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The title mol­ecule, C18H18N2OS, exists as an L-shaped structure with the mean plane of the 4-methyl­phenyl group twisted slightly about the mean plane of the pyrazole-1-carbaldehyde group by 4.7 (2)°, which in turn makes an angle of 82.4 (7)° with the mean plane of the thio­phenyl group. The S-methyl group is slightly twisted out of plane, probably due to steric repulsion between the methyl H and the phenyl H atoms. The crystal packing is stabilized by inter­molecular C—H...O hydrogen bonding between a thio­phenyl H atom and the carbaldehyde O atom, which links the mol­ecules into chains in an alternate inverted pattern parallel oblique to the bc face and along the a axis of the unit cell.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043000/bt2481sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043000/bt2481Isup2.hkl
Contains datablock I

CCDC reference: 663724

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.046
  • wR factor = 0.141
  • Data-to-parameter ratio = 25.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 2000 Deg. PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 17 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C18 H18 N2 O S
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.965 Tmax scaled 0.965 Tmin scaled 0.828 PLAT793_ALERT_1_G Check the Absolute Configuration of C1 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 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 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Pyrazolines have been reported to exhibit a broad spectrum of biological activities such as antibacterial, antifungal, anti-inflammatory, anti-depressent, anti viral activities (Elguero, 1984) and analgesic activities (El-Emary & Bakhite, 1999). Large numbers of pyrazoles are used as antibacterial (Rathelot et al. 2002), anti-inflammatory (Mithun & Holla, 2006; Holla et al. 2000; 2006), antiparasitic (Cottineau et al. 2002) and antidiabetic drugs (Om Prakash et al. 2006). The crystal structures of the following pyrazole aldehydes viz., 5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (Trilleras et al. 2005) and 1-(2,4-dinitrophenyl)-3-(2-hydroxyphenyl)-1H-pyrazole-4-carbaldehyde (Shanmuga Sundara Raj et al. 1999) have been reported. The newly synthesized pyrazolecarbaldehyde, (I), C18H18N2OS, is found to possess good antibacterial activity and its crystal structure is reported.

The title molecule exists as an L-shaped structure with the mean plane of the 4-methylphenyl group twisted slightly about the mean plane of the pyrazole-1-carbaldehyde by 4.7 (2)° which in turn makes an angle of 82.4 (7)° with the mean plane of the thiophenyl group (Fig. 1). The S-methyl group is twisted slightly out of plane with the phenyl group [C7A–S–C4A–C3A torsion angle = 17.81 (16)°] probably due to steric repulsion between the methyl-H and the phenyl-H atoms. The methyl hydrogen atoms on C7B are disordered [H7BA, H7BB, H7BC (0.49 (4) & H7BD, H7BE, H7BF (0.51 (4)].

Crystal packing is stabilized by intermolecular C—H···O hydrogen bonding between a thiophenyl hydrogen [H2AA] and the carbaldehyde oxygen [O] which link the molecules into chains in an alternate inverted pattern parallel and oblique to the bc face and along the a axis of the unit cell (Fig. 2).

Related literature top

For related structures, see: Trilleras et al. (2005); Shanmuga Sundara Raj et al. (1999). For related literature see: Elguero (1984); El-Emary & Bakhite (1999); Rathelot et al. (2002); Mithun & Holla (2006); Holla et al. (2000, 2006); Cottineau et al. (2002); Om Prakash et al. (2006).

Experimental top

A mixture of (2E)-1-(4-methylphenyl)-3-[4-(methylthio)phenyl]prop-2-en-1-one (2.68 g, 0.01 mol) and a molar equivalent of hydrazine hydrate (5 ml, 80%) in formic acid (15 ml) was heated on an oil bath at 373 K for 3–5 hrs (Fig.3). The reaction mass was then poured into ice cold water and neutralized with sodium bicarbonate solution. The solid obtained was filtered, washed with water, dried, and recrystallized from methanol. (yield: 70%; m.p.: 431–433 K). Analysis found: C 69.56, H 5.79, N 8.94, S 10.25%; C18H18N2OS requires: C 69.65, H 5.84, N 9.02, S 10.33%.

