Adducts of 1,1,1-tris(4-hydroxyphenyl)ethane with diamines: three-dimensional hydrogen-bonded frameworks formed with 1,6-diaminohexane and 2,2′-bipyridyl

Zakaria, C.M.; Ferguson, G.; Lough, A.J.; Glidewell, C.

doi:10.1107/S0108270102001488

Adducts of 1,1,1-tris(4-hydroxyphenyl)ethane with diamines: three-dimensional hydrogen-bonded frameworks formed with 1,6-diaminohexane and 2,2'-bipyridyl

C. M. Zakaria, G. Ferguson, A. J. Lough and C. Glidewell

The adduct 1,6-diaminohexane-1,1,1-tris(4-hydroxyphenyl)ethane (1/2) is a salt {hexane-1,6-diyldiammonium-4-[1,1-bis(4-hydroxyphenyl)ethyl]phenolate (1/2)}, C₆H₁₈N₂²⁺·2C₂₀H₁₇O₃^-, in which the cation lies across a centre of inversion in space group P $\overline 1$ . The anions are linked by two short O-H

O hydrogen bonds [H

O 1.74 and 1.76 Å, O

O 2.5702 (12) and 2.5855 (12) Å, and O-H

O 168 and 169°] into a chain containing two types of R ${_2^2}$ (24) ring. Each cation is linked to four different anion chains by three N-H

O hydrogen bonds [H

O 1.76-2.06 Å, N

O 2.6749 (14)-2.9159 (14) Å and N-H

O 156-172°]. In the adduct 2,2'-bipyridyl-1,1,1-tris(4-hydroxyphenyl)ethane (1/2), C₁₀H₈N₂·2C₂₀H₁₈O₃, the neutral diamine lies across a centre of inversion in space group P2₁/n. The tris(phenol) molecules are linked by two O-H

O hydrogen bonds [H

O both 1.90 Å, O

O 2.7303 (14) and 2.7415 (15) Å, and O-H

O 173 and 176°] into sheets built from R ${_4^4}$ (38) rings. Pairs of tris(phenol) sheets are linked via the diamine by means of a single O-H

N hydrogen bond [H

N 1.97 Å, O

N 2.7833 (16) Å and O-H

N 163°].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102001488/sk1534sup1.cif Contains datablocks global, I, II
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270102001488/sk1534Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270102001488/sk1534IIsup3.hkl Contains datablock II

CCDC references: 184486; 184487

Computing details top

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: PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

(I) 1,6-Diaminohexane–1,1,1-tris(4-hydroxyphenyl)ethane (1/2) top

Crystal data top

C₆H₁₈N₂²⁺·2C₂₀H₁₇O₃⁻	Z = 1
M_r = 728.9	F(000) = 390
Triclinic, P1	D_x = 1.239 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4715 (1) Å	Cell parameters from 8773 reflections
b = 12.2447 (3) Å	θ = 2.6–27.5°
c = 13.0098 (4) Å	µ = 0.08 mm⁻¹
α = 77.2052 (10)°	T = 150 K
β = 76.6823 (10)°	Needle, colourless
γ = 84.3491 (16)°	0.32 × 0.18 × 0.16 mm
V = 977.06 (4) Å³

