(2R*,3R*,6S*)-N,6-Bis(4-fluoro­phen­yl)-2-(4-hydroxy­phen­yl)-3,4,5,6-tetra­hydro-2H-pyran-3-carboxamide

Swamy, G.Y.S.K.; Ravikumar, K.; Wadhwa, L.K.; Saxena, R.; Singh, S.

doi:10.1107/S1600536805031818

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(2R,3R,6S*)-N,6-Bis(4-fluorophenyl)-2-(4-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran-3-carboxamide

G. Y. S. K. Swamy, K. Ravikumar, L. K. Wadhwa, R. Saxena and S. Singh

The molecule of the title compound, C₂₄H₂₁F₂NO₂, has a T-shaped form in the crystal structure. The central tetrahydropyran ring shows a chair conformation. All substituents are equatorially attached to this ring. The crystal packing is stabilized by N—H

O, O—H

O and C—H

π(arene) interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031818/bt6753sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031818/bt6753Isup2.hkl Contains datablock I

CCDC reference: 289650

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.004 Å
R factor = 0.044
wR factor = 0.101
Data-to-parameter ratio = 8.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

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           27.97
           From the CIF: _reflns_number_total               2282
           Count of symmetry unique reflns         2396
           Completeness (_total/calc)             95.24%
           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
   0 ALERT level B = Potentially serious problem
   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

N,6-Bis(4-fluorophenyl)-2-(4-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran- 3-carboxamide top

