2-(1H-Benzotriazol-1-yl)-3-(2,6-dichloro-phen-yl)-1-phenyl-propan-1-ol.

The asymmetric unit of the title compound, C(21)H(17)Cl(2)N(3)O, contains two crystallographically independent mol-ecules with similar conformations. The benzotriazole ring is oriented at dihedral angles of 30.61 (5) and 43.36 (5)°, respectively, to the phenyl and dichloro-phenyl rings in one mol-ecule, and 32.25 (5) and 41.04 (5)° in the other. The dihedral angles between the phenyl and dichloro-phenyl rings are 66.38 (7) and 66.14 (6)° in the two mol-ecules. An intra-molecular O-H⋯N hydrogen bond links the benzotriazole ring and phenyl-propanol unit in each mol-ecule. In the crystal, weak inter-molecular C-H⋯N hydrogen bonds link the mol-ecules into chains along the a axis. π-π stacking between the dichloro-phenyl rings [centroid-centroid distances = 3.809 (1) and 3.735 (1) Å] may further stabilize the crystal structure.

Related literature

For the biological activity of azole compounds, see: Cozzi et al. (1994 ▶) and of triazole derivatives, see: Jin et al. (2006 ▶). For related structures, see: Özel Güven et al. (2007 ▶, 2008 ▶, 2010 ▶).

Experimental

Crystal data

C21H17Cl2N3O

M = 398.28

Triclinic,

a = 9.3894 (2) Å

b = 9.4947 (2) Å

c = 21.2687 (3) Å

α = 91.415 (2)°

β = 92.324 (2)°

γ = 90.406 (1)°

V = 1893.90 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 120 K

0.4 × 0.4 × 0.3 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.866, T max = 0.897

40396 measured reflections

8697 independent reflections

7206 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.108

S = 1.07

8697 reflections

487 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.73 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 datablock(s) I, global. DOI: 10.1107/S1600536811034738/xu5297sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034738/xu5297Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034738/xu5297Isup3.cml

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

C21H17Cl2N3O	Z = 4
Mr = 398.28	F(000) = 824
Triclinic, P1	Dx = 1.397 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3894 (2) Å	Cell parameters from 14651 reflections
b = 9.4947 (2) Å	θ = 2.9–27.5°
c = 21.2687 (3) Å	µ = 0.36 mm−1
α = 91.415 (2)°	T = 120 K
β = 92.324 (2)°	Block, colorless
γ = 90.406 (1)°	0.4 × 0.4 × 0.3 mm
V = 1893.90 (6) Å3

Nonius KappaCCD diffractometer	8697 independent reflections
Radiation source: fine-focus sealed tube	7206 reflections with I > 2σ(I)
graphite	Rint = 0.044
φ and ω scans	θmax = 27.6°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −12→12
Tmin = 0.866, Tmax = 0.897	k = −12→11
40396 measured reflections	l = −27→27

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0504P)2 + 0.9534P] where P = (Fo2 + 2Fc2)/3
8697 reflections	(Δ/σ)max = 0.001
487 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.73 e Å−3

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	0.77473 (4)	1.06219 (5)	0.104106 (19)	0.02207 (10)
Cl2	0.97499 (5)	0.66618 (5)	−0.05798 (2)	0.03245 (12)
O1	0.42613 (13)	0.61760 (13)	−0.02537 (6)	0.0256 (3)
H1A	0.4009	0.6380	0.0101	0.038*
N1	0.60715 (15)	0.74669 (14)	0.06575 (6)	0.0162 (3)
N2	0.50172 (15)	0.83379 (15)	0.08432 (7)	0.0200 (3)
N3	0.49164 (16)	0.82583 (16)	0.14548 (7)	0.0206 (3)
C1	0.64956 (17)	0.73778 (17)	0.00021 (7)	0.0149 (3)
H1	0.7061	0.6522	−0.0048	0.018*
C2	0.52030 (18)	0.72524 (18)	−0.04605 (8)	0.0193 (3)
H2	0.4698	0.8152	−0.0462	0.023*
C3	0.57040 (18)	0.69279 (18)	−0.11180 (8)	0.0197 (4)
C4	0.5683 (2)	0.7957 (2)	−0.15719 (9)	0.0284 (4)
H4	0.5318	0.8842	−0.1479	0.034*
C5	0.6205 (3)	0.7673 (2)	−0.21634 (10)	0.0366 (5)
H5	0.6183	0.8366	−0.2465	0.044*
C6	0.6758 (2)	0.6356 (2)	−0.23049 (10)	0.0338 (5)
H6	0.7117	0.6171	−0.2699	0.041*
C7	0.6774 (2)	0.5318 (2)	−0.18587 (9)	0.0295 (4)
H7	0.7136	0.4433	−0.1955	0.035*
C8	0.6248 (2)	0.55996 (19)	−0.12650 (9)	0.0237 (4)
H8	0.6260	0.4901	−0.0966	0.028*
C9	0.66758 (18)	0.68088 (17)	0.11643 (8)	0.0160 (3)
C10	0.7773 (2)	0.58173 (18)	0.12292 (8)	0.0215 (4)
H10	0.8286	0.5502	0.0889	0.026*
C11	0.8040 (2)	0.5342 (2)	0.18290 (9)	0.0258 (4)
H11	0.8748	0.4676	0.1894	0.031*
C12	0.7273 (2)	0.5834 (2)	0.23490 (9)	0.0262 (4)
H12	0.7481	0.5472	0.2744	0.031*
C13	0.6226 (2)	0.6834 (2)	0.22842 (8)	0.0237 (4)
H13	0.5740	0.7172	0.2628	0.028*
C14	0.59246 (18)	0.73200 (17)	0.16758 (8)	0.0173 (3)
C15	0.74540 (17)	0.86394 (17)	−0.01401 (8)	0.0157 (3)
H15A	0.7664	0.8609	−0.0583	0.019*
H15B	0.6948	0.9506	−0.0055	0.019*
C16	0.88295 (17)	0.86400 (17)	0.02488 (8)	0.0166 (3)
C17	0.90693 (18)	0.94709 (18)	0.07957 (8)	0.0183 (3)
C18	1.03235 (19)	0.9434 (2)	0.11631 (9)	0.0238 (4)
H18	1.0437	0.9998	0.1526	0.029*
C19	1.1407 (2)	0.8542 (2)	0.09808 (9)	0.0289 (4)
H19	1.2255	0.8510	0.1222	0.035*
C20	1.12324 (19)	0.7704 (2)	0.04434 (10)	0.0276 (4)
H20	1.1960	0.7113	0.0319	0.033*
C21	0.99607 (19)	0.77537 (19)	0.00931 (9)	0.0225 (4)
Cl1'	0.43627 (5)	1.25631 (4)	0.394633 (19)	0.02133 (10)
Cl2'	0.83607 (5)	1.47909 (5)	0.56172 (2)	0.02874 (12)
O1'	0.88141 (13)	0.93042 (12)	0.52629 (6)	0.0217 (3)
H1B	0.8569	0.8991	0.4912	0.032*
N1'	0.74653 (15)	1.09289 (14)	0.43580 (6)	0.0143 (3)
N2'	0.65658 (15)	0.98414 (14)	0.41974 (7)	0.0184 (3)
N3'	0.65629 (16)	0.96282 (15)	0.35860 (7)	0.0201 (3)
C1'	0.76151 (17)	1.14764 (16)	0.50055 (7)	0.0134 (3)
H1'	0.8488	1.2049	0.5043	0.016*
C2'	0.77665 (18)	1.02758 (17)	0.54764 (8)	0.0163 (3)
H2'	0.6849	0.9782	0.5494	0.020*
C3'	0.81778 (18)	1.08827 (17)	0.61265 (8)	0.0167 (3)
C4'	0.95523 (19)	1.14282 (18)	0.62497 (8)	0.0207 (4)
H4'	1.0218	1.1385	0.5938	0.025*
