Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800017888/ob6001sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536800017888/ob6001Isup2.hkl |
CCDC reference: 155874
The title compound, (I), was prepared by Spa Contract Synthesis. Crystals of (I) were grown from dmf/methanol(1/10) solution.
All H atoms were included in the refinement, at calculated positions, as riding models with C—H set to 0.95 Å (Ar—H), except for the amine H atoms, which were located on difference syntheses and both positional and thermal parameters refined.
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
C16H13N3S2 | F(000) = 648 |
Mr = 311.41 | Dx = 1.345 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7937 (18) Å | Cell parameters from 6016 reflections |
b = 8.3091 (17) Å | θ = 1.0–27.5° |
c = 21.148 (4) Å | µ = 0.34 mm−1 |
β = 95.73 (3)° | T = 150 K |
V = 1537.5 (5) Å3 | Block, colourless |
Z = 4 | 0.34 × 0.18 × 0.16 mm |
Enraf Nonius KappaCCD area-detector diffractometer | 3476 independent reflections |
Radiation source: Enraf Nonius FR591 rotating anode | 2440 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.088 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 1.9° |
ϕ and ω scans | h = −11→10 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −9→10 |
Tmin = 0.893, Tmax = 0.947 | l = −27→27 |
12370 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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0595P)2] where P = (Fo2 + 2Fc2)/3 |
3476 reflections | (Δ/σ)max = 0.009 |
198 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
C16H13N3S2 | V = 1537.5 (5) Å3 |
Mr = 311.41 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.7937 (18) Å | µ = 0.34 mm−1 |
b = 8.3091 (17) Å | T = 150 K |
c = 21.148 (4) Å | 0.34 × 0.18 × 0.16 mm |
β = 95.73 (3)° |
Enraf Nonius KappaCCD area-detector diffractometer | 3476 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 2440 reflections with I > 2σ(I) |
Tmin = 0.893, Tmax = 0.947 | Rint = 0.088 |
12370 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.29 e Å−3 |
3476 reflections | Δρmin = −0.47 e Å−3 |
198 parameters |
Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. |
Geometry. Mean plane data ex SHELXL97 ########################### Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 8.5612 (0.0048) x - 0.7071 (0.0071) y + 6.5153 (0.0178) z = 4.6782 (0.0045) * -0.0065 (0.0013) C7 * -0.0020 (0.0015) C8 * 0.0066 (0.0016) C9 * -0.0026 (0.0016) C10 * -0.0060 (0.0015) C11 * 0.0106 (0.0014) C12 Rms deviation of fitted atoms = 0.0064 - 1.0656 (0.0061) x + 4.0487 (0.0060) y + 18.4531 (0.0125) z = 4.5647 (0.0047) Angle to previous plane (with approximate e.s.d.) = 74.94 (0.07) * 0.0056 (0.0012) N1 * -0.0113 (0.0013) C2 * 0.0060 (0.0012) N3 * 0.0041 (0.0013) C4 * -0.0090 (0.0012) C5 * 0.0046 (0.0012) C6 Rms deviation of fitted atoms = 0.0072 8.7084 (0.0047) x - 0.2201 (0.0064) y - 4.9597 (0.0157) z = 0.1054 (0.0034) Angle to previous plane (with approximate e.s.d.) = 75.47 (0.07) * -0.0031 (0.0012) C13 * 0.0052 (0.0013) C14 * -0.0031 (0.0013) C15 * -0.0009 (0.0015) C16 * 0.0030 (0.0015) C17 * -0.0009 (0.0013) C18 Rms deviation of fitted atoms = 0.0031 |
x | y | z | Uiso*/Ueq | ||
N1 | −0.11796 (16) | 0.86840 (19) | 0.05032 (7) | 0.0250 (4) | |
C2 | −0.2636 (2) | 0.9113 (2) | 0.03158 (9) | 0.0263 (4) | |
N21 | −0.2840 (2) | 1.0482 (2) | −0.00121 (9) | 0.0377 (5) | |
H21 | −0.367 (3) | 1.078 (3) | −0.0130 (11) | 0.046 (7)* | |
H22 | −0.195 (2) | 1.096 (3) | −0.0085 (10) | 0.045 (7)* | |
N3 | −0.38907 (16) | 0.82762 (19) | 0.04364 (7) | 0.0277 (4) | |
C4 | −0.3641 (2) | 0.6896 (2) | 0.07527 (8) | 0.0243 (4) | |
C5 | −0.21929 (18) | 0.6316 (2) | 0.09563 (8) | 0.0225 (4) | |
H5 | −0.2033 | 0.5322 | 0.1175 | 0.028* | |
C6 | −0.09983 (19) | 0.7301 (2) | 0.08166 (8) | 0.0219 (4) | |
S1 | −0.53545 (5) | 0.59059 (7) | 0.08775 (3) | 0.0405 (2) | |
C7 | −0.47507 (19) | 0.4307 (2) | 0.13952 (9) | 0.0263 (4) | |
C8 | −0.4799 (2) | 0.2752 (3) | 0.11697 (11) | 0.0407 (5) | |
H8 | −0.5110 | 0.2544 | 0.0734 | 0.051* | |
C9 | −0.4391 (3) | 0.1490 (3) | 0.15819 (13) | 0.0524 (7) | |
H9 | −0.4433 | 0.0414 | 0.1429 | 0.065* | |
C10 | −0.3931 (2) | 0.1792 (3) | 0.22057 (12) | 0.0480 (6) | |
H10 | −0.3642 | 0.0924 | 0.2485 | 0.060* | |
C11 | −0.3881 (3) | 0.3333 (3) | 0.24326 (11) | 0.0451 (6) | |
H11 | −0.3552 | 0.3535 | 0.2867 | 0.056* | |
C12 | −0.4314 (2) | 0.4599 (3) | 0.20276 (10) | 0.0364 (5) | |
H12 | −0.4308 | 0.5668 | 0.2187 | 0.045* | |
S2 | 0.09499 (5) | 0.69097 (6) | 0.10351 (2) | 0.02865 (17) | |
C13 | 0.09830 (18) | 0.4884 (2) | 0.13030 (9) | 0.0230 (4) | |
C14 | 0.0717 (2) | 0.3629 (3) | 0.08753 (9) | 0.0302 (5) | |
H14 | 0.0485 | 0.3850 | 0.0435 | 0.038* | |
C15 | 0.0789 (2) | 0.2053 (3) | 0.10885 (10) | 0.0343 (5) | |
H15 | 0.0593 | 0.1190 | 0.0797 | 0.043* | |
C16 | 0.1147 (2) | 0.1744 (3) | 0.17267 (10) | 0.0357 (5) | |
H16 | 0.1203 | 0.0663 | 0.1874 | 0.045* | |
C17 | 0.1425 (2) | 0.2983 (3) | 0.21503 (10) | 0.0387 (5) | |
H17 | 0.1675 | 0.2757 | 0.2589 | 0.048* | |
C18 | 0.1342 (2) | 0.4560 (3) | 0.19428 (9) | 0.0299 (5) | |
H18 | 0.1530 | 0.5417 | 0.2237 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0262 (8) | 0.0199 (9) | 0.0286 (9) | 0.0012 (6) | 0.0017 (6) | 0.0019 (7) |
C2 | 0.0319 (11) | 0.0210 (11) | 0.0263 (10) | 0.0065 (8) | 0.0036 (8) | 0.0042 (8) |
N21 | 0.0350 (11) | 0.0288 (11) | 0.0489 (12) | 0.0064 (9) | 0.0029 (9) | 0.0172 (9) |
N3 | 0.0240 (8) | 0.0269 (10) | 0.0324 (9) | 0.0066 (7) | 0.0033 (7) | 0.0086 (7) |
C4 | 0.0236 (10) | 0.0251 (11) | 0.0243 (10) | 0.0030 (7) | 0.0037 (7) | 0.0049 (8) |
C5 | 0.0210 (9) | 0.0213 (10) | 0.0251 (10) | 0.0032 (7) | 0.0013 (7) | 0.0056 (8) |
C6 | 0.0219 (9) | 0.0222 (11) | 0.0216 (10) | 0.0049 (7) | 0.0023 (7) | 0.0000 (8) |
S1 | 0.0180 (3) | 0.0464 (4) | 0.0569 (4) | 0.0036 (2) | 0.0030 (2) | 0.0258 (3) |
C7 | 0.0178 (9) | 0.0294 (12) | 0.0322 (11) | 0.0019 (8) | 0.0045 (7) | 0.0087 (9) |
C8 | 0.0431 (13) | 0.0414 (15) | 0.0374 (13) | 0.0001 (10) | 0.0024 (9) | −0.0034 (11) |
C9 | 0.0602 (16) | 0.0285 (14) | 0.0694 (19) | 0.0039 (11) | 0.0112 (13) | 0.0011 (13) |
C10 | 0.0408 (13) | 0.0454 (17) | 0.0579 (17) | 0.0075 (11) | 0.0060 (11) | 0.0268 (13) |
C11 | 0.0425 (13) | 0.0588 (18) | 0.0339 (13) | −0.0049 (11) | 0.0036 (10) | 0.0152 (12) |
C12 | 0.0378 (12) | 0.0355 (14) | 0.0370 (13) | −0.0040 (9) | 0.0098 (9) | −0.0010 (10) |
S2 | 0.0187 (3) | 0.0248 (3) | 0.0419 (3) | −0.00065 (18) | 0.0004 (2) | 0.0068 (2) |
C13 | 0.0147 (9) | 0.0228 (11) | 0.0313 (11) | 0.0011 (7) | 0.0020 (7) | 0.0023 (8) |
C14 | 0.0315 (11) | 0.0301 (12) | 0.0284 (11) | 0.0042 (8) | 0.0006 (8) | −0.0002 (9) |
C15 | 0.0369 (12) | 0.0275 (12) | 0.0376 (13) | 0.0029 (9) | −0.0002 (9) | −0.0059 (10) |
C16 | 0.0408 (12) | 0.0241 (13) | 0.0418 (13) | 0.0027 (9) | 0.0027 (9) | 0.0068 (10) |
C17 | 0.0509 (14) | 0.0362 (14) | 0.0277 (12) | 0.0051 (10) | −0.0016 (9) | 0.0077 (10) |
C18 | 0.0294 (10) | 0.0275 (12) | 0.0317 (12) | 0.0033 (8) | −0.0025 (8) | −0.0029 (9) |
N1—C6 | 1.328 (2) | C9—H9 | 0.9500 |
N1—C2 | 1.350 (2) | C10—C11 | 1.366 (3) |
C2—N21 | 1.335 (3) | C10—H10 | 0.9500 |
C2—N3 | 1.350 (2) | C11—C12 | 1.386 (3) |
N21—H21 | 0.78 (2) | C11—H11 | 0.9500 |
N21—H22 | 0.90 (2) | C12—H12 | 0.9500 |
N3—C4 | 1.335 (2) | S2—C13 | 1.775 (2) |
C4—C5 | 1.389 (2) | C13—C14 | 1.385 (3) |
C4—S1 | 1.7593 (18) | C13—C18 | 1.385 (3) |
C5—C6 | 1.387 (2) | C14—C15 | 1.384 (3) |
C5—H5 | 0.9500 | C14—H14 | 0.9500 |
C6—S2 | 1.7596 (18) | C15—C16 | 1.379 (3) |
S1—C7 | 1.7693 (19) | C15—H15 | 0.9500 |
C7—C8 | 1.376 (3) | C16—C17 | 1.371 (3) |
C7—C12 | 1.376 (3) | C16—H16 | 0.9500 |
C8—C9 | 1.388 (3) | C17—C18 | 1.381 (3) |
C8—H8 | 0.9500 | C17—H17 | 0.9500 |
C9—C10 | 1.364 (3) | C18—H18 | 0.9500 |
C6—N1—C2 | 115.99 (15) | C9—C10—H10 | 119.7 |
N21—C2—N3 | 117.86 (18) | C11—C10—H10 | 119.7 |
N21—C2—N1 | 116.86 (18) | C10—C11—C12 | 119.8 (2) |
N3—C2—N1 | 125.28 (17) | C10—C11—H11 | 120.1 |
C2—N21—H21 | 120.3 (18) | C12—C11—H11 | 120.1 |
C2—N21—H22 | 113.2 (15) | C7—C12—C11 | 120.0 (2) |
H21—N21—H22 | 127 (2) | C7—C12—H12 | 120.0 |
C4—N3—C2 | 116.17 (15) | C11—C12—H12 | 120.0 |
N3—C4—C5 | 123.56 (16) | C6—S2—C13 | 104.10 (8) |
N3—C4—S1 | 112.12 (13) | C14—C13—C18 | 119.90 (18) |
C5—C4—S1 | 124.32 (14) | C14—C13—S2 | 120.60 (15) |
C6—C5—C4 | 114.83 (17) | C18—C13—S2 | 119.44 (15) |
C6—C5—H5 | 122.6 | C15—C14—C13 | 120.02 (19) |
C4—C5—H5 | 122.6 | C15—C14—H14 | 120.0 |
N1—C6—C5 | 124.14 (16) | C13—C14—H14 | 120.0 |
N1—C6—S2 | 110.87 (13) | C16—C15—C14 | 119.6 (2) |
C5—C6—S2 | 124.99 (14) | C16—C15—H15 | 120.2 |
C4—S1—C7 | 103.61 (9) | C14—C15—H15 | 120.2 |
C8—C7—C12 | 119.90 (19) | C17—C16—C15 | 120.5 (2) |
C8—C7—S1 | 119.57 (16) | C17—C16—H16 | 119.7 |
C12—C7—S1 | 120.43 (16) | C15—C16—H16 | 119.7 |
C7—C8—C9 | 119.6 (2) | C16—C17—C18 | 120.3 (2) |
C7—C8—H8 | 120.2 | C16—C17—H17 | 119.8 |
C9—C8—H8 | 120.2 | C18—C17—H17 | 119.8 |
C10—C9—C8 | 120.1 (2) | C17—C18—C13 | 119.67 (19) |
C10—C9—H9 | 119.9 | C17—C18—H18 | 120.2 |
C8—C9—H9 | 119.9 | C13—C18—H18 | 120.2 |
C9—C10—C11 | 120.5 (2) | ||
C6—N1—C2—N21 | −178.56 (18) | C7—C8—C9—C10 | −0.6 (3) |
C6—N1—C2—N3 | 1.8 (3) | C8—C9—C10—C11 | 0.7 (4) |
N21—C2—N3—C4 | 178.52 (18) | C9—C10—C11—C12 | 0.5 (3) |
N1—C2—N3—C4 | −1.8 (3) | C8—C7—C12—C11 | 1.8 (3) |
C2—N3—C4—C5 | 0.3 (3) | S1—C7—C12—C11 | 178.29 (16) |
C2—N3—C4—S1 | −179.60 (14) | C10—C11—C12—C7 | −1.8 (3) |
N3—C4—C5—C6 | 1.1 (3) | N1—C6—S2—C13 | −169.17 (13) |
S1—C4—C5—C6 | −179.02 (14) | C5—C6—S2—C13 | 11.49 (18) |
C2—N1—C6—C5 | −0.2 (3) | C6—S2—C13—C14 | 72.38 (16) |
C2—N1—C6—S2 | −179.51 (13) | C6—S2—C13—C18 | −110.35 (15) |
C4—C5—C6—N1 | −1.2 (3) | C18—C13—C14—C15 | 0.9 (3) |
C4—C5—C6—S2 | 178.06 (14) | S2—C13—C14—C15 | 178.16 (14) |
N3—C4—S1—C7 | −171.71 (14) | C13—C14—C15—C16 | −0.9 (3) |
C5—C4—S1—C7 | 8.43 (19) | C14—C15—C16—C17 | 0.3 (3) |
C4—S1—C7—C8 | −108.49 (16) | C15—C16—C17—C18 | 0.3 (3) |
C4—S1—C7—C12 | 75.05 (17) | C16—C17—C18—C13 | −0.3 (3) |
C12—C7—C8—C9 | −0.6 (3) | C14—C13—C18—C17 | −0.3 (3) |
S1—C7—C8—C9 | −177.11 (16) | S2—C13—C18—C17 | −177.61 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···N3i | 0.78 (2) | 2.32 (2) | 3.102 (2) | 177 (2) |
N21—H22···S2ii | 0.90 (2) | 2.88 (2) | 3.586 (2) | 136.2 (17) |
Symmetry codes: (i) −x−1, −y+2, −z; (ii) −x, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C16H13N3S2 |
Mr | 311.41 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 150 |
a, b, c (Å) | 8.7937 (18), 8.3091 (17), 21.148 (4) |
β (°) | 95.73 (3) |
V (Å3) | 1537.5 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.34 |
Crystal size (mm) | 0.34 × 0.18 × 0.16 |
Data collection | |
Diffractometer | Enraf Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.893, 0.947 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12370, 3476, 2440 |
Rint | 0.088 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.117, 1.00 |
No. of reflections | 3476 |
No. of parameters | 198 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.29, −0.47 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···N3i | 0.78 (2) | 2.32 (2) | 3.102 (2) | 177 (2) |
N21—H22···S2ii | 0.90 (2) | 2.88 (2) | 3.586 (2) | 136.2 (17) |
Symmetry codes: (i) −x−1, −y+2, −z; (ii) −x, −y+2, −z. |
NO COMMENT