Crystal structure of [2-(tri­ethyl­ammonio)­eth­yl][(2,4,6-triiso­propyl­phen­yl)sulfon­yl]amide tetra­hydrate

The zwitterionic title compound shows a major disorder of the triiso­propyl­phenyl group over two equally occupied locations. An inter­esting feature is the uncommon hydrate structure, exhibiting a tape-like motif which can be classified as a transition of the one-dimensional T4(2)6(2) motif into the two-dimensional L4(6)5(7)6(8) motif.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.049
• wR factor = 0.102
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

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Computing details

Data collection: CrysAlis PRO (Oxford Diffraction, 2013); cell refinement: CrysAlis PRO (Oxford Diffraction, 2013); data reduction: CrysAlis PRO (Oxford Diffraction, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

[2-(Triethylazaniumyl)ethyl][(2,4,6-triisopropylphenyl)sulfonyl]azanide tetrahydrate

Crystal data

C23H42N2O2S·4H2O	Z = 2
Mr = 482.71	F(000) = 532
Triclinic, P1	Dx = 1.191 Mg m^−3
a = 6.6797 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.7345 (5) Å	Cell parameters from 5123 reflections
c = 23.3973 (14) Å	θ = 2.6–28.2°
α = 96.579 (5)°	µ = 0.16 mm^−1
β = 93.734 (5)°	T = 173 K
γ = 95.570 (5)°	Plate, clear colourless
V = 1345.69 (14) Å^3	0.34 × 0.25 × 0.08 mm

Data collection

Agilent Xcalibur Sapphire3 diffractometer	5881 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4239 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
Detector resolution: 16.0560 pixels mm^-1	θmax = 27.0°, θmin = 2.4°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2013)	k = −11→11
Tmin = 0.981, Tmax = 1.000	l = −29→29
34730 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0428P)^2 + 0.1372P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
5881 reflections	Δρmax = 0.24 e Å^−3
472 parameters	Δρmin = −0.33 e Å^−3
36 restraints

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.46930 (6)	0.84811 (5)	0.73798 (2)	0.01893 (12)
O1	0.32141 (17)	0.72141 (14)	0.71224 (5)	0.0225 (3)
O2	0.39889 (18)	1.00090 (14)	0.73798 (6)	0.0295 (3)
O3	1.1266 (2)	1.00237 (18)	0.57740 (7)	0.0300 (3)
O4	1.5372 (2)	0.93656 (17)	0.59417 (7)	0.0322 (4)
O5	1.0118 (2)	1.06162 (16)	0.68669 (6)	0.0262 (3)
O6	1.7836 (2)	0.81480 (17)	0.51262 (7)	0.0312 (4)
N1	0.6732 (2)	0.85102 (16)	0.70803 (6)	0.0186 (3)
C1	0.7592 (3)	0.70129 (19)	0.70154 (7)	0.0186 (4)
H1A	0.7122	0.6373	0.7313	0.022*
H1B	0.9083	0.7186	0.7062	0.022*
