Crystal structure of oxam­yl

Kwon, E.; Park, K.-M.; Park, H.; Kim, T.H.

doi:10.1107/S2056989016018168

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 72| Part 12| December 2016| Pages 1816-1818

https://doi.org/10.1107/S2056989016018168

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Crystal structure of oxamyl

Eunjin Kwon,^a Ki-Min Park,^a ^* Hyunjin Park ^a and Tae Ho Kim ^a ^*

^aDepartment of Chemistry (BK21 plus) and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 52828, Republic of Korea
^*Correspondence e-mail: kmpark@gnu.ac.kr, thkim@gnu.ac.kr

Edited by J. Simpson, University of Otago, New Zealand (Received 8 November 2016; accepted 12 November 2016; online 18 November 2016)

The title compound, C₇H₁₃N₃O₃S [systematic name: (Z)-methyl 2-dimethylamino-N-(methylcarbamoyloxy)-2-oxoethanimidothioate], is an oxime carbamate acaride, insecticide and nematicide. The asymmetric unit comprises two independent molecules, A and B. The dihedral angles between the mean planes [r.m.s. deviations = 0.0017 (A) and 0.0016 Å (B)] of the acetamide and oxyimino groups are 88.80 (8)° for A and 87.05 (8)° for B. In the crystal, N/C—H⋯O hydrogen bonds link adjacent molecules, forming chains along the a axis. The chains are further linked by C—H⋯O hydrogen bonds, resulting in a three-dimensional network with alternating rows of A and B molecules in the bc plane stacked along the a-axis direction. The structure was refined as an inversion twin with a final BASF parameter of 0.16 (9).

Keywords: crystal structure; acaricide; insecticide; nematicide; oxamyl.

CCDC reference: 1516996

1. Chemical context

Oxamyl [(N,N-dimethyl-2-methylcarbamoyloximino-2-(dimethylsulfanyl)acetamide] is a carbamate compound used in a wide range of agricultural situations. It is systemic and active as an insecticide or a nematicide. It is used for the control of nematodes in vegetables, bananas, pineapple, peanuts, cotton, soya beans, tobacco, potatoes, sugar beet, and other crops. It is also used in India for controlling the growth of nematodes on vegetable crops (Mohammad et al., 2015 ; Agarwal et al., 2016 ). In addition, oxamyl was classified by the World Health Organization (WHO) as highly hazardous (class IB) (Al-Dabbas et al., 2014 ). Oxamyl can be integrated with horse manure, sesame-oil-cake, or Bacillus thuringiensis to improve eggplant growth response and reduce development of the nematode Meloidogyne incognita (Osman et al., 2009 ). Also, oxamyl has a very high water solubility (280 g/L at 298 K) and low sorption solubility affinity to soils. As a result of these properties, oxamyl easily migrates into the water compartment (Mazellier et al., 2010 ). Herein, we report the molecular and crystal structure of oxamyl.

2. Structural commentary

The asymmetric unit of oxamyl comprises two independent molecules, A and B (Fig. 1). The compound consists of carbamate, acetamide, methylthio and oxyimino functional groups. The dihedral angles between the mean planes [r.m.s. deviations = 0.0017 (A) and 0.0016 Å (B)] of the acetamide and oxyimino groups are 88.80 (8) for A and 87.05 (8)° for B. All bond lengths and bond angles are normal and comparable to those observed in methomyl [systematic name: (E)-methyl N-(methylcarbamoyl)oxyethanimidothioate] which adopts similar crystal structure (Takusagawa & Jacobson, 1977 ).

Figure 1
The asymmetric unit of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

3. Supramolecular features

The crystal structure is stabilized by several N—H⋯O and C—H⋯O hydrogen bonds (Table 1). Adjacent A molecules form intermolecular N1—H1N⋯O1 hydrogen bonds. In addition, C6—H6B⋯O2 and C7—H7B⋯O1 hydrogen bonds between the carbamate and dimethylamine groups generate R₂²(8) inversion dimers. These contacts link the A molecules into double chains along the a axis. A closely similar situation obtains for the B molecules, with intermolecular N4—H4N⋯O4 hydrogen bonds together with C13—H13B⋯O4 and C14—H14B⋯O5 R₂²(8) inversion dimers also forming a double chain, this time solely of B molecules, parallel to the one described previously, again along the a axis, Fig. 2. The A and B double chains are further linked by C4—H4B⋯O6 and C11—H11B⋯O3 contacts, Table 1, to give a three-dimensional network with alternating rows of A and B molecules in the bc plane stacked along the a-axis direction, Fig. 3.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.88	2.13	2.871 (3)	142
N4—H4N⋯O4ⁱⁱ	0.88	2.04	2.794 (3)	142
C4—H4B⋯O6ⁱⁱⁱ	0.98	2.54	3.075 (4)	114
C6—H6B⋯O2^iv	0.98	2.60	3.518 (4)	156
C7—H7B⋯O1^iv	0.98	2.52	3.431 (4)	155
C11—H11B⋯O3^v	0.98	2.53	3.042 (4)	113
C13—H13B⋯O4^iv	0.98	2.53	3.440 (4)	155
C14—H14B⋯O5^iv	0.98	2.59	3.554 (4)	168
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y, z]$ ; (ii) $[x-{\script{1\over 2}}, -y+1, z]$ ; (iii) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (iv) x-1, y, z; (v) $[-x+1, -y, z-{\script{1\over 2}}]$ .

Figure 2
The double chains formed through intermolecular N—H⋯O (black dashed lines) and C—H⋯O (sky-blue dashed lines) hydrogen bonds. The A and B molecules are shown in green and yellow, respectively. H atoms not involved in intermolecular interactions have been omitted for clarity.

Figure 3
The three-dimensional network made up of molecules A (green) and B (yellow). Black dashed lines represent intermolecular N—H⋯O hydrogen bonds. The C—H⋯O hydrogen bonds are shown as sky-blue (between each molecule A or B) and red (between molecules A and B) dashed lines, respectively. H atoms not involved in intermolecular interactions have been omitted for clarity.

4. Synthesis and crystallization

The title compound was purchased from Dr Ehrenstorfer GmbH. Slow evaporation of its solution in CH₃OH gave single crystals suitable for X-ray analysis.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All C-bound H atoms were positioned geometrically [with d(N—H) = 0.88 Å, U_iso = 1.2U_eq(C) for N—H group, U_iso = 1.5U_eq(C) for methyl group, d(C—H) = 0.98 Å]. The crystal studied was an inversion twin with a 0.84 (9):0.16 (9) domain ratio.

Table 2
Experimental details

Crystal data
Chemical formula	C₇H₁₃N₃O₃S
M_r	219.26
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	173
a, b, c (Å)	8.3367 (4), 10.7752 (5), 24.1016 (12)
V (Å³)	2165.04 (18)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.29
Crystal size (mm)	0.50 × 0.14 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2014 )
T_min, T_max	0.665, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	19300, 5238, 4655
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.090, 1.04
No. of reflections	5238
No. of parameters	262
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.23
Absolute structure	Refined as an inversion twin
Absolute structure parameter	0.16 (9)
Computer programs: APEX2 and SAINT (Bruker, 2014), SHELXS97 and SHELXTL (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), DIAMOND (Brandenburg, 2010 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1516996

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989016018168/sj5514sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016018168/sj5514Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989016018168/sj5514Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

(Z)-[(Dimethylcarbamoyl)(methylsulfanyl)methylidene]amino N-methylcarbamate top

Crystal data top

C₇H₁₃N₃O₃S	D_x = 1.345 Mg m⁻³
M_r = 219.26	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca2₁	Cell parameters from 6335 reflections
a = 8.3367 (4) Å	θ = 2.5–27.8°
b = 10.7752 (5) Å	µ = 0.29 mm⁻¹
c = 24.1016 (12) Å	T = 173 K
V = 2165.04 (18) Å³	Plate, colourless
Z = 8	0.50 × 0.14 × 0.11 mm
F(000) = 928

Data collection top

Bruker APEXII CCD diffractometer	4655 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.035
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θ_max = 28.3°, θ_min = 1.7°
T_min = 0.665, T_max = 0.746	h = −11→11
19300 measured reflections	k = −14→14
5238 independent reflections	l = −32→31

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.0432P)² + 0.3998P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.090	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.21 e Å⁻³
5238 reflections	Δρ_min = −0.23 e Å⁻³
262 parameters	Absolute structure: Refined as an inversion twin
1 restraint	Absolute structure parameter: 0.16 (9)

Special details top

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. 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	0.55678 (10)	0.32807 (7)	0.87717 (3)	0.0373 (2)
S2	0.97239 (10)	0.16264 (7)	0.54545 (3)	0.0376 (2)
O1	0.8636 (3)	0.13823 (18)	0.74085 (9)	0.0308 (5)
O2	0.6589 (2)	0.17413 (17)	0.79576 (8)	0.0270 (4)
O3	0.2966 (3)	0.0966 (2)	0.91570 (10)	0.0431 (6)
O4	1.2851 (3)	0.36802 (18)	0.67471 (9)	0.0307 (5)
O5	1.0771 (3)	0.32628 (17)	0.62210 (9)	0.0282 (5)
O6	0.7167 (3)	0.3997 (2)	0.50123 (10)	0.0403 (6)
N1	0.6479 (3)	0.0112 (2)	0.73350 (10)	0.0290 (5)
H1N	0.5497	−0.0037	0.7451	0.035*
N2	0.5009 (3)	0.1328 (2)	0.81132 (10)	0.0272 (5)
N3	0.1571 (3)	0.2143 (2)	0.85463 (10)	0.0303 (6)
N4	1.0729 (3)	0.4993 (2)	0.67852 (10)	0.0287 (5)
H4N	0.9764	0.5151	0.6655	0.034*
N5	0.9217 (3)	0.3683 (2)	0.60490 (10)	0.0261 (5)
N6	0.5764 (3)	0.2808 (2)	0.56227 (10)	0.0291 (6)
C1	0.7188 (4)	−0.0672 (3)	0.69115 (14)	0.0348 (7)
H1A	0.7844	−0.0164	0.6662	0.052*
H1B	0.6335	−0.1079	0.6699	0.052*
H1C	0.7863	−0.1304	0.7088	0.052*
C2	0.7298 (4)	0.1050 (2)	0.75477 (12)	0.0244 (6)
C3	0.4493 (4)	0.2044 (3)	0.84969 (11)	0.0242 (6)
C4	0.4197 (5)	0.3917 (4)	0.92805 (16)	0.0481 (10)
H4A	0.3255	0.4260	0.9091	0.072*
H4B	0.4736	0.4576	0.9490	0.072*
H4C	0.3858	0.3259	0.9536	0.072*
C5	0.2909 (3)	0.1659 (3)	0.87589 (13)	0.0271 (6)
C6	0.0028 (4)	0.1835 (4)	0.88024 (16)	0.0398 (8)
H6A	0.0171	0.1138	0.9059	0.060*
H6B	−0.0742	0.1604	0.8513	0.060*
H6C	−0.0376	0.2557	0.9007	0.060*
C7	0.1526 (4)	0.3046 (3)	0.80973 (14)	0.0372 (7)
H7A	0.1188	0.3853	0.8243	0.056*
H7B	0.0764	0.2770	0.7813	0.056*
H7C	0.2597	0.3122	0.7933	0.056*
C8	1.1426 (4)	0.5816 (3)	0.71943 (13)	0.0348 (7)
H8A	1.1834	0.5326	0.7507	0.052*
H8B	1.0607	0.6396	0.7327	0.052*
H8C	1.2311	0.6281	0.7026	0.052*
C9	1.1516 (4)	0.4014 (2)	0.66055 (11)	0.0242 (6)
C10	0.8681 (4)	0.2936 (2)	0.56845 (11)	0.0240 (6)
C11	0.8379 (5)	0.0982 (3)	0.49430 (15)	0.0462 (9)
H11A	0.7431	0.0641	0.5129	0.069*
H11B	0.8928	0.0320	0.4739	0.069*
H11C	0.8049	0.1635	0.4684	0.069*
C12	0.7109 (4)	0.3295 (2)	0.54159 (13)	0.0267 (6)
C13	0.5720 (4)	0.1938 (3)	0.60790 (14)	0.0366 (7)
H13A	0.5364	0.1126	0.5944	0.055*
H13B	0.4972	0.2238	0.6363	0.055*
H13C	0.6795	0.1861	0.6240	0.055*
C14	0.4231 (4)	0.3106 (4)	0.53622 (15)	0.0420 (8)
H14A	0.4301	0.3922	0.5184	0.063*
H14B	0.3386	0.3120	0.5645	0.063*
H14C	0.3976	0.2476	0.5083	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0356 (4)	0.0368 (4)	0.0393 (4)	−0.0072 (3)	0.0091 (4)	−0.0137 (4)
S2	0.0352 (4)	0.0330 (4)	0.0447 (5)	0.0083 (3)	−0.0103 (4)	−0.0155 (4)
O1	0.0210 (10)	0.0284 (10)	0.0428 (12)	−0.0018 (9)	0.0060 (9)	−0.0027 (9)
O2	0.0212 (10)	0.0271 (10)	0.0325 (11)	−0.0017 (8)	0.0047 (9)	−0.0055 (8)
O3	0.0392 (14)	0.0478 (13)	0.0423 (13)	0.0036 (11)	0.0085 (11)	0.0196 (11)
O4	0.0246 (11)	0.0275 (10)	0.0401 (12)	−0.0007 (9)	−0.0058 (10)	0.0029 (9)
O5	0.0211 (10)	0.0257 (10)	0.0379 (12)	0.0023 (8)	−0.0061 (9)	−0.0072 (9)
O6	0.0342 (13)	0.0476 (12)	0.0393 (12)	0.0008 (11)	−0.0035 (10)	0.0185 (11)
N1	0.0227 (12)	0.0282 (11)	0.0360 (13)	−0.0003 (10)	0.0061 (10)	−0.0077 (10)
N2	0.0233 (13)	0.0265 (12)	0.0318 (13)	−0.0011 (11)	0.0054 (11)	0.0001 (10)
N3	0.0269 (13)	0.0338 (13)	0.0303 (13)	−0.0022 (11)	0.0031 (11)	0.0026 (10)
N4	0.0259 (12)	0.0261 (11)	0.0343 (12)	0.0015 (10)	−0.0078 (10)	−0.0065 (10)
N5	0.0204 (12)	0.0268 (11)	0.0310 (13)	0.0025 (10)	−0.0039 (10)	−0.0028 (10)
N6	0.0242 (13)	0.0338 (12)	0.0293 (13)	−0.0019 (10)	−0.0014 (10)	−0.0019 (10)
C1	0.0351 (17)	0.0295 (15)	0.0398 (17)	0.0018 (13)	0.0061 (14)	−0.0103 (12)
C2	0.0232 (15)	0.0219 (12)	0.0281 (14)	0.0057 (11)	0.0031 (12)	0.0023 (11)
C3	0.0265 (15)	0.0235 (13)	0.0225 (13)	0.0020 (12)	0.0005 (11)	0.0021 (11)
C4	0.047 (2)	0.052 (2)	0.045 (2)	0.0018 (18)	0.0094 (18)	−0.0225 (17)
C5	0.0276 (15)	0.0256 (13)	0.0282 (14)	−0.0014 (11)	0.0051 (13)	−0.0014 (12)
C6	0.0255 (15)	0.055 (2)	0.0388 (17)	−0.0041 (15)	0.0053 (16)	−0.0005 (16)
C7	0.0364 (18)	0.0385 (17)	0.0368 (17)	0.0014 (14)	−0.0027 (15)	0.0072 (14)
C8	0.0439 (19)	0.0293 (14)	0.0311 (15)	−0.0019 (14)	−0.0055 (14)	−0.0050 (12)
C9	0.0236 (14)	0.0225 (13)	0.0266 (13)	−0.0036 (11)	−0.0002 (12)	0.0020 (11)
C10	0.0262 (15)	0.0210 (12)	0.0249 (13)	0.0001 (12)	0.0008 (11)	0.0001 (11)
C11	0.048 (2)	0.0461 (19)	0.045 (2)	0.0003 (17)	−0.0105 (17)	−0.0213 (16)
C12	0.0277 (15)	0.0253 (12)	0.0271 (14)	0.0005 (11)	−0.0025 (13)	−0.0024 (12)
C13	0.0346 (18)	0.0368 (16)	0.0383 (18)	−0.0050 (14)	0.0050 (14)	0.0040 (14)
C14	0.0240 (15)	0.057 (2)	0.045 (2)	0.0030 (15)	−0.0041 (15)	0.0001 (16)

Geometric parameters (Å, º) top

S1—C3	1.737 (3)	C1—H1A	0.9800
S1—C4	1.811 (3)	C1—H1B	0.9800
S2—C10	1.748 (3)	C1—H1C	0.9800
S2—C11	1.805 (3)	C3—C5	1.521 (4)
O1—C2	1.218 (4)	C4—H4A	0.9800
O2—C2	1.371 (3)	C4—H4B	0.9800
O2—N2	1.440 (3)	C4—H4C	0.9800
O3—C5	1.216 (4)	C6—H6A	0.9800
O4—C9	1.219 (4)	C6—H6B	0.9800
O5—C9	1.378 (3)	C6—H6C	0.9800
O5—N5	1.434 (3)	C7—H7A	0.9800
O6—C12	1.233 (4)	C7—H7B	0.9800
N1—C2	1.323 (4)	C7—H7C	0.9800
N1—C1	1.451 (4)	C8—H8A	0.9800
N1—H1N	0.8800	C8—H8B	0.9800
N2—C3	1.279 (4)	C8—H8C	0.9800
N3—C5	1.334 (4)	C10—C12	1.512 (4)
N3—C7	1.455 (4)	C11—H11A	0.9800
N3—C6	1.464 (4)	C11—H11B	0.9800
N4—C9	1.315 (4)	C11—H11C	0.9800
N4—C8	1.448 (4)	C13—H13A	0.9800
N4—H4N	0.8800	C13—H13B	0.9800
N5—C10	1.272 (4)	C13—H13C	0.9800
N6—C12	1.334 (4)	C14—H14A	0.9800
N6—C13	1.445 (4)	C14—H14B	0.9800
N6—C14	1.460 (4)	C14—H14C	0.9800

C3—S1—C4	102.89 (16)	N3—C6—H6C	109.5
C10—S2—C11	102.61 (16)	H6A—C6—H6C	109.5
C2—O2—N2	114.5 (2)	H6B—C6—H6C	109.5
C9—O5—N5	114.6 (2)	N3—C7—H7A	109.5
C2—N1—C1	120.5 (2)	N3—C7—H7B	109.5
C2—N1—H1N	119.8	H7A—C7—H7B	109.5
C1—N1—H1N	119.8	N3—C7—H7C	109.5
C3—N2—O2	108.1 (2)	H7A—C7—H7C	109.5
C5—N3—C7	124.6 (3)	H7B—C7—H7C	109.5
C5—N3—C6	118.9 (3)	N4—C8—H8A	109.5
C7—N3—C6	116.3 (3)	N4—C8—H8B	109.5
C9—N4—C8	121.0 (3)	H8A—C8—H8B	109.5
C9—N4—H4N	119.5	N4—C8—H8C	109.5
C8—N4—H4N	119.5	H8A—C8—H8C	109.5
C10—N5—O5	108.5 (2)	H8B—C8—H8C	109.5
C12—N6—C13	124.1 (3)	O4—C9—N4	126.9 (3)
C12—N6—C14	119.2 (3)	O4—C9—O5	115.2 (2)
C13—N6—C14	116.6 (3)	N4—C9—O5	117.9 (3)
N1—C1—H1A	109.5	N5—C10—C12	116.0 (2)
N1—C1—H1B	109.5	N5—C10—S2	123.7 (2)
H1A—C1—H1B	109.5	C12—C10—S2	120.1 (2)
N1—C1—H1C	109.5	S2—C11—H11A	109.5
H1A—C1—H1C	109.5	S2—C11—H11B	109.5
H1B—C1—H1C	109.5	H11A—C11—H11B	109.5
O1—C2—N1	126.2 (3)	S2—C11—H11C	109.5
O1—C2—O2	115.7 (2)	H11A—C11—H11C	109.5
N1—C2—O2	118.1 (3)	H11B—C11—H11C	109.5
N2—C3—C5	115.3 (2)	O6—C12—N6	124.7 (3)
N2—C3—S1	124.4 (2)	O6—C12—C10	117.4 (3)
C5—C3—S1	119.9 (2)	N6—C12—C10	117.9 (3)
S1—C4—H4A	109.5	N6—C13—H13A	109.5
S1—C4—H4B	109.5	N6—C13—H13B	109.5
H4A—C4—H4B	109.5	H13A—C13—H13B	109.5
S1—C4—H4C	109.5	N6—C13—H13C	109.5
H4A—C4—H4C	109.5	H13A—C13—H13C	109.5
H4B—C4—H4C	109.5	H13B—C13—H13C	109.5
O3—C5—N3	125.1 (3)	N6—C14—H14A	109.5
O3—C5—C3	117.4 (3)	N6—C14—H14B	109.5
N3—C5—C3	117.4 (3)	H14A—C14—H14B	109.5
N3—C6—H6A	109.5	N6—C14—H14C	109.5
N3—C6—H6B	109.5	H14A—C14—H14C	109.5
H6A—C6—H6B	109.5	H14B—C14—H14C	109.5

