1-[3-(2-Benz­yloxy-6-hy­droxy-4-methyl­phen­yl)-5-[3,5-bis­(tri­fluoro­meth­yl)phen­yl]-4,5-di­hydro-1H-pyrazol-1-yl]propane-1-one

Patel, U.H.; Gandhi, S.A.; Barot, V.M.; Varma, N.V.S.

doi:10.1107/S160053681301180X

1-[3-(2-Benzyloxy-6-hydroxy-4-methylphenyl)-5-[3,5-bis(trifluoromethyl)phenyl]-4,5-dihydro-1H-pyrazol-1-yl]propane-1-one

U. H. Patel, S. A. Gandhi, V. M. Barot and N. V. S. Varma

In the title compound, C₂₈H₂₄F₆N₂O₃, the mean plane of the central pyrazoline ring forms dihedral angles of 2.08 (9) and 69.02 (16)° with the 2-benzyloxy-6-hydroxy-4-methylphenyl and 3,5-bis(trifluoromethyl)phenyl rings, respectively. The dihedral angle between the mean planes of the pyrazoline and 3,5-bis(trifluoromethyl)phenyl rings is 68.97 (9)°. An intramolecular O—H

N hydrogen bond is observed, which forms an S(6) graph-set motif. In the crystal, pairs of weak C—H

F halogen interactions link the molecules into inversion dimers while molecular chains along [100] are formed by C—H

O contacts.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053681301180X/jj2162sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053681301180X/jj2162Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S160053681301180X/jj2162Isup3.cml Supplementary material

CCDC reference: 921608

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.005 Å
R factor = 0.070
wR factor = 0.246
Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C32

Alert level C
PLAT213_ALERT_2_C Atom F33             has ADP max/min Ratio .....        3.1 prola
PLAT213_ALERT_2_C Atom F34             has ADP max/min Ratio .....        3.2 prola
PLAT230_ALERT_2_C Hirshfeld Test Diff for    F35    --  C32     ..        6.3 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C22    --  C23     ..        6.7 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C20
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C36
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0054 Ang
PLAT480_ALERT_4_C Long H...A H-Bond Reported H31    ..  O9      ..       2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21    ..  F37     ..       2.72 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H29    ..  F33     ..       2.64 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.243
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          7
PLAT918_ALERT_3_C Reflection(s) # with I(obs) much smaller I(calc)          1
PLAT926_ALERT_1_C Reported and Calculated   R1 Differ by .........    -0.0011
PLAT939_ALERT_3_C Large Value of Not (SHELXL) Weight Optimized S .      16.54

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ?
PLAT007_ALERT_5_G Note: Number of Unrefined Donor-H Atoms ........          1
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT Unusually Large.       0.15
PLAT128_ALERT_4_G Note: Alternate Setting of Space-group P21/c   .      P21/n
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        273 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        273 K
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C17
PLAT793_ALERT_4_G The Model has Chirality at C5      (Verify) ....          R

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
  15 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Comment top

Pyrazoline derivatives, prominent nitrogen containing heterocyclic compounds, play an important role in medicinal chemistry. These derivatives are found to possess antidepressant, antioxidant, anti- inflammatory (Smith et al., 2001), anticonvulsant, antimicrobial, antiviral, monoamine oxidase (MAO-A and MAO-B) inhibitor, and anticancer activity. Our on-going research is focused on the synthesis and crystal structures of related pyrazoline derivatives of these types of heterocyclic compounds (Patel et al. 2007, Patel et al. 2012). We report here the synthesis and crystal structure of the title compound, C₂₈H₂₄N₂O₃F₆, (I).

In (I), propionaldehyde, 3-benzyloxy-5-methyl-phenol and 1,3-bis-trifluro methyl benzene are bonded to N1, C3 and C5 of the pyrazoline ring, respectively. The dihedral angles between the mean planes of the pyrazoline ring and the 3-benzyloxy-5-methyl-phenol (C10—C15) and 1,3-bis-trifluro methyl benzene rings (C26—C31) are 2.03 (15)° and 69.02 (16)° respectively. An intra-molecular O16—H16···N2 hydrogen bond (Fig.1) forms an S1,1(6) graph set motif configuration (Bernstein et al., 1995). The mean plane of the propionaldehyde group (C6—C8/O9) is inclined by 12.56 (13)° to the meam plane of the pyrazoline ring. Weak C—H···F Halogen intermolecular interactions are observed that form inversion dimers (Fig. 2).

Related literature top

For pharmacalogical and anticancer properties of pyrazoline derivatives, see: Smith et al. (2001). For graph-set motifs, see: Bernstein et al., (1995). For related structures, see: Patel et al. (2007, 2012).

Experimental top

1-[2-benzyloxy-6-hydroxy-4-methyl phenyl]-3-(3, 5-bis (trifluoromethyl) phenyl)prop-2-en-1-one (5 g m, 0.01 mole), hydrazine hydrate (0.70 g m, 0.014 mole) and butanoic acid (20 ml) were heated to 115–120 °C for 4 h. The resulting solution was concentrated and allowed to cool and then poured into ice. The resulting solid was filtered, washed with water, dried and rystallized from methanol as pale yellow needles.

Computing details top

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008 ); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of the title compound,showing the atom labeling scheme with 50% probability displacement ellipsoids. The dashed line represents an O—H···N intramolecular hydrogen bond which forms an S1,1(6) graph set motif.
	Fig. 2. Molecular packing diagram the title compound. Dashed lines indicate weak C—H···F halogen intermolecular interactions which are displayed as inversion dimers. H atoms not involved with these weak intermolecular interactions have been deleted for clarity.

1-[3-(2-Benzyloxy-6-hydroxy-4-methylphenyl)-5-[3,5-bis(trifluoromethyl)phenyl]-4,5-dihydro-1H-pyrazol-1-yl]propane-1-one top

Crystal data top

C₂₈H₂₄F₆N₂O₃	Z = 4
M_r = 550.49	F(000) = 1136
Monoclinic, P2₁/n	D_x = 1.423 Mg m⁻³
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 4.8822 (2) Å	θ = 2.9–27.7°
b = 23.4752 (9) Å	µ = 0.12 mm⁻¹
c = 22.4311 (9) Å	T = 273 K
β = 91.494 (2)°	Needle, white
V = 2569.97 (18) Å³	0.54 × 0.34 × 0.10 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4514 independent reflections
Radiation source: sealed X-ray tube	2491 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
CCD scans	θ_max = 25.0°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −5→5
T_min = 0.951, T_max = 0.988	k = −27→27
19610 measured reflections	l = −26→26

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.246	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1524P)²] where P = (F_o² + 2F_c²)/3
4514 reflections	(Δ/σ)_max < 0.001
352 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₂₈H₂₄F₆N₂O₃	V = 2569.97 (18) Å³
M_r = 550.49	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.8822 (2) Å	µ = 0.12 mm⁻¹
b = 23.4752 (9) Å	T = 273 K
c = 22.4311 (9) Å	0.54 × 0.34 × 0.10 mm
β = 91.494 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4514 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2491 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.988	R_int = 0.075
19610 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.246	H-atom parameters constrained
S = 1.00	Δρ_max = 0.56 e Å⁻³
4514 reflections	Δρ_min = −0.41 e Å⁻³
352 parameters

Special details top

Experimental. IR (cm^-1): 2929 (C—H str. (asym) alkyl), 1458 (C—H def (asym)alkyl), 1387(C—H def (sym) alkyl), 3072 (C—H str.arom.), 1593. (C=Cstr. arom.), 1128 (C—H i.p.def arom.), 847 (C—H o.o.p.def.arom.), 1272 (C—O—C (sym) ether), 1066 (C—O—C (asym) ether), 3380(OH_str. phenol). 1659 (N—CO¬ CH₂CH₃), 1379 (N-COCH₂CH₃ def., pyrazoline), 1588 (C=N str., pyrazoline), 2863 (C—H ring (str.), pyrazoline), 682 (C—H def. of CH₂, pyrazoline), 1197 (C—N str., pyrazoline), 1117 (C—F str.).

1H NMR (CDCl₃) δp.p.m.: 0.96 (trip, 3H, J=7.3 &7.2 Hz), 1.70 (Qur, 2H),2.31(s,3H), 3.36 (dd, 1H, J=15.3 & 3.5 Hz), 3.83 (dd, 1H, J=11.7 & 7.2 Hz), 5.02 (s, 2H), 5.32 (trip, 1H, J= 3.1 & 8.08 Hz), 6.33 (S, 1H), 6.52 (S,1H), 7.16–7.23(m, 8H), 11.24 (s, 1H).

¹³C NMR (CDCl₃) δp.p.m.: 21.98(C-1, CH₃), 70.91 (C-2,CH₂ C6 H5), 159.37(C-3,Pyrazoline), 46.49 (C-4,Pyrazoline), 57.92 (C-5, Pyrazoline), 170.03(C-6,CO CH₂ CH₃), 36.15 (C-7,CO CH₂ CH₃), 13.83 (C-8, CO CH₂ CH₃), 124.44(C-9, CF₃), 124.44 (C-10, CF₃).

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
N1	0.1214 (5)	0.55900 (10)	0.66924 (11)	0.0539 (7)
N2	0.3088 (5)	0.58603 (11)	0.63303 (10)	0.0543 (7)
C3	0.3815 (6)	0.63423 (12)	0.65664 (13)	0.0496 (8)
C4	0.2432 (7)	0.64580 (13)	0.71404 (14)	0.0579 (8)
H4A	0.135	0.6804	0.7115	0.069*
H4B	0.3757	0.6492	0.7468	0.069*
C5	0.0589 (6)	0.59313 (13)	0.72178 (13)	0.0515 (8)
H5	−0.1338	0.6048	0.7195	0.062*
C6	−0.0355 (7)	0.51471 (13)	0.64937 (14)	0.0543 (8)
C7	0.0403 (7)	0.48937 (15)	0.59035 (15)	0.0658 (9)
H7A	0.2281	0.476	0.5933	0.079*
H7B	0.0315	0.519	0.5602	0.079*
C8	−0.1418 (8)	0.44063 (16)	0.57049 (18)	0.0830 (12)
H8A	−0.0827	0.4265	0.5327	0.124*
H8B	−0.3277	0.4537	0.5665	0.124*
H8C	−0.1307	0.4106	0.5995	0.124*
O9	−0.2171 (5)	0.49645 (10)	0.68000 (10)	0.0699 (7)
C10	0.5820 (6)	0.67000 (13)	0.62685 (13)	0.0532 (8)
C11	0.6938 (7)	0.65374 (13)	0.57238 (14)	0.0571 (8)
C12	0.8825 (7)	0.68729 (15)	0.54402 (15)	0.0654 (9)
H12	0.9499	0.6755	0.5076	0.079*
C13	0.9730 (7)	0.73805 (15)	0.56867 (17)	0.0640 (9)
C14	0.8683 (7)	0.75504 (14)	0.62281 (16)	0.0657 (10)
H14	0.9278	0.7889	0.6402	0.079*
C15	0.6766 (7)	0.72210 (14)	0.65103 (15)	0.0605 (9)
O16	0.6203 (5)	0.60455 (10)	0.54461 (10)	0.0770 (8)
H16	0.5078	0.5877	0.5646	0.115*
C17	1.1739 (8)	0.77503 (17)	0.53729 (18)	0.0844 (12)
H17A	1.2123	0.8083	0.5609	0.127*
H17B	1.0976	0.7863	0.4992	0.127*
H17C	1.3404	0.7542	0.5317	0.127*
O18	0.5648 (6)	0.73696 (10)	0.70381 (11)	0.0824 (8)
C19	0.6523 (9)	0.78764 (16)	0.73329 (19)	0.0842 (12)
H19A	0.6385	0.8197	0.7061	0.101*
H19B	0.842	0.7839	0.7467	0.101*
C20	0.4748 (8)	0.79714 (18)	0.78508 (18)	0.0758 (11)
C21	0.3242 (9)	0.8464 (2)	0.7888 (2)	0.0907 (13)
H21	0.3401	0.8733	0.7586	0.109*
C22	0.1532 (11)	0.8579 (3)	0.8341 (3)	0.1063 (15)
H22	0.0572	0.8921	0.8352	0.128*
C23	0.1262 (10)	0.8189 (3)	0.8770 (3)	0.1106 (17)
H23	0.0065	0.8262	0.9077	0.133*
C24	0.2689 (13)	0.7684 (3)	0.8775 (2)	0.1151 (17)
H24	0.2502	0.742	0.908	0.138*
C25	0.4458 (10)	0.7582 (2)	0.8295 (2)	0.0996 (14)
H25	0.5438	0.7242	0.8283	0.12*
C26	0.1172 (6)	0.56381 (12)	0.78105 (13)	0.0485 (8)
C27	0.0104 (7)	0.58758 (14)	0.83107 (14)	0.0611 (9)
H27	−0.1031	0.6192	0.827	0.073*
C28	0.0657 (8)	0.56612 (15)	0.88733 (15)	0.0690 (10)
C29	0.2329 (8)	0.51930 (16)	0.89386 (15)	0.0690 (10)
H29	0.2723	0.5044	0.9315	0.083*
C30	0.3422 (7)	0.49453 (13)	0.84349 (15)	0.0603 (9)
C31	0.2878 (6)	0.51677 (13)	0.78742 (14)	0.0546 (8)
H31	0.365	0.5003	0.7541	0.065*
C32	−0.0504 (12)	0.5936 (2)	0.94053 (18)	0.0946 (14)
C36	0.5136 (10)	0.44223 (17)	0.8505 (2)	0.0807 (12)
F37	0.3614 (6)	0.39586 (11)	0.85326 (17)	0.1375 (12)
F38	0.6768 (7)	0.43269 (13)	0.80719 (16)	0.1480 (14)
F39	0.6615 (8)	0.44101 (13)	0.89967 (16)	0.1546 (14)
F33	−0.1600 (12)	0.56096 (17)	0.97657 (17)	0.219 (3)
F34	0.1149 (8)	0.6254 (3)	0.9680 (2)	0.235 (3)
F35	−0.2551 (10)	0.6284 (2)	0.92844 (15)	0.190 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0651 (17)	0.0526 (16)	0.0442 (15)	−0.0098 (13)	0.0082 (12)	0.0046 (12)
N2	0.0614 (16)	0.0565 (17)	0.0448 (15)	−0.0068 (13)	0.0004 (12)	0.0073 (12)
C3	0.0554 (18)	0.0452 (18)	0.0480 (18)	0.0006 (14)	−0.0038 (14)	0.0049 (14)
C4	0.071 (2)	0.0496 (18)	0.054 (2)	0.0050 (15)	0.0087 (16)	0.0039 (15)
C5	0.0540 (18)	0.0507 (18)	0.0499 (18)	0.0048 (14)	0.0050 (14)	0.0034 (14)
C6	0.0599 (19)	0.0476 (18)	0.055 (2)	−0.0019 (15)	0.0010 (16)	0.0059 (15)
C7	0.074 (2)	0.064 (2)	0.059 (2)	−0.0114 (17)	0.0156 (17)	−0.0002 (16)
C8	0.091 (3)	0.076 (3)	0.083 (3)	−0.017 (2)	0.015 (2)	−0.023 (2)
O9	0.0737 (15)	0.0703 (16)	0.0666 (16)	−0.0161 (12)	0.0206 (12)	0.0007 (12)
C10	0.0591 (19)	0.0504 (18)	0.0498 (19)	−0.0019 (15)	0.0004 (15)	0.0066 (14)
C11	0.067 (2)	0.0492 (18)	0.055 (2)	−0.0003 (16)	−0.0012 (16)	0.0047 (16)
C12	0.073 (2)	0.065 (2)	0.059 (2)	−0.0020 (18)	0.0139 (17)	0.0091 (17)
C13	0.062 (2)	0.059 (2)	0.071 (2)	−0.0037 (17)	0.0012 (17)	0.0181 (18)
C14	0.080 (2)	0.0501 (19)	0.067 (2)	−0.0122 (17)	0.0000 (19)	0.0046 (16)
C15	0.066 (2)	0.059 (2)	0.056 (2)	−0.0091 (16)	−0.0026 (16)	0.0033 (16)
O16	0.0990 (19)	0.0673 (16)	0.0659 (16)	−0.0194 (13)	0.0254 (13)	−0.0101 (12)
C17	0.084 (3)	0.077 (3)	0.093 (3)	−0.017 (2)	0.012 (2)	0.022 (2)
O18	0.108 (2)	0.0729 (17)	0.0669 (17)	−0.0386 (14)	0.0217 (14)	−0.0174 (13)
C19	0.094 (3)	0.067 (2)	0.092 (3)	−0.022 (2)	0.011 (2)	−0.020 (2)
C20	0.082 (3)	0.070 (3)	0.075 (3)	−0.015 (2)	−0.001 (2)	−0.019 (2)
C21	0.095 (3)	0.089 (3)	0.089 (3)	−0.005 (3)	0.003 (2)	−0.026 (2)
C22	0.112 (4)	0.104 (4)	0.103 (4)	−0.005 (3)	0.006 (3)	−0.019 (3)
C23	0.100 (4)	0.123 (5)	0.109 (4)	−0.007 (3)	0.007 (3)	−0.048 (4)
C24	0.147 (5)	0.117 (4)	0.081 (4)	−0.023 (4)	0.004 (3)	−0.006 (3)
C25	0.112 (4)	0.094 (3)	0.093 (4)	−0.004 (3)	0.000 (3)	−0.011 (3)
C26	0.0526 (18)	0.0464 (17)	0.0467 (18)	−0.0022 (13)	0.0056 (14)	0.0002 (13)
C27	0.072 (2)	0.0548 (19)	0.057 (2)	0.0073 (16)	0.0118 (17)	0.0005 (16)
C28	0.095 (3)	0.063 (2)	0.050 (2)	0.003 (2)	0.0152 (18)	−0.0002 (17)
C29	0.090 (3)	0.069 (2)	0.048 (2)	−0.011 (2)	0.0017 (18)	0.0079 (17)
C30	0.071 (2)	0.0503 (19)	0.060 (2)	−0.0009 (16)	0.0009 (17)	0.0112 (16)
C31	0.0609 (19)	0.0533 (19)	0.0497 (19)	0.0025 (15)	0.0049 (15)	0.0012 (15)
C32	0.141 (4)	0.098 (3)	0.046 (2)	0.014 (3)	0.010 (3)	−0.008 (2)
C36	0.099 (3)	0.065 (3)	0.078 (3)	0.011 (2)	−0.009 (3)	0.018 (2)
F37	0.136 (2)	0.0594 (16)	0.216 (3)	0.0071 (15)	−0.006 (2)	0.0306 (18)
F38	0.167 (3)	0.128 (2)	0.152 (3)	0.088 (2)	0.065 (2)	0.053 (2)
F39	0.187 (3)	0.125 (2)	0.148 (3)	0.057 (2)	−0.078 (2)	0.0105 (19)
F33	0.400 (7)	0.148 (3)	0.119 (3)	0.008 (4)	0.160 (4)	−0.001 (2)
F34	0.156 (3)	0.362 (7)	0.188 (4)	−0.068 (4)	0.061 (3)	−0.206 (5)
F35	0.242 (4)	0.229 (4)	0.102 (2)	0.119 (4)	0.033 (3)	−0.038 (2)

Geometric parameters (Å, º) top

N1—C6	1.360 (4)	C17—H17C	0.96
N1—N2	1.392 (3)	O18—C19	1.421 (4)
N1—C5	1.464 (4)	C19—C20	1.484 (5)
N2—C3	1.295 (4)	C19—H19A	0.97
C3—C10	1.464 (4)	C19—H19B	0.97
C3—C4	1.495 (4)	C20—C25	1.362 (6)
C4—C5	1.541 (4)	C20—C21	1.374 (6)
C4—H4A	0.97	C21—C22	1.359 (6)
C4—H4B	0.97	C21—H21	0.93
C5—C26	1.517 (4)	C22—C23	1.338 (7)
C5—H5	0.98	C22—H22	0.93
C6—O9	1.214 (4)	C23—C24	1.376 (8)
C6—C7	1.506 (5)	C23—H23	0.93
C7—C8	1.509 (5)	C24—C25	1.418 (7)
C7—H7A	0.97	C24—H24	0.93
C7—H7B	0.97	C25—H25	0.93
C8—H8A	0.96	C26—C27	1.368 (4)
C8—H8B	0.96	C26—C31	1.388 (4)
C8—H8C	0.96	C27—C28	1.379 (5)
C10—C11	1.404 (4)	C27—H27	0.93
C10—C15	1.411 (4)	C28—C29	1.374 (5)
C11—O16	1.356 (4)	C28—C32	1.482 (5)
C11—C12	1.380 (5)	C29—C30	1.390 (5)
C12—C13	1.381 (5)	C29—H29	0.93
C12—H12	0.93	C30—C31	1.381 (4)
C13—C14	1.389 (5)	C30—C36	1.492 (5)
C13—C17	1.499 (5)	C31—H31	0.93
C14—C15	1.380 (5)	C32—F33	1.244 (6)
C14—H14	0.93	C32—F34	1.251 (6)
C15—O18	1.362 (4)	C32—F35	1.315 (6)
O16—H16	0.82	C36—F38	1.291 (5)
C17—H17A	0.96	C36—F39	1.303 (5)
C17—H17B	0.96	C36—F37	1.320 (5)

