3,3'-Bis(3,4,5-trimethoxy-benzo-yl)-1,1'-(o-phenyl-ene)dithio-urea ethanol solvate.

In the mol-ecule of the title compound, C(28)H(30)N(4)O(8)S(2)·C(2)H(6)O, the benzene ring is oriented at dihedral angles of 38.50 (6) and 5.68 (5)° with respect to the trimethoxy-phenyl rings, while the two trimethoxy-phenyl rings are oriented at a dihedral angle of 44.18 (5)°. Intra-molecular N-H⋯O and N-H⋯S hydrogen bonds result in the formation of non-planar six-, seven- and eight-membered rings. The twisting modes of the two side arms are different [C-N-C-O and C-N-C-N torsion angles = 0.1 (3) and 11.8 (3)°, respectively, in one arm, and 4.6 (3) and -11.5 (3)° in the other]. In the crystal structure, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules.

Related literature

For a related structure, see: Thiam et al. (2008 ▶). For ring conformation puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C28H30N4O8S2·C2H6O

M = 660.75

Triclinic,

a = 7.7619 (15) Å

b = 14.473 (3) Å

c = 15.810 (3) Å

α = 67.113 (10)°

β = 73.069 (9)°

γ = 78.210 (12)°

V = 1556.9 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 113 (2) K

0.14 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.968, T max = 0.977

18692 measured reflections

6824 independent reflections

5694 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.115

S = 1.07

6824 reflections

433 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005 ▶); 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/S1600536808023556/hk2504sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023556/hk2504Isup2.hkl

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

C28H30N4O8S2·C2H6O1	Z = 2
Mr = 660.75	F000 = 696
Triclinic, P1	Dx = 1.409 Mg m−3
Hall symbol: -P 1	Melting point: 475 K
a = 7.7619 (15) Å	Mo Kα radiation λ = 0.71070 Å
b = 14.473 (3) Å	Cell parameters from 4542 reflections
c = 15.810 (3) Å	θ = 2.4–27.2º
α = 67.113 (10)º	µ = 0.23 mm−1
β = 73.069 (9)º	T = 113 (2) K
γ = 78.210 (12)º	Block, colorless
V = 1556.9 (5) Å3	0.14 × 0.12 × 0.10 mm

Rigaku Saturn CCD area-detector diffractometer	6824 independent reflections
Radiation source: rotating anode	5694 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.046
Detector resolution: 14.63 pixels mm-1	θmax = 27.2º
T = 113(2) K	θmin = 2.5º
ω scans	h = −9→9
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)	k = −18→18
Tmin = 0.968, Tmax = 0.977	l = −20→20
18692 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.050	w = 1/[σ2(Fo2) + (0.0441P)2 + 0.4672P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.115	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.26 e Å−3
6824 reflections	Δρmin = −0.32 e Å−3
433 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0140 (12)
Secondary atom site location: difference Fourier map

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 > 2sigma(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	0.47072 (7)	0.74462 (4)	0.51329 (3)	0.02065 (14)
S2	0.93034 (8)	0.44117 (4)	0.34131 (4)	0.02578 (15)
O1	1.02467 (19)	0.81993 (11)	0.48592 (9)	0.0250 (3)
O2	0.6648 (2)	0.51201 (10)	0.60921 (10)	0.0274 (4)
O3	1.2473 (2)	0.92569 (11)	0.70183 (10)	0.0286 (4)
O4	1.0727 (2)	0.82041 (11)	0.87598 (10)	0.0278 (4)
O5	0.7886 (2)	0.72356 (11)	0.90656 (10)	0.0287 (4)
O6	0.7859 (2)	0.27652 (10)	0.93150 (10)	0.0243 (3)
O7	0.7307 (2)	0.09337 (10)	0.94217 (9)	0.0244 (3)
O8	0.6871 (2)	0.06352 (10)	0.79539 (9)	0.0229 (3)
O9	0.5525 (2)	0.62076 (12)	0.74010 (11)	0.0285 (4)
H9	0.568 (4)	0.582 (2)	0.7125 (19)	0.043*
N1	0.8159 (2)	0.76073 (12)	0.41701 (11)	0.0177 (4)
H1	0.923 (3)	0.7772 (17)	0.4133 (16)	0.030 (7)*
N2	0.7346 (2)	0.57673 (12)	0.42050 (12)	0.0200 (4)
H2	0.685 (3)	0.5885 (17)	0.4737 (17)	0.028 (6)*
N3	0.7451 (2)	0.76939 (12)	0.56722 (12)	0.0184 (4)
H3A	0.673 (3)	0.7516 (17)	0.6201 (17)	0.026 (6)*
N4	0.7865 (2)	0.41196 (12)	0.52015 (11)	0.0198 (4)
H4A	0.830 (3)	0.3486 (19)	0.5237 (17)	0.036 (7)*
C1	0.7839 (3)	0.75352 (14)	0.33508 (13)	0.0175 (4)
C2	0.7479 (3)	0.66254 (14)	0.33554 (13)	0.0176 (4)
C3	0.7222 (3)	0.65850 (15)	0.25351 (14)	0.0207 (4)
H3	0.6911	0.5981	0.2539	0.025*
C4	0.7419 (3)	0.74278 (16)	0.17098 (14)	0.0238 (5)
H4	0.7272	0.7392	0.1148	0.029*
C5	0.7829 (3)	0.83206 (16)	0.17021 (14)	0.0249 (5)
H5	0.7987	0.8890	0.1134	0.030*
C6	0.8006 (3)	0.83775 (15)	0.25285 (14)	0.0213 (4)
H6	0.8242	0.8995	0.2532	0.026*
C7	0.6875 (3)	0.75825 (13)	0.49576 (13)	0.0167 (4)
C8	0.9074 (3)	0.79901 (14)	0.56059 (14)	0.0193 (4)
C9	0.9324 (3)	0.80961 (14)	0.64638 (14)	0.0191 (4)
C10	1.0706 (3)	0.86638 (14)	0.63139 (14)	0.0199 (4)
H10	1.1358	0.9001	0.5690	0.024*
C11	1.1123 (3)	0.87340 (15)	0.70806 (14)	0.0207 (4)
C12	1.0173 (3)	0.82339 (15)	0.80012 (14)	0.0217 (4)
C13	0.8750 (3)	0.76923 (15)	0.81379 (13)	0.0215 (4)
C14	0.8326 (3)	0.76151 (15)	0.73745 (14)	0.0219 (4)
H14	0.7370	0.7240	0.7471	0.026*
C15	0.8105 (3)	0.48263 (14)	0.42749 (14)	0.0189 (4)
C16	0.7225 (3)	0.42760 (15)	0.60517 (14)	0.0197 (4)
C17	0.7314 (3)	0.33652 (14)	0.69148 (13)	0.0180 (4)
C18	0.7536 (3)	0.35253 (15)	0.76900 (14)	0.0200 (4)
H18	0.7662	0.4182	0.7647	0.024*
C19	0.7570 (3)	0.27097 (15)	0.85280 (13)	0.0193 (4)
C20	0.7301 (3)	0.17510 (14)	0.86015 (13)	0.0187 (4)
C21	0.7114 (3)	0.16009 (14)	0.78097 (14)	0.0187 (4)
C22	0.7134 (3)	0.24057 (14)	0.69593 (13)	0.0172 (4)
H22	0.7026	0.2304	0.6419	0.021*
C23	1.3530 (3)	0.97237 (17)	0.60921 (16)	0.0301 (5)
H23A	1.4118	0.9209	0.5812	0.045*
H23B	1.4455	1.0069	0.6127	0.045*
H23C	1.2744	1.0214	0.5701	0.045*
C24	0.9843 (3)	0.89960 (16)	0.91201 (15)	0.0274 (5)
H24A	1.0110	0.9651	0.8628	0.041*
H24B	1.0285	0.8918	0.9667	0.041*
H24C	0.8532	0.8958	0.9311	0.041*
C25	0.6375 (3)	0.67215 (18)	0.92291 (16)	0.0349 (6)
H25A	0.5474	0.7192	0.8903	0.052*
H25B	0.5834	0.6455	0.9909	0.052*
H25C	0.6777	0.6164	0.8988	0.052*
C26	0.8306 (3)	0.37088 (16)	0.92470 (15)	0.0277 (5)
H26A	0.9337	0.3926	0.8709	0.042*
H26B	0.8624	0.3629	0.9829	0.042*
H26C	0.7262	0.4217	0.9156	0.042*
C27	0.5853 (3)	0.09950 (17)	1.02149 (16)	0.0348 (6)
H27A	0.6219	0.1337	1.0552	0.052*
H27B	0.5573	0.0314	1.0643	0.052*
H27C	0.4777	0.1376	0.9989	0.052*
C28	0.6740 (3)	0.04397 (15)	0.71577 (14)	0.0249 (5)
H28A	0.5684	0.0849	0.6929	0.037*
H28B	0.6608	−0.0276	0.7343	0.037*
H28C	0.7839	0.0613	0.6654	0.037*
C29	0.3609 (3)	0.63770 (18)	0.77554 (16)	0.0312 (5)
H29A	0.2987	0.6509	0.7249	0.037*
H29B	0.3343	0.6983	0.7937	0.037*
C30	0.2880 (4)	0.5489 (2)	0.85986 (17)	0.0428 (7)
H30A	0.3103	0.4893	0.8416	0.064*
H30B	0.1575	0.5639	0.8824	0.064*
H30C	0.3489	0.5358	0.9103	0.064*

	U11	U22	U33	U12	U13	U23
S1	0.0181 (3)	0.0241 (3)	0.0211 (3)	−0.00133 (19)	−0.0054 (2)	−0.0093 (2)
S2	0.0320 (3)	0.0201 (3)	0.0198 (3)	0.0011 (2)	−0.0011 (2)	−0.0068 (2)
O1	0.0240 (8)	0.0343 (8)	0.0179 (7)	−0.0081 (6)	−0.0015 (6)	−0.0103 (6)
O2	0.0436 (10)	0.0171 (7)	0.0200 (8)	0.0031 (6)	−0.0090 (7)	−0.0070 (6)
O3	0.0308 (9)	0.0363 (9)	0.0256 (8)	−0.0101 (7)	−0.0086 (7)	−0.0137 (7)
O4	0.0350 (9)	0.0317 (8)	0.0237 (8)	0.0064 (6)	−0.0154 (7)	−0.0160 (7)
O5	0.0367 (9)	0.0332 (8)	0.0156 (7)	−0.0084 (7)	−0.0045 (6)	−0.0069 (6)
O6	0.0353 (9)	0.0211 (7)	0.0203 (7)	−0.0044 (6)	−0.0106 (6)	−0.0076 (6)
O7	0.0329 (9)	0.0187 (7)	0.0160 (7)	0.0021 (6)	−0.0059 (6)	−0.0024 (6)
O8	0.0356 (9)	0.0149 (7)	0.0202 (7)	−0.0050 (6)	−0.0100 (6)	−0.0046 (6)
O9	0.0278 (9)	0.0318 (9)	0.0286 (9)	−0.0028 (7)	−0.0046 (7)	−0.0149 (7)
N1	0.0187 (9)	0.0202 (8)	0.0159 (8)	−0.0019 (6)	−0.0051 (7)	−0.0073 (7)
N2	0.0280 (10)	0.0165 (8)	0.0142 (8)	−0.0005 (7)	−0.0056 (7)	−0.0045 (7)
N3	0.0199 (9)	0.0227 (9)	0.0134 (8)	−0.0030 (7)	−0.0032 (7)	−0.0074 (7)
N4	0.0268 (10)	0.0137 (8)	0.0165 (8)	−0.0013 (7)	−0.0036 (7)	−0.0041 (7)
C1	0.0152 (10)	0.0219 (10)	0.0155 (9)	0.0005 (7)	−0.0032 (7)	−0.0084 (8)
C2	0.0171 (10)	0.0183 (9)	0.0158 (9)	0.0013 (7)	−0.0035 (8)	−0.0061 (8)
C3	0.0218 (11)	0.0214 (10)	0.0202 (10)	0.0017 (8)	−0.0066 (8)	−0.0094 (8)
C4	0.0252 (11)	0.0293 (11)	0.0184 (10)	0.0045 (8)	−0.0084 (8)	−0.0112 (9)
C5	0.0285 (12)	0.0248 (11)	0.0155 (10)	0.0012 (8)	−0.0048 (9)	−0.0031 (8)
C6	0.0229 (11)	0.0174 (10)	0.0197 (10)	−0.0010 (8)	−0.0031 (8)	−0.0043 (8)
C7	0.0219 (10)	0.0131 (9)	0.0151 (9)	0.0000 (7)	−0.0069 (8)	−0.0039 (7)
C8	0.0206 (10)	0.0176 (9)	0.0205 (10)	−0.0003 (7)	−0.0067 (8)	−0.0071 (8)
C9	0.0209 (10)	0.0194 (10)	0.0195 (10)	0.0019 (8)	−0.0069 (8)	−0.0098 (8)
C10	0.0201 (10)	0.0198 (10)	0.0190 (10)	0.0009 (8)	−0.0057 (8)	−0.0066 (8)
C11	0.0210 (11)	0.0215 (10)	0.0234 (10)	0.0007 (8)	−0.0072 (8)	−0.0117 (8)
C12	0.0263 (11)	0.0229 (10)	0.0208 (10)	0.0051 (8)	−0.0121 (9)	−0.0119 (8)
C13	0.0254 (11)	0.0217 (10)	0.0151 (10)	0.0019 (8)	−0.0055 (8)	−0.0056 (8)
C14	0.0241 (11)	0.0213 (10)	0.0212 (10)	−0.0013 (8)	−0.0063 (8)	−0.0083 (8)
C15	0.0197 (10)	0.0178 (9)	0.0201 (10)	−0.0032 (7)	−0.0058 (8)	−0.0061 (8)
C16	0.0222 (10)	0.0197 (10)	0.0180 (10)	−0.0037 (8)	−0.0055 (8)	−0.0063 (8)
C17	0.0176 (10)	0.0189 (10)	0.0158 (9)	0.0005 (7)	−0.0034 (8)	−0.0057 (8)
C18	0.0217 (10)	0.0182 (10)	0.0211 (10)	−0.0023 (7)	−0.0051 (8)	−0.0077 (8)
C19	0.0195 (10)	0.0240 (10)	0.0150 (9)	−0.0009 (8)	−0.0047 (8)	−0.0077 (8)
C20	0.0199 (10)	0.0173 (9)	0.0159 (9)	−0.0013 (7)	−0.0047 (8)	−0.0027 (8)
C21	0.0176 (10)	0.0161 (9)	0.0233 (10)	−0.0024 (7)	−0.0054 (8)	−0.0071 (8)
C22	0.0175 (10)	0.0187 (9)	0.0149 (9)	−0.0020 (7)	−0.0037 (7)	−0.0051 (8)
C23	0.0306 (13)	0.0312 (12)	0.0327 (12)	−0.0105 (9)	−0.0052 (10)	−0.0137 (10)
C24	0.0357 (13)	0.0284 (11)	0.0226 (11)	−0.0013 (9)	−0.0092 (9)	−0.0129 (9)
C25	0.0463 (15)	0.0343 (13)	0.0222 (11)	−0.0170 (11)	0.0012 (10)	−0.0083 (10)
C26	0.0365 (13)	0.0264 (11)	0.0263 (11)	−0.0053 (9)	−0.0096 (10)	−0.0129 (9)
C27	0.0348 (13)	0.0300 (12)	0.0250 (12)	−0.0045 (10)	0.0006 (10)	0.0008 (10)
C28	0.0355 (13)	0.0191 (10)	0.0235 (11)	−0.0022 (8)	−0.0110 (9)	−0.0086 (9)
C29	0.0277 (12)	0.0373 (13)	0.0277 (12)	−0.0028 (9)	−0.0076 (10)	−0.0100 (10)
C30	0.0557 (17)	0.0482 (16)	0.0263 (13)	−0.0224 (13)	0.0021 (12)	−0.0150 (12)

S1—C7	1.664 (2)	C9—C10	1.393 (3)
S2—C15	1.659 (2)	C9—C14	1.396 (3)
O1—C8	1.234 (2)	C10—C11	1.386 (3)
O2—C16	1.232 (2)	C10—H10	0.9500
O3—C11	1.373 (2)	C11—C12	1.400 (3)
O3—C23	1.425 (3)	C12—C13	1.402 (3)
O4—C12	1.370 (2)	C13—C14	1.389 (3)
O4—C24	1.438 (2)	C14—H14	0.9500
O5—C13	1.375 (2)	C16—C17	1.491 (3)
O5—C25	1.423 (3)	C17—C18	1.395 (3)
O6—C19	1.361 (2)	C17—C22	1.397 (3)
O6—C26	1.433 (2)	C18—C19	1.393 (3)
O7—C20	1.374 (2)	C18—H18	0.9500
O7—C27	1.441 (3)	C19—C20	1.400 (3)
O8—C21	1.370 (2)	C20—C21	1.402 (3)
O8—C28	1.428 (2)	C21—C22	1.393 (3)
O9—C29	1.434 (3)	C22—H22	0.9500
O9—H9	0.80 (3)	C23—H23A	0.9800
N1—C7	1.342 (2)	C23—H23B	0.9800
N1—C1	1.433 (3)	C23—H23C	0.9800
N1—H1	0.89 (2)	C24—H24A	0.9800
N2—C15	1.344 (3)	C24—H24B	0.9800
N2—C2	1.425 (2)	C24—H24C	0.9800
N2—H2	0.88 (2)	C25—H25A	0.9800
N3—C8	1.375 (3)	C25—H25B	0.9800
N3—C7	1.403 (3)	C25—H25C	0.9800
N3—H3A	0.84 (2)	C26—H26A	0.9800
N4—C16	1.381 (3)	C26—H26B	0.9800
N4—C15	1.407 (2)	C26—H26C	0.9800
N4—H4A	0.90 (2)	C27—H27A	0.9800
C1—C6	1.388 (3)	C27—H27B	0.9800
C1—C2	1.398 (3)	C27—H27C	0.9800
C2—C3	1.393 (3)	C28—H28A	0.9800
C3—C4	1.391 (3)	C28—H28B	0.9800
C3—H3	0.9500	C28—H28C	0.9800
C4—C5	1.387 (3)	C29—C30	1.508 (3)
C4—H4	0.9500	C29—H29A	0.9900
C5—C6	1.388 (3)	C29—H29B	0.9900
C5—H5	0.9500	C30—H30A	0.9800
C6—H6	0.9500	C30—H30B	0.9800
C8—C9	1.493 (3)	C30—H30C	0.9800
C11—O3—C23	116.05 (16)	C18—C17—C22	121.48 (17)
C12—O4—C24	114.05 (15)	C18—C17—C16	116.36 (18)
C13—O5—C25	116.56 (17)	C22—C17—C16	122.13 (18)
C19—O6—C26	117.41 (16)	C19—C18—C17	119.18 (18)
C20—O7—C27	114.85 (15)	C19—C18—H18	120.4
C21—O8—C28	117.05 (15)	C17—C18—H18	120.4
C29—O9—H9	107.2 (19)	O6—C19—C18	124.44 (18)
C7—N1—C1	124.35 (17)	O6—C19—C20	115.37 (17)
C7—N1—H1	116.3 (15)	C18—C19—C20	120.19 (18)
C1—N1—H1	118.6 (15)	O7—C20—C19	121.59 (18)
C15—N2—C2	125.79 (17)	O7—C20—C21	118.60 (17)
C15—N2—H2	117.3 (15)	C19—C20—C21	119.73 (17)
C2—N2—H2	116.3 (15)	O8—C21—C22	124.37 (18)
C8—N3—C7	127.62 (17)	O8—C21—C20	115.14 (17)
C8—N3—H3A	118.5 (16)	C22—C21—C20	120.47 (18)
C7—N3—H3A	113.8 (16)	C21—C22—C17	118.83 (18)
C16—N4—C15	129.46 (17)	C21—C22—H22	120.6
C16—N4—H4A	116.0 (15)	C17—C22—H22	120.6
C15—N4—H4A	114.3 (15)	O3—C23—H23A	109.5
C6—C1—C2	120.34 (18)	O3—C23—H23B	109.5
C6—C1—N1	118.33 (18)	H23A—C23—H23B	109.5
C2—C1—N1	121.21 (17)	O3—C23—H23C	109.5
C3—C2—C1	119.20 (18)	H23A—C23—H23C	109.5
C3—C2—N2	121.58 (18)	H23B—C23—H23C	109.5
C1—C2—N2	119.21 (17)	O4—C24—H24A	109.5
C4—C3—C2	120.1 (2)	O4—C24—H24B	109.5
C4—C3—H3	120.0	H24A—C24—H24B	109.5
C2—C3—H3	120.0	O4—C24—H24C	109.5
C5—C4—C3	120.44 (19)	H24A—C24—H24C	109.5
C5—C4—H4	119.8	H24B—C24—H24C	109.5
C3—C4—H4	119.8	O5—C25—H25A	109.5
C4—C5—C6	119.65 (19)	O5—C25—H25B	109.5
C4—C5—H5	120.2	H25A—C25—H25B	109.5
C6—C5—H5	120.2	O5—C25—H25C	109.5
C5—C6—C1	120.21 (19)	H25A—C25—H25C	109.5
C5—C6—H6	119.9	H25B—C25—H25C	109.5
C1—C6—H6	119.9	O6—C26—H26A	109.5
N1—C7—N3	115.67 (17)	O6—C26—H26B	109.5
N1—C7—S1	125.33 (15)	H26A—C26—H26B	109.5
N3—C7—S1	118.99 (14)	O6—C26—H26C	109.5
O1—C8—N3	121.57 (18)	H26A—C26—H26C	109.5
O1—C8—C9	121.22 (18)	H26B—C26—H26C	109.5
N3—C8—C9	117.16 (17)	O7—C27—H27A	109.5
C10—C9—C14	120.91 (19)	O7—C27—H27B	109.5
C10—C9—C8	115.91 (17)	H27A—C27—H27B	109.5
C14—C9—C8	123.07 (18)	O7—C27—H27C	109.5
C11—C10—C9	119.59 (18)	H27A—C27—H27C	109.5
C11—C10—H10	120.2	H27B—C27—H27C	109.5
C9—C10—H10	120.2	O8—C28—H28A	109.5
O3—C11—C10	124.62 (18)	O8—C28—H28B	109.5
O3—C11—C12	114.95 (18)	H28A—C28—H28B	109.5
C10—C11—C12	120.41 (19)	O8—C28—H28C	109.5
O4—C12—C11	120.25 (19)	H28A—C28—H28C	109.5
O4—C12—C13	120.29 (18)	H28B—C28—H28C	109.5
C11—C12—C13	119.24 (18)	O9—C29—C30	112.1 (2)
O5—C13—C14	124.23 (19)	O9—C29—H29A	109.2
O5—C13—C12	115.03 (18)	C30—C29—H29A	109.2
C14—C13—C12	120.71 (18)	O9—C29—H29B	109.2
C13—C14—C9	119.08 (19)	C30—C29—H29B	109.2
C13—C14—H14	120.5	H29A—C29—H29B	107.9
C9—C14—H14	120.5	C29—C30—H30A	109.5
N2—C15—N4	114.99 (17)	C29—C30—H30B	109.5
N2—C15—S2	128.09 (15)	H30A—C30—H30B	109.5
N4—C15—S2	116.90 (14)	C29—C30—H30C	109.5
O2—C16—N4	121.94 (18)	H30A—C30—H30C	109.5
O2—C16—C17	122.15 (18)	H30B—C30—H30C	109.5
N4—C16—C17	115.90 (17)
C7—N1—C1—C6	112.1 (2)	C11—C12—C13—O5	−179.33 (17)
C7—N1—C1—C2	−71.9 (2)	O4—C12—C13—C14	−171.96 (17)
C6—C1—C2—C3	−2.4 (3)	C11—C12—C13—C14	2.6 (3)
N1—C1—C2—C3	−178.42 (17)	O5—C13—C14—C9	−178.68 (18)
C6—C1—C2—N2	178.93 (17)	C12—C13—C14—C9	−0.8 (3)
N1—C1—C2—N2	2.9 (3)	C10—C9—C14—C13	−1.2 (3)
C15—N2—C2—C3	46.2 (3)	C8—C9—C14—C13	174.92 (18)
C15—N2—C2—C1	−135.2 (2)	C2—N2—C15—N4	176.38 (18)
C1—C2—C3—C4	3.5 (3)	C2—N2—C15—S2	−2.4 (3)
N2—C2—C3—C4	−177.94 (18)	C16—N4—C15—N2	−11.5 (3)
C2—C3—C4—C5	−1.6 (3)	C16—N4—C15—S2	167.45 (17)
C3—C4—C5—C6	−1.3 (3)	C15—N4—C16—O2	4.6 (3)
C4—C5—C6—C1	2.3 (3)	C15—N4—C16—C17	−174.03 (19)
C2—C1—C6—C5	−0.5 (3)	O2—C16—C17—C18	−28.7 (3)
N1—C1—C6—C5	175.64 (18)	N4—C16—C17—C18	149.99 (18)
C1—N1—C7—N3	−178.21 (16)	O2—C16—C17—C22	149.5 (2)
C1—N1—C7—S1	1.0 (3)	N4—C16—C17—C22	−31.8 (3)
C8—N3—C7—N1	11.8 (3)	C22—C17—C18—C19	−0.3 (3)
C8—N3—C7—S1	−167.47 (15)	C16—C17—C18—C19	177.93 (18)
C7—N3—C8—O1	0.1 (3)	C26—O6—C19—C18	−5.4 (3)
C7—N3—C8—C9	177.21 (17)	C26—O6—C19—C20	174.43 (17)
O1—C8—C9—C10	15.1 (3)	C17—C18—C19—O6	176.90 (17)
N3—C8—C9—C10	−162.03 (17)	C17—C18—C19—C20	−2.9 (3)
O1—C8—C9—C14	−161.21 (19)	C27—O7—C20—C19	65.1 (3)
N3—C8—C9—C14	21.6 (3)	C27—O7—C20—C21	−118.3 (2)
C14—C9—C10—C11	1.4 (3)	O6—C19—C20—O7	0.9 (3)
C8—C9—C10—C11	−174.97 (17)	C18—C19—C20—O7	−179.27 (17)
C23—O3—C11—C10	−2.1 (3)	O6—C19—C20—C21	−175.70 (17)
C23—O3—C11—C12	176.46 (17)	C18—C19—C20—C21	4.1 (3)
C9—C10—C11—O3	178.88 (18)	C28—O8—C21—C22	4.0 (3)
C9—C10—C11—C12	0.4 (3)	C28—O8—C21—C20	−177.79 (17)
C24—O4—C12—C11	93.5 (2)	O7—C20—C21—O8	2.8 (3)
C24—O4—C12—C13	−92.0 (2)	C19—C20—C21—O8	179.51 (17)
O3—C11—C12—O4	−6.4 (3)	O7—C20—C21—C22	−178.87 (17)
C10—C11—C12—O4	172.17 (17)	C19—C20—C21—C22	−2.2 (3)
O3—C11—C12—C13	178.98 (17)	O8—C21—C22—C17	177.19 (17)
C10—C11—C12—C13	−2.4 (3)	C20—C21—C22—C17	−1.0 (3)
C25—O5—C13—C14	−5.1 (3)	C18—C17—C22—C21	2.2 (3)
C25—O5—C13—C12	176.94 (18)	C16—C17—C22—C21	−175.89 (18)
O4—C12—C13—O5	6.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1i	0.90 (2)	2.51 (2)	3.403 (2)	173 (2)
N2—H2···S1	0.88 (2)	2.69 (2)	3.3527 (19)	133.0 (18)
N2—H2···O2	0.88 (2)	1.97 (2)	2.677 (2)	136 (2)
N1—H1···O1	0.89 (2)	1.90 (2)	2.621 (2)	137 (2)
N3—H3A···O9	0.84 (2)	2.23 (2)	2.949 (2)	145 (2)
O9—H9···O2	0.80 (3)	2.13 (3)	2.905 (2)	163 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O1i	0.90 (2)	2.51 (2)	3.403 (2)	173 (2)
N2—H2⋯S1	0.88 (2)	2.69 (2)	3.3527 (19)	133.0 (18)
N2—H2⋯O2	0.88 (2)	1.97 (2)	2.677 (2)	136 (2)
N1—H1⋯O1	0.89 (2)	1.90 (2)	2.621 (2)	137 (2)
N3—H3A⋯O9	0.84 (2)	2.23 (2)	2.949 (2)	145 (2)
O9—H9⋯O2	0.80 (3)	2.13 (3)	2.905 (2)	163 (3)

Symmetry code: (i) .