Refinement top

All H atoms were placed in their calculated places and all H atoms were refined using a riding model with C—H = 0.93 to 0.98 Å, and with Uiso(H) = 1.19–1.49Ueq(C).

Structure description top

Pyrazolines have been reported to exhibit a broad spectrum of biological activities such as antibacterial, antifungal, anti-inflammatory, anti-depressent, anti viral activities (Elguero, 1984) and analgesic activities (El-Emary & Bakhite, 1999). Large numbers of pyrazoles are used as antibacterial (Rathelot et al. 2002), anti-inflammatory (Mithun & Holla, 2006; Holla et al. 2000; 2006), antiparasitic (Cottineau et al. 2002) and antidiabetic drugs (Om Prakash et al. 2006). The crystal structures of the following pyrazole aldehydes viz., 5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (Trilleras et al. 2005) and 1-(2,4-dinitrophenyl)-3-(2-hydroxyphenyl)-1H-pyrazole-4-carbaldehyde (Shanmuga Sundara Raj et al. 1999) have been reported. The newly synthesized pyrazolecarbaldehyde, (I), C18H18N2OS, is found to possess good antibacterial activity and its crystal structure is reported.

The title molecule exists as an L-shaped structure with the mean plane of the 4-methylphenyl group twisted slightly about the mean plane of the pyrazole-1-carbaldehyde by 4.7 (2)° which in turn makes an angle of 82.4 (7)° with the mean plane of the thiophenyl group (Fig. 1). The S-methyl group is twisted slightly out of plane with the phenyl group [C7A–S–C4A–C3A torsion angle = 17.81 (16)°] probably due to steric repulsion between the methyl-H and the phenyl-H atoms. The methyl hydrogen atoms on C7B are disordered [H7BA, H7BB, H7BC (0.49 (4) & H7BD, H7BE, H7BF (0.51 (4)].

Crystal packing is stabilized by intermolecular C—H···O hydrogen bonding between a thiophenyl hydrogen [H2AA] and the carbaldehyde oxygen [O] which link the molecules into chains in an alternate inverted pattern parallel and oblique to the bc face and along the a axis of the unit cell (Fig. 2).

For related structures, see: Trilleras et al. (2005); Shanmuga Sundara Raj et al. (1999). For related literature see: Elguero (1984); El-Emary & Bakhite (1999); Rathelot et al. (2002); Mithun & Holla (2006); Holla et al. (2000, 2006); Cottineau et al. (2002); Om Prakash et al. (2006).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing atom labeling and 50% probability displacement ellipsoids. Only the major component of the methyl H atoms on C7B are displayed.
[Figure 2] Fig. 2. Packing diagram of the title compound, viewed down the b axis. Dashed lines indicate intermolecular C—H···O hydrogen bonds. Only the major component of the methyl H atoms on C7B are displayed.
[Figure 3] Fig. 3. Preparation of the title compound.
3-(4-methylphenyl)-5-[4-(methylthio)phenyl]-4, 5-dihydro-1H-pyrazole-1-carbaldehyde top
Crystal data top
C18H18N2OSZ = 2
Mr = 310.40F(000) = 328
Triclinic, P1Dx = 1.313 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.3751 (17) ÅCell parameters from 4927 reflections
b = 6.9998 (17) Åθ = 5.0–32.5°
c = 19.791 (5) ŵ = 0.21 mm1
α = 83.57 (2)°T = 296 K
β = 81.70 (2)°Needle, colourless
γ = 64.16 (2)°0.51 × 0.22 × 0.17 mm
V = 785.3 (4) Å3
Data collection top
Oxford Diffraction Gemini R CCD
diffractometer
5145 independent reflections
Radiation source: fine-focus sealed tube2591 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 10.5081 pixels mm-1θmax = 32.5°, θmin = 5.0°
φ and ω scansh = 98
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
k = 1010
Tmin = 0.858, Tmax = 1.000l = 2928
14289 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.0748P)2]
where P = (Fo2 + 2Fc2)/3
5145 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C18H18N2OSγ = 64.16 (2)°
Mr = 310.40V = 785.3 (4) Å3
Triclinic, P1Z = 2
a = 6.3751 (17) ÅMo Kα radiation
b = 6.9998 (17) ŵ = 0.21 mm1
c = 19.791 (5) ÅT = 296 K
α = 83.57 (2)°0.51 × 0.22 × 0.17 mm
β = 81.70 (2)°
Data collection top
Oxford Diffraction Gemini R CCD
diffractometer
5145 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
2591 reflections with I > 2σ(I)
Tmin = 0.858, Tmax = 1.000Rint = 0.027
14289 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.141H-atom parameters constrained
S = 0.98Δρmax = 0.27 e Å3
5145 reflectionsΔρmin = 0.23 e Å3
202 parameters
Special details top

Experimental. IR(KBr, cm-1): 3058 (Ar—H), 2891 (C—H OF CH3),1651(CHO) 1592, 1495 and 1428 (C=C, C=N); 1H NMR (DMSO-d6): δ 2.39 (s, 3H, CH3), 2.44 (s, 3H, SCH3), 3.14–3.93(dd, 2H, J = 4.8 Hz, J=4.8 Hz), 3.74–3.78(dd, 2H, J = 11.6 Hz, J = 11.6 Hz), 5.45–5.48(dd, 1H, J = 4.8 Hz), 7.24–7.22(d, 2H, J=8 Hz, 4-methylthiophenyl),7.63–7.61(d, 2H, J=8 Hz, 4-methylthiophenyl), 7.17–7.15(d, 2H, J=8.4 Hz 4-methylphenyl),7.22–7.20(d, 2H, J=8.4 Hz -methylphenyl), 8.93(S, 1H, CHO); FAB MS (m/z, %): 310 (M+, 89), 289 (70), 225 (39), 165 (26).

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S0.83477 (8)0.72163 (8)0.04968 (3)0.0731 (2)
O0.97536 (16)1.20267 (18)0.28726 (6)0.0595 (3)
N10.37522 (17)1.42564 (18)0.34594 (6)0.0388 (3)
N20.57960 (17)1.37435 (18)0.30170 (6)0.0398 (3)
C10.5374 (2)1.4618 (2)0.23080 (7)0.0406 (3)
H1A0.63211.54030.21490.049*
C20.2761 (2)1.6180 (2)0.24187 (8)0.0444 (4)
H2A0.25611.76420.23800.053*
H2B0.18731.59990.20920.053*
C30.2027 (2)1.5570 (2)0.31349 (7)0.0350 (3)
C40.7900 (2)1.2526 (2)0.32355 (8)0.0462 (4)
H4A0.79471.20340.36920.055*
C1A0.5975 (2)1.2842 (2)0.18385 (7)0.0364 (3)
C2A0.4479 (2)1.1897 (2)0.18079 (7)0.0415 (3)
H2AA0.30191.24170.20640.050*
C3A0.5116 (2)1.0197 (2)0.14046 (8)0.0446 (3)
H3AA0.40900.95820.13940.054*
C4A0.7287 (2)0.9408 (2)0.10156 (7)0.0425 (3)
C5A0.8778 (2)1.0362 (2)0.10358 (8)0.0461 (4)
H5AA1.02240.98610.07720.055*
C6A0.8144 (2)1.2047 (2)0.14428 (8)0.0434 (3)
H6AA0.91721.26590.14530.052*
C7A0.5825 (3)0.6886 (3)0.03797 (10)0.0661 (5)
H7AA0.62390.58270.00540.099*
H7AB0.46610.82110.02130.099*
H7AC0.52090.64420.08080.099*
C1B0.0388 (2)1.6430 (2)0.34630 (7)0.0350 (3)
C2B0.0923 (2)1.5813 (2)0.41334 (7)0.0460 (4)
H2BA0.02691.48040.43740.055*
C3B0.3186 (2)1.6667 (3)0.44475 (8)0.0492 (4)
H3BA0.34921.62360.48980.059*
C4B0.5018 (2)1.8162 (2)0.41031 (8)0.0435 (3)
C5B0.4506 (2)1.8747 (2)0.34345 (8)0.0455 (4)
H5BA0.57111.97310.31920.055*
C6B0.2231 (2)1.7901 (2)0.31140 (7)0.0414 (3)
