1-[2-(4-Chloro-benz-yloxy)-2-phenyl-ethyl]-1H-benzotriazole.

The asymmetric unit of the title compound, C(21)H(18)ClN(3)O, contains two crystallographically independent mol-ecules which differ slightly in the orientations of chloro-benz-yloxy units. In one of the mol-ecules, the phenyl and chloro-phenyl rings are oriented at dihedral angles of 38.09 (6) and 42.15 (6)°, respectively, with respect to the benzotriazole ring [43.23 (6) and 29.80 (6)° in the other mol-ecule]. The dihedral angle between the phenyl and chloro-phenyl rings is 77.63 (6)° in one of the mol-ecules and 72.97 (6)° in the other. The crystal structure is stabilized by weak C-H⋯π inter-actions.

Related literature

For general background to the biological activity of benzotriazole derivatives, see: Hirokawa et al. (1998 ▶); Yu et al. (2003 ▶); Kopanska et al. (2004 ▶). For related structures, see: Caira et al. (2004 ▶); Freer et al. (1986 ▶); Katritzky et al. (2001 ▶); Özel Güven et al. (2007a ▶,b ▶, 2008a ▶,b ▶,c ▶, 2010 ▶); Peeters et al. (1979a ▶,b ▶, 1996 ▶); Swamy et al. (2006 ▶).

Experimental

Crystal data

C21H18ClN3O

M = 363.83

Monoclinic,

a = 7.2163 (2) Å

b = 36.8545 (9) Å

c = 13.3019 (3) Å

β = 91.529 (1)°

V = 3536.42 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 120 K

0.40 × 0.40 × 0.14 mm

Data collection

Nonius Kappa CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.910, T max = 0.966

26731 measured reflections

7993 independent reflections

5918 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.189

S = 1.07

7993 reflections

470 parameters

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.69 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 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810015692/ci5085sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015692/ci5085Isup2.hkl

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

C21H18ClN3O	F(000) = 1520
Mr = 363.83	Dx = 1.367 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 26277 reflections
a = 7.2163 (2) Å	θ = 2.9–27.5°
b = 36.8545 (9) Å	µ = 0.23 mm−1
c = 13.3019 (3) Å	T = 120 K
β = 91.529 (1)°	Slab, colourless
V = 3536.42 (15) Å3	0.40 × 0.40 × 0.14 mm
Z = 8

Nonius Kappa CCD diffractometer	7993 independent reflections
Radiation source: fine-focus sealed tube	5918 reflections with I > 2σ(I)
graphite	Rint = 0.051
φ and ω scans	θmax = 27.6°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −9→9
Tmin = 0.910, Tmax = 0.966	k = −47→43
26731 measured reflections	l = −17→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065	H-atom parameters constrained
wR(F2) = 0.189	w = 1/[σ2(Fo2) + (0.1171P)2 + 0.2599P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
7993 reflections	Δρmax = 0.64 e Å−3
470 parameters	Δρmin = −0.69 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (2)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	−0.22475 (9)	0.476481 (18)	0.55416 (6)	0.0416 (2)
O1	0.3382 (2)	0.34725 (4)	0.40142 (11)	0.0230 (3)
N1	0.3727 (3)	0.38511 (5)	0.07784 (14)	0.0288 (5)
N2	0.4375 (3)	0.35556 (5)	0.12052 (14)	0.0269 (4)
N3	0.4929 (3)	0.36393 (5)	0.21634 (13)	0.0228 (4)
C1	0.3846 (3)	0.41288 (6)	0.14623 (17)	0.0250 (5)
C2	0.3361 (3)	0.44961 (7)	0.13830 (19)	0.0327 (6)
H2	0.2799	0.4591	0.0785	0.039*
C3	0.3729 (3)	0.47135 (7)	0.2200 (2)	0.0330 (6)
H3	0.3418	0.4964	0.2166	0.040*
C4	0.4559 (3)	0.45739 (7)	0.30917 (19)	0.0313 (5)
H4	0.4821	0.4734	0.3636	0.038*
C5	0.4999 (3)	0.42131 (6)	0.31946 (17)	0.0264 (5)
H5	0.5527	0.4118	0.3801	0.032*
C6	0.4626 (3)	0.39944 (6)	0.23575 (16)	0.0222 (5)
C7	0.5705 (3)	0.33638 (6)	0.28229 (17)	0.0250 (5)
H7A	0.6674	0.3474	0.3266	0.030*
H7B	0.6299	0.3174	0.2414	0.030*
C8	0.4235 (3)	0.31891 (6)	0.34680 (16)	0.0239 (5)
H8	0.3278	0.3074	0.3014	0.029*
C9	0.5062 (3)	0.29013 (6)	0.41518 (15)	0.0209 (5)
C10	0.6548 (3)	0.29873 (6)	0.48017 (16)	0.0234 (5)
H10	0.7022	0.3228	0.4821	0.028*
C11	0.7333 (3)	0.27231 (6)	0.54186 (16)	0.0259 (5)
H11	0.8358	0.2782	0.5851	0.031*
C12	0.6629 (3)	0.23736 (6)	0.54066 (16)	0.0254 (5)
H12	0.7166	0.2193	0.5833	0.030*
C13	0.5145 (3)	0.22873 (6)	0.47732 (16)	0.0248 (5)
H13	0.4654	0.2048	0.4769	0.030*
C14	0.4368 (3)	0.25505 (6)	0.41408 (16)	0.0233 (5)
H14	0.3359	0.2489	0.3700	0.028*
C15	0.1497 (3)	0.33957 (7)	0.4250 (2)	0.0360 (6)
H15A	0.1459	0.3212	0.4791	0.043*
H15B	0.0831	0.3297	0.3649	0.043*
C16	0.0583 (3)	0.37382 (6)	0.45829 (18)	0.0265 (5)
C17	0.0463 (3)	0.40358 (7)	0.39399 (17)	0.0273 (5)
H17	0.0966	0.4020	0.3288	0.033*
C18	−0.0374 (3)	0.43532 (6)	0.42360 (18)	0.0291 (5)
H18	−0.0430	0.4557	0.3799	0.035*
C19	−0.1137 (3)	0.43699 (6)	0.51846 (18)	0.0278 (5)
C20	−0.1040 (3)	0.40812 (6)	0.58310 (18)	0.0276 (5)
H20	−0.1553	0.4097	0.6480	0.033*
C21	−0.0178 (3)	0.37633 (6)	0.55244 (18)	0.0272 (5)
H21	−0.0113	0.3561	0.5967	0.033*
Cl1'	0.19246 (9)	0.026883 (16)	0.22027 (5)	0.0384 (2)
O1'	0.8366 (2)	0.15017 (4)	0.30657 (11)	0.0248 (4)
N1'	0.9026 (3)	0.12718 (5)	0.65649 (14)	0.0294 (5)
N2'	0.9650 (3)	0.15280 (5)	0.59942 (14)	0.0274 (4)
N3'	0.9881 (3)	0.13952 (5)	0.50553 (13)	0.0225 (4)
C1'	0.8871 (3)	0.09601 (6)	0.59982 (17)	0.0247 (5)
C2'	0.8299 (3)	0.06087 (7)	0.62520 (19)	0.0307 (5)
H2'	0.7928	0.0551	0.6913	0.037*
C3'	0.8297 (3)	0.03530 (6)	0.5510 (2)	0.0320 (6)
H3'	0.7897	0.0114	0.5658	0.038*
C4'	0.8873 (3)	0.04340 (6)	0.45265 (19)	0.0296 (5)
H4'	0.8868	0.0247	0.4035	0.036*
C5'	0.9438 (3)	0.07756 (6)	0.42656 (17)	0.0253 (5)
H5'	0.9818	0.0831	0.3605	0.030*
C6'	0.9424 (3)	0.10373 (6)	0.50228 (16)	0.0211 (4)
C7'	1.0704 (3)	0.16200 (6)	0.42962 (16)	0.0235 (5)
H7C	1.1558	0.1471	0.3898	0.028*
H7D	1.1442	0.1814	0.4629	0.028*
C8'	0.9260 (3)	0.17904 (6)	0.35944 (16)	0.0226 (5)
H8'	0.8322	0.1917	0.4010	0.027*
C9'	1.0112 (3)	0.20660 (6)	0.29009 (15)	0.0207 (4)
C10'	1.1563 (3)	0.19730 (6)	0.22767 (17)	0.0241 (5)
H10'	1.2023	0.1731	0.2278	0.029*
C11'	1.2337 (3)	0.22296 (7)	0.16565 (17)	0.0290 (5)
H11'	1.3332	0.2165	0.1239	0.035*
C12'	1.1663 (3)	0.25810 (6)	0.16425 (16)	0.0262 (5)
H12'	1.2187	0.2757	0.1212	0.031*
C13'	1.0226 (3)	0.26762 (6)	0.22557 (16)	0.0243 (5)
H13'	0.9763	0.2917	0.2244	0.029*
C14'	0.9455 (3)	0.24203 (6)	0.28896 (16)	0.0228 (5)
H14'	0.8477	0.2488	0.3316	0.027*
C15'	0.6640 (3)	0.16060 (6)	0.25888 (18)	0.0287 (5)
H15C	0.6864	0.1714	0.1922	0.034*
H15D	0.6006	0.1788	0.3005	0.034*
C16'	0.5460 (3)	0.12733 (6)	0.24718 (17)	0.0246 (5)
C17'	0.4741 (3)	0.11645 (7)	0.15453 (17)	0.0265 (5)
H17'	0.4985	0.1305	0.0965	0.032*
C18'	0.3671 (3)	0.08540 (6)	0.14502 (18)	0.0267 (5)
H18'	0.3189	0.0780	0.0811	0.032*
C19'	0.3319 (3)	0.06545 (6)	0.23027 (18)	0.0272 (5)
C20'	0.4002 (3)	0.07576 (7)	0.32357 (18)	0.0303 (5)
H20'	0.3738	0.0617	0.3814	0.036*
C21'	0.5076 (3)	0.10674 (7)	0.33240 (17)	0.0268 (5)
H21'	0.5553	0.1140	0.3965	0.032*

	U11	U22	U33	U12	U13	U23
Cl1	0.0341 (4)	0.0352 (4)	0.0555 (5)	0.0105 (3)	0.0044 (3)	−0.0115 (3)
O1	0.0185 (8)	0.0235 (8)	0.0271 (8)	−0.0002 (6)	0.0016 (6)	−0.0028 (6)
N1	0.0275 (11)	0.0344 (11)	0.0244 (10)	0.0009 (9)	−0.0033 (8)	0.0026 (9)
N2	0.0290 (11)	0.0310 (11)	0.0205 (10)	−0.0007 (8)	−0.0004 (8)	−0.0020 (8)
N3	0.0245 (10)	0.0243 (9)	0.0197 (9)	0.0029 (7)	0.0006 (7)	0.0003 (7)
C1	0.0201 (11)	0.0300 (12)	0.0249 (11)	−0.0002 (9)	0.0007 (9)	0.0042 (9)
C2	0.0273 (13)	0.0369 (14)	0.0339 (13)	0.0034 (10)	−0.0004 (10)	0.0076 (11)
C3	0.0301 (13)	0.0263 (12)	0.0428 (15)	0.0051 (10)	0.0040 (11)	0.0040 (11)
C4	0.0260 (12)	0.0310 (13)	0.0371 (14)	−0.0006 (10)	0.0045 (10)	−0.0057 (11)
C5	0.0234 (12)	0.0318 (12)	0.0241 (11)	−0.0007 (9)	0.0035 (9)	−0.0004 (9)
C6	0.0182 (10)	0.0247 (11)	0.0239 (11)	0.0010 (9)	0.0018 (9)	0.0026 (9)
C7	0.0236 (11)	0.0264 (11)	0.0252 (11)	0.0053 (9)	0.0034 (9)	0.0025 (9)
C8	0.0219 (11)	0.0268 (11)	0.0229 (11)	0.0025 (9)	0.0012 (9)	−0.0021 (9)
C9	0.0185 (11)	0.0250 (11)	0.0193 (10)	0.0029 (8)	0.0031 (8)	−0.0047 (9)
C10	0.0246 (11)	0.0241 (11)	0.0215 (11)	0.0014 (9)	0.0025 (9)	−0.0010 (9)
C11	0.0256 (12)	0.0306 (12)	0.0215 (11)	0.0004 (9)	−0.0023 (9)	−0.0023 (9)
C12	0.0280 (12)	0.0278 (12)	0.0205 (11)	0.0059 (9)	0.0038 (9)	0.0013 (9)
C13	0.0251 (12)	0.0247 (11)	0.0248 (11)	−0.0002 (9)	0.0058 (9)	−0.0023 (9)
C14	0.0198 (11)	0.0282 (11)	0.0219 (11)	0.0007 (9)	0.0012 (8)	−0.0048 (9)
C15	0.0226 (12)	0.0290 (13)	0.0569 (17)	−0.0013 (10)	0.0100 (11)	−0.0076 (12)
C16	0.0157 (11)	0.0286 (12)	0.0350 (13)	−0.0019 (9)	−0.0002 (9)	−0.0056 (10)
C17	0.0203 (11)	0.0381 (13)	0.0237 (11)	0.0015 (10)	0.0027 (9)	−0.0016 (10)
C18	0.0254 (12)	0.0308 (12)	0.0310 (13)	0.0051 (10)	−0.0034 (10)	0.0038 (10)
C19	0.0186 (11)	0.0300 (12)	0.0348 (13)	0.0012 (9)	−0.0003 (9)	−0.0056 (10)
C20	0.0201 (11)	0.0342 (13)	0.0285 (12)	−0.0028 (9)	0.0032 (9)	−0.0037 (10)
C21	0.0193 (11)	0.0288 (12)	0.0336 (13)	−0.0038 (9)	0.0023 (9)	0.0026 (10)
Cl1'	0.0379 (4)	0.0285 (3)	0.0483 (4)	−0.0063 (3)	−0.0066 (3)	0.0003 (3)
O1'	0.0202 (8)	0.0246 (8)	0.0295 (9)	−0.0014 (6)	−0.0015 (6)	−0.0010 (7)
N1'	0.0327 (11)	0.0292 (10)	0.0267 (10)	0.0066 (9)	0.0044 (8)	0.0024 (8)
N2'	0.0342 (11)	0.0265 (10)	0.0216 (10)	0.0032 (8)	0.0005 (8)	−0.0014 (8)
N3'	0.0248 (10)	0.0205 (9)	0.0220 (9)	−0.0007 (7)	−0.0009 (7)	0.0005 (7)
C1'	0.0231 (11)	0.0235 (11)	0.0275 (12)	0.0040 (9)	0.0028 (9)	0.0016 (9)
C2'	0.0249 (12)	0.0323 (13)	0.0351 (13)	0.0054 (10)	0.0068 (10)	0.0099 (11)
C3'	0.0243 (12)	0.0230 (11)	0.0489 (15)	0.0012 (9)	0.0029 (11)	0.0054 (11)
C4'	0.0264 (12)	0.0226 (11)	0.0398 (14)	0.0019 (9)	−0.0020 (10)	−0.0054 (10)
C5'	0.0222 (11)	0.0261 (12)	0.0276 (12)	0.0023 (9)	−0.0015 (9)	−0.0019 (9)
C6'	0.0180 (10)	0.0200 (10)	0.0253 (11)	0.0013 (8)	−0.0003 (8)	0.0018 (9)
C7'	0.0221 (11)	0.0245 (11)	0.0240 (11)	−0.0042 (9)	−0.0012 (9)	0.0044 (9)
C8'	0.0201 (11)	0.0236 (11)	0.0239 (11)	−0.0009 (9)	−0.0014 (9)	0.0005 (9)
C9'	0.0188 (10)	0.0241 (11)	0.0191 (10)	−0.0010 (8)	−0.0031 (8)	0.0007 (9)
C10'	0.0225 (11)	0.0244 (11)	0.0254 (11)	0.0015 (9)	−0.0003 (9)	−0.0029 (9)
C11'	0.0234 (12)	0.0401 (14)	0.0238 (12)	−0.0014 (10)	0.0050 (9)	−0.0011 (10)
C12'	0.0270 (12)	0.0324 (12)	0.0191 (11)	−0.0086 (10)	−0.0023 (9)	0.0053 (9)
C13'	0.0274 (12)	0.0237 (11)	0.0217 (11)	−0.0026 (9)	−0.0049 (9)	0.0002 (9)
C14'	0.0227 (11)	0.0255 (11)	0.0202 (11)	−0.0002 (9)	−0.0014 (8)	−0.0017 (9)
C15'	0.0226 (12)	0.0334 (13)	0.0298 (12)	−0.0030 (10)	−0.0054 (9)	0.0052 (10)
C16'	0.0166 (10)	0.0295 (12)	0.0277 (12)	0.0022 (9)	0.0008 (9)	0.0035 (10)
C17'	0.0186 (11)	0.0360 (13)	0.0250 (12)	0.0022 (9)	−0.0001 (9)	0.0057 (10)
C18'	0.0211 (11)	0.0325 (12)	0.0264 (11)	0.0035 (9)	−0.0022 (9)	−0.0038 (10)
C19'	0.0210 (11)	0.0260 (11)	0.0346 (13)	0.0010 (9)	−0.0015 (10)	−0.0023 (10)
C20'	0.0265 (12)	0.0382 (14)	0.0264 (12)	−0.0035 (10)	0.0015 (9)	0.0063 (10)
C21'	0.0214 (11)	0.0355 (13)	0.0233 (11)	−0.0013 (9)	−0.0012 (9)	0.0010 (10)

Cl1—C19	1.734 (2)	Cl1'—C19'	1.745 (2)
O1—C8	1.422 (3)	O1'—C8'	1.421 (3)
O1—C15	1.432 (3)	O1'—C15'	1.435 (3)
N1—N2	1.309 (3)	N1'—N2'	1.299 (3)
N1—C1	1.371 (3)	N1'—C1'	1.377 (3)
N2—N3	1.361 (2)	N2'—N3'	1.356 (3)
N3—C6	1.353 (3)	N3'—C6'	1.360 (3)
N3—C7	1.445 (3)	N3'—C7'	1.446 (3)
C1—C6	1.394 (3)	C1'—C6'	1.397 (3)
C1—C2	1.401 (3)	C1'—C2'	1.403 (3)
C2—C3	1.371 (4)	C2'—C3'	1.365 (4)
C2—H2	0.95	C2'—H2'	0.95
C3—C4	1.411 (3)	C3'—C4'	1.415 (3)
C3—H3	0.95	C3'—H3'	0.95
C4—C5	1.373 (3)	C4'—C5'	1.371 (3)
C4—H4	0.95	C4'—H4'	0.95
C5—C6	1.395 (3)	C5'—C6'	1.395 (3)
C5—H5	0.95	C5'—H5'	0.9500
C7—C8	1.525 (3)	C7'—C8'	1.516 (3)
C7—H7A	0.99	C7'—H7C	0.99
C7—H7B	0.99	C7'—H7D	0.99
C8—C9	1.510 (3)	C8'—C9'	1.514 (3)
C8—H8	1.00	C8'—H8'	1.00
C9—C14	1.387 (3)	C9'—C14'	1.389 (3)
C9—C10	1.396 (3)	C9'—C10'	1.397 (3)
C10—C11	1.385 (3)	C10'—C11'	1.382 (3)
C10—H10	0.95	C10'—H10'	0.95
C11—C12	1.385 (3)	C11'—C12'	1.383 (3)
C11—H11	0.95	C11'—H11'	0.95
C12—C13	1.382 (3)	C12'—C13'	1.381 (3)
C12—H12	0.95	C12'—H12'	0.95
C13—C14	1.392 (3)	C13'—C14'	1.391 (3)
C13—H13	0.95	C13'—H13'	0.95
C14—H14	0.95	C14'—H14'	0.95
C15—C16	1.497 (3)	C15'—C16'	1.498 (3)
C15—H15A	0.99	C15'—H15C	0.99
C15—H15B	0.99	C15'—H15D	0.99
C16—C21	1.384 (3)	C16'—C17'	1.384 (3)
C16—C17	1.392 (3)	C16'—C21'	1.398 (3)
C17—C18	1.379 (3)	C17'—C18'	1.384 (3)
C17—H17	0.95	C17'—H17'	0.95
C18—C19	1.391 (3)	C18'—C19'	1.380 (3)
C18—H18	0.95	C18'—H18'	0.95
C19—C20	1.369 (3)	C19'—C20'	1.377 (3)
C20—C21	1.393 (3)	C20'—C21'	1.383 (3)
C20—H20	0.95	C20'—H20'	0.95
C21—H21	0.95	C21'—H21'	0.95
C8—O1—C15	113.13 (17)	C8'—O1'—C15'	113.31 (17)
N2—N1—C1	108.55 (18)	N2'—N1'—C1'	108.11 (18)
N1—N2—N3	108.07 (18)	N1'—N2'—N3'	109.20 (18)
C6—N3—N2	110.69 (17)	N2'—N3'—C6'	110.10 (18)
C6—N3—C7	128.75 (18)	N2'—N3'—C7'	119.96 (18)
N2—N3—C7	120.56 (18)	C6'—N3'—C7'	129.59 (19)
N1—C1—C6	108.6 (2)	N1'—C1'—C6'	108.51 (19)
N1—C1—C2	131.3 (2)	N1'—C1'—C2'	131.2 (2)
C6—C1—C2	120.1 (2)	C6'—C1'—C2'	120.3 (2)
C3—C2—C1	117.5 (2)	C3'—C2'—C1'	117.2 (2)
C3—C2—H2	121.2	C3'—C2'—H2'	121.4
C1—C2—H2	121.2	C1'—C2'—H2'	121.4
C2—C3—C4	121.5 (2)	C2'—C3'—C4'	121.9 (2)
C2—C3—H3	119.3	C2'—C3'—H3'	119.0
C4—C3—H3	119.3	C4'—C3'—H3'	119.0
C5—C4—C3	121.9 (2)	C5'—C4'—C3'	121.6 (2)
C5—C4—H4	119.0	C5'—C4'—H4'	119.2
C3—C4—H4	119.0	C3'—C4'—H4'	119.2
C4—C5—C6	116.2 (2)	C4'—C5'—C6'	116.4 (2)
C4—C5—H5	121.9	C4'—C5'—H5'	121.8
C6—C5—H5	121.9	C6'—C5'—H5'	121.8
N3—C6—C1	104.13 (19)	N3'—C6'—C5'	133.4 (2)
N3—C6—C5	133.0 (2)	N3'—C6'—C1'	104.07 (19)
C1—C6—C5	122.8 (2)	C5'—C6'—C1'	122.5 (2)
N3—C7—C8	111.97 (18)	N3'—C7'—C8'	112.26 (18)
N3—C7—H7A	109.2	N3'—C7'—H7C	109.2
C8—C7—H7A	109.2	C8'—C7'—H7C	109.2
N3—C7—H7B	109.2	N3'—C7'—H7D	109.2
C8—C7—H7B	109.2	C8'—C7'—H7D	109.2
H7A—C7—H7B	107.9	H7C—C7'—H7D	107.9
O1—C8—C9	112.19 (17)	O1'—C8'—C9'	112.79 (17)
O1—C8—C7	107.12 (17)	O1'—C8'—C7'	106.87 (17)
C9—C8—C7	111.46 (18)	C9'—C8'—C7'	111.70 (18)
O1—C8—H8	108.7	O1'—C8'—H8'	108.4
C9—C8—H8	108.7	C9'—C8'—H8'	108.4
C7—C8—H8	108.7	C7'—C8'—H8'	108.4
C14—C9—C10	119.3 (2)	C14'—C9'—C10'	119.0 (2)
C14—C9—C8	120.78 (19)	C14'—C9'—C8'	119.57 (19)
C10—C9—C8	119.91 (19)	C10'—C9'—C8'	121.38 (19)
C11—C10—C9	120.2 (2)	C11'—C10'—C9'	120.5 (2)
C11—C10—H10	119.9	C11'—C10'—H10'	119.7
C9—C10—H10	119.9	C9'—C10'—H10'	119.7
C12—C11—C10	120.2 (2)	C10'—C11'—C12'	120.1 (2)
C12—C11—H11	119.9	C10'—C11'—H11'	120.0
C10—C11—H11	119.9	C12'—C11'—H11'	120.0
C13—C12—C11	120.0 (2)	C13'—C12'—C11'	119.9 (2)
C13—C12—H12	120.0	C13'—C12'—H12'	120.0
C11—C12—H12	120.0	C11'—C12'—H12'	120.0
C12—C13—C14	120.1 (2)	C12'—C13'—C14'	120.3 (2)
C12—C13—H13	120.0	C12'—C13'—H13'	119.9
C14—C13—H13	120.0	C14'—C13'—H13'	119.9
C9—C14—C13	120.3 (2)	C9'—C14'—C13'	120.1 (2)
C9—C14—H14	119.9	C9'—C14'—H14'	119.9
C13—C14—H14	119.9	C13'—C14'—H14'	119.9
O1—C15—C16	109.06 (18)	O1'—C15'—C16'	108.11 (18)
O1—C15—H15A	109.9	O1'—C15'—H15C	110.1
C16—C15—H15A	109.9	C16'—C15'—H15C	110.1
O1—C15—H15B	109.9	O1'—C15'—H15D	110.1
C16—C15—H15B	109.9	C16'—C15'—H15D	110.1
H15A—C15—H15B	108.3	H15C—C15'—H15D	108.4
C21—C16—C17	118.9 (2)	C17'—C16'—C21'	119.1 (2)
C21—C16—C15	120.9 (2)	C17'—C16'—C15'	121.9 (2)
C17—C16—C15	120.2 (2)	C21'—C16'—C15'	119.0 (2)
C18—C17—C16	120.9 (2)	C16'—C17'—C18'	121.1 (2)
C18—C17—H17	119.6	C16'—C17'—H17'	119.5
C16—C17—H17	119.6	C18'—C17'—H17'	119.5
C17—C18—C19	118.9 (2)	C19'—C18'—C17'	118.6 (2)
C17—C18—H18	120.5	C19'—C18'—H18'	120.7
C19—C18—H18	120.5	C17'—C18'—H18'	120.7
C20—C19—C18	121.4 (2)	C20'—C19'—C18'	121.6 (2)
C20—C19—Cl1	119.79 (18)	C20'—C19'—Cl1'	119.05 (18)
C18—C19—Cl1	118.85 (19)	C18'—C19'—Cl1'	119.30 (18)
C19—C20—C21	119.1 (2)	C19'—C20'—C21'	119.4 (2)
C19—C20—H20	120.5	C19'—C20'—H20'	120.3
C21—C20—H20	120.5	C21'—C20'—H20'	120.3
C16—C21—C20	120.8 (2)	C20'—C21'—C16'	120.1 (2)
C16—C21—H21	119.6	C20'—C21'—H21'	119.9
C20—C21—H21	119.6	C16'—C21'—H21'	119.9
C1—N1—N2—N3	−0.4 (2)	C1'—N1'—N2'—N3'	1.1 (2)
N1—N2—N3—C6	0.2 (2)	N1'—N2'—N3'—C6'	−1.2 (2)
N1—N2—N3—C7	179.79 (19)	N1'—N2'—N3'—C7'	−175.07 (19)
N2—N1—C1—C6	0.4 (3)	N2'—N1'—C1'—C6'	−0.6 (3)
N2—N1—C1—C2	179.3 (2)	N2'—N1'—C1'—C2'	178.9 (2)
N1—C1—C2—C3	−177.2 (2)	N1'—C1'—C2'—C3'	−179.9 (2)
C6—C1—C2—C3	1.7 (3)	C6'—C1'—C2'—C3'	−0.5 (3)
C1—C2—C3—C4	−0.2 (4)	C1'—C2'—C3'—C4'	1.0 (4)
C2—C3—C4—C5	−1.6 (4)	C2'—C3'—C4'—C5'	−1.0 (4)
C3—C4—C5—C6	1.7 (3)	C3'—C4'—C5'—C6'	0.4 (3)
N2—N3—C6—C1	0.1 (2)	N2'—N3'—C6'—C5'	−178.8 (2)
C7—N3—C6—C1	−179.5 (2)	C7'—N3'—C6'—C5'	−5.7 (4)
N2—N3—C6—C5	−177.4 (2)	N2'—N3'—C6'—C1'	0.8 (2)
C7—N3—C6—C5	3.0 (4)	C7'—N3'—C6'—C1'	173.9 (2)
N1—C1—C6—N3	−0.3 (2)	C4'—C5'—C6'—N3'	179.7 (2)
C2—C1—C6—N3	−179.4 (2)	C4'—C5'—C6'—C1'	0.1 (3)
N1—C1—C6—C5	177.6 (2)	N1'—C1'—C6'—N3'	−0.2 (2)
C2—C1—C6—C5	−1.5 (3)	C2'—C1'—C6'—N3'	−179.7 (2)
C4—C5—C6—N3	176.9 (2)	N1'—C1'—C6'—C5'	179.5 (2)
C4—C5—C6—C1	−0.2 (3)	C2'—C1'—C6'—C5'	0.0 (3)
C6—N3—C7—C8	85.9 (3)	N2'—N3'—C7'—C8'	−99.2 (2)
N2—N3—C7—C8	−93.6 (2)	C6'—N3'—C7'—C8'	88.3 (3)
C15—O1—C8—C9	−86.2 (2)	C15'—O1'—C8'—C9'	−73.5 (2)
C15—O1—C8—C7	151.18 (19)	C15'—O1'—C8'—C7'	163.40 (18)
N3—C7—C8—O1	−57.0 (2)	N3'—C7'—C8'—O1'	−64.4 (2)
N3—C7—C8—C9	179.89 (17)	N3'—C7'—C8'—C9'	171.82 (18)
O1—C8—C9—C14	115.0 (2)	O1'—C8'—C9'—C14'	116.4 (2)
C7—C8—C9—C14	−124.9 (2)	C7'—C8'—C9'—C14'	−123.2 (2)
O1—C8—C9—C10	−65.3 (2)	O1'—C8'—C9'—C10'	−64.3 (3)
C7—C8—C9—C10	54.9 (3)	C7'—C8'—C9'—C10'	56.1 (3)
C14—C9—C10—C11	0.8 (3)	C14'—C9'—C10'—C11'	0.0 (3)
C8—C9—C10—C11	−178.91 (19)	C8'—C9'—C10'—C11'	−179.3 (2)
C9—C10—C11—C12	−1.1 (3)	C9'—C10'—C11'—C12'	−0.6 (3)
C10—C11—C12—C13	0.4 (3)	C10'—C11'—C12'—C13'	0.6 (3)
C11—C12—C13—C14	0.6 (3)	C11'—C12'—C13'—C14'	0.1 (3)
C10—C9—C14—C13	0.1 (3)	C10'—C9'—C14'—C13'	0.7 (3)
C8—C9—C14—C13	179.87 (19)	C8'—C9'—C14'—C13'	179.99 (19)
C12—C13—C14—C9	−0.8 (3)	C12'—C13'—C14'—C9'	−0.8 (3)
C8—O1—C15—C16	−165.84 (19)	C8'—O1'—C15'—C16'	−154.90 (18)
O1—C15—C16—C21	−121.1 (2)	O1'—C15'—C16'—C17'	−124.1 (2)
O1—C15—C16—C17	59.8 (3)	O1'—C15'—C16'—C21'	55.9 (3)
C21—C16—C17—C18	0.9 (3)	C21'—C16'—C17'—C18'	−0.8 (3)
C15—C16—C17—C18	180.0 (2)	C15'—C16'—C17'—C18'	179.2 (2)
C16—C17—C18—C19	−1.3 (4)	C16'—C17'—C18'—C19'	0.5 (3)
C17—C18—C19—C20	1.2 (4)	C17'—C18'—C19'—C20'	0.1 (3)
C17—C18—C19—Cl1	−178.19 (18)	C17'—C18'—C19'—Cl1'	178.37 (17)
C18—C19—C20—C21	−0.8 (4)	C18'—C19'—C20'—C21'	−0.3 (4)
Cl1—C19—C20—C21	178.61 (17)	Cl1'—C19'—C20'—C21'	−178.62 (18)
C17—C16—C21—C20	−0.5 (3)	C19'—C20'—C21'—C16'	0.0 (4)
C15—C16—C21—C20	−179.5 (2)	C17'—C16'—C21'—C20'	0.5 (3)
C19—C20—C21—C16	0.4 (3)	C15'—C16'—C21'—C20'	−179.5 (2)

Cg1, Cg2 and Cg3 are centroids of the C9–C14, C9'–C14' and C16–C21 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cg2i	0.95	2.62	3.515 (2)	157
C11'—H11'···Cg1ii	0.95	2.79	3.635 (2)	149
C14—H14···Cg2iii	0.95	2.64	3.584 (2)	172
C14'—H14'···Cg1iv	0.95	2.81	3.755 (2)	172
C18'—H18'···Cg3v	0.95	2.83	3.502 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are centroids of the C9–C14, C9′–C14′ and C16–C21 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cg2i	0.95	2.62	3.515 (2)	157
C11′—H11′⋯Cg1ii	0.95	2.79	3.635 (2)	149
C14—H14⋯Cg2iii	0.95	2.64	3.584 (2)	172
C14′—H14′⋯Cg1iv	0.95	2.81	3.755 (2)	172
C18′—H18′⋯Cg3v	0.95	2.83	3.502 (2)	129

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