Di(phenyl­propyl­amino)­gossypol: a derivative of the dimeric natural product gossypol

Di(phenyl­propyl­amino)­gossypol [systematic name: 2,2'-bis­{1,6-dihy­droxy-5-isopropyl-8-[(3-phenyl­propyl­amino)methyl­idene]naphthalen-7-one}, C₄₈H₅₂N₂O₆, was formed by reaction of the dimeric natural product gossypol with 3-phenyl­propyl­amine. The structure of this compound has its two naphthalene ring systems oriented approximately perpendicular to each other, and the two pendant phenyl­propyl groups have different conformations. One of these side groups is considerably disordered at room temperature but less so at 120 K. The enantio­meric mol­ecules form centrosymmetric dimers that are supported by inter­molecular hydrogen bonds and by hydro­phobic inter­actions between a pair of naphthalene rings. Two additional hydrogen bonds tie the dimer pairs into layers. Unlike gossypol and many gossypol Schiff base derivatives, the title compound crystallizes without the inclusion of solvent, which appears to occur because of the size and flexibility of its phenyl­propyl pendent groups.

Computing details

For both compounds, data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(I_296K) 2,2'-Bis{1,6-dihydroxy-5-isopropyl-8-[(3-phenylpropylamino)methylidene]naphthalen-7-one}

Crystal data

C48H52N2O6	F(000) = 1608
Mr = 752.92	Dx = 1.202 Mg m^−3 Dm = 1.19 Mg m^−3 Dm measured by flotation in aqueous KI
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 23192 reflections
a = 12.0729 (10) Å	θ = 2.2–27.1°
b = 29.176 (2) Å	µ = 0.08 mm^−1
c = 11.8511 (9) Å	T = 296 K
β = 94.417 (1)°	Diamond, yellow
V = 4162.0 (6) Å^3	0.60 × 0.40 × 0.20 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer	9074 independent reflections
Radiation source: fine-focus sealed tube	6318 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.954, Tmax = 0.984	k = −37→37
57486 measured reflections	l = −15→15

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0784P)^2 + 0.8499P] where P = (Fo^2 + 2Fc^2)/3
9074 reflections	(Δ/σ)max = 0.011
718 parameters	Δρmax = 0.27 e Å^−3
330 restraints	Δρmin = −0.19 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.03159 (10)	0.10405 (4)	0.40845 (11)	0.0513 (3)
H101	0.0378 (18)	0.1322 (9)	0.4119 (19)	0.076 (7)*
C1	0.11831 (13)	0.08237 (5)	0.46690 (13)	0.0375 (3)
C2	0.19168 (13)	0.10756 (5)	0.53754 (13)	0.0404 (3)
N1	−0.09197 (13)	0.00457 (5)	0.22064 (13)	0.0541 (4)
H111	−0.0755 (17)	−0.0275 (8)	0.2202 (18)	0.074 (6)*
O3	0.01569 (12)	−0.06592 (4)	0.29139 (11)	0.0592 (3)
C3	0.27773 (14)	0.08460 (5)	0.60106 (15)	0.0470 (4)
C4	0.28665 (14)	0.03782 (5)	0.58942 (15)	0.0471 (4)
H4	0.3505 (16)	0.0225 (6)	0.6372 (16)	0.055 (5)*
O5	0.05666 (12)	0.15119 (4)	0.68791 (11)	0.0566 (3)
H105	0.0675 (18)	0.1225 (8)	0.6757 (18)	0.071 (6)*
C5	0.23054 (14)	−0.03771 (5)	0.50491 (14)	0.0456 (4)
N2	−0.07555 (13)	0.24166 (5)	0.87614 (13)	0.0529 (4)
H112	−0.070 (2)	0.2743 (9)	0.879 (2)	0.098 (8)*
C6	0.16297 (15)	−0.06073 (5)	0.42823 (15)	0.0476 (4)
O4	0.17625 (14)	−0.10644 (4)	0.40741 (14)	0.0687 (4)
H104	0.116 (3)	−0.1102 (11)	0.351 (3)	0.123 (11)*
C7	0.07358 (14)	−0.03964 (5)	0.36041 (14)	0.0435 (4)
O7	−0.00972 (13)	0.31778 (4)	0.80541 (13)	0.0745 (4)
C8	0.05471 (13)	0.00819 (5)	0.37036 (13)	0.0382 (3)
O8	0.09906 (15)	0.36915 (4)	0.67585 (14)	0.0763 (5)
H108	0.052 (3)	0.3703 (11)	0.738 (3)	0.129 (11)*
C9	0.12742 (12)	0.03436 (4)	0.45076 (12)	0.0357 (3)
C10	0.21447 (13)	0.01167 (5)	0.51592 (13)	0.0398 (3)
C11	0.11545 (13)	0.17841 (5)	0.62055 (13)	0.0405 (3)
C12	0.18081 (13)	0.15884 (5)	0.54295 (14)	0.0418 (4)
C13	0.23957 (15)	0.18736 (5)	0.47280 (15)	0.0505 (4)
C14	0.22926 (16)	0.23426 (6)	0.48383 (16)	0.0519 (4)
H14	0.2699 (16)	0.2535 (7)	0.4336 (17)	0.061 (5)*
C15	0.15948 (16)	0.30496 (5)	0.57225 (15)	0.0500 (4)
C16	0.10309 (16)	0.32290 (5)	0.65579 (16)	0.0533 (4)
C17	0.04275 (16)	0.29584 (5)	0.73236 (16)	0.0516 (4)
C18	0.04221 (13)	0.24731 (5)	0.72224 (13)	0.0414 (3)
C19	0.10593 (13)	0.22662 (5)	0.63609 (13)	0.0390 (3)
C20	0.16500 (14)	0.25494 (5)	0.56330 (14)	0.0444 (4)
C21	0.35858 (18)	0.11124 (7)	0.6794 (2)	0.0666 (5)
H21A	0.416 (2)	0.0901 (8)	0.724 (2)	0.080*	0.72 (2)
H21B	0.317 (2)	0.1305 (10)	0.737 (2)	0.080*	0.72 (2)
H21C	0.401 (2)	0.1335 (9)	0.629 (2)	0.080*	0.72 (2)
H21D	0.350 (6)	0.1466 (6)	0.686 (6)	0.080*	0.28 (2)
H21E	0.341 (6)	0.096 (2)	0.756 (3)	0.080*	0.28 (2)
H21F	0.441 (2)	0.104 (2)	0.665 (6)	0.080*	0.28 (2)
C22	−0.03030 (14)	0.02755 (5)	0.29787 (14)	0.0448 (4)
H22	−0.0461 (15)	0.0625 (6)	0.3018 (15)	0.052 (5)*
C23	0.32468 (18)	−0.06217 (6)	0.5722 (2)	0.0656 (5)
H23	0.3463 (18)	−0.0433 (8)	0.6340 (19)	0.071 (6)*
C24	0.2927 (3)	−0.10797 (8)	0.6252 (2)	0.0963 (9)
H24A	0.2850	−0.1311	0.5676	0.144*
H24B	0.2235	−0.1045	0.6592	0.144*
H24C	0.3496	−0.1169	0.6821	0.144*
C25	0.4224 (2)	−0.06788 (11)	0.5005 (3)	0.1105 (10)
H25A	0.4014	−0.0873	0.4371	0.166*
H25B	0.4834	−0.0815	0.5453	0.166*
H25C	0.4444	−0.0384	0.4739	0.166*
C26	0.3125 (2)	0.16735 (7)	0.3879 (2)	0.0715 (6)
H26A	0.316 (4)	0.1903 (11)	0.321 (3)	0.086*	0.62 (6)
