Crystal structure of N-[(morpholin-4-yl)(thio-phen-2-yl)meth-yl]benzamide.

In the title compound, C16H18N2O2S, the morpholine ring adopts a chair conformation. The thio-phene ring makes a dihedral angle of 63.54 (14)° with the mean plane of the four C atoms [maximum deviation = 0.010 (3) Å] of the morpholine ring. The benzamide ring is disordered, with four C atoms occupying two sets of sites, with a refined occupancy ratio of 0.502 (4):0.498 (4). These two rings are inclined to one another by 85.2 (4)° and to the thio-phene ring by 72.7 (3) and 13.0 (3)° for the major and minor components, respectively. In the crystal, mol-ecules are linked via N-H⋯O hydrogen bonds, forming chains along [001].

Related literature

For the biological activity of benzamide derivatives, see: Carbonnelle et al. (2005 ▸); Hatzelmann & Schudt (2001 ▸); Simonini et al. (2006 ▸); Suzuki et al. (2005 ▸); Zhou et al. (1999 ▸); For related structures see: Muruganandam et al. (2009 ▸); Khan et al. (2012 ▸).

Experimental

Crystal data

C16H18N2O2S

M = 302.38

Monoclinic,

a = 16.5283 (11) Å

b = 9.9049 (7) Å

c = 9.6831 (5) Å

β = 99.056 (2)°

V = 1565.47 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 295 K

0.40 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T min = 0.920, T max = 0.959

11905 measured reflections

3836 independent reflections

2744 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.182

S = 1.04

3836 reflections

227 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2008 ▸); cell refinement: SAINT (Bruker, 2008 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015011639/su5156sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015011639/su5156Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015011639/su5156Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015011639/su5156fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The minor component of the disordered benzamide ring is shown with dashed lines.

Click here for additional data file.

b . DOI: 10.1107/S2056989015011639/su5156fig2.tif

A view along the b axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details). The C-bound H atoms and the minor component of the disordered benzamide ring have been omitted for clarity.