C5'	0.9927 (2)	1.2033 (2)	0.68340 (9)	0.0251 (4)
H5'	1.0840	1.2402	0.6911	0.030*
C6'	0.8942 (2)	1.2090 (2)	0.73039 (9)	0.0283 (4)
H6'	0.9194	1.2499	0.7695	0.034*
C7'	0.7588 (2)	1.1537 (2)	0.71895 (9)	0.0278 (4)
H7'	0.6932	1.1569	0.7505	0.033*
C8'	0.7202 (2)	1.09329 (19)	0.66023 (8)	0.0224 (4)
H8'	0.6289	1.0562	0.6528	0.027*
C9'	0.80557 (17)	1.14485 (17)	0.38334 (7)	0.0150 (3)
C10'	0.90362 (19)	1.25377 (18)	0.37405 (8)	0.0200 (4)
H10'	0.9412	1.3100	0.4072	0.024*
C11'	0.9407 (2)	1.2722 (2)	0.31273 (9)	0.0272 (4)
H11'	1.0059	1.3427	0.3042	0.033*
C12'	0.8824 (2)	1.1869 (2)	0.26232 (9)	0.0309 (4)
H12'	0.9107	1.2029	0.2217	0.037*
C13'	0.7850 (2)	1.08096 (19)	0.27169 (8)	0.0262 (4)
H13'	0.7465	1.0257	0.2384	0.031*
C14'	0.74682 (19)	1.06059 (17)	0.33400 (8)	0.0180 (3)
C15'	0.63528 (17)	1.24411 (16)	0.51530 (7)	0.0146 (3)
H15C	0.5466	1.1929	0.5066	0.017*
H15D	0.6403	1.2706	0.5597	0.017*
C16'	0.63594 (18)	1.37529 (16)	0.47679 (8)	0.0160 (3)
C17'	0.55197 (18)	1.39105 (17)	0.42163 (8)	0.0167 (3)
C18'	0.5560 (2)	1.51185 (18)	0.38579 (8)	0.0213 (4)
H18'	0.4990	1.5184	0.3492	0.026*
C19'	0.6460 (2)	1.62216 (18)	0.40542 (9)	0.0237 (4)
H19'	0.6494	1.7032	0.3818	0.028*
C20'	0.7307 (2)	1.61274 (18)	0.45971 (9)	0.0238 (4)
H20'	0.7903	1.6871	0.4731	0.029*
C21'	0.72545 (19)	1.49006 (18)	0.49406 (8)	0.0193 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.0183 (2)	0.0301 (2)	0.0176 (2)	0.00322 (16)	0.00066 (16)	−0.00500 (16)
Cl2	0.0273 (2)	0.0317 (3)	0.0388 (3)	0.00458 (19)	0.0124 (2)	−0.0105 (2)
O1	0.0194 (6)	0.0270 (7)	0.0307 (7)	−0.0052 (5)	0.0077 (5)	−0.0054 (5)
N1	0.0161 (7)	0.0160 (7)	0.0170 (7)	0.0044 (5)	0.0052 (5)	0.0029 (5)
N2	0.0157 (7)	0.0215 (7)	0.0233 (8)	0.0046 (6)	0.0058 (6)	−0.0001 (6)
N3	0.0177 (7)	0.0252 (8)	0.0190 (7)	0.0010 (6)	0.0038 (6)	−0.0031 (6)
C1	0.0155 (8)	0.0155 (8)	0.0139 (8)	0.0033 (6)	0.0034 (6)	0.0018 (6)
C2	0.0154 (8)	0.0177 (8)	0.0244 (9)	−0.0001 (6)	0.0000 (7)	−0.0025 (7)
C3	0.0174 (8)	0.0211 (8)	0.0202 (9)	−0.0008 (7)	−0.0030 (7)	−0.0031 (7)
C4	0.0334 (11)	0.0256 (10)	0.0256 (10)	0.0024 (8)	−0.0051 (8)	−0.0002 (8)
C5	0.0459 (13)	0.0398 (12)	0.0240 (10)	−0.0039 (10)	−0.0013 (9)	0.0067 (9)
C6	0.0345 (11)	0.0463 (12)	0.0205 (10)	−0.0060 (9)	0.0039 (8)	−0.0059 (8)
C7	0.0299 (11)	0.0288 (10)	0.0295 (10)	−0.0005 (8)	0.0044 (8)	−0.0115 (8)
C8	0.0251 (9)	0.0219 (9)	0.0239 (9)	−0.0022 (7)	0.0029 (7)	−0.0040 (7)
C9	0.0177 (8)	0.0145 (8)	0.0158 (8)	−0.0008 (6)	0.0018 (6)	0.0006 (6)
C10	0.0256 (9)	0.0210 (9)	0.0183 (8)	0.0065 (7)	0.0037 (7)	0.0012 (7)
C11	0.0294 (10)	0.0244 (9)	0.0238 (9)	0.0067 (8)	−0.0019 (8)	0.0052 (7)
C12	0.0298 (10)	0.0321 (10)	0.0167 (9)	−0.0015 (8)	−0.0021 (7)	0.0052 (7)
