Diafenthiuron: 1-tert-butyl-3-(2,6-diisopropyl-4-phen­oxy­phen­yl)thio­urea

Jeon, Y.; Kang, G.; Cho, S.; Kim, T.H.

doi:10.1107/S1600536814014214

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 7| July 2014| Page o807

https://doi.org/10.1107/S1600536814014214

Open

access

Diafenthiuron: 1-tert-butyl-3-(2,6-diisopropyl-4-phenoxyphenyl)thiourea

Youngeun Jeon,^a Gihaeng Kang,^a Seonghwa Cho ^a and Tae Ho Kim ^a ^*

^aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
^*Correspondence e-mail: thkim@gnu.ac.kr

(Received 16 June 2014; accepted 18 June 2014; online 25 June 2014)

The title compound, C₂₃H₃₂N₂OS, is a thiourea-based insecticide. The dihedral angle between the phenyl ring and the diisopropyl benzene ring plane is 73.18 (6)°, while that between the plane of the thiourea group and the diisopropyl benzene ring is 86.00 (5)°. Disorder was modelled for the S atom and the two methyl C atoms of the isopropyl group over two sets of sites with an occupancy ratio of 0.742 (4):0.258 (4). In the crystal, N—H⋯S hydrogen bonds link adjacent molecules, forming R₂²(8) inversion dimers that pack into chains along the b-axis direction.

Keywords: crystal structure.

CCDC reference: 1008806

Related literature

For information on the toxicity and insecticidal properties of the title compound, see: Ishaaya et al. (1993 ). For a related structure, see: Zhang et al. (2010 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₃H₃₂N₂OS
M_r = 384.57
Monoclinic, P 2₁ /c
a = 12.8656 (2) Å
b = 17.9807 (3) Å
c = 10.1671 (2) Å
β = 102.655 (1)°
V = 2294.84 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 173 K
0.50 × 0.30 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.927, T_max = 0.971
39926 measured reflections
5279 independent reflections
4117 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.119
S = 1.03
5279 reflections
281 parameters
19 restraints
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯S1ⁱ	0.88	2.53	3.3739 (15)	160
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2010 ); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1008806

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536814014214/sj5414sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814014214/sj5414Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814014214/sj5414Isup3.cml

checkCIF report

Comment top

Diafenthiuron (systematic name: 1 - t-butyl-3-(2,6-diisopropyl-4-phenoxyphenyl)thiourea), is a type of thiourea insecticide which acts specifically on phytophagous mites, whiteflies and aphids (Ishaaya et al., 1993), and its crystal structure is reported herein. In this compound (Fig. 1), the dihedral angle between the phenyl ring and diisopropyl phenyl ring is 73.18 (6)°. The diheral angle between thiourea group plane and the diisopropyl phenyl is 86.00 (5)°. Disorder was modeled for one S atom (S1) and two C atoms (C16 and C17) of isopropyl group over two sets of sites with an occupancy ratio of 0.742 (4):0.258 (4). All bond lengths and bond angles are normal and comparable to those observed in the crystal structure of a similar compound (Zhang et al., 2010). In the crystal structure (Fig. 2), N2–H2N···S1 hydrogen bonds link adjacent molecules to form R²₂(8) inversion dimers (Bernstein et al., 1995), packed into chains along the b axis direction.

Related literature top

For information on the toxicity and insecticidal properties of the title compound, see: Ishaaya et al. (1993). For a related structure, see: Zhang et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH₂Cl₂ gave single crystals suitable for X-ray analysis.

Structure description top

For information on the toxicity and insecticidal properties of the title compound, see: Ishaaya et al. (1993). For a related structure, see: Zhang et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius. Only atoms of the major disorder components are shown.
	Fig. 2. Crystal packing of the title compound with N—H···S hydrogen bonds shown as dashed lines. H atoms bonded to C atoms have been omitted for clarity. Only atoms of the major disorder components are shown.

