Ethyl 2-[2-(2,4-diphenyl-3-aza-bicyclo-[3.3.1]nonan-9-yl-idene)hydrazin-1-yl]-4-methyl-1,3-thia-zole-5-carboxyl-ate di-methyl-formamide monosolvate.

In the title mol-ecule, C27H30N4O2S·C3H7NO, the fused piperidine and cyclo-hexane rings adopt a twin chair conformation and the phenyl groups occupy equatorial sites. The phenyl rings make a dihedral angle of 40.74 (2)°. In the crystal, the di-methyl-formamide solvent mol-ecule is connected to the main mol-ecule by an N-H⋯O hydrogen bond. An additional N-H⋯O hydrogen bond connects mol-ecules into chains along [100]. Pairs of weak C-H⋯O hydrogen bonds connect inversion-related chains. The ethyl group was refined as disordered over two sets of sites with an occupancy ratio of 0.660 (17):0.340 (17).

Related literature

For the biological activity of related structures, see: Ramachandran et al. (2009 ▶); Hutchinson et al. (2002 ▶); Bondock et al. (2007 ▶). For bicyclic compounds, see: Jeyaraman & Avila (1981 ▶).

Experimental

Crystal data

C27H30N4O2S·C3H7NO

M = 547.71

Monoclinic,

a = 12.700 (5) Å

b = 19.427 (5) Å

c = 13.203 (5) Å

β = 115.249 (5)°

V = 2946.3 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.15 mm−1

T = 293 K

0.35 × 0.35 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.937, T max = 0.965

25815 measured reflections

5179 independent reflections

3606 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.154

S = 1.01

5179 reflections

379 parameters

40 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.56 e Å−3

Δρmin = −0.37 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: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, 1. DOI: 10.1107/S1600536813033540/lh5671sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033540/lh5671Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033540/lh5671Isup3.cdx

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033540/lh5671Isup4.cml

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

C27H30N4O2S·C3H7NO	F(000) = 1168
Mr = 547.71	Dx = 1.235 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6962 reflections
a = 12.700 (5) Å	θ = 2.1–22.4°
b = 19.427 (5) Å	µ = 0.15 mm−1
c = 13.203 (5) Å	T = 293 K
β = 115.249 (5)°	Block, colourless
V = 2946.3 (18) Å3	0.35 × 0.35 × 0.30 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	5179 independent reflections
Radiation source: fine-focus sealed tube	3606 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω and φ sacn scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −15→15
Tmin = 0.937, Tmax = 0.965	k = −20→23
25815 measured reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0579P)2 + 2.3626P] where P = (Fo2 + 2Fc2)/3
5179 reflections	(Δ/σ)max = 0.001
379 parameters	Δρmax = 0.56 e Å−3
40 restraints	Δρmin = −0.37 e Å−3

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	Occ. (<1)
C1	0.0735 (2)	0.24044 (14)	0.5466 (2)	0.0499 (7)
C2	0.0996 (3)	0.27051 (16)	0.6495 (3)	0.0647 (8)
H2	0.0572	0.2579	0.6892	0.078*
C3	0.1867 (3)	0.31863 (18)	0.6946 (3)	0.0815 (11)
H3	0.2018	0.3387	0.7634	0.098*
C4	0.2508 (3)	0.33680 (19)	0.6382 (4)	0.0891 (12)
H4	0.3109	0.3686	0.6690	0.107*
C5	0.2264 (3)	0.3081 (2)	0.5363 (4)	0.0902 (12)
H5	0.2692	0.3211	0.4972	0.108*
C6	0.1386 (3)	0.25983 (18)	0.4907 (3)	0.0706 (9)
H6	0.1234	0.2403	0.4215	0.085*
C7	−0.0232 (2)	0.18797 (13)	0.5011 (2)	0.0450 (6)
H7	−0.0184	0.1591	0.5638	0.054*
C8	−0.0971 (2)	0.08953 (13)	0.3738 (2)	0.0445 (6)
H8	−0.0939	0.0613	0.4365	0.053*
C9	−0.0710 (2)	0.04318 (13)	0.2953 (2)	0.0452 (6)
C10	−0.0280 (2)	0.06844 (15)	0.2225 (2)	0.0546 (7)
H10	−0.0154	0.1155	0.2208	0.066*
C11	−0.0035 (3)	0.02520 (19)	0.1523 (3)	0.0673 (9)
H11	0.0247	0.0434	0.1036	0.081*
C12	−0.0204 (3)	−0.0437 (2)	0.1539 (3)	0.0750 (10)
H12	−0.0027	−0.0727	0.1073	0.090*
C13	−0.0633 (3)	−0.07009 (17)	0.2242 (3)	0.0743 (10)
H13	−0.0757	−0.1172	0.2248	0.089*
C14	−0.0887 (3)	−0.02709 (15)	0.2951 (3)	0.0613 (8)
H14	−0.1180	−0.0458	0.3427	0.074*
C15	−0.2198 (2)	0.12259 (15)	0.3180 (2)	0.0490 (7)
H15	−0.2783	0.0858	0.2944	0.059*
C16	−0.2341 (2)	0.16510 (14)	0.4064 (2)	0.0472 (6)
C17	−0.1453 (2)	0.22093 (14)	0.4488 (2)	0.0495 (7)
H17	−0.1569	0.2461	0.5076	0.059*
C18	−0.1687 (3)	0.27046 (16)	0.3508 (3)	0.0626 (8)
H18A	−0.2426	0.2933	0.3319	0.075*
H18B	−0.1086	0.3055	0.3749	0.075*
C19	−0.1718 (3)	0.23575 (17)	0.2467 (3)	0.0665 (9)
H19A	−0.0928	0.2250	0.2583	0.080*
H19B	−0.2043	0.2675	0.1841	0.080*
C20	−0.2433 (2)	0.17010 (17)	0.2176 (2)	0.0625 (8)
H20A	−0.2274	0.1449	0.1623	0.075*
H20B	−0.3252	0.1823	0.1837	0.075*
C21	−0.4752 (2)	0.10489 (15)	0.4414 (2)	0.0518 (7)
C22	−0.6309 (2)	0.06611 (18)	0.4541 (3)	0.0641 (9)
C23	−0.5903 (3)	0.10747 (18)	0.5450 (3)	0.0670 (9)
C24	−0.6432 (4)	0.1188 (2)	0.6213 (4)	0.0859 (12)
C27	−0.7378 (3)	0.0215 (2)	0.4136 (4)	0.0902 (12)
H27A	−0.7461	−0.0024	0.3470	0.135*
H27B	−0.8051	0.0498	0.3974	0.135*
H27C	−0.7305	−0.0113	0.4706	0.135*
C28	−0.7208 (4)	−0.0655 (2)	0.1020 (4)	0.1106 (15)
H28A	−0.7792	−0.0754	0.0281	0.166*
H28B	−0.7567	−0.0450	0.1455	0.166*
H28C	−0.6827	−0.1074	0.1371	0.166*
C29	−0.6557 (3)	0.0071 (2)	−0.0138 (3)	0.0943 (12)
H29C	−0.6091	0.0475	−0.0054	0.141*
H29A	−0.7365	0.0185	−0.0551	0.141*
H29B	−0.6344	−0.0275	−0.0534	0.141*
C30	−0.5483 (3)	0.00313 (18)	0.1851 (3)	0.0675 (8)
H30	−0.5396	−0.0152	0.2533	0.081*
N1	−0.00799 (18)	0.14310 (11)	0.41935 (18)	0.0453 (5)
N2	−0.31082 (18)	0.16070 (12)	0.44462 (18)	0.0512 (6)
N3	−0.39631 (19)	0.11185 (14)	0.3983 (2)	0.0567 (6)
N4	−0.56551 (19)	0.06438 (13)	0.3952 (2)	0.0583 (6)
N5	−0.6363 (2)	−0.01846 (13)	0.0948 (2)	0.0637 (7)
O1	−0.7381 (2)	0.09901 (17)	0.6088 (3)	0.1174 (11)
O2	−0.5722 (3)	0.15330 (17)	0.7104 (2)	0.1002 (9)
O3	−0.4768 (2)	0.04548 (16)	0.1866 (2)	0.0917 (8)
S1	−0.46094 (7)	0.14717 (5)	0.56068 (7)	0.0648 (3)
C25	−0.588 (2)	0.1963 (16)	0.8026 (13)	0.120 (6)	0.340 (17)
H25A	−0.5743	0.2446	0.7939	0.144*	0.340 (17)
H25B	−0.6672	0.1914	0.7946	0.144*	0.340 (17)
C26	−0.5059 (18)	0.1725 (11)	0.9147 (13)	0.091 (5)	0.340 (17)
H26A	−0.5358	0.1840	0.9682	0.137*	0.340 (17)
H26B	−0.4319	0.1945	0.9354	0.137*	0.340 (17)
H26C	−0.4965	0.1235	0.9135	0.137*	0.340 (17)
C25'	−0.6228 (7)	0.1578 (6)	0.7918 (6)	0.085 (2)	0.660 (17)
H25C	−0.6998	0.1783	0.7589	0.103*	0.660 (17)
H25D	−0.6268	0.1130	0.8225	0.103*	0.660 (17)
C26'	−0.5381 (12)	0.2028 (9)	0.8765 (14)	0.140 (5)	0.660 (17)
H26D	−0.5628	0.2118	0.9345	0.210*	0.660 (17)
H26E	−0.5326	0.2455	0.8423	0.210*	0.660 (17)
H26F	−0.4633	0.1808	0.9081	0.210*	0.660 (17)
H1A	0.0570 (18)	0.1231 (13)	0.451 (2)	0.051 (8)*
H3A	−0.415 (2)	0.0916 (13)	0.3356 (17)	0.051 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.0418 (14)	0.0513 (16)	0.0553 (16)	−0.0015 (12)	0.0194 (12)	−0.0048 (13)
C2	0.0544 (17)	0.070 (2)	0.073 (2)	−0.0053 (15)	0.0304 (16)	−0.0243 (17)
C3	0.064 (2)	0.075 (2)	0.096 (3)	−0.0101 (18)	0.026 (2)	−0.040 (2)
C4	0.065 (2)	0.070 (2)	0.118 (3)	−0.0231 (18)	0.025 (2)	−0.023 (2)
C5	0.078 (2)	0.093 (3)	0.107 (3)	−0.034 (2)	0.047 (2)	−0.001 (2)
C6	0.069 (2)	0.080 (2)	0.068 (2)	−0.0245 (17)	0.0339 (17)	−0.0077 (17)
C7	0.0438 (14)	0.0508 (15)	0.0434 (14)	−0.0053 (12)	0.0215 (12)	−0.0018 (12)
C8	0.0411 (13)	0.0510 (15)	0.0436 (14)	−0.0048 (12)	0.0203 (11)	−0.0011 (12)
C9	0.0353 (13)	0.0489 (16)	0.0490 (15)	−0.0025 (11)	0.0158 (11)	−0.0046 (12)
C10	0.0482 (16)	0.0595 (17)	0.0653 (18)	−0.0076 (13)	0.0331 (14)	−0.0098 (15)
