supplementary materials


cv5426 scheme

Acta Cryst. (2013). E69, o1593    [ doi:10.1107/S1600536813026123 ]

2,2'-{[(1E,1'E)-(Cyclohexane-1,4-diyl)bis(azanylylidene)]bis(ethan-1-yl-1-ylidene)}diphenol

S. H. A. Lakshmi, M. Kandaswamy and V. Ramkumar

Abstract top

The title compound, C22H26N2O2, crystallizes with three independent molecules, two of which are situated on inversion centers, so the asymmetric unit contains two independent half-molecules and one molecule in a general position. The two hydroxy groups in each molecule are involved in intramolecular O-H...N hydrogen bonds, which generate S(6) rings. In the crystal, weak intermolecular C-H...[pi] interactions link the molecules into two crystallographically independent columns propagating along [001]; one column consists of molecules in general positions, while the other column is built from alternating independent centrosymmetric molecules.

Comment top

The research field dealing with Schiff base coordination chemistry has expanded enormously (Chu et al., 2008; Gao et al., 2002; Hamil et al., 2012); the presence of a lone pair of electrons in an sp2 hybridized orbital of nitrogen atom of the azomethine group is of considerable chemical and biological importance (More et al., 2001). Because of the relative easiness of preparation, synthetic flexibility, and the special property of C=N group, Schiff bases are generally excellent chelating agents (Vigato et al., 2004). In azomethine derivatives, the C=N linkage is essential for biological activity, several azomethines were reported to possess remarkable antibacterial, antifungal, anticancer and diuretic activities. Herewith we present the crystal structure of the title compound.

The title compound crystallizes with two half-molecules situated on inversion centers and one molecule in general position (Fig. 1). Two hydroxy groups in each molecule are involved in intramolecular O—H···N hydrogen bonds (Table 1), which generate S(6) rings. In the crystal, weak intermolecular C—H···π interactions (Table 1) link the molecules into two crystallographically independent columns propagated in [001] - one column consists from the molecules in general positions, while another column is built from the alternating independent centrosymmetric molecules.

Related literature top

For applications of Schiff base ligands in coordination chemistry, see: Gao & Zheng (2002); Hamil et al. (2012); Chu et al. (2008); More et al. (2001); Vigato & Tamburini (2004). For details of the synthesis, see: Huang et al. (2008).

Experimental top

The title compound was prepared by treating trans1, 4-diamino cyclohexane with 2-hydroxy acetophenone in the stoichiometric ratio in the ethanolic solution and refluxed for 5 h. The reaction mixture was then cooled slowly to room temperature; a yellow crystalline product was obtained and further washed with cold ethanol respectively (Huang et al., 2008). It was then recrystallized from chloroform. The yellow like single-crystal of the title compound used in X-ray diffraction studies were grown in a chloroform solution by slow evaporation of the solvent at room temperature.

Refinement top

All hydrogen atoms were fixed geometrically (C—H 0.93–0.98 Å) and refined as riding, with Uiso(H) = 1.2–1.5 Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); 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, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Three crystallographically independent molecules showing the atomic numbering and 30% probability displacement ellipsoids [symmetry codes: (a) -x, 1 - y, -z; (b) 2 - x, 1 - y, 1 - z]. H atoms omitted for clarity.
2,2'-{[(1E,1'E)-(Cyclohexane-1,4-diyl)bis(azanylylidene)]bis(ethan-1-yl-1-ylidene)}diphenol top
Crystal data top
C22H26N2O2Z = 4
Mr = 350.45F(000) = 752
Triclinic, P1Dx = 1.259 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0299 (6) ÅCell parameters from 5628 reflections
b = 11.4718 (8) Åθ = 0.0–0.0°
c = 17.9652 (13) ŵ = 0.08 mm1
α = 92.946 (3)°T = 298 K
β = 95.521 (4)°Block, yellow
γ = 91.204 (3)°0.25 × 0.20 × 0.10 mm
V = 1849.3 (2) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
6387 independent reflections
Radiation source: fine-focus sealed tube2646 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
phi and ω scansθmax = 25.0°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1010
Tmin = 0.980, Tmax = 0.992k = 1313
20050 measured reflectionsl = 2121
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.239H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0873P)2 + 2.2422P]
where P = (Fo2 + 2Fc2)/3
6387 reflections(Δ/σ)max = 0.005
477 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C22H26N2O2γ = 91.204 (3)°
Mr = 350.45V = 1849.3 (2) Å3
Triclinic, P1Z = 4
a = 9.0299 (6) ÅMo Kα radiation
b = 11.4718 (8) ŵ = 0.08 mm1
c = 17.9652 (13) ÅT = 298 K
α = 92.946 (3)°0.25 × 0.20 × 0.10 mm
β = 95.521 (4)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
6387 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
2646 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.992Rint = 0.033
20050 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.239Δρmax = 0.30 e Å3
S = 1.02Δρmin = 0.23 e Å3
6387 reflectionsAbsolute structure: ?
477 parametersAbsolute structure parameter: ?
0 restraintsRogers parameter: ?
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.

