2-(1H-1,2,3-Benzotriazol-1-yl)-1-(2-fluoro­benzoyl)ethyl 2-chloro­benzoate

In the crystal structure of the title compound, C₂₂H₁₅ClFN₃O₃, the crystal packing is controlled by van der Waals forces. Weak intramolecular C—H...O and C—H...F hydrogen bonds link the molecules into chains extended along the c axis.The packing is further stabilized by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.061
• wR factor = 0.208
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    F1     -   C15     ..       8.79 su

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         46 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C15     ..       6.22 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C20    -   C21     ..       5.07 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N1
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C8     = ...          R

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 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
   2 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

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S1. Comment

1H-Benzotriazole and its derivatives 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 the bond lengths and angles in (I) are within their normal ranges (Allen et al., 1987). The benzotriazole ring system is essentially planar, with a dihedral angle of 0.9 (1)° between the triazole ring (atoms N1—N3/C1/C6) and the C1—C6 benzene ring. The dihedral angles between the mean planes of the benzotriazole system and the C10—C15 and C17—C22 aromatic rings are 5.21 (1)° and 61.81 (1)°, respectively. The dihedral angle between rings C10—C15 and C17—C22 is 57.7 (2)°. Molecule (I) is chiral. In the arbitrarily chosen asymmetric molecule, C8 has R configuration, but crystal symmetry generates a racemic mixture.

Related literature

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

S2. Experimental

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-(2-fluorophenyl)propan-1-one (5.38 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-chlorobenzoic acid (3.1 g, 0.02 mol) and triethylamine (2.8 ml) was added. The mixture was stirred with ice–water for 6 h. The solution was then filtered and concentrated. Single crystals of (I) were obtained by slow evaporation of an acetone-ethylacetate (1:1 v/v) solution at room temperature over a period of one week.

S3. Refinement

The H atoms were geometrically placed (C—H = 0.93–0.97 Å), and refined as riding with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C).

Computing details

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

Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids (arbitrary spheres for the H atoms).

2-(1<it>H</it>-1,2,3-Benzotriazol-1-yl)-1-(2-fluorobenzoyl)ethyl 2-chlorobenzoate

Crystal data

C22H15ClFN3O3	F(000) = 872
Mr = 423.82	Dx = 1.433 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1651 reflections
a = 10.858 (3) Å	θ = 2.4–21.0°
b = 8.279 (2) Å	µ = 0.23 mm^−1
c = 22.236 (6) Å	T = 294 K
β = 100.599 (5)°	Block, colourless
V = 1964.9 (9) Å^3	0.20 × 0.16 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3993 independent reflections
Radiation source: fine-focus sealed tube	1838 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
ω scans	θmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −13→10
Tmin = 0.955, Tmax = 0.977	k = −10→10
10896 measured reflections	l = −27→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.208	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.1046P)^2] where P = (Fo^2 + 2Fc^2)/3
3993 reflections	(Δ/σ)max = 0.002
271 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.16809 (12)	0.54811 (16)	1.00954 (5)	0.0998 (5)
F1	0.2942 (2)	0.7314 (3)	0.71581 (10)	0.1010 (9)
O1	0.40423 (19)	0.8137 (2)	0.90054 (9)	0.0485 (6)
O2	0.2520 (3)	0.6305 (3)	0.89726 (11)	0.0778 (8)
O3	0.1967 (3)	0.9868 (4)	0.86057 (13)	0.0912 (10)
N1	0.7216 (4)	0.7326 (5)	0.78904 (19)	0.0916 (11)
N2	0.6068 (4)	0.7844 (4)	0.77393 (14)	0.0773 (10)
N3	0.5786 (3)	0.8780 (3)	0.81969 (12)	0.0537 (7)
C1	0.7691 (4)	0.7934 (5)	0.8454 (2)	0.0678 (11)
C2	0.8887 (4)	0.7754 (6)	0.8829 (3)	0.0968 (16)
H2	0.9516	0.7151	0.8702	0.116*
C3	0.9073 (5)	0.8501 (6)	0.9380 (3)	0.0999 (16)
H3	0.9849	0.8408	0.9636	0.120*
C4	0.8128 (5)	0.9413 (5)	0.9577 (2)	0.0884 (14)
H4	0.8295	0.9884	0.9963	0.106*
C5	0.6996 (4)	0.9625 (4)	0.92264 (18)	0.0664 (11)
H5	0.6383	1.0249	0.9356	0.080*
C6	0.6785 (3)	0.8861 (4)	0.86548 (16)	0.0506 (9)
C7	0.4558 (3)	0.9480 (4)	0.81416 (15)	0.0576 (9)
H7A	0.4250	0.9761	0.7717	0.069*
H7B	0.4614	1.0466	0.8380	0.069*
C8	0.3624 (3)	0.8336 (4)	0.83592 (13)	0.0513 (9)
H8	0.3636	0.7289	0.8155	0.062*
C9	0.2313 (3)	0.9028 (4)	0.82231 (17)	0.0606 (10)
C10	0.1471 (3)	0.8742 (4)	0.76184 (15)	0.0549 (9)
C11	0.0281 (4)	0.9362 (5)	0.7543 (2)	0.0757 (12)
H11	0.0032	0.9919	0.7863	0.091*
C12	−0.0549 (4)	0.9173 (6)	0.7001 (2)	0.0919 (14)
H12	−0.1354	0.9597	0.6961	0.110*
C13	−0.0210 (4)	0.8378 (6)	0.6526 (2)	0.0818 (13)
H13	−0.0782	0.8279	0.6162	0.098*
C14	0.0958 (4)	0.7718 (5)	0.65701 (18)	0.0774 (12)
H14	0.1196	0.7160	0.6247	0.093*
C15	0.1774 (3)	0.7928 (5)	0.71290 (18)	0.0651 (10)
C16	0.3388 (4)	0.7037 (4)	0.92604 (15)	0.0539 (9)
C17	0.3902 (3)	0.6798 (4)	0.99247 (14)	0.0495 (9)
C18	0.5139 (3)	0.7262 (4)	1.01529 (15)	0.0577 (9)
H18	0.5608	0.7757	0.9895	0.069*
C19	0.5670 (4)	0.6991 (5)	1.07574 (18)	0.0751 (12)
H19	0.6492	0.7303	1.0907	0.090*
C20	0.4973 (5)	0.6255 (5)	1.11360 (18)	0.0806 (14)
H20	0.5331	0.6068	1.1543	0.097*
C21	0.3755 (5)	0.5791 (5)	1.09238 (18)	0.0735 (12)
H21	0.3291	0.5304	1.1186	0.088*
C22	0.3228 (4)	0.6054 (4)	1.03192 (16)	0.0590 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0918 (9)	0.1274 (11)	0.0858 (8)	−0.0368 (8)	0.0311 (7)	0.0029 (7)
F1	0.0808 (17)	0.155 (2)	0.0642 (14)	0.0226 (17)	0.0061 (12)	−0.0280 (14)
O1	0.0490 (13)	0.0555 (14)	0.0380 (12)	−0.0029 (11)	0.0005 (10)	0.0016 (10)
O2	0.0747 (19)	0.098 (2)	0.0545 (15)	−0.0333 (17)	−0.0044 (14)	−0.0018 (14)
O3	0.082 (2)	0.113 (2)	0.0746 (19)	0.0369 (18)	0.0036 (16)	−0.0210 (17)
N1	0.079 (3)	0.103 (3)	0.102 (3)	0.003 (2)	0.039 (2)	−0.023 (2)
N2	0.081 (3)	0.095 (3)	0.059 (2)	−0.007 (2)	0.0243 (19)	−0.0179 (18)
N3	0.0548 (19)	0.0581 (18)	0.0495 (17)	−0.0003 (15)	0.0132 (15)	−0.0046 (14)
C1	0.057 (3)	0.064 (2)	0.085 (3)	−0.004 (2)	0.020 (2)	0.000 (2)
C2	0.054 (3)	0.075 (3)	0.164 (5)	0.000 (2)	0.025 (3)	0.012 (3)
C3	0.060 (3)	0.086 (3)	0.139 (5)	−0.010 (3)	−0.019 (3)	0.016 (3)
C4	0.076 (3)	0.084 (3)	0.093 (3)	−0.015 (3)	−0.014 (3)	−0.009 (3)
C5	0.056 (2)	0.062 (2)	0.076 (3)	−0.0047 (19)	−0.001 (2)	−0.010 (2)
C6	0.046 (2)	0.0460 (19)	0.059 (2)	−0.0070 (17)	0.0072 (18)	0.0008 (17)
C7	0.060 (2)	0.059 (2)	0.051 (2)	0.0031 (19)	0.0035 (18)	0.0064 (17)
C8	0.049 (2)	0.063 (2)	0.0385 (18)	0.0026 (17)	0.0007 (15)	0.0003 (16)
C9	0.062 (2)	0.065 (2)	0.054 (2)	0.011 (2)	0.0083 (19)	−0.0019 (18)
C10	0.055 (2)	0.062 (2)	0.046 (2)	−0.0048 (19)	0.0041 (17)	0.0071 (17)
C11	0.060 (3)	0.081 (3)	0.083 (3)	0.012 (2)	0.003 (2)	0.008 (2)
C12	0.067 (3)	0.107 (4)	0.094 (4)	0.018 (3)	−0.005 (3)	0.019 (3)
C13	0.068 (3)	0.100 (3)	0.064 (3)	−0.014 (3)	−0.022 (2)	0.018 (2)
C14	0.075 (3)	0.099 (3)	0.051 (2)	−0.016 (3)	−0.004 (2)	0.004 (2)
C15	0.043 (2)	0.081 (3)	0.070 (3)	0.006 (2)	0.006 (2)	0.014 (2)
C16	0.054 (2)	0.061 (2)	0.047 (2)	0.0004 (19)	0.0075 (18)	−0.0006 (17)
C17	0.059 (2)	0.049 (2)	0.0394 (18)	0.0058 (17)	0.0052 (17)	−0.0060 (15)
C18	0.060 (2)	0.068 (2)	0.041 (2)	0.0046 (19)	0.0000 (18)	−0.0062 (16)
C19	0.073 (3)	0.085 (3)	0.061 (3)	0.021 (2)	−0.006 (2)	−0.017 (2)
C20	0.126 (4)	0.070 (3)	0.042 (2)	0.035 (3)	0.004 (3)	−0.001 (2)
C21	0.109 (4)	0.064 (3)	0.051 (2)	0.009 (3)	0.023 (2)	0.0048 (19)
C22	0.078 (3)	0.053 (2)	0.047 (2)	0.008 (2)	0.0142 (19)	−0.0013 (16)

Geometric parameters (Å, º)

Cl1—C22	1.728 (4)	C8—C9	1.513 (5)
F1—C15	1.357 (4)	C8—H8	0.9800
O1—C16	1.344 (4)	C9—C10	1.499 (5)
O1—C8	1.435 (4)	C10—C15	1.371 (5)
O2—C16	1.201 (4)	C10—C11	1.371 (5)
O3—C9	1.211 (4)	C11—C12	1.374 (6)
N1—N2	1.303 (5)	C11—H11	0.9300
N1—C1	1.361 (5)	C12—C13	1.353 (6)
N2—N3	1.358 (4)	C12—H12	0.9300
N3—C6	1.346 (4)	C13—C14	1.368 (6)
N3—C7	1.438 (4)	C13—H13	0.9300
C1—C6	1.385 (5)	C14—C15	1.398 (5)
C1—C2	1.416 (6)	C14—H14	0.9300
C2—C3	1.354 (7)	C16—C17	1.493 (4)
C2—H2	0.9300	C17—C22	1.386 (5)
C3—C4	1.408 (6)	C17—C18	1.400 (5)
C3—H3	0.9300	C18—C19	1.380 (5)
C4—C5	1.340 (6)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.374 (6)
C5—C6	1.401 (5)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.374 (6)
C7—C8	1.529 (5)	C20—H20	0.9300
C7—H7A	0.9700	C21—C22	1.378 (5)
C7—H7B	0.9700	C21—H21	0.9300
C16—O1—C8	113.9 (2)	C15—C10—C11	116.4 (3)
N2—N1—C1	107.4 (3)	C15—C10—C9	126.4 (3)
N1—N2—N3	109.4 (3)	C11—C10—C9	117.2 (4)
C6—N3—N2	109.5 (3)	C10—C11—C12	121.1 (4)
C6—N3—C7	130.6 (3)	C10—C11—H11	119.5
N2—N3—C7	119.9 (3)	C12—C11—H11	119.5
N1—C1—C6	109.3 (4)	C13—C12—C11	120.7 (4)
N1—C1—C2	130.9 (4)	C13—C12—H12	119.6
C6—C1—C2	119.9 (4)	C11—C12—H12	119.6
C3—C2—C1	116.9 (5)	C12—C13—C14	121.4 (4)
C3—C2—H2	121.6	C12—C13—H13	119.3
C1—C2—H2	121.6	C14—C13—H13	119.3
C2—C3—C4	122.1 (4)	C13—C14—C15	116.2 (4)
C2—C3—H3	118.9	C13—C14—H14	121.9
C4—C3—H3	118.9	C15—C14—H14	121.9
C5—C4—C3	122.1 (4)	F1—C15—C10	120.4 (3)
C5—C4—H4	118.9	F1—C15—C14	115.4 (4)
C3—C4—H4	118.9	C10—C15—C14	124.2 (4)
C4—C5—C6	116.7 (4)	O2—C16—O1	122.8 (3)
C4—C5—H5	121.7	O2—C16—C17	125.1 (3)
C6—C5—H5	121.7	O1—C16—C17	112.1 (3)
N3—C6—C1	104.5 (3)	C22—C17—C18	118.4 (3)
N3—C6—C5	133.2 (3)	C22—C17—C16	122.7 (3)
C1—C6—C5	122.3 (4)	C18—C17—C16	118.8 (3)
N3—C7—C8	112.4 (3)	C19—C18—C17	120.6 (4)
N3—C7—H7A	109.1	C19—C18—H18	119.7
C8—C7—H7A	109.1	C17—C18—H18	119.7
N3—C7—H7B	109.1	C20—C19—C18	119.4 (4)
C8—C7—H7B	109.1	C20—C19—H19	120.3
H7A—C7—H7B	107.8	C18—C19—H19	120.3
O1—C8—C9	110.9 (3)	C19—C20—C21	121.1 (4)
O1—C8—C7	106.4 (3)	C19—C20—H20	119.4
C9—C8—C7	110.9 (3)	C21—C20—H20	119.4
O1—C8—H8	109.5	C20—C21—C22	119.5 (4)
C9—C8—H8	109.5	C20—C21—H21	120.3
C7—C8—H8	109.5	C22—C21—H21	120.3
O3—C9—C10	120.3 (3)	C21—C22—C17	120.9 (4)
O3—C9—C8	118.6 (3)	C21—C22—Cl1	116.4 (3)
C10—C9—C8	121.1 (3)	C17—C22—Cl1	122.6 (3)
C1—N1—N2—N3	−0.1 (5)	C8—C9—C10—C15	−2.8 (6)
N1—N2—N3—C6	−0.1 (4)	O3—C9—C10—C11	−5.0 (6)
N1—N2—N3—C7	−179.1 (3)	C8—C9—C10—C11	177.6 (3)
N2—N1—C1—C6	0.2 (5)	C15—C10—C11—C12	−0.4 (6)
N2—N1—C1—C2	−179.9 (4)	C9—C10—C11—C12	179.3 (4)
N1—C1—C2—C3	−179.0 (4)	C10—C11—C12—C13	−0.4 (7)
C6—C1—C2—C3	0.9 (6)	C11—C12—C13—C14	1.0 (7)
C1—C2—C3—C4	0.1 (7)	C12—C13—C14—C15	−0.6 (6)
C2—C3—C4—C5	−1.4 (7)	C11—C10—C15—F1	178.2 (3)
C3—C4—C5—C6	1.4 (6)	C9—C10—C15—F1	−1.4 (6)
N2—N3—C6—C1	0.2 (4)	C11—C10—C15—C14	0.7 (6)
C7—N3—C6—C1	179.1 (3)	C9—C10—C15—C14	−178.9 (4)
N2—N3—C6—C5	−178.9 (4)	C13—C14—C15—F1	−177.8 (3)
C7—N3—C6—C5	0.0 (6)	C13—C14—C15—C10	−0.2 (6)
N1—C1—C6—N3	−0.2 (4)	C8—O1—C16—O2	−1.0 (5)
C2—C1—C6—N3	179.8 (3)	C8—O1—C16—C17	176.6 (2)
N1—C1—C6—C5	179.0 (3)	O2—C16—C17—C22	−19.1 (5)
C2—C1—C6—C5	−0.9 (6)	O1—C16—C17—C22	163.4 (3)
C4—C5—C6—N3	178.7 (4)	O2—C16—C17—C18	157.3 (3)
C4—C5—C6—C1	−0.3 (6)	O1—C16—C17—C18	−20.3 (4)
C6—N3—C7—C8	−92.6 (4)	C22—C17—C18—C19	−0.3 (5)
N2—N3—C7—C8	86.2 (4)	C16—C17—C18—C19	−176.9 (3)
C16—O1—C8—C9	65.4 (3)	C17—C18—C19—C20	0.1 (5)
C16—O1—C8—C7	−173.9 (3)	C18—C19—C20—C21	−0.3 (6)
N3—C7—C8—O1	66.2 (3)	C19—C20—C21—C22	0.7 (6)
N3—C7—C8—C9	−173.1 (3)	C20—C21—C22—C17	−0.9 (5)
O1—C8—C9—O3	27.6 (5)	C20—C21—C22—Cl1	−178.4 (3)
C7—C8—C9—O3	−90.3 (4)	C18—C17—C22—C21	0.7 (5)
O1—C8—C9—C10	−154.9 (3)	C16—C17—C22—C21	177.1 (3)
C7—C8—C9—C10	87.1 (4)	C18—C17—C22—Cl1	178.1 (3)
O3—C9—C10—C15	174.6 (4)	C16—C17—C22—Cl1	−5.5 (5)