Crystal data top

C₂₄H₂₁F₂NO₃	Z = 1
M_r = 409.42	F(000) = 214
Triclinic, P1	D_x = 1.365 Mg m⁻³
a = 6.1397 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6596 (7) Å	Cell parameters from 2320 reflections
c = 11.1439 (10) Å	θ = 2.8–26.8°
α = 72.484 (1)°	µ = 0.10 mm⁻¹
β = 89.979 (1)°	T = 273 K
γ = 85.553 (2)°	Needle, colourless
V = 498.12 (8) Å³	0.22 × 0.18 × 0.16 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2121 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.024
Graphite monochromator	θ_max = 28.0°, θ_min = 1.9°
ω scans	h = −8→8
5763 measured reflections	k = −10→9
2282 independent reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.051P)² + 0.0636P] where P = (F_o² + 2F_c²)/3
2282 reflections	(Δ/σ)_max < 0.001
272 parameters	Δρ_max = 0.22 e Å⁻³
3 restraints	Δρ_min = −0.20 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.1778 (5)	0.8880 (4)	0.1876 (3)	0.0439 (7)
C2	0.1038 (5)	0.9375 (5)	0.2891 (3)	0.0517 (7)
H2A	−0.0353	0.9959	0.2874	0.062*
C3	0.2384 (5)	0.8995 (4)	0.3940 (3)	0.0473 (7)
H3	0.1898	0.9328	0.4638	0.057*
C4	0.4466 (4)	0.8118 (4)	0.3969 (2)	0.0367 (6)
C5	0.5159 (5)	0.7666 (4)	0.2911 (3)	0.0419 (6)
H5	0.6556	0.7102	0.2912	0.050*
C6	0.3825 (5)	0.8032 (4)	0.1856 (3)	0.0459 (7)
H6	0.4298	0.7713	0.1152	0.055*
C7	0.5906 (5)	0.7532 (4)	0.5138 (2)	0.0397 (6)
H7	0.7417	0.7769	0.4900	0.048*
C8	0.5809 (6)	0.5495 (4)	0.5815 (3)	0.0502 (8)
H8A	0.4307	0.5233	0.6010	0.060*
H8B	0.6350	0.4785	0.5273	0.060*
C9	0.7187 (6)	0.4951 (4)	0.7021 (3)	0.0508 (8)
H9A	0.8708	0.5132	0.6824	0.061*
H9B	0.7077	0.3663	0.7468	0.061*
C10	0.6375 (5)	0.6132 (4)	0.7850 (2)	0.0374 (6)
H10	0.4862	0.5890	0.8079	0.045*
C11	0.6452 (4)	0.8205 (4)	0.7094 (2)	0.0357 (6)
H11	0.7972	0.8455	0.6891	0.043*
C12	0.5523 (4)	0.9486 (4)	0.7789 (2)	0.0354 (5)
C13	0.3430 (5)	1.0373 (4)	0.7519 (3)	0.0447 (7)
H13	0.2585	1.0180	0.6886	0.054*
C14	0.2585 (5)	1.1536 (4)	0.8174 (3)	0.0450 (7)
H14	0.1194	1.2129	0.7971	0.054*
C15	0.3810 (4)	1.1816 (4)	0.9129 (2)	0.0379 (6)
C16	0.5890 (5)	1.0932 (4)	0.9418 (3)	0.0405 (6)
H16	0.6718	1.1108	1.0065	0.049*
C17	0.6728 (4)	0.9800 (4)	0.8753 (3)	0.0382 (6)
H17	0.8131	0.9229	0.8950	0.046*
C18	0.7800 (4)	0.5595 (3)	0.9044 (2)	0.0366 (6)
C19	0.7577 (4)	0.4291 (3)	1.1375 (2)	0.0356 (6)
C20	0.6294 (5)	0.3182 (4)	1.2272 (3)	0.0421 (6)
H20	0.4974	0.2855	1.2029	0.050*
C21	0.6977 (6)	0.2555 (4)	1.3534 (3)	0.0473 (7)
H21	0.6126	0.1821	1.4142	0.057*
C22	0.8943 (5)	0.3056 (4)	1.3850 (3)	0.0502 (8)
C23	1.0221 (5)	0.4144 (5)	1.2997 (3)	0.0496 (7)
H23	1.1537	0.4460	1.3253	0.060*
C24	0.9554 (5)	0.4783 (4)	1.1739 (3)	0.0438 (6)
H24	1.0417	0.5531	1.1146	0.053*
N1	0.6719 (4)	0.4969 (3)	1.0124 (2)	0.0364 (5)
H1	0.5324	0.4982	1.0043	0.044*
O1	0.5202 (3)	0.8589 (2)	0.59474 (16)	0.0395 (4)
O2	0.3061 (3)	1.2942 (3)	0.9820 (2)	0.0485 (5)
H2	0.1895	1.3490	0.9514	0.073*
O3	0.9779 (3)	0.5686 (3)	0.89969 (19)	0.0512 (5)
F1	0.0451 (3)	0.9243 (3)	0.08451 (19)	0.0655 (6)
F2	0.9622 (4)	0.2419 (3)	1.50850 (18)	0.0748 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0523 (17)	0.0422 (15)	0.0361 (14)	0.0006 (12)	−0.0147 (12)	−0.0111 (12)
C2	0.0466 (17)	0.0565 (18)	0.0546 (18)	0.0140 (14)	−0.0103 (14)	−0.0251 (15)
C3	0.0489 (16)	0.0574 (18)	0.0397 (15)	0.0111 (13)	−0.0041 (13)	−0.0245 (13)
C4	0.0428 (14)	0.0350 (13)	0.0300 (12)	0.0034 (11)	−0.0039 (11)	−0.0080 (10)
C5	0.0477 (16)	0.0445 (15)	0.0322 (13)	0.0073 (12)	0.0004 (11)	−0.0123 (11)
C6	0.0603 (18)	0.0497 (16)	0.0303 (13)	0.0012 (13)	−0.0003 (12)	−0.0172 (12)
C7	0.0430 (14)	0.0461 (15)	0.0271 (12)	0.0078 (12)	−0.0036 (11)	−0.0097 (11)
C8	0.076 (2)	0.0415 (16)	0.0342 (14)	0.0122 (14)	−0.0064 (14)	−0.0177 (12)
C9	0.076 (2)	0.0376 (15)	0.0347 (14)	0.0179 (14)	−0.0052 (14)	−0.0099 (12)
C10	0.0466 (15)	0.0345 (13)	0.0291 (13)	0.0063 (11)	−0.0038 (11)	−0.0088 (10)
C11	0.0388 (13)	0.0366 (13)	0.0286 (12)	0.0043 (10)	−0.0047 (10)	−0.0069 (10)
C12	0.0402 (14)	0.0340 (13)	0.0298 (12)	0.0021 (10)	−0.0056 (10)	−0.0077 (10)
C13	0.0408 (15)	0.0535 (17)	0.0440 (16)	0.0064 (13)	−0.0160 (12)	−0.0236 (13)
C14	0.0354 (14)	0.0527 (17)	0.0477 (16)	0.0106 (12)	−0.0142 (12)	−0.0198 (13)
C15	0.0380 (14)	0.0351 (13)	0.0423 (15)	0.0013 (11)	−0.0043 (11)	−0.0150 (11)
C16	0.0430 (14)	0.0394 (14)	0.0402 (14)	0.0033 (11)	−0.0156 (11)	−0.0154 (12)
C17	0.0359 (13)	0.0347 (13)	0.0422 (15)	0.0057 (10)	−0.0116 (11)	−0.0111 (11)
C18	0.0430 (15)	0.0318 (13)	0.0327 (13)	0.0089 (11)	−0.0036 (11)	−0.0093 (10)
C19	0.0445 (14)	0.0325 (12)	0.0306 (13)	0.0072 (11)	−0.0048 (11)	−0.0133 (10)
C20	0.0505 (16)	0.0382 (14)	0.0395 (15)	0.0012 (12)	−0.0003 (12)	−0.0160 (12)
C21	0.064 (2)	0.0412 (15)	0.0336 (14)	0.0046 (13)	0.0043 (13)	−0.0094 (12)
C22	0.066 (2)	0.0522 (18)	0.0314 (14)	0.0201 (15)	−0.0137 (14)	−0.0169 (13)
C23	0.0469 (16)	0.0622 (19)	0.0432 (16)	0.0081 (14)	−0.0117 (13)	−0.0243 (14)
C24	0.0457 (16)	0.0466 (15)	0.0411 (15)	0.0004 (12)	−0.0020 (12)	−0.0173 (12)
N1	0.0386 (12)	0.0403 (12)	0.0310 (11)	0.0016 (9)	−0.0055 (9)	−0.0128 (9)
O1	0.0520 (11)	0.0369 (10)	0.0281 (9)	0.0100 (8)	−0.0104 (8)	−0.0108 (7)
O2	0.0431 (11)	0.0546 (13)	0.0538 (13)	0.0122 (9)	−0.0129 (9)	−0.0292 (10)
O3	0.0439 (11)	0.0609 (13)	0.0400 (11)	0.0102 (9)	−0.0022 (9)	−0.0055 (9)
F1	0.0710 (13)	0.0760 (14)	0.0501 (11)	0.0071 (10)	−0.0271 (9)	−0.0230 (10)
F2	0.0913 (16)	0.0904 (15)	0.0353 (10)	0.0267 (12)	−0.0214 (10)	−0.0159 (10)

Geometric parameters (Å, º) top

C1—F1	1.354 (3)	C12—C17	1.394 (4)
C1—C2	1.364 (4)	C12—C13	1.395 (4)
C1—C6	1.373 (4)	C13—C14	1.384 (4)
C2—C3	1.376 (4)	C13—H13	0.9300
C2—H2A	0.9300	C14—C15	1.381 (4)
C3—C4	1.393 (4)	C14—H14	0.9300
C3—H3	0.9300	C15—O2	1.373 (3)
C4—C5	1.383 (4)	C15—C16	1.389 (4)
C4—C7	1.506 (3)	C16—C17	1.372 (4)
C5—C6	1.377 (4)	C16—H16	0.9300
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—O3	1.223 (3)
C7—O1	1.428 (3)	C18—N1	1.349 (3)
C7—C8	1.521 (4)	C19—C20	1.390 (4)
C7—H7	0.9800	C19—C24	1.394 (4)
C8—C9	1.519 (4)	C19—N1	1.419 (3)
C8—H8A	0.9700	C20—C21	1.396 (4)
C8—H8B	0.9700	C20—H20	0.9300
C9—C10	1.534 (4)	C21—C22	1.372 (5)
C9—H9A	0.9700	C21—H21	0.9300
C9—H9B	0.9700	C22—C23	1.355 (5)
C10—C18	1.523 (4)	C22—F2	1.368 (3)
C10—C11	1.561 (3)	C23—C24	1.389 (4)
C10—H10	0.9800	C23—H23	0.9300
C11—O1	1.431 (3)	C24—H24	0.9300
C11—C12	1.503 (4)	N1—H1	0.8600
C11—H11	0.9800	O2—H2	0.8200

F1—C1—C2	118.9 (3)	C12—C11—H11	109.0
F1—C1—C6	118.6 (3)	C10—C11—H11	109.0
C2—C1—C6	122.5 (2)	C17—C12—C13	117.5 (2)
C1—C2—C3	118.9 (3)	C17—C12—C11	120.6 (2)
C1—C2—H2A	120.6	C13—C12—C11	121.9 (2)
C3—C2—H2A	120.6	C14—C13—C12	121.4 (2)
C2—C3—C4	120.7 (3)	C14—C13—H13	119.3
C2—C3—H3	119.7	C12—C13—H13	119.3
C4—C3—H3	119.7	C15—C14—C13	119.9 (2)
C5—C4—C3	118.4 (2)	C15—C14—H14	120.0
C5—C4—C7	119.3 (2)	C13—C14—H14	120.0
C3—C4—C7	122.1 (2)	O2—C15—C14	122.8 (2)
C6—C5—C4	121.5 (3)	O2—C15—C16	117.7 (2)
C6—C5—H5	119.3	C14—C15—C16	119.5 (2)
C4—C5—H5	119.3	C17—C16—C15	120.2 (2)
C1—C6—C5	118.1 (2)	C17—C16—H16	119.9
C1—C6—H6	121.0	C15—C16—H16	119.9
C5—C6—H6	121.0	C16—C17—C12	121.5 (2)
O1—C7—C4	108.9 (2)	C16—C17—H17	119.3
O1—C7—C8	110.2 (2)	C12—C17—H17	119.3
C4—C7—C8	110.8 (2)	O3—C18—N1	123.9 (2)
O1—C7—H7	109.0	O3—C18—C10	121.2 (2)
C4—C7—H7	109.0	N1—C18—C10	114.9 (2)
C8—C7—H7	109.0	C20—C19—C24	119.8 (3)
C9—C8—C7	109.9 (2)	C20—C19—N1	117.3 (2)
C9—C8—H8A	109.7	C24—C19—N1	122.8 (2)
C7—C8—H8A	109.7	C19—C20—C21	120.4 (3)
C9—C8—H8B	109.7	C19—C20—H20	119.8
C7—C8—H8B	109.7	C21—C20—H20	119.8
H8A—C8—H8B	108.2	C22—C21—C20	117.9 (3)
C8—C9—C10	109.3 (2)	C22—C21—H21	121.0
C8—C9—H9A	109.8	C20—C21—H21	121.0
C10—C9—H9A	109.8	C23—C22—F2	119.2 (3)
C8—C9—H9B	109.8	C23—C22—C21	123.0 (3)
C10—C9—H9B	109.8	F2—C22—C21	117.8 (3)
H9A—C9—H9B	108.3	C22—C23—C24	119.6 (3)
C18—C10—C9	108.6 (2)	C22—C23—H23	120.2
C18—C10—C11	111.9 (2)	C24—C23—H23	120.2
C9—C10—C11	109.2 (2)	C23—C24—C19	119.3 (3)
C18—C10—H10	109.0	C23—C24—H24	120.3
C9—C10—H10	109.0	C19—C24—H24	120.3
C11—C10—H10	109.0	C18—N1—C19	128.6 (2)
O1—C11—C12	107.4 (2)	C18—N1—H1	115.7
O1—C11—C10	109.1 (2)	C19—N1—H1	115.7
C12—C11—C10	113.4 (2)	C7—O1—C11	115.23 (19)
O1—C11—H11	109.0	C15—O2—H2	109.5

F1—C1—C2—C3	179.6 (3)	C13—C14—C15—O2	−179.5 (3)
C6—C1—C2—C3	−0.6 (5)	C13—C14—C15—C16	0.4 (4)
C1—C2—C3—C4	−0.1 (5)	O2—C15—C16—C17	−179.6 (3)
C2—C3—C4—C5	1.0 (5)	C14—C15—C16—C17	0.5 (4)
C2—C3—C4—C7	−174.5 (3)	C15—C16—C17—C12	−0.8 (4)
C3—C4—C5—C6	−1.3 (4)	C13—C12—C17—C16	0.3 (4)
C7—C4—C5—C6	174.4 (3)	C11—C12—C17—C16	−178.5 (3)
F1—C1—C6—C5	−179.9 (3)	C9—C10—C18—O3	57.6 (3)
C2—C1—C6—C5	0.4 (5)	C11—C10—C18—O3	−63.0 (3)
C4—C5—C6—C1	0.6 (4)	C9—C10—C18—N1	−120.3 (3)
C5—C4—C7—O1	162.8 (2)	C11—C10—C18—N1	119.1 (2)
C3—C4—C7—O1	−21.7 (4)	C24—C19—C20—C21	−0.1 (4)
C5—C4—C7—C8	−75.9 (3)	N1—C19—C20—C21	−176.2 (2)
C3—C4—C7—C8	99.5 (3)	C19—C20—C21—C22	−0.5 (4)
O1—C7—C8—C9	−56.9 (3)	C20—C21—C22—C23	0.9 (4)
C4—C7—C8—C9	−177.4 (2)	C20—C21—C22—F2	−179.1 (3)
C7—C8—C9—C10	57.2 (3)	F2—C22—C23—C24	179.4 (3)
C8—C9—C10—C18	−179.0 (3)	C21—C22—C23—C24	−0.6 (5)
C8—C9—C10—C11	−56.7 (3)	C22—C23—C24—C19	−0.1 (4)
C18—C10—C11—O1	176.2 (2)	C20—C19—C24—C23	0.4 (4)
C9—C10—C11—O1	55.9 (3)	N1—C19—C24—C23	176.3 (3)
C18—C10—C11—C12	−64.2 (3)	O3—C18—N1—C19	−0.8 (4)
C9—C10—C11—C12	175.5 (2)	C10—C18—N1—C19	177.0 (2)
O1—C11—C12—C17	−162.4 (2)	C20—C19—N1—C18	−159.1 (2)
C10—C11—C12—C17	77.1 (3)	C24—C19—N1—C18	24.9 (4)
O1—C11—C12—C13	18.9 (4)	C4—C7—O1—C11	−178.9 (2)
C10—C11—C12—C13	−101.7 (3)	C8—C7—O1—C11	59.5 (3)
C17—C12—C13—C14	0.6 (4)	C12—C11—O1—C7	178.0 (2)
C11—C12—C13—C14	179.4 (3)	C10—C11—O1—C7	−58.7 (3)
C12—C13—C14—C15	−0.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.24	2.903 (3)	134
O2—H2···O3ⁱⁱ	0.82	1.98	2.739 (3)	153
C17—H17···F1ⁱⁱⁱ	0.93	2.55	3.178 (3)	125
C24—H24···O3	0.93	2.39	2.929 (4)	117
C2—H2A···Cg2^iv	0.93	2.83	3.515	131
C5—H5···Cg2^v	0.93	2.86	3.575	134
C9—H9B···Cg1ⁱ	0.97	2.78	3.662	152

Symmetry codes: (i) x, y−1, z; (ii) x−1, y+1, z; (iii) x+1, y, z+1; (iv) x−1, y+1, z−1; (v) x, y, z−1.

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