H6BA0.19341.83210.26610.050*
C7B0.7478 (2)1.9114 (3)0.44524 (10)0.0628 (5)
H7BA0.81052.06370.44020.094*0.49 (4)
H7BB0.74661.86750.49300.094*0.49 (4)
H7BC0.84351.86400.42490.094*0.49 (4)
H7BD0.79951.80130.45830.094*0.51 (4)
H7BE0.84982.01460.41450.094*0.51 (4)
H7BF0.75121.97910.48520.094*0.51 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0565 (3)0.0700 (3)0.0936 (4)0.0259 (2)0.0137 (2)0.0406 (3)
O0.0292 (5)0.0737 (8)0.0696 (8)0.0156 (5)0.0024 (5)0.0179 (6)
N10.0286 (5)0.0460 (7)0.0386 (6)0.0128 (5)0.0013 (4)0.0091 (5)
N20.0276 (5)0.0483 (7)0.0388 (7)0.0118 (5)0.0014 (4)0.0093 (5)
C10.0330 (7)0.0414 (8)0.0446 (8)0.0159 (5)0.0056 (6)0.0041 (6)
C20.0381 (7)0.0382 (7)0.0437 (9)0.0069 (6)0.0048 (6)0.0026 (6)
C30.0307 (6)0.0361 (7)0.0362 (7)0.0124 (5)0.0000 (5)0.0068 (5)
C40.0324 (7)0.0550 (9)0.0502 (9)0.0150 (6)0.0063 (6)0.0115 (7)
C1A0.0297 (6)0.0405 (7)0.0334 (7)0.0121 (5)0.0018 (5)0.0012 (5)
C2A0.0325 (6)0.0533 (9)0.0362 (8)0.0185 (6)0.0040 (5)0.0011 (6)
C3A0.0385 (7)0.0569 (9)0.0429 (8)0.0259 (6)0.0003 (6)0.0013 (7)
C4A0.0373 (7)0.0432 (8)0.0428 (8)0.0139 (6)0.0017 (6)0.0030 (6)
C5A0.0301 (6)0.0533 (9)0.0490 (9)0.0144 (6)0.0084 (6)0.0107 (7)
C6A0.0312 (6)0.0516 (8)0.0463 (8)0.0190 (6)0.0060 (6)0.0061 (6)
C7A0.0727 (12)0.0660 (11)0.0649 (12)0.0320 (9)0.0084 (9)0.0127 (9)
C1B0.0290 (6)0.0352 (7)0.0391 (8)0.0112 (5)0.0014 (5)0.0089 (5)
C2B0.0304 (6)0.0595 (9)0.0397 (8)0.0114 (6)0.0051 (6)0.0007 (7)
C3B0.0364 (7)0.0679 (10)0.0382 (8)0.0193 (7)0.0017 (6)0.0031 (7)
C4B0.0290 (6)0.0465 (8)0.0524 (9)0.0131 (6)0.0017 (6)0.0143 (6)
C5B0.0303 (6)0.0402 (8)0.0565 (10)0.0059 (5)0.0069 (6)0.0010 (6)
C6B0.0360 (7)0.0399 (7)0.0411 (8)0.0102 (6)0.0030 (6)0.0008 (6)
C7B0.0317 (7)0.0752 (12)0.0686 (12)0.0121 (7)0.0076 (7)0.0155 (9)
Geometric parameters (Å, º) top
S—C4A1.7641 (16)C5A—H5AA0.9300
S—C7A1.7710 (19)C6A—H6AA0.9300
O—C41.2186 (17)C7A—H7AA0.9600
N1—C31.2874 (17)C7A—H7AB0.9600
N1—N21.3879 (15)C7A—H7AC0.9600
