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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 8| August 2015| Pages o592-o593
https://doi.org/10.1107/S2056989015012268

Crystal structure of 6-chloro-5-(2-chloro­eth­yl)-3-(propan-2-yl­­idene)indolin-2-one

K. R. Roopashree,a* Gangadhar Y. Meti,b Ravindra R. Kambleb and H. C. Devarajegowdaa

aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, and bDepartment of Studies in Chemistry, Karnataka University, Dharwad 580 003, Karnataka, India
*Correspondence e-mail: roopamdy@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 5 June 2015; accepted 26 June 2015; online 22 July 2015)

The title compound, C13H13Cl2NO, has a 3-(propan-2-yl­idene)indolin-2-one core with a Cl atom and a chloro­ethyl substituent attached to the aromatic ring. Two atoms of the aromatic ring and the chloro­ethyl substituent atoms are disordered over two sets of sites with a refined occupancy ratio of 0.826 (3):0.174 (3). In the crystal, mol­ecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers with an R22(8) ring motif.

CCDC reference: 1408952

Similar articles

1. Related literature

For inhibitors of hyaluronidase, see: Shen & Winter (1977[Shen, T. Y. & Winter, C. A. (1977). Adv. Drug Res. 12, 90-245.]). For the anti-inflammatory properties of some pyrido­pyrimidine derivatives, see: La Motta et al. (2007[La Motta, C., Sartini, S., Mugnaini, L., Simorini, F., Taliani, S., Salerno, S., Marini, A. M., Da Settimo, F., Lavecchia, A., Novellino, E., Cantore, M., Failli, P. & Ciuffi, M. (2007). J. Med. Chem. 50, 4917-4927.]). For the synthesis and crystal structures of seven substituted 3-methyl­idene-1H-indol-2(3H)-one derivatives, including 3-(propan-2-yl­idene)indolin-2-one, see: Spencer et al. (2010[Spencer, J., Chowdhry, B. Z., Hamid, S., Mendham, A. P., Male, L., Coles, S. J. & Hursthouse, M. B. (2010). Acta Cryst. C66, o71-o78.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C13H13Cl2NO

  • Mr = 270.14

  • Triclinic, [P \overline 1]

  • a = 8.1079 (10) Å

  • b = 8.8699 (10) Å

  • c = 9.1714 (12) Å

  • α = 101.136 (6)°

  • β = 97.799 (7)°

  • γ = 98.783 (6)°

  • V = 630.22 (14) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.50 mm−1

  • T = 296 K

  • 0.24 × 0.20 × 0.12 mm

2.2. Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.770, Tmax = 1.000

  • 25839 measured reflections

  • 7740 independent reflections

  • 4112 reflections with I > 2σ(I)

  • Rint = 0.026

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.162

  • S = 1.01

  • 7740 reflections

  • 206 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N4—H4N⋯O3i 0.84 (1) 2.02 (1) 2.8349 (11) 166 (2)
Symmetry code: (i) -x, -y-1, -z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL2014 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

CCDC reference: 1408952

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989015012268/su5151sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015012268/su5151Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015012268/su5151Isup3.cml

checkCIF report


Synthesis and crystallization top

A mixture of 3-(2-chloro­ethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (0.009 mol) and cyclic secondary amines (0.0108 mol) in the presence of N,N-diiso­propyl­ethyl­amine (0.015 mol) in aceto­nitrile (25 ml) were refluxed for 10–12 h. The reaction was monitored by TLC. After completion, the reaction mixture was filtered and washed with aceto­nitrile. Aceto­nitrile was then evaporated slowly giving the title compound as colourless plate-like crystals (yield: 70%; m.p.: 411–415 K).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. Atoms C7 and C8 of the aromatic ring and atoms C6—C5—Cl2 of the -CH2—CH2—Cl substituent are disordered over two positions (A and B) with a refined occupancy ratio of 0.826 (3):0.174 (3). The NH H atom was located in a difference Fourier map and refined with a distance restraint of 0.86 (2) Å. The C-bound H atoms were included in calculated positions and treated as riding atoms: C—H = 0.93 - 0.97 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms. The methyl groups were treated as idealized-disordered (AFIX 123) with two positions rotated from each other by 60 °.

Structural commentary top

Indomethacin (Indocin) and anti-allergic agents such as sodium cromoglycate and the natural product sorghumbran have been reported as inhibitors of hyaluronidase (Shen et al., 1977). Some pyrido[1,2-a]pyrimidin-4-one derivatives have also been found to show anti-inflammatory properties (La Motta et al., 2007). In an effort to develop a new class of non-steroidal anti-inflammatory drugs (NSAIDS) that inhibit hyaluronidase we have synthesized the title indoline derivative and report herein on its crystal structure.

The molecular structure of the title compound is shown in Fig. 1. Two atoms of the aromatic ring, C7 and C8, and the -CH2—CH2—Cl substituent (C6—C5—Cl2) are disordered over two positions (A and B) with a refined occupancy ratio of 0.826 (3):0.174 (3).

In the crystal, molecules are linked by a pair of N—H···O hydrogen bonds forming inversion dimers with an R22(8) ring motif (Table 1 and Fig. 2).

Related literature top

For inhibitors of hyaluronidase, see: Shen & Winter (1977). For the anti-inflammatory properties of some pyridopyrimidine derivatives, see: La Motta et al. (2007). For the synthesis and crystal structures of seven substituted 3-methylidene-1H-indol-2(3H)-one derivatives, including 3-(propan-2-ylidene)indolin-2-one, see: Spencer et al. (2010).

Structure description top

Indomethacin (Indocin) and anti-allergic agents such as sodium cromoglycate and the natural product sorghumbran have been reported as inhibitors of hyaluronidase (Shen et al., 1977). Some pyrido[1,2-a]pyrimidin-4-one derivatives have also been found to show anti-inflammatory properties (La Motta et al., 2007). In an effort to develop a new class of non-steroidal anti-inflammatory drugs (NSAIDS) that inhibit hyaluronidase we have synthesized the title indoline derivative and report herein on its crystal structure.

The molecular structure of the title compound is shown in Fig. 1. Two atoms of the aromatic ring, C7 and C8, and the -CH2—CH2—Cl substituent (C6—C5—Cl2) are disordered over two positions (A and B) with a refined occupancy ratio of 0.826 (3):0.174 (3).

In the crystal, molecules are linked by a pair of N—H···O hydrogen bonds forming inversion dimers with an R22(8) ring motif (Table 1 and Fig. 2).

For inhibitors of hyaluronidase, see: Shen & Winter (1977). For the anti-inflammatory properties of some pyridopyrimidine derivatives, see: La Motta et al. (2007). For the synthesis and crystal structures of seven substituted 3-methylidene-1H-indol-2(3H)-one derivatives, including 3-(propan-2-ylidene)indolin-2-one, see: Spencer et al. (2010).

Synthesis and crystallization top

A mixture of 3-(2-chloro­ethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (0.009 mol) and cyclic secondary amines (0.0108 mol) in the presence of N,N-diiso­propyl­ethyl­amine (0.015 mol) in aceto­nitrile (25 ml) were refluxed for 10–12 h. The reaction was monitored by TLC. After completion, the reaction mixture was filtered and washed with aceto­nitrile. Aceto­nitrile was then evaporated slowly giving the title compound as colourless plate-like crystals (yield: 70%; m.p.: 411–415 K).

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. Atoms C7 and C8 of the aromatic ring and atoms C6—C5—Cl2 of the -CH2—CH2—Cl substituent are disordered over two positions (A and B) with a refined occupancy ratio of 0.826 (3):0.174 (3). The NH H atom was located in a difference Fourier map and refined with a distance restraint of 0.86 (2) Å. The C-bound H atoms were included in calculated positions and treated as riding atoms: C—H = 0.93 - 0.97 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms. The methyl groups were treated as idealized-disordered (AFIX 123) with two positions rotated from each other by 60 °.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The dashed lines indicate the bonds involving the minor component atoms, C5B–C8B and Cl2B. The methyl groups have been treated as idealized-disordered with two positions rotated from each other by 60 °.
[Figure 2] Fig. 2. Crystal packing of the title compound, viewed along the a axis, with hydrogen bonds drawn as dashed lines (see Table 1 for details). The C-bound H atoms and the minor components of the disordered atoms have been omitted for clarity.
6-Chloro-5-(2-chloroethyl)-3-(propan-2-ylidene)indolin-2-one top
Crystal data top
C13H13Cl2NOZ = 2
Mr = 270.14F(000) = 280
Triclinic, P1Dx = 1.424 Mg m−3
a = 8.1079 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.8699 (10) ÅCell parameters from 2227 reflections
c = 9.1714 (12) Åθ = 2.3–25.0°
α = 101.136 (6)°µ = 0.50 mm−1
β = 97.799 (7)°T = 296 K
γ = 98.783 (6)°Plate, colourless
V = 630.22 (14) Å30.24 × 0.20 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		7740 independent reflections
Radiation source: fine-focus sealed tube4112 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ω and φ scansθmax = 40.6°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −14→14
Tmin = 0.770, Tmax = 1.000k = −16→15
25839 measured reflectionsl = −16→16
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: mixed
wR(F2) = 0.162H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0793P)2 + 0.0329P]
where P = (Fo2 + 2Fc2)/3
7740 reflections(Δ/σ)max = 0.001
206 parametersΔρmax = 0.32 e Å−3
1 restraintΔρmin = −0.36 e Å−3
Crystal data top
C13H13Cl2NOγ = 98.783 (6)°
Mr = 270.14V = 630.22 (14) Å3
Triclinic, P1Z = 2
a = 8.1079 (10) ÅMo Kα radiation
b = 8.8699 (10) ŵ = 0.50 mm−1
c = 9.1714 (12) ÅT = 296 K
α = 101.136 (6)°0.24 × 0.20 × 0.12 mm
β = 97.799 (7)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		7740 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		4112 reflections with I > 2σ(I)
Tmin = 0.770, Tmax = 1.000Rint = 0.026
25839 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0451 restraint
wR(F2) = 0.162H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.32 e Å−3
7740 reflectionsΔρmin = −0.36 e Å−3
206 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.45520 (4)0.23428 (3)0.16248 (5)0.06608 (12)
O3−0.18925 (11)−0.47480 (8)0.07844 (11)0.0570 (2)
N40.03386 (12)−0.28722 (9)0.06869 (11)0.0481 (2)
H4N0.0900 (19)−0.3448 (17)0.0209 (16)0.060 (4)*
C5A0.14655 (19)0.45717 (14)0.31712 (16)0.0492 (3)0.826 (3)
H5A0.02480.42220.29170.059*0.826 (3)
H5B0.19000.46210.22430.059*0.826 (3)
C6A0.22507 (18)0.34151 (14)0.39194 (15)0.0474 (3)0.826 (3)
H6A0.34730.37350.41170.057*0.826 (3)
H6B0.18730.34200.48790.057*0.826 (3)
C7A0.1785 (2)0.17773 (16)0.2953 (2)0.0415 (3)0.826 (3)
C8A0.0297 (2)0.08170 (18)0.3081 (2)0.0413 (3)0.826 (3)
H8A−0.03880.12030.37440.050*0.826 (3)
Cl2A0.19269 (15)0.64754 (8)0.43853 (13)0.0676 (2)0.826 (3)
C5B0.2356 (13)0.4300 (10)0.4328 (10)0.071 (3)0.174 (3)
H5C0.35130.41220.44050.086*0.174 (3)
H5D0.18060.37490.50000.086*0.174 (3)
C6B0.1481 (12)0.3659 (8)0.2788 (10)0.064 (2)0.174 (3)
H6C0.20720.41570.21050.076*0.174 (3)
H6D0.03440.38870.26910.076*0.174 (3)
C7B0.1384 (12)0.1876 (7)0.2341 (11)0.0481 (17)0.174 (3)
C8B−0.0029 (14)0.0948 (8)0.2517 (10)0.0476 (18)0.174 (3)
H8B−0.09190.13990.28330.057*0.174 (3)
Cl2B0.2382 (6)0.6281 (5)0.4909 (6)0.0703 (10)0.174 (3)
C9−0.01760 (13)−0.07171 (10)0.22234 (11)0.04093 (19)
C100.09453 (12)−0.12925 (9)0.13136 (11)0.04079 (19)
C110.23847 (14)−0.03796 (11)0.11071 (13)0.0458 (2)
H110.3089−0.07790.04710.055*
C120.27408 (14)0.11746 (11)0.18961 (14)0.0485 (2)
C13−0.16019 (13)−0.19963 (10)0.20926 (12)0.04115 (19)
C14−0.11418 (13)−0.33825 (10)0.11333 (12)0.0438 (2)
C15−0.30879 (13)−0.20048 (10)0.26028 (12)0.0436 (2)
C16−0.44740 (16)−0.33957 (14)0.22317 (16)0.0582 (3)
H16A−0.5159−0.33340.30090.087*0.5
H16B−0.3996−0.43280.21620.087*0.5
H16C−0.5161−0.34230.12850.087*0.5
H16D−0.4385−0.40560.12950.087*0.5
H16E−0.5548−0.30620.21420.087*0.5
H16F−0.4383−0.39670.30190.087*0.5
C17−0.34756 (17)−0.05701 (15)0.35607 (17)0.0619 (3)
H17A−0.4680−0.06610.34970.093*0.5
H17B−0.30350.03350.32070.093*0.5
H17C−0.2960−0.04670.45900.093*0.5
H17D−0.24370.01320.40320.093*0.5
H17E−0.4082−0.08640.43220.093*0.5
H17F−0.4156−0.00620.29400.093*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.06298 (19)0.04108 (14)0.0925 (3)−0.00484 (12)0.02704 (16)0.01226 (14)
O30.0557 (4)0.0259 (3)0.0826 (6)0.0007 (3)0.0216 (4)−0.0057 (3)
N40.0511 (5)0.0260 (3)0.0636 (5)0.0041 (3)0.0207 (4)−0.0043 (3)
C5A0.0622 (8)0.0274 (5)0.0539 (7)0.0057 (4)0.0126 (6)−0.0009 (4)
C6A0.0556 (7)0.0301 (5)0.0482 (7)−0.0009 (4)0.0035 (5)−0.0009 (4)
C7A0.0486 (7)0.0261 (5)0.0457 (8)0.0037 (4)0.0028 (6)0.0037 (5)
C8A0.0477 (8)0.0268 (5)0.0470 (9)0.0057 (4)0.0113 (7)0.0005 (6)
Cl2A0.0900 (5)0.02960 (18)0.0798 (5)0.0066 (2)0.0337 (4)−0.0064 (2)
C5B0.085 (6)0.049 (4)0.069 (5)−0.008 (4)0.030 (4)−0.008 (3)
C6B0.087 (5)0.036 (3)0.073 (5)0.009 (3)0.023 (4)0.017 (3)
C7B0.061 (4)0.0186 (19)0.059 (5)0.000 (2)0.010 (4)0.000 (3)
C8B0.068 (5)0.022 (2)0.049 (4)0.007 (2)0.013 (4)−0.001 (3)
Cl2B0.083 (2)0.0326 (11)0.082 (2)−0.0012 (10)0.0189 (16)−0.0141 (12)
C90.0450 (4)0.0249 (3)0.0507 (5)0.0051 (3)0.0128 (4)0.0008 (3)
C100.0457 (5)0.0260 (3)0.0484 (5)0.0051 (3)0.0115 (4)0.0013 (3)
C110.0499 (5)0.0315 (4)0.0555 (5)0.0055 (3)0.0170 (4)0.0046 (4)
C120.0496 (5)0.0303 (4)0.0640 (6)0.0014 (3)0.0150 (4)0.0075 (4)
C130.0454 (4)0.0251 (3)0.0507 (5)0.0055 (3)0.0118 (4)0.0011 (3)
C140.0468 (5)0.0265 (3)0.0544 (5)0.0046 (3)0.0119 (4)−0.0009 (3)
C150.0456 (5)0.0323 (4)0.0511 (5)0.0058 (3)0.0117 (4)0.0036 (3)
C160.0528 (6)0.0435 (5)0.0740 (8)−0.0027 (4)0.0213 (5)0.0046 (5)
C170.0553 (6)0.0478 (6)0.0780 (8)0.0108 (5)0.0236 (6)−0.0069 (5)
Geometric parameters (Å, º) top
Cl1—C121.7396 (11)C7B—C121.413 (8)
O3—C141.2297 (11)C8B—C91.433 (7)
N4—C141.3609 (13)C8B—H8B0.9300
N4—C101.3919 (11)C9—C101.4023 (13)
N4—H4N0.836 (13)C9—C131.4654 (13)
C5A—C6A1.510 (2)C10—C111.3727 (13)
C5A—Cl2A1.7886 (14)C11—C121.3942 (14)
C5A—H5A0.9700C11—H110.9300
C5A—H5B0.9700C13—C151.3500 (14)
C6A—C7A1.5109 (19)C13—C141.4954 (12)
C6A—H6A0.9700C15—C161.4871 (15)
C6A—H6B0.9700C15—C171.5017 (14)
C7A—C121.399 (2)C16—H16A0.9600
C7A—C8A1.399 (2)C16—H16B0.9600
C8A—C91.4008 (18)C16—H16C0.9600
C8A—H8A0.9300C16—H16D0.9600
C5B—C6B1.455 (13)C16—H16E0.9600
C5B—Cl2B1.731 (10)C16—H16F0.9600
C5B—H5C0.9700C17—H17A0.9600
C5B—H5D0.9700C17—H17B0.9600
C6B—C7B1.542 (9)C17—H17C0.9600
C6B—H6C0.9700C17—H17D0.9600
C6B—H6D0.9700C17—H17E0.9600
C7B—C8B1.353 (12)C17—H17F0.9600
C14—N4—C10111.45 (8)C7A—C12—Cl1119.82 (9)
C14—N4—H4N124.9 (11)C7B—C12—Cl1119.4 (3)
C10—N4—H4N123.0 (11)C15—C13—C9130.75 (8)
C6A—C5A—Cl2A111.04 (11)C15—C13—C14124.22 (9)
C6A—C5A—H5A109.4C9—C13—C14104.91 (8)
Cl2A—C5A—H5A109.4O3—C14—N4123.89 (9)
C6A—C5A—H5B109.4O3—C14—C13129.12 (10)
Cl2A—C5A—H5B109.4N4—C14—C13106.99 (8)
H5A—C5A—H5B108.0C13—C15—C16123.31 (9)
C7A—C6A—C5A111.94 (12)C13—C15—C17121.65 (9)
C7A—C6A—H6A109.2C16—C15—C17115.01 (10)
C5A—C6A—H6A109.2C15—C16—H16A109.5
C7A—C6A—H6B109.2C15—C16—H16B109.5
C5A—C6A—H6B109.2H16A—C16—H16B109.5
H6A—C6A—H6B107.9C15—C16—H16C109.5
C12—C7A—C8A117.68 (12)H16A—C16—H16C109.5
C12—C7A—C6A123.44 (13)H16B—C16—H16C109.5
C8A—C7A—C6A118.85 (14)C15—C16—H16D109.5
C7A—C8A—C9120.94 (14)H16A—C16—H16D141.1
C7A—C8A—H8A119.5H16B—C16—H16D56.3
C9—C8A—H8A119.5H16C—C16—H16D56.3
C6B—C5B—Cl2B112.9 (8)C15—C16—H16E109.5
C6B—C5B—H5C109.0H16A—C16—H16E56.3
Cl2B—C5B—H5C109.0H16B—C16—H16E141.1
C6B—C5B—H5D109.0H16C—C16—H16E56.3
Cl2B—C5B—H5D109.0H16D—C16—H16E109.5
H5C—C5B—H5D107.8C15—C16—H16F109.5
C5B—C6B—C7B111.6 (8)H16A—C16—H16F56.3
C5B—C6B—H6C109.3H16B—C16—H16F56.3
C7B—C6B—H6C109.3H16C—C16—H16F141.1
C5B—C6B—H6D109.3H16D—C16—H16F109.5
C7B—C6B—H6D109.3H16E—C16—H16F109.5
H6C—C6B—H6D108.0C15—C17—H17A109.5
C8B—C7B—C12118.7 (5)C15—C17—H17B109.5
C8B—C7B—C6B117.4 (7)H17A—C17—H17B109.5
C12—C7B—C6B123.6 (6)C15—C17—H17C109.5
C7B—C8B—C9121.0 (7)H17A—C17—H17C109.5
C7B—C8B—H8B119.5H17B—C17—H17C109.5
C9—C8B—H8B119.5C15—C17—H17D109.5
C8A—C9—C10117.85 (11)H17A—C17—H17D141.1
C10—C9—C8B114.1 (4)H17B—C17—H17D56.3
C8A—C9—C13134.61 (11)H17C—C17—H17D56.3
C10—C9—C13107.42 (7)C15—C17—H17E109.5
C8B—C9—C13132.8 (4)H17A—C17—H17E56.3
C11—C10—N4127.85 (9)H17B—C17—H17E141.1
C11—C10—C9123.12 (8)H17C—C17—H17E56.3
N4—C10—C9109.03 (8)H17D—C17—H17E109.5
C10—C11—C12116.87 (9)C15—C17—H17F109.5
C10—C11—H11121.6H17A—C17—H17F56.3
C12—C11—H11121.6H17B—C17—H17F56.3
C11—C12—C7A122.91 (10)H17C—C17—H17F141.1
C11—C12—C7B118.4 (3)H17D—C17—H17F109.5
C11—C12—Cl1117.09 (8)H17E—C17—H17F109.5
Cl2A—C5A—C6A—C7A176.40 (11)C10—C11—C12—Cl1−179.38 (8)
C5A—C6A—C7A—C1290.18 (18)C8A—C7A—C12—C11−7.8 (2)
C5A—C6A—C7A—C8A−87.90 (17)C6A—C7A—C12—C11174.13 (13)
C12—C7A—C8A—C92.7 (2)C8A—C7A—C12—Cl1177.11 (12)
C6A—C7A—C8A—C9−179.14 (15)C6A—C7A—C12—Cl1−1.0 (2)
Cl2B—C5B—C6B—C7B−176.5 (6)C8B—C7B—C12—C1124.6 (10)
C5B—C6B—C7B—C8B94.2 (10)C6B—C7B—C12—C11−161.5 (7)
C5B—C6B—C7B—C12−79.7 (11)C8B—C7B—C12—Cl1178.7 (6)
C12—C7B—C8B—C9−1.6 (12)C6B—C7B—C12—Cl1−7.5 (11)
C6B—C7B—C8B—C9−175.8 (8)C8A—C9—C13—C1512.5 (2)
C7A—C8A—C9—C104.3 (2)C10—C9—C13—C15−171.78 (11)
C7A—C8A—C9—C13179.65 (13)C8B—C9—C13—C15−20.8 (5)
C7B—C8B—C9—C10−19.6 (9)C8A—C9—C13—C14−171.37 (15)
C7B—C8B—C9—C13−169.1 (6)C10—C9—C13—C144.33 (11)
C14—N4—C10—C11−179.28 (11)C8B—C9—C13—C14155.4 (5)
C14—N4—C10—C90.11 (13)C10—N4—C14—O3−176.79 (10)
C8A—C9—C10—C11−6.94 (18)C10—N4—C14—C132.67 (13)
C8B—C9—C10—C1119.4 (5)C15—C13—C14—O3−8.40 (19)
C13—C9—C10—C11176.52 (10)C9—C13—C14—O3175.16 (11)
C8A—C9—C10—N4173.63 (12)C15—C13—C14—N4172.17 (11)
C8B—C9—C10—N4−160.0 (5)C9—C13—C14—N4−4.27 (12)
C13—C9—C10—N4−2.90 (12)C9—C13—C15—C16173.69 (11)
N4—C10—C11—C12−178.46 (11)C14—C13—C15—C16−1.76 (18)
C9—C10—C11—C122.23 (16)C9—C13—C15—C17−4.40 (19)
C10—C11—C12—C7A5.36 (18)C14—C13—C15—C17−179.85 (11)
C10—C11—C12—C7B−24.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4N···O3i0.84 (1)2.02 (1)2.8349 (11)166 (2)
Symmetry code: (i) −x, −y−1, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4N···O3i0.836 (13)2.017 (13)2.8349 (11)166.0 (15)
Symmetry code: (i) −x, −y−1, −z.
 

Acknowledgements

We are grateful to the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the CCD X-ray facilities, X-ray data collection, GCMS, IR, CHNS and NMR data. KMK is grateful to Karnatak Science College, Dharwad, for providing laboratory facilities.

References

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ISSN: 2056-9890
Volume 71| Part 8| August 2015| Pages o592-o593
https://doi.org/10.1107/S2056989015012268
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