C13	0.0231 (9)	0.0308 (10)	0.0170 (8)	−0.0040 (7)	0.0038 (7)	−0.0035 (7)
C14	0.0150 (8)	0.0186 (8)	0.0184 (8)	−0.0027 (6)	0.0029 (6)	−0.0023 (6)
C15	0.0155 (8)	0.0176 (8)	0.0140 (8)	0.0000 (6)	0.0010 (6)	0.0005 (6)
C16	0.0139 (8)	0.0198 (8)	0.0165 (8)	−0.0003 (6)	0.0028 (6)	0.0038 (6)
C17	0.0134 (8)	0.0232 (9)	0.0185 (8)	−0.0002 (6)	0.0032 (6)	0.0040 (7)
C18	0.0175 (9)	0.0347 (10)	0.0191 (9)	−0.0029 (7)	−0.0022 (7)	0.0059 (7)
C19	0.0139 (9)	0.0434 (12)	0.0298 (10)	0.0001 (8)	−0.0012 (7)	0.0144 (9)
C20	0.0148 (9)	0.0320 (10)	0.0373 (11)	0.0061 (7)	0.0081 (8)	0.0102 (8)
C21	0.0174 (9)	0.0256 (9)	0.0250 (9)	0.0005 (7)	0.0072 (7)	0.0028 (7)
Cl1'	0.0268 (2)	0.0159 (2)	0.0207 (2)	−0.00349 (16)	−0.00538 (17)	0.00179 (15)
Cl2'	0.0305 (3)	0.0212 (2)	0.0332 (3)	−0.00356 (17)	−0.01093 (19)	−0.00507 (18)
O1'	0.0232 (6)	0.0154 (6)	0.0258 (7)	0.0046 (5)	−0.0037 (5)	−0.0032 (5)
N1'	0.0161 (7)	0.0123 (6)	0.0146 (7)	−0.0029 (5)	0.0016 (5)	−0.0021 (5)
N2'	0.0200 (7)	0.0137 (7)	0.0211 (7)	−0.0041 (5)	−0.0005 (6)	−0.0042 (5)
N3'	0.0253 (8)	0.0154 (7)	0.0189 (7)	−0.0010 (6)	−0.0030 (6)	−0.0025 (5)
C1'	0.0147 (8)	0.0121 (7)	0.0133 (7)	−0.0023 (6)	0.0008 (6)	−0.0014 (6)
C2'	0.0158 (8)	0.0136 (8)	0.0193 (8)	−0.0012 (6)	−0.0009 (6)	0.0027 (6)
C3'	0.0186 (8)	0.0140 (8)	0.0173 (8)	0.0019 (6)	−0.0024 (6)	0.0040 (6)
C4'	0.0184 (9)	0.0237 (9)	0.0200 (9)	0.0011 (7)	−0.0011 (7)	0.0009 (7)
C5'	0.0218 (9)	0.0266 (9)	0.0262 (10)	−0.0010 (7)	−0.0061 (7)	−0.0016 (7)
C6'	0.0340 (11)	0.0314 (10)	0.0189 (9)	0.0071 (8)	−0.0046 (8)	−0.0028 (7)
C7'	0.0307 (10)	0.0322 (10)	0.0210 (9)	0.0047 (8)	0.0052 (8)	0.0021 (8)
C8'	0.0194 (9)	0.0243 (9)	0.0236 (9)	0.0008 (7)	0.0014 (7)	0.0046 (7)
C9'	0.0152 (8)	0.0149 (8)	0.0148 (8)	0.0025 (6)	0.0014 (6)	0.0005 (6)
C10'	0.0203 (9)	0.0204 (8)	0.0192 (8)	−0.0046 (7)	0.0017 (7)	−0.0008 (6)
C11'	0.0325 (11)	0.0261 (10)	0.0235 (9)	−0.0057 (8)	0.0074 (8)	0.0045 (7)
C12'	0.0500 (13)	0.0278 (10)	0.0157 (9)	0.0001 (9)	0.0088 (8)	0.0034 (7)
C13'	0.0429 (12)	0.0204 (9)	0.0148 (8)	0.0000 (8)	−0.0025 (8)	−0.0017 (7)
C14'	0.0217 (9)	0.0145 (8)	0.0177 (8)	0.0025 (6)	−0.0018 (7)	−0.0005 (6)
C15'	0.0170 (8)	0.0129 (7)	0.0140 (8)	0.0005 (6)	0.0022 (6)	0.0007 (6)
C16'	0.0199 (8)	0.0114 (7)	0.0170 (8)	0.0022 (6)	0.0045 (6)	−0.0008 (6)
C17'	0.0207 (8)	0.0125 (7)	0.0170 (8)	0.0000 (6)	0.0041 (6)	−0.0009 (6)
C18'	0.0289 (10)	0.0178 (8)	0.0176 (8)	0.0037 (7)	0.0051 (7)	0.0033 (6)
C19'	0.0334 (10)	0.0126 (8)	0.0259 (9)	0.0000 (7)	0.0105 (8)	0.0040 (7)
C20'	0.0272 (10)	0.0125 (8)	0.0321 (10)	−0.0037 (7)	0.0082 (8)	−0.0026 (7)
C21'	0.0201 (9)	0.0165 (8)	0.0212 (9)	0.0003 (6)	0.0012 (7)	−0.0036 (6)

