3-Hy-droxy-N'-[(E)-2-thienyl-methyl-idene]-2-naphtho-hydrazide.

The asymmetric unit of the title compound, C(16)H(12)N(2)O(2)S, contains three independent mol-ecules. Intra-molecular N-H⋯O hydrogen bonds in the three mol-ecules lead to very similar conformations: the thio-pene ring and naphthalene ring system in the three mol-ecules form dihedral angles of 10.3 (2), 9.1 (2) and 9.3 (3)°. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into chains propagating in [031].

Related literature

For related structures, see: Huang (2009 ▶); Liang et al. (2008 ▶); Shafiq et al. (2009 ▶).

Experimental

Crystal data

C16H12N2O2S

M = 296.34

Orthorhombic,

a = 19.8191 (16) Å

b = 6.2487 (5) Å

c = 33.947 (3) Å

V = 4204.1 (6) Å3

Z = 12

Mo Kα radiation

μ = 0.24 mm−1

T = 298 K

0.41 × 0.17 × 0.06 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.909, T max = 0.986

20887 measured reflections

7258 independent reflections

3449 reflections with I > 2σ(I)

R int = 0.077

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.078

S = 0.97

7258 reflections

569 parameters

11 restraints

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 3473 Friedel pairs

Flack parameter: 0.01 (7)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681005405X/cv5019sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005405X/cv5019Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H12N2O2S	Dx = 1.405 Mg m−3
Mr = 296.34	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 2181 reflections
a = 19.8191 (16) Å	θ = 2.4–26.4°
b = 6.2487 (5) Å	µ = 0.24 mm−1
c = 33.947 (3) Å	T = 298 K
V = 4204.1 (6) Å3	Block, yellow
Z = 12	0.41 × 0.17 × 0.06 mm
F(000) = 1848

Bruker SMART 1000 CCD area-detector diffractometer	7258 independent reflections
Radiation source: fine-focus sealed tube	3449 reflections with I > 2σ(I)
graphite	Rint = 0.077
phi and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→23
Tmin = 0.909, Tmax = 0.986	k = −7→6
20887 measured reflections	l = −40→38

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)] = 0.055	H-atom parameters constrained
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0055P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
7258 reflections	Δρmax = 0.28 e Å−3
569 parameters	Δρmin = −0.24 e Å−3
11 restraints	Absolute structure: Flack (1983), 3473 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (7)

