Crystal structure of (E)-2-{[(6-meth-oxy-1,3-benzo-thia-zol-2-yl)imino]-meth-yl}phenol.

The title compound, C15H12N2O2S, crystallizes in the ortho-rhom-bic space group Pna21 , with two mol-ecules in the asymmetric unit (Z' = 2). Each mol-ecule consists of a 2-hy-droxy Schiff base moiety linked through a spacer to a 2-amino-benzo-thia-zole moiety. Each mol-ecule contains an intra-molecular hydrogen bond between the -OH group and imine N atom, forming a six-membered ring. The two independent molecules are linked by a pair of C-H⋯O hydrogen bonds, forming dimers with an R (2) 2(20) ring motif. These dimers are further lined into sheets in the ab plane by weak inter-molecular C-H⋯N inter-actions. The structure was refined as an inversion twin.

Chemical context

A wide range of biological activities have been attributed to amino­thia­zoles and compounds having similar structures (Tahiliani et al., 2003 ▸) and they have many applications in both human and veterinary medicine (Smith et al., 1999 ▸; Sarhan et al., 2010 ▸). Certain 2-amino­benzo­thia­zole derivatives act on the central nervous system (Funderburk et al., 1953 ▸), possess anti­microbial (Murhekar & Khadsan, 2010 ▸; Ravi et al., 2014 ▸), anti­fungal (Catalano et al., 2013 ▸) and anti­bacterial properties (Asiri et al., 2013 ▸), serve as selective receptors for anion sensing (Hijji & Wairia, 2005 ▸), are active in corrosion inhibition (Quraishi et al., 1997 ▸; Rawat & Quraishi, 2003 ▸) and act as plant-growth regulators (Mahajan et al., 2013 ▸). In addition, some metal complexes of Schiff bases of 2-amino­benzo­thia­zole derivatives have potent anti­bacterial properties (Sharma et al., 2002 ▸; Song et al., 2010 ▸). Among anti­tumor agents discovered in recent years, the identification of various 2-(4-amino­phen­yl)benzo­thia­zoles as potent and selective anti­tumor drugs against breast, ovarian, colon and renal cell lines has stimulated remarkable inter­est (Usman et al., 2003 ▸; Shi et al., 1996 ▸; Havrylyuk et al. 2010 ▸) in this class of compound from both a synthetic, and particularly, a structural point of view. Amino­thia­zole Schiff bases have been prepared as inter­mediate ligands and for complexation with various metals (Liang et al.,1999 ▸; Liu et al., 2009 ▸).

In this context, the synthesis and structural characterization of new 2-amino­benzo­thia­zole Schiff base derivatives is of inter­est (El’tsov & Mokrushin, 2002 ▸).

Structural commentary

The title compound, C15H12N2O2S, crystallizes in the ortho­rhom­bic space group, Pna2, with two mol­ecules (A and B) in the asymmetric unit (Z′ = 2). Each mol­ecule consists of a 2-hy­droxy Schiff base moiety linked through a spacer to a 2-amino­benzo­thia­zole moiety. This spacer is both planar [r.m.s. deviations of fitted atoms of 0.004 (3) and 0.007 (3) Å, respectively for mol­ecules A and B] and very close to coplanar with both the Schiff base and 2-amino­benzo­thia­zole end moieties [making dihedral angles of 2.6 (9) and 4.0 (3)°, respectively, in mol­ecule A and 3.3 (8) and 3.9 (7)° in mol­ecule B]. The mol­ecules themselves are very close to planar, as is shown by the dihedral angles of 4.0 (3) and 6.3 (2) between the two end groups for mol­ecules A and B, respectively. Each mol­ecule contains an intra­molecular hydrogen bond between the OH group and imine N atom, forming a six-membered ring.

Supra­molecular features

In addition to the intra­molecular hydrogen bond mentioned above, the mol­ecules are linked by a pair of C—H⋯O hydrogen bonds (Table 1 ▸), forming dimers with an (20) ring motif, as shown in Fig. 1 ▸. These dimers are further linked into sheets in the ab plane by weak inter­molecular C—H⋯N inter­actions involving C15 and N2B, as shown in Fig. 2 ▸.

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1AH1AN1A	0.84	1.93	2.647(9)	143
C13AH13AO1B	0.95	2.48	3.289(9)	144
C15AH15AN2B i	0.98	2.57	3.525(10)	166
O1BH1BN1B	0.84	1.89	2.636(9)	147
C13BH13BO1A	0.95	2.53	3.356(10)	145

Symmetry code: (i) .

Figure 1

Mol­ecular diagram for mol­ecules A and B of the title compound, showing the atom labeling. Displacement parameters are drawn at the 30% probability level. The diagram shows the two mol­ecules (A and B) linked into dimers by (20) C—H⋯O hydrogen bonds (dashed lines; see Table 1 ▸ for details).

Figure 2

Packing diagram, viewed along the b axis, showing a sheet of (20) C—H⋯O-linked dimers in the ac plane.

Database survey

A search of the Cambridge Structural Database (CSD, Version 5.35, last update November 2014; Groom & Allen, 2014 ▸) for related Schiff base derivatives of 2-amino­benzo­thia­zole gave 23 hits of which the closest example to the title compound was (E)-2-[(6-eth­oxy­benzo­thia­zol-2-yl)imino­meth­yl]-6-meth­oxy­phenol (Kong, 2009 ▸).

Synthesis and crystallization

A mixture of 0.505 g (4.10 mmol) salicyl­aldehyde and 0.746 g (4.10 mmol) 2-amino-6-meth­oxy­benzo­thio­zole was dissolved in 2 ml of aceto­nitrile in a vial. The mixture was reacted in a Biotage initiator eight mono mode microwave at 423 K for 2 min and then allowed to cool for 15 min. The resulting product was recrystallized from aceto­nitrile, filtered and then vacuum dried to afford 0.971 g (86% yield) of a yellow crystalline solid (m.p. 399–403 K). A sample was dissolved in ethanol and allowed to crystallize by slow evaporation to give yellow needles used for X-ray structural determination.

1H NMR (300 MHz, CDCl3): δ 12.07 (s, 1H), 9.36 (s, 1H), 8.81 (dd, J = 9.0, 2.5 Hz, 1H), 8.39 (d, J = 7.5 Hz, 1H), 8.05 (d, J = 9.0 Hz. 1H), 7.55 (m, 2H), 7.09 (d, 7.5 Hz, 1H), 7.04 (t, J = 7.5 Hz, 1H), 3.83 (s, 3H)

13C NMR (300 MHz, CDCl3, p.p.m.): δ 55.07, 105.07, 115.46, 118.4, 121.2, 122.88, 125.26, 130.4, 132.44, 135.07, 145.59, 157.8 162.69, 165.36, 169.49

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. C-bound H atoms were positioned geometrically and refined as riding: C–H = 0.93–0.99 Å with U(H) = 1.5U eq(C) for methyl H atoms and = 1.2U(C) for other H atoms. Phenol H atoms were located in a difference Fourier map and then refined as riding on their attached O atoms.

Table 2

Experimental details

Crystal data
Chemical formula	C15H12N2O2S
M r	284.33
Crystal system, space group	Orthorhombic, P n a21
Temperature (K)	120
a, b, c ()	35.623(2), 3.8172(2), 18.6525(8)
V (3)	2536.4(2)
Z	8
Radiation type	Cu K
(mm1)	2.30
Crystal size (mm)	0.38 0.09 0.06
Data collection
Diffractometer	Agilent SuperNova (Dual, Cu at zero, Atlas)
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012 ▸)
T min, T max	0.573, 0.863
No. of measured, independent and observed [I > 2(I)] reflections	6990, 3895, 3677
R int	0.045
(sin /)max (1)	0.630
Refinement
R[F 2 > 2(F 2)], wR(F 2), S	0.073, 0.189, 1.09
No. of reflections	3895
No. of parameters	364
No. of restraints	1
H-atom treatment	H-atom parameters constrained
max, min (e 3)	1.01, 0.74
Absolute structure	Refined as an inversion twin
Absolute structure parameter	0.65(5)

