C12A	1.3891 (17)	C11B—C12B	1.3897 (16)
C11A—H11A	0.997 (16)	C11B—H11B	0.968 (14)
C12A—C13A	1.3861 (16)	C12B—C13B	1.3859 (15)
C12A—H12A	0.975 (16)	C12B—H12B	0.980 (15)
C13A—H13A	0.996 (16)	C13B—H13B	0.985 (14)
C14A—H14A	0.968 (16)	C14B—H14B	0.982 (16)
C14A—H15A	0.982 (16)	C14B—H15B	0.971 (17)
C14A—H16A	0.997 (16)	C14B—H16B	0.984 (16)
C7A—N1A—C8A	119.62 (9)	C7B—N1B—C8B	118.10 (9)
C4A—O1A—C14A	117.87 (9)	C4B—O1B—C14B	117.26 (9)
C2A—C1A—C6A	118.56 (9)	C2B—C1B—C6B	118.43 (9)
C2A—C1A—C7A	118.65 (9)	C2B—C1B—C7B	118.40 (9)
C6A—C1A—C7A	122.75 (9)	C6B—C1B—C7B	123.14 (9)
C3A—C2A—C1A	121.61 (9)	C3B—C2B—C1B	122.10 (10)
C3A—C2A—H2A	119.8 (8)	C3B—C2B—H2B	119.6 (8)
C1A—C2A—H2A	118.6 (8)	C1B—C2B—H2B	118.3 (8)
C4A—C3A—C2A	118.91 (9)	C2B—C3B—C4B	118.68 (10)
C4A—C3A—H3A	121.1 (8)	C2B—C3B—H3B	120.8 (8)
C2A—C3A—H3A	120.0 (8)	C4B—C3B—H3B	120.5 (8)
O1A—C4A—C3A	124.35 (9)	O1B—C4B—C3B	123.87 (10)
O1A—C4A—C5A	115.39 (9)	O1B—C4B—C5B	115.90 (9)
C3A—C4A—C5A	120.26 (9)	C3B—C4B—C5B	120.24 (9)
C6A—C5A—C4A	120.16 (9)	C6B—C5B—C4B	120.38 (9)
C6A—C5A—H5A	121.5 (9)	C6B—C5B—H5B	121.1 (9)
C4A—C5A—H5A	118.3 (9)	C4B—C5B—H5B	118.5 (9)
C5A—C6A—C1A	120.49 (9)	C5B—C6B—C1B	120.17 (9)
C5A—C6A—H6A	120.2 (8)	C5B—C6B—H6B	120.7 (8)
C1A—C6A—H6A	119.3 (8)	C1B—C6B—H6B	119.1 (8)
N1A—C7A—C1A	123.04 (9)	N1B—C7B—C1B	123.58 (9)
N1A—C7A—H7A	121.9 (8)	N1B—C7B—H7B	121.4 (8)
C1A—C7A—H7A	115.1 (8)	C1B—C7B—H7B	115.1 (8)
C9A—C8A—C13A	118.72 (10)	C9B—C8B—C13B	119.24 (9)
C9A—C8A—N1A	116.35 (9)	C9B—C8B—N1B	117.54 (9)
C13A—C8A—N1A	124.92 (9)	C13B—C8B—N1B	123.17 (9)
C10A—C9A—C8A	120.81 (10)	C10B—C9B—C8B	120.25 (10)
C10A—C9A—H9A	121.1 (8)	C10B—C9B—H9B	120.2 (8)
C8A—C9A—H9A	118.1 (8)	C8B—C9B—H9B	119.6 (8)
C9A—C10A—C11A	120.29 (11)	C11B—C10B—C9B	120.41 (10)
C9A—C10A—H10A	119.0 (9)	C11B—C10B—H10B	119.0 (8)
C11A—C10A—H10A	120.7 (9)	C9B—C10B—H10B	120.5 (8)
C12A—C11A—C10A	119.13 (10)	C10B—C11B—C12B	119.28 (10)
C12A—C11A—H11A	118.9 (9)	C10B—C11B—H11B	120.2 (8)
C10A—C11A—H11A	121.9 (9)	C12B—C11B—H11B	120.6 (8)