	x	y	z	Uiso*/Ueq
C17	0.1250 (3)	1.3649 (9)	0.3320 (2)	0.0772 (16)
H17	0.1041	1.4728	0.3465	0.093*
C18	0.1214 (3)	1.3474 (9)	0.2938 (2)	0.0852 (18)
H18	0.0986	1.4477	0.2785	0.102*
C19	0.1535 (2)	1.1707 (8)	0.27682 (17)	0.0632 (15)
H19	0.1533	1.1341	0.2503	0.076*
C20	0.1862 (3)	1.0582 (9)	0.30730 (18)	0.0638 (14)
C21	0.2286 (3)	0.8714 (9)	0.30409 (19)	0.0645 (17)
H21	0.2388	0.8180	0.2792	0.077*
C22	0.3225 (3)	0.4907 (9)	0.35439 (19)	0.0496 (14)
C23	0.3623 (3)	0.2970 (8)	0.34149 (16)	0.0469 (14)
C24	0.3623 (3)	0.2105 (8)	0.30317 (18)	0.0533 (15)
C25	0.3998 (3)	0.0317 (8)	0.29514 (19)	0.0615 (17)
H25	0.3989	−0.0254	0.2698	0.074*
C26	0.4393 (3)	−0.0666 (9)	0.32362 (19)	0.0524 (16)
C27	0.4776 (3)	−0.2522 (10)	0.3153 (2)	0.076 (2)
H27	0.4769	−0.3107	0.2901	0.091*
C28	0.5149 (3)	−0.3436 (11)	0.3434 (2)	0.084 (2)
H28	0.5397	−0.4657	0.3375	0.101*
C29	0.5173 (3)	−0.2589 (13)	0.3819 (2)	0.092 (2)
H29	0.5430	−0.3244	0.4014	0.111*
C30	0.4813 (3)	−0.0799 (11)	0.3897 (2)	0.078 (2)
H30	0.4836	−0.0205	0.4148	0.094*
C31	0.4410 (3)	0.0179 (10)	0.36158 (19)	0.0547 (16)
C32	0.4021 (3)	0.1999 (9)	0.36920 (17)	0.0573 (16)
H32	0.4032	0.2579	0.3944	0.069*
C33	0.4184 (3)	1.8592 (9)	0.5359 (2)	0.080 (2)
H33	0.4346	1.9553	0.5545	0.096*
C34	0.4305 (3)	1.8749 (10)	0.4964 (2)	0.0744 (19)
H34	0.4572	1.9798	0.4848	0.089*
C35	0.3980 (2)	1.7149 (9)	0.47596 (17)	0.0592 (16)
H35	0.3994	1.7044	0.4486	0.071*
C36	0.3635 (2)	1.5730 (8)	0.49900 (16)	0.0495 (14)
C37	0.3271 (3)	1.3905 (8)	0.48448 (16)	0.0524 (15)
H37	0.3261	1.3596	0.4577	0.063*
C38	0.2277 (3)	0.9641 (9)	0.51485 (17)	0.0455 (15)
C39	0.1955 (2)	0.7777 (8)	0.49573 (14)	0.0381 (13)
C40	0.2039 (2)	0.7167 (8)	0.45615 (16)	0.0461 (14)
C41	0.1721 (3)	0.5405 (9)	0.44212 (16)	0.0573 (16)
H41	0.1794	0.5006	0.4161	0.069*
C42	0.1280 (3)	0.4142 (8)	0.46550 (17)	0.0492 (15)
C43	0.0939 (3)	0.2328 (9)	0.45136 (18)	0.0686 (18)
H43	0.0990	0.1920	0.4252	0.082*
C44	0.0541 (3)	0.1183 (9)	0.47519 (19)	0.0651 (17)
H44	0.0310	0.0003	0.4654	0.078*
C45	0.0470 (2)	0.1750 (9)	0.51481 (19)	0.0633 (17)
H45	0.0196	0.0923	0.5311	0.076*
C46	0.0790 (3)	0.3478 (8)	0.53006 (16)	0.0531 (15)
H46	0.0735	0.3849	0.5564	0.064*
C47	0.1208 (2)	0.4700 (8)	0.50523 (16)	0.0447 (14)
