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In the crystal structure of the title compound, C22H16ClN3O3, weak inter­molecular C—H...N hydrogen bonds link the mol­ecules into chains extended along the c axis. The packing is further stabilized by weak C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806004879/cv6639sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806004879/cv6639Isup2.hkl
Contains datablock I

CCDC reference: 601152

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.046
  • wR factor = 0.116
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C22 H16 Cl N3 O3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

2-(1H-1,2,3-Benzotriazol-1-yl)-1-benzoylethyl 2-chlorobenzoate top
Crystal data top
C22H16ClN3O3F(000) = 840
Mr = 405.83Dx = 1.406 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.9341 (9) ÅCell parameters from 3073 reflections
b = 9.4562 (7) Åθ = 2.5–24.9°
c = 18.1878 (9) ŵ = 0.23 mm1
β = 120.441 (3)°T = 293 K
V = 1917.9 (2) Å3Column, colourless
Z = 40.40 × 0.23 × 0.10 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
3769 independent reflections
Radiation source: fine-focus sealed tube2894 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 1.8°
ω scansh = 1515
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 911
Tmin = 0.914, Tmax = 0.978l = 1622
10521 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0519P)2 + 0.4844P]
where P = (Fo2 + 2Fc2)/3
3769 reflections(Δ/σ)max < 0.001
262 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.31 e Å3
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
Cl10.25271 (5)0.47468 (7)0.11294 (4)0.0730 (2)
O10.30772 (13)0.03438 (16)0.22333 (10)0.0639 (4)
O20.23839 (11)0.22502 (13)0.21066 (8)0.0479 (3)
O30.24809 (14)0.27458 (17)0.32715 (9)0.0634 (4)
N10.12068 (14)0.01438 (16)0.15195 (10)0.0440 (4)
N20.05081 (15)0.12997 (18)0.16688 (11)0.0547 (4)
N30.10494 (17)0.21623 (19)0.10296 (12)0.0619 (5)
C10.00935 (18)0.0806 (2)0.40210 (13)0.0519 (5)
H1A0.02020.01040.40600.062*
C20.0592 (2)0.1808 (3)0.46329 (14)0.0665 (6)
H2B0.13390.15650.50910.080*
C30.0164 (3)0.3164 (3)0.45605 (17)0.0747 (7)
H3B0.06310.38400.49660.090*
C40.0940 (3)0.3525 (3)0.38992 (18)0.0763 (7)
H4A0.12210.44450.38550.092*
C50.1635 (2)0.2538 (2)0.33011 (15)0.0623 (6)
H5A0.23910.27880.28570.075*
C60.12193 (17)0.1162 (2)0.33524 (12)0.0446 (4)
C70.20157 (18)0.0127 (2)0.26979 (12)0.0448 (4)
C80.14600 (16)0.12288 (19)0.25994 (12)0.0432 (4)
H8A0.09210.16230.31670.052*
C90.07555 (16)0.0990 (2)0.21485 (12)0.0457 (5)
H9A0.00700.07810.25740.055*
H9B0.07570.18620.18670.055*
C100.22372 (16)0.0272 (2)0.07511 (12)0.0440 (4)
C110.32396 (18)0.0592 (2)0.02972 (13)0.0569 (5)
H11A0.33070.14650.05040.068*
C120.4116 (2)0.0076 (3)0.04696 (14)0.0672 (6)
H12A0.47990.06180.07960.081*
C130.4020 (2)0.1241 (3)0.07812 (14)0.0708 (7)
H13A0.46430.15500.13050.085*
C140.3043 (2)0.2079 (3)0.03405 (14)0.0684 (6)
H14A0.29840.29510.05520.082*
C150.21266 (19)0.1573 (2)0.04465 (12)0.0510 (5)
C160.27757 (17)0.29958 (19)0.25433 (12)0.0447 (4)
C170.36468 (17)0.41235 (19)0.20297 (12)0.0448 (4)
C180.36377 (18)0.4934 (2)0.13947 (13)0.0495 (5)
C190.4487 (2)0.5965 (2)0.09722 (15)0.0644 (6)
H19A0.44630.65120.05560.077*
C200.5370 (2)0.6183 (3)0.11687 (16)0.0718 (7)
H20A0.59530.68670.08750.086*
C210.5399 (2)0.5405 (3)0.17897 (17)0.0710 (7)
H21A0.60000.55590.19190.085*
C220.4540 (2)0.4399 (2)0.22220 (15)0.0593 (6)
H22A0.45540.38880.26540.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0669 (4)0.0811 (4)0.0823 (4)0.0094 (3)0.0462 (3)0.0283 (3)
O10.0438 (8)0.0650 (10)0.0661 (10)0.0060 (7)0.0155 (7)0.0039 (7)
O20.0518 (8)0.0433 (7)0.0413 (7)0.0108 (6)0.0182 (6)0.0043 (6)
O30.0763 (10)0.0681 (10)0.0481 (8)0.0164 (8)0.0332 (8)0.0119 (7)
N10.0413 (8)0.0403 (9)0.0459 (9)0.0059 (7)0.0188 (7)0.0032 (7)
N20.0540 (10)0.0461 (10)0.0576 (10)0.0111 (8)0.0235 (9)0.0042 (8)
N30.0697 (12)0.0477 (10)0.0613 (11)0.0098 (9)0.0281 (10)0.0017 (9)
C10.0548 (12)0.0488 (12)0.0504 (12)0.0063 (10)0.0253 (10)0.0081 (9)
C20.0647 (14)0.0776 (17)0.0506 (13)0.0158 (12)0.0243 (11)0.0150 (11)
C30.100 (2)0.0647 (16)0.0705 (16)0.0292 (15)0.0514 (16)0.0334 (13)
C40.107 (2)0.0487 (13)0.0840 (18)0.0030 (14)0.0564 (17)0.0172 (12)
C50.0754 (15)0.0512 (13)0.0648 (14)0.0063 (11)0.0388 (12)0.0038 (10)
C60.0513 (11)0.0435 (11)0.0435 (10)0.0035 (8)0.0275 (9)0.0043 (8)
C70.0454 (11)0.0460 (11)0.0420 (10)0.0004 (9)0.0213 (9)0.0022 (8)
C80.0414 (10)0.0392 (10)0.0399 (10)0.0045 (8)0.0138 (8)0.0039 (8)
C90.0407 (10)0.0426 (11)0.0465 (11)0.0003 (8)0.0166 (9)0.0012 (8)
C100.0438 (10)0.0455 (11)0.0416 (10)0.0020 (8)0.0208 (9)0.0025 (8)
C110.0520 (12)0.0546 (13)0.0517 (12)0.0067 (10)0.0170 (10)0.0026 (10)
C120.0537 (13)0.0738 (16)0.0528 (13)0.0019 (11)0.0113 (11)0.0076 (11)
C130.0708 (15)0.0724 (16)0.0469 (13)0.0189 (13)0.0134 (12)0.0047 (12)
C140.0885 (18)0.0547 (14)0.0559 (14)0.0108 (13)0.0321 (13)0.0081 (11)
C150.0602 (13)0.0435 (11)0.0487 (11)0.0016 (9)0.0272 (10)0.0007 (9)
C160.0468 (11)0.0382 (10)0.0465 (11)0.0008 (8)0.0218 (9)0.0002 (8)
C170.0501 (11)0.0364 (10)0.0451 (11)0.0017 (8)0.0220 (9)0.0037 (8)
C180.0507 (11)0.0428 (11)0.0503 (11)0.0004 (9)0.0222 (10)0.0011 (9)
C190.0729 (15)0.0538 (13)0.0597 (14)0.0116 (11)0.0285 (12)0.0136 (10)
C200.0732 (16)0.0572 (14)0.0748 (16)0.0259 (12)0.0298 (14)0.0081 (12)
C210.0715 (16)0.0654 (15)0.0859 (18)0.0194 (12)0.0470 (14)0.0026 (13)
C220.0722 (14)0.0523 (13)0.0637 (13)0.0090 (11)0.0420 (12)0.0028 (10)
Geometric parameters (Å, º) top
Cl1—C181.741 (2)C8—H8A0.9800
O1—C71.211 (2)C9—H9A0.9700
O2—C161.339 (2)C9—H9B0.9700
O2—C81.442 (2)C10—C151.386 (3)
O3—C161.201 (2)C10—C111.395 (3)
N1—N21.355 (2)C11—C121.366 (3)
N1—C101.363 (2)C11—H11A0.9300
N1—C91.457 (2)C12—C131.399 (3)
N2—N31.297 (2)C12—H12A0.9300
N3—C151.371 (3)C13—C141.357 (3)
C1—C61.385 (3)C13—H13A0.9300
C1—C21.387 (3)C14—C151.401 (3)
C1—H1A0.9300C14—H14A0.9300
C2—C31.376 (4)C16—C171.488 (3)
C2—H2B0.9300C17—C181.391 (3)
C3—C41.365 (4)C17—C221.391 (3)
C3—H3B0.9300C18—C191.376 (3)
C4—C51.368 (3)C19—C201.374 (3)
C4—H4A0.9300C19—H19A0.9300
C5—C61.393 (3)C20—C211.364 (3)
C5—H5A0.9300C20—H20A0.9300
C6—C71.481 (3)C21—C221.369 (3)
C7—C81.524 (3)C21—H21A0.9300
C8—C91.520 (3)C22—H22A0.9300
C16—O2—C8115.32 (14)N1—C10—C15104.09 (16)
N2—N1—C10109.89 (15)N1—C10—C11133.47 (18)
N2—N1—C9118.37 (15)C15—C10—C11122.44 (19)
C10—N1—C9131.71 (15)C12—C11—C10115.9 (2)
N3—N2—N1108.98 (16)C12—C11—H11A122.1
N2—N3—C15108.26 (16)C10—C11—H11A122.1
C6—C1—C2119.9 (2)C11—C12—C13122.2 (2)
C6—C1—H1A120.0C11—C12—H12A118.9
C2—C1—H1A120.0C13—C12—H12A118.9
C3—C2—C1119.8 (2)C14—C13—C12121.8 (2)
C3—C2—H2B120.1C14—C13—H13A119.1
C1—C2—H2B120.1C12—C13—H13A119.1
C4—C3—C2120.6 (2)C13—C14—C15117.2 (2)
C4—C3—H3B119.7C13—C14—H14A121.4
C2—C3—H3B119.7C15—C14—H14A121.4
C3—C4—C5120.2 (2)N3—C15—C10108.77 (17)
C3—C4—H4A119.9N3—C15—C14130.8 (2)
C5—C4—H4A119.9C10—C15—C14120.4 (2)
C4—C5—C6120.6 (2)O3—C16—O2123.11 (17)
C4—C5—H5A119.7O3—C16—C17123.34 (18)
C6—C5—H5A119.7O2—C16—C17113.51 (16)
C1—C6—C5118.98 (19)C18—C17—C22117.59 (18)
C1—C6—C7122.59 (18)C18—C17—C16126.44 (18)
C5—C6—C7118.41 (18)C22—C17—C16115.96 (18)
O1—C7—C6122.00 (18)C19—C18—C17121.0 (2)
O1—C7—C8119.74 (17)C19—C18—Cl1117.02 (17)
C6—C7—C8118.23 (16)C17—C18—Cl1121.97 (15)
O2—C8—C9107.37 (14)C20—C19—C18119.6 (2)
O2—C8—C7110.17 (15)C20—C19—H19A120.2
C9—C8—C7112.70 (15)C18—C19—H19A120.2
O2—C8—H8A108.8C21—C20—C19120.7 (2)
C9—C8—H8A108.8C21—C20—H20A119.7
C7—C8—H8A108.8C19—C20—H20A119.7
N1—C9—C8114.94 (15)C20—C21—C22119.7 (2)
N1—C9—H9A108.5C20—C21—H21A120.2
C8—C9—H9A108.5C22—C21—H21A120.2
N1—C9—H9B108.5C21—C22—C17121.4 (2)
C8—C9—H9B108.5C21—C22—H22A119.3
H9A—C9—H9B107.5C17—C22—H22A119.3
C10—N1—N2—N30.2 (2)C15—C10—C11—C120.3 (3)
C9—N1—N2—N3178.26 (16)C10—C11—C12—C130.3 (3)
N1—N2—N3—C150.2 (2)C11—C12—C13—C140.5 (4)
C6—C1—C2—C31.7 (3)C12—C13—C14—C150.2 (4)
C1—C2—C3—C41.2 (4)N2—N3—C15—C100.4 (2)
C2—C3—C4—C50.2 (4)N2—N3—C15—C14179.3 (2)
C3—C4—C5—C60.9 (4)N1—C10—C15—N30.5 (2)
C2—C1—C6—C51.0 (3)C11—C10—C15—N3179.71 (19)
C2—C1—C6—C7177.50 (19)N1—C10—C15—C14179.24 (19)
C4—C5—C6—C10.3 (3)C11—C10—C15—C140.6 (3)
C4—C5—C6—C7178.9 (2)C13—C14—C15—N3180.0 (2)
C1—C6—C7—O1163.38 (19)C13—C14—C15—C100.4 (3)
C5—C6—C7—O115.1 (3)C8—O2—C16—O37.5 (3)
C1—C6—C7—C818.3 (3)C8—O2—C16—C17174.80 (14)
C5—C6—C7—C8163.22 (18)O3—C16—C17—C18147.3 (2)
C16—O2—C8—C9154.85 (15)O2—C16—C17—C1835.0 (3)
C16—O2—C8—C782.08 (18)O3—C16—C17—C2231.4 (3)
O1—C7—C8—O216.6 (2)O2—C16—C17—C22146.24 (18)
C6—C7—C8—O2165.06 (15)C22—C17—C18—C190.2 (3)
O1—C7—C8—C9103.3 (2)C16—C17—C18—C19178.99 (19)
C6—C7—C8—C975.0 (2)C22—C17—C18—Cl1177.01 (16)
N2—N1—C9—C8114.62 (18)C16—C17—C18—Cl11.7 (3)
C10—N1—C9—C867.8 (3)C17—C18—C19—C201.2 (3)
O2—C8—C9—N190.19 (18)Cl1—C18—C19—C20178.55 (19)
C7—C8—C9—N131.3 (2)C18—C19—C20—C211.3 (4)
N2—N1—C10—C150.4 (2)C19—C20—C21—C220.0 (4)
C9—N1—C10—C15178.14 (18)C20—C21—C22—C171.5 (4)
N2—N1—C10—C11179.8 (2)C18—C17—C22—C211.6 (3)
C9—N1—C10—C112.1 (4)C16—C17—C22—C21179.5 (2)
N1—C10—C11—C12179.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···N2i0.982.613.206 (3)119
C8—H8A···N3i0.982.483.296 (3)140
C21—H21A···O1ii0.932.533.330 (3)144
Symmetry codes: (i) x, y1/2, z1/2; (ii) x+1, y1/2, z1/2.
 

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