H26B	0.3917 (18)	0.164 (2)	0.428 (3)	0.086*	0.62 (6)
H26C	0.286 (4)	0.1355 (9)	0.357 (4)	0.086*	0.62 (6)
H26D	0.364 (6)	0.143 (2)	0.429 (4)	0.086*	0.38 (6)
H26F	0.261 (4)	0.151 (3)	0.325 (5)	0.086*	0.38 (6)
H26E	0.362 (6)	0.1913 (16)	0.350 (6)	0.086*	0.38 (6)
C27	−0.02006 (14)	0.22277 (5)	0.79844 (14)	0.0441 (4)
H27	−0.0225 (15)	0.1887 (7)	0.7928 (15)	0.058 (5)*
C28	0.2208 (2)	0.33572 (6)	0.49415 (19)	0.0682 (6)
H28	0.2269 (17)	0.3189 (8)	0.4210 (19)	0.075 (6)*
C29	0.1581 (3)	0.37939 (7)	0.4536 (2)	0.0906 (8)
H29A	0.1608	0.4014	0.5140	0.136*
H29B	0.0821	0.3719	0.4315	0.136*
H29C	0.1922	0.3921	0.3901	0.136*
C30	0.3345 (2)	0.34742 (10)	0.5490 (3)	0.1007 (9)
H30A	0.3267	0.3650	0.6164	0.151*
H30B	0.3747	0.3650	0.4972	0.151*
H30C	0.3744	0.3197	0.5681	0.151*
C31	−0.17321 (19)	0.02641 (8)	0.14102 (19)	0.0661 (5)
H31A	−0.2287 (19)	0.0025 (8)	0.1132 (19)	0.081 (7)*
H31B	−0.215 (2)	0.0514 (10)	0.181 (2)	0.106 (9)*
C32	−0.1201 (3)	0.04872 (14)	0.0435 (3)	0.1055 (12)
H32A	−0.060 (3)	0.0683 (13)	0.067 (3)	0.142 (13)*
H32B	−0.084 (3)	0.0223 (15)	0.004 (4)	0.175 (19)*
C33	−0.2021 (3)	0.07249 (13)	−0.0413 (3)	0.1188 (13)
H33A	−0.166 (4)	0.0916 (17)	−0.092 (4)	0.205 (19)*
H33B	−0.253 (2)	0.0925 (11)	0.012 (3)	0.109 (11)*
C34B	−0.2962 (8)	0.0443 (3)	−0.0919 (6)	0.104 (3)	0.439 (18)
C35B	−0.2808 (15)	0.0093 (4)	−0.1663 (8)	0.139 (4)	0.439 (18)
H35B	−0.2091	0.0031	−0.1856	0.167*	0.439 (18)
C36B	−0.3663 (17)	−0.0170 (5)	−0.2135 (11)	0.158 (4)	0.439 (18)
H36B	−0.3547	−0.0407	−0.2639	0.189*	0.439 (18)
C37B	−0.4698 (15)	−0.0063 (6)	−0.1819 (12)	0.150 (5)	0.439 (18)
H37B	−0.5305	−0.0231	−0.2118	0.180*	0.439 (18)
C38B	−0.4866 (10)	0.0286 (6)	−0.1078 (14)	0.135 (4)	0.439 (18)
H38B	−0.5584	0.0347	−0.0885	0.162*	0.439 (18)
C39B	−0.4006 (7)	0.0545 (5)	−0.0614 (12)	0.118 (3)	0.439 (18)
H39B	−0.4123	0.0781	−0.0110	0.142*	0.439 (18)
C40	−0.13950 (19)	0.21677 (7)	0.95544 (17)	0.0570 (5)
H40A	−0.0896 (18)	0.1973 (8)	1.0048 (19)	0.073 (6)*
H40B	−0.1861 (18)	0.1946 (8)	0.9150 (19)	0.075 (6)*
C41	−0.20324 (17)	0.24965 (7)	1.02361 (17)	0.0537 (4)
H41A	−0.1479 (19)	0.2709 (8)	1.0595 (19)	0.073 (6)*
H41B	−0.2485 (19)	0.2683 (8)	0.9692 (19)	0.075 (7)*
C42	−0.2668 (2)	0.22580 (7)	1.1111 (2)	0.0639 (5)
H42A	−0.213 (2)	0.2071 (9)	1.158 (2)	0.091 (8)*
H42B	−0.314 (2)	0.2035 (9)	1.074 (2)	0.087 (8)*
C43	−0.33201 (16)	0.25663 (7)	1.18402 (16)	0.0569 (4)
C44	−0.3204 (2)	0.30389 (8)	1.18609 (19)	0.0684 (5)
H44	−0.268 (2)	0.3186 (8)	1.136 (2)	0.087 (7)*
C45	−0.3780 (2)	0.33118 (9)	1.2575 (2)	0.0804 (7)
H45	−0.366 (2)	0.3671 (11)	1.258 (2)	0.113 (9)*
C46	−0.4480 (2)	0.31201 (11)	1.3279 (2)	0.0927 (8)
H46	−0.489 (3)	0.3316 (11)	1.383 (3)	0.127 (10)*
C47	−0.4606 (2)	0.26522 (13)	1.3287 (3)	0.1036 (10)
H47	−0.508 (3)	0.2511 (11)	1.391 (3)	0.131 (10)*
C48	−0.4033 (2)	0.23778 (10)	1.2574 (2)	0.0845 (7)
H48	−0.413 (2)	0.2053 (11)	1.257 (3)	0.115 (10)*
C34A	−0.2828 (5)	0.03929 (17)	−0.0997 (3)	0.0766 (18)	0.561 (18)
C35A	−0.2417 (8)	0.0032 (2)	−0.1580 (5)	0.095 (2)	0.561 (18)
H35A	−0.1651	0.0003	−0.1597	0.114*	0.561 (18)
C36A	−0.3082 (9)	−0.0287 (3)	−0.2136 (5)	0.110 (3)	0.561 (18)
H36A	−0.2777	−0.0528	−0.2523	0.132*	0.561 (18)
C37A	−0.4208 (8)	−0.0245 (3)	−0.2111 (6)	0.113 (3)	0.561 (18)
H37A	−0.4674	−0.0459	−0.2485	0.135*	0.561 (18)
C38A	−0.4658 (7)	0.0110 (3)	−0.1541 (9)	0.122 (3)	0.561 (18)
H38A	−0.5425	0.0137	−0.1527	0.146*	0.561 (18)
C39A	−0.3962 (5)	0.0424 (3)	−0.0992 (8)	0.101 (2)	0.561 (18)
H39A	−0.4268	0.0664	−0.0605	0.122*	0.561 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0616 (8)	0.0240 (5)	0.0666 (8)	0.0021 (5)	−0.0071 (6)	0.0001 (5)
C1	0.0437 (8)	0.0268 (6)	0.0426 (8)	0.0005 (6)	0.0079 (6)	−0.0005 (6)
C2	0.0445 (9)	0.0282 (7)	0.0493 (9)	−0.0016 (6)	0.0096 (7)	−0.0079 (6)
N1	0.0624 (9)	0.0428 (8)	0.0554 (9)	−0.0078 (7)	−0.0066 (7)	−0.0010 (7)
O3	0.0818 (9)	0.0307 (5)	0.0634 (8)	−0.0115 (5)	−0.0044 (7)	−0.0079 (5)
C3	0.0454 (9)	0.0391 (8)	0.0565 (10)	−0.0020 (7)	0.0033 (7)	−0.0114 (7)
C4	0.0446 (9)	0.0393 (8)	0.0566 (10)	0.0039 (7)	−0.0003 (8)	−0.0071 (7)
O5	0.0833 (9)	0.0256 (5)	0.0645 (8)	−0.0071 (5)	0.0281 (7)	−0.0064 (5)
C5	0.0513 (10)	0.0314 (7)	0.0546 (9)	0.0066 (6)	0.0063 (7)	−0.0030 (7)
N2	0.0654 (10)	0.0404 (7)	0.0550 (9)	−0.0090 (6)	0.0185 (7)	−0.0115 (6)
C6	0.0601 (10)	0.0245 (7)	0.0590 (10)	0.0026 (6)	0.0102 (8)	−0.0054 (6)
O4	0.0875 (10)	0.0273 (6)	0.0897 (10)	0.0093 (6)	−0.0035 (8)	−0.0133 (6)
C7	0.0548 (10)	0.0288 (7)	0.0475 (9)	−0.0062 (6)	0.0072 (7)	−0.0044 (6)
O7	0.0999 (11)	0.0358 (6)	0.0942 (10)	−0.0123 (6)	0.0494 (9)	−0.0231 (6)
C8	0.0457 (8)	0.0274 (7)	0.0422 (8)	−0.0051 (6)	0.0075 (6)	−0.0010 (6)
O8	0.1195 (13)	0.0262 (6)	0.0887 (10)	−0.0061 (6)	0.0438 (10)	−0.0102 (6)
C9	0.0409 (8)	0.0262 (6)	0.0408 (7)	−0.0019 (5)	0.0094 (6)	−0.0027 (5)
C10	0.0439 (8)	0.0296 (7)	0.0465 (8)	0.0015 (6)	0.0087 (7)	−0.0034 (6)
C11	0.0484 (9)	0.0291 (7)	0.0443 (8)	−0.0061 (6)	0.0050 (7)	−0.0045 (6)
C12	0.0472 (9)	0.0281 (7)	0.0506 (9)	−0.0033 (6)	0.0069 (7)	−0.0089 (6)
C13	0.0572 (10)	0.0356 (8)	0.0609 (10)	−0.0067 (7)	0.0183 (8)	−0.0104 (7)
C14	0.0640 (11)	0.0344 (8)	0.0598 (10)	−0.0107 (7)	0.0215 (9)	−0.0085 (7)
C15	0.0661 (11)	0.0299 (7)	0.0556 (10)	−0.0070 (7)	0.0139 (8)	−0.0053 (7)
C16	0.0718 (12)	0.0253 (7)	0.0645 (11)	−0.0063 (7)	0.0169 (9)	−0.0075 (7)
C17	0.0627 (11)	0.0324 (8)	0.0617 (10)	−0.0049 (7)	0.0170 (8)	−0.0134 (7)
C18	0.0486 (9)	0.0301 (7)	0.0460 (8)	−0.0053 (6)	0.0064 (7)	−0.0083 (6)
C19	0.0447 (9)	0.0286 (7)	0.0434 (8)	−0.0043 (6)	0.0028 (7)	−0.0073 (6)
C20	0.0543 (10)	0.0296 (7)	0.0497 (9)	−0.0056 (6)	0.0077 (7)	−0.0066 (6)
C21	0.0629 (12)	0.0518 (10)	0.0822 (14)	−0.0033 (9)	−0.0133 (11)	−0.0197 (10)
C22	0.0513 (10)	0.0356 (8)	0.0474 (9)	−0.0057 (7)	0.0026 (7)	−0.0010 (7)
C23	0.0729 (14)	0.0414 (9)	0.0795 (14)	0.0179 (9)	−0.0123 (11)	−0.0100 (9)
C24	0.129 (2)	0.0556 (13)	0.0999 (19)	0.0238 (14)	−0.0184 (17)	0.0133 (12)
C25	0.0682 (16)	0.110 (2)	0.153 (3)	0.0323 (15)	0.0098 (17)	0.002 (2)
C26	0.0888 (15)	0.0438 (10)	0.0878 (15)	−0.0087 (10)	0.0436 (12)	−0.0166 (10)
C27	0.0520 (10)	0.0341 (7)	0.0465 (9)	−0.0023 (6)	0.0060 (7)	−0.0066 (6)
C28	0.1062 (17)	0.0357 (9)	0.0674 (12)	−0.0104 (9)	0.0368 (12)	−0.0041 (8)
C29	0.147 (2)	0.0482 (11)	0.0796 (15)	−0.0022 (13)	0.0278 (16)	0.0102 (11)
C30	0.0922 (19)	0.0839 (17)	0.132 (2)	−0.0218 (14)	0.0495 (18)	0.0127 (16)
C31	0.0638 (13)	0.0663 (12)	0.0653 (12)	−0.0040 (10)	−0.0134 (10)	−0.0003 (10)
C32	0.089 (2)	0.117 (3)	0.105 (2)	−0.034 (2)	−0.0261 (18)	0.052 (2)
C33	0.126 (3)	0.108 (2)	0.116 (3)	−0.021 (2)	−0.030 (2)	0.052 (2)
C34B	0.092 (5)	0.122 (6)	0.095 (6)	−0.005 (5)	−0.017 (5)	0.051 (5)
C35B	0.115 (7)	0.188 (9)	0.115 (7)	−0.005 (6)	0.010 (5)	0.012 (5)
C36B	0.150 (9)	0.212 (10)	0.107 (7)	0.001 (8)	−0.020 (7)	−0.012 (7)
C37B	0.122 (7)	0.194 (10)	0.123 (8)	−0.006 (8)	−0.057 (6)	0.005 (7)
C38B	0.099 (5)	0.172 (9)	0.130 (8)	0.002 (5)	−0.020 (5)	0.034 (6)
C39B	0.107 (5)	0.137 (7)	0.108 (6)	0.013 (5)	−0.012 (4)	0.030 (5)
C40	0.0705 (13)	0.0482 (10)	0.0544 (11)	−0.0075 (9)	0.0192 (10)	−0.0050 (8)
C41	0.0568 (11)	0.0547 (10)	0.0508 (10)	−0.0027 (9)	0.0115 (9)	−0.0019 (8)
C42	0.0758 (14)	0.0542 (11)	0.0639 (12)	−0.0055 (10)	0.0203 (11)	−0.0007 (10)
C43	0.0544 (11)	0.0627 (11)	0.0547 (10)	−0.0001 (8)	0.0102 (8)	0.0048 (8)
C44	0.0768 (14)	0.0631 (12)	0.0676 (13)	0.0054 (10)	0.0214 (11)	0.0009 (10)
C45	0.0916 (17)	0.0764 (15)	0.0743 (14)	0.0244 (13)	0.0135 (13)	−0.0004 (12)
C46	0.0867 (18)	0.108 (2)	0.0869 (17)	0.0333 (16)	0.0302 (14)	0.0023 (16)
C47	0.0867 (19)	0.126 (3)	0.105 (2)	0.0018 (17)	0.0516 (17)	0.0051 (19)
C48	0.0839 (17)	0.0793 (16)	0.0946 (18)	−0.0086 (13)	0.0348 (14)	0.0069 (14)
C34A	0.080 (3)	0.087 (4)	0.060 (4)	−0.007 (3)	−0.013 (3)	0.029 (3)
C35A	0.086 (4)	0.140 (5)	0.061 (3)	−0.007 (3)	0.018 (2)	0.010 (3)
C36A	0.127 (5)	0.142 (5)	0.060 (3)	−0.002 (4)	0.003 (3)	−0.005 (3)
C37A	0.105 (5)	0.143 (6)	0.085 (4)	−0.021 (4)	−0.026 (4)	0.012 (3)
C38A	0.086 (4)	0.154 (6)	0.119 (6)	0.003 (4)	−0.037 (4)	0.007 (5)
C39A	0.087 (4)	0.111 (4)	0.102 (4)	0.019 (3)	−0.021 (3)	0.007 (4)

Geometric parameters (Å, º)

O1—C1	1.3654 (19)	C26—H26D	1.044 (12)
O1—H101	0.82 (2)	C26—H26F	1.043 (12)
C1—C2	1.383 (2)	C26—H26E	1.040 (12)
C1—C9	1.4190 (18)	C27—H27	0.996 (19)
C2—C3	1.405 (2)	C28—C30	1.512 (4)
C2—C12	1.5038 (19)	C28—C29	1.540 (3)
N1—C22	1.318 (2)	C28—H28	1.00 (2)
N1—C31	1.455 (3)	C29—H29A	0.9600
N1—H111	0.96 (2)	C29—H29B	0.9600
O3—C7	1.2873 (19)	C29—H29C	0.9600
C3—C4	1.377 (2)	C30—H30A	0.9600
C3—C21	1.510 (2)	C30—H30B	0.9600
C4—C10	1.408 (2)	C30—H30C	0.9600
C4—H4	1.023 (19)	C31—C32	1.511 (4)
O5—C11	1.3635 (18)	C31—H31A	1.01 (2)
O5—H105	0.86 (2)	C31—H31B	1.02 (3)
C5—C6	1.352 (2)	C32—C33	1.523 (4)
C5—C10	1.461 (2)	C32—H32A	0.95 (4)
C5—C23	1.516 (3)	C32—H32B	1.02 (4)
N2—C27	1.302 (2)	C33—C34B	1.491 (8)
N2—C40	1.456 (2)	C33—C34A	1.504 (6)
N2—H112	0.95 (3)	C33—H33A	0.95 (5)
C6—O4	1.3678 (17)	C33—H33B	1.09 (3)
C6—C7	1.434 (2)	C34B—C39B	1.370 (4)
O4—H104	0.95 (3)	C34B—C35B	1.371 (4)
C7—C8	1.420 (2)	C35B—C36B	1.370 (4)
O7—C17	1.283 (2)	C35B—H35B	0.9300
C8—C22	1.405 (2)	C36B—C37B	1.368 (4)
C8—C9	1.460 (2)	C36B—H36B	0.9300
O8—C16	1.3716 (18)	C37B—C38B	1.369 (4)
O8—H108	0.96 (3)	C37B—H37B	0.9300
C9—C10	1.419 (2)	C38B—C39B	1.366 (4)
C11—C12	1.381 (2)	C38B—H38B	0.9300
C11—C19	1.4243 (19)	C39B—H39B	0.9300
C12—C13	1.406 (2)	C40—C41	1.504 (3)
C13—C14	1.381 (2)	C40—H40A	0.99 (2)
C13—C26	1.505 (2)	C40—H40B	0.96 (2)
C14—C20	1.402 (2)	C41—C42	1.507 (3)
C14—H14	0.98 (2)	C41—H41A	0.98 (2)
C15—C16	1.350 (2)	C41—H41B	0.98 (2)
C15—C20	1.465 (2)	C42—C43	1.510 (3)
C15—C28	1.522 (2)	C42—H42A	0.99 (3)
C16—C17	1.442 (2)	C42—H42B	0.95 (3)
C17—C18	1.421 (2)	C43—C48	1.384 (3)
C18—C27	1.414 (2)	C43—C44	1.386 (3)
C18—C19	1.456 (2)	C44—C45	1.387 (3)
C19—C20	1.425 (2)	C44—H44	1.00 (2)
C21—H21A	1.042 (12)	C45—C46	1.353 (4)
C21—H21B	1.043 (12)	C45—H45	1.06 (3)
C21—H21C	1.043 (12)	C46—C47	1.374 (4)
C21—H21D	1.042 (12)	C46—H46	1.03 (3)
C21—H21E	1.044 (12)	C47—C48	1.387 (4)
C21—H21F	1.042 (12)	C47—H47	1.05 (3)
C22—H22	1.038 (18)	C48—H48	0.96 (3)
C23—C25	1.515 (4)	C34A—C39A	1.373 (4)
C23—C24	1.538 (3)	C34A—C35A	1.374 (4)
C23—H23	0.94 (2)	C35A—C36A	1.365 (4)
C24—H24A	0.9600	C35A—H35A	0.9300
C24—H24B	0.9600	C36A—C37A	1.368 (4)
C24—H24C	0.9600	C36A—H36A	0.9300
C25—H25A	0.9600	C37A—C38A	1.370 (4)
C25—H25B	0.9600	C37A—H37A	0.9300
C25—H25C	0.9600	C38A—C39A	1.373 (4)
C26—H26A	1.042 (12)	C38A—H38A	0.9300
C26—H26B	1.041 (12)	C39A—H39A	0.9300
C26—H26C	1.040 (12)
C1—O1—H101	111.9 (16)	H26B—C26—H26F	140 (4)
O1—C1—C2	119.43 (12)	H26C—C26—H26F	36 (3)
O1—C1—C9	116.96 (13)	H26D—C26—H26F	108.5 (16)
C2—C1—C9	123.61 (14)	C13—C26—H26E	114 (3)
C1—C2—C3	118.94 (13)	H26A—C26—H26E	35 (3)
C1—C2—C12	120.05 (14)	H26B—C26—H26E	74 (3)
C3—C2—C12	120.99 (13)	H26C—C26—H26E	128 (4)
C22—N1—C31	122.98 (16)	H26D—C26—H26E	108.5 (16)
C22—N1—H111	113.2 (13)	H26F—C26—H26E	109.3 (16)
C31—N1—H111	123.7 (13)	N2—C27—C18	124.42 (14)
C4—C3—C2	118.63 (14)	N2—C27—H27	117.1 (11)
C4—C3—C21	121.34 (16)	C18—C27—H27	118.5 (11)
C2—C3—C21	120.03 (15)	C30—C28—C15	109.87 (19)
C3—C4—C10	123.33 (16)	C30—C28—C29	110.83 (19)
C3—C4—H4	116.0 (11)	C15—C28—C29	115.30 (19)
C10—C4—H4	120.7 (11)	C30—C28—H28	110.9 (12)
C11—O5—H105	112.0 (15)	C15—C28—H28	108.0 (12)
C6—C5—C10	118.20 (14)	C29—C28—H28	101.6 (13)
C6—C5—C23	120.59 (14)	C28—C29—H29A	109.5
C10—C5—C23	121.11 (15)	C28—C29—H29B	109.5
C27—N2—C40	124.94 (15)	H29A—C29—H29B	109.5
C27—N2—H112	113.8 (16)	C28—C29—H29C	109.5
C40—N2—H112	121.2 (15)	H29A—C29—H29C	109.5
C5—C6—O4	122.18 (16)	H29B—C29—H29C	109.5
C5—C6—C7	123.55 (13)	C28—C30—H30A	109.5
O4—C6—C7	114.26 (15)	C28—C30—H30B	109.5
C6—O4—H104	98.5 (19)	H30A—C30—H30B	109.5
O3—C7—C8	123.73 (15)	C28—C30—H30C	109.5
O3—C7—C6	116.67 (13)	H30A—C30—H30C	109.5
C8—C7—C6	119.58 (14)	H30B—C30—H30C	109.5
C22—C8—C7	117.29 (14)	N1—C31—C32	112.3 (2)
C22—C8—C9	124.23 (13)	N1—C31—H31A	107.9 (13)
C7—C8—C9	118.41 (14)	C32—C31—H31A	111.0 (13)
C16—O8—H108	101 (2)	N1—C31—H31B	110.3 (16)
C1—C9—C10	116.68 (13)	C32—C31—H31B	107.2 (16)
C1—C9—C8	123.72 (13)	H31A—C31—H31B	108.0 (19)
C10—C9—C8	119.59 (12)	C31—C32—C33	114.1 (3)
C4—C10—C9	118.75 (13)	C31—C32—H32A	113 (2)
C4—C10—C5	120.62 (14)	C33—C32—H32A	111 (2)
C9—C10—C5	120.62 (14)	C31—C32—H32B	104 (3)
O5—C11—C12	119.93 (13)	C33—C32—H32B	109 (3)
O5—C11—C19	116.67 (13)	H32A—C32—H32B	104 (3)
C12—C11—C19	123.40 (14)	C34B—C33—C34A	9.2 (6)
C11—C12—C13	119.29 (13)	C34B—C33—C32	116.8 (3)
C11—C12—C2	119.75 (13)	C34A—C33—C32	112.0 (3)
C13—C12—C2	120.92 (13)	C34B—C33—H33A	116 (3)
C14—C13—C12	118.49 (15)	C34A—C33—H33A	113 (3)
C14—C13—C26	120.62 (16)	C32—C33—H33A	113 (3)
C12—C13—C26	120.89 (14)	C34B—C33—H33B	94.7 (17)
C13—C14—C20	123.26 (16)	C34A—C33—H33B	103.8 (16)
C13—C14—H14	117.3 (12)	C32—C33—H33B	103.1 (16)
C20—C14—H14	119.5 (12)	H33A—C33—H33B	111 (3)
C16—C15—C20	117.88 (15)	C39B—C34B—C35B	120.3 (9)
C16—C15—C28	120.92 (14)	C39B—C34B—C33	117.5 (8)
C20—C15—C28	121.10 (15)	C35B—C34B—C33	122.2 (8)
C15—C16—O8	122.36 (15)	C36B—C35B—C34B	122.9 (11)
C15—C16—C17	123.86 (14)	C36B—C35B—H35B	118.5
O8—C16—C17	113.78 (15)	C34B—C35B—H35B	118.5
O7—C17—C18	123.72 (15)	C37B—C36B—C35B	115.8 (12)
O7—C17—C16	116.81 (14)	C37B—C36B—H36B	122.1
C18—C17—C16	119.46 (14)	C35B—C36B—H36B	122.1
C27—C18—C17	116.75 (14)	C36B—C37B—C38B	122.0 (13)
C27—C18—C19	125.01 (13)	C36B—C37B—H37B	119.0
C17—C18—C19	118.24 (14)	C38B—C37B—H37B	119.0
C11—C19—C20	116.44 (13)	C39B—C38B—C37B	121.5 (12)
C11—C19—C18	123.53 (13)	C39B—C38B—H38B	119.2
C20—C19—C18	120.02 (12)	C37B—C38B—H38B	119.2
C14—C20—C19	119.08 (13)	C38B—C39B—C34B	117.4 (11)
C14—C20—C15	120.52 (14)	C38B—C39B—H39B	121.3
C19—C20—C15	120.41 (14)	C34B—C39B—H39B	121.3
C3—C21—H21A	112.5 (17)	N2—C40—C41	110.32 (15)
C3—C21—H21B	111.3 (16)	N2—C40—H40A	109.9 (13)
H21A—C21—H21B	108.4 (13)	C41—C40—H40A	111.3 (13)
C3—C21—H21C	106.7 (16)	N2—C40—H40B	109.5 (13)
H21A—C21—H21C	109.1 (14)	C41—C40—H40B	113.2 (13)
H21B—C21—H21C	108.9 (14)	H40A—C40—H40B	102.4 (18)
C3—C21—H21D	119 (4)	C40—C41—C42	112.57 (16)
H21A—C21—H21D	128 (4)	C40—C41—H41A	106.0 (13)
H21B—C21—H21D	50 (3)	C42—C41—H41A	111.0 (13)
H21C—C21—H21D	59 (3)	C40—C41—H41B	106.5 (13)
C3—C21—H21E	99 (4)	C42—C41—H41B	115.0 (13)
H21A—C21—H21E	59 (4)	H41A—C41—H41B	105.1 (19)
H21B—C21—H21E	61 (4)	C41—C42—C43	115.74 (17)
H21C—C21—H21E	154 (4)	C41—C42—H42A	107.5 (15)
H21D—C21—H21E	108.5 (17)	C43—C42—H42A	110.6 (15)
C3—C21—H21F	112 (4)	C41—C42—H42B	108.8 (15)
H21A—C21—H21F	50 (4)	C43—C42—H42B	110.3 (15)
H21B—C21—H21F	137 (4)	H42A—C42—H42B	103 (2)
H21C—C21—H21F	62 (4)	C48—C43—C44	116.8 (2)
H21D—C21—H21F	109.1 (17)	C48—C43—C42	120.00 (19)
H21E—C21—H21F	108.4 (17)	C44—C43—C42	123.11 (17)
N1—C22—C8	124.54 (15)	C43—C44—C45	121.8 (2)
N1—C22—H22	115.8 (10)	C43—C44—H44	119.0 (14)
C8—C22—H22	119.7 (10)	C45—C44—H44	119.2 (14)
C25—C23—C5	110.0 (2)	C46—C45—C44	120.3 (3)
C25—C23—C24	111.4 (2)	C46—C45—H45	119.9 (16)
C5—C23—C24	114.98 (19)	C44—C45—H45	119.7 (16)
C25—C23—H23	108.7 (13)	C45—C46—C47	119.4 (2)
C5—C23—H23	106.7 (13)	C45—C46—H46	121.4 (18)
C24—C23—H23	104.7 (14)	C47—C46—H46	119.2 (18)
C23—C24—H24A	109.5	C46—C47—C48	120.5 (3)
C23—C24—H24B	109.5	C46—C47—H47	117.6 (18)
H24A—C24—H24B	109.5	C48—C47—H47	121.6 (18)
C23—C24—H24C	109.5	C43—C48—C47	121.2 (3)
H24A—C24—H24C	109.5	C43—C48—H48	118.5 (19)
H24B—C24—H24C	109.5	C47—C48—H48	120.3 (19)
C23—C25—H25A	109.5	C39A—C34A—C35A	116.8 (5)
C23—C25—H25B	109.5	C39A—C34A—C33	124.5 (5)
H25A—C25—H25B	109.5	C35A—C34A—C33	118.7 (5)
C23—C25—H25C	109.5	C36A—C35A—C34A	123.0 (6)
H25A—C25—H25C	109.5	C36A—C35A—H35A	118.5
H25B—C25—H25C	109.5	C34A—C35A—H35A	118.5
C13—C26—H26A	109 (2)	C35A—C36A—C37A	118.4 (6)
C13—C26—H26B	107 (2)	C35A—C36A—H36A	120.8
H26A—C26—H26B	108.7 (15)	C37A—C36A—H36A	120.8
C13—C26—H26C	114 (2)	C36A—C37A—C38A	120.8 (7)
H26A—C26—H26C	109.3 (15)	C36A—C37A—H37A	119.6
H26B—C26—H26C	109.3 (15)	C38A—C37A—H37A	119.6
C13—C26—H26D	108 (3)	C37A—C38A—C39A	119.1 (7)
H26A—C26—H26D	138 (4)	C37A—C38A—H38A	120.5
H26B—C26—H26D	40 (3)	C39A—C38A—H38A	120.5
H26C—C26—H26D	73 (3)	C38A—C39A—C34A	121.9 (6)
C13—C26—H26F	108 (3)	C38A—C39A—H39A	119.1
H26A—C26—H26F	79 (3)	C34A—C39A—H39A	119.1
O1—C1—C2—C3	177.23 (14)	C27—C18—C19—C11	−1.8 (3)
C9—C1—C2—C3	−2.8 (2)	C17—C18—C19—C11	177.48 (16)
O1—C1—C2—C12	−4.6 (2)	C27—C18—C19—C20	179.54 (15)
C9—C1—C2—C12	175.40 (14)	C17—C18—C19—C20	−1.2 (2)
C1—C2—C3—C4	0.8 (2)	C13—C14—C20—C19	−0.7 (3)
C12—C2—C3—C4	−177.33 (15)	C13—C14—C20—C15	178.69 (18)
C1—C2—C3—C21	−179.62 (17)	C11—C19—C20—C14	−1.2 (2)
C12—C2—C3—C21	2.2 (2)	C18—C19—C20—C14	177.58 (15)
C2—C3—C4—C10	0.7 (3)	C11—C19—C20—C15	179.46 (15)
C21—C3—C4—C10	−178.81 (17)	C18—C19—C20—C15	−1.8 (2)
C10—C5—C6—O4	176.00 (16)	C16—C15—C20—C14	−175.15 (18)
C23—C5—C6—O4	−0.3 (3)	C28—C15—C20—C14	1.4 (3)
C10—C5—C6—C7	−2.6 (3)	C16—C15—C20—C19	4.2 (3)
C23—C5—C6—C7	−178.96 (17)	C28—C15—C20—C19	−179.17 (17)
C5—C6—C7—O3	−179.57 (16)	C31—N1—C22—C8	−174.92 (17)
O4—C6—C7—O3	1.7 (2)	C7—C8—C22—N1	−1.1 (2)
C5—C6—C7—C8	1.7 (3)	C9—C8—C22—N1	175.90 (15)
O4—C6—C7—C8	−177.03 (15)	C6—C5—C23—C25	79.4 (2)
O3—C7—C8—C22	−1.8 (2)	C10—C5—C23—C25	−96.9 (2)
C6—C7—C8—C22	176.82 (14)	C6—C5—C23—C24	−47.3 (3)
O3—C7—C8—C9	−179.06 (14)	C10—C5—C23—C24	136.5 (2)
C6—C7—C8—C9	−0.4 (2)	C40—N2—C27—C18	−179.68 (18)
O1—C1—C9—C10	−177.00 (13)	C17—C18—C27—N2	−0.3 (3)
C2—C1—C9—C10	3.0 (2)	C19—C18—C27—N2	179.05 (16)
O1—C1—C9—C8	4.4 (2)	C16—C15—C28—C30	84.0 (2)
C2—C1—C9—C8	−175.58 (14)	C20—C15—C28—C30	−92.5 (2)
C22—C8—C9—C1	1.8 (2)	C16—C15—C28—C29	−42.1 (3)
C7—C8—C9—C1	178.80 (14)	C20—C15—C28—C29	141.4 (2)
C22—C8—C9—C10	−176.76 (14)	C22—N1—C31—C32	79.2 (3)
C7—C8—C9—C10	0.3 (2)	N1—C31—C32—C33	−179.3 (3)
C3—C4—C10—C9	−0.4 (2)	C31—C32—C33—C34B	−54.8 (7)
C3—C4—C10—C5	178.10 (16)	C31—C32—C33—C34A	−63.5 (5)
C1—C9—C10—C4	−1.3 (2)	C34A—C33—C34B—C39B	171.9 (14)
C8—C9—C10—C4	177.30 (14)	C32—C33—C34B—C39B	110.8 (6)
C1—C9—C10—C5	−179.88 (14)	C34A—C33—C34B—C35B	−8.1 (14)
C8—C9—C10—C5	−1.2 (2)	C32—C33—C34B—C35B	−69.2 (6)
C6—C5—C10—C4	−176.12 (16)	C39B—C34B—C35B—C36B	−0.04 (14)
C23—C5—C10—C4	0.2 (2)	C33—C34B—C35B—C36B	179.99 (9)
C6—C5—C10—C9	2.4 (2)	C34B—C35B—C36B—C37B	0.02 (14)
C23—C5—C10—C9	178.71 (16)	C35B—C36B—C37B—C38B	−0.01 (14)
O5—C11—C12—C13	178.99 (15)	C36B—C37B—C38B—C39B	0.01 (14)
C19—C11—C12—C13	−1.7 (2)	C37B—C38B—C39B—C34B	−0.02 (14)
O5—C11—C12—C2	−3.3 (2)	C35B—C34B—C39B—C38B	0.04 (13)
C19—C11—C12—C2	176.04 (14)	C33—C34B—C39B—C38B	−179.99 (8)
C1—C2—C12—C11	90.18 (19)	C27—N2—C40—C41	−173.35 (18)
C3—C2—C12—C11	−91.68 (19)	N2—C40—C41—C42	−177.27 (18)
C1—C2—C12—C13	−92.2 (2)	C40—C41—C42—C43	179.3 (2)
C3—C2—C12—C13	86.0 (2)	C41—C42—C43—C48	172.4 (2)
C11—C12—C13—C14	−0.3 (3)	C41—C42—C43—C44	−11.0 (3)
C2—C12—C13—C14	−177.96 (16)	C48—C43—C44—C45	−0.5 (3)
C11—C12—C13—C26	179.44 (18)	C42—C43—C44—C45	−177.2 (2)
C2—C12—C13—C26	1.8 (3)	C43—C44—C45—C46	−0.1 (4)
C12—C13—C14—C20	1.5 (3)	C44—C45—C46—C47	0.7 (4)
C26—C13—C14—C20	−178.3 (2)	C45—C46—C47—C48	−0.7 (5)
C20—C15—C16—O8	175.71 (18)	C44—C43—C48—C47	0.5 (4)
C28—C15—C16—O8	−0.9 (3)	C42—C43—C48—C47	177.3 (3)
C20—C15—C16—C17	−3.8 (3)	C46—C47—C48—C43	0.1 (5)
C28—C15—C16—C17	179.64 (19)	C34B—C33—C34A—C39A	0.2 (14)
C15—C16—C17—O7	−177.93 (19)	C32—C33—C34A—C39A	122.7 (5)
O8—C16—C17—O7	2.6 (3)	C34B—C33—C34A—C35A	−180 (100)
C15—C16—C17—C18	0.8 (3)	C32—C33—C34A—C35A	−57.4 (5)
O8—C16—C17—C18	−178.70 (17)	C39A—C34A—C35A—C36A	−0.03 (13)
O7—C17—C18—C27	−0.3 (3)	C33—C34A—C35A—C36A	179.99 (9)
C16—C17—C18—C27	−178.90 (16)	C34A—C35A—C36A—C37A	0.03 (14)
O7—C17—C18—C19	−179.61 (17)	C35A—C36A—C37A—C38A	−0.03 (13)
C16—C17—C18—C19	1.7 (3)	C36A—C37A—C38A—C39A	0.02 (14)
O5—C11—C19—C20	−178.27 (14)	C37A—C38A—C39A—C34A	−0.02 (14)
C12—C11—C19—C20	2.4 (2)	C35A—C34A—C39A—C38A	0.02 (13)
O5—C11—C19—C18	3.0 (2)	C33—C34A—C39A—C38A	180.00 (8)
C12—C11—C19—C18	−176.33 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H101···O7^i	0.82 (2)	1.99 (2)	2.617 (2)	133 (2)
N1—H111···O3	0.96 (2)	1.74 (2)	2.540 (2)	139 (2)
O4—H104···O5^ii	0.95 (3)	2.42 (3)	3.225 (2)	142 (3)
O4—H104···O3	0.95 (3)	1.87 (3)	2.576 (2)	128 (3)
O5—H105···O3^ii	0.86 (2)	1.99 (2)	2.654 (2)	134 (2)
N2—H112···O7	0.95 (3)	1.73 (3)	2.524 (2)	138 (2)
O8—H108···O7	0.96 (3)	1.91 (3)	2.577 (2)	124 (3)
O8—H108···O1^iii	0.96 (3)	2.19 (4)	3.036 (2)	146 (3)

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

(I_120K) 2,2'-Bis{1,6-dihydroxy-5-isopropyl-8-[(3-phenylpropylamino)methylidene]naphthalen-7-one}

Crystal data

C48H52N2O6	F(000) = 1608
Mr = 752.92	Dx = 1.234 Mg m^−3 Dm = 1.19 Mg m^−3 Dm measured by flotation in aqueous KI
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 33430 reflections
a = 11.9559 (9) Å	θ = 2.2–27.4°
b = 29.079 (2) Å	µ = 0.08 mm^−1
c = 11.6918 (9) Å	T = 120 K
β = 94.207 (1)°	Diamond, yellow
V = 4053.9 (5) Å^3	0.60 × 0.40 × 0.30 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer	9192 independent reflections
Radiation source: fine-focus sealed tube	7917 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.953, Tmax = 0.976	k = −37→37
58753 measured reflections	l = −15→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0623P)^2 + 1.8081P] where P = (Fo^2 + 2Fc^2)/3
9192 reflections	(Δ/σ)max = 0.001
705 parameters	Δρmax = 0.78 e Å^−3
73 restraints	Δρmin = −0.37 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	0.02818 (8)	0.10415 (3)	0.41306 (8)	0.02308 (19)
H101	0.0321 (17)	0.1332 (8)	0.4181 (17)	0.049 (5)*
C1	0.11754 (10)	0.08263 (4)	0.46898 (10)	0.0180 (2)
N1	−0.09397 (9)	0.00460 (4)	0.21931 (9)	0.0242 (2)
H111	−0.0777 (15)	−0.0266 (7)	0.2155 (15)	0.039 (5)*
C2	0.19342 (10)	0.10806 (4)	0.53868 (10)	0.0191 (2)
N2	−0.08040 (9)	0.24140 (4)	0.88295 (9)	0.0230 (2)
H112	−0.0735 (17)	0.2724 (8)	0.8884 (18)	0.052 (6)*
O3	0.01624 (8)	−0.06586 (3)	0.28800 (8)	0.0264 (2)
C3	0.28144 (10)	0.08517 (4)	0.60136 (11)	0.0215 (2)
O4	0.17734 (9)	−0.10675 (3)	0.40633 (9)	0.0291 (2)
H104	0.1253 (18)	−0.1124 (7)	0.3548 (19)	0.049 (6)*
C4	0.29041 (10)	0.03803 (4)	0.59030 (11)	0.0215 (2)
H4	0.3522 (14)	0.0225 (6)	0.6354 (14)	0.027 (4)*
O5	0.05678 (8)	0.15098 (3)	0.69249 (8)	0.0255 (2)
H105	0.0657 (16)	0.1223 (7)	0.6767 (17)	0.045 (5)*
C5	0.23147 (10)	−0.03789 (4)	0.50624 (11)	0.0208 (2)
C6	0.16359 (11)	−0.06104 (4)	0.42796 (11)	0.0217 (2)
O7	−0.01550 (9)	0.31792 (3)	0.81195 (9)	0.0323 (2)
C7	0.07332 (10)	−0.03959 (4)	0.35899 (10)	0.0204 (2)
C8	0.05371 (10)	0.00830 (4)	0.37107 (10)	0.0187 (2)
O8	0.09452 (9)	0.37003 (3)	0.68062 (9)	0.0318 (2)
H108	0.0551 (17)	0.3721 (7)	0.7403 (19)	0.051 (6)*
C9	0.12733 (10)	0.03445 (4)	0.45210 (10)	0.0172 (2)
C10	0.21612 (10)	0.01168 (4)	0.51679 (10)	0.0186 (2)
C11	0.11489 (10)	0.17878 (4)	0.62356 (10)	0.0190 (2)
C12	0.18174 (10)	0.15936 (4)	0.54448 (10)	0.0195 (2)
C13	0.23984 (11)	0.18842 (4)	0.47261 (11)	0.0223 (3)
C14	0.22792 (11)	0.23547 (4)	0.48321 (11)	0.0221 (2)
H14	0.2663 (13)	0.2543 (5)	0.4313 (13)	0.024 (4)*
C15	0.15550 (11)	0.30600 (4)	0.57399 (11)	0.0222 (2)
C16	0.09885 (11)	0.32380 (4)	0.66003 (12)	0.0238 (3)
C17	0.03806 (11)	0.29603 (4)	0.73742 (11)	0.0232 (3)
C18	0.03867 (10)	0.24748 (4)	0.72660 (10)	0.0195 (2)
C19	0.10394 (10)	0.22699 (4)	0.63909 (10)	0.0184 (2)
C20	0.16209 (10)	0.25592 (4)	0.56460 (10)	0.0198 (2)
C21	0.36362 (12)	0.11190 (5)	0.67936 (13)	0.0283 (3)
H21C	0.4044 (16)	0.1351 (7)	0.6338 (16)	0.042 (5)*
H21B	0.3248 (16)	0.1303 (7)	0.7374 (17)	0.045 (5)*
H21A	0.4211 (16)	0.0913 (7)	0.7185 (17)	0.045 (5)*
C22	−0.03333 (10)	0.02768 (4)	0.29809 (11)	0.0210 (2)
H22A	−0.0519 (13)	0.0603 (5)	0.3034 (13)	0.024 (4)*
C23	0.32598 (12)	−0.06257 (4)	0.57501 (12)	0.0277 (3)
H23	0.3520 (14)	−0.0429 (6)	0.6420 (15)	0.035 (4)*
C24	0.42661 (14)	−0.06743 (7)	0.50281 (18)	0.0454 (4)
H24C	0.4507 (19)	−0.0365 (9)	0.473 (2)	0.068 (7)*
H24B	0.4071 (17)	−0.0869 (8)	0.4376 (19)	0.055 (6)*
H24A	0.4906 (18)	−0.0813 (8)	0.5497 (18)	0.056 (6)*
C25	0.29445 (16)	−0.10921 (5)	0.62566 (15)	0.0383 (4)
H25C	0.3507 (17)	−0.1183 (7)	0.6876 (17)	0.048 (5)*
H25B	0.2937 (17)	−0.1337 (7)	0.5698 (18)	0.052 (6)*
H25A	0.2195 (19)	−0.1086 (7)	0.6600 (19)	0.057 (6)*
C26	0.31375 (13)	0.16848 (5)	0.38591 (13)	0.0307 (3)
H26C	0.3335 (15)	0.1919 (7)	0.3289 (16)	0.041 (5)*
H26B	0.2746 (17)	0.1426 (7)	0.3416 (17)	0.050 (5)*
H26A	0.3829 (18)	0.1567 (7)	0.4239 (18)	0.055 (6)*
C27	−0.02427 (10)	0.22227 (4)	0.80412 (11)	0.0206 (2)
H27	−0.0280 (13)	0.1893 (6)	0.8002 (13)	0.027 (4)*
C28	0.21666 (13)	0.33729 (4)	0.49441 (12)	0.0285 (3)
H28	0.2270 (14)	0.3200 (6)	0.4229 (15)	0.032 (4)*
C29	0.15283 (15)	0.38114 (5)	0.45508 (14)	0.0357 (3)
H29B	0.1543 (14)	0.4049 (6)	0.5159 (15)	0.036 (4)*
H29C	0.1874 (15)	0.3946 (6)	0.3881 (16)	0.037 (5)*
H29A	0.0705 (18)	0.3745 (7)	0.4304 (17)	0.050 (5)*
C30	0.33178 (14)	0.34981 (6)	0.55088 (16)	0.0390 (4)
H30C	0.3254 (14)	0.3668 (6)	0.6238 (16)	0.036 (4)*
H30B	0.3787 (17)	0.3223 (7)	0.5672 (17)	0.048 (5)*
H30A	0.3730 (16)	0.3689 (7)	0.4997 (17)	0.047 (5)*
C31	−0.17656 (12)	0.02684 (5)	0.13941 (12)	0.0280 (3)
H31B	−0.2304 (14)	0.0025 (6)	0.1090 (14)	0.032 (4)*
H31A	−0.2193 (15)	0.0498 (6)	0.1822 (16)	0.040 (5)*
C32	−0.12169 (14)	0.05076 (6)	0.04222 (15)	0.0399 (4)
H32B	−0.0765 (18)	0.0269 (8)	0.0009 (18)	0.055 (6)*
H32A	−0.0663 (18)	0.0738 (8)	0.0753 (19)	0.060 (6)*
C33	−0.20658 (16)	0.07359 (6)	−0.04442 (16)	0.0443 (4)
H33B	−0.2473 (16)	0.0960 (7)	−0.0011 (17)	0.044 (5)*
H33A	−0.1624 (19)	0.0901 (8)	−0.105 (2)	0.063 (6)*
C34	−0.28915 (14)	0.04002 (6)	−0.10122 (13)	0.0380 (3)
C35	−0.24830 (19)	0.00324 (7)	−0.16325 (15)	0.0528 (4)
H35	−0.158 (2)	0.0005 (9)	−0.170 (2)	0.090 (8)*
C36	−0.3173 (2)	−0.02896 (9)	−0.21598 (17)	0.0697 (6)
H36	−0.2870	−0.0536	−0.2572	0.084*
C37	−0.4283 (3)	−0.02542 (10)	−0.2090 (2)	0.0772 (6)
H37	−0.487 (3)	−0.0475 (11)	−0.247 (3)	0.116 (11)*
C38	−0.47539 (18)	0.00983 (10)	−0.1487 (2)	0.0757 (6)
H38	−0.5543	0.0116	−0.1441	0.091*
C39	−0.40283 (16)	0.04364 (8)	−0.0932 (2)	0.0581 (5)
H39	−0.4242 (14)	0.0672 (6)	−0.0457 (15)	0.029 (4)*
C40	−0.14515 (12)	0.21628 (4)	0.96384 (11)	0.0243 (3)
H40B	−0.0941 (14)	0.1972 (6)	1.0133 (14)	0.029 (4)*
H40A	−0.1989 (14)	0.1961 (6)	0.9195 (14)	0.030 (4)*
C41	−0.20643 (11)	0.25041 (4)	1.03490 (11)	0.0229 (3)
H41B	−0.2566 (13)	0.2683 (5)	0.9832 (13)	0.022 (4)*
H41A	−0.1514 (14)	0.2712 (6)	1.0731 (14)	0.028 (4)*
C42	−0.27215 (12)	0.22669 (5)	1.12437 (12)	0.0267 (3)
H42B	−0.2188 (14)	0.2081 (6)	1.1742 (15)	0.030 (4)*
H42A	−0.3255 (15)	0.2050 (6)	1.0846 (15)	0.034 (4)*
C43	−0.33502 (11)	0.25879 (5)	1.19907 (11)	0.0240 (3)
C44	−0.40572 (12)	0.24050 (5)	1.27734 (12)	0.0308 (3)
H44	−0.4172 (15)	0.2069 (7)	1.2818 (16)	0.041 (5)*
C45	−0.46126 (13)	0.26897 (6)	1.35000 (14)	0.0371 (3)
H45	−0.5099 (18)	0.2555 (7)	1.4058 (18)	0.053 (6)*
C46	−0.44767 (13)	0.31624 (6)	1.34521 (13)	0.0356 (3)
H46	−0.4847 (16)	0.3378 (7)	1.3958 (16)	0.044 (5)*
C47	−0.37911 (13)	0.33500 (5)	1.26738 (12)	0.0320 (3)
H47	−0.3676 (15)	0.3682 (7)	1.2635 (16)	0.040 (5)*
C48	−0.32328 (12)	0.30647 (5)	1.19450 (12)	0.0271 (3)
H48	−0.2745 (14)	0.3207 (6)	1.1390 (14)	0.031 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0264 (5)	0.0124 (4)	0.0298 (5)	0.0011 (3)	−0.0021 (4)	0.0002 (3)
C1	0.0203 (5)	0.0149 (5)	0.0192 (5)	0.0004 (4)	0.0050 (4)	0.0009 (4)
N1	0.0275 (6)	0.0205 (5)	0.0241 (5)	−0.0034 (4)	−0.0017 (4)	0.0004 (4)
C2	0.0215 (6)	0.0140 (5)	0.0223 (6)	−0.0013 (4)	0.0059 (4)	−0.0029 (4)
N2	0.0268 (5)	0.0194 (5)	0.0235 (5)	−0.0045 (4)	0.0067 (4)	−0.0044 (4)
O3	0.0360 (5)	0.0161 (4)	0.0264 (5)	−0.0049 (4)	−0.0013 (4)	−0.0027 (3)
C3	0.0216 (6)	0.0190 (6)	0.0242 (6)	−0.0019 (4)	0.0029 (5)	−0.0037 (5)
O4	0.0363 (5)	0.0137 (4)	0.0364 (6)	0.0030 (4)	−0.0025 (4)	−0.0060 (4)
C4	0.0204 (6)	0.0196 (6)	0.0246 (6)	0.0013 (4)	0.0015 (5)	−0.0020 (5)
O5	0.0368 (5)	0.0132 (4)	0.0279 (5)	−0.0031 (4)	0.0123 (4)	−0.0024 (3)
C5	0.0227 (6)	0.0160 (5)	0.0239 (6)	0.0020 (4)	0.0042 (5)	−0.0003 (4)
C6	0.0274 (6)	0.0133 (5)	0.0251 (6)	0.0010 (4)	0.0058 (5)	−0.0010 (4)
O7	0.0404 (6)	0.0183 (4)	0.0407 (6)	−0.0048 (4)	0.0212 (5)	−0.0094 (4)
C7	0.0250 (6)	0.0165 (5)	0.0201 (6)	−0.0036 (4)	0.0037 (5)	−0.0008 (4)
C8	0.0219 (6)	0.0149 (5)	0.0196 (6)	−0.0027 (4)	0.0041 (4)	−0.0001 (4)
O8	0.0475 (6)	0.0132 (4)	0.0370 (6)	−0.0021 (4)	0.0192 (5)	−0.0042 (4)
C9	0.0195 (5)	0.0144 (5)	0.0182 (5)	−0.0016 (4)	0.0050 (4)	−0.0009 (4)
C10	0.0203 (6)	0.0157 (5)	0.0204 (6)	−0.0001 (4)	0.0053 (4)	−0.0014 (4)
C11	0.0213 (6)	0.0155 (5)	0.0202 (6)	−0.0026 (4)	0.0005 (4)	−0.0008 (4)
C12	0.0214 (6)	0.0144 (5)	0.0224 (6)	−0.0018 (4)	0.0008 (4)	−0.0033 (4)
C13	0.0244 (6)	0.0185 (6)	0.0248 (6)	−0.0020 (4)	0.0060 (5)	−0.0041 (5)
C14	0.0256 (6)	0.0173 (6)	0.0242 (6)	−0.0038 (4)	0.0070 (5)	−0.0014 (5)
C15	0.0271 (6)	0.0155 (5)	0.0244 (6)	−0.0025 (4)	0.0043 (5)	−0.0008 (4)
C16	0.0289 (6)	0.0135 (5)	0.0294 (6)	−0.0018 (5)	0.0060 (5)	−0.0026 (5)
C17	0.0253 (6)	0.0181 (6)	0.0268 (6)	−0.0020 (5)	0.0065 (5)	−0.0048 (5)
C18	0.0211 (6)	0.0165 (5)	0.0209 (6)	−0.0020 (4)	0.0016 (5)	−0.0035 (4)
C19	0.0200 (5)	0.0163 (5)	0.0188 (5)	−0.0016 (4)	0.0007 (4)	−0.0026 (4)
C20	0.0219 (6)	0.0159 (5)	0.0217 (6)	−0.0017 (4)	0.0016 (5)	−0.0023 (4)
C21	0.0269 (7)	0.0225 (6)	0.0345 (7)	−0.0020 (5)	−0.0043 (6)	−0.0069 (5)
C22	0.0233 (6)	0.0184 (6)	0.0215 (6)	−0.0029 (4)	0.0035 (5)	0.0005 (4)
C23	0.0296 (7)	0.0196 (6)	0.0331 (7)	0.0060 (5)	−0.0035 (6)	−0.0033 (5)
C24	0.0289 (8)	0.0463 (10)	0.0610 (11)	0.0124 (7)	0.0042 (8)	−0.0026 (9)
C25	0.0501 (10)	0.0224 (7)	0.0408 (9)	0.0074 (6)	−0.0080 (7)	0.0040 (6)
C26	0.0368 (8)	0.0206 (6)	0.0370 (8)	−0.0027 (5)	0.0177 (6)	−0.0051 (6)
C27	0.0229 (6)	0.0178 (6)	0.0211 (6)	−0.0010 (4)	0.0012 (5)	−0.0027 (4)
C28	0.0429 (8)	0.0161 (6)	0.0283 (7)	−0.0020 (5)	0.0149 (6)	−0.0012 (5)
C29	0.0555 (10)	0.0210 (6)	0.0315 (8)	0.0011 (6)	0.0095 (7)	0.0036 (6)
C30	0.0363 (8)	0.0314 (8)	0.0517 (10)	−0.0060 (6)	0.0201 (7)	0.0040 (7)
C31	0.0269 (7)	0.0298 (7)	0.0266 (7)	−0.0015 (5)	−0.0038 (5)	0.0004 (5)
C32	0.0348 (8)	0.0431 (9)	0.0404 (9)	−0.0101 (7)	−0.0068 (7)	0.0165 (7)
C33	0.0482 (10)	0.0379 (8)	0.0446 (9)	−0.0052 (7)	−0.0105 (8)	0.0155 (7)
C34	0.0397 (8)	0.0440 (8)	0.0290 (7)	−0.0048 (6)	−0.0060 (6)	0.0165 (6)
C35	0.0672 (12)	0.0618 (11)	0.0306 (8)	−0.0115 (9)	0.0118 (8)	0.0033 (7)
C36	0.1006 (15)	0.0733 (14)	0.0343 (10)	−0.0202 (12)	−0.0013 (10)	−0.0010 (9)
C37	0.0925 (14)	0.0813 (15)	0.0522 (13)	−0.0266 (12)	−0.0326 (12)	0.0200 (10)
C38	0.0378 (10)	0.0984 (16)	0.0868 (16)	−0.0083 (9)	−0.0237 (10)	0.0408 (12)
C39	0.0405 (9)	0.0657 (12)	0.0664 (13)	0.0084 (8)	−0.0078 (9)	0.0243 (10)
C40	0.0291 (7)	0.0224 (6)	0.0224 (6)	−0.0033 (5)	0.0072 (5)	−0.0015 (5)
C41	0.0236 (6)	0.0246 (6)	0.0208 (6)	−0.0014 (5)	0.0038 (5)	−0.0015 (5)
