1-[2-(4-Fluoro-benz-yloxy)-2-phenyl-ethyl]-1H-benzimidazole.

The asymmetric unit of the title compound, C(22)H(19)FN(2)O, contains two independent mol-ecules. The planar benzimidazole ring systems are oriented with respect to the phen-yl/fluoro-benzene rings at dihedral angles of 31.10 (4)/45.17 (5) and 45.52 (5)/68.63 (5)°, respectively, for the two mol-ecules. In the crystal structure, inter-molecular C-H⋯N and inter-molecular C-H⋯N and C-H⋯F hydrogen bonds link the mol-ecules into a three-dimensional network. There are C-H⋯π contacts between the benzimidazole and fluoro-benzene rings and a π-π contact between the benzimidazole and phenyl ring systems [centroid-centroid distance = 4.575 (1) Å].

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. (1979a ▶,b ▶, 1996 ▶); Caira et al. (2004 ▶).

Experimental

Crystal data

C22H19FN2O

M = 346.39

Monoclinic,

a = 12.6946 (2) Å

b = 18.1279 (4) Å

c = 15.3547 (3) Å

β = 95.747 (1)°

V = 3515.76 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 120 (2) K

0.55 × 0.15 × 0.14 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.953, T max = 0.988

41740 measured reflections

8050 independent reflections

5679 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.142

S = 1.07

8050 reflections

622 parameters

All H-atom parameters refined

Δρmax = 0.43 e Å−3

Δρmin = −0.43 e Å−3

Data collection: COLLECT (Hooft, 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 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021326/xu2436sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021326/xu2436Isup2.hkl

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

C22H19FN2O	F000 = 1456
Mr = 346.39	Dx = 1.309 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8094 reflections
a = 12.6946 (2) Å	θ = 2.9–27.5º
b = 18.1279 (4) Å	µ = 0.09 mm−1
c = 15.3547 (3) Å	T = 120 (2) K
β = 95.747 (1)º	Rod-shaped, colorless
V = 3515.76 (12) Å3	0.55 × 0.15 × 0.14 mm
Z = 8

