25,27-(6-Tosyl-3,9-dioxa-6-aza­un­decane-1,11-diyldioxy)-26,28-(3,6,9-trioxaun­decane-1,11-diyldioxy)­calix­[4]­arene

A new calix­[4]-­crowned aza­crown ether, C₅₁H₅₉NO₁₁S, consisting of four phenyl rings in a 1,3-alternate conformation was synthesized from the reaction of 25,27-bis(5-chloro-3-oxa­pentyl­oxy)­calix­[4]­crown-5 and p-toluene­sulfon­amide in the presence of Cs₂CO₃. A crown-5 loop was attached on the two facing lower rims of the calix­[4]­arene and the N-tosyl aza­crown group was attached on the other set of lower rims of the calix­[4]­arene backbone. This mol­ecule seems to offer an inside cavity for the formation of a host-guest complex.

Computing details

Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELX86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: WinGX publication routines (Farrugia, 1998).

(I)

Crystal data

C51H59NO11S	F(000) = 1904
Mr = 894.05	Dx = 1.291 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
a = 23.547 (2) Å	Cell parameters from 25 reflections
b = 10.922 (3) Å	θ = 11.5–13.4°
c = 19.4876 (18) Å	µ = 0.13 mm^−1
β = 113.340 (7)°	T = 289 K
V = 4601.6 (14) Å^3	Plate, colorless
Z = 4	0.53 × 0.46 × 0.15 mm

Data collection

Enraf Nonius CAD4 diffractometer	3475 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.047
Graphite monochromator	θmax = 25.0°, θmin = 2.1°
non–profiled ω/2θ scans	h = 0→27
Absorption correction: ψ scan (North et al., 1968) Number of ψ scan sets used was 1.	k = 0→12
Tmin = 0.933, Tmax = 0.981	l = −23→21
8225 measured reflections	3 standard reflections every 300 min
8018 independent reflections	intensity decay: 3%

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.206	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.068P)^2 + 2.5027P] where P = (Fo^2 + 2Fc^2)/3
8018 reflections	(Δ/σ)max < 0.001
571 parameters	Δρmax = 0.57 e Å^−3
0 restraints	Δρmin = −0.30 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
S	0.06312 (7)	1.01239 (14)	0.28128 (8)	0.0631 (4)
N	0.1047 (2)	0.8889 (4)	0.2911 (2)	0.0618 (13)
O1	0.39555 (18)	0.5743 (3)	0.2113 (2)	0.0648 (10)
O2	0.48751 (18)	0.5042 (4)	0.1425 (2)	0.0755 (11)
O3	0.46299 (17)	0.2476 (4)	0.0829 (2)	0.0646 (10)
O4	0.34067 (19)	0.1042 (4)	0.0492 (2)	0.0877 (13)
O5	0.2661 (2)	0.3100 (4)	0.1235 (2)	0.0834 (13)
O6	0.24194 (16)	0.5956 (3)	0.09681 (18)	0.0559 (10)
O7	0.1247 (2)	0.7687 (4)	0.1230 (2)	0.0909 (14)
O8	0.17782 (19)	0.6421 (4)	0.3443 (2)	0.0727 (11)
O9	0.26539 (15)	0.4886 (3)	0.30399 (18)	0.0538 (9)
O10	0.10127 (18)	1.1159 (3)	0.2836 (2)	0.0773 (12)
O11	0.03513 (18)	1.0051 (4)	0.3343 (2)	0.0820 (12)
C1	0.3124 (2)	0.4086 (5)	0.3081 (3)	0.0455 (13)
C2	0.2992 (3)	0.2865 (5)	0.2844 (3)	0.0528 (14)
C3	0.3490 (3)	0.2108 (5)	0.2945 (3)	0.0672 (17)
H3	0.3417	0.1289	0.2807	0.081*
C4	0.4087 (3)	0.2526 (5)	0.3242 (3)	0.0639 (16)
H4	0.4414	0.1990	0.3318	0.077*
C5	0.4201 (3)	0.3744 (6)	0.3426 (3)	0.0593 (15)
H5	0.4605	0.4033	0.3612	0.071*
C6	0.3719 (3)	0.4551 (5)	0.3339 (3)	0.0500 (14)
C7	0.3848 (2)	0.5888 (5)	0.3541 (3)	0.0557 (15)
H7A	0.4293	0.6005	0.3755	0.067*
H7B	0.3700	0.6075	0.3929	0.067*
C8	0.3568 (2)	0.6808 (5)	0.2917 (3)	0.0479 (13)
C9	0.3243 (2)	0.7793 (5)	0.3017 (3)	0.0610 (16)
H9	0.3179	0.7854	0.3457	0.073*
C10	0.3012 (3)	0.8688 (5)	0.2482 (4)	0.0765 (19)
H10	0.2807	0.9363	0.2565	0.092*
C11	0.3090 (3)	0.8565 (5)	0.1820 (4)	0.0728 (18)
H11	0.2935	0.9169	0.1458	0.087*
C12	0.3391 (3)	0.7571 (5)	0.1678 (3)	0.0606 (16)
C13	0.3646 (2)	0.6734 (5)	0.2255 (3)	0.0513 (14)
C14	0.4586 (4)	0.5933 (7)	0.2343 (4)	0.1101 (19)
H14A	0.4774	0.6024	0.2882	0.132*
H14B	0.4659	0.6679	0.2121	0.132*
C15	0.4880 (4)	0.4848 (7)	0.2109 (4)	0.1101 (19)
H15A	0.5303	0.4741	0.2467	0.132*
H15B	0.4652	0.4106	0.2105	0.132*
C16	0.5258 (3)	0.4257 (6)	0.1227 (4)	0.0790 (19)
H16A	0.5498	0.3756	0.1655	0.095*
H16B	0.5546	0.4745	0.1097	0.095*
C17	0.4902 (3)	0.3445 (6)	0.0586 (4)	0.0774 (19)
H17A	0.4582	0.3915	0.0204	0.093*
H17B	0.5176	0.3114	0.0369	0.093*
C18	0.4307 (3)	0.1649 (6)	0.0246 (3)	0.0763 (18)
H18A	0.4595	0.1248	0.0076	0.092*
H18B	0.4008	0.2092	−0.0173	0.092*
C19	0.3983 (3)	0.0714 (6)	0.0517 (4)	0.085 (2)
H19A	0.3936	−0.0022	0.0221	0.103*
H19B	0.4247	0.0511	0.1029	0.103*
C20	0.3421 (3)	0.1963 (6)	0.0984 (5)	0.093 (2)
H20A	0.3551	0.2732	0.0843	0.112*
H20B	0.3701	0.1758	0.1490	0.112*
C21	0.2740 (3)	0.2048 (6)	0.0923 (4)	0.102 (2)
H21A	0.2457	0.2022	0.0401	0.123*
H21B	0.2651	0.1356	0.1176	0.123*
C22	0.2051 (3)	0.3291 (5)	0.1174 (3)	0.0589 (15)
C23	0.1906 (2)	0.3022 (5)	0.1779 (3)	0.0499 (14)
C24	0.2345 (2)	0.2380 (5)	0.2476 (3)	0.0618 (15)
H24A	0.2161	0.2398	0.2842	0.074*
H24B	0.2371	0.1529	0.2350	0.074*
C25	0.1310 (3)	0.3300 (5)	0.1703 (3)	0.0615 (15)
H25	0.1193	0.3142	0.2098	0.074*
C26	0.0893 (3)	0.3801 (6)	0.1063 (4)	0.0763 (18)
H26	0.0495	0.3980	0.1025	0.092*
C27	0.1054 (3)	0.4044 (5)	0.0473 (4)	0.0734 (18)
H27	0.0760	0.4373	0.0036	0.088*
C28	0.1646 (3)	0.3809 (5)	0.0515 (3)	0.0594 (15)
C29	0.1802 (3)	0.4094 (6)	−0.0151 (3)	0.084 (2)
H29A	0.1803	0.3320	−0.0395	0.101*
H29B	0.1461	0.4568	−0.0497	0.101*
C30	0.2382 (3)	0.4748 (5)	−0.0072 (3)	0.0554 (14)
C31	0.2661 (3)	0.4443 (5)	−0.0557 (3)	0.0737 (18)
H31	0.2496	0.3809	−0.0897	0.088*
C32	0.3173 (3)	0.5052 (7)	−0.0547 (4)	0.084 (2)
H32	0.3350	0.4835	−0.0880	0.101*
C33	0.3422 (3)	0.5979 (6)	−0.0047 (3)	0.0752 (19)
H33	0.3774	0.6380	−0.0037	0.090*
C34	0.3160 (3)	0.6333 (5)	0.0444 (3)	0.0586 (15)
C35	0.3448 (3)	0.7435 (6)	0.0940 (3)	0.083 (2)
H35A	0.3886	0.7436	0.1039	0.100*
H35B	0.3272	0.8165	0.0649	0.100*
C36	0.2646 (2)	0.5691 (5)	0.0431 (3)	0.0489 (13)
C37	0.1909 (3)	0.6767 (5)	0.0756 (3)	0.0621 (16)
H37A	0.1573	0.6473	0.0310	0.075*
H37B	0.2028	0.7577	0.0657	0.075*
C38	0.1715 (3)	0.6804 (5)	0.1407 (3)	0.0602 (15)
H38A	0.1561	0.6010	0.1477	0.072*
H38B	0.2062	0.7025	0.1863	0.072*
C39	0.0975 (3)	0.7772 (7)	0.1763 (4)	0.090 (2)
H39A	0.0977	0.6972	0.1980	0.108*
H39B	0.0549	0.8039	0.1517	0.108*
C40	0.1336 (3)	0.8685 (5)	0.2384 (3)	0.0686 (17)
H40A	0.1753	0.8378	0.2653	0.082*
H40B	0.1367	0.9460	0.2158	0.082*
C41	0.0963 (3)	0.7844 (5)	0.3328 (3)	0.0729 (18)
H41A	0.0713	0.7232	0.2978	0.087*
H41B	0.0738	0.8109	0.3626	0.087*
C42	0.1561 (3)	0.7274 (6)	0.3832 (3)	0.0767 (18)
H42A	0.1869	0.7910	0.4044	0.092*
H42B	0.1503	0.6861	0.4241	0.092*
C43	0.2265 (3)	0.5706 (6)	0.3920 (3)	0.0746 (18)
H43A	0.2177	0.5455	0.4345	0.090*
H43B	0.2641	0.6192	0.4106	0.090*
C44	0.2364 (3)	0.4613 (5)	0.3542 (3)	0.0663 (17)
H44A	0.2620	0.4036	0.3915	0.080*
H44B	0.1969	0.4224	0.3265	0.080*
C45	0.0055 (2)	1.0045 (5)	0.1908 (3)	0.0551 (14)
C46	0.0086 (3)	1.0763 (5)	0.1344 (4)	0.0626 (16)
H46	0.0401	1.1338	0.1454	0.075*
C47	−0.0339 (3)	1.0645 (5)	0.0620 (4)	0.0671 (16)
H47	−0.0317	1.1157	0.0250	0.080*
C48	−0.0799 (3)	0.9768 (6)	0.0439 (4)	0.0685 (17)