1-tert-Butyl-3-(2,6-diisopropyl-4-phenoxyphenyl)thiourea top

Crystal data top

C₂₃H₃₂N₂OS	F(000) = 832
M_r = 384.57	D_x = 1.113 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9944 reflections
a = 12.8656 (2) Å	θ = 2.6–26.5°
b = 17.9807 (3) Å	µ = 0.16 mm⁻¹
c = 10.1671 (2) Å	T = 173 K
β = 102.655 (1)°	Block, colourless
V = 2294.84 (7) Å³	0.50 × 0.30 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	5279 independent reflections
Radiation source: fine-focus sealed tube	4117 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
T_min = 0.927, T_max = 0.971	k = −23→22
39926 measured reflections	l = −13→13

Refinement top

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) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0479P)² + 0.7379P] where P = (F_o² + 2F_c²)/3
5279 reflections	(Δ/σ)_max = 0.001
281 parameters	Δρ_max = 0.25 e Å⁻³
19 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₃H₃₂N₂OS	V = 2294.84 (7) Å³
M_r = 384.57	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.8656 (2) Å	µ = 0.16 mm⁻¹
b = 17.9807 (3) Å	T = 173 K
c = 10.1671 (2) Å	0.50 × 0.30 × 0.19 mm
β = 102.655 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5279 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4117 reflections with I > 2σ(I)
T_min = 0.927, T_max = 0.971	R_int = 0.034
39926 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	19 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	Δρ_max = 0.25 e Å⁻³
5279 reflections	Δρ_min = −0.23 e Å⁻³
281 parameters

