2,2'-{[2-(2-Hy-droxy-phen-yl)-4-methyl-imidazolidine-1,3-di-yl]bis-(methyl-ene)}diphenol.

The asymmetric unit in the title compound, C24H26N2O3, comprises two independent mol-ecules (A and B). In molecule A, the central 2-hydroxyphenyl ring is inclined to the mean plane of the major component of the imidazolidine ring by 84.52 (14)°, and by 68.08 (9) and 47.48 (9)° to the outer phenol rings. The later are inclined to one another by 66.76 (9)° and by 78.12 (14) and 80.20 (14)° to the imidazoline ring mean plane. In molecule B, the central 2-hydroxyphenyl ring is inclined to the mean plane of the imidazolidine ring by 73.64 (10)°, and by 75.60 (8) and 38.32 (9)° to the outer phenol rings. The later are inclined to one another by 69.47 (9)° and by 82.60 (10) and 64.26 (10)° to the imidazolidine ring mean plane. In each of the independent mol-ecules, two intra-molecular O-H⋯N hydrogen bond form S(6) ring motifs. In disordered mol-ecule A, the O-H groups of the 2-hy-droxy-benzyl groups are also involved in intra-molecular O-H⋯O hydrogen bonds, with the O atom of the hy-droxy-phenyl group acting as the acceptor. In the crystal, A molecules are linked by pairs of O-H⋯O hydrogen bonds forming inversion dimers. These dimers are linked to the B molecules via O-H⋯O hydrogen bonds forming double-layered slabs lying parallel to the bc plane.

Related literature

For related structures, see: Rivera et al. (2012 ▶, 2013b ▶,c ▶). For the synthesis of the title compound, see: Rivera et al. (2013a ▶). For reference bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond graph-set nomenclature, see: Bernstein et al. (1995 ▶). For Cremer–Pople ring-puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C24H26N2O3

M = 390.47

Monoclinic,

a = 24.2482 (10) Å

b = 9.8145 (3) Å

c = 35.1675 (15) Å

β = 102.450 (4)°

V = 8172.5 (6) Å3

Z = 16

Cu Kα radiation

μ = 0.67 mm−1

T = 120 K

0.20 × 0.11 × 0.05 mm

Data collection

Agilent Xcalibur Gemini ultra diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.505, T max = 1.000

15999 measured reflections

7053 independent reflections

5315 reflections with I > 3σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.048

S = 1.68

7053 reflections

556 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813019417/sj5345sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019417/sj5345Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019417/sj5345Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C24H26N2O3	F(000) = 3328
Mr = 390.47	Dx = 1.269 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -C 2yc	Cell parameters from 7208 reflections
a = 24.2482 (10) Å	θ = 3.7–67.0°
b = 9.8145 (3) Å	µ = 0.67 mm−1
c = 35.1675 (15) Å	T = 120 K
β = 102.450 (4)°	Polygon, colourless
V = 8172.5 (6) Å3	0.20 × 0.11 × 0.05 mm
Z = 16

Agilent Xcalibur Gemini ultra diffractometer with Atlas detector	7053 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	5315 reflections with I > 3σ(I)
Mirror monochromator	Rint = 0.027
Detector resolution: 10.3784 pixels mm-1	θmax = 67.1°, θmin = 4.1°
ω scans	h = −24→28
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→10
Tmin = 0.505, Tmax = 1.000	l = −41→40
15999 measured reflections

Refinement on F	231 constraints
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.048	Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2)
S = 1.68	(Δ/σ)max = 0.022
7053 reflections	Δρmax = 0.31 e Å−3
556 parameters	Δρmin = −0.19 e Å−3
7 restraints

Experimental. CrysAlisPro, Agilent, 2010 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement. The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.95371 (6)	0.19541 (14)	0.01694 (4)	0.0419 (5)
O2	0.78858 (5)	0.22409 (14)	0.12403 (4)	0.0378 (4)
O3	0.78818 (5)	0.48488 (14)	0.19668 (4)	0.0387 (5)
O4	0.94590 (5)	−0.01395 (14)	−0.13241 (3)	0.0364 (4)
O5	0.95161 (5)	−0.02816 (13)	−0.04311 (3)	0.0325 (4)
O6	0.94669 (6)	0.28240 (15)	0.34574 (4)	0.0432 (5)
N2	0.87484 (6)	0.35663 (14)	0.24227 (4)	0.0265 (5)
N3	0.86673 (6)	0.19986 (14)	−0.04268 (4)	0.0246 (4)
N4	0.88014 (6)	0.26264 (14)	0.18386 (4)	0.0269 (5)
N1	0.87030 (6)	0.12455 (14)	−0.10395 (4)	0.0270 (5)
C45	0.92473 (8)	0.29225 (19)	0.03307 (5)	0.0320 (6)
C46	0.82322 (7)	0.13953 (18)	0.10878 (5)	0.0295 (6)
C47	0.95436 (9)	0.3752 (2)	0.06230 (5)	0.0418 (7)
C48	0.88388 (7)	0.51481 (17)	0.18940 (4)	0.0270 (5)
C1	0.90105 (7)	0.37983 (17)	0.20879 (5)	0.0264 (5)
C2	0.85171 (7)	−0.04658 (18)	−0.05479 (5)	0.0278 (5)
C3	0.92609 (10)	0.4723 (2)	0.07911 (5)	0.0424 (7)
C4	0.85081 (10)	0.75819 (19)	0.15069 (5)	0.0413 (7)
C5	0.79881 (8)	0.05083 (19)	0.07899 (5)	0.0346 (6)
C6	0.86364 (11)	−0.3038 (2)	−0.01921 (6)	0.0477 (8)
C7	0.82775 (8)	0.55781 (18)	0.18302 (5)	0.0312 (6)
C8	0.83500 (7)	0.21722 (18)	−0.01195 (5)	0.0288 (6)
C9	0.80471 (9)	−0.1247 (2)	−0.05198 (5)	0.0383 (7)
C10	0.84272 (7)	0.09546 (17)	−0.07138 (5)	0.0267 (5)
C11	0.87636 (11)	0.1786 (2)	−0.23652 (5)	0.0477 (8)
C12	0.89522 (8)	0.34332 (18)	0.34300 (5)	0.0312 (6)
C13	0.86650 (8)	0.30750 (17)	0.02005 (5)	0.0277 (5)
C14	0.90529 (8)	−0.10177 (17)	−0.03976 (5)	0.0279 (5)
C15	0.91066 (10)	−0.22970 (19)	−0.02197 (5)	0.0384 (7)
C16	0.81141 (9)	0.67841 (19)	0.16319 (5)	0.0384 (7)
C17	0.88192 (7)	0.14208 (17)	0.12213 (5)	0.0267 (5)
C18	0.86977 (8)	0.20647 (18)	0.24694 (5)	0.0339 (6)
C19	0.86484 (9)	0.3312 (2)	0.37219 (5)	0.0368 (6)
C20	0.84506 (10)	0.1634 (2)	−0.20836 (5)	0.0438 (7)
C21	0.83213 (8)	−0.0343 (2)	0.06214 (5)	0.0360 (6)
C22	0.87397 (8)	0.41967 (18)	0.30986 (5)	0.0290 (6)
C23	0.79147 (9)	0.47089 (19)	0.33567 (5)	0.0384 (7)
C24	0.88997 (8)	−0.03312 (19)	0.07506 (5)	0.0349 (6)
C25	0.91415 (8)	0.05456 (18)	0.10489 (5)	0.0313 (6)
C26	0.86595 (14)	0.3233 (9)	−0.06671 (12)	0.0283 (8)	0.7544
C26'	0.8776 (5)	0.323 (3)	−0.0652 (4)	0.0283 (8)	0.2456
C27	0.88837 (8)	0.14813 (18)	0.21160 (5)	0.0324 (6)
C28	0.90970 (7)	0.24526 (18)	0.15184 (5)	0.0297 (6)
C29	0.92237 (8)	0.05111 (18)	−0.16700 (5)	0.0303 (6)
C30	0.92320 (9)	0.59829 (18)	0.17732 (5)	0.0335 (6)
C31	0.82189 (8)	0.48319 (19)	0.30694 (5)	0.0348 (6)
C32	0.86847 (9)	0.4870 (2)	0.06741 (5)	0.0404 (7)
C33	0.81058 (10)	−0.2528 (2)	−0.03426 (6)	0.0496 (8)
C34	0.86738 (8)	0.09890 (19)	−0.17311 (5)	0.0313 (6)
C35	0.90488 (8)	0.43120 (19)	0.27722 (5)	0.0316 (6)
C36	0.83919 (9)	0.40474 (18)	0.03783 (5)	0.0352 (6)
C37	0.81342 (9)	0.39430 (19)	0.36837 (5)	0.0382 (7)
C38	0.95412 (9)	0.0660 (2)	−0.19492 (6)	0.0419 (7)
C39	0.90683 (10)	0.71999 (19)	0.15794 (5)	0.0412 (7)
C40	0.88940 (11)	0.2730 (3)	−0.10092 (7)	0.0297 (8)	0.7544
C40'	0.8611 (3)	0.2702 (10)	−0.1067 (3)	0.0297 (8)	0.2456
C41	0.93073 (10)	0.1306 (2)	−0.22976 (6)	0.0474 (8)
C42	0.83485 (8)	0.0823 (2)	−0.14163 (5)	0.0390 (7)
C43	0.80854 (9)	0.1690 (2)	0.24714 (6)	0.0444 (7)
C44	0.95226 (11)	0.2901 (3)	−0.09486 (8)	0.0457 (10)	0.7544
H1C47	0.994508	0.365094	0.070848	0.0502*
H1C1	0.941523	0.385416	0.21539	0.0317*
H1C3	0.946827	0.530325	0.09917	0.0508*
H1C4	0.839141	0.841134	0.136801	0.0495*
H1C5	0.758507	0.048774	0.070097	0.0416*
H1C6	0.867804	−0.391325	−0.006743	0.0572*
H1C8	0.828765	0.129791	−0.001377	0.0345*
H2C8	0.798809	0.256682	−0.022827	0.0345*
H1C9	0.767564	−0.089786	−0.062453	0.046*
H1C10	0.80234	0.09867	−0.079694	0.0321*
H1C11	0.860151	0.22247	−0.260745	0.0572*
H1C15	0.94756	−0.266204	−0.011581	0.0461*
H1C16	0.772569	0.706364	0.158165	0.0461*
H1C18	0.892046	0.171781	0.270903	0.0407*
H1C19	0.879891	0.278525	0.395072	0.0442*
H1C20	0.80716	0.197972	−0.213141	0.0525*
H1C21	0.814971	−0.094283	0.041399	0.0432*
H1C23	0.755492	0.514983	0.332976	0.0461*
H1C24	0.913261	−0.092445	0.063519	0.0419*
H1C25	0.954443	0.054698	0.113879	0.0375*
H1C27	0.927746	0.125176	0.218571	0.0389*
H2C27	0.86383	0.074385	0.200981	0.0389*
H1C28	0.948094	0.218689	0.162231	0.0357*
H2C28	0.911812	0.331383	0.139295	0.0357*
H1C30	0.962178	0.571479	0.182448	0.0402*
H1C31	0.806747	0.537041	0.284312	0.0418*
H1C32	0.848835	0.553251	0.07959	0.0485*
H1C33	0.777712	−0.305035	−0.032587	0.0595*
H1C35	0.908257	0.525479	0.270808	0.0379*
H2C35	0.942308	0.394912	0.285534	0.0379*
H1C36	0.799047	0.415411	0.029464	0.0422*
H1C37	0.792598	0.385145	0.388555	0.0458*
H1C38	0.992093	0.031886	−0.190284	0.0503*
H1C39	0.934258	0.77688	0.149677	0.0494*
H1C41	0.952701	0.141814	−0.249219	0.0568*
H1C42	0.801503	0.137883	−0.147465	0.0468*
H2C42	0.824181	−0.011411	−0.14019	0.0468*
H1C43	0.805315	0.071928	0.249169	0.0532*
H2C43	0.79764	0.211737	0.268958	0.0532*
H3C43	0.784286	0.199906	0.223437	0.0532*
H1C44	0.964516	0.259305	−0.117596	0.0548*	0.7544
H2C44	0.961823	0.384565	−0.090395	0.0548*	0.7544
H3C44	0.970606	0.237512	−0.072721	0.0548*	0.7544
H5	0.9826 (6)	−0.0767 (17)	−0.0353 (5)	0.039*
H1	0.9318 (8)	0.172 (2)	−0.0056 (4)	0.0503*
H2	0.8099 (8)	0.260 (2)	0.1452 (4)	0.0454*
H3	0.8089 (8)	0.4317 (18)	0.2144 (5)	0.0464*
H4	0.9296 (8)	0.0246 (19)	−0.1150 (5)	0.0437*
H6	0.9458 (9)	0.2057 (14)	0.3587 (6)	0.0519*
C44'	0.9383 (3)	0.3680 (9)	−0.0554 (2)	0.046 (3)	0.2456
H1C26	0.891045	0.390171	−0.052417	0.0339*	0.7544
H2C26	0.827656	0.352997	−0.075848	0.0339*	0.7544
H1C40	0.876076	0.323585	−0.124471	0.0356*	0.7544
H1C44'	0.961796	0.295871	−0.061466	0.0556*	0.2456
H2C44'	0.942857	0.447344	−0.070407	0.0556*	0.2456
H3C44'	0.949117	0.389126	−0.02818	0.0556*	0.2456
H1C26'	0.857458	0.402884	−0.059874	0.0339*	0.2456
H1C40'	0.821774	0.288173	−0.11693	0.0356*	0.2456
H2C40'	0.885218	0.309841	−0.122001	0.0356*	0.2456

	U11	U22	U33	U12	U13	U23
O1	0.0347 (8)	0.0531 (9)	0.0331 (7)	0.0104 (7)	−0.0034 (6)	−0.0128 (6)
O2	0.0272 (7)	0.0461 (8)	0.0412 (7)	0.0076 (6)	0.0094 (6)	0.0000 (6)
O3	0.0290 (7)	0.0408 (8)	0.0455 (8)	0.0031 (6)	0.0061 (6)	0.0078 (6)
O4	0.0315 (7)	0.0484 (8)	0.0300 (7)	0.0092 (6)	0.0080 (5)	0.0007 (6)
O5	0.0257 (7)	0.0311 (7)	0.0387 (7)	0.0019 (6)	0.0022 (5)	0.0043 (5)
O6	0.0355 (8)	0.0516 (9)	0.0413 (8)	0.0016 (7)	0.0055 (6)	0.0141 (6)
N2	0.0295 (8)	0.0268 (8)	0.0248 (7)	−0.0020 (6)	0.0092 (6)	0.0023 (6)
N3	0.0265 (8)	0.0252 (7)	0.0231 (7)	−0.0003 (6)	0.0078 (6)	0.0002 (5)
N4	0.0295 (8)	0.0246 (7)	0.0288 (7)	0.0011 (6)	0.0111 (6)	0.0044 (6)
N1	0.0283 (8)	0.0307 (8)	0.0214 (7)	−0.0002 (7)	0.0040 (6)	−0.0004 (6)
C45	0.0384 (11)	0.0342 (10)	0.0245 (8)	−0.0008 (9)	0.0090 (7)	−0.0015 (7)
C46	0.0301 (10)	0.0314 (9)	0.0290 (9)	0.0030 (8)	0.0111 (7)	0.0083 (7)
C47	0.0438 (12)	0.0495 (12)	0.0319 (10)	−0.0102 (10)	0.0074 (9)	−0.0068 (9)
C48	0.0333 (10)	0.0249 (9)	0.0233 (8)	−0.0007 (8)	0.0073 (7)	0.0004 (6)
C1	0.0244 (9)	0.0292 (9)	0.0268 (8)	−0.0002 (8)	0.0081 (7)	0.0026 (7)
C2	0.0312 (10)	0.0306 (9)	0.0237 (8)	−0.0072 (8)	0.0102 (7)	−0.0064 (7)
C3	0.0607 (14)	0.0411 (11)	0.0287 (9)	−0.0196 (11)	0.0173 (9)	−0.0084 (8)
C4	0.0696 (15)	0.0242 (10)	0.0299 (10)	0.0028 (10)	0.0102 (9)	0.0040 (7)
C5	0.0285 (10)	0.0416 (11)	0.0329 (9)	−0.0037 (9)	0.0046 (8)	0.0072 (8)
C6	0.0780 (17)	0.0314 (11)	0.0403 (11)	−0.0098 (12)	0.0275 (11)	−0.0033 (8)
C7	0.0351 (10)	0.0299 (9)	0.0279 (9)	−0.0018 (8)	0.0056 (7)	0.0003 (7)
C8	0.0290 (9)	0.0317 (9)	0.0274 (8)	−0.0004 (8)	0.0102 (7)	0.0002 (7)
C9	0.0379 (11)	0.0419 (11)	0.0397 (10)	−0.0140 (9)	0.0184 (9)	−0.0160 (8)
C10	0.0202 (9)	0.0338 (10)	0.0260 (8)	−0.0021 (8)	0.0047 (7)	−0.0033 (7)
C11	0.0825 (18)	0.0329 (11)	0.0263 (10)	−0.0001 (11)	0.0089 (10)	0.0015 (8)
C12	0.0304 (10)	0.0323 (10)	0.0297 (9)	−0.0032 (8)	0.0041 (7)	−0.0005 (7)
C13	0.0352 (10)	0.0272 (9)	0.0230 (8)	−0.0023 (8)	0.0111 (7)	0.0025 (7)
C14	0.0345 (10)	0.0276 (9)	0.0219 (8)	−0.0048 (8)	0.0071 (7)	−0.0034 (7)
C15	0.0586 (14)	0.0296 (10)	0.0278 (9)	−0.0006 (10)	0.0109 (9)	−0.0007 (7)
C16	0.0466 (12)	0.0350 (11)	0.0311 (9)	0.0101 (10)	0.0026 (9)	0.0021 (8)
C17	0.0268 (9)	0.0286 (9)	0.0263 (8)	0.0009 (8)	0.0095 (7)	0.0069 (7)
C18	0.0430 (11)	0.0288 (9)	0.0326 (9)	0.0040 (9)	0.0140 (8)	0.0068 (7)
C19	0.0485 (12)	0.0352 (10)	0.0260 (9)	−0.0087 (9)	0.0063 (8)	0.0026 (8)
C20	0.0532 (13)	0.0447 (12)	0.0296 (10)	0.0138 (10)	0.0004 (9)	−0.0035 (8)
C21	0.0423 (12)	0.0368 (10)	0.0288 (9)	−0.0073 (9)	0.0073 (8)	0.0017 (8)
C22	0.0331 (10)	0.0286 (9)	0.0257 (8)	−0.0065 (8)	0.0074 (7)	−0.0020 (7)
C23	0.0408 (12)	0.0339 (10)	0.0445 (11)	−0.0013 (9)	0.0179 (9)	−0.0031 (8)
C24	0.0419 (11)	0.0328 (10)	0.0331 (9)	0.0023 (9)	0.0149 (8)	0.0010 (8)
C25	0.0284 (10)	0.0352 (10)	0.0317 (9)	0.0024 (8)	0.0100 (8)	0.0046 (7)
C26	0.0286 (17)	0.0292 (10)	0.0274 (9)	−0.001 (2)	0.0069 (11)	0.0027 (8)
C26'	0.0286 (17)	0.0292 (10)	0.0274 (9)	−0.001 (2)	0.0069 (11)	0.0027 (8)
C27	0.0372 (11)	0.0279 (9)	0.0335 (9)	0.0035 (8)	0.0106 (8)	0.0063 (7)
C28	0.0270 (9)	0.0335 (10)	0.0317 (9)	0.0008 (8)	0.0130 (7)	0.0029 (7)
C29	0.0321 (10)	0.0313 (9)	0.0276 (9)	−0.0044 (8)	0.0069 (7)	−0.0031 (7)
C30	0.0405 (11)	0.0320 (10)	0.0294 (9)	−0.0052 (9)	0.0105 (8)	−0.0012 (7)
C31	0.0381 (11)	0.0324 (10)	0.0352 (10)	0.0004 (9)	0.0108 (8)	0.0022 (8)
C32	0.0614 (14)	0.0312 (10)	0.0349 (10)	−0.0032 (10)	0.0244 (9)	−0.0045 (8)
C33	0.0659 (16)	0.0401 (12)	0.0533 (12)	−0.0272 (12)	0.0364 (11)	−0.0151 (10)
C34	0.0322 (10)	0.0358 (10)	0.0251 (9)	0.0022 (8)	0.0042 (7)	−0.0052 (7)
C35	0.0293 (10)	0.0370 (10)	0.0280 (9)	−0.0033 (8)	0.0052 (7)	0.0017 (7)
C36	0.0436 (12)	0.0351 (10)	0.0303 (9)	−0.0011 (9)	0.0156 (8)	0.0012 (8)
C37	0.0496 (12)	0.0357 (10)	0.0343 (10)	−0.0097 (10)	0.0202 (9)	−0.0080 (8)
C38	0.0379 (11)	0.0512 (12)	0.0401 (11)	−0.0100 (10)	0.0161 (9)	−0.0080 (9)
C39	0.0628 (15)	0.0291 (10)	0.0348 (10)	−0.0097 (10)	0.0175 (9)	0.0019 (8)
C40	0.0323 (16)	0.0304 (11)	0.0286 (12)	−0.0050 (15)	0.0117 (14)	−0.0006 (9)
C40'	0.0323 (16)	0.0304 (11)	0.0286 (12)	−0.0050 (15)	0.0117 (14)	−0.0006 (9)
C41	0.0679 (16)	0.0454 (12)	0.0342 (11)	−0.0190 (12)	0.0229 (10)	−0.0054 (9)
C42	0.0252 (10)	0.0641 (14)	0.0255 (9)	0.0040 (10)	0.0006 (7)	−0.0089 (9)
C43	0.0505 (13)	0.0336 (11)	0.0552 (12)	−0.0045 (10)	0.0251 (10)	0.0014 (9)
C44	0.0408 (15)	0.0439 (16)	0.0599 (18)	−0.0174 (13)	0.0277 (13)	−0.0201 (13)
C44'	0.046 (5)	0.058 (6)	0.032 (4)	−0.020 (5)	0.003 (4)	0.007 (4)

O1—C45	1.375 (2)	C18—H1C18	0.96
O1—H1	0.883 (14)	C19—C37	1.372 (3)
O2—C46	1.370 (2)	C19—H1C19	0.96
O2—H2	0.883 (15)	C20—C34	1.393 (2)
O3—C7	1.365 (2)	C20—H1C20	0.96
O3—H3	0.883 (16)	C21—C24	1.378 (3)
O4—C29	1.383 (2)	C21—H1C21	0.96
O4—H4	0.883 (19)	C22—C31	1.392 (3)
O5—C14	1.362 (2)	C22—C35	1.504 (3)
O5—H5	0.883 (14)	C23—C31	1.379 (3)
O6—C12	1.369 (2)	C23—C37	1.381 (3)
O6—H6	0.883 (16)	C23—H1C23	0.96
N2—C1	1.471 (2)	C24—C25	1.385 (2)
N2—C18	1.491 (2)	C24—H1C24	0.96
N2—C35	1.480 (2)	C25—H1C25	0.96
N3—C8	1.466 (2)	C26—C26'	0.277 (11)
N3—C10	1.468 (2)	C26—C40	1.520 (6)
N3—C26	1.475 (7)	C26—C40'	1.479 (10)
N3—C26'	1.50 (2)	C26—H1C26	0.96
N4—C1	1.469 (2)	C26—H2C26	0.96
N4—C27	1.473 (2)	C26—H1C26'	0.8552
N4—C28	1.469 (2)	C26'—C40	1.436 (16)
N1—C10	1.473 (2)	C26'—C40'	1.520 (17)
N1—C40	1.525 (3)	C26'—C44'	1.502 (15)
N1—C40'	1.447 (10)	C26'—H1C26	0.8205
N1—C42	1.475 (2)	C26'—H1C26'	0.96
C45—C47	1.384 (2)	C27—H1C27	0.96
C45—C13	1.395 (3)	C27—H2C27	0.96
C46—C5	1.392 (2)	C28—H1C28	0.96
C46—C17	1.400 (2)	C28—H2C28	0.96
C47—C3	1.380 (3)	C29—C34	1.386 (3)
C47—H1C47	0.96	C29—C38	1.380 (3)
C48—C1	1.507 (2)	C30—C39	1.390 (3)
C48—C7	1.396 (3)	C30—H1C30	0.96
C48—C30	1.391 (3)	C31—H1C31	0.96
C1—H1C1	0.96	C32—C36	1.385 (2)
C2—C9	1.395 (3)	C32—H1C32	0.96
C2—C10	1.509 (2)	C33—H1C33	0.96
C2—C14	1.402 (2)	C34—C42	1.500 (3)
C3—C32	1.376 (3)	C35—H1C35	0.96
C3—H1C3	0.96	C35—H2C35	0.96
C4—C16	1.379 (3)	C36—H1C36	0.96
C4—C39	1.379 (3)	C37—H1C37	0.96
C4—H1C4	0.96	C38—C41	1.388 (3)
C5—C21	1.381 (3)	C38—H1C38	0.96
C5—H1C5	0.96	C39—H1C39	0.96
C6—C15	1.373 (3)	C40—C40'	0.673 (8)
C6—C33	1.376 (3)	C40—C44	1.502 (4)
C6—H1C6	0.96	C40—H1C40	0.96
C7—C16	1.388 (2)	C40—H2C40'	0.8114
C8—C13	1.505 (2)	C40'—H1C40	0.9475
C8—H1C8	0.96	C40'—H1C40'	0.96
C8—H2C8	0.96	C40'—H2C40'	0.96
C9—C33	1.396 (3)	C41—H1C41	0.96
C9—H1C9	0.96	C42—H1C42	0.96
C10—H1C10	0.96	C42—H2C42	0.96
C11—C20	1.379 (3)	C43—H1C43	0.96
C11—C41	1.371 (4)	C43—H2C43	0.96
C11—H1C11	0.96	C43—H3C43	0.96
C12—C19	1.392 (3)	C44—H1C44	0.96
C12—C22	1.388 (2)	C44—H2C44	0.96
C13—C36	1.385 (3)	C44—H3C44	0.96
C14—C15	1.396 (2)	H3C44—H1C44'	0.7529
C15—H1C15	0.96	C44'—H1C44'	0.96
C16—H1C16	0.96	C44'—H2C44'	0.96
C17—C25	1.386 (3)	C44'—H3C44'	0.96
C17—C28	1.506 (2)	H1C26—H1C26'	0.8097
C18—C27	1.522 (3)	H1C40—H2C40'	0.258
C18—C43	1.531 (3)
C45—O1—H1	106.7 (13)	N3—C26'—H1C26	116.81
C46—O2—H2	106.0 (13)	N3—C26'—H1C26'	113.51
C7—O3—H3	102.9 (13)	C26—C26'—C40	102 (3)
C29—O4—H4	104.5 (11)	C26—C26'—C40'	76 (3)
C14—O5—H5	110.5 (11)	C26—C26'—C44'	163 (7)
C12—O6—H6	106.6 (15)	C26—C26'—H1C26	112.21
C1—N2—C18	107.53 (13)	C26—C26'—H1C26'	59.85
C1—N2—C35	111.58 (13)	C40—C26'—C40'	26.1 (4)
C18—N2—C35	115.78 (12)	C40—C26'—C44'	86.0 (7)
C8—N3—C10	113.25 (13)	C40—C26'—H1C26	128.59
C8—N3—C26	112.5 (2)	C40—C26'—H1C26'	130.97
C8—N3—C26'	118.3 (7)	C40'—C26'—C44'	111.2 (9)
C10—N3—C26	103.0 (2)	C40'—C26'—H1C26	142.25
C10—N3—C26'	106.9 (7)	C40'—C26'—H1C26'	115.17
C26—N3—C26'	10.6 (4)	C44'—C26'—H1C26	52.38
C1—N4—C27	102.83 (12)	C44'—C26'—H1C26'	103.56
C1—N4—C28	112.68 (14)	H1C26—C26'—H1C26'	53.4
C27—N4—C28	113.58 (14)	N4—C27—C18	103.41 (14)
C10—N1—C40	108.22 (15)	N4—C27—H1C27	109.47
C10—N1—C40'	98.8 (4)	N4—C27—H2C27	109.47
C10—N1—C42	111.70 (13)	C18—C27—H1C27	109.47
C40—N1—C40'	26.0 (3)	C18—C27—H2C27	109.47
C40—N1—C42	116.13 (15)	H1C27—C27—H2C27	114.92
C40'—N1—C42	99.6 (3)	N4—C28—C17	113.00 (14)
O1—C45—C47	118.88 (17)	N4—C28—H1C28	109.47
O1—C45—C13	120.66 (15)	N4—C28—H2C28	109.47
C47—C45—C13	120.46 (18)	C17—C28—H1C28	109.47
O2—C46—C5	118.46 (15)	C17—C28—H2C28	109.47
O2—C46—C17	121.52 (14)	H1C28—C28—H2C28	105.7
C5—C46—C17	120.01 (17)	O4—C29—C34	119.56 (16)
C45—C47—C3	119.88 (19)	O4—C29—C38	119.14 (16)
C45—C47—H1C47	120.06	C34—C29—C38	121.30 (16)
C3—C47—H1C47	120.06	C48—C30—C39	120.92 (19)
C1—C48—C7	120.21 (16)	C48—C30—H1C30	119.54
C1—C48—C30	121.01 (16)	C39—C30—H1C30	119.54
C7—C48—C30	118.79 (16)	C22—C31—C23	121.81 (16)
N2—C1—N4	101.73 (13)	C22—C31—H1C31	119.1
N2—C1—C48	111.92 (14)	C23—C31—H1C31	119.1
N2—C1—H1C1	114.25	C3—C32—C36	119.13 (19)
N4—C1—C48	113.09 (12)	C3—C32—H1C32	120.43
N4—C1—H1C1	113.11	C36—C32—H1C32	120.44
C48—C1—H1C1	103.16	C6—C33—C9	119.7 (2)
C9—C2—C10	118.91 (15)	C6—C33—H1C33	120.13
C9—C2—C14	117.77 (16)	C9—C33—H1C33	120.13
C10—C2—C14	123.21 (16)	C20—C34—C29	117.91 (18)
C47—C3—C32	120.67 (18)	C20—C34—C42	122.73 (17)
C47—C3—H1C3	119.66	C29—C34—C42	119.35 (15)
C32—C3—H1C3	119.66	N2—C35—C22	111.06 (14)
C16—C4—C39	120.63 (18)	N2—C35—H1C35	109.47
C16—C4—H1C4	119.69	N2—C35—H2C35	109.47
C39—C4—H1C4	119.69	C22—C35—H1C35	109.47
C46—C5—C21	120.52 (17)	C22—C35—H2C35	109.47
C46—C5—H1C5	119.74	H1C35—C35—H2C35	107.83
C21—C5—H1C5	119.74	C13—C36—C32	121.52 (19)
C15—C6—C33	120.14 (19)	C13—C36—H1C36	119.24
C15—C6—H1C6	119.93	C32—C36—H1C36	119.24
C33—C6—H1C6	119.93	C19—C37—C23	120.4 (2)
O3—C7—C48	121.33 (15)	C19—C37—H1C37	119.8
O3—C7—C16	118.56 (17)	C23—C37—H1C37	119.8
C48—C7—C16	120.09 (18)	C29—C38—C41	119.5 (2)
N3—C8—C13	110.95 (14)	C29—C38—H1C38	120.26
N3—C8—H1C8	109.47	C41—C38—H1C38	120.26
N3—C8—H2C8	109.47	C4—C39—C30	119.3 (2)
C13—C8—H1C8	109.47	C4—C39—H1C39	120.33
C13—C8—H2C8	109.47	C30—C39—H1C39	120.33
H1C8—C8—H2C8	107.95	N1—C40—C26	101.9 (3)
C2—C9—C33	121.36 (18)	N1—C40—C26'	106.0 (10)
C2—C9—H1C9	119.32	N1—C40—C40'	70.4 (9)
C33—C9—H1C9	119.32	N1—C40—C44	113.6 (2)
N3—C10—N1	102.71 (13)	N1—C40—H1C40	113.15
N3—C10—C2	112.10 (12)	N1—C40—H2C40'	112.69
N3—C10—H1C10	114.45	C26—C40—C26'	10.2 (4)
N1—C10—C2	115.33 (15)	C26—C40—C40'	73.7 (8)
N1—C10—H1C10	111.16	C26—C40—C44	113.1 (2)
C2—C10—H1C10	101.59	C26—C40—H1C40	113.65
C20—C11—C41	119.70 (18)	C26—C40—H2C40'	125.74
C20—C11—H1C11	120.15	C26'—C40—C40'	83.9 (9)
C41—C11—H1C11	120.15	C26'—C40—C44	103.0 (5)
O6—C12—C19	122.05 (15)	C26'—C40—H1C40	118.92
O6—C12—C22	117.56 (17)	C26'—C40—H2C40'	129.57
C19—C12—C22	120.39 (17)	C40'—C40—C44	170.1 (9)
C45—C13—C8	119.78 (16)	C40'—C40—H1C40	68.34
C45—C13—C36	118.31 (15)	C40'—C40—H2C40'	79.99
C8—C13—C36	121.89 (16)	C44—C40—H1C40	101.93
O5—C14—C2	118.51 (15)	C44—C40—H2C40'	90.15
O5—C14—C15	121.11 (16)	H1C40—C40—H2C40'	13.73
C2—C14—C15	120.38 (18)	N1—C40'—C26	107.8 (6)
C6—C15—C14	120.60 (19)	N1—C40'—C26'	105.8 (11)
C6—C15—H1C15	119.7	N1—C40'—C40	83.5 (9)
C14—C15—H1C15	119.7	N1—C40'—H1C40	120.94
C4—C16—C7	120.16 (19)	N1—C40'—H1C40'	109.47
C4—C16—H1C16	119.92	N1—C40'—H2C40'	109.47
C7—C16—H1C16	119.92	C26—C40'—C26'	10.5 (5)
C46—C17—C25	118.08 (15)	C26—C40'—C40	80.4 (8)
C46—C17—C28	121.01 (16)	C26—C40'—H1C40	118
C25—C17—C28	120.69 (15)	C26—C40'—H1C40'	99.32
N2—C18—C27	103.64 (15)	C26—C40'—H2C40'	117.22
N2—C18—C43	109.93 (15)	C26'—C40'—C40	69.9 (8)
N2—C18—H1C18	113.77	C26'—C40'—H1C40	112.64
C27—C18—C43	111.83 (15)	C26'—C40'—H1C40'	109.47
C27—C18—H1C18	111.94	C26'—C40'—H2C40'	109.47
C43—C18—H1C18	105.87	C40—C40'—H1C40	70.33
C12—C19—C37	120.23 (16)	C40—C40'—H1C40'	166.15
C12—C19—H1C19	119.89	C40—C40'—H2C40'	56.34
C37—C19—H1C19	119.89	H1C40—C40'—H1C40'	98.09
C11—C20—C34	121.3 (2)	H1C40—C40'—H2C40'	15.53
C11—C20—H1C20	119.35	H1C40'—C40'—H2C40'	112.95
C34—C20—H1C20	119.35	C11—C41—C38	120.3 (2)
C5—C21—C24	120.11 (16)	C11—C41—H1C41	119.85
C5—C21—H1C21	119.95	C38—C41—H1C41	119.84
C24—C21—H1C21	119.95	N1—C42—C34	109.58 (15)
C12—C22—C31	118.04 (17)	N1—C42—H1C42	109.47
C12—C22—C35	121.71 (16)	N1—C42—H2C42	109.47
C31—C22—C35	120.23 (15)	C34—C42—H1C42	109.47
C31—C23—C37	119.13 (19)	C34—C42—H2C42	109.47
C31—C23—H1C23	120.44	H1C42—C42—H2C42	109.36
C37—C23—H1C23	120.44	C18—C43—H1C43	109.47
C21—C24—C25	119.29 (18)	C18—C43—H2C43	109.47
C21—C24—H1C24	120.36	C18—C43—H3C43	109.47
C25—C24—H1C24	120.36	H1C43—C43—H2C43	109.47
C17—C25—C24	121.99 (17)	H1C43—C43—H3C43	109.47
C17—C25—H1C25	119	H2C43—C43—H3C43	109.47
C24—C25—H1C25	119	C40—C44—H1C44	109.47
N3—C26—C26'	90 (5)	C40—C44—H2C44	109.47
N3—C26—C40	103.0 (5)	C40—C44—H3C44	109.47
N3—C26—C40'	104.1 (6)	H1C44—C44—H2C44	109.47
N3—C26—H1C26	109.47	H1C44—C44—H3C44	109.47
N3—C26—H2C26	109.47	H2C44—C44—H3C44	109.47
N3—C26—H1C26'	124.3	C44—H3C44—H1C44'	83.26
C26'—C26—C40	67 (3)	C26'—C44'—H1C44'	109.47
C26'—C26—C40'	93 (3)	C26'—C44'—H2C44'	109.47
C26'—C26—H1C26	52.3	C26'—C44'—H3C44'	109.47
C26'—C26—H2C26	160.01	H1C44'—C44'—H2C44'	109.47
C26'—C26—H1C26'	103.89	H1C44'—C44'—H3C44'	109.47
C40—C26—C40'	25.9 (3)	H2C44'—C44'—H3C44'	109.47
C40—C26—H1C26	109.47	C26—H1C26—C26'	15.48
C40—C26—H2C26	109.47	C26—H1C26—H1C26'	57.04
C40—C26—H1C26'	132.3	C26'—H1C26—H1C26'	72.15
C40'—C26—H1C26	130.53	C40—H1C40—C40'	41.33
C40'—C26—H2C26	85.15	C40—H1C40—H2C40'	48.26
C40'—C26—H1C26'	127.88	C40'—H1C40—H2C40'	84.98
H1C26—C26—H2C26	115.22	H3C44—H1C44'—C44'	157.81
H1C26—C26—H1C26'	52.59	C26—H1C26'—C26'	16.26
H2C26—C26—H1C26'	62.8	C26—H1C26'—H1C26	70.37
N3—C26'—C26	79 (5)	C26'—H1C26'—H1C26	54.45
N3—C26'—C40	105.9 (17)	C40—H2C40'—C40'	43.68
N3—C26'—C40'	100.8 (15)	C40—H2C40'—H1C40	118.01
N3—C26'—C44'	112.9 (11)	C40'—H2C40'—H1C40	79.49

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3	0.883 (14)	1.838 (16)	2.6344 (17)	148.9 (19)
O2—H2···N4	0.883 (15)	1.937 (16)	2.7360 (17)	149.7 (18)
O3—H3···N2	0.883 (16)	1.839 (17)	2.6680 (17)	155.5 (19)
O4—H4···N1	0.883 (19)	1.849 (19)	2.646 (2)	149.0 (14)
O1—H1···O5	0.883 (14)	2.472 (19)	3.0381 (18)	122.4 (16)
O4—H4···O5	0.883 (14)	2.523 (17)	3.1167 (15)	125.3 (15)
O5—H5···O1i	0.883 (14)	1.930 (15)	2.8108 (18)	174.9 (16)
O6—H6···O4ii	0.883 (16)	1.907 (14)	2.746 (2)	157.9 (18)
C26—H1C26···C44′	0.96	1.19	1.769 (9)	109.96
C26′—H1C26···C44′	0.82	1.19	1.502 (15)	94.63
C44′—H1C26···N3	1.19	2.01	2.504 (9)	99.67
C44′—H1C26···C26	1.19	0.96	1.769 (9)	109.96
C44′—H1C26···C26′	1.19	0.82	1.502 (15)	94.63
C40′—H1C40···C44	0.95	1.94	2.169 (9)	90.47
C44—H1C44′···C44′	1.15	0.96	1.680 (9)	105.31
C44′—H1C44′···C44	0.96	1.15	1.680 (9)	105.31
C44′—H3C44′···O1	0.96	2.46	3.012 (8)	116.14
C40′—H2C40′···C44	0.96	1.71	2.169 (9)	105.19
C25—H1C25···O4i	0.96	2.40	3.346 (2)	169.82
C35—H2C35···O6	0.96	2.37	2.813 (2)	107.61
O1—H1···C8	0.883 (14)	2.352 (19)	2.847 (2)	115.5 (15)
O2—H2···C28	0.883 (15)	2.385 (19)	2.896 (2)	117.1 (15)
O3—H3···C1	0.883 (16)	2.34 (2)	2.869 (2)	118.5 (16)
O4—H4···C42	0.883 (19)	2.355 (18)	2.806 (2)	111.8 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3	0.883 (14)	1.838 (16)	2.6344 (17)	148.9 (19)
O2—H2⋯N4	0.883 (15)	1.937 (16)	2.7360 (17)	149.7 (18)
O3—H3⋯N2	0.883 (16)	1.839 (17)	2.6680 (17)	155.5 (19)
O4—H4⋯N1	0.883 (19)	1.849 (19)	2.646 (2)	149.0 (14)
O1—H1⋯O5	0.883 (14)	2.472 (19)	3.0381 (18)	122.4 (16)
O4—H4⋯O5	0.883 (14)	2.523 (17)	3.1167 (15)	125.3 (15)
O5—H5⋯O1i	0.883 (14)	1.930 (15)	2.8108 (18)	174.9 (16)
O6—H6⋯O4ii	0.883 (16)	1.907 (14)	2.746 (2)	157.9 (18)

Symmetry codes: (i) ; (ii) .