2-[3,5-Bis-(4-fluoro-phen-yl)-4,5-dihydro-1H-pyrazol-1-yl]-4,6-bis(4-fluoro-phenyl)pyrimidine.

In the title compound, C(31)H(20)F(4)N(4), the pyrazole ring adopts an envelope conformation and forms a dihedral angle of 9.91 (6)° with the adjacent pyrimidine ring. The pyrimidine ring forms dihedral angles of 9.23 (6) and 2.16 (5)° with its adjacent fluoro-substituted benzene rings, whereas these angles are 88.22 (6) and 9.66 (6)° for the pyrazole ring and its adjacent benzene rings. In the crystal, mol-ecules are linked by C-H⋯F hydrogen bonds into ribbons along [01-1]. The crystal packing is further stabilized by C-H⋯π and by π-π inter-actions, with centroid-centroid distances of 3.7428 (7) and 3.7630 (6) Å.

Related literature

For related literature, see: Calabresi et al. (1975 ▶); El-Hashash et al. (1993 ▶); Huang & Huang (2002 ▶); Marquez & Russ (2002 ▶); Townsend & Drach (2002 ▶). For related structures and background to various derivatives of 4,4′-difluoro­chalcone, see: Fun et al. (2010a ▶,b ▶, 2011 ▶, 2012 ▶). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C31H20F4N4

M = 524.51

Triclinic,

a = 10.1020 (1) Å

b = 10.1106 (1) Å

c = 12.3886 (1) Å

α = 104.719 (1)°

β = 98.275 (1)°

γ = 102.167 (1)°

V = 1169.94 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.38 × 0.26 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.959, T max = 0.987

30262 measured reflections

8234 independent reflections

6443 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.132

S = 1.04

8234 reflections

352 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.23 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006976/fj2517sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006976/fj2517Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812006976/fj2517Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C31H20F4N4	Z = 2
Mr = 524.51	F(000) = 540
Triclinic, P1	Dx = 1.489 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.1020 (1) Å	Cell parameters from 9041 reflections
b = 10.1106 (1) Å	θ = 2.6–32.2°
c = 12.3886 (1) Å	µ = 0.11 mm−1
α = 104.719 (1)°	T = 100 K
β = 98.275 (1)°	Block, orange
γ = 102.167 (1)°	0.38 × 0.26 × 0.12 mm
V = 1169.94 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	8234 independent reflections
Radiation source: fine-focus sealed tube	6443 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 32.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.959, Tmax = 0.987	k = −15→15
30262 measured reflections	l = −18→18

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.069P)2 + 0.3191P] where P = (Fo2 + 2Fc2)/3
8234 reflections	(Δ/σ)max < 0.001
352 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
F1	0.89250 (10)	0.66229 (9)	0.65306 (6)	0.0382 (2)
F2	0.46323 (8)	0.14504 (8)	−0.40779 (6)	0.02907 (17)
F3	0.41746 (8)	1.23828 (8)	0.34142 (7)	0.02823 (17)
F4	0.85454 (8)	1.31912 (8)	−0.39439 (6)	0.02724 (17)
N1	0.80575 (9)	0.81293 (10)	0.19025 (7)	0.01531 (16)
N2	0.73090 (9)	0.71218 (9)	−0.01349 (8)	0.01557 (16)
N3	0.82490 (10)	0.95255 (9)	0.07072 (7)	0.01658 (17)
N4	0.81772 (9)	0.97309 (10)	−0.03568 (7)	0.01557 (17)
C1	0.79155 (15)	0.54528 (13)	0.34519 (10)	0.0270 (3)
H1A	0.7638	0.4614	0.2856	0.032*
C2	0.82258 (16)	0.54050 (14)	0.45700 (11)	0.0333 (3)
H2A	0.8166	0.4545	0.4728	0.040*
C3	0.86230 (14)	0.66581 (14)	0.54355 (10)	0.0255 (2)
C4	0.87484 (13)	0.79565 (13)	0.52391 (10)	0.0235 (2)
H4A	0.9030	0.8790	0.5841	0.028*
C5	0.84417 (12)	0.79855 (12)	0.41174 (10)	0.0210 (2)
H5A	0.8523	0.8852	0.3969	0.025*
C6	0.80148 (11)	0.67431 (11)	0.32098 (9)	0.01634 (19)
C7	0.77219 (10)	0.68237 (11)	0.20211 (9)	0.01509 (18)
C8	0.78434 (10)	0.81953 (11)	0.08231 (9)	0.01468 (18)
C9	0.69487 (10)	0.58258 (11)	−0.00015 (9)	0.01464 (18)
C10	0.71525 (11)	0.56267 (11)	0.10790 (9)	0.01625 (19)
H10A	0.6917	0.4727	0.1169	0.019*
C11	0.63204 (10)	0.46548 (11)	−0.10704 (9)	0.01510 (18)
C12	0.61879 (12)	0.49503 (12)	−0.21201 (9)	0.0189 (2)
H12A	0.6493	0.5878	−0.2137	0.023*
C13	0.56065 (13)	0.38780 (13)	−0.31367 (10)	0.0220 (2)
H13A	0.5510	0.4078	−0.3832	0.026*
C14	0.51758 (12)	0.25068 (12)	−0.30883 (10)	0.0210 (2)
C15	0.52830 (12)	0.21662 (12)	−0.20708 (10)	0.0204 (2)
H15A	0.4980	0.1235	−0.2063	0.025*
C16	0.58535 (11)	0.32499 (12)	−0.10650 (9)	0.0180 (2)
H16A	0.5928	0.3041	−0.0373	0.022*
C17	0.86637 (11)	1.08631 (11)	0.16485 (8)	0.01558 (18)
H17A	0.9378	1.0824	0.2256	0.019*
C18	0.92757 (11)	1.19104 (11)	0.10206 (9)	0.01707 (19)
H18A	0.8960	1.2766	0.1209	0.020*
H18B	1.0280	1.2159	0.1198	0.020*
C19	0.87065 (10)	1.10600 (11)	−0.02133 (9)	0.01479 (18)
C20	0.74267 (11)	1.12033 (11)	0.21187 (9)	0.01539 (18)
C21	0.74268 (11)	1.14552 (12)	0.32750 (9)	0.0183 (2)
H21A	0.8178	1.1375	0.3762	0.022*
C22	0.63167 (12)	1.18269 (12)	0.37163 (9)	0.0207 (2)
H22A	0.6310	1.1975	0.4487	0.025*
C23	0.52321 (11)	1.19689 (12)	0.29813 (10)	0.0206 (2)
C24	0.51718 (12)	1.17086 (12)	0.18210 (10)	0.0211 (2)
H24A	0.4418	1.1796	0.1342	0.025*
C25	0.62721 (11)	1.13136 (12)	0.13951 (9)	0.0185 (2)
H25A	0.6247	1.1118	0.0616	0.022*
C26	0.87168 (10)	1.16138 (11)	−0.11947 (9)	0.01481 (18)
C27	0.92096 (11)	1.30626 (11)	−0.10361 (9)	0.01704 (19)
H27A	0.9579	1.3672	−0.0303	0.020*
C28	0.91544 (12)	1.36053 (12)	−0.19632 (10)	0.0193 (2)
H28A	0.9478	1.4570	−0.1860	0.023*
C29	0.86081 (11)	1.26735 (12)	−0.30369 (9)	0.0193 (2)
C30	0.81118 (12)	1.12320 (12)	−0.32338 (9)	0.0197 (2)
H30A	0.7745	1.0632	−0.3971	0.024*
C31	0.81755 (11)	1.07049 (12)	−0.23047 (9)	0.01756 (19)
H31A	0.7856	0.9737	−0.2419	0.021*

	U11	U22	U33	U12	U13	U23
F1	0.0612 (6)	0.0311 (4)	0.0157 (3)	0.0003 (4)	−0.0045 (3)	0.0118 (3)
F2	0.0366 (4)	0.0216 (4)	0.0209 (3)	0.0025 (3)	0.0030 (3)	−0.0020 (3)
F3	0.0246 (3)	0.0301 (4)	0.0304 (4)	0.0098 (3)	0.0107 (3)	0.0046 (3)
F4	0.0355 (4)	0.0302 (4)	0.0214 (3)	0.0086 (3)	0.0041 (3)	0.0180 (3)
N1	0.0177 (4)	0.0148 (4)	0.0152 (4)	0.0044 (3)	0.0035 (3)	0.0072 (3)
N2	0.0183 (4)	0.0132 (4)	0.0158 (4)	0.0036 (3)	0.0034 (3)	0.0059 (3)
N3	0.0254 (4)	0.0127 (4)	0.0124 (4)	0.0038 (3)	0.0040 (3)	0.0057 (3)
N4	0.0196 (4)	0.0151 (4)	0.0140 (4)	0.0047 (3)	0.0043 (3)	0.0071 (3)
C1	0.0418 (7)	0.0163 (5)	0.0174 (5)	−0.0014 (5)	−0.0033 (5)	0.0078 (4)
C2	0.0533 (8)	0.0191 (6)	0.0211 (5)	−0.0027 (5)	−0.0061 (5)	0.0120 (5)
C3	0.0329 (6)	0.0258 (6)	0.0155 (5)	0.0014 (5)	−0.0011 (4)	0.0105 (4)
C4	0.0335 (6)	0.0210 (5)	0.0158 (5)	0.0087 (5)	0.0019 (4)	0.0052 (4)
C5	0.0294 (5)	0.0178 (5)	0.0173 (5)	0.0081 (4)	0.0037 (4)	0.0071 (4)
C6	0.0180 (4)	0.0165 (5)	0.0152 (4)	0.0032 (4)	0.0021 (3)	0.0076 (4)
C7	0.0158 (4)	0.0154 (5)	0.0161 (4)	0.0046 (3)	0.0035 (3)	0.0078 (4)
C8	0.0164 (4)	0.0135 (4)	0.0159 (4)	0.0041 (3)	0.0038 (3)	0.0068 (4)
C9	0.0143 (4)	0.0142 (4)	0.0168 (4)	0.0042 (3)	0.0031 (3)	0.0064 (4)
C10	0.0184 (4)	0.0141 (4)	0.0170 (4)	0.0031 (4)	0.0024 (4)	0.0073 (4)
C11	0.0161 (4)	0.0138 (4)	0.0162 (4)	0.0045 (3)	0.0034 (3)	0.0053 (4)
C12	0.0237 (5)	0.0164 (5)	0.0175 (5)	0.0055 (4)	0.0041 (4)	0.0066 (4)
C13	0.0277 (5)	0.0209 (5)	0.0169 (5)	0.0066 (4)	0.0037 (4)	0.0051 (4)
C14	0.0212 (5)	0.0186 (5)	0.0196 (5)	0.0046 (4)	0.0034 (4)	0.0004 (4)
C15	0.0209 (5)	0.0153 (5)	0.0248 (5)	0.0035 (4)	0.0055 (4)	0.0060 (4)
C16	0.0188 (4)	0.0159 (5)	0.0205 (5)	0.0045 (4)	0.0043 (4)	0.0070 (4)
C17	0.0194 (4)	0.0132 (4)	0.0129 (4)	0.0024 (4)	0.0016 (3)	0.0042 (3)
C18	0.0210 (5)	0.0141 (4)	0.0149 (4)	0.0014 (4)	0.0030 (4)	0.0052 (4)
C19	0.0169 (4)	0.0140 (4)	0.0142 (4)	0.0033 (3)	0.0033 (3)	0.0060 (4)
C20	0.0187 (4)	0.0121 (4)	0.0142 (4)	0.0017 (3)	0.0020 (3)	0.0046 (3)
C21	0.0213 (5)	0.0188 (5)	0.0143 (4)	0.0041 (4)	0.0025 (4)	0.0052 (4)
C22	0.0243 (5)	0.0201 (5)	0.0165 (5)	0.0044 (4)	0.0054 (4)	0.0040 (4)
C23	0.0197 (5)	0.0167 (5)	0.0245 (5)	0.0040 (4)	0.0065 (4)	0.0042 (4)
C24	0.0198 (5)	0.0212 (5)	0.0212 (5)	0.0050 (4)	0.0012 (4)	0.0064 (4)
C25	0.0220 (5)	0.0181 (5)	0.0145 (4)	0.0037 (4)	0.0020 (4)	0.0056 (4)
C26	0.0161 (4)	0.0142 (4)	0.0156 (4)	0.0038 (3)	0.0038 (3)	0.0069 (4)
C27	0.0193 (4)	0.0156 (5)	0.0172 (4)	0.0035 (4)	0.0037 (4)	0.0073 (4)
C28	0.0220 (5)	0.0169 (5)	0.0215 (5)	0.0042 (4)	0.0053 (4)	0.0104 (4)
C29	0.0208 (5)	0.0235 (5)	0.0188 (5)	0.0076 (4)	0.0046 (4)	0.0138 (4)
C30	0.0238 (5)	0.0208 (5)	0.0152 (4)	0.0057 (4)	0.0030 (4)	0.0070 (4)
C31	0.0209 (5)	0.0158 (5)	0.0164 (4)	0.0040 (4)	0.0038 (4)	0.0061 (4)

F1—C3	1.3582 (12)	C13—H13A	0.9300
F2—C14	1.3561 (13)	C14—C15	1.3844 (16)
F3—C23	1.3577 (13)	C15—C16	1.3852 (16)
F4—C29	1.3538 (11)	C15—H15A	0.9300
N1—C7	1.3429 (13)	C16—H16A	0.9300
N1—C8	1.3445 (12)	C17—C20	1.5193 (15)
N2—C8	1.3386 (14)	C17—C18	1.5458 (14)
N2—C9	1.3428 (13)	C17—H17A	0.9800
N3—C8	1.3712 (13)	C18—C19	1.5090 (14)
N3—N4	1.3798 (11)	C18—H18A	0.9700
N3—C17	1.4777 (14)	C18—H18B	0.9700
N4—C19	1.2929 (13)	C19—C26	1.4625 (13)
C1—C2	1.3909 (16)	C20—C21	1.3897 (14)
C1—C6	1.3980 (15)	C20—C25	1.4076 (14)
C1—H1A	0.9300	C21—C22	1.3955 (16)
C2—C3	1.3738 (19)	C21—H21A	0.9300
C2—H2A	0.9300	C22—C23	1.3769 (16)
C3—C4	1.3784 (17)	C22—H22A	0.9300
C4—C5	1.3886 (15)	C23—C24	1.3839 (16)
C4—H4A	0.9300	C24—C25	1.3864 (16)
C5—C6	1.3938 (16)	C24—H24A	0.9300
C5—H5A	0.9300	C25—H25A	0.9300
C6—C7	1.4861 (14)	C26—C27	1.3966 (14)
C7—C10	1.3975 (15)	C26—C31	1.4015 (15)
C9—C10	1.3964 (13)	C27—C28	1.3921 (14)
C9—C11	1.4842 (15)	C27—H27A	0.9300
C10—H10A	0.9300	C28—C29	1.3763 (16)
C11—C12	1.4008 (14)	C28—H28A	0.9300
C11—C16	1.4013 (14)	C29—C30	1.3824 (16)
C12—C13	1.3898 (16)	C30—C31	1.3848 (14)
C12—H12A	0.9300	C30—H30A	0.9300
C13—C14	1.3822 (16)	C31—H31A	0.9300
C7—N1—C8	115.54 (9)	C11—C16—H16A	119.4
C8—N2—C9	116.12 (9)	N3—C17—C20	111.40 (8)
C8—N3—N4	121.04 (9)	N3—C17—C18	100.36 (8)
C8—N3—C17	125.56 (8)	C20—C17—C18	112.75 (8)
N4—N3—C17	113.14 (8)	N3—C17—H17A	110.6
C19—N4—N3	107.85 (8)	C20—C17—H17A	110.6
C2—C1—C6	121.00 (11)	C18—C17—H17A	110.6
C2—C1—H1A	119.5	C19—C18—C17	101.79 (8)
C6—C1—H1A	119.5	C19—C18—H18A	111.4
C3—C2—C1	118.41 (11)	C17—C18—H18A	111.4
C3—C2—H2A	120.8	C19—C18—H18B	111.4
C1—C2—H2A	120.8	C17—C18—H18B	111.4
F1—C3—C2	118.88 (10)	H18A—C18—H18B	109.3
F1—C3—C4	118.40 (11)	N4—C19—C26	120.47 (9)
C2—C3—C4	122.71 (10)	N4—C19—C18	113.62 (8)
C3—C4—C5	118.12 (11)	C26—C19—C18	125.90 (9)
C3—C4—H4A	120.9	C21—C20—C25	118.57 (10)
C5—C4—H4A	120.9	C21—C20—C17	120.88 (9)
C4—C5—C6	121.40 (10)	C25—C20—C17	120.52 (9)
C4—C5—H5A	119.3	C20—C21—C22	120.97 (10)
C6—C5—H5A	119.3	C20—C21—H21A	119.5
C5—C6—C1	118.34 (10)	C22—C21—H21A	119.5
C5—C6—C7	119.64 (9)	C23—C22—C21	118.33 (10)
C1—C6—C7	121.99 (10)	C23—C22—H22A	120.8
N1—C7—C10	121.61 (9)	C21—C22—H22A	120.8
N1—C7—C6	115.61 (9)	F3—C23—C22	118.54 (10)
C10—C7—C6	122.78 (9)	F3—C23—C24	118.54 (10)
N2—C8—N1	127.67 (9)	C22—C23—C24	122.93 (11)
N2—C8—N3	117.20 (9)	C23—C24—C25	117.86 (10)
N1—C8—N3	115.12 (9)	C23—C24—H24A	121.1
N2—C9—C10	121.18 (10)	C25—C24—H24A	121.1
N2—C9—C11	115.31 (9)	C24—C25—C20	121.28 (10)
C10—C9—C11	123.50 (9)	C24—C25—H25A	119.4
C9—C10—C7	117.85 (9)	C20—C25—H25A	119.4
C9—C10—H10A	121.1	C27—C26—C31	119.09 (9)
C7—C10—H10A	121.1	C27—C26—C19	120.48 (9)
C12—C11—C16	118.56 (10)	C31—C26—C19	120.37 (9)
C12—C11—C9	119.53 (9)	C28—C27—C26	120.75 (10)
C16—C11—C9	121.91 (9)	C28—C27—H27A	119.6
C13—C12—C11	120.98 (10)	C26—C27—H27A	119.6
C13—C12—H12A	119.5	C29—C28—C27	118.12 (10)
C11—C12—H12A	119.5	C29—C28—H28A	120.9
C14—C13—C12	118.31 (10)	C27—C28—H28A	120.9
C14—C13—H13A	120.8	F4—C29—C28	118.58 (10)
C12—C13—H13A	120.8	F4—C29—C30	118.33 (10)
F2—C14—C13	118.70 (10)	C28—C29—C30	123.09 (10)
F2—C14—C15	118.61 (10)	C29—C30—C31	118.24 (10)
C13—C14—C15	122.68 (11)	C29—C30—H30A	120.9
C14—C15—C16	118.22 (10)	C31—C30—H30A	120.9
C14—C15—H15A	120.9	C30—C31—C26	120.72 (10)
C16—C15—H15A	120.9	C30—C31—H31A	119.6
C15—C16—C11	121.23 (10)	C26—C31—H31A	119.6
C15—C16—H16A	119.4
C8—N3—N4—C19	−175.75 (9)	C13—C14—C15—C16	−0.36 (17)
C17—N3—N4—C19	9.72 (12)	C14—C15—C16—C11	−0.41 (16)
C6—C1—C2—C3	0.5 (2)	C12—C11—C16—C15	0.57 (16)
C1—C2—C3—F1	179.84 (13)	C9—C11—C16—C15	−179.29 (10)
C1—C2—C3—C4	−1.1 (2)	C8—N3—C17—C20	−71.63 (12)
F1—C3—C4—C5	179.83 (11)	N4—N3—C17—C20	102.61 (9)
C2—C3—C4—C5	0.8 (2)	C8—N3—C17—C18	168.78 (10)
C3—C4—C5—C6	0.17 (19)	N4—N3—C17—C18	−16.98 (11)
C4—C5—C6—C1	−0.74 (18)	N3—C17—C18—C19	16.42 (10)
C4—C5—C6—C7	−178.88 (10)	C20—C17—C18—C19	−102.19 (10)
C2—C1—C6—C5	0.4 (2)	N3—N4—C19—C26	−177.14 (9)
C2—C1—C6—C7	178.49 (12)	N3—N4—C19—C18	2.85 (12)
C8—N1—C7—C10	−1.71 (14)	C17—C18—C19—N4	−13.07 (12)
C8—N1—C7—C6	177.45 (9)	C17—C18—C19—C26	166.92 (10)
C5—C6—C7—N1	7.77 (14)	N3—C17—C20—C21	125.54 (10)
C1—C6—C7—N1	−170.30 (11)	C18—C17—C20—C21	−122.51 (10)
C5—C6—C7—C10	−173.07 (10)	N3—C17—C20—C25	−56.48 (12)
C1—C6—C7—C10	8.86 (17)	C18—C17—C20—C25	55.47 (13)
C9—N2—C8—N1	−0.24 (16)	C25—C20—C21—C22	−0.77 (16)
C9—N2—C8—N3	178.53 (9)	C17—C20—C21—C22	177.25 (10)
C7—N1—C8—N2	1.70 (15)	C20—C21—C22—C23	−1.41 (17)
C7—N1—C8—N3	−177.10 (9)	C21—C22—C23—F3	−177.53 (10)
N4—N3—C8—N2	−3.49 (14)	C21—C22—C23—C24	2.47 (18)
C17—N3—C8—N2	170.33 (9)	F3—C23—C24—C25	178.77 (10)
N4—N3—C8—N1	175.44 (9)	C22—C23—C24—C25	−1.23 (18)
C17—N3—C8—N1	−10.74 (15)	C23—C24—C25—C20	−1.09 (17)
C8—N2—C9—C10	−1.20 (14)	C21—C20—C25—C24	2.06 (16)
C8—N2—C9—C11	178.28 (9)	C17—C20—C25—C24	−175.97 (10)
N2—C9—C10—C7	1.11 (15)	N4—C19—C26—C27	175.99 (10)
C11—C9—C10—C7	−178.34 (9)	C18—C19—C26—C27	−4.00 (16)
N1—C7—C10—C9	0.45 (15)	N4—C19—C26—C31	−1.19 (15)
C6—C7—C10—C9	−178.66 (9)	C18—C19—C26—C31	178.82 (10)
N2—C9—C11—C12	2.11 (14)	C31—C26—C27—C28	0.63 (16)
C10—C9—C11—C12	−178.42 (10)	C19—C26—C27—C28	−176.58 (10)
N2—C9—C11—C16	−178.03 (9)	C26—C27—C28—C29	−0.32 (16)
C10—C9—C11—C16	1.44 (16)	C27—C28—C29—F4	179.78 (10)
C16—C11—C12—C13	0.02 (16)	C27—C28—C29—C30	0.15 (17)
C9—C11—C12—C13	179.89 (10)	F4—C29—C30—C31	−179.93 (10)
C11—C12—C13—C14	−0.74 (17)	C28—C29—C30—C31	−0.31 (17)
C12—C13—C14—F2	−178.73 (10)	C29—C30—C31—C26	0.62 (16)
C12—C13—C14—C15	0.93 (18)	C27—C26—C31—C30	−0.79 (16)
F2—C14—C15—C16	179.29 (10)	C19—C26—C31—C30	176.43 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F4i	0.93	2.43	3.2759 (16)	151
C31—H31A···F3ii	0.93	2.53	3.3208 (14)	143
C1—H1A···Cg5iii	0.93	2.98	3.7144 (14)	137
C15—H15A···Cg5iv	0.93	2.74	3.6459 (13)	166

Table 1

Hydrogen-bond geometry (Å, °)

Cg5 is the centroid of the C20–C25 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯F4i	0.93	2.43	3.2759 (16)	151
C31—H31A⋯F3ii	0.93	2.53	3.3208 (14)	143
C1—H1A⋯Cg5iii	0.93	2.98	3.7144 (14)	137
C15—H15A⋯Cg5iv	0.93	2.74	3.6459 (13)	166

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