Methyl N-({[2-(2-meth­oxy­acetamido)-4-(phenyl­sulfan­yl)phen­yl]amino}[(meth­oxy­carbonyl)imino]methyl)carbamate

Fun, H.-K.; Hemamalini, M.; Divya, K.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812002760

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o581-o582

doi:10.1107/S1600536812002760

Open

access

Methyl N-({[2-(2-methoxyacetamido)-4-(phenylsulfanyl)phenyl]amino}[(methoxycarbonyl)imino]methyl)carbamate

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^a K. Divya,^b B. Narayana ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 18 January 2012; accepted 22 January 2012; online 4 February 2012)

In the title compound, C₂₀H₂₂N₄O₆S, the phenyl and benzene rings form a dihedral angle of 58.75 (5)°. Intramolecular N—H⋯O and N—H⋯N hydrogen bonds generate two S(6) and one S(7) ring motif, respectively. In the crystal, molecules are linked via N—H⋯O, N—H⋯N, C—H⋯S and C—H⋯O hydrogen bonds, forming two-dimensional networks parallel to the bc plane.

Related literature

For the pharmacological properties of febantel, see: Wollweber et al. (1978 ); Delatour et al. (1982 ); Su et al. (2004 ). For a related structure, see: Yıldırım et al. (2007 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₀H₂₂N₄O₆S
M_r = 446.48
Monoclinic, P 2₁ /c
a = 10.6975 (7) Å
b = 10.6921 (7) Å
c = 18.3732 (13) Å
β = 91.068 (1)°
V = 2101.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.54 × 0.34 × 0.29 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.900, T_max = 0.945
22847 measured reflections
6133 independent reflections
5455 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.097
S = 1.05
6133 reflections
295 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H1N4⋯N3	0.867 (15)	2.104 (15)	2.8159 (12)	138.9 (13)
N1—H1N1⋯O1	0.848 (16)	2.058 (15)	2.7224 (11)	134.7 (13)
N1—H1N1⋯O5ⁱ	0.848 (16)	2.425 (16)	3.1162 (11)	139.2 (13)
N2—H1N2⋯O3	0.869 (16)	1.879 (17)	2.6002 (12)	139.3 (15)
C9—H9A⋯O3ⁱⁱ	0.96	2.38	3.2652 (15)	153
C13—H13A⋯S1ⁱⁱⁱ	0.97	2.80	3.7678 (11)	179
C14—H14B⋯O1^iv	0.96	2.52	3.3796 (14)	149
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) x, y-1, z.

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: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812002760/rz2701sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812002760/rz2701Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812002760/rz2701Isup3.cml

checkCIF report

Comment top

Febantel, N-{2-[2,3-bis-(methoxycarbonyl)-guanido]-5-(phenylthio)-phenyl}-2-methoxy acetamide, is used as an anthelmintic against gastrointestinal parasites in animals (Wollweber et al., 1978; Su et al., 2004). It is a pro-drug, which get converted into an active compound soon after administration (Delatour et al., 1982). The metabolic pathway of febantel is converted directly to either fenbendazole or oxfendazole, which is achieved via febantel sulfoxide as an intermediate.

The molecular structure of the title compound is shown in Fig. 1. Each of the two intramolecular N—H···O hydrogen bonds generates an S(6) ring motif and another intramolecular N—H···N hydrogen bond generates an S(7) ring motif (Bernstein et al., 1995). The dihedral angle between the two benzene rings (C1–C6:C15–C20) is 58.75 (5)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to a related structure (Yıldırım et al., 2007).

In the crystal structure (Fig. 2), molecules are linked via N—H···O, N—H···N, C—H···S and C—H···O (Table 1) hydrogen bonds, forming two-dimensional networks parallel to the bc plane.

Related literature top

For the pharmacological properties of febantel, see: Wollweber et al. (1978); Delatour et al. (1982); Su et al. (2004). For a related structure, see: Yıldırım et al. (2007). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987).

Experimental top

A febantel sample was obtained from CAD Pharma Ltd, Bangalore. Crystals of the title compound were obtained from ethanol by slow evaporation method (m.p. 392–395 K).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids. Intramolecular hydrogen bonds shown by dashed lines.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. H atoms not involved in intermolecular hydrogen bonds (dashed lines) are omitted.

