Crystal structure of (4-hy-droxy-piperidin-1-yl)[4-(tri-fluoro-meth-yl)phen-yl]methanone.

The title compound, C13H14NO2F3, crystallises with two mol-ecules, A and B, in the asymmetric unit, with similar conformations. The dihedral angles between the piperidine and phenyl rings are 83.76 (2) and 75.23 (2)° in mol-ecules A and B, respectively. The bond-angle sums around the N atoms [359.1 and 359.7° for mol-ecules A and B, respectively] indicate sp (2) hybridization for these atoms. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into separate [100] chains of A and B mol-ecules. The chains are cross-linked by C-H⋯O inter-actions, generating alternating (001) sheets of A and B mol-ecules.

Related literature

For the synthesis, see: Revathi et al. (2015 ▸). For the biological activities of piperdine derivatives, see: Ramalingan et al. (2004 ▸); Ramachandran et al. (2011 ▸); Lee et al. (2001 ▸); Parthiban et al. (2005 ▸). For a related structure, see: Prathebha et al. (2015 ▸).

Experimental

Crystal data

C13H14F3NO2

M = 273.25

Orthorhombic,

a = 16.1328 (14) Å

b = 6.8283 (6) Å

c = 23.017 (2) Å

V = 2535.5 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.957, T max = 0.969

26641 measured reflections

4823 independent reflections

2950 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.190

S = 1.07

4823 reflections

343 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S205698901501765X/hb7494sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901501765X/hb7494Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901501765X/hb7494Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S205698901501765X/hb7494fig1.tif

The mol­ecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S205698901501765X/hb7494fig2.tif

The packing of the mol­ecules in the crystal structure. The dashed lines indicate the hydrogen bonds.

CCDC reference: 1425996

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H14F3NO2	F(000) = 1136
Mr = 273.25	Dx = 1.432 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	θ = 1.8–25.7°
a = 16.1328 (14) Å	µ = 0.13 mm−1
b = 6.8283 (6) Å	T = 293 K
c = 23.017 (2) Å	Block, colorless
V = 2535.5 (4) Å3	0.35 × 0.30 × 0.25 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	4823 independent reflections
Radiation source: fine-focus sealed tube	2950 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
ω and φ scans	θmax = 25.7°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −19→19
Tmin = 0.957, Tmax = 0.969	k = −8→7
26641 measured reflections	l = −28→28

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0905P)2 + 1.4379P] where P = (Fo2 + 2Fc2)/3
4823 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.27 e Å−3
1 restraint	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
C10	1.0836 (3)	0.3171 (9)	0.0067 (2)	0.0622 (13)
H1	1.1181	0.4072	0.0294	0.075*
C9	1.0108 (3)	0.4279 (8)	−0.0181 (3)	0.0649 (14)
H2A	0.9844	0.5021	0.0127	0.078*
H2B	1.0308	0.5203	−0.0469	0.078*
C8	0.9480 (3)	0.2956 (8)	−0.0457 (2)	0.0593 (13)
H3A	0.9008	0.3719	−0.0587	0.071*
H3B	0.9722	0.2316	−0.0793	0.071*
C12	0.9885 (3)	0.0264 (7)	0.0177 (2)	0.0523 (11)
H4A	1.0121	−0.0478	−0.0142	0.063*
H4B	0.9673	−0.0657	0.0462	0.063*
C11	1.0551 (3)	0.1530 (8)	0.0453 (2)	0.0580 (13)
H5A	1.0338	0.2078	0.0812	0.070*
H5B	1.1023	0.0714	0.0550	0.070*
C7	0.8449 (3)	0.1543 (6)	0.0173 (2)	0.0448 (10)
C1	0.8174 (3)	0.0056 (7)	0.06151 (19)	0.0450 (11)
C2	0.8144 (3)	−0.1940 (7)	0.0494 (2)	0.0495 (11)
H8	0.8348	−0.2411	0.0142	0.059*
C3	0.7815 (3)	−0.3204 (7)	0.0891 (2)	0.0485 (11)
H9	0.7780	−0.4530	0.0802	0.058*
C4	0.7532 (3)	−0.2536 (7)	0.1427 (2)	0.0502 (12)
C5	0.7564 (3)	−0.0557 (7)	0.1542 (2)	0.0606 (13)
H11	0.7372	−0.0091	0.1897	0.073*
C6	0.7873 (3)	0.0733 (7)	0.1142 (2)	0.0570 (13)
H12	0.7881	0.2066	0.1224	0.068*
C13	0.7202 (3)	−0.3921 (7)	0.1854 (2)	0.0589 (12)
C23	0.6591 (3)	0.3211 (8)	0.3540 (2)	0.0612 (13)
H14	0.6260	0.4154	0.3318	0.073*
C22	0.6845 (3)	0.1537 (8)	0.3146 (2)	0.0602 (13)
H15A	0.7085	0.2067	0.2794	0.072*
H15B	0.6355	0.0795	0.3039	0.072*
C21	0.7469 (3)	0.0165 (7)	0.3433 (2)	0.0577 (13)
H16A	0.7206	−0.0528	0.3752	0.069*
H16B	0.7661	−0.0795	0.3153	0.069*
C25	0.7932 (3)	0.2784 (9)	0.4071 (3)	0.0730 (17)
H17A	0.8421	0.3465	0.4209	0.088*
H17B	0.7660	0.2179	0.4401	0.088*
C24	0.7348 (3)	0.4220 (8)	0.3779 (3)	0.0737 (16)
H18A	0.7179	0.5205	0.4058	0.088*
H18B	0.7638	0.4878	0.3465	0.088*
C20	0.8949 (3)	0.1163 (8)	0.3466 (2)	0.0552 (12)
C17	0.9167 (3)	−0.0342 (7)	0.3019 (2)	0.0492 (11)
C18	0.9246 (3)	−0.2314 (8)	0.3153 (2)	0.0548 (13)
H21	0.9102	−0.2764	0.3521	0.066*
C19	0.9537 (3)	−0.3609 (7)	0.2742 (2)	0.0574 (12)
H22	0.9605	−0.4926	0.2833	0.069*
C14	0.9728 (3)	−0.2926 (7)	0.2193 (2)	0.0528 (12)
C15	0.9639 (3)	−0.1019 (8)	0.2054 (2)	0.0688 (15)
H24	0.9766	−0.0586	0.1681	0.083*
C16	0.9363 (4)	0.0281 (8)	0.2465 (2)	0.0688 (15)
H25	0.9306	0.1597	0.2369	0.083*
C26	1.0021 (3)	−0.4353 (8)	0.1751 (2)	0.0635 (14)
N1	0.9207 (2)	0.1482 (6)	−0.00380 (16)	0.0494 (10)
N2	0.8169 (2)	0.1289 (7)	0.36505 (17)	0.0552 (11)
O2	1.13070 (19)	0.2418 (6)	−0.04018 (18)	0.0719 (11)
H1A	1.1781	0.2194	−0.0292	0.108*
O1	0.79406 (18)	0.2827 (5)	0.00270 (16)	0.0574 (9)
O4	0.6124 (2)	0.2524 (6)	0.40139 (18)	0.0712 (10)
H3	0.5629	0.2553	0.3932	0.107*
O3	0.9492 (2)	0.2285 (7)	0.36352 (19)	0.0842 (14)
F1	0.6669 (2)	−0.5173 (6)	0.16460 (16)	0.1029 (13)
F2	0.6821 (3)	−0.3078 (6)	0.22995 (16)	0.1089 (14)
F3	0.7790 (2)	−0.5065 (6)	0.20861 (18)	0.1101 (14)
F4	1.0566 (2)	−0.5623 (6)	0.19448 (16)	0.1038 (13)
F5	1.0359 (3)	−0.3537 (6)	0.12899 (16)	0.1165 (15)
F6	0.9416 (2)	−0.5492 (6)	0.15396 (18)	0.1028 (12)