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. 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.56002 (13)	1.08803 (6)	0.37193 (18)	0.0552 (3)	0.742 (4)
S1'	0.5179 (4)	1.0709 (2)	0.3222 (4)	0.0580 (10)	0.258 (4)
O1	0.85776 (9)	0.69041 (6)	0.51145 (12)	0.0536 (3)
N1	0.69688 (10)	1.00011 (7)	0.27909 (12)	0.0403 (3)
H1N	0.7318	0.9577	0.2897	0.048*
N2	0.61785 (9)	0.95071 (6)	0.43823 (12)	0.0369 (3)
H2N	0.5680	0.9532	0.4851	0.044*
C1	0.72543 (12)	1.05027 (8)	0.17740 (15)	0.0419 (3)
C2	0.80932 (13)	1.00766 (9)	0.12308 (17)	0.0482 (4)
H2A	0.8690	0.9951	0.1976	0.072*
H2B	0.8350	1.0386	0.0575	0.072*
H2C	0.7779	0.9619	0.0792	0.072*
C3	0.62948 (15)	1.06426 (14)	0.0633 (2)	0.0745 (6)
H3A	0.6029	1.0168	0.0218	0.112*
H3B	0.6503	1.0963	−0.0045	0.112*
H3C	0.5734	1.0887	0.0989	0.112*
C4	0.77343 (18)	1.12213 (10)	0.2428 (2)	0.0714 (6)
H4A	0.7195	1.1494	0.2781	0.107*
H4B	0.7977	1.1527	0.1757	0.107*
H4C	0.8340	1.1105	0.3168	0.107*
C5	0.62684 (12)	1.00853 (8)	0.35760 (15)	0.0426 (4)
C6	0.68322 (10)	0.88509 (7)	0.45404 (13)	0.0315 (3)
C7	0.65135 (10)	0.82379 (7)	0.37036 (13)	0.0328 (3)
C8	0.71330 (11)	0.75966 (8)	0.39362 (14)	0.0358 (3)
H8	0.6936	0.7172	0.3382	0.043*
C9	0.80322 (11)	0.75739 (7)	0.49667 (15)	0.0362 (3)
C10	0.83576 (11)	0.81891 (7)	0.57626 (15)	0.0364 (3)
H10	0.8988	0.8168	0.6452	0.044*
C11	0.77584 (11)	0.88429 (7)	0.55526 (14)	0.0344 (3)
C12	0.55233 (12)	0.82694 (9)	0.25731 (15)	0.0431 (4)
H12	0.5328	0.8805	0.2404	0.052*
C13	0.45888 (14)	0.78824 (13)	0.2968 (2)	0.0728 (6)
H13A	0.4768	0.7359	0.3174	0.109*
H13B	0.3963	0.7912	0.2221	0.109*
H13C	0.4432	0.8125	0.3765	0.109*
C14	0.57182 (19)	0.79454 (14)	0.12726 (19)	0.0823 (7)
H14A	0.6319	0.8203	0.1025	0.123*
H14B	0.5079	0.8009	0.0554	0.123*
H14C	0.5882	0.7414	0.1398	0.123*
C15	0.81007 (14)	0.95275 (8)	0.64085 (18)	0.0516 (4)
H15A	0.7900	0.9976	0.5826	0.062*	0.742 (4)
H15B	0.7556	0.9932	0.6208	0.062*	0.258 (4)
C16	0.7452 (3)	0.95541 (14)	0.7595 (2)	0.0611 (8)	0.742 (4)
H16A	0.7684	0.9144	0.8225	0.092*	0.742 (4)
H16B	0.6688	0.9506	0.7205	0.092*	0.742 (4)
H16C	0.7590	1.0029	0.8076	0.092*	0.742 (4)
C17	0.9244 (2)	0.95782 (14)	0.7033 (4)	0.0769 (12)	0.742 (4)
H17A	0.9389	1.0051	0.7519	0.115*	0.742 (4)
H17B	0.9658	0.9553	0.6332	0.115*	0.742 (4)
H17C	0.9447	0.9165	0.7665	0.115*	0.742 (4)
C16'	0.8471 (10)	0.9434 (5)	0.7755 (9)	0.090 (3)	0.258 (4)
H16D	0.9083	0.9096	0.7912	0.136*	0.258 (4)
H16E	0.7906	0.9222	0.8149	0.136*	0.258 (4)
H16F	0.8690	0.9916	0.8174	0.136*	0.258 (4)
C17'	0.9296 (6)	0.9760 (4)	0.5818 (9)	0.062 (2)	0.258 (4)
H17D	0.9606	1.0219	0.6254	0.093*	0.258 (4)
H17E	0.9114	0.9830	0.4839	0.093*	0.258 (4)
H17F	0.9814	0.9354	0.6043	0.093*	0.258 (4)
C18	0.95008 (11)	0.68370 (7)	0.61207 (16)	0.0391 (3)
C19	0.94465 (13)	0.67609 (9)	0.74495 (17)	0.0478 (4)
H19	0.8778	0.6774	0.7702	0.057*
C20	1.03768 (15)	0.66652 (10)	0.84113 (18)	0.0566 (4)
H20	1.0349	0.6615	0.9333	0.068*
C21	1.13450 (14)	0.66421 (9)	0.8046 (2)	0.0599 (5)
H21	1.1983	0.6581	0.8713	0.072*
C22	1.13828 (13)	0.67082 (10)	0.6715 (2)	0.0610 (5)
H22	1.2050	0.6687	0.6460	0.073*
C23	1.04608 (13)	0.68058 (9)	0.57400 (18)	0.0494 (4)
H23	1.0490	0.6851	0.4818	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0692 (7)	0.0346 (4)	0.0751 (8)	0.0234 (4)	0.0446 (6)	0.0193 (4)
S1'	0.074 (2)	0.0464 (16)	0.0643 (19)	0.0307 (14)	0.0377 (16)	0.0220 (13)
O1	0.0517 (6)	0.0351 (6)	0.0629 (7)	0.0185 (5)	−0.0116 (5)	−0.0140 (5)
N1	0.0508 (7)	0.0319 (6)	0.0442 (7)	0.0112 (5)	0.0236 (6)	0.0083 (5)
N2	0.0453 (6)	0.0309 (6)	0.0405 (7)	0.0131 (5)	0.0223 (5)	0.0078 (5)
C1	0.0491 (8)	0.0382 (8)	0.0434 (8)	0.0027 (6)	0.0212 (7)	0.0101 (6)
C2	0.0540 (9)	0.0492 (9)	0.0481 (9)	−0.0023 (7)	0.0256 (8)	0.0016 (7)
C3	0.0602 (11)	0.1049 (17)	0.0611 (12)	0.0191 (11)	0.0191 (10)	0.0378 (12)
C4	0.0924 (14)	0.0408 (10)	0.0954 (15)	−0.0085 (9)	0.0518 (13)	−0.0068 (10)
C5	0.0529 (8)	0.0347 (7)	0.0465 (8)	0.0136 (6)	0.0244 (7)	0.0094 (6)
C6	0.0362 (7)	0.0275 (6)	0.0344 (7)	0.0069 (5)	0.0155 (6)	0.0044 (5)
C7	0.0336 (6)	0.0339 (7)	0.0327 (7)	0.0048 (5)	0.0109 (6)	0.0033 (6)
C8	0.0388 (7)	0.0316 (7)	0.0365 (7)	0.0035 (5)	0.0069 (6)	−0.0048 (6)
C9	0.0371 (7)	0.0282 (7)	0.0433 (8)	0.0073 (5)	0.0087 (6)	−0.0024 (6)
C10	0.0355 (7)	0.0296 (7)	0.0420 (8)	0.0021 (5)	0.0040 (6)	−0.0006 (6)
C11	0.0398 (7)	0.0260 (6)	0.0386 (7)	0.0003 (5)	0.0113 (6)	0.0001 (6)
C12	0.0435 (8)	0.0433 (8)	0.0394 (8)	0.0100 (6)	0.0025 (6)	0.0031 (7)
C13	0.0411 (9)	0.0935 (16)	0.0742 (14)	−0.0062 (9)	−0.0082 (9)	0.0153 (12)
C14	0.0935 (15)	0.1036 (17)	0.0394 (10)	0.0422 (13)	−0.0080 (10)	−0.0099 (11)
C15	0.0663 (10)	0.0259 (7)	0.0555 (10)	0.0003 (7)	−0.0021 (8)	−0.0046 (7)
C16	0.100 (2)	0.0433 (13)	0.0420 (13)	−0.0090 (13)	0.0198 (14)	−0.0127 (10)
C17	0.0589 (15)	0.0409 (14)	0.118 (3)	−0.0077 (11)	−0.0098 (17)	−0.0191 (16)
C16'	0.162 (10)	0.055 (5)	0.056 (5)	−0.022 (6)	0.029 (6)	−0.020 (4)
C17'	0.061 (4)	0.047 (4)	0.075 (5)	−0.018 (3)	0.006 (4)	−0.019 (4)
C18	0.0390 (7)	0.0250 (6)	0.0501 (9)	0.0080 (5)	0.0025 (6)	−0.0045 (6)
C19	0.0459 (8)	0.0450 (9)	0.0539 (10)	0.0050 (7)	0.0140 (7)	−0.0062 (7)
C20	0.0714 (12)	0.0469 (10)	0.0464 (10)	0.0068 (8)	0.0018 (9)	−0.0007 (8)
C21	0.0484 (9)	0.0441 (9)	0.0749 (13)	0.0078 (7)	−0.0133 (9)	−0.0070 (9)
C22	0.0383 (8)	0.0556 (11)	0.0893 (15)	0.0021 (7)	0.0145 (9)	−0.0087 (10)
C23	0.0524 (9)	0.0428 (9)	0.0558 (10)	0.0033 (7)	0.0176 (8)	−0.0010 (7)

