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The title compound crystallizes in space group P1 despite being achiral. Two classical hydrogen bonds link the mol­ecules to form a layer structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021007672/yk2155sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989021007672/yk2155Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989021007672/yk2155Isup3.cml
Supplementary material

CCDC reference: 2099652

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.030
  • wR factor = 0.078
  • Data-to-parameter ratio = 31.5

checkCIF/PLATON results

No syntax errors found



Alert level G PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 2 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 201 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 13 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 0 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2020); cell refinement: CrysAlis PRO (Rigaku OD, 2020); data reduction: CrysAlis PRO (Rigaku OD, 2020); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015b).

N'-[2-(Benzo[d]thiazol-2-yl)acetyl]benzohydrazide top
Crystal data top
C16H13N3O2SZ = 1
Mr = 311.35F(000) = 162
Triclinic, P1Dx = 1.438 Mg m3
a = 4.71248 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 6.96463 (14) ÅCell parameters from 40070 reflections
c = 11.5455 (3) Åθ = 3.0–37.0°
α = 105.6168 (18)°µ = 0.24 mm1
β = 95.7876 (16)°T = 100 K
γ = 95.9993 (16)°Plate, colourless
V = 359.64 (1) Å30.20 × 0.16 × 0.05 mm
Data collection top
XtaLAB Synergy, HyPix
diffractometer
6522 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source6312 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.034
Detector resolution: 10.0000 pixels mm-1θmax = 36.8°, θmin = 3.1°
ω scansh = 77
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2020)
k = 1111
Tmin = 0.844, Tmax = 1.000l = 1819
60895 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.030 w = 1/[σ2(Fo2) + (0.0486P)2 + 0.0499P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.078(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.41 e Å3
6522 reflectionsΔρmin = 0.27 e Å3
207 parametersAbsolute structure: Flack x determined using 2959 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
3 restraintsAbsolute structure parameter: 0.016 (12)
Primary atom site location: structure-invariant direct methods
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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

3.5462 (0.0009) x + 3.6978 (0.0019) y - 0.2128 (0.0045) z = 6.1650 (0.0025)

* -0.0069 (0.0007) S1 * 0.0023 (0.0009) C2 * 0.0044 (0.0009) N3 * -0.0011 (0.0011) C4 * -0.0046 (0.0012) C5 * 0.0007 (0.0012) C6 * 0.0082 (0.0011) C7 * -0.0004 (0.0011) C3A * -0.0026 (0.0011) C7A -0.0318 (0.0015) C8

Rms deviation of fitted atoms = 0.0043

- 3.3343 (0.0019) x + 1.8849 (0.0037) y + 7.6563 (0.0052) z = 0.2749 (0.0019)

Angle to previous plane (with approximate esd) = 75.652 ( 0.033 )

* 0.0041 (0.0009) C11 * 0.0008 (0.0009) C12 * -0.0051 (0.0009) C13 * 0.0044 (0.0010) C14 * 0.0006 (0.0010) C15 * -0.0049 (0.0009) C16 -0.0026 (0.0020) C10

Rms deviation of fitted atoms = 0.0038

=============================================================================

- 0.0418 (0.0830) x - 3.0734 (0.0043) y + 11.3227 (0.0146) z = 3.7743 (0.0598)

* 0.0000 (0.0000) N2 * 0.0000 (0.0001) C9 * 0.0000 (0.0000) H01 0.0634 (0.0123) N1

Rms deviation of fitted atoms = 0.0000

4.0751 (0.0123) x - 3.1432 (0.0992) y - 3.6530 (0.1475) z = 1.0965 (0.0176)

* 0.0000 (0.0001) N1 * 0.0000 (0.0001) C10 * 0.0000 (0.0000) H02 0.1480 (0.0122) N2

Rms deviation of fitted atoms = 0.0000

=============================================================================

Further torsion angles:

97.53 ( 0.11) O2 - C10 ··· C9 - O1 175.44 ( 2.18) H01 - N1 - C9 - O1 165.89 ( 2.18) H02 - N2 - C10 - O2 101.08 ( 2.76) H01 - N1 - N2 - H02