CCDC reference: 1406913

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H18N2O2S	F(000) = 640
Mr = 302.38	Dx = 1.283 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3836 reflections
a = 16.5283 (11) Å	θ = 2.4–28.3°
b = 9.9049 (7) Å	µ = 0.21 mm−1
c = 9.6831 (5) Å	T = 295 K
β = 99.056 (2)°	Block, colourless
V = 1565.47 (17) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Bruker APEXII CCD diffractometer	3836 independent reflections
Radiation source: fine-focus sealed tube	2744 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 0 pixels mm-1	θmax = 28.3°, θmin = 2.4°
ω and φ scans	h = −21→21
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
Tmin = 0.920, Tmax = 0.959	l = −12→7
11905 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.097P)2 + 0.5504P] where P = (Fo2 + 2Fc2)/3
3836 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.62 e Å−3
1 restraint	Δρmin = −0.41 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.94818 (4)	0.28631 (7)	0.23066 (8)	0.0622 (3)
N2	0.81748 (10)	0.05848 (16)	0.16552 (16)	0.0345 (4)
O2	0.81001 (12)	−0.19318 (16)	0.0245 (2)	0.0610 (5)
O1	0.66536 (11)	0.2032 (3)	0.37090 (16)	0.0734 (7)
N1	0.70424 (10)	0.21935 (18)	0.16023 (16)	0.0365 (4)
H1	0.6897	0.2365	0.0728	0.044*
C14	0.82300 (13)	0.4243 (2)	0.1121 (2)	0.0406 (5)
H14	0.7698	0.4523	0.0784	0.049*
C7	0.64812 (12)	0.2222 (2)	0.2448 (2)	0.0402 (5)
C1	0.56136 (13)	0.2450 (2)	0.1788 (2)	0.0450 (5)
C2	0.5166 (4)	0.3348 (8)	0.2408 (8)	0.087 (2)	0.502 (4)
H2	0.5404	0.3854	0.3174	0.105*	0.502 (4)
C6	0.5297 (3)	0.1744 (7)	0.0642 (6)	0.0662 (16)	0.502 (4)
H6	0.5626	0.1187	0.0192	0.079*	0.502 (4)
C2A	0.5393 (3)	0.3477 (7)	0.0839 (7)	0.0745 (18)	0.498 (4)
H2A	0.5798	0.4024	0.0570	0.089*	0.498 (4)
C6A	0.4971 (4)	0.1642 (9)	0.2132 (8)	0.093 (3)	0.498 (4)
H6A	0.5096	0.0944	0.2772	0.112*	0.498 (4)
C15	0.89612 (15)	0.5008 (2)	0.1046 (3)	0.0502 (5)
H15	0.8954	0.5852	0.0624	0.060*
C13	0.84490 (11)	0.29981 (19)	0.1788 (2)	0.0342 (4)
C8	0.79002 (11)	0.1877 (2)	0.21266 (19)	0.0329 (4)
H8	0.7955	0.1831	0.3148	0.039*
C16	0.96545 (15)	0.4401 (2)	0.1637 (3)	0.0570 (6)
H16	1.0172	0.4781	0.1676	0.068*
C9	0.81880 (14)	0.0498 (2)	0.0153 (2)	0.0432 (5)
H9A	0.8509	0.1235	−0.0138	0.052*
H9B	0.7635	0.0569	−0.0355	0.052*
C10	0.85569 (17)	−0.0830 (2)	−0.0167 (3)	0.0549 (6)
H10A	0.8572	−0.0888	−0.1163	0.066*
H10B	0.9116	−0.0881	0.0319	0.066*
C12	0.77106 (14)	−0.0547 (2)	0.2094 (2)	0.0463 (5)
H12A	0.7143	−0.0484	0.1649	0.056*
H12B	0.7725	−0.0516	0.3098	0.056*
C11	0.80761 (16)	−0.1865 (2)	0.1691 (3)	0.0557 (6)
H11A	0.8628	−0.1956	0.2200	0.067*
H11B	0.7753	−0.2612	0.1955	0.067*
C4	0.3980 (2)	0.2798 (6)	0.0732 (5)	0.1096 (16)
H4	0.3428	0.2933	0.0388	0.132*
C3	0.4339 (4)	0.3488 (11)	0.1858 (11)	0.114 (3)	0.502 (4)
H3	0.4023	0.4084	0.2289	0.137*	0.502 (4)
C5	0.4464 (4)	0.1872 (11)	0.0152 (8)	0.106 (3)	0.502 (4)
H5	0.4224	0.1326	−0.0580	0.127*	0.502 (4)
C3A	0.4572 (4)	0.3710 (10)	0.0275 (8)	0.101 (3)	0.498 (4)
H3A	0.4416	0.4407	−0.0354	0.121*	0.498 (4)
C5A	0.4167 (4)	0.1852 (13)	0.1551 (11)	0.114 (3)	0.498 (4)
H5A	0.3762	0.1279	0.1777	0.136*	0.498 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0364 (3)	0.0508 (4)	0.0969 (6)	−0.0011 (2)	0.0025 (3)	0.0151 (3)
N2	0.0359 (8)	0.0349 (8)	0.0319 (8)	−0.0025 (6)	0.0033 (6)	0.0022 (6)
O2	0.0749 (12)	0.0380 (9)	0.0652 (11)	0.0012 (8)	−0.0042 (9)	−0.0067 (7)
O1	0.0502 (10)	0.142 (2)	0.0284 (8)	0.0135 (11)	0.0070 (7)	−0.0040 (9)
N1	0.0306 (8)	0.0520 (10)	0.0258 (7)	0.0022 (7)	0.0014 (6)	0.0014 (7)
C14	0.0478 (10)	0.0426 (11)	0.0307 (9)	−0.0071 (8)	0.0041 (8)	−0.0024 (8)
C7	0.0352 (10)	0.0549 (12)	0.0300 (9)	−0.0002 (8)	0.0039 (7)	−0.0081 (8)
C1	0.0327 (10)	0.0642 (14)	0.0385 (10)	0.0004 (9)	0.0069 (8)	−0.0069 (10)
C2	0.046 (3)	0.120 (6)	0.096 (5)	0.021 (3)	0.013 (3)	−0.035 (4)
C6	0.038 (2)	0.097 (4)	0.062 (3)	−0.006 (2)	0.000 (2)	−0.020 (3)
C2A	0.050 (3)	0.085 (4)	0.086 (4)	0.016 (3)	0.004 (3)	0.003 (3)
C6A	0.046 (3)	0.141 (7)	0.091 (5)	−0.020 (4)	0.006 (3)	0.019 (5)
C15	0.0563 (12)	0.0358 (11)	0.0592 (13)	−0.0036 (9)	0.0115 (11)	0.0041 (10)
C13	0.0313 (9)	0.0365 (10)	0.0339 (9)	0.0006 (7)	0.0029 (7)	−0.0036 (7)
C8	0.0297 (8)	0.0420 (10)	0.0261 (8)	0.0008 (7)	0.0019 (7)	0.0001 (7)
C16	0.0446 (12)	0.0454 (13)	0.0821 (18)	−0.0088 (10)	0.0136 (11)	0.0029 (12)
C9	0.0565 (12)	0.0396 (11)	0.0332 (10)	0.0059 (9)	0.0061 (9)	0.0000 (8)
C10	0.0717 (16)	0.0452 (13)	0.0471 (12)	0.0089 (11)	0.0072 (11)	−0.0057 (10)
C12	0.0441 (11)	0.0448 (12)	0.0488 (12)	−0.0082 (9)	0.0039 (9)	0.0100 (9)
C11	0.0565 (14)	0.0397 (12)	0.0677 (16)	−0.0052 (10)	−0.0004 (12)	0.0114 (11)
C4	0.0342 (15)	0.188 (5)	0.102 (3)	0.011 (2)	−0.0034 (17)	−0.028 (3)
C3	0.050 (4)	0.155 (9)	0.141 (8)	0.040 (5)	0.027 (4)	−0.010 (6)
C5	0.048 (3)	0.179 (9)	0.082 (5)	−0.027 (4)	−0.018 (3)	−0.008 (5)
C3A	0.072 (4)	0.129 (7)	0.094 (5)	0.047 (5)	−0.010 (4)	0.002 (5)
C5A	0.039 (3)	0.176 (10)	0.122 (7)	−0.020 (5)	0.000 (4)	0.008 (7)

