Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008573/ob6488sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008573/ob6488Isup2.hkl |
CCDC reference: 290312
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.008 Å
- R factor = 0.059
- wR factor = 0.178
- Data-to-parameter ratio = 10.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C6
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C6 - C7 .. 5.22 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 25.02 From the CIF: _reflns_number_total 2127 Count of symmetry unique reflns 1559 Completeness (_total/calc) 136.43% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 568 Fraction of Friedel pairs measured 0.364 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.
C18H20ClNO2 | Dx = 1.278 Mg m−3 |
Mr = 317.80 | Melting point = 448–449 K |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
a = 17.492 (3) Å | Cell parameters from 1544 reflections |
b = 9.805 (2) Å | θ = 2.3–19.9° |
c = 9.634 (2) Å | µ = 0.24 mm−1 |
V = 1652.3 (7) Å3 | T = 298 K |
Z = 4 | Block, yellow |
F(000) = 672 | 0.29 × 0.25 × 0.17 mm |
Bruker SMART CCD area-detector diffractometer | 2127 independent reflections |
Radiation source: fine-focus sealed tube | 1321 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
φ and ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −20→18 |
Tmin = 0.934, Tmax = 0.961 | k = −11→11 |
8088 measured reflections | l = −11→7 |
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)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.179 | w = 1/[σ2(Fo2) + (0.1083P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
2127 reflections | Δρmax = 0.42 e Å−3 |
202 parameters | Δρmin = −0.29 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 568 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.14 (17) |
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 | ||
Cl1 | 0.19846 (12) | −0.41262 (17) | 0.3234 (4) | 0.1475 (12) | |
N1 | −0.0080 (2) | 0.2082 (5) | 0.4219 (5) | 0.0699 (13) | |
O1 | −0.0336 (3) | 0.1489 (7) | 0.2017 (5) | 0.1250 (19) | |
O2 | 0.2465 (2) | 0.2864 (4) | 0.5616 (5) | 0.0796 (11) | |
C1 | 0.0128 (4) | 0.1929 (7) | 0.2833 (7) | 0.0773 (17) | |
C2 | 0.0901 (4) | 0.2313 (7) | 0.2432 (6) | 0.0778 (18) | |
H2A | 0.0921 | 0.3292 | 0.2296 | 0.093* | |
H2B | 0.1025 | 0.1882 | 0.1554 | 0.093* | |
C3 | 0.1494 (3) | 0.1909 (5) | 0.3499 (6) | 0.0602 (13) | |
H3 | 0.1975 | 0.2366 | 0.3262 | 0.072* | |
C4 | 0.1218 (3) | 0.2474 (5) | 0.4874 (5) | 0.0529 (12) | |
C5 | 0.1791 (3) | 0.2980 (5) | 0.5846 (6) | 0.0662 (15) | |
C6 | 0.1508 (3) | 0.3728 (9) | 0.7070 (8) | 0.106 (3) | |
H6A | 0.1881 | 0.3628 | 0.7808 | 0.127* | |
H6B | 0.1486 | 0.4689 | 0.6835 | 0.127* | |
C7 | 0.0770 (3) | 0.3332 (6) | 0.7611 (6) | 0.0734 (16) | |
C8 | 0.0171 (3) | 0.3047 (6) | 0.6516 (6) | 0.0648 (14) | |
H8A | −0.0188 | 0.2386 | 0.6885 | 0.078* | |
