Crystal structure of [4-(2-meth-oxy-phen-yl)-3-methyl-1-phenyl-6-tri-fluoro-methyl-1H-pyrazolo-[3,4-b]pyridin-5-yl](thio-phen-2-yl)methanone.

The title compound, C26H18F3N3O2S, a 2-meth-oxy-substituted derivative, is closely related to its 4-methyl- and 4-chloro-substituted analogues and yet displays no structural relationships with them. The thio-phene ring is disorder free and the -CF3 group exhibits disorder, respectively, in contrast and similar to that observed in the 4-methyl- and 4-chloro-substituted derivatives. The torsion angle which defines the twist of the thio-phene ring is -69.6 (2)° (gauche) in the title compound, whereas it is anti-clinal in the 4-methyl- and 4-chloro-substituted derivatives, with respective values of 99.9 (2) and 99.3 (2)°. The absence of disorder in the thio-phene ring facilitates one of its ring C atoms to participate in the lone inter-molecular C-H⋯O hydrogen bond present in the crystal, leading to a characteristic C(5) chain graph-set motif linking mol-ecules related through glides along [010]. An intra-moleculr C-H⋯N hydrogen bond also occurs.

Related literature

For the biological activity of 1H-pyrazolo­[3,4-b]pyridines, see: Hardy (1984 ▶); Chu & Lynch (1975 ▶); Ali (2009 ▶); Wilson et al. (2013 ▶); Souza et al. (2012 ▶). For applications of thio­phene ring systems in solar cells, see: Hara et al. (2003 ▶). For related structures, see: Rajni Swamy et al. (2013 ▶). For the treatment of disorders in crystal structures, see: Müller (2009 ▶). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C26H18F3N3O2S

M = 493.49

Monoclinic,

a = 18.9343 (11) Å

b = 11.6347 (6) Å

c = 20.9800 (12) Å

β = 92.511 (2)°

V = 4617.3 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.19 mm−1

T = 301 K

0.25 × 0.16 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.949, T max = 0.979

23854 measured reflections

5492 independent reflections

3784 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.138

S = 1.02

5492 reflections

346 parameters

142 restraints

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL2013.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814017437/hg5397sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814017437/hg5397Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814017437/hg5397Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814017437/hg5397fig1.tif

Mol­ecular structure of (I) showing the atom numbering scheme and displacement ellipsoids drawn at the 50% probability level. H atoms and atoms of minor disorder components have been omitted for clarity.

Click here for additional data file.

. DOI: 10.1107/S1600536814017437/hg5397fig2.tif

Overlay of the mol­ecular structures of (I) (blue), 4- methyl (red) and 4-chloro (green) analogues. H atoms and atoms of minor disordered components were not included in the least squares fit of the atomic positions.

Click here for additional data file.

. DOI: 10.1107/S1600536814017437/hg5397fig3.tif

C—H⋯O hydrogen bond linking mol­ecules through chains extending infinitely along [010]. Non-participating ring atoms and groups have been omitted for clarity.

CCDC reference: 1016829

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

C26H18F3N3O2S	F(000) = 2032
Mr = 493.49	Dx = 1.420 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.9343 (11) Å	Cell parameters from 2784 reflections
b = 11.6347 (6) Å	θ = 2.1–28.0°
c = 20.9800 (12) Å	µ = 0.19 mm−1
β = 92.511 (2)°	T = 301 K
V = 4617.3 (4) Å3	Needle, yellow
Z = 8	0.25 × 0.16 × 0.12 mm

Bruker SMART APEXII CCD diffractometer	3784 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
ω and φ scans	θmax = 28.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −24→24
Tmin = 0.949, Tmax = 0.979	k = −13→15
23854 measured reflections	l = −27→27
5492 independent reflections

Refinement on F2	142 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.0601P)2 + 3.2782P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
5492 reflections	Δρmax = 0.33 e Å−3
346 parameters	Δρmin = −0.47 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.30751 (9)	0.60534 (13)	0.20858 (9)	0.0688 (5)
O2	0.11454 (7)	0.93337 (12)	0.14944 (7)	0.0548 (4)
N1	0.30027 (8)	1.00767 (14)	0.01120 (7)	0.0406 (4)
N2	0.23413 (8)	1.00212 (16)	−0.01836 (7)	0.0499 (4)
N3	0.36085 (7)	0.91418 (13)	0.10024 (7)	0.0389 (3)
C1	0.19684 (10)	0.92676 (18)	0.01270 (9)	0.0455 (5)
C2	0.23793 (9)	0.88016 (16)	0.06502 (8)	0.0373 (4)
C3	0.22736 (9)	0.80476 (15)	0.11561 (8)	0.0370 (4)
C4	0.28594 (9)	0.78276 (15)	0.15652 (8)	0.0375 (4)
C5	0.35026 (9)	0.83882 (16)	0.14613 (9)	0.0392 (4)
C25	0.41493 (11)	0.8173 (2)	0.18938 (11)	0.0554 (5)
F1	0.46297 (8)	0.89725 (17)	0.18471 (9)	0.0956 (8)	0.958 (3)
F2	0.44581 (9)	0.71752 (16)	0.17541 (10)	0.0964 (7)	0.958 (3)
F3	0.39939 (8)	0.80892 (16)	0.25001 (7)	0.0786 (6)	0.958 (3)
F1A	0.4098 (16)	0.7207 (9)	0.2222 (10)	0.098 (8)	0.042 (3)
F2A	0.4215 (12)	0.9027 (11)	0.2288 (9)	0.089 (8)	0.042 (3)
F3A	0.4718 (10)	0.8067 (10)	0.1573 (10)	0.070 (7)	0.042 (3)
C6	0.30449 (9)	0.93290 (15)	0.06141 (8)	0.0359 (4)
C7	0.27888 (10)	0.69865 (16)	0.21061 (10)	0.0449 (4)
C8	0.23554 (11)	0.73371 (17)	0.26263 (9)	0.0455 (5)
S1	0.20657 (4)	0.63331 (6)	0.31536 (3)	0.0750 (2)
C9	0.16353 (14)	0.7348 (3)	0.35569 (11)	0.0755 (8)
H9	0.1372	0.7189	0.3911	0.091*
C10	0.17100 (13)	0.8413 (2)	0.33156 (10)	0.0654 (6)
H10	0.1514	0.9071	0.3487	0.078*
C11	0.21214 (11)	0.84097 (18)	0.27723 (9)	0.0510 (5)
H11	0.2222	0.9065	0.2539	0.061*
C12	0.34875 (9)	1.09282 (17)	−0.00852 (8)	0.0406 (4)
C13	0.41925 (10)	1.08884 (18)	0.01057 (10)	0.0488 (5)
H13	0.4367	1.0284	0.0357	0.059*
C14	0.46389 (12)	1.1758 (2)	−0.00798 (11)	0.0596 (6)
H14	0.5114	1.1741	0.0053	0.072*
C15	0.43889 (13)	1.2640 (2)	−0.04558 (13)	0.0725 (7)
H15	0.4694	1.3213	−0.0585	0.087*
C16	0.36868 (14)	1.2678 (2)	−0.06417 (15)	0.0842 (9)
H16	0.3515	1.3283	−0.0893	0.101*
C17	0.32333 (12)	1.1824 (2)	−0.04591 (12)	0.0667 (7)
H17	0.2757	1.1852	−0.0588	0.080*
C18	0.15781 (10)	0.75027 (16)	0.12743 (8)	0.0400 (4)
C19	0.10172 (10)	0.81792 (17)	0.14666 (9)	0.0440 (4)
C20	0.03917 (11)	0.7667 (2)	0.16311 (11)	0.0573 (6)
H20	0.0019	0.8116	0.1763	0.069*
C21	0.03220 (12)	0.6485 (2)	0.15987 (12)	0.0641 (6)
H21	−0.0099	0.6144	0.1710	0.077*
C22	0.08657 (13)	0.5807 (2)	0.14044 (11)	0.0613 (6)
H22	0.0812	0.5014	0.1380	0.074*
C23	0.14961 (11)	0.63175 (17)	0.12456 (10)	0.0495 (5)
H23	0.1868	0.5861	0.1119	0.059*
C24	0.12313 (11)	0.8992 (2)	−0.01037 (11)	0.0665 (7)
H24A	0.1138	0.9338	−0.0514	0.100*
H24B	0.0904	0.9288	0.0193	0.100*
H24C	0.1177	0.8174	−0.0138	0.100*
C26	0.06586 (14)	1.0042 (2)	0.18061 (14)	0.0743 (7)
H26A	0.0214	1.0044	0.1567	0.112*
H26B	0.0840	1.0812	0.1835	0.112*
H26C	0.0592	0.9751	0.2227	0.112*

	U11	U22	U33	U12	U13	U23
O1	0.0734 (11)	0.0386 (8)	0.0952 (12)	0.0074 (7)	0.0113 (9)	0.0132 (8)
O2	0.0483 (8)	0.0456 (8)	0.0721 (10)	−0.0016 (6)	0.0197 (7)	−0.0015 (7)
N1	0.0333 (8)	0.0520 (9)	0.0364 (8)	−0.0078 (7)	0.0016 (6)	0.0040 (7)
N2	0.0375 (9)	0.0686 (11)	0.0432 (9)	−0.0097 (8)	−0.0022 (7)	0.0082 (8)
N3	0.0315 (8)	0.0438 (9)	0.0415 (8)	−0.0028 (6)	0.0038 (6)	0.0008 (7)
C1	0.0367 (10)	0.0603 (12)	0.0394 (10)	−0.0101 (9)	0.0013 (8)	0.0003 (9)
C2	0.0309 (9)	0.0444 (10)	0.0371 (9)	−0.0054 (7)	0.0053 (7)	−0.0052 (7)
C3	0.0349 (9)	0.0358 (9)	0.0409 (9)	−0.0054 (7)	0.0076 (7)	−0.0058 (7)
C4	0.0372 (9)	0.0320 (9)	0.0437 (10)	−0.0018 (7)	0.0059 (7)	−0.0018 (7)
C5	0.0345 (9)	0.0388 (9)	0.0443 (10)	−0.0007 (7)	0.0032 (7)	−0.0006 (7)
C25	0.0414 (11)	0.0599 (13)	0.0644 (13)	−0.0066 (9)	−0.0044 (9)	0.0167 (10)
F1	0.0582 (10)	0.1105 (14)	0.1143 (15)	−0.0439 (10)	−0.0387 (9)	0.0573 (12)
F2	0.0649 (11)	0.0951 (13)	0.1280 (16)	0.0346 (9)	−0.0088 (10)	0.0119 (11)
F3	0.0646 (9)	0.1126 (15)	0.0571 (8)	−0.0194 (9)	−0.0157 (7)	0.0211 (8)
F1A	0.098 (17)	0.106 (11)	0.089 (18)	0.005 (15)	−0.005 (13)	0.060 (11)
F2A	0.052 (15)	0.118 (12)	0.093 (16)	0.008 (15)	−0.036 (11)	−0.029 (11)
F3A	0.025 (5)	0.099 (18)	0.084 (15)	−0.028 (11)	−0.011 (6)	−0.006 (11)
C6	0.0335 (9)	0.0407 (9)	0.0339 (8)	−0.0034 (7)	0.0068 (7)	−0.0035 (7)
C7	0.0422 (10)	0.0363 (10)	0.0560 (12)	−0.0066 (8)	−0.0014 (8)	0.0067 (8)
C8	0.0496 (11)	0.0415 (11)	0.0452 (10)	−0.0113 (8)	−0.0014 (8)	0.0121 (8)
S1	0.0858 (5)	0.0661 (4)	0.0737 (4)	−0.0167 (3)	0.0118 (3)	0.0319 (3)
C9	0.0747 (17)	0.104 (2)	0.0486 (13)	−0.0226 (15)	0.0098 (12)	0.0209 (13)
C10	0.0702 (16)	0.0812 (17)	0.0453 (12)	−0.0061 (13)	0.0086 (11)	−0.0028 (11)
C11	0.0610 (13)	0.0492 (12)	0.0433 (10)	−0.0064 (10)	0.0069 (9)	0.0045 (9)
C12	0.0378 (10)	0.0486 (11)	0.0359 (9)	−0.0071 (8)	0.0082 (7)	0.0004 (8)
C13	0.0396 (10)	0.0526 (12)	0.0546 (11)	−0.0029 (9)	0.0067 (9)	0.0088 (9)
C14	0.0400 (11)	0.0694 (15)	0.0698 (14)	−0.0124 (10)	0.0074 (10)	0.0104 (12)
C15	0.0577 (15)	0.0693 (16)	0.0910 (19)	−0.0201 (12)	0.0091 (13)	0.0257 (14)
C16	0.0652 (17)	0.0789 (18)	0.108 (2)	−0.0117 (14)	−0.0018 (15)	0.0485 (17)
C17	0.0458 (12)	0.0777 (16)	0.0758 (15)	−0.0090 (11)	−0.0058 (11)	0.0299 (13)
C18	0.0386 (10)	0.0442 (10)	0.0375 (9)	−0.0105 (8)	0.0044 (7)	−0.0020 (7)
C19	0.0399 (10)	0.0490 (11)	0.0433 (10)	−0.0076 (8)	0.0051 (8)	0.0008 (8)
C20	0.0391 (11)	0.0674 (15)	0.0664 (14)	−0.0090 (10)	0.0127 (10)	0.0022 (11)
C21	0.0473 (13)	0.0717 (16)	0.0743 (15)	−0.0273 (11)	0.0128 (11)	0.0011 (12)
C22	0.0650 (15)	0.0510 (13)	0.0682 (14)	−0.0282 (11)	0.0063 (11)	−0.0068 (11)
C23	0.0504 (12)	0.0463 (11)	0.0523 (11)	−0.0131 (9)	0.0070 (9)	−0.0079 (9)
C24	0.0428 (12)	0.0990 (19)	0.0567 (13)	−0.0215 (12)	−0.0099 (10)	0.0125 (12)
C26	0.0680 (16)	0.0596 (15)	0.0976 (19)	0.0103 (12)	0.0274 (14)	−0.0030 (13)

O1—C7	1.215 (2)	C10—C11	1.408 (3)
O2—C19	1.366 (2)	C10—H10	0.9300
O2—C26	1.418 (3)	C11—H11	0.9300
N1—C6	1.366 (2)	C12—C13	1.378 (3)
N1—N2	1.374 (2)	C12—C17	1.378 (3)
N1—C12	1.424 (2)	C13—C14	1.385 (3)
N2—C1	1.316 (2)	C13—H13	0.9300
N3—C5	1.324 (2)	C14—C15	1.367 (3)
N3—C6	1.332 (2)	C14—H14	0.9300
C1—C2	1.425 (3)	C15—C16	1.370 (4)
C1—C24	1.492 (3)	C15—H15	0.9300
C2—C3	1.398 (2)	C16—C17	1.379 (3)
C2—C6	1.407 (2)	C16—H16	0.9300
C3—C4	1.396 (3)	C17—H17	0.9300
C3—C18	1.492 (2)	C18—C23	1.389 (3)
C4—C5	1.407 (2)	C18—C19	1.396 (3)
C4—C7	1.509 (3)	C19—C20	1.383 (3)
C5—C25	1.512 (3)	C20—C21	1.383 (3)
C25—F2A	1.295 (12)	C20—H20	0.9300
C25—F3A	1.301 (11)	C21—C22	1.373 (3)
C25—F1	1.308 (2)	C21—H21	0.9300
C25—F3	1.322 (3)	C22—C23	1.387 (3)
C25—F1A	1.324 (12)	C22—H22	0.9300
C25—F2	1.338 (3)	C23—H23	0.9300
C7—C8	1.452 (3)	C24—H24A	0.9600
C8—C11	1.364 (3)	C24—H24B	0.9600
C8—S1	1.7153 (18)	C24—H24C	0.9600
S1—C9	1.683 (3)	C26—H26A	0.9600
C9—C10	1.349 (4)	C26—H26B	0.9600
C9—H9	0.9300	C26—H26C	0.9600
C19—O2—C26	118.27 (16)	C8—C11—H11	123.8
C6—N1—N2	109.85 (14)	C10—C11—H11	123.8
C6—N1—C12	130.57 (15)	C13—C12—C17	120.05 (18)
N2—N1—C12	119.19 (15)	C13—C12—N1	121.39 (17)
C1—N2—N1	107.80 (15)	C17—C12—N1	118.53 (17)
C5—N3—C6	114.23 (15)	C12—C13—C14	119.3 (2)
N2—C1—C2	110.39 (16)	C12—C13—H13	120.4
N2—C1—C24	119.79 (18)	C14—C13—H13	120.4
C2—C1—C24	129.78 (18)	C15—C14—C13	120.7 (2)
C3—C2—C6	118.23 (16)	C15—C14—H14	119.6
C3—C2—C1	137.08 (16)	C13—C14—H14	119.6
C6—C2—C1	104.64 (15)	C14—C15—C16	119.7 (2)
C4—C3—C2	116.46 (15)	C14—C15—H15	120.2
C4—C3—C18	120.20 (16)	C16—C15—H15	120.2
C2—C3—C18	123.33 (16)	C15—C16—C17	120.4 (2)
C3—C4—C5	119.31 (16)	C15—C16—H16	119.8
C3—C4—C7	119.15 (15)	C17—C16—H16	119.8
C5—C4—C7	121.54 (16)	C12—C17—C16	119.8 (2)
N3—C5—C4	125.40 (17)	C12—C17—H17	120.1
N3—C5—C25	113.67 (16)	C16—C17—H17	120.1
C4—C5—C25	120.92 (17)	C23—C18—C19	119.18 (17)
F2A—C25—F3A	110.1 (10)	C23—C18—C3	120.83 (17)
F1—C25—F3	108.0 (2)	C19—C18—C3	119.79 (16)
F2A—C25—F1A	109.1 (11)	O2—C19—C20	124.45 (19)
F3A—C25—F1A	105.6 (11)	O2—C19—C18	115.52 (16)
F1—C25—F2	106.8 (2)	C20—C19—C18	119.99 (19)
F3—C25—F2	105.34 (18)	C21—C20—C19	119.8 (2)
F2A—C25—C5	108.0 (12)	C21—C20—H20	120.1
F3A—C25—C5	111.9 (12)	C19—C20—H20	120.1
F1—C25—C5	112.64 (17)	C22—C21—C20	121.0 (2)
F3—C25—C5	112.41 (17)	C22—C21—H21	119.5
F1A—C25—C5	112.1 (15)	C20—C21—H21	119.5
F2—C25—C5	111.24 (19)	C21—C22—C23	119.3 (2)
N3—C6—N1	126.45 (15)	C21—C22—H22	120.3
N3—C6—C2	126.26 (16)	C23—C22—H22	120.3
N1—C6—C2	107.28 (15)	C22—C23—C18	120.7 (2)
O1—C7—C8	123.01 (18)	C22—C23—H23	119.7
O1—C7—C4	119.93 (18)	C18—C23—H23	119.7
C8—C7—C4	117.04 (16)	C1—C24—H24A	109.5
C11—C8—C7	128.73 (17)	C1—C24—H24B	109.5
C11—C8—S1	111.23 (15)	H24A—C24—H24B	109.5
C7—C8—S1	120.04 (15)	C1—C24—H24C	109.5
C9—S1—C8	91.27 (11)	H24A—C24—H24C	109.5
C10—C9—S1	113.26 (19)	H24B—C24—H24C	109.5
C10—C9—H9	123.4	O2—C26—H26A	109.5
S1—C9—H9	123.4	O2—C26—H26B	109.5
C9—C10—C11	111.8 (2)	H26A—C26—H26B	109.5
C9—C10—H10	124.1	O2—C26—H26C	109.5
C11—C10—H10	124.1	H26A—C26—H26C	109.5
C8—C11—C10	112.40 (19)	H26B—C26—H26C	109.5
C6—N1—N2—C1	0.8 (2)	C3—C4—C7—O1	108.7 (2)
C12—N1—N2—C1	−172.79 (16)	C5—C4—C7—O1	−70.8 (3)
N1—N2—C1—C2	0.5 (2)	C3—C4—C7—C8	−69.6 (2)
N1—N2—C1—C24	−177.61 (19)	C5—C4—C7—C8	110.8 (2)
N2—C1—C2—C3	175.6 (2)	O1—C7—C8—C11	165.9 (2)
C24—C1—C2—C3	−6.5 (4)	C4—C7—C8—C11	−15.8 (3)
N2—C1—C2—C6	−1.5 (2)	O1—C7—C8—S1	−14.5 (3)
C24—C1—C2—C6	176.4 (2)	C4—C7—C8—S1	163.82 (14)
C6—C2—C3—C4	−3.8 (2)	C11—C8—S1—C9	0.30 (18)
C1—C2—C3—C4	179.4 (2)	C7—C8—S1—C9	−179.34 (18)
C6—C2—C3—C18	175.34 (16)	C8—S1—C9—C10	−0.9 (2)
C1—C2—C3—C18	−1.5 (3)	S1—C9—C10—C11	1.3 (3)
