Crystal structure analysis of a star-shaped triazine compound: a combination of single-crystal three-dimensional electron diffraction and powder X-ray diffraction

The solid-state structure of star-shaped 2,4,6-tris­{(E)-2-[4-(di­methyl­amino)-phenyl]ethenyl}-1,3,5-triazine is determined from a powder sample by exploiting the respective strengths of single-crystal three-dimensional electron diffraction and powder X-ray diffraction data. The unit-cell parameters were determined from single crystal electron diffraction data. Using this information, the powder X-ray diffraction data were indexed, and the crystal structure was determined from the powder diffraction profile. The compound crystallizes in a noncentrosymmetric space group, P2₁2₁2₁. The molecular conformation in the crystal structure was used to calculate the molecular dipole moment of 3.22 Debye, which enables the material to show nonlinear optical effects.

Computing details

Data collection: WINX^POW (Stoe & Cie, 2004); cell refinement: TOPAS-Academic (Coelho, 2012); data reduction: DASH 3.3 (David et al., 2006); program(s) used to solve structure: DASH 3.3 (David et al., 2006); program(s) used to refine structure: TOPAS-Academic (Coelho, 2012); molecular graphics: Mercury (Macrae et al., 2008).

2,4,6-tris((E)-2-(4-(dimethylamino)phenyl)ethenyl)-1,3,5-triazine

Crystal data

C33H36N6	Z = 4
Mr = 516.69	F(000) = 1104
Orthorhombic, P212121	Dx = 1.194 Mg m^−3
a = 54.631 (3) Å	Cu Kα1 radiation, λ = 1.54056 Å
b = 8.0040 (2) Å	T = 298 K
c = 6.5754 (3) Å	Particle morphology: powder
V = 2875.2 (2) Å^3	dark violet

Data collection

STOE-Stadi-P diffractometer	Scan method: continuous
Ge(111) monochromator	2θmin = 4.000°, 2θmax = 39.980°, 2θstep = 0.02°

Refinement

Least-squares matrix: full with fixed elements per cycle	258 parameters
Rp = 6.269	213 restraints
Rwp = 6.168	0 constraints
Rexp = 5.101	H-atom parameters not refined
RBragg = 0.966	Weighting scheme based on measured s.u.'s w = 1/σ[Yobs]^2
1800 data points	(Δ/σ)max = 0.001
Excluded region(s): none	Background function: Chebyshev function with 15 terms
Profile function: fundamental parameters	Preferred orientation correction: none

Special details

Geometry. H atoms added with Mercury.

