cis-1,2-Di­bromo-1,2-di­phenyl­ethene–di­phenyl­ethyne (2/1)

Barnes, J.C.; Chudek, J.A.

doi:10.1107/S160053680200942X

cis-1,2-Dibromo-1,2-diphenylethene–diphenylethyne (2/1)

The molecular components, 2C₁₄H₁₀Br₂·C₁₄H₁₀, are arranged in separate stacks in this ordered structure. There is no evidence of π–π intermolecular interaction. Diphenylethyne lies on a crystallographic inversion centre. The structure can be represented as centrosymmetric trimolecular units, held together by a C—H

ring interaction between a stilbene and each of the phenyl groups of the diphenylethyne (H

Cg_ring 2.66 Å; Cg_ring indicates a ring centroid).

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680200942X/cm6007sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680200942X/cm6007Isup2.hkl Contains datablock I

CCDC reference: 189416

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.006 Å
R factor = 0.055
wR factor = 0.148
Data-to-parameter ratio = 17.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSTM_02  Alert C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
          Tmin and Tmax reported:      0.946     0.999
          Tmin and Tmax expected:      0.335     0.494
          RR =      1.395
          Please check that your absorption correction is appropriate.

RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.103

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(21)  -   C(22)  =       1.44 Ang.

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      0.495
          Tmax scaled      0.494 Tmin scaled      0.468


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 3 Alert Level C = Please check

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999).

Cis-1,2-dibromo-1,2-diphenylethene, diphenylethyne (2:1) top

Crystal data top

C₁₄H₁₀Br₂·0.5C₁₄H₁₀	D_x = 1.646 Mg m⁻³
M_r = 427.15	Melting point = 68–71 K
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.8445 (5) Å	Cell parameters from 13506 reflections
b = 5.7702 (3) Å	θ = 1.0–27.1°
c = 20.741 (9) Å	µ = 4.70 mm⁻¹
β = 104.037 (2)°	T = 150 K
V = 1723.5 (8) Å³	Block, colourless
Z = 4	0.30 × 0.20 × 0.15 mm
F(000) = 844

Data collection top

Enraf–Nonius KappaCCD area-detector diffractometer	3718 independent reflections
Radiation source: Enraf–Nonius FR591 rotating anode	2614 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.103
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.1°, θ_min = 2.8°
φ and ω scans	h = −19→18
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −6→7
T_min = 0.946, T_max = 0.999	l = −23→26
11791 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0826P)²] where P = (F_o² + 2F_c²)/3
3718 reflections	(Δ/σ)_max = 0.002
208 parameters	Δρ_max = 0.76 e Å⁻³
0 restraints	Δρ_min = −0.95 e Å⁻³

Special details top

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

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 (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.55860 (4)	0.41738 (10)	0.08283 (2)	0.0458 (2)
Br2	0.39224 (3)	0.74326 (8)	0.11248 (2)	0.03678 (19)
C1	0.5219 (3)	0.3848 (8)	0.1643 (2)	0.0270 (9)
C2	0.4530 (3)	0.5159 (8)	0.1751 (2)	0.0268 (9)
C3	0.5766 (3)	0.2153 (8)	0.2110 (2)	0.0268 (10)
C4	0.6070 (3)	0.0098 (8)	0.1873 (2)	0.0293 (10)
H4	0.5929	−0.0190	0.1409	0.038*
C5	0.6576 (3)	−0.1518 (8)	0.2308 (2)	0.0303 (10)
H5	0.6764	−0.2925	0.2141	0.039*
C6	0.6808 (3)	−0.1085 (8)	0.2987 (2)	0.0309 (10)
H6	0.7164	−0.2179	0.3286	0.040*
C7	0.6518 (3)	0.0947 (8)	0.3226 (2)	0.0296 (10)
H7	0.6670	0.1242	0.3690	0.038*
C8	0.6005 (3)	0.2562 (7)	0.2790 (2)	0.0247 (9)
H8	0.5816	0.3963	0.2959	0.032*
C9	0.4140 (3)	0.5057 (8)	0.2344 (2)	0.0277 (9)
C10	0.3636 (3)	0.3103 (8)	0.2446 (2)	0.0307 (10)
H10	0.3551	0.1841	0.2142	0.040*
C11	0.3260 (3)	0.3032 (9)	0.2996 (2)	0.0365 (11)
H11	0.2906	0.1725	0.3065	0.047*
C12	0.3394 (3)	0.4827 (9)	0.3440 (2)	0.0342 (11)
H12	0.3149	0.4740	0.3822	0.044*
C13	0.3885 (3)	0.6765 (9)	0.3335 (2)	0.0323 (10)
H13	0.3965	0.8017	0.3641	0.042*
C14	0.4259 (3)	0.6900 (8)	0.2792 (2)	0.0297 (10)
H14	0.4595	0.8239	0.2723	0.039*
C21	0.0314 (3)	0.4395 (8)	−0.0025 (2)	0.0298 (10)
C22	0.1070 (3)	0.2943 (8)	−0.0099 (2)	0.0272 (9)
C23	0.1989 (3)	0.3597 (9)	0.0163 (2)	0.0327 (10)
H23	0.2122	0.5010	0.0402	0.042*
C24	0.2706 (3)	0.2210 (9)	0.0078 (3)	0.0388 (12)
H24	0.3332	0.2675	0.0253	0.050*
C25	0.2511 (4)	0.0119 (9)	−0.0267 (3)	0.0402 (12)
H25	0.3004	−0.0831	−0.0332	0.052*
C26	0.1613 (4)	−0.0558 (8)	−0.0508 (2)	0.0391 (12)
H26	0.1485	−0.1998	−0.0734	0.051*
C27	0.0886 (3)	0.0822 (8)	−0.0430 (2)	0.0330 (10)
H27	0.0263	0.0330	−0.0601	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0533 (3)	0.0566 (4)	0.0297 (3)	0.0133 (3)	0.0145 (2)	0.0060 (2)
Br2	0.0353 (3)	0.0369 (3)	0.0344 (3)	0.0050 (2)	0.0013 (2)	0.0055 (2)
C1	0.032 (2)	0.026 (3)	0.022 (2)	−0.0041 (19)	0.0041 (18)	−0.0001 (18)
C2	0.0252 (19)	0.024 (2)	0.029 (2)	0.0000 (18)	0.0016 (18)	0.0000 (19)
C3	0.0236 (19)	0.028 (3)	0.030 (2)	−0.0003 (18)	0.0083 (19)	−0.0012 (19)
C4	0.027 (2)	0.030 (3)	0.033 (2)	0.0004 (19)	0.0106 (19)	−0.007 (2)
C5	0.031 (2)	0.023 (2)	0.040 (3)	−0.0023 (19)	0.014 (2)	−0.006 (2)
C6	0.027 (2)	0.026 (3)	0.040 (3)	−0.0009 (18)	0.008 (2)	0.009 (2)
C7	0.032 (2)	0.028 (3)	0.030 (2)	−0.0015 (19)	0.010 (2)	0.003 (2)
C8	0.027 (2)	0.023 (2)	0.025 (2)	0.0010 (17)	0.0064 (18)	−0.0025 (17)
C9	0.0243 (19)	0.030 (3)	0.027 (2)	0.0029 (19)	0.0031 (18)	0.0011 (19)
C10	0.026 (2)	0.027 (3)	0.036 (3)	0.0010 (18)	0.002 (2)	−0.002 (2)
C11	0.031 (2)	0.037 (3)	0.041 (3)	0.002 (2)	0.007 (2)	0.006 (2)
C12	0.030 (2)	0.041 (3)	0.031 (2)	0.008 (2)	0.006 (2)	0.005 (2)
C13	0.033 (2)	0.034 (3)	0.027 (2)	0.005 (2)	0.002 (2)	−0.003 (2)
C14	0.030 (2)	0.022 (2)	0.035 (2)	0.0006 (19)	0.003 (2)	−0.003 (2)
C21	0.031 (2)	0.027 (3)	0.029 (2)	−0.0033 (18)	0.003 (2)	0.003 (2)
C22	0.036 (2)	0.024 (2)	0.023 (2)	0.0034 (19)	0.0087 (19)	0.0035 (18)
C23	0.037 (2)	0.027 (3)	0.033 (2)	0.000 (2)	0.007 (2)	0.000 (2)
C24	0.031 (2)	0.044 (3)	0.041 (3)	0.006 (2)	0.008 (2)	0.010 (2)
C25	0.050 (3)	0.037 (3)	0.039 (3)	0.019 (2)	0.020 (2)	0.012 (2)
C26	0.062 (3)	0.023 (3)	0.035 (3)	0.007 (2)	0.017 (3)	0.001 (2)
C27	0.042 (2)	0.028 (3)	0.030 (2)	−0.007 (2)	0.011 (2)	−0.002 (2)

