[5-Fluoro-2-(4-methyl­benzo­yloxy)phen­yl](4-methyl­phen­yl)methanone

In the title compound, C₂₂H₁₇FO₃, there are weak inter­molecular C—H...O hydrogen bonds resulting in the formation of a polymeric chain.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.038
• wR factor = 0.120
• Data-to-parameter ratio = 6.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT148_ALERT_3_B su on the      c  - Axis is Too Large (x 1000) .         17 Ang.

Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.86
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.02
           From the CIF: _reflns_number_total               1625
           Count of symmetry unique reflns         1649
           Completeness (_total/calc)             98.54%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

   0 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
   3 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: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

[5-Fluoro-2-(4-methylbenzoyloxy)phenyl](4-methylphenyl)methanone

Crystal data

C22H17FO3	F(000) = 728
Mr = 348.36	Dx = 1.298 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2860 reflections
a = 13.519 (10) Å	θ = 2.1–25.0°
b = 9.902 (9) Å	µ = 0.09 mm^−1
c = 13.319 (17) Å	T = 295 K
V = 1783 (3) Å^3	Block, pale yellow
Z = 4	0.25 × 0.20 × 0.20 mm

Data collection

MacScience DIPLabo 32001 diffractometer	1457 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
Graphite monochromator	θmax = 25.0°, θmin = 2.1°
Detector resolution: 10.0 pixels mm^-1	h = −16→16
ω scans	k = −11→11
2860 measured reflections	l = −15→15
1625 independent 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0703P)^2 + 0.2402P] where P = (Fo^2 + 2Fc^2)/3
1625 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 0.11 e Å^−3
1 restraint	Δρmin = −0.14 e Å^−3

Special details

Experimental. ¹H NMR (CDCl₃, 300 MHz): δ 2.3–2.4 (2s, 6H, 2CH₃), 7.16–8.02 (m, 11H, Ar—H). EI–MS: m/z(86%) M⁺364; IR (Nujol): 1667 (C═O), 1760 cm^-1 (COO). Analysis calculated for C₂₂H₁₇FO₃: C 75.85, H 4.92, F 5.45%; found: C 75.84, H 4.91, F 5.44%.

