Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314617001766/su4127sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2414314617001766/su4127Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314617001766/su4127Isup3.cml |
CCDC reference: 1530588
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.007 Å
- Disorder in main residue
- R factor = 0.068
- wR factor = 0.195
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00675 Ang. PLAT397_ALERT_2_C Deviating C-O-C Angle from 120 Deg for O1 105.8 Degree PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 5.635 Check PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 14 Report
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 7 Note PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large 0.11 Report PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 7 Report PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records 2 Report PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1).. 35 % Note PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms .... ! Info PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 2 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 3 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 4 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 4 ALERT level C = Check. Ensure it is not caused by an omission or oversight 10 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C13H11ClN4OS | F(000) = 632 |
Mr = 306.77 | Dx = 1.450 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 4.9309 (2) Å | Cell parameters from 4259 reflections |
b = 17.1173 (8) Å | θ = 3.7–69.9° |
c = 16.6517 (7) Å | µ = 3.81 mm−1 |
β = 91.189 (3)° | T = 150 K |
V = 1405.16 (11) Å3 | Needles, colourless |
Z = 4 | 0.20 × 0.05 × 0.02 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 2632 independent reflections |
Radiation source: INCOATEC IµS micro-focus source | 1759 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.080 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 70.1°, θmin = 3.7° |
ω scans | h = −5→5 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −20→18 |
Tmin = 0.63, Tmax = 0.92 | l = −20→20 |
10669 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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.195 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.106P)2 + 0.4524P] where P = (Fo2 + 2Fc2)/3 |
2632 reflections | (Δ/σ)max = 0.001 |