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

	x	y	z	Uiso*/Ueq
C1	0.13318 (13)	0.0101 (10)	0.4203 (11)	0.050 (2)
C2	0.15500 (12)	−0.0564 (13)	0.5044 (11)	0.050 (2)
N1	0.13479 (15)	0.1003 (10)	0.2479 (12)	0.050 (2)
N3	0.11336 (14)	−0.0291 (11)	0.5273 (13)	0.050 (2)
C3	0.17680 (11)	−0.0298 (13)	0.4164 (12)	0.050 (2)
C12	0.11340 (12)	0.1530 (10)	0.1844 (11)	0.050 (2)
C23	0.09301 (12)	0.0303 (10)	0.4475 (11)	0.050 (2)
C4	0.20034 (12)	−0.0877 (12)	0.4886 (11)	0.050 (2)
N2	0.09232 (14)	0.1218 (11)	0.2758 (13)	0.050 (2)
C13	0.11146 (13)	0.2286 (13)	−0.0021 (10)	0.050 (2)
C24	0.06929 (12)	0.0017 (17)	0.5374 (10)	0.050 (2)
C5	0.20402 (12)	−0.1650 (11)	0.6795 (11)	0.050 (2)
C9	0.22047 (12)	−0.0864 (12)	0.3512 (10)	0.050 (2)
C14	0.13150 (12)	0.2596 (13)	−0.1004 (11)	0.050 (2)
C25	0.06509 (11)	−0.0616 (16)	0.7230 (11)	0.050 (2)
C6	0.22574 (12)	−0.2412 (10)	0.7286 (10)	0.050 (2)
C8	0.24262 (12)	−0.1583 (11)	0.3980 (11)	0.050 (2)
C15	0.13279 (12)	0.3738 (10)	−0.2655 (11)	0.050 (2)
C26	0.04179 (12)	−0.0835 (12)	0.8167 (11)	0.050 (2)
C7	0.24565 (10)	−0.2330 (7)	0.5893 (10)	0.050 (2)
C16	0.15518 (12)	0.4070 (11)	−0.3617 (11)	0.050 (2)
C20	0.11183 (12)	0.4399 (11)	−0.3622 (11)	0.050 (2)
C27	0.01977 (11)	−0.0192 (12)	0.7414 (11)	0.050 (2)
C31	0.04096 (12)	−0.1664 (11)	1.0020 (11)	0.050 (2)
N4	0.26655 (10)	−0.2928 (8)	0.6419 (10)	0.050 (2)
C17	0.15662 (12)	0.4950 (11)	−0.5371 (11)	0.050 (2)
C19	0.11285 (11)	0.5276 (11)	−0.5363 (11)	0.050 (2)
C28	−0.00159 (12)	−0.0366 (12)	0.8441 (11)	0.050 (2)
C30	0.01974 (12)	−0.1854 (12)	1.1103 (11)	0.050 (2)
C10	0.27305 (10)	−0.3594 (7)	0.8412 (10)	0.050 (2)
C11	0.28863 (9)	−0.3096 (7)	0.5102 (9)	0.050 (2)
C18	0.13524 (12)	0.5555 (7)	−0.6284 (10)	0.050 (2)
C29	−0.00237 (12)	−0.1192 (12)	1.0343 (11)	0.050 (2)
N5	0.13561 (12)	0.6352 (8)	−0.7985 (9)	0.050 (2)
N6	−0.02454 (12)	−0.1461 (12)	1.1279 (10)	0.050 (2)
C22	0.11470 (11)	0.7117 (7)	−0.9035 (8)	0.050 (2)
C21	0.15573 (11)	0.6782 (7)	−0.9382 (8)	0.050 (2)
C32	−0.04517 (11)	−0.0555 (8)	1.0442 (10)	0.050 (2)
C33	−0.02750 (13)	−0.2042 (8)	1.3402 (9)	0.050 (2)
H2	0.15404	−0.130483	0.643084	0.060 (2)
H3	0.176785	0.042778	0.276314	0.060 (2)
H13	0.093678	0.261444	−0.065379	0.060 (2)
H24	0.05335	0.034479	0.446307	0.060 (2)
H5	0.18923	−0.164063	0.790536	0.060 (2)
H9	0.218248	−0.026317	0.203757	0.060 (2)
H14	0.14815	0.195073	−0.054317	0.060 (2)
H25	0.081041	−0.100006	0.81064	0.060 (2)
H6	0.227718	−0.307184	0.872502	0.060 (2)
H8	0.257561	−0.157268	0.288377	0.060 (2)
H16	0.17198	0.360395	−0.292947	0.060 (2)
H20	0.094017	0.418818	−0.292439	0.060 (2)
H27	0.019792	0.046578	0.596424	0.060 (2)
H31	0.057831	−0.218298	1.06356	0.060 (2)
H17	0.174358	0.518651	−0.606957	0.060 (2)
H19	0.096147	0.576398	−0.604438	0.060 (2)
H28	−0.018392	0.013696	0.779338	0.060 (2)
H30	0.019930	−0.251569	1.255	0.060 (2)
H10a	0.288443	−0.285724	0.89624	0.060 (2)
H10b	0.278885	−0.488042	0.817581	0.060 (2)
H10c	0.257626	−0.352906	0.94582	0.060 (2)
H11a	0.303201	−0.238653	0.583104	0.060 (2)
H11b	0.285065	−0.263714	0.357125	0.060 (2)
H11c	0.293451	−0.441612	0.50863	0.060 (2)
H22a	0.118912	0.843968	−0.920295	0.060 (2)
H22b	0.097807	0.693423	−0.818436	0.060 (2)
H22c	0.113639	0.653801	−1.05311	0.060 (2)
H21a	0.173197	0.631831	−0.881778	0.060 (2)
H21b	0.155861	0.813799	−0.951729	0.060 (2)
H21c	0.151221	0.623021	−1.08488	0.060 (2)
H32a	−0.052662	0.020080	1.16704	0.060 (2)
H32b	−0.058614	−0.148489	0.997942	0.060 (2)
H32c	−0.039607	0.022019	0.916181	0.060 (2)
H33a	−0.038175	−0.109321	1.4191	0.060 (2)
H33b	−0.009816	−0.223004	1.41312	0.060 (2)
H33c	−0.037896	−0.320171	1.33386	0.060 (2)