C11	0.0583 (18)	0.083 (2)	0.072 (2)	0.0003 (16)	0.0382 (17)	−0.0126 (18)
C12	0.077 (2)	0.079 (3)	0.070 (2)	0.0138 (19)	0.0332 (19)	−0.0153 (19)
C13	0.091 (2)	0.0468 (18)	0.071 (2)	0.0058 (17)	0.0211 (19)	−0.0102 (16)
C14	0.0672 (19)	0.0564 (18)	0.0578 (18)	−0.0036 (15)	0.0242 (15)	0.0037 (15)
C15	0.0359 (13)	0.0662 (18)	0.0490 (15)	−0.0060 (12)	0.0220 (12)	−0.0080 (13)
C16	0.0380 (13)	0.0634 (17)	0.0438 (14)	0.0022 (12)	0.0210 (12)	−0.0036 (13)
C17	0.0449 (14)	0.0598 (17)	0.0525 (16)	−0.0029 (13)	0.0290 (13)	−0.0102 (13)
C18	0.0561 (17)	0.0620 (19)	0.075 (2)	0.0106 (15)	0.0330 (16)	0.0056 (16)
C19	0.0674 (19)	0.078 (2)	0.0617 (19)	0.0187 (17)	0.0348 (16)	0.0212 (17)
C20	0.0484 (16)	0.093 (2)	0.0455 (16)	0.0174 (16)	0.0193 (13)	−0.0005 (16)
C21	0.0392 (14)	0.0680 (18)	0.0523 (16)	0.0086 (13)	0.0235 (13)	0.0115 (14)
C22	0.0426 (16)	0.077 (2)	0.080 (2)	0.0187 (15)	0.0330 (16)	0.0376 (19)
C23	0.0543 (18)	0.085 (2)	0.079 (2)	0.0233 (17)	0.0450 (17)	0.037 (2)
C24	0.080 (3)	0.114 (3)	0.086 (3)	0.041 (2)	0.057 (2)	0.050 (2)
C27	0.0486 (18)	0.098 (3)	0.130 (3)	0.0033 (18)	0.044 (2)	0.033 (2)
C28	0.109 (3)	0.117 (3)	0.105 (3)	−0.050 (3)	0.045 (3)	−0.007 (3)
C29	0.074 (2)	0.134 (4)	0.063 (2)	−0.019 (2)	0.0183 (18)	0.007 (2)
C30	0.061 (2)	0.078 (2)	0.060 (2)	0.0036 (18)	0.0231 (17)	−0.0044 (17)
N1	0.0351 (11)	0.0515 (13)	0.0495 (13)	−0.0012 (10)	0.0182 (10)	−0.0055 (11)
N2	0.0390 (12)	0.0712 (15)	0.0486 (13)	−0.0025 (11)	0.0238 (10)	−0.0022 (12)
N3	0.0427 (13)	0.0850 (18)	0.0492 (14)	−0.0094 (12)	0.0262 (11)	−0.0104 (13)
N4	0.0361 (12)	0.0736 (16)	0.0659 (15)	0.0040 (11)	0.0224 (11)	0.0138 (13)
N5	0.0546 (15)	0.0708 (17)	0.0600 (16)	−0.0065 (13)	0.0190 (13)	−0.0008 (13)
O1	0.0866 (19)	0.164 (3)	0.145 (3)	0.0323 (19)	0.0910 (19)	0.058 (2)
O2	0.096 (2)	0.148 (3)	0.0854 (18)	0.0435 (19)	0.0665 (17)	0.0204 (18)
O3	0.0672 (15)	0.135 (2)	0.0749 (16)	−0.0336 (16)	0.0326 (13)	−0.0304 (15)
S1	0.0582 (5)	0.0880 (6)	0.0615 (5)	0.0065 (4)	0.0383 (4)	0.0060 (4)
C25	0.119 (13)	0.152 (14)	0.117 (11)	0.027 (11)	0.077 (10)	−0.002 (12)
C26	0.121 (11)	0.099 (11)	0.079 (8)	0.025 (8)	0.067 (8)	−0.005 (7)
C25'	0.096 (5)	0.096 (6)	0.099 (4)	−0.001 (4)	0.075 (4)	−0.009 (4)
C26'	0.133 (11)	0.165 (11)	0.147 (12)	−0.027 (9)	0.083 (10)	−0.078 (9)

C1—C6	1.375 (4)	C20—H20A	0.9700
C1—C2	1.383 (4)	C20—H20B	0.9700
C1—C7	1.509 (4)	C21—N4	1.308 (4)
C2—C3	1.375 (4)	C21—N3	1.354 (3)
C2—H2	0.9300	C21—S1	1.716 (3)
C3—C4	1.364 (5)	C22—C23	1.351 (5)
C3—H3	0.9300	C22—N4	1.358 (4)
C4—C5	1.364 (5)	C22—C27	1.503 (5)
C4—H4	0.9300	C23—C24	1.445 (5)
C5—C6	1.383 (5)	C23—S1	1.746 (3)
C5—H5	0.9300	C24—O1	1.208 (5)
C6—H6	0.9300	C24—O2	1.320 (5)
C7—N1	1.462 (3)	C27—H27A	0.9600
C7—C17	1.542 (4)	C27—H27B	0.9600
C7—H7	0.9800	C27—H27C	0.9600
C8—N1	1.464 (3)	C28—N5	1.443 (4)
C8—C9	1.512 (4)	C28—H28A	0.9600
C8—C15	1.551 (4)	C28—H28B	0.9600
C8—H8	0.9800	C28—H28C	0.9600
C9—C10	1.382 (4)	C29—N5	1.435 (4)
C9—C14	1.383 (4)	C29—H29C	0.9600
C10—C11	1.381 (4)	C29—H29A	0.9600
C10—H10	0.9300	C29—H29B	0.9600
C11—C12	1.357 (5)	C30—O3	1.219 (4)
C11—H11	0.9300	C30—N5	1.308 (4)
C12—C13	1.361 (5)	C30—H30	0.9300
C12—H12	0.9300	N1—H1A	0.844 (17)
C13—C14	1.392 (4)	N2—N3	1.374 (3)
C13—H13	0.9300	N3—H3A	0.853 (17)
C14—H14	0.9300	O2—C25'	1.472 (6)
C15—C16	1.502 (4)	O2—C25	1.559 (15)
C15—C20	1.536 (4)	C25—C26	1.474 (16)
C15—H15	0.9800	C25—H25A	0.9700
C16—N2	1.277 (3)	C25—H25B	0.9700
C16—C17	1.491 (4)	C26—H26A	0.9600
C17—C18	1.536 (4)	C26—H26B	0.9600
C17—H17	0.9800	C26—H26C	0.9600
C18—C19	1.517 (4)	C25'—C26'	1.465 (11)
C18—H18A	0.9700	C25'—H25C	0.9700
C18—H18B	0.9700	C25'—H25D	0.9700
C19—C20	1.517 (4)	C26'—H26D	0.9600
C19—H19A	0.9700	C26'—H26E	0.9600
C19—H19B	0.9700	C26'—H26F	0.9600
C6—C1—C2	117.7 (3)	C19—C20—H20A	108.7
C6—C1—C7	123.0 (3)	C15—C20—H20A	108.7
C2—C1—C7	119.3 (2)	C19—C20—H20B	108.7
C3—C2—C1	121.6 (3)	C15—C20—H20B	108.7
C3—C2—H2	119.2	H20A—C20—H20B	107.6
C1—C2—H2	119.2	N4—C21—N3	121.6 (3)
C4—C3—C2	119.8 (3)	N4—C21—S1	116.3 (2)
C4—C3—H3	120.1	N3—C21—S1	122.1 (2)
C2—C3—H3	120.1	C23—C22—N4	115.4 (3)
C3—C4—C5	119.7 (3)	C23—C22—C27	127.1 (3)
C3—C4—H4	120.1	N4—C22—C27	117.5 (3)
C5—C4—H4	120.1	C22—C23—C24	126.5 (3)
C4—C5—C6	120.6 (4)	C22—C23—S1	110.6 (2)
C4—C5—H5	119.7	C24—C23—S1	122.9 (3)
C6—C5—H5	119.7	O1—C24—O2	123.1 (4)
C1—C6—C5	120.6 (3)	O1—C24—C23	126.1 (5)
C1—C6—H6	119.7	O2—C24—C23	110.8 (4)
C5—C6—H6	119.7	C22—C27—H27A	109.5
N1—C7—C1	110.8 (2)	C22—C27—H27B	109.5
N1—C7—C17	110.0 (2)	H27A—C27—H27B	109.5
C1—C7—C17	112.9 (2)	C22—C27—H27C	109.5
N1—C7—H7	107.6	H27A—C27—H27C	109.5
C1—C7—H7	107.6	H27B—C27—H27C	109.5
C17—C7—H7	107.6	N5—C28—H28A	109.5
N1—C8—C9	110.3 (2)	N5—C28—H28B	109.5
N1—C8—C15	110.2 (2)	H28A—C28—H28B	109.5
C9—C8—C15	113.0 (2)	N5—C28—H28C	109.5
N1—C8—H8	107.7	H28A—C28—H28C	109.5
C9—C8—H8	107.7	H28B—C28—H28C	109.5
C15—C8—H8	107.7	N5—C29—H29C	109.5
C10—C9—C14	117.5 (3)	N5—C29—H29A	109.5
C10—C9—C8	122.1 (2)	H29C—C29—H29A	109.5
C14—C9—C8	120.4 (2)	N5—C29—H29B	109.5
C11—C10—C9	121.3 (3)	H29C—C29—H29B	109.5
C11—C10—H10	119.4	H29A—C29—H29B	109.5
C9—C10—H10	119.4	O3—C30—N5	124.9 (3)
C12—C11—C10	120.5 (3)	O3—C30—H30	117.6
C12—C11—H11	119.8	N5—C30—H30	117.6
C10—C11—H11	119.8	C7—N1—C8	113.88 (19)
C11—C12—C13	119.6 (3)	C7—N1—H1A	108.3 (19)
C11—C12—H12	120.2	C8—N1—H1A	107.3 (19)
C13—C12—H12	120.2	C16—N2—N3	117.5 (2)
C12—C13—C14	120.5 (3)	C21—N3—N2	117.9 (2)
C12—C13—H13	119.7	C21—N3—H3A	114.5 (19)
C14—C13—H13	119.7	N2—N3—H3A	126.0 (19)
C9—C14—C13	120.6 (3)	C21—N4—C22	110.3 (3)
C9—C14—H14	119.7	C30—N5—C29	121.0 (3)
C13—C14—H14	119.7	C30—N5—C28	120.9 (3)
C16—C15—C20	107.2 (2)	C29—N5—C28	118.0 (3)
C16—C15—C8	106.8 (2)	C24—O2—C25'	109.6 (4)
C20—C15—C8	116.4 (2)	C24—O2—C25	134.6 (12)
C16—C15—H15	108.7	C21—S1—C23	87.38 (16)
C20—C15—H15	108.7	C26—C25—O2	110.1 (13)
C8—C15—H15	108.7	C26—C25—H25A	109.6
N2—C16—C17	118.8 (2)	O2—C25—H25A	109.6
N2—C16—C15	129.5 (2)	C26—C25—H25B	109.6
C17—C16—C15	111.7 (2)	O2—C25—H25B	109.6
C16—C17—C18	107.2 (2)	H25A—C25—H25B	108.1
C16—C17—C7	108.7 (2)	C25—C26—H26A	109.5
C18—C17—C7	115.7 (2)	C25—C26—H26B	109.5
C16—C17—H17	108.4	H26A—C26—H26B	109.5
C18—C17—H17	108.4	C25—C26—H26C	109.5
C7—C17—H17	108.4	H26A—C26—H26C	109.5
C19—C18—C17	114.0 (2)	H26B—C26—H26C	109.5
C19—C18—H18A	108.8	C26'—C25'—O2	100.7 (9)
C17—C18—H18A	108.8	C26'—C25'—H25C	111.6
C19—C18—H18B	108.8	O2—C25'—H25C	111.6
C17—C18—H18B	108.8	C26'—C25'—H25D	111.6
H18A—C18—H18B	107.7	O2—C25'—H25D	111.6
C18—C19—C20	112.6 (2)	H25C—C25'—H25D	109.4
C18—C19—H19A	109.1	C25'—C26'—H26D	109.5
C20—C19—H19A	109.1	C25'—C26'—H26E	109.5
C18—C19—H19B	109.1	H26D—C26'—H26E	109.5
C20—C19—H19B	109.1	C25'—C26'—H26F	109.5
H19A—C19—H19B	107.8	H26D—C26'—H26F	109.5
C19—C20—C15	114.3 (2)	H26E—C26'—H26F	109.5
C6—C1—C2—C3	0.6 (5)	C7—C17—C18—C19	66.9 (3)
C7—C1—C2—C3	−179.9 (3)	C17—C18—C19—C20	45.7 (3)
C1—C2—C3—C4	−1.1 (5)	C18—C19—C20—C15	−45.1 (3)
C2—C3—C4—C5	1.3 (6)	C16—C15—C20—C19	53.1 (3)
C3—C4—C5—C6	−1.1 (6)	C8—C15—C20—C19	−66.4 (3)
C2—C1—C6—C5	−0.4 (5)	N4—C22—C23—C24	179.7 (3)
C7—C1—C6—C5	−179.9 (3)	C27—C22—C23—C24	−1.6 (5)
C4—C5—C6—C1	0.7 (6)	N4—C22—C23—S1	−0.4 (3)
C6—C1—C7—N1	22.4 (4)	C27—C22—C23—S1	178.2 (3)
C2—C1—C7—N1	−157.1 (3)	C22—C23—C24—O1	−8.7 (6)
C6—C1—C7—C17	−101.5 (3)	S1—C23—C24—O1	171.5 (3)
C2—C1—C7—C17	79.0 (3)	C22—C23—C24—O2	170.0 (3)
N1—C8—C9—C10	−39.0 (3)	S1—C23—C24—O2	−9.8 (4)
C15—C8—C9—C10	84.8 (3)	C1—C7—N1—C8	178.4 (2)
N1—C8—C9—C14	140.4 (3)	C17—C7—N1—C8	−56.0 (3)
C15—C8—C9—C14	−95.8 (3)	C9—C8—N1—C7	−176.8 (2)
C14—C9—C10—C11	−0.1 (4)	C15—C8—N1—C7	57.7 (3)
C8—C9—C10—C11	179.3 (3)	C17—C16—N2—N3	175.5 (2)
C9—C10—C11—C12	−0.5 (5)	C15—C16—N2—N3	−2.0 (4)
C10—C11—C12—C13	0.9 (5)	N4—C21—N3—N2	173.3 (2)
C11—C12—C13—C14	−0.7 (5)	S1—C21—N3—N2	−8.0 (4)
C10—C9—C14—C13	0.4 (4)	C16—N2—N3—C21	177.3 (3)
C8—C9—C14—C13	−179.1 (3)	N3—C21—N4—C22	179.8 (3)
C12—C13—C14—C9	0.0 (5)	S1—C21—N4—C22	1.0 (3)
N1—C8—C15—C16	−57.6 (3)	C23—C22—N4—C21	−0.3 (4)
C9—C8—C15—C16	178.4 (2)	C27—C22—N4—C21	−179.1 (3)
N1—C8—C15—C20	62.0 (3)	O3—C30—N5—C29	0.1 (5)
C9—C8—C15—C20	−61.9 (3)	O3—C30—N5—C28	−176.0 (4)
C20—C15—C16—N2	113.4 (3)	O1—C24—O2—C25'	4.6 (6)
C8—C15—C16—N2	−121.2 (3)	C23—C24—O2—C25'	−174.1 (5)
C20—C15—C16—C17	−64.3 (3)	O1—C24—O2—C25	−20.2 (15)
C8—C15—C16—C17	61.1 (3)	C23—C24—O2—C25	161.0 (14)
N2—C16—C17—C18	−113.0 (3)	N4—C21—S1—C23	−1.0 (2)
C15—C16—C17—C18	65.0 (3)	N3—C21—S1—C23	−179.8 (3)
N2—C16—C17—C7	121.3 (3)	C22—C23—S1—C21	0.8 (2)
C15—C16—C17—C7	−60.7 (3)	C24—C23—S1—C21	−179.4 (3)
N1—C7—C17—C16	55.5 (3)	C24—O2—C25—C26	128.4 (18)
C1—C7—C17—C16	179.9 (2)	C25'—O2—C25—C26	81 (3)
N1—C7—C17—C18	−65.1 (3)	C24—O2—C25'—C26'	−174.6 (10)
C1—C7—C17—C18	59.3 (3)	C25—O2—C25'—C26'	−28.6 (14)
C16—C17—C18—C19	−54.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1i	0.93	2.41	3.284 (4)	156
N1—H1A···O1ii	0.84 (2)	2.59 (2)	3.380 (4)	157 (2)
N3—H3A···O3	0.85 (2)	1.99 (2)	2.843 (4)	173 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O1i	0.93	2.41	3.284 (4)	156
N1—H1A⋯O1ii	0.84 (2)	2.59 (2)	3.380 (4)	157 (2)
N3—H3A⋯O3	0.85 (2)	1.99 (2)	2.843 (4)	173 (3)

Symmetry codes: (i) ; (ii) .