Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031199/cv2083sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031199/cv20832sup2.hkl |
CCDC reference: 620772
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.086
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: CAD-4 EXPRESS; cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wokadlo, (1995); 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).
C14H13ClN2O2 | F(000) = 576 |
Mr = 276.71 | Dx = 1.403 Mg m−3 |
Monoclinic, P21/n | Melting point: 446 K |
Hall symbol: -P 2yn | Cu Kα radiation, λ = 1.5418 Å |
a = 7.1975 (8) Å | Cell parameters from 25 reflections |
b = 9.3817 (10) Å | θ = 30–33° |
c = 19.422 (3) Å | µ = 2.58 mm−1 |
β = 92.314 (9)° | T = 293 K |
V = 1310.4 (3) Å3 | Prism, colourless |
Z = 4 | 0.2 × 0.2 × 0.2 mm |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.090 |
Radiation source: Fine-focus sealed tube | θmax = 74.9°, θmin = 4.6° |
Graphite monochromator | h = −9→9 |
ω scans | k = 0→11 |
2760 measured reflections | l = 0→24 |
2683 independent reflections | 1 standard reflections every 60 min |
1907 reflections with I > 2σ(I) | intensity decay: 4% |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0422P)2] where P = (Fo2 + 2Fc2)/3 |
2683 reflections | (Δ/σ)max = 0.003 |
174 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
Experimental. Spectroscopic analysis: 1H NMR (DMSO-d6/TMS, δ, J, Hz): 2.24 (3H, s, CH3), 2.29 (3H, s, CH3), 5.50 (2H, s, CH2), 6.23 (1H, s, H-5), 7.56 (2H, m, p-ClPh), 8.08 (2H, m, p-ClPh); IR (nujol, νCO, cm-1): 1695, 1610. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.06506 (16) | 0.44796 (13) | 0.72057 (6) | 0.0447 (3) | |
C2 | 0.0976 (2) | 0.54726 (17) | 0.66780 (8) | 0.0525 (4) | |
O2 | 0.24693 (18) | 0.60918 (14) | 0.66857 (7) | 0.0749 (4) | |
N3 | −0.0403 (2) | 0.57024 (15) | 0.61881 (7) | 0.0588 (4) | |
C4 | −0.1962 (2) | 0.49939 (18) | 0.62188 (8) | 0.0543 (4) | |
C41 | −0.3433 (3) | 0.5293 (3) | 0.56670 (10) | 0.0871 (7) | |
H41A | −0.3350 | 0.6270 | 0.5525 | 0.131* | |
H41B | −0.4638 | 0.5118 | 0.5844 | 0.131* | |
H41C | −0.3251 | 0.4681 | 0.5279 | 0.131* | |
C5 | −0.2315 (2) | 0.39954 (17) | 0.67347 (9) | 0.0544 (4) | |
H5 | −0.3440 | 0.3508 | 0.6734 | 0.065* | |
C6 | −0.0981 (2) | 0.37535 (16) | 0.72360 (8) | 0.0460 (3) | |
C61 | −0.1249 (2) | 0.2720 (2) | 0.78081 (10) | 0.0645 (5) | |
