Dimethyl 3,3'-diphenyl-2,2'-[(S)-thio-phene-2,5-diylbis(carbonyl-aza-nedi-yl)]dipropano-ate tetra-hydro-furan monosolvate.

The title compound, C(26)H(26)N(2)O(6)S·C(4)H(8)O, a solvated bis-amide derivative, is also a chiral amino acid ester with l-phenyl-alanine methyl ester groups as amine substituents. The thio-phene-2,5-dicarboxamide core approximates C(2) point symmetry. The tetra-hydro-furan solvent mol-ecule is linked to the main mol-ecule through an inter-molecular N-H⋯O hydrogen bond. The central ring makes dihedral angles of 90.0 (2) and 76.5 (2)° with the pendant rings.

Related literature

For applications of thio­phene derivatives, see: Zhao et al. (2009 ▶). For the synthesis of the title compound, see: Moriuchi et al. (2006 ▶). For the structure of the unsolvated mol­ecule, see: Xia et al. (2010 ▶).

Experimental

Crystal data

C26H26N2O6S·C4H8O

M = 566.65

Orthorhombic,

a = 8.3041 (3) Å

b = 12.1810 (4) Å

c = 29.6787 (11) Å

V = 3002.06 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 293 K

0.40 × 0.21 × 0.08 mm

Data collection

Oxford Xcalibur (Eos) CCD detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 ▶) T min = 0.941, T max = 0.988

7782 measured reflections

5081 independent reflections

3167 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.094

S = 0.91

5081 reflections

363 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1964 Friedel pairs

Flack parameter: −0.05 (9)

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034410/bh2306sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034410/bh2306Isup2.hkl

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

C26H26N2O6S·C4H8O	F(000) = 1200
Mr = 566.65	Dx = 1.254 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3062 reflections
a = 8.3041 (3) Å	θ = 3.0–28.8°
b = 12.1810 (4) Å	µ = 0.16 mm−1
c = 29.6787 (11) Å	T = 293 K
V = 3002.06 (17) Å3	Block, colourless
Z = 4	0.40 × 0.21 × 0.08 mm

Oxford Xcalibur (Eos) CCD detector diffractometer	5081 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3167 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 16.0355 pixels mm-1	θmax = 25.3°, θmin = 3.0°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	k = −14→12
Tmin = 0.941, Tmax = 0.988	l = −15→35
7782 measured reflections

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0458P)2] where P = (Fo2 + 2Fc2)/3
S = 0.91	(Δ/σ)max < 0.001
5081 reflections	Δρmax = 0.19 e Å−3
363 parameters	Δρmin = −0.20 e Å−3
0 restraints	Absolute structure: Flack (1983), 1964 Friedel pairs
0 constraints	Flack parameter: −0.05 (9)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
C1	0.7362 (4)	−0.1856 (4)	−0.38825 (15)	0.0993 (14)
H1A	0.7425	−0.2168	−0.3586	0.149*
H1B	0.7790	−0.1124	−0.3878	0.149*
H1C	0.7976	−0.2297	−0.4088	0.149*
C2	0.4695 (4)	−0.1250 (3)	−0.37793 (13)	0.0615 (9)
C3	0.2978 (3)	−0.1273 (2)	−0.39603 (10)	0.0476 (8)
H3	0.2785	−0.2003	−0.4089	0.057*
C4	0.2776 (4)	−0.0426 (2)	−0.43389 (11)	0.0555 (8)
H4A	0.2911	0.0305	−0.4215	0.067*
H4B	0.3615	−0.0538	−0.4562	0.067*
C5	0.1160 (4)	−0.0496 (2)	−0.45669 (10)	0.0466 (8)
C6	0.0864 (4)	−0.1295 (3)	−0.48868 (12)	0.0638 (9)
H6	0.1673	−0.1793	−0.4960	0.077*
C7	−0.0602 (5)	−0.1369 (3)	−0.50983 (13)	0.0782 (11)
H7	−0.0772	−0.1897	−0.5319	0.094*
C8	−0.1798 (5)	−0.0671 (4)	−0.49844 (15)	0.0794 (12)
H8	−0.2804	−0.0741	−0.5119	0.095*
C9	−0.1543 (5)	0.0131 (3)	−0.46754 (16)	0.0804 (12)
H9	−0.2361	0.0624	−0.4606	0.097*
C10	−0.0064 (4)	0.0216 (2)	−0.44637 (11)	0.0628 (9)
H10	0.0102	0.0761	−0.4249	0.075*
C11	0.1316 (3)	−0.1966 (3)	−0.33570 (10)	0.0476 (7)
C12	0.0384 (3)	−0.1773 (2)	−0.29456 (10)	0.0428 (7)
C13	−0.0220 (4)	−0.0850 (2)	−0.27630 (10)	0.0588 (9)
H13	−0.0123	−0.0160	−0.2894	0.071*
C14	−0.1017 (4)	−0.1042 (2)	−0.23495 (12)	0.0609 (9)
H14	−0.1489	−0.0490	−0.2178	0.073*
C15	−0.1023 (3)	−0.2104 (2)	−0.22293 (9)	0.0425 (7)
C16	−0.1644 (3)	−0.2650 (2)	−0.18143 (10)	0.0410 (7)
C17	−0.7408 (4)	−0.3073 (4)	−0.15049 (14)	0.1109 (16)
H17A	−0.8026	−0.2648	−0.1294	0.166*
H17B	−0.7452	−0.3834	−0.1422	0.166*
H17C	−0.7846	−0.2983	−0.1802	0.166*
C18	−0.4957 (4)	−0.2807 (2)	−0.11222 (12)	0.0541 (8)
C19	−0.3256 (3)	−0.2374 (2)	−0.11366 (10)	0.0449 (7)
H19	−0.2553	−0.2970	−0.1034	0.054*
C20	−0.3044 (3)	−0.1424 (2)	−0.08026 (11)	0.0543 (9)
H20B	−0.3664	−0.0799	−0.0906	0.065*
H20A	−0.3466	−0.1643	−0.0511	0.065*
C21	−0.1327 (4)	−0.1090 (3)	−0.07497 (11)	0.0532 (9)
C22	−0.0324 (4)	−0.1616 (3)	−0.04495 (12)	0.0687 (10)
H22	−0.0732	−0.2182	−0.0273	0.082*
C23	0.1266 (6)	−0.1322 (4)	−0.04062 (16)	0.0960 (14)
H23	0.1916	−0.1688	−0.0200	0.115*
C24	0.1900 (6)	−0.0506 (5)	−0.0661 (2)	0.1118 (18)
H24	0.2977	−0.0309	−0.0634	0.134*
C25	0.0910 (7)	0.0024 (4)	−0.0962 (2)	0.1108 (16)
H25	0.1327	0.0587	−0.1139	0.133*
C26	−0.0682 (5)	−0.0260 (3)	−0.10075 (14)	0.0785 (11)
H26	−0.1327	0.0111	−0.1214	0.094*
C27	−0.5480 (9)	−0.0480 (5)	−0.2287 (2)	0.210 (4)
H27A	−0.4867	−0.0942	−0.2490	0.252*
H27B	−0.6468	−0.0857	−0.2207	0.252*
C28	−0.5824 (9)	0.0546 (6)	−0.2491 (2)	0.184 (3)
H28B	−0.6961	0.0597	−0.2563	0.221*
H28A	−0.5211	0.0629	−0.2767	0.221*
C29	−0.5388 (8)	0.1382 (5)	−0.2175 (2)	0.170 (3)
H29B	−0.6284	0.1875	−0.2121	0.204*
H29A	−0.4480	0.1806	−0.2285	0.204*
C30	−0.4949 (7)	0.0780 (4)	−0.17561 (19)	0.1219 (16)
H30A	−0.4048	0.1133	−0.1607	0.146*
H30B	−0.5854	0.0758	−0.1550	0.146*
N1	0.1852 (3)	−0.11168 (19)	−0.35934 (8)	0.0479 (6)
H1	0.1527	−0.0466	−0.3528	0.057*
N2	−0.2705 (2)	−0.20642 (19)	−0.15812 (8)	0.0430 (6)
H2	−0.3083	−0.1474	−0.1700	0.052*
O1	0.5682 (3)	−0.1824 (2)	−0.40280 (8)	0.0745 (7)
O2	0.5104 (3)	−0.0779 (3)	−0.34523 (11)	0.1289 (13)
O3	0.1599 (3)	−0.29143 (18)	−0.34747 (8)	0.0910 (8)
O4	−0.1172 (2)	−0.35693 (15)	−0.17022 (7)	0.0555 (6)
O5	−0.5526 (3)	−0.3183 (3)	−0.07888 (10)	0.1001 (9)
O6	−0.5731 (3)	−0.2699 (2)	−0.15000 (9)	0.0818 (8)
O7	−0.4551 (4)	−0.0230 (2)	−0.18881 (12)	0.1181 (11)
S1	−0.00131 (10)	−0.28933 (5)	−0.26159 (3)	0.0543 (2)

