Crystal structure of 3-(adamantan-1-yl)-4-(4-chloro­phen­yl)-1H-1,2,4-triazole-5(4H)-thione

Al-Wabli, R.I.; El-Emam, A.A.; Alroqi, O.S.; Chidan Kumar, C.S.; Fun, H.-K.

doi:10.1107/S2056989015000596

Crystal structure of 3-(adamantan-1-yl)-4-(4-chlorophenyl)-1H-1,2,4-triazole-5(4H)-thione

R. I. Al-Wabli, A. A. El-Emam, O. S. Alroqi, C. S. Chidan Kumar and H.-K. Fun

The title compound, C₁₈H₂₀ClN₃S, is a functionalized triazoline-3-thione derivative. The benzene ring is almost perpendicular to the planar 1,2,4-triazole ring [maximum deviation = 0.007 (1) Å] with a dihedral angle of 89.61 (5)° between them and there is an adamantane substituent at the 3-position of the triazolethione ring. In the crystal, N—H

S hydrogen-bonding interactions link the molecules into chains extending along the c-axis direction. The crystal packing is further stabilized by weak C—H

π interactions that link adjacent chains into a two-dimensional structure in the bc plane. The crystal studied was an inversion twin with a 0.50 (3):0.50 (3) domain ratio.

Keywords: crystal structure; adamantane; 1,2,4-triazole; starting material; hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015000596/sj5439sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989015000596/sj5439Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015000596/sj5439Isup3.cml Supplementary material

CCDC reference: 1042916

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R factor = 0.030
wR factor = 0.082
Data-to-parameter ratio = 53.6

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.500
           From the CIF: _refine_ls_abs_structure_Flack_su    0.030
PLAT019_ALERT_1_C  _diffrn_measured_fraction_theta_full/_max < 1.0      0.994 Report
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         47 Ang3
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         11 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          5 Note

Alert level G
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.68 mm
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1 Note
PLAT792_ALERT_1_G The Model has Chirality at C15     (Polar  SPGR)          S Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          2 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   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
   3 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Chemical context top

Adamantane derivatives have long been known for their diverse biological activities (Wang et al., 2013) including antiviral activity against influenza (Vernier et al., 1969) and HIV viruses (El-Emam et al., 2004; Balzarini et al., 2009). In addition, adamantane derivatives are known to exhibit marked antibacterial activity (Kadi et al., 2010; Protopopova et al., 2005). In an earlier publication, we reported the synthesis and potent antimicrobial and anti-inflammatory activities of the title compound and its related derivatives (Al-Deeb et al., 2006).

Structural commentary top

In the title compound (Fig. 1), the 1,2,4-triazole (N1—N3/C7/C8) ring is nearly planar with a maximum deviation of -0.007 (1) Å at atom N1. The phenyl (C1–C6) ring is almost perpendicular to the near planar 1,2,4-triazole ring with a dihedral angle of 89.61 (5) Å between them. An adamantane group is substituted at the 3-position of the triazolethione ring. The crystal studied was an inversion twin with a 0.50 (3):0.50 (3) domain ratio.

Supramolecular features top

In the crystal packing (Fig. 2), the molecules are linked by intermolecular N3–H1N3···S1 hydrogen bonding interactions forming chains extending along along the c axis direction. The crystal packing is further stabilized by weak C–H···π (phenyl) interactions (Table 1) that link the adjacent chains into a two dimensional structure in the bc plane.

Synthesis and crystallization top

The title compound was prepared by a literature procedure (Al-Deeb et al., 2006) and crystallized from EtOH/CHCl₃ (1:1) to yield colorless crystals. M·P.: >300 °C.