C49	−0.0833 (3)	0.9061 (6)	0.1011 (4)	0.0803 (19)
H49	−0.1148	0.8486	0.0902	0.096*
C50	−0.0411 (3)	0.9188 (6)	0.1737 (4)	0.0741 (18)
H50	−0.0440	0.8697	0.2112	0.089*
C51	−0.1257 (3)	0.9606 (6)	−0.0359 (4)	0.097 (2)
H51A	−0.1177	1.0206	−0.0671	0.145*
H51B	−0.1669	0.9710	−0.0384	0.145*
H51C	−0.1214	0.8800	−0.0529	0.145*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0679 (10)	0.0574 (10)	0.0705 (10)	0.0049 (9)	0.0342 (9)	−0.0041 (8)
N	0.076 (3)	0.053 (3)	0.074 (3)	0.011 (3)	0.047 (3)	0.015 (3)
O1	0.083 (3)	0.055 (2)	0.069 (3)	0.000 (2)	0.042 (2)	0.002 (2)
O2	0.093 (3)	0.060 (3)	0.082 (3)	0.020 (2)	0.043 (2)	−0.005 (2)
O3	0.073 (3)	0.066 (3)	0.063 (2)	−0.008 (2)	0.037 (2)	−0.008 (2)
O4	0.070 (3)	0.089 (3)	0.104 (3)	−0.003 (3)	0.034 (3)	−0.019 (3)
O5	0.104 (4)	0.082 (3)	0.067 (3)	−0.002 (3)	0.037 (3)	−0.016 (2)
O6	0.072 (3)	0.053 (2)	0.052 (2)	0.007 (2)	0.035 (2)	0.0016 (18)
O7	0.117 (4)	0.096 (3)	0.081 (3)	0.051 (3)	0.062 (3)	0.022 (3)
O8	0.091 (3)	0.070 (3)	0.059 (2)	0.023 (2)	0.032 (2)	0.000 (2)
O9	0.060 (2)	0.047 (2)	0.061 (2)	0.013 (2)	0.0309 (19)	0.0133 (19)
O10	0.086 (3)	0.056 (3)	0.083 (3)	−0.016 (2)	0.026 (2)	−0.005 (2)
O11	0.096 (3)	0.088 (3)	0.082 (3)	0.017 (3)	0.057 (3)	−0.002 (3)
C1	0.055 (4)	0.043 (3)	0.039 (3)	0.006 (3)	0.019 (3)	0.011 (3)
C2	0.059 (4)	0.040 (3)	0.056 (3)	0.000 (3)	0.020 (3)	0.003 (3)
C3	0.090 (5)	0.037 (4)	0.076 (4)	0.009 (4)	0.034 (4)	0.007 (3)
C4	0.076 (5)	0.045 (4)	0.077 (4)	0.025 (4)	0.037 (4)	0.015 (3)
C5	0.057 (4)	0.070 (5)	0.056 (4)	0.010 (3)	0.029 (3)	0.013 (3)
C6	0.062 (4)	0.044 (3)	0.044 (3)	0.003 (3)	0.021 (3)	0.003 (3)
C7	0.057 (3)	0.062 (4)	0.047 (3)	−0.009 (3)	0.020 (3)	−0.005 (3)
C8	0.055 (3)	0.039 (3)	0.052 (3)	−0.008 (3)	0.023 (3)	−0.003 (3)
C9	0.070 (4)	0.043 (4)	0.076 (4)	−0.009 (3)	0.037 (3)	−0.018 (3)
C10	0.083 (5)	0.038 (4)	0.109 (6)	−0.004 (3)	0.038 (4)	−0.010 (4)
C11	0.084 (5)	0.038 (4)	0.084 (5)	−0.017 (3)	0.019 (4)	0.009 (3)
C12	0.078 (4)	0.037 (3)	0.065 (4)	−0.018 (3)	0.027 (3)	0.005 (3)
C13	0.064 (4)	0.033 (3)	0.066 (4)	−0.006 (3)	0.035 (3)	−0.009 (3)
C14	0.143 (5)	0.091 (4)	0.135 (5)	0.027 (4)	0.097 (4)	0.009 (4)
C15	0.143 (5)	0.091 (4)	0.135 (5)	0.027 (4)	0.097 (4)	0.009 (4)
C16	0.081 (4)	0.059 (4)	0.123 (6)	−0.005 (4)	0.067 (4)	−0.019 (4)
C17	0.102 (5)	0.065 (4)	0.094 (5)	0.013 (4)	0.069 (4)	0.007 (4)
C18	0.084 (5)	0.083 (5)	0.069 (4)	−0.007 (4)	0.037 (4)	−0.020 (4)
C19	0.090 (5)	0.071 (5)	0.104 (5)	−0.013 (4)	0.047 (4)	−0.035 (4)
C20	0.071 (5)	0.062 (5)	0.163 (7)	−0.016 (4)	0.064 (5)	−0.015 (5)
C21	0.097 (6)	0.054 (5)	0.128 (7)	−0.007 (4)	0.016 (5)	0.005 (5)
C22	0.043 (3)	0.065 (4)	0.074 (4)	−0.008 (3)	0.029 (3)	−0.015 (3)
C23	0.052 (4)	0.043 (3)	0.058 (4)	−0.011 (3)	0.025 (3)	−0.002 (3)
C24	0.073 (4)	0.042 (3)	0.069 (4)	−0.005 (3)	0.028 (3)	−0.004 (3)
C25	0.068 (4)	0.053 (4)	0.068 (4)	−0.012 (3)	0.032 (4)	−0.001 (3)
C26	0.068 (4)	0.074 (5)	0.092 (5)	0.000 (4)	0.036 (4)	0.008 (4)
C27	0.066 (4)	0.065 (4)	0.074 (4)	−0.004 (4)	0.011 (4)	0.005 (4)
C28	0.064 (4)	0.057 (4)	0.051 (4)	−0.022 (3)	0.015 (3)	−0.006 (3)
C29	0.096 (5)	0.095 (5)	0.063 (4)	−0.031 (4)	0.033 (4)	−0.011 (4)
C30	0.078 (4)	0.051 (4)	0.041 (3)	−0.005 (3)	0.026 (3)	0.000 (3)
C31	0.116 (6)	0.059 (4)	0.061 (4)	0.004 (4)	0.050 (4)	0.000 (3)
C32	0.112 (6)	0.098 (5)	0.067 (4)	0.013 (5)	0.060 (4)	0.001 (4)
C33	0.079 (4)	0.102 (6)	0.057 (4)	−0.002 (4)	0.040 (4)	0.021 (4)
C34	0.076 (4)	0.056 (4)	0.046 (3)	0.003 (3)	0.028 (3)	0.017 (3)
C35	0.106 (5)	0.078 (5)	0.065 (4)	−0.025 (4)	0.033 (4)	0.014 (4)
C36	0.057 (3)	0.052 (3)	0.042 (3)	0.004 (3)	0.025 (3)	0.009 (3)
C37	0.079 (4)	0.058 (4)	0.062 (4)	0.001 (3)	0.042 (3)	0.000 (3)
C38	0.078 (4)	0.054 (4)	0.061 (4)	0.010 (3)	0.041 (3)	0.004 (3)
C39	0.087 (5)	0.105 (6)	0.090 (5)	0.017 (4)	0.049 (4)	−0.019 (5)
C40	0.078 (4)	0.064 (4)	0.085 (4)	0.018 (3)	0.055 (4)	0.016 (4)
C41	0.092 (5)	0.061 (4)	0.083 (4)	0.007 (4)	0.052 (4)	0.009 (4)
C42	0.107 (5)	0.067 (4)	0.067 (4)	0.020 (4)	0.046 (4)	0.001 (4)
C43	0.082 (5)	0.078 (5)	0.068 (4)	0.014 (4)	0.035 (4)	0.007 (4)
C44	0.086 (4)	0.048 (4)	0.080 (4)	0.016 (3)	0.048 (4)	0.014 (3)
C45	0.056 (4)	0.048 (3)	0.068 (4)	0.006 (3)	0.031 (3)	−0.001 (3)
C46	0.057 (4)	0.052 (4)	0.078 (4)	−0.007 (3)	0.027 (4)	−0.005 (4)
C47	0.077 (4)	0.052 (4)	0.073 (4)	−0.010 (4)	0.031 (4)	−0.004 (3)
C48	0.058 (4)	0.054 (4)	0.093 (5)	−0.004 (3)	0.030 (4)	−0.011 (4)
C49	0.064 (4)	0.065 (4)	0.116 (6)	−0.022 (4)	0.039 (5)	−0.008 (4)
C50	0.069 (4)	0.068 (4)	0.088 (5)	−0.004 (4)	0.034 (4)	0.007 (4)
C51	0.091 (5)	0.086 (5)	0.089 (5)	−0.018 (4)	0.009 (4)	−0.010 (4)

Geometric parameters (Å, º)

S—O11	1.432 (4)	C10—C11	1.379 (8)
S—O10	1.434 (4)	C11—C12	1.383 (8)
S—N	1.632 (4)	C12—C13	1.387 (7)
S—C45	1.751 (6)	C12—C35	1.505 (7)
N—C40	1.459 (6)	C14—C15	1.530 (8)
N—C41	1.459 (6)	C16—C17	1.491 (8)
O1—C14	1.386 (8)	C18—C19	1.490 (8)
O1—C13	1.392 (6)	C20—C21	1.562 (8)
O2—C15	1.346 (7)	C22—C28	1.382 (7)
O2—C16	1.404 (6)	C22—C23	1.382 (7)
O3—C17	1.412 (6)	C23—C25	1.385 (7)
O3—C18	1.414 (6)	C23—C24	1.515 (7)
O4—C20	1.381 (7)	C25—C26	1.360 (8)
O4—C19	1.387 (6)	C26—C27	1.372 (8)
O5—C21	1.347 (7)	C27—C28	1.387 (7)
O5—C22	1.408 (6)	C28—C29	1.517 (7)
O6—C36	1.381 (5)	C29—C30	1.493 (7)
O6—C37	1.416 (6)	C30—C36	1.387 (7)
O7—C38	1.401 (6)	C30—C31	1.389 (7)
O7—C39	1.421 (6)	C31—C32	1.372 (8)
O8—C43	1.395 (6)	C32—C33	1.366 (8)
O8—C42	1.418 (6)	C33—C34	1.384 (7)
O9—C1	1.387 (5)	C34—C36	1.391 (7)
O9—C44	1.428 (5)	C34—C35	1.524 (8)
C1—C6	1.386 (7)	C37—C38	1.510 (6)
C1—C2	1.404 (7)	C39—C40	1.539 (8)
C2—C3	1.383 (7)	C41—C42	1.497 (8)
C2—C24	1.500 (7)	C43—C44	1.470 (7)
C3—C4	1.371 (7)	C45—C46	1.375 (7)
C4—C5	1.376 (7)	C45—C50	1.378 (7)
C5—C6	1.392 (7)	C46—C47	1.374 (7)
C6—C7	1.512 (7)	C47—C48	1.383 (7)
C7—C8	1.512 (7)	C48—C49	1.384 (8)
C8—C13	1.377 (6)	C48—C51	1.511 (8)
C8—C9	1.377 (7)	C49—C50	1.377 (8)
C9—C10	1.374 (8)
O11—S—O10	118.9 (3)	O4—C19—C18	116.3 (6)
O11—S—N	107.2 (2)	O4—C20—C21	104.4 (5)
O10—S—N	108.0 (2)	O5—C21—C20	109.7 (6)
O11—S—C45	109.3 (3)	C28—C22—C23	124.4 (5)
O10—S—C45	107.2 (3)	C28—C22—O5	116.4 (5)
N—S—C45	105.5 (3)	C23—C22—O5	119.0 (5)
C40—N—C41	118.6 (4)	C22—C23—C25	116.4 (5)
C40—N—S	118.0 (4)	C22—C23—C24	123.5 (5)
C41—N—S	120.3 (4)	C25—C23—C24	120.0 (5)
C14—O1—C13	113.4 (5)	C2—C24—C23	118.0 (4)
C15—O2—C16	115.0 (5)	C26—C25—C23	121.3 (5)
C17—O3—C18	112.4 (4)	C25—C26—C27	120.5 (6)
C20—O4—C19	114.2 (5)	C26—C27—C28	121.3 (6)
C21—O5—C22	114.1 (5)	C22—C28—C27	116.1 (5)
C36—O6—C37	116.6 (4)	C22—C28—C29	124.5 (6)
C38—O7—C39	113.8 (4)	C27—C28—C29	119.4 (6)
C43—O8—C42	112.8 (4)	C30—C29—C28	122.2 (5)
C1—O9—C44	114.5 (4)	C36—C30—C31	117.3 (5)
C6—C1—O9	117.3 (5)	C36—C30—C29	124.3 (5)
C6—C1—C2	121.8 (5)	C31—C30—C29	118.3 (5)
O9—C1—C2	120.8 (5)	C32—C31—C30	121.6 (6)
C3—C2—C1	117.2 (5)	C33—C32—C31	119.8 (6)
C3—C2—C24	120.0 (5)	C32—C33—C34	121.2 (6)
C1—C2—C24	122.8 (5)	C33—C34—C36	118.0 (6)
C4—C3—C2	122.1 (5)	C33—C34—C35	116.8 (6)
C3—C4—C5	119.5 (5)	C36—C34—C35	125.1 (5)
C4—C5—C6	121.0 (5)	C12—C35—C34	119.9 (5)
C1—C6—C5	118.1 (5)	O6—C36—C30	119.4 (5)
C1—C6—C7	121.2 (5)	O6—C36—C34	118.4 (5)
C5—C6—C7	120.7 (5)	C30—C36—C34	122.1 (5)
C6—C7—C8	117.0 (4)	O6—C37—C38	106.0 (4)
C13—C8—C9	117.8 (5)	O7—C38—C37	106.5 (4)
C13—C8—C7	122.5 (5)	O7—C39—C40	110.3 (5)
C9—C8—C7	119.7 (5)	N—C40—C39	112.7 (5)
C10—C9—C8	121.6 (6)	N—C41—C42	113.0 (5)
C9—C10—C11	118.7 (6)	O8—C42—C41	111.6 (5)
C10—C11—C12	122.2 (6)	O8—C43—C44	111.9 (5)
C11—C12—C13	116.5 (5)	O9—C44—C43	112.8 (5)
C11—C12—C35	121.1 (6)	C46—C45—C50	118.9 (5)
C13—C12—C35	122.4 (6)	C46—C45—S	120.7 (5)
C8—C13—C12	123.0 (5)	C50—C45—S	120.1 (5)
C8—C13—O1	120.5 (5)	C47—C46—C45	121.2 (5)
C12—C13—O1	116.4 (5)	C46—C47—C48	120.4 (6)
O1—C14—C15	109.9 (7)	C47—C48—C49	118.0 (6)
O2—C15—C14	110.3 (6)	C47—C48—C51	120.7 (6)
O2—C16—C17	112.6 (5)	C49—C48—C51	121.2 (6)
O3—C17—C16	110.2 (5)	C50—C49—C48	121.5 (6)
O3—C18—C19	110.0 (5)	C49—C50—C45	119.9 (6)
O11—S—N—C40	174.4 (4)	C22—C23—C25—C26	0.6 (8)
O10—S—N—C40	−56.4 (5)	C24—C23—C25—C26	−175.5 (5)
C45—S—N—C40	58.0 (5)	C23—C25—C26—C27	0.0 (9)
O11—S—N—C41	14.9 (5)	C25—C26—C27—C28	−1.2 (9)
O10—S—N—C41	144.1 (4)	C23—C22—C28—C27	−1.1 (8)
C45—S—N—C41	−101.5 (5)	O5—C22—C28—C27	−177.3 (5)
C44—O9—C1—C6	−113.8 (5)	C23—C22—C28—C29	−179.4 (5)
C44—O9—C1—C2	68.2 (6)	O5—C22—C28—C29	4.4 (8)
C6—C1—C2—C3	5.9 (7)	C26—C27—C28—C22	1.7 (8)
O9—C1—C2—C3	−176.2 (4)	C26—C27—C28—C29	−179.9 (6)
C6—C1—C2—C24	−172.3 (5)	C22—C28—C29—C30	−47.8 (9)
O9—C1—C2—C24	5.5 (7)	C27—C28—C29—C30	133.9 (6)
C1—C2—C3—C4	−1.9 (8)	C28—C29—C30—C36	−36.9 (9)
C24—C2—C3—C4	176.4 (5)	C28—C29—C30—C31	146.7 (6)
C2—C3—C4—C5	−2.0 (9)	C36—C30—C31—C32	−0.6 (9)
C3—C4—C5—C6	2.2 (8)	C29—C30—C31—C32	176.2 (6)
O9—C1—C6—C5	176.2 (4)	C30—C31—C32—C33	0.4 (10)
C2—C1—C6—C5	−5.9 (7)	C31—C32—C33—C34	−1.2 (10)
O9—C1—C6—C7	−2.2 (7)	C32—C33—C34—C36	2.0 (9)
C2—C1—C6—C7	175.7 (5)	C32—C33—C34—C35	−175.8 (6)
C4—C5—C6—C1	1.7 (7)	C11—C12—C35—C34	−118.5 (6)
C4—C5—C6—C7	−179.9 (5)	C13—C12—C35—C34	63.0 (8)
C1—C6—C7—C8	−63.5 (6)	C33—C34—C35—C12	−154.4 (6)
C5—C6—C7—C8	118.1 (5)	C36—C34—C35—C12	28.0 (9)
C6—C7—C8—C13	−52.5 (7)	C37—O6—C36—C30	−86.1 (6)
C6—C7—C8—C9	130.4 (5)	C37—O6—C36—C34	98.0 (5)
C13—C8—C9—C10	−1.1 (8)	C31—C30—C36—O6	−174.3 (5)
C7—C8—C9—C10	176.2 (5)	C29—C30—C36—O6	9.2 (8)
C8—C9—C10—C11	2.4 (9)	C31—C30—C36—C34	1.5 (8)
C9—C10—C11—C12	0.1 (9)	C29—C30—C36—C34	−175.0 (5)
C10—C11—C12—C13	−3.8 (8)	C33—C34—C36—O6	173.6 (5)
C10—C11—C12—C35	177.6 (5)	C35—C34—C36—O6	−8.8 (8)
C9—C8—C13—C12	−2.8 (8)	C33—C34—C36—C30	−2.2 (8)
C7—C8—C13—C12	179.9 (5)	C35—C34—C36—C30	175.4 (5)
C9—C8—C13—O1	−178.2 (4)	C36—O6—C37—C38	174.5 (4)
C7—C8—C13—O1	4.5 (7)	C39—O7—C38—C37	175.3 (5)
C11—C12—C13—C8	5.2 (8)	O6—C37—C38—O7	174.8 (4)
C35—C12—C13—C8	−176.2 (5)	C38—O7—C39—C40	88.5 (6)
C11—C12—C13—O1	−179.3 (5)	C41—N—C40—C39	59.8 (7)
C35—C12—C13—O1	−0.7 (7)	S—N—C40—C39	−100.1 (5)
C14—O1—C13—C8	−90.7 (6)	O7—C39—C40—N	175.0 (5)
C14—O1—C13—C12	93.6 (6)	C40—N—C41—C42	62.9 (7)
C13—O1—C14—C15	−175.3 (5)	S—N—C41—C42	−137.7 (4)
C16—O2—C15—C14	165.6 (6)	C43—O8—C42—C41	−168.3 (5)
O1—C14—C15—O2	89.8 (7)	N—C41—C42—O8	−84.3 (6)
C15—O2—C16—C17	115.2 (7)	C42—O8—C43—C44	163.4 (5)
C18—O3—C17—C16	−177.6 (5)	C1—O9—C44—C43	136.0 (5)
O2—C16—C17—O3	−77.1 (6)	O8—C43—C44—O9	74.5 (6)
C17—O3—C18—C19	−174.9 (5)	O11—S—C45—C46	140.5 (4)
C20—O4—C19—C18	−67.7 (7)	O10—S—C45—C46	10.4 (5)
O3—C18—C19—O4	84.5 (7)	N—S—C45—C46	−104.6 (5)
C19—O4—C20—C21	−173.2 (5)	O11—S—C45—C50	−44.9 (5)
C22—O5—C21—C20	177.0 (5)	O10—S—C45—C50	−175.0 (4)
O4—C20—C21—O5	−165.2 (6)	N—S—C45—C50	70.0 (5)
C21—O5—C22—C28	−84.2 (7)	C50—C45—C46—C47	0.5 (8)
C21—O5—C22—C23	99.5 (6)	S—C45—C46—C47	175.2 (4)
C28—C22—C23—C25	0.0 (8)	C45—C46—C47—C48	−2.1 (9)
O5—C22—C23—C25	176.1 (5)	C46—C47—C48—C49	2.9 (8)
C28—C22—C23—C24	176.0 (5)	C46—C47—C48—C51	−178.1 (6)
O5—C22—C23—C24	−8.0 (8)	C47—C48—C49—C50	−2.2 (9)
C3—C2—C24—C23	−122.3 (6)	C51—C48—C49—C50	178.8 (6)
C1—C2—C24—C23	56.0 (7)	C48—C49—C50—C45	0.7 (9)
C22—C23—C24—C2	50.0 (7)	C46—C45—C50—C49	0.2 (9)
C25—C23—C24—C2	−134.2 (5)	S—C45—C50—C49	−174.5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20A···O3	0.97	2.57	3.033 (7)	110
C40—H40B···O10	0.97	2.60	3.032 (7)	107
C41—H41B···O11	0.97	2.29	2.814 (7)	113
C46—H46···O10	0.93	2.51	2.894 (7)	105
C51—H51A···O7^i	0.96	2.52	3.413 (8)	154

Symmetry code: (i) −x, −y+2, −z.