Download citation
Download citation
link to html
The title compound, C21H15ClN4OS, was synthesized by the reaction of 2-(1H-benzotriazol-1-yl)-1-(4-chloro­phenyl)­ethanone with phenyl isothiocyanate and potassium hydro­xide in dimethylsulfoxide. There are some inter- and intramol­ecular interactions in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680500019X/ww6347sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680500019X/ww6347Isup2.hkl
Contains datablock I

CCDC reference: 263672

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.035
  • wR factor = 0.090
  • Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C2 -C7 1.37 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 27.72 From the CIF: _reflns_number_total 3055 Count of symmetry unique reflns 2239 Completeness (_total/calc) 136.44% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 816 Fraction of Friedel pairs measured 0.364 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

2-(1H-Benzotriazol-1-yl)-3-(4-chlorophenyl)-3-hydroxy-N-phenylprop- 2-enethioamide top
Crystal data top
C21H15ClN4OSF(000) = 420
Mr = 406.88Dx = 1.422 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 1173 reflections
a = 10.2362 (12) Åθ = 3.0–21.1°
b = 8.9429 (11) ŵ = 0.33 mm1
c = 10.3855 (12) ÅT = 295 K
β = 91.887 (2)°Block, yellow
V = 950.2 (2) Å30.42 × 0.35 × 0.18 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
3055 independent reflections
Radiation source: fine-focus sealed tube2232 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 27.7°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.820, Tmax = 0.942k = 1111
5920 measured reflectionsl = 813
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.090 w = 1/[σ2(Fo2) + 0.0316P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3055 reflectionsΔρmax = 0.13 e Å3
260 parametersΔρmin = 0.15 e Å3
4 restraintsAbsolute structure: Flack (1983), 2239 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (7)
Special details top

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
xyzUiso*/Ueq
S10.21312 (7)0.83418 (9)0.97236 (7)0.0586 (2)
Cl11.00491 (10)0.53128 (16)0.68604 (14)0.1239 (5)
N10.2007 (2)0.9442 (3)0.7374 (2)0.0526 (6)
H10.233 (3)0.960 (3)0.6629 (16)0.053 (8)*
N20.4283 (2)0.8346 (3)0.6540 (2)0.0463 (5)
N30.5194 (2)0.9396 (3)0.6220 (2)0.0541 (6)
N40.5372 (2)0.9318 (3)0.5002 (2)0.0563 (6)
O10.4739 (2)0.7146 (3)0.9859 (2)0.0623 (5)
H20.3963 (17)0.741 (4)1.003 (4)0.094*
C10.2706 (3)0.8658 (3)0.8245 (3)0.0475 (6)
C20.0751 (3)1.0079 (3)0.7515 (3)0.0514 (7)
C30.0531 (4)1.1191 (4)0.8365 (4)0.0806 (11)
H30.12091.15340.89050.097*
C40.0703 (6)1.1819 (6)0.8432 (5)0.1085 (17)
H40.08551.25840.90150.130*
C50.1691 (4)1.1311 (7)0.7640 (6)0.1097 (18)
H50.25261.17090.77000.132*
C60.1463 (4)1.0233 (6)0.6768 (6)0.1063 (16)
H60.21360.99180.62090.128*
C70.0247 (3)0.9595 (4)0.6698 (4)0.0766 (10)
H70.00990.88420.61030.092*
C80.3953 (3)0.8086 (3)0.7844 (3)0.0479 (6)
C90.3886 (3)0.7585 (3)0.5461 (3)0.0445 (6)
C100.4577 (3)0.8213 (3)0.4487 (3)0.0492 (7)
