

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021007672/yk2155sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989021007672/yk2155Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989021007672/yk2155Isup3.cml |
CCDC reference: 2099652
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.030
- wR factor = 0.078
- Data-to-parameter ratio = 31.5
checkCIF/PLATON results
No syntax errors found
Alert level G PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 2 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 201 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 13 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 0 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: CrysAlis PRO (Rigaku OD, 2020); cell refinement: CrysAlis PRO (Rigaku OD, 2020); data reduction: CrysAlis PRO (Rigaku OD, 2020); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015b).
C16H13N3O2S | Z = 1 |
Mr = 311.35 | F(000) = 162 |
Triclinic, P1 | Dx = 1.438 Mg m−3 |
a = 4.71248 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 6.96463 (14) Å | Cell parameters from 40070 reflections |
c = 11.5455 (3) Å | θ = 3.0–37.0° |
α = 105.6168 (18)° | µ = 0.24 mm−1 |
β = 95.7876 (16)° | T = 100 K |
γ = 95.9993 (16)° | Plate, colourless |
V = 359.64 (1) Å3 | 0.20 × 0.16 × 0.05 mm |
XtaLAB Synergy, HyPix diffractometer | 6522 independent reflections |
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source | 6312 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.034 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 36.8°, θmin = 3.1° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020) | k = −11→11 |
Tmin = 0.844, Tmax = 1.000 | l = −18→19 |
60895 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.030 | w = 1/[σ2(Fo2) + (0.0486P)2 + 0.0499P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.078 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.41 e Å−3 |
6522 reflections | Δρmin = −0.27 e Å−3 |
207 parameters | Absolute structure: Flack x determined using 2959 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
3 restraints | Absolute structure parameter: −0.016 (12) |
Primary atom site location: structure-invariant direct methods |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 3.5462 (0.0009) x + 3.6978 (0.0019) y - 0.2128 (0.0045) z = 6.1650 (0.0025) * -0.0069 (0.0007) S1 * 0.0023 (0.0009) C2 * 0.0044 (0.0009) N3 * -0.0011 (0.0011) C4 * -0.0046 (0.0012) C5 * 0.0007 (0.0012) C6 * 0.0082 (0.0011) C7 * -0.0004 (0.0011) C3A * -0.0026 (0.0011) C7A -0.0318 (0.0015) C8 Rms deviation of fitted atoms = 0.0043 - 3.3343 (0.0019) x + 1.8849 (0.0037) y + 7.6563 (0.0052) z = 0.2749 (0.0019) Angle to previous plane (with approximate esd) = 75.652 ( 0.033 ) * 0.0041 (0.0009) C11 * 0.0008 (0.0009) C12 * -0.0051 (0.0009) C13 * 0.0044 (0.0010) C14 * 0.0006 (0.0010) C15 * -0.0049 (0.0009) C16 -0.0026 (0.0020) C10 Rms deviation of fitted atoms = 0.0038 ============================================================================= - 0.0418 (0.0830) x - 3.0734 (0.0043) y + 11.3227 (0.0146) z = 3.7743 (0.0598) * 0.0000 (0.0000) N2 * 0.0000 (0.0001) C9 * 0.0000 (0.0000) H01 0.0634 (0.0123) N1 Rms deviation of fitted atoms = 0.0000 4.0751 (0.0123) x - 3.1432 (0.0992) y - 3.6530 (0.1475) z = 1.0965 (0.0176) * 0.0000 (0.0001) N1 * 0.0000 (0.0001) C10 * 0.0000 (0.0000) H02 0.1480 (0.0122) N2 Rms deviation of fitted atoms = 0.0000 ============================================================================= Further torsion angles: 97.53 ( 0.11) O2 - C10 ··· C9 - O1 175.44 ( 2.18) H01 - N1 - C9 - O1 165.89 ( 2.18) H02 - N2 - C10 - O2 101.08 ( 2.76) H01 - N1 - N2 - H02 |
x | y | z | Uiso*/Ueq | ||
S1 | 0.88408 (5) | 0.86164 (4) | 0.76703 (3) | 0.01738 (7) | |
C2 | 0.8642 (3) | 0.87459 (17) | 0.61788 (11) | 0.01314 (18) | |
N1 | 0.9484 (2) | 0.36700 (15) | 0.44206 (10) | 0.01379 (17) | |
H01 | 1.135 (6) | 0.377 (4) | 0.440 (3) | 0.031 (6)* | |
N2 | 0.7891 (2) | 0.17967 (15) | 0.38503 (10) | 0.01379 (17) | |
H02 | 0.743 (6) | 0.111 (4) | 0.433 (2) | 0.025 (6)* | |
N3 | 0.7208 (2) | 1.01131 (16) | 0.59308 (10) | 0.01420 (17) | |
C3A | 0.6136 (3) | 1.11873 (18) | 0.69578 (11) | 0.01407 (18) | |
C4 | 0.4492 (3) | 1.2765 (2) | 0.70032 (13) | 0.0202 (2) | |
H4 | 0.401227 | 1.318921 | 0.630063 | 0.024* | |
C5 | 0.3581 (3) | 1.3691 (2) | 0.80960 (15) | 0.0232 (3) | |
H5 | 0.245566 | 1.475698 | 0.813913 | 0.028* | |
C6 | 0.4294 (3) | 1.3082 (2) | 0.91385 (13) | 0.0214 (2) | |
H6 | 0.364372 | 1.374379 | 0.987636 | 0.026* | |
C7 | 0.5928 (3) | 1.1534 (2) | 0.91122 (12) | 0.0191 (2) | |
H7 | 0.642508 | 1.113038 | 0.982118 | 0.023* | |
C7A | 0.6821 (3) | 1.05845 (18) | 0.80085 (11) | 0.01465 (19) | |
C8 | 1.0007 (3) | 0.72931 (17) | 0.52744 (11) | 0.01505 (19) | |
H8A | 1.188694 | 0.709803 | 0.566030 | 0.018* | |
H8B | 1.035889 | 0.785089 | 0.459045 | 0.018* | |
C9 | 0.8084 (3) | 0.52723 (17) | 0.47944 (11) | 0.01345 (18) | |
O1 | 0.5458 (2) | 0.51401 (15) | 0.47552 (10) | 0.01766 (17) | |
C10 | 0.6341 (3) | 0.15543 (17) | 0.27343 (11) | 0.01340 (18) | |
O2 | 0.6698 (2) | 0.27818 (15) | 0.21612 (10) | 0.01878 (17) | |
C11 | 0.4201 (3) | −0.03063 (17) | 0.22693 (11) | 0.01309 (18) | |
C12 | 0.4296 (3) | −0.19751 (18) | 0.27175 (12) | 0.01574 (19) | |
H12 | 0.576152 | −0.195084 | 0.335201 | 0.019* | |
C13 | 0.2252 (3) | −0.36724 (18) | 0.22370 (12) | 0.0172 (2) | |
H13 | 0.233253 | −0.481009 | 0.253846 | 0.021* | |
C14 | 0.0089 (3) | −0.37052 (19) | 0.13160 (12) | 0.0180 (2) | |
H14 | −0.132276 | −0.485758 | 0.099661 | 0.022* | |
C15 | −0.0006 (3) | −0.2051 (2) | 0.08620 (13) | 0.0191 (2) | |
H15 | −0.147919 | −0.208041 | 0.022925 | 0.023* | |