¹H NMR (CDCl₃, 700.17 MHz): δ 1.55-1.70 (m, 6H, Adamantane-H), 1.86-2.05 (m, 9H, Adamantane-H), 7.25 (d, 2H, Ar—H, J = 8.5 Hz), 7.45 (d, 2H, Ar—H, J = 8.5 Hz), 11.90 (br. s, 1H, NH). 13C NMR (CDCl₃, 176.08 MHz): δ 27.68, 36.03, 36.44, 39.80 (Adamantane-C), 129.95, 131.02, 134.23, 136.42 (Ar—C), 158.41 (C=N), 170.0 (C=S).

Refinement details top

The nitrogen-bound H-atom was located in a difference Fourier map and its coordinates and isotropic displacement parameter were refined freely with d(N–H) = 0.92 (2) Å. Other H atoms were positioned geometrically (d(C–H) 0.93–0.98 Å) and refined using a riding model with U_iso(H) = 1.2 U_eq(C). The crystal studied was an inversion twin with a 0.50 (3):0.50 (3) domain ratio.

Related literature top

For the biological activity of adamantane derivatives, see: Lorenzo et al. (2008); Wang et al. (2013); Kadi et al. (2010); Balzarini et al. (2009); Protopopova et al. (2005); Vernier et al. (1969). For the biological activity of adamantyl-1,2,4-triazole derivatives, see: El-Emam & Ibrahim (1991); Al-Abdullah et al. (2014); El-Emam et al. (2004, 2013). For related adamantyl-1,2,4-triazole structures, see: El-Emam et al. (2012), Al-Tamimi et al. (2013), Al-Omary et al. (2014); Almutairi et al. (2012). For the synthesis of the title compound, see: Al-Deeb et al. (2006).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids.
	Fig. 2. Crystal packing of the title compound, showing the N–H···S hydrogen bonding interactions (Table 1) as dashed lines linking the molecules into chains extending along the c axis direction. Other H-atoms are omited for clarity.

3-(Adamantan-1-yl)-4-(4-chlorophenyl)-1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₁₈H₂₀ClN₃S	D_x = 1.340 Mg m⁻³
M_r = 345.88	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4	Cell parameters from 9155 reflections
a = 23.1302 (5) Å	θ = 2.5–40.8°
c = 6.4100 (2) Å	µ = 0.35 mm⁻¹
V = 3429.39 (18) Å³	T = 150 K
Z = 8	Needle, colourless
F(000) = 1456	0.68 × 0.29 × 0.26 mm

Data collection top

Bruker APEXII CCD diffractometer	R_int = 0.033
ϕ and ω scans	θ_max = 41.2°, θ_min = 2.5°
106262 measured reflections	h = −42→42
11408 independent reflections	k = −42→42
10584 reflections with I > 2σ(I)	l = −11→11

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.030	w = 1/[σ²(F_o²) + (0.0483P)² + 0.551P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.082	(Δ/σ)_max = 0.002
S = 1.06	Δρ_max = 0.53 e Å⁻³
11408 reflections	Δρ_min = −0.31 e Å⁻³
213 parameters	Absolute structure: Flack (1983), 5353 Friedel pairs
0 restraints	Absolute structure parameter: 0.50 (3)

Crystal data top

C₁₈H₂₀ClN₃S	Z = 8
M_r = 345.88	Mo Kα radiation
Tetragonal, I4	µ = 0.35 mm⁻¹
a = 23.1302 (5) Å	T = 150 K
c = 6.4100 (2) Å	0.68 × 0.29 × 0.26 mm
V = 3429.39 (18) Å³

Data collection top

Bruker APEXII CCD diffractometer	10584 reflections with I > 2σ(I)
106262 measured reflections	R_int = 0.033
11408 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.082	Δρ_max = 0.53 e Å⁻³
S = 1.06	Δρ_min = −0.31 e Å⁻³
11408 reflections	Absolute structure: Flack (1983), 5353 Friedel pairs
213 parameters	Absolute structure parameter: 0.50 (3)
0 restraints