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 > σ(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
C10.8319 (7)1.1440 (5)0.6061 (3)0.0575 (17)
H10.81501.22000.62330.069*
C20.9279 (7)1.0768 (6)0.6478 (3)0.0603 (18)
H20.97651.10780.69270.072*
C30.9532 (6)0.9640 (6)0.6240 (3)0.0594 (17)
H31.01880.91870.65250.071*
C40.8809 (6)0.9185 (5)0.5577 (3)0.0464 (14)
H40.89890.84220.54160.056*
C50.7805 (6)0.9842 (4)0.5136 (3)0.0362 (13)
C60.7589 (6)1.1000 (4)0.5381 (3)0.0439 (14)
C70.7032 (6)0.9339 (4)0.4427 (3)0.0365 (12)
C80.7086 (7)0.8049 (4)0.4243 (3)0.0579 (17)
H8A0.64800.78540.37830.087*
H8B0.67180.76310.46400.087*
H8C0.80950.78380.41890.087*
C90.5504 (6)0.9694 (4)0.3276 (3)0.0353 (13)
H90.50330.89230.33070.042*
C100.6546 (6)0.9646 (4)0.2661 (3)0.0408 (13)
H10A0.72590.90370.27540.049*
H10B0.70951.03830.26690.049*
C110.5697 (6)0.9406 (4)0.1895 (3)0.0398 (13)
H11A0.63910.94160.15160.048*
H11B0.52340.86320.18730.048*
C120.4503 (6)1.0297 (4)0.1724 (3)0.0389 (13)
H120.49781.10670.16940.047*
C130.3456 (6)1.0352 (4)0.2340 (3)0.0418 (13)
H13A0.27501.09660.22470.050*
H13B0.28990.96180.23320.050*
C140.4303 (6)1.0587 (4)0.3110 (3)0.0396 (13)
H14A0.36081.05700.34880.048*
H14B0.47631.13620.31360.048*
C150.2981 (6)1.0670 (4)0.0578 (3)0.0405 (13)
C160.2927 (7)1.1947 (4)0.0751 (3)0.0628 (18)
H16A0.36901.21760.11440.094*
H16B0.19711.21340.09090.094*
H16C0.30851.23560.03110.094*
C170.2196 (6)1.0170 (5)0.0128 (3)0.0425 (14)
C180.2409 (7)0.9003 (5)0.0371 (3)0.0507 (15)
C190.1686 (7)0.8566 (5)0.1058 (3)0.0591 (17)
H190.18660.78100.12330.071*
C200.0720 (7)0.9235 (6)0.1473 (3)0.0608 (18)
H200.02330.89240.19210.073*
C210.0462 (7)1.0362 (6)0.1235 (3)0.0608 (18)
H210.02031.08110.15170.073*
C220.1200 (6)1.0821 (5)0.0574 (3)0.0509 (15)
H220.10291.15880.04190.061*
C230.3019 (7)0.3440 (5)0.3478 (3)0.0517 (15)
H230.27330.26970.36030.062*
C240.4097 (6)0.4066 (5)0.3931 (3)0.0570 (17)
H240.45520.37380.43540.068*
C250.4508 (6)0.5175 (5)0.3762 (3)0.0584 (17)
H250.52390.55950.40710.070*
C260.3841 (6)0.5662 (5)0.3139 (3)0.0487 (15)
H260.41270.64150.30340.058*
C270.2739 (6)0.5058 (4)0.2651 (3)0.0378 (12)
C280.2345 (6)0.3910 (4)0.2828 (3)0.0418 (14)
C290.2037 (6)0.5571 (4)0.1977 (3)0.0398 (13)
