Z/E-Isomerism of 3-[4-(di­methyl­amino)­phen­yl]-2-(2,4,6-tri­bromo­phen­yl)acrylo­nitrile: crystal structures and secondary inter­molecular inter­actions

The Z and E isomers of 3-[4-(di­methyl­amino)­phen­yl]-2-(2,4,6-tri­bromo­phen­yl)acrylo­nitrile, C₁₇H₁₃Br₃N₂, (1), were obtained simultaneously by a Knoevenagel condensation between 4-(di­methyl­amino)­benzaldehyde and 2-(2,4,6-tri­bromo­phen­yl)aceto­nitrile, and were investigated by X-ray diffraction and density functional theory (DFT) quantum-chemical calculations. The (Z)-(1) isomer is monoclinic (space group P2₁/n, Z′ = 1), whereas the (E)-(1) isomer is triclinic (space group P, Z′ = 2). The two crystallographically-independent mol­ecules of (E)-(1) adopt similar geometries. The corresponding bond lengths and angles in the two isomers of (1) are very similar. The difference in the calculated total energies of isolated mol­ecules of (Z)-(1) and (E)-(1) with DFT-optimized geometries is ∼4.47 kJ mol⁻¹, with the minimum value corresponding to the Z isomer. The crystal structure of (Z)-(1) reveals strong inter­molecular nonvalent Br...N [3.100 (2) and 3.216 (3) Å] inter­actions which link the mol­ecules into layers parallel to (10). In contrast, mol­ecules of (E)-(1) in the crystal are bound to each other by strong nonvalent Br...Br [3.5556 (10) Å] and weak Br...N [3.433 (4) Å] inter­actions, forming chains propagating along [110]. The crystal packing of (Z)-(1) is denser than that of (E)-(1), implying that the crystal structure realized for (Z)-(1) is more stable than that for (E)-(1).

Computing details

Data collection: SAINT (Bruker, 2012) for Eacryl; APEX2 (Bruker, 2012) for Zacryl. Cell refinement: APEX2 (Bruker, 2012) for Eacryl; SAINT (Bruker, 2012) for Zacryl. For both structures, data reduction: SAINT (Bruker, 2012). Program(s) used to solve structure: SIR2004 (Burla et al., 2003) for Eacryl; SHELXT (Sheldrick, 2015a) for Zacryl. Program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b) for Eacryl; SHELXL (Sheldrick, 2015b) for Zacryl. Molecular graphics: OLEX2 (Dolomanov et al., 2009) for Eacryl; SHELXTL (Bruker, 2012) for Zacryl. Software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) for Eacryl; SHELXTL (Bruker, 2012) for Zacryl.

(E)-3-[4-(Dimethylamino)phenyl]-2-(2,4,6-tribromophenyl)prop-2-enenitrile (Eacryl)

Crystal data

C17H13Br3N2	Z = 4
Mr = 485.02	F(000) = 936
Triclinic, P1	Dx = 1.830 Mg m^−3
a = 11.965 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.595 (2) Å	Cell parameters from 4669 reflections
c = 13.667 (3) Å	θ = 2.5–26.8°
α = 114.497 (3)°	µ = 6.87 mm^−1
β = 106.139 (4)°	T = 100 K
γ = 93.912 (4)°	Plate, yellow