H8B | −0.0110 | 0.3883 | 0.6341 | 0.078* | |
C9 | 0.0465 (3) | 0.2536 (5) | 0.5195 (6) | 0.0559 (13) | |
C10 | −0.0854 (3) | 0.1780 (8) | 0.4633 (9) | 0.104 (3) | |
H10A | −0.1083 | 0.2581 | 0.5027 | 0.156* | |
H10B | −0.0852 | 0.1062 | 0.5311 | 0.156* | |
H10C | −0.1144 | 0.1496 | 0.3837 | 0.156* | |
C11 | 0.1637 (2) | 0.0402 (5) | 0.3519 (5) | 0.0529 (11) | |
C12 | 0.2105 (3) | −0.0171 (6) | 0.2507 (7) | 0.0748 (15) | |
H12 | 0.2345 | 0.0392 | 0.1863 | 0.090* | |
C13 | 0.2218 (3) | −0.1565 (7) | 0.2447 (8) | 0.0840 (19) | |
H13 | 0.2540 | −0.1930 | 0.1774 | 0.101* | |
C14 | 0.1865 (3) | −0.2398 (6) | 0.3356 (8) | 0.0769 (19) | |
C15 | 0.1413 (3) | −0.1873 (5) | 0.4389 (7) | 0.0665 (14) | |
H15 | 0.1181 | −0.2444 | 0.5034 | 0.080* | |
C16 | 0.1309 (3) | −0.0489 (5) | 0.4451 (6) | 0.0600 (13) | |
H16 | 0.1004 | −0.0135 | 0.5155 | 0.072* | |
C17 | 0.0932 (4) | 0.1822 (6) | 0.8257 (8) | 0.096 (2) | |
H17A | 0.1114 | 0.1227 | 0.7538 | 0.144* | |
H17B | 0.0467 | 0.1461 | 0.8638 | 0.144* | |
H17C | 0.1310 | 0.1888 | 0.8976 | 0.144* | |
C18 | 0.0476 (4) | 0.4086 (7) | 0.8815 (7) | 0.097 (2) | |
H18A | 0.0891 | 0.4297 | 0.9432 | 0.145* | |
H18B | 0.0105 | 0.3538 | 0.9293 | 0.145* | |
H18C | 0.0240 | 0.4917 | 0.8507 | 0.145* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1430 (15) | 0.0754 (10) | 0.224 (3) | 0.0267 (10) | 0.0609 (19) | −0.0065 (15) |
N1 | 0.060 (2) | 0.093 (3) | 0.057 (3) | −0.008 (2) | −0.011 (2) | −0.003 (3) |
O1 | 0.126 (4) | 0.171 (5) | 0.078 (4) | −0.020 (4) | −0.038 (3) | −0.025 (3) |
O2 | 0.059 (2) | 0.106 (3) | 0.074 (3) | −0.003 (2) | 0.000 (2) | −0.008 (3) |
C1 | 0.083 (4) | 0.090 (4) | 0.058 (4) | −0.003 (3) | −0.031 (4) | −0.004 (3) |
C2 | 0.109 (5) | 0.087 (4) | 0.038 (3) | −0.009 (3) | −0.009 (3) | 0.011 (3) |
C3 | 0.069 (3) | 0.064 (3) | 0.047 (3) | −0.008 (2) | 0.005 (3) | 0.006 (3) |
C4 | 0.057 (3) | 0.055 (3) | 0.047 (3) | −0.008 (2) | 0.000 (2) | 0.001 (2) |
C5 | 0.054 (3) | 0.074 (4) | 0.070 (4) | −0.001 (2) | −0.010 (3) | −0.010 (3) |
C6 | 0.084 (4) | 0.153 (7) | 0.080 (5) | −0.003 (5) | −0.012 (4) | −0.061 (5) |
C7 | 0.076 (4) | 0.087 (4) | 0.058 (4) | −0.012 (3) | 0.003 (3) | −0.025 (3) |
C8 | 0.061 (3) | 0.079 (4) | 0.055 (3) | 0.006 (3) | −0.004 (3) | −0.005 (3) |
C9 | 0.065 (3) | 0.054 (3) | 0.049 (3) | −0.002 (2) | −0.013 (3) | −0.003 (3) |
C10 | 0.063 (3) | 0.147 (6) | 0.102 (6) | −0.023 (4) | −0.011 (4) | −0.009 (5) |
C11 | 0.058 (2) | 0.055 (3) | 0.045 (3) | −0.005 (2) | 0.002 (3) | 0.000 (3) |
C12 | 0.082 (3) | 0.076 (4) | 0.067 (4) | −0.009 (3) | 0.026 (3) | 0.001 (4) |
C13 | 0.083 (4) | 0.079 (4) | 0.090 (5) | 0.007 (3) | 0.030 (4) | −0.016 (4) |
C14 | 0.061 (3) | 0.067 (3) | 0.102 (6) | 0.009 (2) | 0.010 (4) | −0.009 (4) |
C15 | 0.071 (3) | 0.060 (3) | 0.068 (4) | −0.004 (3) | 0.007 (3) | 0.008 (3) |
C16 | 0.068 (3) | 0.060 (3) | 0.051 (3) | −0.003 (2) | 0.008 (3) | 0.001 (3) |
