Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805014492/gh6021sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805014492/gh6021Isup2.hkl |
CCDC reference: 274400
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.041
- wR factor = 0.142
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
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 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1997); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: CrystalStructure.
C14H10ClNO | F(000) = 504.00 |
Mr = 243.69 | Dx = 1.406 Mg m−3 |
Monoclinic, P21/n | Melting point: 373 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.7107 Å |
a = 6.8221 (3) Å | Cell parameters from 7263 reflections |
b = 23.023 (1) Å | θ = 2.9–27.4° |
c = 7.6719 (3) Å | µ = 0.31 mm−1 |
β = 107.176 (2)° | T = 293 K |
V = 1151.2 (1) Å3 | Block, colorless |
Z = 4 | 0.52 × 0.50 × 0.40 mm |
Rigaku R-AXIS RAPID diffractometer | 1871 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.025 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi,1995) | h = −8→7 |
Tmin = 0.770, Tmax = 0.883 | k = −29→29 |
8508 measured reflections | l = −9→9 |
2554 independent reflections |
Refinement on F2 | w = 1/[0.004Fo2 + σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.041 | (Δ/σ)max < 0.001 |
wR(F2) = 0.142 | Δρmax = 0.20 e Å−3 |
S = 1.00 | Δρmin = −0.26 e Å−3 |
1871 reflections | Extinction correction: Larson (1970), equation 22 |
155 parameters | Extinction coefficient: 246 (55) |
H-atom parameters constrained |
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 using reflections with F2 > 2.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.2973 (1) | 0.38736 (2) | 0.58020 (8) | 0.0780 (2) | |
O1 | 0.9062 (2) | 0.59633 (6) | 1.0202 (2) | 0.0607 (4) | |
N1 | 0.8241 (3) | 0.69819 (7) | 0.8186 (3) | 0.0559 (5) | |
C1 | 0.7392 (3) | 0.60450 (7) | 0.9104 (3) | 0.0418 (4) | |
C2 | 0.6758 (3) | 0.66636 (7) | 0.8551 (2) | 0.0410 (4) | |
C3 | 0.7803 (4) | 0.7537 (1) | 0.7749 (3) | 0.0685 (7) | |
C4 | 0.5984 (4) | 0.7796 (1) | 0.7693 (4) | 0.0740 (7) | |
C5 | 0.4495 (4) | 0.74639 (9) | 0.8093 (3) | 0.0670 (6) | |
C6 | 0.4864 (3) | 0.68803 (8) | 0.8534 (3) | 0.0482 (5) | |
C7 | 0.3303 (3) | 0.64971 (8) | 0.8978 (3) | 0.0564 (6) | |
C8 | 0.2529 (3) | 0.60225 (9) | 0.7577 (3) | 0.0620 (6) | |
C9 | 0.3962 (3) | 0.55204 (8) | 0.7577 (2) | 0.0446 (5) | |
C10 | 0.3043 (3) | 0.49931 (9) | 0.6857 (2) | 0.0522 (5) | |
C11 | 0.4188 (3) | 0.45142 (8) | 0.6734 (2) | 0.0517 (5) | |
C12 | 0.6300 (3) | 0.45281 (8) | 0.7345 (3) | 0.0525 (5) | |
C13 | 0.7238 (3) | 0.50361 (7) | 0.8128 (2) | 0.0461 (5) | |
C14 | 0.6100 (3) | 0.55362 (7) | 0.8249 (2) | 0.0395 (4) | |
H10 | 0.1543 | 0.4965 | 0.6427 | 0.061* | |
H12 | 0.7104 | 0.4187 | 0.7217 | 0.064* | |
H13 | 0.8736 | 0.5051 | 0.8616 | 0.055* | |
H71 | 0.3937 | 0.6312 | 1.0145 | 0.070* | |
H72 | 0.2157 | 0.6734 | 0.9061 | 0.070* | |
H3 | 0.8857 | 0.7774 | 0.7457 | 0.082* | |
H4 | 0.5732 | 0.8206 | 0.7356 | 0.085* | |
H81 | 0.2213 | 0.6208 | 0.6390 | 0.074* | |
H82 | 0.1283 | 0.5863 | 0.7749 | 0.074* | |
H5 | 0.3180 | 0.7639 | 0.8079 | 0.079* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1060 (6) | 0.0508 (4) | 0.0711 (4) | −0.0291 (3) | 0.0167 (4) | −0.0095 (2) |
O1 | 0.0411 (8) | 0.0452 (7) | 0.083 (1) | 0.0055 (6) | −0.0016 (7) | −0.0033 (7) |
N1 | 0.0505 (9) | 0.0450 (9) | 0.073 (1) | −0.0064 (7) | 0.0197 (8) | 0.0031 (7) |
C1 | 0.0355 (8) | 0.0382 (9) | 0.0530 (9) | 0.0032 (6) | 0.0148 (8) | −0.0006 (7) |
C2 | 0.0422 (9) | 0.0352 (8) | 0.0459 (8) | 0.0019 (6) | 0.0133 (7) | 0.0010 (6) |
C3 | 0.073 (1) | 0.047 (1) | 0.084 (1) | −0.012 (1) | 0.020 (1) | 0.012 (1) |
C4 | 0.079 (2) | 0.042 (1) | 0.092 (2) | 0.005 (1) | 0.011 (1) | 0.020 (1) |
C5 | 0.062 (1) | 0.046 (1) | 0.089 (1) | 0.0171 (9) | 0.016 (1) | 0.010 (1) |
C6 | 0.047 (1) | 0.0400 (9) | 0.057 (1) | 0.0071 (7) | 0.0154 (9) | 0.0023 (7) |
C7 | 0.047 (1) | 0.051 (1) | 0.078 (1) | 0.0110 (8) | 0.029 (1) | 0.0027 (9) |
C8 | 0.0359 (9) | 0.056 (1) | 0.092 (2) | 0.0044 (8) | 0.015 (1) | 0.002 (1) |
C9 | 0.0414 (9) | 0.0448 (9) | 0.0473 (9) | −0.0014 (7) | 0.0125 (7) | 0.0043 (7) |
C10 | 0.049 (1) | 0.051 (1) | 0.053 (1) | −0.0099 (8) | 0.0091 (8) | 0.0046 (8) |
C11 | 0.070 (1) | 0.041 (1) | 0.0430 (9) | −0.0138 (8) | 0.0155 (8) | 0.0013 (7) |
C12 | 0.069 (1) | 0.0367 (9) | 0.054 (1) | 0.0022 (8) | 0.0215 (9) | 0.0021 (7) |
C13 | 0.047 (1) | 0.0367 (9) | 0.0544 (9) | 0.0042 (7) | 0.0149 (8) | 0.0045 (7) |
C14 | 0.0388 (9) | 0.0368 (9) | 0.0427 (8) | 0.0010 (6) | 0.0119 (7) | 0.0038 (6) |
Cl1—C11 | 1.739 (2) | C10—C11 | 1.371 (3) |
O1—C1 | 1.215 (2) | C11—C12 | 1.377 (3) |
N1—C2 | 1.344 (3) | C12—C13 | 1.382 (2) |
N1—C3 | 1.332 (3) | C13—C14 | 1.407 (2) |
C1—C2 | 1.512 (2) | C3—H3 | 0.9800 |
C1—C14 | 1.496 (2) | C4—H4 | 0.9800 |
C2—C6 | 1.381 (3) | C5—H5 | 0.9800 |
C3—C4 | 1.367 (4) | C7—H71 | 0.9700 |
