1-[(7E)-7-(2-Chloro­benzyl­idene)-3-(2-chloro­phen­yl)-3,3a,4,5,6,7-hexa­hydro-2H-indazol-2-yl]ethanone

Adam, F.; Ameram, N.; Samshuddin, S.; Akhilesh Bairy, K.; Shivashankarappa Sunil, M.

doi:10.1107/S2414314616004740

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 3| March 2016| x160474

doi:10.1107/S2414314616004740

Open

access

1-[(7E)-7-(2-Chlorobenzylidene)-3-(2-chlorophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazol-2-yl]ethanone

Farook Adam,^a ^* Nadiah Ameram,^b Seranthimata Samshuddin,^c Kurady Akhilesh Bairy ^d and Madhugiri Shivashankarappa Sunil ^d

^aSchool of Chemical Sciences, Unibersiti Science Malaysia, 11800, Minden, Pulau Pinang., Malaysia, ^bSchool of Chemical Sciences, Universiti Science Malaysia, 11800, Minden, Pulau Pinang., Malaysia, ^cDepartment of P.G. Studies in Chemistry, Alva's College, Moodbidri, Karnataka 574 227, India, and ^dDepartment of Chemistry, SDM Institute of Technology, Ujire, Karnataka 574 240, India
^*Correspondence e-mail: farook@usm.my

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 15 March 2016; accepted 21 March 2016; online 24 March 2016)

In the title compound, C₂₂H₂₀Cl₂N₂O, the diazole ring adopts a shallow envelope conformation with the methine C atom bonded to the adjacent chlorobenzene ring as the flap. The dihedral angles between the heterocyclic ring and the pendant chlorobenzene rings are 61.4 (2) and 80.3 (2)°. In the crystal, weak C—H⋯Cl interactions connect the molecules into [001] chains.

Keywords: crystal structure; indazole derivative; synthesis; C—H⋯Cl interactions.

CCDC reference: 1469641

3D view (loading...)

Chemical scheme

Structure description

Heterocycles containing 1,2-diazole systems such as indazole have attracted much attention for the design and synthesis of novel biologically active agents. They display various biological activities such as analgesic, anti inflammatory, anti-depressant, anti-tumor, anti-hypertensive, anti-viral and anti-cancer activities (Jain et al., 1987 ; Palazzo et al., 1966 ; Popat et al., 2003 ).

The crystal structure of an indazole derivative, viz., 4,6-bis(4-fluorophenyl)-2-phenyl-1H-indazol-3(2H)-one (Butcher et al., 2011 ) has been reported. As part of our studies in this area, the title compound (I) was synthesized and its crystal structure is reported here (Fig. 1). The 1,2-diazole ring adopts a shallow envelope conformation, with C14 as the flap; the dihedral angles between this ring (all atoms) and the C6 and C15 chlorobenzene rings are 61.4 (2) and 80.3 (2)°, respectively. The cyclohexyl ring adopts a distorted chair conformation. In the crystal, weak C—H⋯Cl interactions (Table 1 and (Fig. 2)) connect the molecules into [001] chains.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯Cl1ⁱ	1.00	2.85	3.677 (4)	140
Symmetry code: (i) $[-x+1, -y+1, z-{\script{1\over 2}}]$ .

Figure 1
The molecular structure of (I), showing 50% probability displacement ellipsoids.

Figure 2
The crystal packing of (I), viewed down the b axis, showing the formation of [001] chains linked by C—H⋯Cl interactions (dashed lines).

Synthesis and crystallization

A mixture of 2,6-bis(2-chlorobenzylidene)cyclohexanone (3.43 g, 0.01 mol) and hydrazine hydrate (1 ml) in 30 ml acetic acid was refluxed for 10 h. The reaction mixture was cooled and poured into 50 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from ethanol. Colourless plates were grown from DMF solution by slow evaporation; Yield: 72% (m.p. 458 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₂₀Cl₂N₂O
M_r	399.30
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	100
a, b, c (Å)	20.9334 (17), 10.2009 (8), 9.0493 (7)
V (Å³)	1932.4 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.35
Crystal size (mm)	0.64 × 0.25 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.653, 0.855
No. of measured, independent and observed [I > 2σ(I)] reflections	38855, 3549, 2966
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.094, 1.05
No. of reflections	3549
No. of parameters	245
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.16
Absolute structure	Flack x determined using 1138 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.05 (3)
Computer programs: APEX2 and SAINT (Bruker, 2009), SHELXS97 and SHELXTL (Sheldrick 2008 ) and SHELXL2014 (Sheldrick, 2015 ).