C2—O2—N2—C3	179.8 (2)	S1—C3—C5—N3	93.6 (3)
C9—O5—N5—C10	178.1 (2)	C8—N4—C9—O4	0.0 (5)
C1—N1—C2—O1	3.0 (5)	C8—N4—C9—O5	179.2 (2)
C1—N1—C2—O2	−178.2 (3)	N5—O5—C9—O4	−178.6 (2)
N2—O2—C2—O1	179.9 (2)	N5—O5—C9—N4	2.1 (3)
N2—O2—C2—N1	1.0 (3)	O5—N5—C10—C12	−174.7 (2)
O2—N2—C3—C5	−173.4 (2)	O5—N5—C10—S2	0.4 (3)
O2—N2—C3—S1	−0.5 (3)	C11—S2—C10—N5	−179.2 (3)
C4—S1—C3—N2	179.3 (3)	C11—S2—C10—C12	−4.2 (3)
C4—S1—C3—C5	−8.0 (3)	C13—N6—C12—O6	176.8 (3)
C7—N3—C5—O3	175.0 (3)	C14—N6—C12—O6	0.1 (4)
C6—N3—C5—O3	−0.1 (5)	C13—N6—C12—C10	−1.4 (4)
C7—N3—C5—C3	−2.4 (4)	C14—N6—C12—C10	−178.1 (3)
C6—N3—C5—C3	−177.5 (3)	N5—C10—C12—O6	85.8 (3)
N2—C3—C5—O3	89.3 (3)	S2—C10—C12—O6	−89.5 (3)
S1—C3—C5—O3	−84.0 (3)	N5—C10—C12—N6	−95.9 (3)
N2—C3—C5—N3	−93.1 (3)	S2—C10—C12—N6	88.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.88	2.13	2.871 (3)	142
N4—H4N···O4ⁱⁱ	0.88	2.04	2.794 (3)	142
C4—H4B···O6ⁱⁱⁱ	0.98	2.54	3.075 (4)	114
C6—H6B···O2^iv	0.98	2.60	3.518 (4)	156
C7—H7B···O1^iv	0.98	2.52	3.431 (4)	155
C11—H11B···O3^v	0.98	2.53	3.042 (4)	113
C13—H13B···O4^iv	0.98	2.53	3.440 (4)	155
C14—H14B···O5^iv	0.98	2.59	3.554 (4)	168

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

Acknowledgements

This research was supported by the Basic Science Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2015R1D1A4A01020317).

References

Agarwal, S., Sadeghi, N., Tyagi, I., Gupta, V. K. & Fakhri, A. (2016). J. Colloid Interface Sci. 478, 430–438. CrossRef CAS Google Scholar
Al-Dabbas, M. M., Shaderma, A. M. & Al-Antary, T. M. (2014). Life Sci. J. 11, 68–73. Google Scholar
Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Mazellier, P., Zamy, C. & Sarakha, M. (2010). Environ. Chem. Lett. 8, 19–24. CrossRef CAS Google Scholar
Mohammad, S. G., Ahmed, S. M. & Badawi, A. F. M. (2015). Desalination Water Treatment, 55, 2109–2120. CrossRef CAS Google Scholar
Osman, K. A., Al-Rehiayani, S. M., Al-Deghairi, M. A. & Salama, A. K. (2009). Int. Biodeterior. Biodegradation, 63, 341–346. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Takusagawa, F. & Jacobson, R. A. (1977). J. Agric. Food Chem. 25, 577–581. CSD CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar