Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803023316/cv6240sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803023316/cv6240Isup2.hkl |
CCDC reference: 227014
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C22H19N5O2S | F(000) = 872 |
Mr = 417.48 | Dx = 1.363 Mg m−3 |
Monoclinic, P21/c | Melting point = 480–481 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 19.153 (6) Å | Cell parameters from 1005 reflections |
b = 6.2858 (19) Å | θ = 2.6–24.4° |
c = 16.968 (5) Å | µ = 0.19 mm−1 |
β = 95.218 (5)° | T = 293 K |
V = 2034.3 (11) Å3 | Block, colorless |
Z = 4 | 0.22 × 0.08 × 0.06 mm |
Bruker SMART CCD area-detector diffractometer | 3582 independent reflections |
Radiation source: fine-focus sealed tube | 2218 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
φ and ω scans | θmax = 25.0°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −16→22 |
Tmin = 0.824, Tmax = 0.990 | k = −7→4 |
9314 measured reflections | l = −20→19 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.066 | w = 1/[σ2(Fo2) + (0.084P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.156 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.75 e Å−3 |
3582 reflections | Δρmin = −0.24 e Å−3 |
273 parameters |
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 | 0.25837 (5) | 0.39822 (15) | 0.31535 (6) | 0.0433 (3) | |
O1 | 0.34057 (13) | −0.1422 (4) | 0.38400 (16) | 0.0480 (7) | |
O2 | 0.17105 (14) | 0.4916 (4) | 0.45820 (18) | 0.0508 (8) | |
N1 | 0.36878 (15) | 0.1629 (5) | 0.32126 (18) | 0.0389 (8) | |
N2 | 0.43507 (17) | 0.1312 (6) | 0.2977 (2) | 0.0522 (9) | |
N3 | 0.38667 (19) | 0.4456 (6) | 0.2499 (2) | 0.0546 (10) | |
N4 | 0.23113 (14) | 0.0515 (4) | 0.50634 (17) | 0.0316 (7) | |
N5 | 0.27943 (16) | 0.5807 (5) | 0.51822 (18) | 0.0416 (8) | |
H5 | 0.2709 | 0.7103 | 0.5305 | 0.050* | |
C1 | 0.26123 (17) | 0.1603 (5) | 0.3803 (2) | 0.0311 (8) | |
C2 | 0.32639 (18) | 0.0324 (6) | 0.3633 (2) | 0.0343 (9) | |
C3 | 0.4420 (2) | 0.3024 (8) | 0.2562 (3) | 0.0589 (12) | |
H3 | 0.4826 | 0.3280 | 0.2316 | 0.071* | |
C4 | 0.34224 (19) | 0.3502 (6) | 0.2926 (2) | 0.0394 (9) | |
C5 | 0.19504 (17) | 0.0122 (6) | 0.3706 (2) | 0.0368 (9) | |
H5A | 0.2123 | −0.1321 | 0.3624 | 0.044* | |
C6 | 0.16745 (18) | 0.0141 (6) | 0.4527 (2) | 0.0386 (9) | |
H6A | 0.1335 | 0.1272 | 0.4568 | 0.046* | |
H6B | 0.1459 | −0.1208 | 0.4640 | 0.046* | |
C7 | 0.26784 (17) | 0.2269 (5) | 0.4706 (2) | 0.0310 (8) | |
