Conformational change of N-benzylideneanilines in crystals

Harada, J.; Harakawa, M.; Ogawa, K.

doi:10.1107/S0108768104016623

Conformational change of N-benzylideneanilines in crystals

The crystal structures of N-(4-nitrobenzylidene)aniline (1), N-(4-chlorobenzylidene)-4-methylaniline (2) and N-(4-methylbenzylidene)-4-methylaniline (3) were determined by X-ray diffraction analyses at various temperatures. A dynamic disorder was observed in the crystal structures of all compounds. The dynamic disorder is accounted for in terms of a conformational change involving a pedal motion in the crystals.

Keywords: conformational change; dynamic disorder; pedal motion.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768104016623/bk5008sup1.cif Contains datablocks 1_rt, 1_200K, 1_90K, 2_rt, 2_200K, 2_90K, 3_300K, 3_250K, 3_200K, 3_150K, 3_90K, 3_90K2, 3_90K4, 3_300K2, 3_300K3, 3_90K3
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768104016623/bk50081_rtsup2.hkl Contains datablock 1_rt
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768104016623/bk50081_200Ksup3.hkl Contains datablock shelxtl
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768104016623/bk50081_90Ksup4.hkl Contains datablock 1_90K
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768104016623/bk50082_rtsup5.hkl Contains datablock 2_rt
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768104016623/bk50082_200Ksup6.hkl Contains datablock 2_200K
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768104016623/bk50082_90Ksup7.hkl Contains datablock 2_90K
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768104016623/bk50083_300Ksup8.hkl Contains datablock 3_300K
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768104016623/bk50083_250Ksup9.hkl Contains datablock 3_250K
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768104016623/bk50083_200Ksup10.hkl Contains datablock 3_200K
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768104016623/bk50083_150Ksup11.hkl Contains datablock 3_150K
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768104016623/bk50083_90Ksup12.hkl Contains datablock 3_90K
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768104016623/bk50083_90K2sup13.hkl Contains datablock 3_90K2
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768104016623/bk50083_90K3sup14.hkl Contains datablock 3_90K3
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768104016623/bk50083_90K4sup15.hkl Contains datablock 3_90K4
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768104016623/bk50083_300K2sup16.hkl Contains datablock 3_300K2
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768104016623/bk50083_300K3sup17.hkl Contains datablock 3_300K3

CCDC references: 255104; 255105; 255106; 255107; 255108; 255109; 255110; 255111; 255112; 255113; 255114; 255115; 255116; 255117; 255118; 255119

Computing details top

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 top

(1_rt) N-(4-nitrobenzylidene)aniline top

Crystal data top

C₁₃H₁₀N₂O₂	D_x = 1.318 Mg m⁻³
M_r = 226.23	Melting point: 89.7 C K
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.6363 (11) Å	Cell parameters from 7219 reflections
b = 10.8175 (8) Å	θ = 2.2–28.5°
c = 14.7228 (11) Å	µ = 0.09 mm⁻¹
β = 101.943 (1)°	T = 300 K
V = 2280.6 (3) Å³	Block, yellow
Z = 8	0.46 × 0.40 × 0.28 mm
F(000) = 944

Data collection top

Bruker SMART 1000 CCD diffractometer	6663 independent reflections
Radiation source: fine-focus sealed tube	3616 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 8.192 pixels mm^-1	θ_max = 30.1°, θ_min = 1.8°
ω scan	h = −20→20
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −15→15
T_min = 0.959, T_max = 0.975	l = −20→20
34291 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.174	w = 1/[σ²(F_o²) + (0.0436P)² + 0.878P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
6663 reflections	Δρ_max = 0.18 e Å⁻³
399 parameters	Δρ_min = −0.29 e Å⁻³
5 restraints

Crystal data top

C₁₃H₁₀N₂O₂	V = 2280.6 (3) Å³
M_r = 226.23	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.6363 (11) Å	µ = 0.09 mm⁻¹
b = 10.8175 (8) Å	T = 300 K
c = 14.7228 (11) Å	0.46 × 0.40 × 0.28 mm
β = 101.943 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	6663 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	3616 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.975	R_int = 0.041
34291 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	5 restraints
wR(F²) = 0.174	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.18 e Å⁻³
6663 reflections	Δρ_min = −0.29 e Å⁻³
399 parameters

Special details top

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.

The very long bonds for C1C—C2B and C8C—C9B, and the very short bonds for C1C—C6B and C8C—C13B, are artifacts caused by the fact that the ortho carbon atoms of the two overlapping conformers are not resolved.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.02380 (11)	0.78968 (16)	0.82394 (11)	0.0566 (4)
N2A	0.01744 (14)	0.7417 (2)	1.26015 (12)	0.0711 (5)
O1A	−0.02393 (14)	0.82959 (17)	1.28405 (11)	0.0882 (5)
O2A	0.04782 (18)	0.6563 (2)	1.31135 (12)	0.1138 (7)
C1A	0.04664 (12)	0.72254 (17)	0.98186 (12)	0.0512 (4)
C2A	0.08161 (16)	0.6304 (2)	1.04364 (15)	0.0668 (6)
C3A	0.07394 (16)	0.6370 (2)	1.13535 (16)	0.0684 (6)
C4A	0.02916 (13)	0.73635 (18)	1.16329 (12)	0.0538 (4)
C5A	−0.00515 (14)	0.83065 (19)	1.10426 (14)	0.0562 (5)
C6A	0.00299 (14)	0.82339 (18)	1.01254 (13)	0.0538 (4)
C7A	0.05495 (14)	0.7107 (2)	0.88434 (14)	0.0566 (5)
C8A	0.03092 (13)	0.7670 (2)	0.73054 (13)	0.0569 (5)
C9A	0.05125 (16)	0.8651 (3)	0.67911 (16)	0.0729 (6)
C10A	0.0572 (2)	0.8474 (4)	0.5874 (2)	0.0930 (9)
C11A	0.0413 (2)	0.7333 (4)	0.5475 (2)	0.1061 (12)
C12A	0.0192 (2)	0.6361 (4)	0.5983 (2)	0.1003 (10)
C13A	0.01409 (18)	0.6515 (3)	0.68997 (17)	0.0759 (6)
H2A	0.1131 (16)	0.561 (2)	1.0233 (16)	0.082 (7)*
H3A	0.0964 (16)	0.575 (2)	1.1790 (16)	0.083 (7)*
H5A	−0.0360 (14)	0.8992 (19)	1.1239 (13)	0.061 (6)*
H6A	−0.0220 (15)	0.888 (2)	0.9710 (14)	0.069 (6)*
H7A	0.0878 (15)	0.638 (2)	0.8709 (14)	0.069 (6)*
H9A	0.0640 (17)	0.947 (2)	0.7075 (17)	0.087 (8)*
H10A	0.072 (2)	0.918 (3)	0.558 (2)	0.107 (10)*
H11A	0.045 (2)	0.723 (3)	0.488 (3)	0.139 (12)*
H12A	0.003 (2)	0.555 (3)	0.572 (2)	0.127 (11)*
H13A	−0.0049 (18)	0.584 (2)	0.7234 (17)	0.093 (8)*
N1B	0.23088 (13)	0.9587 (2)	0.14032 (14)	0.0580 (5)	0.90
C1B	0.26273 (16)	0.8968 (3)	−0.00672 (17)	0.0545 (6)	0.90
C7B	0.25692 (15)	0.8776 (2)	0.09118 (16)	0.0578 (5)	0.90
H7B	0.2736	0.8007	0.1177	0.069*	0.90
C8B	0.23050 (19)	0.9338 (3)	0.23442 (17)	0.0513 (7)	0.90
N1C	0.2502 (17)	0.897 (2)	0.1526 (13)	0.075 (7)*	0.10
C1C	0.2673 (18)	0.951 (3)	−0.0016 (15)	0.052 (6)*	0.10
C7C	0.2529 (19)	0.977 (2)	0.0928 (14)	0.079 (7)*	0.10
H7C	0.2453	1.0593	0.1086	0.094*	0.10
C8C	0.246 (2)	0.900 (2)	0.2478 (14)	0.035 (6)*	0.10
N2B	0.28500 (13)	0.9491 (2)	−0.28382 (13)	0.0725 (5)
O1B	0.25627 (16)	1.04339 (19)	−0.32413 (13)	0.1070 (7)
O2B	0.31877 (16)	0.8663 (2)	−0.32122 (13)	0.1148 (7)
C2B	0.29165 (18)	0.8061 (2)	−0.05534 (17)	0.0755 (6)
C3B	0.29928 (17)	0.8224 (2)	−0.14587 (17)	0.0716 (6)
C4B	0.27696 (13)	0.9341 (2)	−0.18690 (14)	0.0593 (5)
C5B	0.24731 (19)	1.0311 (2)	−0.14077 (18)	0.0796 (7)
C6B	0.24128 (19)	1.0134 (3)	−0.04900 (18)	0.0777 (7)
C9B	0.17402 (15)	1.0016 (2)	0.27704 (16)	0.0648 (5)
C10B	0.17214 (18)	0.9853 (3)	0.36921 (17)	0.0773 (7)
C11B	0.22757 (18)	0.8988 (3)	0.42102 (18)	0.0810 (7)
C12B	0.28558 (19)	0.8292 (3)	0.3803 (2)	0.0850 (8)
C13B	0.28819 (18)	0.8440 (2)	0.28846 (18)	0.0739 (6)
H2B	0.3082 (18)	0.724 (3)	−0.0224 (17)	0.096 (8)*
H3B	0.3203 (19)	0.754 (3)	−0.1793 (19)	0.107 (9)*
H5B	0.2365 (17)	1.108 (2)	−0.1717 (17)	0.091 (8)*
H6B	0.2255 (19)	1.081 (3)	−0.0193 (19)	0.106 (9)*
H9B	0.1351 (16)	1.061 (2)	0.2409 (15)	0.076 (7)*
H10B	0.1324 (18)	1.033 (2)	0.3952 (18)	0.097 (8)*
H11B	0.2267 (18)	0.887 (2)	0.4832 (19)	0.095 (8)*
H12B	0.322 (2)	0.772 (3)	0.416 (2)	0.111 (10)*
H13B	0.3280 (18)	0.794 (2)	0.2594 (17)	0.095 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0549 (9)	0.0655 (10)	0.0501 (9)	0.0025 (8)	0.0122 (7)	−0.0044 (8)
N2A	0.0862 (13)	0.0747 (13)	0.0532 (10)	−0.0223 (10)	0.0167 (9)	−0.0030 (9)
O1A	0.1192 (15)	0.0834 (12)	0.0724 (10)	−0.0200 (10)	0.0437 (10)	−0.0183 (9)
O2A	0.177 (2)	0.1066 (15)	0.0592 (10)	0.0106 (14)	0.0266 (12)	0.0186 (10)
C1A	0.0474 (10)	0.0563 (10)	0.0487 (10)	0.0010 (8)	0.0074 (8)	−0.0044 (8)
C2A	0.0717 (14)	0.0652 (13)	0.0632 (13)	0.0190 (11)	0.0134 (10)	−0.0007 (10)
C3A	0.0732 (14)	0.0672 (13)	0.0616 (13)	0.0096 (11)	0.0068 (11)	0.0104 (11)
C4A	0.0572 (11)	0.0586 (11)	0.0451 (9)	−0.0127 (9)	0.0093 (8)	−0.0028 (8)
C5A	0.0621 (12)	0.0518 (11)	0.0566 (11)	−0.0027 (9)	0.0165 (9)	−0.0089 (9)
C6A	0.0591 (11)	0.0513 (10)	0.0504 (10)	0.0004 (9)	0.0097 (9)	−0.0004 (8)
C7A	0.0522 (11)	0.0639 (12)	0.0536 (11)	0.0065 (9)	0.0109 (9)	−0.0088 (9)
C8A	0.0457 (10)	0.0778 (13)	0.0476 (10)	0.0040 (9)	0.0106 (8)	−0.0038 (9)
C9A	0.0673 (14)	0.0894 (17)	0.0645 (14)	0.0035 (12)	0.0195 (11)	0.0034 (13)
C10A	0.0784 (17)	0.136 (3)	0.0698 (17)	0.0099 (17)	0.0269 (14)	0.0227 (19)
C11A	0.089 (2)	0.180 (4)	0.0495 (15)	0.015 (2)	0.0165 (14)	−0.012 (2)
C12A	0.102 (2)	0.133 (3)	0.0645 (16)	−0.0039 (19)	0.0148 (15)	−0.0360 (18)
C13A	0.0789 (16)	0.0890 (18)	0.0597 (13)	−0.0045 (13)	0.0140 (11)	−0.0166 (12)
N1B	0.0564 (11)	0.0603 (12)	0.0573 (12)	0.0033 (10)	0.0119 (9)	0.0018 (10)
C1B	0.0470 (12)	0.0551 (15)	0.0598 (14)	−0.0023 (11)	0.0072 (9)	−0.0006 (11)
C7B	0.0563 (13)	0.0525 (12)	0.0633 (14)	0.0010 (10)	0.0095 (10)	0.0005 (10)
C8B	0.0455 (15)	0.0513 (16)	0.0547 (15)	−0.0005 (12)	0.0050 (10)	0.0038 (11)
N2B	0.0685 (12)	0.0867 (14)	0.0643 (11)	0.0025 (10)	0.0184 (9)	0.0023 (10)
O1B	0.1506 (19)	0.0913 (13)	0.0865 (13)	0.0091 (13)	0.0414 (12)	0.0237 (11)
O2B	0.1327 (17)	0.1440 (18)	0.0741 (12)	0.0543 (15)	0.0364 (11)	0.0011 (12)
C2B	0.0864 (17)	0.0704 (15)	0.0710 (15)	0.0098 (12)	0.0193 (12)	0.0061 (12)
C3B	0.0771 (15)	0.0695 (14)	0.0693 (14)	0.0066 (11)	0.0180 (11)	−0.0016 (12)
C4B	0.0515 (11)	0.0704 (13)	0.0571 (11)	0.0001 (9)	0.0137 (9)	−0.0001 (10)
C5B	0.0981 (18)	0.0696 (15)	0.0733 (16)	0.0167 (13)	0.0233 (13)	0.0061 (12)
C6B	0.0853 (17)	0.0789 (16)	0.0716 (16)	0.0143 (13)	0.0229 (13)	−0.0102 (14)
C9B	0.0615 (13)	0.0640 (13)	0.0664 (13)	0.0064 (10)	0.0072 (10)	−0.0019 (10)
C10B	0.0680 (14)	0.0965 (18)	0.0691 (15)	0.0018 (13)	0.0183 (12)	−0.0169 (13)
C11B	0.0675 (15)	0.116 (2)	0.0590 (14)	−0.0119 (15)	0.0111 (12)	0.0088 (14)
C12B	0.0716 (16)	0.0958 (19)	0.0833 (18)	0.0099 (14)	0.0065 (13)	0.0296 (15)
C13B	0.0672 (14)	0.0792 (16)	0.0757 (15)	0.0154 (12)	0.0156 (12)	0.0063 (13)

Geometric parameters (Å, º) top

N1A—C7A	1.249 (2)	C1B—C7B	1.476 (3)
N1A—C8A	1.422 (2)	C7B—H7B	0.9300
N2A—O2A	1.216 (3)	C8B—C9B	1.353 (3)
N2A—O1A	1.218 (2)	C8B—C13B	1.418 (3)
N2A—C4A	1.472 (2)	N1C—C7C	1.244 (10)
C1A—C2A	1.375 (3)	N1C—C8C	1.415 (10)
C1A—C6A	1.386 (3)	C1C—C6B	0.99 (3)
C1A—C7A	1.471 (3)	C1C—C7C	1.476 (10)
C2A—C3A	1.380 (3)	C1C—C2B	1.82 (2)
C2A—H2A	0.96 (2)	C7C—H7C	0.9300
C3A—C4A	1.366 (3)	C8C—C13B	0.97 (3)
C3A—H3A	0.94 (2)	C8C—C9B	1.64 (2)
C4A—C5A	1.367 (3)	N2B—O2B	1.209 (2)
C5A—C6A	1.382 (3)	N2B—O1B	1.211 (2)
C5A—H5A	0.94 (2)	N2B—C4B	1.465 (3)
C6A—H6A	0.95 (2)	C2B—C3B	1.372 (3)
C7A—H7A	0.96 (2)	C2B—H2B	1.02 (3)
C8A—C9A	1.371 (3)	C3B—C4B	1.361 (3)
C8A—C13A	1.385 (3)	C3B—H3B	0.97 (3)
C9A—C10A	1.384 (4)	C4B—C5B	1.368 (3)
C9A—H9A	0.98 (2)	C5B—C6B	1.385 (4)
C10A—C11A	1.366 (5)	C5B—H5B	0.94 (3)
C10A—H10A	0.93 (3)	C6B—H6B	0.91 (3)
C11A—C12A	1.366 (5)	C9B—C10B	1.374 (3)
C11A—H11A	0.90 (4)	C9B—H9B	0.95 (2)
C12A—C13A	1.378 (4)	C10B—C11B	1.364 (4)
C12A—H12A	0.97 (3)	C10B—H10B	0.92 (3)
C13A—H13A	0.96 (3)	C11B—C12B	1.363 (4)
N1B—C7B	1.246 (3)	C11B—H11B	0.93 (3)
N1B—C8B	1.413 (3)	C12B—C13B	1.370 (4)
C1B—C2B	1.334 (4)	C12B—H12B	0.91 (3)
C1B—C6B	1.413 (4)	C13B—H13B	0.96 (3)

C7A—N1A—C8A	118.81 (17)	C7C—N1C—C8C	134 (2)
O2A—N2A—O1A	123.6 (2)	C6B—C1C—C7C	115 (2)
O2A—N2A—C4A	118.0 (2)	C6B—C1C—C2B	111.3 (16)
O1A—N2A—C4A	118.35 (19)	C7C—C1C—C2B	131 (2)
C2A—C1A—C6A	119.26 (18)	N1C—C7C—C1C	124 (2)
C2A—C1A—C7A	119.21 (18)	N1C—C7C—H7C	117.9
C6A—C1A—C7A	121.52 (17)	C1C—C7C—H7C	117.9
C1A—C2A—C3A	121.0 (2)	C13B—C8C—N1C	116 (2)
C1A—C2A—H2A	119.8 (14)	C13B—C8C—C9B	127.8 (16)
C3A—C2A—H2A	119.2 (14)	N1C—C8C—C9B	116 (2)
C4A—C3A—C2A	118.5 (2)	O2B—N2B—O1B	122.3 (2)
C4A—C3A—H3A	118.6 (14)	O2B—N2B—C4B	119.0 (2)
C2A—C3A—H3A	122.9 (14)	O1B—N2B—C4B	118.7 (2)
C3A—C4A—C5A	122.14 (18)	C1B—C2B—C3B	121.7 (2)
C3A—C4A—N2A	118.80 (19)	C3B—C2B—C1C	112.0 (8)
C5A—C4A—N2A	119.05 (18)	C1B—C2B—H2B	117.2 (14)
C4A—C5A—C6A	118.96 (18)	C3B—C2B—H2B	121.1 (14)
C4A—C5A—H5A	121.8 (12)	C1C—C2B—H2B	126.3 (17)
C6A—C5A—H5A	119.2 (12)	C4B—C3B—C2B	119.0 (2)
C5A—C6A—C1A	120.11 (19)	C4B—C3B—H3B	121.4 (16)
C5A—C6A—H6A	119.2 (13)	C2B—C3B—H3B	119.6 (16)
C1A—C6A—H6A	120.7 (13)	C3B—C4B—C5B	122.2 (2)
N1A—C7A—C1A	122.95 (18)	C3B—C4B—N2B	118.1 (2)
N1A—C7A—H7A	122.4 (12)	C5B—C4B—N2B	119.8 (2)
C1A—C7A—H7A	114.6 (12)	C4B—C5B—C6B	118.0 (2)
C9A—C8A—C13A	120.0 (2)	C4B—C5B—H5B	118.2 (15)
C9A—C8A—N1A	117.9 (2)	C6B—C5B—H5B	123.7 (15)
C13A—C8A—N1A	122.0 (2)	C1C—C6B—C5B	133.5 (13)
C8A—C9A—C10A	119.7 (3)	C1C—C6B—C1B	20.1 (13)
C8A—C9A—H9A	120.4 (14)	C5B—C6B—C1B	120.0 (2)
C10A—C9A—H9A	119.8 (15)	C1C—C6B—H6B	108 (2)
C11A—C10A—C9A	120.3 (3)	C5B—C6B—H6B	115.5 (18)
C11A—C10A—H10A	125.9 (18)	C1B—C6B—H6B	124.5 (18)
C9A—C10A—H10A	113.8 (19)	C8B—C9B—C10B	121.8 (2)
C10A—C11A—C12A	119.9 (3)	C10B—C9B—C8C	108.6 (7)
C10A—C11A—H11A	120 (2)	C8B—C9B—H9B	117.5 (13)
C12A—C11A—H11A	120 (2)	C10B—C9B—H9B	120.6 (13)
C11A—C12A—C13A	120.7 (3)	C8C—C9B—H9B	130.8 (15)
C11A—C12A—H12A	123.2 (19)	C11B—C10B—C9B	120.6 (2)
C13A—C12A—H12A	116.0 (19)	C11B—C10B—H10B	120.5 (17)
C12A—C13A—C8A	119.4 (3)	C9B—C10B—H10B	118.8 (17)
C12A—C13A—H13A	119.4 (16)	C12B—C11B—C10B	119.1 (3)
C8A—C13A—H13A	121.1 (15)	C12B—C11B—H11B	119.9 (17)
C7B—N1B—C8B	120.0 (3)	C10B—C11B—H11B	121.0 (17)
C2B—C1B—C6B	119.1 (2)	C11B—C12B—C13B	121.1 (3)
C2B—C1B—C7B	120.6 (2)	C11B—C12B—H12B	118.2 (18)
C6B—C1B—C7B	120.2 (2)	C13B—C12B—H12B	120.7 (18)
N1B—C7B—C1B	123.7 (2)	C8C—C13B—C12B	122.5 (12)
N1B—C7B—H7B	118.2	C12B—C13B—C8B	119.9 (2)
C1B—C7B—H7B	118.2	C8C—C13B—H13B	116.0 (19)
C9B—C8B—N1B	118.6 (3)	C12B—C13B—H13B	121.3 (15)
C9B—C8B—C13B	117.5 (2)	C8B—C13B—H13B	118.8 (15)
N1B—C8B—C13B	123.9 (2)

C6A—C1A—C2A—C3A	−0.1 (3)	C7C—C1C—C2B—C3B	179 (2)
C7A—C1A—C2A—C3A	−179.0 (2)	C1B—C2B—C3B—C4B	0.2 (4)
C1A—C2A—C3A—C4A	1.2 (3)	C1C—C2B—C3B—C4B	−8.2 (9)
C2A—C3A—C4A—C5A	−2.3 (3)	C2B—C3B—C4B—C5B	0.2 (4)
C2A—C3A—C4A—N2A	177.63 (19)	C2B—C3B—C4B—N2B	−179.6 (2)
O2A—N2A—C4A—C3A	−0.5 (3)	O2B—N2B—C4B—C3B	−6.5 (3)
O1A—N2A—C4A—C3A	−178.8 (2)	O1B—N2B—C4B—C3B	172.4 (2)
O2A—N2A—C4A—C5A	179.4 (2)	O2B—N2B—C4B—C5B	173.8 (2)
O1A—N2A—C4A—C5A	1.1 (3)	O1B—N2B—C4B—C5B	−7.3 (3)
C3A—C4A—C5A—C6A	2.2 (3)	C3B—C4B—C5B—C6B	0.7 (4)
N2A—C4A—C5A—C6A	−177.74 (17)	N2B—C4B—C5B—C6B	−179.6 (2)
C4A—C5A—C6A—C1A	−1.0 (3)	C7C—C1C—C6B—C5B	172.2 (12)
C2A—C1A—C6A—C5A	−0.1 (3)	C2B—C1C—C6B—C5B	−25 (3)
C7A—C1A—C6A—C5A	178.84 (18)	C7C—C1C—C6B—C1B	−134 (5)
C8A—N1A—C7A—C1A	−176.79 (17)	C2B—C1C—C6B—C1B	29 (3)
C2A—C1A—C7A—N1A	179.0 (2)	C4B—C5B—C6B—C1C	17 (2)
C6A—C1A—C7A—N1A	0.1 (3)	C4B—C5B—C6B—C1B	−1.9 (4)
C7A—N1A—C8A—C9A	−141.7 (2)	C2B—C1B—C6B—C1C	−135 (4)
C7A—N1A—C8A—C13A	41.1 (3)	C7B—C1B—C6B—C1C	42 (4)
C13A—C8A—C9A—C10A	−1.6 (3)	C2B—C1B—C6B—C5B	2.2 (4)
N1A—C8A—C9A—C10A	−178.9 (2)	C7B—C1B—C6B—C5B	179.7 (2)
C8A—C9A—C10A—C11A	1.1 (4)	N1B—C8B—C9B—C10B	−177.9 (2)
C9A—C10A—C11A—C12A	0.2 (5)	C13B—C8B—C9B—C10B	0.2 (4)
C10A—C11A—C12A—C13A	−1.1 (5)	N1B—C8B—C9B—C8C	172 (5)
C11A—C12A—C13A—C8A	0.5 (4)	C13B—C8B—C9B—C8C	−10 (4)
C9A—C8A—C13A—C12A	0.8 (4)	C13B—C8C—C9B—C8B	163 (7)
N1A—C8A—C13A—C12A	178.0 (2)	N1C—C8C—C9B—C8B	−15 (3)
C8B—N1B—C7B—C1B	−177.8 (2)	C13B—C8C—C9B—C10B	−8 (3)
C2B—C1B—C7B—N1B	179.7 (2)	N1C—C8C—C9B—C10B	174.5 (17)
C6B—C1B—C7B—N1B	2.3 (4)	C8B—C9B—C10B—C11B	−0.3 (4)
C7B—N1B—C8B—C9B	−157.3 (2)	C8C—C9B—C10B—C11B	2.3 (10)
C7B—N1B—C8B—C13B	24.7 (4)	C9B—C10B—C11B—C12B	0.5 (4)
C8C—N1C—C7C—C1C	173 (3)	C10B—C11B—C12B—C13B	−0.7 (4)
C6B—C1C—C7C—N1C	154 (3)	N1C—C8C—C13B—C12B	−173.7 (14)
C2B—C1C—C7C—N1C	−4 (4)	C9B—C8C—C13B—C12B	8 (3)
C7C—N1C—C8C—C13B	−135 (3)	N1C—C8C—C13B—C8B	127 (19)
C7C—N1C—C8C—C9B	43 (4)	C9B—C8C—C13B—C8B	−51 (15)
C6B—C1B—C2B—C3B	−1.3 (4)	C11B—C12B—C13B—C8C	−4.2 (19)
C7B—C1B—C2B—C3B	−178.8 (2)	C11B—C12B—C13B—C8B	0.6 (4)
C6B—C1B—C2B—C1C	38 (4)	C9B—C8B—C13B—C8C	123 (17)
C7B—C1B—C2B—C1C	−139 (4)	N1B—C8B—C13B—C8C	−59 (17)
C6B—C1C—C2B—C1B	−124 (5)	C9B—C8B—C13B—C12B	−0.4 (4)
C7C—C1C—C2B—C1B	35 (3)	N1B—C8B—C13B—C12B	177.6 (3)
C6B—C1C—C2B—C3B	20 (2)

(1_200K) N-(4-nitrobenzylidene)aniline top

Crystal data top

C₁₃H₁₀N₂O₂	D_x = 1.344 Mg m⁻³
M_r = 226.23	Melting point: 89.7 C K
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.4053 (11) Å	Cell parameters from 10646 reflections
b = 10.7367 (8) Å	θ = 2.4–29.5°
c = 14.7627 (12) Å	µ = 0.09 mm⁻¹
β = 101.617 (2)°	T = 200 K
V = 2236.5 (3) Å³	Block, yellow
Z = 8	0.46 × 0.40 × 0.28 mm
F(000) = 944

Data collection top

Bruker SMART 1000 CCD diffractometer	6529 independent reflections
Radiation source: fine-focus sealed tube	4886 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 8.192 pixels mm^-1	θ_max = 30.0°, θ_min = 1.8°
ω scan	h = −20→20
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −15→15
T_min = 0.959, T_max = 0.974	l = −20→20
33619 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	All H-atom parameters refined
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0542P)² + 0.6974P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
6529 reflections	Δρ_max = 0.27 e Å⁻³
387 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints

Crystal data top

C₁₃H₁₀N₂O₂	V = 2236.5 (3) Å³
M_r = 226.23	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.4053 (11) Å	µ = 0.09 mm⁻¹
b = 10.7367 (8) Å	T = 200 K
c = 14.7627 (12) Å	0.46 × 0.40 × 0.28 mm
β = 101.617 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	6529 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	4886 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.974	R_int = 0.024
33619 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.131	All H-atom parameters refined
S = 1.02	Δρ_max = 0.27 e Å⁻³
6529 reflections	Δρ_min = −0.25 e Å⁻³
387 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1A	0.02534 (7)	0.78734 (10)	0.82414 (7)	0.0353 (2)
N2A	0.01705 (9)	0.74483 (11)	1.25958 (8)	0.0433 (3)
O1A	−0.02553 (8)	0.83413 (10)	1.28260 (7)	0.0530 (3)
O2A	0.04820 (11)	0.65941 (12)	1.31176 (7)	0.0686 (4)
C1A	0.04842 (8)	0.72145 (11)	0.98225 (8)	0.0328 (2)
C2A	0.08396 (10)	0.62832 (13)	1.04475 (9)	0.0417 (3)
C3A	0.07532 (10)	0.63618 (13)	1.13645 (9)	0.0419 (3)
C4A	0.02992 (8)	0.73828 (11)	1.16336 (8)	0.0341 (2)
C5A	−0.00472 (9)	0.83399 (11)	1.10367 (8)	0.0348 (2)
C6A	0.00412 (9)	0.82480 (11)	1.01219 (8)	0.0337 (2)
C7A	0.05736 (9)	0.70758 (12)	0.88540 (8)	0.0360 (3)
C8A	0.03241 (8)	0.76236 (12)	0.73130 (8)	0.0350 (3)
C9A	0.05217 (10)	0.86089 (15)	0.67791 (10)	0.0445 (3)
C10A	0.05795 (12)	0.84085 (19)	0.58617 (11)	0.0554 (4)
C11A	0.04255 (12)	0.7239 (2)	0.54763 (11)	0.0608 (5)
C12A	0.02079 (13)	0.62650 (19)	0.60028 (11)	0.0579 (4)
C13A	0.01573 (11)	0.64443 (15)	0.69220 (10)	0.0450 (3)
H2A	0.1164 (11)	0.5571 (16)	1.0250 (11)	0.052 (4)*
H3A	0.0994 (12)	0.5717 (17)	1.1801 (12)	0.056 (5)*
H5A	−0.0366 (11)	0.9045 (16)	1.1231 (11)	0.046 (4)*
H6A	−0.0205 (11)	0.8891 (15)	0.9682 (11)	0.046 (4)*
H7A	0.0906 (11)	0.6328 (16)	0.8721 (11)	0.050 (4)*
H9A	0.0628 (12)	0.9434 (17)	0.7049 (12)	0.056 (5)*
H10A	0.0722 (13)	0.9107 (19)	0.5532 (13)	0.069 (6)*
H11A	0.0470 (14)	0.7125 (19)	0.4840 (14)	0.077 (6)*
H12A	0.0068 (15)	0.542 (2)	0.5742 (14)	0.079 (6)*
H13A	−0.0011 (12)	0.5749 (17)	0.7278 (12)	0.056 (5)*
N1B	0.23051 (8)	0.95963 (10)	0.14070 (8)	0.0386 (2)
N2B	0.28359 (8)	0.95045 (12)	−0.28440 (8)	0.0446 (3)
O1B	0.25088 (10)	1.04460 (11)	−0.32452 (8)	0.0652 (3)
O2B	0.32207 (10)	0.86931 (13)	−0.32149 (8)	0.0705 (4)
C1B	0.26260 (9)	0.89925 (12)	−0.00638 (9)	0.0364 (3)
C2B	0.29392 (10)	0.80381 (13)	−0.05569 (10)	0.0440 (3)
C3B	0.30156 (10)	0.82055 (13)	−0.14684 (10)	0.0428 (3)
C4B	0.27614 (9)	0.93362 (12)	−0.18750 (9)	0.0377 (3)
C5B	0.24395 (11)	1.03105 (14)	−0.14101 (10)	0.0477 (3)
C6B	0.23833 (11)	1.01342 (14)	−0.04946 (10)	0.0454 (3)
C7B	0.25703 (9)	0.87704 (12)	0.09065 (9)	0.0388 (3)
C8B	0.23092 (8)	0.93247 (12)	0.23496 (8)	0.0346 (2)
C9B	0.17155 (10)	1.00211 (13)	0.27831 (9)	0.0404 (3)
C10B	0.16971 (11)	0.98228 (15)	0.37052 (10)	0.0480 (3)
C11B	0.22713 (11)	0.89296 (16)	0.42069 (10)	0.0504 (4)
C12B	0.28690 (11)	0.82406 (16)	0.37812 (11)	0.0515 (4)
C13B	0.28945 (10)	0.84309 (14)	0.28627 (10)	0.0443 (3)
H2B	0.3093 (12)	0.7243 (16)	−0.0246 (11)	0.054 (5)*
H3B	0.3243 (13)	0.7543 (17)	−0.1799 (12)	0.063 (5)*
H5B	0.2302 (12)	1.1089 (18)	−0.1702 (12)	0.061 (5)*
H6B	0.2180 (12)	1.0807 (17)	−0.0165 (12)	0.060 (5)*
H7B	0.2739 (12)	0.7903 (17)	0.1141 (11)	0.054 (5)*
H9B	0.1315 (12)	1.0634 (16)	0.2436 (11)	0.051 (4)*
H10B	0.1278 (13)	1.0307 (17)	0.3986 (12)	0.060 (5)*
H11B	0.2255 (13)	0.8799 (17)	0.4859 (13)	0.062 (5)*
H12B	0.3256 (15)	0.7625 (19)	0.4112 (14)	0.078 (6)*
H13B	0.3307 (12)	0.7974 (17)	0.2561 (12)	0.059 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0355 (5)	0.0397 (5)	0.0318 (5)	0.0000 (4)	0.0092 (4)	−0.0049 (4)
N2A	0.0536 (7)	0.0439 (6)	0.0333 (5)	−0.0137 (5)	0.0114 (5)	−0.0033 (5)
O1A	0.0718 (7)	0.0477 (6)	0.0462 (6)	−0.0127 (5)	0.0281 (5)	−0.0118 (4)
O2A	0.1076 (10)	0.0626 (7)	0.0361 (5)	0.0058 (7)	0.0155 (6)	0.0093 (5)
C1A	0.0306 (5)	0.0362 (6)	0.0311 (5)	0.0000 (4)	0.0052 (4)	−0.0036 (4)
C2A	0.0445 (7)	0.0407 (7)	0.0397 (7)	0.0120 (6)	0.0081 (5)	−0.0016 (5)
C3A	0.0458 (7)	0.0406 (7)	0.0379 (6)	0.0064 (6)	0.0049 (5)	0.0052 (5)
C4A	0.0360 (6)	0.0376 (6)	0.0288 (5)	−0.0081 (5)	0.0066 (4)	−0.0031 (4)
C5A	0.0388 (6)	0.0316 (6)	0.0352 (6)	−0.0016 (5)	0.0104 (5)	−0.0052 (4)
C6A	0.0370 (6)	0.0319 (6)	0.0324 (6)	0.0004 (5)	0.0070 (5)	−0.0012 (4)
C7A	0.0342 (6)	0.0402 (6)	0.0337 (6)	0.0037 (5)	0.0074 (5)	−0.0066 (5)
C8A	0.0291 (5)	0.0458 (7)	0.0306 (5)	0.0023 (5)	0.0071 (4)	−0.0040 (5)
C9A	0.0425 (7)	0.0509 (8)	0.0419 (7)	0.0021 (6)	0.0130 (6)	0.0014 (6)
C10A	0.0508 (8)	0.0769 (11)	0.0418 (8)	0.0062 (8)	0.0173 (6)	0.0131 (8)
C11A	0.0571 (9)	0.0955 (14)	0.0310 (7)	0.0094 (9)	0.0115 (6)	−0.0059 (8)
C12A	0.0627 (10)	0.0719 (11)	0.0382 (7)	−0.0012 (8)	0.0084 (7)	−0.0192 (7)
C13A	0.0491 (8)	0.0500 (8)	0.0359 (6)	−0.0022 (6)	0.0084 (6)	−0.0083 (6)
N1B	0.0367 (5)	0.0408 (6)	0.0387 (5)	0.0007 (4)	0.0084 (4)	0.0003 (4)
N2B	0.0430 (6)	0.0505 (7)	0.0426 (6)	0.0008 (5)	0.0140 (5)	0.0023 (5)
O1B	0.0903 (9)	0.0536 (7)	0.0574 (7)	0.0099 (6)	0.0283 (6)	0.0158 (5)
O2B	0.0828 (9)	0.0865 (9)	0.0474 (6)	0.0345 (7)	0.0258 (6)	0.0029 (6)
C1B	0.0307 (6)	0.0393 (6)	0.0388 (6)	−0.0014 (5)	0.0062 (5)	−0.0029 (5)
C2B	0.0517 (8)	0.0368 (7)	0.0446 (7)	0.0050 (6)	0.0126 (6)	0.0011 (5)
C3B	0.0462 (7)	0.0394 (7)	0.0448 (7)	0.0037 (6)	0.0140 (6)	−0.0033 (6)
C4B	0.0334 (6)	0.0429 (7)	0.0381 (6)	−0.0002 (5)	0.0104 (5)	−0.0004 (5)
C5B	0.0569 (8)	0.0406 (7)	0.0473 (8)	0.0103 (6)	0.0151 (6)	0.0040 (6)
C6B	0.0515 (8)	0.0412 (7)	0.0457 (7)	0.0081 (6)	0.0150 (6)	−0.0040 (6)
C7B	0.0381 (6)	0.0358 (6)	0.0419 (7)	−0.0009 (5)	0.0071 (5)	−0.0010 (5)
C8B	0.0311 (6)	0.0350 (6)	0.0370 (6)	−0.0037 (4)	0.0052 (5)	−0.0016 (5)
C9B	0.0388 (6)	0.0393 (7)	0.0418 (7)	0.0029 (5)	0.0053 (5)	−0.0029 (5)
C10B	0.0431 (7)	0.0585 (9)	0.0435 (7)	0.0000 (6)	0.0113 (6)	−0.0090 (6)
C11B	0.0438 (7)	0.0678 (10)	0.0393 (7)	−0.0094 (7)	0.0071 (6)	0.0042 (7)
C12B	0.0439 (8)	0.0583 (9)	0.0501 (8)	0.0038 (7)	0.0041 (6)	0.0153 (7)
C13B	0.0388 (7)	0.0469 (7)	0.0476 (7)	0.0066 (6)	0.0093 (6)	0.0038 (6)

Geometric parameters (Å, º) top

N1A—C7A	1.2632 (16)	N1B—C7B	1.2617 (17)
N1A—C8A	1.4202 (15)	N1B—C8B	1.4207 (16)
N2A—O1A	1.2227 (16)	N2B—O1B	1.2175 (16)
N2A—O2A	1.2233 (16)	N2B—O2B	1.2200 (16)
N2A—C4A	1.4708 (15)	N2B—C4B	1.4671 (17)
C1A—C2A	1.3868 (18)	C1B—C2B	1.3841 (18)
C1A—C6A	1.3955 (17)	C1B—C6B	1.3928 (19)
C1A—C7A	1.4687 (16)	C1B—C7B	1.4702 (18)
C2A—C3A	1.3868 (19)	C2B—C3B	1.3838 (19)
C2A—H2A	0.971 (17)	C2B—H2B	0.973 (17)
C3A—C4A	1.3754 (18)	C3B—C4B	1.3710 (19)
C3A—H3A	0.961 (18)	C3B—H3B	0.957 (18)
C4A—C5A	1.3800 (17)	C4B—C5B	1.3815 (19)
C5A—C6A	1.3852 (16)	C5B—C6B	1.383 (2)
C5A—H5A	0.959 (17)	C5B—H5B	0.943 (19)
C6A—H6A	0.965 (16)	C6B—H6B	0.950 (18)
C7A—H7A	0.975 (17)	C7B—H7B	1.006 (18)
C8A—C9A	1.3827 (19)	C8B—C9B	1.3858 (18)
C8A—C13A	1.3922 (19)	C8B—C13B	1.3958 (18)
C9A—C10A	1.390 (2)	C9B—C10B	1.383 (2)
C9A—H9A	0.971 (18)	C9B—H9B	0.953 (17)
C10A—C11A	1.378 (3)	C10B—C11B	1.380 (2)
C10A—H10A	0.94 (2)	C10B—H10B	0.953 (18)
C11A—C12A	1.376 (3)	C11B—C12B	1.379 (2)
C11A—H11A	0.96 (2)	C11B—H11B	0.978 (18)
C12A—C13A	1.387 (2)	C12B—C13B	1.379 (2)
C12A—H12A	0.99 (2)	C12B—H12B	0.94 (2)
C13A—H13A	0.972 (18)	C13B—H13B	0.949 (18)

C7A—N1A—C8A	118.43 (11)	C7B—N1B—C8B	119.16 (11)
O1A—N2A—O2A	123.63 (12)	O1B—N2B—O2B	122.74 (13)
O1A—N2A—C4A	118.28 (11)	O1B—N2B—C4B	118.65 (12)
O2A—N2A—C4A	118.08 (12)	O2B—N2B—C4B	118.60 (12)
C2A—C1A—C6A	119.58 (11)	C2B—C1B—C6B	119.33 (12)
C2A—C1A—C7A	118.79 (11)	C2B—C1B—C7B	118.68 (12)
C6A—C1A—C7A	121.62 (11)	C6B—C1B—C7B	121.99 (12)
C1A—C2A—C3A	120.79 (12)	C3B—C2B—C1B	120.90 (13)
C1A—C2A—H2A	120.2 (10)	C3B—C2B—H2B	121.1 (10)
C3A—C2A—H2A	119.0 (10)	C1B—C2B—H2B	118.0 (10)
C4A—C3A—C2A	118.15 (12)	C4B—C3B—C2B	118.30 (13)
C4A—C3A—H3A	120.6 (10)	C4B—C3B—H3B	121.6 (11)
C2A—C3A—H3A	121.3 (10)	C2B—C3B—H3B	120.1 (11)
C3A—C4A—C5A	122.75 (11)	C3B—C4B—C5B	122.67 (12)
C3A—C4A—N2A	118.47 (11)	C3B—C4B—N2B	118.06 (12)
C5A—C4A—N2A	118.78 (11)	C5B—C4B—N2B	119.27 (12)
C4A—C5A—C6A	118.49 (11)	C4B—C5B—C6B	118.25 (13)
C4A—C5A—H5A	122.0 (9)	C4B—C5B—H5B	120.3 (11)
C6A—C5A—H5A	119.5 (9)	C6B—C5B—H5B	121.3 (11)
C5A—C6A—C1A	120.21 (11)	C5B—C6B—C1B	120.52 (13)
C5A—C6A—H6A	120.7 (9)	C5B—C6B—H6B	118.8 (11)
C1A—C6A—H6A	119.0 (9)	C1B—C6B—H6B	120.7 (11)
N1A—C7A—C1A	122.49 (11)	N1B—C7B—C1B	122.61 (12)
N1A—C7A—H7A	122.5 (9)	N1B—C7B—H7B	122.0 (10)
C1A—C7A—H7A	115.0 (9)	C1B—C7B—H7B	115.4 (10)
C9A—C8A—C13A	119.84 (12)	C9B—C8B—C13B	118.81 (12)
C9A—C8A—N1A	117.95 (12)	C9B—C8B—N1B	117.41 (11)
C13A—C8A—N1A	122.14 (12)	C13B—C8B—N1B	123.76 (12)
C8A—C9A—C10A	119.77 (15)	C10B—C9B—C8B	120.48 (13)
C8A—C9A—H9A	119.8 (10)	C10B—C9B—H9B	120.3 (10)
C10A—C9A—H9A	120.4 (10)	C8B—C9B—H9B	119.2 (10)
C11A—C10A—C9A	120.47 (16)	C11B—C10B—C9B	120.45 (14)
C11A—C10A—H10A	123.2 (12)	C11B—C10B—H10B	120.6 (11)
C9A—C10A—H10A	116.3 (12)	C9B—C10B—H10B	119.0 (11)
C12A—C11A—C10A	119.69 (14)	C12B—C11B—C10B	119.32 (14)
C12A—C11A—H11A	121.5 (13)	C12B—C11B—H11B	120.9 (11)
C10A—C11A—H11A	118.8 (13)	C10B—C11B—H11B	119.8 (11)
C11A—C12A—C13A	120.66 (16)	C13B—C12B—C11B	120.75 (14)
C11A—C12A—H12A	121.8 (12)	C13B—C12B—H12B	119.1 (13)
C13A—C12A—H12A	117.5 (12)	C11B—C12B—H12B	120.1 (13)
C12A—C13A—C8A	119.55 (15)	C12B—C13B—C8B	120.18 (13)
C12A—C13A—H13A	119.4 (10)	C12B—C13B—H13B	121.9 (11)
C8A—C13A—H13A	121.0 (10)	C8B—C13B—H13B	117.9 (11)

C6A—C1A—C2A—C3A	0.5 (2)	C6B—C1B—C2B—C3B	0.2 (2)
C7A—C1A—C2A—C3A	−178.63 (12)	C7B—C1B—C2B—C3B	−179.18 (13)
C1A—C2A—C3A—C4A	0.5 (2)	C1B—C2B—C3B—C4B	−0.8 (2)
C2A—C3A—C4A—C5A	−1.8 (2)	C2B—C3B—C4B—C5B	0.4 (2)
C2A—C3A—C4A—N2A	177.55 (12)	C2B—C3B—C4B—N2B	−179.46 (12)
O1A—N2A—C4A—C3A	−178.11 (12)	O1B—N2B—C4B—C3B	171.42 (14)
O2A—N2A—C4A—C3A	0.67 (18)	O2B—N2B—C4B—C3B	−8.38 (19)
O1A—N2A—C4A—C5A	1.29 (17)	O1B—N2B—C4B—C5B	−8.5 (2)
O2A—N2A—C4A—C5A	−179.92 (13)	O2B—N2B—C4B—C5B	171.75 (14)
C3A—C4A—C5A—C6A	2.03 (19)	C3B—C4B—C5B—C6B	0.7 (2)
N2A—C4A—C5A—C6A	−177.35 (11)	N2B—C4B—C5B—C6B	−179.43 (13)
C4A—C5A—C6A—C1A	−0.91 (18)	C4B—C5B—C6B—C1B	−1.4 (2)
C2A—C1A—C6A—C5A	−0.33 (18)	C2B—C1B—C6B—C5B	1.0 (2)
C7A—C1A—C6A—C5A	178.81 (11)	C7B—C1B—C6B—C5B	−179.70 (13)
C8A—N1A—C7A—C1A	−176.36 (11)	C8B—N1B—C7B—C1B	−177.33 (11)
C2A—C1A—C7A—N1A	178.77 (13)	C2B—C1B—C7B—N1B	178.99 (13)
C6A—C1A—C7A—N1A	−0.37 (19)	C6B—C1B—C7B—N1B	−0.3 (2)
C7A—N1A—C8A—C9A	−142.48 (13)	C7B—N1B—C8B—C9B	−156.92 (12)
C7A—N1A—C8A—C13A	40.62 (17)	C7B—N1B—C8B—C13B	25.13 (19)
C13A—C8A—C9A—C10A	−1.8 (2)	C13B—C8B—C9B—C10B	−0.7 (2)
N1A—C8A—C9A—C10A	−178.81 (12)	N1B—C8B—C9B—C10B	−178.75 (12)
C8A—C9A—C10A—C11A	1.1 (2)	C8B—C9B—C10B—C11B	0.1 (2)
C9A—C10A—C11A—C12A	0.4 (3)	C9B—C10B—C11B—C12B	0.4 (2)
C10A—C11A—C12A—C13A	−1.1 (3)	C10B—C11B—C12B—C13B	−0.3 (2)
C11A—C12A—C13A—C8A	0.3 (2)	C11B—C12B—C13B—C8B	−0.3 (2)
C9A—C8A—C13A—C12A	1.1 (2)	C9B—C8B—C13B—C12B	0.8 (2)
N1A—C8A—C13A—C12A	177.99 (13)	N1B—C8B—C13B—C12B	178.69 (13)

(1_90K) N-(4-nitrobenzylidene)aniline top

Crystal data top

C₁₃H₁₀N₂O₂	D_x = 1.366 Mg m⁻³
M_r = 226.23	Melting point: 89.7 C K
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.2105 (12) Å	Cell parameters from 13353 reflections
b = 10.6596 (9) Å	θ = 2.2–30.0°
c = 14.8045 (12) Å	µ = 0.10 mm⁻¹
β = 101.228 (2)°	T = 90 K
V = 2199.6 (3) Å³	Block, yellow
Z = 8	0.46 × 0.40 × 0.28 mm
F(000) = 944

Data collection top

Bruker SMART 1000 CCD diffractometer	6400 independent reflections
Radiation source: fine-focus sealed tube	5521 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 8.192 pixels mm^-1	θ_max = 30.0°, θ_min = 1.8°
ω scan	h = −20→19
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −15→15
T_min = 0.958, T_max = 0.974	l = −20→20
33043 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	All H-atom parameters refined
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0629P)² + 0.6739P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
6400 reflections	Δρ_max = 0.42 e Å⁻³
387 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints

Crystal data top

C₁₃H₁₀N₂O₂	V = 2199.6 (3) Å³
M_r = 226.23	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.2105 (12) Å	µ = 0.10 mm⁻¹
b = 10.6596 (9) Å	T = 90 K
c = 14.8045 (12) Å	0.46 × 0.40 × 0.28 mm
β = 101.228 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	6400 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	5521 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.974	R_int = 0.023
33043 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.112	All H-atom parameters refined
S = 1.02	Δρ_max = 0.42 e Å⁻³
6400 reflections	Δρ_min = −0.19 e Å⁻³
387 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1A	0.02665 (6)	0.78597 (8)	0.82396 (5)	0.01699 (16)
N2A	0.01711 (6)	0.74674 (8)	1.25887 (6)	0.01987 (17)
O1A	−0.02677 (6)	0.83718 (7)	1.28125 (5)	0.02399 (16)
O2A	0.04904 (7)	0.66109 (8)	1.31161 (5)	0.03077 (19)
C1A	0.04987 (6)	0.72049 (9)	0.98201 (6)	0.01606 (17)
C2A	0.08570 (7)	0.62652 (9)	1.04481 (7)	0.01981 (18)
C3A	0.07661 (7)	0.63512 (9)	1.13643 (7)	0.01996 (19)
C4A	0.03078 (6)	0.73924 (9)	1.16312 (6)	0.01659 (17)
C5A	−0.00405 (7)	0.83618 (9)	1.10289 (6)	0.01669 (17)
C6A	0.00533 (7)	0.82592 (9)	1.01174 (6)	0.01634 (17)
C7A	0.05929 (7)	0.70542 (9)	0.88557 (6)	0.01749 (17)
C8A	0.03366 (6)	0.75941 (9)	0.73156 (6)	0.01659 (17)
C9A	0.05314 (7)	0.85862 (10)	0.67672 (7)	0.02056 (19)
C10A	0.05887 (8)	0.83723 (11)	0.58509 (7)	0.0246 (2)
C11A	0.04337 (8)	0.71799 (12)	0.54722 (7)	0.0264 (2)
C12A	0.02167 (8)	0.61985 (11)	0.60137 (7)	0.0257 (2)
C13A	0.01695 (7)	0.63955 (10)	0.69321 (7)	0.02057 (19)
H2A	0.1189 (10)	0.5553 (13)	1.0259 (9)	0.026 (3)*
H3A	0.1016 (11)	0.5703 (14)	1.1810 (10)	0.031 (4)*
H5A	−0.0354 (10)	0.9090 (14)	1.1229 (9)	0.025 (3)*
H6A	−0.0197 (10)	0.8893 (13)	0.9684 (9)	0.024 (3)*
H7A	0.0927 (10)	0.6292 (14)	0.8718 (10)	0.029 (4)*
H9A	0.0636 (10)	0.9424 (14)	0.7033 (10)	0.029 (3)*
H10A	0.0724 (11)	0.9063 (15)	0.5494 (10)	0.035 (4)*
H11A	0.0468 (11)	0.7040 (15)	0.4841 (10)	0.035 (4)*
H12A	0.0097 (11)	0.5366 (15)	0.5772 (11)	0.037 (4)*
H13A	0.0005 (10)	0.5717 (14)	0.7289 (10)	0.029 (3)*
N1B	0.22998 (6)	0.96054 (8)	0.14065 (6)	0.01827 (16)
N2B	0.28274 (6)	0.95132 (8)	−0.28501 (6)	0.02090 (17)
O1B	0.24644 (6)	1.04503 (8)	−0.32553 (6)	0.02946 (18)
O2B	0.32478 (6)	0.87098 (9)	−0.32167 (6)	0.0326 (2)
C1B	0.26260 (6)	0.89955 (9)	−0.00668 (6)	0.01729 (17)
C2B	0.29571 (7)	0.80304 (9)	−0.05605 (7)	0.02048 (19)
C3B	0.30336 (7)	0.82005 (9)	−0.14734 (7)	0.02014 (18)
C4B	0.27542 (7)	0.93408 (9)	−0.18822 (6)	0.01839 (18)
C5B	0.24149 (8)	1.03233 (10)	−0.14162 (7)	0.0224 (2)
C6B	0.23630 (7)	1.01464 (10)	−0.05004 (7)	0.02113 (19)
C7B	0.25720 (7)	0.87666 (9)	0.09003 (7)	0.01860 (18)
C8B	0.23077 (6)	0.93227 (9)	0.23454 (6)	0.01663 (17)
C9B	0.16985 (7)	1.00160 (9)	0.27880 (7)	0.01933 (18)
C10B	0.16811 (7)	0.97977 (10)	0.37099 (7)	0.0225 (2)
C11B	0.22708 (7)	0.88906 (11)	0.42034 (7)	0.0237 (2)
C12B	0.28840 (7)	0.82031 (11)	0.37656 (7)	0.0237 (2)
C13B	0.29090 (7)	0.84169 (9)	0.28469 (7)	0.02040 (19)
H2B	0.3127 (10)	0.7240 (13)	−0.0261 (9)	0.025 (3)*
H3B	0.3274 (11)	0.7536 (14)	−0.1803 (10)	0.034 (4)*
H5B	0.2251 (11)	1.1103 (15)	−0.1698 (10)	0.032 (4)*
H6B	0.2140 (11)	1.0801 (14)	−0.0163 (10)	0.032 (4)*
H7B	0.2728 (11)	0.7893 (14)	0.1115 (10)	0.030 (4)*
H9B	0.1272 (10)	1.0621 (13)	0.2446 (9)	0.023 (3)*
H10B	0.1257 (10)	1.0291 (14)	0.4001 (10)	0.030 (4)*
H11B	0.2253 (11)	0.8736 (14)	0.4842 (10)	0.032 (4)*
H12B	0.3298 (11)	0.7582 (14)	0.4099 (10)	0.032 (4)*
H13B	0.3352 (10)	0.7958 (14)	0.2559 (9)	0.029 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0170 (3)	0.0195 (4)	0.0151 (3)	−0.0012 (3)	0.0048 (3)	−0.0027 (3)
N2A	0.0244 (4)	0.0198 (4)	0.0159 (4)	−0.0060 (3)	0.0050 (3)	−0.0018 (3)
O1A	0.0309 (4)	0.0213 (3)	0.0228 (3)	−0.0053 (3)	0.0125 (3)	−0.0054 (3)
O2A	0.0474 (5)	0.0276 (4)	0.0171 (3)	0.0017 (4)	0.0060 (3)	0.0039 (3)
C1A	0.0150 (4)	0.0180 (4)	0.0151 (4)	−0.0002 (3)	0.0026 (3)	−0.0022 (3)
C2A	0.0212 (4)	0.0195 (4)	0.0189 (4)	0.0056 (3)	0.0042 (3)	−0.0011 (3)
C3A	0.0217 (4)	0.0195 (4)	0.0179 (4)	0.0030 (3)	0.0020 (3)	0.0017 (3)
C4A	0.0174 (4)	0.0187 (4)	0.0137 (4)	−0.0039 (3)	0.0033 (3)	−0.0016 (3)
C5A	0.0177 (4)	0.0151 (4)	0.0177 (4)	−0.0009 (3)	0.0044 (3)	−0.0024 (3)
C6A	0.0175 (4)	0.0158 (4)	0.0157 (4)	0.0001 (3)	0.0033 (3)	−0.0003 (3)
C7A	0.0167 (4)	0.0195 (4)	0.0164 (4)	0.0016 (3)	0.0037 (3)	−0.0035 (3)
C8A	0.0139 (4)	0.0210 (4)	0.0151 (4)	0.0012 (3)	0.0036 (3)	−0.0020 (3)
C9A	0.0204 (4)	0.0223 (5)	0.0199 (4)	0.0008 (3)	0.0061 (3)	0.0004 (3)
C10A	0.0239 (5)	0.0319 (5)	0.0196 (4)	0.0024 (4)	0.0079 (4)	0.0055 (4)
C11A	0.0257 (5)	0.0388 (6)	0.0154 (4)	0.0039 (4)	0.0056 (4)	−0.0023 (4)
C12A	0.0291 (5)	0.0293 (5)	0.0184 (4)	−0.0001 (4)	0.0038 (4)	−0.0072 (4)
C13A	0.0225 (4)	0.0220 (4)	0.0173 (4)	−0.0009 (4)	0.0040 (3)	−0.0021 (3)
N1B	0.0167 (3)	0.0202 (4)	0.0181 (4)	−0.0001 (3)	0.0037 (3)	0.0006 (3)
N2B	0.0201 (4)	0.0229 (4)	0.0208 (4)	0.0002 (3)	0.0066 (3)	0.0009 (3)
O1B	0.0387 (4)	0.0243 (4)	0.0276 (4)	0.0045 (3)	0.0119 (3)	0.0075 (3)
O2B	0.0378 (5)	0.0386 (5)	0.0240 (4)	0.0155 (4)	0.0126 (3)	0.0011 (3)
C1B	0.0147 (4)	0.0184 (4)	0.0188 (4)	−0.0012 (3)	0.0031 (3)	−0.0014 (3)
C2B	0.0229 (4)	0.0169 (4)	0.0222 (4)	0.0014 (3)	0.0057 (4)	0.0003 (3)
C3B	0.0210 (4)	0.0184 (4)	0.0219 (4)	0.0009 (3)	0.0066 (3)	−0.0025 (3)
C4B	0.0164 (4)	0.0211 (4)	0.0185 (4)	−0.0007 (3)	0.0055 (3)	−0.0005 (3)
C5B	0.0254 (5)	0.0193 (4)	0.0231 (5)	0.0045 (4)	0.0066 (4)	0.0019 (4)
C6B	0.0228 (4)	0.0194 (4)	0.0220 (4)	0.0035 (4)	0.0065 (4)	−0.0019 (3)
C7B	0.0180 (4)	0.0176 (4)	0.0198 (4)	−0.0011 (3)	0.0028 (3)	−0.0005 (3)
C8B	0.0155 (4)	0.0163 (4)	0.0179 (4)	−0.0023 (3)	0.0026 (3)	−0.0011 (3)
C9B	0.0185 (4)	0.0188 (4)	0.0203 (4)	0.0007 (3)	0.0027 (3)	−0.0016 (3)
C10B	0.0203 (4)	0.0264 (5)	0.0215 (5)	−0.0008 (4)	0.0055 (4)	−0.0039 (4)
C11B	0.0207 (4)	0.0309 (5)	0.0192 (4)	−0.0047 (4)	0.0035 (3)	0.0020 (4)
C12B	0.0198 (4)	0.0259 (5)	0.0242 (5)	0.0006 (4)	0.0017 (4)	0.0063 (4)
C13B	0.0171 (4)	0.0215 (4)	0.0228 (4)	0.0019 (3)	0.0042 (3)	0.0010 (4)

Geometric parameters (Å, º) top

N1A—C7A	1.2727 (12)	N1B—C7B	1.2742 (13)
N1A—C8A	1.4192 (11)	N1B—C8B	1.4201 (12)
N2A—O1A	1.2282 (11)	N2B—O1B	1.2261 (12)
N2A—O2A	1.2293 (12)	N2B—O2B	1.2293 (11)
N2A—C4A	1.4700 (11)	N2B—C4B	1.4683 (12)
C1A—C2A	1.3938 (13)	C1B—C2B	1.3957 (13)
C1A—C6A	1.4021 (13)	C1B—C6B	1.4013 (14)
C1A—C7A	1.4684 (12)	C1B—C7B	1.4690 (13)
C2A—C3A	1.3904 (13)	C2B—C3B	1.3887 (13)
C2A—H2A	0.964 (14)	C2B—H2B	0.961 (14)
C3A—C4A	1.3828 (13)	C3B—C4B	1.3811 (14)
C3A—H3A	0.973 (15)	C3B—H3B	0.960 (15)
C4A—C5A	1.3913 (13)	C4B—C5B	1.3910 (13)
C5A—C6A	1.3859 (12)	C5B—C6B	1.3849 (14)
C5A—H5A	0.970 (14)	C5B—H5B	0.938 (15)
C6A—H6A	0.952 (14)	C6B—H6B	0.947 (15)
C7A—H7A	0.982 (15)	C7B—H7B	0.996 (15)
C8A—C9A	1.3934 (13)	C8B—C9B	1.3950 (13)
C8A—C13A	1.3995 (13)	C8B—C13B	1.4023 (13)
C9A—C10A	1.3935 (14)	C9B—C10B	1.3894 (14)
C9A—H9A	0.976 (15)	C9B—H9B	0.960 (14)
C10A—C11A	1.3894 (16)	C10B—C11B	1.3902 (15)
C10A—H10A	0.948 (16)	C10B—H10B	0.963 (14)
C11A—C12A	1.3887 (16)	C11B—C12B	1.3916 (15)
C11A—H11A	0.957 (15)	C11B—H11B	0.965 (15)
C12A—C13A	1.3903 (13)	C12B—C13B	1.3863 (14)
C12A—H12A	0.959 (16)	C12B—H12B	0.956 (15)
C13A—H13A	0.951 (15)	C13B—H13B	0.961 (14)

C7A—N1A—C8A	118.17 (8)	C7B—N1B—C8B	118.77 (8)
O1A—N2A—O2A	123.75 (8)	O1B—N2B—O2B	123.09 (9)
O1A—N2A—C4A	118.18 (8)	O1B—N2B—C4B	118.46 (8)
O2A—N2A—C4A	118.06 (8)	O2B—N2B—C4B	118.46 (8)
C2A—C1A—C6A	119.68 (8)	C2B—C1B—C6B	119.51 (9)
C2A—C1A—C7A	118.64 (8)	C2B—C1B—C7B	118.35 (9)
C6A—C1A—C7A	121.68 (8)	C6B—C1B—C7B	122.14 (8)
C3A—C2A—C1A	120.81 (9)	C3B—C2B—C1B	120.77 (9)
C3A—C2A—H2A	118.6 (8)	C3B—C2B—H2B	120.2 (8)
C1A—C2A—H2A	120.6 (8)	C1B—C2B—H2B	119.0 (8)
C4A—C3A—C2A	118.04 (9)	C4B—C3B—C2B	118.10 (9)
C4A—C3A—H3A	120.4 (9)	C4B—C3B—H3B	121.8 (9)
C2A—C3A—H3A	121.6 (9)	C2B—C3B—H3B	120.1 (9)
C3A—C4A—C5A	122.79 (8)	C3B—C4B—C5B	122.90 (9)
C3A—C4A—N2A	118.50 (8)	C3B—C4B—N2B	117.95 (8)
C5A—C4A—N2A	118.70 (8)	C5B—C4B—N2B	119.15 (9)
C6A—C5A—C4A	118.41 (8)	C6B—C5B—C4B	118.21 (9)
C6A—C5A—H5A	119.9 (8)	C6B—C5B—H5B	119.9 (9)
C4A—C5A—H5A	121.7 (8)	C4B—C5B—H5B	121.8 (9)
C5A—C6A—C1A	120.25 (8)	C5B—C6B—C1B	120.48 (9)
C5A—C6A—H6A	120.4 (8)	C5B—C6B—H6B	120.2 (9)
C1A—C6A—H6A	119.3 (8)	C1B—C6B—H6B	119.3 (9)
N1A—C7A—C1A	122.24 (8)	N1B—C7B—C1B	122.43 (9)
N1A—C7A—H7A	122.2 (8)	N1B—C7B—H7B	122.9 (8)
C1A—C7A—H7A	115.5 (8)	C1B—C7B—H7B	114.6 (8)
C9A—C8A—C13A	119.59 (9)	C9B—C8B—C13B	119.08 (9)
C9A—C8A—N1A	117.99 (8)	C9B—C8B—N1B	117.38 (8)
C13A—C8A—N1A	122.34 (8)	C13B—C8B—N1B	123.52 (8)
C8A—C9A—C10A	119.93 (9)	C10B—C9B—C8B	120.26 (9)
C8A—C9A—H9A	119.4 (8)	C10B—C9B—H9B	120.0 (8)
C10A—C9A—H9A	120.6 (9)	C8B—C9B—H9B	119.6 (8)
C11A—C10A—C9A	120.52 (10)	C9B—C10B—C11B	120.57 (9)
C11A—C10A—H10A	121.3 (9)	C9B—C10B—H10B	118.7 (9)
C9A—C10A—H10A	118.2 (9)	C11B—C10B—H10B	120.7 (9)
C12A—C11A—C10A	119.46 (9)	C10B—C11B—C12B	119.31 (9)
C12A—C11A—H11A	120.4 (9)	C10B—C11B—H11B	120.4 (9)
C10A—C11A—H11A	120.2 (9)	C12B—C11B—H11B	120.3 (9)
C11A—C12A—C13A	120.61 (10)	C13B—C12B—C11B	120.56 (9)
C11A—C12A—H12A	121.6 (9)	C13B—C12B—H12B	119.3 (9)
C13A—C12A—H12A	117.8 (9)	C11B—C12B—H12B	120.2 (9)
C12A—C13A—C8A	119.87 (10)	C12B—C13B—C8B	120.22 (9)
C12A—C13A—H13A	119.4 (9)	C12B—C13B—H13B	119.7 (8)
C8A—C13A—H13A	120.7 (9)	C8B—C13B—H13B	120.0 (8)

C6A—C1A—C2A—C3A	0.93 (14)	C6B—C1B—C2B—C3B	0.36 (15)
C7A—C1A—C2A—C3A	−178.55 (9)	C7B—C1B—C2B—C3B	−179.22 (9)
C1A—C2A—C3A—C4A	0.21 (15)	C1B—C2B—C3B—C4B	−1.32 (15)
C2A—C3A—C4A—C5A	−1.65 (14)	C2B—C3B—C4B—C5B	0.93 (15)
C2A—C3A—C4A—N2A	177.43 (8)	C2B—C3B—C4B—N2B	−179.43 (8)
O1A—N2A—C4A—C3A	−177.35 (9)	O1B—N2B—C4B—C3B	170.36 (9)
O2A—N2A—C4A—C3A	1.58 (13)	O2B—N2B—C4B—C3B	−9.47 (13)
O1A—N2A—C4A—C5A	1.77 (12)	O1B—N2B—C4B—C5B	−9.98 (14)
O2A—N2A—C4A—C5A	−179.30 (9)	O2B—N2B—C4B—C5B	170.19 (10)
C3A—C4A—C5A—C6A	1.87 (14)	C3B—C4B—C5B—C6B	0.44 (15)
N2A—C4A—C5A—C6A	−177.21 (8)	N2B—C4B—C5B—C6B	−179.20 (9)
C4A—C5A—C6A—C1A	−0.65 (13)	C4B—C5B—C6B—C1B	−1.44 (15)
C2A—C1A—C6A—C5A	−0.71 (14)	C2B—C1B—C6B—C5B	1.06 (15)
C7A—C1A—C6A—C5A	178.76 (8)	C7B—C1B—C6B—C5B	−179.38 (9)
C8A—N1A—C7A—C1A	−176.00 (8)	C8B—N1B—C7B—C1B	−177.33 (8)
C2A—C1A—C7A—N1A	178.57 (9)	C2B—C1B—C7B—N1B	178.30 (9)
C6A—C1A—C7A—N1A	−0.91 (14)	C6B—C1B—C7B—N1B	−1.27 (14)
C7A—N1A—C8A—C9A	−143.04 (9)	C7B—N1B—C8B—C9B	−156.52 (9)
C7A—N1A—C8A—C13A	40.28 (13)	C7B—N1B—C8B—C13B	25.26 (13)
C13A—C8A—C9A—C10A	−2.03 (14)	C13B—C8B—C9B—C10B	−0.82 (14)
N1A—C8A—C9A—C10A	−178.81 (9)	N1B—C8B—C9B—C10B	−179.13 (9)
C8A—C9A—C10A—C11A	1.32 (15)	C8B—C9B—C10B—C11B	0.19 (15)
C9A—C10A—C11A—C12A	0.24 (16)	C9B—C10B—C11B—C12B	0.24 (16)
C10A—C11A—C12A—C13A	−1.07 (17)	C10B—C11B—C12B—C13B	−0.02 (16)
C11A—C12A—C13A—C8A	0.35 (16)	C11B—C12B—C13B—C8B	−0.63 (15)
C9A—C8A—C13A—C12A	1.21 (15)	C9B—C8B—C13B—C12B	1.04 (14)
N1A—C8A—C13A—C12A	177.84 (9)	N1B—C8B—C13B—C12B	179.24 (9)

(2_rt) N-(4-chlorobenzylidene)-4-methylaniline top

Crystal data top

C₁₄H₁₂ClN	D_x = 1.275 Mg m⁻³
M_r = 229.70	Melting point: 121.1 C K
Monoclinic, P2₁/a	Mo Kα radiation, λ = 0.71073 Å
a = 5.9663 (5) Å	Cell parameters from 3013 reflections
b = 7.3989 (7) Å	θ = 2.8–30.0°
c = 13.7221 (12) Å	µ = 0.29 mm⁻¹
β = 99.120 (2)°	T = 300 K
V = 598.09 (9) Å³	Block, colourless
Z = 2	0.48 × 0.34 × 0.18 mm
F(000) = 240

Data collection top

Bruker SMART 1000 CCD diffractometer	1760 independent reflections
Radiation source: fine-focus sealed tube	1271 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 8.192 pixels mm^-1	θ_max = 30.0°, θ_min = 1.5°
ω scan	h = −8→8
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −10→10
T_min = 0.874, T_max = 0.950	l = −19→19
8950 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.060	w = 1/[σ²(F_o²) + (0.0841P)² + 0.1347P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.195	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.24 e Å⁻³
1760 reflections	Δρ_min = −0.36 e Å⁻³
72 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.101 (16)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₄H₁₂ClN	V = 598.09 (9) Å³
M_r = 229.70	Z = 2
Monoclinic, P2₁/a	Mo Kα radiation
a = 5.9663 (5) Å	µ = 0.29 mm⁻¹
b = 7.3989 (7) Å	T = 300 K
c = 13.7221 (12) Å	0.48 × 0.34 × 0.18 mm
β = 99.120 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	1760 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	1271 reflections with I > 2σ(I)
T_min = 0.874, T_max = 0.950	R_int = 0.019
8950 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.195	H-atom parameters constrained
S = 1.08	Δρ_max = 0.24 e Å⁻³
1760 reflections	Δρ_min = −0.36 e Å⁻³
72 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.5336 (4)	1.0437 (3)	0.03796 (15)	0.0532 (5)	0.36
C1A	0.4313 (3)	1.0215 (2)	0.12730 (10)	0.0480 (5)	0.36
C2A	0.5525 (2)	1.0861 (3)	0.21527 (13)	0.0565 (6)	0.36
H2A	0.6910	1.1439	0.2154	0.068*	0.72
C3A	0.4668 (3)	1.0643 (4)	0.30300 (11)	0.0640 (7)	0.36
H3A	0.5478	1.1076	0.3619	0.077*	0.72
C4A	0.2598 (4)	0.9779 (4)	0.30275 (11)	0.0562 (6)	0.36
C5A	0.1386 (3)	0.9133 (3)	0.21477 (14)	0.0559 (6)	0.36
H5A	0.0001	0.8555	0.2146	0.067*	0.72
C6A	0.2244 (3)	0.9351 (3)	0.12705 (11)	0.0531 (6)	0.36
H6A	0.1433	0.8918	0.0682	0.064*	0.72
C8A	0.1654 (6)	0.9540 (6)	0.39931 (15)	0.0890 (5)	0.36
H81A	0.2049	1.0571	0.4409	0.134*	0.36
H82A	0.2289	0.8470	0.4324	0.134*	0.36
H83A	0.0032	0.9427	0.3852	0.134*	0.36
N1B	0.4047 (9)	0.9899 (7)	0.0123 (4)	0.0508 (7)*	0.14
C1B	0.3647 (8)	0.9940 (7)	0.1135 (3)	0.0508 (7)*	0.14
C2B	0.5282 (7)	1.0591 (8)	0.1888 (4)	0.0508 (7)*	0.14
H2B	0.6639	1.1055	0.1742	0.061*	0.28
C3B	0.4889 (8)	1.0546 (9)	0.2859 (3)	0.0508 (7)*	0.14
H3B	0.5983	1.0982	0.3364	0.061*	0.28
C4B	0.2861 (9)	0.9852 (9)	0.3077 (3)	0.0508 (7)*	0.14
C5B	0.1226 (8)	0.9202 (10)	0.2324 (4)	0.0508 (7)*	0.14
H5B	−0.0131	0.8737	0.2470	0.061*	0.28
C6B	0.1619 (8)	0.9246 (9)	0.1353 (4)	0.0508 (7)*	0.14
H6B	0.0525	0.8811	0.0848	0.061*	0.28
C8B	0.2428 (15)	0.9803 (15)	0.4147 (4)	0.0508 (7)*	0.14
H81B	0.3853	0.9780	0.4584	0.076*	0.14
H82B	0.1571	0.8741	0.4248	0.076*	0.14
H83B	0.1590	1.0859	0.4278	0.076*	0.14
C1C	0.4313 (3)	1.0215 (2)	0.12730 (10)	0.0480 (5)	0.36
C2C	0.5525 (2)	1.0861 (3)	0.21527 (13)	0.0565 (6)	0.36
C3C	0.4668 (3)	1.0643 (4)	0.30300 (11)	0.0640 (7)	0.36
C4C	0.2598 (4)	0.9779 (4)	0.30275 (11)	0.0562 (6)	0.36
Cl1C	0.2 (3)	1.0 (3)	0.413 (9)	0.0890 (5)	0.36
C5C	0.1386 (3)	0.9133 (3)	0.21477 (14)	0.0559 (6)	0.36
C6C	0.2244 (3)	0.9351 (3)	0.12705 (11)	0.0531 (6)	0.36
C7C	0.5336 (4)	1.0437 (3)	0.03796 (15)	0.0532 (5)	0.36
H7C	0.6520	1.1255	0.0382	0.064*	0.36
C1D	0.3647 (8)	0.9940 (7)	0.1135 (3)	0.0508 (7)*	0.14
C2D	0.5282 (7)	1.0591 (8)	0.1888 (4)	0.0508 (7)*	0.14
C3D	0.4889 (8)	1.0546 (9)	0.2859 (3)	0.0508 (7)*	0.14
C4D	0.2861 (9)	0.9852 (9)	0.3077 (3)	0.0508 (7)*	0.14
Cl1D	0.2 (3)	1.0 (3)	0.429 (9)	0.1184 (16)*	0.14
C5D	0.1226 (8)	0.9202 (10)	0.2324 (4)	0.0508 (7)*	0.14
C6D	0.1619 (8)	0.9246 (9)	0.1353 (4)	0.0508 (7)*	0.14
C7D	0.4047 (9)	0.9899 (7)	0.0123 (4)	0.0508 (7)*	0.14
H7D	0.2811	0.9711	−0.0371	0.061*	0.14

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0564 (10)	0.0502 (10)	0.0549 (10)	−0.0069 (8)	0.0151 (8)	−0.0024 (8)
C1A	0.0504 (11)	0.0414 (10)	0.0549 (12)	0.0023 (8)	0.0165 (9)	0.0012 (8)
C2A	0.0510 (11)	0.0577 (13)	0.0620 (14)	−0.0083 (9)	0.0125 (10)	−0.0087 (11)
C3A	0.0595 (13)	0.0754 (16)	0.0568 (14)	−0.0032 (11)	0.0086 (10)	−0.0118 (12)
C4A	0.0590 (13)	0.0595 (13)	0.0533 (12)	0.0048 (10)	0.0196 (10)	−0.0008 (9)
C5A	0.0496 (11)	0.0563 (12)	0.0645 (16)	−0.0050 (9)	0.0175 (9)	−0.0041 (11)
C6A	0.0503 (11)	0.0564 (12)	0.0529 (11)	−0.0051 (10)	0.0093 (9)	−0.0051 (9)
C8A	0.1002 (10)	0.1199 (12)	0.0546 (6)	−0.0065 (9)	0.0360 (6)	−0.0017 (6)
C1C	0.0504 (11)	0.0414 (10)	0.0549 (12)	0.0023 (8)	0.0165 (9)	0.0012 (8)
C2C	0.0510 (11)	0.0577 (13)	0.0620 (14)	−0.0083 (9)	0.0125 (10)	−0.0087 (11)
C3C	0.0595 (13)	0.0754 (16)	0.0568 (14)	−0.0032 (11)	0.0086 (10)	−0.0118 (12)
C4C	0.0590 (13)	0.0595 (13)	0.0533 (12)	0.0048 (10)	0.0196 (10)	−0.0008 (9)
Cl1C	0.1002 (10)	0.1199 (12)	0.0546 (6)	−0.0065 (9)	0.0360 (6)	−0.0017 (6)
C5C	0.0496 (11)	0.0563 (12)	0.0645 (16)	−0.0050 (9)	0.0175 (9)	−0.0041 (11)
C6C	0.0503 (11)	0.0564 (12)	0.0529 (11)	−0.0051 (10)	0.0093 (9)	−0.0051 (9)
C7C	0.0564 (10)	0.0502 (10)	0.0549 (10)	−0.0069 (8)	0.0151 (8)	−0.0024 (8)

Geometric parameters (Å, º) top

N1A—N1Aⁱ	1.238 (4)	N1B—N1Bⁱ	1.246 (11)
N1A—C1A	1.463 (2)	N1B—C1B	1.445 (7)
C1A—C2A	1.3900	C1B—C2B	1.3900
C1A—C6A	1.3900	C1B—C6B	1.3900
C2A—C3A	1.3900	C2B—C3B	1.3900
C3A—C4A	1.3900	C3B—C4B	1.3900
C4A—C5A	1.3900	C4B—C5B	1.3900
C4A—C8A	1.5300	C4B—C8B	1.5300
C5A—C6A	1.3900	C5B—C6B	1.3900

N1Aⁱ—N1A—C1A	121.6 (2)	N1Bⁱ—N1B—C1B	123.7 (7)
C2A—C1A—C6A	120.0	C2B—C1B—C6B	120.0
C2A—C1A—N1A	117.43 (14)	C2B—C1B—N1B	121.2 (4)
C6A—C1A—N1A	122.55 (14)	C6B—C1B—N1B	118.7 (4)
C1A—C2A—C3A	120.0	C3B—C2B—C1B	120.0
C4A—C3A—C2A	120.0	C2B—C3B—C4B	120.0
C3A—C4A—C5A	120.0	C3B—C4B—C5B	120.0
C3A—C4A—C8A	120.0	C3B—C4B—C8B	120.0
C5A—C4A—C8A	120.0	C5B—C4B—C8B	120.0
C6A—C5A—C4A	120.0	C6B—C5B—C4B	120.0
C5A—C6A—C1A	120.0	C5B—C6B—C1B	120.0

N1Aⁱ—N1A—C1A—C2A	163.3 (3)	N1Bⁱ—N1B—C1B—C2B	14.0 (9)
N1Aⁱ—N1A—C1A—C6A	−14.9 (3)	N1Bⁱ—N1B—C1B—C6B	−163.4 (7)
C6A—C1A—C2A—C3A	0.0	C6B—C1B—C2B—C3B	0.0
N1A—C1A—C2A—C3A	−178.23 (17)	N1B—C1B—C2B—C3B	−177.4 (5)
C1A—C2A—C3A—C4A	0.0	C1B—C2B—C3B—C4B	0.0
C2A—C3A—C4A—C5A	0.0	C2B—C3B—C4B—C5B	0.0
C2A—C3A—C4A—C8A	180.0	C2B—C3B—C4B—C8B	180.0
C3A—C4A—C5A—C6A	0.0	C3B—C4B—C5B—C6B	0.0
C8A—C4A—C5A—C6A	180.0	C8B—C4B—C5B—C6B	180.0
C4A—C5A—C6A—C1A	0.0	C4B—C5B—C6B—C1B	0.0
C2A—C1A—C6A—C5A	0.0	C2B—C1B—C6B—C5B	0.0
N1A—C1A—C6A—C5A	178.14 (18)	N1B—C1B—C6B—C5B	177.4 (5)

Symmetry code: (i) −x+1, −y+2, −z.

(2_200K) N-(4-chlorobenzylidene)-4-methylaniline top

Crystal data top

C₁₄H₁₂ClN	D_x = 1.308 Mg m⁻³
M_r = 229.70	Melting point: 121.1 C K
Monoclinic, P2₁/a	Mo Kα radiation, λ = 0.71073 Å
a = 5.9174 (5) Å	Cell parameters from 5419 reflections
b = 7.2879 (6) Å	θ = 2.8–30.0°
c = 13.70490 (11) Å	µ = 0.30 mm⁻¹
β = 99.233 (2)°	T = 200 K
V = 583.37 (7) Å³	Block, colourless
Z = 2	0.48 × 0.34 × 0.18 mm
F(000) = 240

Data collection top

Bruker SMART 1000 CCD diffractometer	1707 independent reflections
Radiation source: fine-focus sealed tube	1454 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
Detector resolution: 8.192 pixels mm^-1	θ_max = 30.0°, θ_min = 1.5°
ω scan	h = −8→8
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −10→10
T_min = 0.871, T_max = 0.949	l = −19→19
8648 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.053	w = 1/[σ²(F_o²) + (0.0574P)² + 0.1885P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.148	(Δ/σ)_max < 0.001
S = 1.12	Δρ_max = 0.29 e Å⁻³
1707 reflections	Δρ_min = −0.37 e Å⁻³
72 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.083 (10)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₄H₁₂ClN	V = 583.37 (7) Å³
M_r = 229.70	Z = 2
Monoclinic, P2₁/a	Mo Kα radiation
a = 5.9174 (5) Å	µ = 0.30 mm⁻¹
b = 7.2879 (6) Å	T = 200 K
c = 13.70490 (11) Å	0.48 × 0.34 × 0.18 mm
β = 99.233 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	1707 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	1454 reflections with I > 2σ(I)
T_min = 0.871, T_max = 0.949	R_int = 0.016
8648 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.12	Δρ_max = 0.29 e Å⁻³
1707 reflections	Δρ_min = −0.37 e Å⁻³
72 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.5347 (3)	1.0453 (2)	0.03837 (11)	0.0362 (3)	0.39
C1A	0.4331 (2)	1.02233 (17)	0.12787 (7)	0.0324 (3)	0.39
C2A	0.55805 (17)	1.0857 (2)	0.21599 (10)	0.0376 (4)	0.39
H2A	0.7013	1.1445	0.2160	0.045*	0.78
C3A	0.4734 (2)	1.0631 (2)	0.30414 (7)	0.0418 (4)	0.39
H3A	0.5588	1.1064	0.3644	0.050*	0.78
C4A	0.2637 (2)	0.9771 (2)	0.30418 (7)	0.0368 (4)	0.39
C5A	0.13876 (18)	0.9137 (2)	0.21606 (9)	0.0361 (4)	0.39
H5A	−0.0045	0.8549	0.2161	0.043*	0.78
C6A	0.2234 (2)	0.9363 (2)	0.12790 (7)	0.0355 (4)	0.39
H6A	0.1380	0.8930	0.0677	0.043*	0.78
C8A	0.1705 (4)	0.9521 (4)	0.40121 (10)	0.0588 (3)	0.39
H81A	0.2224	1.0540	0.4459	0.088*	0.39
H82A	0.2266	0.8360	0.4321	0.088*	0.39
H83A	0.0028	0.9505	0.3878	0.088*	0.39
N1B	0.4017 (9)	0.9920 (7)	0.0120 (4)	0.0343 (7)*	0.11
C1B	0.3625 (8)	0.9940 (7)	0.1140 (3)	0.0343 (7)*	0.11
C2B	0.5315 (7)	1.0580 (8)	0.1885 (4)	0.0343 (7)*	0.11
H2B	0.6707	1.1052	0.1725	0.041*	0.22
C3B	0.4969 (8)	1.0529 (9)	0.2864 (3)	0.0343 (7)*	0.11
H3B	0.6124	1.0967	0.3373	0.041*	0.22
C4B	0.2933 (9)	0.9839 (9)	0.3099 (3)	0.0343 (7)*	0.11
C5B	0.1243 (7)	0.9199 (9)	0.2354 (4)	0.0343 (7)*	0.11
H5B	−0.0149	0.8727	0.2514	0.041*	0.22
C6B	0.1589 (7)	0.9249 (8)	0.1375 (3)	0.0343 (7)*	0.11
H6B	0.0434	0.8812	0.0865	0.041*	0.22
C8B	0.2552 (14)	0.9783 (14)	0.4176 (3)	0.0343 (7)*	0.11
H81B	0.4033	0.9689	0.4611	0.051*	0.11
H82B	0.1607	0.8717	0.4277	0.051*	0.11
H83B	0.1772	1.0908	0.4330	0.051*	0.11
C1C	0.4331 (2)	1.02233 (17)	0.12787 (7)	0.0324 (3)	0.39
C2C	0.55805 (17)	1.0857 (2)	0.21599 (10)	0.0376 (4)	0.39
C3C	0.4734 (2)	1.0631 (2)	0.30414 (7)	0.0418 (4)	0.39
C4C	0.2637 (2)	0.9771 (2)	0.30418 (7)	0.0368 (4)	0.39
Cl1C	0.2 (5)	0.9 (5)	0.415 (9)	0.0588 (3)	0.39
C5C	0.13876 (18)	0.9137 (2)	0.21606 (9)	0.0361 (4)	0.39
C6C	0.2234 (2)	0.9363 (2)	0.12790 (7)	0.0355 (4)	0.39
C7C	0.5347 (3)	1.0453 (2)	0.03837 (11)	0.0362 (3)	0.39
H7C	0.6560	1.1306	0.0383	0.043*	0.39
C1D	0.3625 (8)	0.9940 (7)	0.1140 (3)	0.0343 (7)*	0.11
C2D	0.5315 (7)	1.0580 (8)	0.1885 (4)	0.0343 (7)*	0.11
C3D	0.4969 (8)	1.0529 (9)	0.2864 (3)	0.0343 (7)*	0.11
C4D	0.2933 (9)	0.9839 (9)	0.3099 (3)	0.0343 (7)*	0.11
Cl1D	0.2 (5)	1.0 (5)	0.432 (9)	0.0984 (10)*	0.11
C5D	0.1243 (7)	0.9199 (9)	0.2354 (4)	0.0343 (7)*	0.11
C6D	0.1589 (7)	0.9249 (8)	0.1375 (3)	0.0343 (7)*	0.11
C7D	0.4017 (9)	0.9920 (7)	0.0120 (4)	0.0343 (7)*	0.11
H7D	0.2737	0.9781	−0.0390	0.041*	0.11

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0392 (7)	0.0339 (7)	0.0374 (7)	−0.0047 (6)	0.0123 (6)	−0.0019 (6)
C1A	0.0339 (8)	0.0282 (7)	0.0373 (8)	0.0005 (6)	0.0121 (6)	−0.0004 (6)
C2A	0.0329 (7)	0.0378 (9)	0.0429 (9)	−0.0051 (6)	0.0081 (6)	−0.0055 (7)
C3A	0.0392 (9)	0.0491 (10)	0.0371 (9)	−0.0024 (7)	0.0061 (7)	−0.0071 (7)
C4A	0.0376 (9)	0.0400 (8)	0.0350 (8)	0.0015 (7)	0.0125 (6)	−0.0016 (6)
C5A	0.0328 (7)	0.0383 (8)	0.0391 (9)	−0.0035 (6)	0.0113 (6)	−0.0040 (7)
C6A	0.0349 (8)	0.0378 (8)	0.0348 (8)	−0.0047 (7)	0.0086 (6)	−0.0041 (6)
C8A	0.0701 (6)	0.0766 (6)	0.0346 (4)	−0.0019 (5)	0.0234 (4)	−0.0010 (4)
C1C	0.0339 (8)	0.0282 (7)	0.0373 (8)	0.0005 (6)	0.0121 (6)	−0.0004 (6)
C2C	0.0329 (7)	0.0378 (9)	0.0429 (9)	−0.0051 (6)	0.0081 (6)	−0.0055 (7)
C3C	0.0392 (9)	0.0491 (10)	0.0371 (9)	−0.0024 (7)	0.0061 (7)	−0.0071 (7)
C4C	0.0376 (9)	0.0400 (8)	0.0350 (8)	0.0015 (7)	0.0125 (6)	−0.0016 (6)
Cl1C	0.0701 (6)	0.0766 (6)	0.0346 (4)	−0.0019 (5)	0.0234 (4)	−0.0010 (4)
C5C	0.0328 (7)	0.0383 (8)	0.0391 (9)	−0.0035 (6)	0.0113 (6)	−0.0040 (7)
C6C	0.0349 (8)	0.0378 (8)	0.0348 (8)	−0.0047 (7)	0.0086 (6)	−0.0041 (6)
C7C	0.0392 (7)	0.0339 (7)	0.0374 (7)	−0.0047 (6)	0.0123 (6)	−0.0019 (6)

Geometric parameters (Å, º) top

N1A—N1Aⁱ	1.253 (3)	N1B—N1Bⁱ	1.264 (10)
N1A—C1A	1.4597 (16)	N1B—C1B	1.454 (7)
C1A—C2A	1.3900	C1B—C2B	1.3900
C1A—C6A	1.3900	C1B—C6B	1.3900
C2A—C3A	1.3900	C2B—C3B	1.3900
C3A—C4A	1.3900	C3B—C4B	1.3900
C4A—C5A	1.3900	C4B—C5B	1.3900
C4A—C8A	1.5300	C4B—C8B	1.5300
C5A—C6A	1.3900	C5B—C6B	1.3900

N1Aⁱ—N1A—C1A	121.42 (17)	N1Bⁱ—N1B—C1B	123.0 (7)
C2A—C1A—C6A	120.0	C2B—C1B—C6B	120.0
C2A—C1A—N1A	117.30 (10)	C2B—C1B—N1B	120.2 (4)
C6A—C1A—N1A	122.67 (10)	C6B—C1B—N1B	119.8 (4)
C1A—C2A—C3A	120.0	C1B—C2B—C3B	120.0
C2A—C3A—C4A	120.0	C4B—C3B—C2B	120.0
C3A—C4A—C5A	120.0	C3B—C4B—C5B	120.0
C3A—C4A—C8A	120.0	C3B—C4B—C8B	120.0
C5A—C4A—C8A	120.0	C5B—C4B—C8B	120.0
C6A—C5A—C4A	120.0	C6B—C5B—C4B	120.0
C5A—C6A—C1A	120.0	C5B—C6B—C1B	120.0

N1Aⁱ—N1A—C1A—C2A	162.12 (18)	N1Bⁱ—N1B—C1B—C2B	15.8 (9)
N1Aⁱ—N1A—C1A—C6A	−16.0 (3)	N1Bⁱ—N1B—C1B—C6B	−161.7 (7)
C6A—C1A—C2A—C3A	0.0	C6B—C1B—C2B—C3B	0.0
N1A—C1A—C2A—C3A	−178.16 (12)	N1B—C1B—C2B—C3B	−177.5 (4)
C1A—C2A—C3A—C4A	0.0	C1B—C2B—C3B—C4B	0.0
C2A—C3A—C4A—C5A	0.0	C2B—C3B—C4B—C5B	0.0
C2A—C3A—C4A—C8A	180.0	C2B—C3B—C4B—C8B	180.0
C3A—C4A—C5A—C6A	0.0	C3B—C4B—C5B—C6B	0.0
C8A—C4A—C5A—C6A	180.0	C8B—C4B—C5B—C6B	180.0
C4A—C5A—C6A—C1A	0.0	C4B—C5B—C6B—C1B	0.0
C2A—C1A—C6A—C5A	0.0	C2B—C1B—C6B—C5B	0.0
N1A—C1A—C6A—C5A	178.06 (13)	N1B—C1B—C6B—C5B	177.5 (4)

Symmetry code: (i) −x+1, −y+2, −z.

(2_90K) N-(4-chlorobenzylidene)-4-methylaniline top

Crystal data top

C₁₄H₁₂ClN	D_x = 1.334 Mg m⁻³
M_r = 229.70	Melting point: 121.1 C K
Monoclinic, P2₁/a	Mo Kα radiation, λ = 0.71073 Å
a = 5.8827 (6) Å	Cell parameters from 5419 reflections
b = 7.1953 (7) Å	θ = 2.8–30.0°
c = 13.6919 (14) Å	µ = 0.30 mm⁻¹
β = 99.385 (2)°	T = 90 K
V = 571.79 (10) Å³	Block, colourless
Z = 2	0.48 × 0.34 × 0.18 mm
F(000) = 240

Data collection top

Bruker SMART 1000 CCD diffractometer	1668 independent reflections
Radiation source: fine-focus sealed tube	1536 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
Detector resolution: 8.192 pixels mm^-1	θ_max = 30.0°, θ_min = 1.5°
ω scan	h = −8→8
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −10→10
T_min = 0.868, T_max = 0.948	l = −19→19
8393 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.059	w = 1/[σ²(F_o²) + (0.0866P)² + 1.6982P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.141	(Δ/σ)_max < 0.001
S = 0.60	Δρ_max = 0.68 e Å⁻³
1668 reflections	Δρ_min = −0.65 e Å⁻³
72 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.106 (10)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₄H₁₂ClN	V = 571.79 (10) Å³
M_r = 229.70	Z = 2
Monoclinic, P2₁/a	Mo Kα radiation
a = 5.8827 (6) Å	µ = 0.30 mm⁻¹
b = 7.1953 (7) Å	T = 90 K
c = 13.6919 (14) Å	0.48 × 0.34 × 0.18 mm
β = 99.385 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	1668 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	1536 reflections with I > 2σ(I)
T_min = 0.868, T_max = 0.948	R_int = 0.017
8393 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 0.60	Δρ_max = 0.68 e Å⁻³
1668 reflections	Δρ_min = −0.65 e Å⁻³
72 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.5356 (3)	1.0467 (2)	0.03858 (11)	0.0210 (3)	0.41
C1A	0.4344 (2)	1.02318 (17)	0.12856 (7)	0.0192 (3)	0.41
C2A	0.56208 (16)	1.08579 (19)	0.21685 (10)	0.0220 (4)	0.41
H2A	0.7066	1.1446	0.2168	0.026*	0.82
C3A	0.4782 (2)	1.0624 (2)	0.30526 (7)	0.0239 (4)	0.41
H3A	0.5654	1.1052	0.3656	0.029*	0.82
C4A	0.2667 (2)	0.9763 (2)	0.30539 (6)	0.0206 (4)	0.41
C5A	0.13905 (17)	0.9137 (2)	0.21710 (9)	0.0204 (4)	0.41
H5A	−0.0055	0.8549	0.2172	0.024*	0.82
C6A	0.2229 (2)	0.9371 (2)	0.12868 (6)	0.0209 (4)	0.41
H6A	0.1357	0.8944	0.0683	0.025*	0.82
C8A	0.1744 (4)	0.9506 (4)	0.40271 (9)	0.0325 (2)	0.41
H81A	0.2237	1.0553	0.4469	0.049*	0.41
H82A	0.2346	0.8345	0.4343	0.049*	0.41
H83A	0.0057	0.9455	0.3893	0.049*	0.41
N1B	0.4013 (11)	0.9932 (9)	0.0121 (5)	0.0179 (7)*	0.09
C1B	0.3632 (10)	0.9937 (9)	0.1145 (3)	0.0179 (7)*	0.09
C2B	0.5360 (8)	1.0578 (10)	0.1883 (4)	0.0179 (7)*	0.09
H2B	0.6752	1.1054	0.1715	0.022*	0.18
C3B	0.5051 (9)	1.0524 (10)	0.2868 (4)	0.0179 (7)*	0.09
H3B	0.6231	1.0963	0.3372	0.022*	0.18
C4B	0.3014 (10)	0.9829 (10)	0.3114 (3)	0.0179 (7)*	0.09
C5B	0.1286 (9)	0.9188 (11)	0.2376 (4)	0.0179 (7)*	0.09
H5B	−0.0106	0.8713	0.2545	0.022*	0.18
C6B	0.1595 (9)	0.9242 (10)	0.1392 (4)	0.0179 (7)*	0.09
H6B	0.0414	0.8804	0.0887	0.022*	0.18
C8B	0.2673 (17)	0.9770 (16)	0.4198 (4)	0.0179 (7)*	0.09
H81B	0.4002	0.9162	0.4596	0.027*	0.09
H82B	0.1270	0.9070	0.4253	0.027*	0.09
H83B	0.2530	1.1040	0.4440	0.027*	0.09
C1C	0.4344 (2)	1.02318 (17)	0.12856 (7)	0.0192 (3)	0.41
C2C	0.56208 (16)	1.08579 (19)	0.21685 (10)	0.0220 (4)	0.41
C3C	0.4782 (2)	1.0624 (2)	0.30526 (7)	0.0239 (4)	0.41
C4C	0.2667 (2)	0.9763 (2)	0.30539 (6)	0.0206 (4)	0.41
Cl1C	0.16 (3)	0.95 (3)	0.416 (13)	0.0325 (2)	0.41
C5C	0.13905 (17)	0.9137 (2)	0.21710 (9)	0.0204 (4)	0.41
C6C	0.2229 (2)	0.9371 (2)	0.12868 (6)	0.0209 (4)	0.41
C7C	0.5356 (3)	1.0467 (2)	0.03858 (11)	0.0210 (3)	0.41
H7C	0.6569	1.1337	0.0381	0.025*	0.41
C1D	0.3632 (10)	0.9937 (9)	0.1145 (3)	0.0179 (7)*	0.09
C2D	0.5360 (8)	1.0578 (10)	0.1883 (4)	0.0179 (7)*	0.09
C3D	0.5051 (9)	1.0524 (10)	0.2868 (4)	0.0179 (7)*	0.09
C4D	0.3014 (10)	0.9829 (10)	0.3114 (3)	0.0179 (7)*	0.09
Cl1D	0.26 (3)	0.98 (3)	0.435 (13)	0.0560 (10)*	0.09
C5D	0.1286 (9)	0.9188 (11)	0.2376 (4)	0.0179 (7)*	0.09
C6D	0.1595 (9)	0.9242 (10)	0.1392 (4)	0.0179 (7)*	0.09
C7D	0.4013 (11)	0.9932 (9)	0.0121 (5)	0.0179 (7)*	0.09
H7D	0.2716	0.9821	−0.0389	0.022*	0.09

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0221 (7)	0.0201 (7)	0.0221 (7)	−0.0029 (5)	0.0079 (5)	−0.0010 (5)
C1A	0.0189 (7)	0.0168 (7)	0.0234 (8)	−0.0005 (6)	0.0082 (6)	−0.0007 (6)
C2A	0.0178 (7)	0.0221 (8)	0.0264 (9)	−0.0031 (6)	0.0049 (6)	−0.0036 (7)
C3A	0.0221 (8)	0.0290 (9)	0.0206 (8)	−0.0022 (7)	0.0036 (6)	−0.0039 (7)
C4A	0.0201 (8)	0.0244 (8)	0.0187 (7)	−0.0009 (6)	0.0067 (6)	−0.0021 (6)
C5A	0.0183 (7)	0.0235 (8)	0.0199 (8)	−0.0021 (6)	0.0052 (6)	−0.0034 (7)
C6A	0.0215 (8)	0.0228 (8)	0.0193 (7)	−0.0040 (7)	0.0061 (6)	−0.0032 (6)
C8A	0.0413 (5)	0.0412 (5)	0.0172 (4)	−0.0008 (3)	0.0111 (3)	−0.0015 (3)
C1C	0.0189 (7)	0.0168 (7)	0.0234 (8)	−0.0005 (6)	0.0082 (6)	−0.0007 (6)
C2C	0.0178 (7)	0.0221 (8)	0.0264 (9)	−0.0031 (6)	0.0049 (6)	−0.0036 (7)
C3C	0.0221 (8)	0.0290 (9)	0.0206 (8)	−0.0022 (7)	0.0036 (6)	−0.0039 (7)
C4C	0.0201 (8)	0.0244 (8)	0.0187 (7)	−0.0009 (6)	0.0067 (6)	−0.0021 (6)
Cl1C	0.0413 (5)	0.0412 (5)	0.0172 (4)	−0.0008 (3)	0.0111 (3)	−0.0015 (3)
C5C	0.0183 (7)	0.0235 (8)	0.0199 (8)	−0.0021 (6)	0.0052 (6)	−0.0034 (7)
C6C	0.0215 (8)	0.0228 (8)	0.0193 (7)	−0.0040 (7)	0.0061 (6)	−0.0032 (6)
C7C	0.0221 (7)	0.0201 (7)	0.0221 (7)	−0.0029 (5)	0.0079 (5)	−0.0010 (5)

Geometric parameters (Å, º) top

N1A—N1Aⁱ	1.265 (3)	N1B—N1Bⁱ	1.262 (13)
N1A—C1A	1.4628 (16)	N1B—C1B	1.456 (8)
C1A—C2A	1.3900	C1B—C2B	1.3900
C1A—C6A	1.3900	C1B—C6B	1.3900
C2A—C3A	1.3900	C2B—C3B	1.3900
C3A—C4A	1.3900	C3B—C4B	1.3900
C4A—C5A	1.3900	C4B—C5B	1.3900
C4A—C8A	1.5300	C4B—C8B	1.5300
C5A—C6A	1.3900	C5B—C6B	1.3900

N1Aⁱ—N1A—C1A	121.13 (18)	N1Bⁱ—N1B—C1B	123.1 (8)
C2A—C1A—C6A	120.0	C2B—C1B—C6B	120.0
C2A—C1A—N1A	117.30 (10)	C2B—C1B—N1B	119.5 (4)
C6A—C1A—N1A	122.68 (10)	C6B—C1B—N1B	120.5 (4)
C3A—C2A—C1A	120.0	C1B—C2B—C3B	120.0
C2A—C3A—C4A	120.0	C4B—C3B—C2B	120.0
C5A—C4A—C3A	120.0	C3B—C4B—C5B	120.0
C5A—C4A—C8A	120.0	C3B—C4B—C8B	120.0
C3A—C4A—C8A	120.0	C5B—C4B—C8B	120.0
C4A—C5A—C6A	120.0	C6B—C5B—C4B	120.0
C5A—C6A—C1A	120.0	C5B—C6B—C1B	120.0

N1Aⁱ—N1A—C1A—C2A	161.21 (18)	N1Bⁱ—N1B—C1B—C2B	16.9 (11)
N1Aⁱ—N1A—C1A—C6A	−16.8 (3)	N1Bⁱ—N1B—C1B—C6B	−160.6 (8)
C6A—C1A—C2A—C3A	0.0	C6B—C1B—C2B—C3B	0.0
N1A—C1A—C2A—C3A	−178.11 (12)	N1B—C1B—C2B—C3B	−177.6 (5)
C1A—C2A—C3A—C4A	0.0	C1B—C2B—C3B—C4B	0.0
C2A—C3A—C4A—C5A	0.0	C2B—C3B—C4B—C5B	0.0
C2A—C3A—C4A—C8A	180.0	C2B—C3B—C4B—C8B	180.0
C3A—C4A—C5A—C6A	0.0	C3B—C4B—C5B—C6B	0.0
C8A—C4A—C5A—C6A	180.0	C8B—C4B—C5B—C6B	180.0
C4A—C5A—C6A—C1A	0.0	C4B—C5B—C6B—C1B	0.0
C2A—C1A—C6A—C5A	0.0	C2B—C1B—C6B—C5B	0.0
N1A—C1A—C6A—C5A	178.01 (12)	N1B—C1B—C6B—C5B	177.5 (5)

Symmetry code: (i) −x+1, −y+2, −z.

(3_300K) N-(4-methylbenzylidene)-4-methylaniline top

Crystal data top

C₁₅H₁₅N	D_x = 1.199 Mg m⁻³
M_r = 209.28	Melting point: 89.4 C K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.8766 (7) Å	Cell parameters from 2827 reflections
b = 4.8839 (4) Å	θ = 3.4–29.9°
c = 12.0187 (9) Å	µ = 0.07 mm⁻¹
β = 90.499 (1)°	T = 300 K
V = 579.72 (8) Å³	Plate, colourless
Z = 2	0.40 × 0.30 × 0.08 mm
F(000) = 224

Data collection top

Bruker SMART 1000 CCD diffractometer	1689 independent reflections
Radiation source: fine-focus sealed tube	1330 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 8.192 pixels mm^-1	θ_max = 30.0°, θ_min = 2.1°
ω scan	h = −13→13
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −6→6
T_min = 0.973, T_max = 0.995	l = −16→16
8496 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.052	w = 1/[σ²(F_o²) + (0.061P)² + 0.122P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.149	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.23 e Å⁻³
1689 reflections	Δρ_min = −0.20 e Å⁻³
89 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.206 (18)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₁₅N	V = 579.72 (8) Å³
M_r = 209.28	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8766 (7) Å	µ = 0.07 mm⁻¹
b = 4.8839 (4) Å	T = 300 K
c = 12.0187 (9) Å	0.40 × 0.30 × 0.08 mm
β = 90.499 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	1689 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	1330 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.995	R_int = 0.022
8496 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.05	Δρ_max = 0.23 e Å⁻³
1689 reflections	Δρ_min = −0.20 e Å⁻³
89 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.45639 (18)	−0.4322 (4)	0.52732 (17)	0.0483 (4)	0.29
C1A	0.36908 (18)	−0.2313 (4)	0.47541 (18)	0.0382 (4)	0.59
C2A	0.2710 (2)	−0.1098 (5)	0.54164 (18)	0.0474 (5)	0.59
H2A	0.2650	−0.1578	0.6163	0.057*	0.59
C3A	0.1822 (3)	0.0826 (6)	0.4972 (3)	0.0512 (6)	0.59
H3A	0.1172	0.1601	0.5430	0.061*	0.59
C4A	0.1873 (3)	0.1624 (6)	0.3872 (3)	0.0398 (5)	0.59
C5A	0.2872 (3)	0.0448 (7)	0.3233 (2)	0.0515 (6)	0.59
H5A	0.2947	0.0972	0.2492	0.062*	0.59
C6A	0.3772 (2)	−0.1495 (5)	0.36584 (19)	0.0485 (5)	0.59
H6A	0.4430	−0.2243	0.3201	0.058*	0.59
C7A	0.45639 (18)	−0.4322 (4)	0.52732 (17)	0.0483 (4)	0.29
H7A	0.4487	−0.4635	0.6033	0.058*	0.29
C8A	0.0876 (7)	0.3734 (14)	0.3467 (5)	0.0648 (8)	0.59
H81A	0.1298	0.5505	0.3470	0.097*	0.59
H82A	0.0105	0.3757	0.3948	0.097*	0.59
H83A	0.0588	0.3288	0.2724	0.097*	0.59
N1B	0.4948 (3)	−0.4416 (6)	0.4528 (2)	0.0455 (4)*	0.21
C1B	0.3901 (3)	−0.2364 (5)	0.4345 (2)	0.0455 (4)*	0.41
C2B	0.3008 (3)	−0.1499 (6)	0.51603 (19)	0.0455 (4)*	0.41
H2B	0.3064	−0.2232	0.5873	0.055*	0.41
C3B	0.2032 (4)	0.0461 (8)	0.4910 (3)	0.0455 (4)*	0.41
H3B	0.1434	0.1040	0.5456	0.055*	0.41
C4B	0.1948 (4)	0.1557 (9)	0.3844 (3)	0.0455 (4)*	0.41
C5B	0.2841 (4)	0.0692 (9)	0.3029 (2)	0.0455 (4)*	0.41
H5B	0.2785	0.1425	0.2316	0.055*	0.41
C6B	0.3817 (3)	−0.1269 (7)	0.3279 (2)	0.0455 (4)*	0.41
H6B	0.4415	−0.1847	0.2733	0.055*	0.41
C7B	0.4948 (3)	−0.4416 (6)	0.4528 (2)	0.0455 (4)*	0.21
H7B	0.5537	−0.4872	0.3958	0.055*	0.21
C8B	0.0928 (9)	0.3659 (18)	0.3466 (5)	0.0455 (4)*	0.41
H81B	0.0044	0.2843	0.3439	0.068*	0.41
H82B	0.1163	0.4308	0.2739	0.068*	0.41
H83B	0.0926	0.5165	0.3979	0.068*	0.41

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0451 (9)	0.0379 (9)	0.0617 (11)	0.0076 (7)	−0.0100 (8)	0.0058 (8)
C1A	0.0315 (8)	0.0317 (8)	0.0512 (10)	0.0017 (6)	−0.0042 (7)	−0.0013 (8)
C2A	0.0463 (11)	0.0477 (11)	0.0481 (11)	0.0152 (8)	0.0016 (8)	0.0020 (9)
C3A	0.0456 (12)	0.0477 (13)	0.0604 (12)	0.0186 (9)	−0.0005 (9)	0.0007 (10)
C4A	0.0352 (9)	0.0251 (7)	0.0589 (11)	−0.0016 (6)	−0.0133 (7)	−0.0027 (7)
C5A	0.0590 (12)	0.0488 (12)	0.0465 (13)	0.0045 (10)	−0.0011 (10)	0.0075 (10)
C6A	0.0456 (10)	0.0513 (12)	0.0487 (12)	0.0115 (8)	0.0091 (9)	−0.0016 (10)
C7A	0.0451 (9)	0.0379 (9)	0.0617 (11)	0.0076 (7)	−0.0100 (8)	0.0058 (8)
C8A	0.0556 (15)	0.0377 (11)	0.101 (2)	0.0126 (10)	−0.0288 (12)	0.0023 (11)

Geometric parameters (Å, º) top

N1A—N1Aⁱ	1.274 (4)	N1B—N1Bⁱ	1.273 (5)
C1A—C6A	1.379 (3)	C1B—C2B	1.3900
C1A—C2A	1.392 (2)	C1B—C6B	1.3900
C2A—C3A	1.390 (3)	C2B—C3B	1.3900
C3A—C4A	1.379 (3)	C3B—C4B	1.3900
C4A—C5A	1.381 (3)	C4B—C5B	1.3900
C4A—C8A	1.503 (6)	C4B—C8B	1.506 (9)
C5A—C6A	1.394 (3)	C5B—C6B	1.3900

C6A—C1A—C2A	117.96 (16)	C2B—C1B—C6B	120.0
C3A—C2A—C1A	120.57 (18)	C1B—C2B—C3B	120.0
C4A—C3A—C2A	122.11 (19)	C4B—C3B—C2B	120.0
C3A—C4A—C5A	116.60 (17)	C5B—C4B—C3B	120.0
C3A—C4A—C8A	118.3 (3)	C5B—C4B—C8B	114.9 (3)
C5A—C4A—C8A	125.0 (3)	C3B—C4B—C8B	125.1 (3)
C4A—C5A—C6A	122.38 (19)	C4B—C5B—C6B	120.0
C1A—C6A—C5A	120.35 (18)	C5B—C6B—C1B	120.0

C6A—C1A—C2A—C3A	1.7 (3)	C6B—C1B—C2B—C3B	0.0
C1A—C2A—C3A—C4A	−0.4 (3)	C1B—C2B—C3B—C4B	0.0
C2A—C3A—C4A—C5A	−1.1 (3)	C2B—C3B—C4B—C5B	0.0
C2A—C3A—C4A—C8A	−179.6 (4)	C2B—C3B—C4B—C8B	179.2 (6)
C3A—C4A—C5A—C6A	1.4 (3)	C3B—C4B—C5B—C6B	0.0
C8A—C4A—C5A—C6A	179.7 (5)	C8B—C4B—C5B—C6B	−179.3 (6)
C2A—C1A—C6A—C5A	−1.4 (3)	C4B—C5B—C6B—C1B	0.0
C4A—C5A—C6A—C1A	−0.2 (3)	C2B—C1B—C6B—C5B	0.0

Symmetry code: (i) −x+1, −y−1, −z+1.

(3_250K) N-(4-methylbenzylidene)-4-methylaniline top

Crystal data top

C₁₅H₁₅N	D_x = 1.212 Mg m⁻³
M_r = 209.28	Melting point: 89.4 C K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.8649 (6) Å	Cell parameters from 3145 reflections
b = 4.8663 (3) Å	θ = 3.4–30.0°
c = 11.9484 (8) Å	µ = 0.07 mm⁻¹
β = 90.518 (1)°	T = 250 K
V = 573.57 (6) Å³	Plate, colourless
Z = 2	0.40 × 0.30 × 0.08 mm
F(000) = 224

Data collection top

Bruker SMART 1000 CCD diffractometer	1677 independent reflections
Radiation source: fine-focus sealed tube	1406 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 8.192 pixels mm^-1	θ_max = 30.0°, θ_min = 2.1°
ω scan	h = −13→13
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −6→6
T_min = 0.972, T_max = 0.994	l = −16→16
8404 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.048	w = 1/[σ²(F_o²) + (0.0552P)² + 0.1239P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.135	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.22 e Å⁻³
1677 reflections	Δρ_min = −0.20 e Å⁻³
89 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.126 (13)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₁₅N	V = 573.57 (6) Å³
M_r = 209.28	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8649 (6) Å	µ = 0.07 mm⁻¹
b = 4.8663 (3) Å	T = 250 K
c = 11.9484 (8) Å	0.40 × 0.30 × 0.08 mm
β = 90.518 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	1677 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	1406 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.994	R_int = 0.019
8404 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.08	Δρ_max = 0.22 e Å⁻³
1677 reflections	Δρ_min = −0.20 e Å⁻³
89 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.45641 (15)	0.5679 (3)	0.52789 (14)	0.0401 (4)	0.31
C1A	0.36895 (15)	0.7700 (3)	0.47611 (15)	0.0314 (3)	0.62
C2A	0.27063 (18)	0.8905 (4)	0.54288 (15)	0.0388 (4)	0.62
H2A	0.2645	0.8406	0.6187	0.047*	0.62
C3A	0.1811 (2)	1.0842 (5)	0.4987 (2)	0.0417 (4)	0.62
H3A	0.1152	1.1618	0.5454	0.050*	0.62
C4A	0.1866 (2)	1.1658 (5)	0.3877 (2)	0.0327 (4)	0.62
C5A	0.2873 (3)	1.0487 (5)	0.32294 (17)	0.0417 (4)	0.62
H5A	0.2951	1.1029	0.2478	0.050*	0.62
C6A	0.37730 (18)	0.8535 (4)	0.36552 (16)	0.0394 (4)	0.62
H6A	0.4440	0.7780	0.3190	0.047*	0.62
C7A	0.45641 (15)	0.5679 (3)	0.52789 (14)	0.0401 (4)	0.31
H7A	0.4489	0.5353	0.6051	0.048*	0.31
C8A	0.0874 (6)	1.3789 (12)	0.3461 (5)	0.0500 (6)	0.62
H81A	0.1290	1.5593	0.3501	0.075*	0.62
H82A	0.0071	1.3759	0.3923	0.075*	0.62
H83A	0.0623	1.3386	0.2691	0.075*	0.62
N1B	0.4945 (3)	0.5594 (6)	0.4527 (2)	0.0378 (4)*	0.19
C1B	0.3899 (2)	0.7656 (5)	0.4341 (2)	0.0378 (4)*	0.38
C2B	0.3005 (3)	0.8518 (6)	0.51626 (18)	0.0378 (4)*	0.38
H2B	0.3062	0.7770	0.5887	0.045*	0.38
C3B	0.2027 (3)	1.0487 (8)	0.4913 (3)	0.0378 (4)*	0.38
H3B	0.1423	1.1070	0.5469	0.045*	0.38
C4B	0.1943 (4)	1.1594 (9)	0.3842 (3)	0.0378 (4)*	0.38
C5B	0.2837 (4)	1.0732 (8)	0.3021 (2)	0.0378 (4)*	0.38
H5B	0.2779	1.1480	0.2297	0.045*	0.38
C6B	0.3814 (3)	0.8763 (6)	0.32702 (19)	0.0378 (4)*	0.38
H6B	0.4419	0.8180	0.2715	0.045*	0.38
C7B	0.4945 (3)	0.5594 (6)	0.4527 (2)	0.0378 (4)*	0.19
H7B	0.5542	0.5138	0.3947	0.045*	0.19
C8B	0.0920 (10)	1.3693 (19)	0.3468 (6)	0.0378 (4)*	0.38
H81B	0.0032	1.2846	0.3419	0.057*	0.38
H82B	0.1170	1.4398	0.2738	0.057*	0.38
H83B	0.0899	1.5191	0.4003	0.057*	0.38

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0378 (7)	0.0311 (7)	0.0511 (9)	0.0063 (6)	−0.0089 (6)	0.0052 (6)
C1A	0.0260 (7)	0.0259 (7)	0.0423 (8)	0.0021 (5)	−0.0036 (6)	−0.0009 (6)
C2A	0.0381 (9)	0.0396 (9)	0.0388 (8)	0.0121 (7)	0.0017 (6)	0.0017 (7)
C3A	0.0377 (10)	0.0386 (10)	0.0487 (10)	0.0158 (7)	−0.0006 (7)	0.0003 (8)
C4A	0.0283 (7)	0.0205 (6)	0.0492 (9)	−0.0010 (5)	−0.0111 (6)	−0.0020 (6)
C5A	0.0471 (9)	0.0391 (10)	0.0388 (10)	0.0033 (7)	−0.0017 (8)	0.0053 (8)
C6A	0.0368 (8)	0.0415 (9)	0.0401 (9)	0.0093 (7)	0.0063 (7)	−0.0010 (8)
C7A	0.0378 (7)	0.0311 (7)	0.0511 (9)	0.0063 (6)	−0.0089 (6)	0.0052 (6)
C8A	0.0445 (11)	0.0296 (9)	0.0754 (13)	0.0104 (7)	−0.0210 (9)	0.0017 (8)

Geometric parameters (Å, º) top

N1A—N1Aⁱ	1.277 (3)	N1B—N1Bⁱ	1.273 (5)
C1A—C6A	1.386 (2)	C1B—C2B	1.3900
C1A—C2A	1.391 (2)	C1B—C6B	1.3900
C2A—C3A	1.392 (2)	C2B—C3B	1.3900
C3A—C4A	1.386 (2)	C3B—C4B	1.3900
C4A—C5A	1.387 (2)	C4B—C5B	1.3900
C4A—C8A	1.507 (6)	C4B—C8B	1.501 (10)
C5A—C6A	1.394 (2)	C5B—C6B	1.3900

C6A—C1A—C2A	118.10 (14)	C2B—C1B—C6B	120.0
C1A—C2A—C3A	120.74 (15)	C1B—C2B—C3B	120.0
C4A—C3A—C2A	121.79 (15)	C4B—C3B—C2B	120.0
C3A—C4A—C5A	116.76 (14)	C5B—C4B—C3B	120.0
C3A—C4A—C8A	118.8 (3)	C5B—C4B—C8B	115.0 (3)
C5A—C4A—C8A	124.4 (3)	C3B—C4B—C8B	125.0 (3)
C4A—C5A—C6A	122.24 (16)	C4B—C5B—C6B	120.0
C1A—C6A—C5A	120.33 (15)	C5B—C6B—C1B	120.0

C6A—C1A—C2A—C3A	1.6 (3)	C6B—C1B—C2B—C3B	0.0
C1A—C2A—C3A—C4A	−0.4 (3)	C1B—C2B—C3B—C4B	0.0
C2A—C3A—C4A—C5A	−1.1 (3)	C2B—C3B—C4B—C5B	0.0
C2A—C3A—C4A—C8A	−179.3 (4)	C2B—C3B—C4B—C8B	179.0 (6)
C3A—C4A—C5A—C6A	1.5 (3)	C3B—C4B—C5B—C6B	0.0
C8A—C4A—C5A—C6A	179.6 (4)	C8B—C4B—C5B—C6B	−179.1 (6)
C2A—C1A—C6A—C5A	−1.3 (3)	C4B—C5B—C6B—C1B	0.0
C4A—C5A—C6A—C1A	−0.3 (3)	C2B—C1B—C6B—C5B	0.0

Symmetry code: (i) −x+1, −y+1, −z+1.

(3_200K) N-(4-methylbenzylidene)-4-methylaniline top

Crystal data top

C₁₅H₁₅N	D_x = 1.225 Mg m⁻³
M_r = 209.28	Melting point: 89.4 C K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.8565 (6) Å	Cell parameters from 3629 reflections
b = 4.8494 (3) Å	θ = 3.4–30.0°
c = 11.8748 (7) Å	µ = 0.07 mm⁻¹
β = 90.561 (1)°	T = 200 K
V = 567.57 (6) Å³	Plate, colourless
Z = 2	0.40 × 0.30 × 0.08 mm
F(000) = 224

Data collection top

Bruker SMART 1000 CCD diffractometer	1661 independent reflections
Radiation source: fine-focus sealed tube	1428 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
Detector resolution: 8.192 pixels mm^-1	θ_max = 30.0°, θ_min = 2.1°
ω scan	h = −13→13
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −6→6
T_min = 0.972, T_max = 0.994	l = −16→16
8329 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.045	w = 1/[σ²(F_o²) + (0.0651P)² + 0.1155P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.134	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.27 e Å⁻³
1661 reflections	Δρ_min = −0.19 e Å⁻³
89 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.074 (12)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₁₅N	V = 567.57 (6) Å³
M_r = 209.28	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8565 (6) Å	µ = 0.07 mm⁻¹
b = 4.8494 (3) Å	T = 200 K
c = 11.8748 (7) Å	0.40 × 0.30 × 0.08 mm
β = 90.561 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	1661 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	1428 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.994	R_int = 0.017
8329 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.08	Δρ_max = 0.27 e Å⁻³
1661 reflections	Δρ_min = −0.19 e Å⁻³
89 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.45675 (13)	0.5686 (3)	0.52860 (11)	0.0327 (3)	0.33
C1A	0.36909 (12)	0.7712 (3)	0.47654 (13)	0.0256 (3)	0.67
C2A	0.27052 (15)	0.8910 (3)	0.54401 (12)	0.0312 (3)	0.67
H2A	0.2646	0.8393	0.6210	0.037*	0.67
C3A	0.18056 (19)	1.0855 (4)	0.50019 (16)	0.0331 (3)	0.67
H3A	0.1138	1.1632	0.5479	0.040*	0.67
C4A	0.1860 (2)	1.1689 (4)	0.38830 (18)	0.0264 (3)	0.67
C5A	0.2870 (2)	1.0522 (4)	0.32238 (14)	0.0330 (3)	0.67
H5A	0.2945	1.1081	0.2460	0.040*	0.67
C6A	0.37737 (14)	0.8560 (3)	0.36488 (13)	0.0317 (3)	0.67
H6A	0.4448	0.7800	0.3174	0.038*	0.67
C7A	0.45675 (13)	0.5686 (3)	0.52860 (11)	0.0327 (3)	0.33
H7A	0.4501	0.5362	0.6073	0.039*	0.33
C8A	0.0869 (5)	1.3832 (10)	0.3447 (4)	0.0378 (5)	0.67
H81A	0.1090	1.5630	0.3778	0.057*	0.67
H82A	−0.0055	1.3307	0.3657	0.057*	0.67
H83A	0.0929	1.3946	0.2625	0.057*	0.67
N1B	0.4942 (3)	0.5603 (6)	0.4524 (2)	0.0311 (4)*	0.17
C1B	0.3899 (2)	0.7677 (5)	0.4336 (2)	0.0311 (4)*	0.33
C2B	0.3002 (3)	0.8531 (6)	0.51626 (18)	0.0311 (4)*	0.33
H2B	0.3058	0.7764	0.5898	0.037*	0.33
C3B	0.2023 (3)	1.0509 (8)	0.4913 (3)	0.0311 (4)*	0.33
H3B	0.1410	1.1092	0.5478	0.037*	0.33
C4B	0.1941 (4)	1.1632 (9)	0.3838 (3)	0.0311 (4)*	0.33
C5B	0.2838 (4)	1.0778 (8)	0.3012 (2)	0.0311 (4)*	0.33
H5B	0.2782	1.1546	0.2277	0.037*	0.33
C6B	0.3817 (3)	0.8801 (6)	0.32610 (19)	0.0311 (4)*	0.33
H6B	0.4430	0.8217	0.2696	0.037*	0.33
C7B	0.4942 (3)	0.5603 (6)	0.4524 (2)	0.0311 (4)*	0.17
H7B	0.5542	0.5140	0.3932	0.037*	0.17
C8B	0.0927 (10)	1.372 (2)	0.3481 (7)	0.0311 (4)*	0.33
H81B	0.0397	1.3007	0.2842	0.047*	0.33
H82B	0.1393	1.5414	0.3257	0.047*	0.33
H83B	0.0319	1.4117	0.4109	0.047*	0.33

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0315 (6)	0.0251 (6)	0.0414 (7)	0.0049 (5)	−0.0080 (5)	0.0042 (5)
C1A	0.0212 (5)	0.0210 (5)	0.0343 (6)	0.0019 (4)	−0.0031 (5)	−0.0008 (5)
C2A	0.0316 (7)	0.0312 (7)	0.0308 (7)	0.0095 (5)	0.0012 (5)	0.0011 (5)
C3A	0.0301 (8)	0.0312 (8)	0.0380 (7)	0.0123 (5)	0.0001 (6)	0.0000 (6)
C4A	0.0229 (6)	0.0171 (5)	0.0391 (7)	−0.0004 (4)	−0.0080 (5)	−0.0019 (5)
C5A	0.0366 (7)	0.0307 (8)	0.0318 (8)	0.0028 (6)	−0.0011 (6)	0.0039 (6)
C6A	0.0285 (6)	0.0330 (7)	0.0336 (7)	0.0074 (5)	0.0047 (5)	0.0000 (6)
C7A	0.0315 (6)	0.0251 (6)	0.0414 (7)	0.0049 (5)	−0.0080 (5)	0.0042 (5)
C8A	0.0346 (8)	0.0233 (8)	0.0552 (10)	0.0087 (6)	−0.0155 (7)	0.0018 (6)

Geometric parameters (Å, º) top

N1A—N1Aⁱ	1.282 (3)	N1B—N1Bⁱ	1.277 (5)
C1A—C6A	1.3916 (19)	C1B—C2B	1.3900
C1A—C2A	1.3924 (17)	C1B—C6B	1.3900
C2A—C3A	1.3921 (18)	C2B—C3B	1.3900
C3A—C4A	1.390 (2)	C3B—C4B	1.3900
C4A—C5A	1.3921 (19)	C4B—C5B	1.3900
C4A—C8A	1.514 (5)	C4B—C8B	1.482 (10)
C5A—C6A	1.3946 (19)	C5B—C6B	1.3900

C6A—C1A—C2A	118.21 (11)	C2B—C1B—C6B	120.0
C3A—C2A—C1A	120.88 (12)	C3B—C2B—C1B	120.0
C4A—C3A—C2A	121.58 (13)	C2B—C3B—C4B	120.0
C3A—C4A—C5A	116.99 (12)	C5B—C4B—C3B	120.0
C3A—C4A—C8A	119.7 (2)	C5B—C4B—C8B	115.7 (4)
C5A—C4A—C8A	123.3 (2)	C3B—C4B—C8B	124.3 (4)
C4A—C5A—C6A	122.10 (13)	C6B—C5B—C4B	120.0
C1A—C6A—C5A	120.22 (12)	C5B—C6B—C1B	120.0

C6A—C1A—C2A—C3A	1.5 (2)	C6B—C1B—C2B—C3B	0.0
C1A—C2A—C3A—C4A	−0.5 (2)	C1B—C2B—C3B—C4B	0.0
C2A—C3A—C4A—C5A	−1.0 (2)	C2B—C3B—C4B—C5B	0.0
C2A—C3A—C4A—C8A	−179.4 (3)	C2B—C3B—C4B—C8B	179.1 (7)
C3A—C4A—C5A—C6A	1.3 (2)	C3B—C4B—C5B—C6B	0.0
C8A—C4A—C5A—C6A	179.7 (3)	C8B—C4B—C5B—C6B	−179.2 (6)
C2A—C1A—C6A—C5A	−1.2 (2)	C4B—C5B—C6B—C1B	0.0
C4A—C5A—C6A—C1A	−0.3 (2)	C2B—C1B—C6B—C5B	0.0

Symmetry code: (i) −x+1, −y+1, −z+1.

(3_150K) N-(4-methylbenzylidene)-4-methylaniline top

Crystal data top

C₁₅H₁₅N	D_x = 1.238 Mg m⁻³
M_r = 209.28	Melting point: 89.4 C K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.8477 (6) Å	Cell parameters from 4040 reflections
b = 4.8327 (3) Å	θ = 3.5–29.9°
c = 11.7991 (7) Å	µ = 0.07 mm⁻¹
β = 90.631 (1)°	T = 150 K
V = 561.50 (6) Å³	Plate, colourless
Z = 2	0.40 × 0.30 × 0.08 mm
F(000) = 224

Data collection top

Bruker SMART 1000 CCD diffractometer	1641 independent reflections
Radiation source: fine-focus sealed tube	1453 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
Detector resolution: 8.192 pixels mm^-1	θ_max = 30.0°, θ_min = 2.1°
ω scan	h = −13→13
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −6→6
T_min = 0.972, T_max = 0.994	l = −16→16
8213 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.043	w = 1/[σ²(F_o²) + (0.0652P)² + 0.132P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.126	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.31 e Å⁻³
1641 reflections	Δρ_min = −0.18 e Å⁻³
89 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.050 (10)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₁₅N	V = 561.50 (6) Å³
M_r = 209.28	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8477 (6) Å	µ = 0.07 mm⁻¹
b = 4.8327 (3) Å	T = 150 K
c = 11.7991 (7) Å	0.40 × 0.30 × 0.08 mm
β = 90.631 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	1641 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	1453 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.994	R_int = 0.015
8213 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.06	Δρ_max = 0.31 e Å⁻³
1641 reflections	Δρ_min = −0.18 e Å⁻³
89 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.45703 (11)	0.5692 (2)	0.52912 (9)	0.0257 (3)	0.36
C1A	0.36926 (11)	0.7727 (2)	0.47704 (11)	0.0199 (2)	0.73
C2A	0.27038 (12)	0.8918 (3)	0.54512 (10)	0.0245 (3)	0.73
H2A	0.2645	0.8391	0.6225	0.029*	0.73
C3A	0.18006 (15)	1.0871 (3)	0.50130 (13)	0.0257 (3)	0.73
H3A	0.1132	1.1644	0.5493	0.031*	0.73
C4A	0.18563 (17)	1.1715 (4)	0.38855 (15)	0.0205 (3)	0.73
C5A	0.28697 (17)	1.0552 (3)	0.32176 (11)	0.0252 (3)	0.73
H5A	0.2945	1.1120	0.2450	0.030*	0.73
C6A	0.37731 (12)	0.8584 (3)	0.36446 (11)	0.0243 (3)	0.73
H6A	0.4447	0.7822	0.3167	0.029*	0.73
C7A	0.45703 (11)	0.5692 (2)	0.52912 (9)	0.0257 (3)	0.36
H7A	0.4511	0.5368	0.6083	0.031*	0.36
C8A	0.0860 (4)	1.3879 (8)	0.3439 (3)	0.0269 (4)	0.73
H81A	0.1116	1.5705	0.3732	0.040*	0.73
H82A	−0.0059	1.3419	0.3689	0.040*	0.73
H83A	0.0881	1.3903	0.2609	0.040*	0.73
N1B	0.4934 (3)	0.5607 (6)	0.4519 (2)	0.0243 (4)*	0.14
C1B	0.3896 (3)	0.7696 (5)	0.4331 (2)	0.0243 (4)*	0.27
C2B	0.3000 (3)	0.8549 (6)	0.51635 (19)	0.0243 (4)*	0.27
H2B	0.3057	0.7773	0.5902	0.029*	0.27
C3B	0.2022 (4)	1.0538 (9)	0.4915 (3)	0.0243 (4)*	0.27
H3B	0.1410	1.1121	0.5484	0.029*	0.27
C4B	0.1940 (5)	1.1674 (10)	0.3834 (4)	0.0243 (4)*	0.27
C5B	0.2835 (4)	1.0821 (9)	0.3002 (3)	0.0243 (4)*	0.27
H5B	0.2779	1.1598	0.2263	0.029*	0.27
C6B	0.3814 (3)	0.8832 (7)	0.3250 (2)	0.0243 (4)*	0.27
H6B	0.4426	0.8249	0.2681	0.029*	0.27
C7B	0.4934 (3)	0.5607 (6)	0.4519 (2)	0.0243 (4)*	0.14
H7B	0.5526	0.5131	0.3919	0.029*	0.14
C8B	0.0948 (11)	1.371 (2)	0.3492 (8)	0.0243 (4)*	0.27
H81B	0.0389	1.2975	0.2870	0.037*	0.27
H82B	0.1414	1.5391	0.3237	0.037*	0.27
H83B	0.0368	1.4165	0.4136	0.037*	0.27

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0252 (5)	0.0191 (5)	0.0326 (5)	0.0032 (4)	−0.0070 (4)	0.0036 (4)
C1A	0.0169 (5)	0.0161 (5)	0.0265 (5)	0.0016 (4)	−0.0028 (4)	−0.0005 (4)
C2A	0.0251 (6)	0.0245 (6)	0.0239 (5)	0.0072 (4)	0.0011 (4)	0.0009 (4)
C3A	0.0237 (7)	0.0245 (6)	0.0290 (6)	0.0092 (4)	0.0006 (4)	−0.0003 (5)
C4A	0.0178 (5)	0.0133 (5)	0.0303 (6)	−0.0004 (4)	−0.0057 (4)	−0.0017 (4)
C5A	0.0276 (6)	0.0230 (6)	0.0250 (6)	0.0019 (4)	−0.0008 (5)	0.0031 (5)
C6A	0.0218 (5)	0.0250 (6)	0.0261 (6)	0.0053 (4)	0.0031 (4)	0.0004 (5)
C7A	0.0252 (5)	0.0191 (5)	0.0326 (5)	0.0032 (4)	−0.0070 (4)	0.0036 (4)
C8A	0.0244 (8)	0.0173 (7)	0.0388 (8)	0.0071 (5)	−0.0110 (6)	0.0021 (5)

Geometric parameters (Å, º) top

N1A—N1Aⁱ	1.284 (2)	N1B—N1Bⁱ	1.283 (6)
C1A—C2A	1.3935 (15)	C1B—C2B	1.3900
C1A—C6A	1.3945 (16)	C1B—C6B	1.3900
C2A—C3A	1.3924 (16)	C2B—C3B	1.3900
C3A—C4A	1.3930 (17)	C3B—C4B	1.3900
C4A—C5A	1.3964 (16)	C4B—C5B	1.3900
C4A—C8A	1.524 (3)	C4B—C8B	1.442 (11)
C5A—C6A	1.3929 (16)	C5B—C6B	1.3900

C2A—C1A—C6A	118.29 (10)	C2B—C1B—C6B	120.0
C3A—C2A—C1A	120.89 (10)	C1B—C2B—C3B	120.0
C2A—C3A—C4A	121.42 (11)	C4B—C3B—C2B	120.0
C3A—C4A—C5A	117.20 (10)	C3B—C4B—C5B	120.0
C3A—C4A—C8A	119.94 (19)	C3B—C4B—C8B	124.0 (5)
C5A—C4A—C8A	122.8 (2)	C5B—C4B—C8B	116.0 (5)
C6A—C5A—C4A	121.88 (11)	C6B—C5B—C4B	120.0
C5A—C6A—C1A	120.30 (10)	C5B—C6B—C1B	120.0

C6A—C1A—C2A—C3A	1.33 (18)	C6B—C1B—C2B—C3B	0.0
C1A—C2A—C3A—C4A	−0.39 (19)	C1B—C2B—C3B—C4B	0.0
C2A—C3A—C4A—C5A	−0.98 (17)	C2B—C3B—C4B—C5B	0.0
C2A—C3A—C4A—C8A	−179.4 (2)	C2B—C3B—C4B—C8B	179.0 (7)
C3A—C4A—C5A—C6A	1.42 (17)	C3B—C4B—C5B—C6B	0.0
C8A—C4A—C5A—C6A	179.8 (3)	C8B—C4B—C5B—C6B	−179.1 (7)
C4A—C5A—C6A—C1A	−0.49 (18)	C4B—C5B—C6B—C1B	0.0
C2A—C1A—C6A—C5A	−0.90 (18)	C2B—C1B—C6B—C5B	0.0

Symmetry code: (i) −x+1, −y+1, −z+1.

(3_90K) N-(4-methylbenzylidene)-4-methylaniline top

Crystal data top

C₁₅H₁₅N	D_x = 1.251 Mg m⁻³
M_r = 209.28	Melting point: 89.4 C K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.8184 (6) Å	Cell parameters from 4495 reflections
b = 4.8159 (3) Å	θ = 3.5–29.9°
c = 11.7536 (7) Å	µ = 0.07 mm⁻¹
β = 90.689 (1)°	T = 90 K
V = 555.72 (6) Å³	Plate, colourless
Z = 2	0.40 × 0.30 × 0.08 mm
F(000) = 224

Data collection top

Bruker SMART 1000 CCD diffractometer	1624 independent reflections
Radiation source: fine-focus sealed tube	1473 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
Detector resolution: 8.192 pixels mm^-1	θ_max = 30.0°, θ_min = 2.1°
ω scan	h = −13→13
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −6→6
T_min = 0.972, T_max = 0.994	l = −16→16
8100 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.041	w = 1/[σ²(F_o²) + (0.0687P)² + 0.1224P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.121	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 0.36 e Å⁻³
1624 reflections	Δρ_min = −0.18 e Å⁻³
89 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.035 (10)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₁₅N	V = 555.72 (6) Å³
M_r = 209.28	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8184 (6) Å	µ = 0.07 mm⁻¹
b = 4.8159 (3) Å	T = 90 K
c = 11.7536 (7) Å	0.40 × 0.30 × 0.08 mm
β = 90.689 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	1624 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	1473 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.994	R_int = 0.013
8100 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.07	Δρ_max = 0.36 e Å⁻³
1624 reflections	Δρ_min = −0.18 e Å⁻³
89 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.45727 (10)	0.57029 (19)	0.52957 (8)	0.0191 (2)	0.37
C1A	0.36916 (9)	0.7746 (2)	0.47705 (9)	0.0142 (2)	0.74
C2A	0.27013 (11)	0.8940 (2)	0.54550 (9)	0.0174 (2)	0.74
H2A	0.2646	0.8412	0.6232	0.021*	0.74
C3A	0.17907 (13)	1.0899 (3)	0.50163 (11)	0.0180 (2)	0.74
H3A	0.1120	1.1671	0.5499	0.022*	0.74
C4A	0.18462 (15)	1.1750 (3)	0.38801 (13)	0.0147 (2)	0.74
C5A	0.28644 (14)	1.0582 (3)	0.32087 (10)	0.0181 (2)	0.74
H5A	0.2939	1.1152	0.2438	0.022*	0.74
C6A	0.37737 (10)	0.8604 (2)	0.36378 (10)	0.0174 (2)	0.74
H6A	0.4450	0.7840	0.3159	0.021*	0.74
C7A	0.45727 (10)	0.57029 (19)	0.52957 (8)	0.0191 (2)	0.37
H7A	0.4521	0.5390	0.6092	0.023*	0.37
C8A	0.0848 (3)	1.3929 (6)	0.3434 (3)	0.0182 (4)	0.74
H81A	0.1110	1.5760	0.3728	0.027*	0.74
H82A	−0.0073	1.3474	0.3687	0.027*	0.74
H83A	0.0865	1.3955	0.2601	0.027*	0.74
N1B	0.4931 (3)	0.5617 (6)	0.4517 (2)	0.0183 (4)*	0.13
C1B	0.3894 (2)	0.7714 (5)	0.4327 (2)	0.0183 (4)*	0.26
C2B	0.2997 (3)	0.8569 (6)	0.51634 (18)	0.0183 (4)*	0.26
H2B	0.3055	0.7790	0.5905	0.022*	0.26
C3B	0.2015 (4)	1.0565 (8)	0.4915 (3)	0.0183 (4)*	0.26
H3B	0.1402	1.1149	0.5487	0.022*	0.26
C4B	0.1929 (4)	1.1706 (9)	0.3830 (3)	0.0183 (4)*	0.26
C5B	0.2826 (4)	1.0851 (8)	0.2994 (2)	0.0183 (4)*	0.26
H5B	0.2768	1.1631	0.2252	0.022*	0.26
C6B	0.3808 (3)	0.8855 (6)	0.32421 (19)	0.0183 (4)*	0.26
H6B	0.4421	0.8271	0.2670	0.022*	0.26
C7B	0.4931 (3)	0.5617 (6)	0.4517 (2)	0.0183 (4)*	0.13
H7B	0.5524	0.5141	0.3914	0.022*	0.13
C8B	0.0937 (10)	1.372 (2)	0.3487 (8)	0.0183 (4)*	0.26
H81B	0.0465	1.3072	0.2797	0.027*	0.26
H82B	0.1389	1.5488	0.3333	0.027*	0.26
H83B	0.0275	1.3966	0.4096	0.027*	0.26

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0185 (4)	0.0130 (4)	0.0257 (5)	0.0017 (3)	−0.0063 (4)	0.0026 (3)
C1A	0.0116 (4)	0.0108 (4)	0.0201 (5)	0.0011 (3)	−0.0027 (3)	−0.0005 (3)
C2A	0.0175 (5)	0.0165 (5)	0.0182 (5)	0.0050 (4)	−0.0001 (4)	0.0006 (4)
C3A	0.0161 (6)	0.0165 (5)	0.0214 (5)	0.0066 (4)	−0.0004 (4)	−0.0006 (4)
C4A	0.0121 (5)	0.0091 (4)	0.0227 (5)	−0.0003 (3)	−0.0043 (3)	−0.0018 (3)
C5A	0.0190 (5)	0.0157 (5)	0.0193 (5)	0.0011 (4)	−0.0011 (4)	0.0023 (4)
C6A	0.0148 (4)	0.0172 (5)	0.0202 (5)	0.0034 (3)	0.0018 (4)	0.0005 (4)
C7A	0.0185 (4)	0.0130 (4)	0.0257 (5)	0.0017 (3)	−0.0063 (4)	0.0026 (3)
C8A	0.0161 (7)	0.0105 (7)	0.0278 (6)	0.0056 (4)	−0.0084 (5)	0.0020 (5)

Geometric parameters (Å, º) top

N1A—N1Aⁱ	1.288 (2)	N1B—N1Bⁱ	1.287 (5)
C1A—C2A	1.3937 (13)	C1B—C2B	1.3900
C1A—C6A	1.3973 (14)	C1B—C6B	1.3900
C2A—C3A	1.3943 (13)	C2B—C3B	1.3900
C3A—C4A	1.3987 (15)	C3B—C4B	1.3900
C4A—C5A	1.3992 (14)	C4B—C5B	1.3900
C4A—C8A	1.525 (3)	C4B—C8B	1.428 (10)
C5A—C6A	1.3956 (14)	C5B—C6B	1.3900

C2A—C1A—C6A	118.46 (9)	C2B—C1B—C6B	120.0
C1A—C2A—C3A	120.96 (9)	C3B—C2B—C1B	120.0
C2A—C3A—C4A	121.28 (9)	C4B—C3B—C2B	120.0
C3A—C4A—C5A	117.19 (9)	C3B—C4B—C5B	120.0
C3A—C4A—C8A	119.86 (16)	C3B—C4B—C8B	124.1 (4)
C5A—C4A—C8A	122.93 (17)	C5B—C4B—C8B	115.9 (4)
C6A—C5A—C4A	121.93 (10)	C6B—C5B—C4B	120.0
C5A—C6A—C1A	120.15 (9)	C5B—C6B—C1B	120.0

C6A—C1A—C2A—C3A	1.49 (15)	C6B—C1B—C2B—C3B	0.0
C1A—C2A—C3A—C4A	−0.56 (16)	C1B—C2B—C3B—C4B	0.0
C2A—C3A—C4A—C5A	−0.86 (15)	C2B—C3B—C4B—C5B	0.0
C2A—C3A—C4A—C8A	−179.1 (2)	C2B—C3B—C4B—C8B	178.5 (7)
C3A—C4A—C5A—C6A	1.36 (15)	C3B—C4B—C5B—C6B	0.0
C8A—C4A—C5A—C6A	179.5 (2)	C8B—C4B—C5B—C6B	−178.6 (6)
C4A—C5A—C6A—C1A	−0.46 (16)	C4B—C5B—C6B—C1B	0.0
C2A—C1A—C6A—C5A	−0.98 (16)	C2B—C1B—C6B—C5B	0.0

Symmetry code: (i) −x+1, −y+1, −z+1.

(3_90K2) N-(4-methylbenzylidene)-4-methylaniline top

Crystal data top

C₁₅H₁₅N	D_x = 1.249 Mg m⁻³
M_r = 209.28	Melting point: 89.4 C K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.7961 (6) Å	Cell parameters from 4202 reflections
b = 4.8169 (3) Å	θ = 3.5–29.8°
c = 11.7947 (7) Å	µ = 0.07 mm⁻¹
β = 90.614 (1)°	T = 90 K
V = 556.52 (6) Å³	Plate, colourless
Z = 2	0.40 × 0.30 × 0.08 mm
F(000) = 224

Data collection top

Bruker SMART 1000 CCD diffractometer	1630 independent reflections
Radiation source: fine-focus sealed tube	1469 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Detector resolution: 8.192 pixels mm^-1	θ_max = 30.0°, θ_min = 2.1°
ω scan	h = −13→13
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −6→6
T_min = 0.972, T_max = 0.994	l = −16→16
8121 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.042	w = 1/[σ²(F_o²) + (0.0688P)² + 0.1328P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.123	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.35 e Å⁻³
1630 reflections	Δρ_min = −0.20 e Å⁻³
89 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.095 (13)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₁₅N	V = 556.52 (6) Å³
M_r = 209.28	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.7961 (6) Å	µ = 0.07 mm⁻¹
b = 4.8169 (3) Å	T = 90 K
c = 11.7947 (7) Å	0.40 × 0.30 × 0.08 mm
β = 90.614 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	1630 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	1469 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.994	R_int = 0.018
8121 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.05	Δρ_max = 0.35 e Å⁻³
1630 reflections	Δρ_min = −0.20 e Å⁻³
89 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.45683 (11)	−0.4299 (2)	0.52918 (10)	0.0200 (2)	0.33
C1A	0.36882 (11)	−0.2256 (2)	0.47667 (11)	0.0145 (2)	0.67
C2A	0.26952 (12)	−0.1057 (2)	0.54476 (10)	0.0176 (3)	0.67
H2A	0.2637	−0.1583	0.6222	0.021*	0.67
C3A	0.17851 (14)	0.0903 (3)	0.50087 (12)	0.0183 (3)	0.67
H3A	0.1113	0.1679	0.5490	0.022*	0.67
C4A	0.18397 (17)	0.1749 (4)	0.38762 (15)	0.0145 (3)	0.67
C5A	0.28625 (17)	0.0576 (3)	0.32091 (11)	0.0189 (3)	0.67
H5A	0.2940	0.1142	0.2441	0.023*	0.67
C6A	0.37726 (12)	−0.1403 (3)	0.36396 (11)	0.0179 (3)	0.67
H6A	0.4451	−0.2170	0.3163	0.021*	0.67
C7A	0.45683 (11)	−0.4299 (2)	0.52918 (10)	0.0200 (2)	0.33
H7A	0.4509	−0.4615	0.6085	0.024*	0.33
C8A	0.0840 (4)	0.3928 (8)	0.3435 (3)	0.0198 (4)	0.67
H81A	0.1077	0.5743	0.3756	0.030*	0.67
H82A	−0.0089	0.3426	0.3658	0.030*	0.67
H83A	0.0888	0.4016	0.2606	0.030*	0.67
N1B	0.4938 (2)	−0.4382 (5)	0.45194 (18)	0.0186 (3)*	0.17
C1B	0.3892 (2)	−0.2287 (4)	0.43321 (18)	0.0186 (3)*	0.33
C2B	0.2992 (2)	−0.1419 (5)	0.51634 (15)	0.0186 (3)*	0.33
H2B	0.3049	−0.2187	0.5904	0.022*	0.33
C3B	0.2009 (3)	0.0574 (7)	0.4911 (2)	0.0186 (3)*	0.33
H3B	0.1394	0.1168	0.5479	0.022*	0.33
C4B	0.1925 (3)	0.1698 (8)	0.3827 (3)	0.0186 (3)*	0.33
C5B	0.2825 (3)	0.0829 (7)	0.29954 (19)	0.0186 (3)*	0.33
H5B	0.2768	0.1597	0.2255	0.022*	0.33
C6B	0.3809 (2)	−0.1164 (5)	0.32481 (16)	0.0186 (3)*	0.33
H6B	0.4424	−0.1757	0.2680	0.022*	0.33
C7B	0.4938 (2)	−0.4382 (5)	0.45194 (18)	0.0186 (3)*	0.17
H7B	0.5539	−0.4845	0.3922	0.022*	0.17
C8B	0.0912 (9)	0.3759 (19)	0.3483 (7)	0.0186 (3)*	0.33
H81B	0.0516	0.3238	0.2746	0.028*	0.33
H82B	0.1349	0.5581	0.3422	0.028*	0.33
H83B	0.0188	0.3842	0.4050	0.028*	0.33

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0189 (5)	0.0128 (5)	0.0281 (5)	0.0020 (4)	−0.0073 (4)	0.0037 (4)
C1A	0.0114 (5)	0.0106 (5)	0.0215 (5)	0.0009 (3)	−0.0027 (4)	0.0000 (4)
C2A	0.0173 (6)	0.0164 (5)	0.0189 (5)	0.0045 (4)	0.0000 (4)	0.0004 (4)
C3A	0.0160 (6)	0.0164 (6)	0.0224 (6)	0.0068 (4)	−0.0005 (4)	−0.0004 (4)
C4A	0.0115 (5)	0.0080 (4)	0.0239 (6)	−0.0003 (4)	−0.0048 (4)	−0.0016 (4)
C5A	0.0205 (6)	0.0163 (6)	0.0198 (6)	0.0007 (4)	−0.0008 (5)	0.0021 (5)
C6A	0.0151 (5)	0.0179 (5)	0.0207 (5)	0.0036 (4)	0.0025 (4)	−0.0004 (5)
C7A	0.0189 (5)	0.0128 (5)	0.0281 (5)	0.0020 (4)	−0.0073 (4)	0.0037 (4)
C8A	0.0174 (7)	0.0102 (7)	0.0316 (8)	0.0059 (5)	−0.0103 (5)	0.0019 (5)

Geometric parameters (Å, º) top

N1A—N1Aⁱ	1.288 (2)	N1B—N1Bⁱ	1.285 (4)
C1A—C2A	1.3934 (14)	C1B—C2B	1.3900
C1A—C6A	1.3949 (15)	C1B—C6B	1.3900
C2A—C3A	1.3943 (15)	C2B—C3B	1.3900
C3A—C4A	1.3982 (16)	C3B—C4B	1.3900
C4A—C5A	1.3998 (15)	C4B—C5B	1.3900
C4A—C8A	1.524 (3)	C4B—C8B	1.458 (9)
C5A—C6A	1.3969 (16)	C5B—C6B	1.3900

C2A—C1A—C6A	118.43 (10)	C2B—C1B—C6B	120.0
C1A—C2A—C3A	120.95 (10)	C1B—C2B—C3B	120.0
C2A—C3A—C4A	121.42 (10)	C4B—C3B—C2B	120.0
C3A—C4A—C5A	117.01 (10)	C3B—C4B—C5B	120.0
C3A—C4A—C8A	119.76 (19)	C3B—C4B—C8B	123.6 (4)
C5A—C4A—C8A	123.2 (2)	C5B—C4B—C8B	116.4 (4)
C6A—C5A—C4A	121.95 (11)	C6B—C5B—C4B	120.0
C1A—C6A—C5A	120.22 (10)	C5B—C6B—C1B	120.0

C6A—C1A—C2A—C3A	1.47 (17)	C6B—C1B—C2B—C3B	0.0
C1A—C2A—C3A—C4A	−0.44 (18)	C1B—C2B—C3B—C4B	0.0
C2A—C3A—C4A—C5A	−1.03 (17)	C2B—C3B—C4B—C5B	0.0
C2A—C3A—C4A—C8A	−179.1 (2)	C2B—C3B—C4B—C8B	178.9 (6)
C3A—C4A—C5A—C6A	1.49 (17)	C3B—C4B—C5B—C6B	0.0
C8A—C4A—C5A—C6A	179.5 (3)	C8B—C4B—C5B—C6B	−179.0 (5)
C2A—C1A—C6A—C5A	−1.01 (17)	C4B—C5B—C6B—C1B	0.0
C4A—C5A—C6A—C1A	−0.48 (18)	C2B—C1B—C6B—C5B	0.0

Symmetry code: (i) −x+1, −y−1, −z+1.

(3_90K4) N-(4-methylbenzylidene)-4-methylaniline top

Crystal data top

C₁₅H₁₅N	D_x = 1.251 Mg m⁻³
M_r = 209.28	Melting point: 89.4 C K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.8177 (5) Å	Cell parameters from 4284 reflections
b = 4.8150 (3) Å	θ = 3.5–29.9°
c = 11.7497 (6) Å	µ = 0.07 mm⁻¹
β = 90.691 (1)°	T = 90 K
V = 555.39 (5) Å³	Plate, colourless
Z = 2	0.40 × 0.30 × 0.08 mm
F(000) = 224

Data collection top

Bruker SMART 1000 CCD diffractometer	1622 independent reflections
Radiation source: fine-focus sealed tube	1455 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 8.192 pixels mm^-1	θ_max = 30.0°, θ_min = 2.1°
ω scan	h = −13→13
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −6→6
T_min = 0.972, T_max = 0.994	l = −16→16
8085 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.040	w = 1/[σ²(F_o²) + (0.065P)² + 0.1346P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.119	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.34 e Å⁻³
1622 reflections	Δρ_min = −0.20 e Å⁻³
89 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.112 (14)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₁₅N	V = 555.39 (5) Å³
M_r = 209.28	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8177 (5) Å	µ = 0.07 mm⁻¹
b = 4.8150 (3) Å	T = 90 K
c = 11.7497 (6) Å	0.40 × 0.30 × 0.08 mm
β = 90.691 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	1622 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	1455 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.994	R_int = 0.019
8085 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.06	Δρ_max = 0.34 e Å⁻³
1622 reflections	Δρ_min = −0.20 e Å⁻³
89 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.45733 (10)	0.5702 (2)	0.52951 (8)	0.0193 (2)	0.37
C1A	0.36916 (10)	0.7746 (2)	0.47706 (10)	0.0145 (2)	0.74
C2A	0.27012 (11)	0.8941 (2)	0.54556 (9)	0.0177 (2)	0.74
H2A	0.2646	0.8412	0.6233	0.021*	0.74
C3A	0.17907 (13)	1.0901 (3)	0.50161 (11)	0.0183 (2)	0.74
H3A	0.1119	1.1673	0.5498	0.022*	0.74
C4A	0.18470 (16)	1.1751 (3)	0.38806 (14)	0.0149 (2)	0.74
C5A	0.28646 (15)	1.0583 (3)	0.32097 (10)	0.0183 (3)	0.74
H5A	0.2939	1.1153	0.2439	0.022*	0.74
C6A	0.37739 (11)	0.8605 (2)	0.36386 (10)	0.0177 (2)	0.74
H6A	0.4450	0.7841	0.3159	0.021*	0.74
C7A	0.45733 (10)	0.5702 (2)	0.52951 (8)	0.0193 (2)	0.37
H7A	0.4522	0.5390	0.6092	0.023*	0.37
C8A	0.0846 (3)	1.3928 (6)	0.3434 (3)	0.0185 (4)	0.74
H81A	0.1109	1.5762	0.3723	0.028*	0.74
H82A	−0.0074	1.3477	0.3691	0.028*	0.74
H83A	0.0858	1.3944	0.2600	0.028*	0.74
N1B	0.4933 (3)	0.5614 (6)	0.4517 (2)	0.0183 (4)*	0.13
C1B	0.3895 (2)	0.7713 (5)	0.4328 (2)	0.0183 (4)*	0.26
C2B	0.2997 (3)	0.8568 (6)	0.51637 (18)	0.0183 (4)*	0.26
H2B	0.3056	0.7790	0.5906	0.022*	0.26
C3B	0.2014 (4)	1.0560 (8)	0.4914 (3)	0.0183 (4)*	0.26
H3B	0.1400	1.1144	0.5485	0.022*	0.26
C4B	0.1928 (4)	1.1697 (10)	0.3828 (3)	0.0183 (4)*	0.26
C5B	0.2825 (4)	1.0843 (9)	0.2992 (2)	0.0183 (4)*	0.26
H5B	0.2767	1.1620	0.2250	0.022*	0.26
C6B	0.3809 (3)	0.8851 (7)	0.3242 (2)	0.0183 (4)*	0.26
H6B	0.4423	0.8266	0.2670	0.022*	0.26
C7B	0.4933 (3)	0.5614 (6)	0.4517 (2)	0.0183 (4)*	0.13
H7B	0.5526	0.5137	0.3914	0.022*	0.13
C8B	0.0944 (10)	1.372 (2)	0.3487 (8)	0.0183 (4)*	0.26
H81B	0.0456	1.3074	0.2805	0.028*	0.26
H82B	0.1405	1.5480	0.3320	0.028*	0.26
H83B	0.0294	1.4010	0.4103	0.028*	0.26

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0188 (4)	0.0128 (4)	0.0261 (5)	0.0016 (4)	−0.0063 (4)	0.0028 (3)
C1A	0.0125 (4)	0.0106 (4)	0.0205 (5)	0.0009 (3)	−0.0022 (3)	−0.0003 (3)
C2A	0.0179 (5)	0.0166 (5)	0.0186 (5)	0.0048 (4)	0.0000 (4)	0.0004 (4)
C3A	0.0169 (6)	0.0161 (5)	0.0219 (5)	0.0066 (4)	−0.0003 (4)	−0.0005 (4)
C4A	0.0126 (5)	0.0089 (4)	0.0231 (5)	−0.0004 (3)	−0.0044 (4)	−0.0017 (3)
C5A	0.0194 (5)	0.0160 (5)	0.0196 (6)	0.0009 (4)	−0.0011 (4)	0.0021 (4)
C6A	0.0156 (4)	0.0173 (5)	0.0203 (5)	0.0036 (4)	0.0022 (4)	0.0004 (4)
C7A	0.0188 (4)	0.0128 (4)	0.0261 (5)	0.0016 (4)	−0.0063 (4)	0.0028 (3)
C8A	0.0163 (7)	0.0107 (7)	0.0283 (7)	0.0057 (5)	−0.0083 (5)	0.0020 (5)

Geometric parameters (Å, º) top

N1A—N1Aⁱ	1.286 (2)	N1B—N1Bⁱ	1.286 (5)
C1A—C2A	1.3940 (13)	C1B—C2B	1.3900
C1A—C6A	1.3963 (14)	C1B—C6B	1.3900
C2A—C3A	1.3949 (14)	C2B—C3B	1.3900
C3A—C4A	1.3974 (15)	C3B—C4B	1.3900
C4A—C5A	1.3981 (14)	C4B—C5B	1.3900
C4A—C8A	1.526 (3)	C4B—C8B	1.427 (10)
C5A—C6A	1.3954 (14)	C5B—C6B	1.3900

C2A—C1A—C6A	118.46 (9)	C2B—C1B—C6B	120.0
C1A—C2A—C3A	120.93 (9)	C3B—C2B—C1B	120.0
C2A—C3A—C4A	121.28 (9)	C2B—C3B—C4B	120.0
C3A—C4A—C5A	117.21 (9)	C5B—C4B—C3B	120.0
C3A—C4A—C8A	119.80 (16)	C5B—C4B—C8B	115.9 (4)
C5A—C4A—C8A	122.97 (17)	C3B—C4B—C8B	124.1 (5)
C6A—C5A—C4A	121.97 (10)	C4B—C5B—C6B	120.0
C5A—C6A—C1A	120.14 (9)	C5B—C6B—C1B	120.0

C6A—C1A—C2A—C3A	1.51 (16)	C6B—C1B—C2B—C3B	0.0
C1A—C2A—C3A—C4A	−0.57 (16)	C1B—C2B—C3B—C4B	0.0
C2A—C3A—C4A—C5A	−0.85 (15)	C2B—C3B—C4B—C5B	0.0
C2A—C3A—C4A—C8A	−179.2 (2)	C2B—C3B—C4B—C8B	179.2 (7)
C3A—C4A—C5A—C6A	1.36 (15)	C3B—C4B—C5B—C6B	0.0
C8A—C4A—C5A—C6A	179.7 (2)	C8B—C4B—C5B—C6B	−179.3 (7)
C4A—C5A—C6A—C1A	−0.43 (16)	C4B—C5B—C6B—C1B	0.0
C2A—C1A—C6A—C5A	−1.02 (16)	C2B—C1B—C6B—C5B	0.0

Symmetry code: (i) −x+1, −y+1, −z+1.

(3_300K2) N-(4-methylbenzylidene)-4-methylaniline top

Crystal data top

C₁₅H₁₅N	D_x = 1.198 Mg m⁻³
M_r = 209.28	Melting point: 89.4 C K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.8781 (7) Å	Cell parameters from 2790 reflections
b = 4.8848 (4) Å	θ = 3.4–29.9°
c = 12.0214 (9) Å	µ = 0.07 mm⁻¹
β = 90.488 (1)°	T = 300 K
V = 580.04 (8) Å³	Plate, colourless
Z = 2	0.40 × 0.30 × 0.08 mm
F(000) = 224

Data collection top

Bruker SMART 1000 CCD diffractometer	1692 independent reflections
Radiation source: fine-focus sealed tube	1326 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 8.192 pixels mm^-1	θ_max = 30.0°, θ_min = 2.1°
ω scan	h = −13→13
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −6→6
T_min = 0.973, T_max = 0.995	l = −16→16
8508 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.051	w = 1/[σ²(F_o²) + (0.0596P)² + 0.1235P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.149	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.22 e Å⁻³
1692 reflections	Δρ_min = −0.21 e Å⁻³
89 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.30 (2)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₁₅N	V = 580.04 (8) Å³
M_r = 209.28	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8781 (7) Å	µ = 0.07 mm⁻¹
b = 4.8848 (4) Å	T = 300 K
c = 12.0214 (9) Å	0.40 × 0.30 × 0.08 mm
β = 90.488 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	1692 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	1326 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.995	R_int = 0.024
8508 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.06	Δρ_max = 0.22 e Å⁻³
1692 reflections	Δρ_min = −0.21 e Å⁻³
89 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.45641 (19)	0.5681 (4)	0.52730 (17)	0.0483 (4)	0.29
C1A	0.36898 (18)	0.7687 (4)	0.47544 (19)	0.0383 (4)	0.59
C2A	0.2709 (2)	0.8898 (5)	0.54164 (18)	0.0474 (5)	0.59
H2A	0.2647	0.8416	0.6163	0.057*	0.59
C3A	0.1821 (3)	1.0823 (6)	0.4972 (3)	0.0510 (6)	0.59
H3A	0.1171	1.1595	0.5430	0.061*	0.59
C4A	0.1873 (3)	1.1627 (6)	0.3872 (3)	0.0398 (5)	0.59
C5A	0.2873 (3)	1.0453 (7)	0.3235 (2)	0.0512 (6)	0.59
H5A	0.2950	1.0980	0.2494	0.061*	0.59
C6A	0.3771 (2)	0.8511 (5)	0.3658 (2)	0.0486 (5)	0.59
H6A	0.4428	0.7763	0.3200	0.058*	0.59
C7A	0.45641 (19)	0.5681 (4)	0.52730 (17)	0.0483 (4)	0.29
H7A	0.4488	0.5371	0.6033	0.058*	0.29
C8A	0.0884 (7)	1.3749 (14)	0.3453 (6)	0.0637 (8)	0.59
H81A	0.0986	1.5399	0.3879	0.096*	0.59
H82A	−0.0023	1.3071	0.3528	0.096*	0.59
H83A	0.1059	1.4128	0.2684	0.096*	0.59
N1B	0.4947 (3)	0.5585 (6)	0.4529 (2)	0.0456 (4)*	0.21
C1B	0.3901 (3)	0.7635 (5)	0.4344 (2)	0.0456 (4)*	0.41
C2B	0.3011 (3)	0.8506 (7)	0.51607 (19)	0.0456 (4)*	0.41
H2B	0.3068	0.7778	0.5874	0.055*	0.41
C3B	0.2034 (4)	1.0464 (8)	0.4910 (3)	0.0456 (4)*	0.41
H3B	0.1438	1.1047	0.5456	0.055*	0.41
C4B	0.1947 (4)	1.1552 (9)	0.3843 (3)	0.0456 (4)*	0.41
C5B	0.2838 (4)	1.0681 (9)	0.3027 (2)	0.0456 (4)*	0.41
H5B	0.2780	1.1409	0.2314	0.055*	0.41
C6B	0.3815 (3)	0.8722 (7)	0.3278 (2)	0.0456 (4)*	0.41
H6B	0.4410	0.8140	0.2732	0.055*	0.41
C7B	0.4947 (3)	0.5585 (6)	0.4529 (2)	0.0456 (4)*	0.21
H7B	0.5538	0.5132	0.3960	0.055*	0.21
C8B	0.0921 (8)	1.3637 (19)	0.3478 (6)	0.0456 (4)*	0.41
H81B	0.0500	1.3049	0.2796	0.068*	0.41
H82B	0.1362	1.5365	0.3363	0.068*	0.41
H83B	0.0245	1.3833	0.4042	0.068*	0.41

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0448 (9)	0.0382 (9)	0.0616 (11)	0.0076 (8)	−0.0098 (8)	0.0055 (8)
C1A	0.0314 (8)	0.0317 (8)	0.0516 (10)	0.0019 (6)	−0.0044 (8)	−0.0010 (8)
C2A	0.0458 (11)	0.0485 (11)	0.0480 (11)	0.0153 (9)	0.0020 (8)	0.0024 (9)
C3A	0.0452 (13)	0.0479 (13)	0.0599 (12)	0.0185 (9)	−0.0011 (9)	0.0000 (10)
C4A	0.0345 (9)	0.0253 (8)	0.0593 (11)	−0.0015 (6)	−0.0138 (8)	−0.0027 (7)
C5A	0.0584 (12)	0.0493 (13)	0.0459 (13)	0.0039 (10)	−0.0016 (11)	0.0067 (10)
C6A	0.0456 (10)	0.0523 (12)	0.0480 (12)	0.0120 (9)	0.0080 (9)	−0.0022 (11)
C7A	0.0448 (9)	0.0382 (9)	0.0616 (11)	0.0076 (8)	−0.0098 (8)	0.0055 (8)
C8A	0.0554 (13)	0.0366 (12)	0.099 (2)	0.0127 (9)	−0.0282 (13)	0.0029 (11)

Geometric parameters (Å, º) top

N1A—N1Aⁱ	1.275 (4)	N1B—N1Bⁱ	1.272 (5)
C1A—C6A	1.381 (3)	C1B—C2B	1.3900
C1A—C2A	1.391 (3)	C1B—C6B	1.3900
C2A—C3A	1.390 (3)	C2B—C3B	1.3900
C3A—C4A	1.380 (3)	C3B—C4B	1.3900
C4A—C5A	1.380 (3)	C4B—C5B	1.3900
C4A—C8A	1.508 (6)	C4B—C8B	1.500 (9)
C5A—C6A	1.392 (3)	C5B—C6B	1.3900

C6A—C1A—C2A	117.92 (17)	C2B—C1B—C6B	120.0
C3A—C2A—C1A	120.53 (19)	C1B—C2B—C3B	120.0
C4A—C3A—C2A	122.19 (19)	C2B—C3B—C4B	120.0
C3A—C4A—C5A	116.49 (17)	C3B—C4B—C5B	120.0
C3A—C4A—C8A	119.1 (3)	C3B—C4B—C8B	124.4 (3)
C5A—C4A—C8A	124.3 (4)	C5B—C4B—C8B	115.5 (3)
C4A—C5A—C6A	122.47 (19)	C4B—C5B—C6B	120.0
C1A—C6A—C5A	120.37 (18)	C5B—C6B—C1B	120.0

C6A—C1A—C2A—C3A	1.6 (3)	C6B—C1B—C2B—C3B	0.0
C1A—C2A—C3A—C4A	−0.4 (3)	C1B—C2B—C3B—C4B	0.0
C2A—C3A—C4A—C5A	−1.1 (3)	C2B—C3B—C4B—C5B	0.0
C2A—C3A—C4A—C8A	−179.4 (4)	C2B—C3B—C4B—C8B	179.0 (6)
C3A—C4A—C5A—C6A	1.4 (3)	C3B—C4B—C5B—C6B	0.0
C8A—C4A—C5A—C6A	179.6 (5)	C8B—C4B—C5B—C6B	−179.1 (6)
C2A—C1A—C6A—C5A	−1.3 (3)	C4B—C5B—C6B—C1B	0.0
C4A—C5A—C6A—C1A	−0.2 (4)	C2B—C1B—C6B—C5B	0.0

Symmetry code: (i) −x+1, −y+1, −z+1.

(3_300K3) N-(4-methylbenzylidene)-4-methylaniline top

Crystal data top

C₁₅H₁₅N	D_x = 1.198 Mg m⁻³
M_r = 209.28	Melting point: 89.4 C K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.8785 (7) Å	Cell parameters from 2644 reflections
b = 4.8853 (3) Å	θ = 3.4–29.8°
c = 12.0209 (8) Å	µ = 0.07 mm⁻¹
β = 90.489 (1)°	T = 300 K
V = 580.10 (7) Å³	Plate, colourless
Z = 2	0.40 × 0.30 × 0.08 mm
F(000) = 224

Data collection top

Bruker SMART 1000 CCD diffractometer	1691 independent reflections
Radiation source: fine-focus sealed tube	1299 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 8.192 pixels mm^-1	θ_max = 30.0°, θ_min = 2.1°
ω scan	h = −13→13
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −6→6
T_min = 0.973, T_max = 0.995	l = −16→16
8524 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.054	w = 1/[σ²(F_o²) + (0.0699P)² + 0.1095P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.158	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 0.22 e Å⁻³
1691 reflections	Δρ_min = −0.23 e Å⁻³
89 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.37 (3)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₁₅N	V = 580.10 (7) Å³
M_r = 209.28	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8785 (7) Å	µ = 0.07 mm⁻¹
b = 4.8853 (3) Å	T = 300 K
c = 12.0209 (8) Å	0.40 × 0.30 × 0.08 mm
β = 90.489 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	1691 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	1299 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.995	R_int = 0.027
8524 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.07	Δρ_max = 0.22 e Å⁻³
1691 reflections	Δρ_min = −0.23 e Å⁻³
89 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.45652 (19)	0.5681 (4)	0.52730 (17)	0.0479 (5)	0.29
C1A	0.36918 (18)	0.7684 (4)	0.47549 (19)	0.0380 (4)	0.59
C2A	0.2710 (2)	0.8901 (5)	0.54178 (19)	0.0469 (5)	0.59
H2A	0.2648	0.8422	0.6164	0.056*	0.59
C3A	0.1821 (3)	1.0826 (6)	0.4972 (3)	0.0507 (6)	0.59
H3A	0.1170	1.1600	0.5430	0.061*	0.59
C4A	0.1873 (3)	1.1623 (6)	0.3873 (3)	0.0394 (5)	0.59
C5A	0.2873 (4)	1.0451 (7)	0.3235 (2)	0.0512 (6)	0.59
H5A	0.2950	1.0978	0.2494	0.061*	0.59
C6A	0.3772 (2)	0.8507 (5)	0.3658 (2)	0.0485 (6)	0.59
H6A	0.4429	0.7759	0.3200	0.058*	0.59
C7A	0.45652 (19)	0.5681 (4)	0.52730 (17)	0.0479 (5)	0.29
H7A	0.4491	0.5374	0.6033	0.057*	0.29
C8A	0.0875 (7)	1.3742 (13)	0.3464 (6)	0.0642 (9)	0.59
H81A	0.1295	1.5514	0.3475	0.096*	0.59
H82A	0.0099	1.3755	0.3940	0.096*	0.59
H83A	0.0596	1.3306	0.2718	0.096*	0.59
N1B	0.4949 (3)	0.5581 (6)	0.4528 (2)	0.0449 (4)*	0.21
C1B	0.3901 (3)	0.7635 (5)	0.4344 (2)	0.0449 (4)*	0.41
C2B	0.3009 (3)	0.8502 (6)	0.51600 (19)	0.0449 (4)*	0.41
H2B	0.3066	0.7771	0.5873	0.054*	0.41
C3B	0.2033 (4)	1.0462 (8)	0.4910 (3)	0.0449 (4)*	0.41
H3B	0.1437	1.1042	0.5456	0.054*	0.41
C4B	0.1948 (4)	1.1554 (9)	0.3844 (3)	0.0449 (4)*	0.41
C5B	0.2840 (4)	1.0686 (9)	0.3028 (2)	0.0449 (4)*	0.41
H5B	0.2783	1.1417	0.2315	0.054*	0.41
C6B	0.3816 (3)	0.8727 (7)	0.3278 (2)	0.0449 (4)*	0.41
H6B	0.4412	0.8146	0.2732	0.054*	0.41
C7B	0.4949 (3)	0.5581 (6)	0.4528 (2)	0.0449 (4)*	0.21
H7B	0.5540	0.5124	0.3959	0.054*	0.21
C8B	0.0929 (9)	1.3651 (18)	0.3467 (6)	0.0449 (4)*	0.41
H81B	0.0048	1.2827	0.3430	0.067*	0.41
H82B	0.1171	1.4320	0.2745	0.067*	0.41
H83B	0.0918	1.5144	0.3986	0.067*	0.41

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0441 (9)	0.0378 (9)	0.0616 (12)	0.0078 (8)	−0.0092 (8)	0.0060 (8)
C1A	0.0312 (8)	0.0318 (8)	0.0509 (10)	0.0015 (6)	−0.0037 (7)	−0.0018 (8)
C2A	0.0450 (11)	0.0475 (11)	0.0482 (11)	0.0148 (9)	0.0027 (8)	0.0022 (9)
C3A	0.0456 (13)	0.0468 (13)	0.0597 (13)	0.0190 (9)	0.0002 (9)	0.0009 (10)
C4A	0.0340 (9)	0.0242 (8)	0.0600 (12)	−0.0016 (6)	−0.0129 (8)	−0.0028 (7)
C5A	0.0595 (13)	0.0490 (13)	0.0452 (13)	0.0041 (10)	−0.0006 (11)	0.0072 (10)
C6A	0.0453 (10)	0.0516 (12)	0.0488 (12)	0.0119 (9)	0.0086 (9)	−0.0019 (11)
C7A	0.0441 (9)	0.0378 (9)	0.0616 (12)	0.0078 (8)	−0.0092 (8)	0.0060 (8)
C8A	0.0553 (15)	0.0365 (11)	0.100 (2)	0.0130 (10)	−0.0282 (13)	0.0022 (12)

Geometric parameters (Å, º) top

N1A—N1Aⁱ	1.273 (4)	N1B—N1Bⁱ	1.272 (5)
C1A—C6A	1.381 (3)	C1B—C2B	1.3900
C1A—C2A	1.394 (3)	C1B—C6B	1.3900
C2A—C3A	1.391 (3)	C2B—C3B	1.3900
C3A—C4A	1.379 (3)	C3B—C4B	1.3900
C4A—C5A	1.381 (3)	C4B—C5B	1.3900
C4A—C8A	1.509 (6)	C4B—C8B	1.503 (9)
C5A—C6A	1.393 (3)	C5B—C6B	1.3900

C6A—C1A—C2A	117.85 (17)	C2B—C1B—C6B	120.0
C3A—C2A—C1A	120.55 (19)	C1B—C2B—C3B	120.0
C4A—C3A—C2A	122.12 (19)	C2B—C3B—C4B	120.0
C3A—C4A—C5A	116.61 (18)	C5B—C4B—C3B	120.0
C3A—C4A—C8A	118.4 (3)	C5B—C4B—C8B	114.9 (3)
C5A—C4A—C8A	124.9 (4)	C3B—C4B—C8B	125.0 (3)
C4A—C5A—C6A	122.43 (19)	C6B—C5B—C4B	120.0
C1A—C6A—C5A	120.40 (18)	C5B—C6B—C1B	120.0

C6A—C1A—C2A—C3A	1.7 (3)	C6B—C1B—C2B—C3B	0.0
C1A—C2A—C3A—C4A	−0.4 (3)	C1B—C2B—C3B—C4B	0.0
C2A—C3A—C4A—C5A	−1.2 (3)	C2B—C3B—C4B—C5B	0.0
C2A—C3A—C4A—C8A	−179.5 (4)	C2B—C3B—C4B—C8B	179.2 (6)
C3A—C4A—C5A—C6A	1.5 (3)	C3B—C4B—C5B—C6B	0.0
C8A—C4A—C5A—C6A	179.7 (5)	C8B—C4B—C5B—C6B	−179.2 (6)
C2A—C1A—C6A—C5A	−1.3 (3)	C4B—C5B—C6B—C1B	0.0
C4A—C5A—C6A—C1A	−0.3 (4)	C2B—C1B—C6B—C5B	0.0

Symmetry code: (i) −x+1, −y+1, −z+1.

(3_90K3) N-(4-methylbenzylidene)-4-methylaniline top

Crystal data top

C₁₅H₁₅N	D_x = 1.249 Mg m⁻³
M_r = 209.28	Melting point: 89.4 C K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.7951 (5) Å	Cell parameters from 4269 reflections
b = 4.8164 (3) Å	θ = 3.5–29.9°
c = 11.7933 (7) Å	µ = 0.07 mm⁻¹
β = 90.617 (1)°	T = 90 K
V = 556.34 (6) Å³	Plate, colourless
Z = 2	0.40 × 0.30 × 0.08 mm
F(000) = 224

Data collection top

Bruker SMART 1000 CCD diffractometer	1629 independent reflections
Radiation source: fine-focus sealed tube	1466 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Detector resolution: 8.192 pixels mm^-1	θ_max = 30.0°, θ_min = 2.1°
ω scan	h = −13→13
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	k = −6→6
T_min = 0.972, T_max = 0.994	l = −16→16
8144 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.043	w = 1/[σ²(F_o²) + (0.0689P)² + 0.1379P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.125	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.35 e Å⁻³
1629 reflections	Δρ_min = −0.21 e Å⁻³
89 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.097 (14)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₁₅N	V = 556.34 (6) Å³
M_r = 209.28	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.7951 (5) Å	µ = 0.07 mm⁻¹
b = 4.8164 (3) Å	T = 90 K
c = 11.7933 (7) Å	0.40 × 0.30 × 0.08 mm
β = 90.617 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	1629 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	1466 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.994	R_int = 0.018
8144 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.05	Δρ_max = 0.35 e Å⁻³
1629 reflections	Δρ_min = −0.21 e Å⁻³
89 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.45688 (11)	−0.4299 (2)	0.52917 (10)	0.0205 (3)	0.33
C1A	0.36881 (11)	−0.2256 (2)	0.47661 (11)	0.0148 (2)	0.67
C2A	0.26945 (12)	−0.1057 (3)	0.54478 (11)	0.0180 (3)	0.67
H2A	0.2636	−0.1583	0.6222	0.022*	0.67
C3A	0.17853 (15)	0.0904 (3)	0.50075 (13)	0.0188 (3)	0.67
H3A	0.1114	0.1683	0.5488	0.023*	0.67
C4A	0.18398 (18)	0.1749 (4)	0.38760 (15)	0.0150 (3)	0.67
C5A	0.28627 (17)	0.0574 (3)	0.32090 (12)	0.0194 (3)	0.67
H5A	0.2940	0.1140	0.2441	0.023*	0.67
C6A	0.37726 (12)	−0.1403 (3)	0.36386 (11)	0.0183 (3)	0.67
H6A	0.4451	−0.2170	0.3162	0.022*	0.67
C7A	0.45688 (11)	−0.4299 (2)	0.52917 (10)	0.0205 (3)	0.33
H7A	0.4510	−0.4614	0.6085	0.025*	0.33
C8A	0.0840 (4)	0.3927 (8)	0.3435 (3)	0.0203 (4)	0.67
H81A	0.1076	0.5742	0.3757	0.030*	0.67
H82A	−0.0089	0.3424	0.3658	0.030*	0.67
H83A	0.0888	0.4018	0.2606	0.030*	0.67
N1B	0.4939 (2)	−0.4384 (5)	0.45192 (18)	0.0190 (3)*	0.17
C1B	0.3893 (2)	−0.2285 (4)	0.43323 (18)	0.0190 (3)*	0.33
C2B	0.2993 (2)	−0.1419 (5)	0.51639 (15)	0.0190 (3)*	0.33
H2B	0.3050	−0.2188	0.5905	0.023*	0.33
C3B	0.2009 (3)	0.0573 (7)	0.4912 (2)	0.0190 (3)*	0.33
H3B	0.1393	0.1165	0.5480	0.023*	0.33
C4B	0.1924 (4)	0.1699 (8)	0.3828 (3)	0.0190 (3)*	0.33
C5B	0.2825 (3)	0.0833 (7)	0.2996 (2)	0.0190 (3)*	0.33
H5B	0.2767	0.1602	0.2256	0.023*	0.33
C6B	0.3809 (2)	−0.1159 (5)	0.32485 (16)	0.0190 (3)*	0.33
H6B	0.4424	−0.1751	0.2680	0.023*	0.33
C7B	0.4939 (2)	−0.4384 (5)	0.45192 (18)	0.0190 (3)*	0.17
H7B	0.5541	−0.4850	0.3922	0.023*	0.17
C8B	0.0913 (9)	0.376 (2)	0.3482 (7)	0.0190 (3)*	0.33
H81B	0.0509	0.3220	0.2751	0.028*	0.33
H82B	0.1354	0.5575	0.3410	0.028*	0.33
H83B	0.0196	0.3863	0.4054	0.028*	0.33

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0193 (5)	0.0133 (5)	0.0287 (5)	0.0021 (4)	−0.0076 (4)	0.0036 (4)
C1A	0.0118 (5)	0.0108 (5)	0.0218 (5)	0.0009 (4)	−0.0027 (4)	0.0001 (4)
C2A	0.0178 (6)	0.0165 (5)	0.0196 (5)	0.0046 (4)	0.0000 (4)	0.0004 (4)
C3A	0.0164 (6)	0.0169 (6)	0.0231 (6)	0.0068 (4)	−0.0006 (4)	−0.0002 (4)
C4A	0.0119 (5)	0.0084 (5)	0.0246 (6)	−0.0005 (4)	−0.0048 (4)	−0.0017 (4)
C5A	0.0207 (6)	0.0169 (6)	0.0206 (6)	0.0006 (4)	−0.0010 (5)	0.0023 (5)
C6A	0.0158 (5)	0.0182 (5)	0.0209 (5)	0.0037 (4)	0.0024 (4)	−0.0002 (5)
C7A	0.0193 (5)	0.0133 (5)	0.0287 (5)	0.0021 (4)	−0.0076 (4)	0.0036 (4)
C8A	0.0177 (7)	0.0107 (8)	0.0322 (8)	0.0059 (5)	−0.0102 (6)	0.0019 (5)

Geometric parameters (Å, º) top

N1A—N1Aⁱ	1.287 (2)	N1B—N1Bⁱ	1.284 (4)
C1A—C2A	1.3941 (15)	C1B—C2B	1.3900
C1A—C6A	1.3951 (16)	C1B—C6B	1.3900
C2A—C3A	1.3948 (15)	C2B—C3B	1.3900
C3A—C4A	1.3966 (17)	C3B—C4B	1.3900
C4A—C5A	1.3998 (16)	C4B—C5B	1.3900
C4A—C8A	1.523 (3)	C4B—C8B	1.457 (9)
C5A—C6A	1.3957 (16)	C5B—C6B	1.3900

C2A—C1A—C6A	118.47 (10)	C2B—C1B—C6B	120.0
C1A—C2A—C3A	120.84 (10)	C1B—C2B—C3B	120.0
C2A—C3A—C4A	121.48 (10)	C2B—C3B—C4B	120.0
C3A—C4A—C5A	117.01 (11)	C5B—C4B—C3B	120.0
C3A—C4A—C8A	119.7 (2)	C5B—C4B—C8B	116.2 (4)
C5A—C4A—C8A	123.2 (2)	C3B—C4B—C8B	123.8 (4)
C6A—C5A—C4A	121.99 (11)	C4B—C5B—C6B	120.0
C1A—C6A—C5A	120.18 (10)	C5B—C6B—C1B	120.0

C6A—C1A—C2A—C3A	1.42 (18)	C6B—C1B—C2B—C3B	0.0
C1A—C2A—C3A—C4A	−0.36 (18)	C1B—C2B—C3B—C4B	0.0
C2A—C3A—C4A—C5A	−1.08 (17)	C2B—C3B—C4B—C5B	0.0
C2A—C3A—C4A—C8A	−179.1 (3)	C2B—C3B—C4B—C8B	178.9 (6)
C3A—C4A—C5A—C6A	1.49 (17)	C3B—C4B—C5B—C6B	0.0
C8A—C4A—C5A—C6A	179.5 (3)	C8B—C4B—C5B—C6B	−179.0 (6)
C2A—C1A—C6A—C5A	−1.01 (18)	C4B—C5B—C6B—C1B	0.0
C4A—C5A—C6A—C1A	−0.46 (18)	C2B—C1B—C6B—C5B	0.0

Symmetry code: (i) −x+1, −y−1, −z+1.

Experimental details

	(1_rt)	(1_200K)	(1_90K)	(2_rt)
Crystal data
Chemical formula	C₁₃H₁₀N₂O₂	C₁₃H₁₀N₂O₂	C₁₃H₁₀N₂O₂	C₁₄H₁₂ClN
M_r	226.23	226.23	226.23	229.70
Crystal system, space group	Monoclinic, P2₁/n	Monoclinic, P2₁/n	Monoclinic, P2₁/n	Monoclinic, P2₁/a
Temperature (K)	300	200	90	300
a, b, c (Å)	14.6363 (11), 10.8175 (8), 14.7228 (11)	14.4053 (11), 10.7367 (8), 14.7627 (12)	14.2105 (12), 10.6596 (9), 14.8045 (12)	5.9663 (5), 7.3989 (7), 13.7221 (12)
β (°)	101.943 (1)	101.617 (2)	101.228 (2)	99.120 (2)
V (Å³)	2280.6 (3)	2236.5 (3)	2199.6 (3)	598.09 (9)
Z	8	8	8	2
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.09	0.09	0.10	0.29
Crystal size (mm)	0.46 × 0.40 × 0.28	0.46 × 0.40 × 0.28	0.46 × 0.40 × 0.28	0.48 × 0.34 × 0.18

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer	Bruker SMART 1000 CCD diffractometer	Bruker SMART 1000 CCD diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan SADABS (Sheldrick, 2002)	Multi-scan SADABS (Sheldrick, 2002)	Multi-scan SADABS (Sheldrick, 2002)	Multi-scan SADABS (Sheldrick, 2002)
T_min, T_max	0.959, 0.975	0.959, 0.974	0.958, 0.974	0.874, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	34291, 6663, 3616	33619, 6529, 4886	33043, 6400, 5521	8950, 1760, 1271
R_int	0.041	0.024	0.023	0.019
(sin θ/λ)_max (Å⁻¹)	0.705	0.704	0.704	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.174, 1.03	0.047, 0.131, 1.02	0.039, 0.112, 1.02	0.060, 0.195, 1.08
No. of reflections	6663	6529	6400	1760
No. of parameters	399	387	387	72
No. of restraints	5	0	0	0
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	All H-atom parameters refined	All H-atom parameters refined	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.29	0.27, −0.25	0.42, −0.19	0.24, −0.36

	(2_200K)	(2_90K)	(3_300K)	(3_250K)
Crystal data
Chemical formula	C₁₄H₁₂ClN	C₁₄H₁₂ClN	C₁₅H₁₅N	C₁₅H₁₅N
M_r	229.70	229.70	209.28	209.28
Crystal system, space group	Monoclinic, P2₁/a	Monoclinic, P2₁/a	Monoclinic, P2₁/c	Monoclinic, P2₁/c
Temperature (K)	200	90	300	250
a, b, c (Å)	5.9174 (5), 7.2879 (6), 13.70490 (11)	5.8827 (6), 7.1953 (7), 13.6919 (14)	9.8766 (7), 4.8839 (4), 12.0187 (9)	9.8649 (6), 4.8663 (3), 11.9484 (8)
β (°)	99.233 (2)	99.385 (2)	90.499 (1)	90.518 (1)
V (Å³)	583.37 (7)	571.79 (10)	579.72 (8)	573.57 (6)
Z	2	2	2	2
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.30	0.30	0.07	0.07
Crystal size (mm)	0.48 × 0.34 × 0.18	0.48 × 0.34 × 0.18	0.40 × 0.30 × 0.08	0.40 × 0.30 × 0.08

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer	Bruker SMART 1000 CCD diffractometer	Bruker SMART 1000 CCD diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan SADABS (Sheldrick, 2002)	Multi-scan SADABS (Sheldrick, 2002)	Multi-scan SADABS (Sheldrick, 2002)	Multi-scan SADABS (Sheldrick, 2002)
T_min, T_max	0.871, 0.949	0.868, 0.948	0.973, 0.995	0.972, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	8648, 1707, 1454	8393, 1668, 1536	8496, 1689, 1330	8404, 1677, 1406
R_int	0.016	0.017	0.022	0.019
(sin θ/λ)_max (Å⁻¹)	0.704	0.704	0.704	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.148, 1.12	0.059, 0.141, 0.60	0.052, 0.149, 1.05	0.048, 0.135, 1.08
No. of reflections	1707	1668	1689	1677
No. of parameters	72	72	89	89
No. of restraints	0	0	0	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.37	0.68, −0.65	0.23, −0.20	0.22, −0.20

	(3_200K)	(3_150K)	(3_90K)	(3_90K2)
Crystal data
Chemical formula	C₁₅H₁₅N	C₁₅H₁₅N	C₁₅H₁₅N	C₁₅H₁₅N
M_r	209.28	209.28	209.28	209.28
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/c	Monoclinic, P2₁/c	Monoclinic, P2₁/c
Temperature (K)	200	150	90	90
a, b, c (Å)	9.8565 (6), 4.8494 (3), 11.8748 (7)	9.8477 (6), 4.8327 (3), 11.7991 (7)	9.8184 (6), 4.8159 (3), 11.7536 (7)	9.7961 (6), 4.8169 (3), 11.7947 (7)
β (°)	90.561 (1)	90.631 (1)	90.689 (1)	90.614 (1)
V (Å³)	567.57 (6)	561.50 (6)	555.72 (6)	556.52 (6)
Z	2	2	2	2
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.07	0.07	0.07	0.07
Crystal size (mm)	0.40 × 0.30 × 0.08	0.40 × 0.30 × 0.08	0.40 × 0.30 × 0.08	0.40 × 0.30 × 0.08

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer	Bruker SMART 1000 CCD diffractometer	Bruker SMART 1000 CCD diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan SADABS (Sheldrick, 2002)	Multi-scan SADABS (Sheldrick, 2002)	Multi-scan SADABS (Sheldrick, 2002)	Multi-scan SADABS (Sheldrick, 2002)
T_min, T_max	0.972, 0.994	0.972, 0.994	0.972, 0.994	0.972, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	8329, 1661, 1428	8213, 1641, 1453	8100, 1624, 1473	8121, 1630, 1469
R_int	0.017	0.015	0.013	0.018
(sin θ/λ)_max (Å⁻¹)	0.703	0.703	0.703	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.134, 1.08	0.043, 0.126, 1.06	0.041, 0.121, 1.07	0.042, 0.123, 1.05
No. of reflections	1661	1641	1624	1630
No. of parameters	89	89	89	89
No. of restraints	0	0	0	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.19	0.31, −0.18	0.36, −0.18	0.35, −0.20

	(3_90K4)	(3_300K2)	(3_300K3)	(3_90K3)
Crystal data
Chemical formula	C₁₅H₁₅N	C₁₅H₁₅N	C₁₅H₁₅N	C₁₅H₁₅N
M_r	209.28	209.28	209.28	209.28
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/c	Monoclinic, P2₁/c	Monoclinic, P2₁/c
Temperature (K)	90	300	300	90
a, b, c (Å)	9.8177 (5), 4.8150 (3), 11.7497 (6)	9.8781 (7), 4.8848 (4), 12.0214 (9)	9.8785 (7), 4.8853 (3), 12.0209 (8)	9.7951 (5), 4.8164 (3), 11.7933 (7)
β (°)	90.691 (1)	90.488 (1)	90.489 (1)	90.617 (1)
V (Å³)	555.39 (5)	580.04 (8)	580.10 (7)	556.34 (6)
Z	2	2	2	2
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.07	0.07	0.07	0.07
Crystal size (mm)	0.40 × 0.30 × 0.08	0.40 × 0.30 × 0.08	0.40 × 0.30 × 0.08	0.40 × 0.30 × 0.08

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer	Bruker SMART 1000 CCD diffractometer	Bruker SMART 1000 CCD diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan SADABS (Sheldrick, 2002)	Multi-scan SADABS (Sheldrick, 2002)	Multi-scan SADABS (Sheldrick, 2002)	Multi-scan SADABS (Sheldrick, 2002)
T_min, T_max	0.972, 0.994	0.973, 0.995	0.973, 0.995	0.972, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	8085, 1622, 1455	8508, 1692, 1326	8524, 1691, 1299	8144, 1629, 1466
R_int	0.019	0.024	0.027	0.018
(sin θ/λ)_max (Å⁻¹)	0.703	0.704	0.704	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.119, 1.06	0.051, 0.149, 1.06	0.054, 0.158, 1.07	0.043, 0.125, 1.05
No. of reflections	1622	1692	1691	1629
No. of parameters	89	89	89	89
No. of restraints	0	0	0	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.20	0.22, −0.21	0.22, −0.23	0.35, −0.21

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.

Format		BIBTeX
		EndNote
		RefMan
		Refer
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Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text