Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011919/sk3105sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011919/sk3105Isup2.hkl |
CCDC reference: 643115
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
C13H12ClNO4 | F(000) = 584 |
Mr = 281.69 | Dx = 1.495 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 6509 reflections |
a = 9.6954 (6) Å | θ = 4.8–56.0° |
b = 11.0961 (6) Å | µ = 0.32 mm−1 |
c = 12.0810 (7) Å | T = 293 K |
β = 105.671 (1)° | Needles, pale yellow |
V = 1251.38 (13) Å3 | 0.21 × 0.20 × 0.17 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 2663 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.017 |
Graphite monochromator | θmax = 28.0°, θmin = 2.4° |
ω scans | h = −12→12 |
10525 measured reflections | k = −14→14 |
2938 independent reflections | l = −15→15 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0598P)2 + 0.263P] where P = (Fo2 + 2Fc2)/3 |
2938 reflections | (Δ/σ)max < 0.001 |
174 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Experimental. 1H NMR (200 MHz, CDCl3): δ 8.22 (d, J = 7.7 Hz, 1H), 8.13 (d, J = 7.7 Hz, 1H), 7.17 (t, J = 2.2 Hz, 1H), 5.89 (s, 1H), 4.01 (s, 3H), 2.65 (m, 2H), 2.5 (m, 2H); 13C NMR (50 MHz, CDCl3): δ 209.3, 164.2, 160.7, 148.8, 146.9, 144.2, 139.8, 137.9, 124.1, 65.7, 52.9, 34.9, 26.7; MS (EI) m/z: 281 (M+), 246, 218, 202, 188, 122, 69; IR (KBr): 3414, 2954, 1723, 1689, 1315 cm-1. Analysis calculated for C13H12ClNO4: C 55.43, H 4.29, N 4.97%; found: C 55.67, H 4.67, N 5.14%. |
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 | 1.21457 (4) | −0.00377 (3) | 0.96935 (3) | 0.04545 (13) | |
O1 | 0.84559 (14) | −0.02271 (10) | 0.72697 (10) | 0.0602 (3) | |
O2 | 1.18862 (13) | 0.21769 (14) | 0.69314 (11) | 0.0713 (4) | |
O3 | 1.06068 (12) | 0.28223 (11) | 1.24012 (8) | 0.0538 (3) | |
O4 | 0.94434 (13) | 0.43440 (9) | 1.13313 (8) | 0.0515 (3) | |
N1 | 1.09248 (11) | 0.17295 (10) | 1.04613 (9) | 0.0361 (2) | |
C1 | 1.08735 (13) | 0.11088 (11) | 0.95204 (10) | 0.0332 (3) | |
C2 | 0.98999 (13) | 0.12958 (11) | 0.84460 (10) | 0.0341 (3) | |
C3 | 0.89915 (14) | 0.22725 (12) | 0.83811 (11) | 0.0398 (3) | |
C4 | 0.90490 (15) | 0.29762 (12) | 0.93384 (11) | 0.0400 (3) | |
C5 | 1.00063 (14) | 0.26542 (11) | 1.03675 (11) | 0.0360 (3) | |
C6 | 1.00671 (14) | 0.32682 (12) | 1.14842 (11) | 0.0400 (3) | |
C7 | 0.9427 (2) | 0.49659 (15) | 1.23831 (15) | 0.0630 (5) | |
C8 | 0.97346 (15) | 0.04595 (12) | 0.74250 (11) | 0.0418 (3) | |
C9 | 0.96391 (14) | 0.11435 (12) | 0.63354 (11) | 0.0393 (3) | |
C10 | 1.07752 (16) | 0.19694 (15) | 0.62099 (12) | 0.0474 (3) | |
C11 | 1.0302 (2) | 0.2514 (2) | 0.50185 (14) | 0.0631 (5) | |
C12 | 0.88990 (18) | 0.18923 (15) | 0.44368 (12) | 0.0513 (4) | |
C13 | 0.86066 (17) | 0.11073 (13) | 0.53538 (12) | 0.0463 (3) | |
H1 | 0.8591 | −0.0772 | 0.7746 | 0.090* | |
H3 | 0.8335 | 0.2458 | 0.7685 | 0.048* | |
H4 | 0.8460 | 0.3647 | 0.9291 | 0.048* | |
H7A | 0.8914 | 0.4491 | 1.2804 | 0.094* | |
H7B | 0.8964 | 0.5733 | 1.2198 | 0.094* | |
H7C | 1.0392 | 0.5086 | 1.2843 | 0.094* | |
H8 | 1.0557 | −0.0088 | 0.7573 | 0.050* | |
H11A | 1.1009 | 0.2367 | 0.4600 | 0.076* | |
H11B | 1.0162 | 0.3377 | 0.5062 | 0.076* | |
H12A | 0.8138 | 0.2477 | 0.4169 | 0.062* | |
H12B | 0.8991 | 0.1414 | 0.3788 | 0.062* | |
H13 | 0.7785 | 0.0640 | 0.5248 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0436 (2) | 0.0473 (2) | 0.0436 (2) | 0.01325 (13) | 0.00857 (15) | 0.00518 (13) |
N1 | 0.0378 (5) | 0.0390 (5) | 0.0302 (5) | 0.0003 (4) | 0.0072 (4) | 0.0031 (4) |
C5 | 0.0406 (6) | 0.0359 (6) | 0.0321 (6) | −0.0014 (5) | 0.0106 (5) | 0.0022 (5) |
C1 | 0.0330 (6) | 0.0340 (6) | 0.0323 (6) | 0.0015 (4) | 0.0085 (5) | 0.0050 (4) |
O4 | 0.0758 (7) | 0.0416 (5) | 0.0378 (5) | 0.0075 (5) | 0.0165 (5) | −0.0032 (4) |
O3 | 0.0667 (7) | 0.0604 (7) | 0.0322 (5) | 0.0103 (5) | 0.0097 (5) | 0.0017 (4) |
C9 | 0.0473 (7) | 0.0385 (6) | 0.0312 (6) | 0.0077 (5) | 0.0089 (5) | −0.0037 (5) |
C4 | 0.0453 (7) | 0.0387 (7) | 0.0354 (6) | 0.0081 (5) | 0.0099 (5) | 0.0037 (5) |
C2 | 0.0374 (6) | 0.0345 (6) | 0.0295 (6) | −0.0010 (5) | 0.0077 (5) | 0.0023 (4) |
C8 | 0.0510 (8) | 0.0366 (7) | 0.0326 (6) | 0.0045 (6) | 0.0024 (5) | −0.0019 (5) |
C3 | 0.0427 (7) | 0.0416 (7) | 0.0315 (6) | 0.0056 (5) | 0.0038 (5) | 0.0039 (5) |
O1 | 0.0786 (8) | 0.0448 (6) | 0.0446 (6) | −0.0206 (5) | −0.0053 (5) | 0.0075 (5) |
C6 | 0.0438 (7) | 0.0422 (7) | 0.0348 (6) | −0.0022 (5) | 0.0118 (5) | −0.0002 (5) |
O2 | 0.0534 (7) | 0.1026 (10) | 0.0511 (7) | −0.0151 (7) | 0.0024 (5) | −0.0012 (7) |
C12 | 0.0618 (9) | 0.0582 (9) | 0.0319 (6) | 0.0109 (7) | 0.0090 (6) | 0.0013 (6) |
C13 | 0.0522 (8) | 0.0467 (7) | 0.0353 (7) | 0.0005 (6) | 0.0039 (6) | −0.0017 (5) |
C10 | 0.0476 (8) | 0.0587 (9) | 0.0363 (7) | 0.0027 (6) | 0.0121 (6) | −0.0041 (6) |
C11 | 0.0651 (10) | 0.0842 (13) | 0.0413 (8) | −0.0058 (9) | 0.0166 (7) | 0.0099 (8) |
C7 | 0.0912 (13) | 0.0520 (10) | 0.0481 (9) | 0.0047 (8) | 0.0228 (9) | −0.0129 (7) |
Cl1—C1 | 1.7447 (12) | C8—O1 | 1.4237 (18) |
N1—C1 | 1.3186 (16) | C8—H8 | 0.9800 |
N1—C5 | 1.3431 (17) | C3—H3 | 0.9300 |
C5—C4 | 1.3825 (18) | O1—H1 | 0.8200 |
C5—C6 | 1.4982 (18) | O2—C10 | 1.2107 (18) |
C1—C2 | 1.3990 (16) | C12—C13 | 1.495 (2) |
O4—C6 | 1.3283 (17) | C12—C11 | 1.517 (2) |
O4—C7 | 1.4497 (18) | C12—H12A | 0.9700 |
O3—C6 | 1.1970 (16) | C12—H12B | 0.9700 |
C9—C13 | 1.3299 (19) | C13—H13 | 0.9300 |
C9—C10 | 1.472 (2) | C10—C11 | 1.514 (2) |
C9—C8 | 1.5006 (18) | C11—H11A | 0.9700 |
C4—C3 | 1.3840 (18) | C11—H11B | 0.9700 |
C4—H4 | 0.9300 | C7—H7A | 0.9600 |
C2—C3 | 1.3853 (18) | C7—H7B | 0.9600 |
C2—C8 | 1.5170 (17) | C7—H7C | 0.9600 |
C1—N1—C5 | 117.16 (11) | O3—C6—O4 | 124.67 (12) |
N1—C5—C4 | 122.83 (12) | O3—C6—C5 | 123.13 (13) |
N1—C5—C6 | 114.04 (11) | O4—C6—C5 | 112.20 (11) |
C4—C5—C6 | 123.08 (12) | C13—C12—C11 | 104.31 (12) |
N1—C1—C2 | 125.54 (11) | C13—C12—H12A | 110.9 |
N1—C1—Cl1 | 114.63 (9) | C11—C12—H12A | 110.9 |
C2—C1—Cl1 | 119.83 (9) | C13—C12—H12B | 110.9 |
C6—O4—C7 | 114.73 (12) | C11—C12—H12B | 110.9 |
C13—C9—C10 | 109.33 (13) | H12A—C12—H12B | 108.9 |
C13—C9—C8 | 128.33 (13) | C9—C13—C12 | 113.29 (14) |
C10—C9—C8 | 122.33 (12) | C9—C13—H13 | 123.4 |
C5—C4—C3 | 118.12 (12) | C12—C13—H13 | 123.4 |
C5—C4—H4 | 120.9 | O2—C10—C9 | 126.11 (14) |
C3—C4—H4 | 120.9 | O2—C10—C11 | 126.23 (16) |
C3—C2—C1 | 115.33 (11) | C9—C10—C11 | 107.66 (13) |
C3—C2—C8 | 120.44 (11) | C10—C11—C12 | 105.23 (14) |
C1—C2—C8 | 124.07 (11) | C10—C11—H11A | 110.7 |
O1—C8—C9 | 108.05 (11) | C12—C11—H11A | 110.7 |
O1—C8—C2 | 109.36 (12) | C10—C11—H11B | 110.7 |
C9—C8—C2 | 111.83 (11) | C12—C11—H11B | 110.7 |
O1—C8—H8 | 109.2 | H11A—C11—H11B | 108.8 |
C9—C8—H8 | 109.2 | O4—C7—H7A | 109.5 |
C2—C8—H8 | 109.2 | O4—C7—H7B | 109.5 |
C4—C3—C2 | 120.84 (12) | H7A—C7—H7B | 109.5 |
C4—C3—H3 | 119.6 | O4—C7—H7C | 109.5 |
C2—C3—H3 | 119.6 | H7A—C7—H7C | 109.5 |
C8—O1—H1 | 109.5 | H7B—C7—H7C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3i | 0.82 | 2.43 | 3.0135 (17) | 129 |
O1—H1···N1i | 0.82 | 2.34 | 3.1247 (15) | 160 |
C3—H3···O3ii | 0.93 | 2.59 | 3.1753 (18) | 121 |
C4—H4···O1iii | 0.93 | 2.58 | 3.3314 (17) | 138 |
C8—H8···Cl1 | 0.98 | 2.61 | 3.1335 (13) | 114 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+3/2, y+1/2, −z+3/2. |