	U11	U22	U33	U12	U13	U23
C1	0.054 (2)	0.142 (4)	0.102 (3)	0.014 (2)	0.001 (2)	0.028 (3)
C2	0.060 (2)	0.079 (2)	0.045 (2)	−0.0056 (19)	0.004 (2)	−0.0055 (19)
C3	0.0561 (19)	0.0494 (17)	0.037 (2)	−0.0002 (15)	0.0048 (17)	−0.0052 (16)
C4	0.064 (2)	0.0541 (19)	0.048 (2)	−0.0067 (16)	0.0060 (19)	−0.0004 (17)
C5	0.0574 (18)	0.0435 (17)	0.039 (2)	−0.0019 (16)	0.0095 (17)	0.0004 (16)
C6	0.073 (2)	0.062 (2)	0.056 (2)	0.0068 (18)	0.002 (2)	−0.015 (2)
C7	0.090 (3)	0.081 (3)	0.064 (3)	−0.006 (2)	−0.011 (2)	−0.014 (2)
C8	0.077 (3)	0.083 (3)	0.079 (3)	−0.003 (2)	−0.019 (3)	0.016 (3)
C9	0.075 (3)	0.073 (3)	0.093 (4)	0.020 (2)	0.006 (3)	0.020 (3)
C10	0.080 (2)	0.0543 (18)	0.054 (2)	0.001 (2)	0.004 (2)	−0.0020 (16)
C11	0.0565 (17)	0.0441 (18)	0.042 (2)	0.0000 (16)	0.0048 (16)	−0.0058 (16)
C12	0.0481 (16)	0.0448 (16)	0.0357 (18)	−0.0063 (13)	0.0065 (15)	−0.0025 (14)
C13	0.083 (2)	0.0396 (16)	0.053 (2)	−0.0001 (17)	0.022 (2)	0.0063 (15)
C14	0.078 (2)	0.0443 (18)	0.061 (2)	0.0057 (15)	0.032 (2)	−0.0004 (17)
C15	0.0430 (14)	0.0451 (17)	0.0396 (19)	−0.0047 (13)	0.0040 (14)	−0.0019 (15)
C16	0.0402 (16)	0.0413 (17)	0.042 (2)	−0.0075 (13)	−0.0025 (15)	−0.0023 (15)
C17	0.058 (2)	0.169 (4)	0.106 (4)	−0.041 (3)	−0.019 (2)	0.003 (3)
C18	0.0449 (17)	0.0638 (18)	0.053 (2)	0.0000 (18)	0.006 (2)	0.0113 (18)
C19	0.0463 (17)	0.0491 (17)	0.0394 (19)	0.0077 (14)	0.0069 (16)	0.0049 (15)
C20	0.059 (2)	0.064 (2)	0.041 (2)	0.0049 (16)	0.0100 (17)	−0.0013 (17)
C21	0.063 (2)	0.052 (2)	0.044 (2)	−0.0059 (17)	0.0036 (19)	−0.0103 (17)
C22	0.070 (3)	0.075 (2)	0.062 (3)	0.0000 (19)	0.000 (2)	0.004 (2)
C23	0.080 (3)	0.123 (4)	0.085 (4)	−0.001 (3)	−0.019 (3)	−0.014 (3)
C24	0.070 (3)	0.142 (5)	0.123 (5)	−0.022 (3)	−0.009 (3)	−0.044 (4)
C25	0.111 (4)	0.107 (4)	0.115 (5)	−0.058 (3)	0.026 (4)	−0.003 (3)
C26	0.090 (3)	0.070 (2)	0.076 (3)	−0.021 (2)	0.004 (2)	0.009 (2)
C27	0.296 (9)	0.128 (4)	0.205 (8)	0.092 (5)	−0.165 (8)	−0.053 (5)
C28	0.273 (8)	0.179 (6)	0.100 (5)	0.115 (6)	−0.059 (5)	−0.021 (5)
C29	0.221 (7)	0.108 (4)	0.183 (7)	0.041 (4)	−0.082 (6)	0.015 (5)
C30	0.136 (4)	0.105 (3)	0.125 (4)	0.033 (3)	−0.008 (4)	−0.011 (3)
N1	0.0621 (15)	0.0417 (14)	0.0399 (17)	0.0044 (12)	0.0133 (14)	−0.0017 (12)
N2	0.0471 (13)	0.0418 (12)	0.0401 (15)	0.0052 (12)	0.0075 (12)	0.0059 (13)
O1	0.0563 (14)	0.0945 (17)	0.0728 (18)	0.0055 (13)	0.0091 (13)	−0.0053 (15)
O2	0.0844 (19)	0.212 (3)	0.090 (2)	0.004 (2)	−0.0221 (19)	−0.072 (2)
O3	0.141 (2)	0.0481 (14)	0.0839 (19)	−0.0028 (15)	0.0556 (17)	−0.0047 (14)
O4	0.0709 (13)	0.0386 (11)	0.0568 (16)	0.0086 (10)	0.0112 (12)	0.0071 (11)
O5	0.0672 (16)	0.151 (2)	0.082 (2)	−0.0221 (15)	0.0101 (14)	0.047 (2)
O6	0.0554 (13)	0.128 (2)	0.0623 (17)	−0.0274 (13)	−0.0090 (13)	0.0150 (16)
O7	0.161 (3)	0.0830 (19)	0.110 (3)	0.054 (2)	−0.056 (2)	−0.0078 (18)
S1	0.0711 (5)	0.0404 (4)	0.0516 (5)	0.0027 (4)	0.0181 (5)	0.0008 (4)

C1—O1	1.461 (4)	C17—H17A	0.9600
C1—H1A	0.9600	C17—H17B	0.9600
C1—H1B	0.9600	C17—H17C	0.9600
C1—H1C	0.9600	C18—O5	1.188 (3)
C2—O2	1.178 (4)	C18—O6	1.299 (4)
C2—O1	1.306 (4)	C18—C19	1.509 (4)
C2—C3	1.524 (4)	C19—N2	1.446 (3)
C3—N1	1.448 (3)	C19—C20	1.533 (4)
C3—C4	1.535 (4)	C19—H19	0.9800
C3—H3	0.9800	C20—C21	1.491 (4)
C4—C5	1.506 (4)	C20—H20B	0.9700
C4—H4A	0.9700	C20—H20A	0.9700
C4—H4B	0.9700	C21—C26	1.377 (4)
C5—C10	1.371 (4)	C21—C22	1.378 (4)
C5—C6	1.382 (4)	C22—C23	1.374 (5)
C6—C7	1.373 (5)	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.357 (6)
C7—C8	1.350 (5)	C23—H23	0.9300
C7—H7	0.9300	C24—C25	1.374 (6)
C8—C9	1.357 (5)	C24—H24	0.9300
C8—H8	0.9300	C25—C26	1.373 (5)
C9—C10	1.383 (5)	C25—H25	0.9300
C9—H9	0.9300	C26—H26	0.9300
C10—H10	0.9300	C27—C28	1.417 (7)
C11—O3	1.229 (3)	C27—O7	1.445 (6)
C11—N1	1.327 (3)	C27—H27A	0.9700
C11—C12	1.465 (4)	C27—H27B	0.9700
C12—C13	1.345 (4)	C28—C29	1.430 (7)
C12—S1	1.711 (3)	C28—H28B	0.9700
C13—C14	1.414 (4)	C28—H28A	0.9700
C13—H13	0.9300	C29—C30	1.489 (6)
C14—C15	1.342 (4)	C29—H29B	0.9700
C14—H14	0.9300	C29—H29A	0.9700
C15—C16	1.491 (4)	C30—O7	1.333 (4)
C15—S1	1.716 (3)	C30—H30A	0.9700
C16—O4	1.232 (3)	C30—H30B	0.9700
C16—N2	1.328 (3)	N1—H1	0.8600
C17—O6	1.465 (4)	N2—H2	0.8600
O1—C1—H1A	109.5	O6—C18—C19	113.8 (3)
O1—C1—H1B	109.5	N2—C19—C18	114.4 (3)
H1A—C1—H1B	109.5	N2—C19—C20	110.9 (2)
O1—C1—H1C	109.5	C18—C19—C20	110.7 (2)
H1A—C1—H1C	109.5	N2—C19—H19	106.8
H1B—C1—H1C	109.5	C18—C19—H19	106.8
O2—C2—O1	123.1 (3)	C20—C19—H19	106.8
O2—C2—C3	124.7 (3)	C21—C20—C19	112.6 (2)
O1—C2—C3	112.2 (3)	C21—C20—H20B	109.1
N1—C3—C2	109.7 (3)	C19—C20—H20B	109.1
N1—C3—C4	113.1 (2)	C21—C20—H20A	109.1
C2—C3—C4	110.3 (2)	C19—C20—H20A	109.1
N1—C3—H3	107.9	H20B—C20—H20A	107.8
C2—C3—H3	107.9	C26—C21—C22	117.8 (3)
C4—C3—H3	107.9	C26—C21—C20	120.9 (3)
C5—C4—C3	112.8 (2)	C22—C21—C20	121.3 (3)
C5—C4—H4A	109.0	C23—C22—C21	121.3 (4)
C3—C4—H4A	109.0	C23—C22—H22	119.3
C5—C4—H4B	109.0	C21—C22—H22	119.3
C3—C4—H4B	109.0	C24—C23—C22	120.8 (4)
H4A—C4—H4B	107.8	C24—C23—H23	119.6
C10—C5—C6	117.9 (3)	C22—C23—H23	119.6
C10—C5—C4	121.7 (3)	C23—C24—C25	118.3 (4)
C6—C5—C4	120.5 (3)	C23—C24—H24	120.8
C7—C6—C5	121.2 (3)	C25—C24—H24	120.8
C7—C6—H6	119.4	C26—C25—C24	121.5 (5)
C5—C6—H6	119.4	C26—C25—H25	119.3
C8—C7—C6	119.8 (4)	C24—C25—H25	119.3
C8—C7—H7	120.1	C25—C26—C21	120.3 (4)
C6—C7—H7	120.1	C25—C26—H26	119.8
C7—C8—C9	120.5 (4)	C21—C26—H26	119.8
C7—C8—H8	119.7	C28—C27—O7	105.8 (5)
C9—C8—H8	119.7	C28—C27—H27A	110.6
C8—C9—C10	119.9 (4)	O7—C27—H27A	110.6
C8—C9—H9	120.0	C28—C27—H27B	110.6
C10—C9—H9	120.0	O7—C27—H27B	110.6
C5—C10—C9	120.7 (3)	H27A—C27—H27B	108.7
C5—C10—H10	119.7	C27—C28—C29	107.3 (5)
C9—C10—H10	119.7	C27—C28—H28B	110.3
O3—C11—N1	121.2 (3)	C29—C28—H28B	110.3
O3—C11—C12	119.3 (3)	C27—C28—H28A	110.3
N1—C11—C12	119.5 (3)	C29—C28—H28A	110.3
C13—C12—C11	131.8 (3)	H28B—C28—H28A	108.5
C13—C12—S1	111.4 (2)	C28—C29—C30	105.0 (5)
C11—C12—S1	116.8 (2)	C28—C29—H29B	110.8
C12—C13—C14	112.7 (3)	C30—C29—H29B	110.8
C12—C13—H13	123.7	C28—C29—H29A	110.8
C14—C13—H13	123.7	C30—C29—H29A	110.8
C15—C14—C13	113.1 (3)	H29B—C29—H29A	108.8
C15—C14—H14	123.4	O7—C30—C29	105.7 (4)
C13—C14—H14	123.4	O7—C30—H30A	110.6
C14—C15—C16	130.6 (3)	C29—C30—H30A	110.6
C14—C15—S1	111.1 (2)	O7—C30—H30B	110.6
C16—C15—S1	118.1 (2)	C29—C30—H30B	110.6
O4—C16—N2	123.9 (3)	H30A—C30—H30B	108.7
O4—C16—C15	121.2 (3)	C11—N1—C3	120.8 (2)
N2—C16—C15	114.8 (2)	C11—N1—H1	119.6
O6—C17—H17A	109.5	C3—N1—H1	119.6
O6—C17—H17B	109.5	C16—N2—C19	123.0 (2)
H17A—C17—H17B	109.5	C16—N2—H2	118.5
O6—C17—H17C	109.5	C19—N2—H2	118.5
H17A—C17—H17C	109.5	C2—O1—C1	116.5 (3)
H17B—C17—H17C	109.5	C18—O6—C17	116.6 (3)
O5—C18—O6	124.1 (3)	C30—O7—C27	107.6 (4)
O5—C18—C19	122.1 (3)	C12—S1—C15	91.70 (14)
O2—C2—C3—N1	−27.1 (5)	N2—C19—C20—C21	−61.3 (3)
O1—C2—C3—N1	152.6 (3)	C18—C19—C20—C21	170.6 (3)
O2—C2—C3—C4	98.1 (4)	C19—C20—C21—C26	93.0 (4)
O1—C2—C3—C4	−82.3 (3)	C19—C20—C21—C22	−85.4 (4)
N1—C3—C4—C5	−63.2 (3)	C26—C21—C22—C23	0.3 (5)
C2—C3—C4—C5	173.6 (3)	C20—C21—C22—C23	178.8 (3)
C3—C4—C5—C10	100.2 (3)	C21—C22—C23—C24	−0.4 (6)
C3—C4—C5—C6	−79.2 (4)	C22—C23—C24—C25	0.4 (7)
C10—C5—C6—C7	0.7 (5)	C23—C24—C25—C26	−0.2 (8)
C4—C5—C6—C7	−179.9 (3)	C24—C25—C26—C21	0.0 (7)
C5—C6—C7—C8	−2.0 (6)	C22—C21—C26—C25	−0.1 (5)
C6—C7—C8—C9	2.7 (6)	C20—C21—C26—C25	−178.6 (4)
C7—C8—C9—C10	−2.1 (6)	O7—C27—C28—C29	−11.0 (9)
C6—C5—C10—C9	−0.1 (5)	C27—C28—C29—C30	−6.4 (9)
C4—C5—C10—C9	−179.6 (3)	C28—C29—C30—O7	23.0 (7)
C8—C9—C10—C5	0.9 (5)	O3—C11—N1—C3	−8.9 (4)
O3—C11—C12—C13	−173.0 (3)	C12—C11—N1—C3	170.4 (2)
N1—C11—C12—C13	7.7 (5)	C2—C3—N1—C11	−87.8 (3)
O3—C11—C12—S1	8.6 (4)	C4—C3—N1—C11	148.6 (3)
N1—C11—C12—S1	−170.8 (2)	O4—C16—N2—C19	9.1 (4)
C11—C12—C13—C14	−178.4 (3)	C15—C16—N2—C19	−170.2 (2)
S1—C12—C13—C14	0.1 (3)	C18—C19—N2—C16	−107.0 (3)
C12—C13—C14—C15	−0.8 (4)	C20—C19—N2—C16	127.0 (3)
C13—C14—C15—C16	176.3 (3)	O2—C2—O1—C1	−0.3 (5)
C13—C14—C15—S1	1.2 (3)	C3—C2—O1—C1	−179.9 (3)
C14—C15—C16—O4	−159.8 (3)	O5—C18—O6—C17	−0.1 (5)
S1—C15—C16—O4	15.0 (3)	C19—C18—O6—C17	−178.2 (3)
C14—C15—C16—N2	19.5 (4)	C29—C30—O7—C27	−30.3 (6)
S1—C15—C16—N2	−165.68 (19)	C28—C27—O7—C30	26.6 (7)
O5—C18—C19—N2	173.3 (3)	C13—C12—S1—C15	0.5 (2)
O6—C18—C19—N2	−8.6 (4)	C11—C12—S1—C15	179.2 (2)
O5—C18—C19—C20	−60.6 (4)	C14—C15—S1—C12	−1.0 (2)
O6—C18—C19—C20	117.5 (3)	C16—C15—S1—C12	−176.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O7	0.86	2.02	2.859 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O7	0.86	2.02	2.859 (3)	164