Diethyl (2'R,4R,4'R)-2-(4'-ethoxy­carbonyl-2'-thia­zolidinyl)-6-methyl-4-(2''-thienyl)-1,4-di­hydro­pyridine-3,5-di­carboxyl­ate

In the title compound, C₂₂H₂₈N₂O₆S₂, the 1,4-di­hydro­pyridine (DHP) ring has a flat-boat conformation. The 2-thio­phene ring is disordered over two orientations and is approximately perpendicular to the DHP ring. For each ester group, at the 3- and 5-positions of the DHP ring, the carbonyl group is cis with respect to the conjugated C=C double bond.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.044
• wR factor = 0.096
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.76 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.20 Ratio
PLAT241_ALERT_2_B Check High   U(eq) as Compared to Neighbors ....        C25
PLAT241_ALERT_2_B Check High   U(eq) as Compared to Neighbors ....        C35
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors ....        C22
PLAT360_ALERT_2_B Short  C(sp3)-C(sp3) Bond  C20    -   C21      =       1.33 Ang.

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT213_ALERT_2_C Atom C24     has ADP max/min Ratio .............       3.30 prolat
PLAT213_ALERT_2_C Atom C26     has ADP max/min Ratio .............       3.10 oblate
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C26
PLAT301_ALERT_3_C Main Residue  Disorder .........................      11.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C15    -   C16      =       1.36 Ang.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C30    -   C31      =       1.35 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N11    -   H11    ...          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C22 H28 N2 O6 S2

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           30.31
           From the CIF: _reflns_number_total               5925
           Count of symmetry unique reflns         3828
           Completeness (_total/calc)            154.78%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2097
           Fraction of Friedel pairs measured     0.548
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   7 ALERT level B = Potentially serious problem
  12 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Diethyl (2'R,4R,4'R)-2-(4'-ethoxycarbonyl-2'-thiazolidinyl)-6-methyl-4-(2''-thienyl)- 1,4-dihydropyridine-3,5-dicarboxylate

Crystal data

C22H28N2O6S2	F(000) = 508