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.88408 (5)0.86164 (4)0.76703 (3)0.01738 (7)
C20.8642 (3)0.87459 (17)0.61788 (11)0.01314 (18)
N10.9484 (2)0.36700 (15)0.44206 (10)0.01379 (17)
H011.135 (6)0.377 (4)0.440 (3)0.031 (6)*
N20.7891 (2)0.17967 (15)0.38503 (10)0.01379 (17)
H020.743 (6)0.111 (4)0.433 (2)0.025 (6)*
N30.7208 (2)1.01131 (16)0.59308 (10)0.01420 (17)
C3A0.6136 (3)1.11873 (18)0.69578 (11)0.01407 (18)
C40.4492 (3)1.2765 (2)0.70032 (13)0.0202 (2)
H40.4012271.3189210.6300630.024*
C50.3581 (3)1.3691 (2)0.80960 (15)0.0232 (3)
H50.2455661.4756980.8139130.028*
C60.4294 (3)1.3082 (2)0.91385 (13)0.0214 (2)
H60.3643721.3743790.9876360.026*
C70.5928 (3)1.1534 (2)0.91122 (12)0.0191 (2)
H70.6425081.1130380.9821180.023*
C7A0.6821 (3)1.05845 (18)0.80085 (11)0.01465 (19)
C81.0007 (3)0.72931 (17)0.52744 (11)0.01505 (19)
H8A1.1886940.7098030.5660300.018*
H8B1.0358890.7850890.4590450.018*
C90.8084 (3)0.52723 (17)0.47944 (11)0.01345 (18)
O10.5458 (2)0.51401 (15)0.47552 (10)0.01766 (17)
C100.6341 (3)0.15543 (17)0.27343 (11)0.01340 (18)
O20.6698 (2)0.27818 (15)0.21612 (10)0.01878 (17)
C110.4201 (3)0.03063 (17)0.22693 (11)0.01309 (18)
C120.4296 (3)0.19751 (18)0.27175 (12)0.01574 (19)
H120.5761520.1950840.3352010.019*
C130.2252 (3)0.36724 (18)0.22370 (12)0.0172 (2)
H130.2332530.4810090.2538460.021*
C140.0089 (3)0.37052 (19)0.13160 (12)0.0180 (2)
H140.1322760.4857580.0996610.022*
C150.0006 (3)0.2051 (2)0.08620 (13)0.0191 (2)
H150.1479190.2080410.0229250.023*
C160.2046 (3)0.03535 (19)0.13308 (12)0.0164 (2)
H160.1984290.0769760.1014560.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01905 (14)0.01772 (12)0.01655 (12)0.00614 (9)0.00163 (9)0.00577 (9)
C20.0104 (5)0.0131 (4)0.0151 (4)0.0011 (3)0.0022 (3)0.0026 (3)
N10.0089 (4)0.0117 (4)0.0194 (4)0.0008 (3)0.0019 (3)0.0024 (3)
N20.0133 (4)0.0114 (4)0.0158 (4)0.0007 (3)0.0011 (3)0.0038 (3)
N30.0136 (4)0.0139 (4)0.0150 (4)0.0025 (3)0.0025 (3)0.0034 (3)
C3A0.0126 (5)0.0129 (4)0.0161 (4)0.0021 (3)0.0019 (3)0.0030 (3)
C40.0209 (6)0.0178 (5)0.0229 (6)0.0084 (4)0.0036 (4)0.0054 (4)
C50.0203 (6)0.0198 (5)0.0274 (6)0.0077 (4)0.0049 (5)0.0008 (5)
C60.0173 (6)0.0214 (6)0.0212 (6)0.0023 (4)0.0051 (4)0.0023 (4)
C70.0182 (6)0.0214 (5)0.0156 (5)0.0017 (4)0.0032 (4)0.0015 (4)
C7A0.0132 (5)0.0146 (4)0.0152 (4)0.0019 (3)0.0023 (3)0.0025 (3)
C80.0104 (5)0.0126 (4)0.0200 (5)0.0006 (3)0.0042 (4)0.0006 (4)
C90.0106 (5)0.0128 (4)0.0160 (4)0.0009 (3)0.0026 (3)0.0025 (3)
O10.0094 (4)0.0163 (4)0.0253 (4)0.0008 (3)0.0032 (3)0.0026 (3)
C100.0128 (5)0.0120 (4)0.0158 (4)0.0013 (3)0.0032 (3)0.0043 (3)
O20.0217 (5)0.0158 (4)0.0194 (4)0.0020 (3)0.0015 (3)0.0081 (3)
C110.0133 (5)0.0113 (4)0.0148 (4)0.0006 (3)0.0029 (3)0.0039 (3)
C120.0158 (5)0.0130 (4)0.0182 (5)0.0005 (4)0.0007 (4)0.0051 (4)
C130.0192 (6)0.0121 (4)0.0198 (5)0.0009 (4)0.0029 (4)0.0047 (4)
C140.0170 (5)0.0156 (5)0.0190 (5)0.0022 (4)0.0028 (4)0.0025 (4)
C150.0167 (6)0.0193 (5)0.0198 (5)0.0015 (4)0.0015 (4)0.0058 (4)