C17 | 0.129 (5) | 0.087 (4) | 0.072 (5) | 0.002 (3) | −0.008 (4) | 0.007 (4) |
C18 | 0.102 (4) | 0.126 (6) | 0.062 (4) | 0.026 (4) | −0.008 (4) | −0.026 (4) |
Cl1—C14 | 1.712 (6) | C8—C9 | 1.462 (8) |
N1—C1 | 1.392 (8) | C8—H8A | 0.9700 |
N1—C9 | 1.410 (6) | C8—H8B | 0.9700 |
N1—C10 | 1.443 (7) | C10—H10A | 0.9600 |
O1—C1 | 1.210 (7) | C10—H10B | 0.9600 |
O2—C5 | 1.205 (6) | C10—H10C | 0.9600 |
C1—C2 | 1.455 (8) | C11—C16 | 1.377 (6) |
C2—C3 | 1.514 (8) | C11—C12 | 1.392 (7) |
C2—H2A | 0.9700 | C12—C13 | 1.382 (8) |
C2—H2B | 0.9700 | C12—H12 | 0.9300 |
C3—C11 | 1.499 (6) | C13—C14 | 1.348 (8) |
C3—C4 | 1.515 (7) | C13—H13 | 0.9300 |
C3—H3 | 0.9800 | C14—C15 | 1.372 (8) |
C4—C9 | 1.354 (7) | C15—C16 | 1.370 (7) |
C4—C5 | 1.459 (8) | C15—H15 | 0.9300 |
C5—C6 | 1.474 (9) | C16—H16 | 0.9300 |
C6—C7 | 1.445 (8) | C17—H17A | 0.9600 |
C6—H6A | 0.9700 | C17—H17B | 0.9600 |
C6—H6B | 0.9700 | C17—H17C | 0.9600 |
C7—C18 | 1.469 (8) | C18—H18A | 0.9600 |
C7—C8 | 1.512 (8) | C18—H18B | 0.9600 |
C7—C17 | 1.631 (9) | C18—H18C | 0.9600 |
C1—N1—C9 | 119.8 (4) | H8A—C8—H8B | 107.5 |
C1—N1—C10 | 119.3 (5) | C4—C9—N1 | 119.4 (4) |
C9—N1—C10 | 120.9 (5) | C4—C9—C8 | 123.8 (4) |
O1—C1—N1 | 119.0 (6) | N1—C9—C8 | 116.9 (4) |
O1—C1—C2 | 122.9 (7) | N1—C10—H10A | 109.5 |
N1—C1—C2 | 118.0 (5) | N1—C10—H10B | 109.5 |
C1—C2—C3 | 112.9 (5) | H10A—C10—H10B | 109.5 |
C1—C2—H2A | 109.0 | N1—C10—H10C | 109.5 |
C3—C2—H2A | 109.0 | H10A—C10—H10C | 109.5 |
C1—C2—H2B | 109.0 | H10B—C10—H10C | 109.5 |
C3—C2—H2B | 109.0 | C16—C11—C12 | 116.4 (4) |
H2A—C2—H2B | 107.8 | C16—C11—C3 | 124.4 (4) |
C11—C3—C2 | 112.3 (5) | C12—C11—C3 | 119.1 (5) |
C11—C3—C4 | 113.7 (4) | C13—C12—C11 | 120.8 (5) |
C2—C3—C4 | 106.2 (4) | C13—C12—H12 | 119.6 |
C11—C3—H3 | 108.1 | C11—C12—H12 | 119.6 |
C2—C3—H3 | 108.1 | C14—C13—C12 | 120.4 (6) |
C4—C3—H3 | 108.1 | C14—C13—H13 | 119.8 |
C9—C4—C5 | 120.4 (5) | C12—C13—H13 | 119.8 |
C9—C4—C3 | 121.8 (4) | C13—C14—C15 | 120.6 (5) |
C5—C4—C3 | 117.8 (4) | C13—C14—Cl1 | 120.0 (5) |
O2—C5—C4 | 121.5 (5) | C15—C14—Cl1 | 119.4 (5) |
O2—C5—C6 | 121.5 (5) | C16—C15—C14 | 118.6 (6) |
C4—C5—C6 | 116.9 (5) | C16—C15—H15 | 120.7 |
C7—C6—C5 | 117.0 (6) | C14—C15—H15 | 120.7 |
C7—C6—H6A | 108.0 | C15—C16—C11 | 123.0 (5) |
C5—C6—H6A | 108.0 | C15—C16—H16 | 118.5 |
C7—C6—H6B | 108.0 | C11—C16—H16 | 118.5 |
C5—C6—H6B | 108.0 | C7—C17—H17A | 109.5 |
H6A—C6—H6B | 107.3 | C7—C17—H17B | 109.5 |
C6—C7—C18 | 117.5 (5) | H17A—C17—H17B | 109.5 |
C6—C7—C8 | 114.6 (5) | C7—C17—H17C | 109.5 |
C18—C7—C8 | 113.7 (5) | H17A—C17—H17C | 109.5 |
C6—C7—C17 | 103.1 (6) | H17B—C17—H17C | 109.5 |
C18—C7—C17 | 102.5 (5) | C7—C18—H18A | 109.5 |
C8—C7—C17 | 102.7 (5) | C7—C18—H18B | 109.5 |
C9—C8—C7 | 115.3 (5) | H18A—C18—H18B | 109.5 |
C9—C8—H8A | 108.4 | C7—C18—H18C | 109.5 |
C7—C8—H8A | 108.4 | H18A—C18—H18C | 109.5 |
C9—C8—H8B | 108.4 | H18B—C18—H18C | 109.5 |
C7—C8—H8B | 108.4 |