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

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ISSN: 2056-9890

6-Chloro-3-[(di­methyl­amino)­methyl­­idene]thio­chroman-4-one

aDepartment of Chemistry, Karnatak University, Dharwad 580 003, India, and bDepartment of Studies in Chemistry, Bangalore University, Bangalore 560 001, Karnataka, India
*Correspondence e-mail: dr_imk@yahoo.com

(Received 22 July 2013; accepted 3 September 2013; online 7 September 2013)

The asymmetric unit of the title compound, C12H12ClNOS, contains three independent mol­ecules, with the thio­chroman ring adopting a sofa conformation in each one. The crystal structure features C—H⋯O inter­actions; one of the O atoms accepts three such bonds. Together, the hydrogen bonds give rise to a molecular tape propagating in [010].

Related literature

For general background and the anti­fungal activity of thio­chromans, see: Wang et al. (2010[Wang, G., Yang, G. L., Ma, Z. Y., Tian, W., Fang, B. L. & Li, L. B. (2010). Int. J. Chem. 1, 19-25.]); Sosnovskikh (2003[Sosnovskikh, V. Y. (2003). Russ. Chem. Rev. 72, 489-516.]). For the crystal structure of a related compound, see: Butt et al. (1988[Butt, G. L., Deady, L. W. & Mackay, M. F. (1988). J. Heterocycl. Chem. 25, 321-326.]).

[Scheme 1]

Experimental

Crystal data
  • C12H12ClNOS

  • Mr = 253.74

  • Monoclinic, P 21

  • a = 11.0031 (3) Å

  • b = 12.5937 (3) Å

  • c = 13.0787 (3) Å

  • β = 100.255 (2)°

  • V = 1783.36 (8) Å3

  • Z = 6

  • Mo Kα radiation

  • μ = 0.47 mm−1

  • T = 296 K

  • 0.18 × 0.16 × 0.16 mm

Data collection
  • Bruker SMART APEX CCD detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.920, Tmax = 0.928

  • 13306 measured reflections

  • 6540 independent reflections

  • 5418 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.087

  • S = 1.01

  • 6540 reflections

  • 440 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C1a—H1a2⋯O1bi 0.97 2.39 3.235 (4) 144
C11a—H11d⋯O1bi 0.96 2.63 3.290 (4) 126
C1b—H1b2⋯O1a 0.97 2.43 3.284 (1) 147
C12a—H12b⋯O1b 0.96 2.59 3.358 (4) 137
Symmetry code: (i) x, y-1, z.

Data collection: SMART (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CAMERON (Watkin et al., 1996)[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]; software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information


Comment top

Thiochromanones belong to an important class of oxygen containing heterocycles; many of their derivatives have been reported to possess important biological activities including antifungal activity (Wang et al.,2010). They also serve as the starting material for the synthesis of novel heterocyclic systems (Sosnovskikh, 2003).

There are three crystallographically independent molecules (A, B and C) in an asymmetric unit of the title compond (Fig. 1) wherein 6-chloro-thiochroman moiety is substituted with the dimethylaminomethylene group at C2. The dimethylamino group is oriented trans with respect to the oxo group of the thiochroman moiety which is described by the torsion angles N1—C3A—C2A –C4A, N2—C3B—C2B—C4B and N3—C3C—C2C—C4C [172.25 (3), -173.45 (2) and -171.53 (3)°] for the molecules A, B and C, respectively. The thiochroman rings in the three molecules are significantly puckered and adopt sofa conformations. A mean-planes calculation shows that the atoms S1A, S1B and S1C deviate from the mean planes of the remaining ring atoms by 0.7536 (1), -0.7360 (1) and -0.6753 (1) Å, respectively. The bond distances and angles in the three molecules of the title compound agree very well with the corresponding bond distances and angles reported in a closely related compound (Butt et al., 1988).

The crystal structure is stabilized by C—H···O type intermolecular interactions (Tab. 1 & Fig. 2); three such interactions form trifurcated bonds from three donors C1A, C11A and C12A to the same acceptor O1B, linking the molecules in a tape like structure. Whereas, another C—H···O interaction results in a one dimensional chain along the b-axis.

Related literature top

For general background and the antifungal activity of thiochromans, see: Wang et al. (2010); Sosnovskikh (2003). For the crystal structure of a related compound, see: Butt et al. (1988).

