Related literature

Acta Crystallogr Sect E Struct Rep Online

Acta Cryst. E

Acta Crystallographica Section E: Structure Reports Online

1600-5368

International Union of Crystallography

22904798

3414191

hb6881

10.1107/S1600536812029510

ACSEBH

S1600536812029510

Organic Papers

5-(Adamantan-1-yl)-3-[(2-methoxyethyl)sulfanyl]-4-phenyl-4H-1,2,4-triazole

C₂₁H₂₇N₃OS

El-Emam

Ali A.

aAl-Abdullah

Ebtehal S.

aAsiri

Hanadi H.

aChantrapromma

Suchada

b‡Fun

Hoong-Kun

c*§aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi ArabiabCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, ThailandcX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia

Correspondence e-mail: hkfun@usm.my‡

Thomson Reuters ResearcherID: A-5085-2009.

Thomson Reuters ResearcherID: A-3561-2009.

0182012

0472012

68Pt 8

e120800

o2326o232627620122862012

2012

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.

A full version of this article is available from Crystallography Journals Online.

In the title adamantyl derivative, C₂₁H₂₇N₃OS, the terminal methoxyethyl unit is disordered over two orientations with a refined site-occupancy ratio of 0.846 (6):0.154 (6). The 1,2,4-triazole ring is statistically planar [r.m.s. deviation = 0.002 (2) Å] and the phenyl substituent is almost perpendicular to its mean plane [dihedral angle = 83.57 (11)°]. No directional intermolecular interactions were observed in the crystal structure.

Related literature

For the biological activity of adamantane derivatives, see: Kadi et al. (2010 ▶). For related adamantyl-1,2,4-triazole structures, see: Al-Abdullah et al. (2012 ▶); Almutairi et al. (2012 ▶); El-Emam et al. (2012 ▶). For substituted sulfanyl-1,2,4-triazole structures, see: Fun et al. (2011 ▶); Wang et al. (2011 ▶).

Experimental <sec id="sec2.1.1"><title>Crystal data

C₂₁H₂₇N₃OS

M _r = 369.53

Monoclinic,

a = 22.5107 (5) Å

b = 9.7642 (2) Å

c = 19.5594 (3) Å

β = 116.679 (1)°

V = 3841.43 (13) Å³

Z = 8

Cu Kα radiation

μ = 1.60 mm⁻¹

T = 296 K

0.59 × 0.56 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.453, T _max = 0.761

12922 measured reflections

3499 independent reflections

3075 reflections with I > 2σ(I)

R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.045

wR(F ²) = 0.130

S = 1.05

3499 reflections

245 parameters

H-atom parameters constrained

Δρ_max = 0.22 e Å⁻³

Δρ_min = −0.30 e Å⁻³

Data collection: <italic>APEX2</italic> (Bruker, 2009<xref ref-type="bibr" rid="bb3"> ▶</xref>); cell refinement: <italic>SAINT</italic> (Bruker, 2009<xref ref-type="bibr" rid="bb3"> ▶</xref>); data reduction: <italic>SAINT</italic>; program(s) used to solve structure: <italic>SHELXTL</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb7"> ▶</xref>); program(s) used to refine structure: <italic>SHELXTL</italic>; molecular graphics: <italic>SHELXTL</italic>; software used to prepare material for publication: <italic>SHELXTL</italic> and <italic>PLATON</italic> (Spek, 2009<xref ref-type="bibr" rid="bb8"> ▶</xref>).</sec></sec><sec sec-type="supplementary-material"><title>Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029510/hb6881sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029510/hb6881Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029510/hb6881Isup3.cml

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

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6881).

The financial support of the Deanship of Scientific Research and the Research Center for Female Scientific and Medical Colleges, King Saud University is greatly appreciated. HKF and SC thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

supplementary crystallographic information Comment

In continuation of our interest in the chemical and pharmacological properties of adamantane derivatives (Kadi et al., 2010), we synthesized the title compound (I) as a potential chemotherapeutic agent and herein its crystal structure is reported.

In the molecule of the title adamantyl derivative, C₂₁H₂₇N₃OS, (Fig. 1) the terminal methoxyethyl unit is disordered over two orientations with the refined site-occupancy ratio of 0.845 (6):0.155 (6). The 1,2,4-triazole ring is planar with an r.m.s. deviation of 0.002 (2) Å. The phenyl substituent is almost perpendicular to the mean plane of the 1,2,4-triazole ring with the dihedral angle of 83.57 (11)°. The adamantyl group is planarly attached to the 1,2,4-triazole ring at atom position 5 or atom C2. The 2-(methoxyethyl)sulfanyl substituent is planarly attached to this five-membered ring with the torsion angle C1–S1–C19–C20 = 179.61 (15)°. The orientation of the terminal disordered methoxyethyl unit can be indicated by the torsion angles C21–O1–C20–C19 = -176.1 (2)° for the major component (A) and 127.7 (7)° for the minor component (B). The bond distances in (I) are comparable with those in related structures (Al-Abdullah et al., 2012; Almutairi et al., 2012; El-Emam et al., 2012; Fun et al., 2011 and Wang et al., 2011).

Even though no intermolecular hydrogen bond was observed in the crystal packing of (I), however the crystal packing was shown in Fig. 2 to illustrate the arrangement of the molecules.

Experimental

A mixture of 3-(adamantan-1-yl)-4-phenyl-4H-1,2,4-triazole-5-thiol (623 mg, 2 mmol), 1-bromo-2-methoxyethane (278 mg, 2 mmol) and anhydrous potassium carbonate (276 mg, 2 mmol) in N,N-dimethylformamide (5 ml) was stirred at room temperature for 24 h. Water (15 ml) was added and the mixture was stirred for 30 min. The separated crude product was filtered, washed with water, dried and crystallized from aqueous ethanol to yield 196 gm (53 %) of the title compound as colorless plate-shaped crystals, M.p. 428-430 K.

FiguresFig. 1.

The molecular structure of the title compound, showing 30% probability displacement ellipsoids. Open bonds show the minor disorder component.

Fig. 2.

The crystal packing of the title compound viewed along the b axis. Only the major component was shown.

Crystal data

C₂₁H₂₇N₃OS	F(000) = 1584
M_r = 369.53	D_x = 1.278 Mg m⁻³
Monoclinic, C2/c	Melting point = 428–430 K
Hall symbol: -C 2yc	Cu Kα radiation, λ = 1.54178 Å
a = 22.5107 (5) Å	Cell parameters from 3499 reflections
b = 9.7642 (2) Å	θ = 5.0–69.0°
c = 19.5594 (3) Å	µ = 1.60 mm⁻¹
β = 116.679 (1)°	T = 296 K
V = 3841.43 (13) Å³	Plate, colorless
Z = 8	0.59 × 0.56 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer	3499 independent reflections
Radiation source: fine-focus sealed tube	3075 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
φ and ω scans	θ_max = 69.0°, θ_min = 5.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −27→26
T_min = 0.453, T_max = 0.761	k = −11→11
12922 measured reflections	l = −23→23

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0809P)² + 1.3248P] where P = (F_o² + 2F_c²)/3
3499 reflections	(Δ/σ)_max = 0.001
245 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Special details

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)

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.08715 (2)	0.28171 (4)	0.23891 (2)	0.05409 (17)
N1	0.11945 (7)	0.33435 (13)	0.38845 (7)	0.0413 (3)
N2	0.10327 (8)	0.11543 (14)	0.35822 (9)	0.0532 (4)
N3	0.11921 (8)	0.13061 (14)	0.43546 (9)	0.0526 (4)
O1A	0.10717 (11)	0.1555 (2)	0.10375 (10)	0.0672 (7)	0.846 (6)
O1B	0.0543 (8)	0.1948 (10)	0.0738 (6)	0.076 (5)	0.154 (6)
C1	0.10350 (8)	0.23789 (17)	0.33203 (9)	0.0444 (4)
C2	0.12860 (8)	0.26011 (16)	0.45299 (9)	0.0424 (3)
C3	0.14495 (8)	0.31590 (16)	0.53129 (9)	0.0417 (3)
C4	0.13939 (12)	0.19832 (18)	0.58035 (11)	0.0593 (5)
H4A	0.0946	0.1616	0.5565	0.071*
H4B	0.1698	0.1254	0.5835	0.071*
C5	0.15593 (12)	0.2492 (2)	0.66116 (11)	0.0655 (5)
H5A	0.1524	0.1727	0.6916	0.079*
C6	0.10653 (11)	0.3612 (2)	0.65583 (11)	0.0627 (5)
H6A	0.0616	0.3249	0.6320	0.075*
H6B	0.1161	0.3931	0.7067	0.075*
C7	0.11237 (9)	0.47934 (19)	0.60849 (10)	0.0529 (4)
H7A	0.0812	0.5520	0.6053	0.063*
C8	0.09607 (8)	0.42908 (18)	0.52755 (9)	0.0463 (4)
H8A	0.0990	0.5050	0.4972	0.056*
H8B	0.0510	0.3938	0.5030	0.056*
C9	0.21600 (9)	0.3739 (2)	0.57084 (11)	0.0568 (4)
H9A	0.2475	0.3035	0.5738	0.068*
H9B	0.2201	0.4496	0.5411	0.068*
C10	0.23171 (9)	0.4233 (2)	0.65161 (11)	0.0649 (5)
H10A	0.2770	0.4604	0.6762	0.078*
C11	0.18282 (10)	0.5350 (2)	0.64632 (11)	0.0629 (5)
H11A	0.1932	0.5681	0.6972	0.076*
H11B	0.1866	0.6113	0.6167	0.076*
C12	0.22647 (12)	0.3049 (3)	0.69881 (11)	0.0755 (6)
H12A	0.2375	0.3359	0.7502	0.091*
H12B	0.2575	0.2333	0.7022	0.091*
C13	0.12558 (8)	0.47952 (16)	0.37871 (9)	0.0433 (4)
C14	0.18701 (10)	0.5351 (2)	0.39749 (12)	0.0607 (5)
H14A	0.2247	0.4800	0.4152	0.073*
C15	0.19180 (14)	0.6760 (2)	0.38947 (15)	0.0795 (7)
H15A	0.2331	0.7154	0.4022	0.095*
C16	0.13615 (16)	0.7570 (2)	0.36300 (13)	0.0793 (7)
H16A	0.1399	0.8511	0.3589	0.095*
C17	0.07556 (13)	0.6996 (2)	0.34282 (12)	0.0694 (6)
H17A	0.0379	0.7549	0.3241	0.083*
C18	0.06922 (10)	0.55996 (19)	0.34984 (10)	0.0544 (4)
H18A	0.0276	0.5210	0.3353	0.065*
C19	0.07046 (11)	0.1108 (2)	0.19793 (11)	0.0597 (5)
H19A	0.1092	0.0533	0.2248	0.072*
H19B	0.0337	0.0708	0.2040	0.072*
C20	0.05380 (13)	0.1161 (3)	0.11512 (13)	0.0738 (6)
H20A	0.0389	0.0263	0.0926	0.089*	0.846 (6)
H20B	0.0175	0.1800	0.0894	0.089*	0.846 (6)
H20C	0.0797	0.0424	0.1098	0.089*	0.154 (6)
H20D	0.0087	0.0837	0.0911	0.089*	0.154 (6)
C21	0.08943 (16)	0.1691 (3)	0.02410 (14)	0.0851 (7)
H21A	0.1278	0.1967	0.0183	0.128*	0.846 (6)
H21B	0.0552	0.2370	0.0017	0.128*	0.846 (6)
H21C	0.0735	0.0829	−0.0011	0.128*	0.846 (6)
H21D	0.0838	0.2477	−0.0077	0.128*	0.154 (6)
H21E	0.1359	0.1547	0.0565	0.128*	0.154 (6)
H21F	0.0711	0.0899	−0.0075	0.128*	0.154 (6)

Atomic displacement parameters (Å2)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0784 (3)	0.0442 (3)	0.0448 (3)	0.00191 (19)	0.0322 (2)	−0.00132 (15)
N1	0.0540 (7)	0.0328 (6)	0.0422 (7)	0.0010 (5)	0.0260 (6)	0.0000 (5)
N2	0.0774 (10)	0.0377 (7)	0.0523 (8)	−0.0018 (6)	0.0360 (8)	−0.0030 (6)
N3	0.0776 (10)	0.0362 (7)	0.0533 (8)	0.0003 (6)	0.0376 (8)	0.0005 (6)
O1A	0.0721 (14)	0.0758 (13)	0.0534 (10)	−0.0075 (10)	0.0280 (10)	−0.0151 (8)
O1B	0.123 (13)	0.055 (5)	0.065 (6)	0.010 (6)	0.056 (7)	0.022 (5)
C1	0.0529 (8)	0.0404 (8)	0.0449 (8)	0.0008 (6)	0.0263 (7)	−0.0019 (6)
C2	0.0520 (8)	0.0356 (8)	0.0456 (8)	0.0027 (6)	0.0272 (7)	0.0032 (6)
C3	0.0490 (8)	0.0377 (8)	0.0413 (8)	0.0026 (6)	0.0228 (7)	0.0023 (6)
C4	0.0881 (13)	0.0434 (9)	0.0560 (10)	0.0048 (9)	0.0408 (10)	0.0079 (8)
C5	0.0989 (16)	0.0556 (11)	0.0519 (10)	0.0053 (10)	0.0425 (11)	0.0125 (8)
C6	0.0718 (12)	0.0775 (13)	0.0489 (10)	−0.0054 (10)	0.0360 (9)	−0.0048 (9)
C7	0.0591 (10)	0.0553 (10)	0.0441 (9)	0.0095 (8)	0.0232 (8)	−0.0048 (7)
C8	0.0502 (8)	0.0471 (9)	0.0409 (8)	0.0059 (7)	0.0198 (7)	−0.0012 (6)
C9	0.0474 (9)	0.0705 (12)	0.0529 (10)	0.0028 (8)	0.0229 (8)	0.0019 (8)
C10	0.0480 (9)	0.0863 (14)	0.0494 (10)	−0.0035 (9)	0.0120 (8)	−0.0056 (9)
C11	0.0776 (12)	0.0604 (11)	0.0467 (10)	−0.0109 (9)	0.0242 (9)	−0.0126 (8)
C12	0.0768 (13)	0.0928 (16)	0.0453 (10)	0.0270 (12)	0.0172 (10)	0.0131 (10)
C13	0.0617 (9)	0.0335 (8)	0.0406 (8)	0.0006 (6)	0.0282 (7)	0.0013 (6)
C14	0.0665 (11)	0.0519 (10)	0.0701 (12)	−0.0058 (8)	0.0365 (10)	0.0029 (8)
C15	0.1005 (17)	0.0571 (13)	0.0889 (16)	−0.0289 (12)	0.0497 (14)	−0.0048 (11)
C16	0.141 (2)	0.0356 (9)	0.0696 (13)	−0.0053 (12)	0.0546 (15)	0.0023 (9)
C17	0.1080 (17)	0.0449 (10)	0.0599 (11)	0.0206 (11)	0.0419 (12)	0.0118 (8)
C18	0.0689 (11)	0.0469 (9)	0.0502 (9)	0.0084 (8)	0.0292 (8)	0.0051 (7)
C19	0.0726 (12)	0.0502 (10)	0.0541 (10)	−0.0017 (8)	0.0264 (9)	−0.0092 (8)
C20	0.0829 (15)	0.0723 (15)	0.0653 (13)	−0.0105 (11)	0.0325 (11)	−0.0228 (11)
C21	0.132 (2)	0.0667 (14)	0.0634 (13)	−0.0083 (14)	0.0501 (14)	−0.0103 (10)

Geometric parameters (Å, º)

S1—C1	1.7418 (17)	C9—H9B	0.9700
S1—C19	1.8161 (19)	C10—C12	1.517 (3)
N1—C1	1.370 (2)	C10—C11	1.519 (3)
N1—C2	1.389 (2)	C10—H10A	0.9800
N1—C13	1.4450 (19)	C11—H11A	0.9700
N2—C1	1.302 (2)	C11—H11B	0.9700
N2—N3	1.395 (2)	C12—H12A	0.9700
N3—C2	1.302 (2)	C12—H12B	0.9700
O1A—C20	1.371 (3)	C13—C14	1.374 (3)
O1A—C21	1.430 (3)	C13—C18	1.379 (2)
O1B—C20	1.119 (9)	C14—C15	1.394 (3)
O1B—C21	1.524 (11)	C14—H14A	0.9300
C2—C3	1.507 (2)	C15—C16	1.371 (4)
C3—C4	1.537 (2)	C15—H15A	0.9300
C3—C8	1.538 (2)	C16—C17	1.359 (4)
C3—C9	1.538 (2)	C16—H16A	0.9300
C4—C5	1.534 (3)	C17—C18	1.384 (3)
C4—H4A	0.9700	C17—H17A	0.9300
C4—H4B	0.9700	C18—H18A	0.9300
C5—C12	1.520 (3)	C19—C20	1.491 (3)
C5—C6	1.530 (3)	C19—H19A	0.9700
C5—H5A	0.9800	C19—H19B	0.9700
C6—C7	1.522 (3)	C20—H20A	0.9700
C6—H6A	0.9700	C20—H20B	0.9700
C6—H6B	0.9700	C20—H20C	0.9601
C7—C11	1.518 (3)	C20—H20D	0.9599
C7—C8	1.536 (2)	C21—H21A	0.9599
C7—H7A	0.9800	C21—H21B	0.9600
C8—H8A	0.9700	C21—H21C	0.9600
C8—H8B	0.9700	C21—H21D	0.9600
C9—C10	1.534 (3)	C21—H21E	0.9598
C9—H9A	0.9700	C21—H21F	0.9600

C1—S1—C19	98.08 (9)	C10—C12—H12B	109.9
C1—N1—C2	104.57 (13)	C5—C12—H12B	109.9
C1—N1—C13	125.03 (13)	H12A—C12—H12B	108.3
C2—N1—C13	130.39 (13)	C14—C13—C18	120.99 (16)
C1—N2—N3	106.50 (13)	C14—C13—N1	119.80 (15)
C2—N3—N2	108.70 (13)	C18—C13—N1	119.21 (15)
C20—O1A—C21	111.5 (2)	C13—C14—C15	118.7 (2)
C21—O1A—H20C	105.5	C13—C14—H14A	120.7
C20—O1A—H21E	146.8	C15—C14—H14A	120.7
H20C—O1A—H21E	117.0	C16—C15—C14	120.5 (2)
C20—O1B—C21	121.6 (9)	C16—C15—H15A	119.7
C20—O1B—H21B	152.8	C14—C15—H15A	119.7
N2—C1—N1	111.12 (14)	C17—C16—C15	120.0 (2)
N2—C1—S1	126.93 (13)	C17—C16—H16A	120.0
N1—C1—S1	121.95 (12)	C15—C16—H16A	120.0
N3—C2—N1	109.10 (14)	C16—C17—C18	120.8 (2)
N3—C2—C3	123.72 (14)	C16—C17—H17A	119.6
N1—C2—C3	127.16 (14)	C18—C17—H17A	119.6
C2—C3—C4	108.26 (13)	C13—C18—C17	119.01 (19)
C2—C3—C8	111.61 (13)	C13—C18—H18A	120.5
C4—C3—C8	108.03 (14)	C17—C18—H18A	120.5
C2—C3—C9	111.62 (13)	C20—C19—S1	110.44 (15)
C4—C3—C9	108.59 (15)	C20—C19—H19A	109.6
C8—C3—C9	108.64 (14)	S1—C19—H19A	109.6
C5—C4—C3	110.57 (15)	C20—C19—H19B	109.6
C5—C4—H4A	109.5	S1—C19—H19B	109.6
C3—C4—H4A	109.5	H19A—C19—H19B	108.1
C5—C4—H4B	109.5	O1B—C20—O1A	52.9 (7)
C3—C4—H4B	109.5	O1B—C20—C19	136.8 (6)
H4A—C4—H4B	108.1	O1A—C20—C19	112.00 (19)
C12—C5—C6	110.26 (19)	O1B—C20—H20A	114.0
C12—C5—C4	109.43 (18)	O1A—C20—H20A	109.2
C6—C5—C4	109.17 (17)	C19—C20—H20A	109.2
C12—C5—H5A	109.3	O1B—C20—H20B	57.4
C6—C5—H5A	109.3	O1A—C20—H20B	109.2
C4—C5—H5A	109.3	C19—C20—H20B	109.2
C7—C6—C5	108.95 (15)	H20A—C20—H20B	107.9
C7—C6—H6A	109.9	O1B—C20—H20C	103.5
C5—C6—H6A	109.9	O1A—C20—H20C	64.8
C7—C6—H6B	109.9	C19—C20—H20C	102.9
C5—C6—H6B	109.9	H20A—C20—H20C	51.4
H6A—C6—H6B	108.3	H20B—C20—H20C	146.7
C11—C7—C6	109.37 (16)	O1B—C20—H20D	103.0
C11—C7—C8	109.30 (15)	O1A—C20—H20D	145.4
C6—C7—C8	109.82 (15)	C19—C20—H20D	102.4
C11—C7—H7A	109.4	H20A—C20—H20D	53.6
C6—C7—H7A	109.4	H20B—C20—H20D	60.0
C8—C7—H7A	109.4	H20C—C20—H20D	105.0
C7—C8—C3	110.23 (13)	O1A—C21—H21A	109.3
C7—C8—H8A	109.6	O1B—C21—H21A	141.5
C3—C8—H8A	109.6	O1A—C21—H21B	109.6
C7—C8—H8B	109.6	O1B—C21—H21B	68.7
C3—C8—H8B	109.6	H21A—C21—H21B	109.5
H8A—C8—H8B	108.1	O1A—C21—H21C	109.6
C10—C9—C3	109.92 (15)	O1B—C21—H21C	106.9
C10—C9—H9A	109.7	H21A—C21—H21C	109.5
C3—C9—H9A	109.7	H21B—C21—H21C	109.5
C10—C9—H9B	109.7	O1A—C21—H21D	132.2
C3—C9—H9B	109.7	O1B—C21—H21D	109.1
H9A—C9—H9B	108.2	H21A—C21—H21D	64.1
C12—C10—C11	109.68 (18)	H21B—C21—H21D	46.1
C12—C10—C9	109.98 (19)	H21C—C21—H21D	117.2
C11—C10—C9	109.32 (15)	O1A—C21—H21E	65.1
C12—C10—H10A	109.3	O1B—C21—H21E	109.0
C11—C10—H10A	109.3	H21A—C21—H21E	49.2
C9—C10—H10A	109.3	H21B—C21—H21E	144.7
C7—C11—C10	110.02 (16)	H21C—C21—H21E	104.8
C7—C11—H11A	109.7	H21D—C21—H21E	109.5
C10—C11—H11A	109.7	O1A—C21—H21F	117.1
C7—C11—H11B	109.7	O1B—C21—H21F	110.3
C10—C11—H11B	109.7	H21A—C21—H21F	107.4
H11A—C11—H11B	108.2	H21B—C21—H21F	103.8
C10—C12—C5	109.14 (16)	H21D—C21—H21F	109.5
C10—C12—H12A	109.9	H21E—C21—H21F	109.5
C5—C12—H12A	109.9

C1—N2—N3—C2	−0.2 (2)	C2—C3—C9—C10	−177.38 (15)
N3—N2—C1—N1	0.5 (2)	C4—C3—C9—C10	−58.1 (2)
N3—N2—C1—S1	179.88 (13)	C8—C3—C9—C10	59.14 (19)
C2—N1—C1—N2	−0.63 (18)	C3—C9—C10—C12	60.3 (2)
C13—N1—C1—N2	178.41 (15)	C3—C9—C10—C11	−60.2 (2)
C2—N1—C1—S1	179.98 (12)	C6—C7—C11—C10	60.1 (2)
C13—N1—C1—S1	−1.0 (2)	C8—C7—C11—C10	−60.1 (2)
C19—S1—C1—N2	0.81 (19)	C12—C10—C11—C7	−60.1 (2)
C19—S1—C1—N1	−179.90 (14)	C9—C10—C11—C7	60.6 (2)
N2—N3—C2—N1	−0.18 (19)	C11—C10—C12—C5	59.3 (2)
N2—N3—C2—C3	178.35 (15)	C9—C10—C12—C5	−60.9 (2)
C1—N1—C2—N3	0.48 (17)	C6—C5—C12—C10	−59.7 (2)
C13—N1—C2—N3	−178.49 (16)	C4—C5—C12—C10	60.4 (2)
C1—N1—C2—C3	−177.99 (15)	C1—N1—C13—C14	−95.7 (2)
C13—N1—C2—C3	3.0 (3)	C2—N1—C13—C14	83.1 (2)
N3—C2—C3—C4	−7.1 (2)	C1—N1—C13—C18	83.7 (2)
N1—C2—C3—C4	171.18 (16)	C2—N1—C13—C18	−97.5 (2)
N3—C2—C3—C8	−125.84 (17)	C18—C13—C14—C15	2.3 (3)
N1—C2—C3—C8	52.4 (2)	N1—C13—C14—C15	−178.32 (18)
N3—C2—C3—C9	112.38 (18)	C13—C14—C15—C16	−0.3 (3)
N1—C2—C3—C9	−69.4 (2)	C14—C15—C16—C17	−1.4 (4)
C2—C3—C4—C5	179.69 (16)	C15—C16—C17—C18	1.1 (3)
C8—C3—C4—C5	−59.3 (2)	C14—C13—C18—C17	−2.6 (3)
C9—C3—C4—C5	58.3 (2)	N1—C13—C18—C17	178.02 (15)
C3—C4—C5—C12	−60.0 (2)	C16—C17—C18—C13	0.9 (3)
C3—C4—C5—C6	60.8 (2)	C1—S1—C19—C20	179.61 (15)
C12—C5—C6—C7	59.8 (2)	C21—O1B—C20—O1A	44.6 (9)
C4—C5—C6—C7	−60.4 (2)	C21—O1B—C20—C19	127.7 (7)
C5—C6—C7—C11	−59.5 (2)	C21—O1A—C20—O1B	−43.2 (7)
C5—C6—C7—C8	60.5 (2)	C21—O1A—C20—C19	−176.1 (2)
C11—C7—C8—C3	59.56 (19)	S1—C19—C20—O1B	8.4 (12)
C6—C7—C8—C3	−60.43 (19)	S1—C19—C20—O1A	67.0 (2)
C2—C3—C8—C7	177.63 (14)	C20—O1A—C21—O1B	34.6 (6)
C4—C3—C8—C7	58.74 (19)	C20—O1B—C21—O1A	−49.5 (9)
C9—C3—C8—C7	−58.88 (18)

References

Al-Abdullah, E. S., Asiri, H. H., El-Emam, A. A. & Ng, S. W. (2012). Acta Cryst. E68, o531.

Almutairi, M. S., Al-Shehri, M. M., El-Emam, A. A., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o656.

Bruker (2009). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.

El-Emam, A. A., Lahsasni, S., Asiri, H. H., Quah, C. K. & Fun, H.-K. (2012). Acta Cryst. E68, o1356.

Fun, H.-K., Asik, S. I. J., Chandrakantha, B., Isloor, A. M. & Shetty, P. (2011). Acta Cryst. E67, o3422–o3423.

Kadi, A. A., Al-Abdullah, E. S., Shehata, I. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2010). Eur. J. Med. Chem 45, 5006–5011.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst D65, 148–155.

Wang, W., Liu, Q., Xu, C., Wu, W. & Gao, Y. (2011). Acta Cryst. E67, o2236.