V = 1760.3 (8) Å^3	0.4 × 0.2 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer	4214 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.036
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	θmax = 25.0°, θmin = 1.8°
Tmin = 0.047, Tmax = 0.154	h = −14→14
13968 measured reflections	k = −14→14
6178 independent reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.080	w = 1/[σ^2(Fo^2) + (0.0409P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max = 0.001
6178 reflections	Δρmax = 0.66 e Å^−3
401 parameters	Δρmin = −0.55 e Å^−3
0 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq
Br1	0.98998 (4)	0.89059 (4)	0.15948 (4)	0.05443 (14)
Br2	0.81943 (6)	0.40862 (5)	−0.15987 (5)	0.08624 (19)
Br3	0.61195 (4)	0.61348 (4)	0.18038 (5)	0.07006 (17)
N1	0.6910 (3)	0.9993 (3)	0.2473 (3)	0.0616 (10)
N2	1.1546 (3)	0.6158 (3)	0.5775 (3)	0.0576 (9)
C1	0.7418 (4)	0.9285 (3)	0.2554 (3)	0.0448 (10)
C2	0.8071 (3)	0.8404 (3)	0.2675 (3)	0.0347 (9)
C3	0.8666 (3)	0.8583 (3)	0.3743 (3)	0.0368 (9)
H3	0.860603	0.930628	0.432105	0.044*
C4	0.8047 (3)	0.7380 (3)	0.1606 (3)	0.0345 (8)
C5	0.8829 (3)	0.7449 (3)	0.1048 (3)	0.0368 (9)
C6	0.8890 (3)	0.6487 (3)	0.0098 (3)	0.0462 (10)
H6	0.945231	0.655996	−0.025495	0.055*
C7	0.8112 (4)	0.5426 (3)	−0.0317 (3)	0.0496 (10)
C8	0.7277 (4)	0.5312 (3)	0.0173 (4)	0.0510 (11)
H8	0.672915	0.457761	−0.013605	0.061*
C9	0.7257 (3)	0.6288 (3)	0.1118 (4)	0.0444 (10)
C10	0.9377 (3)	0.7896 (3)	0.4187 (3)	0.0352 (9)
C11	0.9874 (3)	0.8364 (3)	0.5385 (3)	0.0430 (10)
H11	0.971582	0.910179	0.584838	0.052*
C12	1.0571 (3)	0.7808 (3)	0.5908 (3)	0.0435 (10)
H12	1.087782	0.815862	0.671790	0.052*
C13	1.0843 (3)	0.6710 (3)	0.5253 (4)	0.0445 (10)
C14	1.0346 (3)	0.6234 (3)	0.4059 (3)	0.0445 (10)
H14	1.050264	0.549720	0.359228	0.053*
C15	0.9640 (3)	0.6804 (3)	0.3550 (3)	0.0429 (10)
H15	0.932054	0.644880	0.273950	0.051*
C16	1.2096 (4)	0.6691 (5)	0.7008 (4)	0.0730 (14)
H16A	1.147855	0.683826	0.736332	0.110*
H16B	1.264083	0.744801	0.727575	0.110*
H16C	1.254085	0.614745	0.721586	0.110*
C17	1.1921 (4)	0.5093 (4)	0.5104 (4)	0.0699 (14)
H17A	1.121910	0.445356	0.458370	0.105*
H17B	1.244237	0.483582	0.561782	0.105*
H17C	1.235231	0.527610	0.466086	0.105*
Br4	0.42342 (5)	0.48532 (4)	0.33567 (5)	0.07571 (18)
Br5	0.57610 (4)	0.19548 (4)	−0.01856 (4)	0.06937 (16)
Br6	0.18828 (4)	−0.00305 (4)	0.05300 (4)	0.05723 (14)
N3	0.0283 (4)	0.2885 (4)	0.1784 (4)	0.0813 (13)
N4	0.6575 (3)	0.1389 (3)	0.6178 (3)	0.0461 (8)
C18	0.1202 (4)	0.2712 (4)	0.2135 (4)	0.0558 (11)
C19	0.2362 (3)	0.2501 (3)	0.2580 (4)	0.0446 (10)
C20	0.2635 (3)	0.2411 (3)	0.3556 (4)	0.0439 (10)
H20	0.202042	0.250391	0.388059	0.053*
C21	0.3151 (3)	0.2390 (3)	0.1877 (3)	0.0390 (9)
C22	0.4013 (3)	0.3342 (3)	0.2113 (4)	0.0443 (10)
C23	0.4770 (3)	0.3209 (3)	0.1486 (4)	0.0449 (10)
H23	0.535806	0.386991	0.166671	0.054*
