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

The asymmetric unit of the title compound, C(26)H(26)N(2)O(6)S, contains two independent mol-ecules; each has twofold symmetry with the S atom and the mid-point of the C-C bond of the thio-phene ring located on a twofold rotation axis. In the two mol-ecules, the terminal benzene rings are oriented at dihedral angles of 65.8 (3) and 63.5 (3)° with respect to the central thio-phene rings. The meth-oxy-carbonyl group of one mol-ecule is disordered over two positions with site-occupancy factors of 0.277 (12) and 0.723 (12). Inter-molecular N-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For applications of thio­phene derivatives, see: Xia et al. (2010 ▶).

Experimental

Crystal data

C26H26N2O6S

M = 494.56

Orthorhombic,

a = 9.0769 (3) Å

b = 29.6371 (7) Å

c = 9.3767 (2) Å

V = 2522.45 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 120 K

0.36 × 0.24 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 ▶) T min = 0.867, T max = 1.000

6802 measured reflections

4233 independent reflections

3315 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.187

S = 1.10

4233 reflections

288 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.90 e Å−3

Δρmin = −0.70 e Å−3

Absolute structure: Flack (1983 ▶), 1669 Friedel pairs

Flack parameter: 0.00 (18)

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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033210/xu5003sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033210/xu5003Isup2.hkl

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

C26H26N2O6S	F(000) = 1040
Mr = 494.56	Dx = 1.302 Mg m−3
Orthorhombic, P21212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 4047 reflections
a = 9.0769 (3) Å	θ = 3.4–25.3°
b = 29.6371 (7) Å	µ = 0.17 mm−1
c = 9.3767 (2) Å	T = 120 K
V = 2522.45 (12) Å3	Block, colourless
Z = 4	0.36 × 0.24 × 0.10 mm

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4233 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3315 reflections with I > 2σ(I)
graphite	Rint = 0.051
Detector resolution: 16.0355 pixels mm-1	θmax = 25.0°, θmin = 3.4°
ω scans	h = −6→10
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	k = −28→35
Tmin = 0.867, Tmax = 1.000	l = −7→11
6802 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)] = 0.068	H-atom parameters constrained
wR(F2) = 0.187	w = 1/[σ2(Fo2) + (0.1124P)2 + 0.8367P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
4233 reflections	Δρmax = 0.90 e Å−3
288 parameters	Δρmin = −0.70 e Å−3
1 restraint	Absolute structure: Flack (1983), 1669 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (18)

