Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602099X/er2004sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680602099X/er20043sup2.hkl |
CCDC reference: 613670
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.063
- wR factor = 0.185
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 74.16 From the CIF: _diffrn_reflns_theta_full 74.16 From the CIF: _reflns_number_total 3018 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3257 Completeness (_total/calc) 92.66% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93 PLAT028_ALERT_3_C _diffrn_measured_fraction_theta_max Low ....... 0.93 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C21 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C20 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C19 H18 N2 S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 4 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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).
C19H18N2S | F(000) = 1296 |
Mr = 306.41 | Dx = 1.274 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 18.064 (4) Å | θ = 21.2–42.8° |
b = 7.901 (2) Å | µ = 1.76 mm−1 |
c = 22.401 (7) Å | T = 293 K |
β = 91.76 (2)° | Prism, light brown |
V = 3195.9 (15) Å3 | 0.36 × 0.24 × 0.12 mm |
Z = 8 |
Enraf Nonius TurboCAD-4 diffractometer | Rint = 0.034 |
non–profiled ω scans | θmax = 74.2°, θmin = 4.0° |
Absorption correction: ψ scan (North et al., 1968) | h = −22→0 |
Tmin = 0.632, Tmax = 0.810 | k = 0→9 |
3110 measured reflections | l = −27→27 |
3018 independent reflections | 3 standard reflections every 120 min |
2081 reflections with I > 2σ(I) | intensity decay: none |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.063 | w = 1/[σ2(Fo2) + (0.0984P)2 + 2.0386P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.185 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.59 e Å−3 |
3018 reflections | Δρmin = −0.42 e Å−3 |
199 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. |
x | y | z | Uiso*/Ueq | ||
C2 | 0.1297 (2) | 0.9049 (5) | 0.02442 (17) | 0.0671 (10) | |
H2A | 0.1219 | 0.7908 | 0.0095 | 0.08* | |
H2B | 0.0891 | 0.9333 | 0.0499 | 0.08* | |
C3 | 0.13196 (18) | 1.0293 (5) | −0.02786 (15) | 0.0579 (9) | |
H1A | 0.1048 | 0.9851 | −0.0625 | 0.069* | |
H1B | 0.1109 | 1.1376 | −0.0171 | 0.069* | |
C5 | 0.25152 (17) | 1.1083 (4) | −0.08669 (13) | 0.0442 (7) | |
C6 | 0.32483 (16) | 1.0976 (4) | −0.06574 (13) | 0.0440 (7) | |
C7 | 0.25890 (18) | 1.0033 (4) | 0.00440 (13) | 0.0480 (7) | |
C8 | 0.39419 (16) | 1.1459 (4) | −0.09406 (12) | 0.0426 (7) | |
