3-(4-Bromo­phen­yl)-5-[4-(dimethyl­amino)­phen­yl]-4,5-dihydro-1H-pyrazole-1-carbothio­amide

doi:10.1107/S1600536811006106

Acta Crystallogr Sect E Struct Rep Online. 2011 March 1; 67(Pt 3): o701–o702.

Published online 2011 February 23. doi: 10.1107/S1600536811006106

PMCID: PMC3052174

3-(4-Bromophenyl)-5-[4-(dimethylamino)phenyl]-4,5-dihydro-1H-pyrazole-1-carbothioamide

Hoong-Kun Fun,^a^*^‡ Thitipone Suwunwong,^b and Suchada Chantrapromma^b^§

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia

^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand

Correspondence e-mail: hkfun/at/usm.my

^‡Thomson Reuters ResearcherID: A-3561-2009.

^§Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

Received February 9, 2011; Accepted February 17, 2011.

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

This article has been cited by other articles in PMC.

Abstract

The molecule of the title pyrazole derivative, C₁₈H₁₉BrN₄S, is twisted. The central pyrazole ring, which adopts a flattened envelope conformation, is almost coplanar with the 4-bromophenyl ring, whereas it is inclined to the 4-(dimethylamino)phenyl ring making dihedral angles of 1.68 (6) and 85.12 (6)°, respectively. The dihedral angle between the two benzene rings is 86.56 (6)°. The dimethylamino group is slightly twisted from the attached benzene ring [C—C—N—C torsion angles = 8.4 (2) and 8.9 (2)°]. In the crystal, molecules are linked by intermolecular N—H (...)

S hydrogen bonds into chains along [2 An external file that holds a picture, illustration, etc.
Object name is e-67-0o701-efi1.jpg

0]. The crystal is further stabilized by C—H (...)

π interactions.

Related literature

For background to chalcone synthesis and the biological activity of pyrazole derivatives, see: Bekhit et al. (2008

); Ono et al. (2007

); Cottineau et al. (2002

); Gadakh et al. (2010

); Hall et al. (2008

); Hoepping et al. (2007

); Mikhaylichenko et al. (2009

); Park et al. (2005

) Souza et al. (2002

); Xie et al. (2008

). For related structures, see; Chantrapromma et al. (2009

); Suwunwong et al. (2009

). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986

). For bond-length data, see: Allen et al. (1987

). For puckering parameters, see: Cremer & Pople (1975

An external file that holds a picture, illustration, etc.
Object name is e-67-0o701-scheme1.jpg Object name is e-67-0o701-scheme1.jpg

Experimental

Crystal data

C₁₈H₁₉BrN₄S
M _r = 403.34
Triclinic,
a = 6.9153 (1) Å
b = 9.5122 (1) Å
c = 15.1545 (2) Å
α = 72.196 (1)°
β = 80.941 (1)°
γ = 69.845 (1)°
V = 889.48 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.44 mm⁻¹
T = 100 K
0.55 × 0.32 × 0.31 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T _min = 0.349, T _max = 0.520
28456 measured reflections
7823 independent reflections
6784 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.073
S = 1.05
7823 reflections
227 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.96 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Data collection: APEX2 (Bruker, 2005

); cell refinement: SAINT (Bruker, 2005

); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008

); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009

Table 1

Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006106/rz2558sup1.cif

Click here to view.^{(21K, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006106/rz2558Isup2.hkl

Click here to view.^{(383K, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

TS thanks the Graduate School, Prince of Songkla University for partial financial support. The authors thank the Prince of Songkla University for financial support through the Crystal Materials Research Unit and also thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

The pyrazole moiety is one of the core structures in a number of natural products (Xie et al., 2008). Numerous compounds which contain the pyrazole moiety are known to exhibit a wide range of biological properties such as antihypertensive (Mikhaylichenko et al., 2009), analgesic (Hall et al., 2008), anti-inflammatory (Bekhit et al., 2008), antipyretic (Souza et al., 2002), antimicrobial (Gadakh et al., 2010), hypoglycemic (Cottineau et al., 2002), sedative-hypnotic (Hoepping et al., 2007) and antitumor activities (Park et al., 2005). Our on going research on biological activities of pyrazole derivatives led us to synthesize the title compound by cyclization of the chalcone derivative (Ono et al., 2007) with excess thiosemicarbazide. Herein we report the crystal structure of the title compound.

The molecular structure of the title compound is twisted. The central pyrazole ring adopts a flattened envelope conformation with puckering parameter Q = 0.1775 (11) Å and [var phi]

= 75.9 (3)° (Cremer & Pople, 1975), with the slightly puckered C9 atom having the maximum deviation of 0.1120 (11) Å. The pyrazole ring is coplanar with the 4-bromophenyl whereas inclined to the 4-dimethylaminophenyl rings with dihedral angles of 1.68 (6) and 85.12 (6)°, respectively. The dihedral angle between the two phenyl rings being 86.56 (6)°. The dimethylamino group is slightly twisted from the attached benzene ring with the torsion angles C16–N3–C13–C14 = 8.9 (2)° and C17–N3–C13–C12 = 8.4 (2)°. The carbothioamide is slightly twisted from the pyrazole ring as indicated by the torsions angles N4–C18–N2–N1 = 5.51 (14)° and S1–C18–N2–N1 = -172.28 (7)°. The bond distances agree with the literature values (Allen et al., 1987) and are comparable to those observed in related structures (Chantrapromma et al., 2009; Suwunwong et al., 2009).

In the crystal structure (Fig. 2), the molecules are linked by intermolecular N—H···S hydrogen bonds (Table 1) into chains along the [2 1 0] direction. The crystal is further stabilized by C—H···π interactions (Table 1).

Experimental

The title compound was synthesized by dissolving (E)-1-(4-bromophenyl)-3-(4-(dimethylamino)phenyl)prop-2-en-1-one (Ono et al., 2007) (0.33 g, 1.0 mmol) in a solution of KOH (0.06 g, 1.0 mmol) in ethanol (20 ml). An excess thiosemicarbazide (0.14 g, 1.5 mmol) in ethanol (20 ml) was then added, and the reaction mixture was vigorously stirred and refluxed for 7 h. The yellow solid of the title compound obtained after cooling of the reaction mixture was filtered off under vacuum. Pale yellow block-shaped single crystals of the title compound suitable for X-ray structure determination were recrystalized from acetone/ethanol (1:1 v/v) by slow evaporation of the solvent at room temperature after several days. M.p. 481–482 K.

Figures

Fig. 1.

The molecular structure of the title compound, showing 50% probability displacement ellipsoids.

Fig. 2.

The crystal packing of the title compound viewed along the a axis. Hydrogen bonds are drawn as dashed lines.

Crystal data

C₁₈H₁₉BrN₄S	Z = 2
M_r = 403.34	F(000) = 412
Triclinic, P1	D_x = 1.506 Mg m⁻³
Hall symbol: -P 1	Melting point = 481–482 K
a = 6.9153 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5122 (1) Å	Cell parameters from 7823 reflections
c = 15.1545 (2) Å	θ = 2.4–35.1°
α = 72.196 (1)°	µ = 2.44 mm⁻¹
β = 80.941 (1)°	T = 100 K
γ = 69.845 (1)°	Block, pale yellow
V = 889.48 (2) Å³	0.55 × 0.32 × 0.31 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	7823 independent reflections
Radiation source: sealed tube	6784 reflections with I > 2σ(I)
graphite	R_int = 0.023
and ω scans	θ_max = 35.1°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→10
T_min = 0.349, T_max = 0.520	k = −15→15
28456 measured reflections	l = −24→24

Refinement

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0344P)² + 0.3232P] where P = (F_o² + 2F_c²)/3
7823 reflections	(Δ/σ)_max = 0.003
227 parameters	Δρ_max = 0.96 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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)

	x	y	z	U_iso*/U_eq
Br1	1.641401 (17)	−0.173962 (13)	0.169443 (10)	0.02713 (4)
S1	0.08981 (4)	0.61386 (3)	0.083129 (18)	0.01668 (5)
N1	0.62104 (13)	0.27982 (10)	0.13070 (6)	0.01465 (14)
N2	0.44511 (13)	0.40189 (10)	0.14121 (6)	0.01404 (14)
N3	−0.0497 (2)	0.25372 (15)	0.52890 (9)	0.0346 (3)
N4	0.31575 (15)	0.37031 (12)	0.02111 (7)	0.01857 (16)
C1	1.02110 (17)	0.05782 (12)	0.12650 (8)	0.01819 (18)
H1A	0.9213	0.0544	0.0933	0.022*
C2	1.21950 (17)	−0.04510 (13)	0.12460 (9)	0.02047 (19)
H2A	1.2534	−0.1179	0.0908	0.025*
C3	1.36736 (16)	−0.03752 (12)	0.17431 (8)	0.01850 (18)
C4	1.32036 (16)	0.06853 (12)	0.22612 (8)	0.01758 (18)
H4A	1.4208	0.0711	0.2593	0.021*
C5	1.12052 (15)	0.17132 (12)	0.22782 (7)	0.01604 (17)
H5A	1.0873	0.2432	0.2623	0.019*
C6	0.96924 (15)	0.16730 (11)	0.17801 (7)	0.01418 (16)
C7	0.76209 (15)	0.27851 (11)	0.17797 (7)	0.01395 (15)
C8	0.69425 (15)	0.40713 (12)	0.22566 (7)	0.01553 (16)
H8A	0.7585	0.4870	0.1952	0.019*
H8B	0.7266	0.3671	0.2904	0.019*
C9	0.45956 (15)	0.47007 (11)	0.21552 (7)	0.01428 (16)
H9A	0.4135	0.5839	0.1937	0.017*
C10	0.33157 (15)	0.41586 (12)	0.30181 (7)	0.01506 (16)
C11	0.40552 (17)	0.27201 (13)	0.36660 (8)	0.01809 (18)
H11A	0.5411	0.2104	0.3590	0.022*
C12	0.28225 (18)	0.21843 (14)	0.44205 (8)	0.0221 (2)
H12A	0.3371	0.1226	0.4842	0.027*
C13	0.07487 (19)	0.30739 (14)	0.45555 (8)	0.0219 (2)
C14	0.00187 (17)	0.45394 (14)	0.39134 (8)	0.01970 (19)
H14A	−0.1332	0.5167	0.3988	0.024*
C15	0.12813 (16)	0.50602 (13)	0.31725 (7)	0.01712 (17)
H15A	0.0761	0.6039	0.2765	0.021*
C16	−0.2680 (2)	0.3366 (2)	0.53468 (10)	0.0324 (3)
H16A	−0.3276	0.3493	0.4785	0.049*
H16B	−0.2880	0.4370	0.5428	0.049*
H16C	−0.3334	0.2786	0.5866	0.049*
C17	0.0361 (3)	0.1144 (2)	0.60089 (12)	0.0443 (4)
H17A	0.1564	0.1203	0.6219	0.067*
H17B	0.0737	0.0256	0.5768	0.067*
H17C	−0.0645	0.1046	0.6519	0.067*
C18	0.29283 (15)	0.45225 (12)	0.08212 (7)	0.01415 (16)
H1N4	0.211 (3)	0.386 (2)	−0.0067 (13)	0.028 (4)*
H2N4	0.414 (3)	0.287 (2)	0.0245 (12)	0.027 (4)*

Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01316 (5)	0.01906 (5)	0.05023 (9)	−0.00079 (4)	−0.00226 (5)	−0.01560 (5)
S1	0.01295 (10)	0.01764 (10)	0.01829 (11)	−0.00210 (8)	−0.00309 (8)	−0.00530 (8)
N1	0.0112 (3)	0.0157 (3)	0.0161 (4)	−0.0029 (3)	−0.0005 (3)	−0.0046 (3)
N2	0.0112 (3)	0.0159 (3)	0.0149 (3)	−0.0024 (3)	−0.0014 (3)	−0.0059 (3)
N3	0.0276 (6)	0.0347 (6)	0.0316 (6)	−0.0095 (5)	0.0114 (5)	−0.0020 (5)
N4	0.0150 (4)	0.0224 (4)	0.0189 (4)	−0.0026 (3)	−0.0039 (3)	−0.0088 (3)
C1	0.0155 (4)	0.0180 (4)	0.0224 (5)	−0.0042 (3)	−0.0027 (3)	−0.0078 (4)
C2	0.0165 (4)	0.0178 (4)	0.0284 (5)	−0.0035 (3)	−0.0014 (4)	−0.0102 (4)
C3	0.0125 (4)	0.0140 (4)	0.0282 (5)	−0.0032 (3)	−0.0008 (3)	−0.0060 (4)
C4	0.0128 (4)	0.0158 (4)	0.0251 (5)	−0.0044 (3)	−0.0029 (3)	−0.0061 (4)
C5	0.0131 (4)	0.0150 (4)	0.0210 (4)	−0.0046 (3)	−0.0012 (3)	−0.0060 (3)
C6	0.0112 (4)	0.0140 (4)	0.0170 (4)	−0.0044 (3)	−0.0005 (3)	−0.0034 (3)
C7	0.0120 (4)	0.0142 (4)	0.0153 (4)	−0.0043 (3)	−0.0001 (3)	−0.0035 (3)
C8	0.0122 (4)	0.0167 (4)	0.0194 (4)	−0.0043 (3)	−0.0012 (3)	−0.0073 (3)
C9	0.0124 (4)	0.0153 (4)	0.0164 (4)	−0.0046 (3)	−0.0016 (3)	−0.0055 (3)
C10	0.0133 (4)	0.0168 (4)	0.0161 (4)	−0.0038 (3)	−0.0011 (3)	−0.0068 (3)
C11	0.0154 (4)	0.0189 (4)	0.0185 (4)	−0.0033 (3)	0.0000 (3)	−0.0059 (3)
C12	0.0207 (5)	0.0216 (5)	0.0194 (5)	−0.0046 (4)	0.0007 (4)	−0.0023 (4)
C13	0.0208 (5)	0.0256 (5)	0.0199 (5)	−0.0086 (4)	0.0040 (4)	−0.0078 (4)
C14	0.0147 (4)	0.0244 (5)	0.0204 (5)	−0.0041 (4)	0.0008 (3)	−0.0100 (4)
C15	0.0142 (4)	0.0195 (4)	0.0173 (4)	−0.0027 (3)	−0.0017 (3)	−0.0072 (3)
C16	0.0234 (6)	0.0522 (9)	0.0273 (6)	−0.0184 (6)	0.0087 (5)	−0.0162 (6)
C17	0.0419 (9)	0.0417 (8)	0.0351 (8)	−0.0142 (7)	0.0126 (7)	0.0035 (6)
C18	0.0124 (4)	0.0167 (4)	0.0131 (4)	−0.0051 (3)	−0.0005 (3)	−0.0032 (3)

Geometric parameters (Å, °)

Br1—C3	1.8976 (10)	C7—C8	1.5091 (14)
S1—C18	1.6896 (10)	C8—C9	1.5391 (14)
N1—C7	1.2927 (13)	C8—H8A	0.9700
N1—N2	1.3901 (12)	C8—H8B	0.9700
N2—C18	1.3518 (13)	C9—C10	1.5155 (14)
N2—C9	1.4917 (13)	C9—H9A	0.9800
N3—C13	1.3759 (16)	C10—C11	1.3972 (15)
N3—C17	1.441 (2)	C10—C15	1.3990 (14)
N3—C16	1.4450 (19)	C11—C12	1.3893 (16)
N4—C18	1.3404 (14)	C11—H11A	0.9300
N4—H1N4	0.842 (19)	C12—C13	1.4113 (17)
N4—H2N4	0.841 (19)	C12—H12A	0.9300
C1—C2	1.3859 (15)	C13—C14	1.4090 (17)
C1—C6	1.4049 (15)	C14—C15	1.3848 (16)
C1—H1A	0.9300	C14—H14A	0.9300
C2—C3	1.3945 (16)	C15—H15A	0.9300
C2—H2A	0.9300	C16—H16A	0.9600
C3—C4	1.3848 (15)	C16—H16B	0.9600
C4—C5	1.3926 (14)	C16—H16C	0.9600
C4—H4A	0.9300	C17—H17A	0.9600
C5—C6	1.3999 (14)	C17—H17B	0.9600
C5—H5A	0.9300	C17—H17C	0.9600
C6—C7	1.4583 (14)

C7—N1—N2	107.84 (8)	N2—C9—C8	100.12 (8)
C18—N2—N1	119.42 (8)	C10—C9—C8	114.94 (8)
C18—N2—C9	127.78 (8)	N2—C9—H9A	110.4
N1—N2—C9	112.61 (8)	C10—C9—H9A	110.4
C13—N3—C17	120.35 (12)	C8—C9—H9A	110.4
C13—N3—C16	120.36 (12)	C11—C10—C15	117.01 (10)
C17—N3—C16	119.29 (12)	C11—C10—C9	122.25 (9)
C18—N4—H1N4	117.0 (13)	C15—C10—C9	120.66 (9)
C18—N4—H2N4	120.0 (12)	C12—C11—C10	121.88 (10)
H1N4—N4—H2N4	119.5 (17)	C12—C11—H11A	119.1
C2—C1—C6	120.68 (10)	C10—C11—H11A	119.1
C2—C1—H1A	119.7	C11—C12—C13	120.90 (10)
C6—C1—H1A	119.7	C11—C12—H12A	119.6
C1—C2—C3	118.82 (10)	C13—C12—H12A	119.6
C1—C2—H2A	120.6	N3—C13—C14	121.54 (11)
C3—C2—H2A	120.6	N3—C13—C12	121.30 (11)
C4—C3—C2	121.77 (10)	C14—C13—C12	117.15 (10)
C4—C3—Br1	119.03 (8)	C15—C14—C13	121.01 (10)
C2—C3—Br1	119.19 (8)	C15—C14—H14A	119.5
C3—C4—C5	119.05 (10)	C13—C14—H14A	119.5
C3—C4—H4A	120.5	C14—C15—C10	122.00 (10)
C5—C4—H4A	120.5	C14—C15—H15A	119.0
C4—C5—C6	120.47 (10)	C10—C15—H15A	119.0
C4—C5—H5A	119.8	N3—C16—H16A	109.5
C6—C5—H5A	119.8	N3—C16—H16B	109.5
C5—C6—C1	119.21 (9)	H16A—C16—H16B	109.5
C5—C6—C7	120.05 (9)	N3—C16—H16C	109.5
C1—C6—C7	120.72 (9)	H16A—C16—H16C	109.5
N1—C7—C6	121.29 (9)	H16B—C16—H16C	109.5
N1—C7—C8	113.61 (8)	N3—C17—H17A	109.5
C6—C7—C8	124.98 (9)	N3—C17—H17B	109.5
C7—C8—C9	102.52 (8)	H17A—C17—H17B	109.5
C7—C8—H8A	111.3	N3—C17—H17C	109.5
C9—C8—H8A	111.3	H17A—C17—H17C	109.5
C7—C8—H8B	111.3	H17B—C17—H17C	109.5
C9—C8—H8B	111.3	N4—C18—N2	116.40 (9)
H8A—C8—H8B	109.2	N4—C18—S1	122.21 (8)
N2—C9—C10	110.17 (8)	N2—C18—S1	121.35 (8)

C7—N1—N2—C18	164.20 (9)	C7—C8—C9—N2	−16.35 (9)
C7—N1—N2—C9	−11.12 (11)	C7—C8—C9—C10	101.64 (9)
C6—C1—C2—C3	−0.38 (17)	N2—C9—C10—C11	82.45 (11)
C1—C2—C3—C4	0.78 (18)	C8—C9—C10—C11	−29.71 (13)
C1—C2—C3—Br1	−178.27 (9)	N2—C9—C10—C15	−94.19 (11)
C2—C3—C4—C5	−0.65 (17)	C8—C9—C10—C15	153.64 (9)
Br1—C3—C4—C5	178.40 (8)	C15—C10—C11—C12	1.39 (16)
C3—C4—C5—C6	0.12 (16)	C9—C10—C11—C12	−175.37 (10)
C4—C5—C6—C1	0.25 (16)	C10—C11—C12—C13	0.81 (18)
C4—C5—C6—C7	−178.15 (10)	C17—N3—C13—C14	−170.94 (15)
C2—C1—C6—C5	−0.12 (16)	C16—N3—C13—C14	8.9 (2)
C2—C1—C6—C7	178.27 (10)	C17—N3—C13—C12	8.4 (2)
N2—N1—C7—C6	−177.42 (9)	C16—N3—C13—C12	−171.79 (13)
N2—N1—C7—C8	−1.24 (11)	C11—C12—C13—N3	178.51 (13)
C5—C6—C7—N1	178.25 (10)	C11—C12—C13—C14	−2.16 (18)
C1—C6—C7—N1	−0.12 (15)	N3—C13—C14—C15	−179.34 (12)
C5—C6—C7—C8	2.53 (15)	C12—C13—C14—C15	1.33 (17)
C1—C6—C7—C8	−175.85 (10)	C13—C14—C15—C10	0.88 (17)
N1—C7—C8—C9	12.11 (11)	C11—C10—C15—C14	−2.23 (16)
C6—C7—C8—C9	−171.88 (9)	C9—C10—C15—C14	174.59 (10)
C18—N2—C9—C10	81.36 (12)	N1—N2—C18—N4	5.51 (14)
N1—N2—C9—C10	−103.80 (9)	C9—N2—C18—N4	−179.96 (9)
C18—N2—C9—C8	−157.18 (10)	N1—N2—C18—S1	−172.28 (7)
N1—N2—C9—C8	17.65 (10)	C9—N2—C18—S1	2.25 (15)

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N4···S1ⁱ	0.84 (2)	2.54 (2)	3.3679 (11)	170.8 (17)
C5—H5A···Cg2ⁱⁱ	0.93	2.72	3.5462 (12)	149
C16—H16B···Cg2ⁱⁱⁱ	0.96	2.71	3.6676 (18)	154
C17—H17C···Cg1^iv	0.96	2.74	3.5990 (19)	149

Symmetry codes: (i) −x, −y+1, −z; (ii) x+1, y, z; (iii) −x, −y+1, −z+1; (iv) −x+1, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2558).

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