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	0.3969 (8)	0.6948 (2)	0.3748 (8)	0.0676 (18)
H1A	0.3112	0.6771	0.3529	0.101*
H1B	0.4259	0.7117	0.2920	0.101*
H1C	0.3745	0.7153	0.4512	0.101*
C2	0.6263 (6)	0.68418 (15)	0.4908 (5)	0.0361 (11)
C3	0.7416 (5)	0.65073 (14)	0.5404 (5)	0.0336 (11)
H3	0.7545	0.6551	0.6432	0.040*
C4	0.8884 (6)	0.66076 (14)	0.4700 (5)	0.0338 (11)
H4B	0.9036	0.6932	0.4685	0.041*
H4A	0.8855	0.6503	0.3720	0.041*
C5	1.0183 (6)	0.63839 (14)	0.5462 (4)	0.0325 (10)
C6	1.0574 (6)	0.59423 (18)	0.5155 (7)	0.0529 (15)
H6	1.0076	0.5782	0.4451	0.063*
C7	1.1729 (8)	0.5739 (2)	0.5915 (8)	0.069 (2)
H7	1.2017	0.5446	0.5691	0.083*
C8	1.2438 (6)	0.59686 (19)	0.6990 (7)	0.0549 (15)
H8	1.3177	0.5828	0.7514	0.066*
C9	1.2052 (7)	0.64021 (18)	0.7282 (6)	0.0521 (14)
H9	1.2551	0.6562	0.7985	0.063*
C10	1.0909 (6)	0.66065 (16)	0.6527 (5)	0.0433 (13)
H10	1.0635	0.6900	0.6753	0.052*
C11	0.6350 (5)	0.57915 (14)	0.6197 (4)	0.0281 (10)
C12	0.5668 (5)	0.53566 (13)	0.5707 (4)	0.0281 (10)
C13	0.5371 (6)	0.52036 (15)	0.4374 (4)	0.0352 (12)
H13	0.5639	0.5357	0.3548	0.042*
C14A	0.207 (2)	0.6027 (7)	0.130 (2)	0.047 (4)	0.275 (12)
H14B	0.1740	0.5900	0.0411	0.070*	0.275 (12)
H14C	0.1380	0.6250	0.1616	0.070*	0.275 (12)
H14A	0.2147	0.5792	0.1999	0.070*	0.275 (12)
C14B	0.3361 (17)	0.5483 (4)	0.091 (2)	0.123 (6)	0.725 (12)
H14E	0.2938	0.5485	−0.0026	0.184*	0.725 (12)
H14F	0.2793	0.5674	0.1529	0.184*	0.725 (12)
H14D	0.3359	0.5181	0.1280	0.184*	0.725 (12)
C15	0.4767 (9)	0.6062 (2)	0.0647 (6)	0.0674 (7)
C16	0.6251 (9)	0.6243 (2)	0.0738 (7)	0.0674 (7)
H16	0.6438	0.6299	0.1752	0.081*
C17	0.6498 (9)	0.6692 (2)	−0.0017 (7)	0.0674 (7)
H17A	0.6582	0.6638	−0.1034	0.081*
H17B	0.5646	0.6883	0.0137	0.081*
C18	0.7826 (9)	0.6931 (2)	0.0477 (6)	0.0674 (7)
C19	0.7774 (9)	0.7261 (2)	0.1503 (6)	0.0674 (7)
H19	0.6853	0.7354	0.1822	0.081*
C20	0.9003 (9)	0.7463 (2)	0.2091 (7)	0.0674 (7)
H20	0.8902	0.7686	0.2783	0.081*
C21	1.0373 (9)	0.7331 (2)	0.1643 (6)	0.0674 (7)
H21	1.1207	0.7472	0.2008	0.081*
C22	1.0519 (9)	0.6990 (2)	0.0649 (6)	0.0674 (7)
H22	1.1448	0.6886	0.0389	0.081*
C23	0.9280 (9)	0.6808 (2)	0.0052 (7)	0.0674 (7)
H23	0.9391	0.6594	−0.0666	0.081*
C24	0.8109 (6)	0.56624 (14)	0.1212 (4)	0.0287 (10)
C25	0.9113 (5)	0.53145 (14)	0.0658 (4)	0.0284 (10)
C26	0.9493 (6)	0.51816 (16)	−0.0702 (4)	0.0395 (13)
H26	0.9124	0.5315	−0.1526	0.047*
N1	0.6976 (4)	0.60424 (11)	0.5186 (4)	0.0276 (8)
H1	0.7127	0.5923	0.4364	0.033*
N2	0.7346 (5)	0.59066 (12)	0.0283 (4)	0.0378 (10)
H2	0.7497	0.5867	−0.0614	0.045*
O1	0.5160 (5)	0.66529 (11)	0.4175 (4)	0.0507 (10)
O2	0.6327 (4)	0.72365 (11)	0.5165 (5)	0.0555 (11)
O3	0.6321 (4)	0.59001 (10)	0.7462 (3)	0.0403 (9)
O4A	0.342 (2)	0.6223 (6)	0.111 (2)	0.047 (4)	0.275 (12)
O4B	0.4741 (16)	0.5635 (4)	0.0848 (17)	0.078 (3)	0.725 (12)
O5A	0.443 (6)	0.5668 (8)	0.057 (5)	0.078 (3)	0.275 (12)
O5B	0.3754 (8)	0.6338 (3)	0.0463 (11)	0.070 (2)	0.725 (12)
O6	0.8024 (4)	0.57171 (10)	0.2509 (3)	0.0349 (8)
S1	0.5000	0.5000	0.70005 (14)	0.0268 (4)
S2	1.0000	0.5000	0.19249 (14)	0.0265 (4)

	U11	U22	U33	U12	U13	U23
C1	0.063 (4)	0.068 (4)	0.072 (4)	0.008 (3)	−0.025 (4)	−0.005 (3)
C2	0.042 (3)	0.030 (2)	0.037 (2)	0.007 (2)	0.012 (2)	0.0014 (19)
C3	0.041 (3)	0.033 (2)	0.027 (2)	−0.002 (2)	−0.002 (2)	−0.0013 (18)
C4	0.050 (3)	0.029 (2)	0.022 (2)	−0.007 (2)	0.000 (2)	−0.0004 (17)
C5	0.033 (3)	0.034 (2)	0.030 (2)	−0.001 (2)	0.004 (2)	−0.0016 (18)
C6	0.048 (3)	0.051 (3)	0.059 (3)	0.006 (3)	−0.013 (3)	−0.030 (3)
C7	0.073 (4)	0.055 (3)	0.081 (4)	0.031 (3)	−0.026 (4)	−0.038 (3)
C8	0.046 (3)	0.059 (3)	0.060 (3)	0.018 (3)	−0.018 (3)	−0.013 (3)
C9	0.054 (4)	0.052 (3)	0.051 (3)	0.004 (3)	−0.009 (3)	−0.020 (3)
C10	0.053 (3)	0.033 (2)	0.044 (3)	0.003 (2)	−0.009 (3)	−0.008 (2)
C11	0.035 (3)	0.031 (2)	0.018 (2)	0.004 (2)	−0.0055 (19)	0.0008 (16)
C12	0.041 (3)	0.027 (2)	0.0163 (19)	0.002 (2)	0.0030 (19)	0.0048 (16)
C13	0.056 (4)	0.035 (2)	0.015 (2)	−0.012 (2)	−0.005 (2)	0.0033 (17)
C14A	0.034 (7)	0.053 (8)	0.053 (8)	−0.013 (5)	0.010 (6)	0.002 (6)
C14B	0.110 (12)	0.068 (7)	0.191 (16)	−0.018 (7)	−0.066 (11)	0.014 (8)
C15	0.0996 (18)	0.0573 (12)	0.0455 (11)	0.0261 (13)	0.0108 (12)	−0.0013 (9)
C16	0.0996 (18)	0.0573 (12)	0.0455 (11)	0.0261 (13)	0.0108 (12)	−0.0013 (9)
C17	0.0996 (18)	0.0573 (12)	0.0455 (11)	0.0261 (13)	0.0108 (12)	−0.0013 (9)
C18	0.0996 (18)	0.0573 (12)	0.0455 (11)	0.0261 (13)	0.0108 (12)	−0.0013 (9)
C19	0.0996 (18)	0.0573 (12)	0.0455 (11)	0.0261 (13)	0.0108 (12)	−0.0013 (9)
C20	0.0996 (18)	0.0573 (12)	0.0455 (11)	0.0261 (13)	0.0108 (12)	−0.0013 (9)
C21	0.0996 (18)	0.0573 (12)	0.0455 (11)	0.0261 (13)	0.0108 (12)	−0.0013 (9)
C22	0.0996 (18)	0.0573 (12)	0.0455 (11)	0.0261 (13)	0.0108 (12)	−0.0013 (9)
C23	0.0996 (18)	0.0573 (12)	0.0455 (11)	0.0261 (13)	0.0108 (12)	−0.0013 (9)
C24	0.040 (3)	0.026 (2)	0.020 (2)	−0.002 (2)	0.000 (2)	−0.0021 (17)
C25	0.039 (3)	0.024 (2)	0.022 (2)	−0.0018 (19)	0.000 (2)	0.0001 (16)
C26	0.069 (4)	0.036 (2)	0.013 (2)	0.008 (2)	−0.002 (2)	0.0005 (16)
N1	0.044 (2)	0.0221 (16)	0.0167 (16)	−0.0009 (17)	−0.0006 (17)	−0.0027 (14)
N2	0.065 (3)	0.0338 (19)	0.0141 (16)	0.018 (2)	−0.0050 (19)	−0.0061 (14)
O1	0.054 (2)	0.0389 (18)	0.059 (2)	0.0089 (18)	−0.026 (2)	−0.0115 (16)
O2	0.057 (3)	0.0316 (19)	0.078 (3)	0.0055 (18)	−0.012 (2)	−0.0154 (17)
O3	0.066 (2)	0.0395 (17)	0.0156 (15)	−0.0111 (17)	−0.0077 (16)	−0.0038 (13)
O4A	0.034 (7)	0.053 (8)	0.053 (8)	−0.013 (5)	0.010 (6)	0.002 (6)
O4B	0.047 (8)	0.115 (4)	0.072 (8)	0.011 (4)	−0.005 (4)	0.048 (4)
O5A	0.047 (8)	0.115 (4)	0.072 (8)	0.011 (4)	−0.005 (4)	0.048 (4)
O5B	0.041 (4)	0.070 (5)	0.100 (6)	0.020 (4)	−0.026 (4)	−0.014 (4)
O6	0.049 (2)	0.0383 (16)	0.0170 (15)	0.0106 (16)	−0.0037 (14)	−0.0017 (12)
S1	0.0425 (9)	0.0263 (7)	0.0118 (6)	0.0010 (7)	0.000	0.000
S2	0.0384 (8)	0.0268 (7)	0.0144 (6)	0.0011 (7)	0.000	0.000

