Crystal structure of 2-[(E)-4-benz-yloxy-2-hy-droxy-benzyl-idene]-N-cyclo-hexyl-hydrazinecarbo-thio-amide aceto-nitrile hemisolvate.

The asymmetric unit of the title compound, C21H25N3O2S·0.5C2H3N, contains two independent mol-ecules with almost similar structural properties along with a solvent mol-ecule of aceto-nitrile. The compound exists in the E conformation with respect to the azomethine C=N double bond. The hydrazinecarbo-thio-amide moieties in both independent mol-ecules are almost planar [maximum deviations of 0.013 (2) and 0.007 (2) Å]. The mol-ecular conformation is stabilized in each case by an intra-molecular N-H⋯N hydrogen bond. In the crystal, pairs of N-H⋯S hydrogen bonds link each of the independent mol-ecules into inversion dimers. The dimers are inter-connected by means of three C-H⋯π inter-actions.

Related literature

For anti­microbial application, see: Joseph et al. (2004 ▶). For fluorescence activity, see: Kumar et al. (2013 ▶). For versatile coordination ability, see: Sreekanth et al. (2004 ▶). For the synthesis of related compounds, see: Jacob & Kurup (2012 ▶). For related structures, see: Seena et al. (2006 ▶); Jacob & Kurup (2012 ▶).

Experimental

Crystal data

2C21H25N3O2S·C2H3N

M = 808.07

Triclinic,

a = 10.5345 (4) Å

b = 10.8341 (4) Å

c = 21.8169 (10) Å

α = 97.241 (2)°

β = 92.120 (2)°

γ = 118.901 (2)°

V = 2148.72 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.17 mm−1

T = 296 K

0.50 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan SADABS (Bruker, 2004 ▶) T min = 0.918, T max = 0.942

15933 measured reflections

9260 independent reflections

6918 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.136

S = 1.03

9260 reflections

540 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (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 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) Global, I. DOI: 10.1107/S1600536814017905/bv2235sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814017905/bv2235Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814017905/bv2235Isup3.cml

Click here for additional data file.

ORTEP E N . DOI: 10.1107/S1600536814017905/bv2235fig1.tif

ORTEP diagram of (E)-2-(4-benz­yloxy-2-hy­droxy­benzyl­idene)-N-cyclo­hexyl­hydrazinecarbo­thio­amide with 50% probability ellipsoids.

Click here for additional data file.

21 25 3 2 2 3 . DOI: 10.1107/S1600536814017905/bv2235fig2.tif

Hydrogen-bond inter­actions of the title compound, [C21H25N3O2S]·0.5C2H3N.

Click here for additional data file.

. DOI: 10.1107/S1600536814017905/bv2235fig3.tif

C—H⋯π inter­actions of the title compound.

Click here for additional data file.

a . DOI: 10.1107/S1600536814017905/bv2235fig4.tif

Packing diagram of the title compound along a axis.

CCDC reference: 1017712

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

2C21H25N3O2S·C2H3N	Z = 2
Mr = 808.07	F(000) = 860
Triclinic, P1	Dx = 1.249 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.5345 (4) Å	Cell parameters from 6744 reflections
b = 10.8341 (4) Å	θ = 2.2–28.1°
c = 21.8169 (10) Å	µ = 0.17 mm−1
α = 97.241 (2)°	T = 296 K
β = 92.120 (2)°	Needle, yellow
γ = 118.901 (2)°	0.50 × 0.20 × 0.18 mm
V = 2148.72 (15) Å3

Bruker Kappa APEXII CCD diffractometer	9260 independent reflections
Radiation source: fine-focus sealed tube	6918 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
ω and φ scan	θmax = 27.0°, θmin = 1.0°
Absorption correction: multi-scan SADABS (Bruker, 2004)	h = −13→13
Tmin = 0.918, Tmax = 0.942	k = −13→13
15933 measured reflections	l = −27→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0652P)2 + 0.7212P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
9260 reflections	Δρmax = 0.39 e Å−3
540 parameters	Δρmin = −0.25 e Å−3
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0036 (9)

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.

	x	y	z	Uiso*/Ueq
S1	−0.60227 (5)	0.39508 (6)	0.07407 (3)	0.05080 (16)
S2	0.62422 (6)	0.49312 (6)	0.42617 (3)	0.05093 (16)
O1	0.50839 (13)	0.84763 (15)	0.05748 (7)	0.0500 (4)
O2	0.04715 (15)	0.53001 (16)	0.11875 (8)	0.0542 (4)
O3	0.15464 (15)	1.13678 (15)	0.44214 (7)	0.0484 (4)
O4	0.48815 (17)	0.97664 (18)	0.38472 (8)	0.0576 (4)
N1	−0.18643 (14)	0.53120 (15)	0.06462 (7)	0.0339 (3)
N2	−0.33002 (15)	0.49724 (17)	0.05214 (8)	0.0380 (4)
N3	−0.39713 (15)	0.35494 (16)	0.12662 (7)	0.0364 (3)
N4	0.47289 (17)	0.75978 (16)	0.43719 (7)	0.0378 (3)
N5	0.51039 (18)	0.65922 (17)	0.44969 (8)	0.0420 (4)
N6	0.65106 (19)	0.70656 (17)	0.36985 (8)	0.0451 (4)
N7	0.3302 (6)	0.4151 (5)	0.2682 (2)	0.1717 (19)
C1	0.8362 (2)	0.9162 (3)	0.07453 (12)	0.0616 (6)
H1	0.8023	0.8397	0.0420	0.074*
C2	0.9830 (3)	1.0168 (3)	0.08441 (14)	0.0701 (7)
H2	1.0472	1.0058	0.0591	0.084*
C3	1.0339 (2)	1.1302 (3)	0.12998 (14)	0.0702 (7)
H3	1.1325	1.1982	0.1359	0.084*
C4	0.9401 (3)	1.1445 (3)	0.16734 (16)	0.0886 (10)
H4	0.9744	1.2227	0.1991	0.106*
C5	0.7939 (3)	1.0434 (3)	0.15839 (14)	0.0759 (8)
H5	0.7307	1.0541	0.1844	0.091*
C6	0.74039 (19)	0.9283 (2)	0.11217 (11)	0.0467 (5)
C7	0.5819 (2)	0.8176 (2)	0.10456 (13)	0.0579 (6)
H7A	0.5705	0.7231	0.0928	0.070*
H7B	0.5409	0.8202	0.1435	0.070*
C8	0.35980 (18)	0.78021 (19)	0.05220 (9)	0.0384 (4)
C9	0.27479 (18)	0.67962 (19)	0.08791 (9)	0.0396 (4)
H9	0.3177	0.6486	0.1158	0.048*
C10	0.12462 (18)	0.62556 (18)	0.08164 (9)	0.0357 (4)
C11	0.05770 (17)	0.66738 (17)	0.03884 (9)	0.0333 (4)
C12	0.14739 (19)	0.76540 (19)	0.00217 (9)	0.0390 (4)
H12	0.1049	0.7930	−0.0275	0.047*
C13	0.29580 (19)	0.8219 (2)	0.00862 (10)	0.0416 (4)
H13	0.3530	0.8876	−0.0160	0.050*
C14	−0.09743 (17)	0.61556 (18)	0.03108 (9)	0.0340 (4)
H14	−0.1347	0.6449	0.0002	0.041*
C15	−0.43444 (17)	0.41394 (17)	0.08528 (8)	0.0327 (4)
C16	−0.49581 (18)	0.26337 (18)	0.16725 (8)	0.0345 (4)
H16	−0.5634	0.2984	0.1783	0.041*
C17	−0.4086 (2)	0.2746 (2)	0.22629 (10)	0.0483 (5)
H17A	−0.3572	0.3731	0.2473	0.058*
H17B	−0.3367	0.2461	0.2161	0.058*
C18	−0.5082 (2)	0.1797 (2)	0.26935 (10)	0.0549 (5)
H18A	−0.4495	0.1831	0.3055	0.066*
H18B	−0.5719	0.2160	0.2836	0.066*
C19	−0.5994 (3)	0.0272 (2)	0.23745 (12)	0.0593 (6)
H19A	−0.6665	−0.0283	0.2652	0.071*
H19B	−0.5365	−0.0131	0.2280	0.071*
C20	−0.6847 (2)	0.0171 (2)	0.17822 (12)	0.0580 (6)
H20A	−0.7556	0.0473	0.1881	0.070*
H20B	−0.7374	−0.0814	0.1574	0.070*
C21	−0.5842 (2)	0.1104 (2)	0.13481 (10)	0.0487 (5)
H21A	−0.5191	0.0749	0.1218	0.058*
H21B	−0.6419	0.1059	0.0980	0.058*
C22	−0.0343 (3)	1.1977 (3)	0.34536 (13)	0.0700 (7)
H22	−0.0480	1.1139	0.3215	0.084*
C23	−0.1360 (3)	1.2417 (3)	0.33712 (15)	0.0828 (9)
H23	−0.2180	1.1869	0.3083	0.099*
C24	−0.1165 (3)	1.3645 (3)	0.37091 (13)	0.0654 (7)
H24	−0.1835	1.3956	0.3645	0.078*
C25	0.0003 (3)	1.4413 (3)	0.41389 (14)	0.0728 (7)
H25	0.0134	1.5251	0.4375	0.087*
C26	0.1011 (3)	1.3960 (2)	0.42301 (14)	0.0663 (7)
H26	0.1802	1.4488	0.4534	0.080*
C27	0.0858 (2)	1.2751 (2)	0.38802 (10)	0.0445 (5)
C28	0.1956 (2)	1.2258 (2)	0.39536 (12)	0.0550 (6)
H28A	0.1967	1.1726	0.3563	0.066*
H28B	0.2923	1.3073	0.4075	0.066*
C29	0.22107 (19)	1.05710 (19)	0.44817 (9)	0.0371 (4)
C30	0.1700 (2)	0.9661 (2)	0.49167 (10)	0.0444 (5)
H30	0.0989	0.9654	0.5159	0.053*
C31	0.2259 (2)	0.8774 (2)	0.49842 (10)	0.0420 (4)
H31	0.1922	0.8171	0.5279	0.050*
C32	0.33155 (19)	0.87403 (18)	0.46276 (9)	0.0342 (4)
C33	0.38348 (19)	0.96924 (19)	0.42039 (9)	0.0363 (4)
C34	0.3293 (2)	1.0614 (2)	0.41346 (9)	0.0387 (4)
H34	0.3658	1.1255	0.3856	0.046*
C35	0.38347 (19)	0.77485 (18)	0.47119 (9)	0.0373 (4)
H35	0.3504	0.7199	0.5026	0.045*
C36	0.5958 (2)	0.62855 (19)	0.41394 (9)	0.0365 (4)
C37	0.7455 (2)	0.6898 (2)	0.32651 (9)	0.0426 (4)
H37	0.7157	0.5879	0.3177	0.051*
C38	0.9025 (3)	0.7690 (3)	0.35401 (13)	0.0663 (7)
H38A	0.9126	0.7339	0.3916	0.080*
H38B	0.9340	0.8700	0.3650	0.080*
C39	0.9981 (3)	0.7489 (4)	0.30791 (17)	0.0894 (10)
H39A	0.9722	0.6490	0.2998	0.107*
H39B	1.0995	0.8041	0.3256	0.107*
C40	0.9792 (4)	0.7970 (3)	0.24691 (17)	0.0951 (11)
H40A	1.0133	0.8989	0.2544	0.114*
H40B	1.0376	0.7793	0.2174	0.114*
C41	0.8222 (4)	0.7181 (3)	0.22016 (13)	0.0812 (9)
H41A	0.7916	0.6174	0.2086	0.097*
H41B	0.8117	0.7539	0.1828	0.097*
C42	0.7237 (3)	0.7347 (3)	0.26621 (12)	0.0688 (7)
H42A	0.7459	0.8336	0.2740	0.083*
H42B	0.6225	0.6764	0.2486	0.083*
C43	0.2358 (7)	0.5888 (6)	0.2730 (3)	0.170 (2)
H43A	0.2010	0.5951	0.3127	0.256*
H43B	0.1575	0.5572	0.2405	0.256*
H43C	0.3136	0.6810	0.2682	0.256*
C44	0.2868 (4)	0.4920 (5)	0.2694 (2)	0.1059 (11)
H3'	−0.3084 (13)	0.368 (2)	0.1287 (10)	0.047 (6)*
H6	0.631 (2)	0.7759 (16)	0.3704 (10)	0.046 (6)*
H5'	0.473 (2)	0.611 (2)	0.4799 (8)	0.051 (6)*
H2'	−0.349 (2)	0.533 (2)	0.0218 (8)	0.057 (7)*
H2A	−0.0407 (13)	0.508 (3)	0.1130 (13)	0.078 (9)*
H4'	0.516 (3)	0.920 (2)	0.3942 (12)	0.064 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0261 (2)	0.0718 (3)	0.0646 (4)	0.0249 (2)	0.0140 (2)	0.0391 (3)
S2	0.0694 (4)	0.0562 (3)	0.0588 (3)	0.0499 (3)	0.0283 (3)	0.0274 (3)
O1	0.0206 (6)	0.0553 (8)	0.0659 (10)	0.0111 (6)	0.0027 (6)	0.0155 (7)
O2	0.0293 (7)	0.0642 (9)	0.0646 (10)	0.0139 (7)	0.0056 (7)	0.0353 (8)
O3	0.0501 (8)	0.0593 (8)	0.0634 (9)	0.0430 (7)	0.0211 (7)	0.0294 (7)
O4	0.0688 (10)	0.0879 (11)	0.0613 (10)	0.0645 (9)	0.0364 (8)	0.0435 (9)
N1	0.0213 (6)	0.0393 (8)	0.0391 (8)	0.0130 (6)	0.0025 (6)	0.0082 (6)
N2	0.0224 (7)	0.0496 (9)	0.0448 (9)	0.0164 (6)	0.0067 (6)	0.0218 (7)
N3	0.0230 (7)	0.0445 (8)	0.0432 (9)	0.0151 (6)	0.0057 (6)	0.0182 (7)
N4	0.0445 (8)	0.0399 (8)	0.0437 (9)	0.0305 (7)	0.0082 (7)	0.0130 (7)
N5	0.0544 (10)	0.0471 (9)	0.0483 (10)	0.0393 (8)	0.0204 (8)	0.0224 (8)
N6	0.0562 (10)	0.0451 (9)	0.0538 (10)	0.0361 (8)	0.0229 (8)	0.0221 (8)
N7	0.191 (5)	0.199 (5)	0.184 (5)	0.141 (4)	0.050 (4)	0.026 (4)
C1	0.0497 (13)	0.0629 (14)	0.0688 (16)	0.0271 (11)	0.0060 (11)	0.0017 (12)
C2	0.0409 (12)	0.097 (2)	0.0799 (19)	0.0362 (13)	0.0195 (12)	0.0247 (16)
C3	0.0278 (10)	0.0832 (18)	0.0795 (19)	0.0097 (11)	−0.0039 (11)	0.0250 (15)
C4	0.0506 (15)	0.0773 (18)	0.093 (2)	0.0053 (13)	−0.0019 (14)	−0.0199 (16)
C5	0.0414 (12)	0.0736 (16)	0.093 (2)	0.0185 (12)	0.0145 (13)	−0.0135 (14)
C6	0.0256 (9)	0.0454 (10)	0.0662 (14)	0.0157 (8)	−0.0020 (9)	0.0095 (10)
C7	0.0294 (10)	0.0527 (12)	0.0854 (17)	0.0143 (9)	−0.0028 (10)	0.0183 (12)
C8	0.0220 (8)	0.0373 (9)	0.0488 (11)	0.0103 (7)	0.0027 (7)	0.0017 (8)
C9	0.0264 (8)	0.0402 (9)	0.0490 (11)	0.0142 (7)	−0.0014 (8)	0.0079 (8)
C10	0.0264 (8)	0.0336 (8)	0.0425 (10)	0.0107 (7)	0.0035 (7)	0.0079 (7)
C11	0.0233 (8)	0.0326 (8)	0.0402 (10)	0.0110 (7)	0.0034 (7)	0.0046 (7)
C12	0.0292 (9)	0.0412 (9)	0.0452 (11)	0.0149 (8)	0.0034 (8)	0.0124 (8)
C13	0.0281 (9)	0.0410 (10)	0.0490 (11)	0.0102 (8)	0.0083 (8)	0.0131 (8)
C14	0.0255 (8)	0.0366 (9)	0.0387 (10)	0.0137 (7)	0.0022 (7)	0.0091 (7)
C15	0.0242 (8)	0.0348 (8)	0.0380 (10)	0.0129 (7)	0.0041 (7)	0.0092 (7)
C16	0.0297 (8)	0.0363 (9)	0.0383 (10)	0.0150 (7)	0.0075 (7)	0.0128 (7)
C17	0.0415 (10)	0.0488 (11)	0.0472 (12)	0.0149 (9)	0.0008 (9)	0.0158 (9)
C18	0.0548 (13)	0.0676 (14)	0.0455 (12)	0.0284 (11)	0.0095 (10)	0.0270 (11)
C19	0.0565 (13)	0.0598 (13)	0.0741 (16)	0.0309 (11)	0.0267 (12)	0.0380 (12)
C20	0.0491 (12)	0.0432 (11)	0.0670 (15)	0.0092 (9)	0.0145 (11)	0.0160 (10)
C21	0.0474 (11)	0.0409 (10)	0.0459 (12)	0.0123 (9)	0.0067 (9)	0.0072 (9)
C22	0.0744 (16)	0.0748 (16)	0.0774 (18)	0.0561 (14)	−0.0123 (14)	−0.0097 (13)
C23	0.0769 (18)	0.112 (2)	0.080 (2)	0.0692 (18)	−0.0205 (15)	−0.0063 (17)
C24	0.0754 (16)	0.0935 (18)	0.0693 (16)	0.0695 (16)	0.0170 (14)	0.0320 (14)
C25	0.0910 (19)	0.0588 (14)	0.091 (2)	0.0547 (15)	0.0133 (17)	0.0093 (14)
C26	0.0603 (14)	0.0538 (13)	0.0848 (19)	0.0312 (12)	−0.0106 (13)	0.0033 (12)
C27	0.0422 (10)	0.0472 (10)	0.0598 (13)	0.0303 (9)	0.0115 (9)	0.0236 (10)
C28	0.0467 (11)	0.0628 (13)	0.0794 (16)	0.0383 (11)	0.0190 (11)	0.0393 (12)
C29	0.0362 (9)	0.0419 (9)	0.0457 (11)	0.0275 (8)	0.0064 (8)	0.0131 (8)
C30	0.0419 (10)	0.0558 (11)	0.0542 (12)	0.0347 (9)	0.0208 (9)	0.0218 (9)
C31	0.0424 (10)	0.0477 (10)	0.0506 (12)	0.0292 (9)	0.0182 (9)	0.0238 (9)
C32	0.0348 (9)	0.0364 (9)	0.0398 (10)	0.0227 (7)	0.0063 (7)	0.0112 (7)
C33	0.0370 (9)	0.0469 (10)	0.0375 (10)	0.0282 (8)	0.0103 (8)	0.0148 (8)
C34	0.0406 (10)	0.0464 (10)	0.0435 (11)	0.0289 (8)	0.0117 (8)	0.0214 (8)
C35	0.0405 (9)	0.0381 (9)	0.0429 (10)	0.0247 (8)	0.0098 (8)	0.0144 (8)
C36	0.0409 (9)	0.0384 (9)	0.0394 (10)	0.0259 (8)	0.0072 (8)	0.0094 (8)
C37	0.0469 (11)	0.0385 (9)	0.0473 (11)	0.0228 (8)	0.0161 (9)	0.0127 (8)
C38	0.0500 (13)	0.0692 (15)	0.0706 (17)	0.0236 (12)	0.0104 (12)	0.0043 (13)
C39	0.0498 (14)	0.095 (2)	0.114 (3)	0.0298 (15)	0.0298 (16)	0.0049 (19)
C40	0.090 (2)	0.0655 (16)	0.116 (3)	0.0219 (16)	0.072 (2)	0.0228 (17)
C41	0.108 (2)	0.0781 (18)	0.0607 (17)	0.0425 (17)	0.0419 (16)	0.0292 (14)
C42	0.0760 (17)	0.0828 (17)	0.0606 (15)	0.0430 (14)	0.0248 (13)	0.0340 (13)
C43	0.236 (6)	0.213 (6)	0.147 (5)	0.177 (5)	0.008 (4)	0.031 (4)
C44	0.092 (2)	0.127 (3)	0.106 (3)	0.060 (2)	0.021 (2)	0.011 (2)