Computer programs: CrysAlis PRO (Agilent, 2012 ▸), SUPERFLIP (Palatinus et al., 2007 ▸), SHELXL2013 (Sheldrick, 2015 ▸) and SHELXTL (Sheldrick, 2008 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015005228/hg5435sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015005228/hg5435Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015005228/hg5435Isup3.cml

CCDC reference: 1053989

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H12N2O2S	Dx = 1.489 Mg m−3
Mr = 284.33	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pna21	Cell parameters from 2917 reflections
a = 35.623 (2) Å	θ = 4.7–76.1°
b = 3.8172 (2) Å	µ = 2.30 mm−1
c = 18.6525 (8) Å	T = 120 K
V = 2536.4 (2) Å3	Needle, yellow–orange
Z = 8	0.38 × 0.09 × 0.06 mm
F(000) = 1184

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	3895 independent reflections
Radiation source: sealed X-ray tube	3677 reflections with I > 2σ(I)
Detector resolution: 5.3250 pixels mm-1	Rint = 0.045
ω scans	θmax = 76.2°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −41→44
Tmin = 0.573, Tmax = 0.863	k = −2→4
6990 measured reflections	l = −20→23

Refinement on F2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.073	w = 1/[σ2(Fo2) + (0.0845P)2 + 6.6687P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.189	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 1.01 e Å−3
3895 reflections	Δρmin = −0.74 e Å−3
364 parameters	Absolute structure: Refined as an inversion twin.
1 restraint	Absolute structure parameter: 0.65 (5)

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. Refined as a 2-component inversion twin.

