Isostructuralism among `bridge-flipped' isomeric benzylideneanilines and phenylhydrazones

`Bridge-flipped' isomers may be defined as pairs of molecules related by a reversal of a bridge of atoms connecting two major parts of the individual molecules. This kind of isomerism is commonly found among benzylideneanilines and phenylhydrazones. Isostructural pairs might be suitable for co-crystallization and are thus useful in the preparation of new solid materials. Although most of the examples of bridge-flipped isomeric benzylideneanilines and phenylhydrazones in the crystallographic literature are not isostructural, a small number of isostructural pairs have been reported by previous workers. This paper describes the molecular and crystal structures of four pairs of bridge-flipped isomers: two isostructural phenylhydrazones, (E)-2-bromobenzaldehyde 4-cyanophenylhydrazone (I) and (E)-4-cyanobenzaldehyde 2-bromophenylhydrazone (II); two pairs of isostructural benzylideneanilines, N-(2-trifluoromethylbenzylidene)-2-methylaniline (III) and N-(2-methylbenzylidene)-2-trifluoromethylaniline (IV), and N-(2-bromobenzylidene)-2-methylaniline (V) and N-(2-methylbenzylidene)-2-bromoaniline (VI); and a pair of benzylideneanilines with closely similar unit-cell dimensions but different packing arrangements, N-(4-methylbenzylidene)-4-cyanoaniline (VII) and N-(4-cyanobenzylidene)-4-methylaniline (VIII). The structure of (V) is disordered. The packing arrangement of (VIII) resembles that of the chloro-/methyl-substituted benzylideneanilines MBZCLA/MBZCLB [N-(4-methylbenzylidene)-4-chloroaniline and N-(4-chlorobenzylidene)-4-methylaniline]. Although intermolecular hydrogen bonding plays a part in the isostructuralism of the two phenylhydrazones, the other examples of isostructuralism occur in the absence of similar, relatively strong intermolecular interactions.

S1. Comment

The stucture of the title compound, (I), is shown below. Dimensions are available in the archived CIF.

For related literature, see (type here to add references to related literature).

S2. Experimental

(type here to add preparation details)

S3. Refinement

(type here to add refinement details)

Computing details

For all compounds, data collection: SMART, Bruker; cell refinement: SAINT, Bruker; data reduction: SAINT, Bruker; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

(I) (E)-2-bromobenzaldehyde 4-cyanophenylhydrazone

Crystal data

C14H10BrN3	Dx = 1.577 Mg m^−3
Mr = 300.16	Melting point = 200–230 K
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 4.2021 (3) Å	Cell parameters from 3519 reflections
b = 21.0409 (13) Å	θ = 2.4–25.0°
c = 14.3803 (9) Å	µ = 3.24 mm^−1
β = 96.248 (1)°	T = 173 K
V = 1263.90 (14) Å^3	Needle, yellow
Z = 4	0.50 × 0.20 × 0.20 mm
F(000) = 600

Data collection

Bruker SMART Platform CCD diffractometer	2202 independent reflections
Radiation source: normal-focus sealed tube	2082 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
area detector, ω scans per phi	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan SADABS (Blessing, 1995)	h = −4→4
Tmin = 0.462, Tmax = 0.521	k = −24→24
6085 measured reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.061	w = 1/[σ^2(Fo^2) + (0.0102P)^2 + 1.0482P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2202 reflections	Δρmax = 0.55 e Å^−3
167 parameters	Δρmin = −0.52 e Å^−3
2 restraints	Absolute structure: Flack H D (1983), 1087 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.036 (10)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	1.24368 (8)	0.534957 (17)	0.82315 (4)	0.05691 (13)
C1	0.9177 (7)	0.51504 (14)	0.6390 (2)	0.0302 (6)
C2	1.1188 (7)	0.48836 (16)	0.7118 (2)	0.0373 (7)
C3	1.2345 (8)	0.42662 (17)	0.7064 (3)	0.0451 (9)
H3	1.3711	0.4093	0.7571	0.054*
C4	1.1517 (9)	0.39093 (16)	0.6282 (3)	0.0488 (9)
H4	1.2285	0.3486	0.6247	0.059*
C5	0.9568 (9)	0.41636 (18)	0.5543 (3)	0.0426 (9)
H5	0.9008	0.3917	0.4996	0.051*
C6	0.8435 (8)	0.47732 (14)	0.5597 (2)	0.0358 (7)
H6	0.7108	0.4943	0.5079	0.043*
C7	0.2433 (6)	0.68129 (14)	0.51637 (19)	0.0263 (6)
C8	0.1169 (6)	0.64220 (13)	0.44284 (19)	0.0270 (6)
H8	0.1775	0.5987	0.4413	0.032*
C9	−0.0963 (6)	0.66717 (13)	0.3726 (2)	0.0289 (6)
H9	−0.1811	0.6406	0.3226	0.035*
C10	−0.1897 (7)	0.73063 (14)	0.3738 (2)	0.0288 (6)
C11	−0.0656 (7)	0.76928 (14)	0.4473 (2)	0.0316 (7)
H11	−0.1281	0.8126	0.4488	0.038*
C12	0.1475 (7)	0.74516 (13)	0.5180 (2)	0.0293 (6)
H12	0.2301	0.7719	0.5682	0.035*
C13	0.7886 (7)	0.57951 (14)	0.64407 (19)	0.0297 (6)
H13	0.8647	0.6071	0.6938	0.036*
C14	−0.4140 (8)	0.75415 (15)	0.2993 (2)	0.0338 (7)
H1N	0.542 (7)	0.6811 (15)	0.624 (2)	0.026 (8)*
N1	0.5710 (6)	0.59807 (12)	0.58011 (19)	0.0271 (6)
N2	0.4587 (6)	0.65816 (12)	0.58620 (18)	0.0291 (5)
N3	−0.5938 (7)	0.77063 (14)	0.2381 (2)	0.0447 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0533 (2)	0.0825 (3)	0.03093 (16)	0.0129 (2)	−0.01351 (12)	0.0036 (2)
C1	0.0257 (15)	0.0331 (16)	0.0316 (16)	−0.0047 (12)	0.0024 (12)	0.0095 (12)
C2	0.0273 (16)	0.053 (2)	0.0318 (17)	0.0017 (14)	0.0038 (12)	0.0120 (15)
C3	0.0351 (18)	0.054 (2)	0.047 (2)	0.0149 (16)	0.0069 (15)	0.0256 (18)
C4	0.050 (2)	0.0375 (19)	0.061 (2)	0.0101 (16)	0.0188 (19)	0.0106 (17)
C5	0.044 (2)	0.0324 (19)	0.052 (2)	0.0003 (15)	0.0095 (18)	−0.0010 (17)
C6	0.0338 (17)	0.0363 (18)	0.0362 (17)	−0.0035 (12)	−0.0008 (13)	0.0034 (13)
C7	0.0252 (14)	0.0310 (16)	0.0226 (13)	−0.0036 (11)	0.0021 (11)	0.0017 (11)
C8	0.0254 (15)	0.0239 (14)	0.0309 (15)	−0.0008 (11)	−0.0008 (12)	−0.0021 (12)
C9	0.0264 (15)	0.0316 (16)	0.0276 (15)	−0.0033 (12)	−0.0018 (11)	−0.0044 (12)
C10	0.0250 (15)	0.0374 (18)	0.0238 (15)	0.0006 (13)	0.0024 (12)	0.0049 (13)
C11	0.0334 (17)	0.0280 (15)	0.0339 (17)	0.0053 (12)	0.0065 (13)	0.0017 (13)
C12	0.0312 (16)	0.0284 (16)	0.0278 (14)	−0.0001 (13)	0.0003 (12)	−0.0046 (12)
C13	0.0289 (15)	0.0333 (16)	0.0255 (15)	−0.0035 (12)	−0.0029 (12)	0.0038 (12)
C14	0.0328 (16)	0.0377 (18)	0.0311 (17)	−0.0005 (14)	0.0047 (13)	0.0051 (14)
N1	0.0288 (13)	0.0250 (14)	0.0269 (14)	−0.0028 (10)	0.0005 (11)	0.0037 (11)
N2	0.0327 (13)	0.0262 (13)	0.0261 (13)	−0.0024 (11)	−0.0072 (10)	−0.0047 (11)
N3	0.0445 (18)	0.0488 (17)	0.0391 (17)	0.0064 (13)	−0.0024 (14)	0.0120 (14)

Geometric parameters (Å, º)

Br1—C2	1.902 (3)	C8—C9	1.379 (4)
C1—C2	1.390 (4)	C8—H8	0.95
C1—C6	1.397 (4)	C9—C10	1.392 (4)
C1—C13	1.466 (4)	C9—H9	0.95
C2—C3	1.392 (5)	C10—C11	1.390 (4)
C3—C4	1.366 (5)	C10—C14	1.435 (4)
C3—H3	0.95	C11—C12	1.377 (4)
C4—C5	1.377 (5)	C11—H11	0.95
C4—H4	0.95	C12—H12	0.95
C5—C6	1.373 (5)	C13—N1	1.285 (4)
C5—H5	0.95	C13—H13	0.95
C6—H6	0.95	C14—N3	1.149 (4)
C7—N2	1.366 (4)	N1—N2	1.356 (4)
C7—C8	1.398 (4)	N2—H1N	0.78 (3)
C7—C12	1.404 (4)
C2—C1—C6	116.7 (3)	C9—C8—H8	120
C2—C1—C13	122.3 (3)	C7—C8—H8	120
C6—C1—C13	121.0 (3)	C8—C9—C10	121.2 (3)
C1—C2—C3	121.5 (3)	C8—C9—H9	119
C1—C2—Br1	121.0 (2)	C10—C9—H9	119
C3—C2—Br1	117.5 (2)	C11—C10—C9	119.2 (3)
C4—C3—C2	120.0 (3)	C11—C10—C14	121.8 (3)
C4—C3—H3	120	C9—C10—C14	119.0 (3)
C2—C3—H3	120	C12—C11—C10	120.4 (3)
C3—C4—C5	119.9 (3)	C12—C11—H11	120
C3—C4—H4	120	C10—C11—H11	120
C5—C4—H4	120	C11—C12—C7	120.3 (3)
C6—C5—C4	120.0 (4)	C11—C12—H12	120
C6—C5—H5	120	C7—C12—H12	120
C4—C5—H5	120	N1—C13—C1	118.9 (3)
C5—C6—C1	121.9 (3)	N1—C13—H13	121
C5—C6—H6	119	C1—C13—H13	121
C1—C6—H6	119	N3—C14—C10	177.3 (3)
N2—C7—C8	120.9 (3)	C13—N1—N2	117.6 (3)
N2—C7—C12	119.8 (3)	N1—N2—C7	119.5 (3)
C8—C7—C12	119.3 (2)	N1—N2—H1N	119 (2)
C9—C8—C7	119.5 (3)	C7—N2—H1N	120 (2)
C6—C1—C2—C3	−1.3 (4)	C8—C9—C10—C11	−0.2 (4)
C13—C1—C2—C3	178.9 (3)	C8—C9—C10—C14	−179.6 (3)
C6—C1—C2—Br1	179.1 (2)	C9—C10—C11—C12	0.1 (4)
C13—C1—C2—Br1	−0.7 (4)	C14—C10—C11—C12	179.5 (3)
C1—C2—C3—C4	0.2 (5)	C10—C11—C12—C7	0.4 (4)
Br1—C2—C3—C4	179.8 (3)	N2—C7—C12—C11	179.0 (3)
C2—C3—C4—C5	0.8 (5)	C8—C7—C12—C11	−0.8 (4)
C3—C4—C5—C6	−0.6 (5)	C2—C1—C13—N1	−170.7 (3)
C4—C5—C6—C1	−0.5 (5)	C6—C1—C13—N1	9.5 (4)
C2—C1—C6—C5	1.5 (4)	C1—C13—N1—N2	−179.3 (3)
C13—C1—C6—C5	−178.7 (3)	C13—N1—N2—C7	175.6 (3)
N2—C7—C8—C9	−179.0 (3)	C8—C7—N2—N1	5.4 (4)
C12—C7—C8—C9	0.8 (4)	C12—C7—N2—N1	−174.4 (3)
C7—C8—C9—C10	−0.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···N3^i	0.78 (3)	2.35 (3)	3.108 (4)	164 (3)

Symmetry code: (i) x+3/2, −y+3/2, z+1/2.

(II) (E)-4-cyanobenzaldehyde 2-bromophenylhydrazone

Crystal data

C14H10BrN3	Dx = 1.557 Mg m^−3
Mr = 300.16	Melting point = 158–220 K
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 4.4902 (4) Å	Cell parameters from 2385 reflections
b = 19.9376 (17) Å	θ = 2.5–25.0°
c = 14.3182 (12) Å	µ = 3.20 mm^−1
β = 92.884 (1)°	T = 173 K
V = 1280.20 (19) Å^3	Needle, yellow
Z = 4	0.50 × 0.15 × 0.15 mm
F(000) = 600

Data collection

Siemens SMART Platform CCD diffractometer	2226 independent reflections
Radiation source: normal-focus sealed tube	2132 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
area detector, ω scans per phi	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan SADABS (Blessing, 1995)	h = −5→5
Tmin = 0.565, Tmax = 0.616	k = −23→23
6162 measured reflections	l = −16→16

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.053	w = 1/[σ^2(Fo^2) + (0.0003P)^2 + 0.4653P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.002
2226 reflections	Δρmax = 0.29 e Å^−3
167 parameters	Δρmin = −0.34 e Å^−3
2 restraints	Absolute structure: Flack H D (1983), 1085 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.030 (9)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	1.13943 (7)	0.550056 (15)	0.83579 (4)	0.05249 (11)
C1	0.8386 (5)	0.51825 (13)	0.66030 (18)	0.0285 (6)
C2	1.0395 (6)	0.49538 (15)	0.73042 (19)	0.0350 (6)
C3	1.1681 (7)	0.43223 (16)	0.7258 (2)	0.0432 (8)
H3	1.3056	0.4177	0.7742	0.052*
C4	1.0966 (7)	0.39063 (15)	0.6511 (2)	0.0454 (8)
H4	1.1817	0.3471	0.6483	0.054*
C5	0.9008 (7)	0.41271 (16)	0.5806 (3)	0.0418 (8)
H5	0.8527	0.3844	0.5287	0.050*
C6	0.7729 (6)	0.47606 (14)	0.5846 (2)	0.0349 (6)
H6	0.6393	0.4907	0.5352	0.042*
C7	0.1537 (5)	0.67997 (13)	0.53650 (18)	0.0247 (5)
C8	0.0438 (5)	0.63803 (13)	0.46481 (18)	0.0298 (6)
H8	0.1104	0.5929	0.4622	0.036*
C9	−0.1601 (6)	0.66159 (13)	0.39783 (19)	0.0311 (6)
H9	−0.2360	0.6325	0.3498	0.037*
C10	−0.2552 (5)	0.72776 (14)	0.40034 (19)	0.0292 (6)
C11	−0.1496 (6)	0.77009 (14)	0.47230 (19)	0.0331 (6)
H11	−0.2160	0.8153	0.4747	0.040*
C12	0.0517 (6)	0.74570 (13)	0.53980 (18)	0.0315 (6)
H12	0.1218	0.7742	0.5893	0.038*
C13	0.3783 (5)	0.65707 (13)	0.60761 (18)	0.0277 (6)
H13	0.4371	0.6853	0.6588	0.033*
C14	−0.4640 (6)	0.75373 (15)	0.3291 (2)	0.0362 (7)
H1N	0.757 (6)	0.6049 (14)	0.7038 (19)	0.016 (7)*
N1	0.4941 (5)	0.59865 (12)	0.59998 (16)	0.0267 (5)
N2	0.7051 (5)	0.58045 (12)	0.66635 (17)	0.0308 (5)
N3	−0.6304 (6)	0.77423 (14)	0.27314 (19)	0.0510 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.05700 (18)	0.0653 (2)	0.03371 (15)	0.0195 (2)	−0.01200 (11)	−0.0019 (2)
C1	0.0238 (12)	0.0277 (14)	0.0344 (15)	0.0028 (11)	0.0064 (11)	0.0072 (11)
C2	0.0344 (15)	0.0421 (17)	0.0289 (15)	0.0016 (12)	0.0053 (11)	0.0100 (12)
C3	0.0391 (16)	0.0486 (19)	0.0430 (18)	0.0187 (14)	0.0113 (13)	0.0182 (14)
C4	0.0509 (18)	0.0345 (18)	0.052 (2)	0.0136 (14)	0.0156 (16)	0.0087 (15)
C5	0.0400 (17)	0.0383 (18)	0.0481 (19)	0.0017 (14)	0.0110 (15)	0.0025 (15)
C6	0.0326 (14)	0.0330 (15)	0.0391 (16)	−0.0013 (12)	0.0016 (12)	0.0022 (13)
C7	0.0218 (12)	0.0269 (14)	0.0255 (13)	−0.0036 (10)	0.0012 (9)	−0.0004 (10)
C8	0.0293 (13)	0.0280 (15)	0.0321 (15)	0.0024 (11)	0.0006 (11)	−0.0015 (11)
C9	0.0294 (13)	0.0354 (16)	0.0281 (13)	−0.0032 (11)	−0.0021 (11)	−0.0061 (11)
C10	0.0206 (13)	0.0417 (16)	0.0255 (14)	0.0016 (11)	0.0025 (10)	0.0033 (12)
C11	0.0347 (15)	0.0297 (15)	0.0348 (16)	0.0074 (12)	0.0013 (12)	−0.0007 (12)
C12	0.0319 (14)	0.0326 (15)	0.0295 (14)	0.0006 (12)	−0.0020 (11)	−0.0055 (12)
C13	0.0253 (13)	0.0311 (15)	0.0265 (13)	−0.0006 (11)	−0.0013 (10)	−0.0019 (11)
C14	0.0354 (15)	0.0427 (17)	0.0303 (15)	0.0010 (12)	0.0004 (15)	0.0042 (14)
N1	0.0219 (11)	0.0299 (13)	0.0279 (12)	0.0014 (9)	−0.0016 (9)	0.0041 (10)
N2	0.0313 (12)	0.0305 (13)	0.0298 (13)	0.0026 (11)	−0.0053 (10)	−0.0024 (11)
N3	0.0434 (15)	0.0665 (19)	0.0420 (16)	0.0056 (13)	−0.0087 (13)	0.0144 (14)

Geometric parameters (Å, º)

Br1—C2	1.897 (3)	C8—C9	1.375 (4)
C1—N2	1.382 (3)	C8—H8	0.95
C1—C6	1.392 (4)	C9—C10	1.388 (4)
C1—C2	1.392 (4)	C9—H9	0.95
C2—C3	1.388 (4)	C10—C11	1.396 (4)
C3—C4	1.379 (5)	C10—C14	1.446 (4)
C3—H3	0.95	C11—C12	1.378 (4)
C4—C5	1.377 (5)	C11—H11	0.95
C4—H4	0.95	C12—H12	0.95
C5—C6	1.390 (4)	C13—N1	1.283 (3)
C5—H5	0.95	C13—H13	0.95
C6—H6	0.95	C14—N3	1.143 (3)
C7—C12	1.390 (4)	N1—N2	1.357 (3)
C7—C8	1.395 (3)	N2—H1N	0.75 (3)
C7—C13	1.469 (3)
N2—C1—C6	121.0 (2)	C9—C8—H8	120
N2—C1—C2	121.1 (2)	C7—C8—H8	120
C6—C1—C2	117.9 (2)	C8—C9—C10	120.1 (2)
C3—C2—C1	121.3 (3)	C8—C9—H9	120
C3—C2—Br1	118.4 (2)	C10—C9—H9	120
C1—C2—Br1	120.3 (2)	C9—C10—C11	120.0 (2)
C4—C3—C2	120.1 (3)	C9—C10—C14	120.8 (3)
C4—C3—H3	120	C11—C10—C14	119.2 (2)
C2—C3—H3	120	C12—C11—C10	119.4 (2)
C5—C4—C3	119.5 (3)	C12—C11—H11	120
C5—C4—H4	120	C10—C11—H11	120
C3—C4—H4	120	C11—C12—C7	121.0 (2)
C4—C5—C6	120.7 (3)	C11—C12—H12	120
C4—C5—H5	120	C7—C12—H12	120
C6—C5—H5	120	N1—C13—C7	119.4 (2)
C5—C6—C1	120.6 (3)	N1—C13—H13	120
C5—C6—H6	120	C7—C13—H13	120
C1—C6—H6	120	N3—C14—C10	179.6 (4)
C12—C7—C8	119.0 (2)	C13—N1—N2	117.1 (2)
C12—C7—C13	119.0 (2)	N1—N2—C1	119.1 (2)
C8—C7—C13	121.9 (2)	N1—N2—H1N	120 (2)
C9—C8—C7	120.5 (2)	C1—N2—H1N	120 (2)
N2—C1—C2—C3	178.3 (2)	C8—C9—C10—C11	−1.6 (4)
C6—C1—C2—C3	−0.7 (4)	C8—C9—C10—C14	178.5 (3)
N2—C1—C2—Br1	−0.9 (3)	C9—C10—C11—C12	0.8 (4)
C6—C1—C2—Br1	−179.92 (19)	C14—C10—C11—C12	−179.3 (3)
C1—C2—C3—C4	−0.4 (4)	C10—C11—C12—C7	0.8 (4)
Br1—C2—C3—C4	178.9 (2)	C8—C7—C12—C11	−1.6 (4)
C2—C3—C4—C5	1.1 (4)	C13—C7—C12—C11	177.3 (2)
C3—C4—C5—C6	−0.7 (5)	C12—C7—C13—N1	−173.4 (2)
C4—C5—C6—C1	−0.4 (5)	C8—C7—C13—N1	5.4 (4)
N2—C1—C6—C5	−177.9 (3)	C7—C13—N1—N2	178.6 (2)
C2—C1—C6—C5	1.1 (4)	C13—N1—N2—C1	−179.2 (2)
C12—C7—C8—C9	0.7 (4)	C6—C1—N2—N1	3.9 (4)
C13—C7—C8—C9	−178.2 (2)	C2—C1—N2—N1	−175.1 (2)
C7—C8—C9—C10	0.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···N3^i	0.75 (3)	2.64 (3)	3.341 (4)	155 (3)
N2—H1N···Br1	0.75 (3)	2.72 (3)	3.095 (2)	113 (2)

Symmetry code: (i) x+3/2, −y+3/2, z+1/2.

(III) N-(2-trifluoromethylbenzylidene)-2-methylaniline

Crystal data

C15H12F3N	Dx = 1.395 Mg m^−3
Mr = 263.26	Melting point = 53–56 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.6046 (6) Å	Cell parameters from 2822 reflections
b = 7.7953 (5) Å	θ = 2.6–25.1°
c = 17.2756 (11) Å	µ = 0.11 mm^−1
β = 104.316 (1)°	T = 173 K
V = 1253.27 (14) Å^3	Prism, yellow
Z = 4	0.50 × 0.50 × 0.18 mm
F(000) = 544

Data collection

Siemens SMART Platform CCD diffractometer	2226 independent reflections
Radiation source: normal-focus sealed tube	2044 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
area detector, ω scans per phi	θmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan SADABS (Blessing, 1995)	h = −11→11
Tmin = 0.942, Tmax = 0.977	k = −9→9
11890 measured reflections	l = −20→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0424P)^2 + 0.3704P] where P = (Fo^2 + 2Fc^2)/3
2226 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.81615 (12)	0.31839 (15)	0.67401 (7)	0.0259 (3)
C2	0.83251 (12)	0.29787 (15)	0.59572 (7)	0.0254 (3)
C3	0.86367 (13)	0.43809 (15)	0.55326 (7)	0.0286 (3)
H3	0.8717	0.4235	0.4999	0.034*
C4	0.88304 (13)	0.59866 (16)	0.58824 (7)	0.0319 (3)
H4	0.9041	0.6943	0.5590	0.038*
C5	0.87172 (13)	0.61984 (16)	0.66604 (8)	0.0329 (3)
H5	0.8875	0.7295	0.6906	0.039*
C6	0.83758 (13)	0.48180 (16)	0.70803 (7)	0.0306 (3)
H6	0.8285	0.4984	0.7610	0.037*
C7	0.70149 (12)	0.06438 (16)	0.82767 (7)	0.0279 (3)
C8	0.58432 (13)	0.09306 (17)	0.86128 (7)	0.0317 (3)
C9	0.53825 (14)	−0.04296 (19)	0.90076 (7)	0.0381 (3)
H9	0.4579	−0.0270	0.9229	0.046*
C10	0.60612 (15)	−0.20075 (19)	0.90871 (8)	0.0412 (3)
H10	0.5719	−0.2916	0.9357	0.049*
C11	0.72407 (15)	−0.22637 (18)	0.87726 (7)	0.0376 (3)
H11	0.7721	−0.3339	0.8834	0.045*
C12	0.77132 (13)	−0.09359 (16)	0.83665 (7)	0.0309 (3)
H12	0.8519	−0.1106	0.8148	0.037*
C13	0.77001 (13)	0.17741 (16)	0.71927 (7)	0.0286 (3)
H13	0.7566	0.0656	0.6968	0.034*
C14	0.81929 (14)	0.12502 (16)	0.55689 (7)	0.0327 (3)
C15	0.50997 (15)	0.2643 (2)	0.85248 (9)	0.0434 (3)
H15A	0.4543	0.2790	0.7971	0.065*
H15B	0.5818	0.3558	0.8663	0.065*
H15C	0.4453	0.2697	0.8883	0.065*
F1	0.84711 (10)	0.12733 (10)	0.48491 (5)	0.0467 (2)
F2	0.68798 (9)	0.05598 (11)	0.54664 (5)	0.0496 (2)
F3	0.91184 (10)	0.01162 (10)	0.60088 (5)	0.0489 (2)
N1	0.74822 (11)	0.20368 (13)	0.78761 (6)	0.0302 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0253 (6)	0.0267 (6)	0.0261 (6)	0.0007 (5)	0.0072 (4)	0.0005 (5)
C2	0.0245 (5)	0.0257 (6)	0.0263 (6)	0.0010 (5)	0.0065 (4)	−0.0004 (5)
C3	0.0309 (6)	0.0298 (6)	0.0265 (6)	0.0011 (5)	0.0096 (5)	0.0023 (5)
C4	0.0363 (7)	0.0246 (6)	0.0360 (7)	−0.0001 (5)	0.0111 (5)	0.0048 (5)
C5	0.0366 (7)	0.0238 (6)	0.0387 (7)	−0.0007 (5)	0.0101 (5)	−0.0040 (5)
C6	0.0350 (6)	0.0308 (6)	0.0273 (6)	−0.0005 (5)	0.0099 (5)	−0.0034 (5)
C7	0.0293 (6)	0.0332 (6)	0.0201 (5)	−0.0045 (5)	0.0038 (4)	−0.0001 (5)
C8	0.0274 (6)	0.0434 (7)	0.0231 (6)	−0.0023 (5)	0.0038 (5)	−0.0004 (5)
C9	0.0305 (6)	0.0559 (9)	0.0287 (6)	−0.0081 (6)	0.0089 (5)	0.0027 (6)
C10	0.0456 (8)	0.0461 (8)	0.0315 (7)	−0.0143 (6)	0.0086 (6)	0.0076 (6)
C11	0.0468 (8)	0.0336 (7)	0.0306 (7)	−0.0024 (6)	0.0059 (6)	0.0029 (5)
C12	0.0342 (6)	0.0351 (7)	0.0236 (6)	−0.0019 (5)	0.0077 (5)	−0.0007 (5)
C13	0.0319 (6)	0.0268 (6)	0.0272 (6)	−0.0017 (5)	0.0078 (5)	−0.0008 (5)
C14	0.0427 (7)	0.0290 (6)	0.0294 (6)	−0.0035 (5)	0.0145 (5)	−0.0016 (5)
C15	0.0374 (7)	0.0510 (9)	0.0434 (8)	0.0073 (6)	0.0130 (6)	0.0008 (7)
F1	0.0758 (6)	0.0367 (4)	0.0356 (4)	−0.0064 (4)	0.0292 (4)	−0.0088 (3)
F2	0.0566 (5)	0.0463 (5)	0.0493 (5)	−0.0238 (4)	0.0194 (4)	−0.0176 (4)
F3	0.0714 (6)	0.0266 (4)	0.0507 (5)	0.0114 (4)	0.0191 (4)	0.0020 (3)
N1	0.0320 (5)	0.0323 (6)	0.0277 (5)	−0.0011 (4)	0.0099 (4)	0.0017 (4)

Geometric parameters (Å, º)

C1—C6	1.3967 (17)	C8—C15	1.5038 (19)
C1—C2	1.4088 (16)	C9—C10	1.383 (2)
C1—C13	1.4788 (16)	C9—H9	0.95
C2—C3	1.3896 (16)	C10—C11	1.387 (2)
C2—C14	1.4965 (17)	C10—H10	0.95
C3—C4	1.3824 (17)	C11—C12	1.3881 (18)
C3—H3	0.95	C11—H11	0.95
C4—C5	1.3849 (17)	C12—H12	0.95
C4—H4	0.95	C13—N1	1.2655 (15)
C5—C6	1.3817 (18)	C13—H13	0.95
C5—H5	0.95	C14—F1	1.3349 (14)
C6—H6	0.95	C14—F2	1.3421 (15)
C7—C12	1.3924 (18)	C14—F3	1.3473 (15)
C7—C8	1.4060 (17)	C15—H15A	0.98
C7—N1	1.4189 (15)	C15—H15B	0.98
C8—C9	1.3909 (19)	C15—H15C	0.98
C6—C1—C2	117.89 (11)	C8—C9—H9	119
C6—C1—C13	119.18 (10)	C9—C10—C11	119.99 (12)
C2—C1—C13	122.85 (10)	C9—C10—H10	120
C3—C2—C1	120.48 (11)	C11—C10—H10	120
C3—C2—C14	118.49 (10)	C10—C11—C12	119.44 (13)
C1—C2—C14	121.02 (10)	C10—C11—H11	120
C4—C3—C2	120.31 (11)	C12—C11—H11	120
C4—C3—H3	120	C11—C12—C7	120.47 (12)
C2—C3—H3	120	C11—C12—H12	120
C3—C4—C5	119.86 (11)	C7—C12—H12	120
C3—C4—H4	120	N1—C13—C1	120.89 (11)
C5—C4—H4	120	N1—C13—H13	120
C6—C5—C4	120.16 (11)	C1—C13—H13	120
C6—C5—H5	120	F1—C14—F2	106.29 (10)
C4—C5—H5	120	F1—C14—F3	106.15 (10)
C5—C6—C1	121.25 (11)	F2—C14—F3	106.18 (10)
C5—C6—H6	119	F1—C14—C2	113.02 (10)
C1—C6—H6	119	F2—C14—C2	113.14 (10)
C12—C7—C8	120.49 (11)	F3—C14—C2	111.52 (10)
C12—C7—N1	121.97 (10)	C8—C15—H15A	110
C8—C7—N1	117.50 (11)	C8—C15—H15B	110
C9—C8—C7	117.74 (12)	H15A—C15—H15B	110
C9—C8—C15	121.71 (12)	C8—C15—H15C	110
C7—C8—C15	120.53 (12)	H15A—C15—H15C	110
C10—C9—C8	121.83 (12)	H15B—C15—H15C	110
C10—C9—H9	119	C13—N1—C7	118.45 (11)
C6—C1—C2—C3	−2.36 (17)	C8—C9—C10—C11	0.4 (2)
C13—C1—C2—C3	174.24 (11)	C9—C10—C11—C12	−1.18 (19)
C6—C1—C2—C14	176.60 (11)	C10—C11—C12—C7	0.21 (19)
C13—C1—C2—C14	−6.79 (17)	C8—C7—C12—C11	1.57 (18)
C1—C2—C3—C4	1.85 (17)	N1—C7—C12—C11	179.01 (11)
C14—C2—C3—C4	−177.14 (11)	C6—C1—C13—N1	0.87 (17)
C2—C3—C4—C5	0.17 (18)	C2—C1—C13—N1	−175.69 (11)
C3—C4—C5—C6	−1.62 (19)	C3—C2—C14—F1	3.11 (16)
C4—C5—C6—C1	1.06 (19)	C1—C2—C14—F1	−175.88 (10)
C2—C1—C6—C5	0.92 (18)	C3—C2—C14—F2	−117.76 (12)
C13—C1—C6—C5	−175.81 (11)	C1—C2—C14—F2	63.25 (15)
C12—C7—C8—C9	−2.31 (17)	C3—C2—C14—F3	122.62 (11)
N1—C7—C8—C9	−179.87 (10)	C1—C2—C14—F3	−56.37 (15)
C12—C7—C8—C15	179.25 (11)	C1—C13—N1—C7	178.84 (10)
N1—C7—C8—C15	1.69 (17)	C12—C7—N1—C13	50.18 (16)
C7—C8—C9—C10	1.36 (19)	C8—C7—N1—C13	−132.30 (12)
C15—C8—C9—C10	179.78 (12)

(IV) N-(2-methylbenzylidene)-2-trifluoromethylaniline

Crystal data

C15H12F3N	Dx = 1.395 Mg m^−3
Mr = 263.26	Melting point = 72–74 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.7556 (6) Å	Cell parameters from 3523 reflections
b = 7.8003 (5) Å	θ = 2.7–25.0°
c = 16.8794 (11) Å	µ = 0.11 mm^−1
β = 102.647 (1)°	T = 173 K
V = 1253.30 (14) Å^3	Prism, yellow
Z = 4	0.50 × 0.35 × 0.10 mm
F(000) = 544

Data collection

Siemens SMART Platform CCD diffractometer	2205 independent reflections
Radiation source: normal-focus sealed tube	1947 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
area detector, ω scans per phi	θmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan SADABS (Blessing, 1995)	h = −11→11
Tmin = 0.951, Tmax = 0.986	k = −9→9
10706 measured reflections	l = −20→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.075	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0344P)^2 + 0.3477P] where P = (Fo^2 + 2Fc^2)/3
2205 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.82979 (11)	0.31928 (15)	0.67567 (7)	0.0276 (3)
C2	0.83504 (11)	0.29677 (14)	0.59359 (7)	0.0268 (3)
C3	0.85925 (12)	0.43587 (15)	0.54753 (7)	0.0300 (3)
H3	0.8598	0.4205	0.4918	0.036*
C4	0.88265 (13)	0.59726 (15)	0.58208 (7)	0.0334 (3)
H4	0.8986	0.6923	0.5501	0.040*
C5	0.88267 (13)	0.61948 (16)	0.66321 (8)	0.0351 (3)
H5	0.9007	0.7295	0.6874	0.042*
C6	0.85648 (13)	0.48179 (16)	0.70950 (7)	0.0332 (3)
H6	0.8567	0.4986	0.7653	0.040*
C7	0.68344 (12)	0.05704 (16)	0.81915 (7)	0.0304 (3)
C8	0.56982 (12)	0.07394 (17)	0.85779 (7)	0.0345 (3)
C9	0.53644 (13)	−0.06707 (19)	0.90085 (7)	0.0403 (3)
H9	0.4584	−0.0598	0.9259	0.048*
C10	0.61364 (15)	−0.21678 (19)	0.90811 (8)	0.0444 (3)
H10	0.5876	−0.3112	0.9372	0.053*
C11	0.72905 (15)	−0.22966 (17)	0.87299 (7)	0.0411 (3)
H11	0.7843	−0.3310	0.8795	0.049*
C12	0.76286 (14)	−0.09337 (16)	0.82843 (7)	0.0348 (3)
H12	0.8413	−0.1023	0.8038	0.042*
C13	0.71667 (12)	0.19602 (16)	0.76752 (7)	0.0314 (3)
H13	0.6727	0.3043	0.7688	0.038*
C14	0.81465 (13)	0.12270 (16)	0.55612 (7)	0.0348 (3)
C15	0.48607 (14)	0.2367 (2)	0.85462 (9)	0.0469 (3)
H15A	0.4398	0.2617	0.7982	0.070*
H15B	0.5489	0.3315	0.8765	0.070*
H15C	0.4149	0.2230	0.8871	0.070*
F1	0.81686 (9)	0.12510 (10)	0.47670 (4)	0.0493 (2)
F2	0.69248 (9)	0.04986 (11)	0.56063 (5)	0.0546 (2)
F3	0.91580 (9)	0.01252 (10)	0.59049 (5)	0.0520 (2)
N1	0.80251 (10)	0.17592 (13)	0.72118 (6)	0.0310 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0256 (5)	0.0293 (6)	0.0284 (6)	0.0018 (5)	0.0066 (4)	0.0019 (5)
C2	0.0248 (5)	0.0271 (6)	0.0290 (6)	0.0011 (5)	0.0072 (4)	−0.0007 (5)
C3	0.0317 (6)	0.0317 (6)	0.0279 (6)	0.0014 (5)	0.0091 (5)	0.0018 (5)
C4	0.0367 (6)	0.0263 (6)	0.0389 (7)	0.0005 (5)	0.0115 (5)	0.0042 (5)
C5	0.0361 (6)	0.0277 (6)	0.0416 (7)	−0.0019 (5)	0.0091 (5)	−0.0070 (5)
C6	0.0353 (6)	0.0364 (7)	0.0288 (6)	−0.0008 (5)	0.0092 (5)	−0.0050 (5)
C7	0.0319 (6)	0.0367 (6)	0.0220 (5)	−0.0053 (5)	0.0044 (5)	−0.0017 (5)
C8	0.0287 (6)	0.0471 (7)	0.0260 (6)	−0.0049 (5)	0.0026 (5)	−0.0014 (5)
C9	0.0353 (7)	0.0567 (9)	0.0295 (6)	−0.0117 (6)	0.0083 (5)	0.0008 (6)
C10	0.0552 (8)	0.0459 (8)	0.0322 (7)	−0.0156 (7)	0.0096 (6)	0.0046 (6)
C11	0.0570 (8)	0.0345 (7)	0.0321 (7)	−0.0022 (6)	0.0102 (6)	0.0011 (5)
C12	0.0424 (7)	0.0363 (7)	0.0272 (6)	−0.0020 (6)	0.0112 (5)	−0.0021 (5)
C13	0.0322 (6)	0.0337 (6)	0.0278 (6)	−0.0008 (5)	0.0053 (5)	−0.0007 (5)
C14	0.0424 (7)	0.0307 (6)	0.0342 (6)	−0.0028 (5)	0.0143 (5)	−0.0016 (5)
C15	0.0340 (7)	0.0608 (9)	0.0477 (8)	0.0069 (6)	0.0133 (6)	0.0044 (7)
F1	0.0777 (6)	0.0395 (4)	0.0349 (4)	−0.0067 (4)	0.0215 (4)	−0.0103 (3)
F2	0.0585 (5)	0.0492 (5)	0.0609 (5)	−0.0262 (4)	0.0239 (4)	−0.0188 (4)
F3	0.0693 (6)	0.0289 (4)	0.0586 (5)	0.0124 (4)	0.0160 (4)	−0.0007 (4)
N1	0.0336 (5)	0.0332 (5)	0.0264 (5)	−0.0010 (4)	0.0072 (4)	0.0027 (4)

Geometric parameters (Å, º)

C1—C6	1.3913 (17)	C8—C15	1.5046 (19)
C1—C2	1.4086 (16)	C9—C10	1.380 (2)
C1—N1	1.4145 (15)	C9—H9	0.95
C2—C3	1.3849 (16)	C10—C11	1.386 (2)
C2—C14	1.4927 (17)	C10—H10	0.95
C3—C4	1.3852 (17)	C11—C12	1.3833 (18)
C3—H3	0.95	C11—H11	0.95
C4—C5	1.3803 (17)	C12—H12	0.95
C4—H4	0.95	C13—N1	1.2746 (15)
C5—C6	1.3844 (18)	C13—H13	0.95
C5—H5	0.95	C14—F2	1.3374 (15)
C6—H6	0.95	C14—F3	1.3410 (15)
C7—C12	1.3959 (18)	C14—F1	1.3456 (14)
C7—C8	1.4099 (17)	C15—H15A	0.98
C7—C13	1.4708 (17)	C15—H15B	0.98
C8—C9	1.3956 (18)	C15—H15C	0.98
C6—C1—C2	118.25 (10)	C8—C9—H9	119
C6—C1—N1	122.55 (10)	C9—C10—C11	120.12 (12)
C2—C1—N1	119.16 (10)	C9—C10—H10	120
C3—C2—C1	120.13 (10)	C11—C10—H10	120
C3—C2—C14	119.88 (10)	C12—C11—C10	119.32 (13)
C1—C2—C14	119.99 (10)	C12—C11—H11	120
C2—C3—C4	120.55 (11)	C10—C11—H11	120
C2—C3—H3	120	C11—C12—C7	120.96 (12)
C4—C3—H3	120	C11—C12—H12	120
C5—C4—C3	119.74 (11)	C7—C12—H12	120
C5—C4—H4	120	N1—C13—C7	122.18 (11)
C3—C4—H4	120	N1—C13—H13	119
C4—C5—C6	120.17 (11)	C7—C13—H13	119
C4—C5—H5	120	F2—C14—F3	106.48 (10)
C6—C5—H5	120	F2—C14—F1	105.75 (10)
C5—C6—C1	121.09 (11)	F3—C14—F1	105.61 (10)
C5—C6—H6	120	F2—C14—C2	113.59 (10)
C1—C6—H6	120	F3—C14—C2	112.49 (10)
C12—C7—C8	120.00 (11)	F1—C14—C2	112.31 (10)
C12—C7—C13	119.81 (11)	C8—C15—H15A	110
C8—C7—C13	120.18 (11)	C8—C15—H15B	110
C9—C8—C7	117.65 (12)	H15A—C15—H15B	110
C9—C8—C15	119.79 (11)	C8—C15—H15C	110
C7—C8—C15	122.56 (12)	H15A—C15—H15C	110
C10—C9—C8	121.87 (12)	H15B—C15—H15C	110
C10—C9—H9	119	C13—N1—C1	117.59 (10)
C6—C1—C2—C3	−3.20 (16)	C8—C9—C10—C11	0.8 (2)
N1—C1—C2—C3	178.92 (10)	C9—C10—C11—C12	−2.19 (19)
C6—C1—C2—C14	176.74 (11)	C10—C11—C12—C7	0.69 (19)
N1—C1—C2—C14	−1.15 (16)	C8—C7—C12—C11	2.20 (18)
C1—C2—C3—C4	1.92 (17)	C13—C7—C12—C11	−176.42 (11)
C14—C2—C3—C4	−178.02 (11)	C12—C7—C13—N1	10.36 (17)
C2—C3—C4—C5	0.39 (18)	C8—C7—C13—N1	−168.26 (11)
C3—C4—C5—C6	−1.36 (18)	C3—C2—C14—F2	−122.68 (12)
C4—C5—C6—C1	0.01 (18)	C1—C2—C14—F2	57.39 (15)
C2—C1—C6—C5	2.25 (17)	C3—C2—C14—F3	116.27 (12)
N1—C1—C6—C5	−179.94 (11)	C1—C2—C14—F3	−63.66 (14)
C12—C7—C8—C9	−3.49 (17)	C3—C2—C14—F1	−2.72 (16)
C13—C7—C8—C9	175.13 (11)	C1—C2—C14—F1	177.34 (10)
C12—C7—C8—C15	175.96 (12)	C7—C13—N1—C1	−178.37 (10)
C13—C7—C8—C15	−5.42 (17)	C6—C1—N1—C13	45.47 (16)
C7—C8—C9—C10	2.03 (18)	C2—C1—N1—C13	−136.73 (11)
C15—C8—C9—C10	−177.44 (12)

(V) N-(2-bromobenzylidene)-2-methylaniline

Crystal data

C14H12BrN	Dx = 1.542 Mg m^−3
Mr = 274.16	Melting point = 78–80 K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
a = 13.4669 (10) Å	Cell parameters from 3317 reflections
b = 11.7471 (9) Å	θ = 2.3–25.0°
c = 14.9271 (11) Å	µ = 3.45 mm^−1
V = 2361.4 (3) Å^3	T = 173 K
Z = 8	Prism, yellow
F(000) = 1104	0.50 × 0.50 × 0.08 mm