S1—C16	1.697 (2)	C6A—H6A	0.9300
S1—C13	1.7071 (19)	C15—C16	1.340 (3)
N2—C8	1.455 (2)	C15—H15	0.9300
N2—C12	1.459 (2)	C13—C8	1.502 (3)
N2—C9	1.461 (2)	C8—H8	0.9800
O2—C11	1.408 (3)	C16—H16	0.9300
O2—C10	1.420 (3)	C9—C10	1.503 (3)
O1—C7	1.223 (3)	C9—H9A	0.9700
N1—C7	1.331 (3)	C9—H9B	0.9700
N1—C8	1.463 (2)	C10—H10A	0.9700
N1—H1	0.8600	C10—H10B	0.9700
C14—C13	1.413 (3)	C12—C11	1.516 (3)
C14—C15	1.438 (3)	C12—H12A	0.9700
C14—H14	0.9300	C12—H12B	0.9700
C7—C1	1.493 (3)	C11—H11A	0.9700
C1—C6	1.345 (6)	C11—H11B	0.9700
C1—C2	1.356 (6)	C4—C5A	1.235 (11)
C1—C2A	1.380 (7)	C4—C3	1.344 (11)
C1—C6A	1.411 (7)	C4—C5	1.392 (10)
C2—C3	1.394 (9)	C4—C3A	1.451 (11)
C2—H2	0.9300	C4—H4	0.9300
C6—C5	1.391 (7)	C3—H3	0.9300
C6—H6	0.9300	C5—H5	0.9300
C2A—C3A	1.400 (8)	C3A—H3A	0.9300
C2A—H2A	0.9300	C5A—H5A	0.9300
C6A—C5A	1.375 (10)
C16—S1—C13	92.16 (11)	C15—C16—H16	123.8
C8—N2—C12	112.35 (15)	S1—C16—H16	123.8
C8—N2—C9	114.73 (15)	N2—C9—C10	109.09 (17)
C12—N2—C9	109.61 (16)	N2—C9—H9A	109.9
C11—O2—C10	110.06 (18)	C10—C9—H9A	109.9
C7—N1—C8	121.48 (15)	N2—C9—H9B	109.9
C7—N1—H1	119.3	C10—C9—H9B	109.9
C8—N1—H1	119.3	H9A—C9—H9B	108.3
C13—C14—C15	109.02 (19)	O2—C10—C9	111.3 (2)
C13—C14—H14	125.5	O2—C10—H10A	109.4
C15—C14—H14	125.5	C9—C10—H10A	109.4
O1—C7—N1	122.37 (19)	O2—C10—H10B	109.4
O1—C7—C1	120.54 (19)	C9—C10—H10B	109.4
N1—C7—C1	117.06 (17)	H10A—C10—H10B	108.0
C6—C1—C2	122.5 (4)	N2—C12—C11	109.75 (18)
C6—C1—C2A	78.9 (4)	N2—C12—H12A	109.7
C2—C1—C2A	72.9 (5)	C11—C12—H12A	109.7
C6—C1—C6A	72.0 (4)	N2—C12—H12B	109.7
C2—C1—C6A	77.6 (5)	C11—C12—H12B	109.7
C2A—C1—C6A	116.5 (4)	H12A—C12—H12B	108.2
C6—C1—C7	119.8 (3)	O2—C11—C12	111.78 (19)
C2—C1—C7	117.6 (3)	O2—C11—H11A	109.3
C2A—C1—C7	122.2 (3)	C12—C11—H11A	109.3
C6A—C1—C7	121.4 (4)	O2—C11—H11B	109.3
C1—C2—C3	117.8 (7)	C12—C11—H11B	109.3
C1—C2—H2	121.1	H11A—C11—H11B	107.9
C3—C2—H2	121.1	C5A—C4—C3	80.2 (7)
C1—C6—C5	118.0 (6)	C5A—C4—C5	70.0 (7)
C1—C6—H6	121.0	C3—C4—C5	117.0 (5)
C5—C6—H6	121.0	C5A—C4—C3A	123.7 (5)
C1—C2A—C3A	121.3 (6)	C3—C4—C3A	72.4 (6)
C1—C2A—H2A	119.4	C5—C4—C3A	80.2 (5)
C3A—C2A—H2A	119.4	C5A—C4—H4	118.1
C5A—C6A—C1	122.2 (7)	C3—C4—H4	120.1
C5A—C6A—H6A	118.9	C5—C4—H4	123.0
C1—C6A—H6A	118.9	C3A—C4—H4	118.1
C16—C15—C14	114.3 (2)	C4—C3—C2	122.8 (7)
C16—C15—H15	122.8	C4—C3—H3	118.6
C14—C15—H15	122.8	C2—C3—H3	118.6
C14—C13—C8	128.68 (17)	C6—C5—C4	121.6 (6)
C14—C13—S1	112.05 (15)	C6—C5—H5	119.2
C8—C13—S1	119.20 (14)	C4—C5—H5	119.2
N2—C8—N1	114.37 (15)	C2A—C3A—C4	115.9 (7)
N2—C8—C13	110.65 (14)	C2A—C3A—H3A	122.0
N1—C8—C13	110.57 (16)	C4—C3A—H3A	122.0
N2—C8—H8	106.9	C4—C5A—C6A	120.4 (8)
N1—C8—H8	106.9	C4—C5A—H5A	119.8
C13—C8—H8	106.9	C6A—C5A—H5A	119.8
C15—C16—S1	112.44 (18)
C8—N1—C7—O1	2.6 (3)	C9—N2—C8—C13	−59.9 (2)
C8—N1—C7—C1	−175.38 (18)	C7—N1—C8—N2	111.0 (2)
O1—C7—C1—C6	−130.9 (4)	C7—N1—C8—C13	−123.3 (2)
N1—C7—C1—C6	47.1 (4)	C14—C13—C8—N2	130.5 (2)
O1—C7—C1—C2	47.1 (5)	S1—C13—C8—N2	−52.7 (2)
N1—C7—C1—C2	−134.9 (5)	C14—C13—C8—N1	2.7 (3)
O1—C7—C1—C2A	133.5 (4)	S1—C13—C8—N1	179.57 (13)
N1—C7—C1—C2A	−48.5 (4)	C14—C15—C16—S1	0.7 (3)
O1—C7—C1—C6A	−44.8 (5)	C13—S1—C16—C15	0.3 (2)
N1—C7—C1—C6A	133.1 (5)	C8—N2—C9—C10	174.63 (17)
C6—C1—C2—C3	2.8 (10)	C12—N2—C9—C10	−57.9 (2)
C2A—C1—C2—C3	67.0 (8)	C11—O2—C10—C9	−59.3 (3)
C6A—C1—C2—C3	−56.0 (8)	N2—C9—C10—O2	59.6 (3)
C7—C1—C2—C3	−175.2 (6)	C8—N2—C12—C11	−174.71 (17)
C2—C1—C6—C5	−5.1 (9)	C9—N2—C12—C11	56.5 (2)
C2A—C1—C6—C5	−66.4 (7)	C10—O2—C11—C12	57.7 (3)
C6A—C1—C6—C5	56.4 (7)	N2—C12—C11—O2	−56.9 (2)
C7—C1—C6—C5	172.8 (5)	C5A—C4—C3—C2	64.2 (10)
C6—C1—C2A—C3A	64.4 (7)	C5—C4—C3—C2	2.7 (14)
C2—C1—C2A—C3A	−65.0 (7)	C3A—C4—C3—C2	−66.0 (10)
C6A—C1—C2A—C3A	1.1 (9)	C1—C2—C3—C4	−1.6 (14)
C7—C1—C2A—C3A	−177.3 (5)	C1—C6—C5—C4	6.3 (11)
C6—C1—C6A—C5A	−66.7 (8)	C5A—C4—C5—C6	−72.3 (9)
C2—C1—C6A—C5A	63.9 (9)	C3—C4—C5—C6	−5.1 (12)
C2A—C1—C6A—C5A	0.4 (10)	C3A—C4—C5—C6	59.2 (8)
C7—C1—C6A—C5A	178.9 (7)	C1—C2A—C3A—C4	−1.0 (10)
C13—C14—C15—C16	−1.6 (3)	C5A—C4—C3A—C2A	−1.0 (11)
C15—C14—C13—C8	178.82 (19)	C3—C4—C3A—C2A	63.8 (7)
C15—C14—C13—S1	1.8 (2)	C5—C4—C3A—C2A	−58.7 (7)
C16—S1—C13—C14	−1.24 (17)	C3—C4—C5A—C6A	−58.5 (9)
C16—S1—C13—C8	−178.59 (17)	C5—C4—C5A—C6A	65.1 (9)
C12—N2—C8—N1	−60.4 (2)	C3A—C4—C5A—C6A	2.6 (14)
C9—N2—C8—N1	65.7 (2)	C1—C6A—C5A—C4	−2.3 (14)
C12—N2—C8—C13	173.99 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.02	2.878 (2)	173

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1O1i	0.86	2.02	2.878(2)	173

Symmetry code: (i) .