1,5-Dimethyl-2-phenyl-4-(4,4,4-trifluoro-3-oxo-1-phenyl­but-1-enylamino)-1H-pyrazol-3(2H)-one

In the title compound, C₂₁H₁₈F₃N₃O₂, the pyrazole ring is approximately planar and forms dihedral angles of 47.61 (9) and 69.39 (8)° with the two phenyl rings. An intra­molecular N—H...O hydrogen bond stabilizes the mol­ecular conformation. Inter­molecular N—H...O hydrogen bonds link the mol­ecules into centrosymmetric dimers. The trifluoromethyl group is disordered over two positions in a ratio of ∼0.8:0.2.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.044
• wR factor = 0.131
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found





Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C21

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
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       C21'
PLAT301_ALERT_3_C Main Residue  Disorder .........................      12.00 Perc.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         71

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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

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S1. Comment

In order to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Belloni et al., 2005; Tynan et al., 2005; Parashar et al., 1988), the synthesis of new and designed crystal structures has become a major strand of modern chemistry. Metal complexes based on Schiff bases have attracted much attention because they can be utilized as model compounds of the active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al.,2001). As part of an investigation of the coordination properties of Shiff bases functioning as ligands, we report the synthesis and crystal structure of the title compound, (I).

In the molecular structure of the compound (I) (Fig. 1), the geometric parameters are normal. The pyrazole ring (C1—C3/N1/N2) is approximately planar, with a maximum deviation from the mean plane of 0.046 (1) Å for atom N1. The least-squares plane through the pyrazole ring forms dihedral angles of 47.61 (9) and 69.39 (8)°, respectively, with the C5—C10 and C13—C18 phenyl rings. The two phenyl rings are inclined at an angle of 80.70 (8)°.

An intramolecular N—H···O hydrogen bond stabilizes the molecular conformation. In the crystal structure, intermolecular N—H···O hydrogen bonds link the molecules into centrosymmetric dimers as illustrated in Fig. 2.

Related literature

For general background, see: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).

S2. Experimental

An anhydrous ethanol solution (50 ml) of 4,4,4-trifluoro-1-phenyl- butane-1,3-dione (2.16 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of 4-amino-1,5-dimethyl-2-phenyl-pyrazolidin-3-one (2.03 g, 10 mmol), and the mixture was stirred at 350 K for 6 h under N₂, whereupon a yellow precipitate appeared. The product was isolated, recrystallized from anhydrous ethanol and then dried in vacuo to give pure compound (I) in 79% yield. Yellows single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an anhydrous ethanol solution.

S3. Refinement

The trifluoromethyl group was treated as disordered over two orientations with refined occupancies of 0.802 (8) and 0.198 (8). All C—F bond lengths were restrained to 1.35 (1) Å, and the C20—C21 and C20—C21' distances were restrained to 1.52 (1) Å. The F···F distances were restrained to be equal, within a standard deviation of 0.01 Å. The displacement parameters of the disordered atoms were restrained to approximately isotropic behaviour. The N-bound H atom was located in a difference Fourier map and its positional parameters were refined, with U_iso(H) = 1.2U_eq(N). C-bound H atoms were included in calculated positions, with C—H = 0.93 (aromatic) or 0.96 Å (methyl), and refined using a riding model, with U_iso(H) = 1.2U_eq(C) for aromatic H or 1.5U_eq(C) for methyl H atoms.

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of (I), viwed down the b axis. Hydrogen bonds are indicated by dashed lines.

1,5-Dimethyl-2-phenyl-4-(4,4,4-trifluoro-3-oxo-1-phenylbut-1-enylamino)- 1H-pyrazol-3(2H)-one

Crystal data

C21H18F3N3O2	F(000) = 832
Mr = 401.38	Dx = 1.321 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2616 reflections
a = 13.452 (4) Å	θ = 2.3–23.6°
b = 6.3930 (18) Å	µ = 0.11 mm^−1
c = 23.466 (7) Å	T = 294 K
β = 90.571 (5)°	Block, yellow
V = 2017.9 (10) Å^3	0.22 × 0.20 × 0.14 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3554 independent reflections
Radiation source: fine-focus sealed tube	2134 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→13
Tmin = 0.977, Tmax = 0.985	k = −7→7
9666 measured reflections	l = −27→27

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.059P)^2 + 0.2821P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3554 reflections	Δρmax = 0.19 e Å^−3
306 parameters	Δρmin = −0.16 e Å^−3
71 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0114 (15)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C21	0.0597 (4)	−0.1194 (12)	0.6599 (2)	0.075 (3)	0.802 (8)
F1	0.0622 (5)	−0.3257 (6)	0.65744 (17)	0.1370 (19)	0.802 (8)
F2	−0.0333 (2)	−0.0639 (9)	0.67356 (15)	0.1254 (19)	0.802 (8)
F3	0.1167 (3)	−0.0624 (9)	0.70432 (16)	0.113 (2)	0.802 (8)
C21'	0.0663 (11)	−0.082 (2)	0.6640 (4)	0.077 (14)	0.198 (8)
F1'	0.0020 (11)	−0.242 (3)	0.6645 (5)	0.086 (5)	0.198 (8)
F2'	0.0267 (16)	0.067 (2)	0.6971 (6)	0.132 (7)	0.198 (8)
F3'	0.1472 (9)	−0.151 (3)	0.6925 (8)	0.104 (6)	0.198 (8)
N1	0.28293 (14)	0.2485 (3)	0.36876 (8)	0.0415 (5)
N2	0.21147 (14)	0.4106 (3)	0.36303 (8)	0.0430 (5)
N3	0.15442 (15)	0.2092 (3)	0.50379 (8)	0.0426 (5)
O1	0.31148 (13)	−0.0196 (3)	0.43548 (7)	0.0588 (5)
O2	0.03316 (13)	−0.0629 (3)	0.56238 (8)	0.0630 (6)
C1	0.26854 (17)	0.1439 (4)	0.42103 (10)	0.0397 (6)
C2	0.19382 (16)	0.2675 (4)	0.44969 (9)	0.0376 (6)
C3	0.16334 (17)	0.4250 (4)	0.41474 (10)	0.0422 (6)
C4	0.0920 (2)	0.5991 (5)	0.42645 (13)	0.0660 (8)
H4A	0.0563	0.5693	0.4607	0.099*
H4B	0.0459	0.6119	0.3951	0.099*
H4C	0.1281	0.7277	0.4310	0.099*
C5	0.31870 (18)	0.1449 (4)	0.31851 (10)	0.0433 (6)
C6	0.2606 (2)	0.1327 (4)	0.26916 (11)	0.0561 (7)
H6	0.1983	0.1958	0.2675	0.067*
C7	0.2972 (3)	0.0248 (5)	0.22233 (12)	0.0746 (10)
H7	0.2594	0.0168	0.1890	0.090*
C8	0.3894 (3)	−0.0707 (5)	0.22489 (14)	0.0791 (10)
H8	0.4129	−0.1435	0.1935	0.095*
C9	0.4465 (2)	−0.0581 (5)	0.27394 (14)	0.0691 (9)
H9	0.5084	−0.1231	0.2756	0.083*
C10	0.41182 (19)	0.0510 (4)	0.32061 (11)	0.0537 (7)
H10	0.4509	0.0616	0.3534	0.064*
C11	0.2445 (2)	0.5981 (4)	0.33217 (12)	0.0613 (8)
H11A	0.1883	0.6860	0.3240	0.092*
H11B	0.2751	0.5571	0.2971	0.092*
H11C	0.2917	0.6736	0.3552	0.092*
C12	0.20566 (17)	0.2186 (4)	0.55357 (10)	0.0406 (6)
C13	0.29783 (17)	0.3490 (4)	0.55658 (9)	0.0408 (6)
C14	0.2988 (2)	0.5560 (4)	0.53797 (11)	0.0510 (7)
H14	0.2410	0.6150	0.5229	0.061*
C15	0.3848 (2)	0.6748 (5)	0.54162 (11)	0.0585 (8)
H15	0.3846	0.8128	0.5291	0.070*
C16	0.4714 (2)	0.5874 (5)	0.56408 (11)	0.0611 (8)
H16	0.5293	0.6665	0.5661	0.073*
C17	0.47138 (19)	0.3839 (5)	0.58334 (11)	0.0583 (8)
H17	0.5293	0.3261	0.5985	0.070*
C18	0.38510 (18)	0.2647 (4)	0.58015 (10)	0.0503 (7)
H18	0.3853	0.1280	0.5937	0.060*
C19	0.17242 (18)	0.1156 (4)	0.60245 (10)	0.0483 (7)
H19	0.2078	0.1356	0.6363	0.058*
