4-{[4-(3,5-Dimeth­oxy­benzamido)­phen­yl]sulfan­yl}-N-methyl­pyridine-2-carboxamide

Huang, T.-T.; Meng, N.-N.; Qing, X.-Y.; Yu, L.-T.

doi:10.1107/S1600536811006490

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o856

doi:10.1107/S1600536811006490

Open

access

4-{[4-(3,5-Dimethoxybenzamido)phenyl]sulfanyl}-N-methylpyridine-2-carboxamide

Ting-Ting Huang,^a Na-Na Meng,^a Xiao-Yu Qing ^a and Luo-Ting Yu ^a ^*

^aState Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, People's Republic of China
^*Correspondence e-mail: luodyu@163.com

(Received 15 December 2010; accepted 21 February 2011; online 12 March 2011)

There are two independent molecules in the asymmetric unit of the title compound, C₂₂H₂₁N₃O₄S. The central benzene ring makes dihedral angles of 74.28 (6) and 68.84 (6)° with the pyridine and 3,5-dimethoxyphenyl rings, respectively, in one molecule [86.66 (6) and 81.14 (6)° respectively, in the other]. Each of the molecules forms a centrosymmetric dimer with another molecule via pairs of intermolecular N—H⋯O hydrogen bonds. These hydrogen bonds connect the N—H groups and the O atoms of the carbonyl groups next to the 3,5-dimethoxyphenyl rings. Additional intermolecular N—H⋯O interactions link the dimers in the crystal structure.

Related literature

For related compounds and their biological activity, see: Khire et al. (2004 ); Dominguez et al. (2007 ).

Experimental

Crystal data

C₂₂H₂₁N₃O₄S
M_r = 423.49
Triclinic, $[P \overline 1]$
a = 11.1165 (5) Å
b = 13.5678 (6) Å
c = 15.3183 (6) Å
α = 102.723 (4)°
β = 105.949 (4)°
γ = 90.975 (4)°
V = 2159.51 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 293 K
0.24 × 0.20 × 0.17 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.989, T_max = 1.0
18448 measured reflections
8806 independent reflections
4117 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.065
S = 1.00
8806 reflections
547 parameters
H-atom parameters constrained
Δρ_max = 0.24 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
N1—H1⋯O4ⁱ	0.86	2.12	2.941 (2)	159
N3—H3⋯O7ⁱⁱ	0.86	2.22	2.922 (2)	138
N4—H4⋯O8ⁱⁱⁱ	0.86	2.15	2.985 (2)	163
N6—H6⋯O3^iv	0.86	2.30	2.957 (2)	133
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x, y-1, z; (iii) -x+2, -y+1, -z+2; (iv) x, y+1, z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811006490/im2258sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006490/im2258Isup2.hkl

checkCIF report

Comment top

Sorafenib is of great importance owing to its antitumor properties (Khire et al., 2004; Dominguez et al., 2007). The title compound, as one of its derivatives, possessed even better in vitro anticancer activity against both two tumor cell lines (HCT116 and HEPG2). As a potent antitumor drug, we report here its crystal structure. In the title molecule, C₂₂H₂₁N₃O₄S, (Fig. 1), the phenyl ring makes dihedral angles of 78.54 (6)° and 75.30 (6)° with the pyridine ring and the 3,5-dimethoxyphenyl ring, respectively. In crystal, the molecules form centrosymmetric dimers via a pair of intermolecular N–H···O hydrogen bonds. In the crystal structure, intermolecular N—H···O hydrogen-bonding interactions between the dimers form an infinite three-dimensional structure (Table 1 and Fig. 2).

Related literature top

For related compounds and their biological activity, see: Khire et al. (2004); Dominguez et al. (2007).

Experimental top

To the suspension of anhydrous potassium carbonate (0.69 g, 5.00 mmol) and 4-(4-aminophenylthio)-N-methylpicolinamide (0.52 g, 2.00 mmol) in 7.00 ml THF was added dropwise 3,5-dimethoxybenzoyl chloride (0.42 g, 2.10 mmol). After being stirred at room temperature for 2 h, the mixture was extracted with 30 ml e thyl acetate and 30 ml brine for three times and the combined organic layers were dried over anhydrous sodium sulfate. Then the solution was concentrated under vacuum, and the residue was recrystallized from ethanol to give the title compound, with 32.13% yield. Crystals suitable for X-ray analysis were obtained by slow evaporation from an ethanolic solution at room temperature.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound.

4-{[4-(3,5-Dimethoxybenzamido)phenyl]sulfanyl}-N-methylpyridine- 2-carboxamide top

Crystal data top

C₂₂H₂₁N₃O₄S	Z = 4
M_r = 423.49	F(000) = 888
Triclinic, P1	D_x = 1.303 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 11.1165 (5) Å	Cell parameters from 5046 reflections
b = 13.5678 (6) Å	θ = 2.9–29.2°
c = 15.3183 (6) Å	µ = 0.18 mm⁻¹
α = 102.723 (4)°	T = 293 K
β = 105.949 (4)°	Block, orange
γ = 90.975 (4)°	0.24 × 0.20 × 0.17 mm
V = 2159.51 (16) Å³

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	8806 independent reflections
Radiation source: fine-focus sealed tube	4117 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 16.0874 pixels mm^-1	θ_max = 26.4°, θ_min = 2.9°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −16→16
T_min = 0.989, T_max = 1.0	l = −19→19
18448 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0126P)²] where P = (F_o² + 2F_c²)/3
8806 reflections	(Δ/σ)_max = 0.001
547 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₂H₂₁N₃O₄S	γ = 90.975 (4)°
M_r = 423.49	V = 2159.51 (16) Å³
Triclinic, P1	Z = 4
a = 11.1165 (5) Å	Mo Kα radiation
b = 13.5678 (6) Å	µ = 0.18 mm⁻¹
c = 15.3183 (6) Å	T = 293 K
α = 102.723 (4)°	0.24 × 0.20 × 0.17 mm
β = 105.949 (4)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	8806 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	4117 reflections with I > 2σ(I)
T_min = 0.989, T_max = 1.0	R_int = 0.032
18448 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.065	H-atom parameters constrained
S = 1.00	Δρ_max = 0.24 e Å⁻³
8806 reflections	Δρ_min = −0.23 e Å⁻³
547 parameters

Special details top

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
S1	0.65660 (6)	0.37812 (4)	1.12524 (4)	0.05655 (19)
O1	0.39178 (13)	0.32537 (11)	0.17737 (9)	0.0536 (4)
O2	0.33947 (17)	−0.01920 (13)	0.01326 (11)	0.0862 (6)
O3	0.64974 (15)	0.00594 (12)	0.34157 (10)	0.0708 (5)
O4	0.64438 (14)	−0.26093 (10)	0.57675 (10)	0.0568 (4)
N1	0.56894 (16)	0.13586 (12)	0.42239 (12)	0.0541 (5)
H1	0.5175	0.1823	0.4170	0.065*
N2	0.89197 (18)	−0.23172 (14)	0.78726 (14)	0.0582 (5)
N3	0.74299 (16)	−0.37746 (14)	0.64935 (12)	0.0553 (5)
H3	0.8025	−0.3878	0.6951	0.066*
C1	0.48731 (19)	0.20452 (16)	0.25279 (15)	0.0453 (6)
H1A	0.5205	0.2565	0.3056	0.054*
C2	0.4130 (2)	0.22594 (17)	0.17137 (16)	0.0409 (6)
C3	0.3640 (2)	0.14940 (17)	0.09286 (15)	0.0513 (6)
H3A	0.3123	0.1638	0.0389	0.062*
C4	0.3926 (2)	0.05029 (18)	0.09486 (17)	0.0553 (7)
C5	0.4657 (2)	0.02726 (17)	0.17531 (17)	0.0555 (7)
H5	0.4841	−0.0392	0.1764	0.067*
C6	0.5116 (2)	0.10566 (18)	0.25486 (16)	0.0460 (6)
C7	0.3120 (2)	0.35033 (16)	0.09594 (15)	0.0696 (7)
H7B	0.3508	0.3355	0.0462	0.104*
H7C	0.2990	0.4212	0.1096	0.104*
H7A	0.2327	0.3110	0.0773	0.104*
C8	0.3678 (2)	−0.12126 (17)	0.00739 (16)	0.0935 (10)
H8C	0.4572	−0.1244	0.0242	0.140*
H8B	0.3313	−0.1602	−0.0553	0.140*
H8A	0.3342	−0.1485	0.0493	0.140*
C9	0.5843 (2)	0.07740 (18)	0.34252 (16)	0.0508 (6)
C10	0.6310 (2)	0.12627 (15)	0.51350 (16)	0.0461 (6)
C11	0.7543 (2)	0.10139 (15)	0.53712 (16)	0.0557 (7)
H11	0.7976	0.0900	0.4923	0.067*
C12	0.8126 (2)	0.09347 (15)	0.62633 (16)	0.0520 (6)
H12	0.8951	0.0761	0.6413	0.062*
C13	0.7502 (2)	0.11111 (15)	0.69480 (15)	0.0465 (6)
C14	0.6284 (2)	0.13777 (15)	0.67162 (16)	0.0544 (6)
H14	0.5857	0.1508	0.7168	0.065*
C15	0.5693 (2)	0.14532 (15)	0.58157 (16)	0.0551 (6)
H15	0.4871	0.1634	0.5667	0.066*
C16	0.8519 (2)	−0.02610 (16)	0.79660 (15)	0.0460 (6)
C17	0.9419 (2)	−0.05579 (18)	0.86601 (15)	0.0579 (7)
H17	0.9908	−0.0079	0.9174	0.069*
C18	0.9577 (2)	−0.1577 (2)	0.85779 (17)	0.0688 (8)
H18	1.0190	−0.1761	0.9051	0.083*
C19	0.8052 (2)	−0.20169 (17)	0.72111 (15)	0.0430 (6)
C20	0.78341 (19)	−0.10110 (16)	0.72188 (14)	0.0431 (6)
H20	0.7235	−0.0845	0.6728	0.052*
C21	0.7239 (2)	−0.28288 (18)	0.64210 (16)	0.0450 (6)
C22	0.6663 (2)	−0.46444 (16)	0.58221 (16)	0.0773 (8)
H22B	0.5870	−0.4711	0.5949	0.116*
H22C	0.7088	−0.5248	0.5874	0.116*
H22A	0.6526	−0.4546	0.5201	0.116*
S2	0.83017 (6)	0.10378 (4)	0.80987 (4)	0.06080 (19)
O5	1.15357 (17)	0.53884 (17)	0.58562 (12)	0.0965 (6)
O6	1.08908 (16)	0.18987 (14)	0.57927 (12)	0.0908 (6)
O7	0.84584 (14)	0.49944 (11)	0.78247 (10)	0.0623 (5)
O8	0.83861 (13)	0.74737 (10)	1.12151 (10)	0.0537 (4)
N4	0.93679 (14)	0.37157 (11)	0.84322 (11)	0.0444 (5)
H4	0.9932	0.3291	0.8417	0.053*
N5	0.62508 (15)	0.71220 (13)	1.24900 (12)	0.0482 (5)
N6	0.74652 (15)	0.86110 (13)	1.20748 (11)	0.0523 (5)
H6	0.6911	0.8696	1.2376	0.063*
C23	1.03238 (19)	0.48973 (17)	0.68142 (14)	0.0529 (6)
H23	1.0154	0.5559	0.7038	0.063*
C24	1.1014 (2)	0.4680 (2)	0.61764 (17)	0.0623 (7)
C25	1.1221 (2)	0.3681 (2)	0.58183 (15)	0.0676 (8)
H25	1.1677	0.3542	0.5385	0.081*
C26	1.0758 (2)	0.2906 (2)	0.61010 (17)	0.0612 (7)
C27	1.00969 (19)	0.31162 (17)	0.67610 (15)	0.0547 (7)
H27	0.9795	0.2591	0.6964	0.066*
C28	0.98907 (19)	0.40933 (17)	0.71110 (14)	0.0443 (6)
C29	1.1378 (3)	0.6419 (2)	0.61998 (19)	0.1054 (11)
H29A	1.0500	0.6523	0.6043	0.158*
H29B	1.1800	0.6835	0.5924	0.158*
H29C	1.1728	0.6599	0.6866	0.158*
C30	1.1599 (3)	0.1633 (2)	0.51522 (19)	0.1318 (13)
H30A	1.1195	0.1831	0.4585	0.198*
H30B	1.1658	0.0913	0.5019	0.198*
H30C	1.2426	0.1973	0.5417	0.198*
C31	0.9166 (2)	0.43189 (17)	0.78087 (15)	0.0454 (6)
C32	0.8700 (2)	0.37503 (14)	0.91011 (15)	0.0378 (5)
C33	0.93255 (19)	0.36860 (14)	0.99944 (15)	0.0471 (6)
H33	1.0186	0.3627	1.0155	0.057*
C34	0.8686 (2)	0.37083 (14)	1.06550 (14)	0.0488 (6)
H34	0.9121	0.3669	1.1257	0.059*
C35	0.7406 (2)	0.37881 (14)	1.04267 (15)	0.0407 (6)
C36	0.67767 (19)	0.38272 (14)	0.95225 (15)	0.0464 (6)
H36	0.5913	0.3874	0.9357	0.056*
C37	0.7419 (2)	0.37978 (14)	0.88621 (15)	0.0476 (6)
H37	0.6983	0.3810	0.8253	0.057*
C38	0.64704 (18)	0.50777 (15)	1.17087 (13)	0.0402 (6)
C39	0.57828 (19)	0.53448 (17)	1.23420 (15)	0.0491 (6)
H39	0.5380	0.4849	1.2520	0.059*
C40	0.57063 (19)	0.63515 (18)	1.27021 (14)	0.0540 (6)
H40	0.5241	0.6514	1.3127	0.065*
C41	0.69385 (18)	0.68463 (16)	1.18968 (14)	0.0397 (6)
C42	0.70578 (17)	0.58534 (15)	1.14923 (13)	0.0396 (5)
H42	0.7535	0.5708	1.1074	0.047*
C43	0.76637 (19)	0.76806 (17)	1.16986 (15)	0.0433 (6)
C44	0.8143 (2)	0.94991 (15)	1.20025 (15)	0.0692 (8)
H44B	0.8810	0.9292	1.1734	0.104*
H44C	0.8488	0.9933	1.2613	0.104*
H44A	0.7579	0.9859	1.1612	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0725 (5)	0.0409 (4)	0.0687 (5)	0.0063 (3)	0.0411 (4)	0.0118 (3)
O1	0.0681 (12)	0.0412 (11)	0.0543 (11)	0.0103 (8)	0.0185 (9)	0.0156 (8)
O2	0.1402 (18)	0.0447 (12)	0.0569 (12)	0.0043 (11)	0.0116 (12)	−0.0018 (10)
O3	0.0842 (14)	0.0676 (13)	0.0659 (12)	0.0430 (10)	0.0266 (10)	0.0178 (9)
O4	0.0598 (12)	0.0578 (11)	0.0464 (10)	0.0173 (9)	0.0037 (9)	0.0124 (8)
N1	0.0638 (14)	0.0518 (13)	0.0488 (13)	0.0288 (10)	0.0154 (11)	0.0152 (11)
N2	0.0547 (15)	0.0582 (15)	0.0561 (14)	0.0054 (11)	−0.0018 (12)	0.0238 (12)
N3	0.0542 (14)	0.0488 (14)	0.0595 (14)	0.0101 (11)	0.0065 (11)	0.0175 (11)
C1	0.0493 (16)	0.0411 (16)	0.0460 (15)	0.0011 (12)	0.0184 (13)	0.0056 (12)
C2	0.0459 (16)	0.0332 (16)	0.0488 (16)	0.0037 (12)	0.0204 (13)	0.0118 (13)
C3	0.0671 (18)	0.0427 (17)	0.0466 (16)	0.0053 (13)	0.0183 (14)	0.0132 (13)
C4	0.076 (2)	0.0416 (18)	0.0477 (17)	0.0048 (14)	0.0214 (15)	0.0051 (14)
C5	0.0748 (19)	0.0425 (17)	0.0576 (18)	0.0157 (14)	0.0297 (15)	0.0147 (14)
C6	0.0490 (16)	0.0458 (17)	0.0500 (16)	0.0123 (13)	0.0221 (13)	0.0145 (13)
C7	0.075 (2)	0.0595 (18)	0.0770 (19)	0.0254 (14)	0.0147 (16)	0.0302 (15)
C8	0.154 (3)	0.0420 (19)	0.077 (2)	0.0053 (18)	0.038 (2)	−0.0063 (15)
C9	0.0552 (18)	0.0508 (18)	0.0501 (17)	0.0127 (13)	0.0205 (14)	0.0123 (14)
C10	0.0500 (17)	0.0400 (15)	0.0481 (16)	0.0154 (12)	0.0119 (14)	0.0116 (12)
C11	0.0564 (19)	0.0570 (17)	0.0605 (18)	0.0165 (14)	0.0233 (15)	0.0188 (14)
C12	0.0437 (16)	0.0528 (16)	0.0585 (17)	0.0113 (12)	0.0098 (14)	0.0164 (13)
C13	0.0548 (18)	0.0324 (14)	0.0498 (16)	0.0016 (12)	0.0112 (14)	0.0096 (11)
C14	0.0611 (19)	0.0515 (16)	0.0552 (17)	0.0147 (13)	0.0237 (15)	0.0126 (13)
C15	0.0502 (17)	0.0598 (17)	0.0562 (17)	0.0208 (13)	0.0162 (15)	0.0130 (13)
C16	0.0480 (17)	0.0477 (16)	0.0448 (16)	0.0029 (13)	0.0124 (13)	0.0169 (13)
C17	0.0614 (19)	0.0573 (19)	0.0474 (16)	−0.0049 (14)	−0.0010 (13)	0.0181 (13)
C18	0.065 (2)	0.072 (2)	0.063 (2)	0.0064 (16)	−0.0072 (15)	0.0356 (17)
C19	0.0404 (16)	0.0470 (16)	0.0442 (16)	0.0057 (13)	0.0119 (13)	0.0162 (13)
C20	0.0464 (16)	0.0461 (16)	0.0399 (15)	0.0090 (12)	0.0132 (12)	0.0150 (12)
C21	0.0505 (18)	0.0479 (18)	0.0442 (16)	0.0131 (14)	0.0219 (14)	0.0151 (14)
C22	0.090 (2)	0.0500 (18)	0.075 (2)	−0.0031 (15)	0.0045 (17)	0.0058 (15)
S2	0.0754 (5)	0.0472 (4)	0.0500 (4)	0.0045 (3)	0.0053 (4)	0.0072 (3)
O5	0.1063 (16)	0.1152 (17)	0.0936 (15)	0.0018 (14)	0.0490 (13)	0.0518 (14)
O6	0.1197 (17)	0.0801 (15)	0.0861 (14)	0.0241 (12)	0.0650 (13)	0.0012 (11)
O7	0.0705 (12)	0.0642 (12)	0.0706 (12)	0.0332 (9)	0.0346 (10)	0.0331 (9)
O8	0.0566 (11)	0.0493 (10)	0.0647 (11)	0.0089 (8)	0.0343 (9)	0.0110 (8)
N4	0.0476 (13)	0.0432 (12)	0.0520 (12)	0.0203 (9)	0.0248 (11)	0.0162 (10)
N5	0.0449 (13)	0.0441 (13)	0.0593 (13)	0.0053 (10)	0.0262 (11)	0.0050 (10)
N6	0.0571 (14)	0.0381 (13)	0.0690 (14)	0.0056 (10)	0.0339 (11)	0.0070 (10)
C23	0.0537 (17)	0.0614 (18)	0.0453 (15)	0.0084 (13)	0.0118 (13)	0.0187 (13)
C24	0.0579 (18)	0.085 (2)	0.0496 (17)	−0.0002 (16)	0.0153 (14)	0.0268 (16)
C25	0.0629 (19)	0.100 (2)	0.0521 (18)	0.0106 (17)	0.0323 (15)	0.0220 (17)
C26	0.0529 (18)	0.074 (2)	0.0525 (18)	0.0119 (15)	0.0166 (14)	0.0036 (16)
C27	0.0567 (17)	0.0595 (19)	0.0496 (16)	0.0050 (13)	0.0226 (14)	0.0068 (13)
C28	0.0393 (15)	0.0528 (17)	0.0417 (15)	0.0055 (12)	0.0124 (12)	0.0117 (13)
C29	0.131 (3)	0.091 (3)	0.103 (3)	−0.014 (2)	0.028 (2)	0.049 (2)
C30	0.187 (3)	0.121 (3)	0.125 (3)	0.059 (2)	0.116 (3)	0.011 (2)
C31	0.0425 (16)	0.0466 (17)	0.0475 (16)	0.0037 (12)	0.0138 (13)	0.0107 (13)
C32	0.0397 (16)	0.0284 (13)	0.0468 (15)	0.0076 (11)	0.0155 (13)	0.0079 (11)
C33	0.0343 (15)	0.0554 (16)	0.0507 (16)	0.0089 (11)	0.0116 (13)	0.0107 (12)
C34	0.0554 (18)	0.0485 (16)	0.0423 (15)	0.0078 (13)	0.0127 (14)	0.0116 (12)
C35	0.0438 (16)	0.0297 (14)	0.0507 (16)	0.0057 (11)	0.0186 (13)	0.0070 (11)
C36	0.0343 (15)	0.0469 (16)	0.0611 (17)	0.0100 (11)	0.0167 (14)	0.0144 (12)
C37	0.0424 (16)	0.0548 (16)	0.0483 (15)	0.0105 (12)	0.0111 (13)	0.0192 (12)
C38	0.0393 (15)	0.0389 (15)	0.0434 (15)	0.0061 (11)	0.0142 (12)	0.0085 (11)
C39	0.0476 (16)	0.0501 (17)	0.0545 (16)	0.0026 (12)	0.0240 (13)	0.0105 (13)
C40	0.0509 (17)	0.0596 (18)	0.0563 (17)	0.0062 (13)	0.0317 (14)	0.0023 (14)
C41	0.0337 (14)	0.0412 (15)	0.0450 (15)	0.0061 (11)	0.0140 (12)	0.0079 (12)
C42	0.0384 (14)	0.0412 (15)	0.0413 (14)	0.0093 (11)	0.0170 (11)	0.0064 (11)
C43	0.0436 (16)	0.0383 (16)	0.0470 (16)	0.0098 (12)	0.0116 (13)	0.0091 (12)
C44	0.082 (2)	0.0438 (17)	0.090 (2)	0.0045 (14)	0.0416 (17)	0.0110 (14)

Geometric parameters (Å, º) top

S1—C35	1.7682 (19)	C22—H22C	0.9600
S1—C38	1.761 (2)	C22—H22A	0.9600
O1—C2	1.361 (2)	O5—C24	1.358 (2)
O1—C7	1.430 (2)	O5—C29	1.413 (3)
O2—C4	1.362 (2)	O6—C26	1.368 (3)
O2—C8	1.414 (2)	O6—C30	1.411 (2)
O3—C9	1.222 (2)	O7—C31	1.218 (2)
O4—C21	1.235 (2)	O8—C43	1.231 (2)
N1—H1	0.8600	N4—H4	0.8600
N1—C9	1.359 (2)	N4—C31	1.366 (2)
N1—C10	1.412 (2)	N4—C32	1.415 (2)
N2—C18	1.332 (3)	N5—C40	1.342 (2)
N2—C19	1.335 (2)	N5—C41	1.339 (2)
N3—H3	0.8600	N6—H6	0.8600
N3—C21	1.328 (2)	N6—C43	1.317 (2)
N3—C22	1.458 (2)	N6—C44	1.451 (2)
C1—H1A	0.9300	C23—H23	0.9300
C1—C2	1.387 (3)	C23—C24	1.387 (3)
C1—C6	1.378 (2)	C23—C28	1.396 (2)
C2—C3	1.375 (3)	C24—C25	1.394 (3)
C3—H3A	0.9300	C25—H25	0.9300
C3—C4	1.392 (3)	C25—C26	1.365 (3)
C4—C5	1.380 (3)	C26—C27	1.390 (3)
C5—H5	0.9300	C27—H27	0.9300
C5—C6	1.395 (3)	C27—C28	1.365 (2)
C6—C9	1.498 (3)	C28—C31	1.491 (3)
C7—H7B	0.9600	C29—H29A	0.9600
C7—H7C	0.9600	C29—H29B	0.9600
C7—H7A	0.9600	C29—H29C	0.9600
C8—H8C	0.9600	C30—H30A	0.9600
C8—H8B	0.9600	C30—H30B	0.9600
C8—H8A	0.9600	C30—H30C	0.9600
C10—C11	1.386 (3)	C32—C33	1.377 (2)
C10—C15	1.380 (2)	C32—C37	1.376 (2)
C11—H11	0.9300	C33—H33	0.9300
C11—C12	1.371 (3)	C33—C34	1.383 (2)
C12—H12	0.9300	C34—H34	0.9300
C12—C13	1.391 (2)	C34—C35	1.381 (2)
C13—C14	1.378 (3)	C35—C36	1.383 (3)
C13—S2	1.768 (2)	C36—H36	0.9300
C14—H14	0.9300	C36—C37	1.384 (2)
C14—C15	1.383 (3)	C37—H37	0.9300
C15—H15	0.9300	C38—C39	1.385 (2)
C16—C17	1.382 (3)	C38—C42	1.376 (2)
C16—C20	1.381 (3)	C39—H39	0.9300
C16—S2	1.757 (2)	C39—C40	1.369 (2)
C17—H17	0.9300	C40—H40	0.9300
C17—C18	1.380 (3)	C41—C42	1.378 (2)
C18—H18	0.9300	C41—C43	1.509 (3)
C19—C20	1.388 (2)	C42—H42	0.9300
C19—C21	1.507 (3)	C44—H44B	0.9600
C20—H20	0.9300	C44—H44C	0.9600
C22—H22B	0.9600	C44—H44A	0.9600

O1—C2—C1	115.0 (2)	O5—C24—C23	124.4 (3)
O1—C2—C3	124.5 (2)	O5—C24—C25	115.1 (2)
O1—C7—H7B	109.5	O5—C29—H29A	109.5
O1—C7—H7C	109.5	O5—C29—H29B	109.5
O1—C7—H7A	109.5	O5—C29—H29C	109.5
O2—C4—C3	114.4 (2)	O6—C26—C27	114.7 (2)
O2—C4—C5	124.6 (2)	O6—C30—H30A	109.5
O2—C8—H8C	109.5	O6—C30—H30B	109.5
O2—C8—H8B	109.5	O6—C30—H30C	109.5
O2—C8—H8A	109.5	O7—C31—N4	122.79 (19)
O3—C9—N1	123.0 (2)	O7—C31—C28	122.51 (19)
O3—C9—C6	122.3 (2)	O8—C43—N6	124.05 (19)
O4—C21—N3	123.5 (2)	O8—C43—C41	120.4 (2)
O4—C21—C19	121.2 (2)	N4—C31—C28	114.70 (19)
N1—C9—C6	114.6 (2)	N5—C40—C39	125.08 (19)
N2—C18—C17	124.9 (2)	N5—C40—H40	117.5
N2—C18—H18	117.5	N5—C41—C42	123.90 (18)
N2—C19—C20	124.2 (2)	N5—C41—C43	117.27 (19)
N2—C19—C21	117.5 (2)	N6—C43—C41	115.56 (19)
N3—C21—C19	115.3 (2)	N6—C44—H44B	109.5
N3—C22—H22B	109.5	N6—C44—H44C	109.5
N3—C22—H22C	109.5	N6—C44—H44A	109.5
N3—C22—H22A	109.5	C23—C24—C25	120.5 (2)
C1—C6—C5	120.9 (2)	C23—C28—C31	118.6 (2)
C1—C6—C9	121.8 (2)	C24—O5—C29	118.1 (2)
C2—O1—C7	116.82 (17)	C24—C23—H23	121.0
C2—C1—H1A	120.2	C24—C23—C28	118.1 (2)
C2—C3—H3A	120.3	C24—C25—H25	119.9
C2—C3—C4	119.4 (2)	C25—C26—O6	125.5 (2)
C3—C2—C1	120.5 (2)	C25—C26—C27	119.8 (2)
C4—O2—C8	118.42 (19)	C26—O6—C30	117.80 (19)
C4—C3—H3A	120.3	C26—C25—C24	120.3 (2)
C4—C5—H5	120.7	C26—C25—H25	119.9
C4—C5—C6	118.6 (2)	C26—C27—H27	120.0
C5—C4—C3	121.0 (2)	C27—C28—C23	121.31 (19)
C5—C6—C9	117.3 (2)	C27—C28—C31	120.11 (19)
C6—C1—H1A	120.2	C28—C23—H23	121.0
C6—C1—C2	119.6 (2)	C28—C27—C26	120.0 (2)
C6—C5—H5	120.7	C28—C27—H27	120.0
H7B—C7—H7C	109.5	H29A—C29—H29B	109.5
H7B—C7—H7A	109.5	H29A—C29—H29C	109.5
H7C—C7—H7A	109.5	H29B—C29—H29C	109.5
H8C—C8—H8B	109.5	H30A—C30—H30B	109.5
H8C—C8—H8A	109.5	H30A—C30—H30C	109.5
H8B—C8—H8A	109.5	H30B—C30—H30C	109.5
C9—N1—H1	117.5	C31—N4—H4	118.2
C9—N1—C10	125.04 (19)	C31—N4—C32	123.61 (17)
C10—N1—H1	117.5	C32—N4—H4	118.2
C10—C11—H11	119.9	C32—C33—H33	119.7
C10—C15—C14	120.7 (2)	C32—C33—C34	120.7 (2)
C10—C15—H15	119.7	C32—C37—C36	120.4 (2)
C11—C10—N1	121.4 (2)	C32—C37—H37	119.8
C11—C12—H12	119.5	C33—C32—N4	119.8 (2)
C11—C12—C13	120.9 (2)	C33—C34—H34	119.8
C12—C11—C10	120.2 (2)	C34—C33—H33	119.7
C12—C11—H11	119.9	C34—C35—S1	121.10 (18)
C12—C13—S2	119.56 (18)	C34—C35—C36	118.69 (19)
C13—C12—H12	119.5	C35—C34—C33	120.5 (2)
C13—C14—H14	119.8	C35—C34—H34	119.8
C13—C14—C15	120.4 (2)	C35—C36—H36	119.7
C14—C13—C12	118.7 (2)	C35—C36—C37	120.6 (2)
C14—C13—S2	121.66 (18)	C36—C35—S1	120.15 (17)
C14—C15—H15	119.7	C36—C37—H37	119.8
C15—C10—N1	119.5 (2)	C37—C32—N4	121.0 (2)
C15—C10—C11	119.0 (2)	C37—C32—C33	119.08 (19)
C15—C14—H14	119.8	C37—C36—H36	119.7
C16—C17—H17	120.6	C38—S1—C35	103.42 (9)
C16—C20—C19	119.1 (2)	C38—C39—H39	120.6
C16—C20—H20	120.5	C38—C42—C41	119.88 (17)
C16—S2—C13	102.47 (10)	C38—C42—H42	120.1
C17—C16—S2	118.17 (19)	C39—C38—S1	118.50 (15)
C17—C18—H18	117.5	C39—C40—H40	117.5
C18—N2—C19	115.4 (2)	C40—C39—C38	118.88 (18)
C18—C17—C16	118.8 (2)	C40—C39—H39	120.6
C18—C17—H17	120.6	C41—N5—C40	115.00 (18)
C19—C20—H20	120.5	C41—C42—H42	120.1
C20—C16—C17	117.5 (2)	C42—C38—S1	124.27 (15)
C20—C16—S2	124.28 (18)	C42—C38—C39	117.22 (19)
C20—C19—C21	118.4 (2)	C42—C41—C43	118.77 (18)
C21—N3—H3	118.9	C43—N6—H6	118.7
C21—N3—C22	122.1 (2)	C43—N6—C44	122.66 (17)
C22—N3—H3	118.9	C44—N6—H6	118.7
H22B—C22—H22C	109.5	H44B—C44—H44C	109.5
H22B—C22—H22A	109.5	H44B—C44—H44A	109.5
H22C—C22—H22A	109.5	H44C—C44—H44A	109.5

S1—C35—C36—C37	−177.77 (14)	S2—C13—C14—C15	178.39 (16)
S1—C38—C39—C40	179.83 (17)	S2—C16—C17—C18	178.32 (16)
S1—C38—C42—C41	−179.13 (15)	S2—C16—C20—C19	−177.09 (14)
O1—C2—C3—C4	179.82 (17)	O5—C24—C25—C26	179.0 (2)
O2—C4—C5—C6	−178.31 (19)	O6—C26—C27—C28	−179.1 (2)
N1—C10—C11—C12	179.40 (19)	N4—C32—C33—C34	−179.35 (17)
N1—C10—C15—C14	−179.2 (2)	N4—C32—C37—C36	179.74 (17)
N2—C19—C20—C16	−2.2 (3)	N5—C41—C42—C38	−1.4 (3)
N2—C19—C21—O4	−177.59 (19)	N5—C41—C43—O8	174.55 (19)
N2—C19—C21—N3	3.5 (3)	N5—C41—C43—N6	−5.3 (3)
C1—C2—C3—C4	−1.8 (3)	C23—C24—C25—C26	−0.8 (4)
C1—C6—C9—O3	−149.3 (2)	C23—C28—C31—O7	34.5 (3)
C1—C6—C9—N1	32.3 (3)	C23—C28—C31—N4	−144.92 (19)
C2—C1—C6—C5	2.1 (3)	C24—C23—C28—C27	−2.4 (3)
C2—C1—C6—C9	−176.02 (18)	C24—C23—C28—C31	179.0 (2)
C2—C3—C4—O2	−179.76 (18)	C24—C25—C26—O6	179.3 (2)
C2—C3—C4—C5	2.2 (3)	C24—C25—C26—C27	−1.1 (4)
C3—C4—C5—C6	−0.5 (3)	C25—C26—C27—C28	1.3 (3)
C4—C5—C6—C1	−1.7 (3)	C26—C27—C28—C23	0.5 (3)
C4—C5—C6—C9	176.49 (19)	C26—C27—C28—C31	179.1 (2)
C5—C6—C9—O3	32.5 (3)	C27—C28—C31—O7	−144.2 (2)
C5—C6—C9—N1	−145.87 (19)	C27—C28—C31—N4	36.4 (3)
C6—C1—C2—O1	178.23 (15)	C28—C23—C24—O5	−177.3 (2)
C6—C1—C2—C3	−0.3 (3)	C28—C23—C24—C25	2.5 (3)
C7—O1—C2—C1	−177.90 (17)	C29—O5—C24—C23	0.6 (4)
C7—O1—C2—C3	0.6 (3)	C29—O5—C24—C25	−179.1 (2)
C8—O2—C4—C3	177.17 (18)	C30—O6—C26—C25	2.2 (4)
C8—O2—C4—C5	−4.8 (3)	C30—O6—C26—C27	−177.3 (2)
C9—N1—C10—C11	36.4 (3)	C31—N4—C32—C33	−139.0 (2)
C9—N1—C10—C15	−145.8 (2)	C31—N4—C32—C37	44.2 (3)
C10—N1—C9—O3	4.0 (4)	C32—N4—C31—O7	5.9 (3)
C10—N1—C9—C6	−177.61 (19)	C32—N4—C31—C28	−174.73 (18)
C10—C11—C12—C13	−0.7 (3)	C32—C33—C34—C35	0.5 (3)
C11—C10—C15—C14	−1.3 (3)	C33—C32—C37—C36	2.9 (3)
C11—C12—C13—C14	−0.6 (3)	C33—C34—C35—S1	178.18 (15)
C11—C12—C13—S2	−178.15 (16)	C33—C34—C35—C36	1.1 (3)
C12—C13—C14—C15	0.9 (3)	C34—C35—C36—C37	−0.7 (3)
C12—C13—S2—C16	−68.06 (18)	C35—S1—C38—C39	175.66 (17)
C13—C14—C15—C10	0.1 (3)	C35—S1—C38—C42	−5.7 (2)
C14—C13—S2—C16	114.47 (18)	C35—C36—C37—C32	−1.4 (3)
C15—C10—C11—C12	1.6 (3)	C37—C32—C33—C34	−2.5 (3)
C16—C17—C18—N2	−0.3 (4)	C38—S1—C35—C34	96.53 (17)
C17—C16—C20—C19	1.8 (3)	C38—S1—C35—C36	−86.45 (18)
C17—C16—S2—C13	161.70 (16)	C38—C39—C40—N5	0.1 (3)
C18—N2—C19—C20	1.3 (3)	C39—C38—C42—C41	−0.5 (3)
C18—N2—C19—C21	−177.12 (18)	C40—N5—C41—C42	2.5 (3)
C19—N2—C18—C17	0.0 (3)	C40—N5—C41—C43	−174.82 (18)
C20—C16—C17—C18	−0.6 (3)	C41—N5—C40—C39	−1.8 (3)
C20—C16—S2—C13	−19.4 (2)	C42—C38—C39—C40	1.1 (3)
C20—C19—C21—O4	3.9 (3)	C42—C41—C43—O8	−2.9 (3)
C20—C19—C21—N3	−174.95 (17)	C42—C41—C43—N6	177.22 (19)
C21—C19—C20—C16	176.16 (17)	C43—C41—C42—C38	175.86 (17)
C22—N3—C21—O4	−3.2 (3)	C44—N6—C43—O8	−3.8 (3)
C22—N3—C21—C19	175.66 (17)	C44—N6—C43—C41	176.07 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.86	2.12	2.941 (2)	159
N3—H3···O7ⁱⁱ	0.86	2.22	2.922 (2)	138
N4—H4···O8ⁱⁱⁱ	0.86	2.15	2.985 (2)	163
N6—H6···O3^iv	0.86	2.30	2.957 (2)	133

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₁N₃O₄S
M_r	423.49
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	11.1165 (5), 13.5678 (6), 15.3183 (6)
α, β, γ (°)	102.723 (4), 105.949 (4), 90.975 (4)
V (Å³)	2159.51 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.24 × 0.20 × 0.17

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.989, 1.0
No. of measured, independent and observed [I > 2σ(I)] reflections	18448, 8806, 4117
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.065, 1.00
No. of reflections	8806
No. of parameters	547
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.23

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.86	2.12	2.941 (2)	159
N3—H3···O7ⁱⁱ	0.86	2.22	2.922 (2)	138
N4—H4···O8ⁱⁱⁱ	0.86	2.15	2.985 (2)	163
N6—H6···O3^iv	0.86	2.30	2.957 (2)	133

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

Acknowledgements

We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

References

Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Dominguez, C., Smith, L., Huang, Q., Yuan, C., Ouyang, X., Cai, L., Chen, P., Kim, J., Harvey, T., Syed, R., Kim, T.-S., Tasker, A., Wang, L., Zhang, M., Coxon, A., Bready, J., Starnes, C., Chen, D., Gan, Y., Neervannan, S., Kumar, G., Polverino, A. & Kendall, R. (2007). Bioorg. Med. Chem. Lett. 17, 6003–6008. Web of Science CrossRef PubMed CAS Google Scholar
Khire, U. R., Bankston, D., Barbosa, J., Brittelli, D. R., Caringal, Y., Carlson, R., Dumas, J., Gane, T., Heald, S. L., Hibner, B., Johnson, J. S., Katz, M. E., Kennure, N., Kingery-Wood, J., Lee, W., Liu, X.-G., Lowinger, T. B., McAlexander, I., Monahan, M.-K., Natero, R., Renick, J., Riedl, B., Rong, H., Sibley, R. N., Smith, R. A. & Wolanin, D. (2004). Bioorg. Med. Chem. Lett. 14, 783–786. Web of Science CrossRef PubMed CAS Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS 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 67| Part 4| April 2011| Page o856

doi:10.1107/S1600536811006490

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

4-{[4-(3,5-Dimeth­­oxy­benzamido)­phen­yl]sulfan­yl}-N-methyl­pyridine-2-carboxamide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-{[4-(3,5-Dimethoxybenzamido)phenyl]sulfanyl}-N-methylpyridine-2-carboxamide