N2—C41.3422 (17)C1B—C2B1.390 (2)
N2—C11.4795 (19)C1B—C6B1.3919 (18)
C1—C1A1.516 (2)C2B—C3B1.3774 (19)
C1—C21.5424 (19)C2B—H2BA0.9300
C1—H1A0.9800C3B—C4B1.389 (2)
C2—C31.5024 (19)C3B—H3BA0.9300
C2—H2A0.9700C4B—C5B1.377 (2)
C2—H2B0.9700C4B—C7B1.504 (2)
C3—C1B1.4648 (18)C5B—C6B1.3881 (19)
C4—H4A0.9300C5B—H5BA0.9300
C1A—C2A1.388 (2)C6B—H6BA0.9300
C1A—C6A1.3959 (18)C7B—H7BA0.9600
C2A—C3A1.384 (2)C7B—H7BB0.9600
C2A—H2AA0.9300C7B—H7BC0.9600
C3A—C4A1.391 (2)C7B—H7BD0.9600
C3A—H3AA0.9300C7B—H7BE0.9600
C4A—C5A1.386 (2)C7B—H7BF0.9600
C5A—C6A1.380 (2)
C4A—S—C7A104.73 (8)C4A—C5A—H5AA119.6
C3—N1—N2108.01 (11)C5A—C6A—C1A120.74 (14)
C4—N2—N1120.99 (12)C5A—C6A—H6AA119.6
C4—N2—C1125.62 (11)C1A—C6A—H6AA119.6
N1—N2—C1113.37 (10)S—C7A—H7AA109.5
N2—C1—C1A110.28 (11)S—C7A—H7AB109.5
N2—C1—C2100.34 (10)H7AA—C7A—H7AB109.5
C1A—C1—C2116.00 (12)S—C7A—H7AC109.5
N2—C1—H1A109.9H7AA—C7A—H7AC109.5
C1A—C1—H1A109.9H7AB—C7A—H7AC109.5
C2—C1—H1A109.9C2B—C1B—C6B117.62 (12)
C3—C2—C1102.89 (11)C2B—C1B—C3121.29 (11)
C3—C2—H2A111.2C6B—C1B—C3121.09 (12)
C1—C2—H2A111.2C3B—C2B—C1B121.22 (13)
C3—C2—H2B111.2C3B—C2B—H2BA119.4
C1—C2—H2B111.2C1B—C2B—H2BA119.4
H2A—C2—H2B109.1C2B—C3B—C4B121.14 (14)
N1—C3—C1B121.57 (12)C2B—C3B—H3BA119.4
N1—C3—C2113.67 (11)C4B—C3B—H3BA119.4
C1B—C3—C2124.69 (11)C5B—C4B—C3B117.89 (12)
O—C4—N2124.02 (15)C5B—C4B—C7B121.23 (13)
O—C4—H4A118.0C3B—C4B—C7B120.88 (14)
N2—C4—H4A118.0C4B—C5B—C6B121.41 (12)
C2A—C1A—C6A118.11 (14)C4B—C5B—H5BA119.3
C2A—C1A—C1122.22 (11)C6B—C5B—H5BA119.3
C6A—C1A—C1119.61 (13)C5B—C6B—C1B120.69 (13)
C3A—C2A—C1A121.36 (13)C5B—C6B—H6BA119.7
C3A—C2A—H2AA119.3C1B—C6B—H6BA119.7
C1A—C2A—H2AA119.3C4B—C7B—H7BA109.5
C2A—C3A—C4A120.07 (14)C4B—C7B—H7BB109.5
C2A—C3A—H3AA120.0C4B—C7B—H7BC109.5
C4A—C3A—H3AA120.0C4B—C7B—H7BD109.5
C5A—C4A—C3A118.92 (14)C4B—C7B—H7BE109.5
C5A—C4A—S116.27 (10)H7BD—C7B—H7BE109.5
C3A—C4A—S124.80 (12)C4B—C7B—H7BF109.5
C6A—C5A—C4A120.79 (13)H7BD—C7B—H7BF109.5
C6A—C5A—H5AA119.6H7BE—C7B—H7BF109.5
C3—N1—N2—C4174.68 (13)C2A—C3A—C4A—S178.40 (11)
C3—N1—N2—C16.72 (15)C7A—S—C4A—C5A163.29 (12)
C4—N2—C1—C1A67.84 (17)C7A—S—C4A—C3A17.76 (15)
N1—N2—C1—C1A110.69 (12)C3A—C4A—C5A—C6A1.0 (2)
C4—N2—C1—C2169.31 (14)S—C4A—C5A—C6A177.99 (12)
N1—N2—C1—C212.16 (14)C4A—C5A—C6A—C1A0.6 (2)
N2—C1—C2—C312.10 (14)C2A—C1A—C6A—C5A0.3 (2)
C1A—C1—C2—C3106.65 (13)C1—C1A—C6A—C5A176.90 (13)
N2—N1—C3—C1B179.75 (12)N1—C3—C1B—C2B1.9 (2)
N2—N1—C3—C22.50 (16)C2—C3—C1B—C2B178.86 (14)
C1—C2—C3—N19.91 (16)N1—C3—C1B—C6B177.97 (13)
C1—C2—C3—C1B172.94 (13)C2—C3—C1B—C6B1.0 (2)
N1—N2—C4—O179.83 (13)C6B—C1B—C2B—C3B1.7 (2)
C1—N2—C4—O1.7 (2)C3—C1B—C2B—C3B178.17 (15)
N2—C1—C1A—C2A78.51 (15)C1B—C2B—C3B—C4B0.7 (2)
C2—C1—C1A—C2A34.64 (18)C2B—C3B—C4B—C5B0.7 (2)
N2—C1—C1A—C6A98.57 (14)C2B—C3B—C4B—C7B179.02 (16)
C2—C1—C1A—C6A148.29 (13)C3B—C4B—C5B—C6B0.9 (2)
C6A—C1A—C2A—C3A0.8 (2)C7B—C4B—C5B—C6B178.80 (16)
C1—C1A—C2A—C3A176.32 (12)C4B—C5B—C6B—C1B0.2 (2)
C1A—C2A—C3A—C4A0.4 (2)C2B—C1B—C6B—C5B1.5 (2)
C2A—C3A—C4A—C5A0.5 (2)C3—C1B—C6B—C5B178.40 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2A—H2AA···Oi0.932.533.390 (2)154
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC18H18N2OS
Mr310.40
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)6.3751 (17), 6.9998 (17), 19.791 (5)
α, β, γ (°)83.57 (2), 81.70 (2), 64.16 (2)
V3)785.3 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.51 × 0.22 × 0.17
Data collection
DiffractometerOxford Diffraction Gemini R CCD
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.858, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
14289, 5145, 2591
Rint0.027
(sin θ/λ)max1)0.756
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.141, 0.98
No. of reflections5145
No. of parameters202
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.23

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2A—H2AA···Oi0.932.533.390 (2)153.8
Symmetry code: (i) x1, y, z.
 

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