C16 | 0.2046 (3) | −0.03535 (19) | 0.13308 (12) | 0.0164 (2) | |
H16 | 0.198429 | 0.076976 | 0.101456 | 0.020* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01905 (14) | 0.01772 (12) | 0.01655 (12) | 0.00614 (9) | 0.00163 (9) | 0.00577 (9) |
C2 | 0.0104 (5) | 0.0131 (4) | 0.0151 (4) | 0.0011 (3) | 0.0022 (3) | 0.0026 (3) |
N1 | 0.0089 (4) | 0.0117 (4) | 0.0194 (4) | 0.0008 (3) | 0.0019 (3) | 0.0024 (3) |
N2 | 0.0133 (4) | 0.0114 (4) | 0.0158 (4) | −0.0007 (3) | 0.0011 (3) | 0.0038 (3) |
N3 | 0.0136 (4) | 0.0139 (4) | 0.0150 (4) | 0.0025 (3) | 0.0025 (3) | 0.0034 (3) |
C3A | 0.0126 (5) | 0.0129 (4) | 0.0161 (4) | 0.0021 (3) | 0.0019 (3) | 0.0030 (3) |
C4 | 0.0209 (6) | 0.0178 (5) | 0.0229 (6) | 0.0084 (4) | 0.0036 (4) | 0.0054 (4) |
C5 | 0.0203 (6) | 0.0198 (5) | 0.0274 (6) | 0.0077 (4) | 0.0049 (5) | 0.0008 (5) |
C6 | 0.0173 (6) | 0.0214 (6) | 0.0212 (6) | 0.0023 (4) | 0.0051 (4) | −0.0023 (4) |
C7 | 0.0182 (6) | 0.0214 (5) | 0.0156 (5) | 0.0017 (4) | 0.0032 (4) | 0.0015 (4) |
C7A | 0.0132 (5) | 0.0146 (4) | 0.0152 (4) | 0.0019 (3) | 0.0023 (3) | 0.0025 (3) |
C8 | 0.0104 (5) | 0.0126 (4) | 0.0200 (5) | 0.0006 (3) | 0.0042 (4) | 0.0006 (4) |
C9 | 0.0106 (5) | 0.0128 (4) | 0.0160 (4) | 0.0009 (3) | 0.0026 (3) | 0.0025 (3) |
O1 | 0.0094 (4) | 0.0163 (4) | 0.0253 (4) | 0.0008 (3) | 0.0032 (3) | 0.0026 (3) |
C10 | 0.0128 (5) | 0.0120 (4) | 0.0158 (4) | 0.0013 (3) | 0.0032 (3) | 0.0043 (3) |
O2 | 0.0217 (5) | 0.0158 (4) | 0.0194 (4) | −0.0020 (3) | 0.0015 (3) | 0.0081 (3) |
C11 | 0.0133 (5) | 0.0113 (4) | 0.0148 (4) | 0.0006 (3) | 0.0029 (3) | 0.0039 (3) |
C12 | 0.0158 (5) | 0.0130 (4) | 0.0182 (5) | 0.0005 (4) | 0.0007 (4) | 0.0051 (4) |
C13 | 0.0192 (6) | 0.0121 (4) | 0.0198 (5) | −0.0009 (4) | 0.0029 (4) | 0.0047 (4) |
C14 | 0.0170 (5) | 0.0156 (5) | 0.0190 (5) | −0.0022 (4) | 0.0028 (4) | 0.0025 (4) |
C15 | 0.0167 (6) | 0.0193 (5) | 0.0198 (5) | −0.0015 (4) | −0.0015 (4) | 0.0058 (4) |
C16 | 0.0158 (5) | 0.0156 (5) | 0.0179 (5) | 0.0003 (4) | 0.0005 (4) | 0.0065 (4) |
S1—C7A | 1.7310 (13) | C11—C16 | 1.3994 (17) |
S1—C2 | 1.7422 (12) | C12—C13 | 1.3909 (17) |
C2—N3 | 1.2993 (16) | C13—C14 | 1.390 (2) |
C2—C8 | 1.4933 (17) | C14—C15 | 1.3911 (19) |
N1—C9 | 1.3488 (16) | C15—C16 | 1.3919 (18) |
N1—N2 | 1.3901 (14) | N1—H01 | 0.88 (3) |
N2—C10 | 1.3747 (16) | N2—H02 | 0.85 (3) |
N3—C3A | 1.3939 (16) | C4—H4 | 0.9500 |
C3A—C4 | 1.4018 (18) | C5—H5 | 0.9500 |
C3A—C7A | 1.4056 (17) | C6—H6 | 0.9500 |
C4—C5 | 1.386 (2) | C7—H7 | 0.9500 |
C5—C6 | 1.401 (2) | C8—H8A | 0.9900 |
C6—C7 | 1.385 (2) | C8—H8B | 0.9900 |
C7—C7A | 1.3967 (19) | C12—H12 | 0.9500 |
C8—C9 | 1.5237 (16) | C13—H13 | 0.9500 |
C9—O1 | 1.2266 (15) | C14—H14 | 0.9500 |
C10—O2 | 1.2222 (14) | C15—H15 | 0.9500 |
C10—C11 | 1.4925 (16) | C16—H16 | 0.9500 |
C11—C12 | 1.3967 (17) | ||
C7A—S1—C2 | 89.49 (6) | C14—C15—C16 | 120.28 (12) |
