Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810001154X/bm0034sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810001154X/bm00342sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810001154X/bm00343Xsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810001154X/bm00343Nsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810001154X/bm00344sup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010876810001154X/bm00345sup6.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S010876810001154X/bm0034sup7.pdf |
CCDC references: 156670; 156671; 156672; 156673; 156674
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).
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) Å3 | 0.3 × 0.3 × 0.2 mm |
Z = 2 |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.132 | All H-atom parameters refined |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0618P)2 + 0.2678P] where P = (Fo2 + 2Fc2)/3 |
2964 reflections | (Δ/σ)max = 0.028 |
231 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C17H16O | γ = 101.39 (3)° |
Mr = 236.30 | V = 652.0 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.8286 (14) Å | Mo Kα radiation |
b = 8.2407 (16) Å | µ = 0.07 mm−1 |
c = 12.658 (3) Å | T = 150 K |
α = 106.73 (3)° | 0.3 × 0.3 × 0.2 mm |
β = 98.71 (3)° |
Bruker SMART CCD diffractometer | 2964 independent reflections |
Absorption correction: multi-scan SADABS (Sheldrick 1996) | 2362 reflections with I > 2σ(I) |
Tmin = 0.784, Tmax = 1.000 | Rint = 0.018 |
4775 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.132 | All H-atom parameters refined |
S = 1.03 | Δρmax = 0.21 e Å−3 |
2964 reflections | Δρmin = −0.20 e Å−3 |
231 parameters |
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. |
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)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—HA···C11i | 0.85 (3) | 3.07 (3) | 3.860 (2) | 155 (2) |
O1—HA···C13i | 0.85 (3) | 2.85 (3) | 3.644 (2) | 156 (2) |
O1—HA···C16i | 0.85 (3) | 2.61 (3) | 3.288 (2) | 137 (2) |
Symmetry code: (i) −x+1, −y, −z. |
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) Å3 | 0.5 × 0.4 × 0.4 mm |
Z = 2 |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0467P)2 + 0.3533P] where P = (Fo2 + 2Fc2)/3 |
2826 reflections | (Δ/σ)max < 0.001 |
203 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
C15H10Cl2O | γ = 96.726 (1)° |
Mr = 277.13 | V = 639.73 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.7082 (1) Å | Mo Kα radiation |
b = 11.3645 (2) Å | µ = 0.49 mm−1 |
c = 11.5167 (1) Å | T = 150 K |
α = 117.268 (1)° | 0.5 × 0.4 × 0.4 mm |
β = 99.257 (1)° |
Bruker SMART CCD diffractometer | 2826 independent reflections |
Absorption correction: multi-scan SADABS (Sheldrick 1996) | 2617 reflections with I > 2σ(I) |
Tmin = 0.284, Tmax = 0.332 | Rint = 0.043 |
4371 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.33 e Å−3 |
2826 reflections | Δρmin = −0.35 e Å−3 |
203 parameters |
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. |
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)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | 2.5 × 1.5 × 1.0 mm |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.067 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.128 | All H-atom parameters refined |
S = 5.44 | w = 1/[σ2(Fo2)] |
2929 reflections | (Δ/σ)max < 0.001 |
253 parameters | Extinction correction: Becker-Coppens Lorentzian model |
0 restraints | Extinction coefficient: 0.296 |
C15H10Cl2O | γ = 96.860 (1)° |
Mr = 277.13 | V = 641.87 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.7280 (1) Å | Neutron radiation, λ = 0.5-5.0 Å |
b = 11.3620 (2) Å | µ = 1.45 at 1 angstrom mm−1 |
c = 11.5210 (1) Å | T = 150 K |
α = 117.240 (1)° | 2.5 × 1.5 × 1.0 mm |
β = 99.250 (1)° |
SXD diffractometer | 2929 independent reflections |
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] | 2928 reflections with I > 2σ(I) |
Tmin = 0.51, Tmax = 0.89 | Rint = 0.062 |
10674 measured reflections |
R[F2 > 2σ(F2)] = 0.067 | 253 parameters |
wR(F2) = 0.128 | 0 restraints |
S = 5.44 | All H-atom parameters refined |
2929 reflections |
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. |
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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—Cl1i | 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—Cl1i | 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. |
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) Å3 | 0.4 × 0.3 × 0.2 mm |
Z = 2 |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.028 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.072 | All H-atom parameters refined |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0393P)2 + 0.1818P] where P = (Fo2 + 2Fc2)/3 |
3456 reflections | (Δ/σ)max = 0.001 |
203 parameters | Δρmax = 0.86 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
C15H10Br2O | γ = 97.91 (3)° |
Mr = 366.05 | V = 674.8 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.7906 (12) Å | Mo Kα radiation |
b = 11.325 (2) Å | µ = 5.99 mm−1 |
c = 11.907 (2) Å | T = 150 K |
α = 115.67 (3)° | 0.4 × 0.3 × 0.2 mm |
β = 99.43 (3)° |
Bruker SMART CCD diffractometer | 3456 independent reflections |
Absorption correction: empirical (using intensity measurements) (XPREP in SHELX97; Sheldrick, 1997) | 2879 reflections with I > 2σ(I) |
Tmin = 0.344, Tmax = 0.766 | Rint = 0.029 |
5364 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.072 | All H-atom parameters refined |
S = 1.07 | Δρmax = 0.86 e Å−3 |
3456 reflections | Δρmin = −0.43 e Å−3 |
203 parameters |
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. |
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)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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) Å3 | 0.4 × 0.25 × 0.1 mm |
Z = 2 |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.076 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.234 | All H-atom parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.1193P)2 + 0.578P] where P = (Fo2 + 2Fc2)/3 |
5270 reflections | (Δ/σ)max < 0.001 |
322 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
C27H20O | γ = 95.477 (2)° |
Mr = 360.43 | V = 969.51 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.6413 (3) Å | Mo Kα radiation |
b = 10.2599 (5) Å | µ = 0.07 mm−1 |
c = 17.3238 (9) Å | T = 150 K |
α = 100.450 (2)° | 0.4 × 0.25 × 0.1 mm |
β = 97.790 (2)° |
Bruker SMART CCD diffractometer | 5270 independent reflections |
Absorption correction: empirical (using intensity measurements) (XPREP in SHELX97; Sheldrick, 1997) | 3419 reflections with I > 2σ(I) |
Tmin = 0.681, Tmax = 0.884 | Rint = 0.043 |
12424 measured reflections |
R[F2 > 2σ(F2)] = 0.076 | 0 restraints |
wR(F2) = 0.234 | All H-atom parameters refined |
S = 1.04 | Δρmax = 0.50 e Å−3 |
5270 reflections | Δρmin = −0.43 e Å−3 |
322 parameters |
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. |
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)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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—C12i | 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—C12i | 92.8 (7) | C21—C22—H22 | 118.8 (19) |
C10—C12—C12i | 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. |
Experimental details
(2) | (3X) | (3N) | (4) | |
Crystal data | ||||
Chemical formula | C17H16O | C15H10Cl2O | C15H10Cl2O | C15H10Br2O |
Mr | 236.30 | 277.13 | 277.13 | 366.05 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 150 | 150 | 150 | 150 |
a, b, c (Å) | 6.8286 (14), 8.2407 (16), 12.658 (3) | 5.7082 (1), 11.3645 (2), 11.5167 (1) | 5.7280 (1), 11.3620 (2), 11.5210 (1) | 5.7906 (12), 11.325 (2), 11.907 (2) |
α, β, γ (°) | 106.73 (3), 98.71 (3), 101.39 (3) | 117.268 (1), 99.257 (1), 96.726 (1) | 117.240 (1), 99.250 (1), 96.860 (1) | 115.67 (3), 99.43 (3), 97.91 (3) |
V (Å3) | 652.0 (2) | 639.73 (2) | 641.87 (2) | 674.8 (2) |
Z | 2 | 2 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Neutron, λ = 0.5-5.0 Å | Mo Kα |
µ (mm−1) | 0.07 | 0.49 | 1.45 at 1 angstrom | 5.99 |
Crystal size (mm) | 0.3 × 0.3 × 0.2 | 0.5 × 0.4 × 0.4 | 2.5 × 1.5 × 1.0 | 0.4 × 0.3 × 0.2 |
Data collection | ||||
Diffractometer | Bruker SMART CCD | Bruker SMART CCD | SXD | Bruker SMART CCD |
Absorption correction | Multi-scan SADABS (Sheldrick 1996) | Multi-scan SADABS (Sheldrick 1996) | Empirical (using intensity measurements) The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 0.64 + 0.81 * lambda [cm-1] | Empirical (using intensity measurements) (XPREP in SHELX97; Sheldrick, 1997) |
Tmin, Tmax | 0.784, 1.000 | 0.284, 0.332 | 0.51, 0.89 | 0.344, 0.766 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4775, 2964, 2362 | 4371, 2826, 2617 | 10674, 2929, 2928 | 5364, 3456, 2879 |
Rint | 0.018 | 0.043 | 0.062 | 0.029 |
(sin θ/λ)max (Å−1) | 0.649 | 0.646 | – | 0.707 |
Distance from specimen to detector (mm) | – | – | h = 0→12, k = −20→21, l = −19→10 | – |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.132, 1.03 | 0.038, 0.104, 1.11 | 0.067, 0.128, 5.44 | 0.028, 0.072, 1.07 |
No. of reflections | 2964 | 2826 | 2929 | 3456 |
No. of parameters | 231 | 203 | 253 | 203 |
H-atom treatment | All H-atom parameters refined | H atoms treated by a mixture of independent and constrained refinement | All H-atom parameters refined | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.21, −0.20 | 0.33, −0.35 | ?, ? | 0.86, −0.43 |
(5) | |
Crystal data | |
Chemical formula | C27H20O |
Mr | 360.43 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 5.6413 (3), 10.2599 (5), 17.3238 (9) |
α, β, γ (°) | 100.450 (2), 97.790 (2), 95.477 (2) |
V (Å3) | 969.51 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.4 × 0.25 × 0.1 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Empirical (using intensity measurements) (XPREP in SHELX97; Sheldrick, 1997) |
Tmin, Tmax | 0.681, 0.884 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12424, 5270, 3419 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.713 |
Distance from specimen to detector (mm) | – |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.076, 0.234, 1.04 |
No. of reflections | 5270 |
No. of parameters | 322 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.50, −0.43 |
Computer programs: Bruker SMART (Bruker Systems Inc., 1999a), SXD (Keen & Wilson, 1996), Bruker SAINT (Bruker Systems Inc., 1999b), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—HA···C11i | 0.85 (3) | 3.07 (3) | 3.860 (2) | 155 (2) |
O1—HA···C13i | 0.85 (3) | 2.85 (3) | 3.644 (2) | 156 (2) |
O1—HA···C16i | 0.85 (3) | 2.61 (3) | 3.288 (2) | 137 (2) |
Symmetry code: (i) −x+1, −y, −z. |