N2	0.7612 (2)	0.46079 (15)	0.62443 (6)	0.0155 (3)
C2	0.6901 (2)	0.61873 (18)	0.64150 (7)	0.0164 (4)
H2A	0.5408	0.6063	0.6379	0.020*
H2B	0.7347	0.6877	0.6130	0.020*
C3	0.6882 (3)	0.3436 (2)	0.66417 (8)	0.0216 (4)
H3A	0.7416	0.2440	0.6522	0.026*
H3B	0.7462	0.3807	0.7039	0.026*
C4	0.4624 (3)	0.3141 (2)	0.66513 (9)	0.0320 (5)
H4A	0.4073	0.4116	0.6774	0.048*
H4B	0.4298	0.2395	0.6922	0.048*
H4C	0.4032	0.2722	0.6264	0.048*
C5	0.9904 (2)	0.4708 (2)	0.62907 (8)	0.0213 (4)
H5A	1.0404	0.5092	0.6694	0.026*
H5B	1.0311	0.3652	0.6203	0.026*
C6	1.0912 (3)	0.5746 (2)	0.58966 (8)	0.0291 (5)
H6A	1.0489	0.5345	0.5494	0.044*
H6B	1.2380	0.5770	0.5960	0.044*
H6C	1.0522	0.6798	0.5980	0.044*
C7	0.6761 (3)	0.4100 (2)	0.56254 (7)	0.0198 (4)
H7A	0.5270	0.4016	0.5615	0.024*
H7B	0.7194	0.4918	0.5386	0.024*
C8	0.7380 (3)	0.2575 (2)	0.53547 (8)	0.0281 (5)
H8A	0.8850	0.2656	0.5344	0.042*
H8B	0.6745	0.2333	0.4961	0.042*
H8C	0.6946	0.1750	0.5584	0.042*
C11	0.5230 (8)	0.8325 (6)	0.8086 (2)	0.0128 (14)	0.5020 (15)
C12	0.6299 (5)	0.9594 (4)	0.84523 (15)	0.0160 (7)	0.5020 (15)
C13	0.6466 (5)	0.9557 (4)	0.90455 (14)	0.0179 (8)	0.5020 (15)
H13	0.7179	1.0416	0.9285	0.021*	0.5020 (15)
C14	0.5630 (5)	0.8313 (4)	0.93024 (14)	0.0171 (8)	0.5020 (15)
C15	0.4656 (9)	0.7066 (5)	0.8933 (3)	0.0181 (11)	0.5020 (15)
H15	0.4075	0.6203	0.9100	0.022*	0.5020 (15)
C16	0.4474 (9)	0.6995 (8)	0.8334 (3)	0.0168 (12)	0.5020 (15)
C17	0.7393 (5)	1.1005 (4)	0.82250 (15)	0.0172 (8)	0.5020 (15)
H17	0.7186	1.0852	0.7794	0.021*	0.5020 (15)
C18	0.3527 (5)	0.5456 (4)	0.80066 (16)	0.0203 (8)	0.5020 (15)
H18	0.3777	0.5485	0.7591	0.024*	0.5020 (15)
C19	0.5849 (5)	0.8221 (4)	0.99530 (15)	0.0218 (8)	0.5020 (15)
H19	0.4485	0.7879	1.0074	0.026*	0.5020 (15)
C20	0.9656 (5)	1.1076 (5)	0.83905 (17)	0.0293 (10)	0.5020 (15)
H20A	0.9905	1.1284	0.8811	0.044*	0.5020 (15)
H20B	1.0375	1.1906	0.8211	0.044*	0.5020 (15)
H20C	1.0139	1.0083	0.8255	0.044*	0.5020 (15)
C21	0.6519 (6)	1.2506 (4)	0.84431 (19)	0.0331 (10)	0.5020 (15)
H21A	0.5071	1.2408	0.8328	0.050*	0.5020 (15)
H21B	0.7197	1.3375	0.8276	0.050*	0.5020 (15)
H21C	0.6731	1.2693	0.8865	0.050*	0.5020 (15)
C22	0.1266 (10)	0.5259 (6)	0.8042 (3)	0.0256 (14)	0.5020 (15)
H22A	0.0962	0.5164	0.8441	0.038*	0.5020 (15)
H22B	0.0684	0.4322	0.7792	0.038*	0.5020 (15)
H22C	0.0686	0.6163	0.7914	0.038*	0.5020 (15)
C23	0.4510 (6)	0.4075 (4)	0.82033 (17)	0.0281 (9)	0.5020 (15)
H23A	0.5970	0.4234	0.8172	0.042*	0.5020 (15)
H23B	0.3947	0.3125	0.7958	0.042*	0.5020 (15)
H23C	0.4243	0.3980	0.8605	0.042*	0.5020 (15)
C24	0.6614 (6)	0.9742 (4)	1.03185 (16)	0.0297 (9)	0.5020 (15)
H24A	0.6546	0.9616	1.0728	0.045*	0.5020 (15)
H24B	0.5775	1.0549	1.0221	0.045*	0.5020 (15)
H24C	0.8015	1.0042	1.0243	0.045*	0.5020 (15)
C25	0.7232 (11)	0.6981 (7)	1.0074 (3)	0.0307 (14)	0.5020 (15)
H25A	0.8594	0.7299	0.9969	0.046*	0.5020 (15)
H25B	0.6711	0.5996	0.9845	0.046*	0.5020 (15)
H25C	0.7278	0.6854	1.0485	0.046*	0.5020 (15)
C11'	0.5178 (9)	0.8031 (6)	0.8164 (2)	0.0110 (13)	0.4980 (15)
C16'	0.3975 (9)	0.6931 (8)	0.8416 (3)	0.0122 (15)	0.4980 (15)
C12'	0.7007 (5)	0.8740 (4)	0.84657 (14)	0.0149 (7)	0.4980 (15)
C13'	0.7689 (5)	0.8181 (4)	0.89710 (15)	0.0175 (8)	0.4980 (15)
H13'	0.8919	0.8650	0.9171	0.021*	0.4980 (15)
C14'	0.6617 (5)	0.6952 (4)	0.91930 (14)	0.0165 (8)	0.4980 (15)
C15'	0.4741 (8)	0.6404 (5)	0.8922 (2)	0.0129 (10)	0.4980 (15)
H15'	0.3936	0.5636	0.9086	0.015*	0.4980 (15)
C17'	0.8201 (5)	1.0221 (4)	0.83205 (14)	0.0149 (7)	0.4980 (15)
H17'	0.7618	1.0467	0.7941	0.018*	0.4980 (15)
C18'	0.1755 (5)	0.6347 (5)	0.82125 (16)	0.0201 (8)	0.4980 (15)
H18'	0.1335	0.6925	0.7887	0.024*	0.4980 (15)
C19'	0.7393 (6)	0.6336 (5)	0.97372 (18)	0.0202 (8)	0.4980 (15)
H19'	0.6572	0.5330	0.9764	0.024*	0.4980 (15)
C20'	1.0444 (5)	1.0021 (4)	0.82672 (18)	0.0213 (8)	0.4980 (15)
H20D	1.1134	1.0970	0.8155	0.032*	0.4980 (15)
H20E	1.0571	0.9148	0.7974	0.032*	0.4980 (15)
H20F	1.1056	0.9817	0.8639	0.032*	0.4980 (15)
C21'	0.7914 (6)	1.1560 (4)	0.87833 (16)	0.0231 (8)	0.4980 (15)
H21D	0.8426	1.1322	0.9162	0.035*	0.4980 (15)
H21E	0.6476	1.1696	0.8790	0.035*	0.4980 (15)
H21F	0.8657	1.2516	0.8694	0.035*	0.4980 (15)
C22'	0.0387 (5)	0.6696 (5)	0.87050 (16)	0.0266 (9)	0.4980 (15)
H22D	−0.1029	0.6520	0.8552	0.040*	0.4980 (15)
H22E	0.0701	0.7778	0.8875	0.040*	0.4980 (15)
H22F	0.0618	0.6011	0.9001	0.040*	0.4980 (15)
C23'	0.1484 (11)	0.4617 (6)	0.7993 (3)	0.0250 (13)	0.4980 (15)
H23D	0.1894	0.4026	0.8305	0.037*	0.4980 (15)
H23E	0.2321	0.4417	0.7669	0.037*	0.4980 (15)
H23F	0.0064	0.4298	0.7864	0.037*	0.4980 (15)
C24'	0.7064 (13)	0.7460 (9)	1.0273 (3)	0.0349 (15)	0.4980 (15)
H24D	0.7516	0.7031	1.0622	0.052*	0.4980 (15)
H24E	0.5627	0.7599	1.0280	0.052*	0.4980 (15)
H24F	0.7840	0.8463	1.0257	0.052*	0.4980 (15)
C25'	0.9588 (6)	0.6021 (5)	0.97315 (18)	0.0364 (11)	0.4980 (15)
H25D	0.9743	0.5244	0.9405	0.055*	0.4980 (15)
H25E	1.0009	0.5633	1.0092	0.055*	0.4980 (15)
H25F	1.0428	0.6982	0.9694	0.055*	0.4980 (15)
H4D	1.414 (3)	0.946 (2)	0.5910 (9)	0.036 (7)*
H3C	1.081 (3)	1.025 (3)	0.6124 (11)	0.048 (7)*
H3D	1.036 (4)	0.937 (3)	0.5591 (12)	0.065 (9)*
H5C	1.110 (4)	1.033 (3)	0.7046 (10)	0.049 (8)*
H6D	1.695 (4)	0.853 (3)	0.5332 (10)	0.048 (7)*
H6E	1.794 (4)	0.866 (3)	0.4853 (11)	0.056 (9)*
H5D	0.909 (4)	1.010 (3)	0.6956 (11)	0.065 (9)*
H4E	1.565 (4)	0.923 (3)	0.6322 (14)	0.094 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0136 (2)	0.0180 (2)	0.0234 (2)	0.00158 (17)	−0.00203 (18)	−0.00337 (18)
O1	0.0173 (6)	0.0259 (7)	0.0210 (7)	−0.0049 (5)	−0.0018 (5)	−0.0027 (5)
O2	0.0202 (7)	0.0226 (7)	0.0441 (9)	0.0081 (6)	−0.0053 (6)	−0.0041 (6)
O3	0.0257 (8)	0.0411 (9)	0.0229 (8)	0.0026 (7)	0.0028 (7)	0.0030 (7)
O4	0.0290 (9)	0.0445 (9)	0.0259 (8)	0.0138 (7)	0.0042 (7)	0.0067 (7)
O5	0.0211 (7)	0.0311 (8)	0.0278 (8)	0.0013 (6)	0.0031 (6)	0.0106 (6)
O6	0.0274 (8)	0.0390 (9)	0.0310 (9)	0.0115 (7)	0.0086 (7)	0.0103 (7)
N1	0.0162 (7)	0.0162 (7)	0.0225 (8)	0.0018 (6)	0.0007 (6)	−0.0012 (6)
C1	0.0165 (9)	0.0195 (9)	0.0196 (9)	0.0031 (7)	0.0001 (7)	0.0010 (7)
N2	0.0138 (7)	0.0157 (7)	0.0168 (8)	0.0030 (6)	0.0000 (6)	0.0008 (6)
C2	0.0167 (9)	0.0151 (9)	0.0180 (9)	0.0040 (7)	0.0014 (7)	0.0024 (7)
C3	0.0273 (10)	0.0165 (9)	0.0223 (10)	0.0042 (8)	0.0034 (8)	0.0050 (7)
C4	0.0281 (11)	0.0324 (11)	0.0382 (12)	0.0005 (9)	0.0113 (9)	0.0125 (9)
C5	0.0133 (9)	0.0240 (10)	0.0257 (10)	0.0055 (7)	−0.0027 (8)	−0.0011 (8)
C6	0.0157 (9)	0.0426 (12)	0.0270 (11)	−0.0029 (9)	−0.0011 (8)	0.0025 (9)
C7	0.0153 (9)	0.0247 (10)	0.0173 (9)	−0.0005 (7)	−0.0009 (7)	−0.0028 (7)
C8	0.0256 (10)	0.0279 (10)	0.0281 (11)	0.0022 (8)	0.0035 (9)	−0.0080 (9)
C11	0.0123 (16)	0.0136 (16)	0.0127 (16)	0.0009 (9)	0.0033 (9)	0.0017 (9)
C12	0.0134 (17)	0.0168 (19)	0.0178 (19)	0.0013 (15)	0.0003 (14)	0.0027 (15)
C13	0.0161 (17)	0.0200 (18)	0.0156 (18)	0.0007 (14)	−0.0019 (14)	−0.0033 (14)
C14	0.0153 (17)	0.0248 (19)	0.0129 (17)	0.0077 (14)	0.0028 (14)	0.0037 (15)
C15	0.020 (2)	0.011 (2)	0.025 (2)	0.000 (2)	0.0075 (17)	0.008 (3)
C16	0.013 (3)	0.020 (3)	0.018 (3)	0.003 (2)	0.002 (2)	−0.0006 (19)
C17	0.0174 (19)	0.0157 (19)	0.0170 (19)	−0.0038 (15)	0.0005 (15)	0.0003 (15)
C18	0.0231 (19)	0.0165 (18)	0.0203 (19)	−0.0058 (15)	−0.0003 (15)	0.0057 (15)
C19	0.0206 (19)	0.030 (2)	0.0155 (18)	0.0016 (16)	0.0041 (15)	0.0043 (16)
C20	0.019 (2)	0.038 (2)	0.031 (2)	−0.0049 (19)	−0.0003 (17)	0.0127 (19)
C21	0.036 (2)	0.019 (2)	0.046 (3)	0.0010 (17)	0.013 (2)	0.0055 (18)
C22	0.023 (3)	0.018 (4)	0.035 (3)	−0.003 (3)	−0.009 (2)	0.009 (3)
C23	0.038 (2)	0.0172 (19)	0.028 (2)	0.0010 (17)	0.0011 (18)	0.0013 (16)
C24	0.039 (2)	0.035 (2)	0.0153 (19)	0.0106 (19)	−0.0028 (17)	−0.0014 (17)
C25	0.045 (3)	0.026 (4)	0.022 (4)	0.008 (3)	−0.006 (3)	0.008 (3)
C11'	0.0113 (15)	0.0120 (16)	0.0097 (15)	0.0002 (9)	0.0018 (9)	0.0016 (9)
C16'	0.0128 (18)	0.0110 (16)	0.0132 (17)	0.0016 (10)	0.0013 (10)	0.0022 (9)
C12'	0.0190 (18)	0.0113 (18)	0.0152 (18)	0.0029 (15)	0.0066 (14)	0.0008 (14)
C13'	0.0144 (17)	0.0195 (18)	0.0176 (18)	−0.0010 (14)	−0.0005 (14)	0.0013 (14)
C14'	0.0174 (18)	0.0186 (18)	0.0136 (17)	0.0035 (14)	0.0013 (14)	0.0007 (14)
C15'	0.013 (2)	0.011 (2)	0.014 (2)	−0.003 (2)	0.0009 (15)	0.005 (2)
C17'	0.0159 (18)	0.0177 (19)	0.0104 (17)	−0.0023 (16)	−0.0014 (14)	0.0040 (15)
C18'	0.0189 (19)	0.023 (2)	0.0183 (19)	−0.0041 (16)	0.0020 (15)	0.0064 (17)
C19'	0.023 (2)	0.021 (2)	0.017 (2)	0.0015 (16)	−0.0015 (17)	0.0060 (17)
C20'	0.0162 (18)	0.023 (2)	0.024 (2)	−0.0024 (16)	0.0063 (16)	0.0035 (16)
C21'	0.026 (2)	0.0180 (18)	0.025 (2)	−0.0012 (15)	0.0074 (16)	0.0033 (16)
C22'	0.0156 (18)	0.037 (2)	0.028 (2)	0.0002 (16)	0.0021 (16)	0.0072 (18)
C23'	0.026 (3)	0.022 (3)	0.026 (3)	−0.004 (3)	0.0007 (19)	0.002 (3)
C24'	0.045 (3)	0.049 (5)	0.014 (3)	0.016 (3)	0.006 (3)	0.005 (3)
C25'	0.034 (2)	0.054 (3)	0.027 (2)	0.022 (2)	0.0028 (19)	0.018 (2)

Geometric parameters (Å, º)

S1—O1	1.4563 (12)	C19—C24	1.520 (5)
S1—O2	1.4574 (13)	C19—C25	1.529 (7)
S1—N1	1.5708 (14)	C20—H20A	0.9800
S1—C11	1.692 (6)	C20—H20B	0.9800
S1—C11'	1.934 (6)	C20—H20C	0.9800
O3—H3C	0.90 (2)	C21—H21A	0.9800
O3—H3D	0.85 (3)	C21—H21B	0.9800
O4—H4D	0.83 (2)	C21—H21C	0.9800
O4—H4E	0.92 (3)	C22—H22A	0.9800
O5—H5C	0.83 (3)	C22—H22B	0.9800
O5—H5D	0.84 (3)	C22—H22C	0.9800
O6—H6D	0.86 (2)	C23—H23A	0.9800
O6—H6E	0.82 (3)	C23—H23B	0.9800
N1—C1	1.475 (2)	C23—H23C	0.9800
C1—H1A	0.9900	C24—H24A	0.9800
C1—H1B	0.9900	C24—H24B	0.9800
C1—C2	1.525 (2)	C24—H24C	0.9800
N2—C2	1.521 (2)	C25—H25A	0.9800
N2—C3	1.527 (2)	C25—H25B	0.9800
N2—C5	1.521 (2)	C25—H25C	0.9800
N2—C7	1.521 (2)	C11'—C16'	1.399 (8)
C2—H2A	0.9900	C11'—C12'	1.419 (7)
C2—H2B	0.9900	C16'—C15'	1.403 (9)
C3—H3A	0.9900	C16'—C18'	1.546 (7)
C3—H3B	0.9900	C12'—C13'	1.396 (5)
C3—C4	1.508 (2)	C12'—C17'	1.536 (5)
C4—H4A	0.9800	C13'—H13'	0.9500
C4—H4B	0.9800	C13'—C14'	1.401 (5)
C4—H4C	0.9800	C14'—C15'	1.383 (7)
C5—H5A	0.9900	C14'—C19'	1.518 (5)
C5—H5B	0.9900	C15'—H15'	0.9500
C5—C6	1.510 (3)	C17'—H17'	1.0000
C6—H6A	0.9800	C17'—C20'	1.536 (5)
C6—H6B	0.9800	C17'—C21'	1.535 (5)
C6—H6C	0.9800	C18'—H18'	1.0000
C7—H7A	0.9900	C18'—C22'	1.538 (5)
C7—H7B	0.9900	C18'—C23'	1.529 (5)
C7—C8	1.514 (2)	C19'—H19'	1.0000
C8—H8A	0.9800	C19'—C24'	1.542 (6)
C8—H8B	0.9800	C19'—C25'	1.518 (5)