Geometric parameters (Å, º) top

S1—C5	1.6906 (17)	C13—H13A	0.9800
S1'—C5	1.769 (3)	C13—H13B	0.9800
O1—C9	1.3853 (16)	C13—H13C	0.9800
O1—C18	1.3927 (17)	C14—H14A	0.9800
N1—C5	1.3370 (18)	C14—H14B	0.9800
N1—C1	1.4776 (18)	C14—H14C	0.9800
N1—H1N	0.8800	C15—C16'	1.357 (9)
N2—C5	1.3446 (18)	C15—C17	1.472 (3)
N2—C6	1.4373 (16)	C15—C16	1.610 (3)
N2—H2N	0.8800	C15—C17'	1.818 (8)
C1—C3	1.519 (2)	C15—H15A	1.0000
C1—C4	1.521 (2)	C15—H15B	1.0000
C1—C2	1.523 (2)	C16—H16A	0.9800
C2—H2A	0.9800	C16—H16B	0.9800
C2—H2B	0.9800	C16—H16C	0.9800
C2—H2C	0.9800	C17—H17A	0.9800
C3—H3A	0.9800	C17—H17B	0.9800
C3—H3B	0.9800	C17—H17C	0.9800
C3—H3C	0.9800	C16'—H16D	0.9800
C4—H4A	0.9800	C16'—H16E	0.9800
C4—H4B	0.9800	C16'—H16F	0.9800
C4—H4C	0.9800	C17'—H17D	0.9800
C6—C11	1.3935 (19)	C17'—H17E	0.9800
C6—C7	1.3979 (19)	C17'—H17F	0.9800
C7—C8	1.3923 (18)	C18—C23	1.374 (2)
C7—C12	1.5184 (19)	C18—C19	1.375 (2)
C8—C9	1.3809 (19)	C19—C20	1.380 (2)
C8—H8	0.9500	C19—H19	0.9500
C9—C10	1.3802 (19)	C20—C21	1.376 (3)
C10—C11	1.3963 (18)	C20—H20	0.9500
C10—H10	0.9500	C21—C22	1.370 (3)
C11—C15	1.516 (2)	C21—H21	0.9500
C12—C14	1.515 (2)	C22—C23	1.380 (2)
C12—C13	1.518 (2)	C22—H22	0.9500
C12—H12	1.0000	C23—H23	0.9500

