Crystal structure and Hirshfeld surface analysis of 2-[(1,3-benzoxazol-2-yl)sulfan­yl]-N-(2-meth­oxy­phen­yl)acetamide

Aydin, A.; Celikesir, S.T.; Akkurt, M.; Saylam, M.; Pabuccuoglu, V.

doi:10.1107/S2056989019012908

Crystal structure and Hirshfeld surface analysis of 2-[(1,3-benzoxazol-2-yl)sulfanyl]-N-(2-methoxyphenyl)acetamide

A. Aydin, S. T. Celikesir, M. Akkurt, M. Saylam and V. Pabuccuoglu

In the title compound, there are two intramolecular N—H

O and N—H

N hydrogen bonds, forming S(5) and S(7) ring motifs, respectively. In the crystal, pairs of C—H

O hydrogen bonds link molecules into inversion dimers with $R_{2}^{2}$ (14) ring motifs, stacked along the b-axis direction. The inversion dimers are linked by C—H

π and π–π-stacking interactions, forming a three-dimensional network.

Keywords: crystal structure; 1,3-benzoxazole ring system; dimers; hydrogen bonding; Hirshfeld surface analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019012908/rz5264sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019012908/rz5264Isup2.hkl Contains datablock I

CCDC reference: 1954699

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.006 Å
R factor = 0.092
wR factor = 0.169
Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00623 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     27.097 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.389 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.312 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         38 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3 Note
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1             102.7 Degree
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         23 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...         31 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and WinGX (Farrugia, 2012).

2-[(1,3-Benzoxazol-2-yl)sulfanyl]-N-(2-methoxyphenyl)acetamide top

Crystal data top

C₁₆H₁₄N₂O₃S	F(000) = 656
M_r = 314.35	D_x = 1.398 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.6670 (13) Å	Cell parameters from 6692 reflections
b = 6.8704 (6) Å	θ = 3.2–26.3°
c = 16.7220 (16) Å	µ = 0.23 mm⁻¹
β = 108.020 (4)°	T = 296 K
V = 1493.1 (2) Å³	Block, colourless
Z = 4	0.10 × 0.07 × 0.06 mm

Data collection top

Bruker APEXII CCD diffractometer	2241 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.092
Absorption correction: multi-scan (SADABS; Bruker, 2007)	θ_max = 26.5°, θ_min = 3.1°
T_min = 0.654, T_max = 0.745	h = −17→17
23464 measured reflections	k = −8→8
3019 independent reflections	l = −20→20

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.092	H-atom parameters constrained
wR(F²) = 0.169	w = 1/[σ²(F_o²) + (0.0406P)² + 3.9251P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
3019 reflections	Δρ_max = 0.25 e Å⁻³
200 parameters	Δρ_min = −0.31 e Å⁻³

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.4055 (3)	0.2452 (5)	0.4388 (2)	0.0301 (9)
C2	0.4121 (3)	0.1973 (6)	0.3599 (3)	0.0437 (11)
H2	0.353578	0.186794	0.313350	0.052*
C3	0.5089 (4)	0.1660 (7)	0.3535 (3)	0.0507 (12)
H3	0.515664	0.134545	0.301349	0.061*
C4	0.5962 (4)	0.1801 (6)	0.4223 (3)	0.0515 (13)
H4	0.660182	0.158127	0.415281	0.062*
C5	0.5910 (3)	0.2258 (6)	0.5012 (3)	0.0460 (11)
H5	0.649354	0.234724	0.547961	0.055*
C6	0.4940 (3)	0.2573 (5)	0.5059 (3)	0.0330 (9)
C7	0.3608 (3)	0.3093 (5)	0.5452 (2)	0.0304 (9)
C8	0.1670 (3)	0.3513 (7)	0.5515 (3)	0.0401 (10)
H8A	0.160668	0.258715	0.506432	0.048*
H8B	0.122257	0.308919	0.583244	0.048*
C9	0.1330 (3)	0.5503 (6)	0.5143 (2)	0.0368 (10)
C10	0.1249 (3)	0.7568 (6)	0.3915 (2)	0.0272 (8)
C11	0.0683 (3)	0.9111 (6)	0.4077 (2)	0.0364 (10)
H11	0.044048	0.906129	0.453818	0.044*
C12	0.0479 (3)	1.0720 (7)	0.3557 (3)	0.0438 (11)
H12	0.008978	1.173897	0.366520	0.053*
C13	0.0844 (3)	1.0826 (7)	0.2882 (3)	0.0443 (11)
H13	0.070946	1.191980	0.253773	0.053*
C14	0.1411 (3)	0.9312 (7)	0.2714 (2)	0.0380 (10)
H14	0.165837	0.938978	0.225560	0.046*
C15	0.1615 (3)	0.7687 (6)	0.3217 (2)	0.0290 (9)
C16	0.2621 (5)	0.6219 (9)	0.2449 (3)	0.078 (2)
H16A	0.209173	0.634567	0.191795	0.118*
H16B	0.301214	0.505956	0.244719	0.118*
H16C	0.306739	0.733112	0.253872	0.118*
N1	0.3202 (2)	0.2815 (5)	0.46627 (18)	0.0309 (7)
N2	0.1476 (2)	0.5848 (5)	0.43945 (19)	0.0302 (7)
HN2	0.173630	0.491051	0.418615	0.036*
O1	0.4653 (2)	0.3005 (4)	0.57658 (16)	0.0363 (7)
O2	0.0961 (3)	0.6653 (6)	0.55175 (19)	0.0687 (11)
O3	0.2163 (2)	0.6103 (4)	0.31065 (17)	0.0467 (8)
S1	0.29895 (9)	0.35394 (17)	0.62002 (6)	0.0420 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.036 (2)	0.0217 (18)	0.032 (2)	0.0038 (16)	0.0093 (17)	0.0053 (16)
C2	0.047 (3)	0.045 (3)	0.039 (2)	0.002 (2)	0.013 (2)	0.000 (2)
C3	0.059 (3)	0.046 (3)	0.058 (3)	0.006 (2)	0.033 (3)	0.001 (2)
C4	0.044 (3)	0.036 (2)	0.085 (4)	0.005 (2)	0.035 (3)	0.009 (2)
C5	0.032 (2)	0.035 (2)	0.066 (3)	−0.0031 (19)	0.007 (2)	0.009 (2)
C6	0.038 (2)	0.0217 (19)	0.039 (2)	−0.0024 (17)	0.0112 (18)	0.0046 (17)
C7	0.036 (2)	0.024 (2)	0.029 (2)	0.0016 (16)	0.0067 (17)	0.0061 (16)
C8	0.041 (2)	0.052 (3)	0.034 (2)	−0.009 (2)	0.0208 (19)	0.000 (2)
C9	0.036 (2)	0.053 (3)	0.026 (2)	−0.001 (2)	0.0156 (18)	−0.0053 (19)
C10	0.0190 (18)	0.040 (2)	0.0195 (18)	−0.0011 (16)	0.0007 (15)	−0.0058 (16)
C11	0.027 (2)	0.050 (3)	0.030 (2)	0.0069 (19)	0.0060 (17)	−0.0084 (19)
C12	0.035 (2)	0.049 (3)	0.040 (3)	0.017 (2)	0.002 (2)	−0.010 (2)
C13	0.043 (3)	0.044 (3)	0.038 (2)	0.012 (2)	0.000 (2)	0.005 (2)
C14	0.034 (2)	0.055 (3)	0.022 (2)	0.004 (2)	0.0055 (17)	0.0048 (19)
C15	0.0247 (19)	0.040 (2)	0.0224 (18)	0.0045 (17)	0.0067 (15)	−0.0009 (17)
C16	0.117 (5)	0.081 (4)	0.066 (4)	0.054 (4)	0.071 (4)	0.027 (3)
N1	0.0325 (18)	0.0342 (18)	0.0236 (17)	0.0008 (14)	0.0055 (14)	−0.0010 (14)
N2	0.0334 (18)	0.0369 (18)	0.0261 (16)	0.0024 (14)	0.0177 (14)	−0.0058 (14)
O1	0.0348 (16)	0.0358 (15)	0.0311 (15)	−0.0026 (13)	−0.0002 (12)	0.0042 (12)
O2	0.101 (3)	0.082 (3)	0.0401 (19)	0.035 (2)	0.046 (2)	0.0056 (18)
O3	0.062 (2)	0.0517 (19)	0.0380 (17)	0.0240 (16)	0.0333 (15)	0.0094 (14)
S1	0.0516 (7)	0.0517 (7)	0.0226 (5)	0.0004 (6)	0.0114 (5)	0.0050 (5)

Geometric parameters (Å, º) top

C1—C6	1.375 (6)	C9—O2	1.211 (5)
C1—C2	1.389 (5)	C9—N2	1.348 (5)
C1—N1	1.401 (5)	C10—C11	1.388 (5)
C2—C3	1.377 (6)	C10—C15	1.406 (5)
C2—H2	0.9300	C10—N2	1.408 (5)
C3—C4	1.382 (7)	C11—C12	1.381 (6)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.379 (7)	C12—C13	1.370 (6)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.370 (6)	C13—C14	1.377 (6)
C5—H5	0.9300	C13—H13	0.9300
C6—O1	1.388 (5)	C14—C15	1.374 (6)
C7—N1	1.278 (5)	C14—H14	0.9300
C7—O1	1.362 (5)	C15—O3	1.366 (4)
C7—S1	1.740 (4)	C16—O3	1.426 (5)
C8—C9	1.514 (6)	C16—H16A	0.9600
C8—S1	1.812 (4)	C16—H16B	0.9600
C8—H8A	0.9700	C16—H16C	0.9600
C8—H8B	0.9700	N2—HN2	0.8600

C6—C1—C2	119.4 (4)	C11—C10—N2	124.6 (3)
C6—C1—N1	109.4 (3)	C15—C10—N2	116.7 (3)
C2—C1—N1	131.2 (4)	C12—C11—C10	120.4 (4)
C3—C2—C1	117.2 (4)	C12—C11—H11	119.8
C3—C2—H2	121.4	C10—C11—H11	119.8
C1—C2—H2	121.4	C13—C12—C11	120.4 (4)
C2—C3—C4	121.8 (4)	C13—C12—H12	119.8
C2—C3—H3	119.1	C11—C12—H12	119.8
C4—C3—H3	119.1	C12—C13—C14	120.0 (4)
C5—C4—C3	121.8 (4)	C12—C13—H13	120.0
C5—C4—H4	119.1	C14—C13—H13	120.0
C3—C4—H4	119.1	C15—C14—C13	120.6 (4)
C6—C5—C4	115.3 (4)	C15—C14—H14	119.7
C6—C5—H5	122.3	C13—C14—H14	119.7
C4—C5—H5	122.3	O3—C15—C14	125.4 (3)
C5—C6—C1	124.5 (4)	O3—C15—C10	114.6 (3)
C5—C6—O1	128.0 (4)	C14—C15—C10	120.0 (4)
C1—C6—O1	107.4 (3)	O3—C16—H16A	109.5
N1—C7—O1	117.4 (3)	O3—C16—H16B	109.5
N1—C7—S1	128.1 (3)	H16A—C16—H16B	109.5
O1—C7—S1	114.5 (3)	O3—C16—H16C	109.5
C9—C8—S1	111.7 (3)	H16A—C16—H16C	109.5
C9—C8—H8A	109.3	H16B—C16—H16C	109.5
S1—C8—H8A	109.3	C7—N1—C1	103.1 (3)
C9—C8—H8B	109.3	C9—N2—C10	127.4 (3)
S1—C8—H8B	109.3	C9—N2—HN2	116.3
H8A—C8—H8B	107.9	C10—N2—HN2	116.3
O2—C9—N2	124.7 (4)	C7—O1—C6	102.7 (3)
O2—C9—C8	120.1 (4)	C15—O3—C16	116.7 (3)
N2—C9—C8	115.2 (3)	C7—S1—C8	98.82 (18)
C11—C10—C15	118.7 (4)

