Bis(4-chloro­phenyl)[4-(2,2-di­phenyl­vinyl)­phenyl]­amine

The title compound, C₃₂H₂₃Cl₂N, was synthesized via the Ullmann reaction. The orientations of the three aromatic rings attached to the vinyl group are determined by the sp² state of the vinyl C atoms. The crystal packing is stabilized by weak C—H...π interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• R factor = 0.062
• wR factor = 0.123
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.799     0.970
            Tmin' and Tmax expected:      0.906     0.974
            RR' =      0.885
            Please check that your absorption correction is appropriate.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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

Bis(4-chlorophenyl)[4-(2,2-diphenylvinyl)phenyl]amine

Crystal data

C32H23Cl2N	Dx = 1.248 Mg m^−3
Mr = 492.41	Melting point = 395–399 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.784 (3) Å	Cell parameters from 728 reflections
b = 23.620 (7) Å	θ = 2.2–22.7°
c = 11.752 (4) Å	µ = 0.27 mm^−1
β = 105.228 (5)°	T = 293 K
V = 2620.5 (14) Å^3	Plate, colorless
Z = 4	0.36 × 0.28 × 0.10 mm
F(000) = 1024

Data collection

Bruker SMART CCD area-detector diffractometer	5355 independent reflections
Radiation source: fine-focus sealed tube	2565 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
φ and ω scans	θmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −11→12
Tmin = 0.799, Tmax = 0.970	k = −17→29
14866 measured reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.062	w = 1/[σ^2(Fo^2) + (0.084P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.123	(Δ/σ)max = 0.001
S = 0.99	Δρmax = 0.25 e Å^−3
5355 reflections	Δρmin = −0.29 e Å^−3
316 parameters

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
Cl1	1.39659 (9)	0.38478 (5)	1.24952 (9)	0.0940 (4)
Cl2	0.39923 (11)	0.20774 (4)	1.05194 (9)	0.0929 (4)
N1	0.8032 (2)	0.37674 (10)	0.95587 (19)	0.0457 (6)
C1	0.7814 (3)	0.40466 (11)	0.8451 (2)	0.0392 (7)
C2	0.6552 (3)	0.43210 (12)	0.7938 (2)	0.0420 (7)
H2	0.5828	0.4322	0.8316	0.050*
C3	0.6360 (3)	0.45933 (11)	0.6868 (2)	0.0409 (7)
H3	0.5506	0.4777	0.6542	0.049*
C4	0.7403 (3)	0.46005 (11)	0.6267 (2)	0.0403 (7)
C5	0.8678 (3)	0.43362 (12)	0.6799 (2)	0.0464 (8)
H5	0.9408	0.4343	0.6428	0.056*
C6	0.8883 (3)	0.40626 (12)	0.7876 (2)	0.0465 (8)
H6	0.9747	0.3888	0.8216	0.056*
C7	0.7160 (3)	0.49022 (12)	0.5129 (2)	0.0441 (7)
H7	0.6653	0.5239	0.5068	0.053*
C8	0.7581 (3)	0.47506 (12)	0.4169 (2)	0.0407 (7)
C9	0.7362 (3)	0.51377 (13)	0.3133 (2)	0.0417 (7)
C10	0.7471 (3)	0.57209 (13)	0.3266 (3)	0.0498 (8)
H10	0.7693	0.5875	0.4021	0.060*
C11	0.7260 (3)	0.60778 (14)	0.2310 (3)	0.0614 (9)
H11	0.7335	0.6467	0.2424	0.074*
C12	0.6939 (3)	0.58593 (17)	0.1191 (3)	0.0677 (10)
H12	0.6792	0.6100	0.0544	0.081*
C13	0.6835 (3)	0.52862 (17)	0.1030 (3)	0.0662 (10)
H13	0.6621	0.5138	0.0270	0.079*
C14	0.7047 (3)	0.49236 (14)	0.1992 (3)	0.0550 (8)
H14	0.6977	0.4534	0.1872	0.066*
C15	0.8276 (3)	0.41973 (12)	0.4091 (2)	0.0406 (7)
C16	0.9569 (3)	0.41774 (13)	0.3824 (2)	0.0482 (8)
H16	0.9982	0.4511	0.3654	0.058*
C17	1.0253 (3)	0.36689 (15)	0.3807 (3)	0.0604 (9)
H17	1.1132	0.3664	0.3640	0.072*
C18	0.9658 (4)	0.31695 (15)	0.4032 (3)	0.0684 (10)
H18	1.0124	0.2827	0.4021	0.082*
C19	0.8362 (4)	0.31853 (14)	0.4272 (3)	0.0658 (10)
H19	0.7944	0.2849	0.4419	0.079*
C20	0.7667 (3)	0.36915 (14)	0.4302 (2)	0.0551 (8)
H20	0.6786	0.3693	0.4464	0.066*
C21	0.9439 (3)	0.37743 (12)	1.0314 (2)	0.0397 (7)
C22	1.0227 (3)	0.32861 (13)	1.0609 (3)	0.0551 (8)
H22	0.9817	0.2938	1.0351	0.066*
C23	1.1615 (3)	0.33067 (15)	1.1281 (3)	0.0623 (9)
H23	1.2137	0.2975	1.1477	0.075*
C24	1.2209 (3)	0.38188 (16)	1.1655 (2)	0.0522 (8)
C25	1.1444 (3)	0.43113 (13)	1.1391 (2)	0.0494 (8)
H25	1.1859	0.4658	1.1654	0.059*
C26	1.0053 (3)	0.42857 (13)	1.0732 (2)	0.0450 (7)
H26	0.9523	0.4617	1.0567	0.054*
C27	0.7040 (3)	0.33751 (11)	0.9769 (2)	0.0398 (7)
C28	0.6038 (3)	0.31197 (12)	0.8857 (2)	0.0452 (7)
H28	0.5999	0.3214	0.8080	0.054*
C29	0.5095 (3)	0.27262 (12)	0.9085 (3)	0.0518 (8)
H29	0.4425	0.2558	0.8466	0.062*
C30	0.5155 (3)	0.25862 (13)	1.0232 (3)	0.0559 (9)
C31	0.6130 (4)	0.28372 (14)	1.1143 (3)	0.0618 (9)
H31	0.6160	0.2741	1.1916	0.074*
C32	0.7067 (3)	0.32320 (13)	1.0923 (3)	0.0539 (8)
H32	0.7720	0.3403	1.1549	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0490 (5)	0.1200 (9)	0.0973 (8)	0.0014 (5)	−0.0087 (5)	0.0078 (7)
Cl2	0.1013 (8)	0.0886 (7)	0.0974 (8)	−0.0445 (6)	0.0413 (6)	0.0036 (6)
N1	0.0414 (13)	0.0575 (16)	0.0331 (13)	−0.0112 (13)	0.0009 (11)	0.0108 (12)
C1	0.0384 (16)	0.0464 (18)	0.0319 (16)	−0.0047 (14)	0.0076 (13)	0.0050 (14)
C2	0.0359 (16)	0.056 (2)	0.0363 (17)	−0.0015 (15)	0.0146 (13)	0.0040 (15)
C3	0.0338 (16)	0.0511 (19)	0.0361 (17)	0.0038 (14)	0.0060 (13)	0.0054 (15)
C4	0.0353 (16)	0.0522 (19)	0.0337 (16)	0.0016 (14)	0.0093 (13)	0.0034 (15)
C5	0.0354 (16)	0.070 (2)	0.0369 (17)	0.0040 (15)	0.0151 (13)	0.0045 (16)
C6	0.0399 (17)	0.061 (2)	0.0366 (18)	0.0063 (15)	0.0069 (14)	0.0084 (16)
C7	0.0354 (16)	0.055 (2)	0.0404 (18)	0.0040 (15)	0.0071 (13)	0.0111 (16)
C8	0.0355 (16)	0.0498 (19)	0.0354 (17)	−0.0034 (14)	0.0069 (13)	0.0053 (15)
C9	0.0364 (16)	0.053 (2)	0.0381 (18)	0.0054 (15)	0.0134 (13)	0.0089 (16)
C10	0.0466 (18)	0.059 (2)	0.0454 (19)	0.0079 (16)	0.0152 (15)	0.0106 (17)
C11	0.060 (2)	0.059 (2)	0.070 (3)	0.0106 (18)	0.0246 (18)	0.022 (2)
C12	0.065 (2)	0.085 (3)	0.062 (3)	0.026 (2)	0.0328 (19)	0.036 (2)
C13	0.072 (2)	0.093 (3)	0.039 (2)	0.020 (2)	0.0239 (17)	0.013 (2)
C14	0.058 (2)	0.070 (2)	0.0388 (19)	0.0059 (17)	0.0158 (15)	0.0068 (18)
C15	0.0423 (18)	0.050 (2)	0.0272 (15)	−0.0018 (15)	0.0052 (13)	0.0078 (14)
C16	0.053 (2)	0.048 (2)	0.0469 (19)	0.0020 (16)	0.0185 (15)	0.0071 (15)
C17	0.065 (2)	0.074 (3)	0.049 (2)	0.013 (2)	0.0259 (17)	0.0081 (19)
C18	0.092 (3)	0.051 (2)	0.064 (2)	0.015 (2)	0.024 (2)	0.0100 (18)
C19	0.082 (3)	0.049 (2)	0.064 (2)	−0.013 (2)	0.014 (2)	0.0086 (18)
C20	0.0508 (19)	0.062 (2)	0.052 (2)	−0.0076 (18)	0.0114 (16)	0.0079 (17)
C21	0.0452 (17)	0.0447 (19)	0.0301 (16)	−0.0057 (16)	0.0112 (13)	0.0040 (14)
C22	0.063 (2)	0.043 (2)	0.053 (2)	0.0001 (17)	0.0040 (17)	−0.0065 (16)
C23	0.060 (2)	0.057 (2)	0.063 (2)	0.0144 (19)	0.0052 (18)	0.0030 (19)
C24	0.0395 (17)	0.074 (3)	0.0404 (18)	−0.0006 (18)	0.0057 (14)	0.0070 (18)
C25	0.0490 (19)	0.054 (2)	0.0445 (19)	−0.0127 (17)	0.0112 (15)	−0.0017 (16)
C26	0.0433 (18)	0.050 (2)	0.0423 (18)	−0.0002 (16)	0.0120 (14)	0.0074 (15)
C27	0.0420 (17)	0.0404 (18)	0.0372 (17)	−0.0017 (14)	0.0106 (14)	0.0022 (14)
C28	0.0517 (19)	0.0474 (19)	0.0361 (17)	−0.0002 (16)	0.0109 (15)	0.0011 (15)
C29	0.0511 (19)	0.046 (2)	0.055 (2)	−0.0068 (16)	0.0082 (16)	−0.0035 (17)
C30	0.062 (2)	0.050 (2)	0.060 (2)	−0.0148 (17)	0.0243 (18)	0.0019 (18)
C31	0.078 (2)	0.066 (2)	0.046 (2)	−0.014 (2)	0.0252 (19)	0.0054 (18)
C32	0.060 (2)	0.063 (2)	0.0362 (18)	−0.0129 (17)	0.0086 (15)	0.0010 (16)

Geometric parameters (Å, º)

Cl1—C24	1.744 (3)	C15—C16	1.382 (4)
Cl2—C30	1.748 (3)	C15—C20	1.386 (4)
N1—C27	1.410 (3)	C16—C17	1.378 (4)
N1—C1	1.425 (3)	C16—H16	0.9300
N1—C21	1.429 (3)	C17—C18	1.372 (4)
C1—C2	1.385 (3)	C17—H17	0.9300
C1—C6	1.387 (3)	C18—C19	1.370 (4)
C2—C3	1.380 (3)	C18—H18	0.9300
C2—H2	0.9300	C19—C20	1.380 (4)
C3—C4	1.386 (3)	C19—H19	0.9300
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.388 (4)	C21—C22	1.380 (4)
C4—C7	1.479 (4)	C21—C26	1.380 (4)
C5—C6	1.388 (4)	C22—C23	1.381 (4)
C5—H5	0.9300	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.364 (4)
C7—C8	1.347 (3)	C23—H23	0.9300
C7—H7	0.9300	C24—C25	1.374 (4)
C8—C15	1.487 (4)	C25—C26	1.379 (4)
C8—C9	1.493 (4)	C25—H25	0.9300
C9—C10	1.387 (4)	C26—H26	0.9300
C9—C14	1.389 (4)	C27—C28	1.387 (4)
C10—C11	1.376 (4)	C27—C32	1.391 (4)
C10—H10	0.9300	C28—C29	1.385 (4)
C11—C12	1.370 (4)	C28—H28	0.9300
C11—H11	0.9300	C29—C30	1.374 (4)
C12—C13	1.367 (4)	C29—H29	0.9300
C12—H12	0.9300	C30—C31	1.368 (4)
C13—C14	1.391 (4)	C31—C32	1.379 (4)
C13—H13	0.9300	C31—H31	0.9300
C14—H14	0.9300	C32—H32	0.9300
C27—N1—C1	121.4 (2)	C15—C16—H16	119.7
C27—N1—C21	119.6 (2)	C18—C17—C16	120.9 (3)
C1—N1—C21	116.8 (2)	C18—C17—H17	119.5
C2—C1—C6	118.4 (2)	C16—C17—H17	119.5
C2—C1—N1	121.1 (2)	C19—C18—C17	118.7 (3)
C6—C1—N1	120.5 (2)	C19—C18—H18	120.7
C3—C2—C1	120.5 (2)	C17—C18—H18	120.7
C3—C2—H2	119.8	C18—C19—C20	121.2 (3)
C1—C2—H2	119.8	C18—C19—H19	119.4
C2—C3—C4	121.9 (3)	C20—C19—H19	119.4
C2—C3—H3	119.1	C19—C20—C15	120.3 (3)
C4—C3—H3	119.1	C19—C20—H20	119.9
C3—C4—C5	117.4 (2)	C15—C20—H20	119.9
C3—C4—C7	120.2 (2)	C22—C21—C26	118.7 (3)
C5—C4—C7	122.4 (2)	C22—C21—N1	122.0 (3)
C6—C5—C4	121.2 (3)	C26—C21—N1	119.3 (3)
C6—C5—H5	119.4	C21—C22—C23	121.0 (3)
C4—C5—H5	119.4	C21—C22—H22	119.5
C1—C6—C5	120.6 (3)	C23—C22—H22	119.5
C1—C6—H6	119.7	C24—C23—C22	119.2 (3)
C5—C6—H6	119.7	C24—C23—H23	120.4
C8—C7—C4	128.1 (3)	C22—C23—H23	120.4
C8—C7—H7	115.9	C23—C24—C25	121.1 (3)
C4—C7—H7	115.9	C23—C24—Cl1	119.4 (3)
C7—C8—C15	122.1 (2)	C25—C24—Cl1	119.5 (3)
C7—C8—C9	120.7 (3)	C24—C25—C26	119.3 (3)
C15—C8—C9	117.2 (2)	C24—C25—H25	120.4
C10—C9—C14	117.5 (3)	C26—C25—H25	120.4
C10—C9—C8	121.7 (3)	C25—C26—C21	120.7 (3)
C14—C9—C8	120.8 (3)	C25—C26—H26	119.6
C11—C10—C9	121.7 (3)	C21—C26—H26	119.6
C11—C10—H10	119.1	C28—C27—C32	118.5 (3)
C9—C10—H10	119.1	C28—C27—N1	122.0 (2)
C12—C11—C10	120.0 (3)	C32—C27—N1	119.5 (2)
C12—C11—H11	120.0	C29—C28—C27	120.9 (3)
C10—C11—H11	120.0	C29—C28—H28	119.5
C13—C12—C11	119.8 (3)	C27—C28—H28	119.5
C13—C12—H12	120.1	C30—C29—C28	119.5 (3)
C11—C12—H12	120.1	C30—C29—H29	120.3
C12—C13—C14	120.5 (3)	C28—C29—H29	120.3
C12—C13—H13	119.8	C31—C30—C29	120.4 (3)
C14—C13—H13	119.8	C31—C30—Cl2	120.1 (3)
C9—C14—C13	120.6 (3)	C29—C30—Cl2	119.5 (3)
C9—C14—H14	119.7	C30—C31—C32	120.5 (3)
C13—C14—H14	119.7	C30—C31—H31	119.7
C16—C15—C20	118.3 (3)	C32—C31—H31	119.7
C16—C15—C8	120.3 (3)	C31—C32—C27	120.2 (3)
C20—C15—C8	121.4 (3)	C31—C32—H32	119.9
C17—C16—C15	120.7 (3)	C27—C32—H32	119.9
C17—C16—H16	119.7
C27—N1—C1—C2	50.9 (4)	C8—C15—C16—C17	176.8 (3)
C21—N1—C1—C2	−146.3 (3)	C15—C16—C17—C18	1.2 (5)
C27—N1—C1—C6	−130.8 (3)	C16—C17—C18—C19	0.2 (5)
C21—N1—C1—C6	31.9 (4)	C17—C18—C19—C20	−0.6 (5)
C6—C1—C2—C3	1.3 (4)	C18—C19—C20—C15	−0.2 (5)
N1—C1—C2—C3	179.5 (2)	C16—C15—C20—C19	1.6 (4)
C1—C2—C3—C4	0.4 (4)	C8—C15—C20—C19	−177.3 (3)
C2—C3—C4—C5	−1.9 (4)	C27—N1—C21—C22	48.3 (4)
C2—C3—C4—C7	−179.4 (3)	C1—N1—C21—C22	−114.8 (3)
C3—C4—C5—C6	1.7 (4)	C27—N1—C21—C26	−134.0 (3)
C7—C4—C5—C6	179.1 (3)	C1—N1—C21—C26	62.9 (3)
C2—C1—C6—C5	−1.5 (4)	C26—C21—C22—C23	−1.7 (4)
N1—C1—C6—C5	−179.7 (2)	N1—C21—C22—C23	176.0 (3)
C4—C5—C6—C1	0.0 (4)	C21—C22—C23—C24	−0.1 (5)
C3—C4—C7—C8	−142.8 (3)	C22—C23—C24—C25	1.2 (5)
C5—C4—C7—C8	39.9 (4)	C22—C23—C24—Cl1	−179.5 (2)
C4—C7—C8—C15	6.1 (4)	C23—C24—C25—C26	−0.3 (4)
C4—C7—C8—C9	−173.9 (2)	Cl1—C24—C25—C26	−179.7 (2)
C7—C8—C9—C10	35.5 (4)	C24—C25—C26—C21	−1.6 (4)
C15—C8—C9—C10	−144.5 (3)	C22—C21—C26—C25	2.6 (4)
C7—C8—C9—C14	−144.9 (3)	N1—C21—C26—C25	−175.2 (2)
C15—C8—C9—C14	35.1 (4)	C1—N1—C27—C28	18.6 (4)
C14—C9—C10—C11	0.8 (4)	C21—N1—C27—C28	−143.7 (3)
C8—C9—C10—C11	−179.5 (2)	C1—N1—C27—C32	−162.1 (3)
C9—C10—C11—C12	−0.3 (4)	C21—N1—C27—C32	35.6 (4)
C10—C11—C12—C13	−0.3 (5)	C32—C27—C28—C29	−0.7 (4)
C11—C12—C13—C14	0.3 (5)	N1—C27—C28—C29	178.6 (2)
C10—C9—C14—C13	−0.8 (4)	C27—C28—C29—C30	−0.1 (4)
C8—C9—C14—C13	179.6 (3)	C28—C29—C30—C31	0.6 (5)
C12—C13—C14—C9	0.2 (5)	C28—C29—C30—Cl2	−178.5 (2)
C7—C8—C15—C16	−126.1 (3)	C29—C30—C31—C32	−0.3 (5)
C9—C8—C15—C16	53.9 (3)	Cl2—C30—C31—C32	178.9 (2)
C7—C8—C15—C20	52.7 (4)	C30—C31—C32—C27	−0.6 (5)
C9—C8—C15—C20	−127.2 (3)	C28—C27—C32—C31	1.1 (4)
C20—C15—C16—C17	−2.1 (4)	N1—C27—C32—C31	−178.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···C2g^i	0.93	2.85	3.622 (4)	141
C19—H19···C5g^ii	0.93	2.87	3.776 (5)	164
C25—H25···C1g^iii	0.93	2.65	3.553 (4)	163
C32—H32···C3g^iv	0.93	2.95	3.812 (4)	155

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y−3/2, z−1/2; (iii) −x+2, −y+1, −z+2; (iv) x, y, z+1.