	U11	U22	U33	U12	U13	U23
C10	0.044 (3)	0.079 (3)	0.063 (3)	−0.006 (3)	0.005 (3)	0.000 (3)
C9	0.047 (3)	0.063 (3)	0.085 (4)	−0.002 (2)	0.001 (3)	0.020 (3)
C8	0.041 (3)	0.080 (3)	0.057 (3)	0.003 (2)	0.001 (2)	0.028 (3)
C12	0.046 (2)	0.054 (3)	0.057 (3)	0.014 (2)	0.003 (2)	0.010 (2)
C11	0.044 (3)	0.080 (3)	0.050 (3)	0.010 (2)	−0.002 (2)	0.011 (3)
C7	0.037 (2)	0.048 (2)	0.049 (3)	−0.003 (2)	−0.003 (2)	0.000 (2)
C1	0.039 (2)	0.049 (3)	0.047 (3)	−0.005 (2)	0.002 (2)	−0.002 (2)
C2	0.052 (3)	0.054 (3)	0.042 (3)	−0.001 (2)	0.004 (2)	−0.001 (2)
C3	0.054 (3)	0.043 (2)	0.048 (3)	−0.005 (2)	0.003 (2)	−0.007 (2)
C4	0.042 (3)	0.064 (3)	0.044 (3)	−0.008 (2)	0.001 (2)	0.001 (2)
C5	0.071 (3)	0.057 (3)	0.055 (3)	−0.012 (3)	0.015 (3)	−0.008 (3)
C6	0.069 (3)	0.047 (3)	0.054 (3)	−0.003 (2)	0.013 (2)	−0.008 (2)
C13	0.061 (3)	0.063 (3)	0.052 (3)	−0.008 (3)	0.002 (2)	0.001 (3)
C23	0.048 (3)	0.077 (3)	0.058 (3)	−0.003 (3)	0.001 (3)	0.001 (3)
C22	0.049 (3)	0.075 (3)	0.056 (3)	−0.008 (2)	−0.001 (2)	−0.009 (3)
C21	0.041 (3)	0.065 (3)	0.067 (3)	−0.014 (2)	0.002 (2)	−0.014 (3)
C25	0.046 (3)	0.102 (4)	0.071 (4)	0.003 (3)	−0.005 (3)	−0.044 (4)
C24	0.062 (3)	0.067 (3)	0.093 (4)	−0.009 (3)	0.019 (3)	−0.027 (3)
C20	0.038 (2)	0.072 (3)	0.056 (3)	0.000 (2)	−0.004 (2)	−0.016 (3)
C17	0.034 (2)	0.061 (3)	0.052 (3)	0.000 (2)	0.002 (2)	−0.008 (2)
C18	0.050 (3)	0.068 (3)	0.046 (3)	−0.013 (2)	0.004 (2)	−0.006 (2)
C19	0.065 (3)	0.054 (3)	0.053 (3)	−0.003 (2)	−0.002 (2)	−0.002 (3)
C14	0.045 (2)	0.066 (3)	0.047 (3)	0.008 (2)	0.006 (2)	−0.005 (2)
C15	0.080 (4)	0.078 (4)	0.048 (3)	0.008 (3)	0.017 (3)	0.001 (3)
C16	0.089 (4)	0.055 (3)	0.062 (3)	0.008 (3)	0.013 (3)	0.002 (3)
C26	0.057 (3)	0.071 (3)	0.063 (3)	0.010 (3)	0.003 (3)	−0.012 (3)
N1	0.040 (2)	0.058 (2)	0.050 (2)	0.0036 (18)	0.0025 (17)	0.0156 (19)
N2	0.034 (2)	0.076 (3)	0.056 (3)	−0.0026 (18)	0.0028 (17)	−0.026 (2)
O2	0.0471 (19)	0.108 (3)	0.061 (2)	0.003 (2)	0.0028 (17)	0.005 (2)
O1	0.0420 (18)	0.059 (2)	0.071 (2)	0.0078 (15)	0.0006 (16)	0.0096 (17)
O4	0.0499 (19)	0.096 (3)	0.067 (3)	−0.0026 (19)	0.0084 (18)	0.006 (2)
O3	0.0412 (18)	0.107 (3)	0.105 (3)	−0.013 (2)	−0.0003 (19)	−0.053 (3)
F1	0.110 (3)	0.116 (3)	0.082 (2)	−0.065 (2)	−0.004 (2)	0.014 (2)
F2	0.155 (4)	0.095 (2)	0.076 (2)	−0.016 (2)	0.057 (2)	0.002 (2)
F3	0.087 (2)	0.127 (3)	0.116 (3)	0.004 (2)	0.009 (2)	0.069 (3)
F4	0.097 (3)	0.119 (3)	0.096 (3)	0.053 (2)	−0.008 (2)	−0.029 (2)
F5	0.168 (4)	0.109 (3)	0.072 (2)	0.004 (3)	0.060 (3)	−0.012 (2)
F6	0.079 (2)	0.119 (3)	0.110 (3)	0.003 (2)	0.001 (2)	−0.059 (3)

