1,3-Alternate thia­calix[4]bis­azacrown chloro­form disolvate

In the title compound [systematic name: 5,11,17,23-tert-butyl-25,27:26,28-bis(2,8-dioxo-3,7-diaza­nonane-1,9-diyldioxy)-2,8,14,20-tetra­thia­calix[4]arene chloro­form disolvate], C₅₄H₆₈N₄O₈S₄·2CHCl₃, the thia­calixarene mol­ecule, locked in the 1,3-alternate conformation by two amide bridges, possesses twofold rotation symmetry with an cage-like cavity.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.057
• wR factor = 0.177
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.98 Ratio
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C23

Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.61 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C27
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C29
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for       C29'
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.08
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.

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

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

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

5,11,17,23-tert-butyl-25,27:26,28-bis[oxy(2,8-dioxo-3,7-diazanonamethy lene)oxy]-2,8,14,20-tetrathiacalix[4]arene chloroform disolvate

Crystal data

C54H68N4O8S4·2CHCl3	F(000) = 2656
Mr = 1268.10	Dx = 1.359 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7479 reflections
a = 21.8177 (15) Å	θ = 2.5–28.1°
b = 16.5383 (11) Å	µ = 0.47 mm^−1
c = 17.7990 (12) Å	T = 297 K
β = 105.171 (1)°	Block, colourless
V = 6198.5 (7) Å^3	0.47 × 0.43 × 0.31 mm
Z = 4

Data collection

Bruker SMART APEX II 4K CCD area-detector diffractometer	6416 independent reflections
Radiation source: fine-focus sealed tube	5336 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
φ and ω scans	θmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −27→27
Tmin = 0.811, Tmax = 0.869	k = −10→20
18287 measured reflections	l = −21→22

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.178	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0928P)^2 + 7.5615P] where P = (Fo^2 + 2Fc^2)/3
6416 reflections	(Δ/σ)max < 0.001
390 parameters	Δρmax = 0.65 e Å^−3
65 restraints	Δρmin = −0.53 e Å^−3

Special details

Experimental. Structures of the above mentioned doubly amide-bridged thiacalix[4]arenes in the 1,3-alternate conformation were also proved by ¹H NMR, EA, ESI-MS, and IR spectroscopy. It is obvious that the twofold symmetry of this molecule results in a very simple splitting pattern in the ¹H NMR spectra. Spanning of both distal positions on the lower rim with a symmetrical bridge does not change the symmetry of the starting compound which results in an equivalence of geminal O—CH₂ protons. Similarly, aromatic protons are represented by two singlets in a ratio of 1:1. Analysis, calculated for the dried sample C₅₄H₆₈N₄O₈S₄: C 63.01, H 6.66, N 5.44, S 12.46%; found: C 62.88, H 6.60, N 5.37, S 12.40%.

¹H NMR (CDCl₃, δ, p.p.m.): 1.28 (s, 36H), 1.64 (m, 4H), 3.10 (m, 8H), 4.33 (s, 8H), 5.47 (m, 4H), 7.39 (s, 8H).

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	Occ. (<1)
N1	0.97046 (15)	1.07284 (17)	0.16118 (18)	0.0635 (8)
H1A	0.9920	1.0298	0.1773	0.076*
N2	0.93256 (14)	0.63068 (17)	0.2619 (2)	0.0664 (8)
H2	0.9440	0.6743	0.2431	0.080*
O1	0.87480 (16)	1.12099 (15)	0.09747 (18)	0.0828 (8)
O2	0.89367 (16)	0.58067 (16)	0.3582 (2)	0.0908 (10)
O3	0.92694 (8)	0.78025 (10)	0.30819 (11)	0.0393 (4)
O4	0.93004 (9)	0.92119 (10)	0.14294 (10)	0.0389 (4)
S1	1.02047 (3)	0.88713 (4)	0.04240 (4)	0.0443 (2)
S2	0.81671 (3)	0.81351 (4)	0.16727 (4)	0.0434 (2)
C1	0.95164 (12)	0.74960 (16)	0.02201 (14)	0.0379 (5)
H1	0.9788	0.7346	−0.0081	0.045*
C2	0.96250 (12)	0.82199 (15)	0.06286 (14)	0.0348 (5)
C3	0.92237 (11)	0.84588 (14)	0.10828 (13)	0.0332 (5)
C4	0.87461 (11)	0.79312 (15)	0.11617 (14)	0.0337 (5)
C5	0.86490 (12)	0.72038 (15)	0.07416 (15)	0.0369 (5)
H5	0.8329	0.6857	0.0799	0.044*
C6	0.90133 (12)	0.69859 (15)	0.02461 (15)	0.0371 (5)
C7	1.07804 (11)	0.90956 (15)	0.13031 (14)	0.0344 (5)
C8	1.10897 (12)	0.98360 (16)	0.13034 (15)	0.0375 (5)
H8	1.0934	1.0197	0.0898	0.045*
C9	1.16227 (12)	1.00497 (16)	0.18904 (15)	0.0378 (5)
C10	1.20227 (13)	1.08056 (17)	0.18552 (17)	0.0435 (6)
C11	1.26752 (18)	1.0532 (2)	0.1810 (3)	0.0790 (12)
H11A	1.2638	1.0236	0.1336	0.118*
H11B	1.2860	1.0191	0.2247	0.118*
H11C	1.2941	1.0996	0.1819	0.118*
C12	1.2104 (2)	1.1310 (3)	0.2591 (3)	0.0870 (14)
H12A	1.2352	1.1782	0.2557	0.131*
H12B	1.2318	1.0995	0.3035	0.131*
H12C	1.1695	1.1471	0.2643	0.131*
C13	1.1731 (2)	1.1334 (2)	0.1157 (3)	0.0875 (15)
H13A	1.1317	1.1507	0.1182	0.131*
H13B	1.1696	1.1031	0.0688	0.131*
H13C	1.1996	1.1798	0.1160	0.131*
C14	0.88905 (14)	0.62187 (16)	−0.02581 (17)	0.0444 (6)
C15	0.8314 (2)	0.5732 (2)	−0.0138 (3)	0.0724 (10)
H15A	0.8243	0.5267	−0.0473	0.109*
H15B	0.7942	0.6068	−0.0262	0.109*
H15C	0.8400	0.5559	0.0394	0.109*
C16	0.94675 (19)	0.5688 (2)	−0.0065 (3)	0.0813 (13)
H16A	0.9388	0.5212	−0.0384	0.122*
H16B	0.9563	0.5535	0.0474	0.122*
H16C	0.9821	0.5977	−0.0160	0.122*
C17	0.8725 (2)	0.6449 (2)	−0.1118 (2)	0.0693 (10)
H17A	0.9076	0.6734	−0.1227	0.104*
H17B	0.8356	0.6789	−0.1238	0.104*
H17C	0.8640	0.5968	−0.1431	0.104*
C18	0.81925 (12)	0.95234 (17)	0.24804 (16)	0.0405 (6)
H18	0.7851	0.9662	0.2066	0.049*
C19	0.85042 (12)	0.87977 (16)	0.24558 (15)	0.0366 (5)