Experimental top

A mixture of 6-chloro -thiochroman-4-one (0.01 mol) and dimethylformamide-dimethylacetal (DMF-DMA) (2 mL) was heated under reflux for 10 h. The reaction mixture was triturated with ethanol to give a solid product that was collected by filtration and crystallized from ethanol to give the title compound as deep yellow crystals, melting point 379–381 K. Yield 78%.

Refinement top

The H atoms were placed at calculated positions in the riding model approximation with C—H = 0.97° A, 0.93 Å and 0.96 Å for aromatic, heterocyclic and methyl H-atoms respectively, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and Uiso(H) = 1.2Ueq(N/C). Since the crystals contained racemic twins, an absolute structure could not be established and therefore, 2865 Friedel pairs of reflections were merged.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. ORTEP (Farrugia, 2012) diagram of the three independent molecules present in the asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. A unit cell packing of the title compound showing intermolecular interactions with dotted lines. H-atoms not involved in hydrogen bonding have been excluded.
6-Chloro-3-[(dimethylamino)methylidene]thiochroman-4-one top
Crystal data top
C12H12ClNOSF(000) = 792
Mr = 253.74Dx = 1.418 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 6540 reflections
a = 11.0031 (3) Åθ = 1.6–26.1°
b = 12.5937 (3) ŵ = 0.47 mm1
c = 13.0787 (3) ÅT = 296 K
β = 100.255 (2)°Block, yellow
V = 1783.36 (8) Å30.18 × 0.16 × 0.16 mm
Z = 6
Data collection top
Bruker SMART APEX CCD detector
diffractometer
6540 independent reflections
Radiation source: fine-focus sealed tube5418 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω scansθmax = 26.1°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 1311
Tmin = 0.920, Tmax = 0.928k = 1515
13306 measured reflectionsl = 1516
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0363P)2 + 0.3396P]
where P = (Fo2 + 2Fc2)/3
6540 reflections(Δ/σ)max = 0.001
440 parametersΔρmax = 0.20 e Å3
1 restraintΔρmin = 0.32 e Å3
Crystal data top
C12H12ClNOSV = 1783.36 (8) Å3
Mr = 253.74Z = 6
Monoclinic, P21Mo Kα radiation
a = 11.0031 (3) ŵ = 0.47 mm1
b = 12.5937 (3) ÅT = 296 K
c = 13.0787 (3) Å0.18 × 0.16 × 0.16 mm
β = 100.255 (2)°
Data collection top
Bruker SMART APEX CCD detector
diffractometer