C13A—C12A—C11A	120.92 (11)	C13B—C12B—C11B	120.78 (10)
C13A—C12A—H12A	120.5 (9)	C13B—C12B—H12B	119.5 (8)
C11A—C12A—H12A	118.6 (9)	C11B—C12B—H12B	119.7 (8)
C12A—C13A—C8A	120.07 (10)	C12B—C13B—C8B	120.02 (10)
C12A—C13A—H13A	119.2 (9)	C12B—C13B—H13B	120.1 (8)
C8A—C13A—H13A	120.7 (9)	C8B—C13B—H13B	119.9 (8)
O1A—C14A—H14A	106.0 (9)	O1B—C14B—H14B	111.9 (9)
O1A—C14A—H15A	110.1 (9)	O1B—C14B—H15B	105.0 (10)
H14A—C14A—H15A	108.1 (13)	H14B—C14B—H15B	110.7 (13)
O1A—C14A—H16A	111.2 (9)	O1B—C14B—H16B	110.4 (9)
H14A—C14A—H16A	109.9 (13)	H14B—C14B—H16B	109.0 (13)
H15A—C14A—H16A	111.3 (13)	H15B—C14B—H16B	109.8 (13)
C6A—C1A—C2A—C3A	0.31 (15)	C6B—C1B—C2B—C3B	−0.56 (16)
C7A—C1A—C2A—C3A	−177.55 (9)	C7B—C1B—C2B—C3B	177.31 (10)
C1A—C2A—C3A—C4A	−0.84 (15)	C1B—C2B—C3B—C4B	−0.25 (17)
C14A—O1A—C4A—C3A	−6.75 (16)	C14B—O1B—C4B—C3B	5.56 (15)
C14A—O1A—C4A—C5A	173.38 (10)	C14B—O1B—C4B—C5B	−174.68 (10)
C2A—C3A—C4A—O1A	−179.19 (10)	C2B—C3B—C4B—O1B	−179.18 (10)
C2A—C3A—C4A—C5A	0.68 (15)	C2B—C3B—C4B—C5B	1.06 (16)
O1A—C4A—C5A—C6A	179.87 (10)	O1B—C4B—C5B—C6B	179.16 (9)
C3A—C4A—C5A—C6A	0.00 (16)	C3B—C4B—C5B—C6B	−1.07 (16)
C4A—C5A—C6A—C1A	−0.53 (16)	C4B—C5B—C6B—C1B	0.24 (15)
C2A—C1A—C6A—C5A	0.38 (15)	C2B—C1B—C6B—C5B	0.56 (15)
C7A—C1A—C6A—C5A	178.14 (9)	C7B—C1B—C6B—C5B	−177.20 (9)
C8A—N1A—C7A—C1A	−177.26 (9)	C8B—N1B—C7B—C1B	179.93 (9)
C2A—C1A—C7A—N1A	170.31 (10)	C2B—C1B—C7B—N1B	−177.12 (10)
C6A—C1A—C7A—N1A	−7.45 (15)	C6B—C1B—C7B—N1B	0.65 (16)
C7A—N1A—C8A—C9A	−162.64 (9)	C7B—N1B—C8B—C9B	−146.50 (10)
C7A—N1A—C8A—C13A	18.62 (15)	C7B—N1B—C8B—C13B	35.93 (14)
C13A—C8A—C9A—C10A	−2.89 (16)	C13B—C8B—C9B—C10B	−1.51 (15)
N1A—C8A—C9A—C10A	178.28 (10)	N1B—C8B—C9B—C10B	−179.18 (9)
C8A—C9A—C10A—C11A	1.24 (17)	C8B—C9B—C10B—C11B	0.25 (15)
C9A—C10A—C11A—C12A	0.78 (17)	C9B—C10B—C11B—C12B	0.77 (16)
C10A—C11A—C12A—C13A	−1.10 (17)	C10B—C11B—C12B—C13B	−0.53 (16)
C11A—C12A—C13A—C8A	−0.58 (17)	C11B—C12B—C13B—C8B	−0.74 (16)
C9A—C8A—C13A—C12A	2.56 (15)	C9B—C8B—C13B—C12B	1.75 (15)
N1A—C8A—C13A—C12A	−178.73 (10)	N1B—C8B—C13B—C12B	179.28 (9)

(7_rt) N-(4-methoxybenzylidene)-4-methylaniline

Crystal data

C15H15NO	Dx = 1.192 Mg m^−3
Mr = 225.28	Melting point: 90.2 C K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
a = 12.2403 (8) Å	Cell parameters from 5061 reflections
b = 13.8088 (9) Å	θ = 2.2–26.8°
c = 7.4287 (5) Å	µ = 0.08 mm^−1
V = 1255.63 (14) Å^3	T = 300 K
Z = 4	Rod, pale yellow
F(000) = 480	0.62 × 0.22 × 0.20 mm

Data collection

Bruker SMART 1000 CCD diffractometer	3664 independent reflections
Radiation source: fine-focus sealed tube	2677 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.192 pixels mm^-1	θmax = 30.0°, θmin = 2.2°
ω scan	h = −17→17
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −19→19
Tmin = 0.955, Tmax = 0.985	l = −10→10
18683 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.055	w = 1/[σ^2(Fo^2) + (0.0814P)^2 + 0.1711P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.161	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.26 e Å^−3
3664 reflections	Δρmin = −0.17 e Å^−3
203 parameters	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
8 restraints	Absolute structure parameter: −2 (2)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different ϕ angle (0, 90, 180 and 270°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −32°. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections.

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	Occ. (<1)
N1A	0.16804 (14)	0.53675 (12)	0.4053 (2)	0.0513 (4)*	0.93
C1A	0.06314 (15)	0.39254 (14)	0.3647 (3)	0.0439 (4)*	0.93
C7A	0.08252 (16)	0.49665 (15)	0.3497 (3)	0.0487 (4)*	0.93
H7A	0.0290	0.5349	0.2966	0.058*	0.93
C8A	0.18470 (16)	0.63807 (14)	0.3895 (3)	0.0464 (5)*	0.93
N1B	0.1384 (17)	0.4624 (12)	0.422 (3)	0.051 (3)*	0.07
C1B	0.155 (3)	0.6325 (12)	0.372 (5)	0.051 (3)*	0.07
C7B	0.116 (2)	0.5340 (13)	0.324 (3)	0.051 (3)*	0.07
H7B	0.0752	0.5250	0.2198	0.062*	0.07
C8B	0.085 (3)	0.3721 (14)	0.404 (4)	0.051 (3)*	0.07
O1	0.01692 (14)	0.09537 (11)	0.3920 (3)	0.0766 (5)
C2	−0.02958 (16)	0.35208 (14)	0.2923 (3)	0.0529 (4)
C3	−0.04889 (15)	0.25332 (14)	0.2953 (3)	0.0537 (4)
C4	0.02580 (16)	0.19319 (13)	0.3791 (3)	0.0525 (4)
C5	0.11855 (17)	0.23290 (17)	0.4591 (3)	0.0606 (5)
C6	0.13684 (16)	0.32972 (16)	0.4516 (3)	0.0560 (5)
C9	0.27514 (17)	0.67454 (16)	0.4750 (3)	0.0581 (5)
C10	0.29809 (18)	0.77244 (16)	0.4722 (3)	0.0611 (5)
C11	0.23146 (17)	0.83685 (14)	0.3842 (3)	0.0549 (4)
C12	0.14079 (19)	0.80074 (15)	0.2965 (3)	0.0606 (5)
C13	0.11643 (18)	0.70290 (16)	0.2960 (3)	0.0612 (5)
C14	−0.0665 (3)	0.0506 (2)	0.2903 (7)	0.0898 (10)
C15	0.2550 (3)	0.94549 (19)	0.3818 (5)	0.0752 (7)
H2	−0.085 (2)	0.3941 (17)	0.238 (4)	0.068 (6)*
H3	−0.1187 (19)	0.2288 (16)	0.236 (4)	0.062 (6)*
H5	0.170 (2)	0.192 (2)	0.527 (5)	0.087 (8)*
H6	0.2077 (18)	0.3608 (14)	0.497 (3)	0.057 (6)*
H9	0.320 (2)	0.6345 (18)	0.538 (4)	0.072 (7)*
H10	0.360 (2)	0.7954 (17)	0.545 (4)	0.067 (7)*
H12	0.095 (2)	0.8487 (18)	0.225 (4)	0.071 (7)*
H13	0.052 (2)	0.6835 (18)	0.237 (4)	0.075 (8)*
H141	−0.050 (3)	−0.016 (3)	0.323 (6)	0.113 (11)*
H142	−0.135 (3)	0.062 (2)	0.338 (5)	0.092 (10)*
H143	−0.064 (3)	0.074 (3)	0.162 (6)	0.117 (13)*
H151	0.303 (3)	0.950 (3)	0.450 (7)	0.124 (16)*
H152	0.274 (4)	0.970 (3)	0.271 (8)	0.141 (15)*
H153	0.202 (3)	0.995 (3)	0.374 (5)	0.116 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0810 (10)	0.0507 (8)	0.0980 (13)	−0.0044 (7)	−0.0065 (11)	0.0058 (8)
C2	0.0489 (9)	0.0505 (9)	0.0595 (11)	0.0051 (7)	−0.0096 (9)	−0.0022 (9)
C3	0.0453 (9)	0.0553 (10)	0.0604 (11)	−0.0034 (7)	−0.0060 (9)	−0.0051 (9)
C4	0.0600 (10)	0.0443 (9)	0.0532 (9)	0.0003 (7)	0.0063 (9)	0.0024 (8)
C5	0.0572 (11)	0.0631 (12)	0.0614 (12)	0.0077 (9)	−0.0140 (10)	0.0062 (11)
C6	0.0506 (10)	0.0641 (12)	0.0534 (10)	−0.0019 (9)	−0.0130 (9)	0.0009 (10)
C9	0.0529 (10)	0.0634 (12)	0.0578 (11)	0.0059 (9)	−0.0091 (10)	0.0001 (10)
C10	0.0526 (10)	0.0678 (12)	0.0629 (13)	−0.0090 (9)	−0.0046 (11)	−0.0077 (10)
C11	0.0595 (10)	0.0545 (10)	0.0506 (9)	−0.0093 (8)	0.0099 (9)	−0.0021 (8)
C12	0.0687 (12)	0.0522 (10)	0.0607 (12)	0.0005 (9)	−0.0107 (11)	0.0108 (10)
C13	0.0577 (11)	0.0609 (11)	0.0649 (13)	−0.0092 (9)	−0.0170 (11)	0.0059 (10)
C14	0.0765 (18)	0.0607 (14)	0.132 (3)	−0.0107 (12)	−0.0108 (19)	−0.0075 (18)
C15	0.0893 (19)	0.0607 (13)	0.0757 (16)	−0.0155 (13)	0.0063 (16)	0.0008 (13)