Mr = 480.58	Dx = 1.320 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.347 (2) Å	Cell parameters from 7503 reflections
b = 9.3127 (19) Å	θ = 3.0–30.3°
c = 13.160 (3) Å	µ = 0.26 mm^−1
β = 107.53 (3)°	T = 293 K
V = 1209.1 (4) Å^3	Plate, yellow
Z = 2	0.4 × 0.3 × 0.3 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer	2506 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 30.3°, θmin = 3.0°
Detector resolution: Sapphore CCD detector pixels mm^-1	h = −14→12
Rotation method data acquisition using ω and φ scans	k = −12→12
7507 measured reflections	l = −18→18
5925 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.052P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.013
5925 reflections	Δρmax = 0.17 e Å^−3
330 parameters	Δρmin = −0.19 e Å^−3
11 restraints	Absolute structure: Flack (1983), 2097 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (8)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C2	−0.8636 (3)	−0.8450 (3)	−0.2673 (2)	0.0510 (7)
C3	−0.9371 (2)	−0.7674 (3)	−0.21760 (17)	0.0479 (6)
C4	−0.8678 (2)	−0.6963 (3)	−0.11141 (19)	0.0535 (7)
H4	−0.9280	−0.7042	−0.0667	0.064*
C5	−0.7351 (2)	−0.7719 (4)	−0.05446 (19)	0.0542 (6)
C6	−0.6701 (3)	−0.8515 (3)	−0.1085 (2)	0.0541 (7)
C7	−0.9143 (3)	−0.9094 (3)	−0.37838 (19)	0.0537 (7)
H7	−1.0081	−0.9416	−0.3919	0.064*
C9	−0.8697 (3)	−0.9046 (4)	−0.5614 (2)	0.0723 (9)
H9A	−0.9515	−0.9522	−0.6039	0.087*
H9B	−0.8240	−0.8620	−0.6085	0.087*
C10	−0.7771 (3)	−1.0085 (3)	−0.4839 (2)	0.0606 (8)
H10	−0.7800	−1.1011	−0.5199	0.073*
C12	−0.6313 (3)	−0.9570 (3)	−0.4471 (3)	0.0703 (9)
C15	−0.4452 (3)	−0.8896 (6)	−0.5067 (3)	0.1248 (15)
H15A	−0.4374	−0.7870	−0.4936	0.150*
H15B	−0.3914	−0.9379	−0.4426	0.150*
C16	−0.3951 (4)	−0.9219 (8)	−0.5881 (4)	0.179 (3)
H16C	−0.3027	−0.8903	−0.5706	0.269*
H16A	−0.4481	−0.8745	−0.6518	0.269*
H16B	−0.3991	−1.0239	−0.5994	0.269*
C17	−1.0822 (3)	−0.7467 (3)	−0.2655 (2)	0.0563 (7)
C20	−1.2826 (3)	−0.6586 (5)	−0.2342 (3)	0.1055 (13)
H20A	−1.2992	−0.5777	−0.2829	0.127*
H20B	−1.3295	−0.7415	−0.2728	0.127*
C21	−1.3302 (4)	−0.6293 (6)	−0.1531 (4)	0.156 (2)
H21A	−1.3026	−0.7032	−0.1001	0.234*
H21B	−1.4274	−0.6249	−0.1783	0.234*
H21C	−1.2950	−0.5385	−0.1223	0.234*
C22	−0.8460 (3)	−0.5405 (4)	−0.1279 (3)	0.0608 (9)
C25	−0.848 (2)	−0.2918 (18)	−0.1148 (17)	0.142 (8)	0.531 (6)
H25	−0.8743	−0.2035	−0.0949	0.171*	0.531 (6)
C26	−0.8765 (14)	−0.4269 (11)	−0.0758 (10)	0.083 (4)	0.531 (6)
H26	−0.9131	−0.4359	−0.0197	0.100*	0.531 (6)
C27	−0.6790 (3)	−0.7506 (4)	0.0607 (2)	0.0668 (8)
C30	−0.7211 (4)	−0.6561 (6)	0.2142 (3)	0.1239 (16)
H30B	−0.6872	−0.7441	0.2524	0.149*
H30A	−0.6474	−0.5873	0.2297	0.149*
C31	−0.8230 (5)	−0.6037 (6)	0.2473 (3)	0.1444 (19)
H31C	−0.7935	−0.5957	0.3236	0.217*
H31B	−0.8994	−0.6673	0.2256	0.217*
H31A	−0.8486	−0.5106	0.2164	0.217*
C32	−0.5362 (3)	−0.9261 (4)	−0.0661 (2)	0.0738 (9)
H32A	−0.4737	−0.8645	−0.0163	0.111*
H32B	−0.5011	−0.9484	−0.1240	0.111*
H32C	−0.5480	−1.0132	−0.0310	0.111*
C33	−0.842 (2)	−0.2783 (19)	−0.134 (2)	0.119 (7)	0.469 (6)
H33	−0.8524	−0.1802	−0.1258	0.143*	0.469 (6)
C24	−0.778 (2)	−0.3088 (8)	−0.1831 (18)	0.113 (9)	0.531 (6)
H24	−0.7458	−0.2331	−0.2150	0.135*	0.531 (6)
C35	−0.768 (2)	−0.4829 (17)	−0.1826 (16)	0.136 (12)	0.469 (6)
H35	−0.7198	−0.5404	−0.2162	0.163*	0.469 (6)
C34	−0.762 (2)	−0.3308 (17)	−0.1870 (18)	0.122 (9)	0.469 (6)
H34	−0.7114	−0.2776	−0.2210	0.146*	0.469 (6)
N1	−0.7306 (2)	−0.8738 (2)	−0.21642 (16)	0.0574 (6)
H1	−0.6817	−0.9076	−0.2533	0.069*
N11	−0.8324 (2)	−1.0279 (3)	−0.39538 (18)	0.0626 (6)
H11	−0.8176	−1.1038	−0.3562	0.075*
O13	−0.5633 (2)	−0.9462 (3)	−0.35663 (16)	0.0922 (8)
O14	−0.5871 (2)	−0.9322 (3)	−0.52934 (16)	0.0935 (8)
O18	−1.14931 (16)	−0.7749 (3)	−0.35628 (14)	0.0674 (5)
O19	−1.13832 (18)	−0.6877 (3)	−0.19562 (15)	0.0758 (6)
O28	−0.5687 (2)	−0.7824 (3)	0.11686 (15)	0.0980 (8)
O29	−0.7674 (2)	−0.6847 (3)	0.10118 (15)	0.0877 (7)
S8	−0.90762 (8)	−0.77165 (10)	−0.47575 (6)	0.0737 (3)
S23	−0.7528 (4)	−0.4848 (4)	−0.2061 (5)	0.0915 (12)	0.531 (6)
S32	−0.9232 (6)	−0.4042 (6)	−0.0823 (6)	0.0989 (10)	0.469 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0439 (16)	0.0598 (18)	0.0463 (15)	−0.0013 (14)	0.0091 (13)	0.0097 (14)
C3	0.0351 (14)	0.0632 (16)	0.0422 (13)	−0.0028 (14)	0.0070 (11)	−0.0031 (16)
C4	0.0442 (16)	0.068 (2)	0.0446 (15)	0.0006 (15)	0.0084 (12)	0.0011 (14)
C5	0.0466 (15)	0.0649 (17)	0.0455 (14)	−0.0040 (16)	0.0051 (12)	0.0094 (17)
C6	0.0434 (16)	0.070 (2)	0.0446 (16)	0.0037 (14)	0.0061 (13)	0.0047 (14)
C7	0.0429 (15)	0.0611 (19)	0.0536 (17)	−0.0001 (15)	0.0095 (12)	−0.0036 (15)
C9	0.0554 (18)	0.104 (2)	0.0517 (17)	0.0140 (19)	0.0071 (14)	−0.0147 (18)
C10	0.0499 (18)	0.070 (2)	0.0541 (17)	−0.0009 (16)	0.0032 (15)	−0.0173 (16)
C12	0.052 (2)	0.089 (3)	0.066 (2)	0.0079 (17)	0.0111 (18)	−0.0151 (19)
C15	0.065 (2)	0.203 (5)	0.112 (3)	−0.039 (3)	0.035 (2)	−0.045 (3)
C16	0.083 (3)	0.338 (9)	0.128 (4)	−0.029 (4)	0.047 (3)	−0.083 (5)
