Methyl N-({[2-(2-meth-oxy-acetamido)-4-(phenyl-sulfan-yl)phen-yl]amino}[(meth-oxy-carbonyl)imino]methyl)carbamate.

In the title compound, C(20)H(22)N(4)O(6)S, the phenyl and benzene rings form a dihedral angle of 58.75 (5)°. Intra-molecular N-H⋯O and N-H⋯N hydrogen bonds generate two S(6) and one S(7) ring motif, respectively. In the crystal, mol-ecules 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 = 446.48

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.097

S = 1.05

6133 reflections

295 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.35 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812002760/rz2701sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812002760/rz2701Isup3.cml

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

C20H22N4O6S	F(000) = 936
Mr = 446.48	Dx = 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

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

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(Fo2) + (0.0543P)2 + 0.5625P] where P = (Fo2 + 2Fc2)/3
6133 reflections	(Δ/σ)max = 0.001
295 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···O1iv	0.96	2.52	3.3796 (14)	149

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⋯O1iv	0.96	2.52	3.3796 (14)	149

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .