Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702870X/at2324sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680702870X/at2324Isup2.hkl |
CCDC reference: 654960
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (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
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.
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.
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).
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.
Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids. | |
Fig. 2. The crystal packing of (I), viewed along c axis. Hydrogen bonding interactions are indicated by dashed lines. |
C22H13Cl3N3O3 | F(000) = 964 |
Mr = 473.70 | Dx = 1.469 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3223 reflections |
a = 10.9182 (2) Å | θ = 1.9–26.0° |
b = 19.6123 (3) Å | µ = 0.46 mm−1 |
c = 10.0124 (2) Å | T = 273 K |
β = 92.096 (1)° | Prism, colourless |
V = 2142.53 (7) Å3 | 0.28 × 0.06 × 0.04 mm |
Z = 4 |
Siemens SMART 1000 CCD area-detector diffractometer | 4212 independent reflections |
Radiation source: fine-focus sealed tube | 3192 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 26.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −13→12 |
Tmin = 0.960, Tmax = 0.980 | k = −24→24 |
27918 measured reflections | l = −12→12 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H-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 parameters | Δρmax = 0.68 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−3 |
C22H13Cl3N3O3 | V = 2142.53 (7) Å3 |
Mr = 473.70 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.9182 (2) Å | µ = 0.46 mm−1 |
b = 19.6123 (3) Å | T = 273 K |
c = 10.0124 (2) Å | 0.28 × 0.06 × 0.04 mm |
β = 92.096 (1)° |
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 = 0.980 | Rint = 0.027 |
27918 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.68 e Å−3 |
4212 reflections | Δρmin = −0.46 e Å−3 |
280 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.08295 (7) | 0.21406 (6) | 0.75068 (11) | 0.0959 (4) | |
Cl2 | 0.70830 (11) | −0.05478 (5) | 1.02091 (11) | 0.1040 (4) | |
Cl3 | 1.09105 (14) | 0.01904 (8) | 1.32415 (11) | 0.1447 (6) | |
O1 | 0.75829 (15) | 0.14993 (8) | 0.83033 (16) | 0.0468 (5) | |
O2 | 0.6409 (2) | 0.05810 (10) | 0.8437 (2) | 0.0793 (8) | |
O3 | 0.54692 (17) | 0.20882 (10) | 0.89673 (17) | 0.0562 (6) | |
N1 | 0.75249 (17) | 0.29201 (10) | 0.75969 (18) | 0.0413 (6) | |
N2 | 0.84951 (19) | 0.29393 (12) | 0.8493 (2) | 0.0527 (7) | |
N3 | 0.8438 (2) | 0.35025 (12) | 0.9182 (2) | 0.0594 (8) | |
C1 | 0.7421 (3) | 0.38627 (13) | 0.8729 (2) | 0.0510 (8) | |
C2 | 0.6831 (2) | 0.34902 (11) | 0.7716 (2) | 0.0420 (7) | |
C3 | 0.5776 (3) | 0.37220 (14) | 0.7044 (3) | 0.0555 (9) | |
C4 | 0.5353 (3) | 0.43447 (16) | 0.7439 (3) | 0.0740 (11) | |
C5 | 0.5931 (4) | 0.47225 (16) | 0.8448 (4) | 0.0810 (13) | |
C6 | 0.6956 (3) | 0.44969 (15) | 0.9115 (3) | 0.0713 (13) | |
C7 | 0.7376 (2) | 0.23588 (12) | 0.6664 (2) | 0.0436 (7) | |
C8 | 0.6763 (2) | 0.17327 (12) | 0.7247 (2) | 0.0424 (7) | |
C9 | 0.5515 (2) | 0.18976 (11) | 0.7819 (2) | 0.0406 (7) | |
C10 | 0.4383 (2) | 0.18335 (11) | 0.6947 (2) | 0.0414 (7) | |
C11 | 0.4378 (2) | 0.16088 (14) | 0.5633 (2) | 0.0523 (8) | |
C12 | 0.3277 (3) | 0.15362 (17) | 0.4908 (3) | 0.0659 (10) | |
C13 | 0.2185 (3) | 0.16959 (17) | 0.5473 (3) | 0.0673 (11) | |
C14 | 0.2202 (2) | 0.19297 (15) | 0.6776 (3) | 0.0599 (10) | |
C15 | 0.3280 (2) | 0.19972 (13) | 0.7513 (3) | 0.0520 (8) | |
C16 | 0.7286 (2) | 0.08918 (12) | 0.8832 (3) | 0.0484 (8) | |
C17 | 0.8177 (2) | 0.07003 (13) | 0.9928 (2) | 0.0487 (8) | |
C18 | 0.9089 (2) | 0.11622 (15) | 1.0323 (3) | 0.0564 (9) | |
C19 | 0.9930 (3) | 0.10150 (19) | 1.1342 (3) | 0.0730 (11) | |
C20 | 0.9870 (3) | 0.0400 (2) | 1.1963 (3) | 0.0781 (13) | |
C21 | 0.8994 (4) | −0.00732 (18) | 1.1621 (3) | 0.0806 (13) | |
C22 | 0.8140 (3) | 0.00766 (14) | 1.0588 (3) | 0.0629 (10) | |
H3 | 0.53820 | 0.34700 | 0.63690 | 0.0670* | |
H4 | 0.46510 | 0.45210 | 0.70140 | 0.0890* | |
H5 | 0.56050 | 0.51430 | 0.86750 | 0.0970* | |
H6 | 0.73340 | 0.47510 | 0.97970 | 0.0850* | |
H7A | 0.81760 | 0.22290 | 0.63590 | 0.0520* | |
H7B | 0.68910 | 0.25130 | 0.58910 | 0.0520* | |
H11 | 0.51130 | 0.15070 | 0.52370 | 0.0630* | |
H12 | 0.32780 | 0.13780 | 0.40330 | 0.0790* | |
H13 | 0.14480 | 0.16480 | 0.49870 | 0.0810* | |
H15 | 0.32710 | 0.21520 | 0.83900 | 0.0620* | |
H18 | 0.91310 | 0.15800 | 0.98890 | 0.0680* | |
H19 | 1.05280 | 0.13310 | 1.16010 | 0.0870* | |
H21 | 0.89670 | −0.04880 | 1.20690 | 0.0970* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0421 (4) | 0.1304 (8) | 0.1155 (8) | 0.0145 (5) | 0.0062 (4) | −0.0038 (6) |
Cl2 | 0.1360 (9) | 0.0568 (5) | 0.1168 (8) | −0.0154 (5) | −0.0278 (7) | 0.0304 (5) |
Cl3 | 0.1632 (12) | 0.1765 (13) | 0.0890 (7) | 0.0837 (10) | −0.0691 (8) | −0.0215 (8) |
O1 | 0.0430 (9) | 0.0391 (9) | 0.0573 (10) | 0.0023 (7) | −0.0099 (7) | 0.0053 (7) |
O2 | 0.0795 (15) | 0.0546 (12) | 0.1007 (16) | −0.0224 (11) | −0.0391 (12) | 0.0201 (11) |
O3 | 0.0517 (11) | 0.0731 (12) | 0.0435 (10) | 0.0066 (9) | −0.0009 (7) | −0.0078 (9) |
N1 | 0.0394 (10) | 0.0443 (10) | 0.0401 (10) | 0.0010 (8) | 0.0010 (8) | 0.0055 (8) |
N2 | 0.0447 (12) | 0.0611 (14) | 0.0518 (12) | −0.0035 (10) | −0.0058 (9) | 0.0133 (10) |
N3 | 0.0653 (15) | 0.0611 (14) | 0.0509 (12) | −0.0160 (11) | −0.0094 (11) | 0.0063 (11) |
C1 | 0.0632 (16) | 0.0491 (14) | 0.0407 (12) | −0.0118 (12) | 0.0031 (11) | 0.0031 (11) |
C2 | 0.0504 (14) | 0.0388 (12) | 0.0371 (11) | −0.0001 (10) | 0.0061 (10) | 0.0041 (9) |
C3 | 0.0603 (17) | 0.0520 (15) | 0.0536 (14) | 0.0104 (12) | −0.0057 (12) | −0.0003 (12) |
C4 | 0.081 (2) | 0.0582 (18) | 0.082 (2) | 0.0245 (16) | −0.0064 (17) | −0.0012 (16) |
C5 | 0.111 (3) | 0.0496 (17) | 0.083 (2) | 0.0168 (17) | 0.010 (2) | −0.0103 (16) |
C6 | 0.103 (3) | 0.0523 (16) | 0.0588 (17) | −0.0130 (17) | 0.0054 (17) | −0.0121 (14) |
C7 | 0.0452 (13) | 0.0471 (13) | 0.0388 (11) | 0.0063 (10) | 0.0054 (10) | 0.0012 (10) |
C8 | 0.0410 (13) | 0.0413 (12) | 0.0446 (12) | 0.0068 (10) | −0.0039 (10) | 0.0022 (10) |
C9 | 0.0434 (13) | 0.0374 (11) | 0.0408 (12) | 0.0028 (9) | −0.0002 (9) | 0.0038 (9) |
C10 | 0.0406 (13) | 0.0388 (12) | 0.0446 (12) | 0.0009 (10) | −0.0021 (10) | 0.0060 (9) |
C11 | 0.0482 (14) | 0.0610 (16) | 0.0476 (14) | 0.0007 (12) | −0.0008 (11) | 0.0016 (12) |
C12 | 0.0608 (18) | 0.083 (2) | 0.0528 (16) | −0.0025 (15) | −0.0127 (13) | −0.0021 (14) |
C13 | 0.0495 (17) | 0.079 (2) | 0.0721 (19) | −0.0019 (14) | −0.0169 (14) | 0.0088 (16) |
C14 | 0.0389 (14) | 0.0645 (17) | 0.0761 (19) | 0.0040 (12) | 0.0008 (12) | 0.0085 (14) |
C15 | 0.0456 (14) | 0.0548 (15) | 0.0554 (14) | 0.0029 (11) | 0.0011 (11) | 0.0000 (12) |
C16 | 0.0492 (15) | 0.0380 (12) | 0.0575 (14) | 0.0043 (11) | −0.0062 (11) | 0.0013 (11) |
C17 | 0.0512 (14) | 0.0448 (13) | 0.0499 (14) | 0.0141 (11) | −0.0023 (11) | −0.0034 (11) |
C18 | 0.0491 (15) | 0.0614 (16) | 0.0582 (15) | 0.0127 (12) | −0.0048 (12) | −0.0113 (12) |
C19 | 0.0615 (19) | 0.087 (2) | 0.0691 (19) | 0.0222 (16) | −0.0185 (15) | −0.0238 (17) |
C20 | 0.083 (2) | 0.094 (3) | 0.0555 (17) | 0.043 (2) | −0.0218 (16) | −0.0217 (17) |
C21 | 0.114 (3) | 0.072 (2) | 0.0552 (17) | 0.042 (2) | −0.0043 (18) | 0.0082 (15) |
C22 | 0.080 (2) | 0.0494 (15) | 0.0586 (16) | 0.0167 (14) | −0.0050 (14) | 0.0024 (12) |
Cl1—C14 | 1.741 (3) | C12—C13 | 1.374 (5) |
Cl2—C22 | 1.716 (3) | C13—C14 | 1.382 (4) |
Cl3—C20 | 1.730 (3) | C14—C15 | 1.373 (3) |
O1—C8 | 1.435 (3) | C16—C17 | 1.488 (3) |
O1—C16 | 1.348 (3) | C17—C18 | 1.393 (3) |
O2—C16 | 1.190 (3) | C17—C22 | 1.392 (4) |
O3—C9 | 1.212 (3) | C18—C19 | 1.378 (4) |
N1—N2 | 1.363 (3) | C19—C20 | 1.360 (5) |
N1—C2 | 1.358 (3) | C20—C21 | 1.367 (5) |
N1—C7 | 1.449 (3) | C21—C22 | 1.398 (5) |
N2—N3 | 1.305 (3) | C3—H3 | 0.9300 |
N3—C1 | 1.379 (4) | C4—H4 | 0.9300 |
C1—C2 | 1.389 (3) | C5—H5 | 0.9300 |
C1—C6 | 1.403 (4) | C6—H6 | 0.9300 |
C2—C3 | 1.389 (4) | C7—H7A | 0.9700 |
C3—C4 | 1.369 (4) | C7—H7B | 0.9700 |
C4—C5 | 1.386 (5) | C11—H11 | 0.9300 |
C5—C6 | 1.356 (5) | C12—H12 | 0.9300 |
C7—C8 | 1.525 (3) | C13—H13 | 0.9300 |
C8—C9 | 1.532 (3) | C15—H15 | 0.9300 |
C9—C10 | 1.492 (3) | C18—H18 | 0.9300 |
C10—C11 | 1.387 (3) | C19—H19 | 0.9300 |
C10—C15 | 1.387 (3) | C21—H21 | 0.9300 |
C11—C12 | 1.389 (4) | ||
Cl1···N2i | 3.180 (2) | C7···N3vii | 3.253 (3) |
Cl2···O2 | 2.915 (2) | C9···O2 | 2.821 (3) |
Cl3···C16ii | 3.604 (3) | C9···C2 | 3.441 (3) |
Cl1···H7Ai | 3.0800 | C11···O3vii | 3.298 (3) |
Cl1···H19iii | 3.1500 | C16···Cl3ii | 3.604 (3) |
Cl2···H4iv | 2.8700 | C16···O3 | 3.079 (3) |
Cl3···H6v | 2.8300 | C17···C2vi | 3.574 (3) |
O1···O3 | 2.686 (2) | C18···C2vi | 3.566 (3) |
O1···N1 | 2.875 (3) | C18···N1vi | 3.409 (3) |
O1···N2 | 2.998 (3) | C19···N2vi | 3.398 (4) |
O2···C9 | 2.821 (3) | C20···C1vi | 3.566 (4) |
O2···Cl2 | 2.915 (2) | C20···C22ii | 3.539 (4) |
O2···O3 | 3.180 (3) | C21···C6vi | 3.588 (5) |
O2···C4iv | 3.198 (4) | C22···C20ii | 3.539 (4) |
O3···O2 | 3.180 (3) | C1···H11vi | 3.0700 |
O3···C11vi | 3.298 (3) | C3···H7B | 2.9200 |
O3···O1 | 2.686 (2) | C6···H11vi | 3.0600 |
O3···C16 | 3.079 (3) | C7···H3 | 3.0900 |
O3···N1 | 3.132 (3) | C8···H11 | 2.6900 |
O3···C2 | 3.388 (3) | C11···H5iv | 2.9600 |
O1···H18 | 2.2800 | C12···H15vii | 2.9900 |
O2···H4iv | 2.4100 | H3···C7 | 3.0900 |
O3···H15 | 2.4500 | H3···H7B | 2.5500 |
O3···H3vi | 2.6500 | H3···O3vii | 2.6500 |
O3···H7Bvi | 2.5500 | H4···Cl2ix | 2.8700 |
N1···O1 | 2.875 (3) | H4···O2ix | 2.4100 |
N1···O3 | 3.132 (3) | H5···C11ix | 2.9600 |
N1···C18vii | 3.409 (3) | H6···Cl3x | 2.8300 |
N2···Cl1viii | 3.180 (2) | H7A···Cl1viii | 3.0800 |
N2···O1 | 2.998 (3) | H7A···N2vii | 2.9200 |
N2···C19vii | 3.398 (4) | H7A···N3vii | 2.6300 |
N3···C7vi | 3.253 (3) | H7B···C3 | 2.9200 |
N2···H7Avi | 2.9200 | H7B···H3 | 2.5500 |
N3···H7Avi | 2.6300 | H7B···O3vii | 2.5500 |
C1···C20vii | 3.566 (4) | H11···C8 | 2.6900 |
C2···C17vii | 3.574 (3) | H11···C1vii | 3.0700 |
C2···O3 | 3.388 (3) | H11···C6vii | 3.0600 |
C2···C9 | 3.441 (3) | H15···O3 | 2.4500 |
C2···C18vii | 3.566 (3) | H15···C12vi | 2.9900 |
C4···O2ix | 3.198 (4) | H18···O1 | 2.2800 |
C6···C21vii | 3.588 (5) | H19···Cl1xi | 3.1500 |
C8—O1—C16 | 114.76 (18) | C18—C17—C22 | 118.0 (2) |
N2—N1—C2 | 109.99 (18) | C17—C18—C19 | 121.6 (3) |
N2—N1—C7 | 120.75 (19) | C18—C19—C20 | 118.9 (3) |
C2—N1—C7 | 129.21 (18) | Cl3—C20—C19 | 120.5 (3) |
N1—N2—N3 | 108.7 (2) | Cl3—C20—C21 | 117.3 (3) |
N2—N3—C1 | 108.3 (2) | C19—C20—C21 | 122.2 (3) |
N3—C1—C2 | 108.5 (2) | C20—C21—C22 | 119.0 (3) |
N3—C1—C6 | 131.2 (2) | Cl2—C22—C17 | 123.6 (2) |
C2—C1—C6 | 120.3 (3) | Cl2—C22—C21 | 116.0 (2) |
N1—C2—C1 | 104.6 (2) | C17—C22—C21 | 120.4 (3) |
N1—C2—C3 | 133.0 (2) | C2—C3—H3 | 122.00 |
C1—C2—C3 | 122.4 (2) | C4—C3—H3 | 122.00 |
C2—C3—C4 | 115.8 (3) | C3—C4—H4 | 119.00 |
C3—C4—C5 | 122.6 (3) | C5—C4—H4 | 119.00 |
C4—C5—C6 | 122.0 (3) | C4—C5—H5 | 119.00 |
C1—C6—C5 | 117.0 (3) | C6—C5—H5 | 119.00 |
N1—C7—C8 | 113.92 (17) | C1—C6—H6 | 121.00 |
O1—C8—C7 | 105.56 (17) | C5—C6—H6 | 122.00 |
O1—C8—C9 | 109.34 (16) | N1—C7—H7A | 109.00 |
C7—C8—C9 | 112.46 (19) | N1—C7—H7B | 109.00 |
O3—C9—C8 | 119.2 (2) | C8—C7—H7A | 109.00 |
O3—C9—C10 | 121.3 (2) | C8—C7—H7B | 109.00 |
C8—C9—C10 | 119.51 (17) | H7A—C7—H7B | 108.00 |
C9—C10—C11 | 123.79 (19) | C10—C11—H11 | 120.00 |
C9—C10—C15 | 117.0 (2) | C12—C11—H11 | 120.00 |
C11—C10—C15 | 119.2 (2) | C11—C12—H12 | 120.00 |
C10—C11—C12 | 120.1 (2) | C13—C12—H12 | 120.00 |
C11—C12—C13 | 120.6 (3) | C12—C13—H13 | 121.00 |
C12—C13—C14 | 118.8 (3) | C14—C13—H13 | 121.00 |
Cl1—C14—C13 | 119.6 (2) | C10—C15—H15 | 120.00 |
Cl1—C14—C15 | 119.0 (2) | C14—C15—H15 | 120.00 |
C13—C14—C15 | 121.4 (2) | C17—C18—H18 | 119.00 |
C10—C15—C14 | 119.9 (3) | C19—C18—H18 | 119.00 |
O1—C16—O2 | 121.6 (2) | C18—C19—H19 | 121.00 |
O1—C16—C17 | 110.65 (19) | C20—C19—H19 | 121.00 |
O2—C16—C17 | 127.7 (2) | C20—C21—H21 | 120.00 |
C16—C17—C18 | 119.1 (2) | C22—C21—H21 | 121.00 |
C16—C17—C22 | 122.9 (2) | ||
C8—O1—C16—C17 | −179.15 (18) | C8—C9—C10—C11 | 2.2 (3) |
C16—O1—C8—C7 | −171.37 (19) | C8—C9—C10—C15 | −179.3 (2) |
C16—O1—C8—C9 | 67.4 (2) | O3—C9—C10—C15 | −0.4 (3) |
C8—O1—C16—O2 | 0.1 (3) | O3—C9—C10—C11 | −179.0 (2) |
C7—N1—N2—N3 | 178.03 (19) | C9—C10—C15—C14 | −178.1 (2) |
N2—N1—C2—C1 | 0.1 (2) | C9—C10—C11—C12 | 177.2 (2) |
N2—N1—C7—C8 | 83.0 (2) | C15—C10—C11—C12 | −1.3 (4) |
C2—N1—N2—N3 | 0.2 (3) | C11—C10—C15—C14 | 0.6 (4) |
C7—N1—C2—C3 | 1.4 (4) | C10—C11—C12—C13 | 1.1 (5) |
C7—N1—C2—C1 | −177.5 (2) | C11—C12—C13—C14 | 0.0 (5) |
C2—N1—C7—C8 | −99.7 (3) | C12—C13—C14—Cl1 | 179.6 (3) |
N2—N1—C2—C3 | 179.0 (3) | C12—C13—C14—C15 | −0.7 (5) |
N1—N2—N3—C1 | −0.4 (3) | C13—C14—C15—C10 | 0.5 (4) |
N2—N3—C1—C6 | −179.1 (3) | Cl1—C14—C15—C10 | −179.8 (2) |
N2—N3—C1—C2 | 0.5 (3) | O1—C16—C17—C18 | 4.8 (3) |
C6—C1—C2—N1 | 179.3 (2) | O1—C16—C17—C22 | −175.5 (2) |
C6—C1—C2—C3 | 0.2 (4) | O2—C16—C17—C18 | −174.4 (3) |
N3—C1—C6—C5 | 178.8 (3) | O2—C16—C17—C22 | 5.3 (4) |
C2—C1—C6—C5 | −0.7 (4) | C16—C17—C18—C19 | 179.3 (3) |
N3—C1—C2—N1 | −0.3 (3) | C22—C17—C18—C19 | −0.5 (4) |
N3—C1—C2—C3 | −179.4 (2) | C16—C17—C22—Cl2 | 0.8 (4) |
C1—C2—C3—C4 | 0.3 (4) | C16—C17—C22—C21 | −179.3 (3) |
N1—C2—C3—C4 | −178.5 (3) | C18—C17—C22—Cl2 | −179.4 (2) |
C2—C3—C4—C5 | −0.3 (5) | C18—C17—C22—C21 | 0.4 (4) |
C3—C4—C5—C6 | −0.2 (6) | C17—C18—C19—C20 | 0.7 (4) |
C4—C5—C6—C1 | 0.7 (5) | C18—C19—C20—Cl3 | 179.7 (2) |
N1—C7—C8—O1 | −63.4 (2) | C18—C19—C20—C21 | −0.8 (5) |
N1—C7—C8—C9 | 55.7 (2) | Cl3—C20—C21—C22 | −179.7 (3) |
C7—C8—C9—O3 | −87.3 (2) | C19—C20—C21—C22 | 0.8 (5) |
O1—C8—C9—O3 | 29.6 (3) | C20—C21—C22—Cl2 | 179.3 (3) |
O1—C8—C9—C10 | −151.55 (19) | C20—C21—C22—C17 | −0.6 (5) |
C7—C8—C9—C10 | 91.5 (2) |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y, −z+2; (iii) x−1, −y+1/2, z−1/2; (iv) −x+1, y−1/2, −z+3/2; (v) −x+2, y−1/2, −z+5/2; (vi) x, −y+1/2, z+1/2; (vii) x, −y+1/2, z−1/2; (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. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O2ix | 0.93 | 2.41 | 3.198 (4) | 142 |
C6—H6···Cl3x | 0.93 | 2.83 | 3.719 (3) | 161 |
C7—H7B···O3vii | 0.97 | 2.55 | 3.520 (3) | 176 |
C18—H18···O1 | 0.93 | 2.28 | 2.643 (3) | 102 |
Symmetry codes: (vii) x, −y+1/2, z−1/2; (ix) −x+1, y+1/2, −z+3/2; (x) −x+2, y+1/2, −z+5/2. |
Experimental details
Crystal data | |
Chemical formula | C22H13Cl3N3O3 |
Mr | 473.70 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 10.9182 (2), 19.6123 (3), 10.0124 (2) |
β (°) | 92.096 (1) |
V (Å3) | 2142.53 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.46 |
Crystal size (mm) | 0.28 × 0.06 × 0.04 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.960, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27918, 4212, 3192 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.151, 1.05 |
No. of reflections | 4212 |
No. of parameters | 280 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.68, −0.46 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O2i | 0.93 | 2.41 | 3.198 (4) | 142 |
C6—H6···Cl3ii | 0.93 | 2.83 | 3.719 (3) | 161 |
C7—H7B···O3iii | 0.97 | 2.55 | 3.520 (3) | 176 |
C18—H18···O1 | 0.93 | 2.28 | 2.643 (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, z−1/2. |
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).