Methyl N-({[2-(2-methoxyacetamido)-4- (phenylsulfanyl)phenyl]amino}[(methoxycarbonyl)imino]methyl)carbamate top

Crystal data top

C₂₀H₂₂N₄O₆S	F(000) = 936
M_r = 446.48	D_x = 1.411 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9985 reflections
a = 10.6975 (7) Å	θ = 2.7–30.1°
b = 10.6921 (7) Å	µ = 0.20 mm⁻¹
c = 18.3732 (13) Å	T = 296 K
β = 91.068 (1)°	Block, colourless
V = 2101.1 (2) Å³	0.54 × 0.34 × 0.29 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	6133 independent reflections
Radiation source: fine-focus sealed tube	5455 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 30.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
T_min = 0.900, T_max = 0.945	k = −14→15
22847 measured reflections	l = −25→25

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0543P)² + 0.5625P] where P = (F_o² + 2F_c²)/3
6133 reflections	(Δ/σ)_max = 0.001
295 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₀H₂₂N₄O₆S	V = 2101.1 (2) Å³
M_r = 446.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.6975 (7) Å	µ = 0.20 mm⁻¹
b = 10.6921 (7) Å	T = 296 K
c = 18.3732 (13) Å	0.54 × 0.34 × 0.29 mm
β = 91.068 (1)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	6133 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5455 reflections with I > 2σ(I)
T_min = 0.900, T_max = 0.945	R_int = 0.023
22847 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.38 e Å⁻³
6133 reflections	Δρ_min = −0.35 e Å⁻³
295 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.42127 (3)	0.88419 (2)	0.249402 (14)	0.02036 (7)
O1	0.77450 (7)	1.22767 (7)	0.60941 (4)	0.02052 (16)
O2	0.91564 (7)	1.16372 (8)	0.69502 (4)	0.02151 (16)
O3	1.02647 (7)	0.84660 (8)	0.59724 (4)	0.02269 (16)
O4	0.99201 (7)	0.71932 (7)	0.50204 (4)	0.01985 (15)
O5	0.42655 (7)	0.70638 (7)	0.50505 (4)	0.01913 (15)
O6	0.72299 (7)	0.63922 (7)	0.58737 (4)	0.02042 (16)
N1	0.72953 (7)	1.04818 (8)	0.50714 (4)	0.01405 (15)
N2	0.88185 (8)	1.04196 (8)	0.59968 (5)	0.01607 (16)
N3	0.86819 (7)	0.88433 (8)	0.50935 (5)	0.01461 (16)
N4	0.61754 (8)	0.80419 (8)	0.50169 (5)	0.01422 (16)
C1	0.59824 (8)	0.88924 (9)	0.44371 (5)	0.01307 (17)
C2	0.52211 (9)	0.85788 (9)	0.38387 (5)	0.01432 (17)
H2A	0.4786	0.7826	0.3835	0.017*
C3	0.51118 (9)	0.93868 (9)	0.32487 (5)	0.01544 (18)
C4	0.57771 (9)	1.05126 (10)	0.32423 (5)	0.01744 (19)
H4A	0.5725	1.1040	0.2840	0.021*
C5	0.65156 (9)	1.08331 (9)	0.38420 (5)	0.01613 (18)
H5A	0.6949	1.1587	0.3843	0.019*
C6	0.66180 (8)	1.00409 (9)	0.44448 (5)	0.01342 (17)
C7	0.82806 (8)	0.99016 (9)	0.53816 (5)	0.01355 (17)
C8	0.84971 (9)	1.15290 (10)	0.63288 (5)	0.01655 (18)
C9	0.89359 (11)	1.27827 (12)	0.73505 (7)	0.0272 (2)
H9A	0.9310	1.2718	0.7828	0.041*
H9B	0.8052	1.2914	0.7392	0.041*
H9C	0.9299	1.3474	0.7097	0.041*
C10	0.96600 (9)	0.82134 (9)	0.54164 (5)	0.01516 (18)
C11	1.09167 (10)	0.64191 (10)	0.53104 (6)	0.0216 (2)
H11A	1.0989	0.5678	0.5019	0.032*
H11B	1.0735	0.6189	0.5802	0.032*
H11C	1.1689	0.6875	0.5303	0.032*
C12	0.53768 (9)	0.71360 (9)	0.52285 (5)	0.01480 (17)
C13	0.59492 (9)	0.61584 (10)	0.57286 (6)	0.0188 (2)
H13A	0.5503	0.6150	0.6183	0.023*
H13B	0.5857	0.5340	0.5506	0.023*
