


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810040316/xu5047sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810040316/xu5047Isup2.hkl |
CCDC reference: 799617
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.050
- wR factor = 0.172
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15' PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 2 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 4
Alert level G PLAT301_ALERT_3_G Note: Main Residue Disorder ................... 24.00 Perc. PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 17 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms .... !
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 2 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 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
To a solution of (E)-4-(2,3-dihydro-1,3-benzothiazol-2-ylidene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one (1 g, 3.25 mmol) in DMF (50 ml), was added sodium carbonate (2.5 g, 23 mmol), tetra-n-butyl ammonium bromide (0.15 g, 1 mmol) and allyl bromide (5.6 g, 46 mmol). The mixture was stirred for 24 h at room temperature. The solid material was removed by filtration and the solution was evaporated under reduced. The residue was washed with dichloromethane and hexane, and the recrystallized from ethanol to afford the title compound as colorless crystals.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C).
The allyl and phenyl units are disordered over two positions; the disorder could be refined, and was assumed to be a 1:1 type of disorder. For the allyl unit, the single-bond distances were restrained to 1.50±0.01 Å and the double-bond distances to 1.35±0.01 Å; the anisotropic temperature factors were restrained to be nearly isotropic. The phenyl rings were refined as rigid hexagons of 1.39 Å sides; the N–Cphenyl pair of distances were restrained to within 0.01 Å of each other. Additionally, the temperature factors of the primed atoms were restrained to those of the unprimed ones.
(E)-4-(2,3-Dihydro-1,3-benzothiazol-2-ylidene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one is an amine that can under a nucleophilic substitution with organo bromides to form 2-substituted derivatives if tetra-n-butyl ammonium bromide is used as catalyst. In this study, the compound is reacted with allyl bromide to yield the title compound (Scheme I, Fig. 1).
For the structure of a related compound (E)-4-(2,3-dihydro-1,3-benzothiazol-2-ylidene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one, see: Chakibe et al. (2010).
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
![]() | Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C20H17N3OS at the 50% probability level; hydrogen atoms are drawn as arbitrary radius. The disorder is not shown |
C20H17N3OS | F(000) = 1456 |
Mr = 347.43 | Dx = 1.306 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 3745 reflections |
a = 17.8734 (5) Å | θ = 2.3–22.5° |
b = 10.4297 (2) Å | µ = 0.20 mm−1 |
c = 18.9578 (4) Å | T = 293 K |
V = 3534.00 (14) Å3 | Prism, colorless |
Z = 8 | 0.30 × 0.30 × 0.25 mm |
Bruker X8 APEXII diffractometer | 3678 independent reflections |
Radiation source: fine-focus sealed tube | 2341 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 26.6°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −22→21 |
Tmin = 0.944, Tmax = 0.953 | k = −13→12 |
18349 measured reflections | l = −23→23 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.096P)2 + 0.8646P] where P = (Fo2 + 2Fc2)/3 |
3678 reflections | (Δ/σ)max = 0.001 |
227 parameters | Δρmax = 0.32 e Å−3 |
17 restraints | Δρmin = −0.25 e Å−3 |
C20H17N3OS | V = 3534.00 (14) Å3 |
Mr = 347.43 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 17.8734 (5) Å | µ = 0.20 mm−1 |
b = 10.4297 (2) Å | T = 293 K |
c = 18.9578 (4) Å | 0.30 × 0.30 × 0.25 mm |
Bruker X8 APEXII diffractometer | 3678 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2341 reflections with I > 2σ(I) |
Tmin = 0.944, Tmax = 0.953 | Rint = 0.032 |
18349 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 17 restraints |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.32 e Å−3 |
3678 reflections | Δρmin = −0.25 e Å−3 |
227 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.54022 (4) | 0.59623 (7) | 0.57529 (3) | 0.0590 (2) | |
O1 | 0.63189 (12) | 0.5096 (2) | 0.45761 (10) | 0.0808 (6) | |
N1 | 0.61613 (12) | 0.7853 (2) | 0.62953 (11) | 0.0590 (6) | |
N2 | 0.79529 (13) | 0.6762 (2) | 0.48741 (11) | 0.0593 (6) | |
N3 | 0.75432 (13) | 0.5809 (2) | 0.45335 (11) | 0.0627 (6) | |
C1 | 0.50073 (15) | 0.6812 (2) | 0.64448 (12) | 0.0531 (6) | |
C2 | 0.43115 (17) | 0.6640 (3) | 0.67650 (14) | 0.0669 (7) | |
H2 | 0.3989 | 0.5995 | 0.6617 | 0.080* | |
C3 | 0.41164 (19) | 0.7448 (3) | 0.73035 (15) | 0.0762 (9) | |
H3 | 0.3654 | 0.7349 | 0.7522 | 0.091* | |
C4 | 0.4595 (2) | 0.8412 (3) | 0.75287 (16) | 0.0798 (9) | |
H4 | 0.4454 | 0.8943 | 0.7900 | 0.096* | |
C5 | 0.52717 (19) | 0.8589 (3) | 0.72110 (15) | 0.0743 (8) | |
H5 | 0.5587 | 0.9242 | 0.7362 | 0.089* | |
C6 | 0.54904 (16) | 0.7785 (2) | 0.66569 (12) | 0.0566 (6) | |
C7 | 0.61898 (14) | 0.6956 (2) | 0.58142 (11) | 0.0495 (6) | |
C8 | 0.68208 (17) | 0.5800 (3) | 0.48056 (13) | 0.0603 (7) | |
C9 | 0.68293 (15) | 0.6721 (2) | 0.53608 (12) | 0.0518 (6) | |
C10 | 0.75276 (15) | 0.7255 (2) | 0.53898 (12) | 0.0548 (6) | |
C11 | 0.78327 (19) | 0.8222 (3) | 0.58934 (16) | 0.0760 (8) | |
H11A | 0.8269 | 0.8617 | 0.5693 | 0.114* | |
H11B | 0.7965 | 0.7806 | 0.6327 | 0.114* | |
H11C | 0.7461 | 0.8865 | 0.5984 | 0.114* | |
C12 | 0.87637 (17) | 0.6862 (3) | 0.48056 (16) | 0.0746 (8) | |
H12A | 0.8914 | 0.7755 | 0.4806 | 0.090* | 0.50 |
H12B | 0.8926 | 0.6475 | 0.4366 | 0.090* | 0.50 |
H12C | 0.8825 | 0.7782 | 0.4852 | 0.090* | 0.50 |
H12D | 0.8812 | 0.6708 | 0.4303 | 0.090* | 0.50 |
C13 | 0.9121 (11) | 0.6151 (15) | 0.5440 (7) | 0.101 (3) | 0.50 |
H13 | 0.8915 | 0.5398 | 0.5616 | 0.121* | 0.50 |
C14 | 0.9722 (11) | 0.6652 (18) | 0.5718 (9) | 0.139 (4) | 0.50 |
H14A | 0.9920 | 0.7407 | 0.5535 | 0.166* | 0.50 |
H14B | 0.9953 | 0.6254 | 0.6099 | 0.166* | 0.50 |
C13' | 0.9175 (11) | 0.5938 (15) | 0.5294 (7) | 0.101 (3) | 0.50 |
H13' | 0.9148 | 0.5076 | 0.5171 | 0.121* | 0.50 |
C14' | 0.9555 (11) | 0.6196 (18) | 0.5854 (8) | 0.139 (4) | 0.50 |
H14C | 0.9603 | 0.7041 | 0.6004 | 0.166* | 0.50 |
H14D | 0.9781 | 0.5538 | 0.6107 | 0.166* | 0.50 |
C15 | 0.7691 (10) | 0.5140 (10) | 0.3885 (4) | 0.0510 (18) | 0.50 |
C16 | 0.8277 (10) | 0.4304 (14) | 0.3741 (5) | 0.0863 (18) | 0.50 |
H16 | 0.8561 | 0.3969 | 0.4108 | 0.104* | 0.50 |
C17 | 0.8437 (10) | 0.3967 (13) | 0.3048 (5) | 0.105 (3) | 0.50 |
H17 | 0.8829 | 0.3407 | 0.2951 | 0.126* | 0.50 |
C18 | 0.8012 (11) | 0.4466 (10) | 0.2499 (4) | 0.110 (4) | 0.50 |
H18 | 0.8119 | 0.4241 | 0.2035 | 0.132* | 0.50 |
C19 | 0.7426 (10) | 0.5303 (12) | 0.2643 (6) | 0.102 (3) | 0.50 |
H19 | 0.7142 | 0.5637 | 0.2275 | 0.123* | 0.50 |
C20 | 0.7265 (9) | 0.5640 (12) | 0.3336 (7) | 0.0714 (19) | 0.50 |
H20 | 0.6874 | 0.6199 | 0.3432 | 0.086* | 0.50 |
C15' | 0.7791 (10) | 0.5424 (10) | 0.3848 (5) | 0.0510 (18) | 0.50 |
C16' | 0.8326 (10) | 0.4458 (14) | 0.3884 (4) | 0.0863 (18) | 0.50 |
H16' | 0.8571 | 0.4294 | 0.4308 | 0.104* | 0.50 |
C17' | 0.8494 (11) | 0.3738 (12) | 0.3288 (5) | 0.105 (3) | 0.50 |
H17' | 0.8852 | 0.3092 | 0.3312 | 0.126* | 0.50 |
C18' | 0.8127 (11) | 0.3984 (9) | 0.2656 (4) | 0.110 (4) | 0.50 |
H18' | 0.8240 | 0.3502 | 0.2257 | 0.132* | 0.50 |
C19' | 0.7593 (10) | 0.4949 (13) | 0.2620 (5) | 0.102 (3) | 0.50 |
H19' | 0.7347 | 0.5113 | 0.2197 | 0.123* | 0.50 |
C20' | 0.7425 (9) | 0.5669 (11) | 0.3216 (7) | 0.0714 (19) | 0.50 |
H20' | 0.7067 | 0.6315 | 0.3192 | 0.086* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0542 (4) | 0.0698 (4) | 0.0528 (4) | −0.0033 (3) | 0.0062 (3) | −0.0106 (3) |