Structural data

CCDC reference: 1469641

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616004740/hb4029sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616004740/hb4029Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616004740/hb4029Isup3.cml

checkCIF report

Synthesis and crystallization top

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Experimental top

Structure description top

The crystal structure of an indazole derivative, viz., 4,6-bis(4-fluorophenyl)-2-phenyl-1H-indazol-3(2H)-one (Butcher et al., 2011) has been reported. As part of our studies in this area, the title compound (I) was synthesized and its crystal structure is reported here. The 1,2-diazole ring adopts a shallow envelope conformation, with C14 as the flap; the dihedral angles between this ring (all atoms) and the C6 and C15 chlorobenzene rings are 61.4 (2) and 80.3 (2)°, respectively. The cyclohexyl ring adopts a distorted chair conformation. In the crystal, weak C—H···Cl interactions (Table 1) connect the molecules into [001] chains.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick 2008); software used to prepare material for publication: SHELXTL (Sheldrick 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of (I), viewed down the b axis, showing the formation of [001] chains linked by C—H···Cl interactions (dashed lines).

1-[(7E)-7-(2-Chlorobenzylidene)-3-(2-chlorophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazol-2-yl]ethanone top

Crystal data top

C₂₂H₂₀Cl₂N₂O	D_x = 1.373 Mg m⁻³
M_r = 399.30	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca2₁	Cell parameters from 9969 reflections
a = 20.9334 (17) Å	θ = 2.2–30.1°
b = 10.2009 (8) Å	µ = 0.35 mm⁻¹
c = 9.0493 (7) Å	T = 100 K
V = 1932.4 (3) Å³	Plate, colourless
Z = 4	0.64 × 0.25 × 0.09 mm
F(000) = 832

Data collection top

Bruker APEXII CCD diffractometer	2966 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.058
Absorption correction: multi-scan (SADABS; Bruker, 2009)	θ_max = 25.5°, θ_min = 2.0°
T_min = 0.653, T_max = 0.855	h = −25→25
38855 measured reflections	k = −11→12
3549 independent reflections	l = −10→10

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.041	w = 1/[σ²(F_o²) + (0.0448P)² + 0.3258P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.094	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.14 e Å⁻³
3549 reflections	Δρ_min = −0.16 e Å⁻³
245 parameters	Absolute structure: Flack x determined using 1138 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.05 (3)

Crystal data top

C₂₂H₂₀Cl₂N₂O	V = 1932.4 (3) Å³
M_r = 399.30	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 20.9334 (17) Å	µ = 0.35 mm⁻¹
b = 10.2009 (8) Å	T = 100 K
c = 9.0493 (7) Å	0.64 × 0.25 × 0.09 mm

Data collection top

Bruker APEXII CCD diffractometer	3549 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2966 reflections with I > 2σ(I)
T_min = 0.653, T_max = 0.855	R_int = 0.058
38855 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.094	Δρ_max = 0.14 e Å⁻³
S = 1.05	Δρ_min = −0.16 e Å⁻³
3549 reflections	Absolute structure: Flack x determined using 1138 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
245 parameters	Absolute structure parameter: 0.05 (3)
1 restraint

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Cl1	0.48134 (5)	0.51064 (11)	0.96839 (15)	0.0795 (3)
Cl2	0.31606 (5)	0.76773 (13)	−0.03357 (12)	0.0821 (4)
O1	0.31810 (15)	1.0071 (3)	0.3493 (3)	0.0653 (7)
N1	0.34670 (14)	0.7266 (3)	0.5626 (3)	0.0459 (7)
N2	0.34748 (13)	0.8138 (2)	0.4423 (3)	0.0472 (7)
C1	0.3342 (2)	0.2839 (4)	0.8519 (5)	0.0616 (10)
H1A	0.2995	0.2839	0.7840	0.074*
C2	0.3395 (3)	0.1818 (4)	0.9532 (6)	0.0805 (14)
H2A	0.3086	0.1137	0.9540	0.097*
C3	0.3891 (3)	0.1791 (5)	1.0515 (5)	0.0892 (17)
H3A	0.3933	0.1078	1.1184	0.107*
C4	0.4327 (3)	0.2793 (5)	1.0535 (4)	0.0763 (13)
H4A	0.4670	0.2783	1.1223	0.092*
C5	0.42650 (17)	0.3825 (3)	0.9541 (4)	0.0556 (9)
C6	0.37857 (17)	0.3867 (3)	0.8475 (4)	0.0477 (8)
C7	0.37465 (17)	0.4943 (3)	0.7390 (4)	0.0455 (8)
H7A	0.3896	0.5772	0.7722	0.055*
C8	0.35296 (17)	0.4906 (3)	0.6007 (4)	0.0442 (8)
C9	0.35321 (16)	0.6102 (3)	0.5097 (3)	0.0421 (8)
C10	0.36092 (17)	0.6037 (3)	0.3445 (4)	0.0482 (8)
H10A	0.4069	0.5846	0.3235	0.058*
C11	0.3220 (2)	0.4941 (4)	0.2782 (4)	0.0621 (10)
H11A	0.3306	0.4870	0.1710	0.074*
H11B	0.2758	0.5113	0.2922	0.074*
C12	0.3409 (2)	0.3679 (4)	0.3562 (5)	0.0616 (11)
H12A	0.3871	0.3521	0.3403	0.074*
H12B	0.3172	0.2939	0.3114	0.074*
C13	0.3275 (2)	0.3709 (4)	0.5217 (4)	0.0609 (11)
H13A	0.2807	0.3664	0.5371	0.073*
H13B	0.3466	0.2918	0.5673	0.073*
C14	0.34787 (17)	0.7469 (3)	0.2968 (3)	0.0448 (8)
H14A	0.3049	0.7538	0.2490	0.054*
C15	0.39886 (17)	0.7980 (3)	0.1944 (4)	0.0452 (8)
C16	0.4588 (2)	0.8303 (4)	0.2481 (5)	0.0662 (11)
H16A	0.4665	0.8261	0.3514	0.079*
C17	0.5079 (2)	0.8686 (5)	0.1552 (7)	0.0863 (15)
H17A	0.5487	0.8896	0.1944	0.104*
C18	0.4970 (3)	0.8760 (5)	0.0047 (6)	0.0880 (17)
H18A	0.5305	0.9017	−0.0599	0.106*
C19	0.4382 (2)	0.8463 (4)	−0.0511 (5)	0.0725 (12)
H19A	0.4307	0.8521	−0.1544	0.087*
C20	0.38947 (19)	0.8077 (3)	0.0429 (4)	0.0534 (9)
C21	0.32633 (15)	0.9393 (3)	0.4583 (4)	0.0478 (7)
C22	0.3155 (2)	0.9878 (3)	0.6132 (4)	0.0566 (10)
H22A	0.3542	0.9736	0.6721	0.085*
H22B	0.2798	0.9399	0.6578	0.085*
H22C	0.3055	1.0817	0.6109	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0679 (6)	0.0959 (8)	0.0747 (7)	0.0049 (5)	−0.0093 (6)	−0.0008 (7)
Cl2	0.0839 (7)	0.1218 (9)	0.0406 (5)	0.0197 (6)	−0.0111 (5)	−0.0060 (6)
O1	0.094 (2)	0.0515 (15)	0.0506 (15)	0.0111 (14)	0.0028 (15)	0.0149 (13)
N1	0.0627 (18)	0.0390 (16)	0.0360 (14)	0.0033 (14)	0.0002 (13)	0.0064 (13)
N2	0.0714 (18)	0.0385 (14)	0.0317 (14)	0.0053 (12)	0.0014 (14)	0.0054 (12)
C1	0.082 (3)	0.049 (2)	0.054 (2)	−0.004 (2)	0.021 (2)	0.0027 (19)
C2	0.133 (4)	0.047 (2)	0.061 (3)	−0.005 (2)	0.039 (3)	0.004 (2)
C3	0.161 (5)	0.052 (3)	0.055 (3)	0.023 (3)	0.032 (3)	0.015 (2)
C4	0.112 (4)	0.075 (3)	0.042 (2)	0.040 (3)	0.007 (2)	0.007 (2)
C5	0.070 (2)	0.054 (2)	0.0430 (18)	0.0180 (16)	0.011 (2)	0.0028 (19)
C6	0.061 (2)	0.0409 (19)	0.0413 (18)	0.0114 (16)	0.0148 (18)	0.0039 (15)
C7	0.053 (2)	0.0350 (17)	0.0482 (18)	0.0012 (15)	0.0052 (16)	0.0012 (15)
C8	0.053 (2)	0.0371 (18)	0.043 (2)	0.0014 (15)	0.0071 (16)	0.0004 (15)
C9	0.0513 (19)	0.0380 (19)	0.0370 (17)	0.0011 (15)	0.0018 (14)	−0.0011 (14)
C10	0.056 (2)	0.050 (2)	0.0391 (17)	0.0023 (16)	0.0019 (16)	−0.0013 (15)
C11	0.083 (3)	0.059 (2)	0.0438 (19)	−0.004 (2)	0.0000 (19)	−0.0081 (19)
C12	0.083 (3)	0.048 (2)	0.053 (2)	−0.004 (2)	0.005 (2)	−0.0122 (18)
C13	0.087 (3)	0.039 (2)	0.057 (2)	−0.0069 (19)	0.007 (2)	−0.0037 (17)
C14	0.057 (2)	0.046 (2)	0.0321 (17)	0.0020 (15)	0.0006 (16)	0.0020 (15)
C15	0.053 (2)	0.0418 (18)	0.0402 (17)	0.0076 (16)	0.0014 (16)	0.0065 (15)
C16	0.068 (3)	0.070 (3)	0.060 (2)	−0.001 (2)	0.001 (2)	0.009 (2)
C17	0.062 (3)	0.080 (3)	0.117 (5)	−0.008 (2)	0.015 (3)	0.009 (3)
C18	0.089 (4)	0.070 (3)	0.105 (4)	0.007 (3)	0.047 (3)	0.026 (3)
C19	0.094 (3)	0.069 (3)	0.054 (2)	0.018 (2)	0.029 (2)	0.018 (2)
C20	0.068 (2)	0.049 (2)	0.0424 (19)	0.0176 (18)	0.0053 (18)	0.0045 (16)
C21	0.0599 (19)	0.0390 (17)	0.0445 (18)	−0.0028 (15)	−0.0008 (19)	0.0078 (18)
C22	0.084 (3)	0.0365 (18)	0.049 (2)	0.0012 (18)	0.000 (2)	−0.0046 (17)

Geometric parameters (Å, º) top

Cl1—C5	1.744 (4)	C10—H10A	1.0000
Cl2—C20	1.734 (4)	C11—C12	1.521 (6)
O1—C21	1.218 (4)	C11—H11A	0.9900
N1—C9	1.287 (4)	C11—H11B	0.9900
N1—N2	1.406 (4)	C12—C13	1.525 (5)
N2—C21	1.363 (4)	C12—H12A	0.9900
N2—C14	1.483 (4)	C12—H12B	0.9900
C1—C2	1.392 (6)	C13—H13A	0.9900
C1—C6	1.402 (5)	C13—H13B	0.9900
C1—H1A	0.9500	C14—C15	1.506 (5)
C2—C3	1.368 (7)	C14—H14A	1.0000
C2—H2A	0.9500	C15—C16	1.386 (5)
C3—C4	1.371 (7)	C15—C20	1.389 (5)
C3—H3A	0.9500	C16—C17	1.383 (6)
C4—C5	1.391 (5)	C16—H16A	0.9500
C4—H4A	0.9500	C17—C18	1.383 (7)
C5—C6	1.392 (5)	C17—H17A	0.9500
C6—C7	1.475 (5)	C18—C19	1.365 (7)
C7—C8	1.332 (5)	C18—H18A	0.9500
C7—H7A	0.9500	C19—C20	1.385 (5)
C8—C9	1.472 (5)	C19—H19A	0.9500
C8—C13	1.512 (5)	C21—C22	1.504 (5)
C9—C10	1.505 (5)	C22—H22A	0.9800
C10—C11	1.508 (5)	C22—H22B	0.9800
C10—C14	1.547 (5)	C22—H22C	0.9800

C9—N1—N2	107.2 (3)	C11—C12—H12A	109.0
C21—N2—N1	120.6 (3)	C13—C12—H12A	109.0
C21—N2—C14	121.9 (3)	C11—C12—H12B	109.0
N1—N2—C14	113.3 (2)	C13—C12—H12B	109.0
C2—C1—C6	121.7 (5)	H12A—C12—H12B	107.8
C2—C1—H1A	119.2	C8—C13—C12	114.6 (3)
C6—C1—H1A	119.2	C8—C13—H13A	108.6
C3—C2—C1	120.3 (4)	C12—C13—H13A	108.6
C3—C2—H2A	119.8	C8—C13—H13B	108.6
C1—C2—H2A	119.8	C12—C13—H13B	108.6
C2—C3—C4	119.9 (4)	H13A—C13—H13B	107.6
C2—C3—H3A	120.1	N2—C14—C15	113.0 (3)
C4—C3—H3A	120.1	N2—C14—C10	100.8 (2)
C3—C4—C5	119.6 (5)	C15—C14—C10	111.9 (3)
C3—C4—H4A	120.2	N2—C14—H14A	110.3
C5—C4—H4A	120.2	C15—C14—H14A	110.3
C4—C5—C6	122.6 (4)	C10—C14—H14A	110.3
C4—C5—Cl1	117.2 (4)	C16—C15—C20	117.2 (3)
C6—C5—Cl1	120.2 (3)	C16—C15—C14	120.6 (3)
C5—C6—C1	115.8 (3)	C20—C15—C14	122.1 (3)
C5—C6—C7	121.6 (3)	C17—C16—C15	121.8 (4)
C1—C6—C7	122.6 (3)	C17—C16—H16A	119.1
C8—C7—C6	128.6 (3)	C15—C16—H16A	119.1
C8—C7—H7A	115.7	C18—C17—C16	119.5 (5)
C6—C7—H7A	115.7	C18—C17—H17A	120.2
C7—C8—C9	120.1 (3)	C16—C17—H17A	120.2
C7—C8—C13	126.0 (3)	C19—C18—C17	120.0 (4)
C9—C8—C13	114.0 (3)	C19—C18—H18A	120.0
N1—C9—C8	123.8 (3)	C17—C18—H18A	120.0
N1—C9—C10	114.9 (3)	C18—C19—C20	120.1 (4)
C8—C9—C10	121.3 (3)	C18—C19—H19A	120.0
C9—C10—C11	111.7 (3)	C20—C19—H19A	120.0
C9—C10—C14	102.5 (3)	C19—C20—C15	121.5 (4)
C11—C10—C14	119.6 (3)	C19—C20—Cl2	118.3 (3)
C9—C10—H10A	107.5	C15—C20—Cl2	120.2 (3)
C11—C10—H10A	107.5	O1—C21—N2	119.6 (3)
C14—C10—H10A	107.5	O1—C21—C22	123.2 (3)
C10—C11—C12	107.6 (3)	N2—C21—C22	117.2 (3)
C10—C11—H11A	110.2	C21—C22—H22A	109.5
C12—C11—H11A	110.2	C21—C22—H22B	109.5
C10—C11—H11B	110.2	H22A—C22—H22B	109.5
C12—C11—H11B	110.2	C21—C22—H22C	109.5
H11A—C11—H11B	108.5	H22A—C22—H22C	109.5
C11—C12—C13	113.0 (3)	H22B—C22—H22C	109.5

C9—N1—N2—C21	164.0 (3)	C7—C8—C13—C12	−146.9 (4)
C9—N1—N2—C14	6.5 (4)	C9—C8—C13—C12	32.2 (5)
C6—C1—C2—C3	−0.3 (6)	C11—C12—C13—C8	−50.2 (5)
C1—C2—C3—C4	1.9 (6)	C21—N2—C14—C15	72.4 (4)
C2—C3—C4—C5	−0.7 (6)	N1—N2—C14—C15	−130.5 (3)
C3—C4—C5—C6	−2.3 (6)	C21—N2—C14—C10	−168.0 (3)
C3—C4—C5—Cl1	177.0 (3)	N1—N2—C14—C10	−10.9 (3)
C4—C5—C6—C1	3.8 (5)	C9—C10—C14—N2	10.3 (3)
Cl1—C5—C6—C1	−175.6 (3)	C11—C10—C14—N2	134.5 (3)
C4—C5—C6—C7	−177.2 (3)	C9—C10—C14—C15	130.7 (3)
Cl1—C5—C6—C7	3.5 (4)	C11—C10—C14—C15	−105.1 (4)
C2—C1—C6—C5	−2.4 (5)	N2—C14—C15—C16	39.2 (4)
C2—C1—C6—C7	178.6 (4)	C10—C14—C15—C16	−73.8 (4)
C5—C6—C7—C8	148.7 (4)	N2—C14—C15—C20	−144.6 (3)
C1—C6—C7—C8	−32.4 (6)	C10—C14—C15—C20	102.4 (4)
C6—C7—C8—C9	−180.0 (3)	C20—C15—C16—C17	−1.1 (6)
C6—C7—C8—C13	−0.8 (6)	C14—C15—C16—C17	175.4 (4)
N2—N1—C9—C8	−178.2 (3)	C15—C16—C17—C18	0.5 (7)
N2—N1—C9—C10	1.4 (4)	C16—C17—C18—C19	0.3 (7)
C7—C8—C9—N1	−30.8 (5)	C17—C18—C19—C20	−0.6 (7)
C13—C8—C9—N1	150.0 (4)	C18—C19—C20—C15	−0.1 (6)
C7—C8—C9—C10	149.6 (4)	C18—C19—C20—Cl2	−178.7 (3)
C13—C8—C9—C10	−29.7 (5)	C16—C15—C20—C19	0.9 (5)
N1—C9—C10—C11	−137.2 (3)	C14—C15—C20—C19	−175.5 (3)
C8—C9—C10—C11	42.4 (5)	C16—C15—C20—Cl2	179.5 (3)
N1—C9—C10—C14	−8.0 (4)	C14—C15—C20—Cl2	3.1 (5)
C8—C9—C10—C14	171.6 (3)	N1—N2—C21—O1	−168.8 (3)
C9—C10—C11—C12	−55.0 (4)	C14—N2—C21—O1	−13.3 (5)
C14—C10—C11—C12	−174.6 (3)	N1—N2—C21—C22	12.4 (4)
C10—C11—C12—C13	61.1 (5)	C14—N2—C21—C22	167.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···Cl1ⁱ	1.00	2.85	3.677 (4)	140

Symmetry code: (i) −x+1, −y+1, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···Cl1ⁱ	1.00	2.85	3.677 (4)	140

Symmetry code: (i) −x+1, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₀Cl₂N₂O
M_r	399.30
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	100
a, b, c (Å)	20.9334 (17), 10.2009 (8), 9.0493 (7)
V (Å³)	1932.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.64 × 0.25 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.653, 0.855
No. of measured, independent and observed [I > 2σ(I)] reflections	38855, 3549, 2966
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.094, 1.05
No. of reflections	3549
No. of parameters	245
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.16
Absolute structure	Flack x determined using 1138 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Absolute structure parameter	0.05 (3)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick 2008), SHELXL2014 (Sheldrick, 2015), SHELXTL (Sheldrick 2008).

Acknowledgements

The authors thank Alva's Education Foundation, Moodbidri for provision of research facilities. The authors also thank Universiti Malaysia Kelantan, SLAI, the Malaysian Ministry of Higher Education and the Universiti Sains Malaysia for RU research grants (Nos. PKIMIA/846017 and 1001/PKIMIA/ 811269), which partly supported this work.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Butcher, R. J., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1346–o1347. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Jain, A. C., Mehta, A. & Arya, P. (1987). Indian J. Chem. Sect. B, 26, 150–153. Google Scholar
Palazzo, G., Corsi, G., Baiocchi, L. & Silvestrini, B. (1966). J. Med. Chem. 9, 38–41. CrossRef CAS PubMed Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Popat, K. H., Nimavat, K. S., Vasoya, S. L. & Joshi, H. S. (2003). Indian J. Chem. Sect. B, 42, 1497–1501. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 3| March 2016| x160474

doi:10.1107/S2414314616004740

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-[(7E)-7-(2-Chloro­benzyl­­idene)-3-(2-chloro­phen­yl)-3,3a,4,5,6,7-hexa­hydro-2H-indazol-2-yl]ethanone

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

1-[(7E)-7-(2-Chlorobenzylidene)-3-(2-chlorophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazol-2-yl]ethanone