(2-Ethoxy­phen­yl)[4-(6-fluoro­benzo[d]isoxazol-3-yl)piperidin-1-yl]methanone

In the title compound, C₂₁H₂₁FN₂O₃, the piperidine ring is in a chair conformation with the substituted benzisoxazole ring system in an equatorial position. An inter­molecular C—H...O inter­action is present in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.142
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.92

Author Response: ....We have collected data on kappa IP diffractometer and processed using Denzo; and it is known that the DENZO image processing package has problems with certain strong reflections. They are often excluded from the data set leading to a lower value for the above parameter.

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           25.02
           From the CIF: _diffrn_reflns_theta_full          25.02
           From the CIF: _reflns_number_total               2954
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         3222
           Completeness (_total/calc)             91.68%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.92
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         500 Deg.

   1 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

   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 2003).

(2-Ethoxyphenyl)[4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl]methanone

Crystal data

C21H21FN2O3	Z = 2
Mr = 368.40	F(000) = 388
Triclinic, P1	Dx = 1.346 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.029 (6) Å	Cell parameters from 4897 reflections
b = 9.851 (7) Å	θ = 2.2–25.0°
c = 14.120 (2) Å	µ = 0.10 mm^−1
α = 107.125 (5)°	T = 295 K
β = 94.622 (5)°	Block, colorless
γ = 100.513 (5)°	0.25 × 0.25 × 0.20 mm
V = 909.2 (10) Å^3

Data collection

MacScience DIPLabo 32001 diffractometer	2535 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 25.0°, θmin = 2.2°
Detector resolution: 10.0 pixels mm^-1	h = −8→8
ω scans	k = −11→11
4897 measured reflections	l = −16→16
2954 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H-atom parameters constrained
S = 1.15	w = 1/[σ^2(Fo^2) + (0.052P)^2 + 0.3865P] where P = (Fo^2 + 2Fc^2)/3
2954 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.19 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 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
F27	−0.6076 (2)	0.2443 (2)	0.34580 (15)	0.0935 (7)
O8	0.6471 (3)	0.69735 (19)	0.04217 (14)	0.0705 (6)
O15	0.7032 (2)	0.92471 (17)	0.30064 (11)	0.0538 (5)
O25	−0.0288 (3)	0.6193 (2)	0.44661 (12)	0.0631 (6)
N1	0.3923 (3)	0.77490 (19)	0.11216 (13)	0.0468 (6)
N26	0.0812 (3)	0.6972 (2)	0.38983 (15)	0.0598 (7)
C2	0.2634 (4)	0.6305 (2)	0.07302 (16)	0.0520 (7)
C3	0.1759 (3)	0.5859 (2)	0.15720 (16)	0.0495 (7)
C4	0.0703 (3)	0.6994 (2)	0.21698 (16)	0.0461 (7)
C5	0.2124 (3)	0.8479 (2)	0.25450 (16)	0.0479 (7)
C6	0.2987 (3)	0.8882 (2)	0.16859 (17)	0.0494 (7)
C7	0.5799 (3)	0.7956 (2)	0.09487 (15)	0.0463 (7)
C9	0.7103 (3)	0.9441 (2)	0.13969 (16)	0.0444 (7)
C10	0.7748 (3)	1.0059 (2)	0.24246 (15)	0.0443 (7)
C11	0.9065 (3)	1.1394 (2)	0.27873 (18)	0.0526 (7)
C12	0.9746 (4)	1.2094 (3)	0.2126 (2)	0.0597 (9)
C13	0.9162 (4)	1.1491 (3)	0.1116 (2)	0.0647 (10)
C14	0.7846 (4)	1.0168 (3)	0.07557 (19)	0.0586 (8)
C16	0.7583 (4)	0.9857 (3)	0.40709 (17)	0.0602 (8)
C17	0.6641 (4)	0.8766 (3)	0.45385 (18)	0.0661 (10)
C18	−0.0119 (3)	0.6496 (2)	0.29847 (16)	0.0470 (7)
C19	−0.1855 (3)	0.5402 (2)	0.28899 (16)	0.0449 (7)
C20	−0.3349 (3)	0.4555 (3)	0.21155 (17)	0.0528 (8)
C21	−0.4766 (3)	0.3563 (3)	0.2330 (2)	0.0608 (8)
C22	−0.4668 (3)	0.3461 (3)	0.3289 (2)	0.0612 (9)
C23	−0.3267 (4)	0.4284 (3)	0.40739 (19)	0.0590 (9)
C24	−0.1852 (3)	0.5258 (3)	0.38322 (16)	0.0500 (7)
H2A	0.33700	0.56030	0.04010	0.0620*
H2B	0.15940	0.63120	0.02380	0.0620*
H3A	0.27910	0.57390	0.20200	0.0590*
H3B	0.08410	0.49300	0.12920	0.0590*
H4	−0.03860	0.70570	0.17170	0.0550*
H5A	0.14410	0.92150	0.28800	0.0580*
H5B	0.31710	0.84550	0.30280	0.0580*
H6A	0.19590	0.90140	0.12420	0.0590*
H6B	0.39430	0.97950	0.19490	0.0590*
H11	0.94850	1.18140	0.34710	0.0630*
H12	1.06170	1.29920	0.23720	0.0720*
H13	0.96460	1.19660	0.06770	0.0780*
H14	0.74490	0.97550	0.00690	0.0700*
