Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021901/om6177sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021901/om6177Isup2.hkl |
CCDC reference: 226956
Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
C18H18ClN3 | F(000) = 656 |
Mr = 311.80 | Dx = 1.379 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.2097 (6) Å | Cell parameters from 3431 reflections |
b = 7.5773 (3) Å | θ = 3.4–27.6° |
c = 20.6921 (12) Å | µ = 0.25 mm−1 |
β = 110.203 (3)° | T = 120 K |
V = 1502.29 (14) Å3 | Plate, colourless |
Z = 4 | 0.32 × 0.12 × 0.08 mm |
Nonius KappaCCD diffractometer | 3431 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2068 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.097 |
φ scans and ω scans with κ offsets | θmax = 27.6°, θmin = 3.4° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −13→13 |
Tmin = 0.947, Tmax = 0.987 | k = −9→9 |
22681 measured reflections | l = −26→26 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0682P)2] where P = (Fo2 + 2Fc2)/3 |
3431 reflections | (Δ/σ)max = 0.001 |
220 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl14 | 1.22307 (6) | 0.59681 (8) | 0.22896 (3) | 0.03141 (19) | |
N1 | 0.68101 (18) | 0.3536 (2) | 0.03180 (9) | 0.0226 (4) | |
N2 | 0.65961 (19) | 0.3644 (2) | −0.03784 (10) | 0.0246 (4) | |
C11 | 0.8083 (2) | 0.4149 (3) | 0.07943 (12) | 0.0222 (5) | |
C12 | 0.8423 (2) | 0.3851 (3) | 0.14960 (12) | 0.0295 (6) | |
C13 | 0.9692 (2) | 0.4423 (3) | 0.19559 (12) | 0.0296 (6) | |
C14 | 1.0613 (2) | 0.5305 (3) | 0.17136 (12) | 0.0249 (5) | |
C15 | 1.0280 (2) | 0.5639 (3) | 0.10201 (12) | 0.0265 (5) | |
C16 | 0.9014 (2) | 0.5062 (3) | 0.05599 (13) | 0.0247 (5) | |
C3 | 0.5339 (2) | 0.3012 (3) | −0.07098 (12) | 0.0243 (5) | |
C31 | 0.4786 (2) | 0.3035 (4) | −0.14761 (12) | 0.0305 (6) | |
C3A | 0.4681 (2) | 0.2446 (3) | −0.02350 (11) | 0.0230 (5) | |
C4 | 0.3411 (2) | 0.1655 (3) | −0.02711 (12) | 0.0229 (5) | |
C41 | 0.2379 (2) | 0.1071 (3) | −0.09536 (12) | 0.0279 (5) | |
C4A | 0.3182 (2) | 0.1422 (3) | 0.03487 (12) | 0.0239 (5) | |
C5 | 0.1824 (2) | 0.0602 (3) | 0.03553 (12) | 0.0269 (5) | |
C6 | 0.1503 (5) | 0.0959 (9) | 0.1014 (2) | 0.0309 (13) | 0.738 (13) |
C7 | 0.2783 (5) | 0.0559 (10) | 0.1637 (2) | 0.0296 (13) | 0.738 (13) |
C6A | 0.1946 (15) | 0.002 (3) | 0.1091 (6) | 0.032 (4) | 0.262 (13) |
C7A | 0.2567 (15) | 0.146 (3) | 0.1611 (8) | 0.033 (4) | 0.262 (13) |
C8 | 0.3988 (2) | 0.1796 (3) | 0.16554 (12) | 0.0294 (6) | |
C8A | 0.4218 (2) | 0.1931 (3) | 0.09756 (12) | 0.0235 (5) | |
N9 | 0.54664 (18) | 0.2602 (3) | 0.10215 (9) | 0.0236 (4) | |
C9A | 0.5642 (2) | 0.2835 (3) | 0.04166 (11) | 0.0221 (5) | |
H12 | 0.7783 | 0.3253 | 0.1661 | 0.035* | |
H13 | 0.9927 | 0.4210 | 0.2435 | 0.035* | |
H15 | 1.0915 | 0.6260 | 0.0859 | 0.032* | |
H16 | 0.8780 | 0.5291 | 0.0082 | 0.030* | |
H31A | 0.5491 | 0.3530 | −0.1647 | 0.046* | |
H31B | 0.3940 | 0.3762 | −0.1637 | 0.046* | |
H31C | 0.4561 | 0.1828 | −0.1649 | 0.046* | |
H41A | 0.1760 | 0.0170 | −0.0877 | 0.042* | |
H41B | 0.2882 | 0.0578 | −0.1239 | 0.042* | |
H41C | 0.1823 | 0.2086 | −0.1189 | 0.042* | |
H5A | 0.1868 | −0.0690 | 0.0295 | 0.032* | 0.738 (13) |
H5B | 0.1045 | 0.1063 | −0.0043 | 0.032* | 0.738 (13) |
H5C | 0.1592 | −0.0435 | 0.0045 | 0.032* | 0.262 (13) |
H5D | 0.1058 | 0.1470 | 0.0181 | 0.032* | 0.262 (13) |
H6A | 0.1231 | 0.2210 | 0.1025 | 0.037* | 0.738 (13) |
H6B | 0.0715 | 0.0209 | 0.1022 | 0.037* | 0.738 (13) |
H7A | 0.3070 | −0.0682 | 0.1617 | 0.036* | 0.738 (13) |
H7B | 0.2559 | 0.0712 | 0.2062 | 0.036* | 0.738 (13) |
H6C | 0.1008 | −0.0285 | 0.1098 | 0.038* | 0.262 (13) |
H6D | 0.2538 | −0.1046 | 0.1220 | 0.038* | 0.262 (13) |
H7C | 0.2006 | 0.2547 | 0.1473 | 0.040* | 0.262 (13) |
H7D | 0.2551 | 0.1089 | 0.2068 | 0.040* | 0.262 (13) |
H8A | 0.3792 | 0.2988 | 0.1795 | 0.035* | 0.738 (13) |
H8B | 0.4857 | 0.1367 | 0.2009 | 0.035* | 0.738 (13) |
H8C | 0.4588 | 0.0840 | 0.1928 | 0.035* | 0.262 (13) |
H8D | 0.4299 | 0.2913 | 0.1911 | 0.035* | 0.262 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl14 | 0.0244 (3) | 0.0414 (4) | 0.0271 (3) | −0.0059 (3) | 0.0072 (2) | −0.0056 (3) |
N1 | 0.0217 (9) | 0.0290 (11) | 0.0166 (11) | −0.0001 (8) | 0.0060 (8) | 0.0014 (8) |
N2 | 0.0240 (10) | 0.0308 (11) | 0.0190 (10) | 0.0028 (8) | 0.0074 (8) | 0.0016 (8) |
C11 | 0.0205 (11) | 0.0237 (12) | 0.0226 (13) | 0.0017 (10) | 0.0076 (10) | 0.0002 (9) |
C12 | 0.0253 (12) | 0.0383 (14) | 0.0249 (13) | −0.0052 (11) | 0.0087 (10) | 0.0056 (11) |
C13 | 0.0278 (12) | 0.0403 (15) | 0.0197 (13) | −0.0039 (11) | 0.0069 (10) | 0.0020 (11) |
