Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the mol­ecule of the title compound, C23H17Cl2N3O3, the nearly planar benzotriazole system is oriented at dihedral angles of 19.53 (1) and 62.95 (1)°, respectively, with respect to the tolyl and dichloro­phenyl rings. In the crystal structure, mol­ecules are linked into chains along the a axis by inter­molecular C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807004084/hk2198sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807004084/hk2198Isup2.hkl
Contains datablock I

CCDC reference: 640366

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.063
  • wR factor = 0.141
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C22
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.63 mm PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT213_ALERT_2_C Atom Cl2 has ADP max/min Ratio ............. 3.10 prola PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.33 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.91 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C21 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.11 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C23 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C23 H17 Cl2 N3 O3
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

2-(Benzotriazol-1-yl)-1-(4-methylbenzoyl)ethyl 2,4-dichlorobenzoate top
Crystal data top
C23H17Cl2N3O3F(000) = 936
Mr = 454.30Dx = 1.434 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1296 reflections
a = 5.0020 (6) Åθ = 2.7–19.1°
b = 29.782 (4) ŵ = 0.34 mm1
c = 14.1351 (18) ÅT = 294 K
β = 92.624 (3)°Needle, colorless
V = 2103.5 (5) Å30.63 × 0.11 × 0.05 mm
Z = 4
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
3881 independent reflections
Radiation source: fine-focus sealed tube2214 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
Detector resolution: 8.33 pixels mm-1θmax = 25.5°, θmin = 1.6°
ω scansh = 65
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 3536
Tmin = 0.956, Tmax = 0.983l = 1217
11277 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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0444P)2 + 0.9659P]
where P = (Fo2 + 2Fc2)/3
3881 reflections(Δ/σ)max < 0.001
280 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.30 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
Cl10.2071 (2)0.39172 (4)0.13277 (7)0.0797 (4)
Cl20.3744 (4)0.48482 (4)0.12103 (13)0.1727 (10)
O10.5697 (5)0.34770 (9)0.37141 (18)0.0689 (8)
O20.7546 (5)0.35383 (7)0.19413 (16)0.0531 (6)
O30.7191 (7)0.42626 (9)0.2237 (2)0.1006 (12)
N10.8697 (5)0.26949 (9)0.2929 (2)0.0491 (7)
N20.8268 (7)0.25462 (11)0.3815 (2)0.0681 (9)
N30.6395 (8)0.22433 (11)0.3777 (2)0.0739 (10)
C10.8223 (9)0.38743 (13)0.5299 (3)0.0715 (12)
H1A0.68140.36800.54050.086*
C20.9281 (11)0.41320 (16)0.6034 (3)0.0890 (15)
H2B0.85950.41030.66310.107*
C31.1298 (11)0.44267 (16)0.5906 (4)0.0895 (16)
C41.2277 (10)0.44558 (16)0.5023 (4)0.1037 (17)
H4A1.36490.46580.49200.124*
C51.1294 (8)0.41938 (13)0.4274 (3)0.0751 (12)
H5A1.20320.42160.36840.090*
C60.9226 (7)0.39009 (10)0.4410 (3)0.0487 (9)
C70.7930 (7)0.36301 (11)0.3645 (2)0.0466 (8)
C80.9402 (6)0.35197 (11)0.2752 (2)0.0476 (9)
H8A1.08320.37400.26740.057*
C91.0597 (7)0.30479 (11)0.2781 (3)0.0563 (10)
H9A1.14460.29930.21890.068*
H9B1.19780.30360.32850.068*
C100.7025 (6)0.24793 (10)0.2291 (2)0.0446 (8)
C110.5571 (7)0.21938 (11)0.2841 (3)0.0524 (9)
C120.3608 (8)0.19146 (12)0.2420 (3)0.0684 (11)
H12A0.26120.17200.27790.082*
C130.3217 (8)0.19388 (13)0.1465 (3)0.0715 (12)
H13A0.18930.17620.11690.086*
C140.4747 (8)0.22212 (12)0.0916 (3)0.0657 (11)
H14A0.44380.22220.02620.079*
C150.6690 (7)0.24974 (11)0.1308 (2)0.0515 (9)
H15A0.77160.26840.09420.062*
C160.6482 (7)0.39480 (12)0.1775 (3)0.0558 (10)
C170.4381 (7)0.39449 (11)0.1005 (2)0.0486 (9)
C180.3610 (8)0.35517 (12)0.0564 (2)0.0599 (10)
H18A0.44630.32870.07510.072*
C190.1625 (8)0.35330 (12)0.0146 (2)0.0594 (10)
H19A0.11380.32610.04270.071*
C200.0403 (7)0.39193 (12)0.0424 (2)0.0545 (9)
C210.1098 (9)0.43193 (13)0.0007 (3)0.0823 (14)
H21A0.02560.45830.02090.099*
C220.3054 (8)0.43310 (12)0.0715 (3)0.0694 (12)
C231.2452 (13)0.47127 (19)0.6721 (4)0.149 (3)
H23A1.38570.48990.64980.223*
H23B1.31610.45210.72170.223*
H23C1.10670.48980.69600.223*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0851 (8)0.0869 (7)0.0642 (7)0.0034 (6)0.0286 (6)0.0010 (6)
Cl20.2320 (19)0.0571 (7)0.2135 (18)0.0451 (9)0.1587 (16)0.0508 (9)
O10.0488 (17)0.0825 (18)0.0756 (19)0.0174 (14)0.0034 (14)0.0193 (15)
O20.0540 (15)0.0502 (14)0.0538 (15)0.0007 (12)0.0131 (12)0.0071 (11)
O30.140 (3)0.0501 (16)0.105 (2)0.0028 (17)0.067 (2)0.0135 (16)
N10.0469 (18)0.0511 (17)0.0483 (18)0.0031 (14)0.0095 (14)0.0004 (14)
N20.094 (3)0.063 (2)0.046 (2)0.0062 (19)0.0158 (18)0.0011 (16)
N30.103 (3)0.058 (2)0.060 (2)0.007 (2)0.000 (2)0.0058 (17)
C10.084 (3)0.072 (3)0.058 (3)0.006 (2)0.007 (2)0.003 (2)
C20.120 (4)0.091 (3)0.054 (3)0.016 (3)0.018 (3)0.014 (2)
C30.096 (4)0.078 (3)0.090 (4)0.014 (3)0.035 (3)0.040 (3)
C40.096 (4)0.094 (4)0.120 (4)0.036 (3)0.007 (3)0.049 (3)
C50.071 (3)0.074 (3)0.080 (3)0.017 (2)0.001 (2)0.029 (2)
C60.049 (2)0.0431 (19)0.053 (2)0.0062 (17)0.0092 (18)0.0054 (17)
C70.038 (2)0.0457 (19)0.056 (2)0.0029 (17)0.0052 (17)0.0009 (17)
C80.036 (2)0.054 (2)0.052 (2)0.0079 (16)0.0079 (17)0.0045 (17)
C90.034 (2)0.064 (2)0.070 (3)0.0005 (18)0.0081 (18)0.0095 (19)
C100.043 (2)0.0420 (18)0.049 (2)0.0088 (16)0.0035 (16)0.0051 (16)
C110.061 (2)0.0421 (19)0.054 (2)0.0015 (18)0.0011 (19)0.0047 (18)
C120.072 (3)0.052 (2)0.082 (3)0.007 (2)0.011 (2)0.001 (2)
C130.064 (3)0.057 (2)0.092 (3)0.013 (2)0.015 (2)0.009 (2)
C140.079 (3)0.061 (2)0.056 (2)0.001 (2)0.011 (2)0.011 (2)
C150.055 (2)0.052 (2)0.047 (2)0.0009 (18)0.0056 (17)0.0070 (17)
C160.066 (3)0.044 (2)0.056 (2)0.0061 (19)0.010 (2)0.0015 (18)
C170.057 (2)0.0453 (19)0.043 (2)0.0032 (17)0.0032 (17)0.0033 (16)
C180.072 (3)0.052 (2)0.054 (2)0.0004 (19)0.012 (2)0.0007 (18)
C190.074 (3)0.054 (2)0.049 (2)0.006 (2)0.009 (2)0.0068 (18)
C200.057 (2)0.062 (2)0.043 (2)0.0004 (19)0.0077 (17)0.0047 (18)
C210.099 (4)0.059 (2)0.086 (3)0.019 (2)0.038 (3)0.010 (2)
C220.082 (3)0.050 (2)0.073 (3)0.008 (2)0.027 (2)0.020 (2)
C230.163 (6)0.141 (5)0.137 (5)0.004 (4)0.056 (4)0.087 (4)
Geometric parameters (Å, º) top
Cl1—C201.738 (3)C9—H9A0.9700
Cl2—C221.720 (4)C9—H9B0.9700
O1—C71.214 (4)C10—C111.382 (4)
O2—C161.348 (4)C10—C151.393 (4)
O2—C81.443 (4)C11—C121.399 (5)
O3—C161.187 (4)C12—H12A0.9300
N1—N21.355 (4)C13—C121.356 (5)
N1—C101.362 (4)C13—C141.397 (5)
N1—C91.439 (4)C13—H13A0.9300
N3—N21.300 (4)C14—H14A0.9300
N3—C111.376 (4)C15—C141.370 (5)
C1—C21.378 (5)C15—H15A0.9300
C1—H1A0.9300C17—C181.374 (4)
C4—C31.364 (7)C17—C221.380 (4)
C4—H4A0.9300C17—C161.478 (4)
C2—C31.356 (6)C18—H18A0.9300
C2—H2B0.9300C19—C201.353 (5)
C3—C231.524 (6)C19—C181.380 (4)
C5—C41.387 (5)C19—H19A0.9300
C5—H5A0.9300C20—C211.367 (5)
C6—C51.373 (5)C21—C221.382 (5)
C6—C11.377 (5)C21—H21A0.9300
C6—C71.474 (4)C23—H23A0.9600
C7—C81.526 (5)C23—H23B0.9600
C8—C91.527 (4)C23—H23C0.9600
C8—H8A0.9800
C16—O2—C8114.1 (2)N3—C11—C10109.5 (3)
N2—N1—C10109.9 (3)N3—C11—C12130.3 (4)
N2—N1—C9120.4 (3)C10—C11—C12120.2 (3)
C10—N1—C9129.6 (3)C13—C12—C11117.3 (4)
N3—N2—N1109.4 (3)C13—C12—H12A121.3
N2—N3—C11107.3 (3)C11—C12—H12A121.3
C6—C1—C2120.9 (4)C12—C13—C14121.8 (4)
C6—C1—H1A119.6C12—C13—H13A119.1
C2—C1—H1A119.6C14—C13—H13A119.1
C3—C2—C1121.5 (5)C15—C14—C13122.2 (4)
C3—C2—H2B119.2C15—C14—H14A118.9
C1—C2—H2B119.2C13—C14—H14A118.9
C2—C3—C4117.6 (4)C14—C15—C10115.5 (3)
C2—C3—C23121.3 (6)C14—C15—H15A122.3
C4—C3—C23121.1 (5)C10—C15—H15A122.3
C3—C4—C5122.2 (5)O3—C16—O2120.8 (3)
C3—C4—H4A118.9O3—C16—C17126.5 (3)
C5—C4—H4A118.9O2—C16—C17112.6 (3)
C6—C5—C4119.6 (4)C18—C17—C22117.0 (3)
C6—C5—H5A120.2C18—C17—C16121.0 (3)
C4—C5—H5A120.2C22—C17—C16122.0 (3)
C5—C6—C1118.2 (3)C17—C18—C19122.8 (3)
C5—C6—C7123.6 (3)C17—C18—H18A118.6
C1—C6—C7118.1 (3)C19—C18—H18A118.6
O1—C7—C6121.4 (3)C20—C19—C18118.5 (3)
O1—C7—C8117.8 (3)C20—C19—H19A120.7
C6—C7—C8120.8 (3)C18—C19—H19A120.7
O2—C8—C7109.4 (3)C19—C20—C21120.9 (3)
O2—C8—C9107.1 (2)C19—C20—Cl1120.5 (3)
C7—C8—C9112.3 (3)C21—C20—Cl1118.6 (3)
O2—C8—H8A109.4C20—C21—C22119.9 (3)
C7—C8—H8A109.4C20—C21—H21A120.1
C9—C8—H8A109.4C22—C21—H21A120.1
N1—C9—C8114.6 (3)C17—C22—C21120.8 (3)
N1—C9—H9A108.6C17—C22—Cl2122.7 (3)
C8—C9—H9A108.6C21—C22—Cl2116.4 (3)
N1—C9—H9B108.6C3—C23—H23A109.5
C8—C9—H9B108.6C3—C23—H23B109.5
H9A—C9—H9B107.6H23A—C23—H23B109.5
N1—C10—C11103.9 (3)C3—C23—H23C109.5
N1—C10—C15133.2 (3)H23A—C23—H23C109.5
C11—C10—C15122.9 (3)H23B—C23—H23C109.5
C5—C6—C7—O1158.8 (4)N1—C10—C11—C12179.7 (3)
C1—C6—C7—O118.0 (5)C15—C10—C11—C121.8 (5)
C5—C6—C7—C823.3 (5)N2—N1—C9—C892.7 (4)
C1—C6—C7—C8159.8 (3)C10—N1—C9—C883.7 (4)
C18—C19—C20—C210.5 (6)O2—C8—C9—N163.8 (4)
C18—C19—C20—Cl1178.9 (3)C7—C8—C9—N156.3 (4)
C16—O2—C8—C763.3 (4)C19—C20—C21—C220.7 (7)
C16—O2—C8—C9174.8 (3)Cl1—C20—C21—C22179.8 (3)
O1—C7—C8—O240.3 (4)N1—C10—C15—C14179.9 (3)
C6—C7—C8—O2141.8 (3)C11—C10—C15—C142.0 (5)
O1—C7—C8—C978.5 (4)C18—C17—C22—C211.9 (6)
C6—C7—C8—C999.5 (3)C16—C17—C22—C21179.9 (4)
N2—N1—C10—C110.0 (3)C18—C17—C22—Cl2178.9 (3)
C9—N1—C10—C11176.6 (3)C16—C17—C22—Cl20.8 (6)
N2—N1—C10—C15178.2 (3)C20—C21—C22—C172.0 (7)
C9—N1—C10—C155.1 (6)C20—C21—C22—Cl2178.8 (4)
C8—O2—C16—O34.3 (5)C10—C15—C14—C130.4 (5)
C8—O2—C16—C17173.8 (3)C12—C13—C14—C151.5 (6)
C18—C17—C16—O3175.4 (4)C14—C13—C12—C111.6 (6)
C22—C17—C16—O32.6 (7)N3—C11—C12—C13179.8 (4)
C18—C17—C16—O22.6 (5)C10—C11—C12—C130.1 (5)
C22—C17—C16—O2179.3 (4)C1—C6—C5—C40.9 (6)
C11—N3—N2—N10.2 (4)C7—C6—C5—C4175.9 (4)
C10—N1—N2—N30.1 (4)C5—C6—C1—C20.5 (6)
C9—N1—N2—N3177.1 (3)C7—C6—C1—C2177.5 (3)
C22—C17—C18—C190.6 (6)C6—C5—C4—C31.5 (7)
C16—C17—C18—C19178.8 (4)C6—C1—C2—C31.4 (7)
C20—C19—C18—C170.6 (6)C1—C2—C3—C40.8 (7)
N2—N3—C11—C100.2 (4)C1—C2—C3—C23179.7 (4)
N2—N3—C11—C12179.6 (4)C5—C4—C3—C20.6 (8)
N1—C10—C11—N30.2 (4)C5—C4—C3—C23178.8 (4)
C15—C10—C11—N3178.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9B···O1i0.972.333.094 (4)135
C18—H18A···O20.932.352.705 (4)102
Symmetry code: (i) x1, y, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

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