Cl1—C17	1.7467 (17)	Cl1'—C17'	1.7435 (17)
Cl2—C21	1.7500 (19)	Cl2'—C21'	1.7460 (18)
O1—C2	1.435 (2)	O1'—C2'	1.433 (2)
O1—H1A	0.8200	O1'—H1B	0.8200
N1—N2	1.3591 (19)	N1'—C1'	1.461 (2)
N1—C1	1.466 (2)	N1'—C9'	1.367 (2)
N1—C9	1.365 (2)	N2'—N1'	1.3576 (19)
N2—N3	1.312 (2)	N2'—N3'	1.311 (2)
N3—C14	1.381 (2)	N3'—C14'	1.381 (2)
C1—C2	1.533 (2)	C1'—C2'	1.540 (2)
C1—C15	1.536 (2)	C1'—C15'	1.541 (2)
C1—H1	0.9800	C1'—H1'	0.9800
C2—H2	0.9800	C2'—C3'	1.519 (2)
C3—C2	1.519 (2)	C2'—H2'	0.9800
C3—C4	1.390 (3)	C3'—C4'	1.400 (2)
C3—C8	1.397 (2)	C3'—C8'	1.393 (2)
C4—C5	1.389 (3)	C4'—C5'	1.387 (3)
C4—H4	0.9300	C4'—H4'	0.9300
C5—H5	0.9300	C5'—H5'	0.9300
C6—C5	1.388 (3)	C6'—C7'	1.382 (3)
C6—H6	0.9300	C6'—C5'	1.389 (3)
C7—C6	1.385 (3)	C6'—H6'	0.9300
C7—H7	0.9300	C7'—H7'	0.9300
C8—C7	1.395 (3)	C8'—C7'	1.395 (3)
C8—H8	0.9300	C8'—H8'	0.9300
C9—C10	1.405 (2)	C9'—C10'	1.403 (2)
C9—C14	1.399 (2)	C9'—C14'	1.397 (2)
C10—C11	1.378 (3)	C10'—C11'	1.379 (2)
C10—H10	0.9300	C10'—H10'	0.9300
C11—H11	0.9300	C11'—C12'	1.418 (3)
C12—C11	1.415 (3)	C11'—H11'	0.9300
C12—H12	0.9300	C12'—H12'	0.9300
C13—C12	1.377 (3)	C13'—C12'	1.378 (3)
C13—C14	1.403 (2)	C13'—H13'	0.9300
C13—H13	0.9300	C14'—C13'	1.404 (2)
C15—H15A	0.9700	C15'—H15C	0.9700
C15—H15B	0.9700	C15'—H15D	0.9700
C16—C15	1.505 (2)	C16'—C15'	1.508 (2)
C16—C17	1.399 (2)	C16'—C17'	1.398 (2)
C16—C21	1.405 (2)	C16'—C21'	1.404 (2)
C17—C18	1.388 (2)	C17'—C18'	1.394 (2)
C18—C19	1.390 (3)	C18'—C19'	1.387 (3)
C18—H18	0.9300	C18'—H18'	0.9300
C19—H19	0.9300	C19'—H19'	0.9300
C20—C19	1.380 (3)	C20'—C19'	1.380 (3)
C20—H20	0.9300	C20'—C21'	1.392 (2)
C21—C20	1.383 (3)	C20'—H20'	0.9300
C2—O1—H1A	109.5	C2'—O1'—H1B	109.5
N2—N1—C1	121.83 (13)	N2'—N1'—C1'	121.39 (13)
N2—N1—C9	110.25 (13)	N2'—N1'—C9'	110.31 (13)
C9—N1—C1	127.81 (13)	C9'—N1'—C1'	128.08 (13)
N3—N2—N1	108.75 (13)	N3'—N2'—N1'	108.85 (13)
N2—N3—C14	108.35 (13)	N2'—N3'—C14'	108.13 (13)
N1—C1—C2	111.92 (13)	N1'—C1'—C2'	111.37 (12)
N1—C1—C15	110.06 (13)	N1'—C1'—C15'	110.12 (13)
N1—C1—H1	107.6	N1'—C1'—H1'	107.8
C2—C1—C15	111.85 (13)	C2'—C1'—C15'	111.68 (13)
C2—C1—H1	107.6	C2'—C1'—H1'	107.8
C15—C1—H1	107.6	C15'—C1'—H1'	107.8
O1—C2—C3	111.67 (14)	O1'—C2'—C3'	111.31 (13)
O1—C2—C1	108.97 (14)	O1'—C2'—C1'	109.00 (13)
O1—C2—H2	108.9	O1'—C2'—H2'	108.9
C1—C2—H2	108.9	C1'—C2'—H2'	108.9
C3—C2—C1	109.52 (13)	C3'—C2'—C1'	109.66 (13)
C3—C2—H2	108.9	C3'—C2'—H2'	108.9
C4—C3—C2	120.78 (16)	C4'—C3'—C2'	119.74 (15)
C4—C3—C8	119.18 (17)	C8'—C3'—C2'	121.20 (15)
C8—C3—C2	119.99 (16)	C8'—C3'—C4'	119.05 (16)
C3—C4—H4	119.8	C3'—C4'—H4'	119.8
C5—C4—C3	120.48 (18)	C5'—C4'—C3'	120.41 (17)
C5—C4—H4	119.8	C5'—C4'—H4'	119.8
C4—C5—H5	119.9	C4'—C5'—C6'	120.11 (18)
C6—C5—C4	120.11 (19)	C4'—C5'—H5'	119.9
C6—C5—H5	119.9	C6'—C5'—H5'	119.9
C5—C6—H6	120.0	C5'—C6'—H6'	120.0
C7—C6—C5	119.98 (19)	C7'—C6'—C5'	119.91 (18)
C7—C6—H6	120.0	C7'—C6'—H6'	120.0
C6—C7—C8	120.03 (18)	C6'—C7'—C8'	120.28 (18)
C6—C7—H7	120.0	C6'—C7'—H7'	119.9
C8—C7—H7	120.0	C8'—C7'—H7'	119.9
C3—C8—H8	119.9	C3'—C8'—C7'	120.22 (17)
C7—C8—C3	120.21 (18)	C3'—C8'—H8'	119.9
C7—C8—H8	119.9	C7'—C8'—H8'	119.9
N1—C9—C10	133.02 (15)	N1'—C9'—C10'	133.11 (15)
N1—C9—C14	104.37 (14)	N1'—C9'—C14'	104.09 (14)
C14—C9—C10	122.61 (15)	C14'—C9'—C10'	122.80 (15)
C9—C10—H10	122.1	C9'—C10'—H10'	122.1
C11—C10—C9	115.72 (16)	C11'—C10'—C9'	115.79 (16)
C11—C10—H10	122.1	C11'—C10'—H10'	122.1
C10—C11—C12	122.25 (17)	C10'—C11'—C12'	121.91 (18)
C10—C11—H11	118.9	C10'—C11'—H11'	119.0
C12—C11—H11	118.9	C12'—C11'—H11'	119.0
C11—C12—H12	119.2	C11'—C12'—H12'	119.0
C13—C12—C11	121.64 (17)	C13'—C12'—C11'	122.00 (17)
C13—C12—H12	119.2	C13'—C12'—H12'	119.0
C12—C13—C14	117.06 (16)	C12'—C13'—C14'	116.67 (17)
C12—C13—H13	121.5	C12'—C13'—H13'	121.7
C14—C13—H13	121.5	C14'—C13'—H13'	121.7
N3—C14—C9	108.29 (14)	N3'—C14'—C9'	108.62 (15)
N3—C14—C13	130.99 (16)	N3'—C14'—C13'	130.53 (16)
C9—C14—C13	120.68 (16)	C9'—C14'—C13'	120.83 (16)
C1—C15—H15A	109.2	C1'—C15'—H15C	109.3
C1—C15—H15B	109.2	C1'—C15'—H15D	109.3
C16—C15—C1	111.91 (13)	C16'—C15'—C1'	111.63 (13)
C16—C15—H15A	109.2	C16'—C15'—H15C	109.3
C16—C15—H15B	109.2	C16'—C15'—H15D	109.3
H15A—C15—H15B	107.9	H15C—C15'—H15D	108.0
C17—C16—C15	123.48 (15)	C17'—C16'—C15'	123.46 (15)
C17—C16—C21	115.01 (16)	C17'—C16'—C21'	115.44 (15)
C21—C16—C15	121.47 (15)	C21'—C16'—C15'	121.08 (15)
C16—C17—Cl1	119.61 (13)	C16'—C17'—Cl1'	120.24 (12)
C18—C17—Cl1	117.19 (14)	C18'—C17'—Cl1'	116.96 (14)
C18—C17—C16	123.21 (16)	C18'—C17'—C16'	122.80 (16)
C17—C18—C19	118.98 (18)	C17'—C18'—H18'	120.4
C17—C18—H18	120.5	C19'—C18'—C17'	119.14 (17)
C19—C18—H18	120.5	C19'—C18'—H18'	120.4
C18—C19—H19	119.8	C18'—C19'—H19'	119.7
C20—C19—C18	120.31 (17)	C20'—C19'—C18'	120.56 (16)
C20—C19—H19	119.8	C20'—C19'—H19'	119.7
C19—C20—C21	119.15 (17)	C19'—C20'—C21'	118.90 (16)
C19—C20—H20	120.4	C19'—C20'—H20'	120.6
C21—C20—H20	120.4	C21'—C20'—H20'	120.6
C16—C21—Cl2	118.25 (14)	C20'—C21'—C16'	123.15 (16)
C20—C21—Cl2	118.42 (14)	C20'—C21'—Cl2'	118.11 (14)
C20—C21—C16	123.33 (17)	C16'—C21'—Cl2'	118.74 (13)
C1—N1—N2—N3	−176.70 (14)	N2'—N1'—C1'—C2'	45.82 (19)
C9—N1—N2—N3	−0.29 (19)	N2'—N1'—C1'—C15'	−78.65 (17)
N2—N1—C1—C2	−46.4 (2)	C9'—N1'—C1'—C2'	−140.11 (16)
N2—N1—C1—C15	78.61 (18)	C9'—N1'—C1'—C15'	95.42 (18)
C9—N1—C1—C2	137.85 (17)	N2'—N1'—C9'—C10'	−179.53 (17)
C9—N1—C1—C15	−97.12 (18)	N2'—N1'—C9'—C14'	−0.33 (17)
N2—N1—C9—C10	179.28 (18)	C1'—N1'—C9'—C10'	5.9 (3)
N2—N1—C9—C14	0.33 (18)	C1'—N1'—C9'—C14'	−174.94 (15)
C1—N1—C9—C10	−4.6 (3)	N3'—N2'—N1'—C9'	0.62 (18)
C1—N1—C9—C14	176.47 (15)	N3'—N2'—N1'—C1'	175.64 (13)
N1—N2—N3—C14	0.12 (18)	N1'—N2'—N3'—C14'	−0.63 (17)
N2—N3—C14—C9	0.09 (19)	N2'—N3'—C14'—C9'	0.42 (18)
N2—N3—C14—C13	−177.81 (18)	N2'—N3'—C14'—C13'	179.01 (18)
N1—C1—C2—O1	−48.50 (17)	N1'—C1'—C2'—O1'	48.02 (17)
N1—C1—C2—C3	−170.92 (13)	N1'—C1'—C2'—C3'	170.11 (13)
C15—C1—C2—O1	−172.54 (13)	C15'—C1'—C2'—O1'	171.61 (13)
C15—C1—C2—C3	65.04 (17)	C15'—C1'—C2'—C3'	−66.30 (17)
N1—C1—C15—C16	63.47 (17)	N1'—C1'—C15'—C16'	−65.81 (17)
C2—C1—C15—C16	−171.46 (13)	C2'—C1'—C15'—C16'	169.90 (13)
C4—C3—C2—O1	133.27 (17)	O1'—C2'—C3'—C4'	49.0 (2)
C4—C3—C2—C1	−105.93 (19)	O1'—C2'—C3'—C8'	−132.25 (16)
C8—C3—C2—O1	−49.4 (2)	C1'—C2'—C3'—C4'	−71.69 (19)
C8—C3—C2—C1	71.4 (2)	C1'—C2'—C3'—C8'	107.05 (17)
C8—C3—C4—C5	−0.4 (3)	C2'—C3'—C4'—C5'	177.60 (15)
C2—C3—C4—C5	176.99 (18)	C8'—C3'—C4'—C5'	−1.2 (3)
C2—C3—C8—C7	−176.87 (17)	C2'—C3'—C8'—C7'	−177.86 (16)
C4—C3—C8—C7	0.5 (3)	C4'—C3'—C8'—C7'	0.9 (3)