C17	0.0519 (18)	0.059 (2)	0.0544 (17)	0.0005 (15)	0.0112 (15)	0.0117 (16)
C20	0.054 (2)	0.179 (4)	0.081 (2)	0.040 (2)	0.0165 (19)	0.002 (3)
C21	0.108 (3)	0.237 (6)	0.142 (4)	0.079 (4)	0.067 (3)	0.036 (4)
C22	0.052 (2)	0.072 (3)	0.0498 (19)	0.0091 (18)	0.0022 (15)	−0.0073 (18)
C25	0.156 (18)	0.077 (15)	0.136 (13)	−0.013 (13)	−0.043 (10)	−0.032 (11)
C26	0.075 (7)	0.051 (7)	0.134 (8)	0.046 (5)	0.048 (5)	0.026 (6)
C27	0.064 (2)	0.081 (2)	0.0468 (17)	−0.0062 (19)	0.0042 (16)	0.0069 (18)
C30	0.097 (3)	0.214 (5)	0.052 (2)	0.011 (3)	0.009 (2)	−0.039 (3)
C31	0.146 (4)	0.187 (5)	0.099 (3)	−0.006 (4)	0.035 (3)	−0.065 (3)
C32	0.0509 (17)	0.100 (3)	0.0619 (18)	0.0114 (17)	0.0033 (14)	0.0083 (18)
C33	0.099 (14)	0.075 (14)	0.180 (18)	0.022 (10)	0.038 (12)	0.007 (12)
C24	0.098 (16)	0.038 (7)	0.15 (2)	−0.026 (7)	−0.037 (12)	0.041 (9)
C35	0.21 (2)	0.058 (13)	0.130 (16)	0.043 (12)	0.031 (12)	−0.028 (11)
C34	0.072 (11)	0.167 (19)	0.100 (15)	0.028 (11)	−0.016 (9)	−0.008 (12)
N1	0.0419 (13)	0.0805 (19)	0.0470 (13)	0.0031 (12)	0.0091 (10)	−0.0040 (12)
N11	0.0634 (15)	0.0586 (16)	0.0598 (15)	0.0038 (13)	0.0095 (13)	0.0060 (13)
O13	0.0495 (12)	0.162 (3)	0.0557 (13)	−0.0038 (13)	0.0012 (10)	−0.0178 (14)
O14	0.0609 (14)	0.157 (2)	0.0617 (13)	−0.0190 (14)	0.0167 (11)	−0.0254 (14)
O18	0.0470 (10)	0.0952 (14)	0.0513 (10)	0.0027 (11)	0.0016 (9)	0.0036 (13)
O19	0.0444 (12)	0.1221 (18)	0.0598 (12)	0.0117 (12)	0.0140 (10)	−0.0080 (12)
O28	0.0736 (14)	0.149 (2)	0.0552 (12)	0.0208 (16)	−0.0054 (11)	−0.0075 (16)
O29	0.0751 (14)	0.136 (2)	0.0471 (12)	0.0008 (15)	0.0102 (11)	−0.0169 (13)
S8	0.0842 (6)	0.0792 (5)	0.0546 (4)	0.0198 (5)	0.0164 (4)	0.0078 (5)
S23	0.094 (2)	0.075 (3)	0.105 (2)	−0.0177 (16)	0.0289 (16)	0.0125 (16)
S32	0.096 (5)	0.081 (3)	0.112 (5)	0.0231 (19)	0.0381 (18)	−0.0138 (17)

Geometric parameters (Å, º)

C2—C3	1.352 (3)	C20—H20A	0.9700
C2—N1	1.363 (3)	C20—H20B	0.9700
C2—C7	1.520 (3)	C21—H21A	0.9600
C3—C17	1.456 (3)	C21—H21B	0.9600
C3—C4	1.517 (3)	C21—H21C	0.9600
C4—C22	1.494 (4)	C22—C35	1.344 (5)
C4—C5	1.524 (3)	C22—C26	1.349 (5)
C4—H4	0.9800	C22—S23	1.690 (4)
C5—C6	1.339 (4)	C22—S32	1.702 (4)
C5—C27	1.464 (4)	C25—C24	1.322 (5)
C6—N1	1.385 (3)	C25—C26	1.423 (5)
C6—C32	1.499 (4)	C25—H25	0.9300
C7—N11	1.450 (3)	C26—H26	0.9300
C7—S8	1.829 (3)	C27—O28	1.195 (3)
C7—H7	0.9800	C27—O29	1.338 (3)
C9—C10	1.518 (4)	C30—C31	1.348 (5)
C9—S8	1.795 (3)	C30—O29	1.443 (4)
C9—H9A	0.9700	C30—H30B	0.9700
C9—H9B	0.9700	C30—H30A	0.9700
C10—N11	1.456 (3)	C31—H31C	0.9600
C10—C12	1.517 (4)	C31—H31B	0.9600
C10—H10	0.9800	C31—H31A	0.9600
C12—O13	1.190 (3)	C32—H32A	0.9600
C12—O14	1.317 (3)	C32—H32B	0.9600
C15—C16	1.356 (5)	C32—H32C	0.9600
C15—O14	1.462 (3)	C33—C34	1.322 (5)
C15—H15A	0.9700	C33—S32	1.702 (5)
C15—H15B	0.9700	C33—H33	0.9300
C16—H16C	0.9600	C24—S23	1.700 (5)
C16—H16A	0.9600	C24—H24	0.9300
C16—H16B	0.9600	C35—C34	1.420 (5)
C17—O18	1.216 (3)	C35—H35	0.9300
C17—O19	1.344 (3)	C34—H34	0.9300
C20—C21	1.332 (5)	N1—H1	0.8600
C20—O19	1.450 (3)	N11—H11	0.8600
C3—C2—N1	119.9 (2)	H21A—C21—H21B	109.5
C3—C2—C7	126.5 (2)	C20—C21—H21C	109.5
N1—C2—C7	113.6 (2)	H21A—C21—H21C	109.5
C2—C3—C17	121.2 (2)	H21B—C21—H21C	109.5
C2—C3—C4	120.0 (2)	C35—C22—C4	127.4 (8)
C17—C3—C4	118.7 (2)	C26—C22—C4	128.3 (7)
C22—C4—C3	109.9 (2)	C26—C22—S23	109.4 (7)
C22—C4—C5	111.5 (2)	C4—C22—S23	121.7 (3)
C3—C4—C5	110.9 (2)	C35—C22—S32	108.2 (8)
C22—C4—H4	108.1	C4—C22—S32	124.4 (4)
C3—C4—H4	108.1	C24—C25—C26	110.9 (16)
C5—C4—H4	108.1	C24—C25—H25	124.6
C6—C5—C27	121.2 (3)	C26—C25—H25	124.6
C6—C5—C4	121.1 (2)	C22—C26—C25	113.8 (13)
C27—C5—C4	117.6 (3)	C22—C26—H26	123.1
C5—C6—N1	118.9 (2)	C25—C26—H26	123.1
C5—C6—C32	127.9 (2)	O28—C27—O29	120.5 (3)
N1—C6—C32	113.2 (2)	O28—C27—C5	127.8 (3)
N11—C7—C2	113.6 (2)	O29—C27—C5	111.6 (3)
N11—C7—S8	106.19 (17)	C31—C30—O29	110.6 (3)
C2—C7—S8	108.79 (19)	C31—C30—H30B	109.5
N11—C7—H7	109.4	O29—C30—H30B	109.5
C2—C7—H7	109.4	C31—C30—H30A	109.5
S8—C7—H7	109.4	O29—C30—H30A	109.5
C10—C9—S8	103.40 (18)	H30B—C30—H30A	108.1
C10—C9—H9A	111.1	C30—C31—H31C	109.5
S8—C9—H9A	111.1	C30—C31—H31B	109.5
C10—C9—H9B	111.1	H31C—C31—H31B	109.5
S8—C9—H9B	111.1	C30—C31—H31A	109.5
H9A—C9—H9B	109.0	H31C—C31—H31A	109.5
N11—C10—C9	107.2 (2)	H31B—C31—H31A	109.5
N11—C10—C12	112.1 (2)	C6—C32—H32A	109.5
C9—C10—C12	112.2 (3)	C6—C32—H32B	109.5
N11—C10—H10	108.4	H32A—C32—H32B	109.5
C9—C10—H10	108.4	C6—C32—H32C	109.5
C12—C10—H10	108.4	H32A—C32—H32C	109.5
O13—C12—O14	124.1 (3)	H32B—C32—H32C	109.5
O13—C12—C10	125.3 (3)	C34—C33—S32	114.7 (15)
O14—C12—C10	110.6 (3)	C34—C33—H33	122.7
C16—C15—O14	112.2 (3)	S32—C33—H33	122.7
C16—C15—H15A	109.2	C25—C24—S23	112.3 (12)
O14—C15—H15A	109.2	C25—C24—H24	123.8
C16—C15—H15B	109.2	S23—C24—H24	123.8
O14—C15—H15B	109.2	C22—C35—C34	117.4 (14)
H15A—C15—H15B	107.9	C22—C35—H35	121.3
C15—C16—H16C	109.5	C34—C35—H35	121.3
C15—C16—H16A	109.5	C33—C34—C35	107.9 (17)
H16C—C16—H16A	109.5	C33—C34—H34	126.1
C15—C16—H16B	109.5	C35—C34—H34	126.1
H16C—C16—H16B	109.5	C2—N1—C6	123.5 (2)
H16A—C16—H16B	109.5	C2—N1—H1	118.2
O18—C17—O19	121.6 (2)	C6—N1—H1	118.2
O18—C17—C3	127.3 (3)	C7—N11—C10	114.7 (2)
O19—C17—C3	111.1 (2)	C7—N11—H11	122.7
C21—C20—O19	110.4 (3)	C10—N11—H11	122.7
C21—C20—H20A	109.6	C12—O14—C15	117.2 (3)
O19—C20—H20A	109.6	C17—O19—C20	116.6 (2)
C21—C20—H20B	109.6	C27—O29—C30	116.1 (3)
O19—C20—H20B	109.6	C9—S8—C7	91.01 (15)
H20A—C20—H20B	108.1	C22—S23—C24	92.4 (6)
C20—C21—H21A	109.5	C33—S32—C22	91.8 (8)
C20—C21—H21B	109.5
N1—C2—C3—C17	−173.9 (2)	C4—C22—C26—C25	−177.4 (12)
C7—C2—C3—C17	5.1 (4)	S23—C22—C26—C25	11.7 (15)
N1—C2—C3—C4	7.9 (4)	C24—C25—C26—C22	−10 (3)
C7—C2—C3—C4	−173.2 (3)	C6—C5—C27—O28	9.7 (5)
C2—C3—C4—C22	100.4 (3)	C4—C5—C27—O28	−168.3 (3)
C17—C3—C4—C22	−77.9 (3)	C6—C5—C27—O29	−171.6 (3)
C2—C3—C4—C5	−23.4 (4)	C4—C5—C27—O29	10.4 (4)
C17—C3—C4—C5	158.3 (2)	C26—C25—C24—S23	3 (3)
C22—C4—C5—C6	−100.7 (3)	C4—C22—C35—C34	−179.6 (14)
C3—C4—C5—C6	22.1 (4)	S32—C22—C35—C34	2 (2)
C22—C4—C5—C27	77.2 (3)	S32—C33—C34—C35	−1 (3)
C3—C4—C5—C27	−159.9 (2)	C22—C35—C34—C33	−1 (3)
C27—C5—C6—N1	177.0 (3)	C3—C2—N1—C6	12.4 (4)
C4—C5—C6—N1	−5.1 (4)	C7—C2—N1—C6	−166.6 (2)
C27—C5—C6—C32	−1.4 (5)	C5—C6—N1—C2	−13.9 (4)
C4—C5—C6—C32	176.5 (3)	C32—C6—N1—C2	164.7 (2)
C3—C2—C7—N11	−158.1 (3)	C2—C7—N11—C10	−122.6 (2)
N1—C2—C7—N11	20.9 (3)	S8—C7—N11—C10	−3.1 (3)
C3—C2—C7—S8	83.8 (3)	C9—C10—N11—C7	−25.1 (3)
N1—C2—C7—S8	−97.2 (2)	C12—C10—N11—C7	98.5 (3)
S8—C9—C10—N11	41.3 (3)	O13—C12—O14—C15	0.3 (5)
S8—C9—C10—C12	−82.2 (3)	C10—C12—O14—C15	−176.6 (3)
N11—C10—C12—O13	7.0 (4)	C16—C15—O14—C12	155.2 (5)
C9—C10—C12—O13	127.7 (3)	O18—C17—O19—C20	−0.3 (4)
N11—C10—C12—O14	−176.2 (3)	C3—C17—O19—C20	178.7 (3)
C9—C10—C12—O14	−55.4 (3)	C21—C20—O19—C17	167.0 (4)
C2—C3—C17—O18	−11.3 (5)	O28—C27—O29—C30	−0.1 (5)
C4—C3—C17—O18	166.9 (3)	C5—C27—O29—C30	−178.9 (3)
C2—C3—C17—O19	169.7 (2)	C31—C30—O29—C27	−173.6 (4)
C4—C3—C17—O19	−12.1 (4)	C10—C9—S8—C7	−37.4 (2)
C3—C4—C22—C35	−63.6 (13)	N11—C7—S8—C9	24.23 (18)
C5—C4—C22—C35	59.8 (13)	C2—C7—S8—C9	146.87 (19)
C3—C4—C22—C26	130.7 (8)	C26—C22—S23—C24	−8.4 (11)
C5—C4—C22—C26	−105.9 (8)	C4—C22—S23—C24	179.9 (9)
C3—C4—C22—S23	−59.4 (4)	C25—C24—S23—C22	3 (2)
C5—C4—C22—S23	64.1 (4)	C34—C33—S32—C22	2 (2)
C3—C4—C22—S32	114.0 (4)	C35—C22—S32—C33	−2.4 (15)
C5—C4—C22—S32	−122.5 (4)	C4—C22—S32—C33	179.6 (10)
C35—C22—C26—C25	14.3 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O13	0.86	2.12	2.963 (3)	168