Crystal engineering in the gem-alkynol family; synthon repetitivity and topological similarity in diphenylethynylmethanols: structures that lack O—­H...O hydrogen bonds

The structures of four para-substituted derivatives of diphenylethynylmethanol have been determined [ditolylethynylmethanol, di(4-chlorophenyl)ethynylmethanol, di(4-bromophenyl)ethynylmethanol and bis(4,4′-biphenylyl)ethynylmethanol]. The dimethyl, dichloro, dibromo and diphenyl compounds have been analysed using X-ray diffraction at 150 K, and the dichloro compound has also been studied using neutron diffraction at 150 K. In common with the parent diphenylethynylmethanol [Garcia, Ramos, ­Rodriguez & Fronczek (1995). Acta Cryst. C51, 2674–2676], all four derivatives fail to form the expected strong O—H...O hydrogen bonds due to steric hindrance. Instead, the supramolecular structural organization in this family of gem-alkynols is mediated by a variety of weaker interactions. The two most acidic protons, O—H and C[triple bond]C—H, participate in weak hydrogen bonds to π-acceptors, forming synthons that stabilize all five structures. These primary interactions are reinforced by a variety of other weak hydrogen bonds involving C—H donors and the hydroxy-O as an acceptor, and by halogen...halogen interactions in the dichloro and dibromo compounds.

Computing details

Data collection: Bruker SMART (Bruker Systems Inc., 1999a) for (2), (3X), (4), (5); SXD (Keen & Wilson, 1996) for (3N). Cell refinement: Bruker SMART (Bruker Systems Inc., 1999a) for (2), (3X), (4), (5); SXD (Keen & Wilson, 1996) for (3N). Data reduction: Bruker SAINT (Bruker Systems Inc., 1999b) for (2), (3X), (4), (5); SXD (Keen & Wilson, 1996) for (3N). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

(2)

Crystal data

C17H16O	F(000) = 252
Mr = 236.30	Dx = 1.204 Mg m^−3
Triclinic, P1	Melting point: 95-96 K
a = 6.8286 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.2407 (16) Å	Cell parameters from 512 reflections
c = 12.658 (3) Å	θ = 5.3–29.4°
α = 106.73 (3)°	µ = 0.07 mm^−1
β = 98.71 (3)°	T = 150 K
γ = 101.39 (3)°	Block, colourless
V = 652.0 (2) Å^3	0.3 × 0.3 × 0.2 mm
Z = 2

Data collection

Bruker SMART CCD diffractometer	2964 independent reflections
Radiation source: fine-focus sealed tube	2362 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan SADABS (Sheldrick 1996)	h = −8→8
Tmin = 0.784, Tmax = 1.000	k = −10→7
4775 measured reflections	l = −14→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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F^2) = 0.132	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0618P)^2 + 0.2678P] where P = (Fo^2 + 2Fc^2)/3
2964 reflections	(Δ/σ)max = 0.028
231 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)
H1	0.759 (3)	−0.095 (3)	0.3239 (19)	0.052 (6)*
C1	0.7141 (3)	−0.0109 (2)	0.29487 (14)	0.0344 (4)
C2	0.6603 (2)	0.09261 (19)	0.25638 (13)	0.0266 (3)
C3	0.5790 (2)	0.21385 (18)	0.20481 (12)	0.0229 (3)
O1	0.36138 (16)	0.14659 (15)	0.16398 (10)	0.0278 (3)
HA	0.348 (4)	0.043 (3)	0.119 (2)	0.060 (7)*
C4	0.6155 (2)	0.39365 (18)	0.29666 (12)	0.0224 (3)
C5	0.4550 (2)	0.4686 (2)	0.31962 (14)	0.0277 (3)
H5	0.314 (3)	0.409 (3)	0.2785 (18)	0.044 (6)*
C6	0.4927 (3)	0.6303 (2)	0.40489 (14)	0.0303 (4)
H6	0.378 (3)	0.683 (3)	0.4221 (16)	0.039 (5)*
C7	0.6903 (2)	0.71997 (19)	0.46824 (12)	0.0263 (3)
C8	0.7306 (3)	0.8924 (2)	0.56227 (15)	0.0356 (4)
H8A	0.837 (4)	0.987 (4)	0.554 (2)	0.077 (8)*
H8B	0.606 (5)	0.934 (4)	0.570 (2)	0.088 (9)*
H8C	0.783 (4)	0.882 (4)	0.636 (2)	0.077 (8)*
C9	0.8508 (2)	0.6444 (2)	0.44306 (13)	0.0281 (3)
H9	0.990 (3)	0.702 (2)	0.4848 (16)	0.032 (5)*
C10	0.8142 (2)	0.4830 (2)	0.35843 (13)	0.0272 (3)
H10	0.932 (3)	0.432 (3)	0.3424 (17)	0.043 (5)*
C11	0.6815 (2)	0.23500 (17)	0.10758 (12)	0.0222 (3)
C12	0.5842 (2)	0.29838 (19)	0.02815 (13)	0.0260 (3)
H12	0.453 (3)	0.324 (2)	0.0344 (16)	0.034 (5)*
C13	0.6724 (3)	0.3212 (2)	−0.06040 (13)	0.0282 (3)
H13	0.601 (3)	0.361 (3)	−0.1146 (18)	0.044 (6)*
C14	0.8597 (2)	0.28299 (18)	−0.07268 (13)	0.0266 (3)
C15	0.9529 (3)	0.3045 (2)	−0.17029 (15)	0.0362 (4)
H15A	1.010 (7)	0.206 (6)	−0.202 (4)	0.045 (11)*	0.50
H66	1.112 (7)	0.323 (6)	−0.152 (4)	0.043 (11)*	0.50
H15B	0.994 (5)	0.421 (4)	−0.168 (3)	0.095 (10)*
H15C	0.854 (5)	0.250 (4)	−0.241 (3)	0.090 (9)*
C16	0.9569 (2)	0.22143 (19)	0.00761 (13)	0.0266 (3)
H16	1.086 (3)	0.192 (2)	0.0026 (16)	0.031 (5)*
C17	0.8691 (2)	0.19732 (19)	0.09667 (13)	0.0248 (3)
H17	0.939 (3)	0.152 (2)	0.1506 (15)	0.027 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0441 (10)	0.0283 (8)	0.0350 (9)	0.0110 (7)	0.0101 (7)	0.0148 (7)
C2	0.0292 (8)	0.0220 (7)	0.0261 (7)	0.0033 (6)	0.0066 (6)	0.0061 (6)
C3	0.0223 (7)	0.0198 (7)	0.0249 (7)	0.0039 (5)	0.0031 (5)	0.0065 (6)
O1	0.0227 (5)	0.0230 (5)	0.0319 (6)	0.0013 (4)	0.0030 (4)	0.0050 (5)
C4	0.0269 (7)	0.0197 (6)	0.0215 (7)	0.0053 (5)	0.0056 (5)	0.0084 (5)
C5	0.0243 (8)	0.0247 (7)	0.0314 (8)	0.0051 (6)	0.0039 (6)	0.0072 (6)
C6	0.0307 (8)	0.0263 (8)	0.0356 (9)	0.0111 (6)	0.0101 (7)	0.0088 (7)
C7	0.0351 (8)	0.0216 (7)	0.0229 (7)	0.0057 (6)	0.0082 (6)	0.0088 (6)
C8	0.0460 (10)	0.0252 (8)	0.0309 (9)	0.0070 (7)	0.0106 (7)	0.0026 (7)
C9	0.0279 (8)	0.0263 (7)	0.0253 (7)	0.0019 (6)	0.0023 (6)	0.0064 (6)
C10	0.0253 (8)	0.0253 (7)	0.0294 (8)	0.0066 (6)	0.0060 (6)	0.0063 (6)
C11	0.0239 (7)	0.0161 (6)	0.0227 (7)	0.0028 (5)	0.0027 (5)	0.0035 (5)
C12	0.0253 (8)	0.0237 (7)	0.0284 (8)	0.0073 (6)	0.0033 (6)	0.0081 (6)
C13	0.0341 (8)	0.0240 (7)	0.0252 (7)	0.0070 (6)	0.0018 (6)	0.0087 (6)
C14	0.0328 (8)	0.0172 (6)	0.0243 (7)	0.0007 (6)	0.0068 (6)	0.0020 (5)
C15	0.0494 (11)	0.0275 (8)	0.0296 (9)	0.0053 (8)	0.0157 (8)	0.0055 (7)
C16	0.0243 (7)	0.0218 (7)	0.0313 (8)	0.0056 (6)	0.0066 (6)	0.0051 (6)
C17	0.0254 (7)	0.0205 (7)	0.0262 (7)	0.0053 (6)	0.0024 (6)	0.0063 (6)

Geometric parameters (Å, º)

C1—C2	1.187 (2)	C9—C10	1.395 (2)
C1—H1	0.95 (2)	C9—H9	0.97 (2)
C2—C3	1.489 (2)	C10—H10	1.00 (2)
C3—O1	1.4349 (18)	C11—C17	1.394 (2)
C3—C11	1.540 (2)	C11—C12	1.401 (2)
C3—C4	1.544 (2)	C12—C13	1.391 (2)
O1—HA	0.85 (3)	C12—H12	0.97 (2)
C4—C5	1.389 (2)	C13—C14	1.396 (2)
C4—C10	1.395 (2)	C13—H13	0.95 (2)
C5—C6	1.400 (2)	C14—C16	1.399 (2)
C5—H5	0.98 (2)	C14—C15	1.511 (2)
C6—C7	1.395 (2)	C15—H15A	0.98 (4)
C6—H6	0.99 (2)	C15—H66	1.04 (5)
C7—C9	1.397 (2)	C15—H15B	0.94 (3)
C7—C8	1.511 (2)	C15—H15C	0.97 (3)
C8—H8A	0.99 (3)	C16—C17	1.399 (2)
C8—H8B	0.98 (3)	C16—H16	0.965 (19)
C8—H8C	0.99 (3)	C17—H17	0.974 (18)
C2—C1—H1	178.4 (14)	C9—C10—H10	119.2 (12)
C1—C2—C3	176.11 (17)	C4—C10—H10	120.3 (12)
O1—C3—C2	108.99 (12)	C17—C11—C12	118.62 (14)
O1—C3—C11	110.27 (12)	C17—C11—C3	122.77 (13)
C2—C3—C11	111.00 (12)	C12—C11—C3	118.59 (13)
O1—C3—C4	106.89 (12)	C13—C12—C11	120.51 (14)
C2—C3—C4	109.38 (12)	C13—C12—H12	120.2 (11)
C11—C3—C4	110.21 (11)	C11—C12—H12	119.3 (11)
C3—O1—HA	103.8 (17)	C12—C13—C14	121.45 (14)
C5—C4—C10	119.09 (14)	C12—C13—H13	118.9 (13)
C5—C4—C3	121.53 (13)	C14—C13—H13	119.7 (13)
C10—C4—C3	119.38 (13)	C13—C14—C16	117.71 (14)
C4—C5—C6	120.15 (15)	C13—C14—C15	121.28 (15)
C4—C5—H5	121.1 (12)	C16—C14—C15	121.01 (15)
C6—C5—H5	118.8 (12)	C14—C15—H15A	111 (3)
C7—C6—C5	121.34 (15)	C14—C15—H66	112 (2)
C7—C6—H6	118.3 (12)	H15A—C15—H66	61 (3)
C5—C6—H6	120.3 (12)	C14—C15—H15B	114.0 (19)
C6—C7—C9	117.91 (14)	H15A—C15—H15B	129 (3)
C6—C7—C8	121.42 (15)	H66—C15—H15B	81 (3)
C9—C7—C8	120.66 (15)	C14—C15—H15C	111.2 (19)
C7—C8—H8A	113.0 (16)	H15A—C15—H15C	82 (3)
C7—C8—H8B	113.1 (18)	H66—C15—H15C	130 (3)
H8A—C8—H8B	109 (2)	H15B—C15—H15C	102 (3)
C7—C8—H8C	111.0 (16)	C14—C16—C17	121.30 (14)
H8A—C8—H8C	105 (2)	C14—C16—H16	121.2 (11)
H8B—C8—H8C	105 (2)	C17—C16—H16	117.5 (11)
C10—C9—C7	121.05 (15)	C11—C17—C16	120.41 (14)
C10—C9—H9	118.2 (11)	C11—C17—H17	119.9 (11)
C7—C9—H9	120.7 (11)	C16—C17—H17	119.7 (11)
C9—C10—C4	120.45 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—HA···C11^i	0.85 (3)	3.07 (3)	3.860 (2)	155 (2)
O1—HA···C13^i	0.85 (3)	2.85 (3)	3.644 (2)	156 (2)
O1—HA···C16^i	0.85 (3)	2.61 (3)	3.288 (2)	137 (2)

Symmetry code: (i) −x+1, −y, −z.

(3X)

Crystal data

C15H10Cl2O	F(000) = 284
Mr = 277.13	Dx = 1.439 Mg m^−3
Triclinic, P1	Melting point: 72-73 K
a = 5.7082 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3645 (2) Å	Cell parameters from 500 reflections
c = 11.5167 (1) Å	θ = 5.4–29.2°
α = 117.268 (1)°	µ = 0.49 mm^−1
β = 99.257 (1)°	T = 150 K
γ = 96.726 (1)°	Block, colourless
V = 639.73 (2) Å^3	0.5 × 0.4 × 0.4 mm
Z = 2

Data collection

Bruker SMART CCD diffractometer	2826 independent reflections
Radiation source: fine-focus sealed tube	2617 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: not relevant pixels mm^-1	θmax = 27.3°, θmin = 2.1°
ω scans	h = −6→7
Absorption correction: multi-scan SADABS (Sheldrick 1996)	k = −11→14
Tmin = 0.284, Tmax = 0.332	l = −14→12
4371 measured reflections

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)] = 0.038	Hydrogen site location: difference Fourier map
wR(F^2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0467P)^2 + 0.3533P] where P = (Fo^2 + 2Fc^2)/3
2826 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
H1	1.044 (5)	−0.109 (3)	0.266 (3)	0.051 (7)*
C1	1.0066 (3)	−0.02664 (17)	0.30273 (19)	0.0305 (4)
C2	0.9579 (3)	0.08150 (16)	0.35028 (16)	0.0235 (3)
C3	0.9001 (3)	0.21751 (15)	0.40912 (16)	0.0214 (3)
O1	1.1132 (2)	0.31881 (11)	0.44629 (13)	0.0267 (3)
HA	1.163 (5)	0.298 (2)	0.383 (3)	0.040 (6)*
C4	0.8200 (3)	0.24719 (14)	0.53893 (15)	0.0201 (3)
C5	0.9651 (3)	0.34161 (15)	0.66530 (16)	0.0243 (3)
H5	1.126 (4)	0.391 (2)	0.673 (2)	0.035 (5)*
C6	0.8855 (3)	0.36662 (16)	0.78075 (17)	0.0270 (3)
H6	0.986 (4)	0.430 (2)	0.867 (2)	0.029 (5)*
C7	0.6591 (3)	0.29600 (16)	0.76799 (16)	0.0249 (3)
Cl1	0.04963 (8)	0.26483 (5)	0.05839 (5)	0.03706 (14)
C8	0.5132 (3)	0.20033 (17)	0.64306 (17)	0.0272 (3)
H8	0.357 (4)	0.147 (2)	0.632 (2)	0.040 (6)*
C9	0.5949 (3)	0.17631 (17)	0.52931 (16)	0.0252 (3)
H9	0.494 (4)	0.110 (2)	0.444 (2)	0.036 (6)*
C10	0.6949 (3)	0.22598 (15)	0.31106 (15)	0.0214 (3)
C11	0.6523 (3)	0.35366 (15)	0.33946 (17)	0.0253 (3)
H11	0.751 (4)	0.432 (2)	0.414 (2)	0.026 (5)*
C12	0.4577 (3)	0.36638 (17)	0.26036 (17)	0.0276 (3)
H12	0.435 (4)	0.455 (2)	0.279 (2)	0.036 (6)*
C13	0.3042 (3)	0.25021 (17)	0.15251 (16)	0.0271 (3)
Cl2	0.55431 (8)	0.32701 (5)	0.91110 (4)	0.03824 (15)
C14	0.3448 (3)	0.12307 (17)	0.12157 (17)	0.0291 (3)
H14	0.247 (4)	0.048 (2)	0.050 (2)	0.036 (6)*
C15	0.5417 (3)	0.11124 (16)	0.20127 (17)	0.0264 (3)
H15	0.566 (4)	0.025 (2)	0.179 (2)	0.029 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0236 (7)	0.0274 (8)	0.0405 (9)	0.0084 (6)	0.0108 (7)	0.0149 (7)
C2	0.0164 (6)	0.0271 (7)	0.0270 (8)	0.0029 (5)	0.0064 (5)	0.0134 (6)
C3	0.0176 (6)	0.0196 (6)	0.0249 (7)	0.0004 (5)	0.0058 (5)	0.0097 (6)
O1	0.0208 (5)	0.0248 (5)	0.0316 (6)	−0.0018 (4)	0.0099 (5)	0.0119 (5)
C4	0.0175 (6)	0.0192 (6)	0.0254 (7)	0.0048 (5)	0.0062 (5)	0.0118 (6)
C5	0.0210 (7)	0.0214 (7)	0.0271 (8)	0.0016 (5)	0.0041 (6)	0.0103 (6)
C6	0.0289 (8)	0.0225 (7)	0.0246 (8)	0.0046 (6)	0.0040 (6)	0.0083 (6)
C7	0.0259 (7)	0.0293 (7)	0.0255 (7)	0.0139 (6)	0.0103 (6)	0.0153 (6)
Cl1	0.0344 (2)	0.0452 (3)	0.0350 (2)	0.01327 (19)	0.00330 (18)	0.0229 (2)
C8	0.0186 (7)	0.0352 (8)	0.0312 (9)	0.0057 (6)	0.0075 (6)	0.0185 (7)
C9	0.0175 (7)	0.0299 (8)	0.0253 (8)	0.0006 (6)	0.0035 (6)	0.0124 (6)
C10	0.0208 (7)	0.0216 (7)	0.0230 (7)	0.0034 (5)	0.0082 (5)	0.0111 (6)
C11	0.0268 (7)	0.0205 (7)	0.0280 (8)	0.0027 (6)	0.0074 (6)	0.0115 (6)
C12	0.0301 (8)	0.0252 (7)	0.0330 (8)	0.0078 (6)	0.0103 (7)	0.0176 (7)
C13	0.0259 (7)	0.0359 (8)	0.0252 (8)	0.0090 (6)	0.0086 (6)	0.0184 (7)
Cl2	0.0370 (2)	0.0542 (3)	0.0297 (2)	0.0189 (2)	0.01751 (18)	0.0204 (2)
C14	0.0290 (8)	0.0283 (8)	0.0237 (8)	0.0047 (6)	0.0034 (6)	0.0087 (7)
C15	0.0275 (8)	0.0222 (7)	0.0265 (8)	0.0054 (6)	0.0060 (6)	0.0095 (6)

Geometric parameters (Å, º)

C1—C2	1.183 (2)	Cl1—C13	1.7404 (17)
C1—H1	0.90 (3)	C8—C9	1.381 (2)
C2—C3	1.479 (2)	C8—H8	0.97 (2)
C3—O1	1.4287 (17)	C9—H9	0.95 (2)
C3—C4	1.534 (2)	C10—C15	1.389 (2)
C3—C10	1.535 (2)	C10—C11	1.395 (2)
O1—HA	0.77 (3)	C11—C12	1.385 (2)
C4—C5	1.389 (2)	C11—H11	0.93 (2)
C4—C9	1.394 (2)	C12—C13	1.389 (2)
C5—C6	1.391 (2)	C12—H12	0.95 (2)
C5—H5	0.99 (2)	C13—C14	1.379 (2)
C6—C7	1.387 (2)	C14—C15	1.393 (2)
C6—H6	0.95 (2)	C14—H14	0.90 (2)
C7—C8	1.384 (2)	C15—H15	0.93 (2)
C7—Cl2	1.7415 (16)
C2—C1—H1	179.0 (17)	C7—C8—H8	122.6 (14)
C1—C2—C3	179.12 (17)	C8—C9—C4	120.99 (15)
O1—C3—C2	109.98 (12)	C8—C9—H9	118.5 (14)
O1—C3—C4	106.71 (12)	C4—C9—H9	120.5 (13)
C2—C3—C4	109.22 (12)	C15—C10—C11	119.32 (15)
O1—C3—C10	110.68 (12)	C15—C10—C3	122.36 (13)
C2—C3—C10	111.25 (12)	C11—C10—C3	118.18 (13)
C4—C3—C10	108.87 (12)	C12—C11—C10	120.56 (15)
C3—O1—HA	106.2 (19)	C12—C11—H11	118.5 (12)
C5—C4—C9	119.18 (14)	C10—C11—H11	121.0 (12)
C5—C4—C3	122.08 (13)	C11—C12—C13	119.19 (15)
C9—C4—C3	118.74 (13)	C11—C12—H12	119.5 (14)
C4—C5—C6	120.45 (14)	C13—C12—H12	121.3 (14)
C4—C5—H5	119.4 (13)	C14—C13—C12	121.21 (15)
C6—C5—H5	120.2 (13)	C14—C13—Cl1	119.30 (13)
C7—C6—C5	119.10 (15)	C12—C13—Cl1	119.45 (13)
C7—C6—H6	120.6 (12)	C13—C14—C15	119.21 (15)
C5—C6—H6	120.3 (13)	C13—C14—H14	120.6 (14)
C8—C7—C6	121.27 (15)	C15—C14—H14	120.1 (14)
C8—C7—Cl2	118.85 (12)	C10—C15—C14	120.50 (15)
C6—C7—Cl2	119.88 (13)	C10—C15—H15	121.5 (13)
C9—C8—C7	119.00 (15)	C14—C15—H15	118.0 (13)
C9—C8—H8	118.4 (14)

(3N)

Crystal data

C15H10Cl2O	Z = 2
Mr = 277.13	F(000) = 284
Triclinic, P1	Dx = 1.433 Mg m^−3
a = 5.7280 (1) Å	Melting point: 72-73 K
b = 11.3620 (2) Å	Neutron radiation, λ = 0.5-5.0 Å
c = 11.5210 (1) Å	Cell parameters from 25 reflections
α = 117.240 (1)°	µ = 1.45 at 1 angstrom mm^−1
β = 99.250 (1)°	T = 150 K
γ = 96.860 (1)°	Block, colourless
V = 641.87 (2) Å^3	2.5 × 1.5 × 1.0 mm

Data collection

SXD diffractometer	2929 independent reflections
Radiation source: ISIS spallation source	2928 reflections with I > 2σ(I)
None monochromator	Rint = 0.062
time–of–flight LAUE diffraction scans	θmax = 16.2°, θmin = 1.3°
Absorption correction: empirical (using intensity measurements) The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 0.64 + 0.81 * lambda [cm^-1]	h = 0^→12
Tmin = 0.51, Tmax = 0.89	k = ^−20^→21
10674 measured reflections	l = ^−19^→10

