1-Benzyl-6,8-dimethyl-4-phenyl-2-tosyl-1,2,3,3a,4,6,7,8,9,9b-deca-hydro-pyrrolo[3,4-c]pyrano[6,5-d]pyrimidine-7,9-dione.

The mol-ecule of the title compound, C(31)H(31)N(3)O(5)S, adopts a folded conformation, with the sulfonyl-bound phenyl ring lying over the pyrimidine ring [dihedral angle = 12.04 (6)° and centroid-centroid separation = 3.6986 (8) Å]. The pyrrolidine ring adopts a twist conformation, the dihydro-pyran ring is in a half-chair conformation and the two rings are cis-fused. The tosyl group is attached to the pyrrolidine ring in an equatorial position while the benzyl group is axially attached. The mol-ecular structure is stabilized by weak C-H⋯O hydrogen bonds and C-H⋯π inter-actions. In the crystal, pairs of mol-ecules related by inversion symmetry are linked by C-H⋯O hydrogen bonds, forming chains propagating along the c axis which are cross-linked into a three-dimensional framework by further C-H⋯O links.

Related literature

For the biological activity of pyran­opyrimidine derivatives, see: Abdel Fattah et al. (2004 ▶); Bedair et al. (2000 ▶, 2001 ▶); Bruno et al. (2000 ▶); Eid et al. (2004 ▶); Shamroukh et al. (2007 ▶). For a related structure, see: Chinnakali et al. (2007 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶) and for asymmetry parameters, see: Duax et al. (1976 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C31H31N3O5S

M = 557.65

Monoclinic,

a = 13.2778 (2) Å

b = 15.8888 (2) Å

c = 13.0886 (2) Å

β = 99.019 (1)°

V = 2727.14 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 100 K

0.29 × 0.24 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.875, T max = 0.976

39155 measured reflections

7888 independent reflections

6269 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.127

S = 1.07

7888 reflections

363 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044341/hb5182sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044341/hb5182Isup2.hkl

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

C31H31N3O5S	F(000) = 1176
Mr = 557.65	Dx = 1.358 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9929 reflections
a = 13.2778 (2) Å	θ = 2.6–32.3°
b = 15.8888 (2) Å	µ = 0.17 mm−1
c = 13.0886 (2) Å	T = 100 K
β = 99.019 (1)°	Block, colourless
V = 2727.14 (7) Å3	0.29 × 0.24 × 0.15 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	7888 independent reflections
Radiation source: fine-focus sealed tube	6269 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→18
Tmin = 0.875, Tmax = 0.976	k = −22→21
39155 measured reflections	l = −17→18

