1,5-Dibromo-2,4-bis­[(2-bromo­phen­yl)ethyn­yl]benzene

In the title compound, C₂₂H₁₀Br₄, the two outer aromatic rings are offset from the plane occupied by the central ring.

Key indicators

• Single-crystal X-ray study
• T = 158 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.034
• wR factor = 0.042
• Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      24.70 Deg.

Author Response: Due to the detector configuration employed, data beyond 0.85 \%A was not collected.

Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5880
PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6].....      24.70 Deg.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C6     -   C7     ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C8     -   C9     ...       1.45 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C13    -   C15    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C16    -   C17    ...       1.43 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  Br1     ..       3.49 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br4    ..  Br4     ..       3.50 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         15
            C1  -C6  -C7  -C8    -89.00 12.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         22
            C5  -C6  -C7  -C8     87.00 12.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         23
            C6  -C7  -C8  -C9     76.00 15.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         24
            C7  -C8  -C9  -C10  -138.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         25
            C7  -C8  -C9  -C14    41.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         36
            C12 -C13 -C15 -C16  -148.00  8.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         37
            C13 -C15 -C16 -C17     2.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         38
            C14 -C13 -C15 -C16    29.00  8.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         39
            C15 -C16 -C17 -C18     1.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         40
            C15 -C16 -C17 -C22    17.00  0.00   1.555   1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C22 H10 Br4

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

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

---

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation and Rigaku, 1998); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN.

1,5-Dibromo-2,4-bis[(2-bromophenyl)ethynyl]benzene

Crystal data

C22H10Br4	F(000) = 1128
Mr = 593.94	Dx = 2.036 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
a = 10.0580 (7) Å	Cell parameters from 2451 reflections
b = 8.8663 (6) Å	θ = 2.3–24.6°
c = 21.870 (2) Å	µ = 8.34 mm^−1
β = 96.481 (1)°	T = 158 K
V = 1937.8 (3) Å^3	Tablet, colorless
Z = 4	0.21 × 0.19 × 0.10 mm

Data collection

Bruker SMART 1000 diffractometer	2541 reflections with F^2 > 3σ(F^2)
ω scans	Rint = 0.038
Absorption correction: empirical (using intensity measurements) (Blessing, 1995)	θmax = 24.7°
Tmin = 0.189, Tmax = 0.435	h = 0→11
8588 measured reflections	k = 0→10
3198 independent reflections	l = −25→25

Refinement

Refinement on F	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.034	w = 1/[σ^2(Fo) + 0.00022|Fo|^2]
wR(F^2) = 0.042	(Δ/σ)max < 0.001
S = 1.48	Δρmax = 0.36 e Å^−3
2541 reflections	Δρmin = −0.64 e Å^−3
215 parameters

