1-{2-Phenyl-2-[4-(trifluoro-meth-yl)-benzyl-oxy]eth-yl}-1H-benzimidazole.

The asymmetric unit of the crystal structure of the title compound, C(23)H(19)F(3)N(2)O, contains two independent mol-ecules. In the two mol-ecules the planar benzimidazole ring systems are oriented with respect to the phen-yl/trifluoro-methyl-benzene rings at dihedral angles of 9.62 (6)/78.63 (7) and 2.53 (8)/83.83 (9)°. In the crystal structure, inter-molecular C-H⋯N hydrogen bonds link the mol-ecules into R(2) (2)(6) dimers. The mol-ecules are elongated along [001] and stacked along the b axis.

Related literature

For general background, see: Brammer & Feczko (1988 ▶); Özel Güven et al. (2007a ▶,b ▶). For related literature, see: Song & Shin (1998 ▶); Freer et al. (1986 ▶); Peeters et al. (1996 ▶, 1979a ▶,b ▶); Caira et al. (2004 ▶); Özel Güven et al. (2008a ▶,b ▶). For ring motif details, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C23H19F3N2O

M = 396.40

Monoclinic,

a = 39.3006 (15) Å

b = 9.5834 (2) Å

c = 23.0120 (9) Å

β = 113.668 (1)°

V = 7938.1 (5) Å3

Z = 16

Mo Kα radiation

μ = 0.10 mm−1

T = 120 (2) K

0.35 × 0.2 × 0.14 mm

Data collection

Bruker Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.974, T max = 0.984

28014 measured reflections

8735 independent reflections

5066 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.227

S = 1.06

8735 reflections

524 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.59 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024033/xu2445sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024033/xu2445Isup2.hkl

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

C23H19F3N2O	F000 = 3296
Mr = 396.40	Dx = 1.327 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8156 reflections
a = 39.3006 (15) Å	θ = 2.9–27.5º
b = 9.5834 (2) Å	µ = 0.10 mm−1
c = 23.0120 (9) Å	T = 120 (2) K
β = 113.6680 (10)º	Shard, colourless
V = 7938.1 (5) Å3	0.35 × 0.2 × 0.14 mm
Z = 16

Bruker Nonius KappaCCD diffractometer	8735 independent reflections
Radiation source: fine-focus sealed tube	5066 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.072
Detector resolution: 9.091 pixels mm-1	θmax = 27.5º
T = 120(2) K	θmin = 3.1º
φ and ω scans	h = −50→39
Absorption correction: multi-scan(SADABS; Sheldrick, 2007)	k = −10→11
Tmin = 0.974, Tmax = 0.984	l = −29→29
28014 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.081	w = 1/[σ2(Fo2) + (0.117P)2 + 2.4537P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.227	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.62 e Å−3
8735 reflections	Δρmin = −0.59 e Å−3
524 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0062 (4)
Secondary atom site location: difference Fourier map

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	−0.00131 (8)	0.4243 (2)	0.64336 (15)	0.0898 (10)
F2	0.01662 (7)	0.6106 (3)	0.69271 (12)	0.0802 (8)
F3	−0.02789 (6)	0.6169 (3)	0.60373 (13)	0.0929 (10)
O	0.10852 (5)	0.78467 (16)	0.49859 (8)	0.0227 (4)
N1	0.15853 (6)	1.0225 (2)	0.52907 (10)	0.0225 (5)
N2	0.17053 (6)	1.1149 (2)	0.62514 (11)	0.0299 (6)
C1	0.14498 (8)	1.0792 (3)	0.56973 (13)	0.0268 (6)
H1	0.1197	1.0917	0.5591	0.032*
C2	0.20392 (7)	1.0775 (3)	0.62118 (13)	0.0251 (6)
C3	0.24023 (8)	1.0885 (3)	0.66600 (14)	0.0329 (7)
H3	0.2455	1.1252	0.7061	0.039*
C4	0.26834 (8)	1.0430 (3)	0.64890 (15)	0.0386 (8)
H4	0.2928	1.0494	0.6782	0.046*
C5	0.26089 (8)	0.9874 (3)	0.58851 (15)	0.0347 (7)
H5	0.2805	0.9588	0.5786	0.042*
C6	0.22489 (7)	0.9744 (3)	0.54353 (14)	0.0278 (6)
H6	0.2197	0.9371	0.5036	0.033*
C7	0.19684 (7)	1.0200 (2)	0.56120 (13)	0.0235 (6)
C8	0.13789 (7)	0.9648 (3)	0.46651 (12)	0.0240 (6)
H8A	0.1507	0.9866	0.4393	0.029*
H8B	0.1135	1.0077	0.4483	0.029*
C9	0.13351 (7)	0.8071 (2)	0.46865 (12)	0.0218 (6)
H9	0.1576	0.7659	0.4949	0.026*
C10	0.12009 (7)	0.7464 (2)	0.40188 (12)	0.0229 (6)
C11	0.14588 (8)	0.7186 (3)	0.37625 (14)	0.0295 (6)
H11	0.1711	0.7313	0.4008	0.035*
C12	0.13429 (9)	0.6719 (3)	0.31405 (15)	0.0339 (7)
H12	0.1517	0.6544	0.2969	0.041*
C13	0.09678 (9)	0.6513 (3)	0.27756 (14)	0.0346 (7)
H13	0.0889	0.6201	0.2359	0.042*
C14	0.07127 (8)	0.6773 (3)	0.30323 (14)	0.0336 (7)
H14	0.0461	0.6628	0.2788	0.040*
C15	0.08258 (8)	0.7250 (3)	0.36512 (13)	0.0274 (6)
H15	0.0651	0.7426	0.3819	0.033*
C16	0.10907 (8)	0.6442 (2)	0.51903 (13)	0.0253 (6)
H16A	0.1338	0.6210	0.5498	0.030*
H16B	0.1031	0.5817	0.4831	0.030*
C17	0.08146 (7)	0.6250 (2)	0.54841 (12)	0.0232 (6)
C18	0.07287 (8)	0.4897 (3)	0.56064 (13)	0.0279 (6)
H18	0.0841	0.4140	0.5502	0.033*
C19	0.04785 (8)	0.4669 (3)	0.58808 (14)	0.0306 (7)
H19	0.0423	0.3763	0.5959	0.037*
C20	0.03112 (7)	0.5793 (3)	0.60393 (14)	0.0275 (6)
C21	0.03939 (8)	0.7142 (3)	0.59224 (13)	0.0280 (6)
H21	0.0280	0.7895	0.6026	0.034*
C22	0.06473 (7)	0.7369 (3)	0.56503 (12)	0.0242 (6)
H22	0.0705	0.8276	0.5579	0.029*
C23	0.00440 (9)	0.5567 (3)	0.63439 (16)	0.0389 (7)
F1'	0.24560 (6)	0.5820 (2)	0.09554 (12)	0.0674 (7)
F2'	0.23310 (10)	0.3851 (3)	0.05370 (16)	0.1134 (13)
F3'	0.27574 (8)	0.4034 (4)	0.14267 (18)	0.1280 (15)
O'	0.13628 (5)	0.20393 (16)	0.23713 (9)	0.0240 (4)
N1'	0.08787 (6)	−0.0357 (2)	0.20786 (10)	0.0248 (5)
N2'	0.07698 (7)	−0.1235 (2)	0.11146 (11)	0.0294 (5)
C1'	0.10222 (8)	−0.0896 (3)	0.16771 (13)	0.0277 (6)
H1'	0.1276	−0.1013	0.1790	0.033*
C2'	0.04340 (8)	−0.0877 (3)	0.11429 (13)	0.0262 (6)
C3'	0.00741 (8)	−0.0977 (3)	0.06867 (14)	0.0320 (7)
H3'	0.0027	−0.1349	0.0289	0.038*
C4'	−0.02128 (8)	−0.0513 (3)	0.08355 (15)	0.0371 (7)
H4'	−0.0456	−0.0566	0.0532	0.045*
C5'	−0.01454 (9)	0.0040 (3)	0.14381 (16)	0.0398 (8)
H5'	−0.0345	0.0345	0.1525	0.048*
C6'	0.02114 (8)	0.0140 (3)	0.19057 (15)	0.0341 (7)
H6'	0.0257	0.0499	0.2305	0.041*
C7'	0.04969 (7)	−0.0325 (3)	0.17457 (13)	0.0254 (6)
C8'	0.10849 (8)	0.0217 (3)	0.27057 (13)	0.0262 (6)
H8C	0.1330	−0.0202	0.2885	0.031*
H8D	0.0959	−0.0018	0.2978	0.031*
C9'	0.11245 (7)	0.1798 (3)	0.26909 (13)	0.0235 (6)
H9'	0.0881	0.2213	0.2446	0.028*
C10'	0.12750 (7)	0.2370 (2)	0.33608 (12)	0.0228 (6)
C11'	0.10322 (8)	0.2853 (3)	0.36199 (14)	0.0287 (6)
H11'	0.0779	0.2887	0.3370	0.034*
C12'	0.11659 (9)	0.3284 (3)	0.42489 (15)	0.0356 (7)
H12'	0.1002	0.3594	0.4420	0.043*
C13'	0.15418 (9)	0.3251 (3)	0.46192 (14)	0.0357 (7)
H13'	0.1631	0.3544	0.5039	0.043*
C14'	0.17852 (8)	0.2787 (3)	0.43688 (13)	0.0329 (7)
H14'	0.2039	0.2774	0.4621	0.040*
C15'	0.16558 (7)	0.2334 (3)	0.37403 (13)	0.0275 (6)
H15'	0.1822	0.2010	0.3575	0.033*
C16'	0.13615 (7)	0.3468 (2)	0.21945 (13)	0.0225 (6)
H16C	0.1420	0.4057	0.2565	0.027*
H16D	0.1116	0.3719	0.1886	0.027*
C17'	0.16427 (7)	0.3700 (2)	0.19148 (12)	0.0221 (6)
C18'	0.17043 (7)	0.5057 (3)	0.17587 (13)	0.0250 (6)
H18'	0.1571	0.5791	0.1831	0.030*
C19'	0.19571 (8)	0.5330 (3)	0.15004 (14)	0.0292 (6)
H19'	0.1993	0.6240	0.1397	0.035*
C20'	0.21595 (8)	0.4242 (3)	0.13926 (14)	0.0296 (6)
C21'	0.21006 (8)	0.2884 (3)	0.15450 (14)	0.0284 (6)
H21'	0.2235	0.2153	0.1474	0.034*
C22'	0.18436 (7)	0.2614 (3)	0.18011 (12)	0.0242 (6)
H22'	0.1805	0.1701	0.1898	0.029*
C23'	0.24321 (10)	0.4507 (3)	0.11059 (19)	0.0450 (9)

	U11	U22	U33	U12	U13	U23
F1	0.112 (2)	0.0504 (13)	0.161 (3)	−0.0173 (12)	0.111 (2)	0.0023 (14)
F2	0.0848 (18)	0.120 (2)	0.0586 (16)	−0.0341 (15)	0.0520 (15)	−0.0158 (14)
F3	0.0403 (13)	0.159 (3)	0.092 (2)	0.0345 (14)	0.0405 (14)	0.0613 (18)
O	0.0255 (10)	0.0218 (9)	0.0217 (10)	−0.0001 (7)	0.0105 (8)	0.0015 (7)
N1	0.0235 (12)	0.0243 (11)	0.0194 (12)	−0.0039 (8)	0.0085 (10)	−0.0010 (8)
N2	0.0315 (14)	0.0300 (12)	0.0298 (14)	−0.0060 (9)	0.0141 (12)	−0.0046 (10)
C1	0.0301 (15)	0.0251 (13)	0.0290 (16)	−0.0034 (10)	0.0159 (13)	−0.0008 (11)
C2	0.0263 (14)	0.0235 (12)	0.0236 (15)	−0.0056 (10)	0.0081 (12)	0.0014 (10)
C3	0.0360 (17)	0.0343 (15)	0.0219 (16)	−0.0090 (12)	0.0050 (13)	−0.0018 (11)
C4	0.0251 (16)	0.0440 (17)	0.0346 (19)	−0.0054 (12)	−0.0007 (14)	0.0040 (14)
C5	0.0222 (15)	0.0409 (16)	0.0425 (19)	−0.0034 (12)	0.0143 (14)	0.0031 (13)
C6	0.0256 (15)	0.0330 (14)	0.0253 (16)	−0.0038 (11)	0.0105 (13)	−0.0004 (11)
C7	0.0232 (14)	0.0228 (12)	0.0228 (15)	−0.0042 (10)	0.0077 (12)	0.0013 (10)
C8	0.0232 (14)	0.0281 (13)	0.0191 (14)	−0.0044 (10)	0.0068 (12)	−0.0005 (10)
C9	0.0207 (13)	0.0262 (13)	0.0195 (14)	0.0005 (10)	0.0092 (11)	0.0022 (10)
C10	0.0276 (15)	0.0196 (12)	0.0226 (14)	0.0007 (10)	0.0112 (12)	0.0009 (10)
C11	0.0307 (16)	0.0262 (14)	0.0339 (17)	0.0028 (11)	0.0155 (13)	−0.0027 (11)
C12	0.0438 (19)	0.0306 (14)	0.0354 (18)	0.0029 (12)	0.0243 (16)	−0.0049 (12)
C13	0.053 (2)	0.0256 (14)	0.0233 (16)	0.0008 (12)	0.0134 (15)	−0.0025 (11)
C14	0.0322 (16)	0.0341 (15)	0.0261 (16)	−0.0039 (12)	0.0030 (13)	−0.0043 (12)
C15	0.0288 (15)	0.0285 (14)	0.0260 (16)	0.0007 (11)	0.0123 (13)	0.0004 (11)
C16	0.0338 (16)	0.0188 (12)	0.0247 (15)	0.0033 (10)	0.0133 (13)	0.0029 (10)
C17	0.0240 (14)	0.0262 (13)	0.0171 (14)	−0.0011 (10)	0.0059 (11)	0.0007 (10)
C18	0.0361 (16)	0.0213 (13)	0.0260 (16)	−0.0001 (10)	0.0122 (13)	0.0012 (10)
C19	0.0370 (17)	0.0234 (14)	0.0321 (17)	−0.0046 (11)	0.0148 (14)	0.0032 (11)
C20	0.0233 (14)	0.0316 (14)	0.0277 (16)	−0.0030 (11)	0.0103 (12)	0.0038 (11)
C21	0.0296 (15)	0.0290 (14)	0.0247 (15)	0.0056 (11)	0.0103 (13)	0.0035 (11)
C22	0.0260 (14)	0.0215 (12)	0.0229 (14)	0.0002 (10)	0.0075 (12)	0.0039 (10)
C23	0.0347 (18)	0.0411 (17)	0.043 (2)	−0.0033 (13)	0.0174 (16)	0.0042 (14)
F1'	0.0789 (16)	0.0480 (12)	0.106 (2)	−0.0099 (10)	0.0695 (16)	0.0101 (11)
F2'	0.175 (3)	0.106 (2)	0.126 (3)	−0.068 (2)	0.129 (3)	−0.0539 (19)
F3'	0.0609 (17)	0.180 (3)	0.179 (4)	0.0508 (19)	0.085 (2)	0.112 (3)
O'	0.0301 (10)	0.0218 (9)	0.0262 (11)	−0.0025 (7)	0.0176 (9)	0.0004 (7)
N1'	0.0301 (13)	0.0244 (11)	0.0215 (12)	−0.0065 (9)	0.0120 (11)	−0.0004 (9)
N2'	0.0337 (14)	0.0275 (12)	0.0287 (14)	−0.0057 (9)	0.0143 (11)	−0.0046 (9)
C1'	0.0311 (15)	0.0252 (13)	0.0289 (17)	−0.0043 (11)	0.0141 (13)	−0.0021 (11)
C2'	0.0336 (16)	0.0232 (13)	0.0255 (15)	−0.0082 (10)	0.0157 (13)	−0.0027 (10)
C3'	0.0385 (17)	0.0327 (15)	0.0260 (16)	−0.0113 (12)	0.0142 (14)	−0.0062 (12)
C4'	0.0242 (16)	0.0508 (18)	0.0309 (17)	−0.0106 (12)	0.0053 (13)	−0.0043 (14)
C5'	0.0297 (17)	0.0586 (19)	0.0368 (19)	−0.0087 (14)	0.0192 (15)	−0.0102 (15)
C6'	0.0327 (17)	0.0461 (17)	0.0269 (17)	−0.0099 (13)	0.0155 (14)	−0.0074 (13)
C7'	0.0281 (15)	0.0252 (13)	0.0249 (15)	−0.0098 (10)	0.0128 (12)	−0.0016 (11)
C8'	0.0284 (15)	0.0284 (14)	0.0203 (15)	−0.0072 (10)	0.0082 (12)	0.0001 (11)
C9'	0.0230 (14)	0.0283 (13)	0.0218 (14)	−0.0015 (10)	0.0115 (12)	0.0008 (10)
C10'	0.0267 (14)	0.0199 (12)	0.0224 (14)	−0.0020 (10)	0.0106 (12)	0.0002 (10)
C11'	0.0281 (15)	0.0270 (14)	0.0299 (16)	0.0002 (10)	0.0104 (13)	−0.0022 (11)
C12'	0.048 (2)	0.0298 (14)	0.0359 (18)	−0.0022 (12)	0.0246 (16)	−0.0089 (12)
C13'	0.051 (2)	0.0289 (14)	0.0263 (17)	−0.0093 (13)	0.0145 (15)	−0.0029 (12)
C14'	0.0312 (16)	0.0358 (15)	0.0237 (16)	−0.0106 (12)	0.0025 (13)	0.0032 (12)
C15'	0.0247 (15)	0.0308 (14)	0.0278 (16)	−0.0036 (11)	0.0112 (12)	0.0024 (11)
C16'	0.0242 (14)	0.0210 (12)	0.0231 (14)	−0.0011 (10)	0.0104 (12)	0.0004 (10)
C17'	0.0222 (14)	0.0258 (13)	0.0148 (13)	−0.0036 (10)	0.0036 (11)	−0.0022 (10)
C18'	0.0289 (15)	0.0218 (13)	0.0225 (15)	−0.0002 (10)	0.0085 (12)	−0.0034 (10)
C19'	0.0341 (16)	0.0252 (13)	0.0284 (16)	−0.0070 (11)	0.0127 (13)	0.0019 (11)
C20'	0.0324 (16)	0.0303 (14)	0.0302 (17)	−0.0083 (11)	0.0168 (13)	−0.0022 (11)
C21'	0.0302 (15)	0.0260 (14)	0.0328 (17)	−0.0030 (11)	0.0165 (13)	−0.0043 (11)
C22'	0.0275 (14)	0.0212 (12)	0.0241 (14)	−0.0031 (10)	0.0106 (12)	−0.0014 (10)
C23'	0.047 (2)	0.0380 (18)	0.063 (2)	−0.0060 (14)	0.0353 (19)	0.0021 (15)

F1—C23	1.319 (3)	F1'—C23'	1.318 (3)
F2—C23	1.334 (4)	F2'—C23'	1.360 (4)
F3—C23	1.312 (4)	F3'—C23'	1.276 (4)
O—C9	1.424 (3)	O'—C9'	1.423 (3)
O—C16	1.424 (3)	O'—C16'	1.427 (3)
N1—C1	1.362 (3)	N1'—C1'	1.363 (3)
N1—C7	1.386 (3)	N1'—C7'	1.384 (3)
N1—C8	1.449 (3)	N1'—C8'	1.450 (3)
N2—C1	1.312 (4)	N2'—C1'	1.317 (4)
N2—C2	1.398 (4)	N2'—C2'	1.390 (4)
C1—H1	0.9300	C1'—H1'	0.9300
C2—C3	1.389 (4)	C2'—C3'	1.386 (4)
C3—C4	1.384 (4)	C2'—C7'	1.411 (4)
C3—H3	0.9300	C3'—C4'	1.377 (4)
C4—C5	1.405 (4)	C3'—H3'	0.9300
C4—H4	0.9300	C4'—C5'	1.407 (4)
C5—H5	0.9300	C4'—H4'	0.9300
C6—C5	1.383 (4)	C5'—H5'	0.9300
C6—H6	0.9300	C6'—C5'	1.386 (4)
C7—C2	1.407 (4)	C6'—H6'	0.9300
C7—C6	1.390 (4)	C7'—C6'	1.387 (4)
C8—H8A	0.9700	C8'—H8C	0.9700
C8—H8B	0.9700	C8'—H8D	0.9700
C9—C8	1.524 (3)	C9'—C8'	1.525 (3)
C9—C10	1.525 (4)	C9'—C10'	1.515 (4)
C9—H9	0.9800	C9'—H9'	0.9800
C10—C11	1.388 (4)	C10'—C11'	1.392 (4)
C10—C15	1.389 (4)	C10'—C15'	1.398 (4)
C11—C12	1.390 (4)	C11'—C12'	1.390 (4)
C11—H11	0.9300	C11'—H11'	0.9300
C12—C13	1.387 (4)	C12'—C13'	1.378 (4)
C12—H12	0.9300	C12'—H12'	0.9300
C13—H13	0.9300	C13'—H13'	0.9300
C14—C13	1.375 (4)	C14'—C13'	1.374 (4)
C14—H14	0.9300	C14'—H14'	0.9300
C15—C14	1.388 (4)	C15'—C14'	1.396 (4)
C15—H15	0.9300	C15'—H15'	0.9300
C16—H16A	0.9700	C16'—H16C	0.9700
C16—H16B	0.9700	C16'—H16D	0.9700
C17—C16	1.502 (4)	C17'—C16'	1.502 (4)
C17—C18	1.397 (3)	C17'—C22'	1.394 (4)
C17—C22	1.390 (4)	C18'—C17'	1.396 (3)
C18—C19	1.383 (4)	C18'—C19'	1.372 (4)
C18—H18	0.9300	C18'—H18'	0.9300
C19—H19	0.9300	C19'—C20'	1.393 (4)
C20—C19	1.385 (4)	C19'—H19'	0.9300
C20—C21	1.385 (4)	C20'—C23'	1.488 (4)
C20—C23	1.494 (4)	C21'—C20'	1.391 (4)
C21—H21	0.9300	C21'—H21'	0.9300
C22—C21	1.390 (4)	C22'—C21'	1.383 (4)
C22—H22	0.9300	C22'—H22'	0.9300
C16—O—C9	112.37 (18)	C9'—O'—C16'	112.04 (18)
C1—N1—C7	106.3 (2)	C1'—N1'—C7'	106.5 (2)
C1—N1—C8	128.2 (2)	C1'—N1'—C8'	126.9 (2)
C7—N1—C8	125.4 (2)	C7'—N1'—C8'	126.2 (2)
C1—N2—C2	104.0 (2)	C1'—N2'—C2'	104.3 (2)
N2—C1—N1	114.4 (2)	N2'—C1'—N1'	114.0 (2)
N2—C1—H1	122.8	N2'—C1'—H1'	123.0
N1—C1—H1	122.8	N1'—C1'—H1'	123.0
C3—C2—N2	130.1 (3)	C3'—C2'—N2'	130.3 (3)