N3—C2—C8 | 124.45 (11) | C15—C16—C11 | 119.80 (11) |
N3—C2—S1 | 115.83 (9) | C9—N1—H01 | 123.3 (19) |
C8—C2—S1 | 119.70 (9) | N2—N1—H01 | 116.8 (19) |
C9—N1—N2 | 119.00 (10) | C10—N2—H02 | 123.3 (18) |
C10—N2—N1 | 117.28 (10) | N1—N2—H02 | 114.4 (18) |
C2—N3—C3A | 110.61 (10) | C5—C4—H4 | 120.7 |
N3—C3A—C4 | 125.26 (11) | C3A—C4—H4 | 120.7 |
N3—C3A—C7A | 114.95 (11) | C4—C5—H5 | 119.4 |
C4—C3A—C7A | 119.79 (12) | C6—C5—H5 | 119.4 |
C5—C4—C3A | 118.52 (13) | C7—C6—H6 | 119.4 |
C4—C5—C6 | 121.11 (13) | C5—C6—H6 | 119.4 |
C7—C6—C5 | 121.18 (13) | C6—C7—H7 | 121.1 |
C6—C7—C7A | 117.77 (13) | C7A—C7—H7 | 121.1 |
C7—C7A—C3A | 121.63 (12) | C2—C8—H8A | 109.5 |
C7—C7A—S1 | 129.24 (10) | C9—C8—H8A | 109.5 |
C3A—C7A—S1 | 109.13 (9) | C2—C8—H8B | 109.5 |
C2—C8—C9 | 110.93 (10) | C9—C8—H8B | 109.5 |
O1—C9—N1 | 123.27 (11) | H8A—C8—H8B | 108.0 |
O1—C9—C8 | 121.67 (11) | C13—C12—H12 | 119.9 |
N1—C9—C8 | 115.06 (10) | C11—C12—H12 | 119.9 |
O2—C10—N2 | 122.11 (11) | C14—C13—H13 | 120.0 |
O2—C10—C11 | 122.31 (11) | C12—C13—H13 | 120.0 |
N2—C10—C11 | 115.59 (10) | C13—C14—H14 | 120.0 |
C12—C11—C16 | 119.69 (11) | C15—C14—H14 | 120.0 |
C12—C11—C10 | 122.96 (11) | C14—C15—H15 | 119.9 |
C16—C11—C10 | 117.35 (10) | C16—C15—H15 | 119.9 |
C13—C12—C11 | 120.15 (11) | C15—C16—H16 | 120.1 |
C14—C13—C12 | 120.05 (11) | C11—C16—H16 | 120.1 |
C13—C14—C15 | 120.02 (11) | ||
C7A—S1—C2—N3 | −0.19 (10) | N2—N1—C9—O1 | 6.66 (18) |
C7A—S1—C2—C8 | −178.46 (10) | N2—N1—C9—C8 | −173.21 (10) |
C9—N1—N2—C10 | 66.44 (15) | C2—C8—C9—O1 | 27.72 (16) |
C8—C2—N3—C3A | 178.23 (11) | C2—C8—C9—N1 | −152.41 (11) |
S1—C2—N3—C3A | 0.05 (14) | N1—N2—C10—O2 | 12.34 (18) |
C2—N3—C3A—C4 | −179.93 (12) | N1—N2—C10—C11 | −167.79 (10) |
C2—N3—C3A—C7A | 0.16 (15) | O2—C10—C11—C12 | 161.41 (13) |
N3—C3A—C4—C5 | −179.93 (13) | N2—C10—C11—C12 | −18.46 (17) |
C7A—C3A—C4—C5 | 0.0 (2) | O2—C10—C11—C16 | −17.71 (18) |
C3A—C4—C5—C6 | 0.4 (2) | N2—C10—C11—C16 | 162.42 (11) |
C4—C5—C6—C7 | −0.1 (2) | C16—C11—C12—C13 | −0.29 (19) |
C5—C6—C7—C7A | −0.6 (2) | C10—C11—C12—C13 | −179.40 (12) |
C6—C7—C7A—C3A | 0.96 (19) | C11—C12—C13—C14 | −0.6 (2) |
C6—C7—C7A—S1 | −179.59 (11) | C12—C13—C14—C15 | 0.9 (2) |
N3—C3A—C7A—C7 | 179.25 (12) | C13—C14—C15—C16 | −0.4 (2) |
C4—C3A—C7A—C7 | −0.65 (19) | C14—C15—C16—C11 | −0.5 (2) |
N3—C3A—C7A—S1 | −0.30 (13) | C12—C11—C16—C15 | 0.84 (19) |
C4—C3A—C7A—S1 | 179.80 (10) | C10—C11—C16—C15 | 179.99 (12) |
C2—S1—C7A—C7 | −179.25 (13) | O1—C9—N1—H01 | 175 (2) |
C2—S1—C7A—C3A | 0.26 (9) | O2—C10—N2—H02 | 166 (2) |
N3—C2—C8—C9 | −97.86 (14) | H01—N1—N2—H02 | 101 (3) |
S1—C2—C8—C9 | 80.26 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H01···O1i | 0.88 (3) | 2.02 (3) | 2.8438 (14) | 157 (3) |
N2—H02···N3ii | 0.85 (3) | 2.15 (3) | 2.9736 (15) | 162 (3) |
Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z. |