1-[2-(4-Chloro­benz­yloxy)-2-phenyl­ethyl]-1H-benzotriazole

Özel Güven, Ö.; Bayraktar, M.; Coles, S.J.; Hökelek, T.

doi:10.1107/S1600536810015692

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Pages o1246-o1247

https://doi.org/10.1107/S1600536810015692

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1-[2-(4-Chlorobenzyloxy)-2-phenylethyl]-1H-benzotriazole

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

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

(Received 22 April 2010; accepted 28 April 2010; online 8 May 2010)

The asymmetric unit of the title compound, C₂₁H₁₈ClN₃O, contains two crystallographically independent molecules which differ slightly in the orientations of chlorobenzyloxy units. In one of the molecules, the phenyl and chlorophenyl 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 molecule]. The dihedral angle between the phenyl and chlorophenyl rings is 77.63 (6)° in one of the molecules and 72.97 (6)° in the other. The crystal structure is stabilized by weak C—H⋯π interactions.

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_r = 363.83
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.065
wR(F²) = 0.189
S = 1.07
7993 reflections
470 parameters
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.69 e Å⁻³

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′⋯Cg1^iv	0.95	2.81	3.755 (2)	172
C18′—H18′⋯Cg3^v	0.95	2.83	3.502 (2)	129
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z-1; (iii) $[x-1, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (v) x, y, z-1.

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: https://doi.org/10.1107/S1600536810015692/ci5085sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015692/ci5085Isup2.hkl

checkCIF report

Comment top

In recent years, there has been increasing interest in the syntheses of heterocyclic compounds that have biological and commercial importance. Clotrimazole, miconazole, econazole, ketonazole, itraconazole and fluconazole are well-known imidazoles. 1H-1,2,4-Triazole ring containing azole derivatives have been developed for clinical uses as antifungal agents. Recently, structures containing benzimidazole ring in place of miconazole and econazole have been reported, and these molecules have been shown more antibacterial activity than antifungal activity (Özel Güven et al., 2007a,b). The crystal structures of miconazole (Peeters et al., 1979a), ketonazole (Peeters et al., 1979b), econazole (Freer et al., 1986), itraconazole (Peeters et al., 1996) and fluconazole (Caira et al., 2004) have been reported. Recently, we reported crystal structures of related compounds (Özel Güven et al., 2008a,b,c). Benzotriazole derivatives also exhibit a good degree of analgesic, antiinflammatory, diuretic, antiviral and antihypertensive activities (Hirokawa et al., 1998; Yu et al., 2003; Kopanska et al., 2004). Crystal structures of benzotriazole ring possessing compounds have been reported (Katritzky et al., 2001; Swamy et al., 2006; Özel Güven et al., 2010). Now, we report herein the crystal structure of the title benzotriazole derivative.

The asymmetric unit of the title compound (Fig. 1) contains two crystallographically independent molecules which differ slightly in the orientations of the chlorobenzyloxy units. The bond lengths and angles are generally within normal ranges. In each molecule, the planar benzotriazole rings [A (N1-N3/C1-C6) and A' (N1'-N3'/C1'-C6')] are oriented with respect to the phenyl [B (C9-C14) and B' (C9'-C14')] and benzene [C (C16-C21)] and C' (C16'-C21')] rings at dihedral angles of A/B = 37.98 (9), A/C = 42.27 (9) ° and A'/B' = 43.20 (9), A'/C' = 29.82 (9)°. The dihedral angles between phenyl and benzene rings are B/C = 77.63 (6) and B'/C' = 72.97 (6) °. Atoms C7 and C7' are -0.012 (2) and -0.112 (2) Å away from the planes of the benzotriazole rings, respectively.

In the crystal structure, molecules are stacked along the a-axis (Fig. 2). Weak C—H···π interactions (Table 1) involving the C9-C14, C9'-C14' and C16-C21 rings stabilize the structure.

Related literature top

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 top

The title compound was synthesized by the reaction of 2-(1H-benzotriazol-1-yl)-1-phenylethanol (Özel Güven et al., 2010) with aryl halide using NaH. 2-(1H-Benzotriazol-1-yl)-1-phenylethanol (200 mg, 0.84 mmol) was dissolved in DMF (4 ml). NaH (33 mg, 0.84 mmol) was added to the solution portionwise. After stirring the mixture a few minutes, 4-chlorobenzyl bromide (171.8 mg, 0.84 mmol) was added dropwise. Then, the reaction mixture was stirred additional 3 h at room temperature. The reaction was stopped by adding methanol (5 ml). After evaporation of the solvent, dichloromethane was added to the reaction mixture and extracted with water. Then, the organic phase was separated, dried, filtered and evaporated. The precipitate formed was purified by column chromatography using chloroform and crystallized from iso-propanol to obtain colorless crystals suitable for X-ray analysis (yield; 137 mg, 46%).

Structure description top

In the crystal structure, molecules are stacked along the a-axis (Fig. 2). Weak C—H···π interactions (Table 1) involving the C9-C14, C9'-C14' and C16-C21 rings stabilize the structure.

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).

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 two independent molecules of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
	Fig. 2. Packing diagram of the title compound, viewed along the a axis. H atoms have been omitted for clarity.

1-[2-(4-Chlorobenzyloxy)-2-phenylethyl]-1H-benzotriazole top

Crystal data top

C₂₁H₁₈ClN₃O	F(000) = 1520
M_r = 363.83	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1171P)² + 0.2599P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
7993 reflections	Δρ_max = 0.64 e Å⁻³
470 parameters	Δρ_min = −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)

Crystal data top

C₂₁H₁₈ClN₃O	V = 3536.42 (15) Å³
M_r = 363.83	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.2163 (2) Å	µ = 0.23 mm⁻¹
b = 36.8545 (9) Å	T = 120 K
c = 13.3019 (3) Å	0.40 × 0.40 × 0.14 mm
β = 91.529 (1)°

Data collection top

Nonius Kappa CCD diffractometer	7993 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	5918 reflections with I > 2σ(I)
T_min = 0.910, T_max = 0.966	R_int = 0.051
26731 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.189	H-atom parameters constrained
S = 1.07	Δρ_max = 0.64 e Å⁻³
7993 reflections	Δρ_min = −0.69 e Å⁻³
470 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	−0.22475 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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′···Cg1^iv	0.95	2.81	3.755 (2)	172
C18′—H18′···Cg3^v	0.95	2.83	3.502 (2)	129

Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z−1; (iii) x−1, −y−1/2, z−1/2; (iv) x, −y−1/2, z−3/2; (v) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈ClN₃O
M_r	363.83
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	7.2163 (2), 36.8545 (9), 13.3019 (3)
β (°)	91.529 (1)
V (Å³)	3536.42 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.40 × 0.40 × 0.14

Data collection
Diffractometer	Nonius Kappa CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.910, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	26731, 7993, 5918
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.189, 1.07
No. of reflections	7993
No. of parameters	470
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.69

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

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'···Cg1^iv	0.95	2.81	3.755 (2)	172
C18'—H18'···Cg3^v	0.95	2.83	3.502 (2)	129

Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z−1; (iii) x−1, −y−1/2, z−1/2; (iv) x, −y−1/2, z−3/2; (v) x, y, z−1.

Acknowledgements

The authors acknowledge the Zonguldak Karaelmas University Research Fund for support.

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