C48	0.1555 (2)	0.6543 (8)	0.51967 (15)	0.0448 (14)
H48	0.1508	0.6918	0.5460	0.054*
N3	0.2524 (2)	0.7774 (8)	0.33437 (14)	0.0580 (14)
N4	0.2909 (2)	0.5966 (7)	0.32609 (14)	0.0588 (13)
H53	0.2943	0.5528	0.3022	0.071*
N5	0.2959 (2)	1.2714 (7)	0.50920 (13)	0.0537 (12)
N6	0.2642 (2)	1.0966 (7)	0.49271 (13)	0.0504 (12)
H54	0.2680	1.0729	0.4679	0.061*
O2	0.31792 (19)	0.5390 (6)	0.38926 (11)	0.0695 (12)
O3	0.21923 (17)	1.0000 (5)	0.55059 (11)	0.0628 (10)
O5	0.32458 (17)	0.3078 (5)	0.27397 (10)	0.0675 (11)
H50	0.3139	0.2188	0.2574	0.101*
O6	0.2452 (2)	0.8363 (6)	0.43242 (11)	0.0657 (11)
H51	0.2565	0.7649	0.4133	0.099*
S2	0.17219 (9)	1.1672 (3)	0.35224 (5)	0.0873 (5)
S3	0.36965 (8)	1.6406 (3)	0.54683 (5)	0.0731 (5)
C1	0.1105 (3)	0.8520 (9)	0.1823 (2)	0.078 (2)
H1	0.0887	0.9485	0.1988	0.094*
C2	0.1095 (3)	0.8610 (10)	0.1431 (2)	0.077 (2)
H2	0.0854	0.9638	0.1291	0.093*
C3	0.1482 (2)	0.7003 (8)	0.12479 (16)	0.0556 (16)
H3	0.1535	0.6864	0.0977	0.067*
C4	0.1772 (2)	0.5665 (8)	0.15220 (17)	0.0543 (15)
C5	0.2184 (2)	0.3795 (8)	0.14311 (17)	0.0520 (15)
H5	0.2278	0.3432	0.1171	0.062*
C6	0.3083 (3)	−0.0401 (8)	0.18524 (19)	0.0481 (15)
C7	0.3449 (2)	−0.2287 (8)	0.16877 (15)	0.0398 (13)
C8	0.3466 (2)	−0.2926 (8)	0.12870 (17)	0.0507 (16)
C9	0.3838 (3)	−0.4635 (8)	0.11708 (17)	0.0536 (15)
H9	0.3842	−0.5012	0.0906	0.064*
C10	0.4212 (3)	−0.5836 (8)	0.14371 (19)	0.0493 (15)
C11	0.4587 (3)	−0.7676 (10)	0.13163 (19)	0.0676 (18)
H11	0.4596	−0.8079	0.1053	0.081*
C12	0.4926 (3)	−0.8815 (9)	0.1585 (2)	0.0762 (19)
H12	0.5179	−0.9994	0.1506	0.091*
C13	0.4904 (3)	−0.8241 (10)	0.1989 (2)	0.0767 (19)
H13	0.5135	−0.9056	0.2174	0.092*
C14	0.4548 (3)	−0.6509 (9)	0.21041 (18)	0.0634 (18)
H14	0.4543	−0.6134	0.2369	0.076*
C15	0.4193 (2)	−0.5292 (8)	0.18397 (18)	0.0463 (15)
C16	0.3803 (2)	−0.3475 (8)	0.19406 (16)	0.0495 (14)
H16	0.3792	−0.3078	0.2205	0.059*
N2	0.27772 (19)	0.0878 (6)	0.15848 (14)	0.0506 (12)
H2A	0.2806	0.0598	0.1337	0.061*
O1	0.30712 (18)	−0.0019 (6)	0.22020 (12)	0.0651 (11)
S1	0.15723 (9)	0.6402 (2)	0.19813 (5)	0.0774 (5)
N1	0.2415 (2)	0.2660 (7)	0.17149 (14)	0.0509 (12)
O4	0.31007 (17)	−0.1791 (5)	0.10045 (10)	0.0603 (10)
H4	0.2714	−0.2252	0.0995	0.090*