C9 | 0.46018 (17) | 1.0751 (4) | −0.07258 (14) | 0.0498 (8) | |
H14 | 0.4591 | 0.998 | −0.0413 | 0.06* | |
C10 | 0.52726 (18) | 1.1166 (5) | −0.09666 (15) | 0.0539 (8) | |
H15 | 0.5705 | 1.0687 | −0.0807 | 0.065* | |
C11 | 0.53125 (17) | 1.2283 (5) | −0.14404 (15) | 0.0524 (8) | |
C12 | 0.46545 (18) | 1.2979 (5) | −0.16568 (15) | 0.0550 (8) | |
H17 | 0.4666 | 1.373 | −0.1976 | 0.066* | |
C13 | 0.39789 (18) | 1.2591 (4) | −0.14121 (14) | 0.0525 (8) | |
H18 | 0.3548 | 1.3093 | −0.1565 | 0.063* | |
C14 | 0.21589 (16) | 1.1558 (4) | −0.14387 (13) | 0.0435 (7) | |
C15 | 0.24043 (17) | 1.0918 (4) | −0.19792 (13) | 0.0484 (8) | |
H7 | 0.282 | 1.0224 | −0.198 | 0.058* | |
C16 | 0.20376 (18) | 1.1301 (5) | −0.25136 (14) | 0.0530 (8) | |
H8 | 0.2215 | 1.0868 | −0.2868 | 0.064* | |
C17 | 0.14110 (17) | 1.2317 (4) | −0.25328 (14) | 0.0501 (8) | |
C18 | 0.11741 (18) | 1.2976 (5) | −0.19955 (15) | 0.0555 (9) | |
H10 | 0.0759 | 1.3673 | −0.1997 | 0.067* | |
C19 | 0.15398 (18) | 1.2621 (4) | −0.14583 (15) | 0.0538 (8) | |
H11 | 0.1372 | 1.3093 | −0.1107 | 0.065* | |
C20 | 0.1003 (2) | 1.2702 (5) | −0.31163 (16) | 0.0676 (10) | |
H12A | 0.0586 | 1.3418 | −0.3042 | 0.101* | |
H12B | 0.0832 | 1.1664 | −0.3296 | 0.101* | |
H12C | 0.133 | 1.3266 | −0.3381 | 0.101* | |
C21 | 0.6040 (2) | 1.2703 (6) | −0.17189 (18) | 0.0708 (11) | |
H19A | 0.5957 | 1.3494 | −0.2039 | 0.106* | |
H19B | 0.6257 | 1.1688 | −0.1872 | 0.106* | |
H19C | 0.637 | 1.3195 | −0.1423 | 0.106* | |
N4 | 0.21061 (14) | 1.0462 (3) | −0.03994 (11) | 0.0464 (6) | |
N7 | 0.32813 (14) | 1.0307 (4) | −0.00790 (11) | 0.0491 (6) | |
S1 | 0.21703 (5) | 0.91680 (13) | 0.06671 (4) | 0.0628 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.065 (2) | 0.079 (3) | 0.058 (2) | −0.009 (2) | 0.0117 (17) | 0.007 (2) |
C3 | 0.0467 (19) | 0.074 (2) | 0.0529 (18) | −0.0054 (17) | 0.0063 (14) | −0.0019 (17) |
C5 | 0.0464 (16) | 0.0491 (18) | 0.0374 (15) | 0.0034 (14) | 0.0025 (12) | −0.0027 (13) |
C6 | 0.0458 (17) | 0.0496 (18) | 0.0366 (14) | 0.0015 (14) | 0.0011 (12) | −0.0013 (13) |
C7 | 0.0551 (19) | 0.051 (2) | 0.0382 (15) | 0.0015 (15) | 0.0031 (13) | −0.0016 (14) |
C8 | 0.0429 (15) | 0.0490 (17) | 0.0358 (14) | −0.0011 (13) | 0.0010 (12) | −0.0030 (13) |
C9 | 0.0500 (18) | 0.058 (2) | 0.0408 (16) | 0.0020 (15) | −0.0032 (13) | −0.0027 (14) |
C10 | 0.0420 (17) | 0.068 (2) | 0.0514 (18) | 0.0041 (15) | −0.0032 (14) | −0.0068 (16) |
C11 | 0.0435 (17) | 0.060 (2) | 0.0539 (18) | −0.0062 (15) | 0.0060 (14) | −0.0106 (16) |