C6—N1—N2	122.0 (3)	H17A—C17—H17C	109.5
C6—N1—C5	123.7 (3)	H17B—C17—H17C	109.5
N2—N1—C5	112.0 (2)	C15—O18—C19	119.7 (3)
C3—N2—N1	109.7 (2)	O18—C19—C20	108.4 (3)
N2—C3—C10	119.6 (3)	O18—C19—H19A	110
N2—C3—C4	112.7 (3)	C20—C19—H19A	110
C10—C3—C4	127.7 (3)	O18—C19—H19B	110
C3—C4—C5	103.3 (2)	C20—C19—H19B	110
C3—C4—H4A	111.1	H19A—C19—H19B	108.4
C5—C4—H4A	111.1	C25—C20—C21	117.1 (4)
C3—C4—H4B	111.1	C25—C20—C19	123.0 (4)
C5—C4—H4B	111.1	C21—C20—C19	119.9 (4)
H4A—C4—H4B	109.1	C22—C21—C20	123.5 (5)
N1—C5—C26	114.8 (2)	C22—C21—H21	118.2
N1—C5—C4	102.3 (2)	C20—C21—H21	118.2
C26—C5—C4	111.5 (2)	C23—C22—C21	118.5 (5)
N1—C5—H5	109.3	C23—C22—H22	120.8
C26—C5—H5	109.3	C21—C22—H22	120.8
C4—C5—H5	109.3	C22—C23—C24	122.4 (5)
O9—C6—N1	119.9 (3)	C22—C23—H23	118.8
O9—C6—C7	123.9 (3)	C24—C23—H23	118.8
N1—C6—C7	116.2 (3)	C23—C24—C25	117.3 (5)
C6—C7—C8	113.8 (3)	C23—C24—H24	121.4
C6—C7—H7A	108.8	C25—C24—H24	121.4
C8—C7—H7A	108.8	C20—C25—C24	121.2 (5)
C6—C7—H7B	108.8	C20—C25—H25	119.4
C8—C7—H7B	108.8	C24—C25—H25	119.4
H7A—C7—H7B	107.7	C27—C26—C31	118.7 (3)
C7—C8—H8A	109.5	C27—C26—C5	117.8 (3)
C7—C8—H8B	109.5	C31—C26—C5	123.3 (3)
H8A—C8—H8B	109.5	C26—C27—C28	122.1 (3)
C7—C8—H8C	109.5	C26—C27—H27	118.9
H8A—C8—H8C	109.5	C28—C27—H27	118.9
H8B—C8—H8C	109.5	C29—C28—C27	119.4 (3)
C11—C10—C15	116.1 (3)	C29—C28—C32	120.0 (3)
C11—C10—C3	121.4 (3)	C27—C28—C32	120.6 (4)
C15—C10—C3	122.5 (3)	C28—C29—C30	119.2 (3)
O16—C11—C12	116.5 (3)	C28—C29—H29	120.4
O16—C11—C10	121.8 (3)	C30—C29—H29	120.4
C12—C11—C10	121.7 (3)	C31—C30—C29	120.9 (3)
C11—C12—C13	121.2 (3)	C31—C30—C36	120.1 (3)
C11—C12—H12	119.4	C29—C30—C36	119.0 (3)
C13—C12—H12	119.4	C30—C31—C26	119.7 (3)
C12—C13—C14	118.5 (3)	C30—C31—H31	120.2
C12—C13—C17	121.2 (4)	C26—C31—H31	120.2
C14—C13—C17	120.3 (3)	F33—C32—F34	109.3 (5)
C15—C14—C13	120.6 (3)	F33—C32—F35	100.3 (5)
C15—C14—H14	119.7	F34—C32—F35	101.9 (5)
C13—C14—H14	119.7	F33—C32—C28	115.8 (4)
O18—C15—C14	123.2 (3)	F34—C32—C28	113.7 (5)
O18—C15—C10	114.9 (3)	F35—C32—C28	114.2 (4)
C14—C15—C10	121.9 (3)	F38—C36—F39	107.1 (4)
C11—O16—H16	109.5	F38—C36—F37	104.6 (4)
C13—C17—H17A	109.5	F39—C36—F37	104.0 (3)
C13—C17—H17B	109.5	F38—C36—C30	114.8 (3)
H17A—C17—H17B	109.5	F39—C36—C30	113.8 (4)
C13—C17—H17C	109.5	F37—C36—C30	111.6 (4)

N1—C6—C7—C8	−179.7 (3)	C15—O18—C19—C20	173.2 (3)
C14—C15—O18—C19	−2.2 (5)	O18—C19—C20—C21	−120.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O16—H16···N2	0.82	1.84	2.568 (3)	147
C31—H31···O9ⁱ	0.93	2.67	3.490 (4)	148
C21—H21···F37ⁱⁱ	0.93	2.72	3.488 (6)	140
C29—H29···F33ⁱⁱⁱ	0.93	2.64	3.490 (5)	152

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

Experimental details

Crystal data
Chemical formula	C₂₈H₂₄F₆N₂O₃
M_r	550.49
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	4.8822 (2), 23.4752 (9), 22.4311 (9)
β (°)	91.494 (2)
V (Å³)	2569.97 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.54 × 0.34 × 0.10

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.951, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	19610, 4514, 2491
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.246, 1.00
No. of reflections	4514
No. of parameters	352
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.41

Computer programs: APEX2 (Bruker, 2008 ), SAINT (Bruker, 2008 ), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), publCIF (Westrip, 2010).