S1—C15	1.6834 (17)	C18—H18A	0.9700
S2—C36	1.6824 (17)	C18—H18B	0.9700
O1—C8	1.363 (2)	C19—C20	1.508 (3)
O1—C7	1.424 (3)	C19—H19A	0.9700
O2—C10	1.355 (2)	C19—H19B	0.9700
O2—H2A	0.838 (10)	C20—C21	1.524 (3)
O3—C29	1.3631 (19)	C20—H20A	0.9700
O3—C28	1.427 (2)	C20—H20B	0.9700
O4—C33	1.350 (2)	C21—H21A	0.9700
O4—H4'	0.843 (10)	C21—H21B	0.9700
N1—C14	1.281 (2)	C22—C27	1.364 (3)
N1—N2	1.3798 (19)	C22—C23	1.382 (3)
N2—C15	1.346 (2)	C22—H22	0.9300
N2—H2'	0.872 (9)	C23—C24	1.353 (4)
N3—C15	1.318 (2)	C23—H23	0.9300
N3—C16	1.464 (2)	C24—C25	1.347 (4)
N3—H3'	0.873 (9)	C24—H24	0.9300
N4—C35	1.278 (2)	C25—C26	1.385 (3)
N4—N5	1.3786 (19)	C25—H25	0.9300
N5—C36	1.343 (2)	C26—C27	1.364 (3)
N5—H5'	0.875 (9)	C26—H26	0.9300
N6—C36	1.323 (2)	C27—C28	1.501 (2)
N6—C37	1.455 (2)	C28—H28A	0.9700
N6—H6	0.875 (9)	C28—H28B	0.9700
N7—C44	1.125 (5)	C29—C34	1.378 (2)
C1—C6	1.368 (3)	C29—C30	1.387 (3)
C1—C2	1.383 (3)	C30—C31	1.366 (2)
C1—H1	0.9300	C30—H30	0.9300
C2—C3	1.342 (4)	C31—C32	1.394 (2)
C2—H2	0.9300	C31—H31	0.9300
C3—C4	1.357 (4)	C32—C33	1.396 (2)
C3—H3	0.9300	C32—C35	1.448 (2)
C4—C5	1.380 (3)	C33—C34	1.388 (2)
C4—H4	0.9300	C34—H34	0.9300
C5—C6	1.361 (3)	C35—H35	0.9300
C5—H5	0.9300	C37—C38	1.503 (3)
C6—C7	1.499 (3)	C37—C42	1.506 (3)
C7—H7A	0.9700	C37—H37	0.9800
C7—H7B	0.9700	C38—C39	1.518 (4)
C8—C13	1.385 (3)	C38—H38A	0.9700
C8—C9	1.385 (3)	C38—H38B	0.9700
C9—C10	1.390 (2)	C39—C40	1.529 (5)
C9—H9	0.9300	C39—H39A	0.9700
C10—C11	1.393 (2)	C39—H39B	0.9700
C11—C12	1.400 (2)	C40—C41	1.498 (5)
C11—C14	1.443 (2)	C40—H40A	0.9700
C12—C13	1.370 (2)	C40—H40B	0.9700
C12—H12	0.9300	C41—C42	1.527 (4)
C13—H13	0.9300	C41—H41A	0.9700
C14—H14	0.9300	C41—H41B	0.9700
C16—C21	1.509 (3)	C42—H42A	0.9700
C16—C17	1.511 (3)	C42—H42B	0.9700
C16—H16	0.9800	C43—C44	1.386 (6)
C17—C18	1.521 (3)	C43—H43A	0.9600
C17—H17A	0.9700	C43—H43B	0.9600
C17—H17B	0.9700	C43—H43C	0.9600
C18—C19	1.505 (3)
C8—O1—C7	118.05 (16)	C16—C21—H21A	109.6
C10—O2—H2A	109.1 (19)	C20—C21—H21A	109.6
C29—O3—C28	118.03 (15)	C16—C21—H21B	109.6
C33—O4—H4'	108.7 (17)	C20—C21—H21B	109.6
C14—N1—N2	115.26 (14)	H21A—C21—H21B	108.1
C15—N2—N1	121.70 (15)	C27—C22—C23	121.0 (2)
C15—N2—H2'	122.2 (15)	C27—C22—H22	119.5
N1—N2—H2'	116.1 (15)	C23—C22—H22	119.5
C15—N3—C16	124.67 (14)	C24—C23—C22	120.2 (3)
C15—N3—H3'	117.7 (14)	C24—C23—H23	119.9
C16—N3—H3'	117.6 (14)	C22—C23—H23	119.9
C35—N4—N5	116.27 (15)	C25—C24—C23	119.6 (2)
C36—N5—N4	120.82 (15)	C25—C24—H24	120.2
C36—N5—H5'	120.2 (15)	C23—C24—H24	120.2
N4—N5—H5'	118.9 (15)	C24—C25—C26	120.3 (2)
C36—N6—C37	125.36 (15)	C24—C25—H25	119.9
C36—N6—H6	113.2 (14)	C26—C25—H25	119.9
C37—N6—H6	121.3 (14)	C27—C26—C25	120.9 (2)
C6—C1—C2	120.6 (2)	C27—C26—H26	119.5
C6—C1—H1	119.7	C25—C26—H26	119.5
C2—C1—H1	119.7	C26—C27—C22	117.92 (19)
C3—C2—C1	120.8 (2)	C26—C27—C28	122.2 (2)
C3—C2—H2	119.6	C22—C27—C28	119.9 (2)
C1—C2—H2	119.6	O3—C28—C27	107.81 (16)
C2—C3—C4	119.3 (2)	O3—C28—H28A	110.1
C2—C3—H3	120.3	C27—C28—H28A	110.1
C4—C3—H3	120.3	O3—C28—H28B	110.1
C3—C4—C5	120.2 (3)	C27—C28—H28B	110.1
C3—C4—H4	119.9	H28A—C28—H28B	108.5
C5—C4—H4	119.9	O3—C29—C34	123.98 (16)
C6—C5—C4	121.2 (2)	O3—C29—C30	115.26 (16)
C6—C5—H5	119.4	C34—C29—C30	120.75 (15)
C4—C5—H5	119.4	C31—C30—C29	118.94 (17)
C5—C6—C1	117.9 (2)	C31—C30—H30	120.5
C5—C6—C7	120.2 (2)	C29—C30—H30	120.5
C1—C6—C7	121.9 (2)	C30—C31—C32	122.41 (17)
O1—C7—C6	108.31 (17)	C30—C31—H31	118.8
O1—C7—H7A	110.0	C32—C31—H31	118.8
C6—C7—H7A	110.0	C31—C32—C33	117.39 (15)
O1—C7—H7B	110.0	C31—C32—C35	119.59 (16)
C6—C7—H7B	110.0	C33—C32—C35	123.01 (16)
H7A—C7—H7B	108.4	O4—C33—C34	117.05 (16)
O1—C8—C13	115.07 (16)	O4—C33—C32	121.98 (15)
O1—C8—C9	124.33 (17)	C34—C33—C32	120.97 (16)
C13—C8—C9	120.58 (15)	C29—C34—C33	119.46 (16)
C8—C9—C10	119.27 (17)	C29—C34—H34	120.3
C8—C9—H9	120.4	C33—C34—H34	120.3
C10—C9—H9	120.4	N4—C35—C32	122.63 (16)
O2—C10—C9	116.81 (16)	N4—C35—H35	118.7
O2—C10—C11	121.93 (15)	C32—C35—H35	118.7
C9—C10—C11	121.26 (16)	N6—C36—N5	117.15 (15)
C10—C11—C12	117.46 (15)	N6—C36—S2	123.67 (14)
C10—C11—C14	123.34 (16)	N5—C36—S2	119.17 (14)
C12—C11—C14	119.19 (16)	N6—C37—C38	111.66 (18)
C13—C12—C11	122.03 (17)	N6—C37—C42	109.76 (17)
C13—C12—H12	119.0	C38—C37—C42	112.18 (19)
C11—C12—H12	119.0	N6—C37—H37	107.7
C12—C13—C8	119.33 (17)	C38—C37—H37	107.7
C12—C13—H13	120.3	C42—C37—H37	107.7
C8—C13—H13	120.3	C37—C38—C39	110.4 (2)
N1—C14—C11	123.32 (16)	C37—C38—H38A	109.6
N1—C14—H14	118.3	C39—C38—H38A	109.6
C11—C14—H14	118.3	C37—C38—H38B	109.6
N3—C15—N2	117.35 (15)	C39—C38—H38B	109.6
N3—C15—S1	123.54 (13)	H38A—C38—H38B	108.1
N2—C15—S1	119.07 (13)	C38—C39—C40	110.8 (3)
N3—C16—C21	111.38 (15)	C38—C39—H39A	109.5
N3—C16—C17	109.39 (14)	C40—C39—H39A	109.5
C21—C16—C17	111.35 (16)	C38—C39—H39B	109.5
N3—C16—H16	108.2	C40—C39—H39B	109.5
C21—C16—H16	108.2	H39A—C39—H39B	108.1
C17—C16—H16	108.2	C41—C40—C39	110.5 (2)
C16—C17—C18	110.61 (16)	C41—C40—H40A	109.5
C16—C17—H17A	109.5	C39—C40—H40A	109.5
C18—C17—H17A	109.5	C41—C40—H40B	109.5
C16—C17—H17B	109.5	C39—C40—H40B	109.5
C18—C17—H17B	109.5	H40A—C40—H40B	108.1
H17A—C17—H17B	108.1	C40—C41—C42	111.9 (3)
C19—C18—C17	111.81 (19)	C40—C41—H41A	109.2
C19—C18—H18A	109.3	C42—C41—H41A	109.2
C17—C18—H18A	109.3	C40—C41—H41B	109.2
C19—C18—H18B	109.3	C42—C41—H41B	109.2
C17—C18—H18B	109.3	H41A—C41—H41B	107.9
H18A—C18—H18B	107.9	C37—C42—C41	110.5 (2)
C18—C19—C20	111.37 (17)	C37—C42—H42A	109.5
C18—C19—H19A	109.4	C41—C42—H42A	109.5
C20—C19—H19A	109.4	C37—C42—H42B	109.5
C18—C19—H19B	109.4	C41—C42—H42B	109.5
C20—C19—H19B	109.4	H42A—C42—H42B	108.1
H19A—C19—H19B	108.0	C44—C43—H43A	109.5
C19—C20—C21	111.10 (18)	C44—C43—H43B	109.5
C19—C20—H20A	109.4	H43A—C43—H43B	109.5
C21—C20—H20A	109.4	C44—C43—H43C	109.5
C19—C20—H20B	109.4	H43A—C43—H43C	109.5
C21—C20—H20B	109.4	H43B—C43—H43C	109.5
H20A—C20—H20B	108.0	N7—C44—C43	177.9 (6)
C16—C21—C20	110.36 (17)
C14—N1—N2—C15	−177.55 (17)	C19—C20—C21—C16	−56.4 (2)
C35—N4—N5—C36	175.50 (18)	C27—C22—C23—C24	1.0 (5)
C6—C1—C2—C3	−1.8 (4)	C22—C23—C24—C25	−1.9 (5)
C1—C2—C3—C4	1.1 (4)	C23—C24—C25—C26	0.8 (4)
C2—C3—C4—C5	0.0 (5)	C24—C25—C26—C27	1.4 (4)
C3—C4—C5—C6	−0.3 (5)	C25—C26—C27—C22	−2.3 (4)
C4—C5—C6—C1	−0.3 (4)	C25—C26—C27—C28	178.0 (2)
C4—C5—C6—C7	178.2 (3)	C23—C22—C27—C26	1.1 (4)
C2—C1—C6—C5	1.3 (4)	C23—C22—C27—C28	−179.1 (3)
C2—C1—C6—C7	−177.2 (2)	C29—O3—C28—C27	167.25 (18)
C8—O1—C7—C6	−166.00 (18)	C26—C27—C28—O3	88.5 (3)
C5—C6—C7—O1	97.6 (3)	C22—C27—C28—O3	−91.3 (3)
C1—C6—C7—O1	−83.9 (3)	C28—O3—C29—C34	2.6 (3)
C7—O1—C8—C13	175.50 (19)	C28—O3—C29—C30	−176.06 (19)
C7—O1—C8—C9	−2.8 (3)	O3—C29—C30—C31	176.84 (19)
O1—C8—C9—C10	175.28 (18)	C34—C29—C30—C31	−1.9 (3)
C13—C8—C9—C10	−3.0 (3)	C29—C30—C31—C32	−0.6 (3)
C8—C9—C10—O2	−178.48 (17)	C30—C31—C32—C33	2.1 (3)
C8—C9—C10—C11	2.0 (3)	C30—C31—C32—C35	−178.45 (19)
O2—C10—C11—C12	−179.23 (17)	C31—C32—C33—O4	178.46 (19)
C9—C10—C11—C12	0.3 (3)	C35—C32—C33—O4	−1.0 (3)
O2—C10—C11—C14	1.2 (3)	C31—C32—C33—C34	−1.3 (3)
C9—C10—C11—C14	−179.29 (17)	C35—C32—C33—C34	179.32 (18)
C10—C11—C12—C13	−1.7 (3)	O3—C29—C34—C33	−175.91 (18)
C14—C11—C12—C13	177.95 (18)	C30—C29—C34—C33	2.7 (3)
C11—C12—C13—C8	0.7 (3)	O4—C33—C34—C29	179.20 (18)
O1—C8—C13—C12	−176.74 (17)	C32—C33—C34—C29	−1.1 (3)
C9—C8—C13—C12	1.7 (3)	N5—N4—C35—C32	−178.66 (17)
N2—N1—C14—C11	177.59 (16)	C31—C32—C35—N4	175.26 (19)
C10—C11—C14—N1	3.0 (3)	C33—C32—C35—N4	−5.3 (3)
C12—C11—C14—N1	−176.58 (17)	C37—N6—C36—N5	−179.92 (19)
C16—N3—C15—N2	179.03 (16)	C37—N6—C36—S2	−1.2 (3)
C16—N3—C15—S1	1.3 (3)	N4—N5—C36—N6	5.2 (3)
N1—N2—C15—N3	−6.0 (3)	N4—N5—C36—S2	−173.54 (14)
N1—N2—C15—S1	171.78 (13)	C36—N6—C37—C38	−84.5 (3)
C15—N3—C16—C21	84.1 (2)	C36—N6—C37—C42	150.4 (2)
C15—N3—C16—C17	−152.42 (18)	N6—C37—C38—C39	179.7 (2)
N3—C16—C17—C18	−179.61 (17)	C42—C37—C38—C39	−56.6 (3)
C21—C16—C17—C18	−56.1 (2)	C37—C38—C39—C40	56.6 (3)
C16—C17—C18—C19	54.8 (2)	C38—C39—C40—C41	−56.6 (3)
C17—C18—C19—C20	−54.8 (3)	C39—C40—C41—C42	55.7 (3)
C18—C19—C20—C21	55.5 (3)	N6—C37—C42—C41	179.9 (2)
N3—C16—C21—C20	179.42 (17)	C38—C37—C42—C41	55.1 (3)
C17—C16—C21—C20	57.0 (2)	C40—C41—C42—C37	−54.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···N4	0.88 (1)	2.21 (2)	2.655 (2)	111 (2)
N5—H5′···S2i	0.88 (1)	2.48 (1)	3.3495 (17)	173 (2)
N2—H2′···S1ii	0.87 (1)	2.44 (1)	3.3047 (16)	171 (2)
O2—H2A···N1	0.84 (1)	1.96 (2)	2.696 (2)	146 (3)
O4—H4′···N4	0.84 (1)	1.94 (2)	2.680 (2)	146 (2)
C12—H12···Cg1iii	0.93	2.95	3.811 (2)	154
C20—H20B···Cg2iv	0.96	2.87	3.715 (2)	146
C31—H31···Cg4v	0.93	2.84	3.714 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5′⋯S2i	0.88 (1)	2.48 (1)	3.3495 (17)	173 (2)
N2—H2′⋯S1ii	0.87 (1)	2.44 (1)	3.3047 (16)	171 (2)
O2—H2A⋯N1	0.84 (1)	1.96 (2)	2.696 (2)	146 (3)
O4—H4′⋯N4	0.84 (1)	1.94 (2)	2.680 (2)	146 (2)
C12—H12⋯Cg1iii	0.93	2.95	3.811 (2)	154
C20—H20B⋯Cg2iv	0.96	2.87	3.715 (2)	146
C31—H31⋯Cg4v	0.93	2.84	3.714 (2)	157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .