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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019012908/rz5264sup1.cif
Contains datablock I

hkl

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

CCDC reference: 1954699

Key indicators

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

checkCIF/PLATON results

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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
C16H14N2O3SF(000) = 656
Mr = 314.35Dx = 1.398 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.6670 (13) ÅCell parameters from 6692 reflections
b = 6.8704 (6) Åθ = 3.2–26.3°
c = 16.7220 (16) ŵ = 0.23 mm1
β = 108.020 (4)°T = 296 K
V = 1493.1 (2) Å3Block, colourless
Z = 40.10 × 0.07 × 0.06 mm
Data collection top
Bruker APEXII CCD
diffractometer
2241 reflections with I > 2σ(I)
φ and ω scansRint = 0.092
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
θmax = 26.5°, θmin = 3.1°
Tmin = 0.654, Tmax = 0.745h = 1717
23464 measured reflectionsk = 88
3019 independent reflectionsl = 2020
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.092H-atom parameters constrained
wR(F2) = 0.169 w = 1/[σ2(Fo2) + (0.0406P)2 + 3.9251P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
3019 reflectionsΔρmax = 0.25 e Å3
200 parametersΔρmin = 0.31 e Å3
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
xyzUiso*/Ueq
C10.4055 (3)0.2452 (5)0.4388 (2)0.0301 (9)
C20.4121 (3)0.1973 (6)0.3599 (3)0.0437 (11)
H20.3535780.1867940.3133500.052*
C30.5089 (4)0.1660 (7)0.3535 (3)0.0507 (12)
H30.5156640.1345450.3013490.061*
C40.5962 (4)0.1801 (6)0.4223 (3)0.0515 (13)
H40.6601820.1581270.4152810.062*
C50.5910 (3)0.2258 (6)0.5012 (3)0.0460 (11)
H50.6493540.2347240.5479610.055*
C60.4940 (3)0.2573 (5)0.5059 (3)0.0330 (9)
C70.3608 (3)0.3093 (5)0.5452 (2)0.0304 (9)
C80.1670 (3)0.3513 (7)0.5515 (3)0.0401 (10)
H8A0.1606680.2587150.5064320.048*
H8B0.1222570.3089190.5832440.048*
C90.1330 (3)0.5503 (6)0.5143 (2)0.0368 (10)
C100.1249 (3)0.7568 (6)0.3915 (2)0.0272 (8)
C110.0683 (3)0.9111 (6)0.4077 (2)0.0364 (10)
H110.0440480.9061290.4538180.044*
C120.0479 (3)1.0720 (7)0.3557 (3)0.0438 (11)
H120.0089781.1738970.3665200.053*
C130.0844 (3)1.0826 (7)0.2882 (3)0.0443 (11)
H130.0709461.1919800.2537730.053*
C140.1411 (3)0.9312 (7)0.2714 (2)0.0380 (10)
H140.1658370.9389780.2255600.046*
C150.1615 (3)0.7687 (6)0.3217 (2)0.0290 (9)
C160.2621 (5)0.6219 (9)0.2449 (3)0.078 (2)
H16A0.2091730.6345670.1917950.118*
H16B0.3012140.5059560.2447190.118*
H16C0.3067390.7331120.2538720.118*
N10.3202 (2)0.2815 (5)0.46627 (18)0.0309 (7)
