4,4-Diphenyl-1-propyl-2-propyl­sulfanyl-4,5-di­hydro-1H-imidazol-5-one

Akrad, R.; Guerrab, W.; Lazrak, F.; Ansar, M.; Taoufik, J.; Mague, J.T.; Ramli, Y.

doi:10.1107/S2414314618009343

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 7| July 2018| x180934

https://doi.org/10.1107/S2414314618009343

Open

access

4,4-Diphenyl-1-propyl-2-propylsulfanyl-4,5-dihydro-1H-imidazol-5-one

Rachida Akrad,^a Walid Guerrab,^a Fatima Lazrak,^a Mhammed Ansar,^a Jamal Taoufik,^a Joel T. Mague ^b and Youssef Ramli ^a ^*

^aLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, Mohammed V University, Rabat, Morocco, and ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: y.ramli@um5s.net.ma

Edited by J. Simpson, University of Otago, New Zealand (Received 25 June 2018; accepted 28 June 2018; online 6 July 2018)

In the title molecule, C₂₁H₂₄N₂OS, the five-membered ring is planar with an r.m.s. deviation of 0.0142 Å. The phenyl rings are inclined to the plane of the dihydroimidazolone ring by 60.81 (6) and 79.23 (6)°. In the crystal, inversion dimers are formed by a C—H⋯O hydrogen bond and a C—H⋯π(ring) interaction. Additional C—H⋯O hydrogen bonds and C—H⋯π(ring) interactions connect these dimers into chains along the c-axis direction.

Keywords: crystal structure; dihydroimidazolone; hydrogen bond; C—H⋯π(ring) interaction.

CCDC reference: 1852189

Structure description

Over the past thirty years, imidazolone derivatives of hydantoin or thiohydantoin have been the focus of interest for the synthetic and pharmaceutical industries because of their biological properties. As part of our ongoing studies of 4,4- and 5,5-diphenylimidazolidine-2,4-dione and 5,5-diphenyl-2-thioxoimidazolidin-4-one derivatives (Ramli, Akrad et al., 2017 ; Ramli, Guerrab et al., 2017 ; Akrad et al., 2017 ; Guerrab et al., 2017a ,b ), the title compound was prepared and its crystal structure is reported here.

In the title molecule (Fig. 1), the C10–C15 and C16–C21 benzene rings are inclined to the plane of the central five-membered ring by 60.81 (6) and 79.23 (6)°, respectively. In the crystal, C8—H8A⋯O1 hydrogen bonds and C9—H9A⋯Cg3 interactions, Table 1, form inversion dimers, which are connected into chains extending along the c-axis direction by C19—H19⋯O1 hydrogen bonds and C20—H20⋯Cg2 interactions (Table 1 and Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C10–C15 and C16–C21 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1ⁱ	1.005 (15)	2.607 (15)	3.5908 (14)	166.2 (11)
C9—H9A⋯Cg3ⁱ	0.973 (16)	2.908 (15)	3.7370 (15)	143.8 (12)
C19—H19⋯O1ⁱⁱ	0.955 (16)	2.596 (16)	3.4407 (15)	147.7 (12)
C20—H20⋯Cg2ⁱⁱ	0.997 (16)	2.999 (17)	3.7390 (14)	131.9 (12)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y, z-1.

Figure 1
The title molecule with the atom-labelling scheme and 50% probability ellipsoids.

Figure 2
A portion of a chain of the title molecules viewed along the b-axis direction. C—H⋯O hydrogen bonds and C—H⋯π(ring) interactions are shown by black and green dashed lines, respectively.

Synthesis and crystallization

Thiohydantoin (0.7 g) was placed in a flask with K₂CO₃ (0.9 g, 0.0065 mmol) in absolute dimethylformamide (DMF), and two equivalents of propyl iodide were added. The solution was left stirring for 2 h at room temperature. The solvent was then removed after filtration of the base and the oil obtained was recrystallized from methanol solution to yield colourless block-shaped single crystals (Guerrab et al., 2017c , 2018 ).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₁H₂₄N₂OS
M_r	352.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.898 (2), 14.878 (2), 8.4007 (13)
β (°)	96.780 (2)
V (Å³)	1849.0 (5)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.19
Crystal size (mm)	0.30 × 0.27 × 0.22

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.84, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	35375, 5241, 4279
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.708

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.114, 1.07
No. of reflections	5241
No. of parameters	322
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.19
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1852189

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314618009343/sj4186sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618009343/sj4186Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618009343/sj4186Isup3.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

4,4-Diphenyl-1-propyl-2-propylsulfanyl-4,5-dihydro-1H-imidazol-5-one top

Crystal data top

C₂₁H₂₄N₂OS	F(000) = 752
M_r = 352.48	D_x = 1.266 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.898 (2) Å	Cell parameters from 9958 reflections
b = 14.878 (2) Å	θ = 2.7–30.0°
c = 8.4007 (13) Å	µ = 0.19 mm⁻¹
β = 96.780 (2)°	T = 100 K
V = 1849.0 (5) Å³	Block, colourless
Z = 4	0.30 × 0.27 × 0.22 mm

Data collection top

Bruker SMART APEX CCD diffractometer	5241 independent reflections
Radiation source: fine-focus sealed tube	4279 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 8.3333 pixels mm^-1	θ_max = 30.2°, θ_min = 1.9°
φ and ω scans	h = −21→21
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −20→20
T_min = 0.84, T_max = 0.96	l = −11→11
35375 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	All H-atom parameters refined
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0755P)² + 0.1235P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
5241 reflections	Δρ_max = 0.51 e Å⁻³
322 parameters	Δρ_min = −0.19 e Å⁻³

Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 20 sec/frame.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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

	x	y	z	U_iso*/U_eq
S1	0.28969 (2)	0.21368 (2)	0.56491 (4)	0.02040 (10)
O1	0.40566 (5)	0.52459 (5)	0.63859 (9)	0.01851 (18)
N1	0.36245 (6)	0.37573 (6)	0.62527 (11)	0.01618 (19)
N2	0.22807 (6)	0.37922 (6)	0.46398 (11)	0.01469 (18)
C1	0.26378 (7)	0.47263 (7)	0.47678 (12)	0.0131 (2)
C2	0.35317 (7)	0.46531 (7)	0.59014 (12)	0.0146 (2)
C3	0.28811 (7)	0.33033 (7)	0.54480 (12)	0.0153 (2)
C4	0.18745 (8)	0.18173 (8)	0.44041 (14)	0.0203 (2)
H4A	0.1989 (11)	0.1189 (11)	0.404 (2)	0.037 (4)*
H4B	0.1770 (12)	0.2204 (10)	0.342 (2)	0.038 (5)*
C5	0.10239 (8)	0.18493 (8)	0.52482 (15)	0.0217 (2)
H5A	0.1147 (10)	0.1580 (10)	0.6326 (19)	0.027 (4)*
H5B	0.0847 (10)	0.2504 (11)	0.5396 (17)	0.025 (3)*
C6	0.02608 (9)	0.13272 (9)	0.42926 (17)	0.0264 (3)
H6A	0.0410 (11)	0.0673 (11)	0.4339 (19)	0.038 (4)*
H6B	0.0169 (10)	0.1538 (10)	0.3164 (19)	0.030 (4)*
H6C	−0.0330 (11)	0.1417 (10)	0.4759 (18)	0.032 (4)*
C7	0.44183 (7)	0.33597 (8)	0.71897 (13)	0.0181 (2)
H7A	0.4663 (10)	0.3808 (10)	0.7962 (18)	0.022 (3)*
H7B	0.4168 (11)	0.2821 (9)	0.7763 (18)	0.030 (4)*
C8	0.51335 (8)	0.30657 (8)	0.61454 (14)	0.0189 (2)
H8A	0.5325 (10)	0.3615 (10)	0.5576 (18)	0.025 (4)*
H8B	0.4848 (9)	0.2635 (9)	0.5348 (16)	0.018 (3)*
C9	0.59323 (8)	0.26092 (9)	0.71236 (16)	0.0232 (2)
H9A	0.6227 (10)	0.3009 (10)	0.7940 (19)	0.027 (4)*
H9B	0.6360 (11)	0.2419 (10)	0.6369 (19)	0.031 (4)*
H9C	0.5719 (12)	0.2071 (11)	0.765 (2)	0.038 (4)*
C10	0.19982 (7)	0.53663 (7)	0.54917 (12)	0.0139 (2)
C11	0.11947 (7)	0.50725 (7)	0.59961 (13)	0.0171 (2)
H11	0.1028 (9)	0.4450 (10)	0.5864 (17)	0.022 (3)*
C12	0.06233 (8)	0.56794 (8)	0.66487 (14)	0.0211 (2)
H12	0.0049 (10)	0.5497 (10)	0.7005 (17)	0.024 (4)*
C13	0.08580 (8)	0.65759 (8)	0.68128 (14)	0.0228 (2)
H13	0.0461 (10)	0.6994 (10)	0.7219 (18)	0.025 (4)*
C14	0.16667 (9)	0.68758 (8)	0.63317 (15)	0.0233 (2)
H14	0.1854 (10)	0.7476 (10)	0.6499 (17)	0.023 (3)*
C15	0.22333 (8)	0.62766 (7)	0.56654 (14)	0.0190 (2)
H15	0.2804 (10)	0.6485 (10)	0.5290 (17)	0.025 (4)*
C16	0.28335 (7)	0.50095 (7)	0.30928 (12)	0.0142 (2)
C17	0.36676 (8)	0.48304 (7)	0.25711 (14)	0.0181 (2)
H17	0.4160 (10)	0.4566 (10)	0.3323 (17)	0.027 (4)*
C18	0.38154 (9)	0.50281 (8)	0.10041 (14)	0.0228 (3)
H18	0.4394 (11)	0.4880 (11)	0.0687 (19)	0.038 (4)*
C19	0.31434 (9)	0.54172 (8)	−0.00507 (14)	0.0245 (3)
H19	0.3236 (10)	0.5579 (10)	−0.1119 (19)	0.033 (4)*
C20	0.23084 (9)	0.55984 (8)	0.04611 (14)	0.0236 (2)
H20	0.1804 (11)	0.5876 (11)	−0.026 (2)	0.035 (4)*
C21	0.21515 (8)	0.53930 (8)	0.20199 (13)	0.0189 (2)
H21	0.1559 (10)	0.5492 (9)	0.2374 (17)	0.026 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02010 (16)	0.01411 (15)	0.02723 (17)	0.00107 (9)	0.00377 (12)	0.00478 (10)
O1	0.0172 (4)	0.0200 (4)	0.0179 (4)	−0.0018 (3)	0.0004 (3)	−0.0023 (3)
N1	0.0156 (4)	0.0167 (4)	0.0156 (4)	0.0016 (3)	−0.0007 (3)	0.0024 (3)
N2	0.0165 (4)	0.0126 (4)	0.0154 (4)	−0.0007 (3)	0.0036 (3)	0.0000 (3)
C1	0.0130 (5)	0.0136 (5)	0.0125 (5)	−0.0004 (3)	0.0011 (4)	0.0006 (3)
C2	0.0155 (5)	0.0179 (5)	0.0108 (5)	0.0010 (4)	0.0030 (4)	0.0000 (4)
C3	0.0168 (5)	0.0155 (5)	0.0143 (5)	−0.0004 (4)	0.0048 (4)	0.0017 (4)
C4	0.0239 (6)	0.0158 (5)	0.0219 (6)	−0.0021 (4)	0.0061 (4)	−0.0009 (4)
C5	0.0214 (6)	0.0221 (6)	0.0225 (6)	−0.0015 (4)	0.0064 (5)	−0.0018 (5)
C6	0.0243 (6)	0.0254 (6)	0.0296 (7)	−0.0039 (5)	0.0038 (5)	−0.0027 (5)
C7	0.0171 (5)	0.0219 (5)	0.0149 (5)	0.0044 (4)	0.0002 (4)	0.0029 (4)
C8	0.0180 (5)	0.0226 (5)	0.0159 (5)	0.0016 (4)	0.0018 (4)	0.0016 (4)
C9	0.0205 (6)	0.0237 (6)	0.0248 (6)	0.0053 (5)	0.0007 (5)	0.0013 (5)
C10	0.0146 (5)	0.0158 (5)	0.0110 (5)	0.0015 (4)	0.0005 (4)	0.0011 (4)
C11	0.0175 (5)	0.0184 (5)	0.0155 (5)	−0.0003 (4)	0.0020 (4)	0.0007 (4)
C12	0.0173 (5)	0.0277 (6)	0.0187 (6)	0.0029 (4)	0.0044 (4)	0.0015 (4)
C13	0.0242 (6)	0.0250 (6)	0.0196 (6)	0.0103 (5)	0.0041 (5)	0.0003 (4)
C14	0.0281 (6)	0.0160 (5)	0.0258 (6)	0.0030 (4)	0.0036 (5)	−0.0014 (4)
C15	0.0193 (5)	0.0174 (5)	0.0206 (6)	−0.0001 (4)	0.0031 (4)	0.0001 (4)
C16	0.0175 (5)	0.0129 (5)	0.0122 (5)	−0.0025 (4)	0.0023 (4)	−0.0003 (4)
C17	0.0180 (5)	0.0182 (5)	0.0186 (5)	−0.0014 (4)	0.0040 (4)	−0.0021 (4)
C18	0.0252 (6)	0.0240 (6)	0.0209 (6)	−0.0065 (5)	0.0105 (5)	−0.0063 (4)
C19	0.0390 (7)	0.0230 (6)	0.0125 (5)	−0.0094 (5)	0.0068 (5)	−0.0025 (4)
C20	0.0311 (6)	0.0238 (6)	0.0146 (5)	−0.0026 (5)	−0.0024 (5)	0.0012 (4)
C21	0.0192 (5)	0.0211 (5)	0.0160 (5)	0.0006 (4)	0.0006 (4)	0.0001 (4)

Geometric parameters (Å, º) top

S1—C3	1.7436 (11)	C9—H9A	0.973 (16)
S1—C4	1.8066 (13)	C9—H9B	0.991 (16)
O1—C2	1.2165 (13)	C9—H9C	0.987 (16)
N1—C2	1.3686 (14)	C10—C11	1.3867 (15)
N1—C3	1.4012 (14)	C10—C15	1.4022 (15)
N1—C7	1.4657 (14)	C11—C12	1.3967 (15)
N2—C3	1.2832 (14)	C11—H11	0.961 (15)
N2—C1	1.4874 (13)	C12—C13	1.3816 (18)
C1—C10	1.5236 (14)	C12—H12	0.977 (14)
C1—C16	1.5295 (14)	C13—C14	1.3889 (18)
C1—C2	1.5469 (15)	C13—H13	0.949 (15)
C4—C5	1.5242 (16)	C14—C15	1.3900 (16)
C4—H4A	1.003 (17)	C14—H14	0.941 (15)
C4—H4B	1.002 (17)	C15—H15	0.991 (14)
C5—C6	1.5248 (18)	C16—C17	1.3914 (15)
C5—H5A	0.987 (15)	C16—C21	1.3978 (15)
C5—H5B	1.020 (16)	C17—C18	1.3915 (16)
C6—H6A	0.997 (17)	C17—H17	0.992 (15)
C6—H6B	0.993 (16)	C18—C19	1.3832 (19)
C6—H6C	1.014 (16)	C18—H18	0.958 (16)
C7—C8	1.5222 (15)	C19—C20	1.3897 (18)
C7—H7A	0.971 (15)	C19—H19	0.955 (16)
C7—H7B	1.028 (15)	C20—C21	1.3911 (16)
C8—C9	1.5238 (16)	C20—H20	0.997 (16)
C8—H8A	1.005 (15)	C21—H21	0.976 (15)
C8—H8B	0.987 (14)

C3—S1—C4	101.83 (5)	C9—C8—H8B	108.9 (8)
C2—N1—C3	108.15 (9)	H8A—C8—H8B	109.2 (11)
C2—N1—C7	124.29 (9)	C8—C9—H9A	111.5 (9)
C3—N1—C7	127.32 (9)	C8—C9—H9B	107.6 (9)
C3—N2—C1	105.69 (9)	H9A—C9—H9B	110.8 (13)
N2—C1—C10	112.18 (8)	C8—C9—H9C	109.4 (10)
N2—C1—C16	107.23 (8)	H9A—C9—H9C	108.7 (13)
C10—C1—C16	113.03 (8)	H9B—C9—H9C	108.8 (13)
N2—C1—C2	104.68 (8)	C11—C10—C15	119.12 (10)
C10—C1—C2	109.38 (8)	C11—C10—C1	121.87 (9)
C16—C1—C2	110.00 (8)	C15—C10—C1	119.00 (9)
O1—C2—N1	126.11 (10)	C10—C11—C12	120.28 (10)
O1—C2—C1	128.88 (10)	C10—C11—H11	119.3 (8)
N1—C2—C1	105.01 (8)	C12—C11—H11	120.4 (8)
N2—C3—N1	116.35 (10)	C13—C12—C11	120.30 (11)
N2—C3—S1	128.03 (8)	C13—C12—H12	117.3 (8)
N1—C3—S1	115.61 (8)	C11—C12—H12	122.4 (8)
C5—C4—S1	114.39 (8)	C12—C13—C14	119.94 (11)
C5—C4—H4A	110.5 (9)	C12—C13—H13	120.5 (9)
S1—C4—H4A	105.0 (9)	C14—C13—H13	119.6 (9)
C5—C4—H4B	107.9 (10)	C13—C14—C15	120.01 (11)
S1—C4—H4B	111.3 (10)	C13—C14—H14	120.9 (8)
H4A—C4—H4B	107.6 (13)	C15—C14—H14	119.0 (9)
C4—C5—C6	110.39 (10)	C14—C15—C10	120.34 (11)
C4—C5—H5A	109.8 (8)	C14—C15—H15	120.8 (8)
C6—C5—H5A	108.8 (9)	C10—C15—H15	118.8 (8)
C4—C5—H5B	109.1 (8)	C17—C16—C21	118.90 (10)
C6—C5—H5B	111.3 (8)	C17—C16—C1	120.76 (9)
H5A—C5—H5B	107.3 (12)	C21—C16—C1	120.18 (9)
C5—C6—H6A	109.1 (9)	C16—C17—C18	120.30 (11)
C5—C6—H6B	110.6 (9)	C16—C17—H17	119.8 (8)
H6A—C6—H6B	110.6 (13)	C18—C17—H17	119.9 (8)
C5—C6—H6C	110.9 (9)	C19—C18—C17	120.74 (11)
H6A—C6—H6C	108.2 (12)	C19—C18—H18	121.7 (10)
H6B—C6—H6C	107.4 (12)	C17—C18—H18	117.5 (10)
N1—C7—C8	112.44 (9)	C18—C19—C20	119.32 (11)
N1—C7—H7A	107.3 (9)	C18—C19—H19	122.3 (9)
C8—C7—H7A	110.4 (9)	C20—C19—H19	118.4 (9)
N1—C7—H7B	104.6 (9)	C19—C20—C21	120.30 (11)
C8—C7—H7B	111.3 (8)	C19—C20—H20	121.9 (9)
H7A—C7—H7B	110.6 (12)	C21—C20—H20	117.8 (9)
C7—C8—C9	111.87 (9)	C20—C21—C16	120.44 (11)
C7—C8—H8A	107.4 (8)	C20—C21—H21	120.8 (9)
C9—C8—H8A	111.8 (9)	C16—C21—H21	118.7 (9)
C7—C8—H8B	107.6 (8)

C3—N2—C1—C10	−121.87 (9)	C16—C1—C10—C11	123.08 (10)
C3—N2—C1—C16	113.47 (9)	C2—C1—C10—C11	−114.01 (11)
C3—N2—C1—C2	−3.36 (10)	N2—C1—C10—C15	−178.90 (9)
C3—N1—C2—O1	−179.50 (10)	C16—C1—C10—C15	−57.51 (13)
C7—N1—C2—O1	−4.77 (17)	C2—C1—C10—C15	65.41 (12)
C3—N1—C2—C1	−0.08 (10)	C15—C10—C11—C12	0.83 (16)
C7—N1—C2—C1	174.66 (9)	C1—C10—C11—C12	−179.76 (10)
N2—C1—C2—O1	−178.56 (10)	C10—C11—C12—C13	−0.67 (17)
C10—C1—C2—O1	−58.17 (13)	C11—C12—C13—C14	−0.19 (18)
C16—C1—C2—O1	66.53 (13)	C12—C13—C14—C15	0.89 (18)
N2—C1—C2—N1	2.04 (10)	C13—C14—C15—C10	−0.73 (18)
C10—C1—C2—N1	122.43 (9)	C11—C10—C15—C14	−0.13 (17)
C16—C1—C2—N1	−112.87 (9)	C1—C10—C15—C14	−179.56 (10)
C1—N2—C3—N1	3.68 (12)	N2—C1—C16—C17	−88.04 (11)
C1—N2—C3—S1	−175.29 (8)	C10—C1—C16—C17	147.81 (10)
C2—N1—C3—N2	−2.40 (12)	C2—C1—C16—C17	25.24 (13)
C7—N1—C3—N2	−176.93 (10)	N2—C1—C16—C21	87.17 (11)
C2—N1—C3—S1	176.70 (7)	C10—C1—C16—C21	−36.98 (13)
C7—N1—C3—S1	2.17 (14)	C2—C1—C16—C21	−159.55 (9)
C4—S1—C3—N2	1.13 (11)	C21—C16—C17—C18	−0.24 (16)
C4—S1—C3—N1	−177.84 (8)	C1—C16—C17—C18	175.03 (10)
C3—S1—C4—C5	−85.29 (9)	C16—C17—C18—C19	1.00 (17)
S1—C4—C5—C6	−163.91 (9)	C17—C18—C19—C20	−0.98 (17)
C2—N1—C7—C8	−90.02 (12)	C18—C19—C20—C21	0.20 (18)
C3—N1—C7—C8	83.69 (13)	C19—C20—C21—C16	0.55 (18)
N1—C7—C8—C9	−177.00 (10)	C17—C16—C21—C20	−0.53 (16)
N2—C1—C10—C11	1.68 (14)	C1—C16—C21—C20	−175.83 (10)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C10–C15 and C16–C21 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1ⁱ	1.005 (15)	2.607 (15)	3.5908 (14)	166.2 (11)
C9—H9A···Cg3ⁱ	0.973 (16)	2.908 (15)	3.7370 (15)	143.8 (12)
C19—H19···O1ⁱⁱ	0.955 (16)	2.596 (16)	3.4407 (15)	147.7 (12)
C20—H20···Cg2ⁱⁱ	0.997 (16)	2.999 (17)	3.7390 (14)	131.9 (12)

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

Funding information

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

References

Akrad, R., Mague, J. T., Guerrab, W., Taoufik, J., Ansar, M. & Ramli, Y. (2017). IUCrData, 2, x170033. Google Scholar
Brandenburg, K. & Putz, H. (2012). DIAMOND, Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2016). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Guerrab, W., Akrad, R., Ansar, M., Taoufik, J., Mague, J. T. & Ramli, Y. (2017a). IUCrData, 2, x171534. Google Scholar
Guerrab, W., Akrad, R., Ansar, M., Taoufik, J., Mague, J. T. & Ramli, Y. (2017b). IUCrData, 2, x171591. Google Scholar
Guerrab, W., Akrad, R., Ansar, M., Taoufik, J., Mague, J. T. & Ramli, Y. (2017c). IUCrData, 2, x171693. Google Scholar
Guerrab, W., Mague, J. T., Akrad, R., Ansar, M., Taoufik, J. & Ramli, Y. (2018). IUCrData, 3, x180050. Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Ramli, Y., Akrad, R., Guerrab, W., Taoufik, J., Ansar, M. & Mague, J. T. (2017). IUCrData, 2, x170098. Google Scholar
Ramli, Y., Guerrab, W., Moussaif, A., Taoufik, J., Essassi, E. M. & Mague, J. T. (2017). IUCrData, 2, x171041. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

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