Competition between hydrogen and halogen bonding in the structures of 5,10-dihydroxy-5,10-dihydroboranthrenes

X-ray crystallographic and computational studies are reported for a series of boranthrenes, substituted with halogen atoms. The role of competitive hydrogen (O—H...O, O—H...F, C—H...O) and halogen (Cl...Cl, O...Br, F...F) bonding interactions on the molecular arrangement in the crystal structures is discussed. The structural analysis and calculations reveal that the O—H...O hydrogen bond in the unsubstituted derivative 5,10-dihydroxy-5,10-dihydroboranthrene, C₁₂H₁₀B₂O₂, is of moderate strength (ca −20 kJ mol⁻¹), but weaker than that in the related thiophene derivative 4,8-dihydro-4,8-dihydroxy-p-diborino[2,3-b:5,6-b]dithiophene, C₈H₆B₂O₂S₂ (ca −40 kJ mol⁻¹). This is due to shielding of the OH group by the H atoms in the β-position of the boranthrene unit. Structural diversity derived from the flexibility of the O—H...O hydrogen bond facilitates the occurrence of other competitive interactions. For instance, in the 1,6-difluoro derivative, C₁₂H₈B₂F₂O₂, the crystal packing results from O—H...F and F...F interactions. In turn, the 1,6-dibromo derivative, C₁₂H₈B₂Br₂O₂, is dominated by Br...O halogen-bond interactions. In the most interesting case, the 1,6-dichloro derivative, C₁₂H₈B₂Cl₂O₂, molecular disorder leads to the formation of two different supramolecular arrangements co-existing in the crystal lattice, one based on the Cl...Cl and C—H...O bonds, and the other stabilized by O—H...O hydrogen bonds. Calculations performed with density-functional theory (DFT; CRYSTAL09) and PIXEL methodologies show that both lattices are characterized by similar energy values (ca −100 kJ mol⁻¹). A mixed arrangement with random or short-range-ordered molecular orientations can also be expected.

Computing details

Data collection: CrysAlis PRO (Agilent, 2011) for (I), (II), (III), (IV); APEX2 (Bruker, 2011) for (V). Cell refinement: CrysAlis PRO for (I), (II), (III), (IV); SAINT (Bruker, 2011) for (V). Data reduction: CrysAlis PRO for (I), (II), (III), (IV); SAINT for (V). For all compounds, program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013; molecular graphics: SHELXTL (Bruker, 2011); software used to prepare material for publication: SHELXL2013.

Figures

(I)

Crystal data

C12H10B2O2	Dx = 1.402 Mg m^−3
Mr = 207.82	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 2772 reflections
a = 4.8645 (4) Å	θ = 2.0–34.3°
b = 13.0540 (11) Å	µ = 0.09 mm^−1
c = 15.5080 (14) Å	T = 100 K
V = 984.78 (15) Å^3	Unspecified, colourless
Z = 4	0.10 × 0.07 × 0.06 mm
F(000) = 432

Data collection

KUMA KM4 CCD diffractometer	2096 independent reflections
Radiation source: fine-focus sealed tube	1474 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.079
ω scans	θmax = 26.7°, θmin = 2.0°
Absorption correction: multi-scan CrysAlis PRO (Agilent, 2011)	h = −6→6
Tmin = 0.428, Tmax = 1.000	k = −16→16
10703 measured reflections	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.081	H-atom parameters constrained
wR(F^2) = 0.220	w = 1/[σ^2(Fo^2) + (0.1435P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2096 reflections	Δρmax = 1.01 e Å^−3
145 parameters	Δρmin = −0.36 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
O1	0.1682 (7)	−0.0445 (2)	0.1511 (2)	0.0184 (9)
H1	0.0527	−0.0835	0.1745	0.028*
O2	0.3250 (7)	0.3186 (2)	0.3511 (2)	0.0179 (9)
H2	0.4369	0.3585	0.3271	0.027*
C1	0.4681 (10)	0.2116 (3)	0.2182 (3)	0.0133 (11)
C6	0.6646 (10)	0.2813 (3)	0.1865 (3)	0.0165 (12)
H6	0.6955	0.3433	0.2172	0.020*
C2	0.4211 (10)	0.1204 (3)	0.1699 (3)	0.0145 (11)
C5	0.8128 (10)	0.2629 (4)	0.1130 (3)	0.0177 (12)
H5	0.9462	0.3111	0.0941	0.021*
C7	0.0223 (10)	0.0630 (4)	0.2834 (3)	0.0140 (11)
C3	0.5728 (11)	0.1040 (3)	0.0947 (3)	0.0163 (11)
H3	0.5418	0.0434	0.0621	0.020*
B1	0.1955 (12)	0.0431 (4)	0.1996 (3)	0.0124 (12)
C8	0.0723 (10)	0.1538 (4)	0.3317 (3)	0.0133 (11)
B2	0.2994 (12)	0.2310 (4)	0.3027 (4)	0.0133 (12)
C12	−0.1792 (10)	−0.0060 (3)	0.3131 (3)	0.0132 (11)
H12	−0.2132	−0.0672	0.2816	0.016*
C4	0.7681 (10)	0.1739 (4)	0.0662 (3)	0.0191 (12)
H4	0.8701	0.1609	0.0152	0.023*
C9	−0.0806 (11)	0.1702 (4)	0.4075 (3)	0.0188 (12)
H9	−0.0463	0.2298	0.4410	0.023*
C11	−0.3292 (10)	0.0135 (4)	0.3875 (3)	0.0189 (12)
H11	−0.4658	−0.0336	0.4061	0.023*
C10	−0.2796 (11)	0.1015 (3)	0.4345 (3)	0.0176 (11)
H10	−0.3822	0.1149	0.4854	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0199 (19)	0.0110 (17)	0.024 (2)	−0.0029 (14)	0.0026 (17)	−0.0019 (15)
O2	0.0195 (18)	0.0128 (17)	0.021 (2)	−0.0004 (15)	0.0021 (16)	0.0000 (14)
C1	0.012 (2)	0.012 (2)	0.016 (3)	0.0027 (18)	−0.002 (2)	−0.002 (2)
C6	0.014 (2)	0.010 (2)	0.025 (3)	0.003 (2)	−0.004 (2)	0.004 (2)
C2	0.017 (3)	0.012 (2)	0.015 (2)	0.005 (2)	−0.004 (2)	−0.0024 (19)
C5	0.015 (2)	0.016 (3)	0.022 (3)	−0.003 (2)	−0.003 (2)	0.005 (2)
C7	0.016 (2)	0.009 (2)	0.017 (3)	0.0034 (19)	−0.005 (2)	0.001 (2)
C3	0.019 (2)	0.014 (3)	0.016 (3)	0.000 (2)	−0.003 (2)	0.001 (2)
B1	0.014 (3)	0.007 (2)	0.016 (3)	0.006 (2)	−0.002 (2)	−0.002 (2)
C8	0.013 (2)	0.010 (2)	0.017 (3)	0.0027 (19)	−0.001 (2)	−0.001 (2)
B2	0.013 (3)	0.008 (2)	0.019 (3)	0.000 (2)	−0.002 (2)	0.003 (2)
C12	0.013 (2)	0.005 (2)	0.021 (3)	0.000 (2)	0.001 (2)	0.001 (2)
C4	0.016 (3)	0.023 (3)	0.018 (3)	0.003 (2)	0.004 (2)	0.004 (2)
C9	0.023 (3)	0.010 (2)	0.023 (3)	0.004 (2)	0.002 (2)	−0.004 (2)
C11	0.020 (3)	0.013 (2)	0.024 (3)	0.000 (2)	0.002 (2)	0.004 (2)
C10	0.019 (3)	0.018 (2)	0.016 (3)	0.004 (2)	0.003 (2)	−0.002 (2)

Geometric parameters (Å, º)

O1—B1	1.375 (6)	C7—C12	1.409 (7)
O2—B2	1.373 (6)	C7—C8	1.423 (7)
C1—C6	1.408 (7)	C7—B1	1.570 (7)
C1—C2	1.426 (6)	C3—C4	1.390 (7)
C1—B2	1.567 (7)	C8—C9	1.408 (7)
C6—C5	1.370 (7)	C8—B2	1.562 (7)
C2—C3	1.397 (7)	C12—C11	1.389 (7)
C2—B1	1.560 (7)	C9—C10	1.385 (7)
C5—C4	1.386 (7)	C11—C10	1.382 (7)
C6—C1—C2	117.7 (5)	O1—B1—C7	122.5 (4)
C6—C1—B2	122.9 (4)	C2—B1—C7	121.0 (4)
C2—C1—B2	119.4 (4)	C9—C8—C7	118.4 (4)
C5—C6—C1	122.3 (5)	C9—C8—B2	121.1 (4)
C3—C2—C1	118.8 (4)	C7—C8—B2	120.5 (4)
C3—C2—B1	121.3 (4)	O2—B2—C8	116.4 (4)
C1—C2—B1	119.8 (4)	O2—B2—C1	123.0 (4)
C6—C5—C4	120.0 (5)	C8—B2—C1	120.4 (4)
C12—C7—C8	118.7 (4)	C11—C12—C7	121.3 (4)
C12—C7—B1	122.6 (4)	C5—C4—C3	119.5 (5)
C8—C7—B1	118.8 (4)	C10—C9—C8	121.6 (5)
C4—C3—C2	121.7 (5)	C10—C11—C12	119.9 (5)
O1—B1—C2	116.4 (4)	C11—C10—C9	120.1 (5)
C2—C1—C6—C5	−1.5 (7)	C12—C7—C8—B2	178.3 (4)
B2—C1—C6—C5	179.3 (4)	B1—C7—C8—B2	−1.2 (6)
C6—C1—C2—C3	0.8 (7)	C9—C8—B2—O2	−5.0 (7)
B2—C1—C2—C3	−180.0 (4)	C7—C8—B2—O2	177.3 (4)
C6—C1—C2—B1	−177.0 (4)	C9—C8—B2—C1	179.9 (5)
B2—C1—C2—B1	2.3 (6)	C7—C8—B2—C1	2.2 (7)
C1—C6—C5—C4	1.1 (7)	C6—C1—B2—O2	1.7 (7)
C1—C2—C3—C4	0.2 (7)	C2—C1—B2—O2	−177.5 (5)
B1—C2—C3—C4	177.9 (5)	C6—C1—B2—C8	176.5 (4)
C3—C2—B1—O1	4.2 (7)	C2—C1—B2—C8	−2.8 (6)
C1—C2—B1—O1	−178.1 (4)	C8—C7—C12—C11	0.5 (7)
C3—C2—B1—C7	−179.0 (4)	B1—C7—C12—C11	180.0 (4)
C1—C2—B1—C7	−1.3 (7)	C6—C5—C4—C3	−0.1 (7)
C12—C7—B1—O1	−2.2 (7)	C2—C3—C4—C5	−0.6 (7)
C8—C7—B1—O1	177.3 (4)	C7—C8—C9—C10	−1.4 (7)
C12—C7—B1—C2	−178.7 (4)	B2—C8—C9—C10	−179.1 (5)
C8—C7—B1—C2	0.7 (6)	C7—C12—C11—C10	−0.8 (7)
C12—C7—C8—C9	0.5 (7)	C12—C11—C10—C9	0.0 (7)
B1—C7—C8—C9	−178.9 (4)	C8—C9—C10—C11	1.1 (8)

(II)

Crystal data

C12H8B2F2O2	F(000) = 496
Mr = 243.80	Dx = 1.555 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.909 (6) Å	Cell parameters from 15096 reflections
b = 3.7790 (1) Å	θ = 2.2–34.5°
c = 17.355 (3) Å	µ = 0.12 mm^−1
β = 117.51 (4)°	T = 100 K
V = 1041.7 (5) Å^3	Block, colourless
Z = 4	0.11 × 0.10 × 0.07 mm

Data collection

KUMA KM4 CCD diffractometer	4294 independent reflections
Radiation source: fine-focus sealed tube	3245 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ω scans	θmax = 34.6°, θmin = 2.4°
Absorption correction: multi-scan CrysAlis PRO (Agilent, 2011)	h = −28→28
Tmin = 0.995, Tmax = 1.000	k = −5→5
45182 measured reflections	l = −27→27

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.0642P)^2 + 0.3315P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
4294 reflections	Δρmax = 0.46 e Å^−3
163 parameters	Δρmin = −0.26 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
C5	0.28586 (6)	0.2283 (3)	0.31060 (7)	0.01845 (19)
H5	0.2300	0.1394	0.2810	0.022*
C1	0.41071 (6)	0.3603 (3)	0.44649 (6)	0.01310 (17)
C2	0.45225 (6)	0.4940 (3)	0.40022 (6)	0.01331 (17)
C3	0.40672 (6)	0.4843 (3)	0.31000 (6)	0.01531 (18)
C4	0.32562 (6)	0.3575 (3)	0.26389 (7)	0.01831 (19)
H4	0.2978	0.3586	0.2022	0.022*
C6	0.32842 (6)	0.2300 (3)	0.40087 (6)	0.01593 (18)
H6	0.3010	0.1407	0.4324	0.019*
C7	0.08711 (5)	0.8320 (3)	0.53297 (6)	0.01212 (16)
C8	0.04521 (6)	0.9370 (3)	0.44467 (6)	0.01214 (16)
C9	0.08874 (6)	0.8749 (3)	0.39707 (6)	0.01450 (17)
C10	0.16693 (6)	0.7200 (3)	0.42871 (7)	0.01686 (19)
H10	0.1926	0.6820	0.3922	0.020*
C11	0.20712 (6)	0.6210 (3)	0.51571 (7)	0.01738 (19)
H11	0.2614	0.5156	0.5400	0.021*
C12	0.16717 (6)	0.6777 (3)	0.56694 (6)	0.01534 (18)
H12	0.1948	0.6101	0.6264	0.018*
B1	0.54389 (6)	0.6446 (3)	0.45154 (7)	0.01407 (19)
B2	0.04423 (6)	0.8881 (3)	0.59308 (7)	0.01328 (18)
O1	0.58821 (5)	0.7887 (2)	0.41325 (5)	0.02121 (17)
H1A	0.5583	0.7889	0.3591	0.032*
O2	0.08905 (5)	0.7770 (3)	0.67653 (5)	0.02172 (18)
H2	0.0614	0.8164	0.7037	0.033*
F1	0.44392 (4)	0.61138 (19)	0.26178 (4)	0.02121 (15)
F2	0.05177 (4)	0.9789 (2)	0.31154 (4)	0.02156 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C5	0.0125 (4)	0.0190 (5)	0.0200 (4)	−0.0014 (3)	0.0041 (3)	−0.0032 (4)
C1	0.0108 (4)	0.0129 (4)	0.0155 (4)	0.0004 (3)	0.0059 (3)	−0.0003 (3)
C2	0.0117 (4)	0.0135 (4)	0.0146 (4)	0.0008 (3)	0.0059 (3)	−0.0007 (3)
C3	0.0157 (4)	0.0158 (4)	0.0152 (4)	0.0003 (3)	0.0079 (3)	−0.0009 (3)
C4	0.0164 (4)	0.0192 (5)	0.0152 (4)	−0.0002 (4)	0.0038 (3)	−0.0028 (3)
C6	0.0127 (4)	0.0159 (4)	0.0188 (4)	−0.0011 (3)	0.0069 (3)	−0.0022 (3)
C7	0.0105 (3)	0.0129 (4)	0.0123 (4)	0.0001 (3)	0.0047 (3)	−0.0003 (3)
C8	0.0118 (4)	0.0135 (4)	0.0116 (4)	−0.0008 (3)	0.0059 (3)	−0.0010 (3)
C9	0.0150 (4)	0.0168 (4)	0.0126 (4)	−0.0012 (3)	0.0071 (3)	−0.0020 (3)
C10	0.0153 (4)	0.0173 (5)	0.0217 (4)	−0.0006 (3)	0.0117 (4)	−0.0034 (4)
C11	0.0123 (4)	0.0174 (5)	0.0234 (5)	0.0015 (3)	0.0090 (3)	−0.0011 (4)
C12	0.0121 (4)	0.0159 (4)	0.0165 (4)	0.0015 (3)	0.0053 (3)	0.0011 (3)
B1	0.0114 (4)	0.0150 (5)	0.0161 (4)	0.0006 (3)	0.0067 (4)	−0.0002 (4)
B2	0.0120 (4)	0.0156 (5)	0.0115 (4)	−0.0001 (3)	0.0048 (3)	0.0007 (3)
O1	0.0152 (3)	0.0316 (5)	0.0171 (3)	−0.0035 (3)	0.0077 (3)	0.0028 (3)
O2	0.0164 (3)	0.0364 (5)	0.0126 (3)	0.0068 (3)	0.0068 (3)	0.0066 (3)
F1	0.0215 (3)	0.0286 (4)	0.0157 (3)	−0.0026 (3)	0.0104 (2)	−0.0005 (2)
F2	0.0224 (3)	0.0326 (4)	0.0122 (3)	0.0036 (3)	0.0102 (2)	0.0009 (3)

Geometric parameters (Å, º)

C5—C6	1.3901 (15)	C8—C9	1.3930 (13)
C5—C4	1.3915 (15)	C8—B2^ii	1.5690 (16)
C5—H5	0.9500	C9—F2	1.3741 (12)
C1—C6	1.4011 (15)	C9—C10	1.3763 (15)
C1—C2	1.4162 (13)	C10—C11	1.3906 (16)
C1—B1^i	1.5696 (16)	C10—H10	0.9500
C2—C3	1.3922 (15)	C11—C12	1.3914 (14)
C2—B1	1.5685 (16)	C11—H11	0.9500
C3—F1	1.3748 (12)	C12—H12	0.9500
C3—C4	1.3805 (16)	B1—O1	1.3620 (13)
C4—H4	0.9500	B1—C1^i	1.5696 (16)
C6—H6	0.9500	B2—O2	1.3581 (14)
C7—C12	1.4008 (14)	B2—C8^ii	1.5691 (16)
C7—C8	1.4165 (14)	O1—H1A	0.8400
C7—B2	1.5696 (14)	O2—H2	0.8400
C6—C5—C4	119.55 (9)	C9—C8—B2^ii	124.50 (9)
C6—C5—H5	120.2	C7—C8—B2^ii	119.88 (9)
C4—C5—H5	120.2	F2—C9—C10	116.52 (9)
C6—C1—C2	119.73 (9)	F2—C9—C8	118.03 (9)
C6—C1—B1^i	119.66 (9)	C10—C9—C8	125.44 (9)
C2—C1—B1^i	120.62 (9)	C9—C10—C11	117.95 (9)
C3—C2—C1	116.12 (9)	C9—C10—H10	121.0
C3—C2—B1	124.31 (9)	C11—C10—H10	121.0
C1—C2—B1	119.57 (9)	C10—C11—C12	119.42 (9)
F1—C3—C4	116.37 (9)	C10—C11—H11	120.3
F1—C3—C2	118.60 (9)	C12—C11—H11	120.3
C4—C3—C2	125.02 (10)	C11—C12—C7	121.57 (9)
C3—C4—C5	117.95 (10)	C11—C12—H12	119.2
C3—C4—H4	121.0	C7—C12—H12	119.2
C5—C4—H4	121.0	O1—B1—C2	124.11 (9)
C5—C6—C1	121.64 (10)	O1—B1—C1^i	116.08 (9)
C5—C6—H6	119.2	C2—B1—C1^i	119.81 (9)
C1—C6—H6	119.2	O2—B2—C8^ii	124.19 (9)
C12—C7—C8	119.99 (9)	O2—B2—C7	115.94 (9)
C12—C7—B2	119.77 (9)	C8^ii—B2—C7	119.87 (9)
C8—C7—B2	120.25 (8)	B1—O1—H1A	109.5
C9—C8—C7	115.62 (9)	B2—O2—H2	109.5
C6—C1—C2—C3	−0.24 (14)	C7—C8—C9—F2	−178.59 (9)
B1^i—C1—C2—C3	179.56 (9)	B2^ii—C8—C9—F2	1.19 (15)
C6—C1—C2—B1	179.12 (9)	C7—C8—C9—C10	0.65 (15)
B1^i—C1—C2—B1	−1.08 (16)	B2^ii—C8—C9—C10	−179.56 (10)
C1—C2—C3—F1	179.88 (9)	F2—C9—C10—C11	178.19 (9)
B1—C2—C3—F1	0.56 (15)	C8—C9—C10—C11	−1.06 (16)
C1—C2—C3—C4	0.34 (15)	C9—C10—C11—C12	0.64 (16)
B1—C2—C3—C4	−178.99 (10)	C10—C11—C12—C7	0.11 (16)
F1—C3—C4—C5	−179.71 (9)	C8—C7—C12—C11	−0.52 (15)
C2—C3—C4—C5	−0.16 (17)	B2—C7—C12—C11	179.55 (10)
C6—C5—C4—C3	−0.12 (16)	C3—C2—B1—O1	1.36 (16)
C4—C5—C6—C1	0.21 (16)	C1—C2—B1—O1	−177.95 (10)
C2—C1—C6—C5	−0.02 (15)	C3—C2—B1—C1^i	−179.63 (9)
B1^i—C1—C6—C5	−179.83 (10)	C1—C2—B1—C1^i	1.07 (15)
C12—C7—C8—C9	0.16 (14)	C12—C7—B2—O2	−0.47 (15)
B2—C7—C8—C9	−179.92 (9)	C8—C7—B2—O2	179.60 (9)
C12—C7—C8—B2^ii	−179.64 (9)	C12—C7—B2—C8^ii	179.64 (9)
B2—C7—C8—B2^ii	0.29 (16)	C8—C7—B2—C8^ii	−0.29 (16)

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

(III)

Crystal data

C12H8B2Cl2O2	F(000) = 280
Mr = 276.70	Dx = 1.616 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.3645 (10) Å	Cell parameters from 1683 reflections
b = 3.8696 (6) Å	θ = 2.0–32.1°
c = 20.125 (3) Å	µ = 0.56 mm^−1
β = 97.543 (14)°	T = 100 K
V = 568.55 (15) Å^3	Block, colourless
Z = 2	0.15 × 0.14 × 0.13 mm

Data collection

KUMA KM4 CCD diffractometer	1906 independent reflections
Radiation source: fine-focus sealed tube	977 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.109
ω scans	θmax = 32.2°, θmin = 2.0°
Absorption correction: multi-scan CrysAlis PRO (Agilent, 2011)	h = −10→11
Tmin = 0.421, Tmax = 1.000	k = −5→5
8905 measured reflections	l = −29→29

Refinement

Refinement on F^2	12 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.064	H-atom parameters constrained
wR(F^2) = 0.165	w = 1/[σ^2(Fo^2) + (0.0509P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max < 0.001
1906 reflections	Δρmax = 0.27 e Å^−3
164 parameters	Δρmin = −0.30 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	Occ. (<1)
Cl1A	0.8344 (4)	0.6810 (8)	0.18884 (12)	0.0320 (5)	0.620 (3)
O1A	1.3169 (4)	0.6676 (8)	−0.05950 (15)	0.0325 (8)	0.620 (3)
H1A	1.3260	0.5474	−0.0937	0.049*	0.620 (3)
B1A	1.1643 (9)	0.5740 (15)	−0.0330 (4)	0.0190 (10)	0.620 (3)
C1A	1.1584 (7)	0.6834 (11)	0.0419 (3)	0.0194 (8)	0.620 (3)
C2A	1.0027 (10)	0.6193 (15)	0.0747 (3)	0.0195 (11)	0.620 (3)
C3A	1.0173 (7)	0.7345 (10)	0.1409 (2)	0.0238 (9)	0.620 (3)
C4A	1.1703 (7)	0.8983 (11)	0.1751 (3)	0.0280 (11)	0.620 (3)
H4A	1.1720	0.9695	0.2204	0.034*	0.620 (3)
C5A	1.3210 (16)	0.955 (4)	0.1411 (7)	0.034 (3)	0.620 (3)
H5A	1.4271	1.0674	0.1628	0.040*	0.620 (3)
C6A	1.3146 (5)	0.8457 (10)	0.0753 (2)	0.0243 (9)	0.620 (3)
H6A	1.4178	0.8815	0.0523	0.029*	0.620 (3)
Cl1B	1.3689 (7)	0.9588 (19)	0.1505 (3)	0.0359 (10)	0.380 (3)
O1B	1.3475 (7)	0.8177 (15)	0.0012 (3)	0.0414 (16)	0.380 (3)
H1B	1.3897	0.9007	0.0387	0.062*	0.380 (3)
B1B	1.1834 (12)	0.653 (2)	0.0064 (7)	0.0215 (16)	0.380 (3)
C1B	1.0999 (14)	0.477 (2)	−0.0604 (5)	0.0193 (15)	0.380 (3)
C2B	1.0790 (18)	0.662 (2)	0.0692 (4)	0.0202 (18)	0.380 (3)
C3B	1.1447 (11)	0.807 (2)	0.1331 (5)	0.0308 (17)	0.380 (3)
C4B	1.0403 (11)	0.8242 (19)	0.1841 (4)	0.0294 (16)	0.380 (3)
H4B	1.0873	0.9302	0.2253	0.035*	0.380 (3)
C5B	0.867 (2)	0.688 (5)	0.1754 (8)	0.032 (4)	0.380 (3)
H5B	0.7950	0.6922	0.2112	0.038*	0.380 (3)
C6B	1.2021 (10)	0.4566 (18)	−0.1147 (4)	0.0270 (16)	0.380 (3)
H6B	1.3234	0.5458	−0.1093	0.032*	0.380 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1A	0.0395 (10)	0.0363 (8)	0.0240 (9)	0.0022 (7)	0.0186 (7)	−0.0005 (6)
O1A	0.0235 (16)	0.0496 (19)	0.0275 (18)	−0.0055 (14)	0.0149 (13)	−0.0035 (14)
B1A	0.013 (3)	0.026 (3)	0.019 (4)	0.001 (2)	0.004 (2)	0.003 (2)
C1A	0.023 (3)	0.020 (2)	0.016 (3)	0.0012 (17)	0.003 (2)	0.003 (2)
C2A	0.019 (3)	0.025 (3)	0.016 (2)	0.005 (3)	0.008 (3)	0.006 (2)
C3A	0.028 (2)	0.025 (2)	0.019 (2)	0.0048 (17)	0.0066 (18)	0.0067 (17)
C4A	0.040 (3)	0.027 (2)	0.017 (2)	0.003 (2)	0.000 (2)	0.0001 (18)
C5A	0.037 (6)	0.026 (3)	0.037 (5)	0.007 (4)	0.002 (4)	0.001 (3)
C6A	0.0170 (19)	0.029 (2)	0.027 (2)	−0.0027 (16)	0.0025 (16)	0.0012 (17)
Cl1B	0.037 (2)	0.0402 (15)	0.0302 (17)	−0.0051 (17)	0.0023 (15)	0.0031 (12)
O1B	0.031 (3)	0.065 (4)	0.028 (3)	−0.021 (3)	0.008 (2)	0.005 (3)
B1B	0.020 (4)	0.027 (4)	0.017 (5)	0.000 (3)	−0.002 (5)	0.003 (4)
C1B	0.008 (4)	0.034 (4)	0.017 (5)	0.004 (3)	0.006 (3)	0.011 (3)
C2B	0.027 (6)	0.020 (4)	0.016 (5)	−0.001 (4)	0.012 (5)	0.002 (3)
C3B	0.024 (4)	0.028 (4)	0.041 (5)	0.003 (3)	0.007 (4)	0.014 (4)
C4B	0.034 (5)	0.028 (4)	0.027 (4)	0.004 (3)	0.005 (3)	0.007 (3)
C5B	0.035 (6)	0.033 (5)	0.032 (7)	0.005 (4)	0.020 (4)	0.002 (5)
C6B	0.020 (3)	0.034 (4)	0.030 (4)	0.005 (3)	0.016 (3)	0.002 (3)

Geometric parameters (Å, º)

Cl1A—C3A	1.770 (5)	C5B—C6B^i	1.379 (19)
O1A—B1A	1.355 (6)	C5B—H5B	0.9500
O1A—H1A	0.8400	Cl1B—C3B	1.744 (10)
C1A—C6A	1.402 (6)	C3B—C4B	1.361 (12)
C1A—C2A	1.418 (7)	C3B—C2B	1.429 (15)
C1A—B1A	1.571 (8)	C1B—C6B	1.409 (9)
C2A—C3A	1.395 (8)	C1B—C2B^i	1.412 (11)
C2A—B1A^i	1.583 (9)	C1B—B1B	1.560 (12)
B1A—C2A^i	1.583 (9)	O1B—B1B	1.382 (10)
C3A—C4A	1.394 (7)	O1B—H1B	0.8400
C4A—C5A	1.396 (15)	C2B—C1B^i	1.412 (11)
C4A—H4A	0.9500	C2B—B1B	1.564 (14)
C5A—C6A	1.385 (15)	C4B—H4B	0.9500
C5A—H5A	0.9500	C6B—C5B^i	1.379 (19)
C6A—H6A	0.9500	C6B—H6B	0.9500
C5B—C4B	1.370 (19)
B1A—O1A—H1A	109.5	C4B—C5B—C6B^i	119.9 (10)
C6A—C1A—C2A	121.1 (6)	C4B—C5B—H5B	120.1
C6A—C1A—B1A	117.1 (6)	C6B^i—C5B—H5B	120.1
C2A—C1A—B1A	121.7 (4)	C4B—C3B—C2B	122.6 (9)
C3A—C2A—C1A	115.1 (6)	C4B—C3B—Cl1B	116.5 (8)
C3A—C2A—B1A^i	127.9 (7)	C2B—C3B—Cl1B	120.9 (8)
C1A—C2A—B1A^i	117.0 (5)	C6B—C1B—C2B^i	117.8 (10)
O1A—B1A—C1A	115.8 (7)	C6B—C1B—B1B	120.2 (11)
O1A—B1A—C2A^i	123.0 (7)	C2B^i—C1B—B1B	122.0 (7)
C1A—B1A—C2A^i	121.2 (4)	B1B—O1B—H1B	109.5
C4A—C3A—C2A	125.0 (6)	C1B^i—C2B—C3B	117.5 (9)
C4A—C3A—Cl1A	114.0 (4)	C1B^i—C2B—B1B	116.1 (8)
C2A—C3A—Cl1A	121.0 (5)	C3B—C2B—B1B	126.3 (11)
C3A—C4A—C5A	118.1 (7)	C3B—C4B—C5B	119.6 (10)
C3A—C4A—H4A	120.9	C3B—C4B—H4B	120.2
C5A—C4A—H4A	120.9	C5B—C4B—H4B	120.2
C6A—C5A—C4A	119.5 (9)	O1B—B1B—C1B	112.8 (11)
C6A—C5A—H5A	120.3	O1B—B1B—C2B	125.3 (12)
C4A—C5A—H5A	120.3	C1B—B1B—C2B	121.7 (7)
C5A—C6A—C1A	121.2 (7)	C5B^i—C6B—C1B	122.5 (10)
C5A—C6A—H6A	119.4	C5B^i—C6B—H6B	118.8
C1A—C6A—H6A	119.4	C1B—C6B—H6B	118.8

Symmetry code: (i) −x+2, −y+1, −z.

(IV)

Crystal data

C12H8B2Br2O2	F(000) = 352
Mr = 365.62	Dx = 2.066 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.988 (3) Å	Cell parameters from 4741 reflections
b = 3.9050 (8) Å	θ = 2.3–28.6°
c = 16.841 (5) Å	µ = 6.88 mm^−1
β = 96.11 (3)°	T = 100 K
V = 587.7 (3) Å^3	Block, colourles
Z = 2	0.13 × 0.11 × 0.09 mm

Data collection

KUMA KM4 CCD diffractometer	1402 independent reflections
Radiation source: fine-focus sealed tube	1195 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.083
ω scans	θmax = 28.6°, θmin = 2.7°
Absorption correction: multi-scan CrysAlis PRO (Agilent, 2011)	h = −11→11
Tmin = 0.428, Tmax = 1.000	k = −4→5
8654 measured reflections	l = −22→22

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0686P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
1402 reflections	Δρmax = 1.29 e Å^−3
82 parameters	Δρmin = −1.37 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
Br1	0.96685 (4)	0.05617 (10)	0.76151 (2)	0.01642 (18)
O1	1.2395 (3)	0.6699 (9)	1.11718 (16)	0.0240 (6)
H1	1.2104	0.7683	1.1571	0.036*
B1	1.1195 (4)	0.5889 (10)	1.0647 (2)	0.0133 (8)
C1	1.0983 (4)	0.1722 (10)	0.8556 (2)	0.0143 (7)
C2	1.0475 (3)	0.3228 (10)	0.92270 (19)	0.0116 (6)
C3	1.1577 (4)	0.4025 (9)	0.9868 (2)	0.0123 (7)
C4	1.3083 (4)	0.3233 (11)	0.9817 (2)	0.0156 (7)
H4	1.3796	0.3732	1.0259	0.019*
C5	1.3575 (4)	0.1732 (10)	0.9137 (2)	0.0181 (7)
H5	1.4604	0.1254	0.9105	0.022*
C6	1.2466 (4)	0.0956 (9)	0.8498 (2)	0.0162 (7)
H6	1.2746	−0.0096	0.8027	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0186 (2)	0.0180 (3)	0.0132 (2)	−0.00214 (12)	0.00419 (14)	−0.00445 (12)
O1	0.0146 (12)	0.0416 (18)	0.0156 (13)	0.0062 (12)	0.0004 (10)	−0.0083 (13)
B1	0.0178 (18)	0.012 (2)	0.0106 (18)	0.0001 (14)	0.0024 (15)	0.0037 (14)
C1	0.0185 (16)	0.0117 (17)	0.0129 (16)	−0.0003 (14)	0.0028 (13)	0.0002 (14)
C2	0.0146 (15)	0.0089 (17)	0.0119 (16)	−0.0007 (13)	0.0038 (12)	0.0040 (13)
C3	0.0133 (16)	0.0097 (19)	0.0146 (17)	0.0009 (12)	0.0048 (13)	0.0038 (12)
C4	0.0151 (16)	0.0151 (18)	0.0171 (18)	0.0004 (14)	0.0040 (13)	0.0025 (15)
C5	0.0319 (19)	0.0087 (18)	0.0147 (17)	0.0023 (16)	0.0068 (14)	0.0024 (15)
C6	0.0191 (17)	0.014 (2)	0.0172 (18)	0.0012 (13)	0.0089 (14)	0.0001 (13)

Geometric parameters (Å, º)

C1—C6	1.379 (5)	C4—H4	0.9500
C1—C2	1.393 (5)	C5—C6	1.420 (5)
C1—Br1	1.928 (4)	C5—H5	0.9500
C2—C3	1.419 (5)	C6—H6	0.9500
C2—B1^i	1.576 (5)	O1—B1	1.357 (5)
C3—C4	1.400 (5)	O1—H1	0.8400
C3—B1	1.571 (5)	B1—C2^i	1.576 (5)
C4—C5	1.399 (5)
C6—C1—C2	123.5 (3)	C5—C4—H4	118.8
C6—C1—Br1	113.7 (3)	C4—C5—C6	116.9 (3)
C2—C1—Br1	122.7 (2)	C4—C5—H5	121.6
C1—C2—C3	116.5 (3)	C6—C5—H5	121.6
C1—C2—B1^i	126.9 (3)	C1—C6—C5	120.3 (3)
C3—C2—B1^i	116.6 (3)	C1—C6—H6	119.8
C4—C3—C2	120.4 (3)	C5—C6—H6	119.8
C4—C3—B1	116.9 (3)	B1—O1—H1	109.5
C2—C3—B1	122.7 (3)	O1—B1—C3	115.0 (3)
C3—C4—C5	122.3 (3)	O1—B1—C2^i	124.4 (3)
C3—C4—H4	118.8	C3—B1—C2^i	120.6 (3)
C6—C1—C2—C3	0.9 (6)	B1—C3—C4—C5	−176.7 (4)
Br1—C1—C2—C3	−178.3 (3)	C3—C4—C5—C6	−1.5 (6)
C6—C1—C2—B1^i	−178.5 (4)	C2—C1—C6—C5	−0.7 (6)
Br1—C1—C2—B1^i	2.2 (6)	Br1—C1—C6—C5	178.6 (3)
C1—C2—C3—C4	−1.4 (5)	C4—C5—C6—C1	0.9 (6)
B1^i—C2—C3—C4	178.1 (3)	C4—C3—B1—O1	3.5 (5)
C1—C2—C3—B1	177.0 (3)	C2—C3—B1—O1	−175.0 (3)
B1^i—C2—C3—B1	−3.6 (6)	C4—C3—B1—C2^i	−177.9 (3)
C2—C3—C4—C5	1.8 (6)	C2—C3—B1—C2^i	3.7 (6)

Symmetry code: (i) −x+2, −y+1, −z+2.

(V)

Crystal data

C8H6B2O2S2	Dx = 1.330 Mg m^−3
Mr = 219.87	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3:H	θ = 0.3–26.3°
a = 24.719 (2) Å	µ = 0.45 mm^−1
c = 4.6681 (4) Å	T = 100 K
V = 2470.2 (5) Å^3	Needle, colourless
Z = 9	0.20 × 0.03 × 0.03 mm
F(000) = 1008

Data collection

Bruker Kappa APEX-II Ultra diffractometer	1158 independent reflections
Radiation source: fine-focus sealed tube	1061 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
ω scans	θmax = 26.7°, θmin = 2.9°
Absorption correction: multi-scan SORTAV (Blessing, 1995; Blessing, 1997)	h = −31→30
Tmin = 0.529, Tmax = 1.000	k = −28→31
13594 measured reflections	l = −5→5

Refinement

Refinement on F^2	27 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.193	w = 1/[σ^2(Fo^2) + (0.1152P)^2 + 3.5904P] where P = (Fo^2 + 2Fc^2)/3
S = 1.29	(Δ/σ)max < 0.001
1158 reflections	Δρmax = 1.09 e Å^−3
93 parameters	Δρmin = −0.35 e Å^−3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat operating at 100.0 (2) K.

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. Refined as a 2-component twin.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1A	0.8998 (2)	0.49994 (17)	0.0707 (6)	0.0276 (6)	0.815 (9)
C3A	0.9154 (4)	0.4038 (9)	0.090 (4)	0.040 (5)	0.815 (9)
H3A	0.9140	0.3657	0.0435	0.049*	0.815 (9)
C4A	0.8785 (3)	0.4258 (4)	−0.0370 (14)	0.0299 (14)	0.815 (9)
H4A	0.8455	0.4022	−0.1677	0.036*	0.815 (9)
C3B	0.9118 (14)	0.506 (4)	0.094 (15)	0.05 (3)	0.185 (9)
H3B	0.9085	0.5418	0.0474	0.054*	0.185 (9)
S1B	0.9026 (5)	0.3995 (7)	0.083 (3)	0.017 (3)	0.185 (9)
C4B	0.8788 (16)	0.4497 (18)	−0.022 (7)	0.032 (8)	0.185 (9)
H4B	0.8450	0.4386	−0.1501	0.039*	0.185 (9)
O1	1.00549 (15)	0.38712 (13)	0.5193 (6)	0.0261 (8)
H1	0.9798	0.3606	0.4041	0.039*
C2	0.9556 (2)	0.4481 (2)	0.3008 (9)	0.0225 (9)
C1	0.9547 (2)	0.5035 (2)	0.3061 (8)	0.0240 (10)
B1	1.0024 (3)	0.4405 (2)	0.5021 (10)	0.0222 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0395 (12)	0.0298 (11)	0.0210 (9)	0.0230 (10)	−0.0101 (9)	−0.0048 (7)
C3A	0.041 (5)	0.038 (6)	0.044 (6)	0.021 (4)	0.003 (4)	0.005 (3)
C4A	0.035 (3)	0.030 (3)	0.024 (2)	0.017 (2)	−0.009 (2)	−0.008 (2)
C3B	0.05 (3)	0.04 (3)	0.04 (3)	0.023 (14)	0.003 (5)	−0.002 (5)
S1B	0.021 (4)	0.018 (4)	0.016 (4)	0.012 (4)	0.000 (3)	−0.001 (3)
C4B	0.034 (9)	0.032 (9)	0.031 (9)	0.016 (6)	−0.003 (5)	0.002 (5)
O1	0.0326 (16)	0.0239 (16)	0.0251 (14)	0.0166 (13)	−0.0042 (12)	−0.0037 (12)
C2	0.031 (2)	0.023 (2)	0.0151 (17)	0.0153 (17)	−0.0004 (16)	−0.0005 (15)
C1	0.032 (2)	0.027 (2)	0.0153 (18)	0.017 (2)	−0.0019 (16)	−0.0014 (15)
B1	0.028 (2)	0.024 (2)	0.0166 (18)	0.014 (2)	0.0016 (15)	0.0002 (18)

Geometric parameters (Å, º)

S1A—C4A	1.710 (9)	S1B—C2	1.620 (13)
S1A—C1	1.713 (5)	S1B—C4B	1.69 (4)
C3A—C4A	1.405 (18)	C4B—H4B	0.9500
C3A—C2	1.438 (17)	O1—B1	1.362 (5)
C3A—H3A	0.9500	O1—H1	0.8400
C4A—H4A	0.9500	C2—C1	1.382 (5)
C3B—C4B	1.33 (7)	C2—B1	1.572 (6)
C3B—C1	1.48 (5)	C1—B1^i	1.541 (6)
C3B—H3B	0.9500	B1—C1^i	1.541 (6)
C4A—S1A—C1	93.2 (3)	B1—O1—H1	109.5
C4A—C3A—C2	109.2 (14)	C1—C2—C3A	114.8 (9)
C4A—C3A—H3A	125.4	C1—C2—B1	119.0 (4)
C2—C3A—H3A	125.4	C3A—C2—B1	126.1 (9)
C3A—C4A—S1A	112.3 (9)	C1—C2—S1B	109.7 (6)
C3A—C4A—H4A	123.9	B1—C2—S1B	131.2 (6)
S1A—C4A—H4A	123.9	C2—C1—C3B	114 (3)
C4B—C3B—C1	108 (6)	C2—C1—B1^i	123.8 (4)
C4B—C3B—H3B	126.2	C3B—C1—B1^i	122 (3)
C1—C3B—H3B	126.2	C2—C1—S1A	110.1 (3)
C2—S1B—C4B	95.0 (15)	B1^i—C1—S1A	126.2 (4)
C3B—C4B—S1B	114 (4)	O1—B1—C1^i	119.3 (4)
C3B—C4B—H4B	123.2	O1—B1—C2	123.4 (4)
S1B—C4B—H4B	123.2	C1^i—B1—C2	117.2 (3)
C2—C3A—C4A—S1A	6.9 (14)	C3A—C2—C1—S1A	4.6 (8)
C1—S1A—C4A—C3A	−3.9 (9)	B1—C2—C1—S1A	−179.7 (3)
C1—C3B—C4B—S1B	−7 (6)	S1B—C2—C1—S1A	−2.2 (8)
C2—S1B—C4B—C3B	3 (4)	C4B—C3B—C1—C2	8 (5)
C4A—C3A—C2—C1	−7.4 (13)	C4B—C3B—C1—B1^i	−176 (3)
C4A—C3A—C2—B1	177.3 (7)	C4B—C3B—C1—S1A	−4E1 (4)
C4A—C3A—C2—S1B	45 (9)	C4A—S1A—C1—C2	−0.4 (5)
C4B—S1B—C2—C1	2.1 (14)	C4A—S1A—C1—C3B	13E1 (4)
C4B—S1B—C2—C3A	−128 (11)	C4A—S1A—C1—B1^i	179.3 (4)
C4B—S1B—C2—B1	179.3 (12)	C1—C2—B1—O1	177.8 (4)
C3A—C2—C1—C3B	0 (3)	C3A—C2—B1—O1	−7.1 (10)
B1—C2—C1—C3B	176 (3)	S1B—C2—B1—O1	0.9 (10)
S1B—C2—C1—C3B	−6 (3)	C1—C2—B1—C1^i	−0.5 (7)
C3A—C2—C1—B1^i	−175.1 (8)	C3A—C2—B1—C1^i	174.6 (9)
B1—C2—C1—B1^i	0.5 (7)	S1B—C2—B1—C1^i	−177.4 (8)
S1B—C2—C1—B1^i	178.1 (6)

Symmetry code: (i) −x+2, −y+1, −z+1.