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

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ISSN: 2056-9890

5-Methyl-1,3-di­phenyl-N-(5-phenyl-1,3,4-thia­diazol-2-yl)-1H-pyrazole-4-carboxamide

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, bDepartment of Physics, Acharya Institute of Technology, Bangalore 560 090, India, cDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysore 570 005, India, and dSER-CAT, APS, Argonne National Laboratory, Argonne, IL-60439, USA
*Correspondence e-mail: mahendra@physics.uni-mysore.ac.in

(Received 7 October 2013; accepted 20 October 2013; online 6 November 2013)

The asymmetric unit of the title compound C25H19N5OS, contains two mol­ecules, A and B. In mol­ecule A, the dihedral angles between the pyrazole ring and the C-bound phenyl group, the N-bound phenyl group and the thia­diazole ring are 32.30 (14), 52.25 (14) and 34.94 (12)°, respectively. The corresponding angles in mol­ecule B are 33.32 (14), 50.67 (15), and 70.30 (12)°, respectively. In the crystal, the A and B mol­ecules are linked by pairs of N—H⋯N hydrogen bonds, generating R22(8) loops. This dimer linkage is reinforced by two C—H⋯O hydrogen bonds and one C—H⋯N hydrogen bond.

Related literature

For the synthesis, see: Shridevi Doddaramappa et al. (2013[Shridevi Doddaramappa, D., Chandra., Mahendra, M. & Lokanatha Rai, K. M. (2013). Chem. Heterocycl. Compd, 49, 698-703.]). For a related structure, see: Chandra et al. (2012[Chandra, , Srikantamurthy, N., Umesha, K. B., Jeyaseelan, S. & Mahendra, M. (2012). Acta Cryst. E68, o1661-o1662.]).

[Scheme 1]

Experimental

Crystal data
  • C25H19N5OS

  • Mr = 437.52

  • Triclinic, [P \overline 1]

  • a = 10.7039 (14) Å

  • b = 12.9341 (17) Å

  • c = 17.478 (2) Å

  • α = 77.343 (2)°

  • β = 82.865 (2)°

  • γ = 70.373 (2)°

  • V = 2220.4 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.17 mm−1

  • T = 273 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • 18748 measured reflections

  • 7768 independent reflections

  • 5447 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.133

  • S = 1.02

  • 7768 reflections

  • 579 parameters

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H21⋯N9B 0.86 2.13 2.916 (3) 151
N8B—H53⋯N4A 0.86 2.07 2.902 (3) 163
C4A—H6B⋯O1A 0.96 2.42 3.107 (3) 128
C29B—H38C⋯N5A 0.96 2.59 3.443 (3) 148
C37B—H46⋯O2B 0.93 2.41 3.184 (3) 141

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

As part of our ongoing studies of pyrazole derivatives (Shridevi Doddaramappa, et al., 2013), the title compound, (I), was prepared and characterized by single-crystal X-ray diffraction. It shows potential anticancer activity against the aurora kinase enzyme: the full results will be reported elsewhere.

In the molecular structure of the title compound (Fig. 1), two molecules (A and B) present in an asymmetric unit have heterocyclic ring moieties exhibiting planar conformation, with their maximum deviations found on ring planes from N1A and C19A are 0.011 (2) Å and 0.005 (2) Å, respectively. The bond lengths are comparable to a related structure (Chandra et al., 2012).

In the molecules A and B, pyrazole moiety makes a dihedral angle of 34.94 (12)°, 76.83 (12)°, 50.67 (13)° and 33.32 (14)° with the phenyl rings (C5A–C10A, C11A–C16A and C30B–C35B, C36B–C41B), respectively. Thiadiazole moiety makes a dihedral angle of 58.01 (13)°, 68.82 (13)°, 79.35 (13)° and 70.30 (12)° with pyrazole and benzene rings, for A and B, respectively.

The crystal structure features C—H···N and C—H···O hydrogen bonds. The packing diagram of the molecules exhibit dimers with stacking feature when viewed down the c axis is shown in Fig. 2.

Related literature top

For the synthesis, see: Shridevi Doddaramappa et al. (2013). For a related structure, see: Chandra et al. (2012).

Experimental top

A solution of pyrazole-4-carboxylic acid (1 mmol) in dry dichloromethane (5 ml) was cooled to 0° C and added ethyl-(N',N'-dimethylamino)propylcarbodiimide hydrochloride (EDC·HCl, 1.2 mmol) and HOBt (1.2 mmol). To this reaction mixture 2-amino-5-phenyl-1,3,4- thiadiazole (1 mmol) was added and stirred at room temperature for 6–8 h. After completion of the reaction, the reaction mixture was extracted with ethyl acetate (2 × 25 ml) and the combined organic phase was washed with brine, dried over anhydrous sodium sulfate. Ethyl acetate was distilled off and the residue thus obtained was purified by recrystallization in EtOH to get the title compound as colourless blocks.

Refinement top

H atoms were placed at idealized positions and allowed to ride on their parent atoms with N–H distance is equal to 0.86 Å and C–H distances in the range of 0.93 to 0.96 Å; Uiso(H) = 1.2–1.5Ueq(carrier atom) for all H atoms.

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: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Perspective diagram of (I) with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the molecule viewed down the 'c' axis.
5-Methyl-1,3-diphenyl-N-(5-phenyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-4-carboxamide top
Crystal data top
C25H19N5OSZ = 4
Mr = 437.52F(000) = 912
Triclinic, P1Dx = 1.309 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.7039 (14) ÅCell parameters from 7768 reflections
b = 12.9341 (17) Åθ = 1.7–25.0°
c = 17.478 (2) ŵ = 0.17 mm1
α = 77.343 (2)°T = 273 K
β = 82.865 (2)°Block, colourless
γ = 70.373 (2)°0.30 × 0.25 × 0.20 mm
V = 2220.4 (5) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
Rint = 0.029
ω and ϕ scansθmax = 25.0°, θmin = 1.7°
18748 measured reflectionsh = 1212
7768 independent reflectionsk = 1515
5447 reflections with I > 2σ(I)l = 2020
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0689P)2]
where P = (Fo2 + 2Fc2)/3
7768 reflections(Δ/σ)max < 0.001
579 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C25H19N5OSγ = 70.373 (2)°
Mr = 437.52V = 2220.4 (5) Å3
Triclinic, P1Z = 4
a = 10.7039 (14) ÅMo Kα radiation
b = 12.9341 (17) ŵ = 0.17 mm1
c = 17.478 (2) ÅT = 273 K
α = 77.343 (2)°0.30 × 0.25 × 0.20 mm
β = 82.865 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
5447 reflections with I > 2σ(I)
18748 measured reflectionsRint = 0.029
7768 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.02Δρmax = 0.20 e Å3
7768 reflectionsΔρmin = 0.19 e Å3
579 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S1A0.77966 (6)0.57443 (5)0.11413 (3)0.0486 (2)
O1A0.52592 (17)0.57319 (15)0.14214 (10)0.0696 (7)
N1A0.24119 (19)0.51919 (16)0.32617 (11)0.0509 (7)
N2A0.3029 (2)0.40699 (16)0.34827 (11)0.0528 (7)
N30.66483 (18)0.44976 (15)0.23031 (10)0.0459 (7)
N4A0.89440 (19)0.40837 (15)0.21844 (10)0.0479 (7)
N5A0.99500 (19)0.44439 (16)0.17621 (11)0.0491 (7)
C1A0.4177 (2)0.38576 (19)0.30667 (13)0.0470 (8)
C2A0.4297 (2)0.48482 (19)0.25603 (13)0.0471 (8)
C3A0.3132 (2)0.5683 (2)0.26966 (13)0.0503 (8)
C4A0.2660 (3)0.6889 (2)0.23304 (15)0.0661 (10)
C5A0.1144 (2)0.5672 (2)0.36390 (13)0.0520 (9)
C6A0.0175 (3)0.5179 (2)0.36746 (15)0.0643 (10)
C7A0.1019 (3)0.5587 (3)0.40836 (18)0.0775 (11)
C8A0.1239 (3)0.6480 (3)0.44329 (18)0.0830 (14)
C9A0.0278 (3)0.6974 (3)0.43862 (17)0.0834 (12)
C10A0.0925 (3)0.6563 (2)0.39990 (16)0.0691 (11)
C11A0.5030 (2)0.26915 (19)0.31428 (14)0.0474 (8)
C12A0.5017 (3)0.1949 (2)0.38506 (15)0.0585 (10)
C13A0.5736 (3)0.0835 (2)0.39154 (18)0.0745 (11)
C14A0.6473 (3)0.0437 (3)0.3285 (2)0.0820 (13)
C15A0.6500 (3)0.1148 (2)0.25814 (19)0.0734 (12)
C16A0.5786 (2)0.2267 (2)0.25111 (15)0.0580 (9)
C17A0.5401 (2)0.5061 (2)0.20410 (14)0.0495 (8)
C18A0.7777 (2)0.46898 (18)0.19296 (12)0.0417 (7)
C19A0.9504 (2)0.53004 (18)0.12061 (13)0.0438 (8)
C20A1.0379 (2)0.58313 (18)0.06721 (12)0.0440 (8)
C21A1.1676 (3)0.5616 (2)0.08475 (15)0.0591 (9)
C22A1.2503 (3)0.6097 (2)0.03406 (16)0.0716 (11)
C23A1.2041 (3)0.6815 (2)0.03456 (16)0.0662 (11)
C24A1.0754 (3)0.7045 (2)0.05280 (14)0.0587 (10)
C25A0.9926 (3)0.65537 (19)0.00233 (13)0.0532 (8)
S2B0.81627 (7)0.14175 (5)0.48058 (3)0.0537 (2)
O2B0.98933 (19)0.01874 (14)0.37824 (9)0.0678 (7)
N6B1.2354 (2)0.11455 (16)0.16431 (11)0.0509 (7)
N7B1.1838 (2)0.04476 (16)0.14004 (11)0.0523 (7)
N8B0.91824 (19)0.20392 (15)0.33307 (10)0.0487 (7)
N9B0.7403 (2)0.33063 (16)0.38824 (10)0.0525 (7)
N10B0.6575 (2)0.34209 (16)0.45472 (11)0.0539 (7)
C26B1.0909 (2)0.02892 (18)0.19482 (13)0.0458 (8)
C27B1.0831 (2)0.08937 (18)0.25492 (12)0.0447 (8)
C28B1.1771 (2)0.14337 (19)0.23367 (13)0.0482 (8)
C29B1.2217 (3)0.2113 (2)0.27610 (15)0.0650 (10)
C30B1.3427 (3)0.1439 (2)0.11818 (14)0.0557 (9)
C31B1.4489 (3)0.0614 (3)0.09391 (16)0.0724 (11)
C32B1.5488 (3)0.0908 (3)0.04525 (18)0.0907 (14)
C33B1.5409 (4)0.2004 (4)0.02129 (18)0.0925 (16)
C34B1.4365 (4)0.2816 (3)0.04664 (18)0.0860 (16)
C35B1.3356 (3)0.2547 (2)0.09550 (16)0.0695 (11)
C36B1.0101 (2)0.03876 (18)0.18330 (14)0.0481 (8)
C37B0.9612 (3)0.10363 (19)0.24491 (15)0.0565 (9)
C38B0.8893 (3)0.1677 (2)0.23079 (18)0.0686 (11)
C39B0.8640 (3)0.1672 (2)0.1564 (2)0.0827 (12)
C40B0.9107 (4)0.1026 (3)0.09536 (19)0.1041 (18)
C41B0.9826 (3)0.0384 (3)0.10839 (16)0.0852 (13)
C42B0.9947 (2)0.09754 (19)0.32675 (13)0.0474 (8)
C43B0.8266 (2)0.23077 (19)0.39388 (12)0.0450 (8)
C44B0.6846 (2)0.25151 (19)0.50738 (13)0.0484 (8)
C45B0.6065 (3)0.2402 (2)0.58222 (13)0.0524 (9)
C46B0.6323 (3)0.1389 (2)0.63370 (15)0.0765 (11)
C47B0.5571 (4)0.1274 (3)0.70274 (17)0.0940 (14)
C48B0.4564 (3)0.2173 (3)0.72158 (17)0.0841 (13)
C49B0.4298 (3)0.3172 (3)0.67167 (17)0.0773 (11)
C50B0.5042 (3)0.3306 (2)0.60176 (15)0.0676 (11)
H6A0.178400.707900.215200.0990*
H6B0.325200.703700.189200.0990*
H6C0.263800.733100.271000.0990*
H80.032300.457800.342600.0770*
H90.167400.525200.412000.0930*
H100.204600.675500.470500.1000*
H110.044200.759200.461800.1000*
H120.158700.688600.398100.0830*
H140.451600.221000.428400.0700*
H150.572200.034900.439300.0890*
H160.695600.031800.333400.0980*
H170.700100.087600.215100.0880*
H180.581000.274600.203200.0700*
H210.672800.399600.272400.0550*
H281.199300.514000.131300.0710*
H291.337800.593800.046200.0860*
H301.260100.714400.068500.0790*
H311.044000.753000.099100.0700*
H320.905600.670800.015000.0640*
H38A1.316800.190900.271000.0970*
H38B1.193400.197800.330600.0970*
H38C1.183600.289200.254100.0970*
H401.453800.013300.109900.0870*
H411.621900.035400.028800.1090*
H421.607300.219500.012500.1110*
H431.432800.356000.031000.1030*
H441.264000.310400.112800.0840*
H460.976700.104300.296200.0680*
H470.857700.211800.272800.0820*
H480.815300.210500.147500.0990*
H490.893800.101800.044300.1250*
H501.013100.005900.065900.1020*
H530.928100.257700.296600.0580*
H600.701600.077600.621500.0920*
H610.574900.058500.736600.1130*
H620.406100.210000.768600.1010*
H630.360300.377900.684600.0930*
H640.485300.399900.568200.0810*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0405 (4)0.0475 (3)0.0524 (4)0.0139 (3)0.0025 (3)0.0014 (3)
O1A0.0463 (11)0.0901 (13)0.0533 (10)0.0160 (10)0.0047 (8)0.0176 (10)
N1A0.0368 (12)0.0560 (12)0.0572 (12)0.0135 (10)0.0044 (10)0.0114 (10)
N2A0.0436 (13)0.0564 (13)0.0590 (12)0.0181 (10)0.0026 (10)0.0117 (10)
N30.0370 (12)0.0490 (11)0.0457 (11)0.0141 (9)0.0006 (9)0.0031 (9)
N4A0.0367 (12)0.0549 (12)0.0480 (11)0.0161 (10)0.0002 (9)0.0001 (9)
N5A0.0383 (12)0.0568 (12)0.0491 (11)0.0169 (10)0.0009 (9)0.0019 (9)
C1A0.0371 (14)0.0562 (15)0.0488 (13)0.0160 (12)0.0014 (11)0.0127 (11)
C2A0.0359 (14)0.0560 (14)0.0469 (13)0.0129 (12)0.0020 (11)0.0073 (11)
C3A0.0382 (15)0.0602 (15)0.0510 (14)0.0165 (13)0.0003 (11)0.0078 (12)
C4A0.0471 (17)0.0640 (17)0.0733 (17)0.0092 (13)0.0051 (13)0.0028 (14)
C5A0.0379 (15)0.0636 (16)0.0512 (14)0.0147 (13)0.0033 (11)0.0098 (12)
C6A0.0460 (17)0.0695 (17)0.0750 (18)0.0179 (14)0.0012 (14)0.0122 (14)
C7A0.0440 (18)0.088 (2)0.091 (2)0.0201 (16)0.0068 (16)0.0051 (18)
C8A0.052 (2)0.102 (3)0.078 (2)0.0100 (19)0.0187 (16)0.0174 (19)
C9A0.073 (2)0.096 (2)0.080 (2)0.0194 (19)0.0174 (18)0.0381 (18)
C10A0.0551 (19)0.086 (2)0.0730 (18)0.0249 (16)0.0054 (15)0.0305 (16)
C11A0.0368 (14)0.0545 (14)0.0565 (14)0.0194 (12)0.0008 (11)0.0151 (12)
C12A0.0505 (17)0.0624 (17)0.0636 (16)0.0209 (14)0.0003 (13)0.0111 (13)
C13A0.070 (2)0.0608 (18)0.085 (2)0.0195 (16)0.0054 (17)0.0006 (16)
C14A0.068 (2)0.0597 (18)0.113 (3)0.0102 (16)0.000 (2)0.0242 (19)
C15A0.063 (2)0.073 (2)0.087 (2)0.0178 (16)0.0095 (16)0.0350 (17)
C16A0.0479 (16)0.0666 (17)0.0635 (16)0.0202 (14)0.0009 (13)0.0197 (13)
C17A0.0414 (15)0.0566 (14)0.0475 (14)0.0156 (12)0.0015 (11)0.0040 (12)
C18A0.0385 (14)0.0443 (12)0.0424 (12)0.0143 (11)0.0008 (10)0.0083 (10)
C19A0.0433 (14)0.0446 (13)0.0457 (13)0.0168 (11)0.0011 (11)0.0094 (11)
C20A0.0438 (15)0.0434 (12)0.0496 (13)0.0196 (11)0.0011 (11)0.0117 (10)
C21A0.0543 (17)0.0670 (16)0.0601 (16)0.0306 (14)0.0089 (13)0.0003 (13)
C22A0.0560 (19)0.091 (2)0.0782 (19)0.0424 (17)0.0053 (15)0.0063 (16)
C23A0.069 (2)0.0742 (18)0.0649 (17)0.0431 (16)0.0078 (15)0.0071 (14)
C24A0.069 (2)0.0554 (15)0.0523 (15)0.0265 (14)0.0017 (13)0.0018 (12)
C25A0.0500 (16)0.0549 (14)0.0536 (14)0.0189 (13)0.0047 (12)0.0034 (12)
S2B0.0580 (4)0.0537 (4)0.0400 (3)0.0105 (3)0.0003 (3)0.0026 (3)
O2B0.0840 (14)0.0523 (10)0.0497 (10)0.0100 (10)0.0055 (9)0.0026 (8)
N6B0.0495 (13)0.0572 (12)0.0518 (12)0.0250 (11)0.0016 (10)0.0118 (10)
N7B0.0555 (14)0.0553 (12)0.0515 (12)0.0261 (11)0.0042 (10)0.0120 (10)
N8B0.0518 (13)0.0473 (11)0.0406 (10)0.0137 (10)0.0008 (9)0.0002 (9)
N9B0.0555 (14)0.0518 (12)0.0420 (11)0.0106 (11)0.0018 (10)0.0047 (9)
N10B0.0561 (14)0.0562 (12)0.0444 (11)0.0126 (11)0.0021 (10)0.0105 (10)
C26B0.0481 (15)0.0430 (13)0.0449 (13)0.0149 (11)0.0002 (11)0.0063 (10)
C27B0.0438 (15)0.0433 (12)0.0425 (12)0.0098 (11)0.0035 (11)0.0046 (10)
C28B0.0430 (15)0.0532 (14)0.0471 (13)0.0141 (12)0.0046 (11)0.0078 (11)
C29B0.0605 (18)0.0777 (18)0.0663 (17)0.0273 (15)0.0106 (14)0.0209 (14)
C30B0.0530 (17)0.0725 (18)0.0487 (14)0.0323 (15)0.0037 (12)0.0058 (13)
C31B0.070 (2)0.085 (2)0.0674 (18)0.0339 (18)0.0174 (15)0.0222 (16)
C32B0.073 (2)0.131 (3)0.083 (2)0.050 (2)0.0238 (18)0.039 (2)
C33B0.094 (3)0.140 (3)0.072 (2)0.082 (3)0.0101 (19)0.016 (2)
C34B0.094 (3)0.103 (3)0.077 (2)0.065 (2)0.012 (2)0.0075 (19)
C35B0.065 (2)0.0750 (19)0.0731 (18)0.0354 (16)0.0157 (15)0.0036 (15)
C36B0.0483 (15)0.0417 (13)0.0556 (14)0.0168 (11)0.0073 (12)0.0134 (11)
C37B0.0570 (17)0.0470 (14)0.0613 (15)0.0164 (13)0.0075 (13)0.0082 (12)
C38B0.0621 (19)0.0520 (16)0.091 (2)0.0262 (14)0.0218 (16)0.0141 (15)
C39B0.092 (2)0.081 (2)0.102 (2)0.0551 (19)0.029 (2)0.0482 (19)
C40B0.148 (4)0.136 (3)0.076 (2)0.100 (3)0.022 (2)0.047 (2)
C41B0.127 (3)0.106 (2)0.0583 (17)0.085 (2)0.0142 (17)0.0237 (16)
C42B0.0473 (15)0.0507 (14)0.0413 (13)0.0129 (12)0.0072 (11)0.0043 (11)
C43B0.0450 (15)0.0500 (14)0.0387 (12)0.0142 (12)0.0022 (11)0.0073 (10)
C44B0.0515 (16)0.0536 (14)0.0397 (12)0.0157 (12)0.0042 (11)0.0090 (11)
C45B0.0513 (16)0.0632 (16)0.0434 (13)0.0184 (13)0.0024 (12)0.0116 (12)
C46B0.081 (2)0.0732 (19)0.0565 (17)0.0116 (17)0.0165 (15)0.0057 (14)
C47B0.100 (3)0.097 (2)0.0641 (19)0.025 (2)0.0201 (19)0.0038 (17)
C48B0.071 (2)0.123 (3)0.0550 (17)0.034 (2)0.0165 (16)0.0164 (19)
C49B0.057 (2)0.103 (2)0.0642 (18)0.0075 (18)0.0030 (15)0.0323 (18)
C50B0.065 (2)0.0756 (19)0.0543 (16)0.0101 (16)0.0016 (14)0.0168 (14)
Geometric parameters (Å, º) top
S1A—C18A1.717 (2)C8A—H100.9300
S1A—C19A1.732 (2)C9A—H110.9300
S2B—C43B1.707 (2)C10A—H120.9300
S2B—C44B1.733 (2)C12A—H140.9300
O1A—C17A1.220 (3)C13A—H150.9300
O2B—C42B1.215 (3)C14A—H160.9300
N1A—C5A1.433 (3)C15A—H170.9300
N1A—N2A1.366 (3)C16A—H180.9300
N1A—C3A1.356 (3)C21A—H280.9300
N2A—C1A1.324 (3)C22A—H290.9300
N3—C17A1.370 (3)C23A—H300.9300
N3—C18A1.372 (3)C24A—H310.9300
N4A—C18A1.304 (3)C25A—H320.9300
N4A—N5A1.382 (3)C26B—C27B1.420 (3)
N5A—C19A1.299 (3)C26B—C36B1.478 (3)
N3—H210.8600C27B—C42B1.476 (3)
N6B—C28B1.361 (3)C27B—C28B1.380 (3)
N6B—N7B1.364 (3)C28B—C29B1.485 (4)
N6B—C30B1.429 (4)C30B—C31B1.369 (4)
N7B—C26B1.327 (3)C30B—C35B1.379 (4)
N8B—C42B1.365 (3)C31B—C32B1.385 (5)
N8B—C43B1.373 (3)C32B—C33B1.364 (6)
N9B—C43B1.303 (3)C33B—C34B1.357 (6)
N9B—N10B1.374 (3)C34B—C35B1.382 (5)
N10B—C44B1.292 (3)C36B—C41B1.376 (4)
N8B—H530.8600C36B—C37B1.377 (4)
C1A—C2A1.424 (3)C37B—C38B1.380 (4)
C1A—C11A1.464 (3)C38B—C39B1.359 (5)
C2A—C17A1.462 (3)C39B—C40B1.358 (5)
C2A—C3A1.383 (3)C40B—C41B1.375 (5)
C3A—C4A1.487 (3)C44B—C45B1.469 (3)
C5A—C6A1.377 (4)C45B—C50B1.380 (4)
C5A—C10A1.371 (4)C45B—C46B1.380 (3)
C6A—C7A1.381 (5)C46B—C47B1.374 (4)
C7A—C8A1.361 (5)C47B—C48B1.364 (5)
C8A—C9A1.368 (5)C48B—C49B1.354 (5)
C9A—C10A1.371 (5)C49B—C50B1.384 (4)
C11A—C12A1.392 (3)C29B—H38A0.9600
C11A—C16A1.386 (3)C29B—H38B0.9600
C12A—C13A1.374 (4)C29B—H38C0.9600
C13A—C14A1.364 (5)C31B—H400.9300
C14A—C15A1.368 (5)C32B—H410.9300
C15A—C16A1.377 (4)C33B—H420.9300
C19A—C20A1.468 (3)C34B—H430.9300
C20A—C25A1.389 (3)C35B—H440.9300
C20A—C21A1.381 (4)C37B—H460.9300
C21A—C22A1.375 (4)C38B—H470.9300
C22A—C23A1.377 (4)C39B—H480.9300
C23A—C24A1.371 (5)C40B—H490.9300
C24A—C25A1.381 (4)C41B—H500.9300
C4A—H6C0.9600C46B—H600.9300
C4A—H6B0.9600C47B—H610.9300
C4A—H6A0.9600C48B—H620.9300
C6A—H80.9300C49B—H630.9300
C7A—H90.9300C50B—H640.9300
S1A···O1A2.704 (2)C23A···H42vii3.0000
S1A···N5A2.557 (2)C26B···H31i2.9400
S1A···C34Bi3.626 (4)C27B···H463.0000
S2B···O2Bii3.2950 (19)C28B···H442.9800
S2B···N10B2.555 (2)C28B···H61ii3.0400
S2B···O2B2.7580 (19)C28B···H532.8000
S2B···C13A3.545 (3)C29B···H442.9100
S1A···H48iii3.1100C29B···H532.9900
S1A···H322.7600C30B···H38A2.8300
S2B···H602.7000C31B···H61ii3.0500
O1A···S1A2.704 (2)C31B···H41ix2.9900
O1A···C4A3.107 (3)C32B···H40ix3.1000
O2B···S2B2.7580 (19)C33B···H30vii2.9700
O2B···S2Bii3.2950 (19)C35B···H32i2.8700
O2B···C37B3.184 (3)C35B···H38C3.0800
O1A···H6B2.4200C35B···H38A3.0000
O1A···H29iv2.6900C37B···H163.0200
O2B···H462.4100C37B···H173.0600
N2A···C29Biv3.450 (3)C37B···H6Ax2.8400
N3···C11A3.346 (3)C38B···H162.9400
N3···C16A3.249 (3)C38B···H6Ax2.9800
N3···N9B2.916 (3)C40B···H50xi2.9600
N4A···S1A2.5522 (19)C41B···H50xi2.9800
N4A···N8B2.902 (3)C42B···H462.8500
N5A···S1A2.557 (2)C42B···H38B2.8500
N5A···C29B3.443 (3)C43B···H212.9000
N8B···N4A2.902 (3)C44B···H12v2.8700
N8B···C29B3.304 (4)C45B···H12v3.0300
N9B···N32.916 (3)H6A···C38Bvi2.9800
N9B···S2B2.549 (2)H6A···C5A2.9800
N9B···C11A3.373 (3)H6A···C37Bvi2.8400
N10B···S2B2.555 (2)H6B···O1A2.4200
N10B···C12A3.397 (4)H6B···C17A2.7900
N2A···H142.6100H6C···C10A2.9400
N2A···H82.7600H6C···H122.4100
N3···H63v2.8600H8···N2A2.7600
N3···H182.8500H12···C44Bv2.8700
N4A···H532.0700H12···C45Bv3.0300
N5A···H282.6100H12···H6C2.4100
N5A···H38C2.5900H12···C3A3.0100
N6B···H61ii2.8700H12···C4A2.9700
N7B···H31i2.9400H14···N2A2.6100
N7B···H402.7400H16···C38B2.9400
N7B···H502.6000H16···C37B3.0200
N8B···H38B2.9100H17···C37B3.0600
N9B···H212.1300H18···C17A2.8800
N10B···H642.5900H18···N32.8500
C4A···C10A3.282 (4)H18···C2A2.9400
C4A···C37Bvi3.476 (4)H21···C1A2.7800
C4A···O1A3.107 (3)H21···C11A2.8100
C10A···C4A3.282 (4)H21···N9B2.1300
C11A···N9B3.373 (3)H21···C43B2.9000
C11A···N33.346 (3)H21···C16A2.8500
C11A···C29Biv3.508 (4)H28···N5A2.6100
C12A···N10B3.397 (4)H28···H442.5700
C12A···C44B3.410 (4)H29···O1Aviii2.6900
C13A···S2B3.545 (3)H30···C33Bvii2.9700
C14A···C37B3.571 (5)H30···H42vii2.5700
C15A···C37B3.592 (4)H31···N7Bi2.9400
C16A···C17A3.419 (4)H31···C26Bi2.9400
C16A···N33.249 (3)H32···H44i2.5600
C17A···C16A3.419 (4)H32···S1A2.7600
C17A···C49Bv3.590 (4)H32···C35Bi2.8700
C18A···C24Ai3.548 (3)H38A···C11Aviii2.7600
C19A···C24Ai3.592 (3)H38A···C12Aviii3.0000
C19A···C25Ai3.358 (3)H38A···C16Aviii2.9600
C23A···C33Bvii3.599 (6)H38A···C30B2.8300
C24A···C18Ai3.548 (3)H38A···C35B3.0000
C24A···C19Ai3.592 (3)H38B···N8B2.9100
C25A···C19Ai3.358 (3)H38B···C42B2.8500
C29B···C35B3.239 (4)H38C···N5A2.5900
C29B···N2Aviii3.450 (3)H38C···C35B3.0800
C29B···N5A3.443 (3)H38C···H442.5000
C29B···C11Aviii3.508 (4)H40···N7B2.7400
C29B···N8B3.304 (4)H40···C32Bix3.1000
C31B···C32Bix3.441 (5)H41···C31Bix2.9900
C32B···C31Bix3.441 (5)H42···C22Avii3.0200
C32B···C32Bix3.577 (5)H42···C23Avii3.0000
C33B···C23Avii3.599 (6)H42···H30vii2.5700
C34B···S1Ai3.626 (4)H44···C21A3.0100
C35B···C29B3.239 (4)H44···C28B2.9800
C37B···C15A3.592 (4)H44···C29B2.9100
C37B···C14A3.571 (5)H44···H282.5700
C37B···C4Ax3.476 (4)H44···H38C2.5000
C37B···O2B3.184 (3)H44···H32i2.5600
C37B···C42B3.366 (4)H46···O2B2.4100
C42B···C37B3.366 (4)H46···C27B3.0000
C44B···C12A3.410 (4)H46···C42B2.8500
C49B···C17Av3.590 (4)H48···S1Axii3.1100
C1A···H212.7800H49···H50xi2.3600
C2A···H182.9400H50···N7B2.6000
C3A···H123.0100H50···C40Bxi2.9600
C4A···H122.9700H50···C41Bxi2.9800
C5A···H6A2.9800H50···H49xi2.3600
C10A···H6C2.9400H50···H50xi2.4000
C11A···H212.8100H53···N4A2.0700
C11A···H38Aiv2.7600H53···C18A2.9900
C12A···H38Aiv3.0000H53···C28B2.8000
C16A···H38Aiv2.9600H53···C29B2.9900
C16A···H212.8500H60···S2B2.7000
C17A···H6B2.7900H61···N6Bii2.8700
C17A···H182.8800H61···C28Bii3.0400
C18A···H532.9900H61···C31Bii3.0500
C21A···H443.0100H63···N3v2.8600
C22A···H42vii3.0200H64···N10B2.5900
C18A—S1A—C19A86.67 (11)C20A—C21A—H28120.00
C43B—S2B—C44B86.22 (11)C22A—C21A—H28120.00
N2A—N1A—C3A112.4 (2)C21A—C22A—H29120.00
N2A—N1A—C5A117.77 (19)C23A—C22A—H29120.00
C3A—N1A—C5A129.9 (2)C22A—C23A—H30120.00
N1A—N2A—C1A105.28 (19)C24A—C23A—H30120.00
C17A—N3—C18A123.55 (19)C23A—C24A—H31120.00
N5A—N4A—C18A112.18 (18)C25A—C24A—H31120.00
N4A—N5A—C19A112.3 (2)C20A—C25A—H32120.00
C17A—N3—H21118.00C24A—C25A—H32120.00
C18A—N3—H21118.00N7B—C26B—C27B110.2 (2)
N7B—N6B—C28B112.5 (2)N7B—C26B—C36B118.8 (2)
C28B—N6B—C30B128.8 (2)C27B—C26B—C36B130.9 (2)
N7B—N6B—C30B118.65 (19)C26B—C27B—C28B106.27 (19)
N6B—N7B—C26B105.50 (18)C28B—C27B—C42B124.3 (2)
C42B—N8B—C43B124.31 (19)C26B—C27B—C42B129.5 (2)
N10B—N9B—C43B111.92 (18)N6B—C28B—C29B123.4 (2)
N9B—N10B—C44B112.3 (2)N6B—C28B—C27B105.5 (2)
C43B—N8B—H53118.00C27B—C28B—C29B130.9 (2)
C42B—N8B—H53118.00N6B—C30B—C35B120.0 (2)
N2A—C1A—C2A110.8 (2)N6B—C30B—C31B119.2 (2)
N2A—C1A—C11A117.8 (2)C31B—C30B—C35B120.8 (3)
C2A—C1A—C11A131.2 (2)C30B—C31B—C32B119.0 (3)
C1A—C2A—C17A131.4 (2)C31B—C32B—C33B120.5 (4)
C3A—C2A—C17A123.1 (2)C32B—C33B—C34B120.2 (4)
C1A—C2A—C3A105.3 (2)C33B—C34B—C35B120.6 (3)
N1A—C3A—C2A106.2 (2)C30B—C35B—C34B119.0 (3)
C2A—C3A—C4A130.6 (2)C37B—C36B—C41B118.0 (2)
N1A—C3A—C4A123.2 (2)C26B—C36B—C37B122.6 (2)
N1A—C5A—C10A120.7 (2)C26B—C36B—C41B119.4 (2)
N1A—C5A—C6A118.7 (2)C36B—C37B—C38B120.3 (2)
C6A—C5A—C10A120.5 (2)C37B—C38B—C39B121.0 (3)
C5A—C6A—C7A119.2 (3)C38B—C39B—C40B119.1 (3)
C6A—C7A—C8A120.1 (3)C39B—C40B—C41B120.6 (3)
C7A—C8A—C9A120.3 (3)C36B—C41B—C40B121.0 (3)
C8A—C9A—C10A120.4 (3)O2B—C42B—C27B124.8 (2)
C5A—C10A—C9A119.4 (3)O2B—C42B—N8B120.8 (2)
C1A—C11A—C12A119.9 (2)N8B—C42B—C27B114.41 (19)
C1A—C11A—C16A122.1 (2)N8B—C43B—N9B120.20 (19)
C12A—C11A—C16A117.8 (2)S2B—C43B—N9B115.12 (16)
C11A—C12A—C13A120.7 (2)S2B—C43B—N8B124.67 (17)
C12A—C13A—C14A120.5 (3)S2B—C44B—N10B114.43 (17)
C13A—C14A—C15A120.1 (3)S2B—C44B—C45B122.50 (18)
C14A—C15A—C16A119.9 (3)N10B—C44B—C45B123.0 (2)
C11A—C16A—C15A121.1 (2)C44B—C45B—C46B120.8 (2)
O1A—C17A—C2A123.8 (2)C46B—C45B—C50B118.7 (2)
N3—C17A—C2A116.2 (2)C44B—C45B—C50B120.5 (2)
O1A—C17A—N3119.9 (2)C45B—C46B—C47B120.9 (3)
S1A—C18A—N4A114.62 (17)C46B—C47B—C48B119.9 (3)
S1A—C18A—N3124.69 (17)C47B—C48B—C49B119.9 (3)
N3—C18A—N4A120.63 (19)C48B—C49B—C50B121.2 (3)
S1A—C19A—C20A123.10 (17)C45B—C50B—C49B119.4 (3)
N5A—C19A—C20A122.7 (2)C28B—C29B—H38A109.00
S1A—C19A—N5A114.24 (18)C28B—C29B—H38B109.00
C21A—C20A—C25A118.5 (2)C28B—C29B—H38C109.00
C19A—C20A—C25A120.8 (2)H38A—C29B—H38B110.00
C19A—C20A—C21A120.7 (2)H38A—C29B—H38C109.00
C20A—C21A—C22A120.7 (2)H38B—C29B—H38C109.00
C21A—C22A—C23A120.3 (3)C30B—C31B—H40120.00
C22A—C23A—C24A119.9 (3)C32B—C31B—H40121.00
C23A—C24A—C25A119.9 (2)C31B—C32B—H41120.00
C20A—C25A—C24A120.7 (3)C33B—C32B—H41120.00
C3A—C4A—H6B110.00C32B—C33B—H42120.00
C3A—C4A—H6A110.00C34B—C33B—H42120.00
H6A—C4A—H6C109.00C33B—C34B—H43120.00
C3A—C4A—H6C110.00C35B—C34B—H43120.00
H6B—C4A—H6C109.00C30B—C35B—H44120.00
H6A—C4A—H6B109.00C34B—C35B—H44121.00
C5A—C6A—H8120.00C36B—C37B—H46120.00
C7A—C6A—H8120.00C38B—C37B—H46120.00
C6A—C7A—H9120.00C37B—C38B—H47119.00
C8A—C7A—H9120.00C39B—C38B—H47120.00
C9A—C8A—H10120.00C38B—C39B—H48120.00
C7A—C8A—H10120.00C40B—C39B—H48121.00
C10A—C9A—H11120.00C39B—C40B—H49120.00
C8A—C9A—H11120.00C41B—C40B—H49120.00
C9A—C10A—H12120.00C36B—C41B—H50120.00
C5A—C10A—H12120.00C40B—C41B—H50119.00
C11A—C12A—H14120.00C45B—C46B—H60120.00
C13A—C12A—H14120.00C47B—C46B—H60120.00
C14A—C13A—H15120.00C46B—C47B—H61120.00
C12A—C13A—H15120.00C48B—C47B—H61120.00
C13A—C14A—H16120.00C47B—C48B—H62120.00
C15A—C14A—H16120.00C49B—C48B—H62120.00
C14A—C15A—H17120.00C48B—C49B—H63119.00
C16A—C15A—H17120.00C50B—C49B—H63119.00
C11A—C16A—H18119.00C45B—C50B—H64120.00
C15A—C16A—H18120.00C49B—C50B—H64120.00
C19A—S1A—C18A—N3176.2 (2)C10A—C5A—C6A—C7A0.5 (4)
C19A—S1A—C18A—N4A0.97 (18)C5A—C6A—C7A—C8A1.3 (4)
C18A—S1A—C19A—N5A0.81 (18)C6A—C7A—C8A—C9A0.5 (5)
C18A—S1A—C19A—C20A179.8 (2)C7A—C8A—C9A—C10A1.2 (5)
C44B—S2B—C43B—N9B0.46 (19)C8A—C9A—C10A—C5A1.9 (4)
C43B—S2B—C44B—N10B0.4 (2)C1A—C11A—C12A—C13A175.2 (3)
C44B—S2B—C43B—N8B179.6 (2)C12A—C11A—C16A—C15A0.0 (4)
C43B—S2B—C44B—C45B176.8 (2)C16A—C11A—C12A—C13A0.2 (4)
C3A—N1A—N2A—C1A1.9 (3)C1A—C11A—C16A—C15A174.9 (2)
C5A—N1A—N2A—C1A178.3 (2)C11A—C12A—C13A—C14A0.2 (5)
N2A—N1A—C5A—C6A50.4 (3)C12A—C13A—C14A—C15A0.0 (5)
N2A—N1A—C5A—C10A125.7 (2)C13A—C14A—C15A—C16A0.2 (5)
C3A—N1A—C5A—C6A129.4 (3)C14A—C15A—C16A—C11A0.2 (4)
C3A—N1A—C5A—C10A54.5 (3)S1A—C19A—C20A—C25A14.8 (3)
N2A—N1A—C3A—C4A177.5 (2)N5A—C19A—C20A—C21A15.3 (3)
C5A—N1A—C3A—C2A178.2 (2)S1A—C19A—C20A—C21A165.70 (19)
N2A—N1A—C3A—C2A2.1 (3)N5A—C19A—C20A—C25A164.1 (2)
C5A—N1A—C3A—C4A2.3 (4)C21A—C20A—C25A—C24A0.0 (3)
N1A—N2A—C1A—C2A1.0 (3)C25A—C20A—C21A—C22A0.7 (4)
N1A—N2A—C1A—C11A176.1 (2)C19A—C20A—C25A—C24A179.5 (2)
C18A—N3—C17A—O1A4.2 (4)C19A—C20A—C21A—C22A178.8 (2)
C18A—N3—C17A—C2A172.8 (2)C20A—C21A—C22A—C23A1.0 (4)
C17A—N3—C18A—S1A6.7 (3)C21A—C22A—C23A—C24A0.5 (4)
C17A—N3—C18A—N4A176.3 (2)C22A—C23A—C24A—C25A0.1 (4)
N5A—N4A—C18A—S1A0.9 (2)C23A—C24A—C25A—C20A0.4 (4)
N5A—N4A—C18A—N3176.42 (19)N7B—C26B—C27B—C28B0.0 (3)
C18A—N4A—N5A—C19A0.3 (3)N7B—C26B—C27B—C42B179.6 (2)
N4A—N5A—C19A—S1A0.5 (2)C36B—C26B—C27B—C28B176.1 (2)
N4A—N5A—C19A—C20A179.52 (19)C36B—C26B—C27B—C42B3.5 (4)
C28B—N6B—N7B—C26B0.1 (3)N7B—C26B—C36B—C37B148.1 (2)
N7B—N6B—C28B—C29B175.1 (2)N7B—C26B—C36B—C41B31.5 (3)
C30B—N6B—N7B—C26B177.6 (2)C27B—C26B—C36B—C37B36.2 (4)
N7B—N6B—C28B—C27B0.1 (3)C27B—C26B—C36B—C41B144.3 (3)
N7B—N6B—C30B—C31B48.0 (3)C26B—C27B—C28B—N6B0.1 (3)
N7B—N6B—C30B—C35B129.0 (3)C26B—C27B—C28B—C29B174.7 (2)
C28B—N6B—C30B—C31B129.1 (3)C42B—C27B—C28B—N6B179.6 (2)
C28B—N6B—C30B—C35B54.0 (4)C42B—C27B—C28B—C29B5.7 (4)
C30B—N6B—C28B—C27B177.3 (2)C26B—C27B—C42B—O2B59.4 (4)
C30B—N6B—C28B—C29B2.1 (4)C26B—C27B—C42B—N8B122.2 (3)
N6B—N7B—C26B—C27B0.0 (3)C28B—C27B—C42B—O2B121.1 (3)
N6B—N7B—C26B—C36B176.5 (2)C28B—C27B—C42B—N8B57.4 (3)
C42B—N8B—C43B—S2B14.2 (3)N6B—C30B—C31B—C32B176.1 (3)
C43B—N8B—C42B—C27B178.2 (2)C35B—C30B—C31B—C32B0.8 (4)
C42B—N8B—C43B—N9B166.7 (2)N6B—C30B—C35B—C34B175.8 (3)
C43B—N8B—C42B—O2B3.3 (4)C31B—C30B—C35B—C34B1.1 (4)
N10B—N9B—C43B—S2B0.5 (3)C30B—C31B—C32B—C33B0.6 (5)
N10B—N9B—C43B—N8B179.7 (2)C31B—C32B—C33B—C34B1.7 (5)
C43B—N9B—N10B—C44B0.2 (3)C32B—C33B—C34B—C35B1.4 (6)
N9B—N10B—C44B—S2B0.2 (3)C33B—C34B—C35B—C30B0.1 (5)
N9B—N10B—C44B—C45B176.9 (2)C26B—C36B—C37B—C38B178.2 (2)
N2A—C1A—C2A—C3A0.2 (3)C41B—C36B—C37B—C38B1.3 (4)
N2A—C1A—C2A—C17A174.5 (2)C26B—C36B—C41B—C40B178.3 (3)
C11A—C1A—C2A—C3A174.1 (2)C37B—C36B—C41B—C40B1.3 (5)
C2A—C1A—C11A—C12A154.8 (3)C36B—C37B—C38B—C39B0.8 (4)
C2A—C1A—C11A—C16A30.5 (4)C37B—C38B—C39B—C40B0.1 (5)
N2A—C1A—C11A—C16A143.4 (2)C38B—C39B—C40B—C41B0.0 (5)
C11A—C1A—C2A—C17A11.2 (4)C39B—C40B—C41B—C36B0.6 (6)
N2A—C1A—C11A—C12A31.3 (3)S2B—C44B—C45B—C46B2.4 (4)
C1A—C2A—C3A—C4A178.2 (2)S2B—C44B—C45B—C50B178.7 (2)
C1A—C2A—C17A—O1A147.2 (3)N10B—C44B—C45B—C46B174.4 (3)
C17A—C2A—C3A—N1A174.0 (2)N10B—C44B—C45B—C50B4.5 (4)
C17A—C2A—C3A—C4A6.6 (4)C44B—C45B—C46B—C47B178.2 (3)
C1A—C2A—C3A—N1A1.3 (2)C50B—C45B—C46B—C47B0.7 (5)
C3A—C2A—C17A—O1A38.9 (4)C44B—C45B—C50B—C49B178.3 (3)
C3A—C2A—C17A—N3138.0 (2)C46B—C45B—C50B—C49B0.6 (5)
C1A—C2A—C17A—N335.9 (4)C45B—C46B—C47B—C48B0.8 (5)
N1A—C5A—C6A—C7A175.6 (2)C46B—C47B—C48B—C49B0.9 (6)
N1A—C5A—C10A—C9A177.1 (2)C47B—C48B—C49B—C50B0.8 (5)
C6A—C5A—C10A—C9A1.0 (4)C48B—C49B—C50B—C45B0.7 (5)
Symmetry codes: (i) x+2, y+1, z; (ii) x+2, y, z+1; (iii) x, y+1, z; (iv) x1, y, z; (v) x+1, y+1, z+1; (vi) x1, y+1, z; (vii) x+3, y+1, z; (viii) x+1, y, z; (ix) x+3, y, z; (x) x+1, y1, z; (xi) x+2, y, z; (xii) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H21···N9B0.862.132.916 (3)151
N8B—H53···N4A0.862.072.902 (3)163
C4A—H6B···O1A0.962.423.107 (3)128
C29B—H38C···N5A0.962.593.443 (3)148
C37B—H46···O2B0.932.413.184 (3)141
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H21···N9B0.862.132.916 (3)151
N8B—H53···N4A0.862.072.902 (3)163
C4A—H6B···O1A0.962.423.107 (3)128
C29B—H38C···N5A0.962.593.443 (3)148
C37B—H46···O2B0.932.413.184 (3)141
 

Acknowledgements

Chandra would like to thank the University of Mysore for the award of an RFSMS fellowship under the head DV5/Physics/389/RFSMS/2009–2010/10.07.2012.

References

First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationChandra, , Srikantamurthy, N., Umesha, K. B., Jeyaseelan, S. & Mahendra, M. (2012). Acta Cryst. E68, o1661–o1662.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationShridevi Doddaramappa, D., Chandra., Mahendra, M. & Lokanatha Rai, K. M. (2013). Chem. Heterocycl. Compd, 49, 698–703.
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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