C3—C2—C7	119.9 (3)	C3'—C2'—C7'	119.6 (3)
N2—C2—C7	110.1 (2)	N2'—C2'—C7'	110.1 (2)
C4—C3—C2	117.7 (3)	C4'—C3'—C2'	118.6 (3)
C4—C3—H3	121.2	C4'—C3'—H3'	120.7
C2—C3—H3	121.2	C2'—C3'—H3'	120.7
C3—C4—C5	121.9 (3)	C3'—C4'—C5'	121.2 (3)
C3—C4—H4	119.1	C3'—C4'—H4'	119.4
C5—C4—H4	119.1	C5'—C4'—H4'	119.4
C6—C5—C4	121.2 (3)	C6'—C5'—C4'	121.5 (3)
C6—C5—H5	119.4	C6'—C5'—H5'	119.2
C4—C5—H5	119.4	C4'—C5'—H5'	119.2
C5—C6—C7	116.5 (3)	C5'—C6'—C7'	116.5 (3)
C5—C6—H6	121.8	C5'—C6'—H6'	121.8
C7—C6—H6	121.8	C7'—C6'—H6'	121.8
N1—C7—C6	132.0 (2)	N1'—C7'—C6'	132.3 (3)
N1—C7—C2	105.2 (2)	N1'—C7'—C2'	105.0 (2)
C6—C7—C2	122.9 (2)	C6'—C7'—C2'	122.7 (3)
N1—C8—C9	111.8 (2)	N1'—C8'—C9'	112.1 (2)
N1—C8—H8A	109.2	N1'—C8'—H8C	109.2
C9—C8—H8A	109.2	C9'—C8'—H8C	109.2
N1—C8—H8B	109.2	N1'—C8'—H8D	109.2
C9—C8—H8B	109.2	C9'—C8'—H8D	109.2
H8A—C8—H8B	107.9	H8C—C8'—H8D	107.9
O—C9—C8	105.90 (19)	O'—C9'—C10'	113.5 (2)
O—C9—C10	113.8 (2)	O'—C9'—C8'	105.5 (2)
C8—C9—C10	110.1 (2)	C10'—C9'—C8'	109.8 (2)
O—C9—H9	109.0	O'—C9'—H9'	109.3
C8—C9—H9	109.0	C10'—C9'—H9'	109.3
C10—C9—H9	109.0	C8'—C9'—H9'	109.3
C11—C10—C15	119.4 (3)	C11'—C10'—C15'	119.1 (2)
C11—C10—C9	119.0 (2)	C11'—C10'—C9'	120.1 (2)
C15—C10—C9	121.5 (2)	C15'—C10'—C9'	120.6 (2)
C10—C11—C12	120.4 (3)	C12'—C11'—C10'	120.5 (3)
C10—C11—H11	119.8	C12'—C11'—H11'	119.8
C12—C11—H11	119.8	C10'—C11'—H11'	119.8
C13—C12—C11	119.9 (3)	C13'—C12'—C11'	120.0 (3)
C13—C12—H12	120.0	C13'—C12'—H12'	120.0
C11—C12—H12	120.0	C11'—C12'—H12'	120.0
C14—C13—C12	119.7 (3)	C14'—C13'—C12'	120.1 (3)
C14—C13—H13	120.2	C14'—C13'—H13'	119.9
C12—C13—H13	120.2	C12'—C13'—H13'	119.9
C13—C14—C15	120.8 (3)	C13'—C14'—C15'	120.7 (3)
C13—C14—H14	119.6	C13'—C14'—H14'	119.7
C15—C14—H14	119.6	C15'—C14'—H14'	119.7
C14—C15—C10	119.9 (3)	C14'—C15'—C10'	119.5 (3)
C14—C15—H15	120.1	C14'—C15'—H15'	120.2
C10—C15—H15	120.1	C10'—C15'—H15'	120.2
O—C16—C17	110.26 (19)	O'—C16'—C17'	110.20 (19)
O—C16—H16A	109.6	O'—C16'—H16C	109.6
C17—C16—H16A	109.6	C17'—C16'—H16C	109.6
O—C16—H16B	109.6	O'—C16'—H16D	109.6
C17—C16—H16B	109.6	C17'—C16'—H16D	109.6
H16A—C16—H16B	108.1	H16C—C16'—H16D	108.1
C22—C17—C18	118.8 (2)	C22'—C17'—C18'	118.5 (2)
C22—C17—C16	122.5 (2)	C22'—C17'—C16'	122.6 (2)
C18—C17—C16	118.7 (2)	C18'—C17'—C16'	118.8 (2)
C19—C18—C17	120.8 (2)	C19'—C18'—C17'	121.3 (2)
C19—C18—H18	119.6	C19'—C18'—H18'	119.4
C17—C18—H18	119.6	C17'—C18'—H18'	119.4
C18—C19—C20	119.8 (2)	C18'—C19'—C20'	120.0 (2)
C18—C19—H19	120.1	C18'—C19'—H19'	120.0
C20—C19—H19	120.1	C20'—C19'—H19'	120.0
C19—C20—C21	120.1 (2)	C21'—C20'—C19'	119.4 (2)
C19—C20—C23	120.5 (2)	C21'—C20'—C23'	119.6 (3)
C21—C20—C23	119.3 (2)	C19'—C20'—C23'	121.0 (2)
C20—C21—C22	120.0 (2)	C22'—C21'—C20'	120.4 (2)
C20—C21—H21	120.0	C22'—C21'—H21'	119.8
C22—C21—H21	120.0	C20'—C21'—H21'	119.8
C17—C22—C21	120.5 (2)	C21'—C22'—C17'	120.4 (2)
C17—C22—H22	119.8	C21'—C22'—H22'	119.8
C21—C22—H22	119.8	C17'—C22'—H22'	119.8
F3—C23—F1	108.6 (3)	F3'—C23'—F1'	109.3 (3)
F3—C23—F2	104.5 (3)	F3'—C23'—F2'	103.3 (3)
F1—C23—F2	103.3 (3)	F1'—C23'—F2'	102.2 (3)
F3—C23—C20	113.2 (3)	F3'—C23'—C20'	114.5 (3)
F1—C23—C20	114.1 (3)	F1'—C23'—C20'	114.8 (3)
F2—C23—C20	112.3 (3)	F2'—C23'—C20'	111.3 (3)
C16—O—C9—C8	−164.6 (2)	C16'—O'—C9'—C10'	−72.8 (3)
C16—O—C9—C10	74.4 (3)	C16'—O'—C9'—C8'	167.0 (2)
C9—O—C16—C17	−178.3 (2)	C9'—O'—C16'—C17'	174.7 (2)
C7—N1—C1—N2	0.3 (3)	C7'—N1'—C1'—N2'	−0.7 (3)
C8—N1—C1—N2	175.7 (2)	C8'—N1'—C1'—N2'	−174.4 (2)
C1—N1—C7—C6	−179.8 (3)	C1'—N1'—C7'—C6'	−178.4 (3)
C8—N1—C7—C6	4.7 (4)	C8'—N1'—C7'—C6'	−4.7 (4)
C1—N1—C7—C2	0.0 (3)	C1'—N1'—C7'—C2'	0.3 (3)
C8—N1—C7—C2	−175.6 (2)	C8'—N1'—C7'—C2'	174.1 (2)
C1—N1—C8—C9	−95.0 (3)	C1'—N1'—C8'—C9'	94.8 (3)
C7—N1—C8—C9	79.6 (3)	C7'—N1'—C8'—C9'	−77.7 (3)
C2—N2—C1—N1	−0.5 (3)	C2'—N2'—C1'—N1'	0.8 (3)
C1—N2—C2—C3	−178.9 (3)	C1'—N2'—C2'—C3'	178.9 (3)
C1—N2—C2—C7	0.5 (3)	C1'—N2'—C2'—C7'	−0.6 (3)
N2—C2—C3—C4	−179.8 (3)	N2'—C2'—C3'—C4'	−178.6 (3)
C7—C2—C3—C4	0.8 (4)	C7'—C2'—C3'—C4'	0.8 (4)
C2—C3—C4—C5	0.0 (4)	C3'—C2'—C7'—N1'	−179.4 (2)
C3—C4—C5—C6	−0.7 (4)	N2'—C2'—C7'—N1'	0.1 (3)
C7—C6—C5—C4	0.5 (4)	C3'—C2'—C7'—C6'	−0.5 (4)
N1—C7—C2—C3	179.1 (2)	N2'—C2'—C7'—C6'	179.0 (2)
C6—C7—C2—C3	−1.0 (4)	C2'—C3'—C4'—C5'	−0.6 (4)
N1—C7—C2—N2	−0.3 (3)	C3'—C4'—C5'—C6'	0.0 (5)
C6—C7—C2—N2	179.5 (2)	C7'—C6'—C5'—C4'	0.4 (4)
N1—C7—C6—C5	−179.9 (2)	N1'—C7'—C6'—C5'	178.4 (3)
C2—C7—C6—C5	0.4 (4)	C2'—C7'—C6'—C5'	−0.1 (4)
O—C9—C8—N1	70.0 (3)	O'—C9'—C8'—N1'	−68.2 (3)
C10—C9—C8—N1	−166.6 (2)	C10'—C9'—C8'—N1'	169.3 (2)
O—C9—C10—C11	−158.4 (2)	O'—C9'—C10'—C11'	148.2 (2)
O—C9—C10—C15	24.8 (3)	C8'—C9'—C10'—C11'	−94.0 (3)
C8—C9—C10—C11	82.9 (3)	O'—C9'—C10'—C15'	−36.1 (3)
C8—C9—C10—C15	−93.8 (3)	C8'—C9'—C10'—C15'	81.6 (3)
C9—C10—C11—C12	−175.8 (2)	C15'—C10'—C11'—C12'	−0.5 (4)
C15—C10—C11—C12	1.0 (4)	C9'—C10'—C11'—C12'	175.3 (2)
C9—C10—C15—C14	176.2 (2)	C11'—C10'—C15'—C14'	−0.3 (4)
C11—C10—C15—C14	−0.5 (4)	C9'—C10'—C15'—C14'	−176.0 (2)
C10—C11—C12—C13	−0.8 (4)	C10'—C11'—C12'—C13'	0.8 (4)
C11—C12—C13—C14	0.0 (4)	C11'—C12'—C13'—C14'	−0.3 (4)
C15—C14—C13—C12	0.5 (4)	C15'—C14'—C13'—C12'	−0.5 (4)
C10—C15—C14—C13	−0.3 (4)	C10'—C15'—C14'—C13'	0.8 (4)
C22—C17—C16—O	−13.1 (4)	C22'—C17'—C16'—O'	5.4 (3)
C18—C17—C16—O	168.3 (2)	C18'—C17'—C16'—O'	−175.0 (2)
C22—C17—C18—C19	0.8 (4)	C18'—C17'—C22'—C21'	0.6 (4)
C16—C17—C18—C19	179.5 (2)	C16'—C17'—C22'—C21'	−179.7 (2)
C18—C17—C22—C21	−1.2 (4)	C19'—C18'—C17'—C22'	−0.2 (4)
C16—C17—C22—C21	−179.9 (2)	C19'—C18'—C17'—C16'	−179.8 (2)
C17—C18—C19—C20	−0.2 (4)	C17'—C18'—C19'—C20'	−0.4 (4)
C21—C20—C19—C18	0.1 (4)	C18'—C19'—C20'—C21'	0.4 (4)
C23—C20—C19—C18	−179.2 (3)	C18'—C19'—C20'—C23'	179.3 (3)
C19—C20—C21—C22	−0.5 (4)	C21'—C20'—C23'—F3'	−55.0 (5)
C23—C20—C21—C22	178.8 (3)	C19'—C20'—C23'—F3'	126.2 (4)
C19—C20—C23—F1	−0.6 (4)	C21'—C20'—C23'—F1'	177.3 (3)
C21—C20—C23—F1	−179.9 (3)	C19'—C20'—C23'—F1'	−1.5 (5)
C19—C20—C23—F2	116.5 (3)	C21'—C20'—C23'—F2'	61.8 (4)
C21—C20—C23—F2	−62.8 (4)	C19'—C20'—C23'—F2'	−117.0 (3)
C19—C20—C23—F3	−125.4 (3)	C22'—C21'—C20'—C19'	0.0 (4)
C21—C20—C23—F3	55.3 (4)	C22'—C21'—C20'—C23'	−178.8 (3)
C17—C22—C21—C20	1.1 (4)	C17'—C22'—C21'—C20'	−0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N2'i	0.93	2.45	3.210 (5)	139
C1'—H1'···N2ii	0.93	2.47	3.215 (5)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N2′i	0.93	2.45	3.210 (5)	139
C1′—H1′⋯N2ii	0.93	2.47	3.215 (5)	138

Symmetry codes: (i) ; (ii) .