A long thin mol­ecule, 2,6-di­methyl-6-tetra­decyl-2-tetra­decyl­oxy-1,3,6-­dioxazocan-6-ium iodide

An unusually long thin mol­ecule is found in the crystal structure of 2,6-di­methyl-6-tetra­decyl-2-tetra­decyl­oxy-1,3,6-dioxazocan-6-ium iodide, C₃₅H₇₂NO₃⁺·I^-. The length of the mol­ecule results from two extended tetra­decyl alkyl chains bonded to a central dioxazocine group. From H tip-to-tip it measures 40.336 (5) Å. At its waist, the maximum dimension is 6.770 (3) Å.

Key indicators

• Single-crystal X-ray study
• T = 91 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.084
• Data-to-parameter ratio = 28.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SMART; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELXL97.

2,6-Dimethyl-6-tetradecyl-2-tetradecyloxy-[1,3,6]dioxazocan-6-ium iodide

Crystal data

C35H72NO3^+·I^−	F(000) = 732
Mr = 681.84	Dx = 1.234 Mg m^−3
Triclinic, P1	Melting point: 499 K
a = 6.0194 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.2183 (8) Å	Cell parameters from 510 reflections
c = 42.384 (4) Å	θ = 2.4–30.7°
α = 85.527 (5)°	µ = 0.90 mm^−1
β = 88.810 (4)°	T = 91 K
γ = 87.880 (4)°	Plate, colorless
V = 1834.4 (3) Å^3	0.28 × 0.12 × 0.04 mm
Z = 2

Data collection

Bruker SMART 1000 diffractometer	10499 independent reflections
Radiation source: normal-focus sealed tube	9098 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 8.3 pixels mm^-1	θmax = 30.0°, θmin = 1.9°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −10→10
Tmin = 0.786, Tmax = 0.965	l = −59→59
25283 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0365P)^2 + 0.6504P] where P = (Fo^2 + 2Fc^2)/3
10499 reflections	(Δ/σ)max = 0.001
365 parameters	Δρmax = 1.20 e Å^−3
0 restraints	Δρmin = −1.31 e Å^−3

Special details

Experimental. IR 2922, 2851, 1469, 1053 cm^{-1. 1}H NMR (CDCl₃) δ, J = 6.0, 6H), 1.26 (s, 44H), 1.53 (s, 3H), 1.57 (m, 2H), 1.84 (m, 2H), 3.48 (t, J = 6.8 Hz, 2H), 3.54 (s, 3H), 3.92 (m, 8H), 4.36 (m, 2H); 13 C NMR (CDCl3) 14.3, 19.9, 22.8, 26.4, 29.5, 29.6, 29.7, 29.8, 29.8, 29.8, 30.0, 32.1, 45.6, 57.1, 61.7, 63.5, 114.5; Anal. Calcd. for C₂₁H₄₃NO₃ (357.5818): C, 70.54; H, 12.12; N, 3.92. Found: C, 70.51; H, 112.43; N, 3.69.