Special details

Refinement. Refinement using reflections with F² > 3.0 σ(F²). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 3.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Br1	−0.01123 (6)	0.60201 (7)	0.56742 (3)	0.0481 (2)
Br2	−0.64754 (5)	0.39476 (6)	0.59125 (2)	0.0347 (2)
Br3	−0.65715 (5)	0.03578 (6)	0.37894 (2)	0.0319 (1)
Br4	−0.01904 (6)	−0.12230 (7)	0.43676 (3)	0.0446 (2)
C1	−0.0766 (5)	0.6509 (5)	0.6425 (2)	0.026 (1)
C2	−0.0062 (5)	0.7525 (5)	0.6812 (2)	0.033 (1)
C3	−0.0512 (5)	0.7875 (6)	0.7371 (2)	0.041 (2)
C4	−0.1652 (5)	0.7200 (5)	0.7540 (2)	0.035 (1)
C5	−0.2357 (5)	0.6202 (5)	0.7153 (2)	0.028 (1)
C6	−0.1934 (4)	0.5828 (5)	0.6584 (2)	0.023 (1)
C7	−0.2717 (4)	0.4835 (5)	0.6164 (2)	0.024 (1)
C8	−0.3387 (4)	0.4061 (5)	0.5811 (2)	0.024 (1)
C9	−0.4153 (4)	0.3151 (5)	0.5345 (2)	0.021 (1)
C10	−0.5535 (4)	0.2994 (5)	0.5321 (2)	0.022 (1)
C11	−0.6250 (4)	0.2159 (5)	0.4861 (2)	0.024 (1)
C12	−0.5573 (4)	0.1463 (5)	0.4427 (2)	0.021 (1)
C13	−0.4185 (4)	0.1554 (5)	0.4443 (2)	0.022 (1)
C14	−0.3498 (4)	0.2406 (5)	0.4907 (2)	0.024 (1)
C15	−0.3454 (4)	0.0754 (5)	0.4015 (2)	0.0214 (10)
C16	−0.2798 (4)	0.0087 (5)	0.3684 (2)	0.025 (1)
C17	−0.1999 (4)	−0.0722 (5)	0.3292 (2)	0.024 (1)
C18	−0.0809 (5)	−0.1408 (5)	0.3526 (2)	0.028 (1)
C19	−0.0048 (5)	−0.2246 (6)	0.3150 (3)	0.039 (2)
C20	−0.0479 (5)	−0.2351 (6)	0.2529 (3)	0.039 (2)
C21	−0.1645 (5)	−0.1652 (6)	0.2283 (2)	0.036 (2)
C22	−0.2398 (5)	−0.0850 (5)	0.2661 (2)	0.030 (1)
H(1)	0.0738	0.8013	0.6676	0.0410*
H(2)	0.0023	0.8551	0.7647	0.0462*
H(3)	−0.1974	0.7481	0.7937	0.0442*
H(4)	−0.3166	0.5724	0.7264	0.0336*
H(5)	−0.7221	0.2093	0.4857	0.0302*
H(6)	−0.2531	0.2469	0.4926	0.0322*
H(7)	0.0751	−0.2744	0.3322	0.0455*
H(8)	0.0066	−0.2896	0.2262	0.0477*
H(9)	−0.1940	−0.1777	0.1852	0.0484*
H(10)	−0.3210	−0.0368	0.2473	0.0351*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0505 (4)	0.0535 (4)	0.0456 (4)	−0.0054 (3)	0.0281 (3)	−0.0046 (3)
Br2	0.0384 (3)	0.0347 (3)	0.0335 (3)	0.0030 (2)	0.0154 (2)	−0.0062 (2)
Br3	0.0351 (3)	0.0316 (3)	0.0268 (3)	−0.0032 (2)	−0.0063 (2)	−0.0028 (2)
Br4	0.0393 (3)	0.0597 (4)	0.0328 (3)	0.0082 (3)	−0.0042 (2)	0.0026 (3)
C1	0.027 (3)	0.022 (3)	0.028 (3)	0.002 (2)	0.003 (2)	0.002 (2)
C2	0.024 (3)	0.027 (3)	0.047 (3)	−0.000 (2)	−0.002 (2)	0.001 (3)
C3	0.047 (4)	0.028 (3)	0.041 (3)	0.003 (3)	−0.018 (3)	−0.005 (2)
C4	0.050 (3)	0.029 (3)	0.025 (3)	0.003 (3)	0.002 (2)	−0.005 (2)
C5	0.033 (3)	0.026 (3)	0.025 (3)	0.003 (2)	0.009 (2)	0.003 (2)
C6	0.029 (3)	0.019 (2)	0.022 (2)	0.007 (2)	−0.000 (2)	0.002 (2)
C7	0.02 (8)	0.0241	0.0241	−0.0000	0.0027	−0.0000
C8	0.02 (8)	0.0241	0.0241	−0.0000	0.0027	−0.0000
C9	0.026 (3)	0.018 (2)	0.020 (2)	0.001 (2)	0.004 (2)	0.002 (2)
C10	0.026 (2)	0.021 (2)	0.019 (2)	0.000 (2)	0.007 (2)	−0.001 (2)
C11	0.022 (2)	0.023 (3)	0.027 (3)	0.004 (2)	0.002 (2)	0.006 (2)
C12	0.023 (2)	0.018 (2)	0.021 (2)	−0.000 (2)	−0.002 (2)	0.001 (2)
C13	0.028 (3)	0.019 (2)	0.020 (2)	0.002 (2)	0.002 (2)	0.004 (2)
C14	0.022 (2)	0.026 (3)	0.022 (2)	0.000 (2)	−0.000 (2)	0.004 (2)
C15	0.02 (8)	0.0214	0.0214	−0.0000	0.0024	−0.0000
C16	0.03 (8)	0.0253	0.0253	−0.0000	0.0029	−0.0000
C17	0.026 (3)	0.018 (2)	0.028 (3)	−0.002 (2)	0.006 (2)	−0.002 (2)
C18	0.028 (3)	0.027 (3)	0.030 (3)	−0.005 (2)	0.004 (2)	−0.001 (2)
C19	0.033 (3)	0.032 (3)	0.055 (4)	0.004 (2)	0.014 (3)	−0.003 (3)
C20	0.039 (3)	0.033 (3)	0.049 (3)	−0.008 (3)	0.021 (3)	−0.018 (3)
C21	0.041 (3)	0.038 (3)	0.031 (3)	−0.010 (3)	0.010 (2)	−0.014 (2)
C22	0.031 (3)	0.029 (3)	0.030 (3)	−0.002 (2)	−0.000 (2)	−0.005 (2)

Geometric parameters (Å, º)

Br1—C1	1.885 (5)	C13—C15	1.437 (6)
Br2—C10	1.887 (4)	C15—C16	1.193 (6)
Br3—C12	1.895 (4)	C16—C17	1.433 (6)
Br4—C18	1.882 (5)	C17—C18	1.387 (6)
C1—C2	1.377 (6)	C17—C22	1.398 (6)
C1—C6	1.399 (6)	C18—C19	1.398 (7)
C2—C3	1.386 (7)	C19—C20	1.384 (8)
C3—C4	1.380 (7)	C20—C21	1.381 (7)
C4—C5	1.367 (7)	C21—C22	1.380 (7)
C5—C6	1.401 (6)	C2—H(1)	0.988
C6—C7	1.438 (6)	C3—H(2)	0.970
C7—C8	1.189 (6)	C4—H(3)	0.991
C8—C9	1.449 (6)	C5—H(4)	0.972
C9—C10	1.391 (6)	C11—H(5)	0.978
C9—C14	1.390 (6)	C14—H(6)	0.970
C10—C11	1.384 (6)	C19—H(7)	0.955
C11—C12	1.376 (6)	C20—H(8)	0.973
C12—C13	1.395 (6)	C21—H(9)	0.962
C13—C14	1.387 (6)	C22—H(10)	0.972
Br1···Br1^i	3.489 (1)	C2···C21^iv	3.561 (7)
Br3···C4^ii	3.545 (5)	C5···C20^v	3.486 (7)
Br4···Br4^iii	3.502 (1)	C7···C11^vi	3.561 (6)
C2···C22^iv	3.423 (7)	C16···C21^vii	3.589 (6)
C2···C17^i	3.533 (6)
Br1—C1—C2	118.7 (4)	C16—C17—C22	120.9 (4)
Br1—C1—C6	120.2 (3)	C18—C17—C22	117.9 (4)
C2—C1—C6	121.1 (4)	Br4—C18—C17	119.9 (4)
C1—C2—C3	119.5 (5)	Br4—C18—C19	118.5 (4)
C2—C3—C4	120.2 (4)	C17—C18—C19	121.5 (4)
C3—C4—C5	120.2 (4)	C18—C19—C20	118.8 (5)
C4—C5—C6	121.0 (4)	C19—C20—C21	120.7 (5)
C1—C6—C5	117.9 (4)	C20—C21—C22	119.8 (5)
C1—C6—C7	121.3 (4)	C17—C22—C21	121.2 (4)
C5—C6—C7	120.7 (4)	C1—C2—H(1)	118.767
C6—C7—C8	177.7 (5)	C3—C2—H(1)	121.681
C7—C8—C9	176.0 (5)	C2—C3—H(2)	118.354
C8—C9—C10	122.1 (4)	C4—C3—H(2)	121.305
C8—C9—C14	119.5 (4)	C3—C4—H(3)	119.361
C10—C9—C14	118.4 (4)	C5—C4—H(3)	120.350
Br2—C10—C9	120.3 (3)	C4—C5—H(4)	121.230
Br2—C10—C11	118.6 (3)	C6—C5—H(4)	117.782
C9—C10—C11	121.1 (4)	C10—C11—H(5)	118.322
C10—C11—C12	119.0 (4)	C12—C11—H(5)	122.649
Br3—C12—C11	118.5 (3)	C9—C14—H(6)	119.634
Br3—C12—C13	119.6 (3)	C13—C14—H(6)	118.484
C11—C12—C13	121.9 (4)	C18—C19—H(7)	120.540
C12—C13—C14	117.7 (4)	C20—C19—H(7)	120.679
C12—C13—C15	122.6 (4)	C19—C20—H(8)	119.256
C14—C13—C15	119.7 (4)	C21—C20—H(8)	119.988
C9—C14—C13	121.9 (4)	C20—C21—H(9)	118.998
C13—C15—C16	176.8 (5)	C22—C21—H(9)	121.081
C15—C16—C17	179.3 (5)	C17—C22—H(10)	121.087
C16—C17—C18	121.2 (4)	C21—C22—H(10)	117.753
Br1—C1—C2—C3	−178.7 (4)	C7—C8—C9—C14	41 (6)
Br1—C1—C6—C5	178.5 (3)	C8—C9—C10—C11	177.9 (4)
Br1—C1—C6—C7	−4.8 (6)	C8—C9—C14—C13	−178.3 (4)
Br2—C10—C9—C8	−1.2 (6)	C9—C10—C11—C12	0.8 (7)
Br2—C10—C9—C14	178.8 (3)	C9—C14—C13—C12	−0.0 (7)
Br2—C10—C11—C12	179.9 (3)	C9—C14—C13—C15	−177.5 (4)
Br3—C12—C11—C10	−178.7 (3)	C10—C9—C14—C13	1.7 (7)
Br3—C12—C13—C14	178.3 (3)	C10—C11—C12—C13	1.1 (6)
Br3—C12—C13—C15	−4.3 (6)	C11—C10—C9—C14	−2.1 (6)
Br4—C18—C17—C16	−2.2 (6)	C11—C12—C13—C14	−1.4 (6)
Br4—C18—C17—C22	178.0 (3)	C11—C12—C13—C15	176.0 (4)
Br4—C18—C19—C20	−178.3 (4)	C12—C13—C15—C16	−148 (8)
C1—C2—C3—C4	0.4 (7)	C13—C15—C16—C17	23 (45)
C1—C6—C5—C4	0.0 (7)	C14—C13—C15—C16	29 (8)
C1—C6—C7—C8	−89 (12)	C15—C16—C17—C18	−12 (39)
C2—C1—C6—C5	−0.7 (6)	C15—C16—C17—C22	167 (38)
C2—C1—C6—C7	176.1 (4)	C16—C17—C18—C19	177.7 (4)
C2—C3—C4—C5	−1.1 (7)	C16—C17—C22—C21	−178.8 (5)
C3—C2—C1—C6	0.5 (7)	C17—C18—C19—C20	1.8 (8)
C3—C4—C5—C6	0.9 (7)	C17—C22—C21—C20	0.5 (8)
C4—C5—C6—C7	−176.8 (4)	C18—C17—C22—C21	0.9 (7)
C5—C6—C7—C8	87 (12)	C18—C19—C20—C21	−0.3 (8)
C6—C7—C8—C9	76 (15)	C19—C18—C17—C22	−2.1 (7)
C7—C8—C9—C10	−138 (6)	C19—C20—C21—C22	−0.8 (8)

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