H16A	0.71450	1.07590	0.43170	0.0720*
H16B	0.89930	1.00610	0.42390	0.0720*
H17A	0.52470	0.85670	0.43640	0.0990*
H17B	0.69750	0.91520	0.52530	0.0990*
H17C	0.70980	0.78830	0.42970	0.0990*
H20	−0.33880	0.46560	0.14800	0.0630*
H21	−0.57780	0.29690	0.18340	0.0730*
H23	−0.32600	0.42000	0.47130	0.0710*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F27	0.0669 (10)	0.1082 (14)	0.1088 (14)	−0.0119 (10)	0.0106 (10)	0.0586 (12)
O8	0.0691 (11)	0.0543 (10)	0.0751 (12)	0.0129 (10)	0.0250 (9)	−0.0025 (9)
O15	0.0615 (10)	0.0554 (10)	0.0381 (8)	0.0011 (8)	0.0029 (7)	0.0131 (7)
O25	0.0622 (10)	0.0760 (12)	0.0456 (9)	0.0015 (10)	−0.0007 (8)	0.0211 (8)
N1	0.0508 (10)	0.0395 (10)	0.0445 (9)	0.0058 (9)	0.0076 (8)	0.0072 (8)
N26	0.0560 (11)	0.0685 (14)	0.0497 (11)	0.0014 (11)	0.0021 (9)	0.0197 (10)
C2	0.0586 (13)	0.0435 (12)	0.0429 (11)	0.0013 (11)	0.0057 (10)	0.0036 (9)
C3	0.0548 (13)	0.0404 (12)	0.0458 (11)	0.0041 (11)	0.0039 (10)	0.0071 (9)
C4	0.0413 (11)	0.0506 (13)	0.0455 (11)	0.0097 (10)	0.0009 (9)	0.0152 (10)
C5	0.0448 (11)	0.0449 (12)	0.0518 (12)	0.0137 (10)	0.0084 (10)	0.0091 (10)
C6	0.0488 (12)	0.0437 (12)	0.0566 (13)	0.0133 (11)	0.0074 (10)	0.0154 (10)
C7	0.0526 (12)	0.0456 (12)	0.0382 (10)	0.0094 (11)	0.0065 (9)	0.0102 (9)
C9	0.0458 (11)	0.0440 (12)	0.0446 (11)	0.0111 (10)	0.0098 (9)	0.0141 (9)
C10	0.0423 (11)	0.0454 (12)	0.0467 (11)	0.0121 (11)	0.0092 (9)	0.0146 (10)
C11	0.0455 (12)	0.0484 (13)	0.0581 (13)	0.0102 (11)	0.0020 (10)	0.0097 (11)
C12	0.0480 (13)	0.0476 (13)	0.0838 (18)	0.0079 (12)	0.0098 (12)	0.0225 (13)
C13	0.0691 (16)	0.0572 (16)	0.0768 (18)	0.0097 (14)	0.0210 (14)	0.0341 (14)
C14	0.0696 (15)	0.0584 (15)	0.0525 (13)	0.0133 (13)	0.0151 (12)	0.0231 (11)
C16	0.0591 (14)	0.0749 (17)	0.0392 (12)	0.0118 (13)	0.0040 (10)	0.0095 (11)
C17	0.0745 (17)	0.0857 (19)	0.0475 (13)	0.0301 (15)	0.0154 (12)	0.0256 (13)
C18	0.0446 (11)	0.0501 (13)	0.0446 (11)	0.0125 (11)	0.0042 (9)	0.0116 (10)
C19	0.0420 (11)	0.0479 (12)	0.0459 (11)	0.0135 (10)	0.0089 (9)	0.0134 (10)
C20	0.0455 (12)	0.0628 (15)	0.0474 (12)	0.0116 (12)	0.0043 (10)	0.0142 (11)
C21	0.0431 (12)	0.0655 (16)	0.0655 (15)	0.0026 (12)	0.0018 (11)	0.0152 (13)
C22	0.0460 (13)	0.0682 (16)	0.0752 (17)	0.0076 (13)	0.0136 (12)	0.0331 (14)
C23	0.0558 (14)	0.0713 (17)	0.0579 (14)	0.0164 (13)	0.0130 (12)	0.0294 (13)
C24	0.0487 (12)	0.0552 (13)	0.0465 (12)	0.0137 (11)	0.0058 (10)	0.0153 (10)

Geometric parameters (Å, º)

F27—C22	1.363 (3)	C20—C21	1.381 (4)
O8—C7	1.230 (3)	C21—C22	1.384 (4)
O15—C10	1.369 (3)	C22—C23	1.363 (4)
O15—C16	1.435 (3)	C23—C24	1.388 (4)
O25—N26	1.440 (3)	C2—H2A	0.9705
O25—C24	1.358 (3)	C2—H2B	0.9695
N1—C2	1.461 (3)	C3—H3A	0.9703
N1—C6	1.464 (3)	C3—H3B	0.9698
N1—C7	1.350 (3)	C4—H4	0.9799
N26—C18	1.307 (3)	C5—H5A	0.9703
C2—C3	1.520 (3)	C5—H5B	0.9706
C3—C4	1.537 (3)	C6—H6A	0.9700
C4—C5	1.531 (3)	C6—H6B	0.9700
C4—C18	1.495 (3)	C11—H11	0.9296
C5—C6	1.520 (3)	C12—H12	0.9301
C7—C9	1.501 (3)	C13—H13	0.9302
C9—C10	1.398 (3)	C14—H14	0.9305
C9—C14	1.388 (4)	C16—H16A	0.9697
C10—C11	1.390 (3)	C16—H16B	0.9697
C11—C12	1.381 (4)	C17—H17A	0.9601
C12—C13	1.368 (4)	C17—H17B	0.9594
C13—C14	1.381 (4)	C17—H17C	0.9597
C16—C17	1.503 (4)	C20—H20	0.9300
C18—C19	1.441 (3)	C21—H21	0.9301
C19—C20	1.397 (3)	C23—H23	0.9296
C19—C24	1.378 (3)
C10—O15—C16	117.74 (19)	C3—C2—H2B	109.57
N26—O25—C24	107.44 (17)	H2A—C2—H2B	108.07
C2—N1—C6	114.11 (19)	C2—C3—H3A	109.29
C2—N1—C7	120.52 (19)	C2—C3—H3B	109.26
C6—N1—C7	125.36 (18)	C4—C3—H3A	109.24
O25—N26—C18	106.82 (18)	C4—C3—H3B	109.29
N1—C2—C3	110.53 (17)	H3A—C3—H3B	107.95
C2—C3—C4	111.73 (17)	C3—C4—H4	108.25
C3—C4—C5	108.89 (17)	C5—C4—H4	108.24
C3—C4—C18	109.16 (17)	C18—C4—H4	108.21
C5—C4—C18	113.95 (18)	C4—C5—H5A	109.39
C4—C5—C6	111.22 (17)	C4—C5—H5B	109.39
N1—C6—C5	110.96 (17)	C6—C5—H5A	109.35
O8—C7—N1	122.2 (2)	C6—C5—H5B	109.40
O8—C7—C9	118.7 (2)	H5A—C5—H5B	108.02
N1—C7—C9	119.06 (18)	N1—C6—H6A	109.45
C7—C9—C10	122.67 (19)	N1—C6—H6B	109.43
C7—C9—C14	118.4 (2)	C5—C6—H6A	109.44
C10—C9—C14	118.6 (2)	C5—C6—H6B	109.47
O15—C10—C9	115.43 (18)	H6A—C6—H6B	108.04
O15—C10—C11	124.56 (19)	C10—C11—H11	120.23
C9—C10—C11	119.99 (19)	C12—C11—H11	120.16
C10—C11—C12	119.6 (2)	C11—C12—H12	119.37
C11—C12—C13	121.2 (3)	C13—C12—H12	119.43
C12—C13—C14	119.2 (3)	C12—C13—H13	120.42
C9—C14—C13	121.4 (2)	C14—C13—H13	120.37
O15—C16—C17	107.7 (2)	C9—C14—H14	119.30
N26—C18—C4	121.2 (2)	C13—C14—H14	119.35
N26—C18—C19	111.23 (19)	O15—C16—H16A	110.16
C4—C18—C19	127.44 (19)	O15—C16—H16B	110.18
C18—C19—C20	135.5 (2)	C17—C16—H16A	110.18
C18—C19—C24	104.23 (19)	C17—C16—H16B	110.11
C20—C19—C24	120.3 (2)	H16A—C16—H16B	108.48
C19—C20—C21	117.4 (2)	C16—C17—H17A	109.44
C20—C21—C22	119.4 (2)	C16—C17—H17B	109.46
F27—C22—C21	117.2 (2)	C16—C17—H17C	109.48
F27—C22—C23	117.5 (2)	H17A—C17—H17B	109.44
C21—C22—C23	125.3 (3)	H17A—C17—H17C	109.50
C22—C23—C24	113.9 (2)	H17B—C17—H17C	109.50
O25—C24—C19	110.3 (2)	C19—C20—H20	121.28
O25—C24—C23	126.1 (2)	C21—C20—H20	121.28
C19—C24—C23	123.6 (2)	C20—C21—H21	120.25
N1—C2—H2A	109.51	C22—C21—H21	120.31
N1—C2—H2B	109.57	C22—C23—H23	123.05
C3—C2—H2A	109.54	C24—C23—H23	123.05
C16—O15—C10—C9	−177.5 (2)	N1—C7—C9—C10	69.8 (3)
C16—O15—C10—C11	4.1 (3)	C14—C9—C10—O15	−176.7 (2)
C10—O15—C16—C17	−179.4 (2)	C14—C9—C10—C11	1.8 (3)
C24—O25—N26—C18	0.6 (3)	C10—C9—C14—C13	−1.5 (4)
N26—O25—C24—C19	−1.1 (3)	C7—C9—C10—C11	175.4 (2)
N26—O25—C24—C23	178.8 (3)	C7—C9—C14—C13	−175.4 (2)
C6—N1—C7—O8	−175.9 (2)	C7—C9—C10—O15	−3.1 (3)
C2—N1—C7—C9	−177.56 (18)	C9—C10—C11—C12	−0.8 (3)
C6—N1—C2—C3	−55.9 (2)	O15—C10—C11—C12	177.6 (2)
C2—N1—C7—O8	3.7 (3)	C10—C11—C12—C13	−0.6 (4)
C7—N1—C6—C5	−124.1 (2)	C11—C12—C13—C14	0.9 (4)
C6—N1—C7—C9	2.8 (3)	C12—C13—C14—C9	0.1 (4)
C2—N1—C6—C5	56.3 (2)	N26—C18—C19—C20	179.7 (3)
C7—N1—C2—C3	124.5 (2)	C4—C18—C19—C24	174.3 (2)
O25—N26—C18—C4	−175.30 (19)	N26—C18—C19—C24	−0.8 (3)
O25—N26—C18—C19	0.2 (2)	C4—C18—C19—C20	−5.1 (4)
N1—C2—C3—C4	55.0 (3)	C24—C19—C20—C21	−1.5 (4)
C2—C3—C4—C18	−179.89 (18)	C18—C19—C24—O25	1.2 (3)
C2—C3—C4—C5	−54.9 (2)	C18—C19—C20—C21	177.9 (2)
C3—C4—C5—C6	54.8 (2)	C20—C19—C24—O25	−179.3 (2)
C3—C4—C18—N26	97.3 (2)	C18—C19—C24—C23	−178.7 (2)
C5—C4—C18—N26	−24.6 (3)	C20—C19—C24—C23	0.8 (4)
C3—C4—C18—C19	−77.3 (3)	C19—C20—C21—C22	0.8 (4)
C18—C4—C5—C6	176.94 (18)	C20—C21—C22—C23	0.7 (4)
C5—C4—C18—C19	160.7 (2)	C20—C21—C22—F27	−178.6 (2)
C4—C5—C6—N1	−55.4 (2)	F27—C22—C23—C24	177.9 (2)
O8—C7—C9—C10	−111.4 (2)	C21—C22—C23—C24	−1.3 (4)
N1—C7—C9—C14	−116.5 (2)	C22—C23—C24—C19	0.6 (4)
O8—C7—C9—C14	62.3 (3)	C22—C23—C24—O25	−179.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O8^i	0.97	2.49	3.359 (3)	149

Symmetry code: (i) −x+1, −y+1, −z.