C9—O1—C18	119.03 (11)	H13A—C13—H13C	109.5
C5—N1—C1	130.69 (12)	H13B—C13—H13C	109.5
C5—N1—H1N	114.7	C12—C14—H14A	109.5
C1—N1—H1N	114.7	C12—C14—H14B	109.5
C5—N2—C6	125.21 (11)	H14A—C14—H14B	109.5
C5—N2—H2N	117.4	C12—C14—H14C	109.5
C6—N2—H2N	117.4	H14A—C14—H14C	109.5
N1—C1—C3	110.53 (13)	H14B—C14—H14C	109.5
N1—C1—C4	110.60 (14)	C16'—C15—C17	58.4 (5)
C3—C1—C4	112.18 (16)	C16'—C15—C11	118.1 (4)
N1—C1—C2	104.55 (12)	C17—C15—C11	115.80 (16)
C3—C1—C2	109.17 (14)	C16'—C15—C16	51.2 (5)
C4—C1—C2	109.51 (14)	C17—C15—C16	107.9 (2)
C1—C2—H2A	109.5	C11—C15—C16	108.72 (14)
C1—C2—H2B	109.5	C16'—C15—C17'	103.1 (5)
H2A—C2—H2B	109.5	C17—C15—C17'	44.8 (3)
C1—C2—H2C	109.5	C11—C15—C17'	99.0 (3)
H2A—C2—H2C	109.5	C16—C15—C17'	148.8 (3)
H2B—C2—H2C	109.5	C16'—C15—H15A	133.2
C1—C3—H3A	109.5	C17—C15—H15A	108.1
C1—C3—H3B	109.5	C11—C15—H15A	108.1
H3A—C3—H3B	109.5	C16—C15—H15A	108.1
C1—C3—H3C	109.5	C17'—C15—H15A	75.4
H3A—C3—H3C	109.5	C16'—C15—H15B	111.8
H3B—C3—H3C	109.5	C17—C15—H15B	129.2
C1—C4—H4A	109.5	C11—C15—H15B	111.8
C1—C4—H4B	109.5	C16—C15—H15B	71.1
H4A—C4—H4B	109.5	C17'—C15—H15B	111.8
C1—C4—H4C	109.5	H15A—C15—H15B	38.1
H4A—C4—H4C	109.5	C15—C16—H16A	109.5
H4B—C4—H4C	109.5	C15—C16—H16B	109.5
N1—C5—N2	115.83 (12)	C15—C16—H16C	109.5
N1—C5—S1	124.69 (11)	C15—C17—H17A	109.5
N2—C5—S1	119.21 (11)	C15—C17—H17B	109.5
N1—C5—S1'	123.91 (15)	C15—C17—H17C	109.5
N2—C5—S1'	116.37 (16)	C15—C16'—H16D	109.5
S1—C5—S1'	24.00 (14)	C15—C16'—H16E	109.5
C11—C6—C7	122.05 (11)	H16D—C16'—H16E	109.5
C11—C6—N2	118.41 (12)	C15—C16'—H16F	109.5
C7—C6—N2	119.52 (12)	H16D—C16'—H16F	109.5
C8—C7—C6	117.97 (12)	H16E—C16'—H16F	109.5
C8—C7—C12	120.90 (12)	C15—C17'—H17D	109.5
C6—C7—C12	121.13 (12)	C15—C17'—H17E	109.5
C9—C8—C7	120.44 (13)	H17D—C17'—H17E	109.5
C9—C8—H8	119.8	C15—C17'—H17F	109.5
C7—C8—H8	119.8	H17D—C17'—H17F	109.5
C10—C9—C8	121.15 (12)	H17E—C17'—H17F	109.5
C10—C9—O1	123.49 (12)	C23—C18—C19	121.01 (14)
C8—C9—O1	115.35 (12)	C23—C18—O1	118.12 (15)
C9—C10—C11	119.91 (13)	C19—C18—O1	120.77 (14)
C9—C10—H10	120.0	C18—C19—C20	119.05 (16)
C11—C10—H10	120.0	C18—C19—H19	120.5
C6—C11—C10	118.41 (12)	C20—C19—H19	120.5
C6—C11—C15	120.62 (12)	C21—C20—C19	120.54 (17)
C10—C11—C15	120.97 (13)	C21—C20—H20	119.7
C14—C12—C13	110.29 (18)	C19—C20—H20	119.7
C14—C12—C7	111.99 (13)	C22—C21—C20	119.62 (16)
C13—C12—C7	111.38 (13)	C22—C21—H21	120.2
C14—C12—H12	107.7	C20—C21—H21	120.2
C13—C12—H12	107.7	C21—C22—C23	120.63 (17)
C7—C12—H12	107.7	C21—C22—H22	119.7
C12—C13—H13A	109.5	C23—C22—H22	119.7
C12—C13—H13B	109.5	C18—C23—C22	119.15 (17)
H13A—C13—H13B	109.5	C18—C23—H23	120.4
C12—C13—H13C	109.5	C22—C23—H23	120.4

