1,5-Dimethyl-4-[3-oxo-1,3-bis­(trifluoro­meth­yl)prop-1-enylamino]-2-phenyl-1H-pyrazol-3(2H)-one

In the title mol­ecule, C₁₆H₁₃F₆N₃O₂, the phenyl and pyrazolone rings make a dihedral angle of 43.1 (3)°. Intra­molecular N—H...O hydrogen bonding contributes to the essential coplanarity of the side-chain carbonyl group, the adjacent double bond and the amine N atom; the latter has the largest deviation [0.017 (3) Å] from the mean plane. In the crystal structure, weak inter­molecular C—H...O hydrogen bonds link the mol­ecules into chains extending along the c axis. The F atoms of one CF₃ group are disordered approximately equally over two sets of positions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.043
• wR factor = 0.093
• Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT301_ALERT_3_C Main Residue  Disorder .........................      10.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      21.50 Deg.
              F6'  -C7   -F4      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      30.40 Deg.
              F5'  -C7   -F6      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      34.30 Deg.
              F5   -C7   -F4'     1.555   1.555   1.555

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.969
            Tmax scaled      0.969 Tmin scaled      0.956
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         42

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

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

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S1. Comment

Schiff base ligands derived from 4-aminoantipyrine and their metal complexes have attracted great attentions of several research groups due to their potential biological activities, such as analgesic, anti-inflammatory, antimicrobial and anticancer activity. As a part of our continuing interest on the syntheses of potential bioactive compounds, we have synthesized several novel schiff base ligands with 4-aminoantipyrine in search for antibacterial agents. And we report here the structure of the title compound (I).

A view of the molecule of (I) is shown in Fig. 1. Atoms C4, C5, C6 and O2 of the HFAA moiety and atom N3 of 4-AATP are essentially coplanar, the largest deviation from the mean plane being 0.017 (3) Å for atom C6. This mean plane is nearly perpendicular to the pyrazolone ring with the dihedral angle of 87.34 (2) °, which close to the value of 84.10 (6) ° reported by Yu et al. (2002), reducing their steric hindrance. Bond lengths within this part of the molecule lie between the classical double- and single-bond lengths, clearly indicating that there is electron delocalization over this segment. The dihedral angle between phenyl and pyrazolone rings is 43.1 (3) °. Small torsion angles for O2—C6—C5—C4 [-4.9 (5) °] and N3—C4—C5—C6 [4.0 (4) °] show that atoms O2 and N3 may coordinate with metal ion to form a six-membered chelating ring. Atoms O1, C1, C3 and N3 are also coplanar, the largest deviation from this mean plane being 0.006 (2) Å both for C1 and C3. The dihedral angle between this plane and the adjacent pyrazolone ring of 4-AATP is 6.26 (3) °, closing to the value of 6.64 (3) ° in 4-{[3,4-Dihydro-5-methyl-3-oxo-2-phenyl- 2H-pyrazol-4-ylidene](phenyl)methylamino}- 1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (Wang et al., 2003). The bond lengths in this part of the molecule also indicate delocalization for the antipyrine group. Small torsion angles for O1—C1—C3—N3 [-1.7 (5) °] show that atoms O1 and N3 could chelate with metal and forming a stable five-membered ring. The displacements of atoms C10 and C11 from the pyrazolone ring are -0.588 (7) and 0.397 (5) Å, respectively, showing that the methyl group bonded to N2 and the phenyl group bonded to N1 are on opposite sides of the ring, and the torsion angle of C11—N1—N2—C10 is 54.8 (3) °. These are similar to the related reports (Yu et al., 2002; Wang et al., 2003). A strong intramolecular N—H—O hydrogen bond is observed (Table 1), which shows that the molecule exists as the enamine-keto tautomeric form. This case is completely different from that of 3- (2,3-dihydro-1,5-dimethyl 3-oxo-2-phenylpyrazol-4-ylimino)-4,4,4-trifluoro-1-(2-thienyl)butane -1,2-dione (Wang et al., 2002), but similar to that in 1,5-Dimethyl-4-{[(E)-3-oxo-3-(2-thienyl)- 1-(trifluoromethyl)-1-propenyl] amino}-2-phenyl- 1,2-dihydro-3H-pyrazol-3-one (Yu et al., 2002). In addition, in the crystal the weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into chains extended along c axis.

