2-Methyl-N,N'-bis­[2-(methyl­sulfan­yl)eth­yl]-2-(2-pyrid­yl)-N,N'-ditosyl­propane-1,3-diamine

The crystal structure of the title compound, C₂₉H₃₉N₃O₄S₄, was determined at 97 K and possesses normal geometric parameters.

Key indicators

• Single-crystal X-ray study
• T = 97 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.044
• wR factor = 0.122
• Data-to-parameter ratio = 17.1

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-Methyl-N,N'-bis[2-(methylsulfanyl)ethyl]-2-(2-pyridyl)-N,N'-ditosylpropane- 1,3-diamine

Crystal data

C29H39N3O4S4	Z = 2
Mr = 621.87	F(000) = 660
Triclinic, P1	Dx = 1.306 Mg m^−3
Hall symbol: -P 1	Melting point: 133 K
a = 11.446 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.166 (2) Å	Cell parameters from 8357 reflections
c = 12.584 (2) Å	θ = 2.3–28.2°
α = 92.881 (3)°	µ = 0.34 mm^−1
β = 112.681 (3)°	T = 97 K
γ = 99.595 (3)°	Block, colorless
V = 1581.5 (5) Å^3	0.47 × 0.33 × 0.31 mm

Data collection

Bruker APEX CCD area-detector diffractometer	6174 independent reflections
Radiation source: fine-focus sealed tube	5852 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω scans	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −14→14
Tmin = 0.857, Tmax = 0.902	k = −14→14
17215 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.07P)^2 + 1.42P] where P = (Fo^2 + 2Fc^2)/3
6174 reflections	(Δ/σ)max = 0.001
361 parameters	Δρmax = 0.87 e Å^−3
0 restraints	Δρmin = −0.49 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
S1	0.75533 (5)	0.33871 (4)	1.01094 (4)	0.02591 (13)
S2	0.67767 (4)	0.83010 (4)	0.75225 (4)	0.02516 (13)
S3	0.35658 (5)	0.07589 (5)	0.71799 (5)	0.03773 (15)
S4	0.25374 (5)	0.70166 (5)	0.40892 (4)	0.03546 (15)
O1	0.83288 (14)	0.44693 (12)	1.06528 (12)	0.0321 (3)
O2	0.70896 (14)	0.26431 (12)	1.07715 (13)	0.0329 (3)
O3	0.73572 (14)	0.83224 (12)	0.87597 (12)	0.0331 (3)
O4	0.60220 (14)	0.91117 (12)	0.70178 (13)	0.0327 (3)
N1	0.40474 (16)	0.43917 (13)	0.62605 (14)	0.0254 (3)
N2	0.62683 (16)	0.35930 (14)	0.90318 (15)	0.0274 (3)
N3	0.58348 (15)	0.70575 (13)	0.69758 (13)	0.0239 (3)
C1	0.43375 (18)	0.49436 (15)	0.73140 (16)	0.0222 (4)
C2	0.33813 (19)	0.51382 (17)	0.76842 (17)	0.0273 (4)
H2	0.3611	0.5525	0.8434	0.033*
C3	0.2091 (2)	0.47631 (18)	0.69504 (19)	0.0317 (4)
H3	0.1426	0.4883	0.7191	0.038*
