Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015012980/rz5163sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2056989015012980/rz5163Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015012980/rz5163Isup3.cml |
CCDC reference: 1410873
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- R factor = 0.039
- wR factor = 0.106
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 -- C12 .. 5.1 su PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 7.352 Check
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size .... 0.80 mm PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 3 ALERT level G = General information/check it is not something unexpected 1 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
C14H14ClN3O2 | F(000) = 608 |
Mr = 291.73 | Dx = 1.399 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 11553 reflections |
a = 13.0977 (9) Å | θ = 1.6–28.0° |
b = 7.4932 (4) Å | µ = 0.28 mm−1 |
c = 14.1123 (9) Å | T = 296 K |
β = 90.149 (5)° | Prism, yellow |
V = 1385.03 (15) Å3 | 0.80 × 0.38 × 0.08 mm |
Z = 4 |
Stoe IPDS 2 diffractometer | 2868 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2267 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.028 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.5°, θmin = 1.6° |
ω scans | h = −16→16 |
Absorption correction: integration (XRED-32; Stoe & Cie, 2002) | k = −9→9 |
Tmin = 0.880, Tmax = 0.978 | l = −17→17 |
8760 measured reflections |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0578P)2 + 0.1445P] where P = (Fo2 + 2Fc2)/3 |
2868 reflections | (Δ/σ)max < 0.001 |
181 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | 0.16215 (4) | 0.21784 (11) | 0.00258 (4) | 0.0999 (2) | |
O1 | 0.42246 (7) | 0.04185 (14) | 0.40107 (6) | 0.0472 (3) | |
O2 | 0.99398 (9) | 0.3320 (2) | 0.22281 (11) | 0.0764 (5) | |
N1 | 0.58954 (8) | 0.10751 (17) | 0.41972 (8) | 0.0454 (4) | |
N2 | 0.68499 (9) | 0.16004 (17) | 0.39371 (8) | 0.0465 (4) | |
N3 | 0.78867 (9) | 0.28188 (18) | 0.27895 (9) | 0.0499 (4) | |
C1 | 0.42580 (10) | 0.17384 (18) | 0.20628 (9) | 0.0394 (4) | |
C2 | 0.43734 (11) | 0.1304 (2) | 0.11136 (10) | 0.0500 (5) | |
C3 | 0.35657 (13) | 0.1423 (2) | 0.04893 (11) | 0.0585 (5) | |
C4 | 0.26364 (12) | 0.1993 (2) | 0.08154 (11) | 0.0563 (5) | |
C5 | 0.24891 (11) | 0.2423 (2) | 0.17507 (12) | 0.0534 (5) | |
C6 | 0.33006 (10) | 0.2283 (2) | 0.23759 (10) | 0.0455 (4) | |
C7 | 0.51501 (10) | 0.16802 (18) | 0.27082 (9) | 0.0382 (4) | |
C8 | 0.50364 (10) | 0.10152 (19) | 0.36713 (9) | 0.0393 (4) | |
C9 | 0.69357 (10) | 0.21801 (19) | 0.30668 (10) | 0.0423 (4) | |
C10 | 0.60866 (10) | 0.22402 (19) | 0.24347 (10) | 0.0427 (4) | |
C11 | 0.87216 (12) | 0.2561 (3) | 0.34556 (13) | 0.0625 (6) | |
C12 | 0.96240 (13) | 0.3681 (3) | 0.31683 (15) | 0.0724 (7) | |
C13 | 0.91285 (13) | 0.3718 (4) | 0.16077 (15) | 0.0835 (8) | |
C14 | 0.81944 (13) | 0.2585 (3) | 0.18073 (14) | 0.0745 (7) | |
H1 | 0.58330 | 0.07350 | 0.47760 | 0.0550* | |
H2 | 0.50070 | 0.09260 | 0.08950 | 0.0600* | |
H3 | 0.36500 | 0.11210 | −0.01450 | 0.0700* | |
H5 | 0.18530 | 0.28040 | 0.19610 | 0.0640* | |
H6 | 0.32050 | 0.25550 | 0.30120 | 0.0550* | |
H10 | 0.61770 | 0.26720 | 0.18230 | 0.0510* | |
H11A | 0.89160 | 0.13120 | 0.34680 | 0.0750* | |
H11B | 0.85030 | 0.28970 | 0.40870 | 0.0750* | |
H12A | 0.94450 | 0.49330 | 0.32220 | 0.0870* | |
H12B | 1.01870 | 0.34500 | 0.35990 | 0.0870* | |
H13A | 0.93470 | 0.35190 | 0.09600 | 0.1000* | |
H13B | 0.89500 | 0.49690 | 0.16710 | 0.1000* | |
H14A | 0.76410 | 0.29350 | 0.13890 | 0.0890* | |
H14B | 0.83490 | 0.13390 | 0.16890 | 0.0890* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0672 (3) | 0.1570 (6) | 0.0753 (3) | −0.0021 (3) | −0.0358 (2) | 0.0166 (3) |
O1 | 0.0438 (5) | 0.0619 (6) | 0.0358 (5) | −0.0068 (5) | 0.0003 (4) | 0.0016 (4) |
O2 | 0.0386 (5) | 0.0910 (10) | 0.0996 (10) | 0.0011 (6) | 0.0060 (6) | 0.0097 (8) |
N1 | 0.0441 (6) | 0.0552 (7) | 0.0370 (6) | −0.0050 (5) | −0.0037 (4) | 0.0043 (5) |
N2 | 0.0401 (6) | 0.0511 (7) | 0.0482 (6) | −0.0027 (5) | −0.0062 (5) | 0.0051 (5) |
N3 | 0.0353 (6) | 0.0576 (8) | 0.0569 (7) | −0.0008 (5) | −0.0028 (5) | 0.0103 (6) |
C1 | 0.0399 (7) | 0.0394 (7) | 0.0390 (6) | −0.0022 (5) | −0.0027 (5) | 0.0050 (5) |
C2 | 0.0474 (8) | 0.0604 (9) | 0.0422 (7) | 0.0042 (7) | 0.0001 (6) | 0.0033 (6) |
C3 | 0.0631 (9) | 0.0735 (11) | 0.0389 (7) | −0.0033 (8) | −0.0075 (6) | 0.0036 (7) |
C4 | 0.0480 (8) | 0.0671 (11) | 0.0537 (8) | −0.0070 (7) | −0.0159 (6) | 0.0131 (7) |
C5 | 0.0378 (7) | 0.0626 (10) | 0.0598 (9) | 0.0002 (6) | −0.0038 (6) | 0.0085 (7) |
C6 | 0.0405 (7) | 0.0524 (8) | 0.0437 (7) | −0.0010 (6) | −0.0017 (5) | 0.0017 (6) |
C7 | 0.0389 (6) | 0.0372 (7) | 0.0386 (7) | 0.0030 (5) | −0.0018 (5) | 0.0009 (5) |
C8 | 0.0411 (6) | 0.0404 (7) | 0.0365 (6) | −0.0006 (5) | −0.0019 (5) | −0.0023 (5) |
C9 | 0.0371 (6) | 0.0403 (7) | 0.0496 (7) | 0.0024 (5) | −0.0029 (5) | 0.0037 (6) |
C10 | 0.0399 (7) | 0.0441 (8) | 0.0440 (7) | 0.0039 (6) | −0.0010 (5) | 0.0079 (6) |
C11 | 0.0414 (8) | 0.0720 (11) | 0.0740 (11) | −0.0014 (7) | −0.0124 (7) | 0.0149 (9) |
C12 | 0.0418 (8) | 0.0806 (13) | 0.0947 (14) | −0.0067 (8) | −0.0117 (8) | 0.0124 (11) |
C13 | 0.0474 (9) | 0.1222 (19) | 0.0809 (13) | −0.0066 (10) | 0.0089 (8) | 0.0210 (13) |
C14 | 0.0456 (9) | 0.1111 (16) | 0.0669 (11) | −0.0097 (9) | 0.0074 (8) | 0.0022 (11) |
Cl1—C4 | 1.7379 (17) | C7—C8 | 1.4556 (18) |
O1—C8 | 1.2500 (16) | C7—C10 | 1.3535 (19) |
O2—C12 | 1.417 (3) | C9—C10 | 1.4246 (19) |
O2—C13 | 1.407 (2) | C11—C12 | 1.506 (3) |
N1—N2 | 1.3620 (16) | C13—C14 | 1.516 (3) |
N1—C8 | 1.3470 (17) | C2—H2 | 0.9300 |
N2—C9 | 1.3079 (18) | C3—H3 | 0.9300 |
N3—C9 | 1.3915 (18) | C5—H5 | 0.9300 |
N3—C11 | 1.453 (2) | C6—H6 | 0.9300 |
N3—C14 | 1.455 (2) | C10—H10 | 0.9300 |
N1—H1 | 0.8600 | C11—H11A | 0.9700 |
C1—C2 | 1.3872 (19) | C11—H11B | 0.9700 |
C1—C6 | 1.3918 (19) | C12—H12A | 0.9700 |
C1—C7 | 1.4803 (18) | C12—H12B | 0.9700 |
C2—C3 | 1.378 (2) | C13—H13A | 0.9700 |
C3—C4 | 1.371 (2) | C13—H13B | 0.9700 |
C4—C5 | 1.373 (2) | C14—H14A | 0.9700 |
C5—C6 | 1.384 (2) | C14—H14B | 0.9700 |
C12—O2—C13 | 108.69 (14) | N3—C14—C13 | 109.58 (16) |
N2—N1—C8 | 128.84 (11) | C1—C2—H2 | 119.00 |
N1—N2—C9 | 115.48 (11) | C3—C2—H2 | 119.00 |
C9—N3—C11 | 116.43 (13) | C2—C3—H3 | 120.00 |
C9—N3—C14 | 118.48 (13) | C4—C3—H3 | 120.00 |
C11—N3—C14 | 112.98 (13) | C4—C5—H5 | 120.00 |
C8—N1—H1 | 116.00 | C6—C5—H5 | 120.00 |
N2—N1—H1 | 116.00 | C1—C6—H6 | 120.00 |
C2—C1—C7 | 119.96 (12) | C5—C6—H6 | 120.00 |
C2—C1—C6 | 118.42 (12) | C7—C10—H10 | 119.00 |
C6—C1—C7 | 121.58 (12) | C9—C10—H10 | 119.00 |
C1—C2—C3 | 121.12 (14) | N3—C11—H11A | 110.00 |
C2—C3—C4 | 119.11 (14) | N3—C11—H11B | 110.00 |
Cl1—C4—C3 | 119.21 (12) | C12—C11—H11A | 110.00 |
Cl1—C4—C5 | 119.25 (12) | C12—C11—H11B | 110.00 |
C3—C4—C5 | 121.54 (15) | H11A—C11—H11B | 108.00 |
C4—C5—C6 | 119.06 (14) | O2—C12—H12A | 109.00 |
C1—C6—C5 | 120.73 (13) | O2—C12—H12B | 109.00 |
C8—C7—C10 | 117.86 (12) | C11—C12—H12A | 109.00 |
C1—C7—C10 | 122.00 (12) | C11—C12—H12B | 109.00 |
C1—C7—C8 | 120.14 (11) | H12A—C12—H12B | 108.00 |
O1—C8—N1 | 120.72 (12) | O2—C13—H13A | 109.00 |
O1—C8—C7 | 124.71 (12) | O2—C13—H13B | 109.00 |
N1—C8—C7 | 114.57 (12) | C14—C13—H13A | 109.00 |
N2—C9—N3 | 117.23 (12) | C14—C13—H13B | 109.00 |
N3—C9—C10 | 120.73 (13) | H13A—C13—H13B | 108.00 |
N2—C9—C10 | 121.98 (12) | N3—C14—H14A | 110.00 |
C7—C10—C9 | 121.21 (13) | N3—C14—H14B | 110.00 |
N3—C11—C12 | 109.97 (16) | C13—C14—H14A | 110.00 |
O2—C12—C11 | 112.14 (16) | C13—C14—H14B | 110.00 |
O2—C13—C14 | 111.97 (19) | H14A—C14—H14B | 108.00 |
C13—O2—C12—C11 | 60.9 (2) | C7—C1—C6—C5 | 176.41 (13) |
C12—O2—C13—C14 | −61.1 (2) | C2—C1—C7—C10 | 39.3 (2) |
C8—N1—N2—C9 | 2.5 (2) | C6—C1—C7—C10 | −138.37 (15) |
N2—N1—C8—C7 | −2.9 (2) | C1—C2—C3—C4 | 0.5 (2) |
N2—N1—C8—O1 | 176.78 (13) | C2—C3—C4—Cl1 | 178.98 (12) |
N1—N2—C9—C10 | −0.5 (2) | C2—C3—C4—C5 | −0.9 (2) |
N1—N2—C9—N3 | 176.65 (12) | C3—C4—C5—C6 | 0.3 (2) |
C11—N3—C9—C10 | −175.00 (15) | Cl1—C4—C5—C6 | −179.64 (12) |
C14—N3—C11—C12 | 51.2 (2) | C4—C5—C6—C1 | 0.9 (2) |
C9—N3—C11—C12 | −166.70 (15) | C1—C7—C8—O1 | 2.1 (2) |
C11—N3—C9—N2 | 7.8 (2) | C10—C7—C8—O1 | −178.24 (14) |
C14—N3—C9—N2 | 147.76 (15) | C10—C7—C8—N1 | 1.46 (19) |
C11—N3—C14—C13 | −51.3 (2) | C8—C7—C10—C9 | 0.1 (2) |
C14—N3—C9—C10 | −35.0 (2) | C1—C7—C10—C9 | 179.78 (13) |
C9—N3—C14—C13 | 167.46 (16) | C1—C7—C8—N1 | −178.23 (12) |
C2—C1—C7—C8 | −141.00 (14) | N3—C9—C10—C7 | −177.67 (13) |
C7—C1—C2—C3 | −177.11 (13) | N2—C9—C10—C7 | −0.6 (2) |
C6—C1—C2—C3 | 0.7 (2) | N3—C11—C12—O2 | −55.9 (2) |
C6—C1—C7—C8 | 41.30 (19) | O2—C13—C14—N3 | 56.5 (2) |
C2—C1—C6—C5 | −1.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 1.92 | 2.7705 (15) | 170 |
C5—H5···O2ii | 0.93 | 2.56 | 3.4737 (19) | 166 |
C6—H6···O1 | 0.93 | 2.51 | 2.9538 (17) | 109 |
C10—H10···O1iii | 0.93 | 2.43 | 3.1614 (17) | 136 |
C12—H12B···Cl1iv | 0.97 | 2.79 | 3.754 (2) | 173 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, y, z; (iii) −x+1, y+1/2, −z+1/2; (iv) x+1, −y+1/2, z+1/2. |