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One of our major research efforts has been the synthesis of thermally stable polymers with applications in aerospace and electronic systems. Of particular inter­est is the poly(p-terphenyl­enevinyl­ene) polymer series and the title compound, C30H20Br2, provides a gateway into the synthesis of functionalized polymers with an expected nonpolar organic solubility enhancement by virtue of the polyphenyl backbone.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806052548/fl2059sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806052548/fl2059Isup2.hkl
Contains datablock I

CCDC reference: 633851

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.107
  • Data-to-parameter ratio = 24.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C30 H20 Br2
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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997–2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: OSCAIL (McArdle, 1995) and PLATON (Spek, 2003).

1,4-Bis(4-bromophenyl)-2,3-diphenylbenzene top
Crystal data top
C30H20Br2F(000) = 1080
Mr = 540.28Dx = 1.538 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4413 reflections
a = 10.4922 (6) Åθ = 2.2–30.5°
b = 9.9679 (5) ŵ = 3.49 mm1
c = 22.4589 (12) ÅT = 173 K
β = 96.5800 (14)°Block, colourless
V = 2333.4 (2) Å30.41 × 0.28 × 0.25 mm
Z = 4
Data collection top
Bruker AXS SMART APEX CCD
diffractometer
7124 independent reflections
Radiation source: fine-focus sealed tube6306 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω scansθmax = 30.6°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS in SAINT-Plus; Bruker, 2003)
h = 1414
Tmin = 0.345, Tmax = 0.418k = 1414
26710 measured reflectionsl = 3231
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.18 w = 1/[σ2(Fo2) + (0.0453P)2 + 3P]
where P = (Fo2 + 2Fc2)/3
7124 reflections(Δ/σ)max = 0.001
289 parametersΔρmax = 0.93 e Å3
0 restraintsΔρmin = 0.52 e Å3
Special details top

Experimental. cm-1: 3043, 1599; 1H NMR (300 MHz, CDCl3): δ 6.81 (m, 2H), 6.99 (m, 5H), 7.30 (m, 2H), 7.52 (m, 1H); 13C NMR (300 MHz, CDCl3): δ 120.63, 125.95, 127.17, 129.29, 130.77, 131.40, 131.46, 139.36, 139.99, 140.48, 140.69. Crystals suitable for X-ray crystallographic analysis were obtained from CH2Cl2.

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

3.9984 (0.0092) x + 8.7435 (0.0047) y - 7.4992 (0.0207) z = 10.9820 (0.0059)

* -0.0234 (0.0017) C1 * 0.0070 (0.0016) C2 * 0.0159 (0.0016) C3 * -0.0227 (0.0016) C4 * 0.0065 (0.0017) C5 * 0.0169 (0.0017) C6 - 0.8657 (0.0072) Br1

Rms deviation of fitted atoms = 0.0168

2.6934 (0.0101) x + 8.2288 (0.0055) y + 10.5527 (0.0198) z = 11.4963 (0.0042)

Angle to previous plane (with approximate e.s.d.) = 47.54 (0.07)

* -0.0039 (0.0016) C11 * 0.0084 (0.0017) C12 * -0.0052 (0.0017) C13 * -0.0025 (0.0017) C14 * 0.0069 (0.0018) C15 * -0.0037 (0.0018) C16

Rms deviation of fitted atoms = 0.0055

- 5.9262 (0.0095) x + 8.2251 (0.0062) y + 1.2402 (0.0242) z = 9.5530 (0.0116)

Angle to previous plane (with approximate e.s.d.) = 57.90 (0.07)

* -0.0049 (0.0017) C21 * 0.0075 (0.0018) C22 * -0.0032 (0.0019) C23 * -0.0037 (0.0020) C24 * 0.0063 (0.0019) C25 * -0.0020 (0.0018) C26

Rms deviation of fitted atoms = 0.0050

- 4.0393 (0.0101) x + 3.3632 (0.0098) y - 18.1752 (0.0134) z = 2.4982 (0.0153)

Angle to previous plane (with approximate e.s.d.) = 59.73 (0.09)

* 0.0089 (0.0017) C31 * -0.0040 (0.0017) C32 * -0.0047 (0.0018) C33 * 0.0084 (0.0018) C34 * -0.0034 (0.0018) C35 * -0.0052 (0.0018) C36

Rms deviation of fitted atoms = 0.0062

4.9795 (0.0088) x + 2.7482 (0.0093) y - 19.8714 (0.0101) z = 3.0158 (0.0127)

Angle to previous plane (with approximate e.s.d.) = 51.07 (0.07)

* -0.0053 (0.0016) C41 * -0.0004 (0.0017) C42 * 0.0039 (0.0017) C43 * -0.0018 (0.0017) C44 * -0.0040 (0.0017) C45 * 0.0076 (0.0016) C46 - 0.0335 (0.0033) Br2

Rms deviation of fitted atoms = 0.0045

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
xyzUiso*/Ueq
Br10.78543 (2)0.93268 (3)0.157222 (12)0.02441 (8)
Br20.53736 (2)1.37362 (3)0.094772 (12)0.02435 (8)
C10.2637 (2)1.1966 (2)0.07445 (10)0.0149 (4)
C20.1838 (2)1.2673 (2)0.11019 (10)0.0145 (4)
C30.0586 (2)1.3047 (2)0.08592 (10)0.0139 (4)
C40.0126 (2)1.2702 (2)0.02630 (10)0.0146 (4)
C50.0957 (2)1.2053 (2)0.00896 (10)0.0174 (4)
H50.06671.18480.05000.023*
C60.2188 (2)1.1704 (2)0.01455 (11)0.0172 (4)
H60.27441.12740.01070.022*
C110.3924 (2)1.1429 (2)0.09768 (10)0.0147 (4)
C120.4111 (2)1.0696 (2)0.15124 (11)0.0166 (4)
H120.34231.06270.17590.022*
C130.5273 (2)1.0067 (2)0.16936 (10)0.0167 (4)
H130.53850.95510.20570.022*
C140.6272 (2)1.0197 (3)0.13397 (11)0.0177 (4)
C150.6119 (2)1.0936 (3)0.08110 (11)0.0195 (5)
H150.68181.10290.05730.025*
C160.4945 (2)1.1539 (3)0.06309 (11)0.0184 (5)
H160.48321.20380.02630.024*
C210.2328 (2)1.3025 (2)0.17316 (10)0.0150 (4)
C220.1730 (3)1.2537 (3)0.22115 (11)0.0199 (5)
H220.09611.20130.21360.026*
C230.2245 (3)1.2806 (3)0.28004 (12)0.0275 (6)
H230.18381.24550.31290.036*
C240.3342 (3)1.3579 (3)0.29102 (12)0.0306 (7)
H240.36961.37640.33150.040*
C250.3932 (3)1.4088 (3)0.24360 (13)0.0265 (6)
H250.46861.46350.25130.034*
C260.3431 (2)1.3805 (3)0.18483 (12)0.0204 (5)
H260.38471.41500.15210.026*
C310.0249 (2)1.3821 (2)0.12335 (10)0.0154 (4)
C320.0073 (2)1.5133 (2)0.14117 (11)0.0182 (4)
H320.08591.55230.13140.024*
C330.0744 (3)1.5874 (3)0.17309 (12)0.0225 (5)
H330.05181.67750.18530.029*
C340.1885 (3)1.5320 (3)0.18748 (11)0.0245 (5)
H340.24531.58430.20880.032*
C350.2203 (2)1.4013 (3)0.17100 (12)0.0238 (5)
H350.29831.36240.18150.031*
C360.1387 (2)1.3263 (3)0.13909 (11)0.0191 (5)
H360.16091.23560.12780.025*
C410.1199 (2)1.2999 (2)0.00178 (10)0.0154 (4)
C420.1779 (2)1.4260 (2)0.00090 (10)0.0170 (4)
H420.13181.49760.02230.022*
C430.3011 (2)1.4491 (2)0.02700 (11)0.0183 (4)
H430.33981.53600.02500.024*
C440.3675 (2)1.3449 (3)0.05777 (11)0.0180 (4)
C450.3121 (2)1.2184 (3)0.06128 (11)0.0182 (4)
H450.35881.14680.08240.024*
C460.1886 (2)1.1977 (2)0.03377 (10)0.0171 (4)
H460.14941.11130.03670.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.01810 (12)0.03097 (15)0.02357 (13)0.00907 (10)0.00018 (9)0.00032 (10)
Br20.01606 (12)0.03367 (15)0.02223 (13)0.00058 (10)0.00242 (9)0.00416 (10)
C10.0152 (10)0.0155 (10)0.0139 (10)0.0001 (8)0.0007 (8)0.0003 (8)
C20.0169 (10)0.0136 (10)0.0129 (9)0.0013 (8)0.0012 (8)0.0003 (8)
C30.0150 (10)0.0125 (10)0.0139 (10)0.0006 (8)0.0005 (8)0.0011 (8)
C40.0165 (10)0.0145 (10)0.0127 (10)0.0013 (8)0.0006 (8)0.0001 (8)
C50.0210 (11)0.0193 (11)0.0116 (10)0.0001 (9)0.0004 (8)0.0012 (8)
C60.0175 (11)0.0181 (11)0.0161 (10)0.0010 (8)0.0021 (8)0.0020 (8)
C110.0166 (10)0.0127 (10)0.0142 (10)0.0001 (8)0.0001 (8)0.0018 (8)
C120.0174 (11)0.0166 (10)0.0162 (10)0.0001 (8)0.0032 (8)0.0002 (8)
C130.0194 (11)0.0167 (11)0.0134 (10)0.0010 (8)0.0007 (8)0.0017 (8)
C140.0139 (10)0.0192 (11)0.0194 (11)0.0018 (8)0.0006 (8)0.0048 (9)
C150.0188 (11)0.0233 (12)0.0175 (11)0.0008 (9)0.0064 (9)0.0008 (9)
C160.0207 (11)0.0182 (11)0.0169 (11)0.0001 (9)0.0042 (9)0.0008 (9)
C210.0180 (10)0.0148 (10)0.0117 (9)0.0037 (8)0.0009 (8)0.0032 (8)
C220.0237 (12)0.0221 (12)0.0141 (10)0.0045 (9)0.0027 (9)0.0001 (9)
C230.0328 (14)0.0355 (15)0.0144 (11)0.0137 (12)0.0032 (10)0.0003 (10)
C240.0328 (15)0.0390 (16)0.0175 (12)0.0150 (12)0.0076 (10)0.0103 (11)
C250.0245 (13)0.0252 (13)0.0271 (13)0.0054 (10)0.0087 (10)0.0107 (11)
C260.0211 (11)0.0187 (11)0.0203 (11)0.0020 (9)0.0016 (9)0.0024 (9)
C310.0150 (10)0.0180 (10)0.0132 (10)0.0018 (8)0.0012 (8)0.0001 (8)
C320.0189 (11)0.0175 (11)0.0177 (11)0.0009 (9)0.0003 (8)0.0017 (9)
C330.0260 (13)0.0198 (12)0.0206 (12)0.0081 (10)0.0018 (10)0.0042 (9)
C340.0214 (12)0.0356 (15)0.0159 (11)0.0123 (11)0.0001 (9)0.0030 (10)
C350.0158 (11)0.0370 (15)0.0188 (11)0.0025 (10)0.0026 (9)0.0003 (10)
C360.0182 (11)0.0223 (12)0.0166 (10)0.0014 (9)0.0014 (8)0.0017 (9)
C410.0165 (10)0.0184 (11)0.0115 (9)0.0009 (8)0.0017 (8)0.0018 (8)
C420.0196 (11)0.0163 (10)0.0147 (10)0.0016 (9)0.0000 (8)0.0001 (8)
C430.0224 (11)0.0168 (11)0.0152 (10)0.0029 (9)0.0003 (8)0.0027 (8)
C440.0165 (11)0.0232 (12)0.0139 (10)0.0005 (9)0.0004 (8)0.0033 (9)
C450.0198 (11)0.0197 (11)0.0147 (10)0.0047 (9)0.0001 (8)0.0020 (9)
C460.0211 (11)0.0159 (10)0.0144 (10)0.0003 (9)0.0027 (8)0.0010 (8)
Geometric parameters (Å, º) top
Br1—C141.893 (2)C23—C241.384 (5)
Br2—C441.900 (2)C23—H230.9600
C1—C61.398 (3)C24—C251.387 (5)
C1—C21.414 (3)C24—H240.9600
C1—C111.490 (3)C25—C261.392 (4)
C2—C31.414 (3)C25—H250.9600
C2—C211.490 (3)C26—H260.9600
C3—C41.413 (3)C31—C321.398 (3)
C3—C311.496 (3)C31—C361.399 (3)
C4—C51.401 (3)C32—C331.391 (3)
C4—C411.490 (3)C32—H320.9600
C5—C61.383 (3)C33—C341.390 (4)
C5—H50.9600C33—H330.9600
C6—H60.9600C34—C351.385 (4)
C11—C161.398 (3)C34—H340.9600
C11—C121.402 (3)C35—C361.395 (4)
C12—C131.390 (3)C35—H350.9600
C12—H120.9600C36—H360.9600
C13—C141.392 (3)C41—C461.398 (3)
C13—H130.9600C41—C421.401 (3)
C14—C151.391 (4)C42—C431.389 (3)
C15—C161.389 (4)C42—H420.9600
C15—H150.9600C43—C441.390 (4)
C16—H160.9600C43—H430.9600
C21—C261.394 (3)C44—C451.395 (4)
C21—C221.396 (3)C45—C461.386 (3)
C22—C231.396 (4)C45—H450.9600
C22—H220.9600C46—H460.9600
C6—C1—C2118.9 (2)C23—C24—C25120.1 (2)
C6—C1—C11117.5 (2)C23—C24—H24119.9
C2—C1—C11123.6 (2)C25—C24—H24119.9
C3—C2—C1119.9 (2)C24—C25—C26120.0 (3)
C3—C2—C21120.6 (2)C24—C25—H25120.0
C1—C2—C21119.5 (2)C26—C25—H25120.0
C4—C3—C2120.1 (2)C25—C26—C21120.4 (3)
C4—C3—C31120.0 (2)C25—C26—H26119.8
C2—C3—C31119.9 (2)C21—C26—H26119.8
C5—C4—C3118.8 (2)C32—C31—C36119.0 (2)
C5—C4—C41117.6 (2)C32—C31—C3120.3 (2)
C3—C4—C41123.6 (2)C36—C31—C3120.6 (2)
C6—C5—C4121.0 (2)C33—C32—C31120.1 (2)
C6—C5—H5119.5C33—C32—H32120.0
C4—C5—H5119.5C31—C32—H32120.0
C5—C6—C1121.2 (2)C34—C33—C32120.5 (2)
C5—C6—H6119.4C34—C33—H33119.8
C1—C6—H6119.4C32—C33—H33119.8
C16—C11—C12118.5 (2)C35—C34—C33119.9 (2)
C16—C11—C1119.9 (2)C35—C34—H34120.0
C12—C11—C1121.3 (2)C33—C34—H34120.0
C13—C12—C11121.2 (2)C34—C35—C36120.0 (2)
C13—C12—H12119.4C34—C35—H35120.0
C11—C12—H12119.4C36—C35—H35120.0
C12—C13—C14118.9 (2)C35—C36—C31120.5 (2)
C12—C13—H13120.5C35—C36—H36119.7
C14—C13—H13120.5C31—C36—H36119.7
C15—C14—C13121.1 (2)C46—C41—C42118.4 (2)
C15—C14—Br1119.32 (18)C46—C41—C4118.3 (2)
C13—C14—Br1119.59 (19)C42—C41—C4123.3 (2)
C16—C15—C14119.3 (2)C43—C42—C41121.0 (2)
C16—C15—H15120.4C43—C42—H42119.5
C14—C15—H15120.4C41—C42—H42119.5
C15—C16—C11121.0 (2)C42—C43—C44119.3 (2)
C15—C16—H16119.5C42—C43—H43120.4
C11—C16—H16119.5C44—C43—H43120.4
C26—C21—C22119.1 (2)C43—C44—C45121.0 (2)
C26—C21—C2119.9 (2)C43—C44—Br2119.82 (19)
C22—C21—C2120.9 (2)C45—C44—Br2119.18 (18)
C21—C22—C23120.3 (3)C46—C45—C44119.0 (2)
C21—C22—H22119.8C46—C45—H45120.5
C23—C22—H22119.8C44—C45—H45120.5
C24—C23—C22120.0 (3)C45—C46—C41121.4 (2)
C24—C23—H23120.0C45—C46—H46119.3
C22—C23—H23120.0C41—C46—H46119.3
C6—C1—C2—C32.9 (3)C26—C21—C22—C231.2 (4)
C11—C1—C2—C3174.6 (2)C2—C21—C22—C23176.0 (2)
C6—C1—C2—C21176.7 (2)C21—C22—C23—C241.1 (4)
C11—C1—C2—C215.9 (3)C22—C23—C24—C250.0 (4)
C1—C2—C3—C40.8 (3)C23—C24—C25—C260.9 (4)
C21—C2—C3—C4179.6 (2)C24—C25—C26—C210.7 (4)
C1—C2—C3—C31178.7 (2)C22—C21—C26—C250.3 (4)
C21—C2—C3—C310.9 (3)C2—C21—C26—C25177.0 (2)
C2—C3—C4—C53.6 (3)C4—C3—C31—C32113.0 (3)
C31—C3—C4—C5175.9 (2)C2—C3—C31—C3266.5 (3)
C2—C3—C4—C41176.9 (2)C4—C3—C31—C3664.6 (3)
C31—C3—C4—C413.6 (3)C2—C3—C31—C36115.9 (3)
C3—C4—C5—C62.7 (4)C36—C31—C32—C331.2 (4)
C41—C4—C5—C6177.8 (2)C3—C31—C32—C33176.4 (2)
C4—C5—C6—C11.1 (4)C31—C32—C33—C340.0 (4)
C2—C1—C6—C53.8 (4)C32—C33—C34—C351.2 (4)
C11—C1—C6—C5173.7 (2)C33—C34—C35—C361.1 (4)
C6—C1—C11—C1643.8 (3)C34—C35—C36—C310.2 (4)
C2—C1—C11—C16138.8 (2)C32—C31—C36—C351.4 (4)
C6—C1—C11—C12130.0 (2)C3—C31—C36—C35176.2 (2)
C2—C1—C11—C1247.5 (3)C5—C4—C41—C4647.3 (3)
C16—C11—C12—C131.2 (4)C3—C4—C41—C46133.2 (2)
C1—C11—C12—C13172.6 (2)C5—C4—C41—C42130.9 (2)
C11—C12—C13—C141.4 (4)C3—C4—C41—C4248.6 (3)
C12—C13—C14—C150.3 (4)C46—C41—C42—C430.6 (3)
C12—C13—C14—Br1179.09 (18)C4—C41—C42—C43178.8 (2)
C13—C14—C15—C160.8 (4)C41—C42—C43—C440.3 (4)
Br1—C14—C15—C16177.96 (19)C42—C43—C44—C450.4 (4)
C14—C15—C16—C110.9 (4)C42—C43—C44—Br2178.70 (18)
C12—C11—C16—C150.1 (4)C43—C44—C45—C460.4 (4)
C1—C11—C16—C15173.9 (2)Br2—C44—C45—C46179.45 (17)
C3—C2—C21—C26121.2 (3)C44—C45—C46—C411.3 (4)
C1—C2—C21—C2658.4 (3)C42—C41—C46—C451.4 (3)
C3—C2—C21—C2261.6 (3)C4—C41—C46—C45179.7 (2)
C1—C2—C21—C22118.8 (3)
Table 1. Angles between Least-Squares planes (°) for the rings in (I) top
AtomsAngles
C1-C2-C3-C4-C5-C647.68 (10)59.33 (11)66.42 (11)48.08 (10)
C11-C12-C13-C14-C15-C1658.09 (11)75.22 (11)85.92 (11)
C21-C22-C23-C24-C25-C2659.72 (12)88.13 (12)
C31-C32-C33-C34-C35-C3651.11 (12)
C41-C42-C43-C44-C45-C46
 

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