C14	0.77597 (11)	0.54161 (11)	0.63081 (6)	0.0246 (2)
H14A	0.8636	0.5570	0.6384	0.037*
H14B	0.7646	0.4630	0.6063	0.037*
H14C	0.7353	0.5390	0.6769	0.037*
C15	0.33882 (9)	1.01680 (9)	0.21622 (5)	0.01638 (18)
C16	0.29868 (10)	1.11434 (11)	0.26040 (6)	0.0221 (2)
H16A	0.3188	1.1147	0.3099	0.026*
C17	0.22839 (11)	1.21108 (11)	0.22990 (7)	0.0276 (2)
H17A	0.2022	1.2765	0.2593	0.033*
C18	0.19673 (10)	1.21137 (11)	0.15617 (7)	0.0252 (2)
H18A	0.1502	1.2768	0.1362	0.030*
C19	0.23499 (9)	1.11348 (10)	0.11272 (6)	0.0201 (2)
H19A	0.2127	1.1124	0.0636	0.024*
C20	0.30667 (9)	1.01637 (10)	0.14207 (5)	0.01720 (18)
H20A	0.3331	0.9514	0.1124	0.021*
H1N4	0.6939 (14)	0.7947 (14)	0.5174 (8)	0.026 (4)*
H1N1	0.7094 (14)	1.1187 (15)	0.5245 (8)	0.024 (4)*
H1N2	0.9432 (15)	0.9972 (16)	0.6171 (9)	0.032 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.03029 (14)	0.01510 (12)	0.01531 (13)	−0.00098 (9)	−0.00951 (9)	0.00060 (9)
O1	0.0204 (3)	0.0201 (4)	0.0209 (4)	0.0025 (3)	−0.0047 (3)	−0.0038 (3)
O2	0.0242 (4)	0.0229 (4)	0.0172 (4)	0.0013 (3)	−0.0074 (3)	−0.0051 (3)
O3	0.0247 (4)	0.0224 (4)	0.0206 (4)	0.0052 (3)	−0.0102 (3)	−0.0019 (3)
O4	0.0179 (3)	0.0178 (3)	0.0236 (4)	0.0047 (3)	−0.0061 (3)	−0.0035 (3)
O5	0.0155 (3)	0.0220 (4)	0.0199 (4)	−0.0032 (3)	−0.0014 (3)	0.0031 (3)
O6	0.0190 (3)	0.0193 (4)	0.0227 (4)	−0.0005 (3)	−0.0054 (3)	0.0077 (3)
N1	0.0145 (3)	0.0132 (4)	0.0144 (4)	0.0004 (3)	−0.0033 (3)	−0.0013 (3)
N2	0.0169 (4)	0.0161 (4)	0.0150 (4)	0.0008 (3)	−0.0050 (3)	−0.0008 (3)
N3	0.0136 (3)	0.0148 (4)	0.0153 (4)	0.0004 (3)	−0.0029 (3)	0.0000 (3)
N4	0.0137 (3)	0.0146 (4)	0.0142 (4)	−0.0011 (3)	−0.0032 (3)	0.0035 (3)
C1	0.0130 (4)	0.0134 (4)	0.0127 (4)	0.0007 (3)	−0.0009 (3)	0.0016 (3)
C2	0.0150 (4)	0.0139 (4)	0.0140 (4)	−0.0010 (3)	−0.0017 (3)	0.0003 (3)
C3	0.0174 (4)	0.0157 (4)	0.0131 (4)	0.0002 (3)	−0.0031 (3)	−0.0003 (3)
C4	0.0214 (4)	0.0167 (4)	0.0141 (4)	−0.0013 (3)	−0.0031 (3)	0.0034 (3)
C5	0.0177 (4)	0.0139 (4)	0.0167 (4)	−0.0017 (3)	−0.0020 (3)	0.0015 (3)
C6	0.0127 (4)	0.0140 (4)	0.0134 (4)	0.0008 (3)	−0.0020 (3)	−0.0004 (3)
C7	0.0131 (4)	0.0145 (4)	0.0130 (4)	−0.0024 (3)	−0.0011 (3)	0.0018 (3)
C8	0.0159 (4)	0.0187 (4)	0.0150 (4)	−0.0031 (3)	−0.0018 (3)	−0.0013 (4)
C9	0.0285 (5)	0.0294 (6)	0.0234 (5)	0.0021 (4)	−0.0071 (4)	−0.0124 (5)
C10	0.0141 (4)	0.0151 (4)	0.0162 (4)	−0.0011 (3)	−0.0011 (3)	0.0015 (3)
C11	0.0178 (4)	0.0182 (5)	0.0287 (6)	0.0046 (4)	−0.0034 (4)	0.0016 (4)
C12	0.0178 (4)	0.0139 (4)	0.0127 (4)	−0.0013 (3)	−0.0003 (3)	0.0005 (3)
C13	0.0197 (4)	0.0176 (5)	0.0189 (5)	−0.0037 (3)	−0.0035 (3)	0.0052 (4)
C14	0.0290 (5)	0.0211 (5)	0.0236 (5)	0.0070 (4)	−0.0038 (4)	0.0050 (4)
C15	0.0159 (4)	0.0175 (4)	0.0156 (4)	−0.0018 (3)	−0.0024 (3)	0.0016 (3)
C16	0.0223 (5)	0.0263 (5)	0.0176 (5)	−0.0002 (4)	−0.0012 (4)	−0.0036 (4)
C17	0.0246 (5)	0.0254 (5)	0.0328 (6)	0.0050 (4)	−0.0005 (4)	−0.0077 (5)
C18	0.0192 (5)	0.0223 (5)	0.0338 (6)	0.0023 (4)	−0.0049 (4)	0.0036 (4)
C19	0.0171 (4)	0.0236 (5)	0.0195 (5)	−0.0022 (4)	−0.0049 (3)	0.0055 (4)
C20	0.0166 (4)	0.0194 (5)	0.0156 (4)	−0.0014 (3)	−0.0024 (3)	0.0004 (4)

Geometric parameters (Å, º) top

S1—C3	1.7712 (10)	C4—C5	1.3868 (14)
S1—C15	1.7720 (10)	C4—H4A	0.9300
O1—C8	1.2081 (13)	C5—C6	1.3971 (13)
O2—C8	1.3357 (12)	C5—H5A	0.9300
O2—C9	1.4502 (14)	C9—H9A	0.9600
O3—C10	1.2289 (12)	C9—H9B	0.9600
O4—C10	1.3433 (12)	C9—H9C	0.9600
O4—C11	1.4438 (12)	C11—H11A	0.9600
O5—C12	1.2296 (12)	C11—H11B	0.9600
O6—C13	1.4132 (12)	C11—H11C	0.9600
O6—C14	1.4249 (13)	C12—C13	1.5136 (14)
N1—C7	1.3410 (12)	C13—H13A	0.9700
N1—C6	1.4288 (12)	C13—H13B	0.9700
N1—H1N1	0.848 (16)	C14—H14A	0.9600
N2—C7	1.3752 (12)	C14—H14B	0.9600
N2—C8	1.3803 (13)	C14—H14C	0.9600
N2—H1N2	0.868 (17)	C15—C16	1.3943 (15)
N3—C7	1.3241 (12)	C15—C20	1.3989 (14)
N3—C10	1.3702 (12)	C16—C17	1.3905 (16)
N4—C12	1.3533 (12)	C16—H16A	0.9300
N4—C1	1.4129 (12)	C17—C18	1.3903 (17)
N4—H1N4	0.867 (15)	C17—H17A	0.9300
C1—C2	1.3968 (13)	C18—C19	1.3830 (17)
C1—C6	1.4036 (13)	C18—H18A	0.9300
C2—C3	1.3894 (13)	C19—C20	1.3933 (14)
C2—H2A	0.9300	C19—H19A	0.9300
C3—C4	1.3986 (14)	C20—H20A	0.9300

