1-Acetyl-5-(4-chloro­phen­yl)-3-(4-fluoro­phen­yl)-2-pyrazoline

In the title compound, C₁₇H₁₄ClFN₂O, all bond lengths and angles show normal values. The two benzene rings make a dihehral angle of 82.17 (2)°. Weak inter­molecular C—H...O hydrogen bonds stabilize the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.118
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    F1     -   C3      ..       5.36 su

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

   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

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

1-Acetyl-5-(4-chlorophenyl)-3-(4-fluorophenyl)-2-pyrazoline

Crystal data

C17H14ClFN2O	F(000) = 656
Mr = 316.75	Dx = 1.379 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2140 reflections
a = 6.119 (2) Å	θ = 2.6–24.6°
b = 12.696 (5) Å	µ = 0.26 mm^−1
c = 19.812 (7) Å	T = 294 K
β = 97.549 (7)°	Block, colourless
V = 1525.8 (10) Å^3	0.30 × 0.20 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3118 independent reflections
Radiation source: fine-focus sealed tube	1772 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −6→7
Tmin = 0.925, Tmax = 0.954	k = −15→13
8612 measured reflections	l = −24→24

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0677P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.003
3118 reflections	Δρmax = 0.18 e Å^−3
201 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (2)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.46496 (13)	0.79746 (6)	1.05071 (3)	0.0924 (3)
F1	1.0807 (2)	1.16308 (11)	0.53975 (7)	0.0889 (5)
O1	−0.1341 (2)	0.86440 (13)	0.75617 (7)	0.0690 (5)
N1	0.3123 (3)	0.95275 (13)	0.67707 (7)	0.0488 (4)
N2	0.1687 (3)	0.93816 (13)	0.72473 (8)	0.0523 (4)
C1	0.6290 (3)	1.01792 (17)	0.59328 (11)	0.0591 (6)
H1	0.5370	0.9620	0.5784	0.071*
C2	0.7878 (4)	1.05008 (19)	0.55433 (11)	0.0666 (6)
H2	0.8021	1.0175	0.5131	0.080*
C3	0.9241 (3)	1.13142 (17)	0.57817 (11)	0.0573 (6)
C4	0.9092 (4)	1.18208 (16)	0.63748 (11)	0.0567 (6)
H4	1.0054	1.2365	0.6524	0.068*
C5	0.7459 (4)	1.15006 (16)	0.67525 (10)	0.0542 (5)
H5	0.7309	1.1848	0.7157	0.065*
C6	0.6042 (3)	1.06763 (14)	0.65427 (9)	0.0439 (5)
C7	0.4344 (3)	1.03316 (15)	0.69482 (9)	0.0455 (5)
C8	0.3831 (4)	1.08576 (16)	0.75874 (10)	0.0603 (6)
H8A	0.3284	1.1567	0.7495	0.072*
H8B	0.5124	1.0885	0.7927	0.072*
C9	0.2040 (3)	1.01474 (16)	0.78218 (9)	0.0546 (5)
H9	0.0693	1.0557	0.7842	0.066*
C10	0.2708 (3)	0.96009 (15)	0.84960 (9)	0.0462 (5)
C11	0.4696 (3)	0.90717 (16)	0.86257 (10)	0.0556 (6)
H11	0.5636	0.9047	0.8293	0.067*
C12	0.5300 (3)	0.85781 (17)	0.92453 (11)	0.0607 (6)
H12	0.6637	0.8222	0.9328	0.073*
C13	0.3924 (4)	0.86164 (16)	0.97335 (10)	0.0560 (6)
C14	0.1938 (4)	0.91274 (17)	0.96180 (10)	0.0594 (6)
H14	0.0996	0.9141	0.9950	0.071*
C15	0.1358 (4)	0.96230 (15)	0.89971 (10)	0.0547 (5)
H15	0.0022	0.9979	0.8918	0.066*
C16	−0.0015 (4)	0.86924 (17)	0.71540 (10)	0.0538 (5)
C17	−0.0119 (4)	0.79917 (18)	0.65383 (11)	0.0720 (7)
H17A	−0.1343	0.7517	0.6531	0.108*
H17B	0.1224	0.7595	0.6557	0.108*
H17C	−0.0305	0.8416	0.6134	0.108*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1183 (6)	0.0944 (5)	0.0577 (4)	0.0057 (4)	−0.0134 (4)	0.0154 (3)
F1	0.0825 (10)	0.0916 (10)	0.1008 (10)	−0.0281 (8)	0.0424 (8)	−0.0127 (8)
O1	0.0519 (9)	0.0935 (12)	0.0635 (9)	0.0003 (8)	0.0145 (8)	0.0197 (8)
N1	0.0471 (10)	0.0571 (11)	0.0429 (9)	−0.0030 (9)	0.0080 (7)	0.0010 (8)
N2	0.0560 (11)	0.0601 (11)	0.0424 (9)	−0.0064 (9)	0.0124 (8)	−0.0005 (8)
C1	0.0533 (13)	0.0616 (14)	0.0633 (13)	−0.0117 (11)	0.0116 (11)	−0.0147 (11)
C2	0.0632 (15)	0.0758 (15)	0.0644 (14)	−0.0132 (13)	0.0217 (12)	−0.0195 (12)
C3	0.0512 (13)	0.0563 (13)	0.0674 (14)	−0.0066 (11)	0.0191 (11)	0.0036 (11)
C4	0.0633 (14)	0.0476 (12)	0.0582 (13)	−0.0109 (11)	0.0039 (11)	0.0018 (10)
C5	0.0707 (14)	0.0454 (12)	0.0452 (11)	−0.0028 (11)	0.0028 (10)	0.0005 (9)
C6	0.0472 (12)	0.0409 (11)	0.0426 (10)	0.0020 (9)	0.0024 (9)	0.0020 (9)
C7	0.0497 (12)	0.0436 (11)	0.0419 (10)	0.0028 (10)	0.0014 (9)	0.0012 (9)
C8	0.0827 (16)	0.0483 (12)	0.0515 (12)	−0.0028 (11)	0.0145 (11)	−0.0008 (10)
C9	0.0608 (14)	0.0549 (13)	0.0497 (12)	0.0078 (11)	0.0129 (10)	0.0007 (10)
C10	0.0491 (12)	0.0481 (12)	0.0425 (11)	0.0048 (10)	0.0102 (9)	−0.0054 (9)
C11	0.0499 (13)	0.0634 (14)	0.0563 (13)	0.0035 (11)	0.0173 (10)	−0.0014 (10)
C12	0.0488 (13)	0.0637 (14)	0.0674 (14)	0.0082 (11)	−0.0006 (11)	−0.0018 (11)
C13	0.0660 (14)	0.0551 (13)	0.0448 (11)	−0.0006 (11)	−0.0007 (11)	−0.0031 (9)
C14	0.0701 (15)	0.0661 (14)	0.0448 (12)	0.0089 (12)	0.0189 (11)	−0.0045 (10)
C15	0.0557 (13)	0.0589 (13)	0.0512 (12)	0.0156 (11)	0.0136 (10)	−0.0038 (10)
C16	0.0465 (12)	0.0641 (14)	0.0491 (12)	−0.0008 (11)	−0.0002 (10)	0.0149 (10)
C17	0.0760 (16)	0.0773 (16)	0.0598 (13)	−0.0233 (13)	−0.0018 (12)	0.0014 (12)

Geometric parameters (Å, º)

Cl1—C13	1.741 (2)	C8—C9	1.537 (3)
F1—C3	1.361 (2)	C8—H8A	0.9700
O1—C16	1.219 (2)	C8—H8B	0.9700
N1—C7	1.287 (2)	C9—C10	1.513 (3)
N1—N2	1.384 (2)	C9—H9	0.9800
N2—C16	1.354 (3)	C10—C15	1.373 (3)
N2—C9	1.491 (2)	C10—C11	1.384 (3)
C1—C2	1.380 (3)	C11—C12	1.385 (3)
C1—C6	1.389 (3)	C11—H11	0.9300
C1—H1	0.9300	C12—C13	1.364 (3)
C2—C3	1.371 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.370 (3)
C3—C4	1.353 (3)	C14—C15	1.386 (3)
C4—C5	1.386 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.388 (3)	C16—C17	1.504 (3)
C5—H5	0.9300	C17—H17A	0.9600
C6—C7	1.461 (3)	C17—H17B	0.9600
C7—C8	1.501 (3)	C17—H17C	0.9600
C7—N1—N2	108.53 (16)	N2—C9—C8	100.92 (15)
C16—N2—N1	122.63 (17)	C10—C9—C8	114.54 (17)
C16—N2—C9	123.86 (18)	N2—C9—H9	109.8
N1—N2—C9	113.09 (15)	C10—C9—H9	109.8
C2—C1—C6	121.18 (19)	C8—C9—H9	109.8
C2—C1—H1	119.4	C15—C10—C11	118.24 (18)
C6—C1—H1	119.4	C15—C10—C9	120.74 (18)
C3—C2—C1	118.1 (2)	C11—C10—C9	121.02 (18)
C3—C2—H2	120.9	C10—C11—C12	120.7 (2)
C1—C2—H2	120.9	C10—C11—H11	119.7
C4—C3—F1	118.55 (19)	C12—C11—H11	119.7
C4—C3—C2	123.4 (2)	C13—C12—C11	119.6 (2)
F1—C3—C2	118.1 (2)	C13—C12—H12	120.2
C3—C4—C5	117.70 (19)	C11—C12—H12	120.2
C3—C4—H4	121.1	C12—C13—C14	121.01 (19)
C5—C4—H4	121.1	C12—C13—Cl1	119.85 (17)
C4—C5—C6	121.75 (19)	C14—C13—Cl1	119.11 (18)
C4—C5—H5	119.1	C13—C14—C15	118.8 (2)
C6—C5—H5	119.1	C13—C14—H14	120.6
C5—C6—C1	117.88 (19)	C15—C14—H14	120.6
C5—C6—C7	121.51 (17)	C10—C15—C14	121.65 (19)
C1—C6—C7	120.61 (17)	C10—C15—H15	119.2
N1—C7—C6	121.12 (17)	C14—C15—H15	119.2
N1—C7—C8	113.89 (18)	O1—C16—N2	120.6 (2)
C6—C7—C8	124.99 (17)	O1—C16—C17	123.1 (2)
C7—C8—C9	103.33 (16)	N2—C16—C17	116.3 (2)
C7—C8—H8A	111.1	C16—C17—H17A	109.5
C9—C8—H8A	111.1	C16—C17—H17B	109.5
C7—C8—H8B	111.1	H17A—C17—H17B	109.5
C9—C8—H8B	111.1	C16—C17—H17C	109.5
H8A—C8—H8B	109.1	H17A—C17—H17C	109.5
N2—C9—C10	111.73 (16)	H17B—C17—H17C	109.5
C7—N1—N2—C16	170.40 (17)	C16—N2—C9—C8	−168.22 (18)
C7—N1—N2—C9	−2.4 (2)	N1—N2—C9—C8	4.5 (2)
C6—C1—C2—C3	1.3 (3)	C7—C8—C9—N2	−4.54 (19)
C1—C2—C3—C4	−0.6 (3)	C7—C8—C9—C10	115.63 (18)
C1—C2—C3—F1	180.0 (2)	N2—C9—C10—C15	−114.9 (2)
F1—C3—C4—C5	178.77 (18)	C8—C9—C10—C15	131.2 (2)
C2—C3—C4—C5	−0.7 (3)	N2—C9—C10—C11	65.5 (2)
C3—C4—C5—C6	1.3 (3)	C8—C9—C10—C11	−48.4 (3)
C4—C5—C6—C1	−0.6 (3)	C15—C10—C11—C12	0.0 (3)
C4—C5—C6—C7	179.04 (18)	C9—C10—C11—C12	179.66 (18)
C2—C1—C6—C5	−0.7 (3)	C10—C11—C12—C13	−0.2 (3)
C2—C1—C6—C7	179.64 (19)	C11—C12—C13—C14	0.7 (3)
N2—N1—C7—C6	179.59 (15)	C11—C12—C13—Cl1	178.69 (16)
N2—N1—C7—C8	−1.0 (2)	C12—C13—C14—C15	−1.0 (3)
C5—C6—C7—N1	−175.86 (17)	Cl1—C13—C14—C15	−179.05 (16)
C1—C6—C7—N1	3.8 (3)	C11—C10—C15—C14	−0.4 (3)
C5—C6—C7—C8	4.8 (3)	C9—C10—C15—C14	179.98 (18)
C1—C6—C7—C8	−175.57 (19)	C13—C14—C15—C10	0.9 (3)
N1—C7—C8—C9	3.8 (2)	N1—N2—C16—O1	−174.42 (17)
C6—C7—C8—C9	−176.84 (17)	C9—N2—C16—O1	−2.4 (3)
C16—N2—C9—C10	69.6 (2)	N1—N2—C16—C17	7.0 (3)
N1—N2—C9—C10	−117.65 (18)	C9—N2—C16—C17	179.07 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1^i	0.93	2.48	3.306 (3)	148
C11—H11···O1^ii	0.93	2.55	3.459 (3)	167

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x+1, y, z.