C24	0.4667 (3)	0.2131 (3)	0.0613 (3)	0.0424 (10)
C25	0.3811 (3)	0.1156 (3)	0.0311 (3)	0.0434 (10)
H25	0.373643	0.040537	−0.030950	0.052*
C26	0.3061 (3)	0.1319 (3)	0.0959 (3)	0.0404 (9)
C27	0.3697 (3)	0.2197 (3)	0.4208 (3)	0.0389 (9)
C28	0.3665 (3)	0.2047 (3)	0.5152 (3)	0.0435 (10)
H28	0.296719	0.213284	0.535530	0.052*
C29	0.4585 (3)	0.1783 (3)	0.5804 (3)	0.0429 (10)
H29	0.450666	0.167619	0.643161	0.052*
C30	0.5651 (3)	0.1667 (3)	0.5552 (3)	0.0387 (9)
C31	0.5706 (3)	0.1864 (3)	0.4623 (3)	0.0428 (10)
H31	0.641828	0.182516	0.444196	0.051*
C32	0.4763 (3)	0.2110 (3)	0.3973 (3)	0.0446 (10)
H32	0.483402	0.222403	0.334674	0.054*
C33	0.6464 (4)	0.1123 (4)	0.7093 (4)	0.0554 (11)
H33A	0.626324	0.180228	0.765152	0.083*
H33B	0.722035	0.097663	0.746960	0.083*
H33C	0.583458	0.041247	0.677308	0.083*
C34	0.7615 (4)	0.1172 (4)	0.5841 (4)	0.0570 (11)
H34A	0.805099	0.191839	0.594258	0.085*
H34B	0.736643	0.058036	0.503724	0.085*
H34C	0.813099	0.087035	0.631605	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0559 (3)	0.0553 (3)	0.0536 (3)	−0.00597 (19)	0.0264 (2)	0.0237 (2)
Br2	0.1163 (5)	0.0646 (3)	0.0535 (3)	0.0245 (3)	0.0357 (3)	−0.0009 (3)
Br3	0.0679 (3)	0.0526 (3)	0.0891 (4)	−0.0066 (2)	0.0488 (3)	0.0202 (3)
N1	0.076 (3)	0.058 (2)	0.050 (3)	0.023 (2)	0.019 (2)	0.023 (2)
N2	0.056 (2)	0.069 (2)	0.053 (3)	0.0241 (19)	0.020 (2)	0.029 (2)
C1	0.058 (3)	0.040 (2)	0.032 (2)	0.003 (2)	0.018 (2)	0.011 (2)
C2	0.036 (2)	0.034 (2)	0.034 (2)	0.0031 (16)	0.0176 (19)	0.0116 (18)
C3	0.039 (2)	0.033 (2)	0.037 (2)	0.0044 (16)	0.021 (2)	0.0087 (18)
C4	0.039 (2)	0.035 (2)	0.030 (2)	0.0058 (16)	0.0126 (18)	0.0153 (18)
C5	0.037 (2)	0.040 (2)	0.031 (2)	0.0024 (16)	0.0088 (19)	0.0167 (19)
C6	0.048 (3)	0.061 (3)	0.036 (2)	0.013 (2)	0.019 (2)	0.025 (2)
C7	0.061 (3)	0.047 (2)	0.030 (2)	0.013 (2)	0.016 (2)	0.007 (2)
C8	0.052 (3)	0.034 (2)	0.049 (3)	0.0000 (18)	0.012 (2)	0.007 (2)
C9	0.045 (2)	0.042 (2)	0.051 (3)	0.0046 (18)	0.023 (2)	0.022 (2)
C10	0.035 (2)	0.039 (2)	0.033 (2)	0.0057 (16)	0.0173 (19)	0.0141 (18)
C11	0.048 (2)	0.037 (2)	0.042 (3)	0.0056 (17)	0.021 (2)	0.013 (2)
C12	0.038 (2)	0.055 (2)	0.033 (2)	0.0036 (18)	0.012 (2)	0.017 (2)
C13	0.037 (2)	0.050 (2)	0.049 (3)	0.0086 (18)	0.018 (2)	0.023 (2)
C14	0.048 (2)	0.044 (2)	0.044 (3)	0.0132 (18)	0.024 (2)	0.016 (2)
C15	0.048 (2)	0.045 (2)	0.034 (2)	0.0066 (18)	0.019 (2)	0.013 (2)
C16	0.066 (3)	0.097 (4)	0.056 (4)	0.032 (3)	0.012 (3)	0.038 (3)
C17	0.072 (3)	0.084 (3)	0.074 (4)	0.040 (3)	0.038 (3)	0.042 (3)
Br4	0.0849 (4)	0.0501 (3)	0.0893 (4)	0.0049 (2)	0.0508 (3)	0.0166 (3)
Br5	0.0702 (3)	0.0830 (3)	0.0722 (4)	0.0076 (2)	0.0489 (3)	0.0365 (3)
Br6	0.0465 (3)	0.0572 (3)	0.0723 (3)	−0.00078 (19)	0.0232 (2)	0.0330 (2)
N3	0.054 (3)	0.143 (4)	0.093 (4)	0.042 (3)	0.038 (3)	0.083 (3)
N4	0.050 (2)	0.054 (2)	0.043 (2)	0.0178 (16)	0.0235 (18)	0.0244 (18)
C18	0.050 (3)	0.083 (3)	0.058 (3)	0.021 (2)	0.032 (3)	0.045 (3)
C19	0.041 (2)	0.052 (2)	0.055 (3)	0.0143 (18)	0.024 (2)	0.031 (2)
C20	0.047 (2)	0.045 (2)	0.058 (3)	0.0164 (18)	0.036 (2)	0.028 (2)
C21	0.036 (2)	0.050 (2)	0.045 (3)	0.0114 (17)	0.018 (2)	0.031 (2)
C22	0.043 (2)	0.044 (2)	0.052 (3)	0.0109 (18)	0.021 (2)	0.025 (2)
C23	0.037 (2)	0.055 (3)	0.057 (3)	0.0037 (18)	0.017 (2)	0.038 (2)
C24	0.045 (2)	0.055 (3)	0.043 (3)	0.0101 (19)	0.024 (2)	0.030 (2)
C25	0.049 (2)	0.049 (2)	0.037 (3)	0.0081 (18)	0.018 (2)	0.023 (2)
C26	0.033 (2)	0.049 (2)	0.048 (3)	0.0021 (17)	0.014 (2)	0.032 (2)
C27	0.041 (2)	0.039 (2)	0.043 (3)	0.0082 (16)	0.020 (2)	0.0205 (19)
C28	0.047 (2)	0.048 (2)	0.051 (3)	0.0164 (19)	0.033 (2)	0.025 (2)
C29	0.053 (3)	0.046 (2)	0.044 (3)	0.0152 (19)	0.030 (2)	0.024 (2)
C30	0.046 (2)	0.0319 (19)	0.038 (2)	0.0077 (16)	0.019 (2)	0.0119 (18)
C31	0.040 (2)	0.055 (2)	0.045 (3)	0.0151 (18)	0.025 (2)	0.026 (2)
C32	0.051 (3)	0.054 (2)	0.046 (3)	0.0161 (19)	0.031 (2)	0.028 (2)
C33	0.060 (3)	0.065 (3)	0.053 (3)	0.011 (2)	0.022 (2)	0.037 (2)
C34	0.051 (3)	0.070 (3)	0.055 (3)	0.021 (2)	0.023 (2)	0.028 (2)

Geometric parameters (Å, º)

Br1—C5	1.892 (3)	Br4—C22	1.892 (4)
Br2—C7	1.895 (4)	Br5—C24	1.894 (4)
Br3—C9	1.895 (4)	Br6—C26	1.899 (3)
N1—C1	1.139 (5)	N3—C18	1.146 (5)
N2—C13	1.363 (5)	N4—C30	1.361 (5)
N2—C16	1.451 (5)	N4—C33	1.458 (5)
N2—C17	1.460 (5)	N4—C34	1.448 (5)
C1—C2	1.438 (5)	C18—C19	1.443 (6)
C2—C3	1.347 (5)	C19—C20	1.337 (5)
C2—C4	1.486 (5)	C19—C21	1.498 (5)
C3—H3	0.9500	C20—H20	0.9500
C3—C10	1.446 (5)	C20—C27	1.448 (5)
C4—C5	1.381 (5)	C21—C22	1.390 (5)
C4—C9	1.394 (5)	C21—C26	1.381 (5)
C5—C6	1.385 (5)	C22—C23	1.384 (5)
C6—H6	0.9500	C23—H23	0.9500
C6—C7	1.372 (5)	C23—C24	1.354 (5)
C7—C8	1.379 (5)	C24—C25	1.379 (5)
C8—H8	0.9500	C25—H25	0.9500
C8—C9	1.373 (5)	C25—C26	1.396 (5)
C10—C11	1.411 (5)	C27—C28	1.390 (5)
C10—C15	1.402 (5)	C27—C32	1.399 (5)
C11—H11	0.9500	C28—H28	0.9500
C11—C12	1.364 (5)	C28—C29	1.366 (5)
C12—H12	0.9500	C29—H29	0.9500
C12—C13	1.419 (5)	C29—C30	1.412 (5)
C13—C14	1.406 (5)	C30—C31	1.408 (5)
C14—H14	0.9500	C31—H31	0.9500
C14—C15	1.373 (5)	C31—C32	1.370 (5)
C15—H15	0.9500	C32—H32	0.9500
C16—H16A	0.9800	C33—H33A	0.9800
C16—H16B	0.9800	C33—H33B	0.9800
C16—H16C	0.9800	C33—H33C	0.9800
C17—H17A	0.9800	C34—H34A	0.9800
C17—H17B	0.9800	C34—H34B	0.9800
C17—H17C	0.9800	C34—H34C	0.9800
C13—N2—C16	121.9 (4)	C30—N4—C33	120.6 (3)
C13—N2—C17	120.5 (4)	C30—N4—C34	120.6 (3)
C16—N2—C17	116.9 (3)	C34—N4—C33	118.1 (3)
N1—C1—C2	179.1 (5)	N3—C18—C19	179.7 (7)
C1—C2—C4	116.9 (3)	C18—C19—C21	115.6 (4)
C3—C2—C1	117.5 (3)	C20—C19—C18	118.4 (4)
C3—C2—C4	125.5 (3)	C20—C19—C21	126.0 (3)
C2—C3—H3	113.5	C19—C20—H20	114.1
C2—C3—C10	132.9 (3)	C19—C20—C27	131.8 (4)
C10—C3—H3	113.5	C27—C20—H20	114.1
C5—C4—C2	121.7 (3)	C22—C21—C19	122.4 (4)
C5—C4—C9	115.8 (3)	C26—C21—C19	121.1 (3)
C9—C4—C2	122.5 (3)	C26—C21—C22	116.5 (3)
C4—C5—Br1	119.7 (3)	C21—C22—Br4	120.5 (3)
C4—C5—C6	123.2 (3)	C23—C22—Br4	117.8 (3)
C6—C5—Br1	117.1 (3)	C23—C22—C21	121.6 (4)
C5—C6—H6	121.1	C22—C23—H23	120.2
C7—C6—C5	117.9 (4)	C24—C23—C22	119.7 (3)
C7—C6—H6	121.1	C24—C23—H23	120.2
C6—C7—Br2	118.9 (3)	C23—C24—Br5	118.8 (3)
C6—C7—C8	121.7 (4)	C23—C24—C25	121.9 (4)
C8—C7—Br2	119.4 (3)	C25—C24—Br5	119.3 (3)
C7—C8—H8	120.9	C24—C25—H25	121.5
C9—C8—C7	118.2 (3)	C24—C25—C26	117.1 (4)
C9—C8—H8	120.9	C26—C25—H25	121.5
C4—C9—Br3	118.5 (3)	C21—C26—Br6	120.1 (3)
C8—C9—Br3	118.5 (3)	C21—C26—C25	123.3 (3)
C8—C9—C4	123.0 (4)	C25—C26—Br6	116.6 (3)
C11—C10—C3	117.4 (3)	C28—C27—C20	117.7 (3)
C15—C10—C3	126.7 (3)	C28—C27—C32	116.0 (3)
C15—C10—C11	115.8 (3)	C32—C27—C20	126.2 (3)
C10—C11—H11	118.5	C27—C28—H28	118.3
C12—C11—C10	123.0 (3)	C29—C28—C27	123.4 (3)
C12—C11—H11	118.5	C29—C28—H28	118.3
C11—C12—H12	119.7	C28—C29—H29	119.7
C11—C12—C13	120.7 (4)	C28—C29—C30	120.6 (3)
C13—C12—H12	119.7	C30—C29—H29	119.7
N2—C13—C12	120.7 (4)	N4—C30—C29	121.8 (3)
N2—C13—C14	122.7 (4)	N4—C30—C31	122.0 (3)
C14—C13—C12	116.6 (4)	C31—C30—C29	116.2 (3)
C13—C14—H14	119.1	C30—C31—H31	119.0
C15—C14—C13	121.8 (4)	C32—C31—C30	121.9 (3)
C15—C14—H14	119.1	C32—C31—H31	119.0
C10—C15—H15	119.0	C27—C32—H32	119.1
C14—C15—C10	122.0 (4)	C31—C32—C27	121.7 (4)
C14—C15—H15	119.0	C31—C32—H32	119.1
N2—C16—H16A	109.5	N4—C33—H33A	109.5
N2—C16—H16B	109.5	N4—C33—H33B	109.5
N2—C16—H16C	109.5	N4—C33—H33C	109.5
H16A—C16—H16B	109.5	H33A—C33—H33B	109.5
H16A—C16—H16C	109.5	H33A—C33—H33C	109.5
H16B—C16—H16C	109.5	H33B—C33—H33C	109.5
N2—C17—H17A	109.5	N4—C34—H34A	109.5
N2—C17—H17B	109.5	N4—C34—H34B	109.5
N2—C17—H17C	109.5	N4—C34—H34C	109.5
H17A—C17—H17B	109.5	H34A—C34—H34B	109.5
H17A—C17—H17C	109.5	H34A—C34—H34C	109.5
H17B—C17—H17C	109.5	H34B—C34—H34C	109.5
Br1—C5—C6—C7	−179.4 (3)	Br4—C22—C23—C24	177.8 (3)
Br2—C7—C8—C9	178.3 (3)	Br5—C24—C25—C26	177.2 (3)
N2—C13—C14—C15	−180.0 (4)	N4—C30—C31—C32	178.1 (3)
C1—C2—C3—C10	178.4 (4)	C18—C19—C20—C27	179.5 (4)
C1—C2—C4—C5	85.0 (4)	C18—C19—C21—C22	97.0 (5)
C1—C2—C4—C9	−96.4 (4)	C18—C19—C21—C26	−83.8 (5)
C2—C3—C10—C11	−179.7 (4)	C19—C20—C27—C28	−174.4 (4)
C2—C3—C10—C15	1.0 (6)	C19—C20—C27—C32	4.7 (7)
C2—C4—C5—Br1	−3.9 (5)	C19—C21—C22—Br4	−0.1 (5)
C2—C4—C5—C6	175.1 (3)	C19—C21—C22—C23	177.0 (4)
C2—C4—C9—Br3	3.4 (5)	C19—C21—C26—Br6	2.5 (5)
C2—C4—C9—C8	−175.7 (4)	C19—C21—C26—C25	−176.9 (3)
C3—C2—C4—C5	−94.0 (4)	C20—C19—C21—C22	−83.7 (5)
C3—C2—C4—C9	84.6 (5)	C20—C19—C21—C26	95.6 (5)
C3—C10—C11—C12	−179.3 (3)	C20—C27—C28—C29	176.7 (3)