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0645P)2 + 0.8585P] where P = (Fo2 + 2Fc2)/3
7888 reflections	(Δ/σ)max = 0.001
363 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.45 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)
S1	0.24002 (3)	0.27919 (2)	0.08504 (3)	0.01786 (9)
O1	0.29691 (8)	0.20418 (7)	0.11604 (8)	0.0244 (2)
O2	0.22163 (8)	0.30362 (7)	−0.02164 (8)	0.0227 (2)
O3	0.22116 (7)	0.42241 (7)	0.41969 (7)	0.0192 (2)
O4	−0.12019 (8)	0.44236 (7)	0.32394 (8)	0.0230 (2)
O5	0.07992 (7)	0.55421 (6)	0.10506 (7)	0.0180 (2)
N1	0.30062 (9)	0.35642 (7)	0.14908 (9)	0.0172 (2)
N2	0.05214 (9)	0.43750 (7)	0.37124 (9)	0.0169 (2)
N3	−0.02062 (8)	0.49601 (7)	0.21216 (8)	0.0154 (2)
C1	0.33158 (11)	0.34751 (9)	0.26213 (10)	0.0193 (3)
H1A	0.3954	0.3171	0.2781	0.023*
H1B	0.2797	0.3184	0.2931	0.023*
C2	0.34345 (10)	0.43876 (9)	0.30011 (10)	0.0161 (3)
H2	0.4127	0.4579	0.2954	0.019*
C3	0.26717 (10)	0.48911 (8)	0.22261 (10)	0.0142 (2)
H3	0.2889	0.5479	0.2195	0.017*
C4	0.27054 (10)	0.44416 (8)	0.11846 (10)	0.0151 (2)
H4	0.2019	0.4438	0.0779	0.018*
C5	0.32387 (10)	0.45051 (9)	0.41091 (10)	0.0179 (3)
H5	0.3721	0.4147	0.4558	0.021*
C6	0.14751 (10)	0.44924 (8)	0.34517 (10)	0.0155 (2)
C7	0.16259 (10)	0.48378 (8)	0.25380 (10)	0.0145 (2)
C8	0.12079 (11)	0.26992 (9)	0.12787 (11)	0.0182 (3)
C9	0.03512 (11)	0.31028 (9)	0.07404 (11)	0.0203 (3)
H9	0.0408	0.3436	0.0168	0.024*
C10	−0.05862 (12)	0.30012 (9)	0.10679 (12)	0.0233 (3)
H10	−0.1159	0.3261	0.0701	0.028*
C11	−0.06866 (12)	0.25174 (9)	0.19372 (12)	0.0241 (3)
C12	0.01881 (12)	0.21432 (9)	0.24816 (12)	0.0247 (3)
H12	0.0139	0.1836	0.3077	0.030*
C13	0.11282 (12)	0.22190 (9)	0.21553 (11)	0.0220 (3)
H13	0.1699	0.1953	0.2517	0.026*
C14	−0.17063 (13)	0.23950 (12)	0.22861 (15)	0.0331 (4)
