Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603128X/ym2023sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680603128X/ym2023Isup2.hkl |
CCDC reference: 621561
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.078
- wR factor = 0.162
- Data-to-parameter ratio = 17.8
checkCIF/PLATON results
No syntax errors found
Alert level A DIFF019_ALERT_1_A _diffrn_standards_number is missing Number of standards used in measurement. DIFF020_ALERT_1_A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C20 PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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).
C21H18N4O2S | F(000) = 816 |
Mr = 390.45 | Dx = 1.364 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8200 reflections |
a = 10.6111 (1) Å | θ = 2.1–30.5° |
b = 10.5040 (2) Å | µ = 0.20 mm−1 |
c = 17.3345 (2) Å | T = 294 K |
β = 100.248 (1)° | Block, brown |
V = 1901.26 (5) Å3 | 0.35 × 0.25 × 0.15 mm |
Z = 4 |
Rigaku R-AXIS RAPID-S diffractometer | 5786 independent reflections |
Radiation source: fine-focus sealed tube | 3501 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.077 |
ω scans | θmax = 30.5°, θmin = 2.4° |
Absorption correction: multi-scan (Blessing, 1995) | h = −15→15 |
Tmin = 0.935, Tmax = 0.971 | k = −11→14 |
36040 measured reflections | l = −24→24 |
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)] = 0.078 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.162 | All H-atom parameters refined |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0449P)2 + 0.4823P] where P = (Fo2 + 2Fc2)/3 |
5786 reflections | (Δ/σ)max < 0.001 |
325 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
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 | ||
S1 | 0.43322 (6) | 0.45119 (7) | 0.18283 (4) | 0.0661 (2) | |
O1 | 0.73623 (19) | 0.4843 (2) | 0.42446 (12) | 0.0901 (7) | |
O2 | 0.88710 (15) | 0.62048 (17) | 0.40486 (10) | 0.0635 (5) | |
N | 0.40102 (17) | 0.71137 (19) | 0.18711 (11) | 0.0540 (5) | |
N' | 0.28557 (17) | 0.67645 (19) | 0.15895 (10) | 0.0506 (5) | |
N1 | 0.01480 (19) | 0.8701 (2) | 0.09666 (12) | 0.0570 (5) | |
N3 | 0.59946 (16) | 0.61959 (19) | 0.24134 (11) | 0.0542 (5) | |
C2 | 0.4812 (2) | 0.6065 (2) | 0.20544 (13) | 0.0485 (5) | |
C4 | 0.6573 (2) | 0.5024 (2) | 0.25295 (14) | 0.0537 (6) | |
C5 | 0.5838 (2) | 0.4026 (3) | 0.22541 (17) | 0.0649 (7) | |
C6 | 0.7930 (2) | 0.4974 (3) | 0.29648 (17) | 0.0630 (7) | |
C7 | 0.8008 (2) | 0.5315 (3) | 0.38129 (16) | 0.0621 (7) | |
C8 | 0.9049 (3) | 0.6572 (3) | 0.48832 (17) | 0.0729 (8) | |
C9 | 1.0081 (4) | 0.7528 (5) | 0.5024 (2) | 0.0982 (12) | |
C10 | 0.2016 (2) | 0.7747 (2) | 0.13902 (13) | 0.0496 (5) | |
C11 | 0.2242 (2) | 0.9103 (2) | 0.13926 (13) | 0.0503 (5) | |
C12 | 0.3313 (2) | 0.9894 (3) | 0.15871 (15) | 0.0569 (6) | |
C13 | 0.3143 (3) | 1.1185 (3) | 0.15185 (17) | 0.0668 (7) | |
C14 | 0.1949 (3) | 1.1728 (3) | 0.12612 (17) | 0.0687 (7) | |
C15 | 0.0875 (3) | 1.0974 (3) | 0.10529 (16) | 0.0643 (7) | |
C16 | 0.1048 (2) | 0.9668 (2) | 0.11197 (14) | 0.0528 (6) | |
C17 | 0.0703 (2) | 0.7543 (2) | 0.11305 (13) | 0.0513 (5) | |
C18 | −0.0072 (2) | 0.6374 (2) | 0.10495 (14) | 0.0547 (6) | |
C19 | −0.1262 (3) | 0.6345 (4) | 0.0580 (2) | 0.0941 (11) | |
C20 | −0.2000 (4) | 0.5259 (4) | 0.0525 (3) | 0.1160 (15) | |
C21 | −0.1578 (3) | 0.4194 (4) | 0.0938 (2) | 0.0887 (10) | |
C22 | −0.0405 (3) | 0.4194 (3) | 0.14095 (19) | 0.0699 (7) | |
C23 | 0.0355 (2) | 0.5275 (3) | 0.14619 (16) | 0.0608 (6) | |
H1 | −0.072 (2) | 0.882 (2) | 0.0820 (14) | 0.067 (8)* | |
H5 | 0.607 (3) | 0.320 (3) | 0.2296 (16) | 0.086 (9)* | |
H12 | 0.414 (2) | 0.948 (2) | 0.1802 (14) | 0.071 (8)* | |
H13 | 0.389 (3) | 1.169 (3) | 0.1670 (16) | 0.087 (9)* | |
H14 | 0.186 (3) | 1.264 (3) | 0.1218 (17) | 0.096 (10)* | |
H15 | 0.001 (2) | 1.133 (2) | 0.0839 (14) | 0.068 (7)* | |
H19 | −0.154 (3) | 0.709 (3) | 0.0262 (19) | 0.108 (11)* | |
H20 | −0.280 (4) | 0.530 (4) | 0.016 (2) | 0.140 (14)* | |
H21 | −0.212 (3) | 0.353 (3) | 0.0916 (16) | 0.084 (9)* | |
H22 | −0.012 (3) | 0.343 (3) | 0.1724 (18) | 0.108 (11)* | |
H23 | 0.122 (3) | 0.527 (3) | 0.1844 (15) | 0.076 (8)* | |
H61 | 0.822 (3) | 0.410 (3) | 0.2936 (16) | 0.087 (9)* | |
H62 | 0.853 (3) | 0.551 (3) | 0.2724 (16) | 0.078 (9)* | |
H81 | 0.818 (3) | 0.691 (3) | 0.4973 (15) | 0.082 (9)* | |
H82 | 0.919 (3) | 0.574 (3) | 0.5208 (18) | 0.094 (10)* | |
H91 | 1.093 (4) | 0.723 (4) | 0.486 (2) | 0.132 (14)* | |
H92 | 1.025 (3) | 0.775 (3) | 0.556 (2) | 0.109 (12)* | |
H93 | 0.976 (4) | 0.836 (5) | 0.469 (2) | 0.151 (18)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0545 (4) | 0.0512 (4) | 0.0853 (5) | −0.0006 (3) | −0.0070 (3) | −0.0105 (3) |
O1 | 0.0663 (12) | 0.1207 (19) | 0.0805 (14) | −0.0330 (12) | 0.0052 (10) | 0.0157 (12) |
O2 | 0.0541 (10) | 0.0732 (12) | 0.0629 (11) | −0.0076 (9) | 0.0096 (8) | 0.0004 (9) |
N | 0.0434 (10) | 0.0509 (12) | 0.0660 (12) | 0.0038 (8) | 0.0049 (8) | −0.0023 (9) |
N' | 0.0433 (10) | 0.0531 (12) | 0.0548 (11) | 0.0046 (8) | 0.0070 (8) | 0.0006 (9) |
N1 | 0.0447 (11) | 0.0555 (13) | 0.0686 (13) | 0.0079 (9) | 0.0042 (9) | 0.0068 (10) |
N3 | 0.0402 (10) | 0.0534 (13) | 0.0671 (13) | −0.0001 (8) | 0.0044 (8) | −0.0065 (9) |
C2 | 0.0463 (12) | 0.0442 (13) | 0.0549 (13) | 0.0007 (10) | 0.0087 (9) | −0.0049 (10) |
C4 | 0.0425 (12) | 0.0543 (15) | 0.0624 (15) | 0.0069 (10) | 0.0044 (10) | −0.0038 (11) |
C5 | 0.0569 (15) | 0.0498 (17) | 0.0831 (19) | 0.0091 (12) | −0.0010 (12) | −0.0056 (13) |
C6 | 0.0413 (13) | 0.0686 (19) | 0.0770 (18) | 0.0102 (12) | 0.0046 (11) | −0.0050 (14) |
C7 | 0.0378 (12) | 0.0697 (18) | 0.0748 (17) | 0.0032 (11) | −0.0008 (11) | 0.0078 (14) |
C8 | 0.0671 (18) | 0.088 (2) | 0.0634 (18) | −0.0019 (16) | 0.0118 (13) | 0.0041 (16) |
C9 | 0.100 (3) | 0.120 (4) | 0.075 (2) | −0.027 (2) | 0.017 (2) | −0.026 (2) |
C10 | 0.0447 (12) | 0.0500 (14) | 0.0541 (13) | 0.0030 (10) | 0.0087 (9) | 0.0010 (10) |
C11 | 0.0470 (12) | 0.0533 (15) | 0.0518 (13) | 0.0052 (10) | 0.0120 (9) | 0.0015 (10) |
C12 | 0.0490 (13) | 0.0556 (16) | 0.0667 (16) | 0.0013 (11) | 0.0119 (11) | −0.0039 (12) |
C13 | 0.0625 (17) | 0.0575 (18) | 0.0826 (19) | −0.0046 (13) | 0.0188 (14) | −0.0060 (14) |
C14 | 0.0763 (19) | 0.0498 (17) | 0.0826 (19) | 0.0046 (14) | 0.0209 (14) | 0.0048 (14) |
C15 | 0.0632 (17) | 0.0565 (17) | 0.0736 (18) | 0.0153 (13) | 0.0132 (13) | 0.0089 (13) |
C16 | 0.0491 (13) | 0.0529 (15) | 0.0572 (14) | 0.0043 (10) | 0.0118 (10) | 0.0033 (11) |
C17 | 0.0457 (12) | 0.0535 (14) | 0.0543 (13) | 0.0065 (10) | 0.0081 (10) | 0.0033 (11) |
C18 | 0.0449 (12) | 0.0601 (16) | 0.0580 (14) | −0.0003 (11) | 0.0062 (10) | 0.0005 (11) |
C19 | 0.0664 (19) | 0.079 (2) | 0.121 (3) | −0.0127 (16) | −0.0264 (18) | 0.027 (2) |
C20 | 0.080 (2) | 0.101 (3) | 0.145 (4) | −0.027 (2) | −0.039 (2) | 0.026 (3) |
C21 | 0.070 (2) | 0.071 (2) | 0.120 (3) | −0.0223 (17) | 0.0044 (18) | −0.0050 (19) |
C22 | 0.0641 (17) | 0.0587 (18) | 0.088 (2) | 0.0013 (13) | 0.0166 (14) | 0.0011 (15) |
C23 | 0.0513 (14) | 0.0556 (16) | 0.0746 (17) | 0.0033 (11) | 0.0083 (12) | 0.0024 (12) |
S1—C5 | 1.714 (3) | C10—C11 | 1.444 (3) |
S1—C2 | 1.733 (2) | C11—C12 | 1.400 (3) |
N—C2 | 1.394 (3) | C11—C16 | 1.403 (3) |
N'—N | 1.289 (2) | C12—H12 | 1.00 (3) |
N'—C10 | 1.367 (3) | C13—C12 | 1.371 (4) |
N1—C17 | 1.360 (3) | C13—C14 | 1.388 (4) |
N1—H1 | 0.92 (2) | C13—H13 | 0.95 (3) |
N3—C2 | 1.305 (3) | C14—C15 | 1.382 (4) |
N3—C4 | 1.374 (3) | C14—H14 | 0.96 (3) |
O2—C7 | 1.322 (3) | C15—H15 | 1.00 (2) |
O2—C8 | 1.477 (3) | C16—C15 | 1.386 (4) |
C4—C5 | 1.341 (4) | C16—N1 | 1.387 (3) |
C4—C6 | 1.504 (3) | C17—C18 | 1.470 (3) |
C5—H5 | 0.91 (3) | C18—C19 | 1.375 (3) |
C6—H62 | 1.00 (3) | C18—C23 | 1.391 (3) |
C6—H61 | 0.97 (3) | C19—C20 | 1.377 (5) |
C7—O1 | 1.207 (3) | C19—H19 | 0.97 (3) |
C7—C6 | 1.501 (4) | C20—H20 | 0.96 (4) |
C8—C9 | 1.474 (5) | C21—C20 | 1.361 (5) |
C8—H81 | 1.03 (3) | C21—H21 | 0.90 (3) |
C8—H82 | 1.04 (3) | C22—C21 | 1.363 (4) |
C9—H91 | 1.04 (4) | C22—H22 | 0.99 (3) |
C9—H92 | 0.95 (4) | C23—C22 | 1.386 (4) |
C9—H93 | 1.07 (5) | C23—H23 | 1.03 (3) |
C10—C17 | 1.402 (3) | ||
C5—S1—C2 | 88.19 (13) | C17—C10—C11 | 107.9 (2) |
C7—O2—C8 | 116.7 (2) | C12—C11—C16 | 118.4 (2) |
N'—N—C2 | 111.23 (19) | C12—C11—C10 | 135.5 (2) |
N—N'—C10 | 114.4 (2) | C16—C11—C10 | 106.1 (2) |
C17—N1—C16 | 110.93 (19) | C13—C12—C11 | 118.5 (2) |
C17—N1—H1 | 123.7 (16) | C13—C12—H12 | 124.2 (15) |
C16—N1—H1 | 125.1 (16) | C11—C12—H12 | 117.1 (15) |
C2—N3—C4 | 109.96 (19) | C12—C13—C14 | 122.2 (3) |
N3—C2—N | 121.4 (2) | C12—C13—H13 | 116.1 (19) |
N3—C2—S1 | 115.24 (17) | C14—C13—H13 | 121.7 (19) |
N—C2—S1 | 123.32 (16) | C15—C14—C13 | 120.8 (3) |
C5—C4—N3 | 115.6 (2) | C15—C14—H14 | 119.0 (18) |
C5—C4—C6 | 126.6 (2) | C13—C14—H14 | 120.2 (18) |
N3—C4—C6 | 117.8 (2) | C14—C15—C16 | 117.0 (3) |
C4—C5—S1 | 111.0 (2) | C14—C15—H15 | 123.1 (15) |
C4—C5—H5 | 126.3 (18) | C16—C15—H15 | 119.8 (15) |
S1—C5—H5 | 122.6 (18) | C15—C16—N1 | 129.2 (2) |
C7—C6—C4 | 111.3 (2) | C15—C16—C11 | 123.1 (2) |
C7—C6—H62 | 110.3 (16) | N1—C16—C11 | 107.7 (2) |
C4—C6—H62 | 113.1 (16) | N1—C17—C10 | 107.4 (2) |
C7—C6—H61 | 108.2 (17) | N1—C17—C18 | 120.8 (2) |
C4—C6—H61 | 106.8 (17) | C10—C17—C18 | 131.7 (2) |
H62—C6—H61 | 107 (2) | C19—C18—C23 | 117.8 (3) |
O1—C7—O2 | 122.5 (3) | C19—C18—C17 | 121.0 (2) |
O1—C7—C6 | 124.8 (3) | C23—C18—C17 | 121.2 (2) |
O2—C7—C6 | 112.7 (2) | C18—C19—C20 | 120.7 (3) |
C9—C8—O2 | 107.6 (3) | C18—C19—H19 | 118.2 (19) |
C9—C8—H81 | 113.9 (16) | C20—C19—H19 | 120.9 (19) |
O2—C8—H81 | 106.0 (15) | C21—C20—C19 | 121.0 (3) |
C9—C8—H82 | 117.0 (17) | C21—C20—H20 | 123 (2) |
O2—C8—H82 | 107.0 (17) | C19—C20—H20 | 116 (2) |
H81—C8—H82 | 105 (2) | C20—C21—C22 | 119.7 (3) |
C8—C9—H91 | 114 (2) | C20—C21—H21 | 118.0 (19) |
C8—C9—H92 | 110 (2) | C22—C21—H21 | 122.2 (19) |
H91—C9—H92 | 109 (3) | C21—C22—C23 | 119.9 (3) |
C8—C9—H93 | 108 (2) | C21—C22—H22 | 119.4 (19) |
H91—C9—H93 | 108 (3) | C23—C22—H22 | 120.6 (19) |
H92—C9—H93 | 109 (3) | C22—C23—C18 | 120.9 (2) |
N'—C10—C17 | 122.1 (2) | C22—C23—H23 | 118.4 (15) |
N'—C10—C11 | 130.0 (2) | C18—C23—H23 | 120.5 (15) |
C5—S1—C2—N3 | 0.2 (2) | C11—C10—C17—N1 | 1.1 (3) |
C5—S1—C2—N | −179.9 (2) | C17—C10—C11—C12 | 179.7 (3) |
C2—S1—C5—C4 | 0.2 (2) | C17—C10—C11—C16 | −0.9 (3) |
C7—O2—C8—C9 | 177.8 (3) | C12—C11—C16—C15 | −1.7 (4) |
C8—O2—C7—O1 | 2.1 (4) | C10—C11—C16—C15 | 178.8 (2) |
C8—O2—C7—C6 | −177.9 (2) | C12—C11—C16—N1 | 179.9 (2) |
N'—N—C2—N3 | −173.6 (2) | C10—C11—C16—N1 | 0.4 (3) |
N'—N—C2—S1 | 6.4 (3) | C16—C11—C12—C13 | 1.4 (4) |
C10—N'—N—C2 | −179.50 (18) | C10—C11—C12—C13 | −179.3 (3) |
N—N'—C10—C17 | −175.1 (2) | C14—C13—C12—C11 | −0.2 (4) |
N—N'—C10—C11 | 5.1 (3) | C12—C13—C14—C15 | −0.8 (5) |
C16—N1—C17—C10 | −0.8 (3) | C13—C14—C15—C16 | 0.5 (4) |
C16—N1—C17—C18 | 177.1 (2) | N1—C16—C15—C14 | 178.8 (2) |
C2—N3—C4—C5 | 0.7 (3) | C11—C16—C15—C14 | 0.7 (4) |
C2—N3—C4—C6 | −177.7 (2) | C15—C16—N1—C17 | −178.0 (3) |
C4—N3—C2—N | 179.5 (2) | C11—C16—N1—C17 | 0.2 (3) |
C4—N3—C2—S1 | −0.5 (3) | N1—C17—C18—C19 | 21.4 (4) |
C5—C4—C6—C7 | −109.1 (3) | C10—C17—C18—C19 | −161.2 (3) |
N3—C4—C6—C7 | 69.0 (3) | N1—C17—C18—C23 | −156.6 (2) |
N3—C4—C5—S1 | −0.5 (3) | C10—C17—C18—C23 | 20.7 (4) |
C6—C4—C5—S1 | 177.7 (2) | C19—C18—C23—C22 | −1.0 (4) |
O1—C7—C6—C4 | 51.0 (4) | C17—C18—C23—C22 | 177.1 (2) |
O2—C7—C6—C4 | −128.9 (2) | C23—C18—C19—C20 | 0.1 (5) |
N'—C10—C17—N1 | −178.7 (2) | C17—C18—C19—C20 | −178.1 (4) |
N'—C10—C11—C12 | −0.5 (5) | C18—C19—C20—C21 | 0.6 (7) |
N'—C10—C11—C16 | 178.9 (2) | C22—C21—C20—C19 | −0.5 (7) |
N'—C10—C17—C18 | 3.7 (4) | C23—C22—C21—C20 | −0.5 (6) |
C11—C10—C17—C18 | −176.5 (2) | C18—C23—C22—C21 | 1.2 (5) |