	U11	U22	U33	U12	U13	U23
C17	0.069 (4)	0.070 (4)	0.093 (3)	0.007 (3)	0.021 (4)	−0.023 (3)
C18	0.099 (5)	0.064 (4)	0.093 (3)	0.024 (3)	0.009 (4)	−0.010 (3)
C19	0.066 (4)	0.054 (4)	0.070 (2)	0.017 (3)	0.009 (3)	−0.004 (3)
C20	0.059 (4)	0.060 (4)	0.072 (3)	0.009 (2)	0.007 (3)	−0.009 (3)
C21	0.069 (4)	0.067 (5)	0.058 (5)	−0.002 (3)	0.001 (4)	−0.006 (4)
C22	0.047 (4)	0.059 (4)	0.043 (4)	−0.010 (3)	0.003 (3)	−0.001 (4)
C23	0.046 (4)	0.056 (4)	0.038 (4)	−0.005 (3)	0.007 (3)	−0.007 (3)
C24	0.050 (4)	0.051 (4)	0.059 (4)	0.001 (3)	0.004 (3)	−0.002 (3)
C25	0.065 (4)	0.056 (4)	0.063 (4)	0.013 (3)	−0.007 (3)	−0.018 (3)
C26	0.044 (4)	0.047 (4)	0.067 (5)	0.001 (3)	0.005 (3)	0.005 (3)
C27	0.070 (5)	0.061 (4)	0.097 (6)	0.002 (3)	−0.012 (4)	0.007 (4)
C28	0.065 (5)	0.069 (5)	0.118 (7)	0.008 (4)	0.013 (5)	0.022 (5)
C29	0.073 (5)	0.107 (7)	0.097 (7)	0.001 (5)	−0.002 (5)	0.058 (6)
C30	0.066 (5)	0.090 (6)	0.077 (5)	−0.004 (4)	0.011 (4)	0.023 (4)
C31	0.047 (4)	0.064 (4)	0.053 (5)	−0.004 (3)	0.000 (3)	0.010 (4)
C32	0.056 (4)	0.066 (4)	0.051 (4)	−0.014 (3)	−0.003 (3)	0.002 (3)
C33	0.056 (4)	0.067 (4)	0.118 (7)	−0.016 (3)	−0.017 (4)	−0.015 (5)
C34	0.070 (5)	0.071 (5)	0.082 (5)	−0.011 (4)	−0.009 (4)	0.011 (4)
C35	0.059 (4)	0.063 (4)	0.057 (4)	−0.004 (3)	0.000 (3)	−0.002 (4)
C36	0.044 (3)	0.048 (4)	0.056 (4)	0.007 (3)	−0.002 (3)	0.006 (3)
C37	0.059 (4)	0.054 (4)	0.045 (4)	−0.001 (3)	0.005 (3)	−0.006 (3)
C38	0.043 (4)	0.053 (4)	0.041 (4)	0.009 (3)	−0.002 (3)	−0.006 (3)
C39	0.043 (3)	0.044 (3)	0.028 (3)	0.004 (2)	0.002 (3)	−0.010 (3)
C40	0.043 (4)	0.043 (4)	0.052 (4)	0.005 (3)	0.007 (3)	0.004 (3)
C41	0.061 (4)	0.067 (4)	0.044 (4)	−0.009 (3)	0.006 (3)	−0.021 (3)
C42	0.044 (4)	0.049 (4)	0.055 (4)	0.004 (3)	−0.006 (3)	−0.006 (3)
C43	0.065 (5)	0.075 (5)	0.065 (5)	−0.025 (3)	0.003 (4)	−0.009 (4)
C44	0.061 (4)	0.066 (5)	0.069 (5)	−0.008 (3)	−0.006 (4)	−0.009 (4)
C45	0.051 (4)	0.065 (5)	0.073 (5)	−0.009 (3)	0.008 (3)	0.009 (4)
C46	0.063 (4)	0.053 (4)	0.043 (4)	0.001 (3)	0.001 (3)	0.003 (3)
C47	0.041 (3)	0.042 (3)	0.051 (4)	0.009 (3)	−0.004 (3)	0.002 (3)