O1 | 0.0647 (13) | 0.1020 (15) | 0.0756 (13) | −0.0228 (12) | 0.0166 (10) | −0.0337 (12) |
N1 | 0.0559 (14) | 0.0630 (12) | 0.0580 (12) | 0.0042 (10) | 0.0020 (10) | −0.0066 (10) |
N2 | 0.0529 (14) | 0.0655 (12) | 0.0594 (12) | −0.0072 (11) | 0.0080 (10) | −0.0040 (10) |
N3 | 0.0568 (14) | 0.0740 (13) | 0.0573 (12) | −0.0097 (11) | 0.0118 (11) | −0.0143 (10) |
C1 | 0.0521 (16) | 0.0634 (14) | 0.0438 (12) | 0.0102 (12) | −0.0007 (11) | 0.0048 (10) |
C2 | 0.0615 (18) | 0.0812 (18) | 0.0581 (15) | 0.0026 (15) | 0.0106 (13) | 0.0007 (13) |
C3 | 0.067 (2) | 0.100 (2) | 0.0611 (16) | 0.0151 (18) | 0.0163 (15) | 0.0006 (15) |
C4 | 0.084 (2) | 0.090 (2) | 0.0657 (17) | 0.0216 (19) | 0.0131 (17) | −0.0169 (16) |
C5 | 0.075 (2) | 0.0803 (18) | 0.0677 (17) | 0.0077 (16) | 0.0047 (16) | −0.0213 (15) |
C6 | 0.0589 (17) | 0.0610 (14) | 0.0500 (13) | 0.0111 (13) | −0.0020 (12) | −0.0043 (11) |
C7 | 0.0514 (15) | 0.0534 (12) | 0.0438 (11) | 0.0041 (11) | −0.0018 (10) | 0.0018 (10) |
C8 | 0.0599 (17) | 0.0689 (15) | 0.0521 (13) | −0.0055 (14) | 0.0088 (13) | −0.0060 (12) |
C9 | 0.0538 (16) | 0.0566 (13) | 0.0450 (12) | 0.0004 (12) | 0.0022 (11) | −0.0006 (10) |
C10 | 0.0558 (16) | 0.0580 (13) | 0.0507 (13) | −0.0014 (12) | 0.0024 (12) | −0.0003 (11) |
C11 | 0.070 (2) | 0.0852 (19) | 0.0725 (17) | −0.0151 (16) | 0.0033 (15) | −0.0177 (15) |
C12 | 0.0580 (19) | 0.090 (2) | 0.0763 (19) | −0.0105 (16) | 0.0148 (15) | −0.0134 (16) |
C13 | 0.072 (3) | 0.124 (5) | 0.108 (6) | 0.039 (3) | −0.021 (4) | −0.065 (4) |
C14 | 0.136 (8) | 0.165 (9) | 0.115 (6) | 0.033 (7) | 0.001 (5) | 0.023 (6) |
C13' | 0.072 (3) | 0.124 (5) | 0.108 (6) | 0.039 (3) | −0.021 (4) | −0.065 (4) |
C14' | 0.136 (8) | 0.165 (9) | 0.115 (6) | 0.033 (7) | 0.001 (5) | 0.023 (6) |
C15 | 0.059 (4) | 0.031 (4) | 0.0631 (17) | −0.024 (4) | 0.0240 (16) | −0.001 (2) |
C16 | 0.087 (3) | 0.067 (3) | 0.105 (4) | 0.001 (3) | 0.026 (4) | −0.022 (3) |
C17 | 0.122 (5) | 0.085 (5) | 0.108 (8) | 0.000 (4) | 0.058 (7) | −0.028 (5) |
C18 | 0.133 (8) | 0.098 (8) | 0.098 (5) | −0.045 (8) | 0.057 (6) | −0.038 (5) |
C19 | 0.100 (7) | 0.149 (8) | 0.0579 (19) | −0.034 (6) | 0.029 (3) | −0.017 (3) |
C20 | 0.069 (6) | 0.102 (2) | 0.043 (4) | −0.020 (3) | 0.028 (3) | 0.007 (2) |
C15' | 0.059 (4) | 0.031 (4) | 0.0631 (17) | −0.024 (4) | 0.0240 (16) | −0.001 (2) |
C16' | 0.087 (3) | 0.067 (3) | 0.105 (4) | 0.001 (3) | 0.026 (4) | −0.022 (3) |
C17' | 0.122 (5) | 0.085 (5) | 0.108 (8) | 0.000 (4) | 0.058 (7) | −0.028 (5) |
C18' | 0.133 (8) | 0.098 (8) | 0.098 (5) | −0.045 (8) | 0.057 (6) | −0.038 (5) |
C19' | 0.100 (7) | 0.149 (8) | 0.0579 (19) | −0.034 (6) | 0.029 (3) | −0.017 (3) |
C20' | 0.069 (6) | 0.102 (2) | 0.043 (4) | −0.020 (3) | 0.028 (3) | 0.007 (2) |
S1—C1 | 1.733 (2) | C12—H12C | 0.9701 |
S1—C7 | 1.752 (3) | C12—H12D | 0.9701 |
O1—C8 | 1.238 (3) | C13—C14 | 1.305 (10) |
N1—C7 | 1.307 (3) | C13—H13 | 0.9300 |
N1—C6 | 1.383 (3) | C14—H14A | 0.9300 |
N2—C10 | 1.341 (3) | C14—H14B | 0.9300 |
N2—N3 | 1.393 (3) | C13'—C14' | 1.289 (9) |
N2—C12 | 1.459 (3) | C13'—H13' | 0.9300 |
N3—C8 | 1.391 (4) | C14'—H14C | 0.9300 |
N3—C15' | 1.430 (6) | C14'—H14D | 0.9300 |
N3—C15 | 1.438 (6) | C15—C16 | 1.3900 |
C1—C6 | 1.392 (4) | C15—C20 | 1.3900 |
C1—C2 | 1.395 (4) | C16—C17 | 1.3900 |
C2—C3 | 1.369 (4) | C16—H16 | 0.9300 |
C2—H2 | 0.9300 | C17—C18 | 1.3900 |
C3—C4 | 1.388 (5) | C17—H17 | 0.9300 |
C3—H3 | 0.9300 | C18—C19 | 1.3900 |
C4—C5 | 1.363 (4) | C18—H18 | 0.9300 |
C4—H4 | 0.9300 | C19—C20 | 1.3900 |
C5—C6 | 1.399 (4) | C19—H19 | 0.9300 |
C5—H5 | 0.9300 | C20—H20 | 0.9300 |
C7—C9 | 1.451 (3) | C15'—C16' | 1.3900 |
C8—C9 | 1.425 (3) | C15'—C20' | 1.3900 |
C9—C10 | 1.368 (4) | C16'—C17' | 1.3900 |
C10—C11 | 1.492 (4) | C16'—H16' | 0.9300 |
C11—H11A | 0.9600 | C17'—C18' | 1.3900 |
C11—H11B | 0.9600 | C17'—H17' | 0.9300 |
C11—H11C | 0.9600 | C18'—C19' | 1.3900 |
C12—C13' | 1.525 (9) | C18'—H18' | 0.9300 |
C12—C13 | 1.551 (8) | C19'—C20' | 1.3900 |
C12—H12A | 0.9700 | C19'—H19' | 0.9300 |
C12—H12B | 0.9700 | C20'—H20' | 0.9300 |
C1—S1—C7 | 88.53 (12) | H12A—C12—H12B | 108.5 |
C7—N1—C6 | 110.1 (2) | C13'—C12—H12C | 121.0 |
C10—N2—N3 | 108.3 (2) | C13—C12—H12C | 110.8 |
C10—N2—C12 | 126.9 (2) | C13'—C12—H12D | 116.7 |
N3—N2—C12 | 122.1 (2) | H12C—C12—H12D | 104.1 |
C8—N3—N2 | 108.7 (2) | C14—C13—C12 | 117.5 (15) |
C8—N3—C15' | 128.5 (7) | C14—C13—H13 | 121.3 |
N2—N3—C15' | 117.3 (6) | C12—C13—H13 | 121.3 |
C8—N3—C15 | 118.9 (7) | C13—C14—H14A | 120.0 |
N2—N3—C15 | 130.3 (6) | C13—C14—H14B | 120.0 |
C6—C1—C2 | 121.4 (2) | H14A—C14—H14B | 120.0 |
C6—C1—S1 | 109.81 (19) | C14'—C13'—C12 | 128.4 (15) |
C2—C1—S1 | 128.8 (2) | C14'—C13'—H13' | 115.8 |
C3—C2—C1 | 118.2 (3) | C12—C13'—H13' | 115.8 |
C3—C2—H2 | 120.9 | C13'—C14'—H14C | 120.0 |
C1—C2—H2 | 120.9 | C13'—C14'—H14D | 120.0 |
C2—C3—C4 | 121.2 (3) | H14C—C14'—H14D | 120.0 |
C2—C3—H3 | 119.4 | C16—C15—C20 | 120.0 |
C4—C3—H3 | 119.4 | C16—C15—N3 | 127.6 (11) |
C5—C4—C3 | 120.6 (3) | C20—C15—N3 | 111.0 (10) |
C5—C4—H4 | 119.7 | C15—C16—C17 | 120.0 |
C3—C4—H4 | 119.7 | C15—C16—H16 | 120.0 |
C4—C5—C6 | 119.9 (3) | C17—C16—H16 | 120.0 |
C4—C5—H5 | 120.0 | C18—C17—C16 | 120.0 |
C6—C5—H5 | 120.0 | C18—C17—H17 | 120.0 |
N1—C6—C1 | 115.6 (2) | C16—C17—H17 | 120.0 |
N1—C6—C5 | 125.7 (3) | C17—C18—C19 | 120.0 |
C1—C6—C5 | 118.7 (3) | C17—C18—H18 | 120.0 |
N1—C7—C9 | 124.4 (2) | C19—C18—H18 | 120.0 |
N1—C7—S1 | 115.99 (19) | C20—C19—C18 | 120.0 |
C9—C7—S1 | 119.57 (17) | C20—C19—H19 | 120.0 |
O1—C8—N3 | 123.1 (2) | C18—C19—H19 | 120.0 |
O1—C8—C9 | 131.8 (3) | C19—C20—C15 | 120.0 |
N3—C8—C9 | 105.0 (2) | C19—C20—H20 | 120.0 |
C10—C9—C8 | 108.3 (2) | C15—C20—H20 | 120.0 |
C10—C9—C7 | 128.8 (2) | C16'—C15'—C20' | 120.0 |
C8—C9—C7 | 122.9 (2) | C16'—C15'—N3 | 111.8 (10) |
N2—C10—C9 | 109.4 (2) | C20'—C15'—N3 | 125.8 (11) |
N2—C10—C11 | 121.2 (3) | C15'—C16'—C17' | 120.0 |
C9—C10—C11 | 129.4 (2) | C15'—C16'—H16' | 120.0 |
C10—C11—H11A | 109.5 | C17'—C16'—H16' | 120.0 |
C10—C11—H11B | 109.5 | C18'—C17'—C16' | 120.0 |
H11A—C11—H11B | 109.5 | C18'—C17'—H17' | 120.0 |
C10—C11—H11C | 109.5 | C16'—C17'—H17' | 120.0 |
H11A—C11—H11C | 109.5 | C19'—C18'—C17' | 120.0 |
H11B—C11—H11C | 109.5 | C19'—C18'—H18' | 120.0 |
N2—C12—C13' | 112.3 (9) | C17'—C18'—H18' | 120.0 |
N2—C12—C13 | 107.8 (9) | C18'—C19'—C20' | 120.0 |
N2—C12—H12A | 110.1 | C18'—C19'—H19' | 120.0 |
C13'—C12—H12A | 118.2 | C20'—C19'—H19' | 120.0 |
C13—C12—H12A | 110.1 | C19'—C20'—C15' | 120.0 |
N2—C12—H12B | 110.1 | C19'—C20'—H20' | 120.0 |
C13—C12—H12B | 110.1 | C15'—C20'—H20' | 120.0 |
C10—N2—N3—C8 | 5.6 (3) | C12—N2—C10—C11 | 13.0 (4) |
C12—N2—N3—C8 | 168.3 (2) | C8—C9—C10—N2 | 2.0 (3) |
C10—N2—N3—C15' | 161.9 (8) | C7—C9—C10—N2 | 179.5 (2) |
C12—N2—N3—C15' | −35.5 (8) | C8—C9—C10—C11 | −177.2 (3) |
C10—N2—N3—C15 | 168.7 (9) | C7—C9—C10—C11 | 0.3 (5) |
C12—N2—N3—C15 | −28.7 (9) | C10—N2—C12—C13' | 77.9 (7) |
C7—S1—C1—C6 | 1.10 (18) | N3—N2—C12—C13' | −81.3 (7) |
C7—S1—C1—C2 | 179.7 (2) | C10—N2—C12—C13 | 64.1 (7) |
C6—C1—C2—C3 | −0.8 (4) | N3—N2—C12—C13 | −95.2 (7) |
S1—C1—C2—C3 | −179.3 (2) | N2—C12—C13—C14 | −142.4 (14) |
C1—C2—C3—C4 | −0.1 (4) | C13'—C12—C13—C14 | 106 (7) |
C2—C3—C4—C5 | 0.8 (5) | N2—C12—C13'—C14' | −108 (2) |
C3—C4—C5—C6 | −0.6 (5) | C13—C12—C13'—C14' | −35 (6) |
C7—N1—C6—C1 | 0.3 (3) | C8—N3—C15—C16 | −133.0 (8) |
C7—N1—C6—C5 | 179.4 (3) | N2—N3—C15—C16 | 65.4 (10) |
C2—C1—C6—N1 | −179.8 (2) | C15'—N3—C15—C16 | 91 (6) |
S1—C1—C6—N1 | −1.1 (3) | C8—N3—C15—C20 | 60.6 (8) |
C2—C1—C6—C5 | 1.0 (4) | N2—N3—C15—C20 | −101.0 (10) |
S1—C1—C6—C5 | 179.8 (2) | C15'—N3—C15—C20 | −75 (6) |
C4—C5—C6—N1 | −179.4 (3) | C20—C15—C16—C17 | 0.0 |
C4—C5—C6—C1 | −0.3 (4) | N3—C15—C16—C17 | −165.3 (9) |
C6—N1—C7—C9 | −177.2 (2) | C15—C16—C17—C18 | 0.0 |
C6—N1—C7—S1 | 0.6 (3) | C16—C17—C18—C19 | 0.0 |
C1—S1—C7—N1 | −1.01 (19) | C17—C18—C19—C20 | 0.0 |
C1—S1—C7—C9 | 176.89 (19) | C18—C19—C20—C15 | 0.0 |
N2—N3—C8—O1 | 176.1 (3) | C16—C15—C20—C19 | 0.0 |
C15'—N3—C8—O1 | 23.3 (8) | N3—C15—C20—C19 | 167.6 (9) |
C15—N3—C8—O1 | 10.8 (7) | C8—N3—C15'—C16' | −121.9 (9) |
N2—N3—C8—C9 | −4.3 (3) | N2—N3—C15'—C16' | 87.4 (7) |
C15'—N3—C8—C9 | −157.0 (7) | C15—N3—C15'—C16' | −71 (6) |
C15—N3—C8—C9 | −169.5 (7) | C8—N3—C15'—C20' | 40.7 (11) |
O1—C8—C9—C10 | −178.9 (3) | N2—N3—C15'—C20' | −110.1 (9) |
N3—C8—C9—C10 | 1.4 (3) | C15—N3—C15'—C20' | 92 (6) |
O1—C8—C9—C7 | 3.4 (5) | C20'—C15'—C16'—C17' | 0.0 |
N3—C8—C9—C7 | −176.2 (2) | N3—C15'—C16'—C17' | 163.7 (10) |
N1—C7—C9—C10 | 7.8 (4) | C15'—C16'—C17'—C18' | 0.0 |
S1—C7—C9—C10 | −169.9 (2) | C16'—C17'—C18'—C19' | 0.0 |
N1—C7—C9—C8 | −175.0 (2) | C17'—C18'—C19'—C20' | 0.0 |
S1—C7—C9—C8 | 7.2 (3) | C18'—C19'—C20'—C15' | 0.0 |
N3—N2—C10—C9 | −4.7 (3) | C16'—C15'—C20'—C19' | 0.0 |
C12—N2—C10—C9 | −166.3 (3) | N3—C15'—C20'—C19' | −161.3 (9) |
N3—N2—C10—C11 | 174.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.93 | 2.59 | 3.318 (3) | 135 |
C12—H12A···O1ii | 0.97 | 2.51 | 3.404 (4) | 152 |
C12—H12C···O1ii | 0.97 | 2.48 | 3.404 (4) | 159 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, y+1/2, z. |
Experimental details
Crystal data | |
Chemical formula | C20H17N3OS |
Mr | 347.43 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 293 |
a, b, c (Å) | 17.8734 (5), 10.4297 (2), 18.9578 (4) |
V (Å3) | 3534.00 (14) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.30 × 0.30 × 0.25 |
Data collection | |
Diffractometer | Bruker X8 APEXII |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.944, 0.953 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18349, 3678, 2341 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.629 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.172, 1.00 |
No. of reflections | 3678 |
No. of parameters | 227 |
No. of restraints | 17 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.25 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.93 | 2.59 | 3.318 (3) | 135 |
C12—H12A···O1ii | 0.97 | 2.51 | 3.404 (4) | 152 |
C12—H12C···O1ii | 0.97 | 2.48 | 3.404 (4) | 159 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, y+1/2, z. |
(E)-4-(2,3-Dihydro-1,3-benzothiazol-2-ylidene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one is an amine that can under a nucleophilic substitution with organo bromides to form 2-substituted derivatives if tetra-n-butyl ammonium bromide is used as catalyst. In this study, the compound is reacted with allyl bromide to yield the title compound (Scheme I, Fig. 1).