C2—C3—C4—C5	1.9 (2)	C7—C8—C11—C10	180.0 (2)
C18—C3—C4—C5	−177.30 (16)	S1—C8—C11—C10	0.4 (2)
C2—C3—C4—C7	−177.68 (16)	C9—C10—C11—C8	−1.0 (3)
C18—C3—C4—C7	3.2 (2)	C6—N1—C12—C13	20.4 (3)
C6—N3—C5—C4	−1.6 (3)	N2—N1—C12—C13	−167.57 (18)
C6—N3—C5—C25	179.31 (16)	C6—N1—C12—C17	−157.6 (2)
C3—C4—C5—N3	1.0 (3)	N2—N1—C12—C17	14.4 (3)
C7—C4—C5—N3	−179.50 (17)	C17—C12—C13—C14	0.3 (3)
C3—C4—C5—C25	180.00 (18)	N1—C12—C13—C14	−177.73 (19)
C7—C4—C5—C25	−0.5 (3)	C12—C13—C14—C15	−0.9 (4)
N3—C5—C25—F2A	78.0 (6)	C13—C14—C15—C16	1.2 (4)
C4—C5—C25—F2A	−101.2 (6)	C14—C15—C16—C17	−0.9 (5)
N3—C5—C25—F3A	−43.4 (6)	C13—C12—C17—C16	0.1 (4)
C4—C5—C25—F3A	137.5 (5)	N1—C12—C17—C16	178.1 (2)
N3—C5—C25—F1	17.1 (3)	C15—C16—C17—C12	0.2 (5)
C4—C5—C25—F1	−162.1 (2)	C4—C3—C18—C23	−63.7 (2)
N3—C5—C25—F3	139.40 (19)	C2—C3—C18—C23	117.2 (2)
C4—C5—C25—F3	−39.7 (3)	C4—C3—C18—C19	111.1 (2)
N3—C5—C25—F1A	−161.8 (5)	C2—C3—C18—C19	−68.0 (2)
C4—C5—C25—F1A	19.0 (6)	C26—O2—C19—C20	10.7 (3)
N3—C5—C25—F2	−102.7 (2)	C26—O2—C19—C18	−167.4 (2)
C4—C5—C25—F2	78.1 (2)	C23—C18—C19—O2	178.74 (17)
C5—N3—C6—N1	178.56 (17)	C3—C18—C19—O2	3.9 (3)
C5—N3—C6—C2	−0.6 (3)	C23—C18—C19—C20	0.6 (3)
N2—N1—C6—N3	178.99 (17)	C3—C18—C19—C20	−174.29 (19)
C12—N1—C6—N3	−8.4 (3)	O2—C19—C20—C21	−178.6 (2)
N2—N1—C6—C2	−1.7 (2)	C18—C19—C20—C21	−0.6 (3)
C12—N1—C6—C2	170.89 (17)	C19—C20—C21—C22	−0.1 (4)
C3—C2—C6—N3	3.4 (3)	C20—C21—C22—C23	0.7 (4)
C1—C2—C6—N3	−178.80 (17)	C21—C22—C23—C18	−0.8 (3)
C3—C2—C6—N1	−175.90 (15)	C19—C18—C23—C22	0.1 (3)
C1—C2—C6—N1	1.87 (19)	C3—C18—C23—C22	174.91 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N3	0.93	2.42	3.012 (2)	122
C11—H11···O1i	0.93	2.51	3.114 (3)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯N3	0.93	2.42	3.012 (2)	122
C11—H11⋯O1i	0.93	2.51	3.114 (3)	122

Symmetry code: (i) .