C3—C4—C5—C6	−0.3 (3)	C3'—C4'—C5'—C6'	0.6 (3)
C7—C6—C5—C4	0.8 (3)	C7'—C6'—C5'—C4'	0.3 (3)
C8—C7—C6—C5	−0.6 (3)	C5'—C6'—C7'—C8'	−0.5 (3)
C3—C8—C7—C6	0.0 (3)	C3'—C8'—C7'—C6'	0.0 (3)
N1—C9—C10—C11	−176.93 (18)	N1'—C9'—C10'—C11'	178.29 (18)
C14—C9—C10—C11	1.9 (3)	C14'—C9'—C10'—C11'	−0.8 (3)
N1—C9—C14—N3	−0.25 (18)	N1'—C9'—C14'—N3'	−0.05 (18)
N1—C9—C14—C13	177.90 (16)	N1'—C9'—C14'—C13'	−178.80 (16)
C10—C9—C14—N3	−179.34 (16)	C10'—C9'—C14'—N3'	179.25 (15)
C10—C9—C14—C13	−1.2 (3)	C10'—C9'—C14'—C13'	0.5 (3)
C9—C10—C11—C12	−0.8 (3)	C9'—C10'—C11'—C12'	0.4 (3)
C13—C12—C11—C10	−0.9 (3)	C10'—C11'—C12'—C13'	0.2 (3)
C14—C13—C12—C11	1.6 (3)	C14'—C13'—C12'—C11'	−0.5 (3)
C12—C13—C14—N3	177.08 (18)	N3'—C14'—C13'—C12'	−178.28 (18)
C12—C13—C14—C9	−0.6 (3)	C9'—C14'—C13'—C12'	0.2 (3)
C17—C16—C15—C1	−99.63 (18)	C17'—C16'—C15'—C1'	98.63 (18)
C21—C16—C15—C1	78.26 (19)	C21'—C16'—C15'—C1'	−79.95 (19)
C15—C16—C17—Cl1	−2.1 (2)	C15'—C16'—C17'—Cl1'	1.2 (2)
C15—C16—C17—C18	177.91 (16)	C15'—C16'—C17'—C18'	−178.60 (15)
C21—C16—C17—Cl1	179.90 (12)	C21'—C16'—C17'—Cl1'	179.83 (12)
C21—C16—C17—C18	−0.1 (2)	C21'—C16'—C17'—C18'	0.1 (2)
C15—C16—C21—Cl2	1.3 (2)	C15'—C16'—C21'—C20'	179.40 (16)
C15—C16—C21—C20	−178.87 (16)	C17'—C16'—C21'—C20'	0.7 (2)
C17—C16—C21—Cl2	179.38 (12)	C15'—C16'—C21'—Cl2'	−0.5 (2)
C17—C16—C21—C20	−0.8 (3)	C17'—C16'—C21'—Cl2'	−179.16 (12)
Cl1—C17—C18—C19	−179.39 (14)	Cl1'—C17'—C18'—C19'	179.82 (13)
C16—C17—C18—C19	0.6 (3)	C16'—C17'—C18'—C19'	−0.4 (3)
C17—C18—C19—C20	−0.2 (3)	C17'—C18'—C19'—C20'	0.0 (3)
C21—C20—C19—C18	−0.6 (3)	C21'—C20'—C19'—C18'	0.7 (3)
Cl2—C21—C20—C19	−179.01 (14)	C19'—C20'—C21'—Cl2'	178.75 (14)
C16—C21—C20—C19	1.2 (3)	C19'—C20'—C21'—C16'	−1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2	0.82	2.56	3.1254 (19)	127
O1'—H1B···N2'	0.82	2.52	3.0881 (19)	128
C19—H19···N3i	0.93	2.54	3.420 (2)	158
C19'—H19'···N3'ii	0.93	2.53	3.410 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N2	0.82	2.56	3.1254 (19)	127
O1′—H1B⋯N2′	0.82	2.52	3.0881 (19)	128
C19—H19⋯N3i	0.93	2.54	3.420 (2)	158
C19′—H19′⋯N3′ii	0.93	2.53	3.410 (2)	159

Symmetry codes: (i) ; (ii) .