C48	0.057 (4)	0.041 (3)	0.037 (3)	0.018 (3)	0.000 (3)	−0.005 (3)
N3	0.058 (4)	0.050 (3)	0.066 (4)	−0.005 (3)	0.012 (3)	−0.019 (3)
N4	0.073 (4)	0.061 (4)	0.042 (3)	0.002 (3)	0.008 (3)	−0.018 (3)
N5	0.058 (3)	0.045 (3)	0.058 (4)	0.003 (2)	−0.004 (3)	−0.008 (3)
N6	0.064 (3)	0.047 (3)	0.040 (3)	−0.004 (2)	0.005 (3)	−0.012 (2)
O2	0.090 (3)	0.081 (3)	0.037 (3)	0.003 (2)	0.006 (2)	−0.014 (2)
O3	0.074 (3)	0.068 (3)	0.047 (3)	−0.0139 (19)	0.009 (2)	−0.011 (2)
O5	0.086 (3)	0.064 (3)	0.053 (3)	0.020 (2)	−0.007 (2)	−0.018 (2)
O6	0.079 (3)	0.072 (3)	0.045 (3)	−0.016 (2)	0.012 (2)	−0.017 (2)
S2	0.0958 (14)	0.0883 (13)	0.0779 (13)	0.0070 (10)	0.0068 (11)	−0.0152 (11)
S3	0.0846 (13)	0.0801 (12)	0.0545 (11)	−0.0074 (9)	−0.0003 (10)	−0.0064 (10)
C1	0.071 (5)	0.061 (5)	0.103 (7)	0.009 (3)	0.015 (4)	−0.018 (5)
C2	0.058 (4)	0.057 (5)	0.116 (7)	0.006 (3)	−0.003 (4)	−0.002 (5)
C3	0.062 (4)	0.055 (4)	0.050 (4)	−0.001 (3)	0.009 (3)	0.008 (3)
C4	0.053 (4)	0.040 (4)	0.069 (5)	0.000 (3)	0.008 (3)	−0.006 (3)
C5	0.059 (4)	0.044 (4)	0.052 (4)	−0.001 (3)	−0.002 (3)	−0.002 (3)
C6	0.047 (4)	0.043 (4)	0.055 (4)	−0.006 (3)	−0.001 (3)	−0.002 (3)
C7	0.046 (3)	0.041 (3)	0.032 (4)	0.000 (3)	−0.005 (3)	−0.003 (3)
C8	0.044 (4)	0.052 (4)	0.056 (4)	0.008 (3)	−0.006 (3)	0.004 (3)
C9	0.065 (4)	0.046 (4)	0.050 (4)	0.011 (3)	0.004 (3)	−0.016 (3)
C10	0.040 (4)	0.044 (4)	0.063 (5)	0.001 (3)	0.004 (3)	−0.002 (3)
C11	0.061 (4)	0.069 (5)	0.073 (5)	−0.006 (4)	0.001 (4)	−0.003 (4)
C12	0.060 (5)	0.070 (5)	0.098 (6)	0.012 (3)	−0.003 (5)	−0.012 (5)
C13	0.062 (5)	0.066 (5)	0.102 (6)	0.003 (3)	−0.010 (4)	0.014 (4)
C14	0.057 (4)	0.053 (4)	0.080 (5)	0.014 (3)	0.003 (3)	−0.009 (4)
C15	0.038 (4)	0.043 (4)	0.058 (5)	0.003 (3)	−0.002 (3)	0.003 (3)
C16	0.047 (3)	0.057 (4)	0.045 (4)	−0.007 (3)	−0.005 (3)	−0.008 (3)
N2	0.061 (3)	0.049 (3)	0.042 (3)	0.002 (2)	−0.005 (3)	−0.009 (3)
O1	0.084 (3)	0.065 (3)	0.047 (3)	0.014 (2)	−0.002 (2)	−0.011 (2)
S1	0.0790 (12)	0.0771 (12)	0.0762 (12)	0.0032 (10)	0.0082 (10)	−0.0121 (11)
N1	0.057 (3)	0.039 (3)	0.057 (3)	0.007 (2)	0.004 (3)	−0.003 (2)
O4	0.065 (3)	0.069 (3)	0.048 (3)	0.010 (2)	0.006 (2)	−0.012 (2)

C17—C18	1.306 (8)	C42—C47	1.400 (7)
C17—S2	1.695 (6)	C43—C44	1.337 (7)
C17—H17	0.9300	C43—H43	0.9300
C18—C19	1.398 (6)	C44—C45	1.398 (7)
C18—H18	0.9300	C44—H44	0.9300
C19—C20	1.409 (7)	C45—C46	1.355 (6)
C19—H19	0.9300	C45—H45	0.9300
C20—C21	1.442 (7)	C46—C47	1.407 (6)
C20—S2	1.694 (6)	C46—H46	0.9300
C21—N3	1.274 (6)	C47—C48	1.427 (6)
C21—H21	0.9300	C48—H48	0.9300
C22—O2	1.225 (6)	N3—N4	1.392 (5)
C22—N4	1.323 (6)	N4—H53	0.8600
C22—C23	1.510 (7)	N5—N6	1.379 (5)
C23—C32	1.369 (6)	N6—H54	0.8600
C23—C24	1.408 (7)	O5—O1	2.682 (5)
C24—O5	1.382 (6)	O5—H50	0.8199
C24—C25	1.370 (6)	O6—H51	0.8200
C25—C26	1.387 (7)	C1—C2	1.332 (7)
C25—H25	0.9300	C1—S1	1.702 (6)
C26—C31	1.393 (7)	C1—H1	0.9300
C26—C27	1.415 (7)	C2—C3	1.409 (7)
C27—C28	1.336 (8)	C2—H2	0.9300
C27—H27	0.9300	C3—C4	1.376 (6)
C28—C29	1.409 (9)	C3—H3	0.9300
C28—H28	0.9300	C4—C5	1.459 (7)
C29—C30	1.353 (8)	C4—S1	1.673 (6)
C29—H29	0.9300	C5—N1	1.281 (6)
C30—C31	1.387 (7)	C5—H5	0.9300
C30—H30	0.9300	C6—O1	1.211 (6)
C31—C32	1.398 (6)	C6—N2	1.353 (6)
C32—H32	0.9300	C6—C7	1.493 (7)
C33—C34	1.365 (8)	C7—C16	1.334 (6)
C33—S3	1.713 (6)	C7—C8	1.418 (7)
C33—H33	0.9300	C8—C9	1.356 (6)
C34—C35	1.376 (7)	C8—O4	1.396 (5)
C34—H34	0.9300	C9—C10	1.389 (7)
C35—C36	1.365 (6)	C9—H9	0.9300
C35—H35	0.9300	C10—C15	1.409 (7)
C36—C37	1.437 (6)	C10—C11	1.430 (7)
C36—S3	1.682 (5)	C11—C12	1.338 (7)
C37—N5	1.280 (6)	C11—H11	0.9300
C37—H37	0.9300	C12—C13	1.418 (8)
C38—O3	1.245 (6)	C12—H12	0.9300
C38—N6	1.332 (6)	C13—C14	1.350 (7)
C38—C39	1.478 (6)	C13—H13	0.9300
C39—C48	1.373 (6)	C14—C15	1.370 (7)
C39—C40	1.406 (6)	C14—H14	0.9300
C40—C41	1.356 (6)	C15—C16	1.415 (6)
C40—O6	1.370 (5)	C16—H16	0.9300
C41—C42	1.420 (7)	N2—N1	1.397 (5)
C41—H41	0.9300	N2—H2A	0.8600
C42—C43	1.404 (7)	O4—H4	0.8200
C18—C17—S2	111.8 (5)	C45—C44—H44	119.8
C18—C17—H17	124.1	C46—C45—C44	121.5 (6)
S2—C17—H17	124.1	C46—C45—H45	119.3
C17—C18—C19	116.8 (6)	C44—C45—H45	119.3
C17—C18—H18	121.6	C45—C46—C47	118.7 (5)
C19—C18—H18	121.6	C45—C46—H46	120.7
C18—C19—C20	107.5 (6)	C47—C46—H46	120.7
C18—C19—H19	126.2	C42—C47—C46	120.1 (5)
C20—C19—H19	126.2	C42—C47—C48	118.9 (5)
C19—C20—C21	128.1 (6)	C46—C47—C48	121.0 (5)
C19—C20—S2	112.6 (4)	C39—C48—C47	121.8 (5)
C21—C20—S2	119.3 (5)	C39—C48—H48	119.1
N3—C21—C20	121.8 (6)	C47—C48—H48	119.1
N3—C21—H21	119.1	C21—N3—N4	114.5 (5)
C20—C21—H21	119.1	C22—N4—N3	121.2 (5)
O2—C22—N4	122.9 (5)	C22—N4—H53	119.4
O2—C22—C23	121.1 (5)	N3—N4—H53	119.4
N4—C22—C23	115.9 (5)	C37—N5—N6	114.5 (5)
C32—C23—C24	117.7 (5)	C38—N6—N5	120.7 (4)
C32—C23—C22	117.2 (5)	C38—N6—H54	119.6
C24—C23—C22	125.1 (5)	N5—N6—H54	119.6
O5—C24—C25	120.6 (5)	C24—O5—O1	103.9 (3)
O5—C24—C23	119.6 (5)	C24—O5—H50	109.6
C25—C24—C23	119.8 (6)	O1—O5—H50	7.9
C24—C25—C26	121.9 (6)	C40—O6—H51	109.5
C24—C25—H25	119.0	C17—S2—C20	91.1 (3)
C26—C25—H25	119.0	C36—S3—C33	91.8 (3)
C25—C26—C31	119.4 (5)	C2—C1—S1	110.9 (5)
C25—C26—C27	121.8 (6)	C2—C1—H1	124.6
C31—C26—C27	118.9 (6)	S1—C1—H1	124.6
C28—C27—C26	120.3 (7)	C1—C2—C3	113.7 (7)
C28—C27—H27	119.9	C1—C2—H2	123.1
C26—C27—H27	119.9	C3—C2—H2	123.1
C27—C28—C29	121.4 (7)	C4—C3—C2	111.2 (6)
C27—C28—H28	119.3	C4—C3—H3	124.4
C29—C28—H28	119.3	C2—C3—H3	124.4
C30—C29—C28	118.3 (7)	C3—C4—C5	125.3 (5)
C30—C29—H29	120.8	C3—C4—S1	111.4 (4)
C28—C29—H29	120.8	C5—C4—S1	123.3 (5)
C29—C30—C31	122.2 (7)	N1—C5—C4	119.0 (5)
C29—C30—H30	118.9	N1—C5—H5	120.5
C31—C30—H30	118.9	C4—C5—H5	120.5
C30—C31—C26	118.9 (6)	O1—C6—N2	122.2 (5)
C30—C31—C32	123.3 (6)	O1—C6—C7	122.1 (5)
C26—C31—C32	117.8 (6)	N2—C6—C7	115.6 (5)
C23—C32—C31	123.4 (6)	C16—C7—C8	116.6 (5)
C23—C32—H32	118.3	C16—C7—C6	117.0 (5)
C31—C32—H32	118.3	C8—C7—C6	126.4 (5)
C34—C33—S3	111.7 (5)	C9—C8—O4	118.8 (5)
C34—C33—H33	124.2	C9—C8—C7	120.9 (5)
S3—C33—H33	124.2	O4—C8—C7	120.2 (5)
C33—C34—C35	111.1 (6)	C8—C9—C10	121.7 (5)
C33—C34—H34	124.4	C8—C9—H9	119.1
C35—C34—H34	124.4	C10—C9—H9	119.1
C36—C35—C34	114.6 (6)	C9—C10—C15	119.1 (5)
C36—C35—H35	122.7	C9—C10—C11	121.7 (6)
C34—C35—H35	122.7	C15—C10—C11	119.1 (5)
C35—C36—C37	124.8 (5)	C12—C11—C10	119.6 (6)
C35—C36—S3	110.7 (4)	C12—C11—H11	120.2
C37—C36—S3	124.5 (4)	C10—C11—H11	120.2
N5—C37—C36	118.6 (5)	C11—C12—C13	120.6 (6)
N5—C37—H37	120.7	C11—C12—H12	119.7
C36—C37—H37	120.7	C13—C12—H12	119.7
O3—C38—N6	120.7 (5)	C14—C13—C12	120.0 (6)
O3—C38—C39	120.8 (5)	C14—C13—H13	120.0
N6—C38—C39	118.5 (5)	C12—C13—H13	120.0
C48—C39—C40	118.8 (5)	C13—C14—C15	121.6 (6)
C48—C39—C38	115.6 (5)	C13—C14—H14	119.2
C40—C39—C38	125.6 (5)	C15—C14—H14	119.2
C41—C40—O6	121.0 (5)	C14—C15—C10	119.2 (5)
C41—C40—C39	120.0 (5)	C14—C15—C16	124.5 (6)
O6—C40—C39	119.0 (5)	C10—C15—C16	116.3 (5)
C40—C41—C42	122.8 (5)	C7—C16—C15	125.3 (5)
C40—C41—H41	118.6	C7—C16—H16	117.4
C42—C41—H41	118.6	C15—C16—H16	117.4
C43—C42—C47	118.8 (5)	C6—N2—N1	119.3 (5)
C43—C42—C41	123.6 (5)	C6—N2—H2A	120.4
C47—C42—C41	117.5 (5)	N1—N2—H2A	120.4
C44—C43—C42	120.6 (6)	C6—O1—O5	143.8 (4)
C44—C43—H43	119.7	C4—S1—C1	92.8 (3)
C42—C43—H43	119.7	C5—N1—N2	112.8 (5)
C43—C44—C45	120.4 (6)	C8—O4—H4	109.5
C43—C44—H44	119.8
S2—C17—C18—C19	2.5 (8)	C38—C39—C48—C47	179.6 (4)
C17—C18—C19—C20	−3.3 (8)	C42—C47—C48—C39	−0.1 (7)
C18—C19—C20—C21	−176.7 (6)	C46—C47—C48—C39	−178.8 (5)
C18—C19—C20—S2	2.7 (6)	C20—C21—N3—N4	178.5 (5)
C19—C20—C21—N3	−176.1 (6)	O2—C22—N4—N3	2.8 (8)
S2—C20—C21—N3	4.5 (8)	C23—C22—N4—N3	179.8 (4)
O2—C22—C23—C32	−10.7 (8)	C21—N3—N4—C22	175.6 (5)
N4—C22—C23—C32	172.2 (5)	C36—C37—N5—N6	−178.1 (4)
O2—C22—C23—C24	170.0 (5)	O3—C38—N6—N5	3.0 (7)
N4—C22—C23—C24	−7.1 (8)	C39—C38—N6—N5	−179.2 (4)
C32—C23—C24—O5	−177.9 (5)	C37—N5—N6—C38	−177.3 (5)
C22—C23—C24—O5	1.4 (8)	C25—C24—O5—O1	21.7 (6)
C32—C23—C24—C25	1.7 (8)	C23—C24—O5—O1	−158.7 (4)
C22—C23—C24—C25	−179.0 (5)	C18—C17—S2—C20	−0.6 (6)
O5—C24—C25—C26	178.6 (5)	C19—C20—S2—C17	−1.3 (5)
