3-(1H-Benzotriazol-1-yl)-1-(2-fluoro­phen­yl)propan-1-one

In the title compound, C₁₅H₁₂FN₃O, an intra­molecular C—H...F hydrogen bond forms a six-membered ring. Mol­ecules are linked into a tape along the b axis by an inter­molecular C—H...N hydrogen bond. The crystal packing is further stabilized by C—H...π and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.143
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N2     -   N3      ..       8.46 su

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

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
   1 ALERT level B = Potentially serious problem
   2 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
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

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-(2-fluorophenyl)propan-1-one

Crystal data

C15H12FN3O	F(000) = 560
Mr = 269.28	Dx = 1.398 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.551 (6) Å	Cell parameters from 2022 reflections
b = 5.971 (2) Å	θ = 9.3–24.9°
c = 14.221 (6) Å	µ = 0.10 mm^−1
β = 104.339 (6)°	T = 293 K
V = 1279.4 (8) Å^3	Column, colourless
Z = 4	0.47 × 0.17 × 0.09 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	2520 independent reflections
Radiation source: fine-focus sealed tube	1923 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.33 pixels mm^-1	θmax = 26.1°, θmin = 2.7°
ω scans	h = −19→16
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −7→6
Tmin = 0.954, Tmax = 0.991	l = −17→17
6710 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.143	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
2520 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.19 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
F1	0.73132 (8)	0.0299 (2)	0.82666 (8)	0.0783 (4)
C14	1.07969 (11)	0.3440 (3)	1.17473 (11)	0.0476 (4)
H14A	1.1198	0.2328	1.2026	0.057*
N1	0.84451 (9)	0.5051 (2)	1.09814 (10)	0.0465 (4)
C8	0.74309 (10)	0.2240 (3)	1.00551 (10)	0.0415 (4)
H8A	0.7236	0.3328	0.9540	0.050*
H8B	0.7925	0.1414	0.9922	0.050*
N2	0.82312 (10)	0.7122 (3)	1.06016 (11)	0.0594 (4)
C10	0.93446 (10)	0.4781 (2)	1.12024 (9)	0.0391 (4)
N3	0.89552 (10)	0.8195 (2)	1.05724 (11)	0.0553 (4)
C15	0.99127 (11)	0.3037 (3)	1.16131 (10)	0.0431 (4)
H15A	0.9700	0.1681	1.1785	0.052*
C12	1.05736 (11)	0.7183 (3)	1.10718 (11)	0.0473 (4)
H12A	1.0790	0.8525	1.0891	0.057*
O1	0.63199 (9)	0.0660 (3)	1.07216 (10)	0.0762 (5)
C11	0.96620 (11)	0.6808 (2)	1.09384 (10)	0.0422 (4)
C7	0.66832 (10)	0.0648 (3)	1.00583 (12)	0.0473 (4)
C6	0.63805 (10)	−0.1001 (3)	0.92444 (11)	0.0459 (4)
C5	0.67040 (11)	−0.1186 (3)	0.84222 (12)	0.0516 (4)
C9	0.77424 (11)	0.3463 (3)	1.10168 (12)	0.0532 (5)
H9A	0.7246	0.4255	1.1163	0.064*
H9B	0.7960	0.2385	1.1531	0.064*
C13	1.11281 (11)	0.5484 (3)	1.14793 (11)	0.0484 (4)
H13A	1.1738	0.5676	1.1583	0.058*
C1	0.57469 (11)	−0.2587 (3)	0.93320 (14)	0.0610 (5)
H1A	0.5505	−0.2532	0.9868	0.073*
C4	0.64411 (13)	−0.2827 (3)	0.77343 (14)	0.0631 (5)
H4A	0.6681	−0.2893	0.7198	0.076*
C3	0.58224 (13)	−0.4361 (4)	0.78476 (15)	0.0708 (6)
H3B	0.5640	−0.5486	0.7389	0.085*
C2	0.54705 (13)	−0.4230 (4)	0.86449 (16)	0.0748 (6)
H2B	0.5043	−0.5260	0.8719	0.090*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0938 (9)	0.0897 (9)	0.0622 (7)	−0.0365 (7)	0.0398 (7)	−0.0199 (6)
C14	0.0549 (10)	0.0464 (10)	0.0414 (9)	0.0106 (7)	0.0118 (7)	0.0029 (7)
N1	0.0489 (8)	0.0441 (8)	0.0438 (7)	0.0000 (6)	0.0062 (6)	−0.0044 (6)
C8	0.0418 (9)	0.0432 (9)	0.0400 (8)	0.0029 (7)	0.0111 (6)	0.0017 (6)
N2	0.0608 (10)	0.0499 (9)	0.0610 (9)	0.0133 (7)	0.0025 (7)	−0.0008 (7)
C10	0.0492 (9)	0.0380 (9)	0.0292 (7)	−0.0009 (7)	0.0082 (6)	−0.0068 (6)
N3	0.0607 (10)	0.0417 (9)	0.0591 (9)	0.0062 (7)	0.0068 (7)	0.0016 (6)
C15	0.0586 (10)	0.0347 (8)	0.0360 (8)	0.0018 (7)	0.0119 (7)	−0.0001 (6)
C12	0.0612 (11)	0.0408 (9)	0.0423 (9)	−0.0071 (8)	0.0173 (7)	−0.0022 (6)
O1	0.0708 (9)	0.1059 (12)	0.0634 (9)	−0.0246 (8)	0.0385 (7)	−0.0178 (8)
C11	0.0567 (10)	0.0350 (8)	0.0333 (7)	0.0019 (7)	0.0082 (7)	−0.0024 (6)
C7	0.0403 (9)	0.0574 (11)	0.0448 (9)	0.0019 (7)	0.0117 (7)	0.0032 (7)
C6	0.0383 (8)	0.0490 (10)	0.0474 (9)	0.0001 (7)	0.0047 (7)	0.0043 (7)
C5	0.0507 (10)	0.0533 (10)	0.0496 (9)	−0.0058 (8)	0.0100 (7)	−0.0015 (8)
C9	0.0494 (10)	0.0659 (12)	0.0451 (9)	−0.0060 (8)	0.0134 (7)	−0.0067 (8)
C13	0.0493 (9)	0.0554 (10)	0.0430 (9)	0.0001 (8)	0.0163 (7)	−0.0029 (7)
C1	0.0480 (10)	0.0696 (12)	0.0627 (11)	−0.0102 (9)	0.0082 (8)	0.0077 (9)
C4	0.0666 (12)	0.0625 (12)	0.0558 (11)	−0.0003 (10)	0.0069 (9)	−0.0109 (9)
C3	0.0715 (14)	0.0585 (12)	0.0695 (13)	−0.0058 (10)	−0.0073 (10)	−0.0102 (9)
C2	0.0641 (13)	0.0655 (14)	0.0849 (16)	−0.0216 (10)	−0.0003 (11)	0.0047 (11)

Geometric parameters (Å, º)

F1—C5	1.355 (2)	C12—C11	1.401 (2)
C14—C15	1.362 (2)	C12—H12A	0.9300
C14—C13	1.413 (2)	O1—C7	1.214 (2)
C14—H14A	0.9300	C7—C6	1.503 (2)
N1—N2	1.357 (2)	C6—C5	1.387 (2)
N1—C10	1.365 (2)	C6—C1	1.394 (2)
N1—C9	1.457 (2)	C5—C4	1.373 (3)
C8—C7	1.503 (2)	C9—H9A	0.9700
C8—C9	1.520 (2)	C9—H9B	0.9700
C8—H8A	0.9700	C13—H13A	0.9300
C8—H8B	0.9700	C1—C2	1.377 (3)
N2—N3	1.305 (2)	C1—H1A	0.9300
C10—C11	1.393 (2)	C4—C3	1.367 (3)
C10—C15	1.397 (2)	C4—H4A	0.9300
N3—C11	1.372 (2)	C3—C2	1.378 (3)
C15—H15A	0.9300	C3—H3B	0.9300
C12—C13	1.364 (2)	C2—H2B	0.9300
C15—C14—C13	122.51 (15)	C8—C7—C6	120.46 (13)
C15—C14—H14A	118.7	C5—C6—C1	115.68 (16)
C13—C14—H14A	118.7	C5—C6—C7	126.25 (15)
N2—N1—C10	109.59 (14)	C1—C6—C7	117.98 (15)
N2—N1—C9	119.65 (14)	F1—C5—C4	116.57 (16)
C10—N1—C9	130.50 (14)	F1—C5—C6	119.99 (15)
C7—C8—C9	112.06 (13)	C4—C5—C6	123.44 (17)
C7—C8—H8A	109.2	N1—C9—C8	110.86 (13)
C9—C8—H8A	109.2	N1—C9—H9A	109.5
C7—C8—H8B	109.2	C8—C9—H9A	109.5
C9—C8—H8B	109.2	N1—C9—H9B	109.5
H8A—C8—H8B	107.9	C8—C9—H9B	109.5
N3—N2—N1	109.36 (14)	H9A—C9—H9B	108.1
N1—C10—C11	104.27 (14)	C12—C13—C14	121.50 (16)
N1—C10—C15	133.66 (15)	C12—C13—H13A	119.3
C11—C10—C15	122.06 (15)	C14—C13—H13A	119.3
N2—N3—C11	107.96 (14)	C2—C1—C6	121.61 (18)
C14—C15—C10	116.04 (14)	C2—C1—H1A	119.2
C14—C15—H15A	122.0	C6—C1—H1A	119.2
C10—C15—H15A	122.0	C3—C4—C5	119.24 (19)
C13—C12—C11	116.79 (15)	C3—C4—H4A	120.4
C13—C12—H12A	121.6	C5—C4—H4A	120.4
C11—C12—H12A	121.6	C4—C3—C2	119.59 (19)
N3—C11—C10	108.82 (15)	C4—C3—H3B	120.2
N3—C11—C12	130.09 (15)	C2—C3—H3B	120.2
C10—C11—C12	121.09 (14)	C1—C2—C3	120.44 (19)
O1—C7—C8	120.52 (15)	C1—C2—H2B	119.8
O1—C7—C6	119.02 (15)	C3—C2—H2B	119.8
C10—N1—N2—N3	−0.20 (18)	O1—C7—C6—C5	177.82 (17)
C9—N1—N2—N3	−175.08 (13)	C8—C7—C6—C5	−2.8 (3)
N2—N1—C10—C11	0.23 (16)	O1—C7—C6—C1	−5.7 (2)
C9—N1—C10—C11	174.38 (15)	C8—C7—C6—C1	173.64 (15)
N2—N1—C10—C15	178.92 (15)	C1—C6—C5—F1	179.10 (15)
C9—N1—C10—C15	−6.9 (3)	C7—C6—C5—F1	−4.4 (3)
N1—N2—N3—C11	0.08 (18)	C1—C6—C5—C4	−1.0 (3)
C13—C14—C15—C10	−0.7 (2)	C7—C6—C5—C4	175.50 (16)
N1—C10—C15—C14	−178.02 (15)	N2—N1—C9—C8	83.72 (18)
C11—C10—C15—C14	0.5 (2)	C10—N1—C9—C8	−89.93 (19)
N2—N3—C11—C10	0.07 (17)	C7—C8—C9—N1	−177.98 (13)
N2—N3—C11—C12	−179.16 (15)	C11—C12—C13—C14	0.4 (2)
N1—C10—C11—N3	−0.18 (16)	C15—C14—C13—C12	0.3 (2)
C15—C10—C11—N3	−179.06 (13)	C5—C6—C1—C2	0.4 (3)
N1—C10—C11—C12	179.13 (13)	C7—C6—C1—C2	−176.39 (17)
C15—C10—C11—C12	0.2 (2)	F1—C5—C4—C3	−179.45 (17)
C13—C12—C11—N3	178.45 (15)	C6—C5—C4—C3	0.7 (3)
C13—C12—C11—C10	−0.7 (2)	C5—C4—C3—C2	0.3 (3)
C9—C8—C7—O1	9.6 (2)	C6—C1—C2—C3	0.5 (3)
C9—C8—C7—C6	−169.74 (14)	C4—C3—C2—C1	−0.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···F1	0.97	2.40	2.760 (2)	101
C8—H8B···N3^i	0.97	2.53	3.336 (3)	140
C15—H15A···Cg3^ii	0.93	2.80	3.446 (2)	127

Symmetry codes: (i) x, y−1, z; (ii) −x+2, y−1/2, −z+5/2.