C8 | 0.2315 (2) | 0.4492 (5) | 0.4807 (2) | 0.0359 (9) | |
C9 | 0.34451 (19) | 0.4816 (6) | 0.5347 (2) | 0.0372 (9) | |
C10 | 0.4049 (2) | 0.5661 (6) | 0.5739 (2) | 0.0528 (11) | |
H10 | 0.4063 | 0.7053 | 0.5925 | 0.063* | |
C11 | 0.4629 (2) | 0.4348 (7) | 0.5842 (3) | 0.0550 (12) | |
H11 | 0.5048 | 0.4893 | 0.6081 | 0.066* | |
C12 | 0.4603 (2) | 0.2274 (7) | 0.5604 (2) | 0.0509 (11) | |
H12 | 0.5000 | 0.1422 | 0.5690 | 0.061* | |
C13 | 0.39885 (19) | 0.1425 (6) | 0.5232 (2) | 0.0394 (9) | |
H13 | 0.3968 | 0.0004 | 0.5080 | 0.047* | |
C14 | 0.34094 (18) | 0.2725 (5) | 0.5094 (2) | 0.0320 (8) | |
C15 | 0.14260 (18) | 0.0602 (5) | 0.3008 (2) | 0.0364 (9) | |
C16 | 0.1402 (2) | −0.0693 (7) | 0.2338 (3) | 0.0526 (11) | |
H16 | 0.1683 | −0.1901 | 0.2344 | 0.063* | |
C17 | 0.0969 (2) | −0.0214 (8) | 0.1666 (3) | 0.0593 (12) | |
H17 | 0.0964 | −0.1104 | 0.1228 | 0.071* | |
C18 | 0.0547 (2) | 0.1555 (8) | 0.1634 (3) | 0.0556 (12) | |
C19 | 0.0564 (2) | 0.2809 (8) | 0.2298 (3) | 0.0615 (13) | |
H19 | 0.0279 | 0.4008 | 0.2292 | 0.074* | |
C20 | 0.09934 (19) | 0.2340 (6) | 0.2977 (3) | 0.0512 (11) | |
H20 | 0.0988 | 0.3218 | 0.3417 | 0.061* | |
C21 | 0.0080 (3) | 0.2128 (10) | 0.0891 (3) | 0.0854 (17) | |
H21A | −0.0366 | 0.1432 | 0.0902 | 0.128* | |
H21B | 0.0298 | 0.1672 | 0.0433 | 0.128* | |
H21C | 0.0011 | 0.3640 | 0.0870 | 0.128* | |
C22 | 0.2183 (2) | 0.0854 (6) | 0.5891 (2) | 0.0502 (11) | |
H22A | 0.2621 | 0.1069 | 0.6203 | 0.075* | |
H22B | 0.1951 | −0.0371 | 0.6084 | 0.075* | |
H22C | 0.1891 | 0.2085 | 0.5931 | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0486 (6) | 0.0324 (5) | 0.0487 (6) | 0.0035 (5) | 0.0032 (5) | 0.0094 (5) |
O1 | 0.0469 (17) | 0.0347 (16) | 0.0632 (19) | 0.0081 (13) | 0.0099 (13) | −0.0022 (13) |
O2 | 0.0420 (17) | 0.0333 (15) | 0.076 (2) | 0.0096 (13) | 0.0004 (14) | −0.0040 (14) |
N1 | 0.0360 (19) | 0.0418 (19) | 0.0401 (19) | 0.0000 (15) | 0.0107 (14) | −0.0013 (15) |
N2 | 0.043 (2) | 0.058 (2) | 0.058 (2) | −0.0022 (18) | 0.0191 (17) | −0.0108 (19) |
N3 | 0.068 (2) | 0.052 (2) | 0.046 (2) | −0.021 (2) | 0.0153 (18) | 0.0000 (17) |
N4 | 0.0344 (17) | 0.0262 (15) | 0.0348 (18) | −0.0002 (13) | 0.0069 (13) | 0.0020 (13) |
N5 | 0.055 (2) | 0.0204 (15) | 0.049 (2) | 0.0034 (15) | 0.0017 (16) | −0.0064 (14) |
C1 | 0.035 (2) | 0.0234 (17) | 0.035 (2) | −0.0003 (16) | 0.0018 (15) | 0.0039 (15) |
C2 | 0.042 (2) | 0.027 (2) | 0.034 (2) | 0.0111 (17) | 0.0021 (16) | −0.0033 (16) |
C3 | 0.050 (3) | 0.072 (3) | 0.058 (3) | −0.015 (3) | 0.023 (2) | −0.017 (3) |
C4 | 0.046 (2) | 0.034 (2) | 0.037 (2) | −0.0062 (18) | −0.0012 (18) | −0.0048 (17) |
C5 | 0.035 (2) | 0.0235 (18) | 0.052 (3) | −0.0007 (16) | 0.0027 (18) | −0.0045 (17) |
C6 | 0.032 (2) | 0.0283 (19) | 0.056 (3) | 0.0001 (16) | 0.0075 (18) | 0.0016 (18) |
C7 | 0.030 (2) | 0.0211 (17) | 0.042 (2) | 0.0033 (15) | 0.0042 (16) | 0.0007 (15) |
C8 | 0.041 (2) | 0.0247 (19) | 0.043 (2) | 0.0053 (18) | 0.0066 (17) | 0.0011 (16) |
C9 | 0.043 (2) | 0.0295 (19) | 0.039 (2) | −0.0019 (18) | 0.0015 (17) | 0.0047 (17) |
C10 | 0.068 (3) | 0.036 (2) | 0.051 (3) | −0.013 (2) | −0.013 (2) | −0.0014 (19) |
C11 | 0.052 (3) | 0.059 (3) | 0.050 (3) | −0.014 (2) | −0.016 (2) | 0.004 (2) |
C12 | 0.041 (3) | 0.065 (3) | 0.045 (3) | 0.008 (2) | −0.0055 (19) | 0.004 (2) |
C13 | 0.041 (2) | 0.035 (2) | 0.041 (2) | 0.0054 (18) | 0.0014 (17) | −0.0007 (17) |
C14 | 0.034 (2) | 0.031 (2) | 0.031 (2) | −0.0013 (17) | 0.0049 (15) | 0.0018 (15) |
C15 | 0.031 (2) | 0.0282 (19) | 0.049 (2) | −0.0016 (16) | −0.0035 (17) | −0.0010 (17) |
C16 | 0.048 (2) | 0.045 (2) | 0.064 (3) | 0.008 (2) | −0.001 (2) | −0.009 (2) |
C17 | 0.058 (3) | 0.072 (3) | 0.046 (3) | 0.006 (3) | −0.005 (2) | −0.013 (2) |
C18 | 0.039 (2) | 0.074 (3) | 0.054 (3) | −0.006 (2) | 0.000 (2) | 0.003 (2) |
C19 | 0.043 (3) | 0.060 (3) | 0.079 (4) | 0.014 (2) | −0.005 (2) | 0.002 (3) |
C20 | 0.041 (2) | 0.047 (3) | 0.063 (3) | 0.007 (2) | −0.006 (2) | −0.012 (2) |
C21 | 0.068 (3) | 0.117 (5) | 0.067 (4) | 0.009 (3) | −0.018 (3) | 0.006 (3) |
C22 | 0.058 (3) | 0.045 (2) | 0.051 (3) | 0.001 (2) | 0.017 (2) | 0.001 (2) |
S1—C4 | 1.713 (4) | C9—C14 | 1.383 (5) |
S1—C1 | 1.856 (3) | C9—C10 | 1.385 (5) |
O1—C2 | 1.177 (4) | C10—C11 | 1.382 (6) |
O2—C8 | 1.215 (4) | C10—H10 | 0.9300 |
N1—C4 | 1.355 (5) | C11—C12 | 1.365 (6) |
N1—N2 | 1.380 (4) | C11—H11 | 0.9300 |
N1—C2 | 1.395 (5) | C12—C13 | 1.391 (5) |
N2—C3 | 1.299 (6) | C12—H12 | 0.9300 |
N3—C4 | 1.311 (5) | C13—C14 | 1.380 (5) |
N3—C3 | 1.387 (5) | C13—H13 | 0.9300 |
N4—C22 | 1.464 (5) | C15—C20 | 1.369 (5) |
N4—C7 | 1.468 (4) | C15—C16 | 1.397 (5) |
N4—C6 | 1.473 (4) | C16—C17 | 1.380 (6) |
N5—C8 | 1.351 (4) | C16—H16 | 0.9300 |
N5—C9 | 1.399 (4) | C17—C18 | 1.374 (6) |
N5—H5 | 0.8600 | C17—H17 | 0.9300 |
C1—C2 | 1.534 (5) | C18—C19 | 1.373 (6) |
C1—C5 | 1.569 (5) | C18—C21 | 1.521 (6) |
C1—C7 | 1.582 (5) | C19—C20 | 1.384 (6) |
C3—H3 | 0.9300 | C19—H19 | 0.9300 |
C5—C15 | 1.511 (5) | C20—H20 | 0.9300 |
C5—C6 | 1.534 (5) | C21—H21A | 0.9600 |
C5—H5A | 0.9800 | C21—H21B | 0.9600 |
C6—H6A | 0.9700 | C21—H21C | 0.9600 |
C6—H6B | 0.9700 | C22—H22A | 0.9600 |
C7—C14 | 1.519 (5) | C22—H22B | 0.9600 |
C7—C8 | 1.577 (5) | C22—H22C | 0.9600 |
C4—S1—C1 | 90.81 (17) | C14—C9—C10 | 121.9 (4) |
C4—N1—N2 | 110.3 (3) | C14—C9—N5 | 110.0 (3) |
C4—N1—C2 | 118.5 (3) | C10—C9—N5 | 128.0 (4) |
N2—N1—C2 | 131.1 (3) | C11—C10—C9 | 117.3 (4) |
C3—N2—N1 | 100.3 (3) | C11—C10—H10 | 121.4 |
C4—N3—C3 | 100.9 (3) | C9—C10—H10 | 121.4 |
C22—N4—C7 | 114.6 (3) | C12—C11—C10 | 121.7 (4) |
C22—N4—C6 | 114.5 (3) | C12—C11—H11 | 119.1 |
C7—N4—C6 | 105.4 (3) | C10—C11—H11 | 119.1 |
C8—N5—C9 | 112.2 (3) | C11—C12—C13 | 120.5 (4) |
C8—N5—H5 | 123.9 | C11—C12—H12 | 119.8 |
C9—N5—H5 | 123.9 | C13—C12—H12 | 119.8 |
C2—C1—C5 | 109.4 (3) | C14—C13—C12 | 119.0 (4) |
C2—C1—C7 | 109.1 (3) | C14—C13—H13 | 120.5 |
C5—C1—C7 | 104.6 (3) | C12—C13—H13 | 120.5 |
C2—C1—S1 | 106.9 (2) | C13—C14—C9 | 119.6 (3) |
C5—C1—S1 | 115.8 (2) | C13—C14—C7 | 131.0 (3) |
C7—C1—S1 | 110.9 (2) | C9—C14—C7 | 109.4 (3) |
O1—C2—N1 | 124.9 (3) | C20—C15—C16 | 117.3 (4) |
O1—C2—C1 | 127.0 (3) | C20—C15—C5 | 123.1 (3) |
N1—C2—C1 | 108.0 (3) | C16—C15—C5 | 119.5 (3) |
N2—C3—N3 | 117.7 (4) | C17—C16—C15 | 121.2 (4) |
N2—C3—H3 | 121.1 | C17—C16—H16 | 119.4 |
N3—C3—H3 | 121.1 | C15—C16—H16 | 119.4 |
N3—C4—N1 | 110.8 (3) | C18—C17—C16 | 121.1 (4) |
N3—C4—S1 | 135.5 (3) | C18—C17—H17 | 119.4 |
N1—C4—S1 | 113.6 (3) | C16—C17—H17 | 119.4 |
C15—C5—C6 | 116.7 (3) | C19—C18—C17 | 117.5 (4) |
C15—C5—C1 | 115.9 (3) | C19—C18—C21 | 120.9 (4) |
C6—C5—C1 | 104.0 (3) | C17—C18—C21 | 121.6 (4) |
C15—C5—H5A | 106.5 | C18—C19—C20 | 121.9 (4) |
C6—C5—H5A | 106.5 | C18—C19—H19 | 119.0 |
C1—C5—H5A | 106.5 | C20—C19—H19 | 119.0 |
N4—C6—C5 | 103.2 (3) | C15—C20—C19 | 120.9 (4) |
N4—C6—H6A | 111.1 | C15—C20—H20 | 119.5 |
C5—C6—H6A | 111.1 | C19—C20—H20 | 119.5 |
N4—C6—H6B | 111.1 | C18—C21—H21A | 109.5 |
C5—C6—H6B | 111.1 | C18—C21—H21B | 109.5 |
H6A—C6—H6B | 109.1 | H21A—C21—H21B | 109.5 |
N4—C7—C14 | 114.9 (3) | C18—C21—H21C | 109.5 |
N4—C7—C8 | 112.8 (3) | H21A—C21—H21C | 109.5 |
C14—C7—C8 | 100.6 (3) | H21B—C21—H21C | 109.5 |
N4—C7—C1 | 101.7 (3) | N4—C22—H22A | 109.5 |
C14—C7—C1 | 117.3 (3) | N4—C22—H22B | 109.5 |
C8—C7—C1 | 110.0 (3) | H22A—C22—H22B | 109.5 |
O2—C8—N5 | 126.9 (3) | N4—C22—H22C | 109.5 |
O2—C8—C7 | 125.3 (3) | H22A—C22—H22C | 109.5 |
N5—C8—C7 | 107.8 (3) | H22B—C22—H22C | 109.5 |
C4—N1—N2—C3 | −0.6 (4) | S1—C1—C7—C14 | −84.3 (3) |
C2—N1—N2—C3 | 175.1 (4) | C2—C1—C7—C8 | 147.3 (3) |
C4—S1—C1—C2 | −12.3 (2) | C5—C1—C7—C8 | −95.7 (3) |
C4—S1—C1—C5 | −134.5 (3) | S1—C1—C7—C8 | 29.8 (3) |
C4—S1—C1—C7 | 106.5 (2) | C9—N5—C8—O2 | −179.1 (4) |
C4—N1—C2—O1 | 171.9 (4) | C9—N5—C8—C7 | 0.9 (4) |
N2—N1—C2—O1 | −3.5 (6) | N4—C7—C8—O2 | −57.1 (5) |
C4—N1—C2—C1 | −10.8 (4) | C14—C7—C8—O2 | 180.0 (4) |
N2—N1—C2—C1 | 173.8 (3) | C1—C7—C8—O2 | 55.6 (5) |
C5—C1—C2—O1 | −42.0 (5) | N4—C7—C8—N5 | 122.9 (3) |
C7—C1—C2—O1 | 71.8 (4) | C14—C7—C8—N5 | 0.0 (4) |
S1—C1—C2—O1 | −168.2 (3) | C1—C7—C8—N5 | −124.4 (3) |
C5—C1—C2—N1 | 140.7 (3) | C8—N5—C9—C14 | −1.5 (4) |
C7—C1—C2—N1 | −105.4 (3) | C8—N5—C9—C10 | −178.4 (4) |
S1—C1—C2—N1 | 14.6 (3) | C14—C9—C10—C11 | 2.4 (6) |
N1—N2—C3—N3 | 0.1 (5) | N5—C9—C10—C11 | 179.0 (4) |
C4—N3—C3—N2 | 0.4 (5) | C9—C10—C11—C12 | −3.0 (6) |
C3—N3—C4—N1 | −0.8 (4) | C10—C11—C12—C13 | 1.2 (7) |
C3—N3—C4—S1 | −176.2 (3) | C11—C12—C13—C14 | 1.4 (6) |
N2—N1—C4—N3 | 0.9 (4) | C12—C13—C14—C9 | −2.0 (5) |
C2—N1—C4—N3 | −175.4 (3) | C12—C13—C14—C7 | 179.9 (4) |
N2—N1—C4—S1 | 177.4 (2) | C10—C9—C14—C13 | 0.1 (6) |
C2—N1—C4—S1 | 1.1 (4) | N5—C9—C14—C13 | −177.1 (3) |
C1—S1—C4—N3 | −177.6 (4) | C10—C9—C14—C7 | 178.6 (3) |
C1—S1—C4—N1 | 7.1 (3) | N5—C9—C14—C7 | 1.4 (4) |
C2—C1—C5—C15 | −111.1 (3) | N4—C7—C14—C13 | 55.9 (5) |
C7—C1—C5—C15 | 132.2 (3) | C8—C7—C14—C13 | 177.4 (4) |
S1—C1—C5—C15 | 9.8 (4) | C1—C7—C14—C13 | −63.4 (5) |
C2—C1—C5—C6 | 119.4 (3) | N4—C7—C14—C9 | −122.3 (3) |
C7—C1—C5—C6 | 2.6 (3) | C8—C7—C14—C9 | −0.9 (4) |
S1—C1—C5—C6 | −119.8 (3) | C1—C7—C14—C9 | 118.3 (3) |
C22—N4—C6—C5 | 173.2 (3) | C6—C5—C15—C20 | 50.7 (5) |
C7—N4—C6—C5 | 46.4 (3) | C1—C5—C15—C20 | −72.4 (5) |
C15—C5—C6—N4 | −157.5 (3) | C6—C5—C15—C16 | −133.4 (4) |
C1—C5—C6—N4 | −28.5 (3) | C1—C5—C15—C16 | 103.5 (4) |
C22—N4—C7—C14 | 61.9 (4) | C20—C15—C16—C17 | 1.2 (6) |
C6—N4—C7—C14 | −171.3 (3) | C5—C15—C16—C17 | −174.9 (4) |
C22—N4—C7—C8 | −52.7 (4) | C15—C16—C17—C18 | 0.0 (7) |
C6—N4—C7—C8 | 74.1 (3) | C16—C17—C18—C19 | −0.9 (7) |
C22—N4—C7—C1 | −170.4 (3) | C16—C17—C18—C21 | 178.6 (4) |
C6—N4—C7—C1 | −43.6 (3) | C17—C18—C19—C20 | 0.6 (7) |
C2—C1—C7—N4 | −92.9 (3) | C21—C18—C19—C20 | −178.9 (4) |
C5—C1—C7—N4 | 24.1 (3) | C16—C15—C20—C19 | −1.5 (6) |
S1—C1—C7—N4 | 149.6 (2) | C5—C15—C20—C19 | 174.5 (4) |
C2—C1—C7—C14 | 33.2 (4) | C18—C19—C20—C15 | 0.7 (7) |
C5—C1—C7—C14 | 150.2 (3) |