C3—C10—C15—C14	178.8 (3)	C20—C27—C32—C31	−177.7 (4)
C4—C2—C3—C10	−2.7 (6)	C21—C19—C20—C27	0.2 (7)
C4—C5—C6—C7	1.6 (6)	C21—C22—C23—C24	0.6 (6)
C5—C4—C9—Br3	−178.0 (3)	C22—C21—C26—Br6	−178.2 (3)
C5—C4—C9—C8	3.0 (6)	C22—C21—C26—C25	2.4 (6)
C5—C6—C7—Br2	−178.8 (3)	C22—C23—C24—Br5	−177.0 (3)
C5—C6—C7—C8	1.2 (6)	C22—C23—C24—C25	1.1 (6)
C6—C7—C8—C9	−1.7 (6)	C23—C24—C25—C26	−1.0 (6)
C7—C8—C9—Br3	−179.5 (3)	C24—C25—C26—Br6	179.7 (3)
C7—C8—C9—C4	−0.4 (6)	C24—C25—C26—C21	−0.9 (6)
C9—C4—C5—Br1	177.5 (3)	C26—C21—C22—Br4	−179.4 (3)
C9—C4—C5—C6	−3.5 (6)	C26—C21—C22—C23	−2.3 (6)
C10—C11—C12—C13	0.6 (6)	C27—C28—C29—C30	1.1 (6)
C11—C10—C15—C14	−0.5 (5)	C28—C27—C32—C31	1.4 (5)
C11—C12—C13—N2	179.6 (4)	C28—C29—C30—N4	−179.1 (3)
C11—C12—C13—C14	−0.9 (5)	C28—C29—C30—C31	1.3 (5)
C12—C13—C14—C15	0.5 (5)	C29—C30—C31—C32	−2.4 (5)
C13—C14—C15—C10	0.2 (6)	C30—C31—C32—C27	1.0 (6)
C15—C10—C11—C12	0.1 (5)	C32—C27—C28—C29	−2.5 (6)
C16—N2—C13—C12	−3.4 (6)	C33—N4—C30—C29	4.0 (5)
C16—N2—C13—C14	177.0 (4)	C33—N4—C30—C31	−176.5 (3)
C17—N2—C13—C12	−173.9 (4)	C34—N4—C30—C29	174.5 (3)
C17—N2—C13—C14	6.6 (6)	C34—N4—C30—C31	−6.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···C4	0.95	2.56	3.191 (5)	124
C15—H15···C9	0.95	2.75	3.504 (6)	137
C32—H32···C21	0.95	2.51	3.149 (5)	125
C32—H32···C22	0.95	2.65	3.446 (5)	142

(Z)-3-[4-(Dimethylamino)phenyl]-2-(2,4,6-tribromophenyl)prop-2-enenitrile (Zacryl)

Crystal data

C17H13Br3N2	F(000) = 936
Mr = 484.99	Dx = 1.948 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.082 (2) Å	Cell parameters from 7150 reflections
b = 13.024 (3) Å	θ = 2.5–30.4°
c = 14.266 (3) Å	µ = 7.32 mm^−1
β = 101.467 (3)°	T = 100 K
V = 1653.8 (6) Å^3	Prism, yellow
Z = 4	0.30 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer	3954 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.061
φ and ω scans	θmax = 30.6°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −12→12
Tmin = 0.120, Tmax = 0.222	k = −18→18
25670 measured reflections	l = −20→20
5071 independent reflections

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	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) + (0.034P)^2 + 0.4374P] where P = (Fo^2 + 2Fc^2)/3
5071 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 0.59 e Å^−3
0 restraints	Δρmin = −1.07 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
Br1	0.54668 (3)	0.59083 (2)	0.76907 (2)	0.01443 (7)
Br2	−0.02660 (3)	0.73745 (2)	0.79072 (2)	0.02085 (8)
Br3	0.29258 (3)	0.93565 (2)	0.54218 (2)	0.02020 (7)
N1	0.7073 (3)	0.93211 (17)	0.64818 (18)	0.0194 (5)
N2	1.0562 (2)	0.59048 (16)	0.37878 (16)	0.0150 (4)
C1	0.6333 (3)	0.8607 (2)	0.63280 (18)	0.0139 (5)
C2	0.5420 (3)	0.76963 (19)	0.61470 (18)	0.0119 (5)
C3	0.5751 (3)	0.69145 (18)	0.55982 (18)	0.0115 (5)
H3	0.5027	0.6379	0.5509	0.014*
C4	0.4078 (3)	0.76454 (18)	0.66008 (17)	0.0110 (5)
C5	0.3918 (3)	0.68805 (19)	0.72655 (18)	0.0117 (5)
C6	0.2643 (3)	0.6797 (2)	0.76624 (18)	0.0143 (5)
H6	0.2560	0.6267	0.8106	0.017*
C7	0.1494 (3)	0.7505 (2)	0.73972 (19)	0.0152 (5)
C8	0.1603 (3)	0.8291 (2)	0.67671 (19)	0.0154 (5)
H8	0.0825	0.8786	0.6609	0.018*
C9	0.2879 (3)	0.83430 (19)	0.63691 (18)	0.0138 (5)
C10	0.6993 (3)	0.67368 (18)	0.51219 (17)	0.0111 (5)
C11	0.6945 (3)	0.58412 (19)	0.45657 (18)	0.0137 (5)
H11	0.6087	0.5410	0.4499	0.016*
C12	0.8091 (3)	0.55636 (19)	0.41134 (18)	0.0135 (5)
H12	0.8009	0.4954	0.3741	0.016*
C13	0.9394 (3)	0.61878 (19)	0.42019 (17)	0.0124 (5)
C14	0.9425 (3)	0.71067 (19)	0.47314 (18)	0.0131 (5)
H14	1.0265	0.7553	0.4782	0.016*
C15	0.8263 (3)	0.7370 (2)	0.51759 (19)	0.0149 (5)
H15	0.8320	0.7994	0.5527	0.018*
C16	1.0513 (3)	0.4934 (2)	0.32853 (19)	0.0157 (5)
H16A	0.9681	0.4942	0.2730	0.024*
H16B	1.0362	0.4374	0.3716	0.024*
H16C	1.1462	0.4829	0.3071	0.024*
C17	1.1968 (3)	0.6475 (2)	0.3997 (2)	0.0193 (6)
H17A	1.1806	0.7169	0.3732	0.029*
H17B	1.2723	0.6123	0.3710	0.029*
H17C	1.2321	0.6517	0.4692	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01162 (12)	0.01344 (13)	0.01844 (13)	0.00250 (9)	0.00348 (9)	0.00418 (9)
Br2	0.01221 (12)	0.03001 (16)	0.02206 (15)	−0.00045 (10)	0.00760 (10)	−0.00982 (11)
Br3	0.02015 (14)	0.01703 (14)	0.02199 (14)	0.00415 (10)	0.00073 (11)	0.00642 (10)
N1	0.0199 (11)	0.0173 (11)	0.0227 (12)	−0.0032 (9)	0.0081 (10)	−0.0033 (9)
N2	0.0145 (10)	0.0150 (11)	0.0166 (11)	−0.0008 (8)	0.0054 (9)	−0.0010 (9)
C1	0.0148 (12)	0.0161 (12)	0.0114 (12)	0.0021 (10)	0.0036 (10)	−0.0007 (9)
C2	0.0105 (11)	0.0133 (12)	0.0115 (12)	−0.0004 (9)	0.0012 (9)	−0.0001 (9)
C3	0.0108 (11)	0.0100 (11)	0.0131 (11)	−0.0018 (9)	0.0009 (9)	0.0006 (9)
C4	0.0095 (11)	0.0123 (11)	0.0106 (12)	−0.0013 (9)	0.0006 (9)	−0.0033 (9)
C5	0.0083 (10)	0.0123 (11)	0.0134 (11)	0.0015 (9)	−0.0001 (9)	−0.0027 (9)
C6	0.0122 (11)	0.0167 (12)	0.0141 (12)	−0.0011 (9)	0.0027 (10)	−0.0015 (9)
C7	0.0109 (11)	0.0194 (13)	0.0155 (13)	0.0000 (9)	0.0033 (9)	−0.0080 (10)
C8	0.0103 (11)	0.0153 (13)	0.0186 (13)	0.0028 (9)	−0.0018 (10)	−0.0070 (10)
C9	0.0143 (12)	0.0129 (12)	0.0127 (12)	−0.0001 (9)	−0.0007 (9)	0.0000 (9)
C10	0.0100 (11)	0.0131 (12)	0.0095 (11)	−0.0006 (9)	0.0004 (9)	−0.0008 (9)
C11	0.0102 (11)	0.0130 (12)	0.0177 (12)	−0.0026 (9)	0.0019 (9)	0.0001 (10)
C12	0.0137 (12)	0.0125 (12)	0.0143 (12)	−0.0003 (9)	0.0027 (10)	−0.0017 (9)
C13	0.0121 (11)	0.0153 (12)	0.0096 (11)	−0.0001 (9)	0.0014 (9)	0.0015 (9)
C14	0.0116 (11)	0.0139 (12)	0.0132 (12)	−0.0042 (9)	0.0010 (9)	−0.0002 (9)
C15	0.0164 (12)	0.0124 (12)	0.0148 (12)	−0.0032 (9)	0.0005 (10)	−0.0020 (9)
C16	0.0162 (12)	0.0169 (13)	0.0147 (12)	0.0005 (10)	0.0051 (10)	0.0001 (10)