H61A | −0.2454 | 0.2289 | 0.7752 | 0.097* | |
H61B | −0.1155 | 0.3213 | 0.8241 | 0.097* | |
H61C | −0.0309 | 0.1995 | 0.7798 | 0.097* | |
C7 | 0.2147 (2) | 0.43830 (17) | 0.77377 (8) | 0.0505 (4) | |
H7A | 0.3338 | 0.4357 | 0.7522 | 0.061* | |
H7B | 0.2015 | 0.3507 | 0.7997 | 0.061* | |
C8 | 0.2092 (2) | 0.56504 (18) | 0.82245 (8) | 0.0494 (4) | |
O8 | 0.07713 (17) | 0.64427 (14) | 0.82093 (7) | 0.0755 (4) | |
C9 | 0.3723 (2) | 0.58649 (16) | 0.87126 (7) | 0.0460 (3) | |
C10 | 0.5266 (2) | 0.5011 (2) | 0.87179 (9) | 0.0658 (5) | |
H10 | 0.5316 | 0.4254 | 0.8410 | 0.079* | |
C11 | 0.6757 (2) | 0.5261 (2) | 0.91776 (10) | 0.0695 (5) | |
H11 | 0.7813 | 0.4691 | 0.9172 | 0.083* | |
C12 | 0.6654 (2) | 0.63622 (19) | 0.96415 (8) | 0.0537 (4) | |
C13 | 0.5112 (2) | 0.7211 (2) | 0.96540 (9) | 0.0614 (4) | |
H13 | 0.5053 | 0.7948 | 0.9973 | 0.074* | |
C14 | 0.3639 (2) | 0.69656 (19) | 0.91894 (8) | 0.0564 (4) | |
H14 | 0.2587 | 0.7540 | 0.9196 | 0.068* | |
Cl12 | 0.85163 (7) | 0.66768 (6) | 1.02110 (3) | 0.07873 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0469 (6) | 0.0388 (7) | 0.0486 (7) | −0.0027 (5) | 0.0044 (5) | −0.0018 (6) |
C2 | 0.0634 (9) | 0.0423 (9) | 0.0522 (9) | −0.0095 (7) | 0.0072 (7) | 0.0009 (7) |
O2 | 0.0757 (8) | 0.0680 (9) | 0.0809 (9) | −0.0302 (7) | 0.0020 (7) | 0.0097 (7) |
N3 | 0.0728 (9) | 0.0489 (8) | 0.0543 (8) | −0.0026 (7) | −0.0019 (7) | 0.0066 (7) |
C4 | 0.0579 (9) | 0.0507 (10) | 0.0543 (9) | 0.0038 (7) | 0.0026 (7) | −0.0080 (8) |
C41 | 0.0881 (14) | 0.0882 (16) | 0.0823 (14) | 0.0122 (12) | −0.0283 (11) | −0.0002 (12) |
C5 | 0.0475 (8) | 0.0431 (9) | 0.0728 (11) | −0.0042 (7) | 0.0049 (7) | −0.0064 (8) |
C6 | 0.0491 (7) | 0.0355 (8) | 0.0541 (8) | 0.0028 (6) | 0.0131 (6) | −0.0029 (7) |
C61 | 0.0659 (10) | 0.0556 (11) | 0.0739 (11) | 0.0052 (8) | 0.0272 (9) | 0.0151 (9) |
C7 | 0.0498 (8) | 0.0477 (9) | 0.0539 (8) | 0.0047 (7) | 0.0003 (7) | −0.0031 (7) |
C8 | 0.0525 (8) | 0.0486 (9) | 0.0476 (8) | 0.0068 (7) | 0.0088 (6) | −0.0011 (7) |
O8 | 0.0681 (7) | 0.0770 (9) | 0.0804 (9) | 0.0294 (7) | −0.0095 (6) | −0.0245 (7) |
C9 | 0.0495 (8) | 0.0446 (9) | 0.0446 (7) | 0.0004 (6) | 0.0097 (6) | 0.0003 (7) |
C10 | 0.0693 (10) | 0.0624 (12) | 0.0649 (10) | 0.0143 (9) | −0.0078 (9) | −0.0171 (9) |
C11 | 0.0619 (10) | 0.0684 (12) | 0.0772 (12) | 0.0162 (9) | −0.0076 (9) | −0.0169 (10) |
C12 | 0.0555 (8) | 0.0581 (11) | 0.0481 (8) | −0.0089 (8) | 0.0075 (7) | 0.0014 (7) |
C13 | 0.0679 (10) | 0.0607 (11) | 0.0562 (9) | −0.0067 (9) | 0.0110 (8) | −0.0112 (9) |
C14 | 0.0587 (9) | 0.0547 (11) | 0.0564 (9) | 0.0036 (8) | 0.0092 (7) | −0.0136 (8) |
Cl12 | 0.0758 (3) | 0.0869 (4) | 0.0721 (3) | −0.0159 (3) | −0.0137 (2) | −0.0039 (3) |
N1—C6 | 1.3607 (18) | C7—C8 | 1.521 (2) |
N1—C2 | 1.4116 (19) | C7—H7A | 0.9700 |
N1—C7 | 1.4648 (16) | C7—H7B | 0.9700 |
C2—O2 | 1.2210 (18) | C8—O8 | 1.2061 (18) |
C2—N3 | 1.3645 (18) | C8—C9 | 1.4924 (18) |
N3—C4 | 1.307 (2) | C9—C10 | 1.370 (2) |
C4—C5 | 1.402 (2) | C9—C14 | 1.390 (2) |
C4—C41 | 1.502 (2) | C10—C11 | 1.388 (2) |
C41—H41A | 0.9600 | C10—H10 | 0.9300 |
C41—H41B | 0.9600 | C11—C12 | 1.374 (2) |
C41—H41C | 0.9600 | C11—H11 | 0.9300 |
C5—C6 | 1.3586 (19) | C12—C13 | 1.367 (2) |
C5—H5 | 0.9300 | C12—Cl12 | 1.7284 (15) |
C6—C61 | 1.493 (2) | C13—C14 | 1.383 (2) |
C61—H61A | 0.9600 | C13—H13 | 0.9300 |
C61—H61B | 0.9600 | C14—H14 | 0.9300 |
C61—H61C | 0.9600 | ||
C6—N1—C2 | 122.06 (12) | N1—C7—C8 | 110.70 (12) |
C6—N1—C7 | 123.33 (13) | N1—C7—H7A | 109.5 |
C2—N1—C7 | 114.45 (12) | C8—C7—H7A | 109.5 |
O2—C2—N3 | 123.27 (16) | N1—C7—H7B | 109.5 |
O2—C2—N1 | 118.50 (14) | C8—C7—H7B | 109.5 |
N3—C2—N1 | 118.23 (14) | H7A—C7—H7B | 108.1 |
C4—N3—C2 | 119.31 (15) | O8—C8—C9 | 122.09 (15) |
N3—C4—C5 | 123.56 (14) | O8—C8—C7 | 120.45 (14) |
N3—C4—C41 | 116.99 (17) | C9—C8—C7 | 117.45 (13) |
C5—C4—C41 | 119.45 (16) | C10—C9—C14 | 119.13 (14) |
C4—C41—H41A | 109.5 | C10—C9—C8 | 122.87 (14) |
C4—C41—H41B | 109.5 | C14—C9—C8 | 117.98 (13) |
H41A—C41—H41B | 109.5 | C9—C10—C11 | 120.76 (17) |
C4—C41—H41C | 109.5 | C9—C10—H10 | 119.6 |
H41A—C41—H41C | 109.5 | C11—C10—H10 | 119.6 |
H41B—C41—H41C | 109.5 | C12—C11—C10 | 119.22 (17) |
C6—C5—C4 | 118.71 (15) | C12—C11—H11 | 120.4 |
C6—C5—H5 | 120.6 | C10—C11—H11 | 120.4 |
C4—C5—H5 | 120.6 | C13—C12—C11 | 120.97 (14) |
C5—C6—N1 | 118.13 (15) | C13—C12—Cl12 | 119.89 (13) |
C5—C6—C61 | 122.21 (15) | C11—C12—Cl12 | 119.14 (13) |
N1—C6—C61 | 119.66 (13) | C12—C13—C14 | 119.53 (16) |
C6—C61—H61A | 109.5 | C12—C13—H13 | 120.2 |
C6—C61—H61B | 109.5 | C14—C13—H13 | 120.2 |
H61A—C61—H61B | 109.5 | C13—C14—C9 | 120.36 (16) |
C6—C61—H61C | 109.5 | C13—C14—H14 | 119.8 |
H61A—C61—H61C | 109.5 | C9—C14—H14 | 119.8 |
H61B—C61—H61C | 109.5 |