	x	y	z	Uiso*/Ueq
S1A	0.87402 (5)	0.3471 (4)	0.32176 (9)	0.0241 (4)
O1A	0.97069 (15)	0.6508 (16)	0.4723 (3)	0.0337 (13)
H1A	0.9559	0.6313	0.4376	0.050*
O2A	0.78912 (15)	−0.1334 (15)	0.1150 (3)	0.0283 (12)
N1A	0.94790 (18)	0.3743 (16)	0.3497 (4)	0.0250 (13)
N2A	0.92781 (17)	0.1374 (18)	0.2372 (4)	0.0283 (13)
C1A	1.0055 (2)	0.5657 (19)	0.4512 (4)	0.0261 (15)
C2A	1.0359 (2)	0.648 (2)	0.4958 (4)	0.0306 (16)
H1	1.0314	0.7620	0.5402	0.037*
C3A	1.0718 (2)	0.568 (2)	0.4768 (4)	0.0318 (17)
H2	1.0919	0.6241	0.5082	0.038*
C4A	1.0793 (2)	0.403 (2)	0.4114 (5)	0.0274 (15)
H3	1.1045	0.3592	0.3970	0.033*
C5A	1.0495 (2)	0.303 (2)	0.3674 (4)	0.0274 (16)
H4	1.0542	0.1730	0.3249	0.033*
C6A	1.0126 (2)	0.394 (2)	0.3862 (4)	0.0274 (16)
C7A	0.9824 (2)	0.2951 (18)	0.3370 (4)	0.0238 (15)
H5	0.9884	0.1694	0.2946	0.029*
C8A	0.9213 (2)	0.2730 (17)	0.2996 (4)	0.0225 (14)
C9A	0.89431 (19)	0.0635 (19)	0.2017 (4)	0.0237 (14)
C10A	0.8905 (2)	−0.087 (2)	0.1348 (4)	0.0265 (15)
H10A	0.9120	−0.1510	0.1078	0.032*
C11A	0.8548 (2)	−0.1449 (19)	0.1075 (4)	0.0264 (16)
H11A	0.8521	−0.2508	0.0617	0.032*
C12A	0.8227 (2)	−0.0498 (17)	0.1462 (4)	0.0212 (14)
C13A	0.8255 (2)	0.1077 (19)	0.2129 (4)	0.0254 (15)
H13A	0.8037	0.1706	0.2392	0.031*
C14A	0.8617 (2)	0.1715 (18)	0.2403 (4)	0.0240 (14)
C15A	0.75623 (19)	−0.027 (2)	0.1521 (5)	0.0289 (16)
H15A	0.7340	−0.1033	0.1254	0.043*
H15B	0.7560	0.2289	0.1566	0.043*
H15C	0.7560	−0.1328	0.2000	0.043*
S1B	0.87656 (5)	0.8509 (4)	0.49182 (9)	0.0246 (4)
O1B	0.78077 (16)	0.5412 (16)	0.3390 (3)	0.0361 (14)
H1B	0.7960	0.6119	0.3701	0.054*
O2B	0.95964 (15)	1.3166 (15)	0.7026 (3)	0.0293 (12)
N1B	0.80272 (18)	0.8089 (15)	0.4624 (4)	0.0247 (13)
N2B	0.82255 (17)	1.0626 (16)	0.5746 (4)	0.0263 (13)
C1B	0.7453 (2)	0.5753 (18)	0.3644 (4)	0.0248 (15)
C2B	0.7160 (2)	0.4583 (19)	0.3210 (5)	0.0291 (15)
H6	0.7209	0.3632	0.2749	0.035*
C3B	0.6790 (2)	0.484 (2)	0.3472 (4)	0.0299 (17)
H7	0.6587	0.4020	0.3187	0.036*
C4B	0.6717 (2)	0.628 (2)	0.4136 (4)	0.0287 (16)
H8	0.6466	0.6431	0.4301	0.034*
C5B	0.7005 (2)	0.7494 (18)	0.4564 (4)	0.0243 (15)
H9	0.6950	0.8494	0.5019	0.029*
C6B	0.7381 (2)	0.7258 (16)	0.4329 (4)	0.0204 (14)
C7B	0.7681 (2)	0.8352 (17)	0.4793 (4)	0.0245 (15)
H10	0.7618	0.9319	0.5247	0.029*
C8B	0.8289 (2)	0.9165 (19)	0.5123 (4)	0.0252 (15)
C9B	0.8560 (2)	1.1290 (19)	0.6098 (4)	0.0253 (15)
C10B	0.8589 (2)	1.2798 (19)	0.6777 (4)	0.0262 (16)
H10B	0.8370	1.3415	0.7040	0.031*
C11B	0.8943 (2)	1.3379 (19)	0.7062 (5)	0.0261 (15)
H11B	0.8967	1.4428	0.7522	0.031*
C12B	0.9269 (2)	1.2432 (18)	0.6678 (5)	0.0252 (16)
C13B	0.9242 (2)	1.0870 (17)	0.6009 (4)	0.0246 (14)
H13B	0.9460	1.0207	0.5748	0.029*
C14B	0.8884 (2)	1.0313 (17)	0.5736 (4)	0.0234 (14)
C15B	0.9936 (2)	1.235 (2)	0.6643 (5)	0.0288 (16)
H15D	1.0149	1.3469	0.6882	0.043*
H15E	0.9916	1.3226	0.6150	0.043*
H15F	0.9972	0.9808	0.6635	0.043*

	U11	U22	U33	U12	U13	U23
S1A	0.0280 (8)	0.0261 (8)	0.0182 (9)	−0.0016 (6)	−0.0003 (7)	−0.0049 (7)
O1A	0.029 (3)	0.044 (3)	0.028 (3)	−0.005 (2)	0.000 (2)	0.001 (3)
O2A	0.031 (3)	0.031 (3)	0.023 (3)	−0.003 (2)	−0.002 (2)	−0.004 (2)
N1A	0.032 (3)	0.021 (3)	0.022 (3)	−0.002 (2)	−0.002 (3)	−0.006 (2)
N2A	0.032 (3)	0.033 (3)	0.020 (3)	−0.007 (2)	−0.003 (3)	0.001 (3)
C1A	0.033 (4)	0.025 (3)	0.020 (4)	−0.006 (3)	−0.003 (3)	0.006 (3)
C2A	0.040 (4)	0.034 (4)	0.018 (4)	−0.015 (3)	−0.002 (3)	0.002 (3)
C3A	0.039 (4)	0.033 (4)	0.024 (4)	−0.007 (3)	−0.008 (3)	0.009 (3)
C4A	0.027 (3)	0.026 (3)	0.030 (4)	0.004 (3)	0.001 (3)	0.002 (3)
C5A	0.038 (4)	0.030 (4)	0.014 (4)	−0.001 (3)	−0.001 (3)	0.000 (3)
C6A	0.034 (4)	0.025 (3)	0.023 (4)	−0.002 (3)	0.000 (3)	0.004 (3)
C7A	0.037 (4)	0.022 (3)	0.012 (3)	−0.003 (3)	0.000 (3)	0.003 (3)
C8A	0.034 (4)	0.017 (3)	0.017 (4)	0.000 (2)	0.002 (3)	−0.004 (2)
C9A	0.028 (3)	0.027 (3)	0.016 (3)	−0.004 (3)	0.001 (3)	0.007 (3)
C10A	0.030 (3)	0.028 (4)	0.022 (4)	0.003 (3)	0.003 (3)	−0.002 (3)
C11A	0.041 (4)	0.021 (3)	0.016 (4)	−0.008 (3)	0.000 (3)	0.003 (3)
C12A	0.032 (3)	0.014 (3)	0.018 (3)	−0.004 (2)	−0.003 (3)	0.004 (3)
C13A	0.030 (3)	0.027 (4)	0.019 (3)	0.002 (3)	0.004 (3)	0.004 (3)
C14A	0.033 (3)	0.016 (3)	0.023 (4)	−0.005 (3)	0.003 (3)	0.005 (3)
C15A	0.025 (3)	0.029 (3)	0.033 (4)	−0.003 (3)	−0.002 (3)	−0.005 (3)
S1B	0.0291 (9)	0.0271 (8)	0.0177 (9)	0.0008 (6)	−0.0003 (6)	−0.0047 (7)
O1B	0.033 (3)	0.046 (3)	0.029 (3)	−0.001 (2)	0.002 (2)	−0.013 (3)
O2B	0.029 (3)	0.036 (3)	0.022 (3)	0.004 (2)	−0.001 (2)	−0.001 (2)
N1B	0.032 (3)	0.020 (3)	0.022 (3)	0.002 (2)	−0.004 (3)	0.002 (2)
N2B	0.034 (3)	0.020 (3)	0.024 (3)	−0.002 (2)	−0.004 (3)	−0.003 (3)
C1B	0.033 (4)	0.018 (3)	0.023 (4)	0.001 (3)	−0.003 (3)	0.002 (3)
C2B	0.040 (4)	0.029 (3)	0.018 (4)	0.000 (3)	0.000 (3)	0.003 (3)
C3B	0.036 (4)	0.028 (4)	0.026 (4)	−0.002 (3)	−0.010 (3)	0.009 (3)
C4B	0.030 (4)	0.030 (4)	0.026 (4)	0.000 (3)	0.003 (3)	0.002 (3)
C5B	0.031 (4)	0.020 (3)	0.022 (4)	0.001 (3)	0.003 (3)	0.003 (3)
C6B	0.029 (3)	0.012 (3)	0.021 (4)	0.001 (2)	−0.002 (3)	0.004 (3)
C7B	0.040 (4)	0.014 (3)	0.019 (4)	−0.003 (2)	−0.003 (3)	0.009 (3)
C8B	0.028 (4)	0.022 (3)	0.025 (4)	0.002 (3)	0.001 (3)	0.000 (3)
C9B	0.033 (3)	0.019 (3)	0.024 (4)	−0.004 (2)	−0.001 (3)	−0.001 (3)
C10B	0.040 (4)	0.017 (3)	0.021 (4)	0.001 (3)	0.005 (3)	−0.002 (3)
C11B	0.033 (4)	0.021 (3)	0.024 (4)	−0.002 (3)	0.000 (3)	−0.002 (3)
C12B	0.033 (4)	0.014 (3)	0.028 (4)	−0.004 (2)	−0.003 (3)	0.002 (3)
C13B	0.033 (3)	0.018 (3)	0.023 (4)	0.002 (3)	0.003 (3)	0.006 (3)
C14B	0.045 (4)	0.014 (3)	0.011 (3)	0.000 (3)	0.003 (3)	0.006 (2)
C15B	0.040 (4)	0.025 (3)	0.021 (4)	−0.002 (3)	−0.004 (3)	0.001 (3)