Geometric parameters (Å, º)

N1A—C7A	1.254 (2)	C5—C6	1.357 (3)
N1A—C8A	1.419 (2)	C5—H5	0.98 (3)
C1A—C2	1.374 (3)	C6—H6	1.02 (2)
C1A—C6	1.408 (3)	C9—C10	1.381 (3)
C1A—C7A	1.461 (3)	C9—H9	0.90 (3)
C7A—H7A	0.9300	C10—C11	1.372 (3)
C8A—C9	1.372 (3)	C10—H10	0.99 (3)
C8A—C13	1.408 (3)	C11—C12	1.380 (3)
N1B—C7B	1.259 (10)	C11—C15	1.528 (3)
N1B—C8B	1.413 (10)	C12—C13	1.384 (3)
C1B—C7B	1.485 (10)	C12—H12	1.02 (3)
C7B—H7B	0.9300	C13—H13	0.94 (3)
O1—C4	1.359 (2)	C14—H141	0.97 (4)
O1—C14	1.412 (4)	C14—H142	0.93 (3)
C2—C3	1.384 (3)	C14—H143	1.01 (4)
C2—H2	0.98 (3)	C15—H151	0.78 (5)
C3—C4	1.383 (3)	C15—H152	0.92 (6)
C3—H3	1.02 (2)	C15—H153	0.95 (4)
C4—C5	1.394 (3)
C7A—N1A—C8A	121.88 (17)	C1A—C6—H6	115.7 (12)
C2—C1A—C6	117.25 (17)	C8A—C9—C10	121.1 (2)
C2—C1A—C7A	120.28 (18)	C8A—C9—H9	119.9 (16)
C6—C1A—C7A	122.47 (17)	C10—C9—H9	118.9 (16)
N1A—C7A—C1A	123.02 (18)	C11—C10—C9	121.4 (2)
N1A—C7A—H7A	118.5	C11—C10—H10	120.8 (14)
C1A—C7A—H7A	118.5	C9—C10—H10	117.6 (14)
C9—C8A—C13	118.28 (19)	C10—C11—C12	117.94 (18)
C9—C8A—N1A	116.08 (18)	C10—C11—C15	122.0 (2)
C13—C8A—N1A	125.63 (18)	C12—C11—C15	120.1 (2)
C7B—N1B—C8B	122.4 (13)	C11—C12—C13	121.81 (19)
N1B—C7B—C1B	120.7 (12)	C11—C12—H12	117.1 (14)
N1B—C7B—H7B	119.6	C13—C12—H12	121.0 (14)
C1B—C7B—H7B	119.6	C12—C13—C8A	119.47 (19)
C4—O1—C14	117.1 (2)	C12—C13—H13	117.3 (16)
C1A—C2—C3	122.35 (18)	C8A—C13—H13	123.1 (16)
C1A—C2—H2	119.4 (15)	O1—C14—H141	97 (2)
C3—C2—H2	118.3 (15)	O1—C14—H142	112 (2)
C4—C3—C2	119.08 (17)	H141—C14—H142	105 (3)
C4—C3—H3	123.3 (13)	O1—C14—H143	110 (2)
C2—C3—H3	117.6 (13)	H141—C14—H143	122 (3)
O1—C4—C3	125.15 (19)	H142—C14—H143	110 (3)
O1—C4—C5	115.23 (18)	C11—C15—H151	102 (3)
C3—C4—C5	119.61 (17)	C11—C15—H152	115 (3)
C6—C5—C4	120.29 (18)	H151—C15—H152	111 (4)
C6—C5—H5	118.6 (17)	C11—C15—H153	125 (2)
C4—C5—H5	121.0 (17)	H151—C15—H153	121 (3)
C5—C6—C1A	121.35 (18)	H152—C15—H153	82 (3)
C5—C6—H6	122.6 (12)
C8A—N1A—C7A—C1A	−179.9 (2)	C3—C4—C5—C6	−1.5 (4)
C2—C1A—C7A—N1A	−176.4 (2)	C4—C5—C6—C1A	0.4 (4)
C6—C1A—C7A—N1A	3.5 (3)	C2—C1A—C6—C5	1.8 (3)
C7A—N1A—C8A—C9	172.2 (2)	C7A—C1A—C6—C5	−178.0 (2)
C7A—N1A—C8A—C13	−7.2 (3)	C13—C8A—C9—C10	1.0 (3)
C8B—N1B—C7B—C1B	166 (3)	N1A—C8A—C9—C10	−178.5 (2)
C6—C1A—C2—C3	−3.1 (3)	C8A—C9—C10—C11	0.1 (4)
C7A—C1A—C2—C3	176.8 (2)	C9—C10—C11—C12	−0.6 (3)
C1A—C2—C3—C4	2.1 (3)	C9—C10—C11—C15	179.2 (2)
C14—O1—C4—C3	9.5 (4)	C10—C11—C12—C13	0.1 (3)
C14—O1—C4—C5	−170.8 (3)	C15—C11—C12—C13	−179.8 (2)
C2—C3—C4—O1	179.9 (2)	C11—C12—C13—C8A	0.9 (4)
C2—C3—C4—C5	0.2 (3)	C9—C8A—C13—C12	−1.4 (3)
O1—C4—C5—C6	178.8 (2)	N1A—C8A—C13—C12	177.9 (2)

(7_90K) N-(4-methoxybenzylidene)-4-methylaniline

Crystal data

C15H15NO	Dx = 1.239 Mg m^−3
Mr = 225.28	Melting point: 90.2 C K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
a = 12.0319 (17) Å	Cell parameters from 7926 reflections
b = 13.8190 (19) Å	θ = 2.2–30.0°
c = 7.263 (1) Å	µ = 0.08 mm^−1
V = 1207.6 (3) Å^3	T = 90 K
Z = 4	Rod, pale yellow
F(000) = 480	0.62 × 0.22 × 0.20 mm

Data collection

Bruker SMART 1000 CCD diffractometer	3523 independent reflections
Radiation source: fine-focus sealed tube	3375 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 8.192 pixels mm^-1	θmax = 30.0°, θmin = 2.2°
ω scan	h = −16→16
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −19→19
Tmin = 0.954, Tmax = 0.985	l = −10→10
17826 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.034	w = 1/[σ^2(Fo^2) + (0.0587P)^2 + 0.1458P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.093	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.33 e Å^−3
3523 reflections	Δρmin = −0.15 e Å^−3
186 parameters	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
8 restraints	Absolute structure parameter: −0.8 (10)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different ϕ angle (0, 90, 180 and 270°) for the crystal and each exposure of 5 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −32°. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections.

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	Occ. (<1)
N1A	0.16875 (7)	0.53667 (6)	0.40369 (12)	0.01785 (18)	0.92
O1A	0.01928 (7)	0.09399 (5)	0.38879 (13)	0.02315 (18)	0.92
C1A	0.06035 (8)	0.39217 (7)	0.36829 (14)	0.01486 (18)	0.92
C2A	−0.03563 (8)	0.35094 (7)	0.29512 (15)	0.01550 (19)	0.92
H2A	−0.0904	0.3918	0.2419	0.019*	0.92
C3A	−0.05347 (8)	0.25124 (7)	0.29785 (15)	0.01539 (19)	0.92
H3A	−0.1188	0.2243	0.2454	0.018*	0.92
C4A	0.02630 (9)	0.19185 (7)	0.37899 (15)	0.01597 (19)	0.92
C5A	0.12197 (8)	0.23255 (9)	0.45894 (15)	0.0182 (2)	0.92
H5A	0.1749	0.1921	0.5180	0.022*	0.92
C6A	0.13893 (8)	0.33132 (8)	0.45166 (14)	0.0170 (2)	0.92
H6A	0.2044	0.3583	0.5036	0.020*	0.92
C7A	0.07813 (8)	0.49718 (8)	0.35266 (14)	0.0173 (2)	0.92
H7A	0.0206	0.5365	0.3033	0.021*	0.92
C8A	0.18500 (8)	0.63782 (7)	0.38798 (14)	0.01528 (19)	0.92
C9A	0.27924 (9)	0.67440 (9)	0.47580 (15)	0.01774 (19)	0.92
H9A	0.3282	0.6312	0.5373	0.021*	0.92
C10A	0.30267 (8)	0.77299 (9)	0.47471 (15)	0.0182 (2)	0.92
H10A	0.3672	0.7963	0.5356	0.022*	0.92
C11A	0.23242 (8)	0.83798 (7)	0.38526 (15)	0.01627 (19)	0.92
C12A	0.13899 (9)	0.80100 (8)	0.29456 (16)	0.0184 (2)	0.92
H12A	0.0906	0.8442	0.2319	0.022*	0.92
C13A	0.11524 (9)	0.70224 (7)	0.29398 (17)	0.0184 (2)	0.92
H13A	0.0519	0.6787	0.2300	0.022*	0.92
C14A	−0.06648 (10)	0.04837 (9)	0.2836 (2)	0.0283 (3)	0.92
H14A	−0.1392	0.0657	0.3349	0.043*	0.92
H14B	−0.0569	−0.0220	0.2884	0.043*	0.92
H14C	−0.0621	0.0702	0.1554	0.043*	0.92
C15A	0.25735 (9)	0.94542 (8)	0.38200 (17)	0.0217 (2)	0.92
H15A	0.3089	0.9613	0.4819	0.033*	0.92
H15B	0.1882	0.9818	0.3984	0.033*	0.92
H15C	0.2911	0.9626	0.2636	0.033*	0.92
N1B	0.1372 (10)	0.4672 (6)	0.4227 (17)	0.0314 (9)*	0.08
O1B	0.3034 (9)	0.8989 (8)	0.4354 (15)	0.0314 (9)*	0.08
C1B	0.1483 (10)	0.6400 (6)	0.3535 (19)	0.0314 (9)*	0.08
C2B	0.1054 (9)	0.7269 (8)	0.288 (2)	0.0314 (9)*	0.08
H2B	0.0371	0.7274	0.2225	0.038*	0.08
C3B	0.1624 (11)	0.8128 (6)	0.319 (2)	0.0314 (9)*	0.08
H3B	0.1331	0.8722	0.2742	0.038*	0.08
C4B	0.2623 (10)	0.8120 (7)	0.4149 (19)	0.0314 (9)*	0.08
C5B	0.3052 (8)	0.7251 (10)	0.4802 (16)	0.0314 (9)*	0.08
H5B	0.3735	0.7246	0.5459	0.038*	0.08
C6B	0.2482 (10)	0.6392 (7)	0.4495 (17)	0.0314 (9)*	0.08
H6B	0.2775	0.5798	0.4942	0.038*	0.08
C7B	0.1054 (12)	0.5398 (6)	0.337 (2)	0.0314 (9)*	0.08
H7B	0.0468	0.5301	0.2515	0.038*	0.08
C8B	0.0972 (10)	0.3724 (6)	0.4096 (17)	0.0314 (9)*	0.08
C9B	0.1437 (7)	0.2855 (8)	0.4678 (15)	0.0314 (9)*	0.08
H9B	0.2135	0.2853	0.5289	0.038*	0.08
C10B	0.0880 (10)	0.1989 (6)	0.4366 (16)	0.0314 (9)*	0.08
H10B	0.1198	0.1395	0.4764	0.038*	0.08
C11B	−0.0141 (10)	0.1991 (7)	0.3472 (18)	0.0314 (9)*	0.08
C12B	−0.0606 (8)	0.2860 (9)	0.2890 (18)	0.0314 (9)*	0.08
H12B	−0.1305	0.2862	0.2280	0.038*	0.08
C13B	−0.0050 (10)	0.3726 (6)	0.3202 (18)	0.0314 (9)*	0.08
H13B	−0.0368	0.4320	0.2805	0.038*	0.08
C14B	0.2493 (13)	0.9907 (13)	0.390 (2)	0.0314 (9)*	0.08
H14D	0.1978	0.9810	0.2876	0.047*	0.08
H14E	0.3058	1.0384	0.3555	0.047*	0.08
H14F	0.2082	1.0142	0.4980	0.047*	0.08
C15B	−0.0410 (15)	0.0813 (12)	0.331 (2)	0.0314 (9)*	0.08
H15D	−0.1216	0.0713	0.3262	0.047*	0.08
H15E	−0.0102	0.0477	0.4380	0.047*	0.08
H15F	−0.0071	0.0557	0.2182	0.047*	0.08

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0187 (4)	0.0166 (4)	0.0182 (4)	−0.0014 (3)	−0.0028 (3)	−0.0001 (3)
O1A	0.0232 (4)	0.0157 (3)	0.0305 (4)	−0.0021 (3)	−0.0042 (4)	0.0012 (3)
C1A	0.0141 (4)	0.0164 (4)	0.0141 (4)	−0.0016 (3)	−0.0001 (3)	−0.0018 (4)
C2A	0.0134 (4)	0.0139 (4)	0.0192 (5)	−0.0013 (3)	−0.0027 (4)	−0.0005 (4)
C3A	0.0151 (4)	0.0115 (4)	0.0196 (5)	−0.0005 (3)	−0.0012 (4)	−0.0006 (4)
C4A	0.0163 (4)	0.0158 (4)	0.0158 (4)	0.0022 (3)	0.0010 (4)	0.0012 (4)
C5A	0.0178 (4)	0.0191 (5)	0.0178 (5)	0.0009 (4)	−0.0033 (4)	0.0025 (4)
C6A	0.0158 (4)	0.0194 (5)	0.0159 (4)	0.0005 (4)	−0.0031 (4)	0.0007 (4)
C7A	0.0166 (4)	0.0169 (4)	0.0183 (5)	0.0012 (3)	−0.0016 (4)	−0.0001 (4)
C8A	0.0154 (4)	0.0156 (4)	0.0148 (4)	0.0002 (3)	−0.0009 (4)	0.0000 (4)
C9A	0.0167 (4)	0.0187 (5)	0.0178 (4)	0.0003 (4)	−0.0030 (4)	−0.0005 (4)
C10A	0.0157 (4)	0.0208 (5)	0.0179 (5)	−0.0021 (4)	−0.0025 (4)	−0.0006 (4)
C11A	0.0184 (4)	0.0161 (4)	0.0144 (4)	−0.0021 (3)	0.0019 (4)	−0.0003 (4)
C12A	0.0182 (5)	0.0177 (5)	0.0194 (5)	−0.0010 (3)	−0.0047 (4)	0.0017 (4)
C13A	0.0188 (4)	0.0154 (5)	0.0209 (5)	−0.0015 (4)	−0.0056 (4)	0.0016 (5)
C14A	0.0237 (5)	0.0192 (5)	0.0421 (7)	−0.0040 (4)	−0.0030 (5)	−0.0052 (5)
C15A	0.0246 (5)	0.0169 (5)	0.0236 (5)	−0.0035 (4)	0.0013 (5)	−0.0003 (5)

Geometric parameters (Å, º)

N1A—C7A	1.2744 (13)	N1B—C7B	1.240 (8)
N1A—C8A	1.4159 (12)	N1B—C8B	1.400 (8)
O1A—C4A	1.3568 (12)	O1B—C4B	1.307 (13)
O1A—C14A	1.4303 (15)	O1B—C14B	1.463 (19)
C1A—C2A	1.3931 (13)	C1B—C2B	1.3900
C1A—C6A	1.4027 (14)	C1B—C6B	1.3900
C1A—C7A	1.4712 (13)	C1B—C7B	1.482 (8)
C2A—C3A	1.3945 (13)	C2B—C3B	1.3900
C3A—C4A	1.3936 (14)	C3B—C4B	1.3900
C4A—C5A	1.4066 (14)	C4B—C5B	1.3900
C5A—C6A	1.3810 (15)	C5B—C6B	1.3900
C8A—C9A	1.3957 (14)	C8B—C9B	1.3900
C8A—C13A	1.4012 (14)	C8B—C13B	1.3900
C9A—C10A	1.3913 (14)	C9B—C10B	1.3900
C10A—C11A	1.3940 (14)	C10B—C11B	1.3900
C11A—C12A	1.3995 (14)	C11B—C12B	1.3900
C11A—C15A	1.5149 (15)	C11B—C15B	1.664 (19)
C12A—C13A	1.3943 (14)	C12B—C13B	1.3900
C7A—N1A—C8A	121.16 (9)	C7B—N1B—C8B	128.2 (10)
C4A—O1A—C14A	117.14 (9)	C4B—O1B—C14B	127.1 (12)
C2A—C1A—C6A	118.57 (9)	C2B—C1B—C6B	120.0
C2A—C1A—C7A	119.64 (9)	C2B—C1B—C7B	130.5 (9)
C6A—C1A—C7A	121.78 (9)	C6B—C1B—C7B	109.5 (9)
C1A—C2A—C3A	121.75 (9)	C3B—C2B—C1B	120.0
C4A—C3A—C2A	118.81 (9)	C2B—C3B—C4B	120.0
O1A—C4A—C3A	124.49 (10)	O1B—C4B—C5B	127.8 (11)
O1A—C4A—C5A	115.33 (10)	O1B—C4B—C3B	112.1 (11)
C3A—C4A—C5A	120.18 (9)	C5B—C4B—C3B	120.0
C6A—C5A—C4A	120.02 (9)	C4B—C5B—C6B	120.0
C5A—C6A—C1A	120.63 (9)	C5B—C6B—C1B	120.0
N1A—C7A—C1A	121.63 (9)	N1B—C7B—C1B	127.5 (11)
C9A—C8A—C13A	118.64 (9)	C9B—C8B—C13B	120.0
C9A—C8A—N1A	115.65 (10)	C9B—C8B—N1B	130.5 (9)
C13A—C8A—N1A	125.72 (10)	C13B—C8B—N1B	109.5 (9)
C10A—C9A—C8A	121.11 (9)	C8B—C9B—C10B	120.0
C9A—C10A—C11A	120.71 (9)	C11B—C10B—C9B	120.0
C10A—C11A—C12A	118.11 (9)	C12B—C11B—C10B	120.0
C10A—C11A—C15A	121.24 (10)	C12B—C11B—C15B	138.1 (10)
C12A—C11A—C15A	120.64 (10)	C10B—C11B—C15B	101.7 (10)
C13A—C12A—C11A	121.57 (9)	C11B—C12B—C13B	120.0
C12A—C13A—C8A	119.84 (9)	C12B—C13B—C8B	120.0
C6A—C1A—C2A—C3A	−2.00 (16)	C6B—C1B—C2B—C3B	0.0
C7A—C1A—C2A—C3A	176.55 (10)	C7B—C1B—C2B—C3B	−179.0 (14)
C1A—C2A—C3A—C4A	1.12 (16)	C1B—C2B—C3B—C4B	0.0
C14A—O1A—C4A—C3A	10.37 (16)	C14B—O1B—C4B—C5B	−170.0 (12)
C14A—O1A—C4A—C5A	−169.93 (10)	C14B—O1B—C4B—C3B	8.3 (16)
C2A—C3A—C4A—O1A	−179.31 (10)	C2B—C3B—C4B—O1B	−178.4 (12)
C2A—C3A—C4A—C5A	1.01 (16)	C2B—C3B—C4B—C5B	0.0
O1A—C4A—C5A—C6A	178.08 (9)	O1B—C4B—C5B—C6B	178.1 (14)
C3A—C4A—C5A—C6A	−2.21 (16)	C3B—C4B—C5B—C6B	0.0
C4A—C5A—C6A—C1A	1.31 (15)	C4B—C5B—C6B—C1B	0.0
C2A—C1A—C6A—C5A	0.76 (15)	C2B—C1B—C6B—C5B	0.0
C7A—C1A—C6A—C5A	−177.76 (9)	C7B—C1B—C6B—C5B	179.2 (11)
C8A—N1A—C7A—C1A	179.98 (10)	C8B—N1B—C7B—C1B	179.6 (14)
C2A—C1A—C7A—N1A	−174.01 (10)	C2B—C1B—C7B—N1B	−167.3 (13)
C6A—C1A—C7A—N1A	4.50 (15)	C6B—C1B—C7B—N1B	13.6 (19)
C7A—N1A—C8A—C9A	169.76 (10)	C7B—N1B—C8B—C9B	163.6 (13)
C7A—N1A—C8A—C13A	−10.01 (16)	C7B—N1B—C8B—C13B	−15.5 (18)
C13A—C8A—C9A—C10A	1.59 (16)	C13B—C8B—C9B—C10B	0.0
N1A—C8A—C9A—C10A	−178.20 (9)	N1B—C8B—C9B—C10B	−179.0 (13)
C8A—C9A—C10A—C11A	−0.10 (17)	C8B—C9B—C10B—C11B	0.0
C9A—C10A—C11A—C12A	−0.99 (16)	C9B—C10B—C11B—C12B	0.0
C9A—C10A—C11A—C15A	−179.61 (10)	C9B—C10B—C11B—C15B	176.2 (10)
C10A—C11A—C12A—C13A	0.59 (16)	C10B—C11B—C12B—C13B	0.0
C15A—C11A—C12A—C13A	179.22 (10)	C15B—C11B—C12B—C13B	−174.5 (14)
C11A—C12A—C13A—C8A	0.89 (17)	C11B—C12B—C13B—C8B	0.0
C9A—C8A—C13A—C12A	−1.96 (16)	C9B—C8B—C13B—C12B	0.0
N1A—C8A—C13A—C12A	177.80 (10)	N1B—C8B—C13B—C12B	179.2 (10)