C8—H8C	0.9800	C20'—H20D	0.9800
C11—C12	1.422 (6)	C20'—H20E	0.9800
C11—C16	1.420 (8)	C20'—H20F	0.9800
C12—C13	1.390 (5)	C21'—H21D	0.9800
C12—C17	1.537 (5)	C21'—H21E	0.9800
C13—H13	0.9500	C21'—H21F	0.9800
C13—C14	1.389 (5)	C22'—H22D	0.9800
C14—C15	1.390 (6)	C22'—H22E	0.9800
C14—C19	1.532 (5)	C22'—H22F	0.9800
C15—H15	0.9500	C23'—H23D	0.9800
C15—C16	1.392 (9)	C23'—H23E	0.9800
C16—C18	1.526 (7)	C23'—H23F	0.9800
C17—H17	1.0000	C24'—H24D	0.9800
C17—C20	1.529 (5)	C24'—H24E	0.9800
C17—C21	1.534 (5)	C24'—H24F	0.9800
C18—H18	1.0000	C25'—H25D	0.9800
C18—C22	1.512 (7)	C25'—H25E	0.9800
C18—C23	1.530 (5)	C25'—H25F	0.9800
C19—H19	1.0000
O1—S1—O2	113.94 (7)	C17—C20—H20C	109.5
O1—S1—N1	112.66 (7)	H20A—C20—H20B	109.5
O1—S1—C11	110.2 (2)	H20A—C20—H20C	109.5
O1—S1—C11'	103.48 (18)	H20B—C20—H20C	109.5
O2—S1—N1	107.70 (8)	C17—C21—H21A	109.5
O2—S1—C11	104.22 (18)	C17—C21—H21B	109.5
O2—S1—C11'	109.94 (16)	C17—C21—H21C	109.5
N1—S1—C11	107.6 (2)	H21A—C21—H21B	109.5
N1—S1—C11'	108.99 (18)	H21A—C21—H21C	109.5
H3C—O3—H3D	105 (2)	H21B—C21—H21C	109.5
H4D—O4—H4E	105 (2)	C18—C22—H22A	109.5
H5C—O5—H5D	107 (2)	C18—C22—H22B	109.5
H6D—O6—H6E	107 (2)	C18—C22—H22C	109.5
C1—N1—S1	114.54 (11)	H22A—C22—H22B	109.5
N1—C1—H1A	110.1	H22A—C22—H22C	109.5
N1—C1—H1B	110.1	H22B—C22—H22C	109.5
N1—C1—C2	108.09 (14)	C18—C23—H23A	109.5
H1A—C1—H1B	108.4	C18—C23—H23B	109.5
C2—C1—H1A	110.1	C18—C23—H23C	109.5
C2—C1—H1B	110.1	H23A—C23—H23B	109.5
C2—N2—C3	111.46 (12)	H23A—C23—H23C	109.5
C2—N2—C7	106.21 (12)	H23B—C23—H23C	109.5
C5—N2—C2	110.78 (13)	C19—C24—H24A	109.5
C5—N2—C3	106.66 (13)	C19—C24—H24B	109.5
C5—N2—C7	110.95 (12)	C19—C24—H24C	109.5
C7—N2—C3	110.85 (13)	H24A—C24—H24B	109.5
C1—C2—H2A	107.8	H24A—C24—H24C	109.5
C1—C2—H2B	107.8	H24B—C24—H24C	109.5
N2—C2—C1	117.89 (14)	C19—C25—H25A	109.5
N2—C2—H2A	107.8	C19—C25—H25B	109.5
N2—C2—H2B	107.8	C19—C25—H25C	109.5
H2A—C2—H2B	107.2	H25A—C25—H25B	109.5
N2—C3—H3A	108.5	H25A—C25—H25C	109.5
N2—C3—H3B	108.5	H25B—C25—H25C	109.5
H3A—C3—H3B	107.5	C16'—C11'—S1	123.9 (5)
C4—C3—N2	115.21 (15)	C16'—C11'—C12'	119.4 (5)
C4—C3—H3A	108.5	C12'—C11'—S1	116.3 (4)
C4—C3—H3B	108.5	C11'—C16'—C15'	118.7 (6)
C3—C4—H4A	109.5	C11'—C16'—C18'	124.9 (6)
C3—C4—H4B	109.5	C15'—C16'—C18'	116.1 (5)
C3—C4—H4C	109.5	C11'—C12'—C17'	124.8 (4)
H4A—C4—H4B	109.5	C13'—C12'—C11'	118.9 (4)
H4A—C4—H4C	109.5	C13'—C12'—C17'	115.8 (3)
H4B—C4—H4C	109.5	C12'—C13'—H13'	118.9
N2—C5—H5A	108.6	C12'—C13'—C14'	122.1 (3)
N2—C5—H5B	108.6	C14'—C13'—H13'	118.9
H5A—C5—H5B	107.6	C13'—C14'—C19'	121.6 (3)
C6—C5—N2	114.60 (14)	C15'—C14'—C13'	117.1 (3)