S1A—C14A	1.718 (8)	S1B—C14B	1.726 (8)
S1A—C8A	1.759 (8)	S1B—C8B	1.758 (8)
O1A—C1A	1.341 (10)	O1B—C1B	1.356 (9)
O1A—H1A	0.8399	O1B—H1B	0.8400
O2A—C12A	1.369 (9)	O2B—C12B	1.364 (9)
O2A—C15A	1.421 (9)	O2B—C15B	1.438 (10)
N1A—C7A	1.288 (10)	N1B—C7B	1.278 (10)
N1A—C8A	1.385 (10)	N1B—C8B	1.380 (10)
N2A—C8A	1.295 (10)	N2B—C8B	1.309 (10)
N2A—C9A	1.393 (9)	N2B—C9B	1.383 (9)
C1A—C6A	1.402 (11)	C1B—C2B	1.395 (11)
C1A—C2A	1.402 (11)	C1B—C6B	1.424 (10)
C2A—C3A	1.362 (12)	C2B—C3B	1.409 (11)
C2A—H1	0.9500	C2B—H6	0.9500
C3A—C4A	1.398 (12)	C3B—C4B	1.378 (12)
C3A—H2	0.9500	C3B—H7	0.9500
C4A—C5A	1.395 (11)	C4B—C5B	1.381 (11)
C4A—H3	0.9500	C4B—H8	0.9500
C5A—C6A	1.405 (12)	C5B—C6B	1.412 (10)
C5A—H4	0.9500	C5B—H9	0.9500
C6A—C7A	1.463 (11)	C6B—C7B	1.435 (10)
C7A—H5	0.9500	C7B—H10	0.9500
C9A—C10A	1.382 (11)	C9B—C14B	1.388 (11)
C9A—C14A	1.428 (10)	C9B—C10B	1.396 (11)
C10A—C11A	1.385 (11)	C10B—C11B	1.388 (12)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.401 (11)	C11B—C12B	1.410 (11)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—C13A	1.385 (11)	C12B—C13B	1.387 (11)
C13A—C14A	1.407 (10)	C13B—C14B	1.391 (11)
C13A—H13A	0.9500	C13B—H13B	0.9500
C15A—H15A	0.9800	C15B—H15D	0.9800
C15A—H15B	0.9800	C15B—H15E	0.9800
C15A—H15C	0.9800	C15B—H15F	0.9800
C14A—S1A—C8A	88.5 (4)	C14B—S1B—C8B	89.2 (4)
C1A—O1A—H1A	109.5	C1B—O1B—H1B	109.3
C12A—O2A—C15A	116.6 (6)	C12B—O2B—C15B	116.0 (6)
C7A—N1A—C8A	117.5 (6)	C7B—N1B—C8B	117.6 (7)
C8A—N2A—C9A	110.8 (6)	C8B—N2B—C9B	110.5 (6)
O1A—C1A—C6A	122.3 (7)	O1B—C1B—C2B	117.6 (7)
O1A—C1A—C2A	119.1 (7)	O1B—C1B—C6B	121.3 (6)
C6A—C1A—C2A	118.6 (7)	C2B—C1B—C6B	121.1 (7)
C3A—C2A—C1A	121.4 (8)	C1B—C2B—C3B	118.4 (8)
C3A—C2A—H1	119.3	C1B—C2B—H6	120.8
C1A—C2A—H1	119.3	C3B—C2B—H6	120.8
C2A—C3A—C4A	120.5 (7)	C4B—C3B—C2B	121.0 (7)
C2A—C3A—H2	119.8	C4B—C3B—H7	119.5
C4A—C3A—H2	119.8	C2B—C3B—H7	119.5
C5A—C4A—C3A	119.4 (7)	C3B—C4B—C5B	120.9 (7)
C5A—C4A—H3	120.3	C3B—C4B—H8	119.5
C3A—C4A—H3	120.3	C5B—C4B—H8	119.5
C4A—C5A—C6A	119.9 (7)	C4B—C5B—C6B	120.2 (7)
C4A—C5A—H4	120.1	C4B—C5B—H9	119.9
C6A—C5A—H4	120.1	C6B—C5B—H9	119.9
C1A—C6A—C5A	120.0 (7)	C5B—C6B—C1B	118.3 (7)
C1A—C6A—C7A	122.1 (7)	C5B—C6B—C7B	120.0 (7)
C5A—C6A—C7A	117.9 (7)	C1B—C6B—C7B	121.6 (7)
N1A—C7A—C6A	121.7 (7)	N1B—C7B—C6B	123.1 (7)
N1A—C7A—H5	119.2	N1B—C7B—H10	118.4
C6A—C7A—H5	119.2	C6B—C7B—H10	118.4
N2A—C8A—N1A	126.7 (7)	N2B—C8B—N1B	127.5 (7)
N2A—C8A—S1A	116.5 (6)	N2B—C8B—S1B	114.9 (6)
N1A—C8A—S1A	116.8 (5)	N1B—C8B—S1B	117.6 (6)
C10A—C9A—N2A	126.7 (7)	N2B—C9B—C14B	115.8 (7)
C10A—C9A—C14A	119.7 (7)	N2B—C9B—C10B	124.8 (7)
N2A—C9A—C14A	113.6 (7)	C14B—C9B—C10B	119.3 (7)
C9A—C10A—C11A	119.2 (7)	C11B—C10B—C9B	118.8 (8)
C9A—C10A—H10A	120.4	C11B—C10B—H10B	120.6
C11A—C10A—H10A	120.4	C9B—C10B—H10B	120.6
C10A—C11A—C12A	121.2 (8)	C10B—C11B—C12B	120.8 (8)
C10A—C11A—H11A	119.4	C10B—C11B—H11B	119.6
C12A—C11A—H11A	119.4	C12B—C11B—H11B	119.6
O2A—C12A—C13A	123.1 (7)	O2B—C12B—C13B	125.1 (7)
O2A—C12A—C11A	115.8 (7)	O2B—C12B—C11B	114.2 (7)
C13A—C12A—C11A	121.1 (7)	C13B—C12B—C11B	120.7 (7)
C12A—C13A—C14A	117.8 (7)	C12B—C13B—C14B	117.3 (7)
C12A—C13A—H13A	121.1	C12B—C13B—H13B	121.4
C14A—C13A—H13A	121.1	C14B—C13B—H13B	121.4
C13A—C14A—C9A	120.8 (7)	C9B—C14B—C13B	123.0 (7)
C13A—C14A—S1A	128.5 (6)	C9B—C14B—S1B	109.6 (6)
C9A—C14A—S1A	110.5 (6)	C13B—C14B—S1B	127.4 (6)
O2A—C15A—H15A	109.5	O2B—C15B—H15D	109.5
O2A—C15A—H15B	109.5	O2B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
O2A—C15A—H15C	109.5	O2B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
O1A—C1A—C2A—C3A	−179.9 (7)	O1B—C1B—C2B—C3B	178.6 (6)
C6A—C1A—C2A—C3A	0.7 (11)	C6B—C1B—C2B—C3B	−1.5 (11)
C1A—C2A—C3A—C4A	0.6 (12)	C1B—C2B—C3B—C4B	1.1 (11)
C2A—C3A—C4A—C5A	−3.6 (12)	C2B—C3B—C4B—C5B	−0.1 (12)
C3A—C4A—C5A—C6A	5.3 (12)	C3B—C4B—C5B—C6B	−0.6 (11)
O1A—C1A—C6A—C5A	−178.4 (7)	C4B—C5B—C6B—C1B	0.2 (10)
C2A—C1A—C6A—C5A	1.0 (11)	C4B—C5B—C6B—C7B	−176.6 (6)
O1A—C1A—C6A—C7A	−0.1 (11)	O1B—C1B—C6B—C5B	−179.3 (6)
C2A—C1A—C6A—C7A	179.3 (7)	C2B—C1B—C6B—C5B	0.9 (10)
C4A—C5A—C6A—C1A	−4.0 (11)	O1B—C1B—C6B—C7B	−2.5 (10)
C4A—C5A—C6A—C7A	177.6 (7)	C2B—C1B—C6B—C7B	177.6 (6)
C8A—N1A—C7A—C6A	179.3 (6)	C8B—N1B—C7B—C6B	−178.6 (6)
C1A—C6A—C7A—N1A	2.9 (11)	C5B—C6B—C7B—N1B	177.4 (6)
C5A—C6A—C7A—N1A	−178.8 (7)	C1B—C6B—C7B—N1B	0.7 (10)
C9A—N2A—C8A—N1A	179.1 (7)	C9B—N2B—C8B—N1B	179.2 (7)
C9A—N2A—C8A—S1A	−2.8 (8)	C9B—N2B—C8B—S1B	−0.3 (8)
C7A—N1A—C8A—N2A	−7.7 (11)	C7B—N1B—C8B—N2B	−4.1 (11)
C7A—N1A—C8A—S1A	174.3 (5)	C7B—N1B—C8B—S1B	175.5 (5)
C14A—S1A—C8A—N2A	1.2 (6)	C14B—S1B—C8B—N2B	0.4 (6)
C14A—S1A—C8A—N1A	179.5 (6)	C14B—S1B—C8B—N1B	−179.2 (6)
C8A—N2A—C9A—C10A	−178.8 (7)	C8B—N2B—C9B—C14B	0.0 (9)
C8A—N2A—C9A—C14A	3.3 (9)	C8B—N2B—C9B—C10B	−179.3 (7)
N2A—C9A—C10A—C11A	179.6 (7)	N2B—C9B—C10B—C11B	−178.8 (7)
C14A—C9A—C10A—C11A	−2.7 (11)	C14B—C9B—C10B—C11B	2.0 (11)
C9A—C10A—C11A—C12A	0.6 (11)	C9B—C10B—C11B—C12B	−0.7 (11)
C15A—O2A—C12A—C13A	4.5 (10)	C15B—O2B—C12B—C13B	2.6 (10)
C15A—O2A—C12A—C11A	−177.6 (6)	C15B—O2B—C12B—C11B	−178.0 (6)
C10A—C11A—C12A—O2A	−177.3 (6)	C10B—C11B—C12B—O2B	179.9 (7)
C10A—C11A—C12A—C13A	0.5 (11)	C10B—C11B—C12B—C13B	−0.6 (11)
O2A—C12A—C13A—C14A	178.2 (6)	O2B—C12B—C13B—C14B	179.9 (6)
C11A—C12A—C13A—C14A	0.5 (10)	C11B—C12B—C13B—C14B	0.5 (10)
C12A—C13A—C14A—C9A	−2.6 (10)	N2B—C9B—C14B—C13B	178.5 (6)
C12A—C13A—C14A—S1A	−177.6 (6)	C10B—C9B—C14B—C13B	−2.2 (11)
C10A—C9A—C14A—C13A	3.8 (10)	N2B—C9B—C14B—S1B	0.3 (8)
N2A—C9A—C14A—C13A	−178.3 (6)	C10B—C9B—C14B—S1B	179.6 (6)
C10A—C9A—C14A—S1A	179.6 (6)	C12B—C13B—C14B—C9B	0.9 (10)
N2A—C9A—C14A—S1A	−2.4 (8)	C12B—C13B—C14B—S1B	178.8 (5)
C8A—S1A—C14A—C13A	176.1 (7)	C8B—S1B—C14B—C9B	−0.4 (5)
C8A—S1A—C14A—C9A	0.7 (5)	C8B—S1B—C14B—C13B	−178.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···N1A	0.84	1.93	2.647 (9)	143
C13A—H13A···O1B	0.95	2.48	3.289 (9)	144
C15A—H15A···N2Bi	0.98	2.57	3.525 (10)	166
O1B—H1B···N1B	0.84	1.89	2.636 (9)	147
C13B—H13B···O1A	0.95	2.53	3.356 (10)	145