1-(3-Bromo-2-thien­yl)-3-[4-(dimethyl­amino)phen­yl]prop-2-en-1-one

The title compound, C₁₅H₁₄BrNOS, crystallizes with two mol­ecules in the asymmetric unit. One of the two mol­ecules forms dimers held together by weak C—H...O inter­actions. The twist angles between the thienyl and benzene rings are 2.70 (16) and 4.76 (18)°, smaller than usually observed in chalcone derivatives.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.033
• wR factor = 0.086
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.271     0.590
            Tmin(prime) and Tmax expected:      0.403     0.745
            RR(prime) =      0.848
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.82
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.26
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1B    -   C1B     ..       5.21 su
PLAT432_ALERT_2_C Short Inter X...Y Contact  Br1A   ..  C2B     ..       3.33 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         10
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C15 H14 Br N O S

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      1.262
            Tmax scaled      0.745 Tmin scaled      0.342

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

   1 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
   4 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

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

1-(3-Bromo-2-thienyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one

Crystal data

C15H14BrNOS	Z = 4
Mr = 336.24	F(000) = 680
Triclinic, P1	Dx = 1.528 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6866 (3) Å	Cell parameters from 5101 reflections
b = 12.6923 (4) Å	θ = 2.2–26.3°
c = 12.8555 (5) Å	µ = 2.95 mm^−1
α = 94.444 (1)°	T = 273 K
β = 101.673 (1)°	Plate, colourless
γ = 107.322 (1)°	0.30 × 0.25 × 0.10 mm
V = 1461.51 (9) Å^3

Data collection

Bruker APEX-2 CCD area-detector diffractometer	6034 independent reflections
Radiation source: fine-focus sealed tube	4472 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 26.6°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
Tmin = 0.271, Tmax = 0.590	k = −15→15
13636 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0395P)^2 + 0.3574P] where P = (Fo^2 + 2Fc^2)/3
6034 reflections	(Δ/σ)max = 0.001
347 parameters	Δρmax = 0.54 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

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	0.06599 (3)	0.92909 (2)	0.25692 (2)	0.06868 (10)
Br1B	0.32237 (4)	1.18885 (3)	0.48065 (3)	0.08489 (12)
S1A	−0.40191 (8)	0.72216 (6)	0.19760 (6)	0.0730 (2)
S1B	0.49065 (10)	1.20267 (8)	0.18709 (8)	0.0973 (3)
O1A	−0.43671 (19)	0.89609 (16)	0.08481 (17)	0.0765 (5)
O1B	0.4683 (3)	1.41658 (19)	0.21303 (17)	0.0904 (6)
N1A	0.1525 (3)	1.46271 (18)	−0.07988 (17)	0.0678 (6)
N1B	0.1192 (3)	1.7883 (2)	0.59756 (19)	0.0735 (6)
C1A	−0.2843 (4)	0.6695 (2)	0.2782 (2)	0.0793 (8)
H1AA	−0.3154	0.6035	0.3063	0.095*
C2A	−0.1417 (3)	0.7340 (2)	0.2964 (2)	0.0670 (7)
H2AA	−0.0627	0.7186	0.3394	0.080*
C3A	−0.1261 (3)	0.82743 (19)	0.24306 (18)	0.0522 (5)
C4A	−0.2568 (2)	0.83490 (18)	0.18455 (18)	0.0490 (5)
C5A	−0.3028 (3)	0.91265 (19)	0.11580 (19)	0.0531 (5)
C6A	−0.1923 (3)	1.0037 (2)	0.0884 (2)	0.0577 (6)
H6AA	−0.0925	1.0093	0.1102	0.069*
C7A	−0.2282 (3)	1.0800 (2)	0.03303 (18)	0.0557 (6)
H7AA	−0.3293	1.0696	0.0097	0.067*
C8A	−0.1283 (3)	1.1771 (2)	0.00501 (18)	0.0531 (5)
C9A	0.0267 (3)	1.2116 (2)	0.04324 (19)	0.0582 (6)
H9AA	0.0687	1.1696	0.0883	0.070*
C10A	0.1182 (3)	1.3049 (2)	0.01646 (19)	0.0585 (6)
H10A	0.2204	1.3257	0.0447	0.070*
C11A	0.0608 (3)	1.3700 (2)	−0.05307 (18)	0.0549 (6)
C12A	−0.0942 (3)	1.3352 (2)	−0.09262 (19)	0.0604 (6)
H12A	−0.1362	1.3756	−0.1395	0.072*
C13A	−0.1845 (3)	1.2427 (2)	−0.0634 (2)	0.0610 (6)
H13A	−0.2869	1.2228	−0.0901	0.073*
C14A	0.0942 (4)	1.5228 (2)	−0.1603 (2)	0.0801 (8)
H14A	0.0319	1.4709	−0.2223	0.120*
H14B	0.1753	1.5749	−0.1805	0.120*
H14C	0.0369	1.5624	−0.1311	0.120*
C15A	0.3091 (3)	1.5071 (3)	−0.0280 (3)	0.0842 (9)
H15A	0.3212	1.5203	0.0484	0.126*
H15B	0.3526	1.5759	−0.0529	0.126*
H15C	0.3577	1.4544	−0.0450	0.126*
C1B	0.4765 (4)	1.0823 (3)	0.2352 (4)	0.1081 (13)
H1BA	0.5005	1.0244	0.2025	0.130*
C2B	0.4266 (3)	1.0773 (3)	0.3270 (3)	0.0925 (10)
H2BA	0.4136	1.0168	0.3647	0.111*
C3B	0.3973 (3)	1.1763 (2)	0.3569 (2)	0.0705 (7)
C4B	0.4275 (3)	1.2548 (2)	0.2904 (2)	0.0674 (7)
C5B	0.4222 (3)	1.3686 (2)	0.2848 (2)	0.0658 (7)
C6B	0.3626 (3)	1.4227 (2)	0.3607 (2)	0.0648 (6)
H6BA	0.3370	1.3878	0.4183	0.078*
C7B	0.3441 (3)	1.5209 (2)	0.3492 (2)	0.0611 (6)
H7BA	0.3723	1.5515	0.2903	0.073*
C8B	0.2866 (3)	1.5873 (2)	0.41480 (18)	0.0555 (6)
C9B	0.2278 (3)	1.5515 (2)	0.5017 (2)	0.0647 (7)
H9BA	0.2249	1.4812	0.5190	0.078*
C10B	0.1745 (3)	1.6166 (2)	0.5617 (2)	0.0666 (7)
H10B	0.1361	1.5893	0.6185	0.080*
C11B	0.1761 (3)	1.7236 (2)	0.53986 (19)	0.0584 (6)
C12B	0.2368 (3)	1.7601 (2)	0.4536 (2)	0.0623 (6)
H12B	0.2421	1.8310	0.4369	0.075*
C13B	0.2879 (3)	1.6933 (2)	0.3936 (2)	0.0619 (6)
H13B	0.3253	1.7198	0.3361	0.074*
C14B	0.1387 (4)	1.9031 (3)	0.5831 (3)	0.0912 (10)
H14D	0.2430	1.9440	0.5977	0.137*
H14E	0.0938	1.9354	0.6315	0.137*
H14F	0.0922	1.9061	0.5105	0.137*
C15B	0.0588 (4)	1.7508 (3)	0.6869 (3)	0.0862 (9)
H15D	−0.0113	1.6769	0.6652	0.129*
H15E	0.0095	1.8006	0.7099	0.129*
H15F	0.1380	1.7500	0.7451	0.129*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1A	0.04200 (14)	0.07446 (18)	0.08384 (19)	0.01595 (12)	0.00284 (12)	0.02087 (14)
Br1B	0.0804 (2)	0.0762 (2)	0.0931 (2)	0.01365 (16)	0.02422 (17)	0.01938 (16)
S1A	0.0507 (4)	0.0695 (4)	0.0850 (5)	0.0036 (3)	0.0055 (3)	0.0202 (4)
S1B	0.0802 (6)	0.1069 (7)	0.0984 (6)	0.0260 (5)	0.0277 (5)	−0.0241 (5)
O1A	0.0426 (10)	0.0796 (12)	0.1049 (14)	0.0198 (9)	0.0070 (9)	0.0263 (11)
O1B	0.0984 (17)	0.0974 (15)	0.0812 (13)	0.0247 (12)	0.0435 (13)	0.0153 (12)
N1A	0.0667 (14)	0.0691 (13)	0.0641 (13)	0.0149 (11)	0.0146 (11)	0.0197 (11)
N1B	0.0874 (17)	0.0736 (14)	0.0712 (14)	0.0368 (13)	0.0253 (13)	0.0179 (12)
C1A	0.075 (2)	0.0650 (17)	0.087 (2)	0.0116 (15)	0.0064 (16)	0.0252 (15)
C2A	0.0633 (17)	0.0615 (15)	0.0716 (16)	0.0203 (13)	0.0032 (13)	0.0146 (13)
C3A	0.0488 (13)	0.0519 (13)	0.0545 (13)	0.0166 (10)	0.0104 (10)	0.0024 (10)
C4A	0.0416 (12)	0.0495 (12)	0.0522 (12)	0.0122 (10)	0.0088 (10)	0.0020 (10)
C5A	0.0441 (13)	0.0569 (13)	0.0581 (13)	0.0188 (11)	0.0088 (10)	0.0057 (11)
C6A	0.0429 (13)	0.0633 (14)	0.0659 (14)	0.0186 (11)	0.0071 (11)	0.0132 (12)
C7A	0.0454 (13)	0.0643 (14)	0.0557 (13)	0.0203 (11)	0.0053 (10)	0.0062 (11)
C8A	0.0471 (13)	0.0609 (14)	0.0513 (13)	0.0196 (11)	0.0074 (10)	0.0098 (11)
C9A	0.0511 (14)	0.0731 (16)	0.0547 (13)	0.0265 (12)	0.0083 (11)	0.0194 (12)
C10A	0.0425 (13)	0.0744 (16)	0.0579 (14)	0.0192 (12)	0.0080 (11)	0.0146 (12)
C11A	0.0589 (15)	0.0589 (14)	0.0483 (12)	0.0200 (12)	0.0142 (11)	0.0072 (11)
C12A	0.0629 (16)	0.0648 (15)	0.0547 (14)	0.0262 (13)	0.0055 (12)	0.0151 (12)
C13A	0.0502 (14)	0.0656 (15)	0.0648 (15)	0.0210 (12)	0.0028 (12)	0.0140 (12)
C14A	0.097 (2)	0.0745 (18)	0.0706 (17)	0.0237 (16)	0.0228 (16)	0.0266 (15)
C15A	0.0657 (19)	0.090 (2)	0.093 (2)	0.0115 (16)	0.0269 (16)	0.0237 (17)
C1B	0.066 (2)	0.098 (3)	0.146 (3)	0.0265 (18)	0.015 (2)	−0.039 (2)
C2B	0.0550 (18)	0.0654 (18)	0.141 (3)	0.0137 (14)	0.0047 (19)	−0.0051 (19)
C3B	0.0424 (14)	0.0659 (16)	0.0898 (19)	0.0092 (12)	0.0054 (13)	−0.0077 (15)
C4B	0.0469 (14)	0.0740 (17)	0.0706 (16)	0.0100 (12)	0.0115 (12)	−0.0084 (14)
C5B	0.0529 (15)	0.0718 (17)	0.0642 (16)	0.0102 (12)	0.0134 (12)	0.0014 (13)
C6B	0.0642 (16)	0.0670 (16)	0.0597 (15)	0.0151 (13)	0.0170 (13)	0.0075 (13)
C7B	0.0501 (14)	0.0686 (16)	0.0576 (14)	0.0097 (12)	0.0103 (11)	0.0115 (12)
C8B	0.0462 (13)	0.0624 (14)	0.0532 (13)	0.0129 (11)	0.0072 (10)	0.0117 (11)
C9B	0.0740 (18)	0.0574 (14)	0.0651 (15)	0.0208 (13)	0.0192 (13)	0.0176 (12)
C10B	0.0793 (19)	0.0673 (16)	0.0596 (15)	0.0229 (14)	0.0279 (14)	0.0200 (13)
C11B	0.0532 (14)	0.0651 (15)	0.0546 (13)	0.0201 (12)	0.0049 (11)	0.0119 (12)
C12B	0.0619 (16)	0.0619 (15)	0.0662 (15)	0.0236 (12)	0.0111 (13)	0.0227 (13)
C13B	0.0559 (15)	0.0718 (16)	0.0581 (14)	0.0168 (12)	0.0134 (12)	0.0254 (12)
C14B	0.113 (3)	0.081 (2)	0.097 (2)	0.051 (2)	0.032 (2)	0.0180 (18)
C15B	0.096 (2)	0.092 (2)	0.0793 (19)	0.0348 (19)	0.0330 (18)	0.0127 (17)

Geometric parameters (Å, º)

Br1A—C3A	1.886 (2)	C13A—H13A	0.9300
Br1B—C3B	1.892 (3)	C14A—H14A	0.9600
S1A—C1A	1.703 (3)	C14A—H14B	0.9600
S1A—C4A	1.728 (2)	C14A—H14C	0.9600
S1B—C1B	1.670 (5)	C15A—H15A	0.9600
S1B—C4B	1.735 (3)	C15A—H15B	0.9600
O1A—C5A	1.225 (3)	C15A—H15C	0.9600
O1B—C5B	1.230 (3)	C1B—C2B	1.361 (5)
N1A—C11A	1.363 (3)	C1B—H1BA	0.9300
N1A—C15A	1.445 (4)	C2B—C3B	1.411 (4)
N1A—C14A	1.453 (4)	C2B—H2BA	0.9300
N1B—C11B	1.367 (3)	C3B—C4B	1.367 (4)
N1B—C15B	1.442 (4)	C4B—C5B	1.467 (4)
N1B—C14B	1.443 (4)	C5B—C6B	1.456 (4)
C1A—C2A	1.341 (4)	C6B—C7B	1.325 (4)
C1A—H1AA	0.9300	C6B—H6BA	0.9300
C2A—C3A	1.400 (3)	C7B—C8B	1.447 (3)
C2A—H2AA	0.9300	C7B—H7BA	0.9300
C3A—C4A	1.369 (3)	C8B—C13B	1.390 (3)
C4A—C5A	1.480 (3)	C8B—C9B	1.400 (3)
C5A—C6A	1.444 (3)	C9B—C10B	1.363 (4)
C6A—C7A	1.332 (3)	C9B—H9BA	0.9300
C6A—H6AA	0.9300	C10B—C11B	1.405 (4)
C7A—C8A	1.443 (3)	C10B—H10B	0.9300
C7A—H7AA	0.9300	C11B—C12B	1.404 (4)
C8A—C13A	1.398 (3)	C12B—C13B	1.364 (4)
C8A—C9A	1.401 (3)	C12B—H12B	0.9300
C9A—C10A	1.366 (3)	C13B—H13B	0.9300
C9A—H9AA	0.9300	C14B—H14D	0.9600
C10A—C11A	1.407 (3)	C14B—H14E	0.9600
C10A—H10A	0.9300	C14B—H14F	0.9600
C11A—C12A	1.403 (3)	C15B—H15D	0.9600
C12A—C13A	1.368 (3)	C15B—H15E	0.9600
C12A—H12A	0.9300	C15B—H15F	0.9600
C1A—S1A—C4A	92.22 (13)	H15A—C15A—H15B	109.5
C1B—S1B—C4B	92.33 (18)	N1A—C15A—H15C	109.5
C11A—N1A—C15A	121.9 (2)	H15A—C15A—H15C	109.5
C11A—N1A—C14A	120.7 (2)	H15B—C15A—H15C	109.5
C15A—N1A—C14A	117.4 (2)	C2B—C1B—S1B	113.5 (3)
C11B—N1B—C15B	121.1 (2)	C2B—C1B—H1BA	123.2
C11B—N1B—C14B	121.3 (2)	S1B—C1B—H1BA	123.2
C15B—N1B—C14B	116.8 (2)	C1B—C2B—C3B	110.7 (3)
C2A—C1A—S1A	112.3 (2)	C1B—C2B—H2BA	124.7
C2A—C1A—H1AA	123.8	C3B—C2B—H2BA	124.7
S1A—C1A—H1AA	123.8	C4B—C3B—C2B	114.4 (3)
C1A—C2A—C3A	112.0 (2)	C4B—C3B—Br1B	126.7 (2)
C1A—C2A—H2AA	124.0	C2B—C3B—Br1B	118.9 (3)
C3A—C2A—H2AA	124.0	C3B—C4B—C5B	137.2 (2)
C4A—C3A—C2A	114.7 (2)	C3B—C4B—S1B	109.0 (2)
C4A—C3A—Br1A	126.34 (18)	C5B—C4B—S1B	113.7 (2)
C2A—C3A—Br1A	119.00 (18)	O1B—C5B—C6B	120.9 (3)
C3A—C4A—C5A	136.8 (2)	O1B—C5B—C4B	117.9 (2)
C3A—C4A—S1A	108.81 (18)	C6B—C5B—C4B	121.2 (2)
C5A—C4A—S1A	114.43 (17)	C7B—C6B—C5B	121.1 (3)
O1A—C5A—C6A	122.6 (2)	C7B—C6B—H6BA	119.4
O1A—C5A—C4A	117.0 (2)	C5B—C6B—H6BA	119.4
C6A—C5A—C4A	120.4 (2)	C6B—C7B—C8B	129.5 (2)
C7A—C6A—C5A	122.4 (2)	C6B—C7B—H7BA	115.3
C7A—C6A—H6AA	118.8	C8B—C7B—H7BA	115.3
C5A—C6A—H6AA	118.8	C13B—C8B—C9B	116.0 (2)
C6A—C7A—C8A	127.5 (2)	C13B—C8B—C7B	120.3 (2)
C6A—C7A—H7AA	116.3	C9B—C8B—C7B	123.7 (2)
C8A—C7A—H7AA	116.3	C10B—C9B—C8B	122.0 (2)
C13A—C8A—C9A	116.3 (2)	C10B—C9B—H9BA	119.0
C13A—C8A—C7A	120.2 (2)	C8B—C9B—H9BA	119.0
C9A—C8A—C7A	123.5 (2)	C9B—C10B—C11B	121.7 (2)
C10A—C9A—C8A	122.1 (2)	C9B—C10B—H10B	119.1
C10A—C9A—H9AA	118.9	C11B—C10B—H10B	119.1
C8A—C9A—H9AA	118.9	N1B—C11B—C12B	121.4 (2)
C9A—C10A—C11A	121.2 (2)	N1B—C11B—C10B	122.2 (2)
C9A—C10A—H10A	119.4	C12B—C11B—C10B	116.3 (2)
C11A—C10A—H10A	119.4	C13B—C12B—C11B	121.1 (2)
N1A—C11A—C12A	122.0 (2)	C13B—C12B—H12B	119.4
N1A—C11A—C10A	121.0 (2)	C11B—C12B—H12B	119.4
C12A—C11A—C10A	116.9 (2)	C12B—C13B—C8B	122.9 (2)
C13A—C12A—C11A	121.1 (2)	C12B—C13B—H13B	118.6
C13A—C12A—H12A	119.4	C8B—C13B—H13B	118.6
C11A—C12A—H12A	119.4	N1B—C14B—H14D	109.5
C12A—C13A—C8A	122.3 (2)	N1B—C14B—H14E	109.5
C12A—C13A—H13A	118.8	H14D—C14B—H14E	109.5
C8A—C13A—H13A	118.8	N1B—C14B—H14F	109.5
N1A—C14A—H14A	109.5	H14D—C14B—H14F	109.5
N1A—C14A—H14B	109.5	H14E—C14B—H14F	109.5
H14A—C14A—H14B	109.5	N1B—C15B—H15D	109.5
N1A—C14A—H14C	109.5	N1B—C15B—H15E	109.5
H14A—C14A—H14C	109.5	H15D—C15B—H15E	109.5
H14B—C14A—H14C	109.5	N1B—C15B—H15F	109.5
N1A—C15A—H15A	109.5	H15D—C15B—H15F	109.5
N1A—C15A—H15B	109.5	H15E—C15B—H15F	109.5
C4A—S1A—C1A—C2A	0.9 (3)	C4B—S1B—C1B—C2B	−0.3 (3)
S1A—C1A—C2A—C3A	−0.9 (3)	S1B—C1B—C2B—C3B	0.9 (4)
C1A—C2A—C3A—C4A	0.4 (3)	C1B—C2B—C3B—C4B	−1.2 (4)
C1A—C2A—C3A—Br1A	−179.6 (2)	C1B—C2B—C3B—Br1B	178.7 (2)
C2A—C3A—C4A—C5A	−180.0 (2)	C2B—C3B—C4B—C5B	−178.0 (3)
Br1A—C3A—C4A—C5A	0.0 (4)	Br1B—C3B—C4B—C5B	2.1 (5)
C2A—C3A—C4A—S1A	0.2 (3)	C2B—C3B—C4B—S1B	1.0 (3)
Br1A—C3A—C4A—S1A	−179.80 (13)	Br1B—C3B—C4B—S1B	−178.87 (15)
C1A—S1A—C4A—C3A	−0.59 (19)	C1B—S1B—C4B—C3B	−0.4 (2)
C1A—S1A—C4A—C5A	179.53 (18)	C1B—S1B—C4B—C5B	178.8 (2)
C3A—C4A—C5A—O1A	−172.7 (3)	C3B—C4B—C5B—O1B	175.6 (3)
S1A—C4A—C5A—O1A	7.1 (3)	S1B—C4B—C5B—O1B	−3.4 (3)
C3A—C4A—C5A—C6A	6.9 (4)	C3B—C4B—C5B—C6B	−5.2 (5)
S1A—C4A—C5A—C6A	−173.30 (18)	S1B—C4B—C5B—C6B	175.8 (2)
O1A—C5A—C6A—C7A	4.2 (4)	O1B—C5B—C6B—C7B	6.0 (4)
C4A—C5A—C6A—C7A	−175.3 (2)	C4B—C5B—C6B—C7B	−173.2 (2)
C5A—C6A—C7A—C8A	177.0 (2)	C5B—C6B—C7B—C8B	179.6 (2)
C6A—C7A—C8A—C13A	173.2 (2)	C6B—C7B—C8B—C13B	174.6 (3)
C6A—C7A—C8A—C9A	−7.0 (4)	C6B—C7B—C8B—C9B	−5.2 (4)
C13A—C8A—C9A—C10A	0.8 (4)	C13B—C8B—C9B—C10B	0.2 (4)
C7A—C8A—C9A—C10A	−179.0 (2)	C7B—C8B—C9B—C10B	−180.0 (3)
C8A—C9A—C10A—C11A	−1.3 (4)	C8B—C9B—C10B—C11B	−0.2 (4)
C15A—N1A—C11A—C12A	171.4 (2)	C15B—N1B—C11B—C12B	−179.2 (3)
C14A—N1A—C11A—C12A	−6.7 (4)	C14B—N1B—C11B—C12B	−9.4 (4)
C15A—N1A—C11A—C10A	−8.4 (4)	C15B—N1B—C11B—C10B	2.2 (4)
C14A—N1A—C11A—C10A	173.5 (2)	C14B—N1B—C11B—C10B	172.0 (3)
C9A—C10A—C11A—N1A	−179.8 (2)	C9B—C10B—C11B—N1B	178.1 (3)
C9A—C10A—C11A—C12A	0.5 (3)	C9B—C10B—C11B—C12B	−0.5 (4)
N1A—C11A—C12A—C13A	−179.0 (2)	N1B—C11B—C12B—C13B	−177.4 (2)
C10A—C11A—C12A—C13A	0.7 (3)	C10B—C11B—C12B—C13B	1.3 (4)
C11A—C12A—C13A—C8A	−1.2 (4)	C11B—C12B—C13B—C8B	−1.4 (4)
C9A—C8A—C13A—C12A	0.5 (4)	C9B—C8B—C13B—C12B	0.6 (4)
C7A—C8A—C13A—C12A	−179.8 (2)	C7B—C8B—C13B—C12B	−179.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7AA···O1A^i	0.93	2.52	3.404 (3)	159
C1B—H1BA···O1A^ii	0.93	2.43	3.341 (4)	168

Symmetry codes: (i) −x−1, −y+2, −z; (ii) x+1, y, z.