C1—O1	1.447 (7)	C14B—H14E	0.9600
C1—H1A	0.9600	C14B—H14F	0.9600
C1—H1B	0.9600	C14B—H14D	0.9600
C1—H1C	0.9600	C15—O5A	1.21 (2)
C2—O2	1.196 (5)	C15—O5B	1.243 (9)
C2—O1	1.337 (6)	C15—O4B	1.280 (12)
C2—C3	1.515 (7)	C15—O4A	1.38 (2)
C3—N1	1.449 (6)	C15—C16	1.453 (11)
C3—C4	1.516 (7)	C16—N2	1.471 (7)
C3—H3	0.9800	C16—C17	1.523 (9)
C4—C5	1.530 (7)	C16—H16	0.9800
C4—H4B	0.9700	C17—C18	1.472 (10)
C4—H4A	0.9700	C17—H17A	0.9700
C5—C10	1.366 (7)	C17—H17B	0.9700
C5—C6	1.386 (7)	C18—C19	1.373 (8)
C6—C7	1.404 (9)	C18—C23	1.426 (10)
C6—H6	0.9300	C19—C20	1.381 (10)
C7—C8	1.376 (8)	C19—H19	0.9300
C7—H7	0.9300	C20—C21	1.369 (10)
C8—C9	1.360 (8)	C20—H20	0.9300
C8—H8	0.9300	C21—C22	1.381 (9)
C9—C10	1.395 (8)	C21—H21	0.9300
C9—H9	0.9300	C22—C23	1.367 (10)
C10—H10	0.9300	C22—H22	0.9300
C11—O3	1.229 (5)	C23—H23	0.9300
C11—N1	1.332 (6)	C24—O6	1.229 (5)
C11—C12	1.502 (6)	C24—N2	1.328 (6)
C12—C13	1.357 (6)	C24—C25	1.471 (6)
C12—S1	1.719 (4)	C25—C26	1.378 (6)
C13—C13i	1.383 (9)	C25—S2	1.711 (4)
C13—H13	0.9300	C26—C26ii	1.417 (10)
C14A—O4A	1.37 (3)	C26—H26	0.9300
C14A—H14B	0.9600	N1—H1	0.8600
C14A—H14C	0.9600	N2—H2	0.8600
C14A—H14A	0.9600	S1—C12i	1.719 (4)
C14B—O4B	1.33 (2)	S2—C25ii	1.711 (4)
O1—C1—H1A	109.5	O5A—C15—O4A	97 (3)
O1—C1—H1B	109.5	O4B—C15—O4A	106.1 (13)
H1A—C1—H1B	109.5	O5A—C15—C16	126 (3)
O1—C1—H1C	109.5	O5B—C15—C16	116.8 (7)
H1A—C1—H1C	109.5	O4B—C15—C16	112.0 (8)
H1B—C1—H1C	109.5	O4A—C15—C16	132.5 (9)
O2—C2—O1	123.4 (5)	C15—C16—N2	111.0 (5)
O2—C2—C3	123.0 (5)	C15—C16—C17	115.6 (6)
O1—C2—C3	113.6 (4)	N2—C16—C17	110.9 (6)
N1—C3—C2	112.9 (4)	C15—C16—H16	106.2
N1—C3—C4	111.6 (4)	N2—C16—H16	106.2
C2—C3—C4	110.2 (4)	C17—C16—H16	106.2
N1—C3—H3	107.3	C18—C17—C16	113.2 (6)
C2—C3—H3	107.3	C18—C17—H17A	108.9
C4—C3—H3	107.3	C16—C17—H17A	108.9