C20	0.08888 (19)	−0.0162 (4)	0.60346 (10)	0.0499 (7)
H3	0.0982 (19)	0.129 (4)	0.5052 (10)	0.060 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C21	0.072 (4)	0.092 (4)	0.060 (4)	−0.039 (4)	−0.013 (3)	0.020 (3)
F1	0.187 (5)	0.096 (3)	0.127 (3)	−0.041 (3)	−0.034 (3)	0.058 (2)
F2	0.087 (2)	0.198 (5)	0.092 (2)	−0.018 (3)	0.0368 (17)	0.033 (3)
F3	0.116 (3)	0.171 (5)	0.0502 (18)	−0.072 (3)	−0.021 (2)	0.030 (2)
C21'	0.069 (16)	0.084 (15)	0.077 (17)	−0.017 (9)	−0.012 (10)	0.005 (9)
F1'	0.095 (8)	0.098 (9)	0.065 (6)	−0.059 (7)	−0.018 (6)	0.028 (6)
F2'	0.164 (11)	0.133 (10)	0.100 (8)	0.007 (8)	0.042 (8)	0.004 (7)
F3'	0.113 (9)	0.118 (9)	0.080 (9)	0.023 (7)	−0.015 (6)	0.044 (7)
N1	0.0451 (12)	0.0405 (12)	0.0390 (12)	0.0028 (10)	0.0033 (9)	0.0038 (10)
N2	0.0476 (12)	0.0350 (12)	0.0464 (12)	0.0020 (10)	0.0008 (9)	0.0058 (10)
N3	0.0363 (12)	0.0532 (14)	0.0381 (12)	−0.0100 (11)	0.0011 (9)	−0.0004 (10)
O1	0.0714 (13)	0.0541 (12)	0.0509 (11)	0.0188 (10)	0.0025 (9)	0.0099 (9)
O2	0.0535 (11)	0.0818 (15)	0.0536 (12)	−0.0217 (10)	−0.0111 (9)	0.0076 (10)
C1	0.0414 (14)	0.0397 (15)	0.0378 (14)	−0.0034 (12)	−0.0059 (11)	0.0006 (12)
C2	0.0350 (12)	0.0428 (15)	0.0350 (13)	−0.0037 (11)	−0.0008 (10)	−0.0007 (11)
C3	0.0379 (13)	0.0436 (15)	0.0450 (14)	−0.0007 (12)	−0.0034 (11)	−0.0005 (12)
C4	0.0650 (19)	0.062 (2)	0.071 (2)	0.0186 (16)	0.0049 (15)	0.0022 (16)
C5	0.0517 (15)	0.0386 (14)	0.0396 (14)	−0.0074 (12)	0.0097 (12)	0.0043 (11)
C6	0.0706 (19)	0.0545 (18)	0.0431 (16)	−0.0030 (15)	0.0014 (14)	0.0057 (14)
C7	0.118 (3)	0.065 (2)	0.0412 (17)	−0.003 (2)	0.0051 (17)	0.0016 (15)
C8	0.123 (3)	0.058 (2)	0.057 (2)	0.003 (2)	0.036 (2)	−0.0019 (17)
C9	0.076 (2)	0.059 (2)	0.072 (2)	0.0045 (16)	0.0301 (18)	−0.0011 (17)
C10	0.0529 (17)	0.0498 (17)	0.0587 (17)	−0.0020 (14)	0.0120 (13)	0.0006 (14)
C11	0.077 (2)	0.0433 (17)	0.0640 (19)	−0.0055 (15)	0.0067 (15)	0.0143 (14)
C12	0.0384 (13)	0.0426 (15)	0.0407 (14)	0.0008 (12)	−0.0010 (11)	−0.0055 (12)
C13	0.0406 (14)	0.0467 (16)	0.0351 (13)	−0.0037 (12)	−0.0009 (10)	−0.0038 (11)
C14	0.0545 (16)	0.0457 (17)	0.0527 (16)	−0.0052 (14)	−0.0097 (13)	−0.0047 (13)
C15	0.073 (2)	0.0495 (18)	0.0526 (17)	−0.0183 (16)	−0.0052 (14)	−0.0031 (13)
C16	0.0593 (19)	0.077 (2)	0.0473 (16)	−0.0283 (17)	0.0007 (14)	−0.0087 (16)
C17	0.0441 (16)	0.079 (2)	0.0516 (17)	−0.0075 (15)	−0.0051 (12)	0.0012 (15)
C18	0.0488 (15)	0.0551 (17)	0.0469 (15)	−0.0038 (14)	−0.0046 (12)	0.0039 (13)
C19	0.0469 (15)	0.0584 (18)	0.0395 (15)	−0.0097 (14)	−0.0056 (11)	0.0008 (13)
C20	0.0473 (15)	0.0574 (18)	0.0449 (15)	−0.0058 (14)	−0.0047 (12)	0.0066 (13)

