Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001904/na6290sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001904/na62902sup2.hkl |
CCDC reference: 236069
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.097
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 28.02 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 2590 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2728 Completeness (_total/calc) 94.94% PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C14 H13 Cl
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999) and SHELXTL (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C14H13Cl | F(000) = 456 |
Mr = 216.69 | Dx = 1.278 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2865 reflections |
a = 8.0400 (8) Å | θ = 2.3–28.0° |
b = 7.8514 (7) Å | µ = 0.30 mm−1 |
c = 18.1877 (16) Å | T = 293 K |
β = 101.133 (2)° | Irregular, colourless |
V = 1126.50 (18) Å3 | 0.30 × 0.25 × 0.10 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 1441 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.037 |
Graphite monochromator | θmax = 28.0°, θmin = 2.3° |
Detector resolution: 6.67 pixels mm-1 | h = −8→10 |
φ and ω scans | k = −10→10 |
6442 measured reflections | l = −23→19 |
2590 independent 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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.85 | w = 1/[σ2(Fo2) + (0.047P)2] where P = (Fo2 + 2Fc2)/3 |
2590 reflections | (Δ/σ)max < 0.001 |
172 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
H51 | −0.001 (2) | −0.586 (2) | −0.3153 (9) | 0.045 (5)* | |
H111 | 0.023 (2) | −0.270 (2) | −0.0706 (9) | 0.054 (5)* | |
H131 | 0.384 (2) | −0.227 (2) | −0.0737 (8) | 0.046 (5)* | |
H21 | −0.122 (2) | −0.723 (3) | −0.0803 (11) | 0.073 (7)* | |
H71 | 0.248 (2) | −0.394 (2) | −0.2474 (10) | 0.046 (5)* | |
H101 | 0.133 (2) | −0.538 (2) | −0.0223 (10) | 0.055 (5)* | |
H121 | 0.088 (2) | −0.185 (2) | −0.1903 (9) | 0.051 (5)* | |
H91 | 0.417 (2) | −0.606 (2) | −0.0423 (10) | 0.061 (6)* | |
H81 | 0.474 (3) | −0.521 (2) | −0.1606 (10) | 0.063 (6)* | |
Cl1 | 0.26779 (8) | 0.04040 (7) | 0.02362 (3) | 0.0698 (2) | |
C12 | 0.1643 (2) | −0.2662 (2) | −0.15942 (9) | 0.0403 (4) | |
C6 | 0.0718 (2) | −0.5459 (2) | −0.20451 (9) | 0.0414 (4) | |
C11 | 0.1278 (3) | −0.3136 (2) | −0.08466 (9) | 0.0428 (4) | |
C1 | 0.0369 (2) | −0.5884 (2) | −0.13462 (10) | 0.0452 (5) | |
C13 | 0.2677 (3) | −0.1901 (2) | −0.08898 (10) | 0.0446 (5) | |
C7 | 0.2207 (2) | −0.4247 (2) | −0.19934 (11) | 0.0456 (5) | |
C5 | −0.0265 (3) | −0.6126 (3) | −0.26861 (12) | 0.0528 (5) | |
C10 | 0.1601 (3) | −0.5063 (2) | −0.07054 (11) | 0.0507 (5) | |
C14 | 0.2381 (3) | −0.0061 (2) | −0.07460 (10) | 0.0572 (6) | |
H14A | 0.1234 | 0.0243 | −0.0985 | 0.069* | |
H14B | 0.3156 | 0.0628 | −0.0968 | 0.069* | |
C9 | 0.3356 (3) | −0.5492 (2) | −0.08176 (13) | 0.0575 (6) | |
C8 | 0.3674 (3) | −0.5065 (2) | −0.14771 (14) | 0.0573 (6) | |
C2 | −0.0986 (3) | −0.6909 (2) | −0.12910 (13) | 0.0616 (6) | |
C3 | −0.1979 (3) | −0.7558 (3) | −0.19426 (14) | 0.0723 (7) | |
H3 | −0.2899 | −0.8253 | −0.1912 | 0.087* | |
C4 | −0.1612 (3) | −0.7184 (3) | −0.26259 (14) | 0.0669 (6) | |
H4 | −0.2274 | −0.7644 | −0.3056 | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0940 (5) | 0.0564 (3) | 0.0608 (3) | −0.0179 (3) | 0.0196 (3) | −0.0155 (3) |
C12 | 0.0472 (12) | 0.0327 (10) | 0.0400 (10) | −0.0008 (8) | 0.0060 (9) | 0.0031 (8) |
C6 | 0.0421 (11) | 0.0314 (9) | 0.0482 (11) | 0.0028 (8) | 0.0021 (8) | −0.0057 (8) |
C11 | 0.0525 (12) | 0.0362 (10) | 0.0395 (10) | −0.0054 (9) | 0.0084 (9) | −0.0013 (8) |
C1 | 0.0522 (12) | 0.0297 (9) | 0.0517 (11) | −0.0044 (8) | 0.0046 (9) | −0.0011 (8) |
C13 | 0.0526 (13) | 0.0322 (10) | 0.0467 (11) | −0.0055 (9) | 0.0041 (9) | −0.0018 (8) |
C7 | 0.0513 (13) | 0.0419 (11) | 0.0448 (11) | −0.0015 (9) | 0.0125 (9) | −0.0030 (9) |
C5 | 0.0546 (14) | 0.0486 (12) | 0.0517 (13) | 0.0096 (10) | 0.0012 (10) | −0.0114 (10) |
C10 | 0.0731 (16) | 0.0361 (11) | 0.0395 (11) | −0.0128 (10) | 0.0021 (10) | 0.0055 (8) |
C14 | 0.0823 (16) | 0.0385 (12) | 0.0502 (11) | −0.0055 (10) | 0.0109 (11) | −0.0027 (8) |
C9 | 0.0583 (15) | 0.0327 (10) | 0.0686 (14) | −0.0004 (10) | −0.0197 (12) | −0.0016 (10) |
C8 | 0.0412 (13) | 0.0427 (12) | 0.0833 (17) | 0.0011 (10) | 0.0007 (12) | −0.0144 (11) |
C2 | 0.0723 (16) | 0.0419 (12) | 0.0706 (15) | −0.0184 (11) | 0.0143 (12) | −0.0002 (11) |
C3 | 0.0575 (15) | 0.0523 (13) | 0.104 (2) | −0.0178 (11) | 0.0072 (14) | −0.0118 (13) |
C4 | 0.0544 (15) | 0.0549 (14) | 0.0807 (16) | 0.0005 (11) | −0.0134 (12) | −0.0243 (12) |
Cl1—C14 | 1.7935 (19) | C7—H71 | 0.973 (17) |
C12—C11 | 1.493 (2) | C5—C4 | 1.386 (3) |
C12—C13 | 1.509 (2) | C5—H51 | 0.937 (16) |
C12—C7 | 1.552 (2) | C10—C9 | 1.503 (3) |
C12—H121 | 0.980 (17) | C10—H101 | 0.976 (18) |
C6—C5 | 1.379 (2) | C14—H14A | 0.9700 |
C6—C1 | 1.394 (2) | C14—H14B | 0.9700 |
C6—C7 | 1.518 (2) | C9—C8 | 1.317 (3) |
C11—C13 | 1.499 (2) | C9—H91 | 0.983 (19) |
C11—C10 | 1.549 (2) | C8—H81 | 0.94 (2) |
C11—H111 | 0.986 (17) | C2—C3 | 1.391 (3) |
C1—C2 | 1.373 (3) | C2—H21 | 0.974 (19) |
C1—C10 | 1.519 (3) | C3—C4 | 1.363 (3) |
C13—C14 | 1.495 (2) | C3—H3 | 0.9300 |
C13—H131 | 0.964 (16) | C4—H4 | 0.9300 |
C7—C8 | 1.503 (3) | ||
C11—C12—C13 | 59.91 (11) | C6—C5—C4 | 119.3 (2) |
C11—C12—C7 | 110.67 (15) | C6—C5—H51 | 119.4 (11) |
C13—C12—C7 | 123.51 (16) | C4—C5—H51 | 121.3 (11) |
C11—C12—H121 | 118.2 (10) | C9—C10—C1 | 106.91 (16) |
C13—C12—H121 | 114.2 (10) | C9—C10—C11 | 109.16 (17) |
C7—C12—H121 | 117.3 (10) | C1—C10—C11 | 102.92 (15) |
C5—C6—C1 | 119.80 (18) | C9—C10—H101 | 116.2 (11) |
C5—C6—C7 | 127.33 (18) | C1—C10—H101 | 110.9 (11) |
C1—C6—C7 | 112.87 (15) | C11—C10—H101 | 109.9 (11) |
C12—C11—C13 | 60.60 (11) | C13—C14—Cl1 | 112.06 (13) |
C12—C11—C10 | 109.79 (16) | C13—C14—H14A | 109.2 |
C13—C11—C10 | 122.51 (18) | Cl1—C14—H14A | 109.2 |
C12—C11—H111 | 118.6 (10) | C13—C14—H14B | 109.2 |
C13—C11—H111 | 118.5 (10) | Cl1—C14—H14B | 109.2 |
C10—C11—H111 | 114.7 (10) | H14A—C14—H14B | 107.9 |
C2—C1—C6 | 120.58 (18) | C8—C9—C10 | 114.79 (19) |
C2—C1—C10 | 126.94 (19) | C8—C9—H91 | 124.1 (11) |
C6—C1—C10 | 112.46 (16) | C10—C9—H91 | 121.1 (11) |
C14—C13—C11 | 117.98 (18) | C9—C8—C7 | 114.3 (2) |
C14—C13—C12 | 116.79 (17) | C9—C8—H81 | 123.0 (12) |
C11—C13—C12 | 59.49 (11) | C7—C8—H81 | 122.6 (12) |
C14—C13—H131 | 114.7 (10) | C1—C2—C3 | 119.0 (2) |
C11—C13—H131 | 118.9 (10) | C1—C2—H21 | 120.8 (12) |
C12—C13—H131 | 118.0 (10) | C3—C2—H21 | 120.1 (12) |
C8—C7—C6 | 106.56 (16) | C4—C3—C2 | 120.5 (2) |
C8—C7—C12 | 108.37 (15) | C4—C3—H3 | 119.7 |
C6—C7—C12 | 103.53 (15) | C2—C3—H3 | 119.7 |
C8—C7—H71 | 112.4 (10) | C3—C4—C5 | 120.71 (19) |
C6—C7—H71 | 114.4 (10) | C3—C4—H4 | 119.6 |
C12—C7—H71 | 111.0 (10) | C5—C4—H4 | 119.6 |
C7—C12—C11—C13 | 117.60 (17) | C7—C6—C5—C4 | −178.16 (17) |
C13—C12—C11—C10 | −116.93 (18) | C2—C1—C10—C9 | 129.1 (2) |
C7—C12—C11—C10 | 0.7 (2) | C6—C1—C10—C9 | −52.3 (2) |
C5—C6—C1—C2 | −2.5 (3) | C2—C1—C10—C11 | −115.9 (2) |
C7—C6—C1—C2 | 177.07 (17) | C6—C1—C10—C11 | 62.7 (2) |
C5—C6—C1—C10 | 178.79 (17) | C12—C11—C10—C9 | 53.0 (2) |
C7—C6—C1—C10 | −1.6 (2) | C13—C11—C10—C9 | −14.0 (2) |
C12—C11—C13—C14 | 106.22 (19) | C12—C11—C10—C1 | −60.3 (2) |
C10—C11—C13—C14 | −157.95 (16) | C13—C11—C10—C1 | −127.35 (18) |
C10—C11—C13—C12 | 95.83 (19) | C11—C13—C14—Cl1 | 80.2 (2) |
C11—C12—C13—C14 | −108.2 (2) | C12—C13—C14—Cl1 | 148.09 (15) |
C7—C12—C13—C14 | 155.72 (18) | C1—C10—C9—C8 | 54.8 (2) |
C7—C12—C13—C11 | −96.06 (19) | C11—C10—C9—C8 | −55.8 (2) |
C5—C6—C7—C8 | −125.8 (2) | C10—C9—C8—C7 | −0.7 (2) |
C1—C6—C7—C8 | 54.7 (2) | C6—C7—C8—C9 | −54.3 (2) |
C5—C6—C7—C12 | 120.03 (19) | C12—C7—C8—C9 | 56.6 (2) |
C1—C6—C7—C12 | −59.52 (18) | C6—C1—C2—C3 | 1.8 (3) |
C11—C12—C7—C8 | −54.3 (2) | C10—C1—C2—C3 | −179.71 (19) |
C13—C12—C7—C8 | 12.6 (2) | C1—C2—C3—C4 | 0.0 (3) |
C11—C12—C7—C6 | 58.57 (18) | C2—C3—C4—C5 | −1.2 (3) |
C13—C12—C7—C6 | 125.44 (17) | C6—C5—C4—C3 | 0.5 (3) |
C1—C6—C5—C4 | 1.4 (3) |