C3—C4—C5	112.9 (4)	C18—C17—H17B	108.9
C3—C4—H4B	109.0	C16—C17—H17B	108.9
C5—C4—H4B	109.0	H17A—C17—H17B	107.7
C3—C4—H4A	109.0	C19—C18—C23	114.1 (7)
C5—C4—H4A	109.0	C19—C18—C17	122.4 (7)
H4B—C4—H4A	107.8	C23—C18—C17	123.2 (5)
C10—C5—C6	119.0 (5)	C18—C19—C20	124.2 (7)
C10—C5—C4	120.3 (4)	C18—C19—H19	117.9
C6—C5—C4	120.6 (4)	C20—C19—H19	117.9
C5—C6—C7	119.4 (5)	C21—C20—C19	119.1 (6)
C5—C6—H6	120.3	C21—C20—H20	120.4
C7—C6—H6	120.3	C19—C20—H20	120.4
C8—C7—C6	120.5 (5)	C20—C21—C22	120.2 (7)
C8—C7—H7	119.7	C20—C21—H21	119.9
C6—C7—H7	119.7	C22—C21—H21	119.9
C9—C8—C7	119.7 (5)	C23—C22—C21	119.0 (7)
C9—C8—H8	120.2	C23—C22—H22	120.5
C7—C8—H8	120.2	C21—C22—H22	120.5
C8—C9—C10	120.0 (5)	C22—C23—C18	123.2 (6)
C8—C9—H9	120.0	C22—C23—H23	118.4
C10—C9—H9	120.0	C18—C23—H23	118.4
C5—C10—C9	121.3 (4)	O6—C24—N2	123.0 (4)
C5—C10—H10	119.3	O6—C24—C25	118.7 (4)
C9—C10—H10	119.3	N2—C24—C25	118.3 (4)
O3—C11—N1	123.3 (4)	C26—C25—C24	133.0 (4)
O3—C11—C12	120.7 (4)	C26—C25—S2	111.7 (3)
N1—C11—C12	115.9 (4)	C24—C25—S2	115.4 (3)
C13—C12—C11	130.6 (4)	C25—C26—C26ii	112.3 (3)
C13—C12—S1	112.0 (3)	C25—C26—H26	123.8
C11—C12—S1	117.2 (3)	C26ii—C26—H26	123.8
C12—C13—C13i	112.9 (3)	C11—N1—C3	123.2 (4)
C12—C13—H13	123.6	C11—N1—H1	118.4
C13i—C13—H13	123.6	C3—N1—H1	118.4
O4A—C14A—H14B	109.5	C24—N2—C16	122.1 (4)
O4A—C14A—H14C	109.5	C24—N2—H2	119.0
H14B—C14A—H14C	109.5	C16—N2—H2	119.0
O4A—C14A—H14A	109.5	C2—O1—C1	116.6 (4)
H14B—C14A—H14A	109.5	C14A—O4A—C15	133.5 (17)
H14C—C14A—H14A	109.5	C15—O4B—C14B	111.0 (12)
O5A—C15—O5B	116 (2)	C12i—S1—C12	90.3 (3)
O5B—C15—O4B	131.1 (11)	C25ii—S2—C25	92.1 (3)
O2—C2—C3—N1	169.7 (4)	C17—C18—C19—C20	173.7 (6)
O1—C2—C3—N1	−9.4 (6)	C18—C19—C20—C21	−0.1 (10)
O2—C2—C3—C4	−64.8 (6)	C19—C20—C21—C22	−2.1 (9)
O1—C2—C3—C4	116.1 (4)	C20—C21—C22—C23	4.4 (9)
N1—C3—C4—C5	−71.2 (4)	C21—C22—C23—C18	−4.6 (10)
C2—C3—C4—C5	162.7 (4)	C19—C18—C23—C22	2.4 (9)
C3—C4—C5—C10	−90.3 (5)	C17—C18—C23—C22	−171.2 (6)
C3—C4—C5—C6	85.1 (6)	O6—C24—C25—C26	−177.5 (5)
C10—C5—C6—C7	−1.7 (9)	N2—C24—C25—C26	1.8 (8)
C4—C5—C6—C7	−177.2 (6)	O6—C24—C25—S2	3.2 (6)
C5—C6—C7—C8	2.2 (11)	N2—C24—C25—S2	−177.5 (4)
C6—C7—C8—C9	−2.4 (11)	C24—C25—C26—C26ii	−179.0 (5)
C7—C8—C9—C10	2.2 (10)	S2—C25—C26—C26ii	0.4 (8)
C6—C5—C10—C9	1.5 (8)	O3—C11—N1—C3	−13.2 (7)
C4—C5—C10—C9	177.0 (5)	C12—C11—N1—C3	167.1 (4)
C8—C9—C10—C5	−1.8 (9)	C2—C3—N1—C11	−95.6 (5)
O3—C11—C12—C13	168.5 (5)	C4—C3—N1—C11	139.6 (4)
N1—C11—C12—C13	−11.8 (8)	O6—C24—N2—C16	−4.5 (8)
O3—C11—C12—S1	−5.5 (6)	C25—C24—N2—C16	176.3 (5)
N1—C11—C12—S1	174.2 (3)	C15—C16—N2—C24	−99.5 (6)
C11—C12—C13—C13i	−175.3 (5)	C17—C16—N2—C24	130.5 (6)
S1—C12—C13—C13i	−1.0 (8)	O2—C2—O1—C1	−3.0 (8)
O5A—C15—C16—N2	18 (3)	C3—C2—O1—C1	176.1 (5)
O5B—C15—C16—N2	−153.2 (7)	O5A—C15—O4A—C14A	−6(3)
O4B—C15—C16—N2	30.1 (11)	O5B—C15—O4A—C14A	122 (3)
O4A—C15—C16—N2	171.0 (12)	O4B—C15—O4A—C14A	−22 (3)
O5A—C15—C16—C17	145 (3)	C16—C15—O4A—C14A	−164.4 (18)
O5B—C15—C16—C17	−25.7 (9)	O5A—C15—O4B—C14B	−41 (11)
O4B—C15—C16—C17	157.6 (10)	O5B—C15—O4B—C14B	−3(2)
O4A—C15—C16—C17	−61.5 (14)	O4A—C15—O4B—C14B	22.3 (18)
C15—C16—C17—C18	161.2 (5)	C16—C15—O4B—C14B	173.4 (12)
N2—C16—C17—C18	−71.2 (7)	C13—C12—S1—C12i	0.4 (3)
C16—C17—C18—C19	−96.0 (7)	C11—C12—S1—C12i	175.5 (5)
C16—C17—C18—C23	77.1 (8)	C26—C25—S2—C25ii	−0.1 (3)
C23—C18—C19—C20	0.0 (9)	C24—C25—S2—C25ii	179.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6	0.86	2.01	2.853 (5)	164.
N2—H2···O3iii	0.86	2.10	2.803 (5)	139.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6	0.86	2.01	2.853 (5)	164
N2—H2⋯O3i	0.86	2.10	2.803 (5)	139

Symmetry code: (i) .