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In the crystal structure of the title compound, C22H13Cl3N3O3, weak inter­molecular C—H...Cl hydrogen bonds link the mol­ecules into chains extending 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/S160053680702870X/at2324sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680702870X/at2324Isup2.hkl
Contains datablock I

CCDC reference: 654960

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.051
  • wR factor = 0.151
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C20 - C21 .. 5.71 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20 PLAT320_ALERT_2_C Check Hybridisation of C8 in Main Residue . ? PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. N2 .. 3.18 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

1H-Benzotriazoles and its derivatives are an important class of compounds because they exhibit a broad spectrum of pharmacological activities such as antifungal, antitumor and antineoplastic activities (Chen & Wu, 2005). We report here the synthesis and structure of the title compound, (I) (Fig. 1), as part of our ongoing studies on new benzotriazole compounds with higher bioactivity.

All bond lengths and angles in (I) are within normal ranges (Allen et al., 1987). The benzotriazole ring system is essentially planar, with a dihedral angle of 1.02 (14) ° between the triazole ring (N1—N3/C1/C2) and the benzene ring (C1—C6). The dihedral angles between the mean planes of the benzotriazole system and rings (C17—C22) and rings (C10—C15) are 50.89 (14) and 44.97 (14) °, respectively. The dihedral angle between rings (C17—C22) and rings (C10—C15) is 84.40 (14)°. In the crystal structure, weak inter molecular C—H···Cl hydrogen bonds (Table1) link the molecules into chains extended along the C axis. The packing (Fig. 2) is further stabilized by weak C—H···O interactions (Table 2).

Related literature top

For related literature, see: Chen & Wu (2005). For bond-length data, see: Allen et al. (1987).

Experimental top

Bromine (3.2 g, 0.02 mol) was added dropwise to a solution of 3-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(3-chlorophenyl)propan-1-one (5.7 g,0.02 mol)and sodium acetate (1.6 g, 0.02 mol) in acetic acid (50 ml). The reaction proceeded for 7 h. Water (50 ml) and chloroform (20 ml) were then added. The organic layer was washed successively with saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and the chloroform solution filtered. It was cooled with ice-water, and then an acetone solution (10 ml) of 2,4-dichlorobenzoic acid (3.8 g, 0.02 mol) and tri ethylamine (2.8 ml) was added. The mixture was stirred with ice-water for about 6 h. The solution was then filtered and concentrated. Single crystals were obtained by slow evaporation of ethanol solution at room temperature over a period of one week.

Refinement top

All H atoms were located in difference Fourier maps and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and with Uiso(H) = 1.2 Ueq(C) and 1.5 Ueq(methyl C) H atoms.

Structure description top

1H-Benzotriazoles and its derivatives are an important class of compounds because they exhibit a broad spectrum of pharmacological activities such as antifungal, antitumor and antineoplastic activities (Chen & Wu, 2005). We report here the synthesis and structure of the title compound, (I) (Fig. 1), as part of our ongoing studies on new benzotriazole compounds with higher bioactivity.

All bond lengths and angles in (I) are within normal ranges (Allen et al., 1987). The benzotriazole ring system is essentially planar, with a dihedral angle of 1.02 (14) ° between the triazole ring (N1—N3/C1/C2) and the benzene ring (C1—C6). The dihedral angles between the mean planes of the benzotriazole system and rings (C17—C22) and rings (C10—C15) are 50.89 (14) and 44.97 (14) °, respectively. The dihedral angle between rings (C17—C22) and rings (C10—C15) is 84.40 (14)°. In the crystal structure, weak inter molecular C—H···Cl hydrogen bonds (Table1) link the molecules into chains extended along the C axis. The packing (Fig. 2) is further stabilized by weak C—H···O interactions (Table 2).

For related literature, see: Chen & Wu (2005). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids.
[Figure 2] Fig. 2. The crystal packing of (I), viewed along c axis. Hydrogen bonding interactions are indicated by dashed lines.
2-(1H-Benzotriazol-1-yl)-1-(3-chlorobenzoyl)ethyl 2,4-dichlorobenzoate top
Crystal data top
C22H13Cl3N3O3F(000) = 964
Mr = 473.70Dx = 1.469 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3223 reflections
a = 10.9182 (2) Åθ = 1.9–26.0°
b = 19.6123 (3) ŵ = 0.46 mm1
c = 10.0124 (2) ÅT = 273 K
β = 92.096 (1)°Prism, colourless
V = 2142.53 (7) Å30.28 × 0.06 × 0.04 mm
Z = 4
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
4212 independent reflections
Radiation source: fine-focus sealed tube3192 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1312
Tmin = 0.960, Tmax = 0.980k = 2424
27918 measured reflectionsl = 1212
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0691P)2 + 1.3064P]
where P = (Fo2 + 2Fc2)/3
4212 reflections(Δ/σ)max = 0.001
280 parametersΔρmax = 0.68 e Å3
0 restraintsΔρmin = 0.46 e Å3
Crystal data top
C22H13Cl3N3O3V = 2142.53 (7) Å3
Mr = 473.70Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.9182 (2) ŵ = 0.46 mm1
b = 19.6123 (3) ÅT = 273 K
c = 10.0124 (2) Å0.28 × 0.06 × 0.04 mm
β = 92.096 (1)°
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
4212 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
3192 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.980Rint = 0.027
27918 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.151H-atom parameters constrained
S = 1.05Δρmax = 0.68 e Å3
4212 reflectionsΔρmin = 0.46 e Å3
280 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl10.08295 (7)0.21406 (6)0.75068 (11)0.0959 (4)
Cl20.70830 (11)0.05478 (5)1.02091 (11)0.1040 (4)
Cl31.09105 (14)0.01904 (8)1.32415 (11)0.1447 (6)
O10.75829 (15)0.14993 (8)0.83033 (16)0.0468 (5)
O20.6409 (2)0.05810 (10)0.8437 (2)0.0793 (8)
O30.54692 (17)0.20882 (10)0.89673 (17)0.0562 (6)
N10.75249 (17)0.29201 (10)0.75969 (18)0.0413 (6)
N20.84951 (19)0.29393 (12)0.8493 (2)0.0527 (7)
N30.8438 (2)0.35025 (12)0.9182 (2)0.0594 (8)
C10.7421 (3)0.38627 (13)0.8729 (2)0.0510 (8)
C20.6831 (2)0.34902 (11)0.7716 (2)0.0420 (7)
C30.5776 (3)0.37220 (14)0.7044 (3)0.0555 (9)
C40.5353 (3)0.43447 (16)0.7439 (3)0.0740 (11)
C50.5931 (4)0.47225 (16)0.8448 (4)0.0810 (13)
C60.6956 (3)0.44969 (15)0.9115 (3)0.0713 (13)
C70.7376 (2)0.23588 (12)0.6664 (2)0.0436 (7)
C80.6763 (2)0.17327 (12)0.7247 (2)0.0424 (7)
C90.5515 (2)0.18976 (11)0.7819 (2)0.0406 (7)
C100.4383 (2)0.18335 (11)0.6947 (2)0.0414 (7)
C110.4378 (2)0.16088 (14)0.5633 (2)0.0523 (8)
C120.3277 (3)0.15362 (17)0.4908 (3)0.0659 (10)
C130.2185 (3)0.16959 (17)0.5473 (3)0.0673 (11)
C140.2202 (2)0.19297 (15)0.6776 (3)0.0599 (10)
C150.3280 (2)0.19972 (13)0.7513 (3)0.0520 (8)
C160.7286 (2)0.08918 (12)0.8832 (3)0.0484 (8)
C170.8177 (2)0.07003 (13)0.9928 (2)0.0487 (8)
C180.9089 (2)0.11622 (15)1.0323 (3)0.0564 (9)
C190.9930 (3)0.10150 (19)1.1342 (3)0.0730 (11)
C200.9870 (3)0.0400 (2)1.1963 (3)0.0781 (13)
C210.8994 (4)0.00732 (18)1.1621 (3)0.0806 (13)
C220.8140 (3)0.00766 (14)1.0588 (3)0.0629 (10)
H30.538200.347000.636900.0670*
H40.465100.452100.701400.0890*
H50.560500.514300.867500.0970*
H60.733400.475100.979700.0850*
H7A0.817600.222900.635900.0520*
H7B0.689100.251300.589100.0520*
H110.511300.150700.523700.0630*
H120.327800.137800.403300.0790*
H130.144800.164800.498700.0810*
H150.327100.215200.839000.0620*
H180.913100.158000.988900.0680*
H191.052800.133101.160100.0870*
H210.896700.048801.206900.0970*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0421 (4)0.1304 (8)0.1155 (8)0.0145 (5)0.0062 (4)0.0038 (6)
Cl20.1360 (9)0.0568 (5)0.1168 (8)0.0154 (5)0.0278 (7)0.0304 (5)
Cl30.1632 (12)0.1765 (13)0.0890 (7)0.0837 (10)0.0691 (8)0.0215 (8)
O10.0430 (9)0.0391 (9)0.0573 (10)0.0023 (7)0.0099 (7)0.0053 (7)
O20.0795 (15)0.0546 (12)0.1007 (16)0.0224 (11)0.0391 (12)0.0201 (11)
O30.0517 (11)0.0731 (12)0.0435 (10)0.0066 (9)0.0009 (7)0.0078 (9)
N10.0394 (10)0.0443 (10)0.0401 (10)0.0010 (8)0.0010 (8)0.0055 (8)
N20.0447 (12)0.0611 (14)0.0518 (12)0.0035 (10)0.0058 (9)0.0133 (10)
N30.0653 (15)0.0611 (14)0.0509 (12)0.0160 (11)0.0094 (11)0.0063 (11)
C10.0632 (16)0.0491 (14)0.0407 (12)0.0118 (12)0.0031 (11)0.0031 (11)
C20.0504 (14)0.0388 (12)0.0371 (11)0.0001 (10)0.0061 (10)0.0041 (9)
C30.0603 (17)0.0520 (15)0.0536 (14)0.0104 (12)0.0057 (12)0.0003 (12)
C40.081 (2)0.0582 (18)0.082 (2)0.0245 (16)0.0064 (17)0.0012 (16)
C50.111 (3)0.0496 (17)0.083 (2)0.0168 (17)0.010 (2)0.0103 (16)
C60.103 (3)0.0523 (16)0.0588 (17)0.0130 (17)0.0054 (17)0.0121 (14)
C70.0452 (13)0.0471 (13)0.0388 (11)0.0063 (10)0.0054 (10)0.0012 (10)
C80.0410 (13)0.0413 (12)0.0446 (12)0.0068 (10)0.0039 (10)0.0022 (10)
C90.0434 (13)0.0374 (11)0.0408 (12)0.0028 (9)0.0002 (9)0.0038 (9)
C100.0406 (13)0.0388 (12)0.0446 (12)0.0009 (10)0.0021 (10)0.0060 (9)
C110.0482 (14)0.0610 (16)0.0476 (14)0.0007 (12)0.0008 (11)0.0016 (12)
C120.0608 (18)0.083 (2)0.0528 (16)0.0025 (15)0.0127 (13)0.0021 (14)
C130.0495 (17)0.079 (2)0.0721 (19)0.0019 (14)0.0169 (14)0.0088 (16)
C140.0389 (14)0.0645 (17)0.0761 (19)0.0040 (12)0.0008 (12)0.0085 (14)
C150.0456 (14)0.0548 (15)0.0554 (14)0.0029 (11)0.0011 (11)0.0000 (12)
C160.0492 (15)0.0380 (12)0.0575 (14)0.0043 (11)0.0062 (11)0.0013 (11)
C170.0512 (14)0.0448 (13)0.0499 (14)0.0141 (11)0.0023 (11)0.0034 (11)
C180.0491 (15)0.0614 (16)0.0582 (15)0.0127 (12)0.0048 (12)0.0113 (12)
C190.0615 (19)0.087 (2)0.0691 (19)0.0222 (16)0.0185 (15)0.0238 (17)
C200.083 (2)0.094 (3)0.0555 (17)0.043 (2)0.0218 (16)0.0217 (17)
C210.114 (3)0.072 (2)0.0552 (17)0.042 (2)0.0043 (18)0.0082 (15)
C220.080 (2)0.0494 (15)0.0586 (16)0.0167 (14)0.0050 (14)0.0024 (12)
Geometric parameters (Å, º) top
Cl1—C141.741 (3)C12—C131.374 (5)
Cl2—C221.716 (3)C13—C141.382 (4)
Cl3—C201.730 (3)C14—C151.373 (3)
O1—C81.435 (3)C16—C171.488 (3)
O1—C161.348 (3)C17—C181.393 (3)
O2—C161.190 (3)C17—C221.392 (4)
O3—C91.212 (3)C18—C191.378 (4)
N1—N21.363 (3)C19—C201.360 (5)
N1—C21.358 (3)C20—C211.367 (5)
N1—C71.449 (3)C21—C221.398 (5)
N2—N31.305 (3)C3—H30.9300
N3—C11.379 (4)C4—H40.9300
C1—C21.389 (3)C5—H50.9300
C1—C61.403 (4)C6—H60.9300
C2—C31.389 (4)C7—H7A0.9700
C3—C41.369 (4)C7—H7B0.9700
C4—C51.386 (5)C11—H110.9300
C5—C61.356 (5)C12—H120.9300
C7—C81.525 (3)C13—H130.9300
C8—C91.532 (3)C15—H150.9300
C9—C101.492 (3)C18—H180.9300
C10—C111.387 (3)C19—H190.9300
C10—C151.387 (3)C21—H210.9300
C11—C121.389 (4)
Cl1···N2i3.180 (2)C7···N3vii3.253 (3)
Cl2···O22.915 (2)C9···O22.821 (3)
Cl3···C16ii3.604 (3)C9···C23.441 (3)
Cl1···H7Ai3.0800C11···O3vii3.298 (3)
Cl1···H19iii3.1500C16···Cl3ii3.604 (3)
Cl2···H4iv2.8700C16···O33.079 (3)
Cl3···H6v2.8300C17···C2vi3.574 (3)
O1···O32.686 (2)C18···C2vi3.566 (3)
O1···N12.875 (3)C18···N1vi3.409 (3)
O1···N22.998 (3)C19···N2vi3.398 (4)
O2···C92.821 (3)C20···C1vi3.566 (4)
O2···Cl22.915 (2)C20···C22ii3.539 (4)
O2···O33.180 (3)C21···C6vi3.588 (5)
O2···C4iv3.198 (4)C22···C20ii3.539 (4)
O3···O23.180 (3)C1···H11vi3.0700
O3···C11vi3.298 (3)C3···H7B2.9200
O3···O12.686 (2)C6···H11vi3.0600
O3···C163.079 (3)C7···H33.0900
O3···N13.132 (3)C8···H112.6900
O3···C23.388 (3)C11···H5iv2.9600
O1···H182.2800C12···H15vii2.9900
O2···H4iv2.4100H3···C73.0900
O3···H152.4500H3···H7B2.5500
O3···H3vi2.6500H3···O3vii2.6500
O3···H7Bvi2.5500H4···Cl2ix2.8700
N1···O12.875 (3)H4···O2ix2.4100
N1···O33.132 (3)H5···C11ix2.9600
N1···C18vii3.409 (3)H6···Cl3x2.8300
N2···Cl1viii3.180 (2)H7A···Cl1viii3.0800
N2···O12.998 (3)H7A···N2vii2.9200
N2···C19vii3.398 (4)H7A···N3vii2.6300
N3···C7vi3.253 (3)H7B···C32.9200
N2···H7Avi2.9200H7B···H32.5500
N3···H7Avi2.6300H7B···O3vii2.5500
C1···C20vii3.566 (4)H11···C82.6900
C2···C17vii3.574 (3)H11···C1vii3.0700
C2···O33.388 (3)H11···C6vii3.0600
C2···C93.441 (3)H15···O32.4500
C2···C18vii3.566 (3)H15···C12vi2.9900
C4···O2ix3.198 (4)H18···O12.2800
C6···C21vii3.588 (5)H19···Cl1xi3.1500
C8—O1—C16114.76 (18)C18—C17—C22118.0 (2)
N2—N1—C2109.99 (18)C17—C18—C19121.6 (3)
N2—N1—C7120.75 (19)C18—C19—C20118.9 (3)
C2—N1—C7129.21 (18)Cl3—C20—C19120.5 (3)
N1—N2—N3108.7 (2)Cl3—C20—C21117.3 (3)
N2—N3—C1108.3 (2)C19—C20—C21122.2 (3)
N3—C1—C2108.5 (2)C20—C21—C22119.0 (3)
N3—C1—C6131.2 (2)Cl2—C22—C17123.6 (2)
C2—C1—C6120.3 (3)Cl2—C22—C21116.0 (2)
N1—C2—C1104.6 (2)C17—C22—C21120.4 (3)
N1—C2—C3133.0 (2)C2—C3—H3122.00
C1—C2—C3122.4 (2)C4—C3—H3122.00
C2—C3—C4115.8 (3)C3—C4—H4119.00
C3—C4—C5122.6 (3)C5—C4—H4119.00
C4—C5—C6122.0 (3)C4—C5—H5119.00
C1—C6—C5117.0 (3)C6—C5—H5119.00
N1—C7—C8113.92 (17)C1—C6—H6121.00
O1—C8—C7105.56 (17)C5—C6—H6122.00
O1—C8—C9109.34 (16)N1—C7—H7A109.00
C7—C8—C9112.46 (19)N1—C7—H7B109.00
O3—C9—C8119.2 (2)C8—C7—H7A109.00
O3—C9—C10121.3 (2)C8—C7—H7B109.00
C8—C9—C10119.51 (17)H7A—C7—H7B108.00
C9—C10—C11123.79 (19)C10—C11—H11120.00
C9—C10—C15117.0 (2)C12—C11—H11120.00
C11—C10—C15119.2 (2)C11—C12—H12120.00
C10—C11—C12120.1 (2)C13—C12—H12120.00
C11—C12—C13120.6 (3)C12—C13—H13121.00
C12—C13—C14118.8 (3)C14—C13—H13121.00
Cl1—C14—C13119.6 (2)C10—C15—H15120.00
Cl1—C14—C15119.0 (2)C14—C15—H15120.00
C13—C14—C15121.4 (2)C17—C18—H18119.00
C10—C15—C14119.9 (3)C19—C18—H18119.00
O1—C16—O2121.6 (2)C18—C19—H19121.00
O1—C16—C17110.65 (19)C20—C19—H19121.00
O2—C16—C17127.7 (2)C20—C21—H21120.00
C16—C17—C18119.1 (2)C22—C21—H21121.00
C16—C17—C22122.9 (2)
C8—O1—C16—C17179.15 (18)C8—C9—C10—C112.2 (3)
C16—O1—C8—C7171.37 (19)C8—C9—C10—C15179.3 (2)
C16—O1—C8—C967.4 (2)O3—C9—C10—C150.4 (3)
C8—O1—C16—O20.1 (3)O3—C9—C10—C11179.0 (2)
C7—N1—N2—N3178.03 (19)C9—C10—C15—C14178.1 (2)
N2—N1—C2—C10.1 (2)C9—C10—C11—C12177.2 (2)
N2—N1—C7—C883.0 (2)C15—C10—C11—C121.3 (4)
C2—N1—N2—N30.2 (3)C11—C10—C15—C140.6 (4)
C7—N1—C2—C31.4 (4)C10—C11—C12—C131.1 (5)
C7—N1—C2—C1177.5 (2)C11—C12—C13—C140.0 (5)
C2—N1—C7—C899.7 (3)C12—C13—C14—Cl1179.6 (3)
N2—N1—C2—C3179.0 (3)C12—C13—C14—C150.7 (5)
N1—N2—N3—C10.4 (3)C13—C14—C15—C100.5 (4)
N2—N3—C1—C6179.1 (3)Cl1—C14—C15—C10179.8 (2)
N2—N3—C1—C20.5 (3)O1—C16—C17—C184.8 (3)
C6—C1—C2—N1179.3 (2)O1—C16—C17—C22175.5 (2)
C6—C1—C2—C30.2 (4)O2—C16—C17—C18174.4 (3)
N3—C1—C6—C5178.8 (3)O2—C16—C17—C225.3 (4)
C2—C1—C6—C50.7 (4)C16—C17—C18—C19179.3 (3)
N3—C1—C2—N10.3 (3)C22—C17—C18—C190.5 (4)
N3—C1—C2—C3179.4 (2)C16—C17—C22—Cl20.8 (4)
C1—C2—C3—C40.3 (4)C16—C17—C22—C21179.3 (3)
N1—C2—C3—C4178.5 (3)C18—C17—C22—Cl2179.4 (2)
C2—C3—C4—C50.3 (5)C18—C17—C22—C210.4 (4)
C3—C4—C5—C60.2 (6)C17—C18—C19—C200.7 (4)
C4—C5—C6—C10.7 (5)C18—C19—C20—Cl3179.7 (2)
N1—C7—C8—O163.4 (2)C18—C19—C20—C210.8 (5)
N1—C7—C8—C955.7 (2)Cl3—C20—C21—C22179.7 (3)
C7—C8—C9—O387.3 (2)C19—C20—C21—C220.8 (5)
O1—C8—C9—O329.6 (3)C20—C21—C22—Cl2179.3 (3)
O1—C8—C9—C10151.55 (19)C20—C21—C22—C170.6 (5)
C7—C8—C9—C1091.5 (2)
Symmetry codes: (i) x1, y, z; (ii) x+2, y, z+2; (iii) x1, y+1/2, z1/2; (iv) x+1, y1/2, z+3/2; (v) x+2, y1/2, z+5/2; (vi) x, y+1/2, z+1/2; (vii) x, y+1/2, z1/2; (viii) x+1, y, z; (ix) x+1, y+1/2, z+3/2; (x) x+2, y+1/2, z+5/2; (xi) x+1, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O2ix0.932.413.198 (4)142
C6—H6···Cl3x0.932.833.719 (3)161
C7—H7B···O3vii0.972.553.520 (3)176
C18—H18···O10.932.282.643 (3)102
Symmetry codes: (vii) x, y+1/2, z1/2; (ix) x+1, y+1/2, z+3/2; (x) x+2, y+1/2, z+5/2.

Experimental details

Crystal data
Chemical formulaC22H13Cl3N3O3
Mr473.70
Crystal system, space groupMonoclinic, P21/c
Temperature (K)273
a, b, c (Å)10.9182 (2), 19.6123 (3), 10.0124 (2)
β (°) 92.096 (1)
V3)2142.53 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.46
Crystal size (mm)0.28 × 0.06 × 0.04
Data collection
DiffractometerSiemens SMART 1000 CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.960, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
27918, 4212, 3192
Rint0.027
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.151, 1.05
No. of reflections4212
No. of parameters280
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.68, 0.46

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O2i0.932.413.198 (4)142
C6—H6···Cl3ii0.932.833.719 (3)161
C7—H7B···O3iii0.972.553.520 (3)176
C18—H18···O10.932.282.643 (3)102
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+2, y+1/2, z+5/2; (iii) x, y+1/2, z1/2.
 

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