C23—C24—C25—C26	−1.0 (8)	C21—C20—S2—C17	178.1 (5)
C24—C25—C26—C31	0.0 (8)	C35—C36—S3—C33	0.0 (4)
C24—C25—C26—C27	179.5 (5)	C37—C36—S3—C33	179.9 (4)
C25—C26—C27—C28	−179.7 (6)	C34—C33—S3—C36	−1.4 (5)
C31—C26—C27—C28	−0.2 (9)	S1—C1—C2—C3	−1.8 (8)
C26—C27—C28—C29	−0.2 (10)	C1—C2—C3—C4	1.5 (8)
C27—C28—C29—C30	−0.6 (10)	C2—C3—C4—C5	177.8 (5)
C28—C29—C30—C31	1.9 (10)	C2—C3—C4—S1	−0.4 (6)
C29—C30—C31—C26	−2.2 (9)	C3—C4—C5—N1	−178.9 (5)
C29—C30—C31—C32	178.4 (6)	S1—C4—C5—N1	−0.9 (7)
C25—C26—C31—C30	−179.1 (5)	O1—C6—C7—C16	−4.1 (8)
C27—C26—C31—C30	1.4 (8)	N2—C6—C7—C16	174.5 (5)
C25—C26—C31—C32	0.2 (8)	O1—C6—C7—C8	176.8 (5)
C27—C26—C31—C32	−179.3 (5)	N2—C6—C7—C8	−4.7 (7)
C24—C23—C32—C31	−1.5 (8)	C16—C7—C8—C9	−1.4 (7)
C22—C23—C32—C31	179.2 (5)	C6—C7—C8—C9	177.7 (5)
C30—C31—C32—C23	179.9 (5)	C16—C7—C8—O4	179.0 (4)
C26—C31—C32—C23	0.5 (8)	C6—C7—C8—O4	−1.9 (8)
S3—C33—C34—C35	2.3 (7)	O4—C8—C9—C10	−179.9 (5)
C33—C34—C35—C36	−2.4 (8)	C7—C8—C9—C10	0.5 (8)
C34—C35—C36—C37	−178.6 (5)	C8—C9—C10—C15	1.3 (8)
C34—C35—C36—S3	1.4 (6)	C8—C9—C10—C11	178.1 (5)
C35—C36—C37—N5	−178.9 (5)	C9—C10—C11—C12	−178.3 (5)
S3—C36—C37—N5	1.1 (7)	C15—C10—C11—C12	−1.6 (8)
O3—C38—C39—C48	1.5 (7)	C10—C11—C12—C13	1.4 (9)
N6—C38—C39—C48	−176.4 (5)	C11—C12—C13—C14	−1.2 (9)
O3—C38—C39—C40	−177.1 (5)	C12—C13—C14—C15	1.0 (9)
N6—C38—C39—C40	5.0 (7)	C13—C14—C15—C10	−1.2 (8)
C48—C39—C40—C41	0.8 (8)	C13—C14—C15—C16	179.2 (5)
C38—C39—C40—C41	179.3 (5)	C9—C10—C15—C14	178.3 (5)
C48—C39—C40—O6	−178.4 (4)	C11—C10—C15—C14	1.5 (8)
C38—C39—C40—O6	0.2 (7)	C9—C10—C15—C16	−2.1 (7)
O6—C40—C41—C42	−178.9 (5)	C11—C10—C15—C16	−178.9 (4)
C39—C40—C41—C42	2.0 (8)	C8—C7—C16—C15	0.6 (7)
C40—C41—C42—C43	179.1 (5)	C6—C7—C16—C15	−178.6 (5)
C40—C41—C42—C47	−3.7 (8)	C14—C15—C16—C7	−179.2 (5)
C47—C42—C43—C44	1.5 (9)	C10—C15—C16—C7	1.2 (8)
C41—C42—C43—C44	178.7 (6)	O1—C6—N2—N1	−2.4 (8)
C42—C43—C44—C45	−1.4 (9)	C7—C6—N2—N1	179.1 (4)
C43—C44—C45—C46	1.0 (9)	N2—C6—O1—O5	−46.8 (9)
C44—C45—C46—C47	−0.8 (8)	C7—C6—O1—O5	131.6 (5)
C43—C42—C47—C46	−1.3 (7)	C24—O5—O1—C6	−136.0 (7)
C41—C42—C47—C46	−178.6 (5)	C3—C4—S1—C1	−0.5 (4)
C43—C42—C47—C48	180.0 (5)	C5—C4—S1—C1	−178.8 (5)
C41—C42—C47—C48	2.7 (7)	C2—C1—S1—C4	1.3 (5)
C45—C46—C47—C42	0.9 (7)	C4—C5—N1—N2	177.6 (4)
C45—C46—C47—C48	179.6 (5)	C6—N2—N1—C5	176.4 (5)
C40—C39—C48—C47	−1.7 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H51···O2	0.82	2.03	2.771 (5)	149
N6—H54···O6	0.86	1.96	2.641 (5)	135
N2—H2A···O4	0.86	1.96	2.660 (5)	138
N4—H53···O5	0.86	1.90	2.614 (5)	139
O5—H50···O1	0.82	1.87	2.682 (5)	169
O4—H4···O3i	0.82	2.40	2.688 (5)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H51⋯O2	0.82	2.03	2.771 (5)	149
N6—H54⋯O6	0.86	1.96	2.641 (5)	135
N2—H2A⋯O4	0.86	1.96	2.660 (5)	138
N4—H53⋯O5	0.86	1.90	2.614 (5)	139
O5—H50⋯O1	0.82	1.87	2.682 (5)	169
O4—H4⋯O3i	0.82	2.40	2.688 (5)	102

Symmetry code: (i) .