H14A	−0.2101	0.2902	0.2164	0.050*	0.50
H14B	−0.1605	0.2266	0.3011	0.050*	0.50
H14C	−0.2063	0.1940	0.1905	0.050*	0.50
H14D	−0.1745	0.1836	0.2557	0.050*	0.50
H14E	−0.2241	0.2472	0.1709	0.050*	0.50
H14F	−0.1782	0.2798	0.2815	0.050*	0.50
C15	−0.03560 (10)	0.45740 (9)	0.30321 (10)	0.0168 (3)
C16	0.07514 (10)	0.51458 (8)	0.18497 (10)	0.0141 (2)
C17	0.34013 (11)	0.54080 (9)	0.44869 (10)	0.0192 (3)
C18	0.42511 (12)	0.58588 (10)	0.42851 (12)	0.0237 (3)
H18	0.4716	0.5604	0.3921	0.028*
C19	0.44095 (13)	0.66829 (11)	0.46223 (14)	0.0316 (4)
H19	0.4976	0.6979	0.4480	0.038*
C20	0.37218 (15)	0.70650 (12)	0.51717 (15)	0.0389 (4)
H20	0.3824	0.7619	0.5395	0.047*
C21	0.28856 (15)	0.66214 (13)	0.53870 (14)	0.0388 (4)
H21	0.2426	0.6878	0.5757	0.047*
C22	0.27261 (13)	0.57937 (11)	0.50547 (12)	0.0282 (3)
H22	0.2167	0.5497	0.5212	0.034*
C23	0.03991 (12)	0.39397 (11)	0.46792 (11)	0.0257 (3)
H23A	0.0907	0.4137	0.5231	0.039*
H23B	0.0477	0.3344	0.4593	0.039*
H23C	−0.0267	0.4054	0.4844	0.039*
C24	−0.11133 (10)	0.51453 (10)	0.13584 (11)	0.0194 (3)
H24A	−0.1674	0.4807	0.1501	0.029*
H24B	−0.0974	0.5020	0.0677	0.029*
H24C	−0.1285	0.5730	0.1398	0.029*
C25	0.34547 (10)	0.48309 (9)	0.05318 (10)	0.0173 (3)
H25A	0.3490	0.4471	−0.0060	0.021*
H25B	0.3193	0.5373	0.0274	0.021*
C26	0.45176 (10)	0.49478 (10)	0.11237 (11)	0.0195 (3)
C27	0.51924 (12)	0.42716 (11)	0.13215 (13)	0.0274 (3)
H27	0.5021	0.3748	0.1027	0.033*
C28	0.61285 (13)	0.43864 (14)	0.19648 (14)	0.0385 (5)
H28	0.6568	0.3931	0.2109	0.046*
C29	0.64105 (13)	0.51625 (15)	0.23891 (13)	0.0411 (5)
H29	0.7032	0.5228	0.2821	0.049*
C30	0.57666 (13)	0.58375 (14)	0.21684 (13)	0.0364 (4)
H30	0.5959	0.6366	0.2435	0.044*
C31	0.48241 (12)	0.57272 (11)	0.15439 (12)	0.0254 (3)
H31	0.4390	0.6186	0.1405	0.030*

	U11	U22	U33	U12	U13	U23
S1	0.02082 (17)	0.01614 (16)	0.01588 (16)	0.00094 (12)	0.00059 (12)	−0.00164 (12)
O1	0.0276 (6)	0.0181 (5)	0.0265 (5)	0.0056 (4)	0.0010 (4)	−0.0017 (4)
O2	0.0285 (5)	0.0242 (5)	0.0148 (5)	−0.0001 (4)	0.0019 (4)	−0.0030 (4)
O3	0.0159 (5)	0.0257 (5)	0.0149 (4)	−0.0012 (4)	−0.0014 (3)	0.0062 (4)
O4	0.0166 (5)	0.0317 (6)	0.0213 (5)	−0.0017 (4)	0.0048 (4)	0.0035 (4)
O5	0.0201 (5)	0.0194 (5)	0.0143 (4)	0.0030 (4)	0.0025 (4)	0.0036 (4)
N1	0.0193 (6)	0.0157 (5)	0.0155 (5)	0.0001 (4)	−0.0008 (4)	0.0001 (4)
N2	0.0173 (5)	0.0196 (6)	0.0137 (5)	−0.0011 (4)	0.0018 (4)	0.0049 (4)
N3	0.0137 (5)	0.0182 (5)	0.0137 (5)	0.0014 (4)	0.0002 (4)	0.0012 (4)
C1	0.0216 (7)	0.0191 (7)	0.0156 (6)	0.0030 (5)	−0.0024 (5)	0.0004 (5)
C2	0.0149 (6)	0.0175 (6)	0.0147 (6)	0.0003 (5)	−0.0011 (5)	−0.0008 (5)
C3	0.0136 (6)	0.0158 (6)	0.0126 (5)	−0.0003 (5)	0.0001 (4)	0.0014 (4)
C4	0.0150 (6)	0.0163 (6)	0.0134 (6)	−0.0001 (5)	0.0001 (4)	0.0005 (5)
C5	0.0152 (6)	0.0237 (7)	0.0138 (6)	0.0000 (5)	−0.0008 (5)	0.0017 (5)
C6	0.0157 (6)	0.0149 (6)	0.0150 (6)	0.0002 (5)	−0.0006 (5)	0.0008 (5)
C7	0.0151 (6)	0.0146 (6)	0.0132 (6)	0.0000 (5)	0.0002 (4)	0.0005 (4)
C8	0.0210 (7)	0.0141 (6)	0.0183 (6)	−0.0017 (5)	−0.0003 (5)	−0.0019 (5)
C9	0.0252 (7)	0.0159 (6)	0.0185 (6)	0.0005 (5)	−0.0004 (5)	−0.0008 (5)
C10	0.0230 (7)	0.0178 (7)	0.0274 (7)	0.0027 (5)	−0.0013 (6)	−0.0029 (6)
C11	0.0260 (7)	0.0169 (7)	0.0297 (7)	−0.0018 (6)	0.0056 (6)	−0.0053 (6)
C12	0.0308 (8)	0.0196 (7)	0.0238 (7)	−0.0039 (6)	0.0041 (6)	0.0014 (5)
C13	0.0242 (7)	0.0176 (7)	0.0225 (7)	−0.0013 (5)	−0.0010 (5)	0.0031 (5)
C14	0.0290 (8)	0.0312 (9)	0.0410 (9)	−0.0012 (7)	0.0117 (7)	−0.0034 (7)
C15	0.0178 (6)	0.0176 (6)	0.0147 (6)	0.0010 (5)	0.0021 (5)	0.0004 (5)
C16	0.0160 (6)	0.0135 (6)	0.0126 (5)	0.0012 (5)	0.0010 (4)	−0.0011 (4)
C17	0.0200 (7)	0.0240 (7)	0.0120 (6)	0.0001 (5)	−0.0022 (5)	−0.0008 (5)
C18	0.0213 (7)	0.0272 (8)	0.0215 (7)	−0.0011 (6)	−0.0001 (5)	−0.0031 (6)
C19	0.0292 (8)	0.0299 (9)	0.0335 (9)	−0.0066 (7)	−0.0023 (7)	−0.0040 (7)
C20	0.0445 (10)	0.0314 (9)	0.0379 (10)	−0.0029 (8)	−0.0024 (8)	−0.0151 (8)
C21	0.0434 (10)	0.0434 (11)	0.0306 (9)	0.0022 (8)	0.0091 (8)	−0.0166 (8)
C22	0.0299 (8)	0.0360 (9)	0.0195 (7)	−0.0016 (7)	0.0061 (6)	−0.0063 (6)
C23	0.0256 (7)	0.0331 (8)	0.0189 (7)	−0.0027 (6)	0.0050 (5)	0.0124 (6)
C24	0.0149 (6)	0.0253 (7)	0.0166 (6)	0.0025 (5)	−0.0014 (5)	0.0002 (5)
C25	0.0166 (6)	0.0207 (7)	0.0145 (6)	0.0000 (5)	0.0020 (5)	0.0012 (5)
C26	0.0163 (6)	0.0268 (7)	0.0160 (6)	−0.0005 (5)	0.0043 (5)	0.0034 (5)
C27	0.0222 (7)	0.0347 (9)	0.0277 (8)	0.0071 (6)	0.0108 (6)	0.0083 (6)
C28	0.0204 (8)	0.0622 (13)	0.0346 (9)	0.0161 (8)	0.0095 (7)	0.0195 (9)
C29	0.0188 (8)	0.0798 (15)	0.0239 (8)	−0.0074 (9)	0.0011 (6)	0.0083 (9)
C30	0.0258 (8)	0.0571 (12)	0.0256 (8)	−0.0166 (8)	0.0023 (6)	−0.0016 (8)
C31	0.0227 (7)	0.0303 (8)	0.0228 (7)	−0.0057 (6)	0.0020 (6)	0.0032 (6)

S1—O2	1.4328 (10)	C12—H12	0.93
S1—O1	1.4351 (11)	C13—H13	0.93
S1—N1	1.6261 (12)	C14—H14A	0.96
S1—C8	1.7664 (15)	C14—H14B	0.96
O3—C6	1.3380 (15)	C14—H14C	0.96
O3—C5	1.4566 (16)	C14—H14D	0.96
O4—C15	1.2198 (17)	C14—H14E	0.96
O5—C16	1.2309 (15)	C14—H14F	0.96
N1—C1	1.4791 (17)	C17—C22	1.393 (2)
N1—C4	1.4878 (17)	C17—C18	1.396 (2)
N2—C6	1.3748 (18)	C18—C19	1.387 (2)
N2—C15	1.3873 (17)	C18—H18	0.93
N2—C23	1.4733 (17)	C19—C20	1.388 (3)
N3—C15	1.3822 (17)	C19—H19	0.93
N3—C16	1.4043 (17)	C20—C21	1.381 (3)
N3—C24	1.4690 (16)	C20—H20	0.93
C1—C2	1.5327 (19)	C21—C22	1.391 (3)
C1—H1A	0.97	C21—H21	0.93
C1—H1B	0.97	C22—H22	0.93
C2—C5	1.5245 (18)	C23—H23A	0.96
C2—C3	1.5403 (17)	C23—H23B	0.96
C2—H2	0.98	C23—H23C	0.96
C3—C7	1.5100 (18)	C24—H24A	0.96
C3—C4	1.5457 (18)	C24—H24B	0.96
C3—H3	0.98	C24—H24C	0.96
C4—C25	1.5391 (19)	C25—C26	1.5111 (19)
C4—H4	0.98	C25—H25A	0.97
C5—C17	1.522 (2)	C25—H25B	0.97
C5—H5	0.98	C26—C31	1.390 (2)
C6—C7	1.3589 (18)	C26—C27	1.397 (2)
C7—C16	1.4392 (17)	C27—C28	1.400 (2)
C8—C13	1.396 (2)	C27—H27	0.93
C8—C9	1.3965 (19)	C28—C29	1.380 (3)
C9—C10	1.388 (2)	C28—H28	0.93
C9—H9	0.93	C29—C30	1.374 (3)
C10—C11	1.397 (2)	C29—H29	0.93
C10—H10	0.93	C30—C31	1.394 (2)
C11—C12	1.397 (2)	C30—H30	0.93
C11—C14	1.508 (2)	C31—H31	0.93
C12—C13	1.386 (2)
O2—S1—O1	120.15 (7)	C11—C14—H14D	109.5
O2—S1—N1	107.03 (6)	H14A—C14—H14D	141.1
O1—S1—N1	106.55 (6)	H14B—C14—H14D	56.3
O2—S1—C8	107.91 (6)	H14C—C14—H14D	56.3
O1—S1—C8	107.41 (7)	C11—C14—H14E	109.5
N1—S1—C8	107.15 (6)	H14A—C14—H14E	56.3
C6—O3—C5	115.54 (10)	H14B—C14—H14E	141.1
C1—N1—C4	112.33 (10)	H14C—C14—H14E	56.3
C1—N1—S1	118.75 (9)	H14D—C14—H14E	109.5
C4—N1—S1	118.55 (8)	C11—C14—H14F	109.5
C6—N2—C15	121.56 (11)	H14A—C14—H14F	56.3
C6—N2—C23	120.44 (11)	H14B—C14—H14F	56.3
C15—N2—C23	117.62 (12)	H14C—C14—H14F	141.1
C15—N3—C16	124.76 (11)	H14D—C14—H14F	109.5
C15—N3—C24	117.50 (11)	H14E—C14—H14F	109.5
C16—N3—C24	117.64 (11)	O4—C15—N3	122.73 (12)
N1—C1—C2	103.43 (11)	O4—C15—N2	121.50 (12)
N1—C1—H1A	111.1	N3—C15—N2	115.76 (12)
C2—C1—H1A	111.1	O5—C16—N3	119.48 (11)
N1—C1—H1B	111.1	O5—C16—C7	124.18 (12)
C2—C1—H1B	111.1	N3—C16—C7	116.33 (11)
H1A—C1—H1B	109.0	C22—C17—C18	118.82 (14)
C5—C2—C1	113.59 (12)	C22—C17—C5	121.18 (14)
C5—C2—C3	111.73 (11)	C18—C17—C5	119.99 (13)
C1—C2—C3	104.73 (10)	C19—C18—C17	120.71 (15)
C5—C2—H2	108.9	C19—C18—H18	119.6
C1—C2—H2	108.9	C17—C18—H18	119.6
C3—C2—H2	108.9	C18—C19—C20	119.91 (17)
C7—C3—C2	109.29 (11)	C18—C19—H19	120.0
C7—C3—C4	111.56 (10)	C20—C19—H19	120.0
C2—C3—C4	103.52 (10)	C21—C20—C19	119.86 (17)
C7—C3—H3	110.7	C21—C20—H20	120.1
C2—C3—H3	110.7	C19—C20—H20	120.1
C4—C3—H3	110.7	C20—C21—C22	120.44 (17)
N1—C4—C25	110.89 (11)	C20—C21—H21	119.8
N1—C4—C3	103.83 (10)	C22—C21—H21	119.8
C25—C4—C3	114.49 (11)	C21—C22—C17	120.24 (16)
N1—C4—H4	109.1	C21—C22—H22	119.9
C25—C4—H4	109.1	C17—C22—H22	119.9
C3—C4—H4	109.1	N2—C23—H23A	109.5
O3—C5—C17	110.50 (11)	N2—C23—H23B	109.5
O3—C5—C2	109.81 (10)	H23A—C23—H23B	109.5
C17—C5—C2	112.83 (11)	N2—C23—H23C	109.5
O3—C5—H5	107.8	H23A—C23—H23C	109.5
C17—C5—H5	107.8	H23B—C23—H23C	109.5
C2—C5—H5	107.8	N3—C24—H24A	109.5
O3—C6—C7	125.35 (12)	N3—C24—H24B	109.5
O3—C6—N2	111.86 (11)	H24A—C24—H24B	109.5
C7—C6—N2	122.79 (12)	N3—C24—H24C	109.5
C6—C7—C16	118.20 (12)	H24A—C24—H24C	109.5
C6—C7—C3	121.95 (11)	H24B—C24—H24C	109.5
C16—C7—C3	119.84 (11)	C26—C25—C4	113.45 (11)
C13—C8—C9	120.33 (14)	C26—C25—H25A	108.9
C13—C8—S1	119.58 (11)	C4—C25—H25A	108.9
C9—C8—S1	120.08 (11)	C26—C25—H25B	108.9
C10—C9—C8	119.33 (14)	C4—C25—H25B	108.9
C10—C9—H9	120.3	H25A—C25—H25B	107.7
C8—C9—H9	120.3	C31—C26—C27	118.19 (14)
C9—C10—C11	121.35 (14)	C31—C26—C25	120.30 (13)
C9—C10—H10	119.3	C27—C26—C25	121.39 (14)
C11—C10—H10	119.3	C26—C27—C28	119.64 (17)
C10—C11—C12	118.17 (15)	C26—C27—H27	120.2
C10—C11—C14	121.51 (15)	C28—C27—H27	120.2
C12—C11—C14	120.33 (15)	C29—C28—C27	121.20 (17)
C13—C12—C11	121.51 (14)	C29—C28—H28	119.4
C13—C12—H12	119.2	C27—C28—H28	119.4
C11—C12—H12	119.2	C30—C29—C28	119.50 (16)
C12—C13—C8	119.26 (14)	C30—C29—H29	120.3
C12—C13—H13	120.4	C28—C29—H29	120.3
C8—C13—H13	120.4	C29—C30—C31	119.80 (18)
C11—C14—H14A	109.5	C29—C30—H30	120.1
C11—C14—H14B	109.5	C31—C30—H30	120.1
H14A—C14—H14B	109.5	C26—C31—C30	121.62 (17)
C11—C14—H14C	109.5	C26—C31—H31	119.2
H14A—C14—H14C	109.5	C30—C31—H31	119.2
H14B—C14—H14C	109.5
O2—S1—N1—C1	−178.78 (10)	S1—C8—C9—C10	177.94 (11)
O1—S1—N1—C1	−49.05 (12)	C8—C9—C10—C11	1.3 (2)
C8—S1—N1—C1	65.68 (11)	C9—C10—C11—C12	0.8 (2)
O2—S1—N1—C4	38.87 (12)	C9—C10—C11—C14	−179.07 (14)
O1—S1—N1—C4	168.59 (10)	C10—C11—C12—C13	−2.3 (2)
C8—S1—N1—C4	−76.68 (11)	C14—C11—C12—C13	177.51 (14)
C4—N1—C1—C2	−12.74 (15)	C11—C12—C13—C8	1.8 (2)
S1—N1—C1—C2	−157.29 (9)	C9—C8—C13—C12	0.4 (2)
N1—C1—C2—C5	151.72 (11)	S1—C8—C13—C12	−179.44 (11)
N1—C1—C2—C3	29.54 (14)	C16—N3—C15—O4	179.99 (13)
C5—C2—C3—C7	−39.77 (15)	C24—N3—C15—O4	−3.7 (2)
C1—C2—C3—C7	83.61 (13)	C16—N3—C15—N2	0.86 (19)
C5—C2—C3—C4	−158.76 (11)	C24—N3—C15—N2	177.18 (12)
C1—C2—C3—C4	−35.38 (13)	C6—N2—C15—O4	175.59 (13)
C1—N1—C4—C25	114.32 (12)	C23—N2—C15—O4	2.7 (2)
S1—N1—C4—C25	−101.05 (11)	C6—N2—C15—N3	−5.27 (19)
C1—N1—C4—C3	−9.10 (14)	C23—N2—C15—N3	−178.21 (12)
S1—N1—C4—C3	135.53 (10)	C15—N3—C16—O5	−175.14 (12)
C7—C3—C4—N1	−90.39 (12)	C24—N3—C16—O5	8.55 (18)
C2—C3—C4—N1	27.02 (13)	C15—N3—C16—C7	5.83 (19)
C7—C3—C4—C25	148.58 (11)	C24—N3—C16—C7	−170.48 (12)
C2—C3—C4—C25	−94.01 (12)	C6—C7—C16—O5	172.74 (13)
C6—O3—C5—C17	78.79 (14)	C3—C7—C16—O5	−8.3 (2)
C6—O3—C5—C2	−46.30 (15)	C6—C7—C16—N3	−8.28 (18)
C1—C2—C5—O3	−58.54 (14)	C3—C7—C16—N3	170.68 (11)
C3—C2—C5—O3	59.67 (14)	O3—C5—C17—C22	14.05 (17)
C1—C2—C5—C17	177.71 (11)	C2—C5—C17—C22	137.41 (13)
C3—C2—C5—C17	−64.08 (14)	O3—C5—C17—C18	−167.34 (12)
C5—O3—C6—C7	14.77 (19)	C2—C5—C17—C18	−43.98 (17)
C5—O3—C6—N2	−165.52 (11)	C22—C17—C18—C19	−1.5 (2)
C15—N2—C6—O3	−177.06 (12)	C5—C17—C18—C19	179.87 (14)
C23—N2—C6—O3	−4.32 (18)	C17—C18—C19—C20	0.4 (2)
C15—N2—C6—C7	2.6 (2)	C18—C19—C20—C21	0.4 (3)
C23—N2—C6—C7	175.40 (13)	C19—C20—C21—C22	−0.1 (3)
O3—C6—C7—C16	−175.88 (12)	C20—C21—C22—C17	−1.0 (3)
N2—C6—C7—C16	4.4 (2)	C18—C17—C22—C21	1.8 (2)
O3—C6—C7—C3	5.2 (2)	C5—C17—C22—C21	−179.60 (15)
N2—C6—C7—C3	−174.49 (12)	N1—C4—C25—C26	−65.58 (15)
C2—C3—C7—C6	8.60 (17)	C3—C4—C25—C26	51.48 (16)
C4—C3—C7—C6	122.47 (13)	C4—C25—C26—C31	−98.15 (16)
C2—C3—C7—C16	−170.33 (11)	C4—C25—C26—C27	77.65 (17)
C4—C3—C7—C16	−56.46 (16)	C31—C26—C27—C28	2.7 (2)
O2—S1—C8—C13	159.31 (11)	C25—C26—C27—C28	−173.20 (14)
O1—S1—C8—C13	28.42 (13)	C26—C27—C28—C29	−1.6 (2)
N1—S1—C8—C13	−85.74 (12)	C27—C28—C29—C30	−0.7 (3)
O2—S1—C8—C9	−20.53 (13)	C28—C29—C30—C31	1.8 (3)
O1—S1—C8—C9	−151.41 (11)	C27—C26—C31—C30	−1.6 (2)
N1—S1—C8—C9	94.43 (12)	C25—C26—C31—C30	174.38 (14)
C13—C8—C9—C10	−1.9 (2)	C29—C30—C31—C26	−0.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O5	0.98	2.45	3.0586 (16)	120
C2—H2···Cg1	0.98	2.67	3.5377 (15)	148
C22—H22···O4i	0.93	2.57	3.258 (2)	132
C24—H24B···O5ii	0.96	2.48	3.4236 (17)	169
C30—H30···O1iii	0.93	2.40	3.180 (2)	142
C25—H25A···Cg1iv	0.97	2.88	3.5110 (15)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O5	0.98	2.45	3.0586 (16)	120
C2—H2⋯Cg1	0.98	2.67	3.5377 (15)	148
C22—H22⋯O4i	0.93	2.57	3.258 (2)	132
C24—H24B⋯O5ii	0.96	2.48	3.4236 (17)	169
C30—H30⋯O1iii	0.93	2.40	3.180 (2)	142

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C26–C31 ring.