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)] = 0.067	Hydrogen site location: difference Fourier map
wR(F^2) = 0.128	All H-atom parameters refined
S = 5.44	w = 1/[σ^2(Fo^2)]
2929 reflections	(Δ/σ)max < 0.001
253 parameters	Extinction correction: Becker-Coppens Lorentzian model
0 restraints	Extinction coefficient: 0.296

Special details

Experimental. For peak integration a local UB matrix refined for each frame, using approximately 25 reflections. Hence _cell_measurement_reflns_used 25

For final cell dimensions an average of all local cells was performed and estimated standard uncertainties were obtained from the spread of the local observations

Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. Instead, we can give values of

cell_measurement_sin(theta)/lambda_min 0.17 cell_measurement_sin(theta)/lambda_max 0.77

The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.5-5.0 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.7-2.5 Angstroms.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given It is also difficult to estimate realistic values of maximum sin(theta)/lambda values for two reasons: (i) Different sin(theta)/lambda ranges are accessed in different parts of the detectors (ii) The nature of the data collection occasionally allows some reflections at very high sin(theta)/lambda to be observed even when no real attempt has been made to measure data in this region. However, we can attempt to estimate the sin(theta)/lambda limits as follows:

diffrn_reflns_sin(theta)/lambda_min 0.087 diffrn_reflns_sin(theta)/lambda_max 1.116

Note also that reflections for which the standard profile fitting integration procedure fails are excluded from the data set, thus resulting in a high elimination rate of very weak or "unobserved" peaks from the final data set.

The extinction coefficient reported in _refine_ls_extinction_coef is in this case the refined value of the mosaic spread in units of 10^{-4 rad}-1 The reference for the extinction method used is: Becker, P. & Coppens, P. (1974). Acta Cryst. A30, 129-148.

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

	x	y	z	Uiso*/Ueq
C1	1.0047 (4)	−0.02661 (18)	0.3033 (2)	0.0333 (5)
C2	0.9559 (3)	0.08311 (16)	0.35113 (19)	0.0223 (4)
C3	0.8984 (3)	0.21786 (15)	0.40894 (17)	0.0187 (3)
O1	1.1102 (4)	0.3181 (2)	0.4452 (3)	0.0268 (5)
C4	0.8194 (3)	0.24703 (14)	0.53838 (16)	0.0171 (3)
C5	0.9649 (3)	0.34106 (16)	0.66423 (18)	0.0236 (4)
C6	0.8860 (4)	0.36646 (17)	0.78000 (19)	0.0269 (4)
C7	0.6603 (3)	0.29618 (17)	0.76792 (18)	0.0236 (4)
Cl1	0.0542 (3)	0.26511 (16)	0.05897 (17)	0.0421 (4)
C8	0.5148 (4)	0.2012 (2)	0.6435 (2)	0.0278 (4)
C9	0.5950 (3)	0.17659 (18)	0.52866 (19)	0.0247 (4)
C10	0.6940 (3)	0.22635 (15)	0.31199 (17)	0.0193 (3)
C11	0.6513 (4)	0.35329 (16)	0.34004 (19)	0.0248 (4)
C12	0.4579 (4)	0.36662 (18)	0.2611 (2)	0.0282 (4)
C13	0.3053 (4)	0.25032 (18)	0.15295 (19)	0.0266 (4)
Cl2	0.5579 (3)	0.32699 (17)	0.91032 (17)	0.0434 (4)
C14	0.3467 (4)	0.12323 (18)	0.1226 (2)	0.0299 (4)
C15	0.5422 (4)	0.11157 (17)	0.20187 (19)	0.0265 (4)
H11	0.7679 (9)	0.4433 (4)	0.4257 (5)	0.0482 (12)
H15	0.5713 (10)	0.0116 (4)	0.1802 (5)	0.0514 (13)
H5	1.1370 (10)	0.3966 (5)	0.6715 (5)	0.0532 (12)
H9	0.4800 (9)	0.1024 (5)	0.4320 (5)	0.0549 (12)
H6	0.9997 (11)	0.4397 (5)	0.8769 (5)	0.0602 (14)
H8	0.3403 (10)	0.1454 (6)	0.6355 (6)	0.0570 (13)
H14	0.2271 (10)	0.0345 (5)	0.0377 (5)	0.0556 (13)
H12	0.4225 (10)	0.4649 (4)	0.2825 (5)	0.0560 (14)
HA	1.1791 (10)	0.2951 (5)	0.3698 (6)	0.0572 (13)
H1	1.0485 (11)	−0.1217 (5)	0.2613 (7)	0.0671 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0287 (11)	0.0237 (8)	0.0470 (13)	0.0100 (8)	0.0121 (9)	0.0148 (8)
C2	0.0192 (9)	0.0190 (7)	0.0289 (9)	0.0048 (6)	0.0085 (7)	0.0108 (7)
C3	0.0153 (8)	0.0174 (6)	0.0221 (8)	0.0006 (6)	0.0049 (6)	0.0090 (6)
O1	0.0202 (11)	0.0236 (9)	0.0343 (13)	−0.0032 (8)	0.0080 (10)	0.0136 (9)
C4	0.0151 (8)	0.0152 (6)	0.0199 (8)	0.0012 (6)	0.0034 (6)	0.0083 (6)
C5	0.0220 (10)	0.0198 (7)	0.0235 (9)	−0.0017 (6)	0.0035 (7)	0.0081 (7)
C6	0.0285 (10)	0.0229 (8)	0.0229 (9)	0.0023 (7)	0.0036 (8)	0.0076 (7)
C7	0.0234 (10)	0.0264 (8)	0.0242 (9)	0.0113 (7)	0.0077 (7)	0.0129 (7)
Cl1	0.0406 (10)	0.0509 (9)	0.0404 (9)	0.0138 (7)	0.0027 (7)	0.0282 (7)
C8	0.0196 (10)	0.0382 (9)	0.0264 (10)	0.0037 (8)	0.0073 (8)	0.0164 (8)
C9	0.0151 (9)	0.0315 (9)	0.0232 (9)	−0.0041 (7)	0.0031 (7)	0.0123 (7)
C10	0.0215 (9)	0.0156 (6)	0.0209 (8)	0.0024 (6)	0.0062 (7)	0.0090 (6)
C11	0.0281 (10)	0.0165 (7)	0.0283 (9)	0.0010 (7)	0.0030 (8)	0.0118 (7)
C12	0.0324 (11)	0.0241 (8)	0.0333 (10)	0.0069 (7)	0.0071 (8)	0.0183 (8)
C13	0.0287 (10)	0.0302 (8)	0.0245 (9)	0.0065 (7)	0.0057 (8)	0.0164 (7)
Cl2	0.0442 (10)	0.0591 (10)	0.0338 (8)	0.0204 (8)	0.0194 (7)	0.0230 (7)
C14	0.0303 (11)	0.0274 (9)	0.0260 (10)	0.0048 (8)	0.0012 (8)	0.0101 (8)
C15	0.0301 (11)	0.0187 (7)	0.0241 (9)	0.0044 (7)	0.0022 (8)	0.0067 (6)
H11	0.051 (3)	0.0268 (17)	0.053 (3)	−0.0004 (17)	−0.002 (2)	0.0147 (18)
H15	0.057 (3)	0.0279 (18)	0.053 (3)	0.0089 (18)	−0.002 (2)	0.0118 (17)
H5	0.042 (3)	0.052 (2)	0.045 (3)	−0.018 (2)	0.003 (2)	0.016 (2)
H9	0.035 (3)	0.071 (3)	0.036 (2)	−0.022 (2)	−0.001 (2)	0.019 (2)
H6	0.063 (4)	0.054 (3)	0.034 (2)	−0.008 (2)	0.001 (2)	0.005 (2)
H8	0.035 (3)	0.079 (3)	0.059 (3)	−0.003 (2)	0.015 (2)	0.038 (3)
H14	0.053 (3)	0.044 (2)	0.044 (3)	0.002 (2)	−0.007 (2)	0.008 (2)
H12	0.063 (3)	0.037 (2)	0.070 (3)	0.015 (2)	0.005 (3)	0.031 (2)
HA	0.052 (3)	0.057 (3)	0.059 (3)	−0.005 (2)	0.032 (3)	0.023 (2)
H1	0.070 (4)	0.039 (2)	0.093 (4)	0.029 (2)	0.029 (3)	0.026 (3)

Geometric parameters (Å, º)

C1—C2	1.200 (2)	Cl1—C13	1.730 (2)
C1—H1	1.044 (4)	C8—C9	1.389 (3)
C2—C3	1.467 (2)	C8—H8	1.084 (6)
C3—O1	1.420 (3)	C9—H9	1.075 (5)
C3—C10	1.528 (2)	C10—C15	1.388 (2)
C3—C4	1.529 (3)	C10—C11	1.388 (2)
O1—HA	0.951 (7)	C11—C12	1.385 (3)
C4—C5	1.385 (2)	C11—H11	1.080 (5)
C4—C9	1.390 (3)	C12—C13	1.389 (3)
C5—C6	1.393 (3)	C12—H12	1.080 (4)
C5—H5	1.074 (6)	C13—C14	1.382 (2)
C6—C7	1.386 (3)	Cl2—Cl1^i	3.394 (2)
C6—H6	1.072 (5)	C14—C15	1.387 (3)
C7—C8	1.378 (3)	C14—H14	1.077 (5)
C7—Cl2	1.729 (3)	C15—H15	1.086 (4)
C2—C1—H1	179.4 (5)	C9—C8—H8	120.3 (4)
C1—C2—C3	179.3 (2)	C8—C9—C4	120.58 (17)
O1—C3—C2	109.59 (16)	C8—C9—H9	118.8 (3)
O1—C3—C10	110.84 (15)	C4—C9—H9	120.6 (3)
C2—C3—C10	111.64 (14)	C15—C10—C11	119.24 (15)
O1—C3—C4	107.04 (16)	C15—C10—C3	122.25 (13)
C2—C3—C4	108.89 (13)	C11—C10—C3	118.41 (14)
C10—C3—C4	108.70 (14)	C12—C11—C10	120.99 (16)
C3—O1—HA	109.4 (4)	C12—C11—H11	119.1 (3)
C5—C4—C9	119.38 (17)	C10—C11—H11	119.9 (3)
C5—C4—C3	121.94 (16)	C11—C12—C13	118.87 (15)
C9—C4—C3	118.69 (15)	C11—C12—H12	121.6 (3)
C4—C5—C6	120.45 (18)	C13—C12—H12	119.6 (3)
C4—C5—H5	119.3 (3)	C14—C13—C12	120.92 (16)
C6—C5—H5	120.2 (3)	C14—C13—Cl1	119.74 (15)
C7—C6—C5	119.22 (17)	C12—C13—Cl1	119.29 (13)
C7—C6—H6	120.9 (4)	C7—Cl2—Cl1^i	93.85 (9)
C5—C6—H6	119.9 (4)	C13—C14—C15	119.54 (17)
C8—C7—C6	120.99 (19)	C13—C14—H14	119.7 (3)
C8—C7—Cl2	119.03 (17)	C15—C14—H14	120.8 (3)
C6—C7—Cl2	119.98 (15)	C14—C15—C10	120.42 (14)
C7—C8—C9	119.38 (19)	C14—C15—H15	119.6 (3)
C7—C8—H8	120.3 (4)	C10—C15—H15	119.9 (3)

Symmetry code: (i) x+1, y, z+1.

(4)

Crystal data

C15H10Br2O	F(000) = 356
Mr = 366.05	Dx = 1.801 Mg m^−3
Triclinic, P1	Melting point: 97 K
a = 5.7906 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.325 (2) Å	Cell parameters from 998 reflections
c = 11.907 (2) Å	θ = 4.3–30.5°
α = 115.67 (3)°	µ = 5.99 mm^−1
β = 99.43 (3)°	T = 150 K
γ = 97.91 (3)°	Block, colourless
V = 674.8 (2) Å^3	0.4 × 0.3 × 0.2 mm
Z = 2

Data collection

Bruker SMART CCD diffractometer	3456 independent reflections
Radiation source: fine-focus sealed tube	2879 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: not relevant pixels mm^-1	θmax = 30.2°, θmin = 2.0°
ω scans	h = −6→8
Absorption correction: empirical (using intensity measurements) (XPREP in SHELX97; Sheldrick, 1997)	k = −15→12
Tmin = 0.344, Tmax = 0.766	l = −15→16
5364 measured reflections

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)] = 0.028	Hydrogen site location: difference Fourier map
wR(F^2) = 0.072	All H-atom parameters refined
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0393P)^2 + 0.1818P] where P = (Fo^2 + 2Fc^2)/3
3456 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.86 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	1.45503 (4)	0.23580 (3)	1.44526 (2)	0.03392 (8)
Br2	0.95564 (5)	0.17469 (3)	0.60197 (2)	0.03739 (8)
O1	0.3788 (3)	0.17949 (17)	1.05754 (17)	0.0280 (3)
C10	0.6726 (4)	0.2554 (2)	0.9690 (2)	0.0208 (4)
C15	0.8996 (4)	0.3258 (2)	0.9790 (2)	0.0250 (4)
C14	0.9833 (4)	0.3029 (2)	0.8698 (2)	0.0263 (4)
C3	0.5921 (4)	0.2826 (2)	1.0935 (2)	0.0222 (4)
C2	0.5352 (4)	0.4170 (2)	1.1473 (2)	0.0243 (4)
C12	0.6082 (4)	0.1394 (2)	0.7376 (2)	0.0260 (4)
C11	0.5266 (4)	0.1636 (2)	0.8476 (2)	0.0242 (4)
C5	0.9410 (4)	0.3879 (2)	1.2966 (2)	0.0283 (5)
C1	0.4884 (4)	0.5239 (3)	1.1907 (3)	0.0314 (5)
C4	0.7950 (4)	0.2749 (2)	1.1894 (2)	0.0220 (4)
C13	0.8365 (4)	0.2090 (2)	0.7505 (2)	0.0247 (4)
C7	1.1801 (4)	0.2507 (2)	1.3444 (2)	0.0261 (4)
C8	1.0325 (4)	0.1356 (2)	1.2387 (2)	0.0274 (4)
C6	1.1362 (4)	0.3768 (2)	1.3750 (2)	0.0297 (5)
C9	0.8406 (4)	0.1481 (2)	1.1613 (2)	0.0263 (4)
H5	0.909 (5)	0.474 (3)	1.312 (3)	0.028 (7)*
H8	1.066 (5)	0.052 (3)	1.219 (3)	0.038 (8)*
H15	0.994 (5)	0.384 (3)	1.057 (3)	0.028 (7)*
H6	1.216 (6)	0.454 (3)	1.441 (3)	0.054 (10)*
H14	1.135 (6)	0.350 (3)	0.878 (3)	0.039 (8)*
H11	0.387 (6)	0.115 (3)	0.834 (3)	0.036 (8)*
H9	0.758 (5)	0.075 (3)	1.094 (3)	0.037 (8)*
H12	0.513 (5)	0.076 (3)	0.654 (3)	0.034 (7)*
H1A	0.327 (6)	0.199 (3)	1.117 (3)	0.047 (10)*
H1	0.434 (7)	0.600 (4)	1.213 (4)	0.064 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.03509 (14)	0.03848 (14)	0.02954 (13)	0.01039 (10)	0.00334 (9)	0.01819 (11)
Br2	0.03590 (14)	0.05276 (17)	0.02461 (12)	0.01797 (11)	0.01266 (9)	0.01505 (11)
O1	0.0243 (8)	0.0249 (8)	0.0304 (9)	−0.0017 (6)	0.0089 (7)	0.0105 (7)
C10	0.0208 (9)	0.0189 (9)	0.0228 (10)	0.0041 (7)	0.0050 (8)	0.0102 (8)
C15	0.0214 (10)	0.0274 (11)	0.0221 (10)	0.0008 (8)	0.0027 (8)	0.0102 (9)
C14	0.0200 (10)	0.0329 (11)	0.0252 (11)	0.0049 (8)	0.0061 (8)	0.0130 (9)
C3	0.0206 (9)	0.0191 (9)	0.0243 (10)	0.0009 (7)	0.0064 (8)	0.0089 (8)
C2	0.0199 (9)	0.0262 (10)	0.0247 (10)	0.0035 (8)	0.0056 (8)	0.0106 (9)
C12	0.0281 (11)	0.0220 (10)	0.0204 (10)	0.0052 (8)	−0.0006 (8)	0.0057 (9)
C11	0.0212 (10)	0.0191 (10)	0.0283 (11)	0.0006 (8)	0.0033 (8)	0.0097 (9)
C5	0.0337 (12)	0.0226 (11)	0.0245 (11)	0.0070 (9)	0.0046 (9)	0.0080 (9)
C1	0.0262 (11)	0.0278 (12)	0.0372 (13)	0.0077 (9)	0.0076 (9)	0.0122 (10)
C4	0.0255 (10)	0.0205 (10)	0.0220 (10)	0.0044 (8)	0.0089 (8)	0.0109 (8)
C13	0.0281 (11)	0.0277 (11)	0.0235 (10)	0.0138 (9)	0.0094 (8)	0.0134 (9)
C7	0.0272 (10)	0.0315 (12)	0.0230 (10)	0.0075 (9)	0.0070 (8)	0.0153 (9)
C8	0.0301 (11)	0.0231 (11)	0.0311 (11)	0.0057 (8)	0.0075 (9)	0.0147 (9)
C6	0.0340 (12)	0.0248 (11)	0.0216 (11)	0.0040 (9)	0.0015 (9)	0.0058 (9)
C9	0.0290 (11)	0.0208 (10)	0.0254 (11)	0.0016 (8)	0.0050 (8)	0.0094 (9)

Geometric parameters (Å, º)

Br1—C7	1.904 (2)	C12—C11	1.393 (3)
Br2—C13	1.906 (2)	C12—H12	0.95 (3)
O1—C3	1.438 (3)	C11—H11	0.86 (3)
O1—H1A	0.76 (3)	C5—C4	1.384 (3)
C10—C11	1.393 (3)	C5—C6	1.400 (3)
C10—C15	1.398 (3)	C5—H5	0.97 (3)
C10—C3	1.543 (3)	C1—H1	0.90 (4)
C15—C14	1.394 (3)	C4—C9	1.401 (3)
C15—H15	0.90 (3)	C7—C6	1.385 (3)
C14—C13	1.385 (3)	C7—C8	1.390 (3)
C14—H14	0.93 (3)	C8—C9	1.387 (3)
C3—C2	1.483 (3)	C8—H8	0.93 (3)
C3—C4	1.538 (3)	C6—H6	0.88 (4)
C2—C1	1.184 (3)	C9—H9	0.86 (3)
C12—C13	1.391 (3)
C3—O1—H1A	107 (3)	C4—C5—C6	120.7 (2)
C11—C10—C15	119.2 (2)	C4—C5—H5	117.6 (17)
C11—C10—C3	122.18 (19)	C6—C5—H5	121.6 (17)
C15—C10—C3	118.60 (19)	C2—C1—H1	172 (3)
C14—C15—C10	121.0 (2)	C5—C4—C9	119.3 (2)
C14—C15—H15	119.6 (18)	C5—C4—C3	122.84 (19)
C10—C15—H15	119.4 (18)	C9—C4—C3	117.7 (2)
C13—C14—C15	118.6 (2)	C14—C13—C12	121.6 (2)
C13—C14—H14	121 (2)	C14—C13—Br2	118.38 (17)
C15—C14—H14	120 (2)	C12—C13—Br2	120.01 (17)
O1—C3—C2	109.93 (18)	C6—C7—C8	121.2 (2)
O1—C3—C4	110.93 (17)	C6—C7—Br1	119.26 (18)
C2—C3—C4	111.32 (18)	C8—C7—Br1	119.49 (17)
O1—C3—C10	106.56 (17)	C9—C8—C7	119.2 (2)
C2—C3—C10	109.10 (17)	C9—C8—H8	120.7 (19)
C4—C3—C10	108.86 (17)	C7—C8—H8	120.1 (19)
C1—C2—C3	179.4 (2)	C7—C6—C5	119.0 (2)
C13—C12—C11	119.1 (2)	C7—C6—H6	127 (2)
C13—C12—H12	118.7 (17)	C5—C6—H6	114 (2)
C11—C12—H12	122.1 (17)	C8—C9—C4	120.5 (2)
C12—C11—C10	120.4 (2)	C8—C9—H9	117 (2)
C12—C11—H11	115 (2)	C4—C9—H9	123 (2)
C10—C11—H11	125 (2)

(5)

Crystal data

C27H20O	F(000) = 380
Mr = 360.43	Dx = 1.235 Mg m^−3
Triclinic, P1	Melting point: 157 K
a = 5.6413 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2599 (5) Å	Cell parameters from 927 reflections
c = 17.3238 (9) Å	θ = 10.2–26.5°
α = 100.450 (2)°	µ = 0.07 mm^−1
β = 97.790 (2)°	T = 150 K
γ = 95.477 (2)°	Plate, colourless
V = 969.51 (9) Å^3	0.4 × 0.25 × 0.1 mm
Z = 2

Data collection

Bruker SMART CCD diffractometer	5270 independent reflections
Radiation source: fine-focus sealed tube	3419 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: not relevant pixels mm^-1	θmax = 30.5°, θmin = 1.2°
ω scans	h = −7→7
Absorption correction: empirical (using intensity measurements) (XPREP in SHELX97; Sheldrick, 1997)	k = −14→13
Tmin = 0.681, Tmax = 0.884	l = −21→23
12424 measured reflections

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)] = 0.076	Hydrogen site location: difference Fourier map
wR(F^2) = 0.234	All H-atom parameters refined
S = 1.04	w = 1/[σ^2(Fo^2) + (0.1193P)^2 + 0.578P] where P = (Fo^2 + 2Fc^2)/3
5270 reflections	(Δ/σ)max < 0.001
322 parameters	Δρmax = 0.50 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)
C1	0.0423 (4)	−0.0743 (3)	0.29797 (15)	0.0354 (5)
H1	−0.037 (6)	−0.155 (3)	0.2918 (18)	0.049 (8)*
C2	0.1443 (4)	0.0348 (2)	0.30668 (13)	0.0297 (5)
C3	0.2633 (4)	0.1735 (2)	0.31647 (13)	0.0277 (4)
O1	0.0883 (3)	0.26591 (16)	0.32794 (10)	0.0326 (4)
H1A	−0.003 (8)	0.238 (4)	0.360 (3)	0.096 (14)*
C4	0.3638 (4)	0.1901 (2)	0.24024 (13)	0.0275 (4)
C5	0.2812 (6)	0.2778 (3)	0.19456 (17)	0.0510 (8)
H5	0.149 (7)	0.331 (4)	0.211 (2)	0.085 (12)*
C6	0.3804 (7)	0.2913 (4)	0.12649 (19)	0.0662 (10)
H6	0.294 (8)	0.355 (4)	0.093 (3)	0.098 (14)*
C7	0.5632 (4)	0.2191 (2)	0.10295 (15)	0.0387 (5)*
C8	0.6933 (12)	0.2569 (7)	0.0337 (4)	0.0444 (16)*	0.50
C9	0.7488 (13)	0.1532 (8)	−0.0184 (4)	0.0479 (17)*	0.50
C11	0.8695 (17)	0.1854 (10)	−0.0857 (6)	0.070 (2)*	0.50
C10	0.9392 (17)	0.3032 (10)	−0.0909 (6)	0.079 (2)*	0.50
C12	0.9046 (16)	0.4169 (8)	−0.0341 (5)	0.076 (2)*	0.50
C13	0.7765 (13)	0.3910 (7)	0.0277 (4)	0.0614 (16)*	0.50
C8A	0.6508 (10)	0.2181 (6)	0.0279 (3)	0.0345 (13)*	0.50
C9A	0.8893 (16)	0.1860 (9)	0.0183 (5)	0.0309 (18)*	0.25
C10A	0.984 (2)	0.1971 (11)	−0.0516 (7)	0.045 (2)*	0.25
C11A	0.776 (3)	0.2539 (14)	−0.1172 (8)	0.051 (4)*	0.25
C12A	0.595 (2)	0.2654 (12)	−0.1054 (7)	0.051 (3)*	0.25
C13A	0.5090 (19)	0.2510 (11)	−0.0363 (7)	0.042 (2)*	0.25
C9B	0.755 (2)	0.1131 (15)	−0.0142 (9)	0.047 (3)*	0.25
C10B	0.8428 (18)	0.1373 (12)	−0.0838 (6)	0.032 (2)*	0.25
C11B	0.857 (2)	0.2489 (10)	−0.1105 (6)	0.0241 (19)*	0.25
C12B	0.758 (2)	0.3675 (13)	−0.0672 (8)	0.054 (3)*	0.25
C13B	0.654 (2)	0.3512 (11)	−0.0001 (7)	0.044 (2)*	0.25
C14	0.6400 (5)	0.1299 (3)	0.14867 (16)	0.0410 (6)
H14	0.770 (6)	0.076 (3)	0.134 (2)	0.064 (10)*
C15	0.5424 (5)	0.1155 (3)	0.21671 (17)	0.0418 (6)
H15	0.594 (5)	0.052 (3)	0.2491 (19)	0.051 (8)*
C16	0.4697 (4)	0.2080 (2)	0.38763 (13)	0.0265 (4)
C17	0.5842 (4)	0.1103 (2)	0.41913 (14)	0.0302 (5)
H17	0.528 (5)	0.014 (3)	0.3960 (16)	0.034 (7)*
C18	0.7747 (4)	0.1467 (2)	0.48245 (14)	0.0291 (5)
H18	0.844 (5)	0.079 (3)	0.5071 (16)	0.033 (6)*
C19	0.8535 (3)	0.2812 (2)	0.51612 (12)	0.0248 (4)
C20	1.0514 (3)	0.3190 (2)	0.58493 (12)	0.0247 (4)
C21	1.2571 (4)	0.2522 (2)	0.58795 (14)	0.0287 (5)
H21	1.280 (4)	0.184 (3)	0.5441 (16)	0.030 (6)*
C22	1.4380 (4)	0.2851 (2)	0.65346 (15)	0.0342 (5)
H22	1.568 (5)	0.238 (3)	0.6546 (18)	0.047 (8)*
C23	1.4181 (5)	0.3860 (3)	0.71682 (16)	0.0414 (6)
H23	1.546 (6)	0.409 (3)	0.761 (2)	0.063 (10)*
C24	1.2180 (4)	0.4552 (3)	0.71411 (15)	0.0385 (6)
H24	1.204 (5)	0.529 (3)	0.7583 (19)	0.049 (8)*
C25	1.0358 (4)	0.4217 (2)	0.64876 (14)	0.0299 (5)
H25	0.895 (5)	0.470 (2)	0.6447 (15)	0.032 (6)*
C26	0.7358 (4)	0.3784 (2)	0.48418 (13)	0.0262 (4)
H26	0.789 (5)	0.472 (3)	0.5058 (16)	0.032 (6)*
C27	0.5500 (4)	0.3425 (2)	0.42013 (13)	0.0272 (4)
H27	0.480 (4)	0.413 (2)	0.3993 (15)	0.029 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0339 (12)	0.0358 (13)	0.0369 (13)	0.0007 (9)	0.0085 (9)	0.0081 (10)
C2	0.0264 (10)	0.0353 (12)	0.0279 (11)	0.0050 (8)	0.0066 (8)	0.0052 (9)
C3	0.0245 (9)	0.0285 (10)	0.0301 (11)	0.0059 (7)	0.0052 (8)	0.0041 (8)
O1	0.0271 (8)	0.0353 (9)	0.0371 (9)	0.0112 (6)	0.0084 (7)	0.0056 (7)
C4	0.0241 (9)	0.0288 (10)	0.0266 (10)	0.0010 (7)	0.0016 (8)	0.0008 (8)
C5	0.0592 (17)	0.0696 (19)	0.0394 (15)	0.0392 (15)	0.0208 (13)	0.0244 (14)
C6	0.079 (2)	0.096 (3)	0.0475 (18)	0.055 (2)	0.0288 (16)	0.0400 (18)
C14	0.0375 (12)	0.0429 (14)	0.0463 (15)	0.0099 (10)	0.0192 (11)	0.0066 (11)
C15	0.0414 (13)	0.0413 (14)	0.0526 (16)	0.0166 (11)	0.0213 (12)	0.0185 (12)
C16	0.0245 (9)	0.0287 (10)	0.0268 (10)	0.0046 (7)	0.0068 (8)	0.0038 (8)
C17	0.0309 (10)	0.0238 (10)	0.0356 (12)	0.0064 (8)	0.0055 (9)	0.0028 (8)
C18	0.0302 (10)	0.0250 (10)	0.0332 (11)	0.0089 (8)	0.0047 (8)	0.0058 (8)
C19	0.0238 (9)	0.0265 (10)	0.0257 (10)	0.0035 (7)	0.0080 (7)	0.0060 (8)
C20	0.0231 (9)	0.0269 (10)	0.0264 (10)	0.0030 (7)	0.0073 (7)	0.0092 (8)
C21	0.0271 (10)	0.0305 (11)	0.0308 (11)	0.0057 (8)	0.0094 (8)	0.0073 (9)
C22	0.0265 (10)	0.0387 (12)	0.0403 (13)	0.0080 (9)	0.0061 (9)	0.0124 (10)
C23	0.0334 (12)	0.0521 (15)	0.0345 (13)	0.0078 (10)	−0.0038 (10)	0.0030 (11)
C24	0.0372 (12)	0.0439 (14)	0.0309 (12)	0.0080 (10)	0.0029 (9)	−0.0010 (10)
C25	0.0271 (10)	0.0324 (11)	0.0317 (11)	0.0062 (8)	0.0075 (8)	0.0066 (9)
C26	0.0279 (10)	0.0226 (10)	0.0293 (11)	0.0035 (7)	0.0079 (8)	0.0051 (8)
C27	0.0288 (10)	0.0263 (10)	0.0286 (11)	0.0061 (8)	0.0066 (8)	0.0076 (8)

Geometric parameters (Å, º)

C1—C2	1.182 (3)	C9A—C10A	1.406 (15)
C1—H1	0.89 (3)	C10A—C11A	1.74 (2)
C2—C3	1.485 (3)	C11A—C12A	1.078 (18)
C3—O1	1.441 (2)	C12A—C13A	1.380 (16)
C3—C4	1.536 (3)	C9B—C10B	1.418 (18)
C3—C16	1.541 (3)	C10B—C11B	1.309 (15)
O1—H1A	0.87 (5)	C11B—C12B	1.507 (16)
C4—C5	1.375 (3)	C12B—C13B	1.399 (17)
C4—C15	1.383 (3)	C14—C15	1.392 (4)
C5—C6	1.395 (4)	C14—H14	0.99 (3)
C5—H5	1.01 (4)	C15—H15	0.97 (3)
C6—C7	1.388 (4)	C16—C17	1.396 (3)
C6—H6	1.06 (4)	C16—C27	1.398 (3)
C7—C14	1.378 (4)	C17—C18	1.397 (3)
C7—C8A	1.451 (6)	C17—H17	1.00 (3)
C7—C8	1.576 (7)	C18—C19	1.401 (3)
C8—C13B	1.240 (13)	C18—H18	0.96 (3)
C8—C9	1.356 (10)	C19—C26	1.403 (3)
C8—C9A	1.409 (11)	C19—C20	1.485 (3)
C8—C13	1.436 (10)	C20—C25	1.401 (3)
C8—C13A	1.474 (12)	C20—C21	1.403 (3)
C8—C9B	1.649 (16)	C21—C22	1.387 (3)
C9—C8A	1.179 (9)	C21—H21	0.97 (3)
C9—C11	1.498 (12)	C22—C23	1.390 (4)
C11—C10	1.257 (14)	C22—H22	0.92 (3)
C10—C12	1.431 (12)	C23—C24	1.390 (3)
C12—C13	1.419 (11)	C23—H23	0.96 (3)
C12—C12^i	2.009 (18)	C24—C25	1.390 (3)
C13—C8A	1.847 (10)	C24—H24	0.99 (3)
C8A—C13A	1.391 (12)	C25—H25	0.98 (3)
C8A—C9B	1.410 (16)	C26—C27	1.389 (3)
C8A—C9A	1.439 (10)	C26—H26	0.97 (3)
C8A—C13B	1.529 (13)	C27—H27	0.96 (2)
C2—C1—H1	179 (2)	C9A—C8A—C13B	100.9 (7)
C1—C2—C3	177.7 (2)	C7—C8A—C13B	114.5 (6)
O1—C3—C2	109.60 (17)	C9—C8A—C13	103.2 (6)
O1—C3—C4	107.55 (17)	C13A—C8A—C13	76.2 (6)
C2—C3—C4	109.28 (18)	C9B—C8A—C13	117.8 (7)
O1—C3—C16	109.25 (16)	C9A—C8A—C13	84.9 (5)
C2—C3—C16	111.68 (18)	C7—C8A—C13	107.3 (4)
C4—C3—C16	109.38 (16)	C13B—C8A—C13	25.7 (4)
C3—O1—H1A	107 (3)	C10A—C9A—C8	117.0 (8)
C5—C4—C15	118.8 (2)	C10A—C9A—C8A	121.1 (8)
C5—C4—C3	121.7 (2)	C8—C9A—C8A	17.4 (3)
C15—C4—C3	119.5 (2)	C9A—C10A—C11A	110.2 (9)
C4—C5—C6	119.8 (2)	C12A—C11A—C10A	121.6 (13)
C4—C5—H5	119 (2)	C11A—C12A—C13A	125.9 (14)
C6—C5—H5	121 (2)	C12A—C13A—C8A	122.6 (9)
C7—C6—C5	122.1 (3)	C12A—C13A—C8	115.8 (9)
C7—C6—H6	124 (2)	C8A—C13A—C8	17.1 (4)
C5—C6—H6	114 (2)	C8A—C9B—C10B	116.2 (12)
C14—C7—C6	117.2 (2)	C8A—C9B—C8	13.6 (4)
C14—C7—C8A	118.5 (3)	C10B—C9B—C8	107.3 (11)
C6—C7—C8A	123.7 (3)	C11B—C10B—C9B	128.0 (11)
C14—C7—C8	123.6 (3)	C10B—C11B—C12B	119.0 (9)
C6—C7—C8	118.6 (3)	C13B—C12B—C11B	117.3 (11)
C8A—C7—C8	15.8 (3)	C8—C13B—C12B	121.1 (10)
C13B—C8—C9	110.1 (8)	C8—C13B—C8A	13.4 (4)
C13B—C8—C9A	119.4 (8)	C12B—C13B—C8A	120.1 (9)
C9—C8—C9A	39.6 (5)	C7—C14—C15	121.3 (2)
C13B—C8—C13	34.3 (6)	C7—C14—H14	120 (2)
C9—C8—C13	119.2 (7)	C15—C14—H14	119 (2)
C9A—C8—C13	103.8 (6)	C4—C15—C14	120.8 (2)
C13B—C8—C13A	54.5 (7)	C4—C15—H15	117.1 (19)
C9—C8—C13A	78.1 (6)	C14—C15—H15	122.1 (19)
C9A—C8—C13A	114.7 (7)	C17—C16—C27	118.86 (19)
C13—C8—C13A	88.5 (6)	C17—C16—C3	122.48 (19)
C13B—C8—C7	125.4 (7)	C27—C16—C3	118.63 (18)
C9—C8—C7	116.0 (6)	C16—C17—C18	120.3 (2)
C9A—C8—C7	114.6 (6)	C16—C17—H17	119.2 (15)
C13—C8—C7	124.5 (6)	C18—C17—H17	120.4 (15)
C13A—C8—C7	108.4 (6)	C17—C18—C19	121.09 (19)
C13B—C8—C9B	122.2 (9)	C17—C18—H18	120.2 (15)
C9—C8—C9B	12.3 (6)	C19—C18—H18	118.5 (15)
C9A—C8—C9B	38.7 (6)	C18—C19—C26	117.96 (19)
C13—C8—C9B	130.0 (7)	C18—C19—C20	120.75 (18)
C13A—C8—C9B	85.3 (7)	C26—C19—C20	121.27 (18)
C7—C8—C9B	104.4 (7)	C25—C20—C21	118.40 (19)
C8A—C9—C8	18.0 (4)	C25—C20—C19	120.66 (18)
C8A—C9—C11	132.2 (8)	C21—C20—C19	120.94 (19)
C8—C9—C11	117.4 (7)	C22—C21—C20	120.7 (2)
C10—C11—C9	122.5 (8)	C22—C21—H21	117.7 (15)
C11—C10—C12	122.7 (9)	C20—C21—H21	121.6 (15)
C13—C12—C10	116.5 (8)	C21—C22—C23	120.2 (2)
C13—C12—C12^i	92.8 (7)	C21—C22—H22	118.8 (19)
C10—C12—C12^i	139.5 (9)	C23—C22—H22	121.0 (19)
C12—C13—C8	121.3 (7)	C22—C23—C24	119.9 (2)
C12—C13—C8A	119.6 (6)	C22—C23—H23	119 (2)
C8—C13—C8A	4.8 (4)	C24—C23—H23	121 (2)
C9—C8A—C13A	87.6 (7)	C25—C24—C23	120.0 (2)
C9—C8A—C9B	16.4 (7)	C25—C24—H24	119.4 (17)
C13A—C8A—C9B	98.4 (8)	C23—C24—H24	120.7 (17)
C9—C8A—C9A	40.5 (5)	C24—C25—C20	120.8 (2)
C13A—C8A—C9A	118.1 (7)	C24—C25—H25	121.6 (15)
C9B—C8A—C9A	42.7 (7)	C20—C25—H25	117.5 (15)
C9—C8A—C7	142.1 (6)	C27—C26—C19	121.04 (19)
C13A—C8A—C7	121.0 (6)	C27—C26—H26	119.4 (15)
C9B—C8A—C7	125.9 (7)	C19—C26—H26	119.5 (15)
C9A—C8A—C7	120.9 (5)	C26—C27—C16	120.68 (19)
C9—C8A—C13B	102.8 (7)	C26—C27—H27	117.4 (15)
C13A—C8A—C13B	50.9 (6)	C16—C27—H27	121.9 (15)
C9B—C8A—C13B	119.2 (9)

Symmetry code: (i) −x+2, −y+1, −z.