C17	0.0119 (12)	0.0210 (14)	0.0265 (15)	−0.0020 (10)	0.0076 (11)	0.0035 (11)

Geometric parameters (Å, º)

Br1—C5	1.900 (2)	C8—C9	1.390 (4)
Br2—C7	1.891 (3)	C8—H8	0.9500
Br3—C9	1.896 (3)	C10—C11	1.407 (3)
N1—C1	1.143 (3)	C10—C15	1.408 (3)
N2—C13	1.364 (3)	C11—C12	1.377 (3)
N2—C16	1.450 (3)	C11—H11	0.9500
N2—C17	1.456 (3)	C12—C13	1.421 (3)
C1—C2	1.440 (4)	C12—H12	0.9500
C2—C3	1.354 (3)	C13—C14	1.413 (3)
C2—C4	1.491 (3)	C14—C15	1.378 (4)
C3—C10	1.446 (3)	C14—H14	0.9500
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.403 (3)	C16—H16A	0.9800
C4—C9	1.406 (3)	C16—H16B	0.9800
C5—C6	1.391 (3)	C16—H16C	0.9800
C6—C7	1.387 (4)	C17—H17A	0.9800
C6—H6	0.9500	C17—H17B	0.9800
C7—C8	1.379 (4)	C17—H17C	0.9800
C13—N2—C16	120.0 (2)	C11—C10—C3	117.3 (2)
C13—N2—C17	120.0 (2)	C15—C10—C3	126.0 (2)
C16—N2—C17	119.1 (2)	C12—C11—C10	122.7 (2)
N1—C1—C2	178.9 (3)	C12—C11—H11	118.6
C3—C2—C1	122.5 (2)	C10—C11—H11	118.6
C3—C2—C4	120.8 (2)	C11—C12—C13	120.1 (2)
C1—C2—C4	116.7 (2)	C11—C12—H12	119.9
C2—C3—C10	132.5 (2)	C13—C12—H12	119.9
C2—C3—H3	113.8	N2—C13—C14	121.7 (2)
C10—C3—H3	113.8	N2—C13—C12	120.9 (2)
C5—C4—C9	116.0 (2)	C14—C13—C12	117.4 (2)
C5—C4—C2	121.9 (2)	C15—C14—C13	121.4 (2)
C9—C4—C2	122.1 (2)	C15—C14—H14	119.3
C6—C5—C4	122.5 (2)	C13—C14—H14	119.3
C6—C5—Br1	116.22 (19)	C14—C15—C10	121.5 (2)
C4—C5—Br1	121.28 (18)	C14—C15—H15	119.2
C7—C6—C5	118.7 (2)	C10—C15—H15	119.2
C7—C6—H6	120.7	N2—C16—H16A	109.5
C5—C6—H6	120.7	N2—C16—H16B	109.5
C8—C7—C6	121.5 (2)	H16A—C16—H16B	109.5
C8—C7—Br2	119.55 (19)	N2—C16—H16C	109.5
C6—C7—Br2	118.9 (2)	H16A—C16—H16C	109.5
C7—C8—C9	118.4 (2)	H16B—C16—H16C	109.5
C7—C8—H8	120.8	N2—C17—H17A	109.5
C9—C8—H8	120.8	N2—C17—H17B	109.5
C8—C9—C4	122.8 (2)	H17A—C17—H17B	109.5
C8—C9—Br3	117.61 (19)	N2—C17—H17C	109.5
C4—C9—Br3	119.44 (19)	H17A—C17—H17C	109.5
C11—C10—C15	116.7 (2)	H17B—C17—H17C	109.5
C1—C2—C3—C10	3.3 (4)	C2—C4—C9—C8	178.3 (2)
C4—C2—C3—C10	−176.3 (2)	C5—C4—C9—Br3	−176.24 (18)
C3—C2—C4—C5	61.4 (3)	C2—C4—C9—Br3	2.1 (3)
C1—C2—C4—C5	−118.3 (3)	C2—C3—C10—C11	−177.3 (3)
C3—C2—C4—C9	−116.8 (3)	C2—C3—C10—C15	3.8 (5)
C1—C2—C4—C9	63.5 (3)	C15—C10—C11—C12	2.0 (4)
C9—C4—C5—C6	1.2 (4)	C3—C10—C11—C12	−177.0 (2)
C2—C4—C5—C6	−177.1 (2)	C10—C11—C12—C13	0.4 (4)
C9—C4—C5—Br1	−177.69 (17)	C16—N2—C13—C14	177.3 (2)
C2—C4—C5—Br1	4.0 (3)	C17—N2—C13—C14	8.8 (4)
C4—C5—C6—C7	−0.6 (4)	C16—N2—C13—C12	−2.8 (4)
Br1—C5—C6—C7	178.28 (19)	C17—N2—C13—C12	−171.3 (2)
C5—C6—C7—C8	−1.2 (4)	C11—C12—C13—N2	177.6 (2)
C5—C6—C7—Br2	178.31 (18)	C11—C12—C13—C14	−2.5 (4)
C6—C7—C8—C9	2.3 (4)	N2—C13—C14—C15	−177.7 (2)
Br2—C7—C8—C9	−177.15 (18)	C12—C13—C14—C15	2.4 (4)
C7—C8—C9—C4	−1.8 (4)	C13—C14—C15—C10	0.0 (4)
C7—C8—C9—Br3	174.57 (19)	C11—C10—C15—C14	−2.1 (4)
C5—C4—C9—C8	0.0 (4)	C3—C10—C15—C14	176.7 (2)