Data collection

Siemens SMART Platform CCD diffractometer	2088 independent reflections
Radiation source: normal-focus sealed tube	1788 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
area detector, ω scans per phi	θmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan SADABS (Blessing, 1995)	h = −16→16
Tmin = 0.194, Tmax = 0.756	k = −13→13
21446 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.063	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0232P)^2 + 1.5024P] where P = (Fo^2 + 2Fc^2)/3
2088 reflections	(Δ/σ)max = 0.001
196 parameters	Δρmax = 0.26 e Å^−3
45 restraints	Δρmin = −0.22 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.09885 (3)	0.54056 (5)	0.68020 (4)	0.03447 (13)	0.6457 (7)
C1	0.2856 (4)	0.4965 (7)	0.5924 (6)	0.0238 (5)	0.6457 (7)
C2	0.2344 (5)	0.5690 (13)	0.6514 (10)	0.0243 (9)	0.6457 (7)
C3	0.2801 (7)	0.6593 (15)	0.6941 (11)	0.0273 (17)	0.6457 (7)
H3	0.2435	0.7075	0.7331	0.033*	0.6457 (7)
C4	0.3799 (10)	0.678 (2)	0.6790 (16)	0.0321 (12)	0.6457 (7)
H4	0.4120	0.7409	0.7065	0.039*	0.6457 (7)
C5	0.4340 (7)	0.6049 (13)	0.6237 (12)	0.030 (2)	0.6457 (7)
H5	0.5034	0.6161	0.6158	0.036*	0.6457 (7)
C6	0.3869 (5)	0.5164 (10)	0.5803 (8)	0.0246 (18)	0.6457 (7)
H6	0.4239	0.4682	0.5416	0.030*	0.6457 (7)
C7	0.2278 (3)	0.2648 (5)	0.4331 (4)	0.0195 (12)	0.6457 (7)
C8	0.2787 (3)	0.1686 (8)	0.4042 (8)	0.0222 (14)	0.6457 (7)
C9	0.2269 (4)	0.0894 (9)	0.3519 (10)	0.0266 (16)	0.6457 (7)
H9	0.2609	0.0239	0.3305	0.032*	0.6457 (7)
C10	0.1277 (9)	0.1037 (19)	0.3303 (18)	0.0342 (16)	0.6457 (7)
H10	0.0938	0.0473	0.2965	0.041*	0.6457 (7)
C11	0.0783 (6)	0.2005 (14)	0.3581 (12)	0.032 (2)	0.6457 (7)
H11	0.0107	0.2121	0.3424	0.038*	0.6457 (7)
C12	0.1284 (4)	0.2803 (7)	0.4091 (5)	0.0267 (16)	0.6457 (7)
H12	0.0946	0.3470	0.4282	0.032*	0.6457 (7)
C13	0.2373 (5)	0.4000 (5)	0.5460 (5)	0.0234 (12)	0.6457 (7)
H13	0.1725	0.3770	0.5635	0.028*	0.6457 (7)
C14	0.3857 (3)	0.1474 (6)	0.4285 (6)	0.050*	0.6457 (7)
H14A	0.4286	0.1721	0.3791	0.075*	0.6457 (7)
H14B	0.3958	0.0659	0.4394	0.075*	0.6457 (7)
H14C	0.4025	0.1903	0.4827	0.075*	0.6457 (7)
N1	0.2813 (3)	0.3475 (3)	0.48306 (19)	0.0244 (9)	0.6457 (7)
Br1A	0.40214 (6)	0.13289 (7)	0.42988 (8)	0.0342 (2)	0.3543 (7)
C1A	0.2171 (5)	0.2541 (10)	0.4506 (9)	0.0195 (12)	0.3543 (7)
C2A	0.2639 (5)	0.1590 (15)	0.4121 (16)	0.0222 (14)	0.3543 (7)
C3A	0.2134 (7)	0.0816 (18)	0.3594 (19)	0.0266 (16)	0.3543 (7)
H3A	0.2445	0.0133	0.3402	0.032*	0.3543 (7)
C4A	0.1167 (17)	0.106 (3)	0.335 (3)	0.0342 (16)	0.3543 (7)
H4A	0.0830	0.0578	0.2940	0.041*	0.3543 (7)
C5A	0.0681 (11)	0.201 (3)	0.371 (2)	0.032 (2)	0.3543 (7)
H5A	0.0005	0.2146	0.3565	0.038*	0.3543 (7)
C6A	0.1181 (7)	0.2736 (14)	0.4275 (12)	0.0267 (16)	0.3543 (7)
H6A	0.0848	0.3383	0.4510	0.032*	0.3543 (7)
C7A	0.2794 (6)	0.5023 (12)	0.5926 (11)	0.0238 (5)	0.3543 (7)
C8A	0.2260 (9)	0.563 (2)	0.6568 (19)	0.0243 (9)	0.3543 (7)
C9A	0.2751 (12)	0.650 (3)	0.703 (2)	0.0273 (17)	0.3543 (7)
H9A	0.2396	0.6920	0.7469	0.033*	0.3543 (7)
C10A	0.3737 (18)	0.676 (4)	0.687 (3)	0.0321 (12)	0.3543 (7)
H10A	0.4059	0.7334	0.7211	0.039*	0.3543 (7)
C11A	0.4248 (13)	0.619 (3)	0.621 (2)	0.030 (2)	0.3543 (7)
H11A	0.4915	0.6388	0.6069	0.036*	0.3543 (7)
C12A	0.3779 (9)	0.532 (2)	0.5744 (16)	0.0246 (18)	0.3543 (7)
H12A	0.4133	0.4918	0.5294	0.030*	0.3543 (7)
C13A	0.2696 (7)	0.3358 (8)	0.5093 (6)	0.0244 (9)	0.3543 (7)
H13A	0.3364	0.3216	0.5262	0.029*	0.3543 (7)
C14A	0.1168 (5)	0.5428 (12)	0.6722 (9)	0.050*	0.3543 (7)
H14D	0.1074	0.4701	0.7032	0.075*	0.3543 (7)
H14E	0.0822	0.5408	0.6145	0.075*	0.3543 (7)
H14F	0.0898	0.6046	0.7090	0.075*	0.3543 (7)
N1A	0.2260 (7)	0.4250 (8)	0.5373 (9)	0.0234 (12)	0.3543 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02272 (19)	0.0463 (2)	0.0344 (2)	0.00246 (18)	0.00429 (16)	−0.00775 (17)
C1	0.0287 (11)	0.0218 (12)	0.0208 (9)	−0.0006 (10)	0.0006 (9)	0.0012 (8)
C2	0.0273 (14)	0.0241 (18)	0.0214 (18)	−0.0001 (12)	0.0025 (12)	0.0047 (17)
C3	0.0397 (15)	0.023 (3)	0.020 (3)	0.0027 (10)	0.0005 (10)	0.000 (3)
C4	0.040 (2)	0.0257 (13)	0.030 (4)	−0.0068 (16)	−0.0067 (13)	−0.001 (3)
C5	0.0257 (18)	0.026 (4)	0.0371 (17)	−0.003 (3)	−0.002 (2)	0.006 (3)
C6	0.0263 (15)	0.019 (3)	0.0282 (19)	0.002 (2)	0.0035 (17)	0.002 (2)
C7	0.0286 (13)	0.0192 (14)	0.011 (3)	−0.0055 (12)	0.0082 (14)	0.0061 (17)
C8	0.0267 (15)	0.0216 (17)	0.018 (2)	−0.0052 (18)	0.008 (2)	0.0057 (18)
C9	0.0375 (19)	0.0199 (16)	0.022 (3)	−0.0064 (18)	0.012 (2)	0.0001 (19)
C10	0.043 (3)	0.0320 (14)	0.028 (3)	−0.010 (2)	−0.002 (4)	−0.0038 (11)
C11	0.0296 (19)	0.0381 (12)	0.028 (5)	−0.0030 (18)	−0.004 (3)	0.003 (2)
C12	0.0312 (15)	0.0268 (14)	0.022 (4)	0.0017 (14)	0.0025 (18)	0.002 (2)
C13	0.0264 (16)	0.020 (3)	0.0241 (18)	−0.0008 (15)	0.0018 (13)	0.004 (2)
N1	0.0289 (14)	0.0214 (12)	0.023 (2)	0.0002 (10)	−0.0004 (15)	0.0013 (15)
Br1A	0.0274 (4)	0.0299 (4)	0.0454 (4)	0.0031 (3)	0.0012 (3)	−0.0044 (3)
C1A	0.0286 (13)	0.0192 (14)	0.011 (3)	−0.0055 (12)	0.0082 (14)	0.0061 (17)
C2A	0.0267 (15)	0.0216 (17)	0.018 (2)	−0.0052 (18)	0.008 (2)	0.0057 (18)
C3A	0.0375 (19)	0.0199 (16)	0.022 (3)	−0.0064 (18)	0.012 (2)	0.0001 (19)
C4A	0.043 (3)	0.0320 (14)	0.028 (3)	−0.010 (2)	−0.002 (4)	−0.0038 (11)
C5A	0.0296 (19)	0.0381 (12)	0.028 (5)	−0.0030 (18)	−0.004 (3)	0.003 (2)
C6A	0.0312 (15)	0.0268 (14)	0.022 (4)	0.0017 (14)	0.0025 (18)	0.002 (2)
C7A	0.0287 (11)	0.0218 (12)	0.0208 (9)	−0.0006 (10)	0.0006 (9)	0.0012 (8)
C8A	0.0273 (14)	0.0241 (18)	0.0214 (18)	−0.0001 (12)	0.0025 (12)	0.0047 (17)
C9A	0.0397 (15)	0.023 (3)	0.020 (3)	0.0027 (10)	0.0005 (10)	0.000 (3)
C10A	0.040 (2)	0.0257 (13)	0.030 (4)	−0.0068 (16)	−0.0067 (13)	−0.001 (3)
C11A	0.0257 (18)	0.026 (4)	0.0371 (17)	−0.003 (3)	−0.002 (2)	0.006 (3)
C12A	0.0263 (15)	0.019 (3)	0.0282 (19)	0.002 (2)	0.0035 (17)	0.002 (2)
C13A	0.0289 (14)	0.0214 (12)	0.023 (2)	0.0002 (10)	−0.0004 (15)	0.0013 (15)
N1A	0.0264 (16)	0.020 (3)	0.0241 (18)	−0.0008 (15)	0.0018 (13)	0.004 (2)

Geometric parameters (Å, º)

Br1—C2	1.906 (3)	Br1A—C2A	1.905 (3)
C1—C6	1.396 (6)	C1A—C6A	1.396 (6)
C1—C2	1.405 (6)	C1A—C2A	1.404 (7)
C1—C13	1.479 (6)	C1A—C13A	1.480 (6)
C2—C3	1.381 (6)	C2A—C3A	1.382 (7)
C3—C4	1.381 (8)	C3A—C4A	1.381 (8)
C3—H3	0.95	C3A—H3A	0.95
C4—C5	1.397 (12)	C4A—C5A	1.397 (12)
C4—H4	0.95	C4A—H4A	0.95
C5—C6	1.379 (7)	C5A—C6A	1.379 (7)
C5—H5	0.95	C5A—H5A	0.95
C6—H6	0.95	C6A—H6A	0.95
C7—C8	1.390 (6)	C7A—C8A	1.391 (6)
C7—C12	1.398 (6)	C7A—C12A	1.399 (6)
C7—N1	1.421 (6)	C7A—N1A	1.422 (6)
C8—C9	1.401 (6)	C8A—C9A	1.400 (6)
C8—C14	1.507 (3)	C8A—C14A	1.508 (3)
C9—C10	1.385 (7)	C9A—C10A	1.385 (8)
C9—H9	0.95	C9A—H9A	0.95
C10—C11	1.381 (10)	C10A—C11A	1.381 (10)
C10—H10	0.95	C10A—H10A	0.95
C11—C12	1.384 (7)	C11A—C12A	1.384 (8)
C11—H11	0.95	C11A—H11A	0.95
C12—H12	0.95	C12A—H12A	0.95
C13—N1	1.271 (5)	C13A—N1A	1.271 (5)
C13—H13	0.95	C13A—H13A	0.95
C14—H14A	0.98	C14A—H14D	0.98
C14—H14B	0.98	C14A—H14E	0.98
C14—H14C	0.98	C14A—H14F	0.98
C6—C1—C2	117.3 (4)	C3A—C2A—C1A	122.3 (4)
C6—C1—C13	119.8 (4)	C3A—C2A—Br1A	117.0 (4)
C2—C1—C13	122.8 (3)	C1A—C2A—Br1A	120.6 (4)
C3—C2—C1	122.4 (3)	C4A—C3A—C2A	118.6 (7)
C3—C2—Br1	117.2 (4)	C4A—C3A—H3A	121
C1—C2—Br1	120.3 (4)	C2A—C3A—H3A	121
C4—C3—C2	118.7 (6)	C3A—C4A—C5A	120.4 (7)
C4—C3—H3	121	C3A—C4A—H4A	120
C2—C3—H3	121	C5A—C4A—H4A	120
C3—C4—C5	120.5 (6)	C6A—C5A—C4A	120.0 (6)
C3—C4—H4	120	C6A—C5A—H5A	120
C5—C4—H4	120	C4A—C5A—H5A	120
C6—C5—C4	120.0 (5)	C5A—C6A—C1A	121.0 (6)
C6—C5—H5	120	C5A—C6A—H6A	120
C4—C5—H5	120	C1A—C6A—H6A	120
C5—C6—C1	121.0 (5)	C8A—C7A—C12A	119.8 (5)
C5—C6—H6	120	C8A—C7A—N1A	117.6 (4)
C1—C6—H6	120	C12A—C7A—N1A	121.7 (5)
C8—C7—C12	119.9 (4)	C7A—C8A—C9A	118.0 (4)
C8—C7—N1	118.0 (3)	C7A—C8A—C14A	122.0 (5)
C12—C7—N1	122.0 (4)	C9A—C8A—C14A	119.9 (5)
C7—C8—C9	117.9 (3)	C10A—C9A—C8A	122.0 (6)
C7—C8—C14	122.1 (4)	C10A—C9A—H9A	119
C9—C8—C14	120.0 (4)	C8A—C9A—H9A	119
C10—C9—C8	122.0 (5)	C11A—C10A—C9A	119.6 (7)
C10—C9—H9	119	C11A—C10A—H10A	120
C8—C9—H9	119	C9A—C10A—H10A	120
C11—C10—C9	119.7 (6)	C10A—C11A—C12A	119.2 (6)
C11—C10—H10	120	C10A—C11A—H11A	120
C9—C10—H10	120	C12A—C11A—H11A	120
C10—C11—C12	119.2 (5)	C11A—C12A—C7A	121.4 (6)
C10—C11—H11	120	C11A—C12A—H12A	119
C12—C11—H11	120	C7A—C12A—H12A	119
C11—C12—C7	121.3 (5)	N1A—C13A—C1A	120.6 (5)
C11—C12—H12	119	N1A—C13A—H13A	120
C7—C12—H12	119	C1A—C13A—H13A	120
N1—C13—C1	120.8 (5)	C8A—C14A—H14D	110
N1—C13—H13	120	C8A—C14A—H14E	110
C1—C13—H13	120	H14D—C14A—H14E	110
C13—N1—C7	118.9 (3)	C8A—C14A—H14F	110
C6A—C1A—C2A	117.3 (5)	H14D—C14A—H14F	110
C6A—C1A—C13A	119.7 (5)	H14E—C14A—H14F	110
C2A—C1A—C13A	123.0 (4)	C13A—N1A—C7A	118.9 (4)
C6—C1—C2—C3	2 (2)	C6A—C1A—C2A—C3A	−5 (3)
C13—C1—C2—C3	−179.7 (15)	C13A—C1A—C2A—C3A	178 (2)
C6—C1—C2—Br1	−174.5 (13)	C6A—C1A—C2A—Br1A	173.9 (16)
C13—C1—C2—Br1	3.6 (19)	C13A—C1A—C2A—Br1A	−3 (3)
C1—C2—C3—C4	−1 (3)	C1A—C2A—C3A—C4A	8 (4)
Br1—C2—C3—C4	176 (2)	Br1A—C2A—C3A—C4A	−171 (3)
C2—C3—C4—C5	−2 (4)	C2A—C3A—C4A—C5A	−7 (6)
C3—C4—C5—C6	3 (4)	C3A—C4A—C5A—C6A	3 (7)
C4—C5—C6—C1	−2 (3)	C4A—C5A—C6A—C1A	−1 (6)
C2—C1—C6—C5	−1 (2)	C2A—C1A—C6A—C5A	2 (4)
C13—C1—C6—C5	−179.2 (14)	C13A—C1A—C6A—C5A	178 (3)
C12—C7—C8—C9	−0.5 (14)	C12A—C7A—C8A—C9A	−2 (4)
N1—C7—C8—C9	−177.4 (9)	N1A—C7A—C8A—C9A	−172 (3)
C12—C7—C8—C14	−179.7 (9)	C12A—C7A—C8A—C14A	173 (3)
N1—C7—C8—C14	3.4 (14)	N1A—C7A—C8A—C14A	4 (4)
C7—C8—C9—C10	−1 (2)	C7A—C8A—C9A—C10A	0 (6)
C14—C8—C9—C10	178 (2)	C14A—C8A—C9A—C10A	−176 (4)
C8—C9—C10—C11	2 (3)	C8A—C9A—C10A—C11A	3 (8)
C9—C10—C11—C12	−2 (4)	C9A—C10A—C11A—C12A	−3 (8)
C10—C11—C12—C7	0 (3)	C10A—C11A—C12A—C7A	1 (6)
C8—C7—C12—C11	1.2 (16)	C8A—C7A—C12A—C11A	2 (4)
N1—C7—C12—C11	178.0 (12)	N1A—C7A—C12A—C11A	171 (3)
C6—C1—C13—N1	−12.9 (10)	C6A—C1A—C13A—N1A	−2 (2)
C2—C1—C13—N1	169.0 (11)	C2A—C1A—C13A—N1A	174.9 (18)
C1—C13—N1—C7	−172.4 (4)	C1A—C13A—N1A—C7A	−179.1 (10)
C8—C7—N1—C13	−144.2 (8)	C8A—C7A—N1A—C13A	−148 (2)
C12—C7—N1—C13	38.9 (9)	C12A—C7A—N1A—C13A	42 (2)

(VI) N-(2-methylbenzylidene)-2-bromoaniline

Crystal data

C14H12BrN	Dx = 1.563 Mg m^−3
Mr = 274.16	Melting point = 79–82 K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
a = 13.3550 (12) Å	Cell parameters from 3828 reflections
b = 11.6667 (11) Å	θ = 2.3–25.0°
c = 14.9529 (14) Å	µ = 3.50 mm^−1
V = 2329.8 (4) Å^3	T = 173 K
Z = 8	Prism, yellow
F(000) = 1104	0.45 × 0.30 × 0.15 mm

Data collection

Siemens SMART Platform CCD diffractometer	2059 independent reflections
Radiation source: normal-focus sealed tube	1865 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
area detector, ω scans per phi	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan SADABS (Blessing, 1995)	h = −15→15
Tmin = 0.293, Tmax = 0.589	k = −13→13
21202 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.067	H-atom parameters constrained
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0269P)^2 + 2.7709P] where P = (Fo^2 + 2Fc^2)/3
2059 reflections	(Δ/σ)max = 0.001
146 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.403961 (19)	0.13753 (2)	0.436421 (19)	0.03074 (11)
C1	0.22137 (18)	0.2653 (2)	0.43832 (15)	0.0205 (5)
C2	0.26762 (18)	0.1651 (2)	0.40779 (16)	0.0204 (5)
C3	0.2174 (2)	0.0840 (2)	0.35753 (16)	0.0248 (6)
H3	0.2505	0.0160	0.3388	0.030*
C4	0.1181 (2)	0.1031 (2)	0.33470 (18)	0.0280 (6)
H4	0.0829	0.0482	0.2997	0.034*
C5	0.0702 (2)	0.2017 (2)	0.36277 (18)	0.0286 (6)
H5	0.0022	0.2145	0.3472	0.034*
C6	0.12122 (19)	0.2820 (2)	0.41361 (17)	0.0242 (6)
H6	0.0876	0.3498	0.4321	0.029*
C7	0.28321 (18)	0.4964 (2)	0.59680 (16)	0.0196 (5)
C8	0.23004 (19)	0.5637 (2)	0.65885 (15)	0.0216 (5)
C9	0.2798 (2)	0.6546 (2)	0.69962 (17)	0.0261 (6)
H9	0.2447	0.7019	0.7408	0.031*
C10	0.3793 (2)	0.6774 (2)	0.68137 (18)	0.0292 (6)
H10	0.4119	0.7394	0.7105	0.035*
C11	0.4320 (2)	0.6107 (2)	0.62096 (18)	0.0272 (6)
H11	0.5004	0.6264	0.6086	0.033*
C12	0.38379 (18)	0.5211 (2)	0.57910 (16)	0.0234 (6)
H12	0.4195	0.4753	0.5374	0.028*
C13	0.23428 (18)	0.4020 (2)	0.54873 (15)	0.0206 (5)
H13	0.1682	0.3807	0.5654	0.025*
C14	0.11913 (18)	0.5398 (2)	0.68217 (17)	0.0246 (6)
H14A	0.0959	0.5960	0.7263	0.037*
H14B	0.1129	0.4624	0.7071	0.037*
H14C	0.0783	0.5457	0.6279	0.037*
N1	0.27694 (15)	0.34772 (17)	0.48573 (13)	0.0217 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02397 (16)	0.02797 (16)	0.04027 (18)	0.00210 (11)	0.00054 (12)	−0.00165 (12)
C1	0.0245 (13)	0.0204 (12)	0.0166 (11)	−0.0029 (10)	0.0022 (10)	0.0015 (10)
C2	0.0205 (13)	0.0223 (13)	0.0184 (12)	−0.0016 (10)	0.0013 (10)	0.0027 (10)
C3	0.0356 (15)	0.0187 (12)	0.0202 (13)	−0.0032 (11)	0.0037 (11)	−0.0006 (11)
C4	0.0345 (15)	0.0255 (14)	0.0241 (14)	−0.0092 (12)	−0.0048 (11)	−0.0005 (11)
C5	0.0252 (14)	0.0342 (16)	0.0264 (14)	−0.0032 (12)	−0.0050 (11)	0.0013 (12)
C6	0.0260 (13)	0.0237 (13)	0.0229 (13)	0.0018 (11)	0.0022 (10)	0.0007 (11)
C7	0.0240 (13)	0.0189 (12)	0.0160 (11)	0.0001 (10)	−0.0018 (10)	0.0018 (10)
C8	0.0274 (14)	0.0211 (12)	0.0163 (12)	0.0018 (10)	−0.0013 (10)	0.0023 (10)
C9	0.0353 (15)	0.0219 (13)	0.0211 (13)	0.0044 (11)	−0.0013 (11)	−0.0035 (11)
C10	0.0382 (16)	0.0208 (13)	0.0285 (14)	−0.0046 (11)	−0.0097 (12)	0.0001 (12)
C11	0.0244 (13)	0.0241 (14)	0.0331 (15)	−0.0043 (11)	−0.0032 (11)	0.0030 (11)
C12	0.0232 (13)	0.0234 (14)	0.0236 (14)	0.0000 (10)	0.0031 (10)	0.0007 (11)
C13	0.0206 (12)	0.0210 (12)	0.0202 (13)	−0.0013 (10)	−0.0011 (10)	0.0018 (10)
C14	0.0280 (14)	0.0262 (13)	0.0196 (13)	0.0046 (11)	0.0070 (10)	−0.0057 (11)
N1	0.0238 (11)	0.0185 (10)	0.0229 (11)	−0.0027 (8)	−0.0002 (9)	−0.0004 (9)

Geometric parameters (Å, º)