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
I1	−0.13296 (2)	1.71292 (2)	0.294219 (3)	0.01709 (5)
O1	0.6452 (2)	0.5467 (2)	0.78740 (3)	0.0132 (3)
O2	0.4805 (3)	0.6604 (2)	0.82958 (3)	0.0174 (3)
O3	0.3706 (2)	0.7792 (2)	0.78140 (3)	0.0140 (3)
N6	0.7069 (3)	0.7930 (2)	0.72444 (4)	0.0113 (3)
C1	0.2499 (4)	0.4806 (3)	0.79689 (5)	0.0169 (4)
H1A	0.2919	0.3610	0.8081	0.025*
H1B	0.2210	0.4623	0.7747	0.025*
H1C	0.1154	0.5326	0.8068	0.025*
C2	0.4374 (4)	0.6136 (3)	0.79855 (5)	0.0141 (4)
C4	0.5396 (4)	0.9127 (3)	0.77602 (5)	0.0151 (4)
H4A	0.6768	0.8662	0.7869	0.018*
H4B	0.4900	1.0306	0.7849	0.018*
C5	0.5882 (4)	0.9481 (3)	0.74097 (5)	0.0135 (4)
H5A	0.6792	1.0598	0.7379	0.016*
H5B	0.4454	0.9781	0.7302	0.016*
C6	0.9435 (3)	0.7725 (3)	0.73516 (5)	0.0153 (4)
H6A	1.0188	0.8892	0.7298	0.023*
H6B	1.0203	0.6721	0.7245	0.023*
H60C	0.9456	0.7429	0.7581	0.023*
C7	0.5902 (3)	0.6088 (3)	0.72859 (5)	0.0128 (4)
H7A	0.4282	0.6366	0.7301	0.015*
H7B	0.6180	0.5431	0.7092	0.015*
C8	0.6536 (4)	0.4761 (3)	0.75678 (5)	0.0142 (4)
H8A	0.5545	0.3694	0.7573	0.017*
H8B	0.8069	0.4272	0.7530	0.017*
C9	0.7134 (4)	0.8551 (3)	0.68916 (5)	0.0141 (4)
H9A	0.8225	0.7740	0.6785	0.017*
H9B	0.7668	0.9835	0.6865	0.017*
C10	0.4896 (4)	0.8502 (3)	0.67279 (5)	0.0150 (4)
H10A	0.4588	0.7202	0.6689	0.018*
H10B	0.3699	0.8963	0.6868	0.018*
C11	0.4899 (4)	0.9695 (3)	0.64146 (5)	0.0162 (4)
H11A	0.5100	1.1010	0.6455	0.019*
H11B	0.6161	0.9291	0.6280	0.019*
C12	0.2729 (4)	0.9538 (3)	0.62409 (5)	0.0172 (4)
H12A	0.1470	0.9868	0.6382	0.021*
H12B	0.2576	0.8231	0.6192	0.021*
C13	0.2589 (4)	1.0786 (3)	0.59342 (5)	0.0171 (4)
H13A	0.3884	1.0496	0.5797	0.020*
H13B	0.2674	1.2099	0.5984	0.020*
C14	0.0451 (4)	1.0559 (3)	0.57536 (5)	0.0175 (4)
H14A	0.0393	0.9255	0.5698	0.021*
H14B	−0.0842	1.0807	0.5894	0.021*
C15	0.0261 (4)	1.1842 (3)	0.54530 (5)	0.0171 (4)
H15A	0.1577	1.1619	0.5315	0.020*
H15B	0.0278	1.3147	0.5509	0.020*
C16	−0.1835 (4)	1.1587 (3)	0.52669 (5)	0.0166 (4)
H16A	−0.3152	1.1797	0.5405	0.020*
H16B	−0.1844	1.0288	0.5208	0.020*
C17	−0.2022 (4)	1.2900 (3)	0.49673 (5)	0.0169 (4)
H17A	−0.2011	1.4199	0.5027	0.020*
H17B	−0.0703	1.2690	0.4830	0.020*
C18	−0.4113 (4)	1.2651 (3)	0.47801 (5)	0.0169 (4)
H18A	−0.4123	1.1355	0.4720	0.020*
H18B	−0.5434	1.2858	0.4918	0.020*
C19	−0.4289 (4)	1.3971 (3)	0.44825 (5)	0.0171 (4)
H19A	−0.2963	1.3763	0.4346	0.021*
H19B	−0.4273	1.5266	0.4544	0.021*
C20	−0.6373 (4)	1.3746 (3)	0.42914 (5)	0.0167 (4)
H20A	−0.6398	1.2448	0.4232	0.020*
H20B	−0.7700	1.3970	0.4427	0.020*
C21	−0.6519 (4)	1.5053 (3)	0.39933 (5)	0.0208 (5)
H21A	−0.5212	1.4811	0.3855	0.025*
H21B	−0.6465	1.6351	0.4052	0.025*
C22	−0.8636 (4)	1.4839 (4)	0.38085 (6)	0.0249 (5)
H22A	−0.8710	1.3553	0.3752	0.037*
H22B	−0.8618	1.5680	0.3616	0.037*
H22C	−0.9936	1.5148	0.3940	0.037*
C23	0.5373 (4)	0.5058 (3)	0.85193 (5)	0.0190 (4)
H23A	0.5862	0.3968	0.8404	0.023*
H23B	0.4052	0.4719	0.8651	0.023*
C24	0.7216 (4)	0.5583 (3)	0.87279 (5)	0.0172 (4)
H24A	0.6838	0.6805	0.8810	0.021*
H24B	0.8611	0.5700	0.8601	0.021*
C25	0.7572 (4)	0.4128 (3)	0.90050 (5)	0.0163 (4)
H25A	0.7830	0.2894	0.8921	0.020*
H25B	0.6200	0.4076	0.9138	0.020*
C26	0.9526 (4)	0.4515 (3)	0.92121 (5)	0.0165 (4)
H26A	1.0914	0.4482	0.9083	0.020*
H26B	0.9318	0.5782	0.9285	0.020*
C27	0.9774 (4)	0.3126 (3)	0.95001 (5)	0.0163 (4)
H27A	0.9942	0.1856	0.9428	0.020*
H27B	0.8401	0.3183	0.9632	0.020*
C28	1.1761 (4)	0.3486 (3)	0.97019 (5)	0.0164 (4)
H28A	1.3135	0.3410	0.9570	0.020*
H28B	1.1604	0.4764	0.9771	0.020*
C29	1.2002 (4)	0.2122 (3)	0.99933 (5)	0.0160 (4)
H29A	1.0629	0.2199	1.0125	0.019*
H29B	1.2157	0.0844	0.9925	0.019*
C30	1.3985 (4)	0.2480 (3)	1.01945 (5)	0.0165 (4)
H30A	1.3828	0.3759	1.0263	0.020*
H30B	1.5357	0.2405	1.0062	0.020*
C31	1.4236 (4)	0.1118 (3)	1.04866 (5)	0.0160 (4)
H31A	1.2864	0.1190	1.0619	0.019*
H31B	1.4403	−0.0161	1.0418	0.019*
C32	1.6225 (4)	0.1496 (3)	1.06872 (5)	0.0153 (4)
H32A	1.7600	0.1407	1.0556	0.018*
H32B	1.6070	0.2782	1.0753	0.018*
C33	1.6452 (4)	0.0153 (3)	1.09806 (5)	0.0158 (4)
H33A	1.6692	−0.1125	1.0914	0.019*
H33B	1.5044	0.0190	1.1105	0.019*
C34	1.8360 (4)	0.0592 (3)	1.11911 (5)	0.0166 (4)
H34A	1.9777	0.0513	1.1069	0.020*
H34B	1.8148	0.1882	1.1253	0.020*
C35	1.8515 (4)	−0.0727 (3)	1.14882 (5)	0.0195 (4)
H35A	1.8777	−0.2011	1.1426	0.023*
H35B	1.7075	−0.0682	1.1605	0.023*
C36	2.0362 (4)	−0.0273 (4)	1.17086 (6)	0.0252 (5)
H36A	2.1798	−0.0335	1.1596	0.038*
H36B	2.0384	−0.1174	1.1894	0.038*
H36C	2.0090	0.0982	1.1777	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01616 (7)	0.01440 (7)	0.02085 (7)	0.00078 (5)	−0.00200 (5)	−0.00229 (5)
O1	0.0124 (7)	0.0149 (7)	0.0120 (7)	0.0005 (6)	−0.0026 (5)	0.0003 (5)
O2	0.0250 (8)	0.0169 (8)	0.0097 (7)	0.0015 (6)	−0.0026 (6)	0.0022 (5)
O3	0.0155 (7)	0.0143 (7)	0.0115 (7)	0.0018 (6)	0.0000 (5)	0.0028 (5)
N6	0.0106 (8)	0.0105 (8)	0.0127 (8)	−0.0014 (6)	−0.0014 (6)	0.0007 (6)
C1	0.0169 (11)	0.0195 (11)	0.0136 (10)	−0.0019 (9)	−0.0004 (8)	0.0036 (8)
C2	0.0156 (10)	0.0160 (10)	0.0102 (9)	0.0009 (8)	−0.0001 (7)	0.0018 (7)
C4	0.0196 (11)	0.0130 (10)	0.0125 (9)	−0.0011 (8)	−0.0021 (8)	0.0003 (7)
C5	0.0160 (10)	0.0100 (9)	0.0142 (9)	0.0016 (8)	0.0003 (7)	−0.0001 (7)
C6	0.0099 (10)	0.0154 (10)	0.0204 (10)	−0.0003 (8)	−0.0030 (8)	0.0010 (8)
C7	0.0124 (10)	0.0117 (9)	0.0146 (9)	−0.0020 (7)	−0.0005 (7)	−0.0018 (7)
C8	0.0166 (10)	0.0112 (9)	0.0145 (9)	0.0006 (8)	−0.0007 (7)	0.0002 (7)
C9	0.0153 (10)	0.0163 (10)	0.0101 (9)	−0.0015 (8)	0.0006 (7)	0.0021 (7)
C10	0.0153 (10)	0.0179 (10)	0.0120 (9)	−0.0035 (8)	−0.0015 (7)	0.0001 (7)
C11	0.0161 (10)	0.0190 (11)	0.0130 (9)	−0.0016 (8)	−0.0003 (8)	0.0030 (8)
C12	0.0166 (11)	0.0206 (11)	0.0142 (10)	−0.0024 (9)	−0.0023 (8)	0.0021 (8)
C13	0.0170 (11)	0.0202 (11)	0.0136 (10)	−0.0029 (8)	−0.0024 (8)	0.0025 (8)
C14	0.0164 (11)	0.0204 (11)	0.0154 (10)	−0.0023 (9)	−0.0029 (8)	0.0018 (8)
C15	0.0161 (11)	0.0191 (11)	0.0157 (10)	−0.0013 (8)	−0.0033 (8)	0.0023 (8)
C16	0.0167 (11)	0.0205 (11)	0.0121 (9)	−0.0025 (8)	−0.0024 (8)	0.0032 (8)
C17	0.0175 (11)	0.0197 (11)	0.0131 (9)	−0.0023 (9)	−0.0020 (8)	0.0023 (8)
C18	0.0159 (11)	0.0197 (11)	0.0150 (10)	−0.0025 (8)	−0.0024 (8)	0.0015 (8)
C19	0.0168 (11)	0.0195 (11)	0.0149 (10)	−0.0033 (8)	−0.0029 (8)	0.0010 (8)
C20	0.0157 (10)	0.0193 (11)	0.0150 (10)	−0.0011 (8)	−0.0035 (8)	0.0008 (8)
C21	0.0210 (12)	0.0240 (12)	0.0170 (10)	−0.0025 (9)	−0.0038 (8)	0.0015 (8)
C22	0.0262 (13)	0.0294 (13)	0.0187 (11)	0.0017 (10)	−0.0082 (9)	0.0006 (9)
C23	0.0242 (12)	0.0187 (11)	0.0135 (10)	−0.0026 (9)	−0.0045 (8)	0.0052 (8)
C24	0.0197 (11)	0.0177 (10)	0.0139 (10)	−0.0001 (9)	−0.0012 (8)	0.0007 (8)
C25	0.0191 (11)	0.0165 (10)	0.0131 (9)	−0.0026 (8)	−0.0025 (8)	0.0018 (7)
C26	0.0172 (11)	0.0182 (10)	0.0139 (10)	−0.0024 (8)	−0.0015 (8)	0.0008 (8)
C27	0.0175 (11)	0.0168 (10)	0.0141 (10)	−0.0009 (8)	−0.0014 (8)	0.0022 (7)
C28	0.0173 (11)	0.0175 (10)	0.0144 (10)	−0.0032 (8)	−0.0018 (8)	0.0004 (8)
C29	0.0172 (11)	0.0165 (10)	0.0141 (9)	−0.0022 (8)	−0.0014 (8)	0.0016 (7)
C30	0.0163 (11)	0.0176 (10)	0.0157 (10)	−0.0025 (8)	−0.0028 (8)	0.0003 (8)
C31	0.0169 (11)	0.0179 (10)	0.0131 (9)	−0.0023 (8)	−0.0017 (8)	0.0011 (7)
C32	0.0166 (10)	0.0164 (10)	0.0127 (9)	−0.0028 (8)	−0.0015 (7)	0.0018 (7)
C33	0.0164 (10)	0.0163 (10)	0.0144 (10)	−0.0031 (8)	−0.0015 (8)	0.0014 (7)
C34	0.0181 (11)	0.0174 (10)	0.0143 (10)	−0.0033 (8)	−0.0022 (8)	0.0009 (8)
C35	0.0202 (11)	0.0211 (11)	0.0168 (10)	−0.0034 (9)	−0.0030 (8)	0.0031 (8)
C36	0.0275 (13)	0.0274 (13)	0.0205 (11)	−0.0066 (10)	−0.0086 (9)	0.0042 (9)

Geometric parameters (Å, º)

O1—C2	1.410 (3)	C18—H18B	0.9900
O1—C8	1.430 (2)	C19—C20	1.528 (3)
O2—C2	1.414 (2)	C19—H19A	0.9900
O2—C23	1.442 (2)	C19—H19B	0.9900
O3—C2	1.400 (2)	C20—C21	1.519 (3)
O3—C4	1.430 (3)	C20—H20A	0.9900
N6—C6	1.503 (3)	C20—H20B	0.9900
N6—C5	1.516 (3)	C21—C22	1.528 (3)
N6—C7	1.523 (3)	C21—H21A	0.9900
N6—C9	1.527 (3)	C21—H21B	0.9900
C1—C2	1.515 (3)	C22—H22A	0.9800
C1—H1A	0.9800	C22—H22B	0.9800
C1—H1B	0.9800	C22—H22C	0.9800
C1—H1C	0.9800	C23—C24	1.510 (3)
C4—C5	1.512 (3)	C23—H23A	0.9900
C4—H4A	0.9900	C23—H23B	0.9900
C4—H4B	0.9900	C24—C25	1.527 (3)
C5—H5A	0.9900	C24—H24A	0.9900
C5—H5B	0.9900	C24—H24B	0.9900
C6—H6A	0.9800	C25—C26	1.529 (3)
C6—H6B	0.9800	C25—H25A	0.9900
C6—H60C	0.9800	C25—H25B	0.9900
C7—C8	1.518 (3)	C26—C27	1.524 (3)
C7—H7A	0.9900	C26—H26A	0.9900
C7—H7B	0.9900	C26—H26B	0.9900
C8—H8A	0.9900	C27—C28	1.527 (3)
C8—H8B	0.9900	C27—H27A	0.9900
C9—C10	1.531 (3)	C27—H27B	0.9900
C9—H9A	0.9900	C28—C29	1.524 (3)
C9—H9B	0.9900	C28—H28A	0.9900
C10—C11	1.525 (3)	C28—H28B	0.9900
C10—H10A	0.9900	C29—C30	1.523 (3)
C10—H10B	0.9900	C29—H29A	0.9900
C11—C12	1.525 (3)	C29—H29B	0.9900
C11—H11A	0.9900	C30—C31	1.526 (3)
C11—H11B	0.9900	C30—H30A	0.9900
C12—C13	1.524 (3)	C30—H30B	0.9900
C12—H12A	0.9900	C31—C32	1.527 (3)
C12—H12B	0.9900	C31—H31A	0.9900
C13—C14	1.532 (3)	C31—H31B	0.9900
C13—H13A	0.9900	C32—C33	1.521 (3)
C13—H13B	0.9900	C32—H32A	0.9900
C14—C15	1.519 (3)	C32—H32B	0.9900
C14—H14A	0.9900	C33—C34	1.526 (3)
C14—H14B	0.9900	C33—H33A	0.9900
C15—C16	1.526 (3)	C33—H33B	0.9900
C15—H15A	0.9900	C34—C35	1.521 (3)
C15—H15B	0.9900	C34—H34A	0.9900
C16—C17	1.528 (3)	C34—H34B	0.9900
C16—H16A	0.9900	C35—C36	1.528 (3)
C16—H16B	0.9900	C35—H35A	0.9900
C17—C18	1.525 (3)	C35—H35B	0.9900
C17—H17A	0.9900	C36—H36A	0.9800
C17—H17B	0.9900	C36—H36B	0.9800
C18—C19	1.523 (3)	C36—H36C	0.9800
C18—H18A	0.9900
C2—O1—C8	117.53 (16)	H18A—C18—H18B	107.8
C2—O2—C23	115.47 (17)	C18—C19—C20	113.99 (18)
C2—O3—C4	115.14 (17)	C18—C19—H19A	108.8
C6—N6—C5	109.37 (16)	C20—C19—H19A	108.8
C6—N6—C7	111.57 (16)	C18—C19—H19B	108.8
C5—N6—C7	113.70 (16)	C20—C19—H19B	108.8
C6—N6—C9	107.15 (15)	H19A—C19—H19B	107.6
C5—N6—C9	106.75 (15)	C21—C20—C19	113.58 (19)
C7—N6—C9	107.97 (15)	C21—C20—H20A	108.9
C2—C1—H1A	109.5	C19—C20—H20A	108.9
C2—C1—H1B	109.5	C21—C20—H20B	108.9
H1A—C1—H1B	109.5	C19—C20—H20B	108.9
C2—C1—H1C	109.5	H20A—C20—H20B	107.7
H1A—C1—H1C	109.5	C20—C21—C22	112.9 (2)
H1B—C1—H1C	109.5	C20—C21—H21A	109.0
O3—C2—O1	110.95 (16)	C22—C21—H21A	109.0
O3—C2—O2	106.48 (17)	C20—C21—H21B	109.0
O1—C2—O2	103.91 (16)	C22—C21—H21B	109.0
O3—C2—C1	106.79 (17)	H21A—C21—H21B	107.8
O1—C2—C1	114.69 (18)	C21—C22—H22A	109.5
O2—C2—C1	113.79 (17)	C21—C22—H22B	109.5
O3—C4—C5	110.41 (17)	H22A—C22—H22B	109.5
O3—C4—H4A	109.6	C21—C22—H22C	109.5
C5—C4—H4A	109.6	H22A—C22—H22C	109.5
O3—C4—H4B	109.6	H22B—C22—H22C	109.5
C5—C4—H4B	109.6	O2—C23—C24	109.66 (18)
H4A—C4—H4B	108.1	O2—C23—H23A	109.7
C4—C5—N6	117.22 (17)	C24—C23—H23A	109.7
C4—C5—H5A	108.0	O2—C23—H23B	109.7
N6—C5—H5A	108.0	C24—C23—H23B	109.7
C4—C5—H5B	108.0	H23A—C23—H23B	108.2
N6—C5—H5B	108.0	C23—C24—C25	111.11 (18)
H5A—C5—H5B	107.2	C23—C24—H24A	109.4
N6—C6—H6A	109.5	C25—C24—H24A	109.4
N6—C6—H6B	109.5	C23—C24—H24B	109.4
H6A—C6—H6B	109.5	C25—C24—H24B	109.4
N6—C6—H60C	109.5	H24A—C24—H24B	108.0
H6A—C6—H60C	109.5	C24—C25—C26	113.52 (18)
H6B—C6—H60C	109.5	C24—C25—H25A	108.9
C8—C7—N6	117.56 (17)	C26—C25—H25A	108.9
C8—C7—H7A	107.9	C24—C25—H25B	108.9
N6—C7—H7A	107.9	C26—C25—H25B	108.9
C8—C7—H7B	107.9	H25A—C25—H25B	107.7
N6—C7—H7B	107.9	C27—C26—C25	113.12 (18)
H7A—C7—H7B	107.2	C27—C26—H26A	109.0
O1—C8—C7	117.74 (17)	C25—C26—H26A	109.0
O1—C8—H8A	107.9	C27—C26—H26B	109.0
C7—C8—H8A	107.9	C25—C26—H26B	109.0
O1—C8—H8B	107.9	H26A—C26—H26B	107.8
C7—C8—H8B	107.9	C26—C27—C28	113.01 (18)
H8A—C8—H8B	107.2	C26—C27—H27A	109.0
N6—C9—C10	114.44 (16)	C28—C27—H27A	109.0
N6—C9—H9A	108.6	C26—C27—H27B	109.0
C10—C9—H9A	108.6	C28—C27—H27B	109.0
N6—C9—H9B	108.6	H27A—C27—H27B	107.8
C10—C9—H9B	108.6	C29—C28—C27	113.41 (18)
H9A—C9—H9B	107.6	C29—C28—H28A	108.9
C11—C10—C9	111.08 (17)	C27—C28—H28A	108.9
C11—C10—H10A	109.4	C29—C28—H28B	108.9
C9—C10—H10A	109.4	C27—C28—H28B	108.9
C11—C10—H10B	109.4	H28A—C28—H28B	107.7
C9—C10—H10B	109.4	C30—C29—C28	113.42 (18)
H10A—C10—H10B	108.0	C30—C29—H29A	108.9
C12—C11—C10	111.04 (18)	C28—C29—H29A	108.9
C12—C11—H11A	109.4	C30—C29—H29B	108.9
C10—C11—H11A	109.4	C28—C29—H29B	108.9
C12—C11—H11B	109.4	H29A—C29—H29B	107.7
C10—C11—H11B	109.4	C29—C30—C31	113.69 (18)
H11A—C11—H11B	108.0	C29—C30—H30A	108.8
C11—C12—C13	113.27 (18)	C31—C30—H30A	108.8
C11—C12—H12A	108.9	C29—C30—H30B	108.8
C13—C12—H12A	108.9	C31—C30—H30B	108.8
C11—C12—H12B	108.9	H30A—C30—H30B	107.7
C13—C12—H12B	108.9	C32—C31—C30	113.19 (18)
H12A—C12—H12B	107.7	C32—C31—H31A	108.9
C12—C13—C14	113.00 (18)	C30—C31—H31A	108.9
C12—C13—H13A	109.0	C32—C31—H31B	108.9
C14—C13—H13A	109.0	C30—C31—H31B	108.9
C12—C13—H13B	109.0	H31A—C31—H31B	107.8
C14—C13—H13B	109.0	C33—C32—C31	113.05 (18)
H13A—C13—H13B	107.8	C33—C32—H32A	109.0
C15—C14—C13	113.41 (18)	C31—C32—H32A	109.0
C15—C14—H14A	108.9	C33—C32—H32B	109.0
C13—C14—H14A	108.9	C31—C32—H32B	109.0
C15—C14—H14B	108.9	H32A—C32—H32B	107.8
C13—C14—H14B	108.9	C32—C33—C34	113.22 (18)
H14A—C14—H14B	107.7	C32—C33—H33A	108.9
C14—C15—C16	113.72 (18)	C34—C33—H33A	108.9
C14—C15—H15A	108.8	C32—C33—H33B	108.9
C16—C15—H15A	108.8	C34—C33—H33B	108.9
C14—C15—H15B	108.8	H33A—C33—H33B	107.7
C16—C15—H15B	108.8	C35—C34—C33	112.46 (18)
H15A—C15—H15B	107.7	C35—C34—H34A	109.1
C15—C16—C17	113.27 (18)	C33—C34—H34A	109.1
C15—C16—H16A	108.9	C35—C34—H34B	109.1
C17—C16—H16A	108.9	C33—C34—H34B	109.1
C15—C16—H16B	108.9	H34A—C34—H34B	107.8
C17—C16—H16B	108.9	C34—C35—C36	113.42 (19)
H16A—C16—H16B	107.7	C34—C35—H35A	108.9
C18—C17—C16	113.53 (18)	C36—C35—H35A	108.9
C18—C17—H17A	108.9	C34—C35—H35B	108.9
C16—C17—H17A	108.9	C36—C35—H35B	108.9
C18—C17—H17B	108.9	H35A—C35—H35B	107.7
C16—C17—H17B	108.9	C35—C36—H36A	109.5
H17A—C17—H17B	107.7	C35—C36—H36B	109.5
C19—C18—C17	113.12 (18)	H36A—C36—H36B	109.5
C19—C18—H18A	109.0	C35—C36—H36C	109.5
C17—C18—H18A	109.0	H36A—C36—H36C	109.5
C19—C18—H18B	109.0	H36B—C36—H36C	109.5
C17—C18—H18B	109.0
C4—O3—C2—O1	−45.0 (2)	C10—C11—C12—C13	176.86 (19)
C4—O3—C2—O2	67.4 (2)	C11—C12—C13—C14	177.49 (19)
C4—O3—C2—C1	−170.66 (16)	C12—C13—C14—C15	178.13 (19)
C8—O1—C2—O3	−69.8 (2)	C13—C14—C15—C16	178.42 (19)
C8—O1—C2—O2	176.12 (15)	C14—C15—C16—C17	179.33 (19)
C8—O1—C2—C1	51.3 (2)	C15—C16—C17—C18	179.98 (19)
C23—O2—C2—O3	175.84 (17)	C16—C17—C18—C19	179.79 (19)
C23—O2—C2—O1	−66.9 (2)	C17—C18—C19—C20	−179.97 (19)
C23—O2—C2—C1	58.5 (2)	C18—C19—C20—C21	−179.36 (19)
C2—O3—C4—C5	117.09 (19)	C19—C20—C21—C22	−178.8 (2)
O3—C4—C5—N6	−70.4 (2)	C2—O2—C23—C24	139.66 (19)
C6—N6—C5—C4	−70.3 (2)	O2—C23—C24—C25	169.56 (18)
C7—N6—C5—C4	55.2 (2)	C23—C24—C25—C26	176.03 (19)
C9—N6—C5—C4	174.11 (18)	C24—C25—C26—C27	176.25 (19)
C6—N6—C7—C8	34.3 (2)	C25—C26—C27—C28	178.52 (19)
C5—N6—C7—C8	−90.0 (2)	C26—C27—C28—C29	179.07 (19)
C9—N6—C7—C8	151.75 (18)	C27—C28—C29—C30	179.94 (19)
C2—O1—C8—C7	61.5 (2)	C28—C29—C30—C31	−179.96 (19)
N6—C7—C8—O1	52.5 (3)	C29—C30—C31—C32	−179.75 (18)
C6—N6—C9—C10	169.75 (17)	C30—C31—C32—C33	179.21 (18)
C5—N6—C9—C10	−73.2 (2)	C31—C32—C33—C34	−176.81 (19)
C7—N6—C9—C10	49.4 (2)	C32—C33—C34—C35	178.18 (19)
N6—C9—C10—C11	161.63 (17)	C33—C34—C35—C36	−178.0 (2)
C9—C10—C11—C12	176.03 (18)