C110.4425 (3)0.7702 (4)0.3218 (3)0.0612 (8)
H110.48820.81230.25490.073*
C120.3565 (4)0.6546 (4)0.3019 (3)0.0724 (10)
H120.34340.61730.21890.087*
C130.2881 (4)0.5911 (4)0.4018 (3)0.0671 (9)
H130.23140.51210.38340.081*
C140.3010 (3)0.6407 (3)0.5260 (3)0.0569 (7)
H140.25460.59880.59260.068*
C150.4875 (3)0.7376 (3)0.8615 (3)0.0517 (7)
C160.6146 (3)0.6851 (3)0.8161 (3)0.0538 (7)
C170.7266 (3)0.7255 (4)0.8839 (4)0.0678 (8)
H170.72080.78540.95670.081*
C180.8468 (4)0.6784 (5)0.8454 (4)0.0819 (11)
H180.92230.70630.89150.098*
C190.8542 (3)0.5898 (4)0.7383 (4)0.0767 (11)
C200.7447 (3)0.5444 (4)0.6707 (4)0.0730 (9)
H200.75100.48170.59970.088*
C210.6240 (3)0.5935 (4)0.7100 (3)0.0634 (8)
H210.54860.56440.66440.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0634 (4)0.0734 (5)0.0397 (4)0.0041 (4)0.0124 (3)0.0005 (4)
Cl10.0583 (5)0.1609 (11)0.1542 (12)0.0357 (6)0.0284 (6)0.0409 (9)
N10.0471 (13)0.0718 (15)0.0393 (14)0.0065 (11)0.0081 (11)0.0102 (11)
N20.0409 (11)0.0615 (13)0.0365 (12)0.0000 (10)0.0015 (10)0.0017 (11)
N30.0466 (12)0.0677 (14)0.0483 (15)0.0091 (11)0.0041 (11)0.0039 (12)
N40.0523 (14)0.0716 (16)0.0456 (15)0.0064 (12)0.0084 (12)0.0002 (12)
O10.0635 (12)0.0864 (14)0.0369 (12)0.0094 (11)0.0012 (10)0.0076 (10)
C10.0497 (15)0.0539 (15)0.0389 (15)0.0016 (13)0.0006 (13)0.0043 (13)
C20.0446 (15)0.0607 (17)0.0489 (17)0.0004 (13)0.0039 (13)0.0092 (14)
C30.073 (2)0.089 (2)0.079 (3)0.0202 (19)0.0033 (19)0.016 (2)
C40.112 (4)0.117 (4)0.097 (4)0.058 (3)0.022 (3)0.001 (3)
C50.061 (3)0.143 (4)0.126 (4)0.039 (3)0.026 (3)0.054 (4)
C60.049 (2)0.126 (4)0.142 (5)0.010 (2)0.010 (3)0.033 (4)
C70.060 (2)0.081 (2)0.087 (3)0.0036 (17)0.0078 (19)0.003 (2)
C80.0479 (14)0.0624 (17)0.0334 (14)0.0026 (12)0.0030 (12)0.0008 (13)
C90.0434 (14)0.0543 (15)0.0355 (15)0.0015 (12)0.0024 (11)0.0037 (12)
C100.0520 (16)0.0569 (16)0.0389 (16)0.0056 (13)0.0028 (13)0.0026 (13)
C110.073 (2)0.0715 (19)0.0394 (17)0.0039 (16)0.0109 (15)0.0007 (15)
C120.103 (3)0.072 (2)0.0417 (18)0.0035 (19)0.0085 (19)0.0055 (16)
C130.084 (2)0.0641 (19)0.053 (2)0.0127 (17)0.0127 (17)0.0002 (16)
C140.0569 (17)0.0656 (18)0.0477 (18)0.0032 (14)0.0049 (14)0.0094 (14)
C150.0553 (16)0.0599 (16)0.0399 (16)0.0017 (13)0.0008 (13)0.0009 (14)
C160.0474 (15)0.0680 (17)0.0456 (17)0.0063 (13)0.0050 (13)0.0082 (14)
C170.0586 (19)0.085 (2)0.059 (2)0.0016 (16)0.0067 (16)0.0099 (17)
C180.0506 (19)0.114 (3)0.081 (3)0.0053 (19)0.0105 (17)0.027 (2)
C190.0499 (19)0.092 (3)0.089 (3)0.0158 (18)0.0080 (19)0.030 (2)
C200.063 (2)0.085 (2)0.071 (2)0.0189 (18)0.0058 (18)0.0017 (18)
C210.0499 (16)0.0779 (19)0.062 (2)0.0105 (15)0.0045 (15)0.0040 (18)
Geometric parameters (Å, º) top
S1—C11.686 (3)C7—H70.9300
Cl1—C191.733 (4)C8—C151.373 (4)
N1—C11.334 (4)C9—C101.373 (4)
N1—C21.418 (4)C9—C141.395 (4)
N1—H10.863 (10)C10—C111.398 (4)
N2—C91.362 (3)C11—C121.369 (5)
N2—N31.373 (3)C11—H110.9300
N2—C81.426 (4)C12—C131.392 (5)
N3—N41.285 (3)C12—H120.9300
N4—C101.377 (4)C13—C141.366 (5)
O1—C151.320 (3)C13—H130.9300
O1—H20.853 (10)C14—H140.9300
C1—C81.448 (4)C15—C161.476 (4)
C2—C31.354 (5)C16—C171.373 (5)
C2—C71.376 (5)C16—C211.379 (4)
C3—C41.387 (6)C17—C181.372 (5)
C3—H30.9300C17—H170.9300
C4—C51.360 (8)C18—C191.370 (6)
C4—H40.9300C18—H180.9300
C5—C61.348 (7)C19—C201.365 (6)
C5—H50.9300C20—C211.386 (4)
C6—C71.374 (6)C20—H200.9300
C6—H60.9300C21—H210.9300
C1—N1—C2127.6 (2)C9—C10—N4108.6 (2)
C1—N1—H1119 (2)C9—C10—C11121.1 (3)
C2—N1—H1114 (2)N4—C10—C11130.3 (3)
C9—N2—N3109.2 (2)C12—C11—C10116.1 (3)
C9—N2—C8128.8 (2)C12—C11—H11121.9
N3—N2—C8121.8 (2)C10—C11—H11121.9
N4—N3—N2108.7 (2)C11—C12—C13122.2 (3)
N3—N4—C10108.7 (2)C11—C12—H12118.9
C15—O1—H2107 (3)C13—C12—H12118.9
N1—C1—C8116.7 (2)C14—C13—C12122.4 (3)
N1—C1—S1120.7 (2)C14—C13—H13118.8
C8—C1—S1122.6 (2)C12—C13—H13118.8
C3—C2—C7119.8 (3)C13—C14—C9115.3 (3)
C3—C2—N1122.2 (3)C13—C14—H14122.3
C7—C2—N1117.9 (3)C9—C14—H14122.3
C2—C3—C4120.1 (4)O1—C15—C8123.4 (3)
C2—C3—H3120.0O1—C15—C16112.7 (2)
C4—C3—H3120.0C8—C15—C16123.9 (3)
C5—C4—C3119.7 (5)C17—C16—C21119.1 (3)
C5—C4—H4120.2C17—C16—C15118.8 (3)
C3—C4—H4120.2C21—C16—C15122.0 (3)
C6—C5—C4120.3 (4)C18—C17—C16120.7 (4)
C6—C5—H5119.9C18—C17—H17119.6
C4—C5—H5119.9C16—C17—H17119.6
C5—C6—C7120.6 (5)C19—C18—C17119.2 (4)
C5—C6—H6119.7C19—C18—H18120.4
C7—C6—H6119.7C17—C18—H18120.4
C6—C7—C2119.5 (4)C20—C19—C18121.6 (3)
C6—C7—H7120.2C20—C19—Cl1118.2 (3)
C2—C7—H7120.2C18—C19—Cl1120.2 (3)
C15—C8—N2116.7 (2)C19—C20—C21118.6 (3)
C15—C8—C1126.2 (2)C19—C20—H20120.7
N2—C8—C1117.0 (2)C21—C20—H20120.7
N2—C9—C10104.8 (2)C16—C21—C20120.7 (3)
N2—C9—C14132.3 (3)C16—C21—H21119.7
C10—C9—C14122.9 (3)C20—C21—H21119.7
C9—N2—N3—N40.1 (3)N2—C9—C10—C11179.7 (3)
C8—N2—N3—N4175.2 (2)C14—C9—C10—C110.7 (4)
N2—N3—N4—C100.1 (3)N3—N4—C10—C90.3 (3)
C2—N1—C1—C8178.1 (3)N3—N4—C10—C11179.6 (3)
C2—N1—C1—S10.9 (4)C9—C10—C11—C120.6 (4)
C1—N1—C2—C364.9 (4)N4—C10—C11—C12178.6 (3)
C1—N1—C2—C7118.9 (4)C10—C11—C12—C130.1 (5)
C7—C2—C3—C41.3 (6)C11—C12—C13—C140.7 (5)
N1—C2—C3—C4177.5 (4)C12—C13—C14—C90.6 (5)
C2—C3—C4—C50.1 (7)N2—C9—C14—C13178.8 (3)
C3—C4—C5—C61.9 (8)C10—C9—C14—C130.1 (4)
C4—C5—C6—C72.4 (7)N2—C8—C15—O1175.5 (2)
C5—C6—C7—C20.9 (6)C1—C8—C15—O11.3 (4)
C3—C2—C7—C60.9 (5)N2—C8—C15—C161.5 (4)
N1—C2—C7—C6177.2 (3)C1—C8—C15—C16178.3 (3)
C9—N2—C8—C15102.3 (3)O1—C15—C16—C1748.6 (4)
N3—N2—C8—C1571.7 (3)C8—C15—C16—C17128.7 (3)
C9—N2—C8—C180.6 (3)O1—C15—C16—C21129.5 (3)
N3—N2—C8—C1105.4 (3)C8—C15—C16—C2153.2 (4)
N1—C1—C8—C15173.6 (3)C21—C16—C17—C181.4 (5)
S1—C1—C8—C157.4 (4)C15—C16—C17—C18179.6 (3)
N1—C1—C8—N23.2 (4)C16—C17—C18—C190.2 (5)
S1—C1—C8—N2175.8 (2)C17—C18—C19—C201.6 (5)
N3—N2—C9—C100.3 (3)C17—C18—C19—Cl1179.0 (3)
C8—N2—C9—C10174.9 (2)C18—C19—C20—C212.0 (5)
N3—N2—C9—C14178.6 (3)Cl1—C19—C20—C21178.5 (3)
C8—N2—C9—C144.0 (5)C17—C16—C21—C201.0 (5)
N2—C9—C10—N40.4 (3)C15—C16—C21—C20179.1 (3)
C14—C9—C10—N4178.7 (3)C19—C20—C21—C160.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S1i0.86 (1)2.70 (2)3.398 (2)138 (2)
O1—H2···S10.85 (1)2.07 (2)2.875 (2)157 (4)
Symmetry code: (i) x, y+2, z1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds