Supporting information
Crystallographic Information File (CIF) | |
Structure factor file (CIF format) |
CCDC reference: 136449
Data collection: Recentering 2T/T (Operations Manual SYTENX P21; Cupertino, 1973); cell refinement: Least-Squares Orientation Matrix Program (Cupertino, 1973); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: SHELXL93 (Sheldrick, 1993).
C13H8Cl2O | F(000) = 512 |
Mr = 251.09 | Dx = 1.527 Mg m−3 |
Monoclinic, I2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 24.527 (6) Å | Cell parameters from 15 reflections |
b = 6.064 (1) Å | θ = 15–16° |
c = 7.457 (4) Å | µ = 0.57 mm−1 |
β = 100.10 (2)° | T = 164 K |
V = 1091.9 (7) Å3 | Plate, transparent |
Z = 4 | 0.50 × 0.50 × 0.30 mm |
SYNTEX P21 diffractometer | Rint = 0.116 |
Radiation source: fine-focus sealed tube | θmax = 25.1°, θmin = 3.4° |
Graphite monochromator | h = 0→29 |
ω–2θ scans | k = −1→7 |
1025 measured reflections | l = −8→8 |
945 independent reflections | 3 standard reflections every 97 reflections |
842 reflections with F > 4σ(F) | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | Isotropic |
wR(F2) = 0.145 | Calculated w = 1/[σ2(Fo2) + (0.0457P)2 + 2.5539P] where P = (Fo2 + 2Fc2)/3 |
S = 1.19 | (Δ/σ)max < 0.001 |
898 reflections | Δρmax = 0.33 e Å−3 |
91 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL93 (Sheldrick, 1993), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0040 (13) |
C13H8Cl2O | V = 1091.9 (7) Å3 |
Mr = 251.09 | Z = 4 |
Monoclinic, I2/c | Mo Kα radiation |
a = 24.527 (6) Å | µ = 0.57 mm−1 |
b = 6.064 (1) Å | T = 164 K |
c = 7.457 (4) Å | 0.50 × 0.50 × 0.30 mm |
β = 100.10 (2)° |
SYNTEX P21 diffractometer | Rint = 0.116 |
1025 measured reflections | 3 standard reflections every 97 reflections |
945 independent reflections | intensity decay: none |
842 reflections with F > 4σ(F) |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.145 | Isotropic |
S = 1.19 | Δρmax = 0.33 e Å−3 |
898 reflections | Δρmin = −0.32 e Å−3 |
91 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement on F2 for ALL reflections except for 47 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterio of F2 > 2sigma(F2) is used only for calculating _R_factor_obs etc. and 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 | ||
Cl | 0.21473 (3) | 0.50763 (12) | 0.79785 (10) | 0.0386 (3) | |
C1 | 0.05324 (10) | 0.1400 (4) | 0.7610 (3) | 0.0215 (6) | |
C2 | 0.05524 (11) | 0.3485 (4) | 0.6832 (3) | 0.0232 (6) | |
C3 | 0.10497 (11) | 0.4589 (4) | 0.6909 (3) | 0.0256 (6) | |
C4 | 0.15300 (11) | 0.3594 (4) | 0.7796 (3) | 0.0254 (6) | |
C5 | 0.15266 (11) | 0.1522 (5) | 0.8563 (3) | 0.0268 (6) | |
C6 | 0.10284 (11) | 0.0428 (4) | 0.8460 (3) | 0.0245 (6) | |
C7 | 0.0000 | 0.0162 (5) | 0.7500 | 0.0236 (8) | |
O | 0.0000 | −0.1838 (4) | 0.7500 | 0.0389 (8) | |
H2 | 0.0227 (12) | 0.416 (5) | 0.621 (4) | 0.028 (7)* | |
H3 | 0.1061 (12) | 0.590 (5) | 0.640 (4) | 0.028 (7)* | |
H5 | 0.1866 (13) | 0.103 (5) | 0.921 (4) | 0.034 (8)* | |
H6 | 0.1003 (12) | −0.103 (6) | 0.901 (4) | 0.033 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.0284 (5) | 0.0454 (5) | 0.0419 (5) | −0.0131 (3) | 0.0055 (3) | 0.0010 (3) |
C1 | 0.0225 (13) | 0.0191 (12) | 0.0230 (12) | 0.0018 (9) | 0.0044 (10) | −0.0022 (9) |
C2 | 0.0256 (13) | 0.0206 (13) | 0.0227 (13) | 0.0018 (10) | 0.0024 (10) | −0.0009 (10) |
C3 | 0.0325 (15) | 0.0194 (13) | 0.0258 (13) | −0.0043 (11) | 0.0074 (10) | 0.0001 (10) |
C4 | 0.0258 (13) | 0.0272 (13) | 0.0237 (13) | −0.0066 (11) | 0.0061 (10) | −0.0058 (10) |
C5 | 0.0221 (13) | 0.0312 (14) | 0.0261 (13) | 0.0056 (11) | 0.0018 (11) | 0.0033 (11) |
C6 | 0.0282 (14) | 0.0212 (13) | 0.0238 (12) | 0.0035 (10) | 0.0037 (10) | 0.0045 (10) |
C7 | 0.027 (2) | 0.016 (2) | 0.026 (2) | 0.000 | 0.0015 (15) | 0.000 |
O | 0.0308 (15) | 0.0150 (13) | 0.068 (2) | 0.000 | 0.0017 (14) | 0.000 |
Cl—C4 | 1.746 (3) | C3—H3 | 0.88 (3) |
C1—C2 | 1.396 (4) | C4—C5 | 1.381 (4) |
C1—C6 | 1.400 (3) | C5—C6 | 1.381 (4) |
C1—C7 | 1.496 (3) | C5—H5 | 0.93 (3) |
C2—C3 | 1.384 (4) | C6—H6 | 0.98 (3) |
C2—H2 | 0.94 (3) | C7—O | 1.213 (4) |
C3—C4 | 1.384 (4) | C7—C1i | 1.496 (3) |
C2—C1—C6 | 118.6 (2) | C3—C4—Cl | 117.8 (2) |
C2—C1—C7 | 121.7 (2) | C6—C5—C4 | 118.9 (2) |
C6—C1—C7 | 119.6 (2) | C6—C5—H5 | 125 (2) |
C3—C2—C1 | 121.1 (2) | C4—C5—H5 | 116 (2) |
C3—C2—H2 | 118.2 (19) | C5—C6—C1 | 120.9 (2) |
C1—C2—H2 | 120.7 (19) | C5—C6—H6 | 122.0 (17) |
C2—C3—C4 | 118.6 (2) | C1—C6—H6 | 117.1 (17) |
C2—C3—H3 | 120.7 (19) | O—C7—C1 | 120.11 (14) |
C4—C3—H3 | 120.6 (19) | O—C7—C1i | 120.11 (15) |
C5—C4—C3 | 121.9 (2) | C1—C7—C1i | 119.8 (3) |
C5—C4—Cl | 120.3 (2) | ||
C6—C1—C2—C3 | −0.6 (4) | C4—C5—C6—C1 | −0.6 (4) |
C7—C1—C2—C3 | −178.5 (2) | C2—C1—C6—C5 | 1.3 (4) |
C1—C2—C3—C4 | −0.8 (4) | C7—C1—C6—C5 | 179.3 (2) |
C2—C3—C4—C5 | 1.5 (4) | C2—C1—C7—O | 150.8 (2) |
C2—C3—C4—Cl | −176.7 (2) | C6—C1—C7—O | −27.1 (2) |
C3—C4—C5—C6 | −0.8 (4) | C2—C1—C7—C1i | −29.2 (2) |
Cl—C4—C5—C6 | 177.4 (2) | C6—C1—C7—C1i | 152.9 (2) |
Symmetry code: (i) −x, y, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C13H8Cl2O |
Mr | 251.09 |
Crystal system, space group | Monoclinic, I2/c |
Temperature (K) | 164 |
a, b, c (Å) | 24.527 (6), 6.064 (1), 7.457 (4) |
β (°) | 100.10 (2) |
V (Å3) | 1091.9 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.57 |
Crystal size (mm) | 0.50 × 0.50 × 0.30 |
Data collection | |
Diffractometer | SYNTEX P21 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [F > 4σ(F)] reflections | 1025, 945, 842 |
Rint | 0.116 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.145, 1.19 |
No. of reflections | 898 |
No. of parameters | 91 |
H-atom treatment | Isotropic |
Δρmax, Δρmin (e Å−3) | 0.33, −0.32 |
Computer programs: Recentering 2T/T (Operations Manual SYTENX P21; Cupertino, 1973), Least-Squares Orientation Matrix Program (Cupertino, 1973), SHELXS86 (Sheldrick, 1990), SHELXL93 (Sheldrick, 1993).