C4	0.1788 (2)	0.42086 (18)	0.58567 (19)	0.0339 (4)
H4	0.0914	0.3950	0.5328	0.041*
C5	0.2798 (2)	0.40439 (17)	0.55603 (18)	0.0307 (4)
H5	0.2591	0.3661	0.4814	0.037*
C6	0.57781 (17)	0.53480 (15)	0.80568 (15)	0.0224 (4)
C7	0.60514 (19)	0.60056 (16)	0.92228 (16)	0.0267 (4)
H7A	0.5686	0.5526	0.9667	0.040*
H7B	0.5656	0.6668	0.9089	0.040*
H7C	0.6988	0.6244	0.9659	0.040*
C8	0.64954 (19)	0.43523 (16)	0.82283 (17)	0.0272 (4)
H8A	0.6229	0.3908	0.7463	0.033*
H8B	0.7435	0.4660	0.8518	0.033*
C9	0.84951 (18)	0.27029 (16)	0.95628 (16)	0.0244 (4)
C10	0.93981 (18)	0.33397 (16)	0.92324 (17)	0.0272 (4)
H10	0.9493	0.4134	0.9279	0.033*
C11	1.01582 (19)	0.28030 (17)	0.88342 (17)	0.0294 (4)
H11	1.0767	0.3236	0.8599	0.035*
C12	1.00456 (19)	0.16445 (17)	0.87736 (16)	0.0283 (4)
C13	0.91367 (19)	0.10233 (16)	0.91144 (16)	0.0276 (4)
H13	0.9051	0.0231	0.9080	0.033*
C14	0.83566 (18)	0.15434 (16)	0.95023 (16)	0.0257 (4)
H14	0.7736	0.1111	0.9724	0.031*
C15	1.0890 (2)	0.1070 (2)	0.8358 (2)	0.0389 (5)
H15A	1.1619	0.0926	0.9028	0.058*
H15B	1.1217	0.1555	0.7893	0.058*
H15C	1.0383	0.0357	0.7882	0.058*
C16	0.50846 (19)	0.27030 (17)	0.85919 (18)	0.0297 (4)
H16A	0.4322	0.3061	0.8310	0.036*
H16B	0.5049	0.2295	0.9244	0.036*
C17	0.4994 (2)	0.18583 (19)	0.76170 (19)	0.0340 (4)
H17A	0.5772	0.1520	0.7879	0.041*
H17B	0.4972	0.2251	0.6942	0.041*
C18	0.4059 (3)	−0.0071 (2)	0.8363 (2)	0.0456 (6)
H18A	0.4857	−0.0309	0.8424	0.068*
H18B	0.3377	−0.0734	0.8220	0.068*
H18C	0.4212	0.0380	0.9089	0.068*
C19	0.64090 (18)	0.60788 (15)	0.73732 (16)	0.0233 (4)
H19A	0.7338	0.6348	0.7872	0.028*
H19B	0.6349	0.5600	0.6687	0.028*
C20	0.80224 (18)	0.83753 (15)	0.70159 (16)	0.0241 (4)
C21	0.91252 (18)	0.79675 (17)	0.76479 (17)	0.0285 (4)
H21	0.9239	0.7711	0.8375	0.034*
C22	1.00546 (19)	0.79425 (17)	0.71972 (19)	0.0318 (4)
H22	1.0804	0.7658	0.7619	0.038*
C23	0.99098 (19)	0.83252 (17)	0.61406 (18)	0.0303 (4)
C24	0.8815 (2)	0.87490 (17)	0.55403 (17)	0.0303 (4)
H24	0.8715	0.9025	0.4824	0.036*
C25	0.78677 (19)	0.87773 (16)	0.59645 (17)	0.0266 (4)
H25	0.7123	0.9067	0.5543	0.032*
C26	1.0915 (2)	0.8277 (2)	0.5651 (2)	0.0420 (5)
H26A	1.0495	0.8141	0.4802	0.063*
H26B	1.1364	0.7666	0.5944	0.063*
H26C	1.1541	0.8992	0.5890	0.063*
C27	0.49354 (18)	0.69485 (16)	0.57297 (16)	0.0260 (4)
H27A	0.4878	0.6201	0.5341	0.031*
H27B	0.5283	0.7527	0.5343	0.031*
C28	0.35967 (19)	0.70854 (17)	0.55996 (17)	0.0283 (4)
H28A	0.3658	0.7818	0.6018	0.034*
H28B	0.3230	0.6485	0.5952	0.034*
C29	0.2931 (3)	0.8470 (2)	0.3908 (2)	0.0464 (6)
H29A	0.2672	0.8936	0.4404	0.070*
H29B	0.2470	0.8573	0.3094	0.070*
H29C	0.3864	0.8693	0.4127	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0294 (2)	0.0268 (2)	0.0245 (2)	0.00960 (19)	0.01206 (19)	0.00514 (18)
S2	0.0270 (2)	0.0240 (2)	0.0257 (2)	0.00298 (18)	0.01282 (19)	0.00307 (17)
S3	0.0319 (3)	0.0394 (3)	0.0324 (3)	0.0003 (2)	0.0055 (2)	0.0036 (2)
S4	0.0343 (3)	0.0437 (3)	0.0240 (3)	0.0137 (2)	0.0053 (2)	−0.0002 (2)
O1	0.0350 (8)	0.0320 (8)	0.0313 (7)	0.0074 (6)	0.0154 (6)	0.0018 (6)
O2	0.0361 (8)	0.0360 (8)	0.0323 (7)	0.0099 (6)	0.0181 (6)	0.0090 (6)
O3	0.0388 (8)	0.0341 (8)	0.0258 (7)	−0.0005 (6)	0.0157 (6)	−0.0002 (6)
O4	0.0348 (8)	0.0270 (7)	0.0431 (8)	0.0095 (6)	0.0212 (7)	0.0073 (6)
N1	0.0288 (8)	0.0232 (8)	0.0264 (8)	0.0032 (6)	0.0144 (7)	0.0006 (6)
N2	0.0257 (8)	0.0277 (8)	0.0313 (9)	0.0067 (6)	0.0129 (7)	0.0100 (7)
N3	0.0238 (8)	0.0246 (8)	0.0220 (8)	0.0027 (6)	0.0084 (6)	0.0051 (6)
C1	0.0262 (9)	0.0202 (8)	0.0232 (9)	0.0053 (7)	0.0128 (7)	0.0051 (7)
C2	0.0305 (10)	0.0303 (10)	0.0258 (9)	0.0074 (8)	0.0158 (8)	0.0046 (7)
C3	0.0291 (10)	0.0367 (11)	0.0360 (11)	0.0074 (8)	0.0197 (9)	0.0054 (8)
C4	0.0253 (10)	0.0351 (11)	0.0373 (11)	−0.0005 (8)	0.0115 (9)	−0.0020 (9)
C5	0.0318 (10)	0.0294 (10)	0.0290 (10)	0.0006 (8)	0.0133 (8)	−0.0036 (8)
C6	0.0246 (9)	0.0243 (9)	0.0209 (8)	0.0051 (7)	0.0115 (7)	0.0053 (7)
C7	0.0316 (10)	0.0287 (10)	0.0210 (9)	0.0048 (8)	0.0123 (8)	0.0043 (7)
C8	0.0284 (9)	0.0293 (10)	0.0285 (10)	0.0097 (8)	0.0142 (8)	0.0090 (8)
C9	0.0231 (9)	0.0277 (9)	0.0202 (8)	0.0080 (7)	0.0055 (7)	0.0015 (7)
C10	0.0270 (9)	0.0233 (9)	0.0281 (9)	0.0053 (7)	0.0077 (8)	0.0015 (7)
C11	0.0246 (9)	0.0315 (10)	0.0302 (10)	0.0040 (8)	0.0100 (8)	0.0015 (8)
C12	0.0261 (9)	0.0317 (10)	0.0231 (9)	0.0079 (8)	0.0053 (7)	−0.0032 (7)
C13	0.0294 (10)	0.0229 (9)	0.0238 (9)	0.0058 (7)	0.0038 (8)	−0.0007 (7)
C14	0.0235 (9)	0.0264 (9)	0.0227 (9)	0.0037 (7)	0.0050 (7)	0.0026 (7)
C15	0.0402 (12)	0.0397 (12)	0.0409 (12)	0.0136 (10)	0.0192 (10)	−0.0026 (9)
C16	0.0277 (10)	0.0324 (10)	0.0315 (10)	0.0054 (8)	0.0142 (8)	0.0070 (8)
C17	0.0327 (11)	0.0383 (11)	0.0313 (10)	0.0042 (9)	0.0143 (9)	0.0047 (9)
C18	0.0557 (15)	0.0397 (13)	0.0384 (12)	0.0041 (11)	0.0173 (11)	0.0091 (10)
C19	0.0240 (9)	0.0249 (9)	0.0242 (9)	0.0054 (7)	0.0127 (7)	0.0055 (7)
C20	0.0238 (9)	0.0228 (9)	0.0242 (9)	0.0011 (7)	0.0096 (7)	0.0018 (7)
C21	0.0245 (9)	0.0294 (10)	0.0274 (9)	0.0015 (7)	0.0072 (8)	0.0050 (8)
C22	0.0225 (9)	0.0316 (10)	0.0367 (11)	0.0041 (8)	0.0075 (8)	0.0030 (8)
C23	0.0272 (10)	0.0275 (10)	0.0339 (10)	−0.0028 (8)	0.0140 (8)	−0.0047 (8)
C24	0.0326 (10)	0.0313 (10)	0.0256 (9)	−0.0007 (8)	0.0131 (8)	0.0032 (8)
C25	0.0267 (9)	0.0241 (9)	0.0265 (9)	0.0028 (7)	0.0088 (8)	0.0048 (7)
C26	0.0330 (11)	0.0451 (13)	0.0505 (14)	−0.0011 (9)	0.0242 (10)	−0.0033 (10)
C27	0.0290 (10)	0.0288 (10)	0.0218 (9)	0.0056 (7)	0.0118 (8)	0.0036 (7)
C28	0.0296 (10)	0.0328 (10)	0.0234 (9)	0.0079 (8)	0.0105 (8)	0.0063 (8)
C29	0.0579 (15)	0.0559 (15)	0.0417 (13)	0.0283 (12)	0.0281 (12)	0.0263 (11)

Geometric parameters (Å, º)

S1—O1	1.4286 (16)	C12—C13	1.397 (3)
S1—O2	1.4325 (15)	C12—C15	1.508 (3)
S1—N2	1.6381 (17)	C13—C14	1.389 (3)
S1—C9	1.7724 (19)	C13—H13	0.9500
S2—O4	1.4305 (15)	C14—H14	0.9500
S2—O3	1.4347 (15)	C15—H15A	0.9801
S2—N3	1.6443 (16)	C15—H15B	0.9799
S2—C20	1.7638 (19)	C15—H15C	0.9800
S3—C18	1.802 (2)	C16—C17	1.520 (3)
S3—C17	1.808 (2)	C16—H16A	0.9900
S4—C29	1.799 (3)	C16—H16B	0.9900
S4—C28	1.806 (2)	C17—H17A	0.9900
N1—C5	1.337 (3)	C17—H17B	0.9900
N1—C1	1.347 (2)	C18—H18A	0.9800
N2—C8	1.470 (2)	C18—H18B	0.9800
N2—C16	1.479 (3)	C18—H18C	0.9800
N3—C19	1.472 (2)	C19—H19A	0.9900
N3—C27	1.492 (2)	C19—H19B	0.9900
C1—C2	1.393 (3)	C20—C25	1.391 (3)
C1—C6	1.526 (3)	C20—C21	1.395 (3)
C2—C3	1.387 (3)	C21—C22	1.389 (3)
C2—H2	0.9500	C21—H21	0.9500
C3—C4	1.389 (3)	C22—C23	1.389 (3)
C3—H3	0.9500	C22—H22	0.9500
C4—C5	1.385 (3)	C23—C24	1.389 (3)
C4—H4	0.9500	C23—C26	1.507 (3)
C5—H5	0.9500	C24—C25	1.385 (3)
C6—C7	1.528 (2)	C24—H24	0.9500
C6—C19	1.547 (2)	C25—H25	0.9500
C6—C8	1.552 (3)	C26—H26A	0.9800
C7—H7A	0.9800	C26—H26B	0.9800
C7—H7B	0.9799	C26—H26C	0.9800
C7—H7C	0.9800	C27—C28	1.516 (3)
C8—H8A	0.9900	C27—H27A	0.9900
C8—H8B	0.9900	C27—H27B	0.9900
C9—C14	1.388 (3)	C28—H28A	0.9900
C9—C10	1.392 (3)	C28—H28B	0.9900
C10—C11	1.388 (3)	C29—H29A	0.9800
C10—H10	0.9500	C29—H29B	0.9800
C11—C12	1.389 (3)	C29—H29C	0.9800
C11—H11	0.9500
O1—S1—O2	119.64 (9)	C12—C15—H15A	109.5
O1—S1—N2	107.00 (9)	C12—C15—H15B	109.5
O2—S1—N2	106.15 (9)	H15A—C15—H15B	109.5
O1—S1—C9	105.99 (9)	C12—C15—H15C	109.5
O2—S1—C9	108.04 (9)	H15A—C15—H15C	109.5
N2—S1—C9	109.83 (9)	H15B—C15—H15C	109.5
O4—S2—O3	120.37 (9)	N2—C16—C17	114.24 (16)
O4—S2—N3	106.59 (9)	N2—C16—H16A	108.7
O3—S2—N3	107.56 (8)	C17—C16—H16A	108.7
O4—S2—C20	108.19 (9)	N2—C16—H16B	108.7
O3—S2—C20	107.43 (9)	C17—C16—H16B	108.7
N3—S2—C20	105.84 (8)	H16A—C16—H16B	107.6
C18—S3—C17	100.42 (11)	C16—C17—S3	111.55 (14)
C29—S4—C28	98.76 (11)	C16—C17—H17A	109.3
C5—N1—C1	117.85 (16)	S3—C17—H17A	109.3
C8—N2—C16	118.57 (16)	C16—C17—H17B	109.3
C8—N2—S1	116.49 (13)	S3—C17—H17B	109.3
C16—N2—S1	118.99 (13)	H17A—C17—H17B	108.0
C19—N3—C27	116.72 (15)	S3—C18—H18A	109.5
C19—N3—S2	116.48 (12)	S3—C18—H18B	109.5
C27—N3—S2	115.53 (12)	H18A—C18—H18B	109.5
N1—C1—C2	121.88 (17)	S3—C18—H18C	109.5
N1—C1—C6	115.28 (15)	H18A—C18—H18C	109.5
C2—C1—C6	122.84 (17)	H18B—C18—H18C	109.5
C3—C2—C1	119.49 (18)	N3—C19—C6	115.02 (15)
C3—C2—H2	120.3	N3—C19—H19A	108.5
C1—C2—H2	120.3	C6—C19—H19A	108.5
C2—C3—C4	118.77 (18)	N3—C19—H19B	108.5
C2—C3—H3	120.6	C6—C19—H19B	108.5
C4—C3—H3	120.6	H19A—C19—H19B	107.5
C5—C4—C3	118.01 (19)	C25—C20—C21	120.69 (18)
C5—C4—H4	121.0	C25—C20—S2	120.02 (15)
C3—C4—H4	121.0	C21—C20—S2	119.20 (15)
N1—C5—C4	123.98 (19)	C22—C21—C20	118.96 (18)
N1—C5—H5	118.0	C22—C21—H21	120.5
C4—C5—H5	118.0	C20—C21—H21	120.5
C1—C6—C7	113.12 (15)	C21—C22—C23	121.24 (19)
C1—C6—C19	109.46 (14)	C21—C22—H22	119.4
C7—C6—C19	109.87 (15)	C23—C22—H22	119.4
C1—C6—C8	110.87 (15)	C22—C23—C24	118.63 (18)
C7—C6—C8	111.04 (15)	C22—C23—C26	120.8 (2)
C19—C6—C8	101.91 (14)	C24—C23—C26	120.6 (2)
C6—C7—H7A	109.5	C25—C24—C23	121.41 (19)
C6—C7—H7B	109.5	C25—C24—H24	119.3
H7A—C7—H7B	109.5	C23—C24—H24	119.3
C6—C7—H7C	109.5	C24—C25—C20	119.05 (18)
H7A—C7—H7C	109.5	C24—C25—H25	120.5
H7B—C7—H7C	109.5	C20—C25—H25	120.5
N2—C8—C6	115.19 (15)	C23—C26—H26A	109.5
N2—C8—H8A	108.5	C23—C26—H26B	109.5
C6—C8—H8A	108.5	H26A—C26—H26B	109.5
N2—C8—H8B	108.5	C23—C26—H26C	109.5
C6—C8—H8B	108.5	H26A—C26—H26C	109.5
H8A—C8—H8B	107.5	H26B—C26—H26C	109.5
C14—C9—C10	120.59 (17)	N3—C27—C28	111.47 (15)
C14—C9—S1	119.86 (15)	N3—C27—H27A	109.3
C10—C9—S1	119.52 (15)	C28—C27—H27A	109.3
C11—C10—C9	119.33 (18)	N3—C27—H27B	109.3
C11—C10—H10	120.3	C28—C27—H27B	109.3
C9—C10—H10	120.3	H27A—C27—H27B	108.0
C10—C11—C12	121.21 (19)	C27—C28—S4	111.05 (13)