Bruker–Nonius KappaCCD diffractometer	8050 independent reflections
Radiation source: fine-focus sealed tube	5679 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.065
Detector resolution: 9.091 pixels mm-1	θmax = 27.5º
T = 120(2) K	θmin = 3.0º
φ and ω scans	h = −16→14
Absorption correction: multi-scan(SADABS; Sheldrick, 2007)	k = −23→23
Tmin = 0.953, Tmax = 0.988	l = −19→19
41740 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.055	w = 1/[σ2(Fo2) + (0.0671P)2 + 0.7368P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.142	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.43 e Å−3
8050 reflections	Δρmin = −0.43 e Å−3
622 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: 0.0237 (14)
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
F	1.32492 (8)	0.12305 (7)	1.08865 (8)	0.0437 (3)
O	0.89904 (9)	0.13207 (7)	0.84616 (8)	0.0271 (3)
N1	0.83956 (11)	0.19499 (8)	0.67743 (9)	0.0249 (3)
N2	0.98761 (11)	0.20522 (9)	0.61001 (10)	0.0288 (4)
C1	0.94433 (14)	0.21182 (11)	0.68318 (12)	0.0289 (4)
H1	0.9829 (14)	0.2262 (11)	0.7390 (12)	0.027 (5)*
C2	0.90500 (13)	0.18153 (9)	0.54985 (11)	0.0236 (4)
C3	0.90444 (14)	0.16519 (10)	0.46108 (12)	0.0280 (4)
H3	0.9686 (16)	0.1703 (12)	0.4301 (13)	0.038 (6)*
C4	0.81070 (14)	0.14160 (10)	0.41732 (12)	0.0292 (4)
H4	0.8070 (16)	0.1292 (12)	0.3561 (15)	0.039 (6)*
C5	0.71803 (14)	0.13502 (10)	0.45929 (12)	0.0283 (4)
H5	0.6542 (15)	0.1181 (11)	0.4275 (13)	0.030 (5)*
C6	0.71679 (13)	0.15155 (10)	0.54705 (12)	0.0255 (4)
H6	0.6538 (16)	0.1488 (12)	0.5780 (13)	0.036 (5)*
C7	0.81188 (13)	0.17443 (9)	0.59110 (11)	0.0227 (4)
C8	0.77179 (14)	0.19141 (11)	0.74888 (12)	0.0274 (4)
H81	0.7859 (15)	0.2378 (13)	0.7864 (13)	0.037 (6)*
H82	0.6946 (16)	0.1908 (11)	0.7251 (13)	0.032 (5)*
C9	0.79393 (13)	0.12350 (10)	0.80559 (11)	0.0257 (4)
H9	0.7892 (14)	0.0767 (12)	0.7672 (13)	0.030 (5)*
C10	0.71281 (13)	0.11680 (10)	0.87108 (11)	0.0239 (4)
C11	0.63294 (14)	0.06463 (11)	0.85919 (12)	0.0275 (4)
H11	0.6307 (14)	0.0317 (12)	0.8102 (13)	0.030 (5)*
C12	0.55543 (14)	0.06074 (11)	0.91698 (12)	0.0294 (4)
H12	0.5013 (16)	0.0250 (12)	0.9071 (13)	0.036 (5)*
C13	0.55847 (14)	0.10849 (11)	0.98734 (12)	0.0302 (4)
H13	0.5027 (16)	0.1064 (11)	1.0291 (13)	0.034 (5)*
C14	0.63851 (14)	0.16059 (11)	0.99970 (12)	0.0300 (4)
H14	0.6394 (16)	0.1942 (13)	1.0485 (14)	0.042 (6)*
C15	0.71528 (14)	0.16487 (10)	0.94216 (12)	0.0277 (4)
H15	0.7732 (15)	0.2003 (11)	0.9511 (12)	0.028 (5)*
C16	0.93679 (14)	0.06654 (11)	0.89152 (13)	0.0294 (4)
H161	0.9424 (17)	0.0256 (14)	0.8473 (15)	0.048 (6)*
H162	0.8831 (15)	0.0495 (11)	0.9330 (13)	0.030 (5)*
C17	1.04175 (13)	0.08265 (10)	0.94178 (11)	0.0259 (4)
C18	1.05046 (14)	0.13885 (11)	1.00380 (12)	0.0301 (4)
H18	0.9877 (18)	0.1682 (13)	1.0149 (14)	0.048 (6)*
C19	1.14550 (15)	0.15275 (11)	1.05316 (13)	0.0323 (4)
H19	1.1513 (16)	0.1897 (13)	1.0964 (14)	0.038 (6)*
C20	1.23161 (14)	0.10960 (11)	1.03963 (12)	0.0297 (4)
C21	1.22666 (15)	0.05391 (11)	0.97882 (12)	0.0317 (4)
H21	1.2875 (16)	0.0263 (12)	0.9714 (13)	0.037 (6)*
C22	1.13085 (14)	0.04091 (11)	0.92987 (12)	0.0295 (4)
H22	1.1258 (15)	−0.0001 (12)	0.8881 (14)	0.036 (5)*
F'	0.72117 (9)	0.07392 (7)	0.18637 (7)	0.0422 (3)
O'	0.35374 (9)	0.09943 (7)	0.42429 (9)	0.0319 (3)
N1'	0.32870 (11)	0.19095 (8)	0.57339 (9)	0.0250 (3)
N2'	0.49161 (11)	0.21227 (8)	0.63993 (10)	0.0274 (3)
C1'	0.43292 (13)	0.20470 (10)	0.56517 (12)	0.0265 (4)
H1A	0.4581 (15)	0.2084 (11)	0.5054 (13)	0.033 (5)*
C2'	0.42077 (13)	0.20278 (9)	0.70299 (12)	0.0242 (4)
C3'	0.43907 (14)	0.20280 (10)	0.79409 (12)	0.0277 (4)
H3A	0.5121 (16)	0.2104 (11)	0.8237 (13)	0.035 (5)*
C4'	0.35328 (14)	0.19125 (11)	0.84097 (12)	0.0290 (4)
H4A	0.3623 (15)	0.1912 (11)	0.9025 (14)	0.034 (5)*
C5'	0.25116 (14)	0.18014 (10)	0.79938 (12)	0.0284 (4)
H5A	0.1897 (14)	0.1719 (10)	0.8350 (12)	0.023 (5)*
C6'	0.23161 (13)	0.17905 (10)	0.70912 (12)	0.0252 (4)
H6A	0.1612 (15)	0.1685 (11)	0.6825 (12)	0.029 (5)*
C7'	0.31895 (13)	0.18983 (9)	0.66247 (11)	0.0234 (4)
C8'	0.24572 (14)	0.17291 (10)	0.50377 (12)	0.0267 (4)
H8A	0.2466 (15)	0.2088 (12)	0.4553 (13)	0.034 (5)*
H8B	0.1797 (16)	0.1747 (12)	0.5281 (13)	0.034 (5)*
C9'	0.25876 (14)	0.09658 (10)	0.46651 (12)	0.0282 (4)
H9A	0.2690 (15)	0.0595 (12)	0.5175 (13)	0.033 (5)*
C10'	0.16396 (13)	0.07542 (10)	0.40381 (12)	0.0278 (4)
C11'	0.10205 (14)	0.01572 (11)	0.42324 (13)	0.0311 (4)
H11A	0.1273 (17)	−0.0142 (13)	0.4771 (15)	0.046 (6)*
C12'	0.01201 (15)	−0.00234 (12)	0.36915 (13)	0.0356 (5)
H12A	−0.0308 (18)	−0.0463 (14)	0.3827 (15)	0.051 (6)*
C13'	−0.01693 (15)	0.03929 (12)	0.29548 (13)	0.0367 (5)
H13A	−0.0804 (18)	0.0252 (13)	0.2610 (14)	0.045 (6)*
C14'	0.04507 (16)	0.09780 (12)	0.27391 (13)	0.0380 (5)
H14A	0.0274 (17)	0.1268 (13)	0.2198 (15)	0.046 (6)*
C15'	0.13594 (16)	0.11604 (12)	0.32758 (13)	0.0334 (4)
H15A	0.1795 (16)	0.1575 (13)	0.3127 (14)	0.042 (6)*
C16'	0.38651 (15)	0.02982 (11)	0.39365 (14)	0.0313 (4)
H16A	0.3236 (17)	0.0054 (12)	0.3565 (14)	0.041 (6)*
H16B	0.4113 (16)	−0.0028 (13)	0.4487 (14)	0.041 (6)*
C17'	0.47598 (13)	0.04194 (10)	0.33826 (11)	0.0263 (4)
C18'	0.47972 (15)	0.10525 (11)	0.28687 (12)	0.0295 (4)
H18A	0.4234 (15)	0.1408 (12)	0.2871 (13)	0.031 (5)*
C19'	0.56238 (15)	0.11670 (11)	0.23553 (12)	0.0316 (4)
H19A	0.5682 (16)	0.1634 (13)	0.2001 (14)	0.040 (6)*
C20'	0.63892 (14)	0.06312 (11)	0.23568 (12)	0.0295 (4)
C21'	0.63728 (15)	−0.00091 (11)	0.28360 (13)	0.0330 (4)
H21A	0.6947 (18)	−0.0365 (14)	0.2804 (14)	0.049 (6)*
C22'	0.55530 (14)	−0.01061 (11)	0.33574 (12)	0.0300 (4)
H22A	0.5502 (16)	−0.0561 (13)	0.3701 (14)	0.039 (6)*

	U11	U22	U33	U12	U13	U23
F	0.0279 (6)	0.0494 (8)	0.0519 (7)	−0.0033 (5)	−0.0053 (5)	0.0001 (6)
O	0.0248 (6)	0.0294 (7)	0.0266 (6)	0.0005 (5)	0.0007 (5)	0.0048 (5)
N1	0.0223 (7)	0.0297 (8)	0.0225 (7)	−0.0015 (6)	0.0014 (6)	0.0024 (6)
N2	0.0240 (7)	0.0334 (9)	0.0287 (8)	−0.0050 (6)	0.0007 (6)	0.0060 (7)
C1	0.0260 (9)	0.0331 (11)	0.0269 (10)	−0.0049 (7)	−0.0012 (8)	0.0041 (8)
C2	0.0214 (8)	0.0222 (9)	0.0272 (9)	−0.0001 (7)	0.0019 (7)	0.0047 (7)
C3	0.0272 (9)	0.0295 (10)	0.0281 (10)	0.0026 (8)	0.0073 (7)	0.0052 (8)
C4	0.0342 (10)	0.0290 (10)	0.0244 (9)	0.0038 (8)	0.0024 (7)	−0.0012 (8)
C5	0.0266 (9)	0.0277 (10)	0.0295 (10)	−0.0008 (7)	−0.0022 (7)	−0.0001 (8)
C6	0.0223 (8)	0.0254 (9)	0.0286 (9)	−0.0003 (7)	0.0025 (7)	0.0022 (7)
C7	0.0248 (8)	0.0220 (9)	0.0212 (8)	0.0021 (7)	0.0017 (7)	0.0027 (7)
C8	0.0262 (9)	0.0321 (10)	0.0241 (9)	0.0010 (8)	0.0045 (7)	0.0021 (8)
C9	0.0237 (9)	0.0295 (10)	0.0235 (9)	0.0007 (7)	0.0013 (7)	0.0003 (8)
C10	0.0223 (8)	0.0270 (9)	0.0221 (9)	0.0022 (7)	0.0010 (6)	0.0026 (7)
C11	0.0292 (9)	0.0285 (10)	0.0242 (9)	−0.0014 (7)	−0.0004 (7)	0.0001 (8)
C12	0.0238 (9)	0.0318 (10)	0.0318 (10)	−0.0051 (8)	−0.0010 (7)	0.0077 (8)
C13	0.0271 (9)	0.0342 (11)	0.0297 (10)	0.0036 (8)	0.0054 (8)	0.0082 (8)
C14	0.0323 (10)	0.0306 (10)	0.0279 (10)	0.0013 (8)	0.0069 (8)	0.0010 (8)
C15	0.0285 (9)	0.0269 (10)	0.0277 (9)	−0.0036 (8)	0.0026 (7)	0.0003 (8)
C16	0.0293 (9)	0.0268 (10)	0.0315 (10)	0.0040 (7)	0.0006 (8)	0.0030 (8)
C17	0.0269 (9)	0.0259 (9)	0.0252 (9)	0.0017 (7)	0.0045 (7)	0.0053 (7)
C18	0.0280 (9)	0.0291 (10)	0.0340 (10)	0.0032 (8)	0.0065 (8)	−0.0001 (8)
C19	0.0344 (10)	0.0299 (11)	0.0326 (10)	−0.0023 (8)	0.0029 (8)	−0.0018 (9)
C20	0.0236 (9)	0.0330 (10)	0.0319 (10)	−0.0035 (8)	−0.0003 (7)	0.0071 (8)
C21	0.0285 (9)	0.0352 (11)	0.0322 (10)	0.0083 (8)	0.0072 (8)	0.0070 (8)
C22	0.0343 (10)	0.0318 (10)	0.0224 (9)	0.0069 (8)	0.0039 (7)	0.0034 (8)
F'	0.0391 (6)	0.0524 (8)	0.0372 (6)	0.0111 (5)	0.0142 (5)	0.0048 (6)
O'	0.0283 (7)	0.0285 (7)	0.0400 (8)	−0.0007 (5)	0.0087 (6)	−0.0077 (6)
N1'	0.0237 (7)	0.0277 (8)	0.0237 (8)	−0.0014 (6)	0.0032 (6)	−0.0005 (6)
N2'	0.0243 (7)	0.0276 (8)	0.0307 (8)	−0.0024 (6)	0.0043 (6)	−0.0004 (6)
C1'	0.0255 (9)	0.0256 (9)	0.0289 (10)	−0.0011 (7)	0.0056 (7)	−0.0002 (7)
C2'	0.0235 (8)	0.0197 (9)	0.0296 (9)	0.0003 (7)	0.0034 (7)	−0.0005 (7)
C3'	0.0257 (9)	0.0253 (10)	0.0310 (10)	0.0012 (7)	−0.0018 (7)	−0.0015 (8)
C4'	0.0329 (10)	0.0288 (10)	0.0251 (10)	0.0055 (8)	0.0020 (8)	0.0003 (8)
C5'	0.0282 (9)	0.0269 (10)	0.0310 (10)	0.0029 (7)	0.0077 (8)	0.0018 (8)
C6'	0.0216 (8)	0.0241 (9)	0.0298 (10)	0.0009 (7)	0.0030 (7)	−0.0016 (7)
C7'	0.0250 (8)	0.0191 (8)	0.0261 (9)	0.0026 (7)	0.0020 (7)	−0.0005 (7)
C8'	0.0249 (9)	0.0305 (10)	0.0244 (9)	−0.0005 (7)	0.0007 (7)	−0.0009 (8)
C9'	0.0256 (9)	0.0286 (10)	0.0308 (10)	−0.0014 (7)	0.0041 (7)	0.0003 (8)
C10'	0.0265 (9)	0.0299 (10)	0.0269 (9)	0.0031 (7)	0.0023 (7)	−0.0064 (8)
C11'	0.0317 (10)	0.0282 (10)	0.0333 (10)	0.0015 (8)	0.0025 (8)	−0.0043 (8)
C12'	0.0332 (10)	0.0344 (11)	0.0399 (11)	−0.0034 (9)	0.0060 (8)	−0.0106 (9)
C13'	0.0291 (10)	0.0464 (13)	0.0337 (11)	0.0032 (9)	−0.0011 (8)	−0.0144 (9)
C14'	0.0444 (12)	0.0448 (13)	0.0241 (10)	0.0092 (10)	0.0001 (8)	−0.0034 (9)
C15'	0.0384 (11)	0.0324 (11)	0.0302 (10)	−0.0002 (9)	0.0074 (8)	−0.0035 (8)
C16'	0.0297 (9)	0.0264 (10)	0.0381 (11)	0.0013 (8)	0.0049 (8)	−0.0026 (8)
C17'	0.0263 (9)	0.0253 (9)	0.0265 (9)	0.0006 (7)	−0.0011 (7)	−0.0049 (7)
C18'	0.0295 (9)	0.0300 (10)	0.0286 (10)	0.0074 (8)	0.0011 (7)	−0.0026 (8)
C19'	0.0365 (10)	0.0316 (11)	0.0265 (10)	0.0066 (8)	0.0032 (8)	0.0013 (8)
C20'	0.0283 (9)	0.0362 (11)	0.0245 (9)	0.0031 (8)	0.0048 (7)	−0.0029 (8)
C21'	0.0323 (10)	0.0306 (11)	0.0359 (11)	0.0080 (8)	0.0028 (8)	−0.0049 (8)
C22'	0.0336 (10)	0.0237 (10)	0.0323 (10)	0.0027 (8)	0.0006 (8)	−0.0013 (8)

F—C20	1.360 (2)	F'—C20'	1.364 (2)
O—C9	1.423 (2)	O'—C9'	1.426 (2)
O—C16	1.435 (2)	O'—C16'	1.423 (2)
N1—C1	1.359 (2)	N1'—C1'	1.365 (2)
N1—C7	1.388 (2)	N1'—C7'	1.386 (2)
N1—C8	1.462 (2)	N1'—C8'	1.461 (2)
N2—C1	1.305 (2)	N2'—C1'	1.312 (2)
N2—C2	1.394 (2)	N2'—C2'	1.397 (2)
C1—H1	0.980 (19)	C1'—H1A	1.00 (2)
C2—C3	1.394 (3)	C2'—C7'	1.397 (2)
C2—C7	1.402 (2)	C3'—C2'	1.395 (3)
C3—H3	0.99 (2)	C3'—C4'	1.380 (3)
C4—C3	1.375 (3)	C3'—H3A	1.00 (2)
C4—C5	1.402 (3)	C4'—C5'	1.401 (3)
C4—H4	0.96 (2)	C4'—H4A	0.94 (2)
C5—H5	0.95 (2)	C5'—C6'	1.383 (3)
C6—C5	1.382 (3)	C5'—H5A	1.008 (18)
C6—H6	0.97 (2)	C6'—H6A	0.964 (19)
C7—C6	1.387 (2)	C7'—C6'	1.393 (2)
C8—H81	1.03 (2)	C8'—C9'	1.513 (3)
C8—H82	1.011 (19)	C8'—H8A	0.99 (2)
C9—C8	1.518 (3)	C8'—H8B	0.95 (2)
C9—C10	1.514 (2)	C9'—C10'	1.513 (2)
C9—H9	1.03 (2)	C9'—H9A	1.03 (2)
C10—C15	1.395 (3)	C10'—C11'	1.387 (3)
C11—C10	1.385 (3)	C10'—C15'	1.398 (3)
C11—C12	1.391 (3)	C11'—C12'	1.383 (3)
C11—H11	0.96 (2)	C11'—H11A	1.01 (2)
C12—C13	1.382 (3)	C12'—H12A	1.00 (2)
C12—H12	0.95 (2)	C13'—C12'	1.379 (3)
C13—H13	1.00 (2)	C13'—C14'	1.381 (3)
C14—C13	1.386 (3)	C13'—H13A	0.95 (2)
C14—C15	1.382 (3)	C14'—H14A	0.99 (2)
C14—H14	0.97 (2)	C15'—C14'	1.389 (3)
C15—H15	0.97 (2)	C15'—H15A	0.97 (2)
C16—H161	1.01 (2)	C16'—H16A	1.03 (2)
C16—H162	1.03 (2)	C16'—H16B	1.05 (2)
C17—C16	1.500 (2)	C17'—C16'	1.502 (3)
C17—C18	1.391 (3)	C17'—C18'	1.396 (3)
C17—C22	1.388 (2)	C17'—C22'	1.389 (3)
C18—C19	1.382 (3)	C18'—C19'	1.390 (3)
C18—H18	0.99 (2)	C18'—H18A	0.96 (2)
C19—H19	0.94 (2)	C19'—H19A	1.01 (2)
C20—C19	1.377 (3)	C20'—C19'	1.374 (3)
C20—C21	1.372 (3)	C20'—C21'	1.376 (3)
C21—C22	1.384 (3)	C21'—C22'	1.386 (3)
C21—H21	0.94 (2)	C21'—H21A	0.98 (2)
C22—H22	0.98 (2)	C22'—H22A	0.98 (2)
C9—O—C16	112.02 (13)	C16'—O'—C9'	113.99 (14)
C1—N1—C7	105.96 (14)	C1'—N1'—C7'	106.09 (14)
C1—N1—C8	127.37 (15)	C1'—N1'—C8'	127.44 (15)
C7—N1—C8	126.37 (14)	C7'—N1'—C8'	126.15 (14)
C1—N2—C2	104.19 (14)	C1'—N2'—C2'	104.19 (14)
N1—C1—H1	121.1 (11)	N1'—C1'—H1A	119.8 (11)
N2—C1—N1	114.66 (16)	N2'—C1'—N1'	114.16 (16)
N2—C1—H1	124.2 (11)	N2'—C1'—H1A	126.0 (11)
N2—C2—C7	109.96 (15)	N2'—C2'—C7'	110.07 (15)
C3—C2—N2	130.02 (16)	C3'—C2'—N2'	129.88 (16)
C3—C2—C7	120.02 (15)	C3'—C2'—C7'	120.03 (16)
C2—C3—H3	121.8 (12)	C2'—C3'—H3A	120.6 (11)
C4—C3—C2	117.60 (16)	C4'—C3'—C2'	117.52 (16)
C4—C3—H3	120.6 (12)	C4'—C3'—H3A	121.8 (11)
C3—C4—C5	121.79 (17)	C3'—C4'—C5'	121.77 (17)
C3—C4—H4	120.3 (12)	C3'—C4'—H4A	120.1 (12)
C5—C4—H4	117.9 (12)	C5'—C4'—H4A	118.2 (12)
C4—C5—H5	120.1 (12)	C4'—C5'—H5A	120.3 (10)
C6—C5—C4	121.45 (16)	C6'—C5'—C4'	121.58 (17)
C6—C5—H5	118.5 (12)	C6'—C5'—H5A	118.1 (10)
C5—C6—C7	116.49 (16)	C5'—C6'—C7'	116.17 (16)
C5—C6—H6	123.8 (12)	C5'—C6'—H6A	119.6 (11)
C7—C6—H6	119.7 (12)	C7'—C6'—H6A	124.2 (11)
N1—C7—C2	105.22 (14)	N1'—C7'—C6'	131.61 (15)
C6—C7—N1	132.15 (16)	N1'—C7'—C2'	105.49 (14)
C6—C7—C2	122.63 (16)	C6'—C7'—C2'	122.90 (16)
N1—C8—C9	112.17 (15)	N1'—C8'—C9'	112.54 (15)
N1—C8—H81	107.6 (11)	N1'—C8'—H8A	110.0 (11)
N1—C8—H82	110.6 (11)	N1'—C8'—H8B	107.7 (12)
C9—C8—H81	109.3 (11)	C9'—C8'—H8A	107.9 (12)
C9—C8—H82	108.4 (12)	C9'—C8'—H8B	108.2 (13)
H81—C8—H82	108.7 (16)	H8A—C8'—H8B	110.5 (17)
O—C9—C8	105.91 (14)	O'—C9'—C8'	105.57 (14)
O—C9—C10	112.84 (14)	O'—C9'—C10'	112.01 (15)
O—C9—H9	109.7 (10)	O'—C9'—H9A	108.7 (11)
C8—C9—H9	110.0 (11)	C8'—C9'—C10'	111.24 (15)
C10—C9—C8	110.29 (14)	C8'—C9'—H9A	108.7 (11)
C10—C9—H9	108.0 (11)	C10'—C9'—H9A	110.4 (11)
C11—C10—C9	120.31 (16)	C11'—C10'—C15'	119.25 (17)
C11—C10—C15	119.24 (16)	C11'—C10'—C9'	119.50 (17)
C15—C10—C9	120.40 (16)	C15'—C10'—C9'	121.22 (17)
C10—C11—C12	120.38 (17)	C10'—C11'—H11A	117.0 (13)
C10—C11—H11	119.5 (12)	C12'—C11'—C10'	120.49 (19)
C12—C11—H11	120.1 (12)	C12'—C11'—H11A	122.5 (13)
C11—C12—H12	118.8 (13)	C11'—C12'—H12A	119.9 (13)
C13—C12—C11	120.05 (17)	C13'—C12'—C11'	120.0 (2)
C13—C12—H12	121.2 (13)	C13'—C12'—H12A	120.1 (13)
C12—C13—C14	119.77 (17)	C12'—C13'—C14'	120.38 (18)
C12—C13—H13	120.6 (12)	C12'—C13'—H13A	116.8 (14)
C14—C13—H13	119.6 (12)	C14'—C13'—H13A	122.8 (14)
C13—C14—H14	119.2 (13)	C13'—C14'—C15'	120.01 (19)
C15—C14—C13	120.33 (18)	C13'—C14'—H14A	121.5 (13)
C15—C14—H14	120.5 (13)	C15'—C14'—H14A	118.5 (13)
C10—C15—H15	118.6 (11)	C10'—C15'—H15A	120.0 (13)
C14—C15—C10	120.22 (17)	C14'—C15'—C10'	119.85 (19)
C14—C15—H15	121.2 (11)	C14'—C15'—H15A	120.1 (12)
O—C16—C17	108.96 (15)	O'—C16'—C17'	108.67 (15)
O—C16—H161	108.9 (13)	O'—C16'—H16A	109.1 (12)
O—C16—H162	109.9 (11)	O'—C16'—H16B	107.8 (12)
C17—C16—H162	110.5 (10)	C17'—C16'—H16A	109.7 (12)
C17—C16—H161	111.6 (12)	C17'—C16'—H16B	110.8 (11)
H162—C16—H161	106.9 (17)	H16A—C16'—H16B	110.7 (17)
C18—C17—C16	120.02 (16)	C18'—C17'—C16'	120.72 (16)
C22—C17—C18	118.64 (17)	C22'—C17'—C18'	118.82 (17)
C22—C17—C16	121.30 (17)	C22'—C17'—C16'	120.45 (17)
C17—C18—H18	120.2 (13)	C17'—C18'—H18A	118.8 (12)
C19—C18—C17	120.93 (17)	C19'—C18'—C17'	120.91 (17)
C19—C18—H18	118.8 (13)	C19'—C18'—H18A	120.3 (12)
C18—C19—H19	121.3 (13)	C18'—C19'—H19A	121.9 (12)
C20—C19—C18	118.45 (19)	C20'—C19'—C18'	117.87 (18)
C20—C19—H19	120.2 (13)	C20'—C19'—H19A	120.2 (12)
F—C20—C19	118.38 (17)	F'—C20'—C19'	118.57 (17)
F—C20—C21	119.09 (16)	F'—C20'—C21'	118.13 (16)
C21—C20—C19	122.53 (17)	C19'—C20'—C21'	123.30 (18)
C20—C21—C22	118.19 (17)	C20'—C21'—C22'	117.92 (18)
C20—C21—H21	119.6 (13)	C20'—C21'—H21A	118.6 (14)
C22—C21—H21	122.2 (13)	C22'—C21'—H21A	123.5 (14)
C17—C22—H22	119.9 (12)	C17'—C22'—H22A	118.2 (12)
C21—C22—C17	121.26 (18)	C21'—C22'—C17'	121.14 (18)
C21—C22—H22	118.8 (12)	C21'—C22'—H22A	120.6 (12)
C16—O—C9—C8	−171.09 (14)	C16'—O'—C9'—C8'	172.99 (15)
C16—O—C9—C10	68.15 (19)	C16'—O'—C9'—C10'	−65.8 (2)
C9—O—C16—C17	−172.87 (14)	C9'—O'—C16'—C17'	170.86 (14)
C7—N1—C1—N2	0.7 (2)	C7'—N1'—C1'—N2'	0.3 (2)
C8—N1—C1—N2	174.73 (17)	C8'—N1'—C1'—N2'	−173.60 (17)
C1—N1—C7—C2	−0.70 (18)	C1'—N1'—C7'—C6'	179.34 (18)
C1—N1—C7—C6	179.78 (19)	C8'—N1'—C7'—C6'	−6.7 (3)
C8—N1—C7—C2	−174.84 (16)	C1'—N1'—C7'—C2'	−0.44 (18)
C8—N1—C7—C6	5.6 (3)	C8'—N1'—C7'—C2'	173.54 (16)
C1—N1—C8—C9	−73.6 (2)	C1'—N1'—C8'—C9'	70.5 (2)
C7—N1—C8—C9	99.33 (19)	C7'—N1'—C8'—C9'	−102.2 (2)
C2—N2—C1—N1	−0.3 (2)	C2'—N2'—C1'—N1'	0.0 (2)
C1—N2—C2—C3	−179.88 (19)	C1'—N2'—C2'—C3'	177.92 (19)
C1—N2—C2—C7	−0.15 (19)	C1'—N2'—C2'—C7'	−0.30 (19)
N2—C2—C3—C4	179.03 (18)	C3'—C2'—C7'—N1'	−177.96 (16)
C7—C2—C3—C4	−0.7 (3)	N2'—C2'—C7'—N1'	0.47 (19)
N2—C2—C7—N1	0.54 (19)	C3'—C2'—C7'—C6'	2.2 (3)
N2—C2—C7—C6	−179.88 (16)	N2'—C2'—C7'—C6'	−179.33 (16)
C3—C2—C7—N1	−179.70 (16)	C4'—C3'—C2'—N2'	−179.40 (17)
C3—C2—C7—C6	−0.1 (3)	C4'—C3'—C2'—C7'	−1.3 (3)
C5—C4—C3—C2	0.9 (3)	C2'—C3'—C4'—C5'	−0.2 (3)
C3—C4—C5—C6	−0.4 (3)	C3'—C4'—C5'—C6'	1.0 (3)
C7—C6—C5—C4	−0.4 (3)	C4'—C5'—C6'—C7'	−0.2 (3)
N1—C7—C6—C5	−179.90 (18)	N1'—C7'—C6'—C5'	178.82 (18)
C2—C7—C6—C5	0.6 (3)	C2'—C7'—C6'—C5'	−1.4 (3)
O—C9—C8—N1	65.00 (18)	N1'—C8'—C9'—O'	−66.22 (19)
C10—C9—C8—N1	−172.60 (14)	N1'—C8'—C9'—C10'	172.07 (15)
O—C9—C10—C11	−136.59 (17)	O'—C9'—C10'—C11'	125.14 (18)
O—C9—C10—C15	45.8 (2)	C8'—C9'—C10'—C11'	−116.98 (19)
C8—C9—C10—C11	105.18 (19)	O'—C9'—C10'—C15'	−56.5 (2)
C8—C9—C10—C15	−72.4 (2)	C8'—C9'—C10'—C15'	61.4 (2)
C9—C10—C15—C14	177.27 (16)	C9'—C10'—C11'—C12'	176.72 (17)
C11—C10—C15—C14	−0.3 (3)	C15'—C10'—C11'—C12'	−1.7 (3)
C12—C11—C10—C9	−176.91 (16)	C9'—C10'—C15'—C14'	−176.33 (17)
C12—C11—C10—C15	0.7 (3)	C11'—C10'—C15'—C14'	2.1 (3)
C10—C11—C12—C13	−0.8 (3)	C10'—C11'—C12'—C13'	−0.2 (3)
C11—C12—C13—C14	0.5 (3)	C14'—C13'—C12'—C11'	1.8 (3)
C15—C14—C13—C12	−0.1 (3)	C12'—C13'—C14'—C15'	−1.4 (3)
C13—C14—C15—C10	0.1 (3)	C10'—C15'—C14'—C13'	−0.5 (3)
C18—C17—C16—O	57.8 (2)	C18'—C17'—C16'—O'	−33.7 (2)
C22—C17—C16—O	−124.31 (18)	C22'—C17'—C16'—O'	147.83 (17)
C16—C17—C18—C19	177.53 (17)	C16'—C17'—C18'—C19'	179.98 (17)
C22—C17—C18—C19	−0.4 (3)	C22'—C17'—C18'—C19'	−1.5 (3)
C16—C17—C22—C21	−177.36 (17)	C18'—C17'—C22'—C21'	0.2 (3)
C18—C17—C22—C21	0.6 (3)	C16'—C17'—C22'—C21'	178.70 (17)
C17—C18—C19—C20	−0.1 (3)	C17'—C18'—C19'—C20'	1.3 (3)
F—C20—C19—C18	−179.59 (16)	F'—C20'—C19'—C18'	−179.30 (16)
C21—C20—C19—C18	0.4 (3)	C21'—C20'—C19'—C18'	0.3 (3)
F—C20—C21—C22	179.72 (16)	F'—C20'—C21'—C22'	178.03 (16)
C19—C20—C21—C22	−0.3 (3)	C19'—C20'—C21'—C22'	−1.6 (3)
C20—C21—C22—C17	−0.2 (3)	C20'—C21'—C22'—C17'	1.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N2'	0.97 (2)	2.62 (2)	3.498 (2)	150.5 (17)
C6'—H6A···N2i	0.964 (19)	2.459 (19)	3.345 (2)	152.7 (16)
C13—H13···Fi	1.00 (2)	2.54 (2)	3.493 (2)	159.6 (16)
C19'—H19A···N2'ii	1.01 (2)	2.59 (2)	3.509 (2)	151.1 (16)
C5—H5···Cg8iii	0.95 (2)	2.662 (19)	3.514 (2)	149.0 (15)
C22'—H22A···Cg2iv	0.98 (2)	2.62 (9)	3.518 (2)	141.9 (16)

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the N1′/N2′/C1′/C2′/C7′ ring and Cg8 is the centroid of the C17′–C22′ ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯N2′	0.97 (2)	2.62 (2)	3.498 (2)	150.5 (17)
C6′—H6A⋯N2i	0.964 (19)	2.459 (19)	3.345 (2)	152.7 (16)
C13—H13⋯Fi	1.00 (2)	2.54 (2)	3.493 (2)	159.6 (16)
C19′—H19A⋯N2′ii	1.01 (2)	2.59 (2)	3.509 (2)	151.1 (16)
C5—H5⋯Cg8iii	0.95 (2)	2.662 (19)	3.514 (2)	149.0 (15)
C22′—H22A⋯Cg2iv	0.98 (2)	2.62 (9)	3.518 (2)	141.9 (16)

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