C10—O2	1.417 (7)	C23—C24	1.508 (7)
C10—C11	1.501 (8)	C23—C22	1.514 (7)
C10—C9	1.509 (7)	C23—H14	0.9800
C10—H1	0.9800	C22—C21	1.526 (7)
C9—C8	1.499 (8)	C22—H15A	0.9700
C9—H2A	0.9700	C22—H15B	0.9700
C9—H2B	0.9700	C21—N2	1.455 (6)
C8—N1	1.462 (6)	C21—H16A	0.9700
C8—H3A	0.9700	C21—H16B	0.9700
C8—H3B	0.9700	C25—N2	1.457 (6)
C12—N1	1.460 (6)	C25—C24	1.516 (9)
C12—C11	1.519 (7)	C25—H17A	0.9700
C12—H4A	0.9700	C25—H17B	0.9700
C12—H4B	0.9700	C24—H18A	0.9700
C11—H5A	0.9700	C24—H18B	0.9700
C11—H5B	0.9700	C20—O3	1.228 (6)
C7—O1	1.247 (5)	C20—N2	1.330 (6)
C7—N1	1.316 (6)	C20—C17	1.496 (7)
C7—C1	1.505 (6)	C17—C16	1.381 (8)
C1—C6	1.386 (6)	C17—C18	1.387 (7)
C1—C2	1.392 (7)	C18—C19	1.378 (7)
C2—C3	1.364 (7)	C18—H21	0.9300
C2—H8	0.9300	C19—C14	1.380 (7)
C3—C4	1.394 (7)	C19—H22	0.9300
C3—H9	0.9300	C14—C15	1.349 (7)
C4—C5	1.378 (7)	C14—C26	1.486 (7)
C4—C13	1.464 (7)	C15—C16	1.372 (7)
C5—C6	1.368 (7)	C15—H24	0.9300
C5—H11	0.9300	C16—H25	0.9300
C6—H12	0.9300	C26—F4	1.313 (6)
C13—F1	1.304 (6)	C26—F5	1.317 (7)
C13—F2	1.327 (6)	C26—F6	1.339 (6)
C13—F3	1.339 (6)	O2—H1A	0.8200
C23—O4	1.407 (6)	O4—H3	0.8200
O2—C10—C11	110.1 (5)	C24—C23—H14	109.4
O2—C10—C9	108.1 (5)	C22—C23—H14	109.4
C11—C10—C9	111.1 (4)	C23—C22—C21	112.6 (4)
O2—C10—H1	109.2	C23—C22—H15A	109.1
C11—C10—H1	109.2	C21—C22—H15A	109.1
C9—C10—H1	109.2	C23—C22—H15B	109.1
C8—C9—C10	112.6 (5)	C21—C22—H15B	109.1
C8—C9—H2A	109.1	H15A—C22—H15B	107.8
C10—C9—H2A	109.1	N2—C21—C22	109.7 (4)
C8—C9—H2B	109.1	N2—C21—H16A	109.7
C10—C9—H2B	109.1	C22—C21—H16A	109.7
H2A—C9—H2B	107.8	N2—C21—H16B	109.7
N1—C8—C9	109.8 (4)	C22—C21—H16B	109.7
N1—C8—H3A	109.7	H16A—C21—H16B	108.2
C9—C8—H3A	109.7	N2—C25—C24	108.8 (5)
N1—C8—H3B	109.7	N2—C25—H17A	109.9
C9—C8—H3B	109.7	C24—C25—H17A	109.9
H3A—C8—H3B	108.2	N2—C25—H17B	109.9
N1—C12—C11	110.3 (4)	C24—C25—H17B	109.9
N1—C12—H4A	109.6	H17A—C25—H17B	108.3
C11—C12—H4A	109.6	C23—C24—C25	111.7 (5)
N1—C12—H4B	109.6	C23—C24—H18A	109.3
C11—C12—H4B	109.6	C25—C24—H18A	109.3
H4A—C12—H4B	108.1	C23—C24—H18B	109.3
C10—C11—C12	113.2 (4)	C25—C24—H18B	109.3
C10—C11—H5A	108.9	H18A—C24—H18B	107.9
C12—C11—H5A	108.9	O3—C20—N2	122.3 (4)
C10—C11—H5B	108.9	O3—C20—C17	118.5 (4)
C12—C11—H5B	108.9	N2—C20—C17	119.1 (4)
H5A—C11—H5B	107.7	C16—C17—C18	118.8 (5)
O1—C7—N1	122.3 (4)	C16—C17—C20	118.5 (5)
O1—C7—C1	117.6 (4)	C18—C17—C20	122.4 (5)
N1—C7—C1	120.1 (4)	C19—C18—C17	120.2 (5)
C6—C1—C2	119.3 (4)	C19—C18—H21	119.9
C6—C1—C7	118.1 (4)	C17—C18—H21	119.9
C2—C1—C7	122.4 (4)	C18—C19—C14	119.2 (5)
C3—C2—C1	119.9 (5)	C18—C19—H22	120.4
C3—C2—H8	120.0	C14—C19—H22	120.4
C1—C2—H8	120.0	C15—C14—C19	121.3 (5)
C2—C3—C4	120.9 (4)	C15—C14—C26	120.3 (5)
C2—C3—H9	119.5	C19—C14—C26	118.4 (5)
C4—C3—H9	119.5	C14—C15—C16	119.7 (5)
C5—C4—C3	118.6 (5)	C14—C15—H24	120.2
C5—C4—C13	121.2 (5)	C16—C15—H24	120.2
C3—C4—C13	120.2 (4)	C15—C16—C17	120.8 (5)
C6—C5—C4	121.1 (5)	C15—C16—H25	119.6
C6—C5—H11	119.5	C17—C16—H25	119.6
C4—C5—H11	119.5	F4—C26—F5	106.0 (5)
C5—C6—C1	120.1 (5)	F4—C26—F6	103.2 (4)
C5—C6—H12	119.9	F5—C26—F6	104.7 (5)
C1—C6—H12	119.9	F4—C26—C14	114.5 (5)
F1—C13—F2	105.2 (5)	F5—C26—C14	114.0 (5)
F1—C13—F3	103.4 (4)	F6—C26—C14	113.4 (4)
F2—C13—F3	105.8 (4)	C7—N1—C12	126.1 (4)
F1—C13—C4	114.7 (4)	C7—N1—C8	120.0 (4)
F2—C13—C4	114.0 (4)	C12—N1—C8	113.0 (4)
F3—C13—C4	112.8 (4)	C20—N2—C21	126.2 (4)
O4—C23—C24	107.6 (4)	C20—N2—C25	120.3 (4)
O4—C23—C22	110.9 (5)	C21—N2—C25	113.2 (4)
C24—C23—C22	110.1 (4)	C10—O2—H1A	109.5
O4—C23—H14	109.4	C23—O4—H3	109.5
O2—C10—C9—C8	70.2 (6)	O3—C20—C17—C18	106.8 (6)
C11—C10—C9—C8	−50.8 (7)	N2—C20—C17—C18	−75.7 (6)
C10—C9—C8—N1	55.5 (6)	C16—C17—C18—C19	1.8 (7)
O2—C10—C11—C12	−71.0 (5)	C20—C17—C18—C19	−172.8 (4)
C9—C10—C11—C12	48.7 (6)	C17—C18—C19—C14	−1.7 (7)
N1—C12—C11—C10	−51.7 (6)	C18—C19—C14—C15	0.5 (8)
O1—C7—C1—C6	−55.1 (6)	C18—C19—C14—C26	−178.5 (4)
N1—C7—C1—C6	123.6 (5)	C19—C14—C15—C16	0.6 (8)
O1—C7—C1—C2	119.0 (5)	C26—C14—C15—C16	179.5 (5)
N1—C7—C1—C2	−62.2 (6)	C14—C15—C16—C17	−0.5 (9)
C6—C1—C2—C3	0.4 (7)	C18—C17—C16—C15	−0.8 (8)
C7—C1—C2—C3	−173.7 (4)	C20—C17—C16—C15	174.1 (5)
C1—C2—C3—C4	−2.2 (7)	C15—C14—C26—F4	137.5 (5)
C2—C3—C4—C5	2.3 (7)	C19—C14—C26—F4	−43.5 (7)
C2—C3—C4—C13	−178.3 (4)	C15—C14—C26—F5	15.3 (8)
C3—C4—C5—C6	−0.6 (8)	C19—C14—C26—F5	−165.7 (5)
C13—C4—C5—C6	180.0 (5)	C15—C14—C26—F6	−104.4 (6)
C4—C5—C6—C1	−1.1 (8)	C19—C14—C26—F6	74.6 (6)
C2—C1—C6—C5	1.2 (7)	O1—C7—N1—C12	168.7 (4)
C7—C1—C6—C5	175.6 (4)	C1—C7—N1—C12	−10.0 (7)
C5—C4—C13—F1	132.1 (5)	O1—C7—N1—C8	0.2 (7)
C3—C4—C13—F1	−47.2 (7)	C1—C7—N1—C8	−178.5 (4)
C5—C4—C13—F2	10.8 (7)	C11—C12—N1—C7	−111.8 (5)
C3—C4—C13—F2	−168.6 (5)	C11—C12—N1—C8	57.4 (5)
C5—C4—C13—F3	−109.9 (6)	C9—C8—N1—C7	110.3 (5)
C3—C4—C13—F3	70.7 (6)	C9—C8—N1—C12	−59.5 (6)
O4—C23—C22—C21	−67.9 (5)	O3—C20—N2—C21	173.3 (5)
C24—C23—C22—C21	51.1 (6)	C17—C20—N2—C21	−4.0 (8)
C23—C22—C21—N2	−53.0 (5)	O3—C20—N2—C25	−0.5 (9)
O4—C23—C24—C25	67.5 (6)	C17—C20—N2—C25	−177.9 (5)
C22—C23—C24—C25	−53.5 (6)	C22—C21—N2—C20	−115.5 (6)
N2—C25—C24—C23	57.8 (6)	C22—C21—N2—C25	58.7 (6)
O3—C20—C17—C16	−67.8 (7)	C24—C25—N2—C20	113.5 (5)
N2—C20—C17—C16	109.6 (6)	C24—C25—N2—C21	−61.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1A···O1i	0.82	2.01	2.819 (4)	169
O4—H3···O3ii	0.82	1.96	2.775 (5)	173
C3—H9···O1iii	0.93	2.55	3.367 (6)	147
C18—H21···O2iv	0.93	2.58	3.445 (7)	156

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O2H1AO1i	0.82	2.01	2.819(4)	169
O4H3O3ii	0.82	1.96	2.775(5)	173
C3H9O1iii	0.93	2.55	3.367(6)	147
C18H21O2iv	0.93	2.58	3.445(7)	156

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .