3,3',5,5'-Tetra­bromo-4,4'-dihydroxy­biphen­yl

The dihedral angle between the benzene rings in the title compound, C₁₃H₆Cl₆O, is 49.06 (8)°. The molecule has crystallographic twofold rotation symmetry.

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.022
• wR factor = 0.048
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.183     0.541
            Tmin and Tmax expected:      0.123     0.541
            RR =      1.486
            Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.45
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  Br1     ..       3.53 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  Br1     ..       3.53 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.42
           From the CIF: _reflns_number_total               1403
           Count of symmetry unique reflns          849
           Completeness (_total/calc)            165.25%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       554
           Fraction of Friedel pairs measured     0.653
           Are heavy atom types Z>Si present        yes

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

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

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1994); software used to prepare material for publication: SHELX97-2 (Sheldrick, 1997) and local procedures.

3,3',5,5'-Tetrabromo-4,4'-dihydroxybiphenyl

Crystal data

C12H6Br4O2	F(000) = 468
Mr = 501.77	Dx = 2.547 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 3354 reflections
a = 23.4583 (9) Å	θ = 1.0–27.5°
b = 3.8928 (2) Å	µ = 12.29 mm^−1
c = 7.5495 (3) Å	T = 90 K
β = 108.376 (2)°	Flattened rod, colourless
V = 654.26 (5) Å^3	0.38 × 0.15 × 0.05 mm
Z = 2

Data collection

Nonius KappaCCD diffractometer	1403 independent reflections
Radiation source: fine-focus sealed tube	1341 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 18 pixels mm^-1	θmax = 27.4°, θmin = 1.8°
ω scans at fixed χ = 90°	h = −27→30
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	k = −5→4
Tmin = 0.183, Tmax = 0.541	l = −9→9
3668 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.022	w = 1/[σ^2(Fo^2) + (0.0142P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.048	(Δ/σ)max = 0.005
S = 1.07	Δρmax = 0.55 e Å^−3
1403 reflections	Δρmin = −0.56 e Å^−3
84 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0014 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 554 Freidel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.055 (17)

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
O1	0.79585 (10)	0.0368 (7)	0.0480 (3)	0.0136 (6)
H1	0.7755	−0.1217	−0.0177	0.020*
Br1	0.800271 (14)	−0.27253 (8)	−0.32434 (4)	0.01155 (11)
Br2	0.882855 (15)	0.35008 (11)	0.38611 (4)	0.01348 (11)
C1	0.96912 (15)	0.0543 (9)	0.0062 (5)	0.0120 (8)
C2	0.92158 (15)	−0.0757 (8)	−0.1405 (5)	0.0105 (8)
H2	0.9287	−0.1587	−0.2500	0.013*
C3	0.86460 (15)	−0.0841 (9)	−0.1271 (4)	0.0095 (8)
C4	0.85181 (14)	0.0389 (9)	0.0304 (5)	0.0089 (7)
C5	0.89905 (15)	0.1718 (9)	0.1743 (4)	0.0113 (8)
C6	0.95698 (14)	0.1774 (9)	0.1646 (4)	0.0101 (8)
H6	0.9888	0.2656	0.2663	0.012*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0103 (12)	0.0165 (16)	0.0151 (13)	−0.0001 (11)	0.0053 (10)	−0.0023 (11)
Br1	0.00859 (17)	0.01384 (18)	0.01063 (17)	−0.00060 (15)	0.00076 (12)	−0.00128 (15)
Br2	0.01527 (19)	0.01576 (19)	0.01113 (18)	−0.00011 (14)	0.00664 (14)	−0.00244 (14)
C1	0.0123 (17)	0.0126 (18)	0.0119 (18)	−0.0016 (15)	0.0048 (14)	0.0022 (15)
C2	0.0129 (17)	0.011 (2)	0.0065 (16)	−0.0008 (14)	0.0020 (14)	−0.0013 (14)
C3	0.0095 (16)	0.008 (2)	0.0077 (16)	0.0019 (14)	−0.0016 (13)	0.0005 (13)
C4	0.0055 (16)	0.0096 (19)	0.0129 (16)	0.0023 (14)	0.0048 (13)	0.0037 (13)
C5	0.0161 (17)	0.012 (2)	0.0067 (15)	−0.0002 (15)	0.0048 (13)	0.0000 (14)
C6	0.0082 (16)	0.009 (2)	0.0130 (17)	−0.0008 (14)	0.0039 (13)	−0.0005 (15)

Geometric parameters (Å, º)

O1—C4	1.361 (4)	C2—C3	1.372 (5)
O1—H1	0.8400	C2—H2	0.9500
Br1—C3	1.902 (3)	C3—C4	1.399 (5)
Br2—C5	1.888 (3)	C4—C5	1.385 (5)
C1—C2	1.395 (5)	C5—C6	1.384 (4)
C1—C6	1.398 (4)	C6—H6	0.9500
C1—C1^i	1.481 (7)
C4—O1—H1	109.5	O1—C4—C5	118.9 (3)
C2—C1—C6	118.4 (3)	O1—C4—C3	123.6 (3)
C2—C1—C1^i	120.2 (4)	C5—C4—C3	117.5 (3)
C6—C1—C1^i	121.4 (4)	C6—C5—C4	121.4 (3)
C3—C2—C1	120.3 (3)	C6—C5—Br2	120.1 (3)
C3—C2—H2	119.9	C4—C5—Br2	118.5 (3)
C1—C2—H2	119.9	C5—C6—C1	120.5 (3)
C2—C3—C4	121.9 (3)	C5—C6—H6	119.7
C2—C3—Br1	120.2 (2)	C1—C6—H6	119.7
C4—C3—Br1	117.9 (3)
C6—C1—C2—C3	−0.6 (5)	O1—C4—C5—C6	179.4 (3)
C1^i—C1—C2—C3	178.3 (3)	C3—C4—C5—C6	−1.2 (5)
C1—C2—C3—C4	0.8 (5)	O1—C4—C5—Br2	−1.0 (5)
C1—C2—C3—Br1	−178.3 (3)	C3—C4—C5—Br2	178.5 (2)
C2—C3—C4—O1	179.6 (3)	C4—C5—C6—C1	1.3 (5)
Br1—C3—C4—O1	−1.4 (5)	Br2—C5—C6—C1	−178.3 (3)
C2—C3—C4—C5	0.1 (5)	C2—C1—C6—C5	−0.4 (5)
Br1—C3—C4—C5	179.2 (3)	C1^i—C1—C6—C5	−179.3 (3)

Symmetry code: (i) −x+2, y, −z.