C3—S1—C15	105.41 (5)	H9B—C9—H9C	109.5
C8—O2—C9	114.73 (9)	O3—C10—O4	121.17 (9)
C10—O4—C11	115.12 (8)	O3—C10—N3	129.63 (9)
C13—O6—C14	110.50 (8)	O4—C10—N3	109.19 (8)
C7—N1—C6	124.93 (8)	O4—C11—H11A	109.5
C7—N1—H1N1	117.1 (10)	O4—C11—H11B	109.5
C6—N1—H1N1	117.9 (10)	H11A—C11—H11B	109.5
C7—N2—C8	127.26 (9)	O4—C11—H11C	109.5
C7—N2—H1N2	112.4 (11)	H11A—C11—H11C	109.5
C8—N2—H1N2	120.3 (11)	H11B—C11—H11C	109.5
C7—N3—C10	119.84 (8)	O5—C12—N4	125.52 (9)
C12—N4—C1	126.38 (8)	O5—C12—C13	119.76 (9)
C12—N4—H1N4	114.6 (10)	N4—C12—C13	114.73 (8)
C1—N4—H1N4	116.7 (10)	O6—C13—C12	111.85 (8)
C2—C1—C6	119.55 (9)	O6—C13—H13A	109.2
C2—C1—N4	120.92 (8)	C12—C13—H13A	109.2
C6—C1—N4	119.44 (8)	O6—C13—H13B	109.2
C3—C2—C1	120.28 (9)	C12—C13—H13B	109.2
C3—C2—H2A	119.9	H13A—C13—H13B	107.9
C1—C2—H2A	119.9	O6—C14—H14A	109.5
C2—C3—C4	120.42 (9)	O6—C14—H14B	109.5
C2—C3—S1	116.29 (7)	H14A—C14—H14B	109.5
C4—C3—S1	123.06 (8)	O6—C14—H14C	109.5
C5—C4—C3	119.24 (9)	H14A—C14—H14C	109.5
C5—C4—H4A	120.4	H14B—C14—H14C	109.5
C3—C4—H4A	120.4	C16—C15—C20	119.78 (9)
C4—C5—C6	121.01 (9)	C16—C15—S1	123.70 (8)
C4—C5—H5A	119.5	C20—C15—S1	116.38 (8)
C6—C5—H5A	119.5	C17—C16—C15	119.46 (10)
C5—C6—C1	119.45 (9)	C17—C16—H16A	120.3
C5—C6—N1	118.02 (8)	C15—C16—H16A	120.3
C1—C6—N1	122.35 (9)	C18—C17—C16	120.96 (11)
N3—C7—N1	118.91 (9)	C18—C17—H17A	119.5
N3—C7—N2	122.61 (9)	C16—C17—H17A	119.5
N1—C7—N2	118.46 (9)	C19—C18—C17	119.43 (10)
O1—C8—O2	125.82 (10)	C19—C18—H18A	120.3
O1—C8—N2	125.50 (9)	C17—C18—H18A	120.3
O2—C8—N2	108.68 (9)	C18—C19—C20	120.48 (10)
O2—C9—H9A	109.5	C18—C19—H19A	119.8
O2—C9—H9B	109.5	C20—C19—H19A	119.8
H9A—C9—H9B	109.5	C19—C20—C15	119.87 (10)
O2—C9—H9C	109.5	C19—C20—H20A	120.1
H9A—C9—H9C	109.5	C15—C20—H20A	120.1

C12—N4—C1—C2	−27.56 (14)	C8—N2—C7—N1	−3.23 (15)
C12—N4—C1—C6	155.89 (9)	C9—O2—C8—O1	−1.40 (15)
C6—C1—C2—C3	1.22 (14)	C9—O2—C8—N2	178.50 (9)
N4—C1—C2—C3	−175.32 (9)	C7—N2—C8—O1	−6.22 (17)
C1—C2—C3—C4	1.01 (15)	C7—N2—C8—O2	173.88 (9)
C1—C2—C3—S1	175.56 (7)	C11—O4—C10—O3	1.94 (14)
C15—S1—C3—C2	142.14 (8)	C11—O4—C10—N3	−178.42 (8)
C15—S1—C3—C4	−43.47 (10)	C7—N3—C10—O3	1.18 (16)
C2—C3—C4—C5	−2.11 (15)	C7—N3—C10—O4	−178.42 (8)
S1—C3—C4—C5	−176.27 (8)	C1—N4—C12—O5	−15.45 (16)
C3—C4—C5—C6	0.98 (15)	C1—N4—C12—C13	164.86 (9)
C4—C5—C6—C1	1.23 (14)	C14—O6—C13—C12	−176.40 (9)
C4—C5—C6—N1	−174.02 (9)	O5—C12—C13—O6	−179.96 (9)
C2—C1—C6—C5	−2.32 (14)	N4—C12—C13—O6	−0.25 (13)
N4—C1—C6—C5	174.27 (9)	C3—S1—C15—C16	−31.93 (10)
C2—C1—C6—N1	172.71 (8)	C3—S1—C15—C20	152.41 (8)
N4—C1—C6—N1	−10.69 (13)	C20—C15—C16—C17	−0.84 (16)
C7—N1—C6—C5	−123.35 (10)	S1—C15—C16—C17	−176.36 (9)
C7—N1—C6—C1	61.54 (13)	C15—C16—C17—C18	0.54 (17)
C10—N3—C7—N1	−177.78 (8)	C16—C17—C18—C19	0.49 (18)
C10—N3—C7—N2	0.88 (14)	C17—C18—C19—C20	−1.21 (16)
C6—N1—C7—N3	0.55 (14)	C18—C19—C20—C15	0.90 (15)
C6—N1—C7—N2	−178.17 (8)	C16—C15—C20—C19	0.14 (15)
C8—N2—C7—N3	178.10 (9)	S1—C15—C20—C19	175.98 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N4···N3	0.867 (15)	2.104 (15)	2.8159 (12)	138.9 (13)
N1—H1N1···O1	0.848 (16)	2.058 (15)	2.7224 (11)	134.7 (13)
N1—H1N1···O5ⁱ	0.848 (16)	2.425 (16)	3.1162 (11)	139.2 (13)
N2—H1N2···O3	0.869 (16)	1.879 (17)	2.6002 (12)	139.3 (15)
C9—H9A···O3ⁱⁱ	0.96	2.38	3.2652 (15)	153
C13—H13A···S1ⁱⁱⁱ	0.97	2.80	3.7678 (11)	179
C14—H14B···O1^iv	0.96	2.52	3.3796 (14)	149

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₂N₄O₆S
M_r	446.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.6975 (7), 10.6921 (7), 18.3732 (13)
β (°)	91.068 (1)
V (Å³)	2101.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.54 × 0.34 × 0.29

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.900, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	22847, 6133, 5455
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.097, 1.05
No. of reflections	6133
No. of parameters	295
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.35

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N4···N3	0.867 (15)	2.104 (15)	2.8159 (12)	138.9 (13)
N1—H1N1···O1	0.848 (16)	2.058 (15)	2.7224 (11)	134.7 (13)
N1—H1N1···O5ⁱ	0.848 (16)	2.425 (16)	3.1162 (11)	139.2 (13)
N2—H1N2···O3	0.869 (16)	1.879 (17)	2.6002 (12)	139.3 (15)
C9—H9A···O3ⁱⁱ	0.9600	2.3800	3.2652 (15)	153.00
C13—H13A···S1ⁱⁱⁱ	0.9700	2.8000	3.7678 (11)	179.00
C14—H14B···O1^iv	0.9600	2.5200	3.3796 (14)	149.00

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a postdoctoral research fellowship. BN thanks the UGC, India, for financial assistance through SAP and a BSR one-time grant for the purchase of chemicals.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
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
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Delatour, P., Yoshimura, H., Garnier, F. & Benoit, E. (1982). Recl Med. Vet. 158, 369–373. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Su, S.-C., Chou, H.-H., Chang, P.-C., Liu, C.-H. & Chou, S.-S. (2004). J. Food Drug Anal. 12, 244–253. CAS Google Scholar
Wollweber, H., Kölling, H., Widdig, H., Thomas, H., Schulz, H.-P. & Mürmann, P. (1978). Arzneim Forsch. (Drug. Res.), 28, 2193–2195. CAS Google Scholar
Yıldırım, S. Ö., Akkurt, M., Jarrahpour, A. A., Rezaei, S. & Heinemann, F. W. (2007). Acta Cryst. E63, o3478–o3479. Web of Science CSD 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o581-o582

doi:10.1107/S1600536812002760

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Methyl N-({[2-(2-meth­­oxy­acetamido)-4-(phenyl­sulfan­yl)phen­yl]amino}[(meth­­oxy­carbonyl)imino]methyl)carbamate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Methyl N-({[2-(2-methoxyacetamido)-4-(phenylsulfanyl)phenyl]amino}[(methoxycarbonyl)imino]methyl)carbamate