(2E)-1-(3-Bromo­thien-2-yl)-3-phenyl­prop-2-en-1-one

The title compound, C₁₃H₉BrOS, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. The mean planes of the 3-bromo­thien-2-yl and 3-phenyl groups in A and B form dihedral angles of 4.9 (7) and 12.2 (4)°, respectively. The angles between the mean plane of the prop-2-en-1-one group and those of the 3-bromo­thien-2-yl and 3-phenyl groups are 2.8 (2) and 3.8 (2)°, respectively, in mol­ecule A, and 5.1 (1) and 9.8 (9)° in mol­ecule B. Essentially planar groups of mol­ecule A pack zigzag to similar groups of mol­ecule B along the a axis of the unit cell.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.011 Å
• R factor = 0.069
• wR factor = 0.178
• Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.105
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.10
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.70
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.69 mm
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.18
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.16
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         11
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         10

Alert level G
ABSTM02_ALERT_3_G  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      0.703
            Tmax scaled      0.703 Tmin scaled      0.236
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           28.65
           From the CIF: _reflns_number_total               5590
           Count of symmetry unique reflns         3048
           Completeness (_total/calc)            183.40%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2542
           Fraction of Friedel pairs measured     0.834
           Are heavy atom types Z>Si present        yes
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   3 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
   6 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Chalcones and their heterocyclic derivatives show numerous biological effects. Among several organic compounds reported for non-linear optical (NLO) property, chalcone derivatives are noticeable materials for their excellent blue light transmittance and good crystallizability. Chalcones provide a necessary configuration to show NLO property with two planar rings connected through a conjugated double bond. The NLO effect in organic molecules originates from a strong intermolecular donor-acceptor interaction, a delocalized π-electron system, and the ability to crystallize in a non-centrosymmetric structure. Secondly, the backbone is usually twisted, and this twist is inherently chiral and often results in these compounds crystallizing in non-centrosymmetric space groups. Substitution on either of the phenyl rings greatly influences non-centrosymmetric crystal packing. It is speculated that, in order to improve the activity, more bulky substituents should be introduced to increase the spontaneous polarization of a non-centrosymmetric crystal structure The molecular hyperpolarizability, β, is strongly influenced not only by the electronic effect, but also by the steric effect of the subsistent. Prompted by this, and in continuation of our quest to synthesize new materials which can find use in the photonics industries, we have synthesized a new chalcone and the present paper reports the crystal structure of a newly synthesized chalcone, (I), C₁₃H₉BrOS.

The mean planes of the 3-Bromothien-2-yl and 3-phenyl groups in molecules A and B form dihedral angles of 4.9 (7)° and 12.2 (4)°, respectively, with each other (Fig. 1). The angles between the mean plane of the prop-2-en-1-one group and those of the 3-Bromothien-2-yl and 3-phenyl groups are 2.8 (2)° and 3.8 (2)° in molecule A, and 5.1 (1)° and 9.8 (9)° in molecule B.

The packing diagram displays a zigzag array of mean planes of adjacent planar arranged groups of molecules A located next to mean planes of molecules B located diagonal along the a axis of the unit cell (Fig. 2). The closest centroid-centroid distance of 4.63 (2) Å occurs between the nearby mean planes of the inverted 3-Bromothien-2-yl and 3-phenyl groups for molecule A.

Related literature

For related structures, see: Baxter et al. (1990); Ng et al. (2006); Yathirajan, Sarojini, Narayana, Ashalatha & Bolte (2006); Yathirajan, Sarojini, Narayana, Bindya & Bolte (2006); Harrison et al. (2006); Butcher et al. (2007a,b,c). For related background, see: Fichou et al. (1988); Goto et al. (1991); Cho et al. (1996); Uchida et al. (1998); Tam et al. (1989); Indira et al. (2002); Opletalova & Sedivy (1999); Butcher, Yathirajan, Sarojini et al. (2006); Butcher et al. (2006a,b).

S2. Experimental

3-bromo-2-acetylthiophene (10 g, 0.048 mol) in 50 ml me thanol is mixed with benzaldehyde (5.0 g, 0.048 mol) and the mixture was treated with an 10 ml of 30% potassium hydroxide solution at 278 K (Fig. 3). The reaction mixture was then brought to room temperature and stirred for 3 h. The solid precipated was filtered and washed with water, dried and recrytallized from toluene (m.p.: 339 K).

S3. Refinement

The high value of R_int is probably due to poor crystal quality. The H atoms were included in the riding model approximation with C—H = 0.95 Å, and with U_iso(H) = 1.18–1.21U_eq(C). The maximum residual electron density peaks of 2.40 and -1.49 e ų, were located at 0.90 and 0.76 Å from the Br1A and Br1B atoms, respectively.

Computing details

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures

	Fig. 1. Molecular structure of C13H9BrOS, (I), showing atom labeling and 50% probability displacement ellipsoids for independent molecules A and B in the asymmetric unit.
	Fig. 2. Packing diagram of C13H9BrOS viewed down the b axis.
	Fig. 3. Synthesis scheme of C13H9BrOS.

(2E)-1-(3-Bromothien-2-yl)-3-phenylprop-2-en-1-one

Crystal data

C13H9BrOS	Dx = 1.683 Mg m^−3
Mr = 293.17	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 5433 reflections
a = 17.321 (4) Å	θ = 2.4–28.3°
b = 5.4295 (12) Å	µ = 3.71 mm^−1
c = 24.600 (5) Å	T = 123 K
V = 2313.5 (9) Å^3	Rectangular, colourless
Z = 8	0.69 × 0.32 × 0.10 mm
F(000) = 1168

Data collection

Bruker APEXII CCD area-detector diffractometer	5590 independent reflections
Radiation source: fine-focus sealed tube	4041 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.105
φ and ω scans	θmax = 28.7°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→23
Tmin = 0.335, Tmax = 1.000	k = −5→7
17031 measured reflections	l = −31→33

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.069	H-atom parameters constrained
wR(F^2) = 0.178	w = 1/[σ^2(Fo^2) + (0.114P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.001
5590 reflections	Δρmax = 2.41 e Å^−3
289 parameters	Δρmin = −1.49 e Å^−3
1 restraint	Absolute structure: Flack (1983), 2580 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.014 (15)

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
Br1A	0.19487 (4)	−0.04060 (15)	0.04400 (3)	0.0344 (2)
Br1B	−0.10871 (5)	0.54938 (16)	0.45589 (3)	0.0362 (2)
S1A	0.25796 (9)	−0.2937 (3)	0.20837 (8)	0.0247 (4)
S1B	−0.15628 (9)	0.7896 (3)	0.28805 (8)	0.0242 (4)
O1A	0.1645 (3)	0.1132 (10)	0.2363 (2)	0.0248 (10)
O1B	−0.0611 (3)	0.3863 (11)	0.2652 (2)	0.0309 (12)
C1A	0.2977 (4)	−0.4717 (15)	0.1588 (4)	0.0274 (17)
H1AA	0.3305	−0.6085	0.1656	0.033*
C2A	0.2771 (4)	−0.3951 (16)	0.1081 (3)	0.0291 (17)
H2AA	0.2935	−0.4729	0.0755	0.035*
C3A	0.2279 (4)	−0.1846 (13)	0.1098 (3)	0.0218 (14)
C4A	0.2109 (4)	−0.1080 (15)	0.1615 (3)	0.0224 (15)
C5A	0.1631 (3)	0.0939 (14)	0.1870 (3)	0.0220 (15)
C6A	0.1159 (3)	0.2476 (14)	0.1517 (3)	0.0233 (15)
H6AA	0.1161	0.2209	0.1135	0.028*
C7A	0.0719 (4)	0.4273 (14)	0.1731 (3)	0.0258 (16)
H7AA	0.0741	0.4479	0.2114	0.031*
C8A	0.0203 (4)	0.5969 (14)	0.1426 (3)	0.0234 (15)
C9A	−0.0133 (3)	0.7948 (14)	0.1707 (4)	0.0282 (16)
H9AA	−0.0033	0.8184	0.2083	0.034*
C10A	−0.0618 (4)	0.9568 (14)	0.1427 (4)	0.0323 (19)
H10A	−0.0856	1.0885	0.1617	0.039*
C11A	−0.0754 (4)	0.9286 (14)	0.0882 (4)	0.0329 (19)
H11A	−0.1064	1.0446	0.0693	0.040*
C12A	−0.0432 (4)	0.7272 (16)	0.0604 (3)	0.0350 (19)
H12A	−0.0541	0.7031	0.0229	0.042*
C13A	0.0046 (4)	0.5632 (16)	0.0877 (3)	0.0321 (18)
H13A	0.0267	0.4278	0.0688	0.039*
C1B	−0.1999 (4)	0.9667 (14)	0.3363 (4)	0.0276 (16)
H1BA	−0.2330	1.1005	0.3276	0.033*
C2B	−0.1839 (4)	0.9028 (15)	0.3871 (3)	0.0253 (16)
H2BA	−0.2026	0.9852	0.4185	0.030*
C3B	−0.1345 (4)	0.6920 (14)	0.3877 (3)	0.0243 (14)
C4B	−0.1132 (3)	0.6062 (15)	0.3372 (3)	0.0220 (15)
C5B	−0.0641 (4)	0.4081 (12)	0.3151 (3)	0.0206 (14)
C6B	−0.0212 (4)	0.2400 (15)	0.3516 (3)	0.0272 (16)
H6BA	−0.0264	0.2568	0.3899	0.033*
C7B	0.0246 (4)	0.0655 (14)	0.3314 (3)	0.0250 (15)
H7BA	0.0260	0.0508	0.2929	0.030*
C8B	0.0732 (3)	−0.1073 (13)	0.3625 (3)	0.0252 (16)
C9B	0.1140 (4)	−0.2874 (13)	0.3332 (3)	0.0254 (15)
H9BA	0.1109	−0.2924	0.2946	0.030*
C10B	0.1595 (4)	−0.4607 (15)	0.3615 (4)	0.0330 (18)
H10B	0.1873	−0.5822	0.3417	0.040*
C11B	0.1642 (4)	−0.4563 (15)	0.4168 (4)	0.0354 (19)
H11B	0.1947	−0.5741	0.4356	0.042*
C12B	0.1238 (5)	−0.2768 (18)	0.4451 (4)	0.046 (2)
H12B	0.1277	−0.2700	0.4836	0.055*
C13B	0.0778 (5)	−0.1073 (16)	0.4182 (4)	0.0320 (17)
H13B	0.0492	0.0102	0.4385	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1A	0.0368 (4)	0.0379 (5)	0.0284 (4)	0.0097 (3)	−0.0013 (3)	0.0006 (4)
Br1B	0.0410 (4)	0.0391 (5)	0.0286 (4)	0.0139 (3)	0.0015 (3)	0.0031 (5)
S1A	0.0172 (7)	0.0230 (9)	0.0340 (9)	0.0013 (6)	−0.0024 (6)	0.0024 (8)
S1B	0.0190 (7)	0.0232 (9)	0.0303 (9)	0.0022 (6)	−0.0020 (6)	−0.0003 (7)
O1A	0.020 (2)	0.022 (3)	0.032 (3)	0.003 (2)	0.003 (2)	0.001 (2)
O1B	0.031 (3)	0.027 (3)	0.034 (3)	0.011 (2)	0.004 (2)	0.001 (2)
C1A	0.009 (3)	0.028 (4)	0.045 (5)	0.005 (3)	−0.002 (3)	−0.002 (3)
C2A	0.017 (3)	0.033 (5)	0.037 (4)	−0.005 (3)	0.000 (3)	−0.004 (3)
C3A	0.021 (3)	0.017 (4)	0.027 (4)	0.000 (2)	−0.003 (3)	0.006 (3)
C4A	0.018 (3)	0.021 (4)	0.029 (4)	−0.008 (3)	0.002 (3)	−0.008 (3)
C5A	0.007 (2)	0.026 (4)	0.034 (4)	0.001 (2)	0.001 (2)	0.002 (3)
C6A	0.017 (3)	0.021 (4)	0.031 (4)	0.003 (3)	0.000 (3)	−0.001 (3)
C7A	0.016 (3)	0.022 (4)	0.040 (4)	0.001 (2)	−0.002 (3)	0.001 (3)
C8A	0.013 (3)	0.022 (4)	0.035 (4)	0.000 (2)	0.002 (3)	0.003 (3)
C9A	0.012 (3)	0.021 (4)	0.051 (5)	−0.004 (3)	0.002 (3)	−0.001 (3)
C10A	0.014 (3)	0.020 (4)	0.063 (6)	0.003 (3)	0.007 (3)	0.011 (4)
C11A	0.019 (3)	0.020 (4)	0.060 (6)	0.001 (3)	0.000 (3)	0.014 (4)
C12A	0.029 (3)	0.038 (5)	0.038 (5)	0.005 (3)	0.000 (3)	0.011 (3)
C13A	0.027 (3)	0.030 (5)	0.040 (5)	0.004 (3)	0.003 (3)	0.004 (4)
C1B	0.018 (3)	0.020 (4)	0.045 (5)	0.000 (3)	−0.002 (3)	−0.001 (3)
C2B	0.015 (3)	0.025 (4)	0.035 (4)	−0.005 (3)	0.007 (3)	−0.006 (3)
C3B	0.023 (3)	0.021 (4)	0.028 (4)	−0.007 (3)	−0.003 (3)	0.003 (3)
C4B	0.008 (2)	0.022 (4)	0.036 (4)	0.000 (2)	0.002 (2)	0.006 (3)
C5B	0.021 (3)	0.007 (3)	0.034 (4)	−0.002 (2)	0.000 (3)	−0.003 (3)
C6B	0.020 (3)	0.030 (4)	0.032 (4)	0.005 (3)	−0.005 (3)	0.000 (3)
C7B	0.014 (3)	0.025 (4)	0.036 (4)	0.001 (3)	−0.002 (3)	−0.001 (3)
C8B	0.012 (3)	0.011 (3)	0.053 (5)	0.003 (2)	−0.003 (3)	−0.004 (3)
C9B	0.018 (3)	0.012 (3)	0.046 (4)	0.000 (2)	0.004 (3)	−0.001 (3)
C10B	0.014 (3)	0.025 (4)	0.060 (6)	0.003 (3)	0.001 (3)	0.001 (4)
C11B	0.020 (3)	0.030 (5)	0.056 (6)	0.009 (3)	−0.003 (3)	0.004 (4)
C12B	0.050 (5)	0.038 (5)	0.050 (6)	0.019 (4)	−0.009 (4)	0.006 (4)
C13B	0.033 (4)	0.023 (4)	0.039 (4)	0.015 (3)	−0.009 (3)	−0.008 (3)

Geometric parameters (Å, º)

Br1A—C3A	1.886 (7)	C11A—H11A	0.9500
Br1B—C3B	1.900 (7)	C12A—C13A	1.389 (11)
S1A—C1A	1.702 (8)	C12A—H12A	0.9500
S1A—C4A	1.736 (8)	C13A—H13A	0.9500
S1B—C1B	1.705 (8)	C1B—C2B	1.324 (12)
S1B—C4B	1.735 (8)	C1B—H1BA	0.9500
O1A—C5A	1.216 (9)	C2B—C3B	1.429 (11)
O1B—C5B	1.235 (9)	C2B—H2BA	0.9500
C1A—C2A	1.361 (12)	C3B—C4B	1.378 (11)
C1A—H1AA	0.9500	C4B—C5B	1.475 (10)
C2A—C3A	1.426 (10)	C5B—C6B	1.480 (10)
C2A—H2AA	0.9500	C6B—C7B	1.332 (10)
C3A—C4A	1.371 (10)	C6B—H6BA	0.9500
C4A—C5A	1.510 (10)	C7B—C8B	1.476 (10)
C5A—C6A	1.457 (10)	C7B—H7BA	0.9500
C6A—C7A	1.345 (10)	C8B—C13B	1.371 (12)
C6A—H6AA	0.9500	C8B—C9B	1.406 (10)
C7A—C8A	1.487 (10)	C9B—C10B	1.412 (11)
C7A—H7AA	0.9500	C9B—H9BA	0.9500
C8A—C13A	1.390 (11)	C10B—C11B	1.363 (13)
C8A—C9A	1.403 (10)	C10B—H10B	0.9500
C9A—C10A	1.397 (11)	C11B—C12B	1.388 (12)
C9A—H9AA	0.9500	C11B—H11B	0.9500
C10A—C11A	1.370 (13)	C12B—C13B	1.386 (11)
C10A—H10A	0.9500	C12B—H12B	0.9500
C11A—C12A	1.405 (12)	C13B—H13B	0.9500
C1A—S1A—C4A	92.5 (4)	C8A—C13A—H13A	119.9
C1B—S1B—C4B	91.7 (4)	C2B—C1B—S1B	114.6 (6)
C2A—C1A—S1A	112.1 (6)	C2B—C1B—H1BA	122.7
C2A—C1A—H1AA	123.9	S1B—C1B—H1BA	122.7
S1A—C1A—H1AA	123.9	C1B—C2B—C3B	110.2 (7)
C1A—C2A—C3A	112.0 (7)	C1B—C2B—H2BA	124.9
C1A—C2A—H2AA	124.0	C3B—C2B—H2BA	124.9
C3A—C2A—H2AA	124.0	C4B—C3B—C2B	114.9 (7)
C4A—C3A—C2A	113.5 (6)	C4B—C3B—Br1B	126.5 (6)
C4A—C3A—Br1A	127.2 (6)	C2B—C3B—Br1B	118.5 (6)
C2A—C3A—Br1A	119.3 (5)	C3B—C4B—C5B	137.1 (7)
C3A—C4A—C5A	136.4 (7)	C3B—C4B—S1B	108.6 (6)
C3A—C4A—S1A	109.8 (6)	C5B—C4B—S1B	114.2 (6)
C5A—C4A—S1A	113.7 (5)	O1B—C5B—C4B	117.4 (6)
O1A—C5A—C6A	123.8 (6)	O1B—C5B—C6B	121.5 (6)
O1A—C5A—C4A	117.8 (6)	C4B—C5B—C6B	121.1 (6)
C6A—C5A—C4A	118.3 (7)	C7B—C6B—C5B	120.7 (7)
C7A—C6A—C5A	120.0 (7)	C7B—C6B—H6BA	119.6
C7A—C6A—H6AA	120.0	C5B—C6B—H6BA	119.6
C5A—C6A—H6AA	120.0	C6B—C7B—C8B	126.8 (8)
C6A—C7A—C8A	126.4 (7)	C6B—C7B—H7BA	116.6
C6A—C7A—H7AA	116.8	C8B—C7B—H7BA	116.6
C8A—C7A—H7AA	116.8	C13B—C8B—C9B	118.9 (7)
C13A—C8A—C9A	119.9 (7)	C13B—C8B—C7B	123.5 (7)
C13A—C8A—C7A	121.7 (7)	C9B—C8B—C7B	117.5 (7)
C9A—C8A—C7A	118.4 (7)	C8B—C9B—C10B	119.4 (8)
C10A—C9A—C8A	119.2 (8)	C8B—C9B—H9BA	120.3
C10A—C9A—H9AA	120.4	C10B—C9B—H9BA	120.3
C8A—C9A—H9AA	120.4	C11B—C10B—C9B	120.9 (7)
C11A—C10A—C9A	121.1 (8)	C11B—C10B—H10B	119.5
C11A—C10A—H10A	119.5	C9B—C10B—H10B	119.5
C9A—C10A—H10A	119.5	C10B—C11B—C12B	118.9 (8)
C10A—C11A—C12A	119.6 (7)	C10B—C11B—H11B	120.5
C10A—C11A—H11A	120.2	C12B—C11B—H11B	120.5
C12A—C11A—H11A	120.2	C13B—C12B—C11B	121.1 (9)
C13A—C12A—C11A	120.0 (8)	C13B—C12B—H12B	119.5
C13A—C12A—H12A	120.0	C11B—C12B—H12B	119.5
C11A—C12A—H12A	120.0	C8B—C13B—C12B	120.7 (8)
C12A—C13A—C8A	120.1 (8)	C8B—C13B—H13B	119.6
C12A—C13A—H13A	119.9	C12B—C13B—H13B	119.6
C4A—S1A—C1A—C2A	0.3 (6)	C4B—S1B—C1B—C2B	1.1 (6)
S1A—C1A—C2A—C3A	0.4 (8)	S1B—C1B—C2B—C3B	−1.6 (8)
C1A—C2A—C3A—C4A	−1.2 (9)	C1B—C2B—C3B—C4B	1.4 (9)
C1A—C2A—C3A—Br1A	178.0 (5)	C1B—C2B—C3B—Br1B	−175.8 (5)
C2A—C3A—C4A—C5A	−179.2 (7)	C2B—C3B—C4B—C5B	178.3 (7)
Br1A—C3A—C4A—C5A	1.6 (12)	Br1B—C3B—C4B—C5B	−4.8 (12)
C2A—C3A—C4A—S1A	1.4 (7)	C2B—C3B—C4B—S1B	−0.6 (7)
Br1A—C3A—C4A—S1A	−177.7 (4)	Br1B—C3B—C4B—S1B	176.3 (4)
C1A—S1A—C4A—C3A	−1.0 (5)	C1B—S1B—C4B—C3B	−0.2 (5)
C1A—S1A—C4A—C5A	179.5 (5)	C1B—S1B—C4B—C5B	−179.4 (5)
C3A—C4A—C5A—O1A	−176.5 (7)	C3B—C4B—C5B—O1B	178.2 (8)
S1A—C4A—C5A—O1A	2.8 (8)	S1B—C4B—C5B—O1B	−2.9 (8)
C3A—C4A—C5A—C6A	5.9 (12)	C3B—C4B—C5B—C6B	−0.8 (12)
S1A—C4A—C5A—C6A	−174.8 (5)	S1B—C4B—C5B—C6B	178.1 (5)
O1A—C5A—C6A—C7A	1.8 (11)	O1B—C5B—C6B—C7B	2.7 (11)
C4A—C5A—C6A—C7A	179.2 (6)	C4B—C5B—C6B—C7B	−178.3 (7)
C5A—C6A—C7A—C8A	−179.3 (6)	C5B—C6B—C7B—C8B	177.1 (7)
C6A—C7A—C8A—C13A	8.7 (11)	C6B—C7B—C8B—C13B	−0.6 (12)
C6A—C7A—C8A—C9A	−171.5 (7)	C6B—C7B—C8B—C9B	176.4 (7)
C13A—C8A—C9A—C10A	−0.5 (10)	C13B—C8B—C9B—C10B	−1.0 (10)
C7A—C8A—C9A—C10A	179.7 (6)	C7B—C8B—C9B—C10B	−178.2 (6)
C8A—C9A—C10A—C11A	−1.6 (10)	C8B—C9B—C10B—C11B	0.2 (11)
C9A—C10A—C11A—C12A	3.0 (11)	C9B—C10B—C11B—C12B	−0.4 (12)
C10A—C11A—C12A—C13A	−2.5 (11)	C10B—C11B—C12B—C13B	1.4 (13)
C11A—C12A—C13A—C8A	0.4 (12)	C9B—C8B—C13B—C12B	2.1 (12)
C9A—C8A—C13A—C12A	1.0 (11)	C7B—C8B—C13B—C12B	179.1 (8)
C7A—C8A—C13A—C12A	−179.2 (7)	C11B—C12B—C13B—C8B	−2.3 (14)