2-(1H-Benzotriazol-1-yl)-3-(2,6-dichloro­phen­yl)-1-phenyl­propan-1-ol

Özel Güven, Ö.; Çapanlar, S.; Coles, S.J.; Hökelek, T.

doi:10.1107/S1600536811034738

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2510

doi:10.1107/S1600536811034738

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2-(1H-Benzotriazol-1-yl)-3-(2,6-dichlorophenyl)-1-phenylpropan-1-ol

Özden Özel Güven,^a Seval Çapanlar,^a Simon J. Coles ^b and Tuncer Hökelek ^c ^*

^aDepartment of Chemistry, Zonguldak Karaelmas University, 67100 Zonguldak, Turkey, ^bDepartment of Chemistry, Southampton University, SO17 1BJ Southampton, England, and ^cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 12 August 2011; accepted 24 August 2011; online 27 August 2011)

The asymmetric unit of the title compound, C₂₁H₁₇Cl₂N₃O, contains two crystallographically independent molecules with similar conformations. The benzotriazole ring is oriented at dihedral angles of 30.61 (5) and 43.36 (5)°, respectively, to the phenyl and dichlorophenyl rings in one molecule, and 32.25 (5) and 41.04 (5)° in the other. The dihedral angles between the phenyl and dichlorophenyl rings are 66.38 (7) and 66.14 (6)° in the two molecules. An intramolecular O—H⋯N hydrogen bond links the benzotriazole ring and phenylpropanol unit in each molecule. In the crystal, weak intermolecular C—H⋯N hydrogen bonds link the molecules into chains along the a axis. π–π stacking between the dichlorophenyl 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_r = 398.28
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.108
S = 1.07
8697 reflections
487 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.73 e Å⁻³

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) x+1, y, z; (ii) x, y+1, z.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811034738/xu5297sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811034738/xu5297Isup3.cml

checkCIF report

Comment top

Azole compounds have important biological activities. In literature 2-(1H-imidazol-1-yl)-1,3-diphenylpropan-1-one and its derivatives have been reported that they show both high and selective thromboxane A2 receptor antagonist and thromboxane A2 synthase inhibitory activity (Cozzi et al., 1994). Some 1H-1,2,4-triazole derivatives have been known as antifungal and plant growth regulatory agents (Jin et al., 2006). Crystal structures of similar compounds like ketone having benzimidazole and furan rings (Özel Güven et al., 2007) and alcohols having 1,2,4-triazole and benzotriazole rings have been reported (Özel Güven et al., 2008; Özel Güven et al., 2010). Now, we report herein the crystal structure of the title benzotriazole derivative, (I).

The asymmetric unit of the title compound (Fig. 1) contains two crystallographically independent molecules, in which they differ slightly in the orientations of the 2-6-dichlorophenyl units and the bond lengths and angles are generally within normal ranges. The intramolecular O—H···N hydrogen bonds (Table 1) link the benzotriazole rings and phenylpropan units. In each molecule, the planar benzotriazole rings [A (N1-N3/C9-C14) and A' (N1'-N3'/C9'-C14')] are oriented with respect to the phenyl [B (C3-C8) and B' (C3'-C8')] and 2-6-dichlorophenyl [C (C16-C21)] and C' (C16'-C21')] rings at dihedral angles of A/B = 30.61 (5), A/C = 43.36 (5) ° and A'/B' = 32.25 (5), A'/C' = 41.04 (5) °. The dihedral angles between phenyl rings are B/C = 66.38 (7) and B'/C' = 66.14 (6) °. Atoms C1 and C1' are -0.044 (2) and 0.086 (2) Å away from the planes of the benzotriazole rings, respectively.

In the crystal structure, intermolecular C—H···N hydrogen bonds (Table 1) link the molecules into chains along the a-axis (Fig. 2). The π–π contacts between the 2-6-dichlorophenyl rings, Cg3—Cg3ⁱ and Cg3'—Cg3'ⁱⁱ, [symmetry codes: (i) 2 - x, 2 - y, - z, (ii) 1 - x, 1 - y, 1 - z, where Cg3 and Cg3' are the centroids of the rings C (C16-C21)] and C' (C16'-C21'), respectively], may further stabilize the structure, with centroid-centroid distances of 3.809 (1) and 3.735 (1) Å, respectively.

Related literature top

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 top

The title compound, (I), was synthesized by the reduction of 2-(1H-benzotriazol-1-yl)-3-(2,6-dichlorophenyl)-1-phenylpropane-1-one. Sodiumborohydride (38.21 mg, 1.01 mmol) was added to a solution of 2-(1H-benzotriazol-1-yl)-3-(2,6-dichlorophenyl)-1-phenylpropane-1-one (200 mg, 0.505 mmol) in ethanol (15 ml). The mixture was refluxed for 5 h. The solvent was removed and the mixture was neutralized with dilute HCl, and then refluxed for 30 min. After cooling the mixture, it was alkalinized with dilute NaOH. The precipitate was filtered and washed with ethanol. The filtrate was extracted with chloroform, then the organic phase was dried and solvents were removed by rotary evaporator. The residue was purified with column chromatography using hexane: ethyl acetate (7:3) mixture as solvent. The product was crystallized from benzene to obtain colorless single crystals suitable for X-ray analysis (yield; 82 mg, 41%).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); 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).

Figures top

	Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H-atoms have been omitted for clarity.
	Fig. 2. A view of the crystal packing of the title compound. The intermolecular C—H···N hydrogen bonds are shown as dashed lines [H-atoms not involved in hydrogen bonding have been omitted for clarity].

2-(1H-Benzotriazol-1-yl)-3-(2,6-dichlorophenyl)-1-phenylpropan-1-ol top

Crystal data top

C₂₁H₁₇Cl₂N₃O	Z = 4
M_r = 398.28	F(000) = 824
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0504P)² + 0.9534P] where P = (F_o² + 2F_c²)/3
8697 reflections	(Δ/σ)_max = 0.001
487 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.73 e Å⁻³

Crystal data top

C₂₁H₁₇Cl₂N₃O	γ = 90.406 (1)°
M_r = 398.28	V = 1893.90 (6) Å³
Triclinic, P1	Z = 4
a = 9.3894 (2) Å	Mo Kα radiation
b = 9.4947 (2) Å	µ = 0.36 mm⁻¹
c = 21.2687 (3) Å	T = 120 K
α = 91.415 (2)°	0.4 × 0.4 × 0.3 mm
β = 92.324 (2)°

Data collection top

Nonius KappaCCD diffractometer	8697 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	7206 reflections with I > 2σ(I)
T_min = 0.866, T_max = 0.897	R_int = 0.044
40396 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.07	Δρ_max = 0.43 e Å⁻³
8697 reflections	Δρ_min = −0.73 e Å⁻³
487 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₇Cl₂N₃O
M_r	398.28
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	9.3894 (2), 9.4947 (2), 21.2687 (3)
α, β, γ (°)	91.415 (2), 92.324 (2), 90.406 (1)
V (Å³)	1893.90 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.4 × 0.4 × 0.3

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.866, 0.897
No. of measured, independent and observed [I > 2σ(I)] reflections	40396, 8697, 7206
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.108, 1.07
No. of reflections	8697
No. of parameters	487
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.73

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) x, y+1, z.

Acknowledgements

The authors acknowledge Zonguldak Karaelmas University Research Fund (project No: 2010-13-02-06).

References

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