3-(1H-Benzotriazol-1-yl)-1-(3-chloro­phen­yl)propan-1-one

In the title compound, C₁₅H₁₂ClN₃O, the mol­ecules are linked into centrosymmetric dimers by C—H...O inter­molecular hydrogen bonds. The mol­ecular packing is further stabilized by π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.111
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         200 Deg.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

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).

3-(1H-Benzotriazol-1-yl)-1-(3-chlorophenyl)propan-1-one

Crystal data

C15H12ClN3O	Z = 2
Mr = 285.73	F(000) = 296
Triclinic, P1	Dx = 1.435 Mg m^−3
a = 7.4919 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.9858 (10) Å	Cell parameters from 1725 reflections
c = 11.4486 (14) Å	θ = 2.6–25.8°
α = 92.948 (2)°	µ = 0.29 mm^−1
β = 96.711 (2)°	T = 293 K
γ = 102.841 (2)°	Needle, colourless
V = 661.13 (14) Å^3	0.46 × 0.17 × 0.10 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	2526 independent reflections
Radiation source: fine-focus sealed tube	2102 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 1.8°
ω scans	h = −9→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→9
Tmin = 0.879, Tmax = 0.972	l = −10→14
3726 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0522P)^2 + 0.1689P] where P = (Fo^2 + 2Fc^2)/3
2526 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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 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	0.14037 (8)	−0.43424 (6)	0.39153 (5)	0.0706 (2)
O1	0.4402 (2)	0.22567 (18)	0.40850 (12)	0.0733 (5)
N1	0.7001 (2)	0.61446 (18)	0.21712 (12)	0.0460 (4)
N2	0.7110 (2)	0.5790 (2)	0.10179 (13)	0.0561 (5)
N3	0.7867 (2)	0.7204 (2)	0.05711 (13)	0.0568 (5)
C1	0.3694 (3)	−0.0547 (2)	0.14055 (16)	0.0528 (6)
C2	0.3000 (3)	−0.2259 (3)	0.10167 (17)	0.0592 (7)
C3	0.2292 (3)	−0.3442 (2)	0.17718 (16)	0.0543 (6)
C4	0.2304 (2)	−0.2878 (2)	0.29377 (15)	0.0478 (6)
C5	0.3016 (2)	−0.1186 (2)	0.33466 (15)	0.0462 (6)
C6	0.3714 (2)	0.0005 (2)	0.25782 (14)	0.0433 (5)
C7	0.4457 (2)	0.1837 (2)	0.30602 (15)	0.0477 (6)
C8	0.5279 (3)	0.3142 (2)	0.22500 (15)	0.0491 (6)
C9	0.6213 (3)	0.4836 (2)	0.29285 (16)	0.0525 (6)
C10	0.7725 (2)	0.7847 (2)	0.24888 (14)	0.0416 (5)
C11	0.8273 (2)	0.8519 (2)	0.14540 (14)	0.0443 (5)
C12	0.9104 (3)	1.0273 (2)	0.14475 (16)	0.0521 (6)
C13	0.9347 (3)	1.1259 (2)	0.24887 (17)	0.0564 (6)
C14	0.8786 (3)	1.0560 (3)	0.35232 (17)	0.0586 (7)
C15	0.7964 (3)	0.8852 (2)	0.35501 (15)	0.0516 (6)
H1A	0.41510	0.02400	0.08800	0.0630*
H2B	0.30100	−0.26180	0.02320	0.0710*
H3A	0.18160	−0.45930	0.15060	0.0650*
H5A	0.30310	−0.08400	0.41360	0.0550*
H8A	0.61710	0.27070	0.18450	0.0590*
H8B	0.43110	0.33160	0.16600	0.0590*
H9A	0.53220	0.52510	0.33460	0.0630*
H9B	0.71880	0.46560	0.35110	0.0630*
H12A	0.94740	1.07440	0.07640	0.0630*
H13A	0.98990	1.24270	0.25140	0.0680*
H14A	0.89790	1.12810	0.42130	0.0700*
H15A	0.75880	0.83920	0.42350	0.0620*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0926 (4)	0.0509 (3)	0.0588 (3)	−0.0071 (3)	0.0147 (3)	0.0107 (2)
O1	0.1080 (12)	0.0554 (8)	0.0474 (8)	−0.0082 (8)	0.0283 (8)	−0.0018 (6)
N1	0.0546 (8)	0.0443 (8)	0.0366 (7)	0.0049 (6)	0.0081 (6)	0.0047 (6)
N2	0.0772 (11)	0.0491 (9)	0.0367 (8)	0.0023 (8)	0.0111 (7)	−0.0005 (6)
N3	0.0775 (11)	0.0499 (9)	0.0384 (8)	0.0024 (8)	0.0127 (7)	0.0028 (7)
C1	0.0649 (12)	0.0534 (11)	0.0410 (9)	0.0107 (9)	0.0149 (8)	0.0073 (8)
C2	0.0784 (13)	0.0585 (12)	0.0402 (10)	0.0144 (10)	0.0121 (9)	−0.0041 (8)
C3	0.0635 (11)	0.0453 (10)	0.0518 (11)	0.0104 (8)	0.0050 (9)	−0.0024 (8)
C4	0.0502 (10)	0.0464 (9)	0.0461 (10)	0.0077 (8)	0.0082 (7)	0.0075 (8)
C5	0.0515 (10)	0.0479 (10)	0.0380 (9)	0.0075 (8)	0.0094 (7)	0.0027 (7)
C6	0.0446 (9)	0.0470 (9)	0.0391 (9)	0.0104 (7)	0.0089 (7)	0.0052 (7)
C7	0.0521 (10)	0.0485 (10)	0.0427 (10)	0.0088 (8)	0.0120 (7)	0.0053 (8)
C8	0.0576 (10)	0.0460 (10)	0.0437 (9)	0.0086 (8)	0.0106 (8)	0.0081 (8)
C9	0.0615 (11)	0.0508 (10)	0.0418 (10)	0.0027 (8)	0.0107 (8)	0.0084 (8)
C10	0.0441 (9)	0.0438 (9)	0.0369 (8)	0.0092 (7)	0.0070 (7)	0.0035 (7)
C11	0.0490 (9)	0.0462 (9)	0.0377 (9)	0.0099 (7)	0.0081 (7)	0.0033 (7)
C12	0.0589 (11)	0.0486 (10)	0.0485 (10)	0.0073 (8)	0.0138 (8)	0.0089 (8)
C13	0.0607 (11)	0.0446 (10)	0.0622 (12)	0.0066 (8)	0.0133 (9)	0.0006 (9)
C14	0.0673 (12)	0.0551 (11)	0.0500 (11)	0.0087 (9)	0.0113 (9)	−0.0106 (9)
C15	0.0597 (11)	0.0574 (11)	0.0375 (9)	0.0109 (9)	0.0121 (8)	0.0006 (8)

Geometric parameters (Å, º)

Cl1—C4	1.7423 (17)	C10—C15	1.392 (2)
O1—C7	1.211 (2)	C11—C12	1.401 (2)
N1—N2	1.352 (2)	C12—C13	1.365 (3)
N1—C9	1.460 (2)	C13—C14	1.404 (3)
N1—C10	1.360 (2)	C14—C15	1.370 (3)
N2—N3	1.304 (2)	C1—H1A	0.9304
N3—C11	1.376 (2)	C2—H2B	0.9302
C1—C2	1.380 (3)	C3—H3A	0.9300
C1—C6	1.389 (2)	C5—H5A	0.9294
C2—C3	1.375 (3)	C8—H8A	0.9702
C3—C4	1.385 (2)	C8—H8B	0.9703
C4—C5	1.373 (2)	C9—H9A	0.9698
C5—C6	1.387 (2)	C9—H9B	0.9704
C6—C7	1.496 (2)	C12—H12A	0.9302
C7—C8	1.508 (2)	C13—H13A	0.9300
C8—C9	1.506 (2)	C14—H14A	0.9304
C10—C11	1.393 (2)	C15—H15A	0.9297
N2—N1—C9	122.94 (14)	C13—C14—C15	122.16 (18)
N2—N1—C10	110.15 (14)	C10—C15—C14	115.90 (16)
C9—N1—C10	126.91 (14)	C2—C1—H1A	119.87
N1—N2—N3	109.17 (14)	C6—C1—H1A	119.88
N2—N3—C11	107.93 (14)	C1—C2—H2B	119.55
C2—C1—C6	120.25 (16)	C3—C2—H2B	119.48
C1—C2—C3	120.97 (18)	C2—C3—H3A	120.79
C2—C3—C4	118.39 (16)	C4—C3—H3A	120.81
Cl1—C4—C3	119.53 (12)	C4—C5—H5A	120.09
Cl1—C4—C5	118.93 (13)	C6—C5—H5A	120.10
C3—C4—C5	121.54 (15)	C7—C8—H8A	109.42
C4—C5—C6	119.81 (15)	C7—C8—H8B	109.42
C1—C6—C5	119.02 (15)	C9—C8—H8A	109.43
C1—C6—C7	123.05 (14)	C9—C8—H8B	109.40
C5—C6—C7	117.93 (14)	H8A—C8—H8B	108.05
O1—C7—C6	120.34 (15)	N1—C9—H9A	109.05
O1—C7—C8	120.84 (15)	N1—C9—H9B	109.04
C6—C7—C8	118.82 (14)	C8—C9—H9A	109.05
C7—C8—C9	111.06 (14)	C8—C9—H9B	109.01
N1—C9—C8	112.73 (14)	H9A—C9—H9B	107.83
N1—C10—C11	104.15 (14)	C11—C12—H12A	121.47
N1—C10—C15	133.14 (15)	C13—C12—H12A	121.49
C11—C10—C15	122.71 (15)	C12—C13—H13A	119.11
N3—C11—C10	108.60 (14)	C14—C13—H13A	119.03
N3—C11—C12	131.07 (15)	C13—C14—H14A	118.90
C10—C11—C12	120.33 (15)	C15—C14—H14A	118.94
C11—C12—C13	117.04 (16)	C10—C15—H15A	122.04
C12—C13—C14	121.86 (16)	C14—C15—H15A	122.07
C9—N1—N2—N3	179.79 (16)	C4—C5—C6—C7	179.36 (14)
C10—N1—N2—N3	−0.47 (19)	C1—C6—C7—C8	−2.0 (3)
N2—N1—C9—C8	−9.0 (3)	C5—C6—C7—O1	−1.7 (2)
C10—N1—C9—C8	171.26 (17)	C1—C6—C7—O1	178.29 (18)
N2—N1—C10—C11	0.45 (18)	C5—C6—C7—C8	178.03 (16)
N2—N1—C10—C15	−179.18 (19)	C6—C7—C8—C9	−171.14 (16)
C9—N1—C10—C11	−179.82 (17)	O1—C7—C8—C9	8.6 (3)
C9—N1—C10—C15	0.5 (3)	C7—C8—C9—N1	−179.04 (16)
N1—N2—N3—C11	0.27 (19)	N1—C10—C11—C12	−179.68 (16)
N2—N3—C11—C10	0.00 (19)	C15—C10—C11—N3	179.40 (17)
N2—N3—C11—C12	179.32 (19)	C15—C10—C11—C12	0.0 (3)
C2—C1—C6—C7	179.57 (18)	N1—C10—C11—N3	−0.29 (18)
C2—C1—C6—C5	−0.4 (3)	N1—C10—C15—C14	179.30 (19)
C6—C1—C2—C3	1.0 (3)	C11—C10—C15—C14	−0.3 (3)
C1—C2—C3—C4	−0.5 (3)	N3—C11—C12—C13	−178.96 (19)
C2—C3—C4—Cl1	179.60 (16)	C10—C11—C12—C13	0.3 (3)
C2—C3—C4—C5	−0.6 (3)	C11—C12—C13—C14	−0.3 (3)
Cl1—C4—C5—C6	−179.03 (12)	C12—C13—C14—C15	0.0 (4)
C3—C4—C5—C6	1.2 (3)	C13—C14—C15—C10	0.3 (3)
C4—C5—C6—C1	−0.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O1^i	0.93	2.57	3.454 (2)	158

Symmetry code: (i) −x+1, −y+1, −z+1.