C6—C5—H5A	108.6	C15'—C14'—C19'	121.1 (3)
C6—C5—H5B	108.6	C16'—C15'—H15'	118.5
C5—C6—H6A	109.5	C14'—C15'—C16'	122.9 (5)
C5—C6—H6B	109.5	C14'—C15'—H15'	118.5
C5—C6—H6C	109.5	C12'—C17'—H17'	108.2
H6A—C6—H6B	109.5	C12'—C17'—C20'	112.1 (3)
H6A—C6—H6C	109.5	C20'—C17'—H17'	108.2
H6B—C6—H6C	109.5	C21'—C17'—C12'	108.5 (3)
N2—C7—H7A	108.5	C21'—C17'—H17'	108.2
N2—C7—H7B	108.5	C21'—C17'—C20'	111.6 (3)
H7A—C7—H7B	107.5	C16'—C18'—H18'	108.1
C8—C7—N2	115.17 (15)	C22'—C18'—C16'	110.1 (4)
C8—C7—H7A	108.5	C22'—C18'—H18'	108.1
C8—C7—H7B	108.5	C23'—C18'—C16'	112.1 (5)
C7—C8—H8A	109.5	C23'—C18'—H18'	108.1
C7—C8—H8B	109.5	C23'—C18'—C22'	110.3 (4)
C7—C8—H8C	109.5	C14'—C19'—H19'	107.6
H8A—C8—H8B	109.5	C14'—C19'—C24'	110.1 (4)
H8A—C8—H8C	109.5	C14'—C19'—C25'	113.0 (3)
H8B—C8—H8C	109.5	C24'—C19'—H19'	107.6
C12—C11—S1	119.8 (4)	C25'—C19'—H19'	107.6
C16—C11—S1	121.0 (4)	C25'—C19'—C24'	110.8 (5)
C16—C11—C12	118.9 (5)	C17'—C20'—H20D	109.5
C11—C12—C17	123.3 (4)	C17'—C20'—H20E	109.5
C13—C12—C11	119.7 (4)	C17'—C20'—H20F	109.5
C13—C12—C17	116.9 (3)	H20D—C20'—H20E	109.5
C12—C13—H13	118.7	H20D—C20'—H20F	109.5
C14—C13—C12	122.5 (3)	H20E—C20'—H20F	109.5
C14—C13—H13	118.7	C17'—C21'—H21D	109.5
C13—C14—C15	116.5 (4)	C17'—C21'—H21E	109.5
C13—C14—C19	123.6 (3)	C17'—C21'—H21F	109.5
C15—C14—C19	119.8 (4)	H21D—C21'—H21E	109.5
C14—C15—H15	117.8	H21D—C21'—H21F	109.5
C14—C15—C16	124.5 (5)	H21E—C21'—H21F	109.5
C16—C15—H15	117.8	C18'—C22'—H22D	109.5
C11—C16—C18	126.4 (5)	C18'—C22'—H22E	109.5
C15—C16—C11	117.6 (5)	C18'—C22'—H22F	109.5
C15—C16—C18	115.9 (5)	H22D—C22'—H22E	109.5
C12—C17—H17	108.0	H22D—C22'—H22F	109.5
C20—C17—C12	109.2 (3)	H22E—C22'—H22F	109.5
C20—C17—H17	108.0	C18'—C23'—H23D	109.5
C20—C17—C21	112.3 (3)	C18'—C23'—H23E	109.5
C21—C17—C12	111.3 (3)	C18'—C23'—H23F	109.5
C21—C17—H17	108.0	H23D—C23'—H23E	109.5
C16—C18—H18	107.1	H23D—C23'—H23F	109.5
C16—C18—C23	112.2 (4)	H23E—C23'—H23F	109.5
C22—C18—C16	111.4 (4)	C19'—C24'—H24D	109.5
C22—C18—H18	107.1	C19'—C24'—H24E	109.5
C22—C18—C23	111.6 (3)	C19'—C24'—H24F	109.5
C23—C18—H18	107.1	H24D—C24'—H24E	109.5
C14—C19—H19	107.6	H24D—C24'—H24F	109.5
C24—C19—C14	114.7 (3)	H24E—C24'—H24F	109.5
C24—C19—H19	107.6	C19'—C25'—H25D	109.5
C24—C19—C25	109.8 (4)	C19'—C25'—H25E	109.5
C25—C19—C14	109.3 (3)	C19'—C25'—H25F	109.5
C25—C19—H19	107.6	H25D—C25'—H25E	109.5
C17—C20—H20A	109.5	H25D—C25'—H25F	109.5
C17—C20—H20B	109.5	H25E—C25'—H25F	109.5
S1—N1—C1—C2	94.86 (14)	C13—C12—C17—C20	60.6 (4)
S1—C11—C12—C13	170.0 (3)	C13—C12—C17—C21	−63.9 (4)
S1—C11—C12—C17	−13.0 (6)	C13—C14—C15—C16	0.0 (7)
S1—C11—C16—C15	−168.3 (4)	C13—C14—C19—C24	14.0 (5)
S1—C11—C16—C18	13.7 (8)	C13—C14—C19—C25	−109.8 (4)
S1—C11'—C16'—C15'	163.2 (4)	C14—C15—C16—C11	−3.9 (9)
S1—C11'—C16'—C18'	−22.9 (8)	C14—C15—C16—C18	174.2 (4)
S1—C11'—C12'—C13'	−164.4 (3)	C15—C14—C19—C24	−170.1 (4)
S1—C11'—C12'—C17'	23.3 (5)	C15—C14—C19—C25	66.1 (5)
O1—S1—N1—C1	−50.19 (14)	C15—C16—C18—C22	75.9 (6)
O1—S1—C11—C12	−166.8 (3)	C15—C16—C18—C23	−50.0 (6)
O1—S1—C11—C16	7.5 (5)	C16—C11—C12—C13	−4.3 (6)
O2—S1—N1—C1	−176.69 (12)	C16—C11—C12—C17	172.6 (4)
O2—S1—C11—C12	−44.1 (4)	C17—C12—C13—C14	−176.8 (3)
O2—S1—C11—C16	130.1 (4)	C19—C14—C15—C16	−176.3 (5)
N1—S1—C11—C12	70.0 (4)	C11'—S1—N1—C1	64.1 (2)
N1—S1—C11—C16	−115.7 (5)	C11'—C16'—C15'—C14'	1.7 (8)
N1—C1—C2—N2	179.67 (13)	C11'—C16'—C18'—C22'	−120.3 (6)
C2—N2—C3—C4	60.00 (19)	C11'—C16'—C18'—C23'	116.5 (6)
C2—N2—C5—C6	−62.17 (18)	C11'—C12'—C13'—C14'	−0.6 (5)
C2—N2—C7—C8	176.93 (14)	C11'—C12'—C17'—C20'	−129.7 (4)
C3—N2—C2—C1	61.08 (19)	C11'—C12'—C17'—C21'	106.5 (4)
C3—N2—C5—C6	176.37 (15)	C16'—C11'—C12'—C13'	8.1 (6)
C3—N2—C7—C8	−61.84 (18)	C16'—C11'—C12'—C17'	−164.2 (4)
C5—N2—C2—C1	−57.52 (18)	C12'—C11'—C16'—C15'	−8.7 (8)
C5—N2—C3—C4	−178.96 (15)	C12'—C11'—C16'—C18'	165.2 (5)
C5—N2—C7—C8	56.47 (19)	C12'—C13'—C14'—C15'	−6.2 (5)
C7—N2—C2—C1	−178.09 (14)	C12'—C13'—C14'—C19'	178.9 (3)
C7—N2—C3—C4	−58.08 (19)	C13'—C12'—C17'—C20'	57.7 (4)
C7—N2—C5—C6	55.54 (19)	C13'—C12'—C17'—C21'	−66.0 (4)
C11—S1—N1—C1	71.5 (2)	C13'—C14'—C15'—C16'	5.6 (7)
C11—C12—C13—C14	0.3 (5)	C13'—C14'—C19'—C24'	75.7 (5)
C11—C12—C17—C20	−116.4 (4)	C13'—C14'—C19'—C25'	−48.8 (5)
C11—C12—C17—C21	119.1 (4)	C15'—C16'—C18'—C22'	53.7 (6)
C11—C16—C18—C22	−106.2 (6)	C15'—C16'—C18'—C23'	−69.5 (6)
C11—C16—C18—C23	127.9 (6)	C15'—C14'—C19'—C24'	−99.0 (5)
C12—C11—C16—C15	6.0 (8)	C15'—C14'—C19'—C25'	136.5 (4)
C12—C11—C16—C18	−172.0 (4)	C17'—C12'—C13'—C14'	172.4 (3)
C12—C13—C14—C15	1.9 (5)	C18'—C16'—C15'—C14'	−172.7 (4)
C12—C13—C14—C19	178.0 (3)	C19'—C14'—C15'—C16'	−179.4 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4D···O3	0.83 (2)	2.04 (2)	2.867 (2)	171 (2)
O3—H3C···O5	0.90 (2)	1.83 (2)	2.725 (2)	174 (2)
O3—H3D···O6^i	0.85 (3)	2.08 (3)	2.912 (2)	169 (2)
O5—H5C···O2^ii	0.83 (3)	2.09 (3)	2.901 (2)	165 (2)
O6—H6D···O4	0.86 (2)	1.95 (2)	2.787 (2)	167 (2)
O6—H6E···O3^iii	0.82 (3)	2.03 (3)	2.845 (2)	170 (2)
O5—H5D···N1	0.84 (3)	2.05 (3)	2.881 (2)	170 (2)
O4—H4E···N1^ii	0.92 (3)	2.06 (3)	2.959 (2)	165 (3)

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+3, −y+2, −z+1.