C12 | 0.0551 (19) | 0.058 (2) | 0.0519 (18) | −0.0023 (16) | 0.0078 (15) | 0.0064 (16) |
C13 | 0.0479 (18) | 0.057 (2) | 0.0523 (18) | 0.0071 (15) | 0.0030 (14) | 0.0035 (16) |
C14 | 0.0411 (15) | 0.0484 (17) | 0.0411 (15) | 0.0004 (13) | 0.0015 (12) | 0.0007 (13) |
C15 | 0.0411 (16) | 0.058 (2) | 0.0462 (17) | 0.0076 (14) | 0.0041 (13) | 0.0000 (15) |
C16 | 0.0515 (18) | 0.068 (2) | 0.0403 (16) | −0.0012 (16) | 0.0057 (13) | 0.0000 (15) |
C17 | 0.0447 (17) | 0.054 (2) | 0.0509 (17) | −0.0080 (15) | −0.0042 (13) | 0.0084 (15) |
C18 | 0.0451 (17) | 0.060 (2) | 0.061 (2) | 0.0100 (16) | −0.0041 (15) | 0.0051 (17) |
C19 | 0.0499 (18) | 0.061 (2) | 0.0511 (18) | 0.0077 (16) | 0.0064 (14) | −0.0050 (16) |
C20 | 0.064 (2) | 0.078 (3) | 0.060 (2) | −0.0080 (19) | −0.0169 (17) | 0.015 (2) |
C21 | 0.054 (2) | 0.080 (3) | 0.079 (3) | −0.0100 (19) | 0.0130 (18) | −0.004 (2) |
N4 | 0.0452 (14) | 0.0520 (15) | 0.0422 (13) | −0.0001 (12) | 0.0058 (10) | −0.0001 (11) |
N7 | 0.0511 (15) | 0.0579 (16) | 0.0383 (13) | 0.0014 (13) | −0.0007 (11) | 0.0008 (12) |
S1 | 0.0678 (6) | 0.0772 (7) | 0.0437 (5) | −0.0071 (5) | 0.0087 (4) | 0.0076 (4) |
C2—C3 | 1.530 (5) | C11—C21 | 1.509 (5) |
C2—S1 | 1.818 (4) | C12—C13 | 1.388 (4) |
C2—H2A | 0.97 | C12—H17 | 0.93 |
C2—H2B | 0.97 | C13—H18 | 0.93 |
C3—N4 | 1.461 (4) | C14—C19 | 1.398 (4) |
C3—H1A | 0.97 | C14—C15 | 1.397 (4) |
C3—H1B | 0.97 | C15—C16 | 1.384 (4) |
C5—N4 | 1.390 (4) | C15—H7 | 0.93 |
C5—C6 | 1.394 (4) | C16—C17 | 1.387 (5) |
C5—C14 | 1.465 (4) | C16—H8 | 0.93 |
C6—N7 | 1.399 (4) | C17—C18 | 1.391 (5) |
C6—C8 | 1.472 (4) | C17—C20 | 1.512 (4) |
C7—N7 | 1.307 (4) | C18—C19 | 1.384 (4) |
C7—N4 | 1.345 (4) | C18—H10 | 0.93 |
C7—S1 | 1.747 (3) | C19—H11 | 0.93 |
C8—C13 | 1.387 (4) | C20—H12A | 0.96 |
C8—C9 | 1.389 (4) | C20—H12B | 0.96 |
C9—C10 | 1.381 (5) | C20—H12C | 0.96 |
C9—H14 | 0.93 | C21—H19A | 0.96 |
C10—C11 | 1.384 (5) | C21—H19B | 0.96 |
C10—H15 | 0.93 | C21—H19C | 0.96 |
C11—C12 | 1.384 (5) | ||
C3—C2—S1 | 108.8 (2) | C12—C13—H18 | 119.8 |
C3—C2—H2A | 109.9 | C8—C13—H18 | 119.8 |
S1—C2—H2A | 109.9 | C19—C14—C15 | 117.7 (3) |
C3—C2—H2B | 109.9 | C19—C14—C5 | 120.7 (3) |
S1—C2—H2B | 109.9 | C15—C14—C5 | 121.5 (3) |
H2A—C2—H2B | 108.3 | C16—C15—C14 | 121.0 (3) |
N4—C3—C2 | 104.5 (3) | C16—C15—H7 | 119.5 |
N4—C3—H1A | 110.9 | C14—C15—H7 | 119.5 |
C2—C3—H1A | 110.9 | C15—C16—C17 | 121.5 (3) |
N4—C3—H1B | 110.9 | C15—C16—H8 | 119.3 |
C2—C3—H1B | 110.9 | C17—C16—H8 | 119.3 |
H1A—C3—H1B | 108.9 | C18—C17—C16 | 117.5 (3) |
N4—C5—C6 | 104.3 (3) | C18—C17—C20 | 121.2 (3) |
N4—C5—C14 | 121.3 (3) | C16—C17—C20 | 121.3 (3) |
C6—C5—C14 | 134.2 (3) | C17—C18—C19 | 121.7 (3) |
C5—C6—N7 | 110.3 (3) | C17—C18—H10 | 119.2 |
C5—C6—C8 | 130.7 (3) | C19—C18—H10 | 119.2 |
N7—C6—C8 | 119.0 (3) | C18—C19—C14 | 120.6 (3) |
N7—C7—N4 | 113.9 (3) | C18—C19—H11 | 119.7 |
N7—C7—S1 | 132.4 (3) | C14—C19—H11 | 119.7 |
N4—C7—S1 | 113.7 (2) | C17—C20—H12A | 109.5 |
C13—C8—C9 | 117.5 (3) | C17—C20—H12B | 109.5 |
C13—C8—C6 | 123.8 (3) | H12A—C20—H12B | 109.5 |
C9—C8—C6 | 118.6 (3) | C17—C20—H12C | 109.5 |
C10—C9—C8 | 121.5 (3) | H12A—C20—H12C | 109.5 |
C10—C9—H14 | 119.2 | H12B—C20—H12C | 109.5 |
C8—C9—H14 | 119.2 | C11—C21—H19A | 109.5 |
C9—C10—C11 | 121.2 (3) | C11—C21—H19B | 109.5 |
C9—C10—H15 | 119.4 | H19A—C21—H19B | 109.5 |
C11—C10—H15 | 119.4 | C11—C21—H19C | 109.5 |
C10—C11—C12 | 117.2 (3) | H19A—C21—H19C | 109.5 |
C10—C11—C21 | 121.6 (3) | H19B—C21—H19C | 109.5 |
C12—C11—C21 | 121.2 (3) | C7—N4—C5 | 107.3 (3) |
C13—C12—C11 | 122.0 (3) | C7—N4—C3 | 116.9 (3) |
C13—C12—H17 | 119 | C5—N4—C3 | 135.6 (3) |
C11—C12—H17 | 119 | C7—N7—C6 | 104.1 (3) |
C12—C13—C8 | 120.5 (3) | C7—S1—C2 | 89.66 (16) |
S1—C2—C3—N4 | 26.2 (3) | C14—C15—C16—C17 | −0.7 (5) |
N4—C5—C6—N7 | 0.1 (3) | C15—C16—C17—C18 | 1.6 (5) |
C14—C5—C6—N7 | −175.0 (3) | C15—C16—C17—C20 | −178.7 (3) |
N4—C5—C6—C8 | −179.1 (3) | C16—C17—C18—C19 | −0.9 (5) |
C14—C5—C6—C8 | 5.8 (6) | C20—C17—C18—C19 | 179.4 (3) |
C5—C6—C8—C13 | 20.4 (5) | C17—C18—C19—C14 | −0.9 (5) |
N7—C6—C8—C13 | −158.8 (3) | C15—C14—C19—C18 | 1.9 (5) |
C5—C6—C8—C9 | −159.8 (3) | C5—C14—C19—C18 | −175.6 (3) |
N7—C6—C8—C9 | 21.0 (4) | N7—C7—N4—C5 | 0.1 (4) |
C13—C8—C9—C10 | 0.7 (5) | S1—C7—N4—C5 | −178.4 (2) |
C6—C8—C9—C10 | −179.2 (3) | N7—C7—N4—C3 | −176.2 (3) |
C8—C9—C10—C11 | −1.3 (5) | S1—C7—N4—C3 | 5.3 (4) |
C9—C10—C11—C12 | 0.8 (5) | C6—C5—N4—C7 | −0.1 (3) |
C9—C10—C11—C21 | −178.1 (3) | C14—C5—N4—C7 | 175.8 (3) |
C10—C11—C12—C13 | 0.2 (5) | C6—C5—N4—C3 | 175.1 (3) |
C21—C11—C12—C13 | 179.1 (3) | C14—C5—N4—C3 | −9.0 (6) |
C11—C12—C13—C8 | −0.8 (5) | C2—C3—N4—C7 | −20.6 (4) |
C9—C8—C13—C12 | 0.4 (5) | C2—C3—N4—C5 | 164.4 (3) |
C6—C8—C13—C12 | −179.8 (3) | N4—C7—N7—C6 | −0.1 (4) |
N4—C5—C14—C19 | 49.8 (5) | S1—C7—N7—C6 | 178.1 (3) |
C6—C5—C14—C19 | −135.7 (4) | C5—C6—N7—C7 | 0.0 (3) |
N4—C5—C14—C15 | −127.6 (3) | C8—C6—N7—C7 | 179.3 (3) |
C6—C5—C14—C15 | 46.9 (5) | N7—C7—S1—C2 | −168.4 (4) |
C19—C14—C15—C16 | −1.1 (5) | N4—C7—S1—C2 | 9.9 (3) |
C5—C14—C15—C16 | 176.3 (3) | C3—C2—S1—C7 | −21.1 (3) |
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