C20	0.90064 (11)	0.85615 (15)	0.30799 (15)	0.0345 (5)
C21	0.89776 (15)	0.72187 (17)	0.34760 (17)	0.0472 (6)
H21A	0.8525	0.7322	0.3357	0.057*
H21B	0.9151	0.7274	0.4034	0.057*
C22	0.90884 (14)	0.63746 (18)	0.3234 (2)	0.0527 (7)
C24	1.0000	0.5127 (3)	0.2500	0.089 (2)
H24A	0.9966	0.4777	0.2925	0.107*	0.50
H24B	1.0034	0.4777	0.2075	0.107*	0.50
C23	0.9405 (2)	0.5551 (3)	0.2245 (4)	0.110 (2)
H23A	0.9073	0.5187	0.2304	0.131*
H23B	0.9332	0.5656	0.1693	0.131*
C25	0.88791 (14)	0.98004 (16)	0.09734 (17)	0.0462 (6)
H25A	0.8457	0.9730	0.1047	0.055*
H25B	0.8852	0.9716	0.0426	0.055*
C26	0.91046 (17)	1.06502 (17)	0.11988 (18)	0.0517 (7)
C27	1.0010 (3)	1.1501 (3)	0.1802 (3)	0.114 (2)
H27A	1.0451	1.1435	0.1801	0.137*
H27B	0.9821	1.1869	0.1380	0.137*
C28	1.0000	1.1887 (3)	0.2500	0.132 (4)
H28A	0.9632	1.2239	0.2375	0.159*	0.50
H28B	1.0368	1.2239	0.2625	0.159*	0.50
Cl1	0.8580 (3)	0.3419 (4)	0.1870 (3)	0.154 (3)	0.550 (8)
Cl2	0.7424 (2)	0.3322 (4)	0.0760 (5)	0.185 (3)	0.550 (8)
Cl3	0.8542 (5)	0.3443 (3)	0.0257 (4)	0.196 (3)	0.550 (8)
C29	0.8211 (5)	0.3068 (10)	0.0964 (5)	0.099 (2)	0.550 (8)
H29	0.8245	0.2477	0.0967	0.119*	0.550 (8)
Cl1'	0.8284 (6)	0.3307 (6)	0.1803 (6)	0.185 (4)	0.450 (8)
Cl2'	0.7693 (4)	0.3544 (3)	0.0236 (5)	0.168 (3)	0.450 (8)
Cl3'	0.9047 (4)	0.3520 (3)	0.0775 (5)	0.164 (2)	0.450 (8)
C29'	0.8343 (5)	0.3117 (12)	0.0875 (7)	0.099 (2)	0.450 (8)
H29'	0.8341	0.2531	0.0789	0.119*	0.450 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.078 (2)	0.0428 (15)	0.0701 (18)	−0.0185 (14)	0.0203 (15)	−0.0110 (13)
N2	0.0631 (17)	0.0418 (14)	0.098 (2)	0.0010 (13)	0.0276 (16)	−0.0181 (15)
O1	0.113 (2)	0.0416 (13)	0.096 (2)	0.0235 (14)	0.0324 (17)	0.0120 (13)
O2	0.103 (2)	0.0501 (15)	0.111 (2)	−0.0068 (14)	0.0150 (18)	0.0328 (15)
O3	0.0405 (10)	0.0305 (9)	0.0496 (10)	0.0037 (7)	0.0168 (8)	−0.0014 (8)
O4	0.0466 (10)	0.0273 (9)	0.0395 (9)	−0.0040 (7)	0.0057 (8)	−0.0055 (7)
S1	0.0472 (4)	0.0512 (4)	0.0335 (3)	−0.0161 (3)	0.0087 (3)	0.0028 (3)
S2	0.0325 (3)	0.0476 (4)	0.0503 (4)	−0.0064 (3)	0.0115 (3)	−0.0161 (3)
C1	0.0402 (13)	0.0372 (13)	0.0360 (12)	0.0008 (10)	0.0094 (10)	−0.0049 (10)
C2	0.0358 (12)	0.0331 (12)	0.0336 (12)	−0.0040 (10)	0.0055 (9)	0.0009 (9)
C3	0.0385 (12)	0.0264 (11)	0.0314 (11)	−0.0027 (9)	0.0031 (9)	−0.0033 (9)
C4	0.0317 (12)	0.0325 (12)	0.0352 (12)	0.0004 (9)	0.0058 (9)	−0.0034 (10)
C5	0.0352 (12)	0.0315 (12)	0.0425 (13)	−0.0045 (10)	0.0073 (10)	−0.0028 (10)
C6	0.0420 (13)	0.0289 (12)	0.0371 (13)	0.0017 (10)	0.0044 (10)	−0.0051 (10)
C7	0.0308 (11)	0.0374 (13)	0.0358 (12)	−0.0040 (10)	0.0103 (9)	−0.0008 (10)
C8	0.0381 (13)	0.0353 (13)	0.0386 (13)	−0.0043 (10)	0.0093 (10)	0.0068 (10)
C9	0.0356 (13)	0.0352 (13)	0.0428 (13)	−0.0049 (10)	0.0106 (10)	0.0022 (10)
C10	0.0412 (14)	0.0384 (14)	0.0498 (15)	−0.0117 (11)	0.0100 (11)	0.0037 (12)
C11	0.062 (2)	0.061 (2)	0.126 (4)	−0.0120 (18)	0.047 (2)	0.013 (2)
C12	0.108 (3)	0.067 (2)	0.096 (3)	−0.046 (2)	0.044 (3)	−0.026 (2)
C13	0.086 (3)	0.060 (2)	0.094 (3)	−0.036 (2)	−0.016 (2)	0.034 (2)
C14	0.0499 (15)	0.0322 (13)	0.0467 (15)	0.0012 (11)	0.0050 (12)	−0.0118 (11)
C15	0.083 (3)	0.0507 (19)	0.085 (3)	−0.0219 (18)	0.023 (2)	−0.0257 (18)
C16	0.071 (2)	0.057 (2)	0.100 (3)	0.0213 (18)	−0.005 (2)	−0.033 (2)
C17	0.087 (3)	0.063 (2)	0.0526 (19)	−0.0067 (19)	0.0084 (17)	−0.0178 (16)
C18	0.0347 (13)	0.0433 (14)	0.0417 (13)	0.0053 (11)	0.0066 (10)	−0.0034 (11)
C19	0.0334 (12)	0.0379 (13)	0.0398 (13)	−0.0014 (10)	0.0121 (10)	−0.0065 (10)
C20	0.0336 (12)	0.0307 (12)	0.0422 (13)	0.0019 (10)	0.0152 (10)	−0.0025 (10)
C21	0.0530 (16)	0.0411 (15)	0.0501 (16)	−0.0038 (12)	0.0180 (13)	0.0017 (12)
C22	0.0447 (15)	0.0370 (15)	0.068 (2)	0.0001 (12)	−0.0006 (14)	0.0067 (13)
C24	0.065 (3)	0.031 (2)	0.172 (7)	0.000	0.034 (4)	0.000
C23	0.065 (2)	0.074 (3)	0.179 (5)	0.007 (2)	0.013 (3)	−0.070 (3)
C25	0.0526 (16)	0.0352 (14)	0.0468 (15)	0.0013 (12)	0.0060 (12)	0.0014 (11)
C26	0.079 (2)	0.0331 (14)	0.0502 (16)	0.0029 (14)	0.0285 (15)	0.0017 (12)
C27	0.170 (5)	0.071 (3)	0.117 (4)	−0.071 (3)	0.065 (4)	−0.033 (3)
C28	0.247 (11)	0.036 (3)	0.072 (4)	0.000	−0.033 (5)	0.000
Cl1	0.205 (5)	0.092 (3)	0.126 (3)	0.032 (3)	−0.026 (3)	−0.035 (2)
Cl2	0.134 (3)	0.124 (4)	0.298 (8)	0.006 (2)	0.057 (4)	−0.062 (4)
Cl3	0.328 (9)	0.115 (3)	0.208 (5)	−0.004 (4)	0.184 (6)	0.009 (3)
C29	0.141 (6)	0.055 (3)	0.100 (4)	0.013 (4)	0.031 (4)	0.006 (3)
Cl1'	0.284 (9)	0.135 (5)	0.173 (6)	0.026 (5)	0.126 (6)	0.031 (4)
Cl2'	0.172 (5)	0.086 (2)	0.194 (5)	−0.001 (3)	−0.048 (4)	0.008 (3)
Cl3'	0.179 (5)	0.109 (3)	0.210 (6)	−0.016 (3)	0.063 (4)	0.018 (3)
C29'	0.141 (6)	0.055 (3)	0.100 (4)	0.013 (4)	0.031 (4)	0.006 (3)

Geometric parameters (Å, º)

N1—C26	1.329 (5)	C14—C16	1.499 (4)
N1—C27	1.440 (4)	C14—C17	1.526 (5)
N1—H1A	0.8600	C14—C15	1.555 (5)
N2—C22	1.332 (5)	C15—H15A	0.9600
N2—C23	1.448 (4)	C15—H15B	0.9600
N2—H2	0.8600	C15—H15C	0.9600
O1—C26	1.208 (4)	C16—H16A	0.9600
O2—C22	1.218 (4)	C16—H16B	0.9600
O3—C20	1.380 (3)	C16—H16C	0.9600
O3—C21	1.437 (3)	C17—H17A	0.9600
O4—C3	1.380 (3)	C17—H17B	0.9600
O4—C25	1.435 (3)	C17—H17C	0.9600
S1—C2	1.770 (2)	C18—C19	1.386 (4)
S1—C7	1.771 (2)	C18—C9^i	1.392 (4)
S2—C4	1.772 (3)	C18—H18	0.9300
S2—C19	1.774 (3)	C19—C20	1.396 (4)
C1—C2	1.389 (3)	C20—C7^i	1.391 (4)
C1—C6	1.395 (4)	C21—C22	1.499 (4)
C1—H1	0.9300	C21—H21A	0.9700
C2—C3	1.395 (3)	C21—H21B	0.9700
C3—C4	1.394 (3)	C24—C23^i	1.439 (5)
C4—C5	1.403 (3)	C24—C23	1.439 (5)
C5—C6	1.381 (4)	C24—H24A	0.9700
C5—H5	0.9300	C24—H24B	0.9700
C6—C14	1.537 (3)	C23—H23A	0.9700
C7—C20^i	1.391 (4)	C23—H23B	0.9700
C7—C8	1.398 (3)	C25—C26	1.508 (4)
C8—C9	1.390 (4)	C25—H25A	0.9700
C8—H8	0.9300	C25—H25B	0.9700
C9—C18^i	1.392 (4)	C27—C28	1.402 (5)
C9—C10	1.535 (3)	C27—H27A	0.9700
C10—C11	1.516 (5)	C27—H27B	0.9700
C10—C13	1.516 (5)	C28—C27^i	1.402 (5)
C10—C12	1.523 (5)	C28—H28A	0.9700
C11—H11A	0.9600	C28—H28B	0.9700
C11—H11B	0.9600	Cl1—C29	1.705 (10)
C11—H11C	0.9600	Cl2—C29	1.711 (10)
C12—H12A	0.9600	Cl3—C29	1.723 (10)
C12—H12B	0.9600	C29—H29	0.9800
C12—H12C	0.9600	Cl1'—C29'	1.719 (11)
C13—H13A	0.9600	Cl2'—C29'	1.720 (11)
C13—H13B	0.9600	Cl3'—C29'	1.727 (12)
C13—H13C	0.9600	C29'—H29'	0.9800
C26—N1—C27	123.0 (4)	C14—C16—H16B	109.5
C26—N1—H1A	118.5	H16A—C16—H16B	109.5
C27—N1—H1A	118.5	C14—C16—H16C	109.5
C22—N2—C23	124.7 (4)	H16A—C16—H16C	109.5
C22—N2—H2	117.6	H16B—C16—H16C	109.5
C23—N2—H2	117.6	C14—C17—H17A	109.5
C20—O3—C21	112.06 (19)	C14—C17—H17B	109.5
C3—O4—C25	111.98 (19)	H17A—C17—H17B	109.5
C2—S1—C7	109.00 (11)	C14—C17—H17C	109.5
C4—S2—C19	108.43 (11)	H17A—C17—H17C	109.5
C2—C1—C6	122.1 (2)	H17B—C17—H17C	109.5
C2—C1—H1	118.9	C19—C18—C9^i	121.7 (2)
C6—C1—H1	118.9	C19—C18—H18	119.1
C1—C2—C3	120.0 (2)	C9^i—C18—H18	119.1
C1—C2—S1	116.75 (19)	C18—C19—C20	120.4 (2)
C3—C2—S1	122.50 (19)	C18—C19—S2	117.0 (2)
O4—C3—C4	121.8 (2)	C20—C19—S2	122.00 (19)
O4—C3—C2	119.5 (2)	O3—C20—C7^i	121.5 (2)
C4—C3—C2	118.7 (2)	O3—C20—C19	119.7 (2)
C3—C4—C5	119.7 (2)	C7^i—C20—C19	118.8 (2)
C3—C4—S2	125.79 (19)	O3—C21—C22	111.1 (2)
C5—C4—S2	114.10 (19)	O3—C21—H21A	109.4
C6—C5—C4	122.2 (2)	C22—C21—H21A	109.4
C6—C5—H5	118.9	O3—C21—H21B	109.4
C4—C5—H5	118.9	C22—C21—H21B	109.4
C5—C6—C1	116.9 (2)	H21A—C21—H21B	108.0
C5—C6—C14	123.2 (2)	O2—C22—N2	124.7 (3)
C1—C6—C14	119.9 (2)	O2—C22—C21	119.1 (3)
C20^i—C7—C8	119.6 (2)	N2—C22—C21	116.2 (3)
C20^i—C7—S1	125.30 (19)	C23^i—C24—C23	121.8 (5)
C8—C7—S1	114.49 (19)	C23^i—C24—H24A	106.9
C9—C8—C7	122.1 (2)	C23—C24—H24A	106.9
C9—C8—H8	118.9	C23^i—C24—H24B	106.9
C7—C8—H8	118.9	C23—C24—H24B	106.9
C8—C9—C18^i	117.0 (2)	H24A—C24—H24B	106.7
C8—C9—C10	123.3 (2)	C24—C23—N2	118.8 (4)
C18^i—C9—C10	119.6 (2)	C24—C23—H23A	107.6
C11—C10—C13	109.1 (3)	N2—C23—H23A	107.6
C11—C10—C12	108.0 (3)	C24—C23—H23B	107.6
C13—C10—C12	108.6 (3)	N2—C23—H23B	107.6
C11—C10—C9	108.1 (2)	H23A—C23—H23B	107.0
C13—C10—C9	112.4 (2)	O4—C25—C26	111.4 (2)
C12—C10—C9	110.5 (3)	O4—C25—H25A	109.3
C10—C11—H11A	109.5	C26—C25—H25A	109.3
C10—C11—H11B	109.5	O4—C25—H25B	109.3
H11A—C11—H11B	109.5	C26—C25—H25B	109.3
C10—C11—H11C	109.5	H25A—C25—H25B	108.0
H11A—C11—H11C	109.5	O1—C26—N1	124.3 (3)
H11B—C11—H11C	109.5	O1—C26—C25	119.3 (3)
C10—C12—H12A	109.5	N1—C26—C25	116.3 (3)
C10—C12—H12B	109.5	C28—C27—N1	119.9 (4)
H12A—C12—H12B	109.5	C28—C27—H27A	107.3
C10—C12—H12C	109.5	N1—C27—H27A	107.3
H12A—C12—H12C	109.5	C28—C27—H27B	107.3
H12B—C12—H12C	109.5	N1—C27—H27B	107.3
C10—C13—H13A	109.5	H27A—C27—H27B	106.9
C10—C13—H13B	109.5	C27—C28—C27^i	125.8 (6)
H13A—C13—H13B	109.5	C27—C28—H28A	105.9
C10—C13—H13C	109.5	C27^i—C28—H28A	105.9
H13A—C13—H13C	109.5	C27—C28—H28B	105.9
H13B—C13—H13C	109.5	C27^i—C28—H28B	105.9
C16—C14—C17	109.9 (3)	H28A—C28—H28B	106.2
C16—C14—C6	110.0 (2)	Cl1—C29—Cl2	108.4 (7)
C17—C14—C6	109.8 (2)	Cl1—C29—Cl3	112.6 (8)
C16—C14—C15	109.0 (3)	Cl2—C29—Cl3	110.2 (7)
C17—C14—C15	106.3 (3)	Cl1—C29—H29	108.5
C6—C14—C15	111.8 (3)	Cl2—C29—H29	108.5
C14—C15—H15A	109.5	Cl3—C29—H29	108.5
C14—C15—H15B	109.5	Cl1'—C29'—Cl2'	107.7 (9)
H15A—C15—H15B	109.5	Cl1'—C29'—Cl3'	108.7 (9)
C14—C15—H15C	109.5	Cl2'—C29'—Cl3'	112.0 (9)
H15A—C15—H15C	109.5	Cl1'—C29'—H29'	109.5
H15B—C15—H15C	109.5	Cl2'—C29'—H29'	109.5
C14—C16—H16A	109.5	Cl3'—C29'—H29'	109.5
C6—C1—C2—C3	−0.1 (4)	C8—C9—C10—C12	127.7 (3)
C6—C1—C2—S1	−170.8 (2)	C18^i—C9—C10—C12	−55.1 (4)
C7—S1—C2—C1	−124.7 (2)	C5—C6—C14—C16	−121.3 (3)
C7—S1—C2—C3	64.9 (2)	C1—C6—C14—C16	58.2 (4)
C25—O4—C3—C4	−82.7 (3)	C5—C6—C14—C17	117.7 (3)
C25—O4—C3—C2	96.1 (3)	C1—C6—C14—C17	−62.9 (3)
C1—C2—C3—O4	−174.1 (2)	C5—C6—C14—C15	0.0 (4)
S1—C2—C3—O4	−4.1 (3)	C1—C6—C14—C15	179.5 (3)
C1—C2—C3—C4	4.7 (4)	C9^i—C18—C19—C20	1.9 (4)
S1—C2—C3—C4	174.76 (18)	C9^i—C18—C19—S2	173.3 (2)
O4—C3—C4—C5	174.1 (2)	C4—S2—C19—C18	122.9 (2)
C2—C3—C4—C5	−4.6 (4)	C4—S2—C19—C20	−65.9 (2)
O4—C3—C4—S2	1.8 (3)	C21—O3—C20—C7^i	86.0 (3)
C2—C3—C4—S2	−176.97 (19)	C21—O3—C20—C19	−92.5 (3)
C19—S2—C4—C3	−31.0 (3)	C18—C19—C20—O3	173.4 (2)
C19—S2—C4—C5	156.29 (19)	S2—C19—C20—O3	2.5 (3)
C3—C4—C5—C6	0.0 (4)	C18—C19—C20—C7^i	−5.1 (4)
S2—C4—C5—C6	173.2 (2)	S2—C19—C20—C7^i	−175.96 (19)
C4—C5—C6—C1	4.4 (4)	C20—O3—C21—C22	159.4 (2)
C4—C5—C6—C14	−176.1 (2)	C23—N2—C22—O2	3.7 (6)
C2—C1—C6—C5	−4.4 (4)	C23—N2—C22—C21	−173.3 (3)
C2—C1—C6—C14	176.1 (2)	O3—C21—C22—O2	171.4 (3)
C2—S1—C7—C20^i	35.6 (3)	O3—C21—C22—N2	−11.4 (4)
C2—S1—C7—C8	−153.31 (19)	C23^i—C24—C23—N2	−34.8 (4)
C20^i—C7—C8—C9	2.3 (4)	C22—N2—C23—C24	−91.6 (6)
S1—C7—C8—C9	−169.3 (2)	C3—O4—C25—C26	−160.9 (2)
C7—C8—C9—C18^i	−5.4 (4)	C27—N1—C26—O1	−3.7 (6)
C7—C8—C9—C10	171.9 (2)	C27—N1—C26—C25	173.3 (3)
C8—C9—C10—C11	−114.2 (3)	O4—C25—C26—O1	−166.5 (3)
C18^i—C9—C10—C11	63.0 (4)	O4—C25—C26—N1	16.3 (4)
C8—C9—C10—C13	6.3 (4)	C26—N1—C27—C28	91.7 (6)
C18^i—C9—C10—C13	−176.5 (3)	N1—C27—C28—C27^i	31.1 (4)

Symmetry code: (i) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4	0.86	2.24	2.650 (3)	110
N2—H2···O3	0.86	2.19	2.620 (3)	111
C16—H16A···O2^ii	0.96	2.50	3.435 (4)	165
C29—H29···O1^iii	0.98	2.36	3.287 (16)	157

Symmetry codes: (ii) x, −y+1, z−1/2; (iii) x, y−1, z.