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 on F^2 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 F^2, conventional R-factors R are based on F, with F set to zero for negative F^2. The observed criterion of F^2 > σ(F^2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2 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
F7	−0.12130 (16)	0.2488 (2)	0.3594 (2)	0.0819 (9)
O9	0.2053 (2)	0.0360 (3)	0.2595 (3)	0.0957 (13)
O17	0.25446 (18)	0.2085 (2)	0.51195 (18)	0.0530 (7)
O19	0.27596 (18)	0.4228 (2)	0.5642 (3)	0.0783 (10)
C1	0.0472 (3)	0.1988 (3)	0.3361 (3)	0.0537 (11)
C2	0.1436 (2)	0.1942 (3)	0.3741 (2)	0.0467 (9)
C3	0.1601 (2)	0.2338 (3)	0.4733 (2)	0.0486 (10)
C4	0.0829 (3)	0.2786 (4)	0.5334 (3)	0.0579 (11)
C5	−0.0115 (3)	0.2844 (4)	0.4946 (3)	0.0637 (14)
C6	−0.0276 (3)	0.2442 (3)	0.3971 (3)	0.0573 (13)
C8	0.2238 (2)	0.1365 (3)	0.3084 (3)	0.0561 (11)
C10	0.3226 (2)	0.2015 (3)	0.3031 (2)	0.0483 (10)
C11	0.4059 (3)	0.1235 (3)	0.2843 (3)	0.0581 (11)
C12	0.4994 (3)	0.1807 (4)	0.2841 (3)	0.0657 (12)
C13	0.5121 (3)	0.3168 (4)	0.3000 (3)	0.0607 (12)
C14	0.4287 (3)	0.3953 (3)	0.3132 (3)	0.0625 (11)
C15	0.3350 (3)	0.3399 (3)	0.3166 (3)	0.0563 (11)
C16	0.6150 (3)	0.3788 (5)	0.3040 (4)	0.0910 (17)
C18	0.3092 (2)	0.3128 (3)	0.5501 (3)	0.0524 (11)
C20	0.4128 (3)	0.2711 (3)	0.5659 (2)	0.0512 (11)
C21	0.4457 (3)	0.1404 (3)	0.5488 (3)	0.0568 (11)
C22	0.5452 (3)	0.1104 (4)	0.5560 (3)	0.0658 (11)
C23	0.6145 (3)	0.2084 (4)	0.5774 (3)	0.0640 (12)
C24	0.5811 (3)	0.3380 (4)	0.5971 (3)	0.0703 (14)
C25	0.4819 (3)	0.3685 (4)	0.5916 (3)	0.0634 (13)
C26	0.7246 (3)	0.1793 (5)	0.5785 (5)	0.098 (2)
H1	0.03390	0.17150	0.27070	0.0640*
H4	0.09480	0.30450	0.59940	0.0690*
H5	−0.06380	0.31500	0.53390	0.0770*
H11	0.39880	0.03170	0.27160	0.0700*
H12	0.55440	0.12620	0.27310	0.0790*
H14	0.43580	0.48820	0.32010	0.0750*
H15	0.28030	0.39480	0.32780	0.0670*
H16A	0.63320	0.41020	0.23840	0.1370*
H16B	0.66160	0.31210	0.32610	0.1370*
H16C	0.61500	0.45340	0.35010	0.1370*
H21	0.40070	0.07290	0.53240	0.0680*
H22	0.56590	0.02180	0.54620	0.0790*
H24	0.62620	0.40510	0.61410	0.0850*
H25	0.46080	0.45600	0.60530	0.0760*
H26A	0.73920	0.10940	0.53080	0.1470*
H26B	0.74390	0.15030	0.64440	0.1470*
H26C	0.76020	0.25970	0.56100	0.1470*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F7	0.0488 (13)	0.1000 (16)	0.0970 (18)	−0.0015 (11)	−0.0080 (13)	−0.0018 (13)
O9	0.0722 (17)	0.094 (2)	0.121 (3)	−0.0220 (15)	0.0181 (18)	−0.057 (2)
O17	0.0479 (13)	0.0547 (12)	0.0565 (13)	−0.0002 (10)	−0.0053 (11)	−0.0010 (10)
O19	0.0657 (17)	0.0593 (14)	0.110 (2)	0.0102 (12)	−0.0083 (16)	−0.0212 (16)
C1	0.0499 (19)	0.0551 (18)	0.0561 (18)	−0.0063 (15)	−0.0004 (15)	0.0011 (14)
C2	0.0455 (17)	0.0447 (15)	0.0499 (17)	−0.0039 (13)	0.0060 (15)	−0.0016 (13)
C3	0.0448 (19)	0.0475 (16)	0.0535 (19)	−0.0009 (13)	0.0010 (14)	0.0020 (14)
C4	0.055 (2)	0.065 (2)	0.0536 (19)	−0.0046 (15)	0.0078 (17)	−0.0064 (16)
C5	0.047 (2)	0.069 (2)	0.075 (3)	−0.0028 (16)	0.0130 (18)	−0.0088 (19)
C6	0.0414 (19)	0.0584 (19)	0.072 (3)	−0.0048 (14)	−0.0015 (16)	0.0057 (17)
C8	0.052 (2)	0.0562 (17)	0.060 (2)	−0.0040 (14)	0.0029 (17)	−0.0105 (16)
C10	0.0455 (17)	0.0507 (17)	0.0486 (17)	0.0012 (13)	0.0024 (15)	−0.0018 (15)
C11	0.058 (2)	0.0514 (17)	0.065 (2)	0.0048 (15)	0.0035 (18)	−0.0025 (16)
C12	0.052 (2)	0.074 (2)	0.071 (2)	0.0102 (17)	0.0043 (18)	0.008 (2)
C13	0.057 (2)	0.074 (2)	0.051 (2)	−0.0098 (17)	−0.0011 (17)	0.0044 (18)
C14	0.071 (2)	0.0505 (17)	0.066 (2)	−0.0092 (16)	0.0087 (18)	−0.0006 (17)
C15	0.058 (2)	0.0499 (17)	0.061 (2)	0.0054 (15)	0.0120 (16)	−0.0013 (16)
C16	0.065 (3)	0.117 (3)	0.091 (3)	−0.030 (3)	0.002 (2)	0.008 (3)
C18	0.051 (2)	0.0526 (18)	0.0536 (19)	−0.0007 (14)	−0.0033 (16)	−0.0019 (15)
C20	0.056 (2)	0.0485 (17)	0.0492 (18)	−0.0016 (14)	−0.0017 (16)	0.0015 (14)
C21	0.057 (2)	0.0515 (17)	0.062 (2)	0.0004 (15)	−0.0056 (17)	−0.0008 (17)
C22	0.063 (2)	0.0603 (19)	0.074 (2)	0.0105 (17)	−0.0022 (19)	0.0006 (19)
C23	0.050 (2)	0.080 (2)	0.062 (2)	−0.0019 (18)	−0.0033 (17)	0.0155 (19)
C24	0.060 (2)	0.066 (2)	0.085 (3)	−0.0150 (18)	−0.011 (2)	0.012 (2)
C25	0.062 (2)	0.0511 (18)	0.077 (3)	−0.0028 (16)	−0.0063 (19)	0.0012 (17)
C26	0.053 (3)	0.122 (4)	0.118 (4)	0.007 (2)	−0.005 (3)	0.033 (4)

Geometric parameters (Å, º)

F7—C6	1.363 (5)	C21—C22	1.381 (6)
O9—C8	1.215 (5)	C22—C23	1.379 (6)
O17—C3	1.398 (4)	C23—C24	1.385 (6)
O17—C18	1.368 (4)	C23—C26	1.516 (6)
O19—C18	1.193 (4)	C24—C25	1.377 (6)
C1—C2	1.399 (5)	C1—H1	0.9296
C1—C6	1.373 (6)	C4—H4	0.9297
C2—C3	1.396 (4)	C5—H5	0.9304
C2—C8	1.506 (5)	C11—H11	0.9296
C3—C4	1.388 (5)	C12—H12	0.9304
C4—C5	1.378 (6)	C14—H14	0.9294
C5—C6	1.376 (6)	C15—H15	0.9298
C8—C10	1.484 (4)	C16—H16A	0.9595
C10—C11	1.388 (5)	C16—H16B	0.9590
C10—C15	1.392 (5)	C16—H16C	0.9606
C11—C12	1.385 (6)	C21—H21	0.9298
C12—C13	1.375 (6)	C22—H22	0.9301
C13—C14	1.381 (6)	C24—H24	0.9298
C13—C16	1.521 (6)	C25—H25	0.9302
C14—C15	1.381 (6)	C26—H26A	0.9600
C18—C20	1.475 (5)	C26—H26B	0.9597
C20—C21	1.387 (5)	C26—H26C	0.9590
C20—C25	1.386 (6)
F7···H14^i	2.7662	C20···H1^vi	2.9887
O9···C26^ii	3.355 (8)	C21···H1^vi	2.9843
O17···C15	3.106 (6)	C25···H1^vi	3.0889
O17···C10	2.931 (5)	H1···O9	2.6817
O19···C4	3.003 (6)	H1···C20^v	2.9887
O9···H1	2.6817	H1···C21^v	2.9843
O9···H12^iii	2.6027	H1···C25^v	3.0889
O9···H26B^ii	2.4950	H4···O19	2.7550
O9···H11	2.6212	H4···C18	2.9731
O17···H21	2.4053	H4···C11^vi	3.0458
O19···H4	2.7550	H4···C12^vi	3.0292
O19···H25	2.5791	H4···C13^vi	3.0400
O19···H24^i	2.7285	H4···C14^vi	3.0030
C3···C15	3.324 (6)	H4···C15^vi	3.0647
C4···O19	3.003 (6)	H5···H26C^vii	2.4681
C10···C18	3.474 (6)	H5···H25^i	2.4813
C10···O17	2.931 (5)	H11···O9	2.6212
C11···C21	3.568 (7)	H12···H16B	2.4468
C14···C20	3.590 (7)	H12···O9^viii	2.6027
C15···C3	3.324 (6)	H14···H16C	2.4794
C15···C18	3.141 (7)	H14···F7^ix	2.7662
C15···C20	3.549 (7)	H14···C6^ix	2.8841
C15···O17	3.106 (6)	H15···C2	2.7823
C18···C10	3.474 (6)	H15···C3	2.9896
C18···C15	3.141 (7)	H15···C18	3.0949
C20···C15	3.549 (7)	H16A···H25^x	2.5520
C20···C14	3.590 (7)	H16B···H12	2.4468
C21···C11	3.568 (7)	H16C···H14	2.4794
C26···O9^iv	3.355 (8)	H21···O17	2.4053
C2···H15	2.7823	H22···H26A	2.5067
C3···H15	2.9896	H22···C3^viii	2.9950
C3···H22^iii	2.9950	H22···C4^viii	2.9883
C4···H22^iii	2.9883	H24···H26C	2.4197
C5···H25^i	2.9870	H24···O19^ix	2.7285
C6···H14^i	2.8841	H25···O19	2.5791
C11···H4^v	3.0458	H25···H16A^xi	2.5520
C12···H4^v	3.0292	H25···C5^ix	2.9870
C13···H4^v	3.0400	H25···H5^ix	2.4813
C14···H4^v	3.0030	H26A···H22	2.5067
C15···H4^v	3.0647	H26B···O9^iv	2.4950
C18···H4	2.9731	H26C···H5^xii	2.4681
C18···H15	3.0949	H26C···H24	2.4197
C3—O17—C18	119.7 (2)	C23—C24—C25	120.7 (4)
C2—C1—C6	118.9 (3)	C20—C25—C24	121.1 (4)
C1—C2—C3	118.8 (3)	C2—C1—H1	120.65
C1—C2—C8	118.2 (3)	C6—C1—H1	120.48
C3—C2—C8	122.8 (3)	C3—C4—H4	120.22
O17—C3—C2	116.4 (2)	C5—C4—H4	120.22
O17—C3—C4	122.1 (3)	C4—C5—H5	120.42
C2—C3—C4	121.0 (3)	C6—C5—H5	120.34
C3—C4—C5	119.6 (3)	C10—C11—H11	119.54
C4—C5—C6	119.2 (4)	C12—C11—H11	119.59
F7—C6—C1	118.5 (3)	C11—C12—H12	119.50
F7—C6—C5	119.0 (3)	C13—C12—H12	119.54
C1—C6—C5	122.5 (4)	C13—C14—H14	119.04
O9—C8—C2	118.3 (3)	C15—C14—H14	118.98
O9—C8—C10	121.0 (3)	C10—C15—H15	120.03
C2—C8—C10	120.7 (3)	C14—C15—H15	120.16
C8—C10—C11	119.8 (3)	C13—C16—H16A	109.47
C8—C10—C15	121.9 (3)	C13—C16—H16B	109.48
C11—C10—C15	118.2 (3)	C13—C16—H16C	109.43
C10—C11—C12	120.9 (3)	H16A—C16—H16B	109.52
C11—C12—C13	121.0 (4)	H16A—C16—H16C	109.44
C12—C13—C14	118.0 (4)	H16B—C16—H16C	109.48
C12—C13—C16	121.0 (4)	C20—C21—H21	119.96
C14—C13—C16	121.0 (4)	C22—C21—H21	119.94
C13—C14—C15	122.0 (3)	C21—C22—H22	119.10
C10—C15—C14	119.8 (3)	C23—C22—H22	119.24
O17—C18—O19	122.9 (3)	C23—C24—H24	119.62
O17—C18—C20	110.8 (2)	C25—C24—H24	119.67
O19—C18—C20	126.2 (3)	C20—C25—H25	119.34
C18—C20—C21	122.8 (3)	C24—C25—H25	119.51
C18—C20—C25	118.7 (3)	C23—C26—H26A	109.42
C21—C20—C25	118.3 (4)	C23—C26—H26B	109.43
C20—C21—C22	120.1 (3)	C23—C26—H26C	109.42
C21—C22—C23	121.7 (4)	H26A—C26—H26B	109.49
C22—C23—C24	118.0 (4)	H26A—C26—H26C	109.54
C22—C23—C26	122.4 (4)	H26B—C26—H26C	109.53
C24—C23—C26	119.6 (4)
C3—O17—C18—C20	−167.5 (3)	C8—C10—C15—C14	178.6 (3)
C3—O17—C18—O19	9.9 (5)	C8—C10—C11—C12	−176.7 (3)
C18—O17—C3—C4	−65.0 (4)	C15—C10—C11—C12	3.3 (5)
C18—O17—C3—C2	123.5 (3)	C11—C10—C15—C14	−1.4 (5)
C6—C1—C2—C8	176.4 (3)	C10—C11—C12—C13	−1.6 (6)
C2—C1—C6—C5	−0.5 (5)	C11—C12—C13—C16	177.5 (4)
C6—C1—C2—C3	1.1 (4)	C11—C12—C13—C14	−1.9 (6)
C2—C1—C6—F7	179.8 (3)	C12—C13—C14—C15	3.8 (6)
C8—C2—C3—C4	−175.9 (3)	C16—C13—C14—C15	−175.6 (4)
C1—C2—C8—C10	138.3 (3)	C13—C14—C15—C10	−2.2 (6)
C3—C2—C8—O9	133.9 (4)	O17—C18—C20—C21	−3.4 (5)
C1—C2—C8—O9	−41.3 (5)	O17—C18—C20—C25	171.6 (3)
C1—C2—C3—C4	−0.7 (5)	O19—C18—C20—C21	179.3 (4)
C8—C2—C3—O17	−4.3 (4)	O19—C18—C20—C25	−5.7 (6)
C3—C2—C8—C10	−46.5 (4)	C18—C20—C21—C22	174.0 (3)
C1—C2—C3—O17	170.8 (3)	C25—C20—C21—C22	−1.0 (5)
O17—C3—C4—C5	−171.2 (3)	C18—C20—C25—C24	−173.2 (4)
C2—C3—C4—C5	−0.1 (5)	C21—C20—C25—C24	2.0 (5)
C3—C4—C5—C6	0.7 (6)	C20—C21—C22—C23	−1.8 (6)
C4—C5—C6—F7	179.3 (3)	C21—C22—C23—C24	3.4 (6)
C4—C5—C6—C1	−0.4 (6)	C21—C22—C23—C26	−175.7 (4)
C2—C8—C10—C11	150.0 (3)	C22—C23—C24—C25	−2.4 (6)
C2—C8—C10—C15	−29.9 (5)	C26—C23—C24—C25	176.7 (4)
O9—C8—C10—C15	149.6 (4)	C23—C24—C25—C20	−0.3 (6)
O9—C8—C10—C11	−30.5 (5)

Symmetry codes: (i) x−1/2, −y+1, z; (ii) −x+1, −y, z−1/2; (iii) x−1/2, −y, z; (iv) −x+1, −y, z+1/2; (v) −x+1/2, y, z−1/2; (vi) −x+1/2, y, z+1/2; (vii) x−1, y, z; (viii) x+1/2, −y, z; (ix) x+1/2, −y+1, z; (x) −x+1, −y+1, z−1/2; (xi) −x+1, −y+1, z+1/2; (xii) x+1, y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26B···O9^iv	0.96	2.49	3.355 (8)	149

Symmetry code: (iv) −x+1, −y, z+1/2.