Data collection top

Nonius KappaCCD area-detector diffractometer	3584 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	R_int = 0.047
Graphite monochromator	θ_max = 27.5°, θ_min = 2.6°
φ scans, and ω scans with κ offsets	h = −8→8
14162 measured reflections	k = −15→15
4471 independent reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0453P)² + 0.2476P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
4471 reflections	Δρ_max = 0.22 e Å⁻³
249 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.027 (4)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.46206 (13)	0.17863 (7)	1.29742 (7)	0.0215 (2)
O2	0.91048 (15)	0.72346 (8)	0.68778 (9)	0.0320 (2)
O3	0.78819 (15)	−0.01661 (7)	0.61002 (7)	0.0253 (2)
C1	1.00037 (18)	0.25565 (10)	0.87322 (10)	0.0186 (3)
C2	1.23623 (19)	0.22336 (12)	0.87968 (11)	0.0258 (3)
C11	0.85741 (18)	0.23639 (10)	0.98734 (9)	0.0184 (2)
C12	0.9016 (2)	0.14895 (11)	1.06886 (10)	0.0247 (3)
C13	0.7691 (2)	0.12814 (11)	1.17105 (10)	0.0246 (3)
C14	0.58596 (19)	0.19561 (10)	1.19584 (10)	0.0194 (3)
C15	0.5379 (2)	0.28247 (11)	1.11402 (10)	0.0242 (3)
C16	0.67145 (19)	0.30182 (11)	1.01219 (10)	0.0231 (3)
C21	0.97889 (18)	0.38048 (10)	0.81977 (9)	0.0194 (3)
C22	1.0757 (2)	0.46124 (11)	0.85086 (11)	0.0276 (3)
C23	1.0498 (2)	0.57479 (11)	0.80874 (11)	0.0290 (3)
C24	0.92535 (19)	0.61094 (10)	0.73298 (11)	0.0246 (3)
C25	0.8252 (2)	0.53310 (11)	0.70231 (12)	0.0299 (3)
C26	0.8511 (2)	0.41937 (11)	0.74539 (11)	0.0267 (3)
C31	0.93804 (18)	0.18072 (10)	0.80557 (10)	0.0191 (3)
C32	1.0530 (2)	0.18280 (11)	0.69972 (10)	0.0240 (3)
C33	1.0048 (2)	0.11611 (11)	0.63607 (10)	0.0244 (3)
C34	0.83690 (19)	0.04494 (10)	0.67673 (10)	0.0198 (3)
C35	0.72024 (19)	0.04140 (10)	0.78138 (10)	0.0221 (3)
C36	0.77161 (19)	0.10883 (10)	0.84418 (10)	0.0206 (3)
N4	0.71985 (16)	0.16715 (9)	0.43375 (8)	0.0217 (2)
C42	0.5892 (2)	0.23900 (11)	0.50599 (10)	0.0265 (3)
C43	0.6269 (2)	0.36078 (11)	0.46004 (11)	0.0272 (3)
C44	0.4805 (2)	0.43863 (11)	0.52468 (11)	0.0264 (3)
H2	0.7821	0.7462	0.6975	0.048*
H3	0.6993	−0.0638	0.6460	0.038*
H2A	1.2730	0.2579	0.9338	0.039*
H2B	1.3287	0.2502	0.8091	0.039*
H2C	1.2556	0.1416	0.9002	0.039*
H12	1.0261	0.1019	1.0544	0.030*
H13	0.8039	0.0671	1.2246	0.030*
H15	0.4125	0.3289	1.1281	0.029*
H16	0.6348	0.3615	0.9579	0.028*
H22	1.1620	0.4376	0.9025	0.033*
H23	1.1172	0.6277	0.8318	0.035*
H25	0.7377	0.5573	0.6513	0.036*
H26	0.7800	0.3671	0.7235	0.032*
H32	1.1673	0.2314	0.6708	0.029*
H33	1.0861	0.1189	0.5648	0.029*
H35	0.6055	−0.0070	0.8100	0.027*
H36	0.6904	0.1056	0.9155	0.025*
H4A	0.8452	0.1994	0.4002	0.033*
H4B	0.6480	0.1599	0.3834	0.033*
H4C	0.7461	0.0982	0.4736	0.033*
H42A	0.6258	0.2179	0.5779	0.032*
H42B	0.4367	0.2261	0.5154	0.032*
H43A	0.6060	0.3791	0.3850	0.033*
H43B	0.7764	0.3744	0.4577	0.033*
H44A	0.3308	0.4246	0.5281	0.032*
H44B	0.5032	0.4217	0.5994	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0239 (4)	0.0223 (4)	0.0164 (4)	−0.0040 (3)	−0.0007 (3)	−0.0023 (3)
O2	0.0236 (5)	0.0187 (5)	0.0443 (6)	−0.0011 (4)	0.0037 (4)	0.0015 (4)
O3	0.0368 (5)	0.0214 (5)	0.0174 (4)	−0.0091 (4)	−0.0019 (4)	−0.0039 (4)
C1	0.0174 (5)	0.0190 (6)	0.0187 (6)	−0.0003 (4)	−0.0031 (4)	−0.0035 (5)
C2	0.0193 (6)	0.0292 (7)	0.0282 (7)	0.0013 (5)	−0.0046 (5)	−0.0061 (5)
C11	0.0197 (5)	0.0182 (6)	0.0183 (6)	−0.0021 (4)	−0.0046 (4)	−0.0050 (5)
C12	0.0255 (6)	0.0235 (6)	0.0226 (6)	0.0062 (5)	−0.0038 (5)	−0.0043 (5)
C13	0.0298 (6)	0.0216 (6)	0.0198 (6)	0.0032 (5)	−0.0064 (5)	0.0001 (5)
C14	0.0215 (6)	0.0202 (6)	0.0170 (6)	−0.0051 (5)	−0.0031 (4)	−0.0042 (5)
C15	0.0204 (6)	0.0253 (7)	0.0233 (7)	0.0026 (5)	−0.0017 (5)	−0.0022 (5)
C16	0.0224 (6)	0.0243 (6)	0.0199 (6)	0.0023 (5)	−0.0049 (5)	0.0000 (5)
C21	0.0184 (5)	0.0203 (6)	0.0175 (6)	−0.0022 (4)	0.0004 (4)	−0.0032 (5)
C22	0.0322 (7)	0.0276 (7)	0.0248 (7)	−0.0069 (5)	−0.0095 (5)	−0.0033 (5)
C23	0.0333 (7)	0.0232 (7)	0.0314 (7)	−0.0090 (5)	−0.0049 (6)	−0.0061 (6)
C24	0.0220 (6)	0.0185 (6)	0.0278 (7)	−0.0022 (5)	0.0043 (5)	−0.0028 (5)
C25	0.0314 (7)	0.0250 (7)	0.0339 (8)	0.0002 (5)	−0.0140 (6)	−0.0011 (6)
C26	0.0286 (6)	0.0213 (6)	0.0330 (7)	−0.0025 (5)	−0.0125 (6)	−0.0046 (5)
C31	0.0191 (5)	0.0175 (6)	0.0198 (6)	0.0015 (4)	−0.0036 (4)	−0.0037 (5)
C32	0.0245 (6)	0.0221 (6)	0.0227 (6)	−0.0059 (5)	0.0017 (5)	−0.0042 (5)
C33	0.0276 (6)	0.0244 (6)	0.0182 (6)	−0.0042 (5)	0.0021 (5)	−0.0044 (5)
C34	0.0259 (6)	0.0151 (6)	0.0182 (6)	0.0009 (5)	−0.0053 (5)	−0.0030 (5)
C35	0.0226 (6)	0.0209 (6)	0.0210 (6)	−0.0050 (5)	−0.0017 (5)	−0.0019 (5)
C36	0.0200 (6)	0.0215 (6)	0.0181 (6)	−0.0010 (5)	0.0001 (5)	−0.0040 (5)
N4	0.0242 (5)	0.0204 (5)	0.0194 (5)	−0.0018 (4)	−0.0028 (4)	−0.0035 (4)
C42	0.0301 (7)	0.0268 (7)	0.0203 (6)	0.0020 (5)	−0.0003 (5)	−0.0070 (5)
C43	0.0271 (6)	0.0243 (7)	0.0275 (7)	−0.0001 (5)	0.0003 (5)	−0.0066 (5)
C44	0.0269 (6)	0.0255 (7)	0.0246 (7)	0.0002 (5)	−0.0010 (5)	−0.0062 (5)