C300.2285 (6)0.6845 (4)0.1877 (3)0.0567 (16)
H30A0.16190.70840.14670.085*
H30B0.32940.69860.17730.085*
H30C0.21000.72840.23270.085*
C310.0496 (6)0.5264 (4)0.0803 (3)0.0379 (13)
H310.00890.60390.08880.045*
C320.1573 (6)0.5315 (4)0.0199 (3)0.0424 (13)
H32A0.23440.59050.03500.051*
H32B0.20460.45680.01460.051*
C330.0771 (6)0.4398 (4)0.0546 (3)0.0420 (13)
H33A0.03770.36190.05020.050*
H33B0.14760.43980.09210.050*
C340.6985 (7)0.6551 (5)0.1526 (3)0.0535 (16)
H340.72730.72950.14040.064*
C350.5913 (7)0.5937 (6)0.1067 (3)0.0614 (18)
H350.54710.62670.06410.074*
C360.5488 (6)0.4827 (6)0.1238 (3)0.0605 (18)
H360.47500.44110.09320.073*
C370.6156 (6)0.4339 (5)0.1860 (3)0.0521 (15)
H370.58730.35850.19640.063*
C380.7259 (6)0.4945 (4)0.2347 (3)0.0403 (13)
C390.7655 (6)0.6083 (4)0.2172 (3)0.0450 (14)
C400.7956 (6)0.4409 (4)0.3026 (3)0.0382 (13)
C410.7717 (7)0.3141 (4)0.3121 (3)0.0582 (18)
H41A0.83260.29150.35550.087*
H41B0.79820.27030.26860.087*
H41C0.66890.29870.31840.087*
C420.9513 (5)0.4732 (4)0.4197 (3)0.0382 (13)
H420.99220.39570.41130.046*
C430.8430 (5)0.4678 (4)0.4798 (3)0.0398 (13)
H43A0.79470.54220.48460.048*
H43B0.76660.40830.46470.048*
C441.0776 (6)0.5597 (4)0.4452 (3)0.0391 (13)
H44A1.14860.55880.40790.047*
H44B1.03830.63760.44890.047*
N10.6309 (5)1.0050 (3)0.3999 (2)0.0394 (11)
N20.3692 (5)0.9952 (3)0.1003 (2)0.0408 (11)
N30.1238 (5)0.4889 (3)0.1507 (2)0.0397 (11)
N40.8768 (5)0.5101 (3)0.3495 (2)0.0406 (11)
O10.6695 (6)1.1708 (3)0.4976 (2)0.0688 (13)
H1A0.63491.13550.45880.103*
O20.3297 (6)0.8290 (3)0.0025 (2)0.0714 (13)
H2A0.37070.86530.03970.107*
O50.1332 (5)0.3254 (3)0.2392 (2)0.0574 (11)
H50.10700.35980.20140.086*
O60.8666 (5)0.6742 (3)0.2608 (2)0.0581 (11)
H60.89220.64020.29870.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.079 (5)0.054 (3)0.039 (3)0.023 (3)0.012 (3)0.002 (3)
C20.056 (4)0.088 (5)0.035 (3)0.022 (3)0.002 (3)0.007 (3)
C30.044 (4)0.093 (5)0.041 (4)0.001 (3)0.002 (3)0.012 (3)
C40.040 (4)0.060 (3)0.041 (3)0.004 (3)0.007 (3)0.007 (3)
C50.036 (3)0.042 (3)0.031 (3)0.005 (2)0.004 (3)0.006 (2)
C60.057 (4)0.041 (3)0.035 (3)0.007 (3)0.008 (3)0.006 (2)
C70.035 (3)0.040 (3)0.036 (3)0.002 (2)0.010 (3)0.007 (2)
C80.077 (5)0.044 (3)0.051 (4)0.012 (3)0.007 (3)0.004 (3)