N20.1476 (2)0.5848 (5)0.43945 (19)0.0302 (7)
HN20.1736300.4910510.4186150.036*
O10.4653 (2)0.3005 (4)0.57658 (16)0.0363 (7)
O20.0961 (3)0.6653 (6)0.55175 (19)0.0687 (11)
O30.2163 (2)0.6103 (4)0.31065 (17)0.0467 (8)
S10.29895 (9)0.35394 (17)0.62002 (6)0.0420 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.036 (2)0.0217 (18)0.032 (2)0.0038 (16)0.0093 (17)0.0053 (16)
C20.047 (3)0.045 (3)0.039 (2)0.002 (2)0.013 (2)0.000 (2)
C30.059 (3)0.046 (3)0.058 (3)0.006 (2)0.033 (3)0.001 (2)
C40.044 (3)0.036 (2)0.085 (4)0.005 (2)0.035 (3)0.009 (2)
C50.032 (2)0.035 (2)0.066 (3)0.0031 (19)0.007 (2)0.009 (2)
C60.038 (2)0.0217 (19)0.039 (2)0.0024 (17)0.0112 (18)0.0046 (17)
C70.036 (2)0.024 (2)0.029 (2)0.0016 (16)0.0067 (17)0.0061 (16)
C80.041 (2)0.052 (3)0.034 (2)0.009 (2)0.0208 (19)0.000 (2)
C90.036 (2)0.053 (3)0.026 (2)0.001 (2)0.0156 (18)0.0053 (19)
C100.0190 (18)0.040 (2)0.0195 (18)0.0011 (16)0.0007 (15)0.0058 (16)
C110.027 (2)0.050 (3)0.030 (2)0.0069 (19)0.0060 (17)0.0084 (19)
C120.035 (2)0.049 (3)0.040 (3)0.017 (2)0.002 (2)0.010 (2)
C130.043 (3)0.044 (3)0.038 (2)0.012 (2)0.000 (2)0.005 (2)
C140.034 (2)0.055 (3)0.022 (2)0.004 (2)0.0055 (17)0.0048 (19)
C150.0247 (19)0.040 (2)0.0224 (18)0.0045 (17)0.0067 (15)0.0009 (17)
C160.117 (5)0.081 (4)0.066 (4)0.054 (4)0.071 (4)0.027 (3)
N10.0325 (18)0.0342 (18)0.0236 (17)0.0008 (14)0.0055 (14)0.0010 (14)
N20.0334 (18)0.0369 (18)0.0261 (16)0.0024 (14)0.0177 (14)0.0058 (14)
O10.0348 (16)0.0358 (15)0.0311 (15)0.0026 (13)0.0002 (12)0.0042 (12)
O20.101 (3)0.082 (3)0.0401 (19)0.035 (2)0.046 (2)0.0056 (18)
O30.062 (2)0.0517 (19)0.0380 (17)0.0240 (16)0.0333 (15)0.0094 (14)
S10.0516 (7)0.0517 (7)0.0226 (5)0.0004 (6)0.0114 (5)0.0050 (5)
Geometric parameters (Å, º) top
C1—C61.375 (6)C9—O21.211 (5)
C1—C21.389 (5)C9—N21.348 (5)
C1—N11.401 (5)C10—C111.388 (5)
C2—C31.377 (6)C10—C151.406 (5)
C2—H20.9300C10—N21.408 (5)
C3—C41.382 (7)C11—C121.381 (6)
C3—H30.9300C11—H110.9300
C4—C51.379 (7)C12—C131.370 (6)
C4—H40.9300C12—H120.9300
C5—C61.370 (6)C13—C141.377 (6)
C5—H50.9300C13—H130.9300
C6—O11.388 (5)C14—C151.374 (6)
C7—N11.278 (5)C14—H140.9300
C7—O11.362 (5)C15—O31.366 (4)
C7—S11.740 (4)C16—O31.426 (5)
C8—C91.514 (6)C16—H16A0.9600
C8—S11.812 (4)C16—H16B0.9600
C8—H8A0.9700C16—H16C0.9600
C8—H8B0.9700N2—HN20.8600
C6—C1—C2119.4 (4)C11—C10—N2124.6 (3)
C6—C1—N1109.4 (3)C15—C10—N2116.7 (3)
C2—C1—N1131.2 (4)C12—C11—C10120.4 (4)
C3—C2—C1117.2 (4)C12—C11—H11119.8
C3—C2—H2121.4C10—C11—H11119.8
C1—C2—H2121.4C13—C12—C11120.4 (4)
C2—C3—C4121.8 (4)C13—C12—H12119.8
C2—C3—H3119.1C11—C12—H12119.8
C4—C3—H3119.1C12—C13—C14120.0 (4)
C5—C4—C3121.8 (4)C12—C13—H13120.0
C5—C4—H4119.1C14—C13—H13120.0
C3—C4—H4119.1C15—C14—C13120.6 (4)
C6—C5—C4115.3 (4)C15—C14—H14119.7
C6—C5—H5122.3C13—C14—H14119.7
C4—C5—H5122.3O3—C15—C14125.4 (3)
C5—C6—C1124.5 (4)O3—C15—C10114.6 (3)
C5—C6—O1128.0 (4)C14—C15—C10120.0 (4)
C1—C6—O1107.4 (3)O3—C16—H16A109.5
N1—C7—O1117.4 (3)O3—C16—H16B109.5
N1—C7—S1128.1 (3)H16A—C16—H16B109.5
O1—C7—S1114.5 (3)O3—C16—H16C109.5
C9—C8—S1111.7 (3)H16A—C16—H16C109.5
C9—C8—H8A109.3H16B—C16—H16C109.5
S1—C8—H8A109.3C7—N1—C1103.1 (3)
C9—C8—H8B109.3C9—N2—C10127.4 (3)
S1—C8—H8B109.3C9—N2—HN2116.3
H8A—C8—H8B107.9C10—N2—HN2116.3
O2—C9—N2124.7 (4)C7—O1—C6102.7 (3)
O2—C9—C8120.1 (4)C15—O3—C16116.7 (3)
N2—C9—C8115.2 (3)C7—S1—C898.82 (18)
C11—C10—C15118.7 (4)
C6—C1—C2—C30.6 (6)N2—C10—C15—O31.0 (5)
N1—C1—C2—C3178.6 (4)C11—C10—C15—C140.2 (5)
C1—C2—C3—C40.4 (7)N2—C10—C15—C14179.1 (3)
C2—C3—C4—C50.1 (7)O1—C7—N1—C11.2 (4)
C3—C4—C5—C60.5 (6)S1—C7—N1—C1177.6 (3)
C4—C5—C6—C10.3 (6)C6—C1—N1—C70.9 (4)
C4—C5—C6—O1178.3 (4)C2—C1—N1—C7177.2 (4)
C2—C1—C6—C50.3 (6)O2—C9—N2—C100.9 (7)
N1—C1—C6—C5178.7 (4)C8—C9—N2—C10178.8 (3)
C2—C1—C6—O1178.1 (3)C11—C10—N2—C910.6 (6)
N1—C1—C6—O10.3 (4)C15—C10—N2—C9170.5 (4)
S1—C8—C9—O288.1 (5)N1—C7—O1—C61.1 (4)
S1—C8—C9—N291.6 (4)S1—C7—O1—C6177.9 (2)
C15—C10—C11—C120.5 (6)C5—C6—O1—C7177.9 (4)
N2—C10—C11—C12178.3 (4)C1—C6—O1—C70.4 (4)
C10—C11—C12—C131.0 (6)C14—C15—O3—C164.8 (6)
C11—C12—C13—C140.7 (7)C10—C15—O3—C16175.1 (4)
C12—C13—C14—C150.1 (6)N1—C7—S1—C80.8 (4)
C13—C14—C15—O3179.7 (4)O1—C7—S1—C8179.7 (3)
C13—C14—C15—C100.5 (6)C9—C8—S1—C787.7 (3)
C11—C10—C15—O3180.0 (3)
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C10–C15 benzene ring of the methoxy phenyl group.
D—H···AD—HH···AD···AD—H···A
N2—HN2···O30.862.222.608 (4)107
N2—HN2···N10.862.393.075 (4)136
C8—H8A···N10.972.482.914 (5)107
C11—H11···O20.932.282.869 (5)121
C12—H12···O2i0.932.523.378 (6)153
C13—H13···Cg3ii0.932.893.634 (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
ContactDistanceSymmetry operation
H5···O32.721 - x, 1 - y, 1 - z
S1···H23.10x, 1/2 - y, 1/2 + z
C5···C13.381 - x, -y, 1 - z
H8B···C113.06-x, 1 - y, 1 - z
H12···O22.52-x, 2 - y, 1 - z
O2···H16A2.74x, 3/2 - y, 1/2 + z
C10···H133.04-x, -1/2 + y, 1/2 - z
C12···H8A2.82x, 1 + y, z
Percentage contributions of interatomic contacts to the Hirshfeld surface of the title compound top
ContactPercentage contribution
H···H39.3
H···C/C···H18.0
O···H/H···O15.6
S···H/H···S10.2
C···O/O···C6.0
C···C4.5
N···H/H···N4.1
C···N/N···C1.4
C···S/S···C0.6
N···O/O···N0.1
 

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