Br1—C2	1.898 (2)	C8—C9	1.392 (4)
C1—C2	1.398 (3)	C8—C14	1.547 (3)
C1—C6	1.401 (3)	C9—C10	1.383 (4)
C1—N1	1.407 (3)	C9—H9	0.95
C2—C3	1.383 (4)	C10—C11	1.385 (4)
C3—C4	1.388 (4)	C10—H10	0.95
C3—H3	0.95	C11—C12	1.377 (4)
C4—C5	1.382 (4)	C11—H11	0.95
C4—H4	0.95	C12—H12	0.95
C5—C6	1.385 (4)	C13—N1	1.270 (3)
C5—H5	0.95	C13—H13	0.95
C6—H6	0.95	C14—H14A	0.98
C7—C12	1.399 (3)	C14—H14B	0.98
C7—C8	1.408 (3)	C14—H14C	0.98
C7—C13	1.469 (3)
C2—C1—C6	116.9 (2)	C7—C8—C14	122.1 (2)
C2—C1—N1	120.2 (2)	C10—C9—C8	121.3 (2)
C6—C1—N1	122.8 (2)	C10—C9—H9	119
C3—C2—C1	122.4 (2)	C8—C9—H9	119
C3—C2—Br1	118.14 (19)	C9—C10—C11	120.6 (2)
C1—C2—Br1	119.48 (18)	C9—C10—H10	120
C2—C3—C4	119.2 (2)	C11—C10—H10	120
C2—C3—H3	120	C12—C11—C10	119.0 (2)
C4—C3—H3	120	C12—C11—H11	121
C5—C4—C3	120.1 (2)	C10—C11—H11	121
C5—C4—H4	120	C11—C12—C7	121.3 (2)
C3—C4—H4	120	C11—C12—H12	119
C4—C5—C6	120.1 (2)	C7—C12—H12	119
C4—C5—H5	120	N1—C13—C7	122.5 (2)
C6—C5—H5	120	N1—C13—H13	119
C5—C6—C1	121.3 (2)	C7—C13—H13	119
C5—C6—H6	119	C8—C14—H14A	110
C1—C6—H6	119	C8—C14—H14B	110
C12—C7—C8	119.6 (2)	H14A—C14—H14B	110
C12—C7—C13	119.3 (2)	C8—C14—H14C	110
C8—C7—C13	121.1 (2)	H14A—C14—H14C	110
C9—C8—C7	118.2 (2)	H14B—C14—H14C	110
C9—C8—C14	119.7 (2)	C13—N1—C1	118.6 (2)
C6—C1—C2—C3	−1.7 (3)	C13—C7—C8—C14	2.1 (3)
N1—C1—C2—C3	−177.1 (2)	C7—C8—C9—C10	−1.2 (4)
C6—C1—C2—Br1	178.79 (18)	C14—C8—C9—C10	179.0 (2)
N1—C1—C2—Br1	3.4 (3)	C8—C9—C10—C11	0.7 (4)
C1—C2—C3—C4	1.4 (4)	C9—C10—C11—C12	0.1 (4)
Br1—C2—C3—C4	−179.09 (19)	C10—C11—C12—C7	−0.3 (4)
C2—C3—C4—C5	−0.6 (4)	C8—C7—C12—C11	−0.3 (4)
C3—C4—C5—C6	0.1 (4)	C13—C7—C12—C11	178.4 (2)
C4—C5—C6—C1	−0.5 (4)	C12—C7—C13—N1	−6.3 (4)
C2—C1—C6—C5	1.2 (4)	C8—C7—C13—N1	172.3 (2)
N1—C1—C6—C5	176.5 (2)	C7—C13—N1—C1	−174.6 (2)
C12—C7—C8—C9	1.0 (3)	C2—C1—N1—C13	−144.3 (2)
C13—C7—C8—C9	−177.6 (2)	C6—C1—N1—C13	40.6 (3)
C12—C7—C8—C14	−179.2 (2)

(VII) N-(4-methylbenzylidene)-4-cyanoaniline

Crystal data

C15H12N2	Dx = 1.259 Mg m^−3
Mr = 220.27	Melting point = 129–131 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.1535 (9) Å	Cell parameters from 2898 reflections
b = 7.199 (1) Å	θ = 2.9–25.0°
c = 26.253 (4) Å	µ = 0.08 mm^−1
β = 92.285 (2)°	T = 173 K
V = 1162.1 (3) Å^3	Plate, yellow
Z = 4	0.50 × 0.48 × 0.05 mm
F(000) = 464

Data collection

Siemens SMART Platform CCD diffractometer	2062 independent reflections
Radiation source: normal-focus sealed tube	1727 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
area detector, ω scans per phi	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan SADABS (Blessing, 1995)	h = −7→7
Tmin = 0.960, Tmax = 0.993	k = −8→8
10066 measured reflections	l = −31→31

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0412P)^2 + 0.2659P] where P = (Fo^2 + 2Fc^2)/3
2062 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.11 e Å^−3
0 restraints	Δρmin = −0.14 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.12634 (19)	0.62561 (17)	0.23721 (5)	0.0300 (3)
C2	0.2057 (2)	0.66676 (17)	0.28623 (5)	0.0329 (3)
H2	0.3488	0.7149	0.2911	0.039*
C3	0.0798 (2)	0.63883 (18)	0.32804 (5)	0.0359 (3)
H3	0.1376	0.6677	0.3612	0.043*
C4	−0.1307 (2)	0.56890 (17)	0.32214 (5)	0.0343 (3)
C5	−0.20890 (19)	0.52425 (18)	0.27303 (5)	0.0348 (3)
H5	−0.3510	0.4740	0.2682	0.042*
C6	−0.0833 (2)	0.55182 (18)	0.23131 (5)	0.0338 (3)
H6	−0.1398	0.5203	0.1982	0.041*
C7	0.3380 (2)	0.65482 (18)	0.10791 (5)	0.0329 (3)
C8	0.2723 (2)	0.75943 (18)	0.06526 (5)	0.0362 (3)
H8	0.1328	0.8163	0.0638	0.043*
C9	0.4086 (2)	0.78061 (19)	0.02530 (5)	0.0365 (3)
H9	0.3631	0.8520	−0.0036	0.044*
C10	0.6139 (2)	0.69711 (18)	0.02730 (5)	0.0336 (3)
C11	0.6790 (2)	0.58880 (18)	0.06915 (5)	0.0352 (3)
H11	0.8171	0.5296	0.0703	0.042*
C12	0.5412 (2)	0.56824 (18)	0.10896 (5)	0.0348 (3)
H12	0.5851	0.4941	0.1375	0.042*
C13	0.2619 (2)	0.65643 (17)	0.19341 (5)	0.0325 (3)
H13	0.4080	0.6960	0.1994	0.039*
C14	−0.2709 (2)	0.5429 (2)	0.36732 (5)	0.0479 (4)
H14A	−0.1785	0.5165	0.3977	0.072*	0.794 (18)
H14B	−0.3709	0.4388	0.3608	0.072*	0.794 (18)
H14C	−0.3546	0.6565	0.3728	0.072*	0.794 (18)
H14D	−0.4242	0.5580	0.3565	0.072*	0.206 (18)
H14E	−0.2318	0.6357	0.3934	0.072*	0.206 (18)
H14F	−0.2481	0.4181	0.3814	0.072*	0.206 (18)
C15	0.7588 (2)	0.7234 (2)	−0.01390 (5)	0.0388 (3)
N1	0.19196 (17)	0.63233 (16)	0.14759 (4)	0.0363 (3)
N2	0.8756 (2)	0.74750 (19)	−0.04616 (5)	0.0532 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0295 (6)	0.0269 (6)	0.0338 (7)	0.0034 (5)	0.0038 (5)	0.0021 (5)
C2	0.0305 (7)	0.0304 (7)	0.0378 (7)	−0.0006 (5)	0.0024 (5)	−0.0021 (5)
C3	0.0405 (7)	0.0361 (7)	0.0314 (7)	0.0040 (6)	0.0024 (6)	−0.0029 (6)
C4	0.0362 (7)	0.0297 (7)	0.0376 (7)	0.0073 (5)	0.0081 (6)	0.0041 (5)
C5	0.0278 (6)	0.0336 (7)	0.0434 (7)	0.0009 (5)	0.0046 (6)	0.0029 (6)
C6	0.0322 (7)	0.0361 (7)	0.0331 (7)	0.0022 (5)	−0.0006 (5)	0.0001 (5)
C7	0.0305 (6)	0.0373 (7)	0.0308 (7)	−0.0063 (5)	0.0020 (5)	0.0002 (5)
C8	0.0309 (6)	0.0421 (8)	0.0357 (7)	0.0014 (6)	0.0013 (5)	0.0024 (6)
C9	0.0388 (7)	0.0398 (7)	0.0308 (7)	−0.0028 (6)	−0.0004 (6)	0.0036 (6)
C10	0.0355 (7)	0.0356 (7)	0.0300 (7)	−0.0049 (5)	0.0044 (5)	−0.0030 (5)
C11	0.0313 (7)	0.0377 (7)	0.0365 (7)	−0.0004 (5)	0.0018 (5)	−0.0010 (6)
C12	0.0335 (7)	0.0385 (7)	0.0323 (7)	−0.0025 (6)	−0.0013 (5)	0.0046 (6)
C13	0.0290 (6)	0.0318 (7)	0.0369 (7)	−0.0005 (5)	0.0026 (5)	0.0021 (5)
C14	0.0473 (8)	0.0547 (9)	0.0426 (8)	0.0062 (7)	0.0144 (7)	0.0076 (7)
C15	0.0399 (7)	0.0428 (8)	0.0338 (7)	−0.0007 (6)	0.0032 (6)	−0.0003 (6)
N1	0.0326 (6)	0.0433 (6)	0.0331 (6)	−0.0015 (5)	0.0039 (5)	0.0041 (5)
N2	0.0504 (7)	0.0674 (9)	0.0427 (7)	0.0017 (6)	0.0132 (6)	0.0057 (6)

Geometric parameters (Å, º)

C1—C2	1.3898 (17)	C9—C10	1.3982 (18)
C1—C6	1.3979 (17)	C9—H9	0.95
C1—C13	1.4644 (17)	C10—C11	1.3931 (18)
C2—C3	1.3834 (17)	C10—C15	1.4413 (17)
C2—H2	0.95	C11—C12	1.3801 (17)
C3—C4	1.3923 (18)	C11—H11	0.95
C3—H3	0.95	C12—H12	0.95
C4—C5	1.3956 (19)	C13—N1	1.2734 (16)
C4—C14	1.5061 (17)	C13—H13	0.95
C5—C6	1.3798 (17)	C14—H14A	0.98
C5—H5	0.95	C14—H14B	0.98
C6—H6	0.95	C14—H14C	0.98
C7—C8	1.3959 (18)	C14—H14D	0.98
C7—C12	1.3961 (18)	C14—H14E	0.98
C7—N1	1.4120 (15)	C14—H14F	0.98
C8—C9	1.3775 (17)	C15—N2	1.1458 (16)
C8—H8	0.95
C2—C1—C6	118.18 (11)	C11—C10—C9	120.10 (11)
C2—C1—C13	120.30 (11)	C11—C10—C15	119.89 (12)
C6—C1—C13	121.51 (11)	C9—C10—C15	120.02 (12)
C3—C2—C1	121.09 (12)	C12—C11—C10	119.41 (12)
C3—C2—H2	120	C12—C11—H11	120
C1—C2—H2	120	C10—C11—H11	120
C2—C3—C4	120.81 (12)	C11—C12—C7	120.94 (12)
C2—C3—H3	120	C11—C12—H12	120
C4—C3—H3	120	C7—C12—H12	120
C3—C4—C5	118.10 (11)	N1—C13—C1	122.65 (12)
C3—C4—C14	121.12 (12)	N1—C13—H13	119
C5—C4—C14	120.78 (12)	C1—C13—H13	119
C6—C5—C4	121.11 (12)	C4—C14—H14A	110
C6—C5—H5	119	C4—C14—H14B	110
C4—C5—H5	119	H14A—C14—H14B	110
C5—C6—C1	120.69 (12)	C4—C14—H14C	110
C5—C6—H6	120	H14A—C14—H14C	110
C1—C6—H6	120	H14B—C14—H14C	110
C8—C7—C12	119.17 (11)	C4—C14—H14D	110
C8—C7—N1	118.74 (11)	C4—C14—H14E	110
C12—C7—N1	122.00 (11)	H14D—C14—H14E	110
C9—C8—C7	120.31 (12)	C4—C14—H14F	110
C9—C8—H8	120	H14D—C14—H14F	110
C7—C8—H8	120	H14E—C14—H14F	110
C8—C9—C10	120.04 (12)	N2—C15—C10	178.60 (15)
C8—C9—H9	120	C13—N1—C7	118.69 (11)
C10—C9—H9	120
C6—C1—C2—C3	−1.15 (18)	C8—C9—C10—C11	1.49 (19)
C13—C1—C2—C3	179.89 (11)	C8—C9—C10—C15	−178.33 (12)
C1—C2—C3—C4	−0.14 (19)	C9—C10—C11—C12	−1.40 (19)
C2—C3—C4—C5	1.34 (18)	C15—C10—C11—C12	178.42 (12)
C2—C3—C4—C14	−178.35 (12)	C10—C11—C12—C7	−0.20 (19)
C3—C4—C5—C6	−1.25 (18)	C8—C7—C12—C11	1.70 (19)
C14—C4—C5—C6	178.44 (12)	N1—C7—C12—C11	178.45 (12)
C4—C5—C6—C1	−0.04 (19)	C2—C1—C13—N1	−175.35 (12)
C2—C1—C6—C5	1.24 (18)	C6—C1—C13—N1	5.73 (19)
C13—C1—C6—C5	−179.81 (11)	C1—C13—N1—C7	−176.31 (11)
C12—C7—C8—C9	−1.60 (19)	C8—C7—N1—C13	−133.53 (13)
N1—C7—C8—C9	−178.47 (12)	C12—C7—N1—C13	49.70 (17)
C7—C8—C9—C10	0.0 (2)

(VIII) N-(4-cyanobenzylidene)-4-methylaniline

Crystal data

C15H12N2	Dx = 1.242 Mg m^−3
Mr = 220.27	Melting point = 144–146 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.1878 (12) Å	Cell parameters from 2582 reflections
b = 7.3785 (15) Å	θ = 2.9–27.5°
c = 25.895 (5) Å	µ = 0.07 mm^−1
β = 94.635 (3)°	T = 173 K
V = 1178.4 (4) Å^3	Prism, yellow
Z = 4	0.43 × 0.30 × 0.30 mm
F(000) = 464

Data collection

Siemens SMART Platform CCD diffractometer	2677 independent reflections
Radiation source: normal-focus sealed tube	2218 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
area detector, ω scans per phi	θmax = 27.6°, θmin = 1.6°
Absorption correction: multi-scan SADABS (Blessing, 1995)	h = −7→7
Tmin = 0.971, Tmax = 0.975	k = 0→9
2677 measured reflections	l = 0→33

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.186	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.091P)^2 + 0.6802P] where P = (Fo^2 + 2Fc^2)/3
2677 reflections	(Δ/σ)max = 0.013
155 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.0972 (3)	0.6698 (2)	0.20117 (7)	0.0290 (4)
C2	0.0085 (3)	0.7243 (2)	0.15264 (7)	0.0333 (4)
H2	−0.1316	0.7778	0.1493	0.040*
C3	0.1214 (3)	0.7018 (3)	0.10901 (7)	0.0357 (4)
H3	0.0562	0.7369	0.0761	0.043*
C4	0.3292 (3)	0.6284 (2)	0.11289 (8)	0.0352 (4)
C5	0.4204 (3)	0.5802 (2)	0.16193 (8)	0.0363 (4)
H5	0.5640	0.5336	0.1655	0.044*
C6	0.3069 (3)	0.5985 (2)	0.20561 (7)	0.0326 (4)
H6	0.3717	0.5626	0.2385	0.039*
C7	−0.1337 (3)	0.6358 (2)	0.32840 (7)	0.0294 (4)
C8	−0.0674 (3)	0.5683 (2)	0.37745 (7)	0.0330 (4)
H8	0.0685	0.5087	0.3830	0.040*
C9	−0.1977 (3)	0.5874 (3)	0.41809 (7)	0.0351 (4)
H9	−0.1513	0.5419	0.4515	0.042*
C10	−0.3973 (3)	0.6739 (2)	0.40960 (7)	0.0318 (4)
C11	−0.4645 (3)	0.7441 (2)	0.36070 (7)	0.0320 (4)
H11	−0.6003	0.8040	0.3552	0.038*
C12	−0.3328 (3)	0.7259 (2)	0.32065 (7)	0.0307 (4)
H12	−0.3773	0.7747	0.2875	0.037*
C13	0.0051 (3)	0.6113 (2)	0.28558 (7)	0.0315 (4)
H13	0.1271	0.5330	0.2899	0.038*
C14	0.4529 (4)	0.6017 (3)	0.06553 (9)	0.0494 (6)
H14C	0.4060	0.4888	0.0481	0.074*
H14B	0.6085	0.5952	0.0760	0.074*
H14A	0.4245	0.7038	0.0417	0.074*
C15	−0.5399 (3)	0.6877 (3)	0.45064 (7)	0.0385 (5)
N1	−0.0358 (2)	0.6935 (2)	0.24277 (6)	0.0316 (4)
N2	−0.6566 (3)	0.6967 (3)	0.48255 (7)	0.0553 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0317 (9)	0.0187 (8)	0.0367 (9)	−0.0020 (6)	0.0041 (7)	−0.0016 (6)
C2	0.0327 (9)	0.0267 (9)	0.0407 (10)	0.0029 (7)	0.0037 (7)	0.0046 (7)
C3	0.0398 (10)	0.0309 (9)	0.0365 (9)	−0.0025 (8)	0.0043 (8)	0.0050 (7)
C4	0.0382 (10)	0.0234 (8)	0.0455 (10)	−0.0076 (7)	0.0128 (8)	−0.0023 (7)
C5	0.0311 (9)	0.0240 (8)	0.0544 (11)	−0.0006 (7)	0.0083 (8)	−0.0004 (8)
C6	0.0330 (9)	0.0230 (8)	0.0411 (10)	−0.0023 (7)	−0.0008 (7)	0.0002 (7)
C7	0.0357 (9)	0.0184 (7)	0.0340 (9)	−0.0024 (7)	0.0022 (7)	−0.0011 (6)
C8	0.0343 (9)	0.0255 (8)	0.0388 (9)	0.0037 (7)	0.0002 (7)	0.0017 (7)
C9	0.0418 (10)	0.0302 (9)	0.0323 (9)	0.0023 (8)	−0.0022 (7)	0.0035 (7)
C10	0.0373 (9)	0.0253 (8)	0.0326 (9)	−0.0004 (7)	0.0022 (7)	−0.0031 (7)
C11	0.0342 (9)	0.0249 (8)	0.0363 (9)	0.0032 (7)	−0.0002 (7)	−0.0003 (7)
C12	0.0372 (9)	0.0228 (8)	0.0315 (8)	0.0006 (7)	−0.0013 (7)	0.0024 (6)
C13	0.0347 (9)	0.0211 (8)	0.0388 (9)	0.0011 (7)	0.0040 (7)	−0.0003 (7)
C14	0.0546 (13)	0.0429 (12)	0.0537 (13)	−0.0070 (10)	0.0233 (10)	−0.0040 (10)
C15	0.0434 (11)	0.0369 (10)	0.0348 (9)	0.0075 (8)	0.0011 (8)	0.0018 (8)
N1	0.0357 (8)	0.0253 (7)	0.0336 (8)	−0.0007 (6)	0.0029 (6)	−0.0015 (6)
N2	0.0611 (12)	0.0659 (13)	0.0401 (10)	0.0195 (10)	0.0124 (9)	0.0071 (9)

Geometric parameters (Å, º)

C1—C2	1.390 (3)	C8—C9	1.383 (3)
C1—C6	1.396 (3)	C8—H8	0.95
C1—N1	1.418 (2)	C9—C10	1.392 (3)
C2—C3	1.386 (3)	C9—H9	0.95
C2—H2	0.95	C10—C11	1.400 (3)
C3—C4	1.391 (3)	C10—C15	1.439 (3)
C3—H3	0.95	C11—C12	1.376 (2)
C4—C5	1.394 (3)	C11—H11	0.95
C4—C14	1.510 (3)	C12—H12	0.95
C5—C6	1.385 (3)	C13—N1	1.271 (2)
C5—H5	0.95	C13—H13	0.95
C6—H6	0.95	C14—H14C	0.98
C7—C8	1.395 (2)	C14—H14B	0.98
C7—C12	1.400 (3)	C14—H14A	0.98
C7—C13	1.468 (2)	C15—N2	1.142 (3)
C2—C1—C6	118.69 (16)	C8—C9—C10	119.39 (16)
C2—C1—N1	116.11 (15)	C8—C9—H9	120
C6—C1—N1	125.20 (16)	C10—C9—H9	120
C3—C2—C1	120.95 (17)	C9—C10—C11	120.49 (17)
C3—C2—H2	120	C9—C10—C15	120.35 (16)
C1—C2—H2	120	C11—C10—C15	119.14 (16)
C2—C3—C4	120.79 (17)	C12—C11—C10	119.67 (16)
C2—C3—H3	120	C12—C11—H11	120
C4—C3—H3	120	C10—C11—H11	120
C3—C4—C5	117.96 (17)	C11—C12—C7	120.40 (16)
C3—C4—C14	121.22 (18)	C11—C12—H12	120
C5—C4—C14	120.81 (18)	C7—C12—H12	120
C6—C5—C4	121.63 (17)	N1—C13—C7	120.84 (16)
C6—C5—H5	119	N1—C13—H13	120
C4—C5—H5	119	C7—C13—H13	120
C5—C6—C1	119.92 (17)	C4—C14—H14C	110
C5—C6—H6	120	C4—C14—H14B	110
C1—C6—H6	120	H14C—C14—H14B	110
C8—C7—C12	119.38 (16)	C4—C14—H14A	110
C8—C7—C13	119.81 (16)	H14C—C14—H14A	110
C12—C7—C13	120.81 (16)	H14B—C14—H14A	110
C9—C8—C7	120.66 (16)	N2—C15—C10	178.5 (2)
C9—C8—H8	120	C13—N1—C1	121.12 (16)
C7—C8—H8	120
C6—C1—C2—C3	2.7 (3)	C8—C9—C10—C11	−1.2 (3)
N1—C1—C2—C3	−177.86 (15)	C8—C9—C10—C15	177.05 (17)
C1—C2—C3—C4	−1.8 (3)	C9—C10—C11—C12	0.6 (3)
C2—C3—C4—C5	−0.6 (3)	C15—C10—C11—C12	−177.66 (16)
C2—C3—C4—C14	179.43 (17)	C10—C11—C12—C7	0.7 (3)
C3—C4—C5—C6	2.1 (3)	C8—C7—C12—C11	−1.5 (3)
C14—C4—C5—C6	−177.99 (17)	C13—C7—C12—C11	178.30 (15)
C4—C5—C6—C1	−1.1 (3)	C8—C7—C13—N1	−169.70 (17)
C2—C1—C6—C5	−1.2 (3)	C12—C7—C13—N1	10.5 (3)
N1—C1—C6—C5	179.34 (15)	C7—C13—N1—C1	−179.73 (15)
C12—C7—C8—C9	0.9 (3)	C2—C1—N1—C13	163.14 (17)
C13—C7—C8—C9	−178.90 (16)	C6—C1—N1—C13	−17.4 (3)
C7—C8—C9—C10	0.4 (3)