C5—N1—C1—C3	−62.1 (2)	N2—C6—C11—C15	−3.65 (19)
C5—N1—C1—C4	62.8 (2)	C9—C10—C11—C6	0.6 (2)
C5—N1—C1—C2	−179.42 (16)	C9—C10—C11—C15	−179.73 (14)
C1—N1—C5—N2	178.36 (15)	C8—C7—C12—C14	−45.2 (2)
C1—N1—C5—S1	−7.7 (3)	C6—C7—C12—C14	134.69 (17)
C1—N1—C5—S1'	21.4 (3)	C8—C7—C12—C13	78.84 (19)
C6—N2—C5—N1	5.7 (2)	C6—C7—C12—C13	−101.27 (17)
C6—N2—C5—S1	−168.61 (14)	C6—C11—C15—C16'	137.5 (6)
C6—N2—C5—S1'	164.4 (2)	C10—C11—C15—C16'	−42.1 (6)
C5—N2—C6—C11	90.80 (18)	C6—C11—C15—C17	−156.1 (2)
C5—N2—C6—C7	−90.60 (18)	C10—C11—C15—C17	24.3 (3)
C11—C6—C7—C8	2.2 (2)	C6—C11—C15—C16	82.22 (19)
N2—C6—C7—C8	−176.32 (12)	C10—C11—C15—C16	−97.40 (19)
C11—C6—C7—C12	−177.67 (13)	C6—C11—C15—C17'	−112.3 (3)
N2—C6—C7—C12	3.78 (19)	C10—C11—C15—C17'	68.1 (3)
C6—C7—C8—C9	0.1 (2)	C9—O1—C18—C23	−108.24 (16)
C12—C7—C8—C9	179.97 (13)	C9—O1—C18—C19	75.44 (18)
C7—C8—C9—C10	−2.0 (2)	C23—C18—C19—C20	1.2 (2)
C7—C8—C9—O1	179.17 (13)	O1—C18—C19—C20	177.37 (14)
C18—O1—C9—C10	0.5 (2)	C18—C19—C20—C21	−0.3 (2)
C18—O1—C9—C8	179.27 (14)	C19—C20—C21—C22	−0.6 (3)
C8—C9—C10—C11	1.6 (2)	C20—C21—C22—C23	0.7 (3)
O1—C9—C10—C11	−179.64 (14)	C19—C18—C23—C22	−1.0 (2)
C7—C6—C11—C10	−2.6 (2)	O1—C18—C23—C22	−177.33 (14)
N2—C6—C11—C10	175.98 (12)	C21—C22—C23—C18	0.1 (3)
C7—C6—C11—C15	177.79 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···S1ⁱ	0.88	2.53	3.3739 (15)	160

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···S1ⁱ	0.88	2.53	3.3739 (15)	160

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2012R1A1B3003337).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ishaaya, I., Mendelson, Z. & Horowitz, A. R. (1993). Phytoparasitica, 21, 199–204. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, X., Huang, J., Song, J., Xu, K. & Ban, Q. (2010). Chin. J. Chem. 28, 1902–1906. Web of Science CrossRef CAS Google Scholar