C10—C11—H11	119.4	C27—C28—H28A	109.4
C12—C11—H11	119.4	S4—C28—H28A	109.4
C11—C12—C13	118.44 (18)	C27—C28—H28B	109.4
C11—C12—C15	120.85 (19)	S4—C28—H28B	109.4
C13—C12—C15	120.71 (19)	H28A—C28—H28B	108.0
C14—C13—C12	121.21 (18)	S4—C29—H29A	109.5
C14—C13—H13	119.4	S4—C29—H29B	109.5
C12—C13—H13	119.4	H29A—C29—H29B	109.5
C9—C14—C13	119.21 (18)	S4—C29—H29C	109.5
C9—C14—H14	120.4	H29A—C29—H29C	109.5
C13—C14—H14	120.4	H29B—C29—H29C	109.5
O1—S1—N2—C8	50.28 (16)	S1—C9—C10—C11	178.28 (14)
O2—S1—N2—C8	179.10 (14)	C9—C10—C11—C12	−0.8 (3)
C9—S1—N2—C8	−64.34 (16)	C10—C11—C12—C13	0.6 (3)
O1—S1—N2—C16	−157.23 (14)	C10—C11—C12—C15	−179.04 (19)
O2—S1—N2—C16	−28.40 (17)	C11—C12—C13—C14	0.2 (3)
C9—S1—N2—C16	88.16 (16)	C15—C12—C13—C14	179.81 (18)
O4—S2—N3—C19	180.00 (13)	C10—C9—C14—C13	0.4 (3)
O3—S2—N3—C19	−49.64 (15)	S1—C9—C14—C13	−177.52 (14)
C20—S2—N3—C19	64.97 (14)	C12—C13—C14—C9	−0.7 (3)
O4—S2—N3—C27	37.38 (15)	C8—N2—C16—C17	61.6 (2)
O3—S2—N3—C27	167.74 (13)	S1—N2—C16—C17	−90.32 (19)
C20—S2—N3—C27	−77.65 (14)	N2—C16—C17—S3	176.98 (14)
C5—N1—C1—C2	1.0 (3)	C18—S3—C17—C16	−75.92 (18)
C5—N1—C1—C6	−178.28 (17)	C27—N3—C19—C6	−101.63 (18)
N1—C1—C2—C3	−0.5 (3)	S2—N3—C19—C6	116.19 (15)
C6—C1—C2—C3	178.75 (18)	C1—C6—C19—N3	57.0 (2)
C1—C2—C3—C4	−0.5 (3)	C7—C6—C19—N3	−67.7 (2)
C2—C3—C4—C5	0.9 (3)	C8—C6—C19—N3	174.47 (15)
C1—N1—C5—C4	−0.6 (3)	O4—S2—C20—C25	−25.02 (18)
C3—C4—C5—N1	−0.4 (3)	O3—S2—C20—C25	−156.39 (15)
N1—C1—C6—C7	177.87 (15)	N3—S2—C20—C25	88.91 (16)
C2—C1—C6—C7	−1.4 (2)	O4—S2—C20—C21	158.62 (15)
N1—C1—C6—C19	55.0 (2)	O3—S2—C20—C21	27.25 (18)
C2—C1—C6—C19	−124.26 (18)	N3—S2—C20—C21	−87.45 (17)
N1—C1—C6—C8	−56.6 (2)	C25—C20—C21—C22	−1.6 (3)
C2—C1—C6—C8	124.09 (18)	S2—C20—C21—C22	174.75 (15)
C16—N2—C8—C6	82.2 (2)	C20—C21—C22—C23	0.7 (3)
S1—N2—C8—C6	−125.16 (15)	C21—C22—C23—C24	0.7 (3)
C1—C6—C8—N2	−73.7 (2)	C21—C22—C23—C26	−179.03 (19)
C7—C6—C8—N2	53.0 (2)	C22—C23—C24—C25	−1.1 (3)
C19—C6—C8—N2	169.94 (16)	C26—C23—C24—C25	178.58 (19)
O1—S1—C9—C14	148.76 (15)	C23—C24—C25—C20	0.2 (3)
O2—S1—C9—C14	19.39 (18)	C21—C20—C25—C24	1.2 (3)
N2—S1—C9—C14	−95.98 (16)	S2—C20—C25—C24	−175.15 (15)
O1—S1—C9—C10	−29.20 (17)	C19—N3—C27—C28	119.73 (17)
O2—S1—C9—C10	−158.57 (15)	S2—N3—C27—C28	−97.74 (17)
N2—S1—C9—C10	86.06 (17)	N3—C27—C28—S4	177.34 (13)
C14—C9—C10—C11	0.3 (3)	C29—S4—C28—C27	−86.41 (16)