organic compounds
1-[(7E)-7-(2-Chlorobenzylidene)-3-(2-chlorophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazol-2-yl]ethanone
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
In the title compound, C22H20Cl2N2O, the diazole ring adopts a shallow 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
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 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 is reported here (Fig. 1). The 1,2-diazole ring adopts a shallow 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.
of an indazole derivative,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 .
details are summarized in Table 2Structural data
CCDC reference: 1469641
10.1107/S2414314616004740/hb4029sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616004740/hb4029Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616004740/hb4029Isup3.cml
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).
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).
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
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 is reported here. The 1,2-diazole ring adopts a shallow 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.Data collection: APEX2 (Bruker, 2009); cell
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).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). |
C22H20Cl2N2O | Dx = 1.373 Mg m−3 |
Mr = 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 |
Bruker APEXII CCD diffractometer | 2966 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.058 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | θmax = 25.5°, θmin = 2.0° |
Tmin = 0.653, Tmax = 0.855 | h = −25→25 |
38855 measured reflections | k = −11→12 |
3549 independent reflections | l = −10→10 |
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(Fo2) + (0.0448P)2 + 0.3258P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.094 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.14 e Å−3 |
3549 reflections | Δρmin = −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) |
C22H20Cl2N2O | V = 1932.4 (3) Å3 |
Mr = 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 |
Bruker APEXII CCD diffractometer | 3549 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2966 reflections with I > 2σ(I) |
Tmin = 0.653, Tmax = 0.855 | Rint = 0.058 |
38855 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.094 | Δρmax = 0.14 e Å−3 |
S = 1.05 | Δρmin = −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 |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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. |
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 |
Mr | 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) |
Tmin, Tmax | 0.653, 0.855 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 38855, 3549, 2966 |
Rint | 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 |
Δρmax, Δρmin (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.
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