Geometric parameters (Å, º) top

O1—C14	1.3622 (14)	C24—C25	1.3771 (19)
O2—C24	1.3764 (15)	C25—C26	1.3905 (19)
O2—H2	0.84	C25—H25	0.95
O3—C34	1.3723 (14)	C26—H26	0.95
O3—H3	0.84	C31—C36	1.3888 (17)
C1—C11	1.5398 (16)	C31—C32	1.4022 (17)
C1—C21	1.5398 (17)	C32—C33	1.3851 (18)
C1—C31	1.5406 (16)	C32—H32	0.95
C1—C2	1.5552 (16)	C33—C34	1.3918 (17)
C2—H2A	0.98	C33—H33	0.95
C2—H2B	0.98	C34—C35	1.3900 (17)
C2—H2C	0.98	C35—C36	1.3921 (17)
C11—C12	1.3892 (18)	C35—H35	0.95
C11—C16	1.3929 (17)	C36—H36	0.95
C12—C13	1.3914 (18)	N4—C42	1.4920 (16)
C12—H12	0.95	N4—H4A	0.91
C13—C14	1.3928 (17)	N4—H4B	0.91
C13—H13	0.95	N4—H4C	0.91
C14—C15	1.3953 (17)	C42—C43	1.5002 (19)
C15—C16	1.3899 (17)	C42—H42A	0.99
C15—H15	0.95	C42—H42B	0.99
C16—H16	0.95	C43—C44	1.5245 (18)
C21—C26	1.3905 (18)	C43—H43A	0.99
C21—C22	1.3964 (17)	C43—H43B	0.99
C22—C23	1.3859 (19)	C44—C44ⁱ	1.519 (3)
C22—H22	0.95	C44—H44A	0.99
C23—C24	1.385 (2)	C44—H44B	0.99
C23—H23	0.95

C24—O2—H2	109.5	C26—C25—H25	119.7
C34—O3—H3	109.5	C25—C26—C21	121.48 (12)
C11—C1—C21	108.71 (9)	C25—C26—H26	119.3
C11—C1—C31	110.49 (9)	C21—C26—H26	119.3
C21—C1—C31	110.90 (10)	C36—C31—C32	116.98 (11)
C11—C1—C2	110.12 (10)	C36—C31—C1	123.26 (11)
C21—C1—C2	109.45 (10)	C32—C31—C1	119.76 (10)
C31—C1—C2	107.15 (10)	C33—C32—C31	121.97 (11)
C1—C2—H2A	109.5	C33—C32—H32	119.0
C1—C2—H2B	109.5	C31—C32—H32	119.0
H2A—C2—H2B	109.5	C32—C33—C34	119.86 (11)
C1—C2—H2C	109.5	C32—C33—H33	120.1
H2A—C2—H2C	109.5	C34—C33—H33	120.1
H2B—C2—H2C	109.5	O3—C34—C35	122.34 (11)
C12—C11—C16	116.75 (11)	O3—C34—C33	118.31 (11)
C12—C11—C1	121.50 (11)	C35—C34—C33	119.31 (11)
C16—C11—C1	121.65 (11)	C34—C35—C36	119.95 (11)
C11—C12—C13	121.97 (11)	C34—C35—H35	120.0
C11—C12—H12	119.0	C36—C35—H35	120.0
C13—C12—H12	119.0	C31—C36—C35	121.92 (11)
C12—C13—C14	120.83 (11)	C31—C36—H36	119.0
C12—C13—H13	119.6	C35—C36—H36	119.0
C14—C13—H13	119.6	C42—N4—H4A	109.5
O1—C14—C13	120.75 (11)	C42—N4—H4B	109.5
O1—C14—C15	121.53 (11)	H4A—N4—H4B	109.5
C13—C14—C15	117.69 (11)	C42—N4—H4C	109.5
C16—C15—C14	120.76 (11)	H4A—N4—H4C	109.5
C16—C15—H15	119.6	H4B—N4—H4C	109.5
C14—C15—H15	119.6	N4—C42—C43	111.04 (10)
C15—C16—C11	121.96 (11)	N4—C42—H42A	109.4
C15—C16—H16	119.0	C43—C42—H42A	109.4
C11—C16—H16	119.0	N4—C42—H42B	109.4
C26—C21—C22	116.80 (12)	C43—C42—H42B	109.4
C26—C21—C1	122.40 (11)	H42A—C42—H42B	108.0
C22—C21—C1	120.62 (11)	C42—C43—C44	113.18 (11)
C23—C22—C21	122.07 (12)	C42—C43—H43A	108.9
C23—C22—H22	119.0	C44—C43—H43A	108.9
C21—C22—H22	119.0	C42—C43—H43B	108.9
C24—C23—C22	119.86 (12)	C44—C43—H43B	108.9
C24—C23—H23	120.1	H43A—C43—H43B	107.8
C22—C23—H23	120.1	C44ⁱ—C44—C43	112.07 (13)
O2—C24—C25	121.70 (12)	C44ⁱ—C44—H44A	109.2
O2—C24—C23	119.06 (12)	C43—C44—H44A	109.2
C25—C24—C23	119.21 (12)	C44ⁱ—C44—H44B	109.2
C24—C25—C26	120.56 (12)	C43—C44—H44B	109.2
C24—C25—H25	119.7	H44A—C44—H44B	107.9

C21—C1—C11—C12	−154.06 (11)	C22—C23—C24—O2	−176.59 (12)
C31—C1—C11—C12	84.02 (13)	C22—C23—C24—C25	1.4 (2)
C2—C1—C11—C12	−34.16 (15)	O2—C24—C25—C26	176.86 (12)
C21—C1—C11—C16	29.54 (15)	C23—C24—C25—C26	−1.0 (2)
C31—C1—C11—C16	−92.38 (13)	C24—C25—C26—C21	−0.4 (2)
C2—C1—C11—C16	149.44 (11)	C22—C21—C26—C25	1.43 (19)
C16—C11—C12—C13	−0.89 (19)	C1—C21—C26—C25	176.59 (12)
C1—C11—C12—C13	−177.45 (11)	C11—C1—C31—C36	1.44 (15)
C11—C12—C13—C14	−0.5 (2)	C21—C1—C31—C36	−119.18 (12)
C12—C13—C14—O1	−176.68 (11)	C2—C1—C31—C36	121.41 (12)
C12—C13—C14—C15	1.63 (19)	C11—C1—C31—C32	−178.12 (11)
O1—C14—C15—C16	176.98 (11)	C21—C1—C31—C32	61.26 (14)
C13—C14—C15—C16	−1.32 (19)	C2—C1—C31—C32	−58.15 (14)
C14—C15—C16—C11	−0.1 (2)	C36—C31—C32—C33	−0.34 (19)
C12—C11—C16—C15	1.20 (19)	C1—C31—C32—C33	179.25 (11)
C1—C11—C16—C15	177.76 (11)	C31—C32—C33—C34	0.5 (2)
C11—C1—C21—C26	−100.42 (13)	C32—C33—C34—O3	177.43 (11)
C31—C1—C21—C26	21.25 (16)	C32—C33—C34—C35	−0.35 (19)
C2—C1—C21—C26	139.26 (12)	O3—C34—C35—C36	−177.53 (11)
C11—C1—C21—C22	74.56 (13)	C33—C34—C35—C36	0.15 (18)
C31—C1—C21—C22	−163.78 (11)	C32—C31—C36—C35	0.13 (18)
C2—C1—C21—C22	−45.77 (15)	C1—C31—C36—C35	−179.44 (11)
C26—C21—C22—C23	−1.09 (19)	C34—C35—C36—C31	−0.05 (19)
C1—C21—C22—C23	−176.34 (12)	N4—C42—C43—C44	174.00 (11)
C21—C22—C23—C24	−0.3 (2)	C42—C43—C44—C44ⁱ	−179.02 (14)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱⁱ	0.84	1.74	2.5702 (12)	168
O3—H3···O1ⁱⁱⁱ	0.84	1.76	2.5855 (12)	169
N4—H4A···O2^iv	0.91	1.92	2.8227 (14)	172
N4—H4B···O1^v	0.91	1.79	2.6749 (14)	164
N4—H4C···O3	0.91	2.06	2.9159 (14)	156

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

(II) 2,2'-Bipyridyl–1,1,1-tris(4-hydroxyphenyl)ethane (1/2) top

Crystal data top

C₁₀H₈N₂·2C₂₀H₁₈O₃	F(000) = 812
M_r = 768.88	D_x = 1.288 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8697 reflections
a = 12.1021 (4) Å	θ = 2.7–27.5°
b = 10.7710 (4) Å	µ = 0.08 mm⁻¹
c = 15.2142 (6) Å	T = 150 K
β = 90.2800 (17)°	Block, colourless
V = 1983.17 (13) Å³	0.32 × 0.30 × 0.16 mm
Z = 2

Data collection top

Nonius KappaCCD area-detector diffractometer	3423 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	R_int = 0.051
Graphite monochromator	θ_max = 27.5°, θ_min = 2.7°
φ scans, and ω scans with κ offsets	h = −15→15
12870 measured reflections	k = −13→13
4511 independent reflections	l = −19→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0454P)² + 0.4013P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
4511 reflections	Δρ_max = 0.24 e Å⁻³
267 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (3)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.23588 (8)	0.48459 (10)	0.66499 (6)	0.0320 (3)
O2	0.52357 (8)	−0.04513 (9)	1.12120 (7)	0.0282 (2)
O3	0.42111 (9)	0.78209 (10)	1.22503 (7)	0.0347 (3)
C1	0.24707 (11)	0.36947 (13)	1.03311 (9)	0.0236 (3)
C2	0.12710 (11)	0.34008 (14)	1.06157 (10)	0.0292 (3)
C11	0.24587 (11)	0.39412 (13)	0.93330 (9)	0.0243 (3)
C12	0.17249 (12)	0.48280 (14)	0.89915 (10)	0.0311 (3)
C13	0.17043 (12)	0.51237 (15)	0.81091 (10)	0.0321 (3)
C14	0.24210 (11)	0.45398 (14)	0.75348 (9)	0.0263 (3)
C15	0.31504 (12)	0.36589 (15)	0.78501 (10)	0.0312 (3)
C16	0.31634 (11)	0.33658 (14)	0.87434 (9)	0.0287 (3)
C21	0.32276 (11)	0.25920 (13)	1.05718 (8)	0.0235 (3)
C22	0.28760 (11)	0.13663 (13)	1.04678 (9)	0.0275 (3)
C23	0.35429 (11)	0.03662 (13)	1.06848 (9)	0.0279 (3)
C24	0.46029 (11)	0.05728 (13)	1.10088 (9)	0.0236 (3)
C25	0.49778 (11)	0.17707 (13)	1.11205 (9)	0.0263 (3)
C26	0.42926 (11)	0.27670 (13)	1.09074 (9)	0.0253 (3)
C31	0.28898 (11)	0.48527 (13)	1.08198 (9)	0.0240 (3)
C32	0.27011 (12)	0.49959 (14)	1.17192 (10)	0.0307 (3)
C33	0.31436 (13)	0.59832 (15)	1.21887 (10)	0.0334 (3)
C34	0.37854 (11)	0.68614 (13)	1.17644 (9)	0.0267 (3)
C35	0.39807 (11)	0.67445 (13)	1.08714 (9)	0.0261 (3)
C36	0.35390 (11)	0.57450 (13)	1.04097 (9)	0.0250 (3)
C41	0.51149 (11)	0.54965 (13)	0.53285 (10)	0.0267 (3)
N42	0.44216 (10)	0.55602 (12)	0.60265 (8)	0.0340 (3)
C43	0.45989 (14)	0.64522 (17)	0.66240 (11)	0.0420 (4)
C44	0.54567 (14)	0.72983 (17)	0.65730 (11)	0.0421 (4)
C45	0.61528 (12)	0.72441 (15)	0.58626 (11)	0.0364 (4)
C46	0.59770 (12)	0.63309 (14)	0.52340 (11)	0.0332 (3)
H1	0.3000	0.4905	0.6444	0.048*
H2	0.5891	−0.0229	1.1304	0.042*
H3	0.4538	0.8320	1.1916	0.052*
H2A	0.1274	0.3089	1.1221	0.044*
H2B	0.0957	0.2769	1.0224	0.044*
H2C	0.0824	0.4158	1.0582	0.044*
H12	0.1229	0.5236	0.9378	0.037*
H13	0.1198	0.5728	0.7895	0.038*
H15	0.3643	0.3253	0.7460	0.037*
H16	0.3668	0.2757	0.8953	0.034*
H22	0.2156	0.1213	1.0241	0.033*
H23	0.3277	−0.0457	1.0612	0.033*
H25	0.5701	0.1917	1.1342	0.032*
H26	0.4557	0.3589	1.0993	0.030*
H32	0.2259	0.4402	1.2017	0.037*
H33	0.3007	0.6057	1.2801	0.040*
H35	0.4416	0.7346	1.0575	0.031*
H36	0.3684	0.5670	0.9799	0.030*
H43	0.4110	0.6507	0.7109	0.050*
H44	0.5562	0.7904	0.7020	0.051*
H45	0.6742	0.7820	0.5803	0.044*
H46	0.6449	0.6278	0.4738	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0243 (5)	0.0480 (7)	0.0236 (5)	−0.0032 (5)	−0.0020 (4)	0.0077 (5)
O2	0.0252 (5)	0.0271 (5)	0.0322 (6)	0.0019 (4)	−0.0044 (4)	0.0024 (4)
O3	0.0455 (6)	0.0319 (6)	0.0269 (5)	−0.0078 (5)	0.0020 (5)	−0.0045 (4)
C1	0.0210 (6)	0.0258 (7)	0.0240 (7)	0.0010 (5)	−0.0013 (5)	0.0013 (6)
C2	0.0227 (7)	0.0355 (8)	0.0293 (7)	0.0000 (6)	0.0017 (6)	0.0034 (6)
C11	0.0211 (6)	0.0274 (7)	0.0242 (7)	−0.0020 (5)	−0.0031 (5)	0.0004 (6)
C12	0.0294 (7)	0.0372 (8)	0.0268 (7)	0.0092 (6)	−0.0006 (6)	0.0002 (6)
C13	0.0298 (7)	0.0362 (8)	0.0301 (8)	0.0084 (6)	−0.0053 (6)	0.0037 (6)
C14	0.0237 (6)	0.0339 (8)	0.0212 (7)	−0.0054 (6)	−0.0031 (5)	0.0041 (6)
C15	0.0286 (7)	0.0398 (8)	0.0252 (7)	0.0060 (6)	0.0018 (6)	−0.0007 (6)
C16	0.0254 (7)	0.0337 (8)	0.0268 (7)	0.0063 (6)	−0.0017 (6)	0.0017 (6)
C21	0.0229 (6)	0.0285 (7)	0.0190 (6)	0.0002 (5)	−0.0011 (5)	0.0021 (5)
C22	0.0219 (6)	0.0301 (8)	0.0305 (7)	−0.0011 (5)	−0.0059 (5)	−0.0005 (6)
C23	0.0274 (7)	0.0255 (7)	0.0307 (7)	−0.0027 (5)	−0.0035 (6)	−0.0011 (6)
C24	0.0250 (7)	0.0259 (7)	0.0200 (6)	0.0028 (5)	−0.0010 (5)	0.0014 (5)
C25	0.0220 (6)	0.0298 (7)	0.0272 (7)	−0.0009 (5)	−0.0039 (5)	0.0003 (6)
C26	0.0242 (7)	0.0246 (7)	0.0269 (7)	−0.0021 (5)	−0.0013 (5)	0.0005 (6)
C31	0.0217 (6)	0.0260 (7)	0.0243 (7)	0.0036 (5)	−0.0007 (5)	0.0005 (5)
C32	0.0354 (8)	0.0302 (7)	0.0264 (7)	−0.0038 (6)	0.0036 (6)	0.0028 (6)
C33	0.0432 (8)	0.0351 (8)	0.0220 (7)	−0.0029 (7)	0.0030 (6)	−0.0008 (6)
C34	0.0286 (7)	0.0269 (7)	0.0246 (7)	0.0016 (6)	−0.0017 (5)	−0.0029 (6)
C35	0.0240 (7)	0.0287 (7)	0.0255 (7)	−0.0003 (5)	0.0021 (5)	0.0015 (6)
C36	0.0234 (6)	0.0306 (8)	0.0211 (6)	0.0025 (5)	0.0005 (5)	−0.0006 (6)
C41	0.0210 (6)	0.0275 (7)	0.0314 (7)	0.0019 (5)	−0.0043 (5)	0.0023 (6)
N42	0.0310 (6)	0.0400 (7)	0.0310 (7)	−0.0055 (6)	−0.0021 (5)	−0.0004 (6)
C43	0.0395 (9)	0.0505 (10)	0.0362 (9)	−0.0111 (8)	0.0047 (7)	−0.0080 (8)
C44	0.0390 (9)	0.0467 (10)	0.0405 (9)	−0.0098 (7)	−0.0025 (7)	−0.0085 (8)
C45	0.0264 (7)	0.0375 (9)	0.0454 (9)	−0.0063 (6)	−0.0038 (7)	−0.0042 (7)
C46	0.0245 (7)	0.0330 (8)	0.0421 (9)	−0.0014 (6)	0.0013 (6)	0.0001 (7)

Geometric parameters (Å, º) top

O1—C14	1.3877 (16)	C23—C24	1.3900 (19)
O1—H1	0.84	C23—H23	0.95
O2—C24	1.3770 (16)	C24—C25	1.3780 (19)
O2—H2	0.84	C25—C26	1.3935 (19)
O3—C34	1.3698 (17)	C25—H25	0.95
O3—H3	0.84	C26—H26	0.95
C1—C31	1.5369 (19)	C31—C36	1.3911 (19)
C1—C11	1.5415 (18)	C31—C32	1.3970 (19)
C1—C21	1.5429 (18)	C32—C33	1.387 (2)
C1—C2	1.5497 (18)	C32—H32	0.95
C2—H2A	0.98	C33—C34	1.386 (2)
C2—H2B	0.98	C33—H33	0.95
C2—H2C	0.98	C34—C35	1.3860 (19)
C11—C16	1.387 (2)	C35—C36	1.3909 (19)
C11—C12	1.4023 (19)	C35—H35	0.95
C12—C13	1.380 (2)	C36—H36	0.95
C12—H12	0.95	C41—N42	1.3583 (19)
C13—C14	1.385 (2)	C41—C46	1.385 (2)
C13—H13	0.95	C41—C41ⁱ	1.489 (3)
C14—C15	1.380 (2)	N42—C43	1.339 (2)
C15—C16	1.395 (2)	C43—C44	1.384 (2)
C15—H15	0.95	C43—H43	0.95
C16—H16	0.95	C44—C45	1.375 (2)
C21—C22	1.3958 (19)	C44—H44	0.95
C21—C26	1.3968 (18)	C45—C46	1.388 (2)
C22—C23	1.385 (2)	C45—H45	0.95
C22—H22	0.95	C46—H46	0.95

C14—O1—H1	109.5	O2—C24—C23	117.56 (12)
C24—O2—H2	109.5	C25—C24—C23	119.76 (12)
C34—O3—H3	109.5	C24—C25—C26	119.82 (12)
C31—C1—C11	109.77 (11)	C24—C25—H25	120.1
C31—C1—C21	108.41 (10)	C26—C25—H25	120.1
C11—C1—C21	111.66 (11)	C25—C26—C21	121.88 (13)
C31—C1—C2	109.76 (11)	C25—C26—H26	119.1
C11—C1—C2	107.82 (10)	C21—C26—H26	119.1
C21—C1—C2	109.41 (11)	C36—C31—C32	117.29 (13)
C1—C2—H2A	109.5	C36—C31—C1	121.97 (12)
C1—C2—H2B	109.5	C32—C31—C1	120.56 (12)
H2A—C2—H2B	109.5	C33—C32—C31	121.64 (14)
C1—C2—H2C	109.5	C33—C32—H32	119.2
H2A—C2—H2C	109.5	C31—C32—H32	119.2
H2B—C2—H2C	109.5	C34—C33—C32	119.96 (14)
C16—C11—C12	117.07 (13)	C34—C33—H33	120.0
C16—C11—C1	123.87 (12)	C32—C33—H33	120.0
C12—C11—C1	119.03 (12)	O3—C34—C33	118.28 (12)
C13—C12—C11	121.74 (13)	O3—C34—C35	122.15 (13)
C13—C12—H12	119.1	C33—C34—C35	119.56 (13)
C11—C12—H12	119.1	C34—C35—C36	119.90 (13)
C12—C13—C14	120.04 (13)	C34—C35—H35	120.1
C12—C13—H13	120.0	C36—C35—H35	120.1
C14—C13—H13	120.0	C35—C36—C31	121.65 (13)
C15—C14—C13	119.61 (13)	C35—C36—H36	119.2
C15—C14—O1	122.15 (13)	C31—C36—H36	119.2
C13—C14—O1	118.23 (13)	N42—C41—C46	121.12 (14)
C14—C15—C16	119.89 (13)	N42—C41—C41ⁱ	116.55 (15)
C14—C15—H15	120.1	C46—C41—C41ⁱ	122.32 (17)
C16—C15—H15	120.1	C43—N42—C41	117.99 (13)
C11—C16—C15	121.65 (13)	N42—C43—C44	123.51 (15)
C11—C16—H16	119.2	N42—C43—H43	118.2
C15—C16—H16	119.2	C44—C43—H43	118.2
C22—C21—C26	116.70 (12)	C45—C44—C43	118.61 (16)
C22—C21—C1	121.39 (11)	C45—C44—H44	120.7
C26—C21—C1	121.90 (12)	C43—C44—H44	120.7
C23—C22—C21	122.12 (12)	C44—C45—C46	118.65 (14)
C23—C22—H22	118.9	C44—C45—H45	120.7
C21—C22—H22	118.9	C46—C45—H45	120.7
C22—C23—C24	119.72 (13)	C41—C46—C45	120.10 (15)
C22—C23—H23	120.1	C41—C46—H46	120.0
C24—C23—H23	120.1	C45—C46—H46	120.0
O2—C24—C25	122.68 (12)

C2—C1—C11—C12	53.23 (16)	C2—C1—C31—C32	44.22 (17)
C2—C1—C21—C22	39.62 (17)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N42	0.84	1.97	2.7833 (16)	163
O2—H2···O1ⁱⁱ	0.84	1.90	2.7303 (14)	173
O3—H3···O2ⁱⁱⁱ	0.84	1.90	2.7415 (15)	176

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

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