C160.0158 (5)0.0156 (5)0.0179 (5)0.0003 (4)0.0005 (4)0.0065 (4)
Geometric parameters (Å, º) top
S1—C7A1.7310 (13)C11—C161.3994 (17)
S1—C21.7422 (12)C12—C131.3909 (17)
C2—N31.2993 (16)C13—C141.390 (2)
C2—C81.4933 (17)C14—C151.3911 (19)
N1—C91.3488 (16)C15—C161.3919 (18)
N1—N21.3901 (14)N1—H010.88 (3)
N2—C101.3747 (16)N2—H020.85 (3)
N3—C3A1.3939 (16)C4—H40.9500
C3A—C41.4018 (18)C5—H50.9500
C3A—C7A1.4056 (17)C6—H60.9500
C4—C51.386 (2)C7—H70.9500
C5—C61.401 (2)C8—H8A0.9900
C6—C71.385 (2)C8—H8B0.9900
C7—C7A1.3967 (19)C12—H120.9500
C8—C91.5237 (16)C13—H130.9500
C9—O11.2266 (15)C14—H140.9500
C10—O21.2222 (14)C15—H150.9500
C10—C111.4925 (16)C16—H160.9500
C11—C121.3967 (17)
C7A—S1—C289.49 (6)C14—C15—C16120.28 (12)
N3—C2—C8124.45 (11)C15—C16—C11119.80 (11)
N3—C2—S1115.83 (9)C9—N1—H01123.3 (19)
C8—C2—S1119.70 (9)N2—N1—H01116.8 (19)
C9—N1—N2119.00 (10)C10—N2—H02123.3 (18)
C10—N2—N1117.28 (10)N1—N2—H02114.4 (18)
C2—N3—C3A110.61 (10)C5—C4—H4120.7
N3—C3A—C4125.26 (11)C3A—C4—H4120.7
N3—C3A—C7A114.95 (11)C4—C5—H5119.4
C4—C3A—C7A119.79 (12)C6—C5—H5119.4
C5—C4—C3A118.52 (13)C7—C6—H6119.4
C4—C5—C6121.11 (13)C5—C6—H6119.4
C7—C6—C5121.18 (13)C6—C7—H7121.1
C6—C7—C7A117.77 (13)C7A—C7—H7121.1
C7—C7A—C3A121.63 (12)C2—C8—H8A109.5
C7—C7A—S1129.24 (10)C9—C8—H8A109.5
C3A—C7A—S1109.13 (9)C2—C8—H8B109.5
C2—C8—C9110.93 (10)C9—C8—H8B109.5
O1—C9—N1123.27 (11)H8A—C8—H8B108.0
O1—C9—C8121.67 (11)C13—C12—H12119.9
N1—C9—C8115.06 (10)C11—C12—H12119.9
O2—C10—N2122.11 (11)C14—C13—H13120.0
O2—C10—C11122.31 (11)C12—C13—H13120.0
N2—C10—C11115.59 (10)C13—C14—H14120.0
C12—C11—C16119.69 (11)C15—C14—H14120.0
C12—C11—C10122.96 (11)C14—C15—H15119.9
C16—C11—C10117.35 (10)C16—C15—H15119.9
C13—C12—C11120.15 (11)C15—C16—H16120.1
C14—C13—C12120.05 (11)C11—C16—H16120.1
C13—C14—C15120.02 (11)
C7A—S1—C2—N30.19 (10)N2—N1—C9—O16.66 (18)
C7A—S1—C2—C8178.46 (10)N2—N1—C9—C8173.21 (10)
C9—N1—N2—C1066.44 (15)C2—C8—C9—O127.72 (16)
C8—C2—N3—C3A178.23 (11)C2—C8—C9—N1152.41 (11)
S1—C2—N3—C3A0.05 (14)N1—N2—C10—O212.34 (18)
C2—N3—C3A—C4179.93 (12)N1—N2—C10—C11167.79 (10)
C2—N3—C3A—C7A0.16 (15)O2—C10—C11—C12161.41 (13)
N3—C3A—C4—C5179.93 (13)N2—C10—C11—C1218.46 (17)
C7A—C3A—C4—C50.0 (2)O2—C10—C11—C1617.71 (18)
C3A—C4—C5—C60.4 (2)N2—C10—C11—C16162.42 (11)
C4—C5—C6—C70.1 (2)C16—C11—C12—C130.29 (19)
C5—C6—C7—C7A0.6 (2)C10—C11—C12—C13179.40 (12)
C6—C7—C7A—C3A0.96 (19)C11—C12—C13—C140.6 (2)
C6—C7—C7A—S1179.59 (11)C12—C13—C14—C150.9 (2)
N3—C3A—C7A—C7179.25 (12)C13—C14—C15—C160.4 (2)
C4—C3A—C7A—C70.65 (19)C14—C15—C16—C110.5 (2)
N3—C3A—C7A—S10.30 (13)C12—C11—C16—C150.84 (19)
C4—C3A—C7A—S1179.80 (10)C10—C11—C16—C15179.99 (12)
C2—S1—C7A—C7179.25 (13)O1—C9—N1—H01175 (2)
C2—S1—C7A—C3A0.26 (9)O2—C10—N2—H02166 (2)
N3—C2—C8—C997.86 (14)H01—N1—N2—H02101 (3)
S1—C2—C8—C980.26 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H01···O1i0.88 (3)2.02 (3)2.8438 (14)157 (3)
N2—H02···N3ii0.85 (3)2.15 (3)2.9736 (15)162 (3)
Symmetry codes: (i) x+1, y, z; (ii) x, y1, z.
 

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