Geometric parameters (Å, º)

C21—F1	1.320 (7)	C6—H6	0.93
C21—F3	1.338 (6)	C7—C8	1.382 (5)
C21—F2	1.342 (5)	C7—H7	0.93
C21—C20	1.535 (5)	C8—C9	1.380 (4)
C21'—F1'	1.337 (10)	C8—H8	0.93
C21'—F2'	1.342 (10)	C9—C10	1.384 (4)
C21'—F3'	1.345 (10)	C9—H9	0.93
C21'—C20	1.516 (10)	C10—H10	0.93
N1—C1	1.412 (3)	C11—H11A	0.96
N1—N2	1.419 (3)	C11—H11B	0.96
N1—C5	1.440 (3)	C11—H11C	0.96
N2—C3	1.384 (3)	C12—C19	1.400 (3)
N2—C11	1.472 (3)	C12—C13	1.495 (3)
N3—C12	1.352 (3)	C13—C14	1.394 (4)
N3—C2	1.430 (3)	C13—C18	1.401 (3)
N3—H3	0.92 (3)	C14—C15	1.387 (3)
O1—C1	1.240 (3)	C14—H14	0.93
O2—C20	1.251 (3)	C15—C16	1.390 (4)
C1—C2	1.450 (3)	C15—H15	0.93
C2—C3	1.359 (3)	C16—C17	1.377 (4)
C3—C4	1.497 (4)	C16—H16	0.93
C4—H4A	0.96	C17—C18	1.390 (4)
C4—H4B	0.96	C17—H17	0.93
C4—H4C	0.96	C18—H18	0.93
C5—C10	1.389 (3)	C19—C20	1.405 (3)
C5—C6	1.393 (3)	C19—H19	0.93
C6—C7	1.392 (4)
F1—C21—F3	107.0 (4)	C9—C8—C7	120.1 (3)
F1—C21—F2	107.4 (6)	C9—C8—H8	119.9
F3—C21—F2	105.7 (5)	C7—C8—H8	119.9
F1—C21—C20	112.6 (5)	C8—C9—C10	120.0 (3)
F3—C21—C20	113.9 (5)	C8—C9—H9	120.0
F2—C21—C20	109.8 (4)	C10—C9—H9	120.0
F1'—C21'—F2'	106.0 (8)	C9—C10—C5	120.0 (3)
F1'—C21'—F3'	105.5 (8)	C9—C10—H10	120.0
F2'—C21'—F3'	105.5 (8)	C5—C10—H10	120.0
F1'—C21'—C20	110.8 (10)	N2—C11—H11A	109.5
F2'—C21'—C20	115.5 (11)	N2—C11—H11B	109.5
F3'—C21'—C20	112.8 (13)	H11A—C11—H11B	109.5
C1—N1—N2	109.25 (17)	N2—C11—H11C	109.5
C1—N1—C5	122.9 (2)	H11A—C11—H11C	109.5
N2—N1—C5	119.35 (18)	H11B—C11—H11C	109.5
C3—N2—N1	106.72 (17)	N3—C12—C19	121.5 (2)
C3—N2—C11	121.6 (2)	N3—C12—C13	118.8 (2)
N1—N2—C11	115.72 (19)	C19—C12—C13	119.7 (2)
C12—N3—C2	124.4 (2)	C14—C13—C18	118.6 (2)
C12—N3—H3	114.0 (16)	C14—C13—C12	121.6 (2)
C2—N3—H3	119.6 (16)	C18—C13—C12	119.7 (2)
O1—C1—N1	124.7 (2)	C15—C14—C13	120.7 (3)
O1—C1—C2	131.0 (2)	C15—C14—H14	119.6
N1—C1—C2	104.3 (2)	C13—C14—H14	119.6
C3—C2—N3	128.1 (2)	C14—C15—C16	119.9 (3)
C3—C2—C1	109.3 (2)	C14—C15—H15	120.1
N3—C2—C1	122.3 (2)	C16—C15—H15	120.1
C2—C3—N2	109.8 (2)	C17—C16—C15	120.1 (3)
C2—C3—C4	129.0 (2)	C17—C16—H16	119.9
N2—C3—C4	121.1 (2)	C15—C16—H16	119.9
C3—C4—H4A	109.5	C16—C17—C18	120.2 (3)
C3—C4—H4B	109.5	C16—C17—H17	119.9
H4A—C4—H4B	109.5	C18—C17—H17	119.9
C3—C4—H4C	109.5	C17—C18—C13	120.4 (3)
H4A—C4—H4C	109.5	C17—C18—H18	119.8
H4B—C4—H4C	109.5	C13—C18—H18	119.8
C10—C5—C6	120.3 (2)	C12—C19—C20	123.9 (2)
C10—C5—N1	118.6 (2)	C12—C19—H19	118.0
C6—C5—N1	121.2 (2)	C20—C19—H19	118.0
C7—C6—C5	118.9 (3)	O2—C20—C19	127.1 (2)
C7—C6—H6	120.5	O2—C20—C21'	122.1 (6)
C5—C6—H6	120.5	C19—C20—C21'	110.5 (6)
C8—C7—C6	120.6 (3)	O2—C20—C21	113.9 (3)
C8—C7—H7	119.7	C19—C20—C21	118.9 (3)
C6—C7—H7	119.7
C1—N1—N2—C3	8.5 (2)	N3—C12—C13—C14	50.5 (3)
C5—N1—N2—C3	157.42 (19)	C19—C12—C13—C14	−127.2 (3)
C1—N1—N2—C11	147.2 (2)	N3—C12—C13—C18	−131.4 (2)
C5—N1—N2—C11	−63.9 (3)	C19—C12—C13—C18	50.9 (3)
N2—N1—C1—O1	171.3 (2)	C18—C13—C14—C15	1.3 (4)
C5—N1—C1—O1	23.7 (3)	C12—C13—C14—C15	179.4 (2)
N2—N1—C1—C2	−7.2 (2)	C13—C14—C15—C16	0.0 (4)
C5—N1—C1—C2	−154.8 (2)	C14—C15—C16—C17	−0.8 (4)
C12—N3—C2—C3	−116.3 (3)	C15—C16—C17—C18	0.3 (4)
C12—N3—C2—C1	71.0 (3)	C16—C17—C18—C13	1.0 (4)
O1—C1—C2—C3	−175.0 (2)	C14—C13—C18—C17	−1.8 (4)
N1—C1—C2—C3	3.4 (2)	C12—C13—C18—C17	−179.9 (2)
O1—C1—C2—N3	−1.1 (4)	N3—C12—C19—C20	4.7 (4)
N1—C1—C2—N3	177.23 (19)	C13—C12—C19—C20	−177.6 (2)
N3—C2—C3—N2	−171.6 (2)	C12—C19—C20—O2	0.7 (5)
C1—C2—C3—N2	1.8 (3)	C12—C19—C20—C21'	−173.4 (6)
N3—C2—C3—C4	10.3 (4)	C12—C19—C20—C21	−179.7 (3)
C1—C2—C3—C4	−176.2 (2)	F1'—C21'—C20—O2	19.4 (13)
N1—N2—C3—C2	−6.3 (2)	F2'—C21'—C20—O2	−101.2 (12)
C11—N2—C3—C2	−142.0 (2)	F3'—C21'—C20—O2	137.3 (11)
N1—N2—C3—C4	172.0 (2)	F1'—C21'—C20—C19	−166.2 (10)
C11—N2—C3—C4	36.2 (3)	F2'—C21'—C20—C19	73.2 (13)
C1—N1—C5—C10	−60.4 (3)	F3'—C21'—C20—C19	−48.2 (13)
N2—N1—C5—C10	155.0 (2)	F1'—C21'—C20—C21	−19 (3)
C1—N1—C5—C6	117.7 (3)	F2'—C21'—C20—C21	−140 (5)
N2—N1—C5—C6	−26.8 (3)	F3'—C21'—C20—C21	99 (4)
C10—C5—C6—C7	0.2 (4)	F1—C21—C20—O2	60.7 (6)
N1—C5—C6—C7	−177.9 (2)	F3—C21—C20—O2	−177.3 (5)
C5—C6—C7—C8	0.6 (4)	F2—C21—C20—O2	−58.9 (6)
C6—C7—C8—C9	−0.6 (5)	F1—C21—C20—C19	−119.0 (5)
C7—C8—C9—C10	−0.3 (5)	F3—C21—C20—C19	3.1 (7)
C8—C9—C10—C5	1.2 (4)	F2—C21—C20—C19	121.4 (5)
C6—C5—C10—C9	−1.1 (4)	F1—C21—C20—C21'	−155 (4)
N1—C5—C10—C9	177.0 (2)	F3—C21—C20—C21'	−33 (4)
C2—N3—C12—C19	−164.9 (2)	F2—C21—C20—C21'	86 (4)
C2—N3—C12—C13	17.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2	0.92 (3)	2.02 (3)	2.761 (3)	137 (2)
N3—H3···O2^i	0.92 (3)	2.40 (3)	3.094 (3)	133 (2)

Symmetry code: (i) −x, −y, −z+1.