C90.036 (3)0.038 (3)0.032 (3)0.002 (2)0.004 (3)0.004 (2)
C100.031 (3)0.049 (3)0.042 (3)0.003 (2)0.001 (3)0.001 (2)
C110.035 (3)0.048 (3)0.037 (3)0.003 (2)0.004 (3)0.002 (2)
C120.039 (3)0.039 (3)0.039 (3)0.001 (2)0.001 (3)0.001 (2)
C130.036 (3)0.051 (3)0.039 (3)0.004 (2)0.006 (3)0.003 (2)
C140.038 (4)0.047 (3)0.035 (3)0.004 (2)0.009 (3)0.001 (2)
C150.040 (3)0.049 (3)0.032 (3)0.001 (2)0.005 (3)0.006 (3)
C160.077 (5)0.051 (3)0.058 (4)0.006 (3)0.009 (4)0.003 (3)
C170.039 (4)0.055 (3)0.036 (3)0.004 (3)0.011 (3)0.007 (3)
C180.055 (4)0.056 (4)0.040 (3)0.008 (3)0.002 (3)0.009 (3)
C190.070 (5)0.061 (4)0.045 (4)0.017 (3)0.007 (4)0.002 (3)
C200.053 (5)0.087 (5)0.040 (4)0.021 (3)0.000 (3)0.001 (3)
C210.037 (4)0.097 (5)0.048 (4)0.001 (3)0.005 (3)0.014 (3)
C220.042 (4)0.069 (4)0.042 (3)0.006 (3)0.002 (3)0.009 (3)
C230.061 (4)0.053 (3)0.044 (3)0.018 (3)0.015 (3)0.006 (3)
C240.051 (4)0.083 (4)0.038 (3)0.019 (3)0.004 (3)0.007 (3)
C250.040 (4)0.087 (4)0.046 (4)0.000 (3)0.000 (3)0.005 (3)
C260.043 (4)0.062 (4)0.041 (3)0.007 (3)0.008 (3)0.002 (3)
C270.038 (3)0.045 (3)0.030 (3)0.003 (2)0.008 (3)0.005 (2)
C280.040 (4)0.047 (3)0.039 (3)0.005 (3)0.010 (3)0.002 (3)
C290.041 (3)0.043 (3)0.037 (3)0.001 (2)0.007 (3)0.002 (2)
C300.069 (4)0.051 (3)0.049 (3)0.006 (3)0.004 (3)0.001 (3)
C310.038 (4)0.042 (3)0.033 (3)0.005 (2)0.002 (3)0.001 (2)
C320.034 (3)0.052 (3)0.042 (3)0.001 (2)0.005 (3)0.005 (2)
C330.039 (3)0.053 (3)0.035 (3)0.000 (2)0.007 (3)0.008 (2)
C340.059 (4)0.058 (3)0.045 (3)0.016 (3)0.009 (3)0.009 (3)
C350.050 (4)0.089 (5)0.046 (4)0.023 (4)0.002 (3)0.005 (3)
C360.040 (4)0.092 (5)0.047 (4)0.007 (3)0.008 (3)0.006 (3)
C370.039 (4)0.064 (4)0.053 (4)0.005 (3)0.007 (3)0.004 (3)
C380.035 (4)0.052 (3)0.035 (3)0.006 (3)0.011 (3)0.001 (2)
C390.052 (4)0.043 (3)0.041 (3)0.009 (3)0.009 (3)0.005 (3)
C400.035 (4)0.045 (3)0.036 (3)0.001 (2)0.014 (3)0.006 (2)
C410.074 (5)0.046 (3)0.052 (4)0.007 (3)0.004 (4)0.004 (3)
C420.039 (3)0.039 (3)0.038 (3)0.005 (2)0.006 (3)0.006 (2)
C430.032 (3)0.049 (3)0.039 (3)0.000 (2)0.003 (3)0.005 (2)
C440.035 (3)0.045 (3)0.039 (3)0.001 (2)0.011 (3)0.007 (2)
N10.041 (3)0.040 (2)0.037 (2)0.0011 (19)0.002 (2)0.0043 (19)
N20.041 (3)0.048 (3)0.034 (3)0.001 (2)0.002 (2)0.003 (2)
N30.040 (3)0.046 (2)0.034 (2)0.002 (2)0.004 (2)0.0005 (19)
N40.044 (3)0.044 (2)0.035 (2)0.002 (2)0.005 (2)0.0022 (19)
O10.111 (4)0.040 (2)0.052 (3)0.008 (2)0.008 (3)0.0017 (19)
O20.104 (4)0.046 (2)0.059 (3)0.008 (2)0.015 (3)0.000 (2)
O50.077 (3)0.044 (2)0.048 (2)0.008 (2)0.005 (2)0.0011 (18)
O60.079 (3)0.043 (2)0.050 (3)0.006 (2)0.004 (2)0.0034 (18)
Geometric parameters (Å, º) top
C1—C21.367 (8)C24—C251.374 (7)
C1—C61.397 (7)C24—H240.9300
C1—H10.9300C25—C261.370 (7)
C2—C31.373 (8)C25—H250.9300
C2—H20.9300C26—C271.407 (6)
C3—C41.375 (7)C26—H260.9300
C3—H30.9300C27—C281.417 (7)
C4—C51.403 (6)C27—C291.468 (7)
C4—H40.9300C28—O51.338 (5)
C5—C61.402 (6)C29—N31.279 (6)
C5—C71.476 (6)C29—C301.497 (6)
C6—O11.346 (6)C30—H30A0.9600
C7—N11.293 (6)C30—H30B0.9600
C7—C81.502 (6)C30—H30C0.9600
C8—H8A0.9600C31—N31.462 (6)
C8—H8B0.9600C31—C331.522 (6)
C8—H8C0.9600C31—C321.528 (7)
C9—N11.460 (5)C31—H310.9800
C9—C101.519 (7)C32—C33i1.514 (6)
C9—C141.526 (6)C32—H32A0.9700
C9—H90.9800C32—H32B0.9700
C10—C111.519 (6)C33—C32i1.514 (6)
C10—H10A0.9700C33—H33A0.9700
C10—H10B0.9700C33—H33B0.9700
C11—C121.522 (6)C34—C351.367 (7)
C11—H11A0.9700C34—C391.394 (7)
C11—H11B0.9700C34—H340.9300
C12—N21.457 (6)C35—C361.381 (8)
C12—C131.524 (7)C35—H350.9300
C12—H120.9800C36—C371.368 (7)
C13—C141.523 (6)C36—H360.9300
C13—H13A0.9700C37—C381.407 (7)
C13—H13B0.9700C37—H370.9300
C14—H14A0.9700C38—C391.406 (7)
C14—H14B0.9700C38—C401.485 (7)
C15—N21.291 (6)C39—O61.338 (6)
C15—C171.474 (7)C40—N41.290 (6)
C15—C161.484 (7)C40—C411.487 (6)
C16—H16A0.9600C41—H41A0.9600
C16—H16B0.9600C41—H41B0.9600
C16—H16C0.9600C41—H41C0.9600
C17—C221.400 (7)C42—N41.459 (6)
C17—C181.409 (7)C42—C441.517 (6)
C18—O21.341 (6)C42—C431.528 (6)
C18—C191.403 (7)C42—H420.9800
C19—C201.367 (8)C43—C44ii1.516 (6)
C19—H190.9300C43—H43A0.9700
C20—C211.372 (8)C43—H43B0.9700
C20—H200.9300C44—C43ii1.516 (6)
C21—C221.379 (7)C44—H44A0.9700
C21—H210.9300C44—H44B0.9700
C22—H220.9300O1—H1A0.8200
C23—C241.373 (7)O2—H2A0.8200
C23—C281.402 (7)O5—H50.8201
C23—H230.9300O6—H60.8201
C2—C1—C6120.8 (6)C23—C24—H24119.6
C2—C1—H1119.4C25—C24—H24120.0
C6—C1—H1119.8C26—C25—C24120.0 (5)
C3—C2—C1120.6 (5)C26—C25—H25120.0
C3—C2—H2119.7C24—C25—H25120.0
C1—C2—H2119.7C25—C26—C27122.1 (5)
C2—C3—C4119.5 (5)C25—C26—H26119.0
C2—C3—H3120.4C27—C26—H26118.9
C4—C3—H3120.1C26—C27—C28117.1 (5)
C3—C4—C5121.7 (5)C26—C27—C29122.2 (5)
C3—C4—H4119.2C28—C27—C29120.6 (4)
C5—C4—H4119.1O5—C28—C23118.5 (5)
C4—C5—C6117.9 (4)O5—C28—C27121.8 (5)
C4—C5—C7121.1 (4)C23—C28—C27119.8 (5)
C6—C5—C7121.0 (4)N3—C29—C27117.3 (4)
O1—C6—C1118.7 (5)N3—C29—C30123.8 (5)
O1—C6—C5121.8 (4)C27—C29—C30118.9 (4)
C1—C6—C5119.5 (5)C29—C30—H30A109.5
N1—C7—C5117.1 (4)C29—C30—H30B109.7
N1—C7—C8123.3 (4)H30A—C30—H30B109.5
C5—C7—C8119.6 (4)C29—C30—H30C109.2
C7—C8—H8A109.6H30A—C30—H30C109.5
C7—C8—H8B109.5H30B—C30—H30C109.5
H8A—C8—H8B109.5N3—C31—C33108.2 (4)
C7—C8—H8C109.4N3—C31—C32111.4 (4)
H8A—C8—H8C109.5C33—C31—C32109.6 (4)
H8B—C8—H8C109.5N3—C31—H31109.3
N1—C9—C10110.9 (4)C33—C31—H31109.1
N1—C9—C14107.6 (4)C32—C31—H31109.2
C10—C9—C14110.1 (4)C33i—C32—C31111.1 (4)
N1—C9—H9109.4C33i—C32—H32A109.4
C10—C9—H9109.4C31—C32—H32A109.3
C14—C9—H9109.3C33i—C32—H32B109.6
C9—C10—C11111.4 (4)C31—C32—H32B109.4
C9—C10—H10A109.2H32A—C32—H32B108.0
C11—C10—H10A109.4C32i—C33—C31112.3 (4)
C9—C10—H10B109.6C32i—C33—H33A109.3
C11—C10—H10B109.3C31—C33—H33A109.0
H10A—C10—H10B107.9C32i—C33—H33B109.1
C12—C11—C10112.4 (4)C31—C33—H33B109.2
C12—C11—H11A109.1H33A—C33—H33B107.9
C10—C11—H11A109.1C35—C34—C39121.3 (5)
C12—C11—H11B109.1C35—C34—H34119.3
C10—C11—H11B109.2C39—C34—H34119.4
H11A—C11—H11B107.9C34—C35—C36119.8 (5)
N2—C12—C11108.3 (4)C34—C35—H35120.3
N2—C12—C13110.7 (4)C36—C35—H35119.9
C11—C12—C13110.0 (4)C37—C36—C35119.9 (5)
N2—C12—H12109.2C37—C36—H36120.0
C11—C12—H12109.3C35—C36—H36120.1
C13—C12—H12109.2C36—C37—C38122.0 (5)
C14—C13—C12111.6 (4)C36—C37—H37119.0
C14—C13—H13A109.3C38—C37—H37119.1
C12—C13—H13A109.5C39—C38—C37117.3 (5)
C14—C13—H13B109.3C39—C38—C40121.4 (4)
C12—C13—H13B109.1C37—C38—C40121.3 (5)
H13A—C13—H13B108.0O6—C39—C34118.3 (5)
C13—C14—C9112.3 (4)O6—C39—C38122.0 (5)
C13—C14—H14A109.2C34—C39—C38119.7 (5)
C9—C14—H14A109.2N4—C40—C38116.0 (4)
C13—C14—H14B109.0N4—C40—C41124.3 (5)
C9—C14—H14B109.2C38—C40—C41119.7 (4)
H14A—C14—H14B107.8C40—C41—H41A109.4
N2—C15—C17116.7 (4)C40—C41—H41B109.8
N2—C15—C16124.4 (5)H41A—C41—H41B109.5
C17—C15—C16118.9 (4)C40—C41—H41C109.2
C15—C16—H16A109.4H41A—C41—H41C109.5
C15—C16—H16B109.5H41B—C41—H41C109.5
H16A—C16—H16B109.5N4—C42—C44108.4 (4)
C15—C16—H16C109.5N4—C42—C43111.0 (4)
H16A—C16—H16C109.5C44—C42—C43109.9 (4)
H16B—C16—H16C109.5N4—C42—H42109.1
C22—C17—C18117.5 (5)C44—C42—H42109.2
C22—C17—C15121.7 (5)C43—C42—H42109.2
C18—C17—C15120.7 (5)C44ii—C43—C42111.3 (4)
O2—C18—C19118.2 (5)C44ii—C43—H43A109.2
O2—C18—C17122.5 (5)C42—C43—H43A109.4
C19—C18—C17119.3 (5)C44ii—C43—H43B109.4
C20—C19—C18120.9 (6)C42—C43—H43B109.4
C20—C19—H19119.8H43A—C43—H43B108.0
C18—C19—H19119.4C43ii—C44—C42112.3 (4)
C19—C20—C21120.7 (5)C43ii—C44—H44A109.2
C19—C20—H20119.7C42—C44—H44A109.1
C21—C20—H20119.6C43ii—C44—H44B109.0
C20—C21—C22119.3 (6)C42—C44—H44B109.3
C20—C21—H21120.2H44A—C44—H44B107.9
C22—C21—H21120.5C7—N1—C9123.8 (4)
C21—C22—C17122.2 (6)C15—N2—C12123.8 (4)
C21—C22—H22118.8C29—N3—C31123.6 (4)
C17—C22—H22119.0C40—N4—C42123.5 (4)
C24—C23—C28120.6 (5)C6—O1—H1A109.4
C24—C23—H23119.8C18—O2—H2A109.6
C28—C23—H23119.6C28—O5—H5109.4
C23—C24—C25120.4 (5)C39—O6—H6109.5
C6—C1—C2—C30.8 (9)C26—C27—C28—O5178.5 (5)
C1—C2—C3—C40.1 (9)C29—C27—C28—O50.1 (8)
C2—C3—C4—C50.4 (9)C26—C27—C28—C231.9 (8)
C3—C4—C5—C61.9 (8)C29—C27—C28—C23179.5 (5)
C3—C4—C5—C7179.7 (5)C26—C27—C29—N3168.5 (5)
C2—C1—C6—O1177.6 (6)C28—C27—C29—N310.1 (8)
C2—C1—C6—C52.2 (9)C26—C27—C29—C3011.7 (8)
C4—C5—C6—O1177.1 (5)C28—C27—C29—C30169.7 (5)
C7—C5—C6—O11.3 (8)N3—C31—C32—C33i175.1 (4)
C4—C5—C6—C12.7 (8)C33—C31—C32—C33i55.4 (6)
C7—C5—C6—C1178.9 (5)N3—C31—C33—C32i177.7 (4)
C4—C5—C7—N1169.6 (5)C32—C31—C33—C32i56.0 (6)
C6—C5—C7—N18.8 (7)C39—C34—C35—C360.7 (9)
C4—C5—C7—C811.7 (8)C34—C35—C36—C370.9 (9)
C6—C5—C7—C8169.9 (5)C35—C36—C37—C381.2 (9)
N1—C9—C10—C11173.8 (4)C36—C37—C38—C390.1 (8)
C14—C9—C10—C1154.9 (5)C36—C37—C38—C40179.1 (6)
C9—C10—C11—C1256.3 (5)C35—C34—C39—O6178.1 (5)
C10—C11—C12—N2176.4 (4)C35—C34—C39—C382.0 (8)
C10—C11—C12—C1355.2 (5)C37—C38—C39—O6178.4 (5)
N2—C12—C13—C14174.1 (4)C40—C38—C39—O60.6 (8)
C11—C12—C13—C1454.3 (5)C37—C38—C39—C341.6 (8)
C12—C13—C14—C955.5 (5)C40—C38—C39—C34179.4 (5)
N1—C9—C14—C13176.0 (4)C39—C38—C40—N49.9 (8)
C10—C9—C14—C1355.0 (5)C37—C38—C40—N4169.1 (5)
N2—C15—C17—C22169.6 (5)C39—C38—C40—C41169.0 (5)
C16—C15—C17—C2211.2 (8)C37—C38—C40—C4112.0 (8)
N2—C15—C17—C189.4 (8)N4—C42—C43—C44ii174.8 (4)
C16—C15—C17—C18169.9 (5)C44—C42—C43—C44ii54.9 (6)
C22—C17—C18—O2177.6 (5)N4—C42—C44—C43ii176.9 (4)
C15—C17—C18—O21.4 (9)C43—C42—C44—C43ii55.4 (6)
C22—C17—C18—C193.2 (8)C5—C7—N1—C9179.2 (4)
C15—C17—C18—C19177.8 (5)C8—C7—N1—C92.2 (8)
O2—C18—C19—C20177.3 (6)C10—C9—N1—C783.5 (6)
C17—C18—C19—C203.4 (9)C14—C9—N1—C7156.0 (5)
C18—C19—C20—C211.5 (10)C17—C15—N2—C12178.9 (5)
C19—C20—C21—C220.6 (9)C16—C15—N2—C121.8 (9)
C20—C21—C22—C170.8 (9)C11—C12—N2—C15155.7 (5)
C18—C17—C22—C211.1 (9)C13—C12—N2—C1583.6 (6)
C15—C17—C22—C21179.9 (5)C27—C29—N3—C31178.6 (5)
C28—C23—C24—C251.4 (8)C30—C29—N3—C311.6 (8)
C23—C24—C25—C260.0 (9)C33—C31—N3—C29158.9 (5)
C24—C25—C26—C270.5 (9)C32—C31—N3—C2980.6 (6)
C25—C26—C27—C280.5 (8)C38—C40—N4—C42178.8 (5)
C25—C26—C27—C29179.1 (5)C41—C40—N4—C422.4 (8)
C24—C23—C28—O5178.0 (5)C44—C42—N4—C40159.2 (5)
C24—C23—C28—C272.4 (8)C43—C42—N4—C4080.0 (6)
Symmetry codes: (i) x, y+1, z; (ii) x+2, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3 and Cg4 are the centroiods of the C17–C22, C1–C6, C34–C39 and C23–C28 benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
O6—H6···N40.821.792.526 (5)147
O5—H5···N30.821.802.523 (5)147
O2—H2A···N20.821.802.516 (5)145
O1—H1A···N10.821.792.520 (5)147
C11—H11A···Cg1iii0.972.643.552 (3)155
C14—H14A···Cg2iv0.972.633.540 (1)156
C33—H33B···Cg3v0.972.623.510 (4)151
C44—H44A···Cg4vi0.972.613.504 (4)152
Symmetry codes: (iii) x+1, y, z; (iv) x+1, y, z+1; (v) x1, y, z; (vi) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3 and Cg4 are the centroiods of the C17–C22, C1–C6, C34–C39 and C23–C28 benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
O6—H6···N40.821.792.526 (5)146.6
O5—H5···N30.821.802.523 (5)147.0
O2—H2A···N20.821.802.516 (5)145.4
O1—H1A···N10.821.792.520 (5)147.2
C11—H11A···Cg1i0.972.643.552 (3)155
C14—H14A···Cg2ii0.972.633.540 (1)156
C33—H33B···Cg3iii0.972.623.510 (4)151
C44—H44A···Cg4iv0.972.613.504 (4)152
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z+1; (iii) x1, y, z; (iv) x+1, y, z.
Acknowledgements top

The authors acknowledge the Department of Chemistry, IIT Madras, for the data collection.

references
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