Special details top

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. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.25120 (2)	0.81338 (2)	0.20570 (4)	0.01558 (4)
Cl1	0.10286 (2)	0.98207 (2)	0.89359 (5)	0.03118 (7)
N1	0.15119 (3)	0.77326 (3)	0.38819 (12)	0.01309 (10)
N2	0.13872 (4)	0.68822 (4)	0.23712 (14)	0.01734 (13)
N3	0.18691 (3)	0.71564 (4)	0.16208 (13)	0.01642 (12)
C1	0.16658 (4)	0.83033 (4)	0.70574 (15)	0.01686 (13)
H1A	0.1901	0.8012	0.7588	0.020*
C2	0.15555 (5)	0.87980 (4)	0.82355 (16)	0.01990 (15)
H2A	0.1715	0.8840	0.9558	0.024*
C3	0.12041 (5)	0.92258 (4)	0.74046 (17)	0.01972 (15)
C4	0.09818 (5)	0.91871 (4)	0.53962 (19)	0.02225 (17)
H4A	0.0761	0.9486	0.4843	0.027*
C5	0.10952 (4)	0.86925 (4)	0.42249 (16)	0.01916 (15)
H5A	0.0953	0.8660	0.2874	0.023*
C6	0.14220 (4)	0.82486 (4)	0.50837 (14)	0.01374 (12)
C7	0.19637 (3)	0.76715 (4)	0.25068 (13)	0.01323 (12)
C8	0.11738 (4)	0.72353 (4)	0.37613 (14)	0.01404 (12)
C9	0.06417 (3)	0.70942 (4)	0.50180 (14)	0.01456 (12)
C10	0.04492 (5)	0.64750 (5)	0.4465 (2)	0.02441 (19)
H10A	0.0368	0.6450	0.2983	0.029*
H10B	0.0758	0.6206	0.4784	0.029*
C11	−0.00943 (6)	0.63104 (5)	0.5707 (2)	0.0292 (2)
H11A	−0.0214	0.5918	0.5330	0.035*
C12	−0.05832 (5)	0.67338 (6)	0.5199 (2)	0.0292 (2)
H12A	−0.0673	0.6716	0.3722	0.035*
H12B	−0.0928	0.6628	0.5971	0.035*
C13	−0.03997 (4)	0.73459 (6)	0.5782 (2)	0.02497 (19)
H13A	−0.0715	0.7615	0.5465	0.030*
C14	−0.02609 (5)	0.73732 (7)	0.8112 (2)	0.0307 (2)
H14A	−0.0145	0.7763	0.8487	0.037*
H14B	−0.0602	0.7274	0.8916	0.037*
C15	0.02267 (5)	0.69501 (7)	0.86116 (18)	0.0303 (3)
H15A	0.0313	0.6967	1.0107	0.036*
C16	0.07706 (4)	0.71160 (6)	0.73728 (16)	0.0253 (2)
H16A	0.1082	0.6850	0.7703	0.030*
H16B	0.0893	0.7503	0.7759	0.030*
C17	0.00415 (6)	0.63344 (7)	0.8040 (3)	0.0356 (3)
H17A	0.0349	0.6065	0.8369	0.043*
H17B	−0.0298	0.6226	0.8838	0.043*
C18	0.01416 (4)	0.75172 (5)	0.45273 (18)	0.02095 (16)
H18A	0.0256	0.7908	0.4888	0.025*
H18B	0.0055	0.7507	0.3047	0.025*
H1N3	0.2084 (9)	0.6995 (9)	0.057 (4)	0.029 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01413 (8)	0.01610 (8)	0.01653 (8)	−0.00195 (6)	0.00022 (6)	0.00131 (6)
Cl1	0.04393 (16)	0.01649 (9)	0.03312 (14)	0.00301 (9)	0.01278 (12)	−0.00681 (9)
N1	0.0119 (2)	0.0135 (2)	0.0139 (3)	0.00076 (19)	0.0009 (2)	−0.0017 (2)
N2	0.0145 (3)	0.0176 (3)	0.0200 (3)	−0.0026 (2)	0.0042 (2)	−0.0047 (2)
N3	0.0140 (3)	0.0175 (3)	0.0178 (3)	−0.0019 (2)	0.0040 (2)	−0.0052 (2)
C1	0.0189 (3)	0.0158 (3)	0.0158 (3)	0.0034 (2)	−0.0032 (3)	−0.0026 (3)
C2	0.0251 (4)	0.0178 (3)	0.0168 (4)	0.0013 (3)	−0.0005 (3)	−0.0038 (3)
C3	0.0226 (4)	0.0136 (3)	0.0230 (4)	0.0011 (3)	0.0052 (3)	−0.0030 (3)
C4	0.0248 (4)	0.0151 (3)	0.0269 (5)	0.0065 (3)	−0.0008 (3)	0.0000 (3)
C5	0.0211 (4)	0.0170 (3)	0.0193 (4)	0.0048 (3)	−0.0030 (3)	0.0002 (3)
C6	0.0133 (3)	0.0127 (3)	0.0152 (3)	0.0021 (2)	0.0000 (2)	−0.0015 (2)
C7	0.0117 (3)	0.0146 (3)	0.0134 (3)	0.0007 (2)	0.0000 (2)	−0.0005 (2)
C8	0.0120 (3)	0.0152 (3)	0.0149 (3)	0.0001 (2)	0.0010 (2)	−0.0016 (2)
C9	0.0113 (3)	0.0177 (3)	0.0146 (3)	−0.0002 (2)	0.0011 (2)	0.0002 (3)
C10	0.0227 (4)	0.0184 (4)	0.0322 (5)	−0.0046 (3)	0.0090 (4)	−0.0016 (3)
C11	0.0251 (5)	0.0242 (4)	0.0382 (6)	−0.0082 (4)	0.0103 (4)	0.0016 (4)
C12	0.0150 (4)	0.0438 (6)	0.0288 (5)	−0.0089 (4)	−0.0016 (3)	0.0016 (5)
C13	0.0125 (3)	0.0319 (5)	0.0305 (5)	0.0038 (3)	0.0031 (3)	0.0058 (4)
C14	0.0208 (4)	0.0435 (7)	0.0280 (5)	−0.0009 (4)	0.0101 (4)	−0.0069 (5)
C15	0.0181 (4)	0.0568 (8)	0.0161 (4)	−0.0046 (4)	0.0023 (3)	0.0064 (4)
C16	0.0140 (3)	0.0462 (6)	0.0157 (4)	−0.0035 (4)	−0.0010 (3)	0.0036 (4)
C17	0.0241 (5)	0.0438 (7)	0.0388 (7)	0.0009 (5)	0.0085 (5)	0.0235 (6)
C18	0.0134 (3)	0.0238 (4)	0.0256 (4)	0.0034 (3)	0.0018 (3)	0.0055 (3)

Geometric parameters (Å, º) top

S1—C7	1.6836 (9)	C10—H10A	0.9700
Cl1—C3	1.7384 (10)	C10—H10B	0.9700
N1—C7	1.3744 (11)	C11—C17	1.529 (2)
N1—C8	1.3931 (11)	C11—C12	1.531 (2)
N1—C6	1.4355 (11)	C11—H11A	0.9800
N2—C8	1.3056 (12)	C12—C13	1.5246 (19)
N2—N3	1.3696 (11)	C12—H12A	0.9700
N3—C7	1.3379 (12)	C12—H12B	0.9700
N3—H1N3	0.92 (2)	C13—C14	1.529 (2)
C1—C6	1.3909 (13)	C13—C18	1.5399 (15)
C1—C2	1.3946 (13)	C13—H13A	0.9800
C1—H1A	0.9300	C14—C15	1.527 (2)
C2—C3	1.3869 (14)	C14—H14A	0.9700
C2—H2A	0.9300	C14—H14B	0.9700
C3—C4	1.3892 (16)	C15—C17	1.532 (2)
C4—C5	1.3933 (14)	C15—C16	1.5362 (15)
C4—H4A	0.9300	C15—H15A	0.9800
C5—C6	1.3889 (12)	C16—H16A	0.9700
C5—H5A	0.9300	C16—H16B	0.9700
C8—C9	1.5067 (12)	C17—H17A	0.9700
C9—C16	1.5394 (14)	C17—H17B	0.9700
C9—C10	1.5413 (14)	C18—H18A	0.9700
C9—C18	1.5473 (13)	C18—H18B	0.9700
C10—C11	1.5359 (15)

C7—N1—C8	107.83 (7)	C17—C11—H11A	109.4
C7—N1—C6	122.67 (7)	C12—C11—H11A	109.4
C8—N1—C6	129.42 (7)	C10—C11—H11A	109.4
C8—N2—N3	104.93 (7)	C13—C12—C11	109.64 (9)
C7—N3—N2	113.35 (7)	C13—C12—H12A	109.7
C7—N3—H1N3	125.9 (14)	C11—C12—H12A	109.7
N2—N3—H1N3	120.7 (14)	C13—C12—H12B	109.7
C6—C1—C2	119.54 (8)	C11—C12—H12B	109.7
C6—C1—H1A	120.2	H12A—C12—H12B	108.2
C2—C1—H1A	120.2	C12—C13—C14	109.65 (11)
C3—C2—C1	118.99 (9)	C12—C13—C18	109.72 (10)
C3—C2—H2A	120.5	C14—C13—C18	109.20 (9)
C1—C2—H2A	120.5	C12—C13—H13A	109.4
C2—C3—C4	121.80 (9)	C14—C13—H13A	109.4
C2—C3—Cl1	119.00 (8)	C18—C13—H13A	109.4
C4—C3—Cl1	119.20 (8)	C15—C14—C13	109.46 (10)
C3—C4—C5	118.85 (9)	C15—C14—H14A	109.8
C3—C4—H4A	120.6	C13—C14—H14A	109.8
C5—C4—H4A	120.6	C15—C14—H14B	109.8
C6—C5—C4	119.73 (9)	C13—C14—H14B	109.8
C6—C5—H5A	120.1	H14A—C14—H14B	108.2
C4—C5—H5A	120.1	C14—C15—C17	109.82 (10)
C5—C6—C1	120.93 (8)	C14—C15—C16	109.66 (11)
C5—C6—N1	118.74 (8)	C17—C15—C16	109.74 (11)
C1—C6—N1	120.33 (7)	C14—C15—H15A	109.2
N3—C7—N1	103.86 (7)	C17—C15—H15A	109.2
N3—C7—S1	128.03 (7)	C16—C15—H15A	109.2
N1—C7—S1	128.11 (7)	C15—C16—C9	109.88 (8)
N2—C8—N1	110.01 (8)	C15—C16—H16A	109.7
N2—C8—C9	122.57 (8)	C9—C16—H16A	109.7
N1—C8—C9	127.42 (8)	C15—C16—H16B	109.7
C8—C9—C16	111.04 (7)	C9—C16—H16B	109.7
C8—C9—C10	108.32 (7)	H16A—C16—H16B	108.2
C16—C9—C10	108.17 (9)	C11—C17—C15	108.97 (10)
C8—C9—C18	111.41 (8)	C11—C17—H17A	109.9
C16—C9—C18	108.87 (8)	C15—C17—H17A	109.9
C10—C9—C18	108.96 (8)	C11—C17—H17B	109.9
C11—C10—C9	110.34 (9)	C15—C17—H17B	109.9
C11—C10—H10A	109.6	H17A—C17—H17B	108.3
C9—C10—H10A	109.6	C13—C18—C9	109.81 (8)
C11—C10—H10B	109.6	C13—C18—H18A	109.7
C9—C10—H10B	109.6	C9—C18—H18A	109.7
H10A—C10—H10B	108.1	C13—C18—H18B	109.7
C17—C11—C12	109.66 (11)	C9—C18—H18B	109.7
C17—C11—C10	109.25 (11)	H18A—C18—H18B	108.2
C12—C11—C10	109.63 (10)

C8—N2—N3—C7	0.12 (11)	N1—C8—C9—C10	−175.22 (9)
C6—C1—C2—C3	−0.08 (15)	N2—C8—C9—C18	−115.92 (10)
C1—C2—C3—C4	−3.09 (16)	N1—C8—C9—C18	64.95 (12)
C1—C2—C3—Cl1	175.90 (8)	C8—C9—C10—C11	−179.89 (10)
C2—C3—C4—C5	2.89 (17)	C16—C9—C10—C11	59.67 (12)
Cl1—C3—C4—C5	−176.10 (9)	C18—C9—C10—C11	−58.54 (13)
C3—C4—C5—C6	0.48 (16)	C9—C10—C11—C17	−60.75 (14)
C4—C5—C6—C1	−3.62 (15)	C9—C10—C11—C12	59.44 (14)
C4—C5—C6—N1	177.30 (9)	C17—C11—C12—C13	59.98 (13)
C2—C1—C6—C5	3.41 (14)	C10—C11—C12—C13	−59.96 (14)
C2—C1—C6—N1	−177.52 (9)	C11—C12—C13—C14	−59.57 (12)
C7—N1—C6—C5	88.15 (11)	C11—C12—C13—C18	60.37 (13)
C8—N1—C6—C5	−88.12 (12)	C12—C13—C14—C15	59.55 (12)
C7—N1—C6—C1	−90.93 (11)	C18—C13—C14—C15	−60.70 (14)
C8—N1—C6—C1	92.80 (11)	C13—C14—C15—C17	−59.99 (13)
N2—N3—C7—N1	−0.81 (10)	C13—C14—C15—C16	60.67 (14)
N2—N3—C7—S1	178.68 (7)	C14—C15—C16—C9	−60.06 (15)
C8—N1—C7—N3	1.15 (9)	C17—C15—C16—C9	60.65 (14)
C6—N1—C7—N3	−175.82 (8)	C8—C9—C16—C15	−178.05 (10)
C8—N1—C7—S1	−178.34 (7)	C10—C9—C16—C15	−59.33 (13)
C6—N1—C7—S1	4.69 (12)	C18—C9—C16—C15	58.94 (13)
N3—N2—C8—N1	0.64 (10)	C12—C11—C17—C15	−59.90 (12)
N3—N2—C8—C9	−178.62 (8)	C10—C11—C17—C15	60.27 (13)
C7—N1—C8—N2	−1.17 (10)	C14—C15—C17—C11	60.10 (13)
C6—N1—C8—N2	175.53 (9)	C16—C15—C17—C11	−60.52 (13)
C7—N1—C8—C9	178.05 (8)	C12—C13—C18—C9	−59.95 (12)
C6—N1—C8—C9	−5.25 (15)	C14—C13—C18—C9	60.26 (13)
N2—C8—C9—C16	122.54 (11)	C8—C9—C18—C13	178.01 (9)
N1—C8—C9—C16	−56.58 (13)	C16—C9—C18—C13	−59.20 (12)
N2—C8—C9—C10	3.91 (13)	C10—C9—C18—C13	58.56 (12)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···S1ⁱ	0.92 (2)	2.46 (2)	3.3253 (9)	158.4 (19)
C13—H13A···Cg2ⁱⁱ	0.98	2.97	3.8881 (13)	156

Symmetry codes: (i) −x+1/2, −y+3/2, z−1/2; (ii) y−1, −x+1, −z+1.