C6—C1—C2—C3	−0.6 (6)	N2—C10—C15—O3	−1.0 (5)
N1—C1—C2—C3	−178.6 (4)	C11—C10—C15—C14	0.2 (5)
C1—C2—C3—C4	0.4 (7)	N2—C10—C15—C14	179.1 (3)
C2—C3—C4—C5	0.1 (7)	O1—C7—N1—C1	1.2 (4)
C3—C4—C5—C6	−0.5 (6)	S1—C7—N1—C1	−177.6 (3)
C4—C5—C6—C1	0.3 (6)	C6—C1—N1—C7	−0.9 (4)
C4—C5—C6—O1	178.3 (4)	C2—C1—N1—C7	177.2 (4)
C2—C1—C6—C5	0.3 (6)	O2—C9—N2—C10	0.9 (7)
N1—C1—C6—C5	178.7 (4)	C8—C9—N2—C10	−178.8 (3)
C2—C1—C6—O1	−178.1 (3)	C11—C10—N2—C9	−10.6 (6)
N1—C1—C6—O1	0.3 (4)	C15—C10—N2—C9	170.5 (4)
S1—C8—C9—O2	−88.1 (5)	N1—C7—O1—C6	−1.1 (4)
S1—C8—C9—N2	91.6 (4)	S1—C7—O1—C6	177.9 (2)
C15—C10—C11—C12	0.5 (6)	C5—C6—O1—C7	−177.9 (4)
N2—C10—C11—C12	−178.3 (4)	C1—C6—O1—C7	0.4 (4)
C10—C11—C12—C13	−1.0 (6)	C14—C15—O3—C16	4.8 (6)
C11—C12—C13—C14	0.7 (7)	C10—C15—O3—C16	−175.1 (4)
C12—C13—C14—C15	0.1 (6)	N1—C7—S1—C8	−0.8 (4)
C13—C14—C15—O3	179.7 (4)	O1—C7—S1—C8	−179.7 (3)
C13—C14—C15—C10	−0.5 (6)	C9—C8—S1—C7	−87.7 (3)
C11—C10—C15—O3	−180.0 (3)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C10–C15 benzene ring of the methoxy phenyl group.

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN2···O3	0.86	2.22	2.608 (4)	107
N2—HN2···N1	0.86	2.39	3.075 (4)	136
C8—H8A···N1	0.97	2.48	2.914 (5)	107
C11—H11···O2	0.93	2.28	2.869 (5)	121
C12—H12···O2ⁱ	0.93	2.52	3.378 (6)	153
C13—H13···Cg3ⁱⁱ	0.93	2.89	3.634 (5)	138

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

Summary of selected short interatomic contacts (Å) in the title compound top

Contact	Distance	Symmetry operation
H5···O3	2.72	1 - x, 1 - y, 1 - z
S1···H2	3.10	x, 1/2 - y, 1/2 + z
C5···C1	3.38	1 - x, -y, 1 - z
H8B···C11	3.06	-x, 1 - y, 1 - z
H12···O2	2.52	-x, 2 - y, 1 - z
O2···H16A	2.74	x, 3/2 - y, 1/2 + z
C10···H13	3.04	-x, -1/2 + y, 1/2 - z
C12···H8A	2.82	x, 1 + y, z

Percentage contributions of interatomic contacts to the Hirshfeld surface of the title compound top

Contact	Percentage contribution
H···H	39.3
H···C/C···H	18.0
O···H/H···O	15.6
S···H/H···S	10.2
C···O/O···C	6.0
C···C	4.5
N···H/H···N	4.1
C···N/N···C	1.4
C···S/S···C	0.6
N···O/O···N	0.1

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Crystal structure and Hirshfeld surface analysis of 2-[(1,3-benzoxazol-2-yl)sulfan­yl]-N-(2-meth­oxy­phen­yl)acetamide

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure and Hirshfeld surface analysis of 2-[(1,3-benzoxazol-2-yl)sulfanyl]-N-(2-methoxyphenyl)acetamide