C4—C5 | 1.377 (4) | C7—H72 | 0.9700 |
C5—C6 | 1.390 (3) | C8—H81 | 0.9700 |
C6—C7 | 1.498 (3) | C8—H82 | 0.9700 |
C7—C8 | 1.514 (3) | C10—H10 | 0.9800 |
C8—C9 | 1.514 (3) | C12—H12 | 0.9800 |
C9—C10 | 1.403 (3) | C13—H13 | 0.9800 |
C9—C14 | 1.397 (2) | ||
Cl1—C11—C10 | 119.9 (2) | C11—C12—C13 | 118.1 (2) |
Cl1—C11—C12 | 118.9 (2) | C12—C13—C14 | 121.9 (2) |
O1—C1—C2 | 118.2 (1) | N1—C3—H3 | 117.8385 |
O1—C1—C14 | 119.5 (1) | H3—C3—C4 | 118.0048 |
N1—C2—C1 | 113.7 (2) | C3—C4—H4 | 121.0825 |
N1—C2—C6 | 124.1 (2) | H4—C4—C5 | 120.7095 |
C3—N1—C2 | 116.7 (2) | C4—C5—H5 | 120.1502 |
N1—C3—C4 | 124.2 (2) | H5—C5—C6 | 119.9215 |
C1—C2—C6 | 122.1 (2) | C6—C7—H71 | 108.3647 |
C14—C1—C2 | 122.1 (1) | C6—C7—H72 | 108.9981 |
C1—C14—C13 | 113.9 (1) | H71—C7—C8 | 107.8055 |
C1—C14—C9 | 126.7 (2) | C7—C8—H81 | 106.4728 |
C2—C6—C5 | 116.9 (2) | H72—C7—C8 | 109.4416 |
C2—C6—C7 | 120.7 (2) | C7—C8—H82 | 108.2342 |
C3—C4—C5 | 118.2 (2) | H72—C7—H71 | 109.4611 |
C4—C5—C6 | 119.9 (2) | H81—C8—C9 | 107.4585 |
C5—C6—C7 | 122.3 (2) | H82—C8—C9 | 107.5925 |
C6—C7—C8 | 112.7 (2) | H82—C8—H81 | 109.4607 |
C7—C8—C9 | 117.5 (1) | C9—C10—H10 | 119.3193 |
C8—C9—C10 | 116.6 (2) | H10—C10—C11 | 118.9397 |
C8—C9—C14 | 125.7 (2) | C11—C12—H12 | 120.4822 |
C9—C10—C11 | 121.7 (2) | H12—C12—C13 | 121.4332 |
C14—C9—C10 | 117.7 (2) | C12—C13—H13 | 119.4861 |
C9—C14—C13 | 119.4 (1) | H13—C13—C14 | 118.6629 |
C10—C11—C12 | 121.2 (2) | ||
C3—N1—C2—C1 | −177.9 (2) | C2—C6—C7—C8 | −66.0 (2) |
C3—N1—C2—C6 | −1.4 (3) | C5—C6—C7—C8 | 114.1 (2) |
C2—N1—C3—C4 | 1.5 (3) | C6—C7—C8—C9 | 73.6 (2) |
O1—C1—C2—N1 | 45.1 (3) | C7—C8—C9—C10 | 155.1 (2) |
O1—C1—C2—C6 | −131.4 (2) | C7—C8—C9—C14 | −24.1 (3) |
C14—C1—C2—N1 | −130.6 (2) | C8—C9—C10—C11 | 177.9 (2) |
C14—C1—C2—C6 | 52.9 (3) | C14—C9—C10—C11 | −2.8 (3) |
O1—C1—C14—C9 | 152.8 (2) | C8—C9—C14—C1 | 0.4 (3) |
O1—C1—C14—C13 | −27.9 (3) | C8—C9—C14—C13 | −178.9 (2) |
C2—C1—C14—C9 | −31.6 (3) | C10—C9—C14—C1 | −178.8 (2) |
C2—C1—C14—C13 | 147.7 (2) | C10—C9—C14—C13 | 2.0 (3) |
N1—C2—C6—C5 | 0.6 (3) | C9—C10—C11—Cl1 | −179.2 (2) |
N1—C2—C6—C7 | −179.3 (2) | C9—C10—C11—C12 | 1.1 (3) |
C1—C2—C6—C5 | 176.7 (2) | Cl1—C11—C12—C13 | −178.2 (2) |
C1—C2—C6—C7 | −3.2 (3) | C10—C11—C12—C13 | 1.5 (3) |
N1—C3—C4—C5 | −0.8 (4) | C11—C12—C13—C14 | −2.3 (3) |
C3—C4—C5—C6 | −0.1 (3) | C12—C13—C14—C1 | −178.7 (2) |
C4—C5—C6—C2 | 0.2 (3) | C12—C13—C14—C9 | 0.6 (3) |
C4—C5—C6—C7 | −179.9 (2) |