6540 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
5418 reflections with I > 2σ(I)
Tmin = 0.920, Tmax = 0.928Rint = 0.023
13306 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0391 restraint
wR(F2) = 0.087H-atom parameters constrained
S = 1.01Δρmax = 0.20 e Å3
6540 reflectionsΔρmin = 0.32 e Å3
440 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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
xyzUiso*/Ueq
S1C3.42533 (9)0.93986 (6)0.35478 (6)0.0616 (2)
S1B3.07997 (9)1.52311 (6)0.62968 (7)0.0660 (2)
Cl1C3.52910 (9)1.26958 (9)0.02286 (7)0.0825 (3)
S1A3.07889 (9)2.03016 (7)0.89801 (6)0.0696 (3)
Cl1B3.19333 (10)1.20168 (9)0.29486 (7)0.0839 (3)
C6B3.1874 (3)1.2629 (3)0.4910 (2)0.0522 (8)
H6B3.21901.19570.50950.063*
C4C3.5168 (3)1.1744 (2)0.4045 (2)0.0437 (7)
O1C3.5194 (2)1.27163 (15)0.41754 (16)0.0634 (6)
C6C3.5265 (3)1.2055 (3)0.2193 (2)0.0481 (7)
H6C3.56141.27130.23890.058*
O1A3.1373 (2)1.69412 (16)0.86749 (15)0.0683 (7)
N13.2097 (2)1.3641 (2)0.95226 (19)0.0548 (6)
C5B3.1633 (3)1.3321 (2)0.5676 (2)0.0469 (7)
C2C3.5249 (3)1.0987 (2)0.4879 (2)0.0417 (7)
C5C3.5017 (2)1.1352 (2)0.2945 (2)0.0401 (6)
C2B3.1897 (3)1.3663 (2)0.7622 (2)0.0480 (7)
N23.1930 (2)1.85555 (19)0.61376 (18)0.0487 (6)
C6A3.1601 (3)1.7658 (2)1.0679 (2)0.0470 (7)
H6A3.18301.69591.05820.056*
C3B3.1897 (3)1.3229 (2)0.8579 (2)0.0486 (7)
H3B3.17241.25060.85630.058*
N33.5292 (2)1.0987 (2)0.67712 (19)0.0542 (7)
C5A3.1416 (3)1.8353 (2)0.9845 (2)0.0429 (7)
C9B3.0975 (3)1.4623 (3)0.4334 (3)0.0611 (9)
H9B3.06741.52970.41370.073*
C10C3.4542 (3)1.0344 (2)0.2642 (2)0.0455 (7)
C3C3.5134 (3)1.1407 (2)0.5828 (2)0.0455 (7)
H3C3.49021.21180.58030.055*
C3A3.1682 (3)1.8183 (2)0.7022 (2)0.0449 (7)
H3A3.14471.74730.69870.054*
C4A3.1493 (3)1.7912 (2)0.8782 (2)0.0465 (7)
O1B3.1807 (3)1.19390 (17)0.68895 (17)0.0804 (8)
C2A3.1701 (3)1.8629 (2)0.7978 (2)0.0454 (7)
C10B3.1184 (3)1.4340 (2)0.5381 (2)0.0494 (7)
C8B3.1206 (3)1.3923 (3)0.3592 (3)0.0618 (9)
H8B3.10631.41180.28950.074*
C4B3.1791 (3)1.2914 (2)0.6772 (2)0.0515 (8)
C9C3.4249 (3)1.0108 (3)0.1581 (2)0.0600 (9)
H9C3.38960.94550.13710.072*
C12A3.1723 (3)1.7894 (3)0.5204 (2)0.0600 (9)
H12A3.13801.72240.53580.090*
H12B3.11601.82460.46650.090*
H12C3.24941.77760.49750.090*
C10A3.1085 (3)1.9398 (2)1.0013 (2)0.0478 (7)
C12B3.1897 (3)1.3005 (3)1.0410 (2)0.0672 (10)
H12D3.16121.23111.01760.101*
H12E3.26591.29431.08950.101*
H12F3.12891.33431.07430.101*
C7A3.1449 (3)1.7990 (2)1.1649 (2)0.0503 (7)
C1B3.1963 (3)1.4825 (2)0.7383 (2)0.0601 (9)
H1B13.18601.52320.79920.072*
H1B23.27731.49860.72300.072*
C12C3.4992 (4)1.1612 (3)0.7633 (2)0.0730 (11)
H12G3.46881.22960.73830.109*
H12H3.43711.12510.79320.109*
H12I3.57211.17010.81520.109*
C8C3.4473 (3)1.0822 (3)0.0849 (3)0.0650 (10)
H8C3.42731.06560.01460.078*
C9A3.0919 (3)1.9717 (2)1.1001 (2)0.0542 (8)
H9A3.06772.04111.11040.065*
C8A3.1110 (3)1.9021 (2)1.1819 (2)0.0546 (8)
H8A3.10111.92401.24790.066*
C7B3.1653 (3)1.2924 (3)0.3887 (2)0.0566 (8)
C1C3.5392 (3)0.9836 (2)0.4629 (2)0.0525 (8)
H1C13.62100.97220.44690.063*
H1C23.53220.94120.52350.063*
C7C3.4997 (3)1.1785 (3)0.1159 (2)0.0527 (8)
C11B3.2578 (4)1.4694 (3)0.9776 (3)0.0897 (13)
H11A3.30901.49030.92880.134*
H11B3.19061.51850.97450.134*
H11C3.30601.46931.04650.134*
C1A3.1902 (4)1.9785 (2)0.8248 (2)0.0615 (9)
H1A13.27251.98760.86510.074*
H1A23.18542.01910.76130.074*
C11A3.2427 (4)1.9601 (3)0.5984 (3)0.0751 (10)
H11D3.17742.01160.59040.113*
H11E3.30431.97830.65740.113*
H11F3.27941.95950.53700.113*
C11C3.5908 (4)0.9984 (3)0.7056 (3)0.0877 (13)
H11G3.53080.94240.69890.131*
H11H3.64900.98460.66060.131*
H11I3.63351.00200.77630.131*
Cl1A3.16764 (10)1.70872 (8)1.26739 (6)0.0761 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1C0.0853 (6)0.0400 (4)0.0618 (5)0.0166 (4)0.0197 (4)0.0109 (4)
S1B0.0957 (7)0.0386 (4)0.0702 (5)0.0110 (5)0.0320 (5)0.0116 (4)
Cl1C0.0880 (7)0.1115 (8)0.0503 (5)0.0071 (6)0.0187 (5)0.0184 (5)
S1A0.1128 (8)0.0386 (4)0.0568 (5)0.0172 (5)0.0133 (5)0.0039 (4)
Cl1B0.0925 (7)0.1090 (8)0.0526 (5)0.0087 (6)0.0194 (5)0.0158 (5)
C6B0.0514 (18)0.0576 (19)0.0489 (18)0.0055 (15)0.0125 (14)0.0025 (15)
C4C0.0505 (17)0.0363 (16)0.0447 (16)0.0032 (13)0.0098 (14)0.0079 (13)
O1C0.1068 (19)0.0324 (12)0.0515 (13)0.0062 (12)0.0155 (12)0.0053 (10)
C6C0.0482 (17)0.0466 (17)0.0499 (17)0.0011 (14)0.0096 (14)0.0033 (15)
O1A0.125 (2)0.0362 (12)0.0446 (12)0.0043 (12)0.0184 (13)0.0032 (10)
N10.0678 (17)0.0477 (15)0.0473 (15)0.0021 (13)0.0064 (13)0.0003 (12)
C5B0.0487 (17)0.0460 (17)0.0477 (17)0.0008 (13)0.0134 (14)0.0023 (14)
C2C0.0479 (17)0.0335 (15)0.0431 (16)0.0022 (13)0.0061 (13)0.0032 (12)
C5C0.0400 (15)0.0379 (15)0.0436 (16)0.0017 (13)0.0102 (13)0.0043 (13)
C2B0.0581 (19)0.0429 (16)0.0461 (17)0.0021 (14)0.0181 (15)0.0002 (14)
N20.0630 (16)0.0437 (13)0.0413 (14)0.0006 (12)0.0147 (12)0.0034 (11)
C6A0.0568 (18)0.0449 (16)0.0393 (16)0.0040 (14)0.0087 (14)0.0046 (13)
C3B0.0571 (19)0.0392 (16)0.0507 (18)0.0042 (14)0.0127 (15)0.0006 (14)
N30.0687 (17)0.0522 (16)0.0400 (14)0.0030 (13)0.0052 (12)0.0006 (12)
C5A0.0489 (16)0.0438 (16)0.0354 (14)0.0019 (13)0.0056 (13)0.0064 (12)
C9B0.061 (2)0.059 (2)0.063 (2)0.0057 (17)0.0113 (17)0.0163 (18)
C10C0.0439 (16)0.0463 (17)0.0468 (16)0.0012 (14)0.0098 (13)0.0093 (14)
C3C0.0500 (18)0.0395 (16)0.0466 (17)0.0057 (13)0.0077 (14)0.0042 (13)
C3A0.0538 (18)0.0386 (15)0.0415 (16)0.0007 (13)0.0062 (14)0.0019 (13)
C4A0.063 (2)0.0355 (16)0.0392 (15)0.0063 (14)0.0040 (14)0.0059 (12)
O1B0.152 (2)0.0398 (13)0.0529 (13)0.0160 (14)0.0292 (15)0.0045 (11)
C2A0.0602 (18)0.0367 (15)0.0373 (15)0.0003 (14)0.0028 (13)0.0036 (12)
C10B0.0513 (17)0.0404 (16)0.0595 (18)0.0021 (14)0.0181 (15)0.0091 (14)
C8B0.058 (2)0.080 (3)0.0480 (19)0.0077 (18)0.0098 (16)0.0125 (17)
C4B0.068 (2)0.0373 (17)0.0514 (18)0.0077 (14)0.0155 (15)0.0042 (13)
C9C0.066 (2)0.056 (2)0.0575 (19)0.0087 (17)0.0102 (16)0.0185 (17)
C12A0.080 (2)0.065 (2)0.0366 (16)0.0002 (18)0.0161 (16)0.0089 (15)
C10A0.0505 (17)0.0430 (15)0.0480 (16)0.0014 (14)0.0040 (13)0.0084 (14)
C12B0.080 (2)0.082 (2)0.0405 (17)0.008 (2)0.0133 (17)0.0061 (17)
C7A0.0535 (18)0.0584 (19)0.0404 (15)0.0002 (15)0.0124 (14)0.0010 (14)
C1B0.089 (3)0.0401 (16)0.0564 (19)0.0102 (16)0.0270 (18)0.0038 (14)
C12C0.092 (3)0.084 (3)0.0468 (19)0.013 (2)0.0222 (19)0.0105 (18)
C8C0.066 (2)0.089 (3)0.0405 (17)0.002 (2)0.0099 (16)0.0137 (17)
C9A0.0592 (19)0.0485 (18)0.0567 (19)0.0008 (15)0.0152 (16)0.0180 (15)
C8A0.0575 (19)0.064 (2)0.0455 (18)0.0075 (16)0.0185 (15)0.0153 (15)
C7B0.0487 (18)0.078 (2)0.0445 (17)0.0041 (17)0.0123 (14)0.0021 (17)
C1C0.069 (2)0.0399 (16)0.0499 (17)0.0041 (14)0.0140 (15)0.0014 (13)
C7C0.0477 (18)0.068 (2)0.0431 (17)0.0013 (16)0.0102 (14)0.0022 (16)
C11B0.131 (4)0.069 (3)0.061 (2)0.016 (2)0.005 (2)0.0070 (19)
C1A0.102 (3)0.0403 (16)0.0446 (16)0.0135 (17)0.0193 (17)0.0056 (14)
C11A0.101 (3)0.060 (2)0.076 (2)0.025 (2)0.047 (2)0.0089 (19)
C11C0.123 (4)0.071 (3)0.057 (2)0.016 (2)0.014 (2)0.0074 (19)
Cl1A0.1077 (7)0.0810 (6)0.0412 (4)0.0031 (6)0.0176 (4)0.0045 (4)
Geometric parameters (Å, º) top
S1C—C10C1.749 (3)C10C—C9C1.399 (4)
S1C—C1C1.801 (3)C3C—H3C0.9300
S1B—C10B1.748 (3)C3A—C2A1.367 (4)
S1B—C1B1.808 (4)C3A—H3A0.9300
Cl1C—C7C1.743 (3)C4A—C2A1.434 (4)
S1A—C10A1.752 (3)O1B—C4B1.238 (3)
S1A—C1A1.804 (3)C2A—C1A1.505 (4)
Cl1B—C7B1.744 (3)C8B—C7B1.380 (4)
C6B—C7B1.369 (4)C8B—H8B0.9300
C6B—C5B1.389 (4)C9C—C8C1.368 (4)
C6B—H6B0.9300C9C—H9C0.9300
C4C—O1C1.236 (3)C12A—H12A0.9600
C4C—C2C1.439 (4)C12A—H12B0.9600
C4C—C5C1.503 (4)C12A—H12C0.9600
C6C—C7C1.375 (4)C10A—C9A1.395 (4)
C6C—C5C1.386 (4)C12B—H12D0.9600
C6C—H6C0.9300C12B—H12E0.9600
O1A—C4A1.235 (3)C12B—H12F0.9600
N1—C3B1.320 (4)C7A—C8A1.381 (4)
N1—C11B1.445 (4)C7A—Cl1A1.742 (3)
N1—C12B1.458 (4)C1B—H1B10.9700
C5B—C10B1.404 (4)C1B—H1B20.9700
C5B—C4B1.503 (4)C12C—H12G0.9600
C2C—C3C1.376 (4)C12C—H12H0.9600
C2C—C1C1.500 (4)C12C—H12I0.9600
C5C—C10C1.402 (4)C8C—C7C1.373 (4)
C2B—C3B1.365 (4)C8C—H8C0.9300
C2B—C4B1.447 (4)C9A—C8A1.371 (4)
C2B—C1B1.501 (4)C9A—H9A0.9300
N2—C3A1.321 (3)C8A—H8A0.9300
N2—C11A1.454 (4)C1C—H1C10.9700
N2—C12A1.462 (3)C1C—H1C20.9700
C6A—C7A1.373 (4)C11B—H11A0.9600
C6A—C5A1.386 (4)C11B—H11B0.9600
C6A—H6A0.9300C11B—H11C0.9600
C3B—H3B0.9300C1A—H1A10.9700
N3—C3C1.324 (3)C1A—H1A20.9700
N3—C11C1.450 (4)C11A—H11D0.9600
N3—C12C1.460 (4)C11A—H11E0.9600
C5A—C10A1.393 (4)C11A—H11F0.9600
C5A—C4A1.513 (4)C11C—H11G0.9600
C9B—C8B1.368 (4)C11C—H11H0.9600
C9B—C10B1.394 (4)C11C—H11I0.9600
C9B—H9B0.9300
C10C—S1C—C1C97.97 (14)H12A—C12A—H12B109.5
C10B—S1B—C1B97.68 (15)N2—C12A—H12C109.5
C10A—S1A—C1A97.13 (14)H12A—C12A—H12C109.5
C7B—C6B—C5B120.7 (3)H12B—C12A—H12C109.5
C7B—C6B—H6B119.6C5A—C10A—C9A120.0 (3)
C5B—C6B—H6B119.6C5A—C10A—S1A120.7 (2)
O1C—C4C—C2C123.7 (3)C9A—C10A—S1A119.3 (2)
O1C—C4C—C5C117.0 (3)N1—C12B—H12D109.5
C2C—C4C—C5C119.3 (2)N1—C12B—H12E109.5
C7C—C6C—C5C120.3 (3)H12D—C12B—H12E109.5
C7C—C6C—H6C119.8N1—C12B—H12F109.5
C5C—C6C—H6C119.8H12D—C12B—H12F109.5
C3B—N1—C11B124.6 (3)H12E—C12B—H12F109.5
C3B—N1—C12B120.4 (3)C6A—C7A—C8A121.1 (3)
C11B—N1—C12B115.0 (3)C6A—C7A—Cl1A119.2 (2)
C6B—C5B—C10B118.6 (3)C8A—C7A—Cl1A119.7 (2)
C6B—C5B—C4B118.0 (3)C2B—C1B—S1B112.7 (2)
C10B—C5B—C4B123.3 (3)C2B—C1B—H1B1109.1
C3C—C2C—C4C115.2 (2)S1B—C1B—H1B1109.1
C3C—C2C—C1C126.7 (3)C2B—C1B—H1B2109.1
C4C—C2C—C1C118.0 (2)S1B—C1B—H1B2109.1
C6C—C5C—C10C119.3 (3)H1B1—C1B—H1B2107.8
C6C—C5C—C4C117.8 (2)N3—C12C—H12G109.5
C10C—C5C—C4C122.7 (2)N3—C12C—H12H109.5
C3B—C2B—C4B115.5 (3)H12G—C12C—H12H109.5
C3B—C2B—C1B126.1 (3)N3—C12C—H12I109.5
C4B—C2B—C1B118.4 (3)H12G—C12C—H12I109.5
C3A—N2—C11A125.8 (3)H12H—C12C—H12I109.5
C3A—N2—C12A120.2 (2)C9C—C8C—C7C119.5 (3)
C11A—N2—C12A114.0 (2)C9C—C8C—H8C120.2
C7A—C6A—C5A120.6 (3)C7C—C8C—H8C120.2
C7A—C6A—H6A119.7C8A—C9A—C10A120.8 (3)
C5A—C6A—H6A119.7C8A—C9A—H9A119.6
N1—C3B—C2B132.3 (3)C10A—C9A—H9A119.6
N1—C3B—H3B113.9C9A—C8A—C7A118.9 (3)
C2B—C3B—H3B113.9C9A—C8A—H8A120.5
C3C—N3—C11C124.4 (3)C7A—C8A—H8A120.5
C3C—N3—C12C119.6 (3)C6B—C7B—C8B120.9 (3)
C11C—N3—C12C115.5 (3)C6B—C7B—Cl1B119.2 (3)
C6A—C5A—C10A118.6 (3)C8B—C7B—Cl1B119.9 (3)
C6A—C5A—C4A117.9 (2)C2C—C1C—S1C112.4 (2)
C10A—C5A—C4A123.4 (3)C2C—C1C—H1C1109.1
C8B—C9B—C10B120.8 (3)S1C—C1C—H1C1109.1
C8B—C9B—H9B119.6C2C—C1C—H1C2109.1
C10B—C9B—H9B119.6S1C—C1C—H1C2109.1
C9C—C10C—C5C118.7 (3)H1C1—C1C—H1C2107.9
C9C—C10C—S1C119.3 (2)C8C—C7C—C6C120.9 (3)
C5C—C10C—S1C121.9 (2)C8C—C7C—Cl1C119.7 (2)
N3—C3C—C2C132.0 (3)C6C—C7C—Cl1C119.3 (3)
N3—C3C—H3C114.0N1—C11B—H11A109.5
C2C—C3C—H3C114.0N1—C11B—H11B109.5
N2—C3A—C2A133.1 (3)H11A—C11B—H11B109.5
N2—C3A—H3A113.4N1—C11B—H11C109.5
C2A—C3A—H3A113.4H11A—C11B—H11C109.5
O1A—C4A—C2A124.6 (3)H11B—C11B—H11C109.5
O1A—C4A—C5A116.4 (3)C2A—C1A—S1A112.9 (2)
C2A—C4A—C5A119.0 (2)C2A—C1A—H1A1109.0
C3A—C2A—C4A115.7 (2)S1A—C1A—H1A1109.0
C3A—C2A—C1A126.1 (3)C2A—C1A—H1A2109.0
C4A—C2A—C1A118.2 (2)S1A—C1A—H1A2109.0
C9B—C10B—C5B119.5 (3)H1A1—C1A—H1A2107.8
C9B—C10B—S1B119.4 (2)N2—C11A—H11D109.5
C5B—C10B—S1B120.9 (2)N2—C11A—H11E109.5
C9B—C8B—C7B119.4 (3)H11D—C11A—H11E109.5
C9B—C8B—H8B120.3N2—C11A—H11F109.5
C7B—C8B—H8B120.3H11D—C11A—H11F109.5
O1B—C4B—C2B123.6 (3)H11E—C11A—H11F109.5
O1B—C4B—C5B117.0 (3)N3—C11C—H11G109.5
C2B—C4B—C5B119.4 (3)N3—C11C—H11H109.5
C8C—C9C—C10C121.1 (3)H11G—C11C—H11H109.5
C8C—C9C—H9C119.5N3—C11C—H11I109.5
C10C—C9C—H9C119.5H11G—C11C—H11I109.5
N2—C12A—H12A109.5H11H—C11C—H11I109.5
N2—C12A—H12B109.5
C7B—C6B—C5B—C10B1.5 (4)C4B—C5B—C10B—S1B1.3 (4)
C7B—C6B—C5B—C4B174.7 (3)C1B—S1B—C10B—C9B150.2 (3)
O1C—C4C—C2C—C3C11.4 (4)C1B—S1B—C10B—C5B33.6 (3)
C5C—C4C—C2C—C3C167.4 (3)C10B—C9B—C8B—C7B0.0 (5)
O1C—C4C—C2C—C1C171.2 (3)C3B—C2B—C4B—O1B6.2 (5)
C5C—C4C—C2C—C1C10.0 (4)C1B—C2B—C4B—O1B175.4 (3)
C7C—C6C—C5C—C10C2.8 (4)C3B—C2B—C4B—C5B172.9 (3)
C7C—C6C—C5C—C4C171.9 (3)C1B—C2B—C4B—C5B5.6 (4)
O1C—C4C—C5C—C6C17.8 (4)C6B—C5B—C4B—O1B18.5 (5)
C2C—C4C—C5C—C6C163.3 (3)C10B—C5B—C4B—O1B157.6 (3)
O1C—C4C—C5C—C10C156.7 (3)C6B—C5B—C4B—C2B162.5 (3)
C2C—C4C—C5C—C10C22.2 (4)C10B—C5B—C4B—C2B21.5 (5)
C11B—N1—C3B—C2B10.6 (6)C5C—C10C—C9C—C8C3.1 (5)
C12B—N1—C3B—C2B172.9 (3)S1C—C10C—C9C—C8C179.3 (3)
C4B—C2B—C3B—N1172.3 (3)C6A—C5A—C10A—C9A1.4 (4)
C1B—C2B—C3B—N19.4 (6)C4A—C5A—C10A—C9A173.9 (3)
C7A—C6A—C5A—C10A0.6 (4)C6A—C5A—C10A—S1A177.9 (2)
C7A—C6A—C5A—C4A175.0 (3)C4A—C5A—C10A—S1A2.6 (4)
C6C—C5C—C10C—C9C4.6 (4)C1A—S1A—C10A—C5A33.8 (3)
C4C—C5C—C10C—C9C169.9 (3)C1A—S1A—C10A—C9A149.7 (3)
C6C—C5C—C10C—S1C177.9 (2)C5A—C6A—C7A—C8A0.0 (5)
C4C—C5C—C10C—S1C7.7 (4)C5A—C6A—C7A—Cl1A179.4 (2)
C1C—S1C—C10C—C9C154.8 (2)C3B—C2B—C1B—S1B131.1 (3)
C1C—S1C—C10C—C5C27.7 (3)C4B—C2B—C1B—S1B47.1 (4)
C11C—N3—C3C—C2C14.4 (5)C10B—S1B—C1B—C2B56.2 (3)
C12C—N3—C3C—C2C174.5 (3)C10C—C9C—C8C—C7C0.1 (5)
C4C—C2C—C3C—N3171.5 (3)C5A—C10A—C9A—C8A1.6 (4)
C1C—C2C—C3C—N311.3 (6)S1A—C10A—C9A—C8A178.2 (2)
C11A—N2—C3A—C2A6.0 (6)C10A—C9A—C8A—C7A1.0 (5)
C12A—N2—C3A—C2A174.9 (3)C6A—C7A—C8A—C9A0.2 (5)
C6A—C5A—C4A—O1A19.5 (4)Cl1A—C7A—C8A—C9A179.2 (2)
C10A—C5A—C4A—O1A155.8 (3)C5B—C6B—C7B—C8B1.2 (5)
C6A—C5A—C4A—C2A160.3 (3)C5B—C6B—C7B—Cl1B178.4 (2)
C10A—C5A—C4A—C2A24.4 (4)C9B—C8B—C7B—C6B0.4 (5)
N2—C3A—C2A—C4A173.4 (3)C9B—C8B—C7B—Cl1B179.2 (2)
N2—C3A—C2A—C1A7.3 (6)C3C—C2C—C1C—S1C126.0 (3)
O1A—C4A—C2A—C3A4.2 (5)C4C—C2C—C1C—S1C51.1 (3)
C5A—C4A—C2A—C3A176.0 (3)C10C—S1C—C1C—C2C55.0 (2)
O1A—C4A—C2A—C1A176.5 (3)C9C—C8C—C7C—C6C2.0 (5)
C5A—C4A—C2A—C1A3.2 (4)C9C—C8C—C7C—Cl1C179.7 (2)
C8B—C9B—C10B—C5B0.3 (5)C5C—C6C—C7C—C8C0.5 (5)
C8B—C9B—C10B—S1B176.6 (2)C5C—C6C—C7C—Cl1C178.8 (2)
C6B—C5B—C10B—C9B1.0 (4)C3A—C2A—C1A—S1A132.5 (3)
C4B—C5B—C10B—C9B175.0 (3)C4A—C2A—C1A—S1A46.7 (4)
C6B—C5B—C10B—S1B177.3 (2)C10A—S1A—C1A—C2A57.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1a—H1a2···O1bi0.972.393.235 (4)144
C11a—H11d···O1bi0.962.633.290 (4)126
C1b—H1b2···O1a0.972.433.284 (1)147
C12a—H12b···O1b0.962.593.358 (4)137
Symmetry code: (i) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1a—H1a2···O1bi0.972.3933.235 (4)144
C11a—H11d···O1bi0.962.6303.290 (4)126
C1b—H1b2···O1a0.972.4303.284 (1)147
C12a—H12b···O1b0.962.5903.358 (4)137
Symmetry code: (i) x, y1, z.
 

Acknowledgements

IMK is thankful to the University Grants Commission (UGC), India, for financial assistance.

References

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First citationWatkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.

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