C14 | 0.0217 (11) | 0.0286 (13) | 0.0243 (14) | 0.0011 (10) | 0.0079 (10) | −0.0027 (10) |
C15 | 0.0231 (11) | 0.0307 (14) | 0.0290 (14) | −0.0015 (10) | 0.0132 (10) | 0.0010 (10) |
C16 | 0.0241 (11) | 0.0288 (13) | 0.0227 (13) | 0.0016 (10) | 0.0100 (10) | 0.0005 (10) |
C3 | 0.0239 (11) | 0.0262 (12) | 0.0225 (13) | 0.0047 (10) | 0.0076 (10) | 0.0016 (10) |
C31 | 0.0279 (12) | 0.0417 (15) | 0.0212 (13) | 0.0017 (11) | 0.0076 (10) | 0.0002 (11) |
C3A | 0.0225 (11) | 0.0254 (13) | 0.0211 (13) | 0.0044 (10) | 0.0074 (10) | 0.0002 (10) |
C4 | 0.0233 (12) | 0.0225 (12) | 0.0225 (13) | 0.0035 (9) | 0.0071 (10) | −0.0015 (9) |
C41 | 0.0205 (11) | 0.0340 (14) | 0.0282 (14) | 0.0022 (10) | 0.0071 (10) | −0.0055 (11) |
C4A | 0.0224 (11) | 0.0215 (13) | 0.0271 (13) | 0.0021 (9) | 0.0078 (10) | −0.0010 (9) |
C5 | 0.0246 (12) | 0.0301 (14) | 0.0247 (14) | −0.0040 (10) | 0.0068 (10) | −0.0019 (10) |
C6 | 0.023 (2) | 0.038 (3) | 0.032 (2) | −0.002 (2) | 0.0104 (17) | −0.001 (2) |
C7 | 0.027 (2) | 0.037 (3) | 0.026 (2) | −0.004 (2) | 0.0109 (18) | 0.001 (2) |
C6A | 0.023 (6) | 0.034 (9) | 0.044 (7) | −0.007 (6) | 0.018 (5) | −0.003 (6) |
C7A | 0.038 (7) | 0.032 (9) | 0.035 (7) | −0.001 (6) | 0.020 (6) | −0.006 (7) |
C8 | 0.0274 (12) | 0.0382 (14) | 0.0220 (13) | −0.0022 (11) | 0.0079 (10) | 0.0018 (11) |
C8A | 0.0199 (11) | 0.0251 (12) | 0.0251 (13) | 0.0025 (10) | 0.0074 (10) | 0.0012 (10) |
N9 | 0.0206 (9) | 0.0276 (11) | 0.0228 (11) | 0.0005 (8) | 0.0077 (8) | 0.0020 (8) |
C9A | 0.0203 (11) | 0.0230 (12) | 0.0226 (13) | 0.0028 (9) | 0.0070 (9) | 0.0012 (9) |
Cl14—C14 | 1.744 (2) | C4A—C8A | 1.415 (3) |
N1—N2 | 1.383 (3) | C4A—C5 | 1.524 (3) |
N1—C9A | 1.384 (3) | C5—C6 | 1.532 (5) |
N1—C11 | 1.411 (3) | C5—C6A | 1.548 (13) |
N2—C3 | 1.319 (3) | C5—H5A | 0.99 |
C11—C12 | 1.390 (3) | C5—H5B | 0.99 |
C11—C16 | 1.391 (3) | C5—H5C | 0.99 |
C12—C13 | 1.386 (3) | C5—H5D | 0.99 |
C12—H12 | 0.95 | C6—C7 | 1.515 (9) |
C13—C14 | 1.381 (3) | C6—H6A | 0.99 |
C13—H13 | 0.95 | C6—H6B | 0.99 |
C14—C15 | 1.379 (3) | C7—C8 | 1.536 (5) |
C15—C16 | 1.385 (3) | C7—H7A | 0.99 |
C15—H15 | 0.95 | C7—H7B | 0.99 |
C16—H16 | 0.95 | C6A—C7A | 1.51 (2) |
C3—C3A | 1.434 (3) | C6A—H6C | 0.99 |
C3—C31 | 1.488 (3) | C6A—H6D | 0.99 |
C31—H31A | 0.98 | C7A—C8 | 1.445 (14) |
C31—H31B | 0.98 | C7A—H7C | 0.99 |
C31—H31C | 0.98 | C7A—H7D | 0.99 |
C3A—C9A | 1.398 (3) | C8—C8A | 1.507 (3) |
C3A—C4 | 1.407 (3) | C8—H8A | 0.99 |
C4—C4A | 1.392 (3) | C8—H8B | 0.99 |
C4—C41 | 1.508 (3) | C8—H8C | 0.99 |
C41—H41A | 0.98 | C8—H8D | 0.99 |
C41—H41B | 0.98 | C8A—N9 | 1.345 (3) |
C41—H41C | 0.98 | N9—C9A | 1.336 (3) |
N2—N1—C9A | 110.02 (17) | C6—C5—H5B | 108.7 |
N2—N1—C11 | 118.96 (17) | H5A—C5—H5B | 107.6 |
C9A—N1—C11 | 131.00 (19) | C4A—C5—H5C | 109.4 |
C3—N2—N1 | 107.18 (17) | C6A—C5—H5C | 109.4 |
C12—C11—C16 | 119.4 (2) | C4A—C5—H5D | 109.4 |
C12—C11—N1 | 120.91 (19) | C6A—C5—H5D | 109.4 |
C16—C11—N1 | 119.7 (2) | H5C—C5—H5D | 108.0 |
C13—C12—C11 | 120.2 (2) | C7—C6—C5 | 109.5 (5) |
C13—C12—H12 | 119.9 | C7—C6—H6A | 109.8 |
C11—C12—H12 | 119.9 | C5—C6—H6A | 109.8 |
C14—C13—C12 | 119.6 (2) | C7—C6—H6B | 109.8 |
C14—C13—H13 | 120.2 | C5—C6—H6B | 109.8 |
C12—C13—H13 | 120.2 | H6A—C6—H6B | 108.2 |
C15—C14—C13 | 120.8 (2) | C6—C7—C8 | 110.3 (5) |
C15—C14—Cl14 | 119.54 (17) | C6—C7—H7A | 109.6 |
C13—C14—Cl14 | 119.62 (18) | C8—C7—H7A | 109.6 |
C14—C15—C16 | 119.6 (2) | C6—C7—H7B | 109.6 |
C14—C15—H15 | 120.2 | C8—C7—H7B | 109.6 |
C16—C15—H15 | 120.2 | H7A—C7—H7B | 108.1 |
C15—C16—C11 | 120.3 (2) | C7A—C6A—C5 | 111.6 (14) |
C15—C16—H16 | 119.8 | C7A—C6A—H6C | 109.3 |
C11—C16—H16 | 119.8 | C5—C6A—H6C | 109.3 |
N2—C3—C3A | 110.8 (2) | C7A—C6A—H6D | 109.3 |
N2—C3—C31 | 119.5 (2) | C5—C6A—H6D | 109.3 |
C3A—C3—C31 | 129.7 (2) | H6C—C6A—H6D | 108.0 |
C3—C31—H31A | 109.5 | C8—C7A—C6A | 109.9 (13) |
C3—C31—H31B | 109.5 | C8—C7A—H7C | 109.7 |
H31A—C31—H31B | 109.5 | C6A—C7A—H7C | 109.7 |
C3—C31—H31C | 109.5 | C8—C7A—H7D | 109.7 |
H31A—C31—H31C | 109.5 | C6A—C7A—H7D | 109.7 |
H31B—C31—H31C | 109.5 | H7C—C7A—H7D | 108.2 |
C9A—C3A—C4 | 117.9 (2) | C7A—C8—C8A | 115.4 (6) |
C9A—C3A—C3 | 105.03 (19) | C8A—C8—C7 | 113.5 (3) |
C4—C3A—C3 | 137.1 (2) | C8A—C8—H8A | 108.9 |
C4A—C4—C3A | 116.8 (2) | C7—C8—H8A | 108.9 |
C4A—C4—C41 | 122.7 (2) | C8A—C8—H8B | 108.9 |
C3A—C4—C41 | 120.5 (2) | C7—C8—H8B | 108.9 |
C4—C41—H41A | 109.5 | H8A—C8—H8B | 107.7 |
C4—C41—H41B | 109.5 | C7A—C8—H8C | 108.4 |
H41A—C41—H41B | 109.5 | C8A—C8—H8C | 108.4 |
C4—C41—H41C | 109.5 | C7A—C8—H8D | 108.4 |
H41A—C41—H41C | 109.5 | C8A—C8—H8D | 108.4 |
H41B—C41—H41C | 109.5 | H8C—C8—H8D | 107.5 |
C4—C4A—C8A | 120.0 (2) | N9—C8A—C4A | 123.9 (2) |
C4—C4A—C5 | 120.2 (2) | N9—C8A—C8 | 114.1 (2) |
C8A—C4A—C5 | 119.8 (2) | C4A—C8A—C8 | 122.0 (2) |
C4A—C5—C6 | 114.2 (2) | C9A—N9—C8A | 114.46 (19) |
C4A—C5—C6A | 111.1 (4) | N9—C9A—N1 | 126.2 (2) |
C4A—C5—H5A | 108.7 | N9—C9A—C3A | 126.9 (2) |
C6—C5—H5A | 108.7 | N1—C9A—C3A | 106.98 (19) |
C4A—C5—H5B | 108.7 | ||
C9A—N1—N2—C3 | −0.7 (2) | C4—C4A—C5—C6A | 165.1 (8) |
C11—N1—N2—C3 | −179.32 (19) | C8A—C4A—C5—C6A | −14.3 (9) |
N2—N1—C11—C12 | −171.2 (2) | C4A—C5—C6—C7 | −48.6 (7) |
C9A—N1—C11—C12 | 10.6 (4) | C6A—C5—C6—C7 | 42.5 (9) |
N2—N1—C11—C16 | 8.7 (3) | C5—C6—C7—C8 | 63.0 (8) |
C9A—N1—C11—C16 | −169.6 (2) | C4A—C5—C6A—C7A | 48.0 (17) |
C16—C11—C12—C13 | −1.5 (4) | C6—C5—C6A—C7A | −54.3 (14) |
N1—C11—C12—C13 | 178.4 (2) | C5—C6A—C7A—C8 | −65 (2) |
C11—C12—C13—C14 | 0.5 (4) | C6A—C7A—C8—C8A | 45.0 (19) |
C12—C13—C14—C15 | 0.7 (4) | C6A—C7A—C8—C7 | −47.4 (15) |
C12—C13—C14—Cl14 | −178.15 (19) | C6—C7—C8—C7A | 52.6 (14) |
C13—C14—C15—C16 | −0.9 (4) | C6—C7—C8—C8A | −47.7 (7) |
Cl14—C14—C15—C16 | 177.93 (18) | C4—C4A—C8A—N9 | −2.0 (3) |
C14—C15—C16—C11 | −0.1 (3) | C5—C4A—C8A—N9 | 177.4 (2) |
C12—C11—C16—C15 | 1.2 (3) | C4—C4A—C8A—C8 | 176.6 (2) |
N1—C11—C16—C15 | −178.6 (2) | C5—C4A—C8A—C8 | −3.9 (3) |
N1—N2—C3—C3A | −0.5 (2) | C7A—C8—C8A—N9 | 166.9 (9) |
N1—N2—C3—C31 | 177.2 (2) | C7—C8—C8A—N9 | −163.0 (4) |
N2—C3—C3A—C9A | 1.5 (3) | C7A—C8—C8A—C4A | −11.9 (10) |
C31—C3—C3A—C9A | −175.9 (2) | C7—C8—C8A—C4A | 18.2 (4) |
N2—C3—C3A—C4 | −178.2 (3) | C4A—C8A—N9—C9A | 3.0 (3) |
C31—C3—C3A—C4 | 4.4 (4) | C8—C8A—N9—C9A | −175.8 (2) |
C9A—C3A—C4—C4A | 3.7 (3) | C8A—N9—C9A—N1 | 178.5 (2) |
C3—C3A—C4—C4A | −176.5 (2) | C8A—N9—C9A—C3A | −0.5 (3) |
C9A—C3A—C4—C41 | −175.2 (2) | N2—N1—C9A—N9 | −177.5 (2) |
C3—C3A—C4—C41 | 4.5 (4) | C11—N1—C9A—N9 | 0.9 (4) |
C3A—C4—C4A—C8A | −1.5 (3) | N2—N1—C9A—C3A | 1.7 (2) |
C41—C4—C4A—C8A | 177.4 (2) | C11—N1—C9A—C3A | −179.9 (2) |
C3A—C4—C4A—C5 | 179.0 (2) | C4—C3A—C9A—N9 | −2.9 (3) |
C41—C4—C4A—C5 | −2.1 (3) | C3—C3A—C9A—N9 | 177.3 (2) |
C4—C4A—C5—C6 | −161.3 (4) | C4—C3A—C9A—N1 | 177.91 (19) |
C8A—C4A—C5—C6 | 19.3 (4) | C3—C3A—C9A—N1 | −1.9 (2) |