Geometric parameters (Å, º)

C1—C2	1.42 (1)	C20—H20	1.0890
C1—N1	1.35 (1)	C27—C28	1.355 (9)
C1—N3	1.33 (1)	C27—H27	1.0890
C2—C3	1.341 (9)	C31—C30	1.37 (1)
C2—H2	1.0890	C31—H31	1.0890
N1—C12	1.31 (1)	N4—C10	1.459 (9)
N3—C23	1.32 (1)	N4—C11	1.491 (8)
C3—C4	1.45 (1)	C17—C18	1.40 (1)
C3—H3	1.0890	C17—H17	1.0890
C12—N2	1.32 (1)	C19—C18	1.383 (9)
C12—C13	1.37 (1)	C19—H19	1.0890
C23—N2	1.35 (1)	C28—C29	1.42 (1)
C23—C24	1.44 (1)	C28—H28	1.0890
C4—C5	1.41 (1)	C30—C29	1.41 (1)
C4—C9	1.423 (9)	C30—H30	1.0890
C13—C14	1.30 (1)	C10—H10a	1.0890
C13—H13	1.0890	C10—H10b	1.0890
C24—C25	1.34 (1)	C10—H10c	1.0890
C24—H24	1.0890	C11—H11a	1.0890
C5—C6	1.37 (1)	C11—H11b	1.0890
C5—H5	1.0890	C11—H11c	1.0890
C9—C8	1.37 (1)	C18—N5	1.288 (9)
C9—H9	1.0890	C29—N6	1.38 (1)
C14—C15	1.42 (1)	N5—C22	1.469 (9)
C14—H14	1.0890	N5—C21	1.473 (9)
C25—C26	1.425 (9)	N6—C32	1.45 (1)
C25—H25	1.0890	N6—C33	1.480 (9)
C6—C7	1.424 (9)	C22—H22a	1.0890
C6—H6	1.0890	C22—H22b	1.0890
C8—C7	1.40 (1)	C22—H22c	1.0890
C8—H8	1.0890	C21—H21a	1.0890
C15—C16	1.40 (1)	C21—H21b	1.0890
C15—C20	1.41 (1)	C21—H21c	1.0890
C26—C27	1.40 (1)	C32—H32a	1.0890
C26—C31	1.39 (1)	C32—H32b	1.0890
C7—N4	1.285 (8)	C32—H32c	1.0890
C16—C17	1.35 (1)	C33—H33a	1.0890
C16—H16	1.0890	C33—H33b	1.0890
C20—C19	1.34 (1)	C33—H33c	1.0890
C2—C1—N1	118.3 (7)	C30—C31—H31	118.75
C2—C1—N3	113.0 (7)	C7—N4—C10	126.4 (6)
N1—C1—N3	128.7 (8)	C7—N4—C11	126.6 (6)
C1—C2—C3	121.2 (7)	C10—N4—C11	107.0 (5)
C1—C2—H2	119.376	C16—C17—C18	119.8 (7)
C3—C2—H2	119.374	C16—C17—H17	120.102
C1—N1—C12	112.5 (7)	C18—C17—H17	120.1
C1—N3—C23	113.0 (8)	C20—C19—C18	119.6 (7)
C2—C3—C4	126.6 (8)	C20—C19—H19	120.199
C2—C3—H3	116.678	C18—C19—H19	120.199
C4—C3—H3	116.68	C27—C28—C29	120.9 (7)
N1—C12—N2	124.8 (8)	C27—C28—H28	119.528
N1—C12—C13	119.7 (7)	C29—C28—H28	119.528
N2—C12—C13	115.0 (7)	C31—C30—C29	119.9 (7)
N3—C23—N2	123.6 (7)	C31—C30—H30	120.028
N3—C23—C24	122.5 (7)	C29—C30—H30	120.028
N2—C23—C24	113.9 (7)	N4—C10—H10a	106.779
C3—C4—C5	123.9 (7)	N4—C10—H10b	106.779
C3—C4—C9	118.4 (7)	N4—C10—H10c	111.206
C5—C4—C9	117.2 (7)	H10a—C10—H10b	109.473
C12—N2—C23	117.3 (8)	H10a—C10—H10c	111.206
C12—C13—C14	117.7 (8)	H10b—C10—H10c	111.205
C12—C13—H13	121.134	N4—C11—H11a	106.779
C14—C13—H13	121.134	N4—C11—H11b	111.206
C23—C24—C25	125.9 (8)	N4—C11—H11c	106.779
C23—C24—H24	117.045	H11a—C11—H11b	111.206
C25—C24—H24	117.046	H11a—C11—H11c	109.471
C4—C5—C6	121.7 (7)	H11b—C11—H11c	111.206
C4—C5—H5	119.125	C17—C18—C19	119.6 (6)
C6—C5—H5	119.127	C17—C18—N5	122.1 (6)
C4—C9—C8	122.3 (7)	C19—C18—N5	118.3 (6)
C4—C9—H9	118.83	C28—C29—C30	117.6 (7)
C8—C9—H9	118.831	C28—C29—N6	119.7 (7)
C13—C14—C15	123.1 (8)	C30—C29—N6	122.5 (7)
C13—C14—H14	118.441	C18—N5—C22	127.1 (6)
C15—C14—H14	118.44	C18—N5—C21	132.0 (6)
C24—C25—C26	126.4 (8)	C22—N5—C21	100.9 (5)
C24—C25—H25	116.825	C29—N6—C32	115.9 (7)
C26—C25—H25	116.825	C29—N6—C33	124.6 (7)
C5—C6—C7	119.3 (6)	C32—N6—C33	115.5 (6)
C5—C6—H6	120.373	N5—C22—H22a	106.777
C7—C6—H6	120.372	N5—C22—H22b	111.206
C9—C8—C7	118.9 (7)	N5—C22—H22c	106.779
C9—C8—H8	120.556	H22a—C22—H22b	111.207
C7—C8—H8	120.558	H22a—C22—H22c	109.472
C14—C15—C16	120.6 (7)	H22b—C22—H22c	111.205
C14—C15—C20	123.0 (7)	N5—C21—H21a	111.206
C16—C15—C20	115.7 (7)	N5—C21—H21b	106.778
C25—C26—C27	124.7 (7)	N5—C21—H21c	106.78
C25—C26—C31	117.9 (7)	H21a—C21—H21b	111.206
C27—C26—C31	117.3 (7)	H21a—C21—H21c	111.205
C6—C7—C8	120.4 (6)	H21b—C21—H21c	109.471
C6—C7—N4	119.2 (6)	N6—C32—H32a	106.779
C8—C7—N4	120.3 (6)	N6—C32—H32b	106.779
C15—C16—C17	122.2 (7)	N6—C32—H32c	111.206
C15—C16—H16	118.877	H32a—C32—H32b	109.471
C17—C16—H16	118.878	H32a—C32—H32c	111.206
C15—C20—C19	123.1 (7)	H32b—C32—H32c	111.206
C15—C20—H20	118.474	N6—C33—H33a	106.78
C19—C20—H20	118.474	N6—C33—H33b	111.206
C26—C27—C28	121.7 (7)	N6—C33—H33c	106.777
C26—C27—H27	119.126	H33a—C33—H33b	111.205
C28—C27—H27	119.126	H33a—C33—H33c	109.472
C26—C31—C30	122.5 (7)	H33b—C33—H33c	111.207
C26—C31—H31	118.747