Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806044795/ci2200sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806044795/ci2200Isup2.hkl |
CCDC reference: 629472
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- R factor = 0.034
- wR factor = 0.097
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.63 mm
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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).
C13H15ClN2O3 | F(000) = 592 |
Mr = 282.72 | Dx = 1.341 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 34794 reflections |
a = 7.2025 (4) Å | θ = 2.0–27.1° |
b = 19.3625 (14) Å | µ = 0.28 mm−1 |
c = 10.6093 (6) Å | T = 296 K |
β = 108.852 (4)° | Prism, brown |
V = 1400.19 (15) Å3 | 0.63 × 0.48 × 0.23 mm |
Z = 4 |
Stoe IPDS-II diffractometer | 2743 independent reflections |
Radiation source: fine-focus sealed tube | 2060 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.1° |
ω scans | h = −8→8 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −23→23 |
Tmin = 0.869, Tmax = 0.933 | l = −13→13 |
24033 measured reflections |
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)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.054P)2 + 0.0706P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2743 reflections | Δρmax = 0.16 e Å−3 |
178 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0090 (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 | ||
C1 | 0.74015 (19) | 0.45587 (7) | 0.46323 (14) | 0.0543 (3) | |
C2 | 0.7195 (2) | 0.40259 (8) | 0.54448 (14) | 0.0616 (4) | |
H2 | 0.7243 | 0.4115 | 0.6316 | 0.074* | |
C3 | 0.6916 (2) | 0.33608 (8) | 0.49541 (15) | 0.0636 (4) | |
H3 | 0.6786 | 0.3005 | 0.5507 | 0.076* | |
C4 | 0.6827 (2) | 0.32085 (7) | 0.36596 (15) | 0.0604 (4) | |
C5 | 0.7076 (2) | 0.37482 (8) | 0.28806 (15) | 0.0655 (4) | |
H5 | 0.7049 | 0.3659 | 0.2014 | 0.079* | |
C6 | 0.7365 (2) | 0.44164 (8) | 0.33510 (14) | 0.0622 (4) | |
H6 | 0.7534 | 0.4770 | 0.2806 | 0.075* | |
C7 | 0.6425 (3) | 0.24842 (9) | 0.31146 (18) | 0.0797 (5) | |
H7A | 0.6653 | 0.2163 | 0.3838 | 0.120* | |
H7B | 0.7280 | 0.2379 | 0.2610 | 0.120* | |
H7C | 0.5085 | 0.2450 | 0.2549 | 0.120* | |
C8 | 0.7891 (2) | 0.60625 (7) | 0.66683 (13) | 0.0559 (3) | |
C9 | 0.7977 (2) | 0.66393 (8) | 0.57809 (15) | 0.0593 (3) | |
C10 | 0.8164 (3) | 0.78326 (8) | 0.54468 (17) | 0.0740 (4) | |
H10A | 0.6970 | 0.7831 | 0.4687 | 0.089* | |
H10B | 0.9277 | 0.7798 | 0.5125 | 0.089* | |
C11 | 0.8294 (3) | 0.84787 (8) | 0.6240 (2) | 0.0911 (6) | |
H11A | 0.8299 | 0.8872 | 0.5689 | 0.137* | |
H11B | 0.9481 | 0.8473 | 0.6987 | 0.137* | |
H11C | 0.7186 | 0.8506 | 0.6553 | 0.137* | |
C12 | 0.7972 (2) | 0.61422 (7) | 0.80682 (14) | 0.0599 (4) | |
C13 | 0.7698 (3) | 0.54771 (8) | 0.87467 (15) | 0.0683 (4) | |
H13A | 0.8764 | 0.5163 | 0.8783 | 0.082* | |
H13B | 0.6481 | 0.5259 | 0.8222 | 0.082* | |
Cl1 | 0.76430 (9) | 0.56215 (3) | 1.03745 (5) | 0.0942 (2) | |
N1 | 0.76387 (18) | 0.52491 (7) | 0.50608 (13) | 0.0593 (3) | |
N2 | 0.77012 (16) | 0.54170 (6) | 0.62658 (11) | 0.0551 (3) | |
O1 | 0.81609 (17) | 0.72584 (5) | 0.63345 (10) | 0.0687 (3) | |
O2 | 0.78578 (18) | 0.65502 (5) | 0.46214 (10) | 0.0726 (3) | |
O3 | 0.8245 (2) | 0.66844 (6) | 0.86612 (11) | 0.0902 (4) | |
H1 | 0.772 (2) | 0.5554 (9) | 0.4522 (17) | 0.077 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0547 (8) | 0.0527 (7) | 0.0570 (8) | 0.0013 (6) | 0.0199 (6) | −0.0008 (6) |
C2 | 0.0745 (9) | 0.0596 (8) | 0.0528 (7) | 0.0013 (7) | 0.0236 (7) | 0.0018 (6) |
C3 | 0.0746 (9) | 0.0547 (8) | 0.0633 (8) | 0.0031 (7) | 0.0247 (7) | 0.0062 (7) |
C4 | 0.0602 (8) | 0.0574 (8) | 0.0644 (8) | 0.0045 (6) | 0.0211 (7) | −0.0028 (7) |
C5 | 0.0781 (10) | 0.0660 (9) | 0.0576 (8) | 0.0009 (7) | 0.0290 (7) | −0.0057 (7) |
C6 | 0.0735 (9) | 0.0612 (9) | 0.0576 (8) | 0.0000 (7) | 0.0293 (7) | 0.0043 (6) |
C7 | 0.0977 (12) | 0.0605 (9) | 0.0825 (11) | 0.0010 (9) | 0.0312 (9) | −0.0084 (8) |
C8 | 0.0566 (8) | 0.0537 (8) | 0.0572 (8) | 0.0015 (6) | 0.0179 (6) | 0.0014 (6) |
C9 | 0.0629 (8) | 0.0542 (8) | 0.0619 (8) | 0.0002 (6) | 0.0217 (7) | 0.0008 (6) |
C10 | 0.1014 (12) | 0.0527 (8) | 0.0747 (10) | −0.0003 (8) | 0.0378 (9) | 0.0079 (7) |
C11 | 0.1302 (16) | 0.0569 (10) | 0.0997 (14) | −0.0033 (10) | 0.0557 (13) | 0.0000 (9) |
C12 | 0.0649 (9) | 0.0537 (8) | 0.0573 (8) | 0.0019 (6) | 0.0148 (7) | 0.0005 (6) |
C13 | 0.0846 (11) | 0.0621 (9) | 0.0572 (8) | 0.0081 (8) | 0.0217 (8) | 0.0067 (7) |
Cl1 | 0.1391 (5) | 0.0849 (3) | 0.0714 (3) | 0.0100 (3) | 0.0517 (3) | 0.0103 (2) |
N1 | 0.0698 (8) | 0.0544 (7) | 0.0575 (7) | −0.0008 (5) | 0.0257 (6) | 0.0014 (5) |
N2 | 0.0549 (6) | 0.0546 (6) | 0.0555 (6) | 0.0019 (5) | 0.0174 (5) | −0.0004 (5) |
O1 | 0.0935 (8) | 0.0508 (6) | 0.0665 (6) | −0.0010 (5) | 0.0324 (6) | 0.0028 (5) |
O2 | 0.1006 (8) | 0.0595 (6) | 0.0641 (6) | −0.0027 (5) | 0.0354 (6) | 0.0034 (5) |
O3 | 0.1433 (12) | 0.0628 (7) | 0.0629 (6) | −0.0142 (7) | 0.0313 (7) | −0.0076 (6) |
C1—C6 | 1.3788 (19) | C8—C12 | 1.4755 (19) |
C1—C2 | 1.383 (2) | C9—O2 | 1.2175 (16) |
C1—N1 | 1.4045 (18) | C9—O1 | 1.3225 (17) |
C2—C3 | 1.379 (2) | C10—O1 | 1.4575 (18) |
C2—H2 | 0.93 | C10—C11 | 1.493 (2) |
C3—C4 | 1.386 (2) | C10—H10A | 0.97 |
C3—H3 | 0.93 | C10—H10B | 0.97 |
C4—C5 | 1.380 (2) | C11—H11A | 0.96 |
C4—C7 | 1.509 (2) | C11—H11B | 0.96 |
C5—C6 | 1.378 (2) | C11—H11C | 0.96 |
C5—H5 | 0.93 | C12—O3 | 1.2069 (18) |
C6—H6 | 0.93 | C12—C13 | 1.519 (2) |
C7—H7A | 0.96 | C13—Cl1 | 1.7626 (16) |
C7—H7B | 0.96 | C13—H13A | 0.97 |
C7—H7C | 0.96 | C13—H13B | 0.97 |
C8—N2 | 1.3135 (18) | N1—N2 | 1.3057 (17) |
C8—C9 | 1.475 (2) | N1—H1 | 0.836 (18) |
C6—C1—C2 | 119.60 (13) | O2—C9—C8 | 122.27 (13) |
C6—C1—N1 | 118.08 (13) | O1—C9—C8 | 114.95 (13) |
C2—C1—N1 | 122.32 (13) | O1—C10—C11 | 106.73 (13) |
C3—C2—C1 | 119.54 (13) | O1—C10—H10A | 110.4 |
C3—C2—H2 | 120.2 | C11—C10—H10A | 110.4 |
C1—C2—H2 | 120.2 | O1—C10—H10B | 110.4 |
C2—C3—C4 | 121.84 (14) | C11—C10—H10B | 110.4 |
C2—C3—H3 | 119.1 | H10A—C10—H10B | 108.6 |
C4—C3—H3 | 119.1 | C10—C11—H11A | 109.5 |
C5—C4—C3 | 117.33 (14) | C10—C11—H11B | 109.5 |
C5—C4—C7 | 121.36 (14) | H11A—C11—H11B | 109.5 |
C3—C4—C7 | 121.29 (14) | C10—C11—H11C | 109.5 |
C6—C5—C4 | 121.86 (14) | H11A—C11—H11C | 109.5 |
C6—C5—H5 | 119.1 | H11B—C11—H11C | 109.5 |
C4—C5—H5 | 119.1 | O3—C12—C8 | 124.23 (14) |
C5—C6—C1 | 119.81 (13) | O3—C12—C13 | 120.98 (14) |
C5—C6—H6 | 120.1 | C8—C12—C13 | 114.80 (12) |
C1—C6—H6 | 120.1 | C12—C13—Cl1 | 112.17 (11) |
C4—C7—H7A | 109.5 | C12—C13—H13A | 109.2 |
C4—C7—H7B | 109.5 | Cl1—C13—H13A | 109.2 |
H7A—C7—H7B | 109.5 | C12—C13—H13B | 109.2 |
C4—C7—H7C | 109.5 | Cl1—C13—H13B | 109.2 |
H7A—C7—H7C | 109.5 | H13A—C13—H13B | 107.9 |
H7B—C7—H7C | 109.5 | N2—N1—C1 | 121.07 (12) |
N2—C8—C9 | 122.31 (12) | N2—N1—H1 | 120.4 (12) |
N2—C8—C12 | 113.13 (12) | C1—N1—H1 | 118.6 (12) |
C9—C8—C12 | 124.55 (13) | N1—N2—C8 | 121.49 (12) |
O2—C9—O1 | 122.77 (13) | C9—O1—C10 | 115.17 (12) |
C6—C1—C2—C3 | −1.2 (2) | N2—C8—C12—O3 | 175.96 (15) |
N1—C1—C2—C3 | 178.35 (13) | C9—C8—C12—O3 | −5.0 (2) |
C1—C2—C3—C4 | −0.3 (2) | N2—C8—C12—C13 | −3.55 (18) |
C2—C3—C4—C5 | 1.6 (2) | C9—C8—C12—C13 | 175.46 (14) |
C2—C3—C4—C7 | −177.02 (15) | O3—C12—C13—Cl1 | 4.6 (2) |
C3—C4—C5—C6 | −1.3 (2) | C8—C12—C13—Cl1 | −175.89 (11) |
C7—C4—C5—C6 | 177.32 (15) | C6—C1—N1—N2 | −179.45 (12) |
C4—C5—C6—C1 | −0.3 (2) | C2—C1—N1—N2 | 1.0 (2) |
C2—C1—C6—C5 | 1.5 (2) | C1—N1—N2—C8 | −178.88 (12) |
N1—C1—C6—C5 | −178.07 (13) | C9—C8—N2—N1 | 2.1 (2) |
N2—C8—C9—O2 | 0.7 (2) | C12—C8—N2—N1 | −178.81 (12) |
C12—C8—C9—O2 | −178.22 (14) | O2—C9—O1—C10 | 1.5 (2) |
N2—C8—C9—O1 | 179.71 (12) | C8—C9—O1—C10 | −177.55 (13) |
C12—C8—C9—O1 | 0.8 (2) | C11—C10—O1—C9 | 177.54 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.836 (18) | 1.933 (18) | 2.5762 (16) | 133 (2) |