180 parameters | Δρmax = 0.51 e Å−3 |
2 restraints | Δρmin = −0.49 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. The 4-chlorophenyl group is rotationally disordered by 27.1 (4)° in approximately equal amounts. The two components of the disorder were refined as rigid hexagons. H-atoms were placed in calculated positions (C—H = 0.95 - 0.9 Å; N—H = 0.88 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 1.3239 (3) | 0.90840 (8) | 0.71546 (7) | 0.0599 (4) | |
O1 | 0.9335 (6) | 0.86722 (16) | 0.60987 (18) | 0.0498 (7) | |
N1 | 0.9888 (7) | 0.9914 (2) | 0.6167 (2) | 0.0491 (8) | |
H1 | 1.0495 | 1.0379 | 0.6307 | 0.059* | |
N2 | 0.7856 (7) | 0.9795 (2) | 0.5597 (2) | 0.0482 (8) | |
N3 | 0.7160 (7) | 0.8117 (2) | 0.4491 (2) | 0.0489 (9) | |
N4 | 0.8597 (7) | 0.8490 (2) | 0.3914 (2) | 0.0511 (9) | |
C1 | 1.0829 (8) | 0.9253 (2) | 0.6482 (2) | 0.0473 (10) | |
C2 | 0.7581 (8) | 0.9051 (2) | 0.5581 (3) | 0.0476 (10) | |
C3 | 0.5703 (9) | 0.8592 (3) | 0.5072 (3) | 0.0556 (11) | |
H3A | 0.4608 | 0.8246 | 0.5415 | 0.067* | |
H3B | 0.4447 | 0.8950 | 0.4782 | 0.067* | |
C4 | 0.7085 (9) | 0.7334 (3) | 0.4378 (3) | 0.0526 (11) | |
C5 | 0.8504 (10) | 0.7191 (3) | 0.3686 (3) | 0.0564 (12) | |
H5 | 0.8798 | 0.6700 | 0.3438 | 0.068* | |
C6 | 0.9417 (9) | 0.7919 (3) | 0.3426 (3) | 0.0527 (11) | |
C7 | 1.1209 (10) | 0.8099 (3) | 0.2742 (3) | 0.0613 (12) | |
H7A | 1.0721 | 0.7764 | 0.2284 | 0.092* | |
H7B | 1.3103 | 0.8004 | 0.2903 | 0.092* | |
H7C | 1.0983 | 0.8649 | 0.2588 | 0.092* | |
Cl1A | 0.1985 (12) | 0.4995 (3) | 0.6544 (5) | 0.0542 (10) | 0.506 (5) |
C8A | 0.5677 (16) | 0.6786 (3) | 0.4912 (5) | 0.0459 (10) | 0.506 (5) |
C9A | 0.5994 (16) | 0.6831 (4) | 0.5742 (5) | 0.049 (2) | 0.506 (5) |
H9A | 0.6967 | 0.7255 | 0.5979 | 0.059* | 0.506 (5) |
C10A | 0.4886 (18) | 0.6258 (5) | 0.6227 (3) | 0.0514 (17) | 0.506 (5) |
H10A | 0.5102 | 0.6289 | 0.6794 | 0.062* | 0.506 (5) |
C11A | 0.3461 (18) | 0.5638 (4) | 0.5881 (4) | 0.0418 (16) | 0.506 (5) |
C12A | 0.3145 (15) | 0.5593 (4) | 0.5051 (5) | 0.0475 (15) | 0.506 (5) |
H12A | 0.2171 | 0.5169 | 0.4815 | 0.057* | 0.506 (5) |
C13A | 0.4252 (16) | 0.6167 (4) | 0.4567 (3) | 0.0433 (18) | 0.506 (5) |
H13A | 0.4036 | 0.6136 | 0.3999 | 0.052* | 0.506 (5) |
Cl1B | 0.1220 (12) | 0.5135 (4) | 0.6530 (5) | 0.0542 (10) | 0.494 (5) |
C8B | 0.5833 (15) | 0.6771 (4) | 0.4934 (5) | 0.0459 (10) | 0.494 (5) |
C9B | 0.6805 (13) | 0.6650 (5) | 0.5714 (6) | 0.049 (2) | 0.494 (5) |
H9B | 0.8412 | 0.6906 | 0.5897 | 0.059* | 0.494 (5) |
C10B | 0.5427 (17) | 0.6154 (5) | 0.6226 (4) | 0.0514 (17) | 0.494 (5) |
H10B | 0.6091 | 0.6072 | 0.6759 | 0.062* | 0.494 (5) |
C11B | 0.3076 (16) | 0.5780 (4) | 0.5958 (4) | 0.0418 (16) | 0.494 (5) |
C12B | 0.2104 (13) | 0.5901 (4) | 0.5178 (5) | 0.0475 (15) | 0.494 (5) |
H12B | 0.0498 | 0.5644 | 0.4995 | 0.057* | 0.494 (5) |
C13B | 0.3483 (16) | 0.6396 (5) | 0.4666 (4) | 0.0433 (18) | 0.494 (5) |
H13B | 0.2819 | 0.6479 | 0.4134 | 0.052* | 0.494 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0586 (7) | 0.0667 (8) | 0.0547 (6) | 0.0081 (5) | 0.0091 (5) | 0.0061 (5) |
O1 | 0.0478 (16) | 0.0355 (15) | 0.0665 (19) | 0.0006 (12) | 0.0149 (14) | −0.0005 (13) |
N1 | 0.055 (2) | 0.041 (2) | 0.0515 (19) | −0.0032 (16) | 0.0035 (17) | −0.0019 (15) |
N2 | 0.051 (2) | 0.042 (2) | 0.052 (2) | −0.0013 (15) | 0.0075 (16) | −0.0023 (14) |
N3 | 0.049 (2) | 0.0377 (19) | 0.061 (2) | −0.0072 (15) | 0.0139 (17) | −0.0069 (15) |
N4 | 0.051 (2) | 0.0371 (19) | 0.066 (2) | −0.0013 (15) | 0.0133 (17) | 0.0025 (15) |
C1 | 0.048 (2) | 0.042 (2) | 0.053 (2) | 0.0021 (17) | 0.0185 (19) | 0.0016 (17) |
C2 | 0.043 (2) | 0.042 (2) | 0.058 (2) | 0.0014 (17) | 0.0153 (19) | −0.0005 (18) |
C3 | 0.052 (3) | 0.041 (2) | 0.074 (3) | −0.0029 (19) | 0.014 (2) | −0.012 (2) |
C4 | 0.050 (2) | 0.042 (2) | 0.066 (3) | −0.0030 (18) | 0.013 (2) | −0.0052 (19) |
C5 | 0.060 (3) | 0.038 (2) | 0.072 (3) | 0.0026 (19) | 0.023 (2) | −0.004 (2) |
C6 | 0.051 (3) | 0.041 (2) | 0.066 (3) | −0.0018 (18) | 0.015 (2) | 0.0029 (19) |
C7 | 0.066 (3) | 0.051 (3) | 0.068 (3) | 0.002 (2) | 0.024 (2) | 0.009 (2) |
Cl1A | 0.069 (3) | 0.0373 (19) | 0.0567 (7) | 0.0002 (16) | 0.001 (2) | 0.0098 (13) |
C8A | 0.038 (2) | 0.036 (2) | 0.064 (3) | 0.0009 (16) | 0.0118 (19) | −0.0029 (18) |
C9A | 0.025 (5) | 0.070 (5) | 0.053 (3) | −0.010 (4) | 0.023 (3) | −0.023 (3) |
C10A | 0.036 (4) | 0.069 (4) | 0.050 (3) | −0.004 (3) | 0.009 (2) | −0.008 (2) |
C11A | 0.046 (3) | 0.028 (3) | 0.052 (3) | 0.007 (3) | 0.009 (2) | −0.006 (2) |
C12A | 0.045 (4) | 0.040 (4) | 0.058 (4) | −0.003 (3) | 0.002 (3) | 0.002 (3) |
C13A | 0.031 (5) | 0.040 (5) | 0.058 (3) | 0.009 (3) | −0.005 (3) | 0.008 (3) |
Cl1B | 0.069 (3) | 0.0373 (19) | 0.0567 (7) | 0.0002 (16) | 0.001 (2) | 0.0098 (13) |
C8B | 0.038 (2) | 0.036 (2) | 0.064 (3) | 0.0009 (16) | 0.0118 (19) | −0.0029 (18) |
C9B | 0.025 (5) | 0.070 (5) | 0.053 (3) | −0.010 (4) | 0.023 (3) | −0.023 (3) |
C10B | 0.036 (4) | 0.069 (4) | 0.050 (3) | −0.004 (3) | 0.009 (2) | −0.008 (2) |
C11B | 0.046 (3) | 0.028 (3) | 0.052 (3) | 0.007 (3) | 0.009 (2) | −0.006 (2) |
C12B | 0.045 (4) | 0.040 (4) | 0.058 (4) | −0.003 (3) | 0.002 (3) | 0.002 (3) |
C13B | 0.031 (5) | 0.040 (5) | 0.058 (3) | 0.009 (3) | −0.005 (3) | 0.008 (3) |
S1—C1 | 1.642 (5) | Cl1A—C11A | 1.730 (3) |
O1—C2 | 1.371 (5) | C8A—C9A | 1.3900 |
O1—C1 | 1.386 (5) | C8A—C13A | 1.3900 |
N1—C1 | 1.327 (5) | C9A—C10A | 1.3900 |
N1—N2 | 1.380 (5) | C9A—H9A | 0.9500 |
N1—H1 | 0.8800 | C10A—C11A | 1.3900 |
N2—C2 | 1.282 (5) | C10A—H10A | 0.9500 |
N3—C4 | 1.355 (6) | C11A—C12A | 1.3900 |
N3—N4 | 1.364 (5) | C12A—C13A | 1.3900 |
N3—C3 | 1.463 (5) | C12A—H12A | 0.9500 |
N4—C6 | 1.339 (6) | C13A—H13A | 0.9500 |
C2—C3 | 1.470 (6) | Cl1B—C11B | 1.732 (3) |
C3—H3A | 0.9900 | C8B—C9B | 1.3900 |
C3—H3B | 0.9900 | C8B—C13B | 1.3900 |
C4—C5 | 1.383 (6) | C9B—C10B | 1.3900 |
C4—C8A | 1.476 (5) | C9B—H9B | 0.9500 |
C4—C8B | 1.480 (5) | C10B—C11B | 1.3900 |
C5—C6 | 1.396 (6) | C10B—H10B | 0.9500 |
C5—H5 | 0.9500 | C11B—C12B | 1.3900 |
C6—C7 | 1.488 (6) | C12B—C13B | 1.3900 |
C7—H7A | 0.9800 | C12B—H12B | 0.9500 |
C7—H7B | 0.9800 | C13B—H13B | 0.9500 |
C7—H7C | 0.9800 | ||
C2—O1—C1 | 105.8 (3) | H7B—C7—H7C | 109.5 |
C1—N1—N2 | 112.8 (4) | C9A—C8A—C13A | 120.0 |
C1—N1—H1 | 123.6 | C9A—C8A—C4 | 121.3 (7) |
N2—N1—H1 | 123.6 | C13A—C8A—C4 | 118.4 (7) |
C2—N2—N1 | 103.7 (3) | C10A—C9A—C8A | 120.0 |
C4—N3—N4 | 112.2 (3) | C10A—C9A—H9A | 120.0 |
C4—N3—C3 | 129.0 (4) | C8A—C9A—H9A | 120.0 |
N4—N3—C3 | 118.4 (3) | C11A—C10A—C9A | 120.0 |
C6—N4—N3 | 104.8 (3) | C11A—C10A—H10A | 120.0 |
N1—C1—O1 | 104.6 (4) | C9A—C10A—H10A | 120.0 |
N1—C1—S1 | 131.5 (4) | C10A—C11A—C12A | 120.0 |
O1—C1—S1 | 123.9 (3) | C10A—C11A—Cl1A | 115.9 (6) |
N2—C2—O1 | 113.0 (4) | C12A—C11A—Cl1A | 123.9 (6) |
N2—C2—C3 | 127.5 (4) | C13A—C12A—C11A | 120.0 |
O1—C2—C3 | 119.5 (4) | C13A—C12A—H12A | 120.0 |
N3—C3—C2 | 111.5 (4) | C11A—C12A—H12A | 120.0 |
N3—C3—H3A | 109.3 | C12A—C13A—C8A | 120.0 |
C2—C3—H3A | 109.3 | C12A—C13A—H13A | 120.0 |
N3—C3—H3B | 109.3 | C8A—C13A—H13A | 120.0 |
C2—C3—H3B | 109.3 | C9B—C8B—C13B | 120.0 |
H3A—C3—H3B | 108.0 | C9B—C8B—C4 | 122.8 (7) |
N3—C4—C5 | 106.1 (4) | C13B—C8B—C4 | 117.1 (7) |
N3—C4—C8A | 123.8 (5) | C8B—C9B—C10B | 120.0 |
C5—C4—C8A | 130.0 (5) | C8B—C9B—H9B | 120.0 |
N3—C4—C8B | 124.6 (5) | C10B—C9B—H9B | 120.0 |
C5—C4—C8B | 129.2 (5) | C11B—C10B—C9B | 120.0 |
C4—C5—C6 | 105.9 (4) | C11B—C10B—H10B | 120.0 |
C4—C5—H5 | 127.1 | C9B—C10B—H10B | 120.0 |
C6—C5—H5 | 127.1 | C10B—C11B—C12B | 120.0 |
N4—C6—C5 | 111.1 (4) | C10B—C11B—Cl1B | 124.4 (6) |
N4—C6—C7 | 120.3 (4) | C12B—C11B—Cl1B | 115.6 (6) |
C5—C6—C7 | 128.5 (4) | C13B—C12B—C11B | 120.0 |
C6—C7—H7A | 109.5 | C13B—C12B—H12B | 120.0 |
C6—C7—H7B | 109.5 | C11B—C12B—H12B | 120.0 |
H7A—C7—H7B | 109.5 | C12B—C13B—C8B | 120.0 |
C6—C7—H7C | 109.5 | C12B—C13B—H13B | 120.0 |
H7A—C7—H7C | 109.5 | C8B—C13B—H13B | 120.0 |
C1—N1—N2—C2 | 0.5 (5) | N3—C4—C8A—C9A | −46.9 (7) |
C4—N3—N4—C6 | 0.5 (5) | C5—C4—C8A—C9A | 134.3 (6) |
C3—N3—N4—C6 | −172.9 (4) | N3—C4—C8A—C13A | 140.1 (5) |
N2—N1—C1—O1 | 0.0 (4) | C5—C4—C8A—C13A | −38.8 (9) |
N2—N1—C1—S1 | 178.6 (3) | C13A—C8A—C9A—C10A | 0.0 |
C2—O1—C1—N1 | −0.5 (4) | C4—C8A—C9A—C10A | −173.0 (7) |
C2—O1—C1—S1 | −179.2 (3) | C8A—C9A—C10A—C11A | 0.0 |
N1—N2—C2—O1 | −0.8 (4) | C9A—C10A—C11A—C12A | 0.0 |
N1—N2—C2—C3 | −179.3 (4) | C9A—C10A—C11A—Cl1A | −175.9 (7) |
C1—O1—C2—N2 | 0.8 (4) | C10A—C11A—C12A—C13A | 0.0 |
C1—O1—C2—C3 | 179.5 (3) | Cl1A—C11A—C12A—C13A | 175.6 (7) |
C4—N3—C3—C2 | 123.0 (5) | C11A—C12A—C13A—C8A | 0.0 |
N4—N3—C3—C2 | −64.9 (5) | C9A—C8A—C13A—C12A | 0.0 |
N2—C2—C3—N3 | 113.1 (5) | C4—C8A—C13A—C12A | 173.2 (7) |
O1—C2—C3—N3 | −65.3 (5) | N3—C4—C8B—C9B | −64.5 (7) |
N4—N3—C4—C5 | −1.0 (5) | C5—C4—C8B—C9B | 111.6 (7) |
C3—N3—C4—C5 | 171.5 (4) | N3—C4—C8B—C13B | 111.0 (6) |
N4—N3—C4—C8A | 179.9 (6) | C5—C4—C8B—C13B | −72.9 (7) |
C3—N3—C4—C8A | −7.6 (9) | C13B—C8B—C9B—C10B | 0.0 |
N4—N3—C4—C8B | 175.8 (6) | C4—C8B—C9B—C10B | 175.4 (7) |
C3—N3—C4—C8B | −11.7 (9) | C8B—C9B—C10B—C11B | 0.0 |
N3—C4—C5—C6 | 1.1 (6) | C9B—C10B—C11B—C12B | 0.0 |
C8A—C4—C5—C6 | −179.9 (7) | C9B—C10B—C11B—Cl1B | 178.6 (7) |
C8B—C4—C5—C6 | −175.5 (6) | C10B—C11B—C12B—C13B | 0.0 |
N3—N4—C6—C5 | 0.3 (5) | Cl1B—C11B—C12B—C13B | −178.7 (7) |
N3—N4—C6—C7 | −176.2 (4) | C11B—C12B—C13B—C8B | 0.0 |
C4—C5—C6—N4 | −0.9 (6) | C9B—C8B—C13B—C12B | 0.0 |
C4—C5—C6—C7 | 175.3 (5) | C4—C8B—C13B—C12B | −175.7 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N4i | 0.88 | 2.02 | 2.836 (5) | 153 |
C3—H3B···N2ii | 0.99 | 2.51 | 3.445 (6) | 158 |
C7—H7C···Cl1Biii | 0.98 | 2.73 | 3.635 (10) | 153 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x+1, −y+3/2, z−1/2. |