Two triethylammonium ion complexes of monoanionic calix[4]arene

Two complexes between mono-deprotonated calix­[4]­arene and Et₃HN⁺ are reported. The first, triethylammonium 26,27,28-tri­hydroxy­penta­cyclo­[19.3.1.1^3,7.1^9,13.1^15,19]­octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaen-25-olate, C₆H₁₆N⁺·C₂₈H₂₃O₄⁻, comprises only the cationic and anionic species, whereas the second, tris­(triethyl­ammonium) tris[26,27,28-tri­hydroxy­penta­cyclo­[19.3.1.1^3,7.1^9,13.1^15,19]­octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaen-25-olate] aceto­nitrile solvate, 3C₆H₁₆N⁺·3C₂₈H₂₃O₄⁻·C₂H₃N, comprises one aceto­nitrile solvent mol­ecule for three such units. In both cases, the units are stacked in columns so that the ammonium cation is hydrogen bonded to a phenolic or phenolate O atom of one mol­ecule and included in the hydro­phobic cavity of another neighbouring calixarene. The short contacts present indicate that cation...π and C—H...π interactions are likely to be involved in the inclusion phenomena.

Computing details

For both compounds, data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL and PARST97 (Nardelli, 1995).

(I) triethylammonium 26,27,28-trihydroxypentacyclo[19.3.1.1^3,7.1^9,13.1^15,19]octacosa- 1(25),3,5,7(28),9,11,13 (27),15,17,19 (26),21,23-dodecaen-25-olate

Crystal data

C6H16N^+·C28H23O4^−	F(000) = 1128
Mr = 525.66	Dx = 1.266 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 15424 reflections
a = 18.3531 (18) Å	θ = 2.7–25.7°
b = 10.8710 (12) Å	µ = 0.08 mm^−1
c = 13.8210 (12) Å	T = 100 K
V = 2757.5 (5) Å^3	Platelet, colourless
Z = 4	0.25 × 0.25 × 0.10 mm

Data collection

Nonius KappaCCD area-detector diffractometer	1909 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.089
Graphite monochromator	θmax = 25.7°, θmin = 2.7°
Detector resolution: 18 pixels mm^-1	h = 0→22
φ scans	k = 0→13
15424 measured reflections	l = 0→16
2702 independent 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.047P)^2] where P = (Fo^2 + 2Fc^2)/3
2702 reflections	(Δ/σ)max < 0.001
353 parameters	Δρmax = 0.23 e Å^−3
1 restraint	Δρmin = −0.25 e Å^−3

Special details

Experimental. A 180° range in φ was scanned during both data collections, with 2° φ steps. The crystal-to-detector distance was fixed at 28 mm.

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. Structure solved by direct methods and expanded by subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. Ammonium and phenolic H atoms have been found on the Fourier-difference map and introduced as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. The O—H bond lengths, being somewhat larger than usual, have been reset to 0.82 Å. All other hydrogen atoms were introduced at calculated positions as riding atoms with an isotropic displacement parameter equal to 1.2 (CH, CH2) or 1.5 (CH3) times that of the parent atom. 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
O1	0.22569 (18)	0.7184 (3)	0.3797 (3)	0.0297 (9)
H1	0.2470	0.7826	0.3648	0.036*
O2	0.26739 (18)	0.9379 (3)	0.3475 (3)	0.0269 (8)
H2	0.2323	0.9821	0.3604	0.032*
O3	0.15176 (19)	1.0451 (3)	0.3858 (3)	0.0319 (9)
O4	0.08297 (18)	0.8361 (3)	0.4355 (3)	0.0301 (9)
H4	0.1023	0.9013	0.4201	0.036*
C1	0.2195 (3)	0.6348 (4)	0.5403 (4)	0.0240 (11)
C2	0.2608 (3)	0.6838 (5)	0.4641 (4)	0.0242 (11)
C3	0.3365 (3)	0.6978 (4)	0.4707 (4)	0.0255 (11)
C4	0.3714 (3)	0.6578 (5)	0.5545 (4)	0.0278 (12)
H4A	0.4216	0.6665	0.5604	0.033*
C5	0.3316 (3)	0.6050 (4)	0.6293 (4)	0.0279 (11)
H5A	0.3553	0.5764	0.6844	0.033*
C6	0.2571 (2)	0.5951 (4)	0.6217 (4)	0.0255 (11)
H6A	0.2311	0.5607	0.6727	0.031*
C7	0.3794 (3)	0.7612 (5)	0.3921 (4)	0.0271 (12)
H7A	0.3553	0.7479	0.3305	0.032*
H7B	0.4275	0.7247	0.3883	0.032*
C8	0.3871 (3)	0.8990 (5)	0.4092 (3)	0.0258 (12)
C9	0.3297 (3)	0.9800 (5)	0.3869 (4)	0.0254 (11)
C10	0.3387 (3)	1.1081 (5)	0.4060 (4)	0.0268 (11)
C11	0.4039 (3)	1.1493 (5)	0.4472 (4)	0.0276 (12)
H11A	0.4102	1.2329	0.4589	0.033*
C12	0.4593 (3)	1.0688 (5)	0.4707 (4)	0.0322 (13)
H12A	0.5021	1.0975	0.4990	0.039*
C13	0.4504 (3)	0.9443 (5)	0.4516 (4)	0.0317 (13)
H13A	0.4876	0.8899	0.4675	0.038*
C14	0.2789 (3)	1.1987 (5)	0.3819 (4)	0.0293 (12)
H14A	0.2568	1.1744	0.3211	0.035*
H14B	0.3007	1.2791	0.3724	0.035*
C15	0.2196 (3)	1.2099 (4)	0.4573 (4)	0.0273 (12)
C16	0.1573 (3)	1.1349 (4)	0.4558 (4)	0.0269 (11)
C17	0.1019 (3)	1.1469 (5)	0.5242 (4)	0.0243 (11)
C18	0.1114 (3)	1.2341 (5)	0.5982 (4)	0.0291 (12)
H18A	0.0754	1.2429	0.6451	0.035*
C19	0.1728 (3)	1.3072 (5)	0.6031 (4)	0.0330 (13)
H19A	0.1786	1.3629	0.6535	0.040*
C20	0.2261 (3)	1.2969 (5)	0.5320 (4)	0.0302 (12)
H20A	0.2666	1.3482	0.5340	0.036*
C21	0.0363 (3)	1.0626 (5)	0.5250 (4)	0.0280 (12)
H21A	−0.0048	1.1044	0.5545	0.034*
H21B	0.0231	1.0413	0.4592	0.034*
C22	0.0535 (3)	0.9475 (5)	0.5811 (4)	0.0264 (12)
C23	0.0798 (3)	0.8417 (5)	0.5344 (3)	0.0255 (12)
C24	0.1014 (3)	0.7368 (5)	0.5867 (4)	0.0262 (12)
C25	0.0917 (3)	0.7361 (5)	0.6863 (4)	0.0301 (13)
H25A	0.1037	0.6663	0.7216	0.036*
C26	0.0640 (3)	0.8392 (5)	0.7337 (4)	0.0336 (13)
H26A	0.0578	0.8377	0.8005	0.040*
C27	0.0456 (3)	0.9439 (5)	0.6818 (4)	0.0301 (13)
H27A	0.0279	1.0126	0.7143	0.036*
C28	0.1367 (3)	0.6287 (5)	0.5357 (4)	0.0275 (12)
H28A	0.1214	0.6278	0.4685	0.033*
H28B	0.1203	0.5529	0.5655	0.033*
N	0.1534 (2)	0.5612 (4)	0.2522 (3)	0.0303 (10)
H5	0.1859	0.6081	0.2822	0.036*
C29	0.1884 (3)	0.5361 (5)	0.1561 (4)	0.0368 (14)
H29A	0.1526	0.4985	0.1138	0.044*
H29B	0.2026	0.6139	0.1273	0.044*
C30	0.2537 (3)	0.4547 (6)	0.1605 (6)	0.0552 (18)
H30A	0.2730	0.4435	0.0965	0.083*
H30B	0.2401	0.3763	0.1869	0.083*
H30C	0.2901	0.4918	0.2009	0.083*
C31	0.0874 (3)	0.6412 (5)	0.2431 (4)	0.0355 (14)
H31A	0.0637	0.6472	0.3056	0.043*
H31B	0.0533	0.6030	0.1985	0.043*
C32	0.1053 (3)	0.7695 (5)	0.2072 (4)	0.0411 (15)
H32A	0.0612	0.8165	0.2016	0.062*
H32B	0.1285	0.7642	0.1451	0.062*
H32C	0.1375	0.8091	0.2523	0.062*
C33	0.1374 (3)	0.4448 (5)	0.3092 (4)	0.0370 (14)
H33A	0.1825	0.3996	0.3178	0.044*
H33B	0.1198	0.4677	0.3729	0.044*
C34	0.0823 (3)	0.3612 (6)	0.2627 (5)	0.0489 (17)
H34A	0.0750	0.2901	0.3028	0.073*
H34B	0.0998	0.3358	0.2003	0.073*
H34C	0.0370	0.4042	0.2553	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0279 (19)	0.033 (2)	0.0286 (19)	−0.0060 (16)	−0.0058 (17)	0.0042 (16)
O2	0.0235 (19)	0.029 (2)	0.0283 (18)	0.0032 (15)	−0.0035 (16)	−0.0024 (16)
O3	0.036 (2)	0.031 (2)	0.0281 (19)	−0.0019 (17)	−0.0012 (17)	−0.0061 (17)
O4	0.033 (2)	0.029 (2)	0.028 (2)	−0.0014 (17)	0.0006 (16)	0.0003 (16)
C1	0.025 (3)	0.019 (2)	0.028 (3)	0.003 (2)	−0.002 (2)	−0.003 (2)
C2	0.026 (3)	0.023 (3)	0.023 (3)	0.004 (2)	−0.004 (2)	−0.003 (2)
C3	0.024 (3)	0.027 (3)	0.026 (3)	−0.004 (2)	0.001 (2)	−0.002 (2)
C4	0.023 (3)	0.032 (3)	0.029 (3)	0.004 (2)	−0.001 (2)	0.001 (2)
C5	0.026 (3)	0.025 (3)	0.033 (3)	0.001 (2)	−0.008 (2)	0.002 (2)
C6	0.024 (3)	0.025 (3)	0.028 (3)	−0.002 (2)	0.000 (2)	−0.005 (2)
C7	0.022 (3)	0.034 (3)	0.025 (3)	0.009 (2)	0.002 (2)	−0.001 (2)
C8	0.024 (3)	0.034 (3)	0.019 (3)	0.006 (2)	0.005 (2)	0.003 (2)
C9	0.027 (3)	0.028 (3)	0.022 (2)	−0.005 (2)	0.000 (2)	0.001 (2)
C10	0.029 (3)	0.027 (3)	0.024 (3)	0.002 (2)	0.004 (2)	0.002 (2)
C11	0.027 (3)	0.030 (3)	0.026 (3)	−0.003 (2)	0.001 (2)	−0.001 (2)
C12	0.025 (3)	0.040 (3)	0.032 (3)	−0.005 (2)	−0.001 (2)	−0.002 (3)
C13	0.022 (3)	0.040 (3)	0.033 (3)	−0.001 (2)	−0.003 (2)	0.002 (3)
C14	0.031 (3)	0.032 (3)	0.025 (3)	−0.003 (2)	0.002 (2)	0.002 (2)
C15	0.034 (3)	0.023 (3)	0.025 (3)	0.003 (2)	0.004 (2)	0.003 (2)
C16	0.036 (3)	0.020 (3)	0.025 (3)	0.001 (2)	−0.004 (2)	−0.003 (2)
C17	0.023 (3)	0.022 (3)	0.028 (3)	0.006 (2)	−0.004 (2)	0.001 (2)
C18	0.028 (3)	0.029 (3)	0.030 (3)	0.006 (2)	0.004 (2)	0.003 (2)
C19	0.045 (3)	0.027 (3)	0.027 (3)	0.002 (3)	0.000 (3)	−0.004 (2)
C20	0.034 (3)	0.020 (3)	0.037 (3)	0.001 (2)	−0.001 (3)	0.001 (2)
C21	0.029 (3)	0.029 (3)	0.025 (3)	0.005 (2)	0.001 (2)	0.000 (2)
C22	0.018 (2)	0.032 (3)	0.029 (3)	−0.003 (2)	0.003 (2)	0.001 (2)
C23	0.027 (3)	0.029 (3)	0.020 (3)	−0.002 (2)	0.000 (2)	0.003 (2)
C24	0.017 (3)	0.030 (3)	0.031 (3)	−0.001 (2)	0.001 (2)	−0.001 (2)
C25	0.025 (3)	0.030 (3)	0.035 (3)	−0.002 (2)	−0.001 (2)	0.006 (3)
C26	0.031 (3)	0.036 (3)	0.034 (3)	0.002 (3)	0.001 (3)	0.005 (3)
C27	0.022 (3)	0.036 (3)	0.032 (3)	0.001 (2)	0.005 (2)	−0.004 (3)
C28	0.020 (3)	0.030 (3)	0.033 (3)	0.000 (2)	−0.002 (2)	−0.001 (2)
N	0.028 (2)	0.033 (3)	0.030 (2)	0.003 (2)	−0.004 (2)	0.003 (2)
C29	0.033 (3)	0.038 (3)	0.039 (3)	0.004 (3)	0.008 (3)	0.005 (3)
C30	0.042 (4)	0.042 (4)	0.082 (5)	0.013 (3)	0.018 (3)	0.013 (4)
C31	0.031 (3)	0.044 (4)	0.031 (3)	0.011 (3)	−0.005 (3)	−0.007 (3)
C32	0.051 (4)	0.039 (4)	0.033 (3)	0.015 (3)	−0.011 (3)	0.001 (3)
C33	0.040 (3)	0.037 (3)	0.034 (3)	−0.007 (3)	0.007 (3)	−0.003 (3)
C34	0.051 (4)	0.039 (4)	0.057 (4)	−0.011 (3)	0.011 (3)	−0.004 (3)

Geometric parameters (Å, º)

O1—C2	1.386 (6)	C18—C19	1.381 (7)
O1—O2	2.544 (5)	C18—H18A	0.9300
O1—N	2.790 (6)	C19—C20	1.390 (7)
O1—H1	0.8251	C19—H19A	0.9300
O2—C9	1.346 (6)	C20—H20A	0.9300
O2—O3	2.478 (5)	C21—C22	1.505 (7)
O2—H2	0.8234	C21—H21A	0.9700
O3—C16	1.378 (6)	C21—H21B	0.9700
O3—O4	2.689 (5)	C22—C27	1.400 (7)
O4—C23	1.370 (7)	C22—C23	1.404 (7)
O4—H4	0.8213	C23—C24	1.407 (7)
C1—C6	1.389 (7)	C24—C25	1.388 (7)
C1—C2	1.403 (7)	C24—C28	1.515 (7)
C1—C28	1.522 (7)	C25—C26	1.394 (7)
C2—C3	1.400 (6)	C25—H25A	0.9300
C3—C4	1.393 (7)	C26—C27	1.388 (7)
C3—C7	1.508 (7)	C26—H26A	0.9300
C4—C5	1.390 (7)	C27—H27A	0.9300
C4—H4A	0.9300	C28—H28A	0.9700
C5—C6	1.375 (6)	C28—H28B	0.9700
C5—H5A	0.9300	N—C31	1.497 (6)
C6—H6A	0.9300	N—C29	1.501 (7)
C7—C8	1.522 (7)	N—C33	1.520 (7)
C7—H7A	0.9700	N—H5	0.8872
C7—H7B	0.9700	C29—C30	1.491 (7)
C8—C13	1.391 (7)	C29—H29A	0.9700
C8—C9	1.408 (7)	C29—H29B	0.9700
C9—C10	1.427 (7)	C30—H30A	0.9600
C10—C11	1.400 (7)	C30—H30B	0.9600
C10—C14	1.511 (7)	C30—H30C	0.9600
C11—C12	1.380 (7)	C31—C32	1.516 (8)
C11—H11A	0.9300	C31—H31A	0.9700
C12—C13	1.388 (7)	C31—H31B	0.9700
C12—H12A	0.9300	C32—H32A	0.9600
C13—H13A	0.9300	C32—H32B	0.9600
C14—C15	1.512 (7)	C32—H32C	0.9600
C14—H14A	0.9700	C33—C34	1.504 (8)
C14—H14B	0.9700	C33—H33A	0.9700
C15—C20	1.405 (7)	C33—H33B	0.9700
C15—C16	1.405 (7)	C34—H34A	0.9600
C16—C17	1.394 (7)	C34—H34B	0.9600
C17—C18	1.405 (7)	C34—H34C	0.9600
C17—C21	1.513 (7)
C2—O1—H1	102.7	C17—C21—H21A	109.7
C9—O2—H2	112.2	C22—C21—H21B	109.7
C23—O4—H4	103.7	C17—C21—H21B	109.7
C6—C1—C2	117.2 (4)	H21A—C21—H21B	108.2
C6—C1—C28	121.1 (5)	C27—C22—C23	118.0 (5)
C2—C1—C28	121.7 (4)	C27—C22—C21	120.9 (5)
O1—C2—C3	119.2 (4)	C23—C22—C21	121.1 (4)
O1—C2—C1	118.9 (4)	O4—C23—C22	120.7 (4)
C3—C2—C1	121.9 (5)	O4—C23—C24	117.7 (5)
C4—C3—C2	118.5 (5)	C22—C23—C24	121.6 (4)
C4—C3—C7	120.1 (4)	C25—C24—C23	118.5 (5)
C2—C3—C7	121.3 (5)	C25—C24—C28	120.8 (5)
C3—C4—C5	120.4 (5)	C23—C24—C28	120.7 (4)
C3—C4—H4A	119.8	C24—C25—C26	120.6 (5)
C5—C4—H4A	119.8	C24—C25—H25A	119.7
C6—C5—C4	119.8 (5)	C26—C25—H25A	119.7
C6—C5—H5A	120.1	C27—C26—C25	120.3 (5)
C4—C5—H5A	120.1	C27—C26—H26A	119.8
C5—C6—C1	122.1 (5)	C25—C26—H26A	119.8
C5—C6—H6A	118.9	C26—C27—C22	120.8 (5)
C1—C6—H6A	118.9	C26—C27—H27A	119.6
C3—C7—C8	112.8 (4)	C22—C27—H27A	119.6
C3—C7—H7A	109.0	C24—C28—C1	112.0 (4)
C8—C7—H7A	109.0	C24—C28—H28A	109.2
C3—C7—H7B	109.0	C1—C28—H28A	109.2
C8—C7—H7B	109.0	C24—C28—H28B	109.2
H7A—C7—H7B	107.8	C1—C28—H28B	109.2
C13—C8—C9	119.7 (5)	H28A—C28—H28B	107.9
C13—C8—C7	119.5 (5)	C31—N—C29	112.2 (4)
C9—C8—C7	120.7 (4)	C31—N—C33	111.8 (4)
O2—C9—C8	120.8 (4)	C29—N—C33	113.0 (4)
O2—C9—C10	120.3 (4)	C31—N—H5	104.5
C8—C9—C10	118.9 (5)	C29—N—H5	103.3
C11—C10—C9	119.1 (5)	C33—N—H5	111.5
C11—C10—C14	120.2 (5)	C30—C29—N	114.6 (5)
C9—C10—C14	120.7 (5)	C30—C29—H29A	108.6
C12—C11—C10	121.6 (5)	N—C29—H29A	108.6
C12—C11—H11A	119.2	C30—C29—H29B	108.6
C10—C11—H11A	119.2	N—C29—H29B	108.6
C11—C12—C13	119.1 (5)	H29A—C29—H29B	107.6
C11—C12—H12A	120.5	C29—C30—H30A	109.5
C13—C12—H12A	120.5	C29—C30—H30B	109.5
C12—C13—C8	121.6 (5)	H30A—C30—H30B	109.5
C12—C13—H13A	119.2	C29—C30—H30C	109.5
C8—C13—H13A	119.2	H30A—C30—H30C	109.5
C10—C14—C15	115.0 (4)	H30B—C30—H30C	109.5
C10—C14—H14A	108.5	N—C31—C32	112.7 (5)
C15—C14—H14A	108.5	N—C31—H31A	109.0
C10—C14—H14B	108.5	C32—C31—H31A	109.0
C15—C14—H14B	108.5	N—C31—H31B	109.0
H14A—C14—H14B	107.5	C32—C31—H31B	109.0
C20—C15—C16	118.1 (5)	H31A—C31—H31B	107.8
C20—C15—C14	120.0 (5)	C31—C32—H32A	109.5
C16—C15—C14	122.0 (4)	C31—C32—H32B	109.5
O3—C16—C17	119.3 (4)	H32A—C32—H32B	109.5
O3—C16—C15	118.8 (4)	C31—C32—H32C	109.5
C17—C16—C15	122.0 (4)	H32A—C32—H32C	109.5
C16—C17—C18	117.8 (5)	H32B—C32—H32C	109.5
C16—C17—C21	121.9 (4)	C34—C33—N	114.3 (5)
C18—C17—C21	120.1 (4)	C34—C33—H33A	108.7
C19—C18—C17	121.6 (5)	N—C33—H33A	108.7
C19—C18—H18A	119.2	C34—C33—H33B	108.7
C17—C18—H18A	119.2	N—C33—H33B	108.7
C18—C19—C20	119.6 (5)	H33A—C33—H33B	107.6
C18—C19—H19A	120.2	C33—C34—H34A	109.5
C20—C19—H19A	120.2	C33—C34—H34B	109.5
C19—C20—C15	120.9 (5)	H34A—C34—H34B	109.5
C19—C20—H20A	119.6	C33—C34—H34C	109.5
C15—C20—H20A	119.6	H34A—C34—H34C	109.5
C22—C21—C17	109.9 (4)	H34B—C34—H34C	109.5
C22—C21—H21A	109.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N—H5···O1	0.89	1.95	2.790 (6)	158
O1—H1···O2	0.83	1.75	2.544 (5)	162
O2—H2···O3	0.82	1.67	2.478 (5)	169
O4—H4···O3	0.82	1.87	2.689 (5)	177

(II) tris(triethylammonium) tris{26,27,28-trihydroxypentacyclo[19.3.1.1^3,7.1^9,13.1^15,19]octacosa- 1(25),3,5,7(28),9,11,13 (27),15,17,19 (26),21,23-dodecaen-25-olate} acetonitrile solvate

Crystal data

3C6H16N^+·3C28H23O4^−·C2H3N	F(000) = 3472
Mr = 1618.04	Dx = 1.228 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 15261 reflections
a = 20.1364 (14) Å	θ = 2.6–25.7°
b = 30.9080 (14) Å	µ = 0.08 mm^−1
c = 16.0088 (10) Å	T = 100 K
β = 118.587 (3)°	Parallelepipedic, colourless
V = 8748.9 (9) Å^3	0.6 × 0.3 × 0.2 mm
Z = 4

Data collection

Nonius KappaCCD area-detector diffractometer	5760 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.066
Graphite monochromator	θmax = 25.7°, θmin = 2.6°
Detector resolution: 18 pixels mm^-1	h = −21→24
φ scans	k = −37→37
15261 measured reflections	l = −18→0
8240 independent 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0624P)^2 + 4.066P] where P = (Fo^2 + 2Fc^2)/3
8240 reflections	(Δ/σ)max = 0.001
1082 parameters	Δρmax = 0.52 e Å^−3
32 restraints	Δρmin = −0.28 e Å^−3

Special details

Experimental. A 180° range in φ was scanned during both data collections, with 2° φ steps. The crystal-to-detector distance was fixed at 28 mm.

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. Structure solved by direct methods and expanded by subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. Some constraints have been applied to the displacement parameters of the acetonitrile solvent molecule. The H atoms bound to N and O atoms were found on the Fourier-difference map and introduced as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. All other hydrogen atoms were introduced at calculated positions as riding atoms, with an isotropic displacement parameter equal to 1.2 (CH, CH2) or 1.5 (CH3) times that of the parent atom. 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
O1A	0.3258 (2)	−0.09436 (13)	0.4135 (2)	0.0375 (10)
H1A	0.3441	−0.0745	0.3974	0.045*
O2A	0.3594 (2)	−0.02650 (12)	0.3510 (2)	0.0290 (8)
O3A	0.2218 (2)	−0.00448 (12)	0.2907 (3)	0.0313 (9)
H3A	0.2739	−0.0042	0.3149	0.038*
O4A	0.1651 (2)	−0.08192 (12)	0.3296 (2)	0.0310 (9)
H4A	0.1912	−0.0654	0.3097	0.037*
C1A	0.3678 (3)	−0.09980 (17)	0.5095 (4)	0.0301 (12)
C2A	0.3324 (3)	−0.11892 (17)	0.5573 (4)	0.0316 (13)
C3A	0.3735 (3)	−0.1259 (2)	0.6541 (4)	0.0400 (15)
H3D	0.3501	−0.1387	0.6858	0.048*
C4A	0.4488 (3)	−0.1141 (2)	0.7048 (4)	0.0470 (17)
H4D	0.4758	−0.1191	0.7700	0.056*
C5A	0.4837 (3)	−0.0949 (2)	0.6574 (4)	0.0452 (16)
H5D	0.5342	−0.0866	0.6916	0.054*
C6A	0.4439 (3)	−0.0878 (2)	0.5586 (4)	0.0356 (14)
C7A	0.4836 (3)	−0.06739 (19)	0.5077 (4)	0.0355 (14)
H7D	0.5370	−0.0743	0.5429	0.043*
H7E	0.4638	−0.0804	0.4452	0.043*
C8A	0.4749 (3)	−0.0188 (2)	0.4965 (4)	0.0346 (14)
C9A	0.4110 (3)	−0.00039 (19)	0.4185 (4)	0.0285 (12)
C10A	0.4022 (3)	0.04474 (19)	0.4118 (4)	0.0298 (12)
C11A	0.4576 (3)	0.0706 (2)	0.4804 (4)	0.0354 (14)
H11D	0.4518	0.1005	0.4760	0.042*
C12A	0.5216 (3)	0.0528 (2)	0.5556 (4)	0.0407 (15)
H12D	0.5586	0.0707	0.6006	0.049*
C13A	0.5298 (3)	0.0090 (2)	0.5633 (4)	0.0392 (15)
H13D	0.5728	−0.0028	0.6138	0.047*
C14A	0.3324 (3)	0.06474 (19)	0.3295 (3)	0.0294 (12)
H14D	0.3187	0.0475	0.2730	0.035*
H14E	0.3455	0.0934	0.3175	0.035*
C15A	0.2632 (3)	0.06862 (17)	0.3442 (3)	0.0284 (12)
C16A	0.2120 (3)	0.03482 (17)	0.3242 (3)	0.0264 (11)
C17A	0.1465 (3)	0.03909 (17)	0.3339 (4)	0.0276 (12)
C18A	0.1353 (3)	0.07844 (17)	0.3669 (4)	0.0309 (12)
H18D	0.0926	0.0820	0.3745	0.037*
C19A	0.1855 (3)	0.11266 (18)	0.3890 (4)	0.0338 (13)
H19D	0.1770	0.1386	0.4116	0.041*
C20A	0.2482 (3)	0.10739 (17)	0.3769 (4)	0.0299 (12)
H20D	0.2817	0.1304	0.3909	0.036*
C21A	0.0948 (3)	0.00096 (18)	0.3175 (4)	0.0318 (12)
H21D	0.0450	0.0112	0.3033	0.038*
H21E	0.0899	−0.0156	0.2634	0.038*
C22A	0.1260 (3)	−0.02765 (17)	0.4044 (4)	0.0266 (12)
C23A	0.1643 (3)	−0.06620 (18)	0.4098 (4)	0.0282 (12)
C24A	0.2001 (3)	−0.09031 (17)	0.4944 (4)	0.0284 (12)
C25A	0.1927 (3)	−0.07573 (19)	0.5725 (4)	0.0341 (13)
H25D	0.2162	−0.0910	0.6294	0.041*
C26A	0.1517 (3)	−0.0397 (2)	0.5669 (4)	0.0373 (14)
H26D	0.1454	−0.0314	0.6185	0.045*
C27A	0.1196 (3)	−0.01539 (19)	0.4842 (4)	0.0352 (13)
H27D	0.0932	0.0097	0.4818	0.042*
C28A	0.2484 (3)	−0.12934 (19)	0.5036 (4)	0.0354 (13)
H28D	0.2357	−0.1399	0.4406	0.042*
H28E	0.2374	−0.1522	0.5367	0.042*
O1B	0.3893 (2)	0.26491 (12)	0.2371 (2)	0.0314 (9)
H1B	0.3681	0.2875	0.2126	0.038*
O2B	0.3178 (2)	0.33412 (11)	0.1614 (2)	0.0261 (8)
O3B	0.1983 (2)	0.30118 (12)	0.1573 (3)	0.0337 (9)
H3B	0.2394	0.3127	0.1497	0.040*
O4B	0.2753 (2)	0.21439 (12)	0.2247 (2)	0.0333 (9)
H4B	0.3110	0.2316	0.2209	0.040*
C1B	0.4569 (3)	0.26997 (17)	0.3171 (3)	0.0256 (11)
C2B	0.4801 (3)	0.23716 (16)	0.3850 (3)	0.0248 (11)
C3B	0.5490 (3)	0.24122 (18)	0.4677 (4)	0.0291 (12)
H3F	0.5642	0.2196	0.5137	0.035*
C4B	0.5959 (3)	0.27708 (18)	0.4831 (4)	0.0307 (13)
H4F	0.6420	0.2795	0.5384	0.037*
C5B	0.5715 (3)	0.30907 (18)	0.4131 (4)	0.0288 (12)
H5F	0.6022	0.3330	0.4225	0.035*
C6B	0.5026 (3)	0.30636 (16)	0.3296 (3)	0.0236 (11)
C7B	0.4781 (3)	0.34220 (17)	0.2552 (4)	0.0257 (11)
H7F	0.5229	0.3565	0.2608	0.031*
H7G	0.4520	0.3292	0.1925	0.031*
C8B	0.4273 (3)	0.37566 (17)	0.2634 (3)	0.0272 (12)
C9B	0.3475 (3)	0.36959 (17)	0.2157 (3)	0.0232 (11)
C10B	0.3010 (3)	0.40104 (17)	0.2263 (4)	0.0282 (12)
C11B	0.3347 (3)	0.43743 (18)	0.2825 (4)	0.0295 (12)
H11F	0.3042	0.4580	0.2897	0.035*
C12B	0.4112 (3)	0.44365 (17)	0.3272 (4)	0.0311 (13)
H12F	0.4320	0.4684	0.3633	0.037*
C13B	0.4579 (3)	0.41269 (17)	0.3184 (4)	0.0298 (12)
H13F	0.5100	0.4168	0.3495	0.036*
C14B	0.2160 (3)	0.39480 (18)	0.1801 (4)	0.0322 (13)
H14F	0.1987	0.3824	0.1174	0.039*
H14G	0.1924	0.4230	0.1717	0.039*
C15B	0.1887 (3)	0.36599 (19)	0.2350 (4)	0.0338 (13)
C16B	0.1824 (3)	0.32093 (18)	0.2221 (4)	0.0298 (12)
C17B	0.1588 (3)	0.29461 (19)	0.2748 (4)	0.0334 (13)
C18B	0.1406 (3)	0.3144 (2)	0.3388 (4)	0.0375 (14)
H18F	0.1245	0.2975	0.3736	0.045*
C19B	0.1458 (4)	0.3587 (2)	0.3522 (5)	0.0427 (15)
H19F	0.1324	0.3712	0.3948	0.051*
C20B	0.1711 (3)	0.3847 (2)	0.3016 (4)	0.0411 (15)
H20F	0.1762	0.4144	0.3122	0.049*
C21B	0.1597 (3)	0.24547 (18)	0.2671 (4)	0.0317 (13)
H21F	0.1194	0.2332	0.2766	0.038*
H21G	0.1506	0.2375	0.2040	0.038*
C22B	0.2352 (3)	0.22722 (17)	0.3409 (4)	0.0295 (12)
C23B	0.2920 (3)	0.21610 (16)	0.3197 (3)	0.0258 (12)
C24B	0.3651 (3)	0.20592 (17)	0.3911 (4)	0.0278 (12)
C25B	0.3773 (4)	0.20453 (18)	0.4841 (4)	0.0342 (13)
H25F	0.4256	0.1984	0.5330	0.041*
C26B	0.3197 (4)	0.21199 (18)	0.5060 (4)	0.0349 (13)
H26F	0.3280	0.2091	0.5681	0.042*
C27B	0.2502 (3)	0.22367 (17)	0.4343 (4)	0.0315 (13)
H27F	0.2116	0.2294	0.4490	0.038*
C28B	0.4306 (3)	0.19773 (18)	0.3708 (4)	0.0307 (12)
H28F	0.4618	0.1747	0.4121	0.037*
H28G	0.4104	0.1878	0.3056	0.037*
O1C	0.4981 (2)	0.35958 (12)	−0.1380 (2)	0.0294 (8)
H1C	0.4624	0.3606	−0.1917	0.035*
O2C	0.3867 (2)	0.35283 (12)	−0.3027 (2)	0.0276 (8)
O3C	0.4118 (2)	0.26924 (13)	−0.2783 (3)	0.0356 (9)
H3C	0.4106	0.2968	−0.2708	0.043*
O4C	0.5546 (2)	0.27903 (13)	−0.1001 (3)	0.0366 (9)
H4C	0.5441	0.3064	−0.1133	0.044*
C1C	0.5342 (3)	0.37637 (18)	0.0223 (4)	0.0303 (12)
C2C	0.4902 (3)	0.38592 (18)	−0.0741 (4)	0.0277 (12)
C3C	0.4425 (3)	0.42177 (17)	−0.1048 (3)	0.0278 (12)
C4C	0.4362 (4)	0.44719 (19)	−0.0376 (4)	0.0371 (14)
H4H	0.4034	0.4707	−0.0573	0.045*
C5C	0.4786 (4)	0.43779 (19)	0.0596 (4)	0.0379 (14)
H5H	0.4736	0.4548	0.1042	0.045*
C6C	0.5278 (3)	0.40314 (19)	0.0888 (4)	0.0344 (13)
H6H	0.5571	0.3975	0.1534	0.041*
C7C	0.3974 (4)	0.43328 (19)	−0.2098 (4)	0.0365 (14)
H7H	0.3861	0.4640	−0.2154	0.044*
H7I	0.4286	0.4278	−0.2398	0.044*
C8C	0.3244 (3)	0.40857 (19)	−0.2627 (3)	0.0321 (13)
C9C	0.3226 (3)	0.36770 (18)	−0.3052 (3)	0.0274 (12)
C10C	0.2562 (3)	0.3434 (2)	−0.3472 (4)	0.0327 (13)
C11C	0.1914 (3)	0.3603 (2)	−0.3496 (4)	0.0382 (14)
H11H	0.1466	0.3445	−0.3784	0.046*
C12C	0.1921 (4)	0.4006 (2)	−0.3095 (4)	0.0451 (17)
H12H	0.1482	0.4116	−0.3121	0.054*
C13C	0.2583 (4)	0.4237 (2)	−0.2662 (4)	0.0400 (15)
H13H	0.2588	0.4502	−0.2385	0.048*
C14C	0.2555 (3)	0.2987 (2)	−0.3865 (4)	0.0367 (14)
H14H	0.2044	0.2924	−0.4357	0.044*
H14I	0.2876	0.2991	−0.4162	0.044*
C15C	0.2814 (3)	0.26248 (18)	−0.3144 (3)	0.0304 (12)
C16C	0.3578 (3)	0.24982 (18)	−0.2636 (4)	0.0309 (13)
C17C	0.3809 (3)	0.21496 (18)	−0.1987 (4)	0.0333 (13)
C18C	0.3238 (4)	0.1929 (2)	−0.1880 (4)	0.0439 (16)
H18H	0.3370	0.1689	−0.1480	0.053*
C19C	0.2496 (4)	0.2058 (2)	−0.2351 (4)	0.0426 (16)
H19H	0.2136	0.1912	−0.2249	0.051*
C20C	0.2282 (3)	0.2402 (2)	−0.2975 (4)	0.0405 (15)
H20H	0.1778	0.2488	−0.3288	0.049*
C21C	0.4631 (4)	0.2036 (2)	−0.1385 (4)	0.0408 (15)
H21H	0.4907	0.2109	−0.1722	0.049*
H21I	0.4682	0.1727	−0.1261	0.049*
C22C	0.4963 (3)	0.22823 (18)	−0.0444 (4)	0.0333 (13)
C23C	0.5335 (3)	0.26771 (19)	−0.0333 (4)	0.0326 (13)
C24C	0.5518 (3)	0.29450 (19)	0.0455 (4)	0.0309 (13)
C25C	0.5361 (3)	0.2796 (2)	0.1167 (4)	0.0335 (13)
H25H	0.5479	0.2968	0.1696	0.040*
C26C	0.5029 (3)	0.23912 (19)	0.1091 (4)	0.0368 (14)
H26H	0.4943	0.2291	0.1579	0.044*
C27C	0.4827 (3)	0.21383 (19)	0.0289 (4)	0.0357 (13)
H27H	0.4600	0.1871	0.0238	0.043*
C28C	0.5890 (3)	0.33834 (19)	0.0563 (4)	0.0332 (13)
H28H	0.6169	0.3381	0.0208	0.040*
H28I	0.6252	0.3427	0.1228	0.040*
N1	0.3684 (3)	−0.05258 (15)	0.1980 (3)	0.0330 (11)
H1	0.3675	−0.0374	0.2472	0.040*
N2	0.2777 (2)	0.32100 (14)	−0.0234 (3)	0.0268 (10)
H2	0.3032	0.3260	0.0460	0.032*
N3	0.4512 (3)	0.36830 (17)	−0.4158 (3)	0.0375 (12)
H3	0.4174	0.3593	−0.3929	0.045*
C1	0.2899 (3)	−0.0530 (2)	0.1170 (4)	0.0390 (14)
H1J	0.2912	−0.0629	0.0603	0.047*
H1K	0.2704	−0.0237	0.1053	0.047*
C2	0.2360 (4)	−0.0819 (2)	0.1344 (5)	0.0529 (18)
H2J	0.1865	−0.0807	0.0802	0.079*
H2K	0.2338	−0.0720	0.1898	0.079*
H2L	0.2541	−0.1112	0.1440	0.079*
C3	0.4173 (4)	−0.0214 (2)	0.1774 (4)	0.0385 (14)
H3J	0.3928	0.0066	0.1608	0.046*
H3K	0.4216	−0.0319	0.1230	0.046*
C4	0.4967 (4)	−0.0162 (2)	0.2620 (5)	0.0524 (18)
H4J	0.5251	0.0038	0.2455	0.079*
H4K	0.5218	−0.0437	0.2777	0.079*
H4L	0.4929	−0.0053	0.3157	0.079*
C5	0.4036 (4)	−0.0962 (2)	0.2299 (4)	0.0397 (14)
H5J	0.3718	−0.1132	0.2476	0.048*
H5K	0.4522	−0.0927	0.2863	0.048*
C6	0.4151 (4)	−0.1211 (2)	0.1562 (5)	0.0505 (17)
H6J	0.4385	−0.1484	0.1823	0.076*
H6K	0.4471	−0.1047	0.1388	0.076*
H6L	0.3671	−0.1259	0.1009	0.076*
C7	0.1947 (3)	0.3165 (2)	−0.0593 (4)	0.0345 (13)
H7J	0.1763	0.3429	−0.0446	0.041*
H7K	0.1863	0.2931	−0.0252	0.041*
C8	0.1483 (3)	0.3079 (3)	−0.1652 (4)	0.0506 (18)
H8J	0.0958	0.3057	−0.1820	0.076*
H8K	0.1646	0.2812	−0.1804	0.076*
H8L	0.1552	0.3311	−0.2000	0.076*
C9	0.2995 (4)	0.35976 (18)	−0.0612 (4)	0.0358 (13)
H9J	0.2789	0.3567	−0.1294	0.043*
H9K	0.3542	0.3608	−0.0330	0.043*
C10	0.2715 (4)	0.4020 (2)	−0.0405 (5)	0.0451 (15)
H10J	0.2863	0.4257	−0.0668	0.068*
H10K	0.2932	0.4058	0.0271	0.068*
H10L	0.2174	0.4013	−0.0686	0.068*
C11	0.3143 (3)	0.28116 (17)	−0.0380 (4)	0.0306 (12)
H11J	0.3688	0.2849	−0.0050	0.037*
H11K	0.2983	0.2780	−0.1053	0.037*
C12	0.2943 (4)	0.23983 (19)	−0.0022 (4)	0.0409 (15)
H12J	0.3181	0.2155	−0.0142	0.061*
H12K	0.2404	0.2359	−0.0348	0.061*
H12L	0.3118	0.2422	0.0649	0.061*
C13	0.4616 (4)	0.4208 (3)	−0.4099 (5)	0.0565 (19)
H13J	0.4941	0.4295	−0.3445	0.068*
H13K	0.4852	0.4299	−0.4475	0.068*
C14	0.3852 (5)	0.4419 (3)	−0.4471 (6)	0.068 (2)
H14J	0.3911	0.4728	−0.4435	0.103*
H14K	0.3623	0.4330	−0.4093	0.103*
H14L	0.3535	0.4335	−0.5120	0.103*
C15	0.4171 (5)	0.3543 (3)	−0.5184 (5)	0.065 (2)
H15J	0.3933	0.3791	−0.5588	0.078*
H15K	0.4574	0.3446	−0.5308	0.078*
C16	0.3620 (4)	0.3201 (2)	−0.5440 (5)	0.0553 (19)
H16J	0.3432	0.3127	−0.6098	0.083*
H16K	0.3209	0.3298	−0.5343	0.083*
H16L	0.3853	0.2952	−0.5051	0.083*
C17	0.5239 (3)	0.3474 (2)	−0.3454 (5)	0.0413 (15)
H17J	0.5336	0.3551	−0.2818	0.050*
H17K	0.5177	0.3163	−0.3517	0.050*
C18	0.5916 (4)	0.3596 (2)	−0.3556 (5)	0.0464 (16)
H18J	0.6350	0.3440	−0.3097	0.070*
H18K	0.6006	0.3902	−0.3451	0.070*
H18L	0.5827	0.3525	−0.4185	0.070*
N4	0.2019 (4)	0.4979 (2)	0.3624 (5)	0.0724 (18)
C19	0.1996 (5)	0.4935 (3)	0.4311 (6)	0.0685 (19)
C20	0.1965 (6)	0.4890 (3)	0.5193 (6)	0.092 (3)
H20J	0.1484	0.4992	0.5103	0.138*
H20K	0.2362	0.5058	0.5681	0.138*
H20L	0.2027	0.4592	0.5379	0.138*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.047 (3)	0.031 (2)	0.029 (2)	−0.0115 (19)	0.014 (2)	0.0006 (17)
O2A	0.028 (2)	0.033 (2)	0.0252 (18)	−0.0023 (17)	0.0124 (17)	−0.0014 (16)
O3A	0.029 (2)	0.026 (2)	0.038 (2)	0.0003 (17)	0.0156 (18)	−0.0052 (16)
O4A	0.037 (2)	0.031 (2)	0.0271 (19)	−0.0061 (17)	0.0164 (18)	−0.0053 (16)
C1A	0.031 (3)	0.024 (3)	0.031 (3)	0.007 (2)	0.012 (3)	0.002 (2)
C2A	0.030 (3)	0.026 (3)	0.033 (3)	0.005 (2)	0.010 (3)	0.007 (2)
C3A	0.033 (4)	0.053 (4)	0.035 (3)	0.011 (3)	0.017 (3)	0.017 (3)
C4A	0.033 (4)	0.069 (5)	0.034 (3)	0.010 (3)	0.011 (3)	0.024 (3)
C5A	0.026 (3)	0.067 (5)	0.040 (3)	0.010 (3)	0.014 (3)	0.021 (3)
C6A	0.029 (3)	0.047 (4)	0.035 (3)	0.012 (3)	0.019 (3)	0.014 (3)
C7A	0.026 (3)	0.046 (4)	0.037 (3)	0.010 (3)	0.017 (3)	0.014 (3)
C8A	0.028 (3)	0.055 (4)	0.029 (3)	0.004 (3)	0.020 (3)	0.008 (3)
C9A	0.026 (3)	0.041 (3)	0.024 (3)	−0.002 (3)	0.015 (2)	0.001 (2)
C10A	0.021 (3)	0.044 (4)	0.028 (3)	−0.001 (3)	0.015 (2)	0.001 (2)
C11A	0.028 (3)	0.044 (4)	0.037 (3)	−0.007 (3)	0.018 (3)	0.000 (3)
C12A	0.029 (3)	0.059 (5)	0.038 (3)	−0.012 (3)	0.019 (3)	−0.004 (3)
C13A	0.023 (3)	0.069 (5)	0.028 (3)	0.001 (3)	0.014 (3)	0.005 (3)
C14A	0.028 (3)	0.033 (3)	0.027 (3)	−0.005 (2)	0.013 (3)	0.002 (2)
C15A	0.035 (3)	0.025 (3)	0.026 (3)	0.001 (3)	0.015 (3)	0.003 (2)
C16A	0.026 (3)	0.024 (3)	0.024 (3)	−0.001 (2)	0.008 (2)	−0.001 (2)
C17A	0.025 (3)	0.026 (3)	0.027 (3)	0.003 (2)	0.008 (2)	0.004 (2)
C18A	0.027 (3)	0.028 (3)	0.037 (3)	0.002 (2)	0.015 (3)	0.006 (2)
C19A	0.036 (3)	0.028 (3)	0.036 (3)	0.007 (3)	0.015 (3)	0.005 (2)
C20A	0.037 (3)	0.020 (3)	0.030 (3)	−0.006 (2)	0.014 (3)	0.005 (2)
C21A	0.024 (3)	0.025 (3)	0.040 (3)	−0.005 (2)	0.010 (3)	0.003 (2)
C22A	0.019 (3)	0.032 (3)	0.031 (3)	−0.005 (2)	0.013 (2)	−0.003 (2)
C23A	0.026 (3)	0.031 (3)	0.024 (3)	−0.009 (2)	0.009 (2)	−0.002 (2)
C24A	0.022 (3)	0.027 (3)	0.031 (3)	−0.007 (2)	0.008 (2)	0.000 (2)
C25A	0.026 (3)	0.041 (4)	0.030 (3)	−0.010 (3)	0.010 (3)	0.002 (3)
C26A	0.037 (3)	0.049 (4)	0.033 (3)	−0.011 (3)	0.022 (3)	−0.010 (3)
C27A	0.027 (3)	0.033 (3)	0.047 (3)	−0.002 (3)	0.019 (3)	−0.004 (3)
C28A	0.032 (3)	0.028 (3)	0.039 (3)	−0.004 (3)	0.011 (3)	0.006 (3)
O1B	0.029 (2)	0.032 (2)	0.0276 (19)	−0.0010 (17)	0.0089 (18)	0.0013 (16)
O2B	0.029 (2)	0.024 (2)	0.0260 (18)	−0.0044 (16)	0.0136 (17)	−0.0035 (15)
O3B	0.036 (2)	0.039 (2)	0.0308 (19)	−0.0080 (19)	0.0197 (19)	−0.0060 (17)
O4B	0.035 (2)	0.038 (2)	0.0289 (19)	−0.0090 (19)	0.0173 (18)	−0.0028 (17)
C1B	0.021 (3)	0.031 (3)	0.025 (3)	−0.002 (2)	0.012 (2)	−0.004 (2)
C2B	0.029 (3)	0.021 (3)	0.029 (3)	0.004 (2)	0.018 (3)	0.004 (2)
C3B	0.025 (3)	0.032 (3)	0.028 (3)	0.008 (3)	0.012 (3)	0.007 (2)
C4B	0.022 (3)	0.039 (4)	0.029 (3)	0.003 (2)	0.010 (2)	−0.003 (2)
C5B	0.026 (3)	0.031 (3)	0.032 (3)	0.002 (2)	0.015 (3)	−0.001 (2)
C6B	0.022 (3)	0.026 (3)	0.029 (3)	−0.002 (2)	0.016 (2)	−0.004 (2)
C7B	0.023 (3)	0.028 (3)	0.029 (3)	−0.006 (2)	0.014 (2)	−0.003 (2)
C8B	0.030 (3)	0.030 (3)	0.024 (3)	−0.002 (2)	0.015 (2)	0.005 (2)
C9B	0.021 (3)	0.025 (3)	0.022 (2)	0.000 (2)	0.010 (2)	0.004 (2)
C10B	0.030 (3)	0.027 (3)	0.031 (3)	−0.004 (2)	0.018 (3)	0.000 (2)
C11B	0.032 (3)	0.030 (3)	0.029 (3)	0.009 (3)	0.017 (3)	0.007 (2)
C12B	0.046 (4)	0.020 (3)	0.028 (3)	−0.005 (3)	0.019 (3)	−0.003 (2)
C13B	0.028 (3)	0.028 (3)	0.032 (3)	−0.006 (2)	0.014 (3)	0.000 (2)
C14B	0.030 (3)	0.030 (3)	0.038 (3)	0.007 (3)	0.017 (3)	0.007 (2)
C15B	0.030 (3)	0.037 (3)	0.038 (3)	0.002 (3)	0.019 (3)	0.005 (3)
C16B	0.020 (3)	0.038 (3)	0.032 (3)	−0.001 (2)	0.014 (2)	−0.001 (2)
C17B	0.029 (3)	0.035 (3)	0.036 (3)	−0.005 (3)	0.015 (3)	0.001 (3)
C18B	0.035 (3)	0.043 (4)	0.043 (3)	0.004 (3)	0.026 (3)	0.005 (3)
C19B	0.046 (4)	0.039 (4)	0.055 (4)	0.003 (3)	0.034 (3)	−0.001 (3)
C20B	0.037 (4)	0.039 (4)	0.053 (4)	0.003 (3)	0.027 (3)	0.001 (3)
C21B	0.035 (3)	0.030 (3)	0.033 (3)	−0.004 (3)	0.018 (3)	−0.001 (2)
C22B	0.039 (3)	0.020 (3)	0.031 (3)	−0.007 (2)	0.018 (3)	−0.005 (2)
C23B	0.035 (3)	0.021 (3)	0.022 (2)	−0.011 (2)	0.014 (2)	0.000 (2)
C24B	0.031 (3)	0.022 (3)	0.030 (3)	0.000 (2)	0.014 (3)	0.003 (2)
C25B	0.041 (4)	0.030 (3)	0.028 (3)	−0.004 (3)	0.014 (3)	−0.002 (2)
C26B	0.049 (4)	0.029 (3)	0.033 (3)	−0.009 (3)	0.025 (3)	−0.006 (2)
C27B	0.036 (3)	0.027 (3)	0.036 (3)	−0.005 (3)	0.020 (3)	−0.004 (2)
C28B	0.035 (3)	0.029 (3)	0.032 (3)	0.000 (3)	0.019 (3)	0.004 (2)
O1C	0.026 (2)	0.037 (2)	0.0227 (17)	−0.0046 (17)	0.0099 (16)	−0.0037 (16)
O2C	0.024 (2)	0.037 (2)	0.0214 (17)	−0.0022 (17)	0.0098 (16)	−0.0006 (15)
O3C	0.036 (2)	0.034 (2)	0.040 (2)	−0.0032 (18)	0.021 (2)	−0.0038 (18)
O4C	0.035 (2)	0.048 (3)	0.033 (2)	0.006 (2)	0.0212 (19)	0.0048 (18)
C1C	0.031 (3)	0.035 (3)	0.026 (3)	−0.003 (3)	0.016 (3)	−0.002 (2)
C2C	0.023 (3)	0.033 (3)	0.026 (3)	−0.003 (2)	0.011 (2)	−0.004 (2)
C3C	0.037 (3)	0.027 (3)	0.023 (2)	−0.006 (2)	0.017 (3)	0.000 (2)
C4C	0.052 (4)	0.026 (3)	0.034 (3)	−0.003 (3)	0.022 (3)	−0.003 (2)
C5C	0.053 (4)	0.033 (3)	0.030 (3)	−0.008 (3)	0.022 (3)	−0.005 (3)
C6C	0.039 (4)	0.040 (4)	0.025 (3)	−0.010 (3)	0.016 (3)	−0.005 (3)
C7C	0.053 (4)	0.030 (3)	0.031 (3)	−0.003 (3)	0.024 (3)	0.004 (2)
C8C	0.036 (3)	0.039 (4)	0.019 (2)	0.000 (3)	0.011 (3)	0.000 (2)
C9C	0.026 (3)	0.036 (3)	0.022 (2)	0.005 (2)	0.013 (2)	0.004 (2)
C10C	0.024 (3)	0.053 (4)	0.018 (2)	0.004 (3)	0.008 (2)	0.003 (2)
C11C	0.026 (3)	0.061 (4)	0.026 (3)	−0.002 (3)	0.012 (3)	0.003 (3)
C12C	0.032 (4)	0.077 (5)	0.028 (3)	0.017 (3)	0.016 (3)	0.012 (3)
C13C	0.046 (4)	0.048 (4)	0.027 (3)	0.017 (3)	0.019 (3)	0.007 (3)
C14C	0.028 (3)	0.051 (4)	0.031 (3)	−0.016 (3)	0.014 (3)	−0.013 (3)
C15C	0.033 (3)	0.037 (3)	0.020 (2)	−0.012 (3)	0.011 (2)	−0.010 (2)
C16C	0.042 (4)	0.027 (3)	0.031 (3)	−0.014 (3)	0.023 (3)	−0.010 (2)
C17C	0.040 (4)	0.025 (3)	0.040 (3)	−0.008 (3)	0.023 (3)	−0.012 (3)
C18C	0.065 (5)	0.036 (4)	0.039 (3)	−0.015 (3)	0.032 (4)	−0.008 (3)
C19C	0.050 (4)	0.048 (4)	0.031 (3)	−0.029 (3)	0.021 (3)	−0.014 (3)
C20C	0.029 (3)	0.058 (4)	0.035 (3)	−0.014 (3)	0.015 (3)	−0.007 (3)
C21C	0.054 (4)	0.029 (3)	0.043 (3)	0.011 (3)	0.026 (3)	0.006 (3)
C22C	0.035 (3)	0.030 (3)	0.036 (3)	0.011 (3)	0.017 (3)	0.006 (3)
C23C	0.026 (3)	0.043 (4)	0.030 (3)	0.013 (3)	0.014 (3)	0.007 (3)
C24C	0.018 (3)	0.042 (4)	0.028 (3)	0.007 (2)	0.007 (2)	0.002 (2)
C25C	0.020 (3)	0.048 (4)	0.031 (3)	0.009 (3)	0.011 (2)	0.006 (3)
C26C	0.030 (3)	0.042 (4)	0.040 (3)	0.006 (3)	0.018 (3)	0.009 (3)
C27C	0.041 (4)	0.035 (3)	0.034 (3)	0.005 (3)	0.020 (3)	0.006 (3)
C28C	0.025 (3)	0.045 (4)	0.024 (3)	−0.001 (3)	0.008 (2)	−0.001 (2)
N1	0.037 (3)	0.036 (3)	0.030 (2)	0.002 (2)	0.020 (2)	0.001 (2)
N2	0.021 (2)	0.033 (3)	0.023 (2)	−0.002 (2)	0.008 (2)	0.0009 (19)
N3	0.034 (3)	0.054 (3)	0.028 (2)	−0.011 (2)	0.018 (2)	−0.010 (2)
C1	0.031 (3)	0.048 (4)	0.034 (3)	−0.006 (3)	0.013 (3)	−0.010 (3)
C2	0.048 (4)	0.061 (5)	0.050 (4)	−0.012 (4)	0.025 (4)	−0.011 (3)
C3	0.042 (4)	0.041 (4)	0.039 (3)	−0.002 (3)	0.025 (3)	0.002 (3)
C4	0.045 (4)	0.067 (5)	0.054 (4)	−0.010 (4)	0.031 (4)	−0.009 (4)
C5	0.042 (4)	0.039 (4)	0.036 (3)	0.005 (3)	0.017 (3)	−0.001 (3)
C6	0.069 (5)	0.046 (4)	0.044 (4)	0.007 (4)	0.033 (4)	0.001 (3)
C7	0.024 (3)	0.053 (4)	0.027 (3)	−0.006 (3)	0.013 (2)	0.001 (3)
C8	0.027 (3)	0.091 (6)	0.030 (3)	−0.007 (3)	0.011 (3)	−0.008 (3)
C9	0.042 (4)	0.033 (3)	0.040 (3)	−0.002 (3)	0.025 (3)	0.006 (3)
C10	0.051 (4)	0.038 (4)	0.047 (4)	0.006 (3)	0.024 (3)	0.004 (3)
C11	0.032 (3)	0.033 (3)	0.030 (3)	0.000 (3)	0.018 (3)	−0.002 (2)
C12	0.048 (4)	0.037 (4)	0.035 (3)	−0.012 (3)	0.018 (3)	−0.001 (3)
C13	0.037 (4)	0.081 (6)	0.052 (4)	0.016 (4)	0.022 (3)	0.024 (4)
C14	0.081 (6)	0.067 (5)	0.068 (5)	0.007 (5)	0.044 (5)	0.006 (4)
C15	0.069 (5)	0.076 (6)	0.047 (4)	−0.018 (4)	0.026 (4)	−0.013 (4)
C16	0.075 (5)	0.042 (4)	0.063 (4)	−0.023 (4)	0.045 (4)	−0.022 (3)
C17	0.037 (4)	0.032 (3)	0.057 (4)	0.001 (3)	0.024 (3)	0.007 (3)
C18	0.045 (4)	0.049 (4)	0.054 (4)	−0.007 (3)	0.031 (3)	−0.020 (3)
N4	0.097 (5)	0.060 (4)	0.078 (4)	−0.019 (3)	0.057 (4)	−0.016 (3)
C19	0.082 (4)	0.073 (4)	0.070 (4)	−0.012 (4)	0.053 (4)	0.000 (3)
C20	0.095 (5)	0.117 (6)	0.080 (5)	0.004 (5)	0.056 (4)	0.012 (4)

Geometric parameters (Å, º)

O1A—C1A	1.364 (6)	O4C—H4C	0.8737
O1A—H1A	0.8182	C1C—C2C	1.394 (7)
O2A—C9A	1.351 (6)	C1C—C6C	1.402 (7)
O3A—C16A	1.380 (6)	C1C—C28C	1.524 (8)
O3A—H3A	0.9290	C2C—C3C	1.393 (8)
O4A—C23A	1.380 (6)	C3C—C4C	1.386 (7)
O4A—H4A	0.8945	C3C—C7C	1.522 (7)
C1A—C6A	1.397 (8)	C4C—C5C	1.401 (8)
C1A—C2A	1.403 (7)	C4C—H4H	0.9300
C2A—C3A	1.379 (8)	C5C—C6C	1.380 (8)
C2A—C28A	1.520 (8)	C5C—H5H	0.9300
C3A—C4A	1.382 (9)	C6C—H6H	0.9300
C3A—H3D	0.9300	C7C—C8C	1.507 (8)
C4A—C5A	1.391 (8)	C7C—H7H	0.9700
C4A—H4D	0.9300	C7C—H7I	0.9700
C5A—C6A	1.408 (8)	C8C—C13C	1.387 (8)
C5A—H5D	0.9300	C8C—C9C	1.427 (8)
C6A—C7A	1.523 (7)	C9C—C10C	1.394 (8)
C7A—C8A	1.512 (8)	C10C—C11C	1.389 (8)
C7A—H7D	0.9700	C10C—C14C	1.515 (8)
C7A—H7E	0.9700	C11C—C12C	1.399 (9)
C8A—C13A	1.405 (8)	C11C—H11H	0.9300
C8A—C9A	1.414 (8)	C12C—C13C	1.372 (9)
C9A—C10A	1.404 (8)	C12C—H12H	0.9300
C10A—C11A	1.385 (8)	C13C—H13H	0.9300
C10A—C14A	1.524 (7)	C14C—C15C	1.510 (8)
C11A—C12A	1.389 (9)	C14C—H14H	0.9700
C11A—H11D	0.9300	C14C—H14I	0.9700
C12A—C13A	1.363 (9)	C15C—C20C	1.404 (7)
C12A—H12D	0.9300	C15C—C16C	1.409 (8)
C13A—H13D	0.9300	C16C—C17C	1.411 (8)
C14A—C15A	1.524 (7)	C17C—C18C	1.415 (8)
C14A—H14D	0.9700	C17C—C21C	1.506 (8)
C14A—H14E	0.9700	C18C—C19C	1.372 (9)
C15A—C16A	1.394 (7)	C18C—H18H	0.9300
C15A—C20A	1.397 (7)	C19C—C20C	1.380 (9)
C16A—C17A	1.405 (7)	C19C—H19H	0.9300
C17A—C18A	1.387 (7)	C20C—H20H	0.9300
C17A—C21A	1.510 (7)	C21C—C22C	1.527 (8)
C18A—C19A	1.387 (8)	C21C—H21H	0.9700
C18A—H18D	0.9300	C21C—H21I	0.9700
C19A—C20A	1.375 (8)	C22C—C27C	1.398 (7)
C19A—H19D	0.9300	C22C—C23C	1.398 (8)
C20A—H20D	0.9300	C23C—C24C	1.403 (8)
C21A—C22A	1.509 (7)	C24C—C25C	1.399 (7)
C21A—H21D	0.9700	C24C—C28C	1.518 (8)
C21A—H21E	0.9700	C25C—C26C	1.396 (8)
C22A—C27A	1.396 (7)	C25C—H25H	0.9300
C22A—C23A	1.399 (7)	C26C—C27C	1.388 (8)
C23A—C24A	1.406 (7)	C26C—H26H	0.9300
C24A—C25A	1.403 (8)	C27C—H27H	0.9300
C24A—C28A	1.512 (8)	C28C—H28H	0.9700
C25A—C26A	1.364 (8)	C28C—H28I	0.9700
C25A—H25D	0.9300	N1—C1	1.490 (7)
C26A—C27A	1.383 (8)	N1—C5	1.494 (7)
C26A—H26D	0.9300	N1—C3	1.522 (7)
C27A—H27D	0.9300	N1—H1	0.9262
C28A—H28D	0.9700	N2—C7	1.491 (7)
C28A—H28E	0.9700	N2—C9	1.499 (6)
O1B—C1B	1.360 (6)	N2—C11	1.510 (7)
O1B—H1B	0.8145	N2—H2	0.9881
O2B—C9B	1.347 (6)	N3—C17	1.500 (8)
O3B—C16B	1.367 (6)	N3—C15	1.509 (8)
O3B—H3B	0.9604	N3—C13	1.633 (9)
O4B—C23B	1.392 (6)	N3—H3	0.9556
O4B—H4B	0.9194	C1—C2	1.530 (8)
C1B—C2B	1.393 (7)	C1—H1J	0.9700
C1B—C6B	1.406 (7)	C1—H1K	0.9700
C2B—C3B	1.391 (7)	C2—H2J	0.9600
C2B—C28B	1.522 (7)	C2—H2K	0.9600
C3B—C4B	1.399 (8)	C2—H2L	0.9600
C3B—H3F	0.9300	C3—C4	1.530 (9)
C4B—C5B	1.396 (7)	C3—H3J	0.9700
C4B—H4F	0.9300	C3—H3K	0.9700
C5B—C6B	1.395 (7)	C4—H4J	0.9600
C5B—H5F	0.9300	C4—H4K	0.9600
C6B—C7B	1.525 (7)	C4—H4L	0.9600
C7B—C8B	1.504 (7)	C5—C6	1.516 (8)
C7B—H7F	0.9700	C5—H5J	0.9700
C7B—H7G	0.9700	C5—H5K	0.9700
C8B—C13B	1.395 (7)	C6—H6J	0.9600
C8B—C9B	1.424 (7)	C6—H6K	0.9600
C9B—C10B	1.414 (7)	C6—H6L	0.9600
C10B—C11B	1.397 (8)	C7—C8	1.516 (7)
C10B—C14B	1.518 (7)	C7—H7J	0.9700
C11B—C12B	1.365 (8)	C7—H7K	0.9700
C11B—H11F	0.9300	C8—H8J	0.9600
C12B—C13B	1.395 (8)	C8—H8K	0.9600
C12B—H12F	0.9300	C8—H8L	0.9600
C13B—H13F	0.9300	C9—C10	1.520 (8)
C14B—C15B	1.526 (7)	C9—H9J	0.9700
C14B—H14F	0.9700	C9—H9K	0.9700
C14B—H14G	0.9700	C10—H10J	0.9600
C15B—C20B	1.400 (8)	C10—H10K	0.9600
C15B—C16B	1.405 (8)	C10—H10L	0.9600
C16B—C17B	1.408 (7)	C11—C12	1.531 (7)
C17B—C18B	1.385 (8)	C11—H11J	0.9700
C17B—C21B	1.525 (8)	C11—H11K	0.9700
C18B—C19B	1.381 (8)	C12—H12J	0.9600
C18B—H18F	0.9300	C12—H12K	0.9600
C19B—C20B	1.399 (8)	C12—H12L	0.9600
C19B—H19F	0.9300	C13—C14	1.509 (10)
C20B—H20F	0.9300	C13—H13J	0.9700
C21B—C22B	1.518 (8)	C13—H13K	0.9700
C21B—H21F	0.9700	C14—H14J	0.9600
C21B—H21G	0.9700	C14—H14K	0.9600
C22B—C27B	1.381 (7)	C14—H14L	0.9600
C22B—C23B	1.385 (7)	C15—C16	1.441 (9)
C23B—C24B	1.400 (8)	C15—H15J	0.9700
C24B—C25B	1.389 (7)	C15—H15K	0.9700
C24B—C28B	1.523 (7)	C16—H16J	0.9600
C25B—C26B	1.383 (8)	C16—H16K	0.9600
C25B—H25F	0.9300	C16—H16L	0.9600
C26B—C27B	1.367 (8)	C17—C18	1.497 (8)
C26B—H26F	0.9300	C17—H17J	0.9700
C27B—H27F	0.9300	C17—H17K	0.9700
C28B—H28F	0.9700	C18—H18J	0.9600
C28B—H28G	0.9700	C18—H18K	0.9600
O1C—C2C	1.376 (6)	C18—H18L	0.9600
O1C—H1C	0.8158	N4—C19	1.129 (9)
O2C—C9C	1.354 (6)	C19—C20	1.451 (10)
O3C—C16C	1.359 (6)	C20—H20J	0.9600
O3C—H3C	0.8636	C20—H20K	0.9600
O4C—C23C	1.372 (6)	C20—H20L	0.9600
C1A—O1A—H1A	108.5	C4C—C5C—H5H	120.2
C16A—O3A—H3A	100.0	C5C—C6C—C1C	120.8 (5)
C23A—O4A—H4A	113.6	C5C—C6C—H6H	119.6
O1A—C1A—C6A	121.5 (5)	C1C—C6C—H6H	119.6
O1A—C1A—C2A	117.6 (5)	C8C—C7C—C3C	114.1 (4)
C6A—C1A—C2A	120.8 (5)	C8C—C7C—H7H	108.7
C3A—C2A—C1A	119.3 (5)	C3C—C7C—H7H	108.7
C3A—C2A—C28A	120.7 (5)	C8C—C7C—H7I	108.7
C1A—C2A—C28A	119.9 (5)	C3C—C7C—H7I	108.7
C2A—C3A—C4A	121.3 (5)	H7H—C7C—H7I	107.6
C2A—C3A—H3D	119.4	C13C—C8C—C9C	118.2 (5)
C4A—C3A—H3D	119.4	C13C—C8C—C7C	120.8 (5)
C3A—C4A—C5A	119.4 (5)	C9C—C8C—C7C	120.9 (5)
C3A—C4A—H4D	120.3	O2C—C9C—C10C	120.8 (5)
C5A—C4A—H4D	120.3	O2C—C9C—C8C	118.7 (5)
C4A—C5A—C6A	121.0 (6)	C10C—C9C—C8C	120.5 (5)
C4A—C5A—H5D	119.5	C11C—C10C—C9C	118.8 (5)
C6A—C5A—H5D	119.5	C11C—C10C—C14C	120.6 (5)
C1A—C6A—C5A	118.2 (5)	C9C—C10C—C14C	120.6 (5)
C1A—C6A—C7A	121.6 (5)	C10C—C11C—C12C	121.3 (6)
C5A—C6A—C7A	120.2 (5)	C10C—C11C—H11H	119.4
C8A—C7A—C6A	114.4 (4)	C12C—C11C—H11H	119.4
C8A—C7A—H7D	108.6	C13C—C12C—C11C	119.3 (6)
C6A—C7A—H7D	108.6	C13C—C12C—H12H	120.4
C8A—C7A—H7E	108.6	C11C—C12C—H12H	120.4
C6A—C7A—H7E	108.6	C12C—C13C—C8C	121.8 (6)
H7D—C7A—H7E	107.6	C12C—C13C—H13H	119.1
C13A—C8A—C9A	118.5 (6)	C8C—C13C—H13H	119.1
C13A—C8A—C7A	120.8 (5)	C15C—C14C—C10C	115.3 (4)
C9A—C8A—C7A	120.6 (5)	C15C—C14C—H14H	108.4
O2A—C9A—C10A	120.8 (5)	C10C—C14C—H14H	108.4
O2A—C9A—C8A	119.5 (5)	C15C—C14C—H14I	108.4
C10A—C9A—C8A	119.8 (5)	C10C—C14C—H14I	108.4
C11A—C10A—C9A	119.3 (5)	H14H—C14C—H14I	107.5
C11A—C10A—C14A	120.7 (5)	C20C—C15C—C16C	118.4 (5)
C9A—C10A—C14A	120.0 (5)	C20C—C15C—C14C	119.6 (5)
C10A—C11A—C12A	121.3 (6)	C16C—C15C—C14C	122.0 (5)
C10A—C11A—H11D	119.4	O3C—C16C—C15C	121.4 (5)
C12A—C11A—H11D	119.4	O3C—C16C—C17C	117.1 (5)
C13A—C12A—C11A	119.7 (6)	C15C—C16C—C17C	121.4 (5)
C13A—C12A—H12D	120.2	C16C—C17C—C18C	117.2 (6)
C11A—C12A—H12D	120.2	C16C—C17C—C21C	121.6 (5)
C12A—C13A—C8A	121.4 (6)	C18C—C17C—C21C	121.1 (5)
C12A—C13A—H13D	119.3	C19C—C18C—C17C	121.8 (6)
C8A—C13A—H13D	119.3	C19C—C18C—H18H	119.1
C10A—C14A—C15A	115.6 (4)	C17C—C18C—H18H	119.1
C10A—C14A—H14D	108.4	C18C—C19C—C20C	120.2 (6)
C15A—C14A—H14D	108.4	C18C—C19C—H19H	119.9
C10A—C14A—H14E	108.4	C20C—C19C—H19H	119.9
C15A—C14A—H14E	108.4	C19C—C20C—C15C	121.0 (6)
H14D—C14A—H14E	107.4	C19C—C20C—H20H	119.5
C16A—C15A—C20A	117.4 (5)	C15C—C20C—H20H	119.5
C16A—C15A—C14A	122.4 (5)	C17C—C21C—C22C	110.1 (4)
C20A—C15A—C14A	120.1 (5)	C17C—C21C—H21H	109.6
O3A—C16A—C15A	121.4 (5)	C22C—C21C—H21H	109.6
O3A—C16A—C17A	116.2 (4)	C17C—C21C—H21I	109.6
C15A—C16A—C17A	122.3 (5)	C22C—C21C—H21I	109.6
C18A—C17A—C16A	117.2 (5)	H21H—C21C—H21I	108.2
C18A—C17A—C21A	121.8 (5)	C27C—C22C—C23C	118.6 (5)
C16A—C17A—C21A	120.8 (5)	C27C—C22C—C21C	120.0 (5)
C17A—C18A—C19A	122.3 (5)	C23C—C22C—C21C	121.0 (5)
C17A—C18A—H18D	118.8	O4C—C23C—C22C	118.1 (5)
C19A—C18A—H18D	118.8	O4C—C23C—C24C	120.3 (5)
C20A—C19A—C18A	118.7 (5)	C22C—C23C—C24C	121.6 (5)
C20A—C19A—H19D	120.7	C25C—C24C—C23C	118.3 (5)
C18A—C19A—H19D	120.7	C25C—C24C—C28C	119.6 (5)
C19A—C20A—C15A	122.1 (5)	C23C—C24C—C28C	122.1 (5)
C19A—C20A—H20D	119.0	C26C—C25C—C24C	120.6 (5)
C15A—C20A—H20D	119.0	C26C—C25C—H25H	119.7
C22A—C21A—C17A	110.4 (4)	C24C—C25C—H25H	119.7
C22A—C21A—H21D	109.6	C27C—C26C—C25C	120.1 (5)
C17A—C21A—H21D	109.6	C27C—C26C—H26H	120.0
C22A—C21A—H21E	109.6	C25C—C26C—H26H	120.0
C17A—C21A—H21E	109.6	C26C—C27C—C22C	120.6 (6)
H21D—C21A—H21E	108.1	C26C—C27C—H27H	119.7
C27A—C22A—C23A	117.7 (5)	C22C—C27C—H27H	119.7
C27A—C22A—C21A	120.4 (5)	C24C—C28C—C1C	114.4 (5)
C23A—C22A—C21A	121.9 (5)	C24C—C28C—H28H	108.7
O4A—C23A—C22A	119.6 (5)	C1C—C28C—H28H	108.7
O4A—C23A—C24A	118.7 (5)	C24C—C28C—H28I	108.7
C22A—C23A—C24A	121.6 (5)	C1C—C28C—H28I	108.7
C25A—C24A—C23A	117.6 (5)	H28H—C28C—H28I	107.6
C25A—C24A—C28A	120.5 (5)	C1—N1—C5	115.0 (5)
C23A—C24A—C28A	121.8 (5)	C1—N1—C3	110.1 (4)
C26A—C25A—C24A	121.5 (5)	C5—N1—C3	113.3 (4)
C26A—C25A—H25D	119.2	C1—N1—H1	107.4
C24A—C25A—H25D	119.2	C5—N1—H1	111.4
C25A—C26A—C27A	119.8 (5)	C3—N1—H1	98.3
C25A—C26A—H26D	120.1	C7—N2—C9	114.1 (4)
C27A—C26A—H26D	120.1	C7—N2—C11	113.9 (4)
C26A—C27A—C22A	121.5 (5)	C9—N2—C11	109.3 (4)
C26A—C27A—H27D	119.2	C7—N2—H2	109.4
C22A—C27A—H27D	119.2	C9—N2—H2	103.5
C24A—C28A—C2A	112.1 (5)	C11—N2—H2	105.8
C24A—C28A—H28D	109.2	C17—N3—C15	117.8 (5)
C2A—C28A—H28D	109.2	C17—N3—C13	109.4 (5)
C24A—C28A—H28E	109.2	C15—N3—C13	109.1 (5)
C2A—C28A—H28E	109.2	C17—N3—H3	101.8
H28D—C28A—H28E	107.9	C15—N3—H3	107.3
C1B—O1B—H1B	114.4	C13—N3—H3	111.2
C16B—O3B—H3B	117.3	N1—C1—C2	113.3 (5)
C23B—O4B—H4B	105.2	N1—C1—H1J	108.9
O1B—C1B—C2B	117.6 (5)	C2—C1—H1J	108.9
O1B—C1B—C6B	121.2 (4)	N1—C1—H1K	108.9
C2B—C1B—C6B	121.2 (5)	C2—C1—H1K	108.9
C3B—C2B—C1B	119.1 (5)	H1J—C1—H1K	107.7
C3B—C2B—C28B	119.9 (5)	C1—C2—H2J	109.5
C1B—C2B—C28B	121.0 (5)	C1—C2—H2K	109.5
C2B—C3B—C4B	121.4 (5)	H2J—C2—H2K	109.5
C2B—C3B—H3F	119.3	C1—C2—H2L	109.5
C4B—C3B—H3F	119.3	H2J—C2—H2L	109.5
C5B—C4B—C3B	118.1 (5)	H2K—C2—H2L	109.5
C5B—C4B—H4F	121.0	N1—C3—C4	112.7 (5)
C3B—C4B—H4F	121.0	N1—C3—H3J	109.1
C6B—C5B—C4B	122.3 (5)	C4—C3—H3J	109.1
C6B—C5B—H5F	118.9	N1—C3—H3K	109.1
C4B—C5B—H5F	118.9	C4—C3—H3K	109.1
C5B—C6B—C1B	117.9 (5)	H3J—C3—H3K	107.8
C5B—C6B—C7B	120.4 (5)	C3—C4—H4J	109.5
C1B—C6B—C7B	121.7 (4)	C3—C4—H4K	109.5
C8B—C7B—C6B	114.2 (4)	H4J—C4—H4K	109.5
C8B—C7B—H7F	108.7	C3—C4—H4L	109.5
C6B—C7B—H7F	108.7	H4J—C4—H4L	109.5
C8B—C7B—H7G	108.7	H4K—C4—H4L	109.5
C6B—C7B—H7G	108.7	N1—C5—C6	114.6 (5)
H7F—C7B—H7G	107.6	N1—C5—H5J	108.6
C13B—C8B—C9B	119.4 (5)	C6—C5—H5J	108.6
C13B—C8B—C7B	120.4 (5)	N1—C5—H5K	108.6
C9B—C8B—C7B	120.2 (5)	C6—C5—H5K	108.6
O2B—C9B—C10B	121.5 (4)	H5J—C5—H5K	107.6
O2B—C9B—C8B	119.4 (5)	C5—C6—H6J	109.5
C10B—C9B—C8B	119.1 (5)	C5—C6—H6K	109.5
C11B—C10B—C9B	119.0 (5)	H6J—C6—H6K	109.5
C11B—C10B—C14B	120.2 (5)	C5—C6—H6L	109.5
C9B—C10B—C14B	120.7 (5)	H6J—C6—H6L	109.5
C12B—C11B—C10B	122.0 (5)	H6K—C6—H6L	109.5
C12B—C11B—H11F	119.0	N2—C7—C8	115.2 (4)
C10B—C11B—H11F	119.0	N2—C7—H7J	108.5
C11B—C12B—C13B	119.7 (5)	C8—C7—H7J	108.5
C11B—C12B—H12F	120.1	N2—C7—H7K	108.5
C13B—C12B—H12F	120.1	C8—C7—H7K	108.5
C8B—C13B—C12B	120.7 (5)	H7J—C7—H7K	107.5
C8B—C13B—H13F	119.6	C7—C8—H8J	109.5
C12B—C13B—H13F	119.6	C7—C8—H8K	109.5
C10B—C14B—C15B	115.2 (5)	H8J—C8—H8K	109.5
C10B—C14B—H14F	108.5	C7—C8—H8L	109.5
C15B—C14B—H14F	108.5	H8J—C8—H8L	109.5
C10B—C14B—H14G	108.5	H8K—C8—H8L	109.5
C15B—C14B—H14G	108.5	N2—C9—C10	112.8 (4)
H14F—C14B—H14G	107.5	N2—C9—H9J	109.0
C20B—C15B—C16B	119.0 (5)	C10—C9—H9J	109.0
C20B—C15B—C14B	119.3 (5)	N2—C9—H9K	109.0
C16B—C15B—C14B	121.7 (5)	C10—C9—H9K	109.0
O3B—C16B—C15B	121.2 (4)	H9J—C9—H9K	107.8
O3B—C16B—C17B	117.7 (5)	C9—C10—H10J	109.5
C15B—C16B—C17B	121.1 (5)	C9—C10—H10K	109.5
C18B—C17B—C16B	118.2 (5)	H10J—C10—H10K	109.5
C18B—C17B—C21B	121.2 (5)	C9—C10—H10L	109.5
C16B—C17B—C21B	120.5 (5)	H10J—C10—H10L	109.5
C19B—C18B—C17B	121.7 (5)	H10K—C10—H10L	109.5
C19B—C18B—H18F	119.1	N2—C11—C12	112.8 (4)
C17B—C18B—H18F	119.1	N2—C11—H11J	109.0
C18B—C19B—C20B	120.1 (5)	C12—C11—H11J	109.0
C18B—C19B—H19F	120.0	N2—C11—H11K	109.0
C20B—C19B—H19F	120.0	C12—C11—H11K	109.0
C19B—C20B—C15B	119.9 (6)	H11J—C11—H11K	107.8
C19B—C20B—H20F	120.1	C11—C12—H12J	109.5
C15B—C20B—H20F	120.1	C11—C12—H12K	109.5
C22B—C21B—C17B	110.7 (5)	H12J—C12—H12K	109.5
C22B—C21B—H21F	109.5	C11—C12—H12L	109.5
C17B—C21B—H21F	109.5	H12J—C12—H12L	109.5
C22B—C21B—H21G	109.5	H12K—C12—H12L	109.5
C17B—C21B—H21G	109.5	C14—C13—N3	109.2 (6)
H21F—C21B—H21G	108.1	C14—C13—H13J	109.8
C27B—C22B—C23B	117.9 (5)	N3—C13—H13J	109.8
C27B—C22B—C21B	119.4 (5)	C14—C13—H13K	109.8
C23B—C22B—C21B	122.7 (4)	N3—C13—H13K	109.8
C22B—C23B—O4B	118.8 (5)	H13J—C13—H13K	108.3
C22B—C23B—C24B	121.6 (4)	C13—C14—H14J	109.5
O4B—C23B—C24B	119.6 (4)	C13—C14—H14K	109.5
C25B—C24B—C23B	117.5 (5)	H14J—C14—H14K	109.5
C25B—C24B—C28B	119.7 (5)	C13—C14—H14L	109.5
C23B—C24B—C28B	122.8 (4)	H14J—C14—H14L	109.5
C26B—C25B—C24B	121.8 (6)	H14K—C14—H14L	109.5
C26B—C25B—H25F	119.1	C16—C15—N3	114.0 (6)
C24B—C25B—H25F	119.1	C16—C15—H15J	108.7
C27B—C26B—C25B	118.5 (5)	N3—C15—H15J	108.7
C27B—C26B—H26F	120.7	C16—C15—H15K	108.7
C25B—C26B—H26F	120.7	N3—C15—H15K	108.7
C26B—C27B—C22B	122.4 (5)	H15J—C15—H15K	107.6
C26B—C27B—H27F	118.8	C15—C16—H16J	109.5
C22B—C27B—H27F	118.8	C15—C16—H16K	109.5
C2B—C28B—C24B	114.1 (4)	H16J—C16—H16K	109.5
C2B—C28B—H28F	108.7	C15—C16—H16L	109.5
C24B—C28B—H28F	108.7	H16J—C16—H16L	109.5
C2B—C28B—H28G	108.7	H16K—C16—H16L	109.5
C24B—C28B—H28G	108.7	C18—C17—N3	115.0 (5)
H28F—C28B—H28G	107.6	C18—C17—H17J	108.5
C2C—O1C—H1C	113.9	N3—C17—H17J	108.5
C16C—O3C—H3C	109.5	C18—C17—H17K	108.5
C23C—O4C—H4C	107.7	N3—C17—H17K	108.5
C2C—C1C—C6C	118.3 (5)	H17J—C17—H17K	107.5
C2C—C1C—C28C	121.7 (5)	C17—C18—H18J	109.5
C6C—C1C—C28C	119.9 (5)	C17—C18—H18K	109.5
O1C—C2C—C3C	120.9 (4)	H18J—C18—H18K	109.5
O1C—C2C—C1C	117.4 (5)	C17—C18—H18L	109.5
C3C—C2C—C1C	121.6 (5)	H18J—C18—H18L	109.5
C4C—C3C—C2C	118.8 (5)	H18K—C18—H18L	109.5
C4C—C3C—C7C	119.8 (5)	N4—C19—C20	178.5 (10)
C2C—C3C—C7C	121.5 (4)	C19—C20—H20J	109.5
C3C—C4C—C5C	120.7 (6)	C19—C20—H20K	109.5
C3C—C4C—H4H	119.7	H20J—C20—H20K	109.5
C5C—C4C—H4H	119.7	C19—C20—H20L	109.5
C6C—C5C—C4C	119.7 (5)	H20J—C20—H20L	109.5
C6C—C5C—H5H	120.2	H20K—C20—H20L	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2A	0.82	1.75	2.551 (5)	165
O3A—H3A···O2A	0.93	1.68	2.552 (5)	155
O4A—H4A···O3A	0.89	2.05	2.846 (5)	148
N1—H1···O2A	0.93	1.78	2.667 (5)	160
O1B—H1B···O2B	0.81	1.73	2.539 (5)	176
O3B—H3B···O2B	0.96	1.64	2.585 (5)	168
O4B—H4B···O1B	0.92	1.79	2.703 (5)	169
N2—H2···O2B	0.99	1.74	2.699 (5)	161
O1C—H1C···O2C	0.82	1.72	2.523 (5)	170
O3C—H3C···O2C	0.86	1.80	2.625 (5)	158
O4C—H4C···O1C	0.87	1.83	2.683 (5)	164
N3—H3···O2C	0.96	1.83	2.729 (5)	155