Related literature

For related crystal structures, see: Wang et al. (2002, 2003); Yu et al. (2002).

S2. Experimental

The ethanol solutions of 4-aminoantipyrine (0.01 mol) and HFAA (0.01 mol) were refluxed together for 3 h over a steam bath. The excess solvent was removed by evaporation and the concentrated solution was cooled in an ice bath with stirring. Title compound separated out as a cream-colored powder, which was filtered and washed with ethanol, then dried in a vacuum over CaCl₂. Melting point: 440–442 K, Elemental analysis for C₁₆H₁₃F₆N₃O₂, calculated: C 48.86, H 3.33, N 10.69%; found: C 48.71, H 3.42, N 10.56%. Bright-yellow single crystals suitable for X-ray analysis were obtained by slow cooling of the warmed solution in ethanol.

S3. Refinement

C-bound H atoms were included in calculated positions (C—H 0.93, 0.96 Å) and treated in the subsequent refinement as riding atoms, with U_iso(H) = 1.2 or 1.5 U_eq(C). Atom H3 was located in Fourier difference map and refined isotropically. One CF₃ group (at C7) was treated as disordered between two orientations with the refined occupancies of 0.54 (3) and 0.46 (3), respectively. The C7—F' bond lengths were restrained to 1.32 (2) Å.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL (Bruker, 1998).

Figures

Fig. 1. The molecular structure of (I) showing atomic numbering, disordered CF3 group and 20% probability displacement ellipsoids. Dashed line denotes hydrogen bond.

1,5-Dimethyl-4-[3-oxo-1,3-bis(trifluoromethyl)prop-1-enylamino]-2-phenyl- 1H-pyrazol-3(2H)-one

Crystal data

C16H13F6N3O2	F(000) = 800
Mr = 393.29	Dx = 1.519 Mg m^−3
Monoclinic, P21/c	Melting point = 440–442 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.807 (5) Å	Cell parameters from 2548 reflections
b = 8.324 (3) Å	θ = 2.7–25.0°
c = 13.715 (5) Å	µ = 0.15 mm^−1
β = 107.644 (6)°	T = 293 K
V = 1719.6 (11) Å^3	Block, yellow
Z = 4	0.30 × 0.30 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3008 independent reflections
Radiation source: fine-focus sealed tube	1508 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
ϕ and ω scan	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→18
Tmin = 0.987, Tmax = 1.000	k = −9→8
6854 measured reflections	l = −15→16

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.093	w = 1/[σ^2(Fo^2) + (0.0307P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
3008 reflections	Δρmax = 0.17 e Å^−3
279 parameters	Δρmin = −0.14 e Å^−3
42 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0223 (11)

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)
O1	0.60740 (12)	0.2162 (3)	0.45906 (15)	0.0638 (6)
O2	0.85903 (15)	0.5621 (3)	0.51390 (17)	0.0811 (8)
N1	0.56744 (14)	0.1180 (3)	0.29188 (15)	0.0447 (6)
N2	0.60661 (14)	0.1235 (3)	0.21240 (15)	0.0440 (6)
N3	0.78198 (15)	0.2900 (4)	0.41904 (18)	0.0497 (7)
C4	0.85016 (16)	0.2205 (4)	0.4883 (2)	0.0433 (7)
C8	0.8539 (2)	0.0401 (4)	0.4874 (2)	0.0559 (8)
F1	0.78609 (13)	−0.0247 (2)	0.51143 (15)	0.0811 (6)
F2	0.85204 (11)	−0.0198 (2)	0.39737 (13)	0.0770 (6)
F3	0.92697 (12)	−0.0163 (2)	0.55386 (14)	0.0882 (7)
C6	0.91335 (19)	0.4700 (5)	0.5685 (2)	0.0550 (9)
C7	0.9825 (2)	0.5457 (5)	0.6604 (3)	0.0662 (10)
C1	0.62664 (18)	0.1871 (3)	0.3800 (2)	0.0463 (8)
C2	0.69184 (17)	0.1733 (3)	0.2536 (2)	0.0431 (7)
C3	0.70543 (16)	0.2138 (3)	0.35296 (19)	0.0423 (7)
C5	0.91552 (17)	0.3029 (4)	0.55891 (19)	0.0490 (8)
H5	0.9629	0.2461	0.6019	0.059*
C9	0.75420 (18)	0.1735 (4)	0.1918 (2)	0.0632 (9)
H9A	0.8061	0.2348	0.2265	0.095*
H9B	0.7258	0.2208	0.1262	0.095*
H9C	0.7712	0.0651	0.1827	0.095*
C11	0.47364 (17)	0.1192 (3)	0.2692 (2)	0.0449 (7)
C12	0.4196 (2)	0.1857 (4)	0.1797 (2)	0.0599 (9)
H12	0.4439	0.2289	0.1316	0.072*
C13	0.3289 (2)	0.1871 (4)	0.1628 (3)	0.0823 (12)
H13	0.2918	0.2286	0.1019	0.099*
C14	0.2929 (2)	0.1281 (5)	0.2345 (4)	0.0886 (13)
H14	0.2319	0.1317	0.2228	0.106*
C15	0.3469 (3)	0.0638 (4)	0.3232 (3)	0.0791 (11)
H15	0.3222	0.0246	0.3720	0.095*
C16	0.4372 (2)	0.0562 (4)	0.3413 (2)	0.0566 (9)
H16	0.4735	0.0095	0.4010	0.068*
C10	0.58075 (19)	0.0024 (4)	0.1319 (2)	0.0580 (9)
H10A	0.5903	0.0436	0.0706	0.087*
H10B	0.5191	−0.0234	0.1186	0.087*
H10C	0.6159	−0.0926	0.1534	0.087*
F4	0.9963 (12)	0.6977 (12)	0.6454 (13)	0.114 (5)	0.54 (3)
F5	0.9608 (7)	0.524 (2)	0.7431 (5)	0.092 (3)	0.54 (3)
F6	1.0624 (5)	0.4819 (17)	0.6763 (13)	0.110 (4)	0.54 (3)
F4'	0.9411 (9)	0.609 (3)	0.7246 (13)	0.111 (4)	0.46 (3)
F5'	1.0448 (10)	0.4480 (14)	0.7120 (11)	0.107 (4)	0.46 (3)
F6'	1.0209 (11)	0.6712 (16)	0.6377 (12)	0.085 (4)	0.46 (3)
H3	0.7816 (18)	0.391 (4)	0.423 (2)	0.060 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0513 (13)	0.0989 (18)	0.0381 (13)	−0.0008 (11)	0.0090 (10)	−0.0144 (12)
O2	0.0821 (17)	0.0659 (17)	0.0671 (16)	−0.0058 (12)	−0.0198 (13)	−0.0016 (13)
N1	0.0341 (14)	0.0650 (18)	0.0309 (13)	−0.0040 (12)	0.0036 (11)	−0.0015 (12)
N2	0.0380 (14)	0.0610 (17)	0.0293 (13)	−0.0061 (12)	0.0047 (11)	−0.0065 (12)
N3	0.0417 (16)	0.055 (2)	0.0415 (15)	−0.0024 (14)	−0.0043 (11)	−0.0037 (15)
C4	0.0354 (17)	0.059 (2)	0.0333 (16)	−0.0008 (14)	0.0066 (14)	0.0005 (15)
C8	0.045 (2)	0.073 (3)	0.0419 (19)	0.0023 (17)	0.0021 (15)	−0.0001 (18)
F1	0.0845 (14)	0.0723 (14)	0.0914 (14)	−0.0154 (11)	0.0341 (12)	0.0030 (11)
F2	0.0842 (13)	0.0816 (15)	0.0581 (12)	0.0151 (10)	0.0109 (10)	−0.0187 (11)
F3	0.0791 (13)	0.0793 (15)	0.0773 (13)	0.0174 (10)	−0.0196 (11)	0.0024 (11)
C6	0.044 (2)	0.078 (3)	0.0373 (18)	−0.0119 (18)	0.0040 (15)	−0.0011 (19)
C7	0.062 (3)	0.072 (3)	0.055 (2)	−0.016 (2)	0.002 (2)	0.001 (2)
C1	0.0436 (19)	0.058 (2)	0.0303 (16)	0.0028 (15)	0.0013 (14)	−0.0025 (15)
C2	0.0340 (17)	0.057 (2)	0.0338 (16)	−0.0016 (14)	0.0033 (13)	0.0006 (15)
C3	0.0290 (16)	0.060 (2)	0.0333 (16)	−0.0019 (14)	0.0028 (13)	−0.0048 (15)
C5	0.0397 (18)	0.067 (2)	0.0350 (17)	−0.0062 (16)	0.0037 (13)	0.0002 (17)
C9	0.0502 (19)	0.094 (3)	0.0461 (18)	−0.0017 (17)	0.0160 (15)	−0.0013 (18)
C11	0.0347 (17)	0.046 (2)	0.0461 (17)	−0.0042 (14)	−0.0006 (14)	−0.0053 (15)
C12	0.050 (2)	0.053 (2)	0.062 (2)	−0.0039 (15)	−0.0066 (16)	0.0052 (17)
C13	0.046 (2)	0.074 (3)	0.096 (3)	0.0039 (19)	−0.023 (2)	−0.002 (2)
C14	0.040 (2)	0.085 (3)	0.134 (4)	−0.010 (2)	0.016 (3)	−0.019 (3)
C15	0.067 (3)	0.077 (3)	0.103 (3)	−0.020 (2)	0.039 (2)	−0.018 (2)
C16	0.051 (2)	0.055 (2)	0.064 (2)	−0.0056 (16)	0.0172 (17)	−0.0026 (17)
C10	0.068 (2)	0.064 (2)	0.0358 (16)	−0.0081 (16)	0.0064 (14)	−0.0108 (16)
F4	0.116 (8)	0.084 (5)	0.112 (6)	−0.029 (4)	−0.010 (5)	−0.013 (4)
F5	0.097 (5)	0.133 (8)	0.036 (3)	−0.051 (4)	0.007 (3)	−0.008 (3)
F6	0.055 (4)	0.130 (7)	0.119 (7)	−0.011 (4)	−0.012 (4)	−0.028 (5)
F4'	0.108 (6)	0.155 (9)	0.079 (6)	−0.052 (6)	0.043 (5)	−0.057 (6)
F5'	0.097 (7)	0.101 (5)	0.077 (6)	−0.025 (5)	−0.044 (4)	0.010 (4)
F6'	0.075 (6)	0.109 (7)	0.068 (4)	−0.048 (5)	0.014 (4)	0.005 (5)

Geometric parameters (Å, º)

O1—C1	1.236 (3)	C7—F4'	1.352 (8)
O2—C6	1.223 (3)	C1—C3	1.420 (3)
N1—C1	1.408 (3)	C2—C3	1.356 (3)
N1—N2	1.408 (3)	C2—C9	1.482 (3)
N1—C11	1.420 (3)	C5—H5	0.9300
N2—C2	1.358 (3)	C9—H9A	0.9600
N2—C10	1.459 (3)	C9—H9B	0.9600
N3—C4	1.333 (3)	C9—H9C	0.9600
N3—C3	1.422 (3)	C11—C12	1.381 (4)
N3—H3	0.85 (3)	C11—C16	1.389 (4)
C4—C5	1.367 (3)	C12—C13	1.381 (4)
C4—C8	1.503 (4)	C12—H12	0.9300
C8—F3	1.322 (3)	C13—C14	1.367 (5)
C8—F2	1.323 (3)	C13—H13	0.9300
C8—F1	1.328 (3)	C14—C15	1.365 (5)
C6—C5	1.398 (4)	C14—H14	0.9300
C6—C7	1.532 (4)	C15—C16	1.375 (4)
C7—F6'	1.293 (8)	C15—H15	0.9300
C7—F5	1.294 (7)	C16—H16	0.9300
C7—F5'	1.307 (8)	C10—H10A	0.9600
C7—F4	1.310 (8)	C10—H10B	0.9600
C7—F6	1.325 (7)	C10—H10C	0.9600
C1—N1—N2	108.5 (2)	O1—C1—N1	123.9 (3)
C1—N1—C11	124.3 (2)	O1—C1—C3	131.8 (2)
N2—N1—C11	120.3 (2)	N1—C1—C3	104.3 (2)
C2—N2—N1	107.5 (2)	C3—C2—N2	109.2 (2)
C2—N2—C10	122.7 (2)	C3—C2—C9	130.1 (2)
N1—N2—C10	118.4 (2)	N2—C2—C9	120.7 (2)
C4—N3—C3	127.5 (3)	C2—C3—C1	109.8 (2)
C4—N3—H3	114 (2)	C2—C3—N3	126.6 (3)
C3—N3—H3	117.7 (19)	C1—C3—N3	123.2 (2)
N3—C4—C5	124.1 (3)	C4—C5—C6	122.1 (3)
N3—C4—C8	116.9 (3)	C4—C5—H5	119.0
C5—C4—C8	118.9 (3)	C6—C5—H5	119.0
F3—C8—F2	106.1 (3)	C2—C9—H9A	109.5
F3—C8—F1	106.7 (3)	C2—C9—H9B	109.5
F2—C8—F1	106.7 (3)	H9A—C9—H9B	109.5
F3—C8—C4	112.2 (3)	C2—C9—H9C	109.5
F2—C8—C4	113.2 (3)	H9A—C9—H9C	109.5
F1—C8—C4	111.6 (3)	H9B—C9—H9C	109.5
O2—C6—C5	126.8 (3)	C12—C11—C16	120.4 (3)
O2—C6—C7	116.1 (3)	C12—C11—N1	121.4 (3)
C5—C6—C7	117.0 (3)	C16—C11—N1	118.2 (3)
F6'—C7—F5	126.5 (9)	C13—C12—C11	118.9 (3)
F6'—C7—F5'	107.6 (9)	C13—C12—H12	120.5
F5—C7—F5'	78.2 (6)	C11—C12—H12	120.5
F6'—C7—F4	21.5 (11)	C14—C13—C12	120.9 (3)
F5—C7—F4	112.1 (8)	C14—C13—H13	119.6
F5'—C7—F4	123.5 (8)	C12—C13—H13	119.6
F6'—C7—F6	82.6 (8)	C15—C14—C13	119.9 (4)
F5—C7—F6	107.0 (6)	C15—C14—H14	120.1
F5'—C7—F6	30.4 (6)	C13—C14—H14	120.1
F4—C7—F6	102.6 (8)	C14—C15—C16	120.9 (4)
F6'—C7—F4'	101.5 (9)	C14—C15—H15	119.6
F5—C7—F4'	34.3 (6)	C16—C15—H15	119.6
F5'—C7—F4'	108.9 (8)	C15—C16—C11	119.1 (3)
F4—C7—F4'	82.2 (8)	C15—C16—H16	120.5
F6—C7—F4'	132.3 (7)	C11—C16—H16	120.5
F6'—C7—C6	113.8 (8)	N2—C10—H10A	109.5
F5—C7—C6	110.5 (5)	N2—C10—H10B	109.5
F5'—C7—C6	115.0 (6)	H10A—C10—H10B	109.5
F4—C7—C6	112.3 (7)	N2—C10—H10C	109.5
F6—C7—C6	112.1 (6)	H10A—C10—H10C	109.5
F4'—C7—C6	109.2 (6)	H10B—C10—H10C	109.5
C1—N1—N2—C2	8.2 (3)	C10—N2—C2—C3	−148.5 (3)
C11—N1—N2—C2	160.4 (2)	N1—N2—C2—C9	172.9 (2)
C1—N1—N2—C10	152.8 (2)	C10—N2—C2—C9	30.1 (4)
C11—N1—N2—C10	−55.0 (3)	N2—C2—C3—C1	1.2 (3)
C3—N3—C4—C5	−170.5 (3)	C9—C2—C3—C1	−177.2 (3)
C3—N3—C4—C8	9.3 (4)	N2—C2—C3—N3	−171.6 (3)
N3—C4—C8—F3	175.5 (2)	C9—C2—C3—N3	10.0 (5)
C5—C4—C8—F3	−4.7 (4)	O1—C1—C3—C2	−174.8 (3)
N3—C4—C8—F2	55.5 (4)	N1—C1—C3—C2	3.8 (3)
C5—C4—C8—F2	−124.7 (3)	O1—C1—C3—N3	−1.7 (5)
N3—C4—C8—F1	−64.9 (3)	N1—C1—C3—N3	176.9 (3)
C5—C4—C8—F1	115.0 (3)	C4—N3—C3—C2	−98.4 (4)
O2—C6—C7—F6'	−49.1 (11)	C4—N3—C3—C1	89.7 (4)
C5—C6—C7—F6'	134.5 (10)	N3—C4—C5—C6	4.0 (4)
O2—C6—C7—F5	100.1 (10)	C8—C4—C5—C6	−175.8 (3)
C5—C6—C7—F5	−76.3 (10)	O2—C6—C5—C4	−4.9 (5)
O2—C6—C7—F5'	−173.8 (11)	C7—C6—C5—C4	171.1 (3)
C5—C6—C7—F5'	9.8 (11)	C1—N1—C11—C12	122.3 (3)
O2—C6—C7—F4	−25.8 (11)	N2—N1—C11—C12	−25.3 (4)
C5—C6—C7—F4	157.8 (11)	C1—N1—C11—C16	−55.6 (4)
O2—C6—C7—F6	−140.6 (10)	N2—N1—C11—C16	156.8 (3)
C5—C6—C7—F6	42.9 (10)	C16—C11—C12—C13	−0.6 (4)
O2—C6—C7—F4'	63.5 (14)	N1—C11—C12—C13	−178.4 (3)
C5—C6—C7—F4'	−112.9 (13)	C11—C12—C13—C14	1.9 (5)
N2—N1—C1—O1	171.6 (3)	C12—C13—C14—C15	−1.4 (6)
C11—N1—C1—O1	20.7 (4)	C13—C14—C15—C16	−0.5 (6)
N2—N1—C1—C3	−7.2 (3)	C14—C15—C16—C11	1.8 (5)
C11—N1—C1—C3	−158.1 (2)	C12—C11—C16—C15	−1.2 (4)
N1—N2—C2—C3	−5.7 (3)	N1—C11—C16—C15	176.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2	0.85 (3)	2.04 (3)	2.710 (4)	136 (3)
C9—H9B···O1^i	0.96	2.54	3.453 (3)	160 (3)
C10—H10A···O1^i	0.96	2.58	3.448 (3)	150 (3)

Symmetry code: (i) x, −y+1/2, z−1/2.