Geometric parameters (Å, º) top

Br1—C1	1.907 (4)	C11—C12	1.368 (7)
Br2—C2	1.912 (4)	C11—H11	0.9500
C1—C2	1.334 (6)	C12—C13	1.381 (7)
C1—C3	1.474 (6)	C12—H12	0.9500
C2—C9	1.481 (6)	C13—C14	1.371 (6)
C3—C8	1.388 (6)	C13—H13	0.9500
C3—C4	1.400 (6)	C14—H14	0.9500
C4—C5	1.384 (7)	C21—C21ⁱ	1.188 (9)
C4—H4	0.9500	C21—C22	1.439 (6)
C5—C6	1.390 (7)	C22—C23	1.393 (6)
C5—H5	0.9500	C22—C27	1.397 (6)
C6—C7	1.381 (7)	C23—C24	1.377 (7)
C6—H6	0.9500	C23—H23	0.9500
C7—C8	1.390 (6)	C24—C25	1.396 (7)
C7—H7	0.9500	C24—H24	0.9500
C8—H8	0.9500	C25—C26	1.362 (8)
C9—C14	1.396 (6)	C25—H25	0.9500
C9—C10	1.398 (6)	C26—C27	1.382 (7)
C10—C11	1.387 (7)	C26—H26	0.9500
C10—H10	0.9500	C27—H27	0.9500

C2—C1—C3	126.1 (4)	C12—C11—H11	119.7
C2—C1—Br1	119.2 (3)	C10—C11—H11	119.7
C3—C1—Br1	114.7 (3)	C11—C12—C13	120.2 (4)
C1—C2—C9	125.9 (4)	C11—C12—H12	119.9
C1—C2—Br2	122.0 (3)	C13—C12—H12	119.9
C9—C2—Br2	112.1 (3)	C14—C13—C12	120.6 (5)
C8—C3—C4	118.4 (4)	C14—C13—H13	119.7
C8—C3—C1	121.3 (4)	C12—C13—H13	119.7
C4—C3—C1	120.3 (4)	C13—C14—C9	119.5 (4)
C5—C4—C3	120.8 (4)	C13—C14—H14	120.2
C5—C4—H4	119.6	C9—C14—H14	120.2
C3—C4—H4	119.6	C21ⁱ—C21—C22	178.8 (6)
C4—C5—C6	120.1 (4)	C23—C22—C27	119.0 (4)
C4—C5—H5	120.0	C23—C22—C21	121.1 (4)
C6—C5—H5	120.0	C27—C22—C21	119.9 (4)
C7—C6—C5	119.6 (4)	C24—C23—C22	120.5 (5)
C7—C6—H6	120.2	C24—C23—H23	119.8
C5—C6—H6	120.2	C22—C23—H23	119.8
C6—C7—C8	120.4 (4)	C23—C24—C25	119.8 (5)
C6—C7—H7	119.8	C23—C24—H24	120.1
C8—C7—H7	119.8	C25—C24—H24	120.1
C3—C8—C7	120.7 (4)	C26—C25—C24	120.0 (4)
C3—C8—H8	119.6	C26—C25—H25	120.0
C7—C8—H8	119.6	C24—C25—H25	120.0
C14—C9—C10	119.9 (4)	C25—C26—C27	120.9 (5)
C14—C9—C2	120.8 (4)	C25—C26—H26	119.5
C10—C9—C2	119.3 (4)	C27—C26—H26	119.5
C11—C10—C9	119.0 (4)	C26—C27—C22	119.8 (5)
C11—C10—H10	120.5	C26—C27—H27	120.1
C9—C10—H10	120.5	C22—C27—H27	120.1
C12—C11—C10	120.6 (5)

C4—C3—C1—C2	144.5 (5)	C10—C9—C2—Br2	111.1 (4)
C3—C1—C2—C9	−4.2 (7)	C14—C9—C2—C1	112.5 (5)
C1—C2—C9—C10	−68.6 (6)	Br1—C1—C2—Br2	−2.0 (5)
C4—C3—C1—Br1	−37.2 (5)

Symmetry code: (i) −x, −y+1, −z.

Torsion Angles (°) in cis-stilbenes. top

Compound	C4-C3-C1-C2	C14-C9-C2-C1	C3-C1-C2-C9
1,2-dibromo_(obs)	144.5 (4)	112.9 (5)	-4.4 (7)
1,2-dibromo_(calc)	120	114	0.2
1,2-dichloro_(obs)	133.7	111.3	-8.7
1,2-dichloro_(calc)	122	115	0.3
4-ClPh-1,2-dichloro_(obs)	129.3	128.0	7.1
4-ClPh-1,2-dichloro_(calc)	118	115	0.1
cis-stilbene_(calc)	121	117	0.1

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cis-1,2-Di­bromo-1,2-di­phenyl­ethene–di­phenyl­ethyne (2/1)

Supporting information

Key indicators

checkCIF results

cis-1,2-Dibromo-1,2-diphenylethene–diphenylethyne (2/1)