C42	0.0318 (7)	0.0246 (6)	0.0244 (6)	−0.0013 (5)	0.0078 (5)	−0.0005 (5)
C43	0.0233 (6)	0.0289 (6)	0.0199 (6)	0.0009 (5)	0.0016 (5)	0.0006 (5)
C44	0.0302 (7)	0.0335 (7)	0.0294 (7)	−0.0010 (6)	0.0073 (6)	0.0029 (6)
C45	0.0310 (7)	0.0496 (9)	0.0322 (8)	0.0039 (6)	0.0118 (6)	0.0034 (7)
C46	0.0314 (7)	0.0461 (9)	0.0299 (7)	0.0145 (6)	0.0059 (6)	−0.0035 (6)
C47	0.0349 (7)	0.0310 (7)	0.0298 (7)	0.0085 (6)	0.0000 (6)	−0.0017 (6)
C48	0.0284 (7)	0.0283 (7)	0.0251 (6)	0.0020 (5)	0.0041 (5)	0.0010 (5)

Geometric parameters (Å, º)

O1—C1	1.3630 (14)	C25—H25C	0.99 (2)
O1—H101	0.85 (2)	C25—H25B	0.97 (2)
C1—C2	1.3876 (17)	C25—H25A	1.01 (2)
C1—C9	1.4210 (15)	C26—H26C	0.993 (19)
N1—C22	1.3139 (16)	C26—H26B	1.01 (2)
N1—C31	1.4596 (17)	C26—H26A	0.97 (2)
N1—H111	0.930 (19)	C27—H27	0.962 (16)
C2—C3	1.4051 (17)	C28—C30	1.526 (2)
C2—C12	1.5003 (15)	C28—C29	1.539 (2)
N2—C27	1.3039 (16)	C28—H28	0.991 (17)
N2—C40	1.4610 (16)	C29—H29B	0.990 (18)
N2—H112	0.91 (2)	C29—H29C	0.992 (19)
O3—C7	1.2865 (15)	C29—H29A	1.02 (2)
C3—C4	1.3819 (17)	C30—H30C	0.993 (18)
C3—C21	1.5065 (17)	C30—H30B	0.99 (2)
O4—C6	1.3652 (14)	C30—H30A	0.98 (2)
O4—H104	0.85 (2)	C31—C32	1.521 (2)
C4—C10	1.4151 (17)	C31—H31B	1.004 (17)
C4—H4	0.985 (16)	C31—H31A	0.997 (19)
O5—C11	1.3665 (14)	C32—C33	1.532 (2)
O5—H105	0.86 (2)	C32—H32B	1.02 (2)
C5—C6	1.3566 (18)	C32—H32A	1.00 (2)
C5—C10	1.4596 (16)	C33—C34	1.507 (2)
C5—C23	1.5182 (17)	C33—H33B	0.98 (2)
C6—C7	1.4411 (18)	C33—H33A	1.03 (2)
O7—C17	1.2871 (15)	C34—C39	1.373 (3)
C7—C8	1.4209 (16)	C34—C35	1.400 (3)
C8—C22	1.4136 (17)	C35—C36	1.365 (3)
C8—C9	1.4588 (16)	C35—H35	1.09 (3)
O8—C16	1.3674 (14)	C36—C37	1.339 (4)
O8—H108	0.87 (2)	C36—H36	0.9500
C9—C10	1.4211 (16)	C37—C38	1.387 (4)
C11—C12	1.3859 (17)	C37—H37	1.03 (3)
C11—C19	1.4211 (16)	C38—C39	1.434 (3)
C12—C13	1.4101 (17)	C38—H38	0.9500
C13—C14	1.3822 (17)	C39—H39	0.930 (17)
C13—C26	1.5086 (17)	C40—C41	1.5169 (17)
C14—C20	1.4101 (17)	C40—H40B	0.980 (17)
C14—H14	0.959 (16)	C40—H40A	0.989 (17)
C15—C16	1.3560 (18)	C41—C42	1.5192 (18)
C15—C20	1.4628 (16)	C41—H41B	0.972 (16)
C15—C28	1.5259 (17)	C41—H41A	0.977 (17)
C16—C17	1.4476 (17)	C42—C43	1.5151 (18)
C17—C18	1.4175 (16)	C42—H42B	0.992 (17)
C18—C27	1.4230 (17)	C42—H42A	0.989 (18)
C18—C19	1.4587 (16)	C43—C48	1.3949 (19)
C19—C20	1.4278 (16)	C43—C44	1.3959 (18)
C21—H21C	1.007 (19)	C44—C45	1.389 (2)
C21—H21B	1.00 (2)	C44—H44	0.988 (19)
C21—H21A	1.00 (2)	C45—C46	1.386 (2)
C22—H22A	0.976 (16)	C45—H45	0.99 (2)
C23—C24	1.526 (2)	C46—C47	1.381 (2)
C23—C25	1.538 (2)	C46—H46	0.99 (2)
C23—H23	1.001 (18)	C47—C48	1.3939 (19)
C24—H24C	1.01 (3)	C47—H47	0.98 (2)
C24—H24B	0.97 (2)	C48—H48	0.994 (17)
C24—H24A	0.99 (2)
C1—O1—H101	112.7 (14)	C13—C26—H26B	111.0 (11)
O1—C1—C2	119.53 (10)	H26C—C26—H26B	106.9 (15)
O1—C1—C9	117.10 (10)	C13—C26—H26A	110.4 (12)
C2—C1—C9	123.37 (11)	H26C—C26—H26A	108.2 (16)
C22—N1—C31	122.33 (11)	H26B—C26—H26A	108.5 (17)
C22—N1—H111	115.2 (11)	N2—C27—C18	123.65 (11)
C31—N1—H111	122.4 (11)	N2—C27—H27	115.8 (9)
C1—C2—C3	119.10 (10)	C18—C27—H27	120.6 (9)
C1—C2—C12	119.82 (11)	C15—C28—C30	109.62 (12)
C3—C2—C12	121.07 (11)	C15—C28—C29	115.27 (12)
C27—N2—C40	124.67 (11)	C30—C28—C29	110.08 (12)
C27—N2—H112	115.2 (13)	C15—C28—H28	107.9 (10)
C40—N2—H112	120.0 (13)	C30—C28—H28	108.8 (10)
C4—C3—C2	118.78 (11)	C29—C28—H28	104.9 (10)
C4—C3—C21	121.11 (12)	C28—C29—H29B	112.4 (10)
C2—C3—C21	120.11 (11)	C28—C29—H29C	109.6 (10)
C6—O4—H104	103.1 (14)	H29B—C29—H29C	107.9 (14)
C3—C4—C10	122.98 (11)	C28—C29—H29A	111.9 (12)
C3—C4—H4	117.7 (9)	H29B—C29—H29A	107.5 (15)
C10—C4—H4	119.3 (9)	H29C—C29—H29A	107.4 (15)
C11—O5—H105	111.7 (13)	C28—C30—H30C	111.5 (10)
C6—C5—C10	118.32 (11)	C28—C30—H30B	111.9 (12)
C6—C5—C23	120.52 (11)	H30C—C30—H30B	108.3 (16)
C10—C5—C23	121.02 (11)	C28—C30—H30A	110.5 (12)
C5—C6—O4	122.27 (11)	H30C—C30—H30A	108.5 (15)
C5—C6—C7	123.30 (11)	H30B—C30—H30A	105.9 (16)
O4—C6—C7	114.41 (11)	N1—C31—C32	111.84 (12)
O3—C7—C8	124.24 (11)	N1—C31—H31B	107.5 (10)
O3—C7—C6	116.35 (11)	C32—C31—H31B	111.0 (10)
C8—C7—C6	119.40 (11)	N1—C31—H31A	108.9 (11)
C22—C8—C7	116.75 (11)	C32—C31—H31A	109.5 (11)
C22—C8—C9	124.52 (10)	H31B—C31—H31A	108.1 (14)
C7—C8—C9	118.64 (11)	C31—C32—C33	113.02 (14)
C16—O8—H108	103.7 (14)	C31—C32—H32B	108.3 (12)
C1—C9—C10	116.83 (10)	C33—C32—H32B	109.2 (12)
C1—C9—C8	123.52 (11)	C31—C32—H32A	109.1 (13)
C10—C9—C8	119.63 (10)	C33—C32—H32A	110.7 (13)
C4—C10—C9	118.83 (10)	H32B—C32—H32A	106.2 (17)
C4—C10—C5	120.59 (11)	C34—C33—C32	113.05 (14)
C9—C10—C5	120.58 (11)	C34—C33—H33B	109.0 (12)
O5—C11—C12	119.71 (10)	C32—C33—H33B	106.1 (11)
O5—C11—C19	116.91 (10)	C34—C33—H33A	110.6 (13)
C12—C11—C19	123.38 (11)	C32—C33—H33A	107.9 (13)
C11—C12—C13	119.14 (10)	H33B—C33—H33A	110.1 (17)
C11—C12—C2	119.70 (10)	C39—C34—C35	118.57 (19)
C13—C12—C2	121.15 (11)	C39—C34—C33	122.68 (19)
C14—C13—C12	118.76 (11)	C35—C34—C33	118.74 (16)
C14—C13—C26	120.67 (11)	C36—C35—C34	122.4 (2)
C12—C13—C26	120.57 (11)	C36—C35—H35	118.9 (15)
C13—C14—C20	122.98 (11)	C34—C35—H35	118.7 (15)
C13—C14—H14	116.8 (9)	C37—C36—C35	119.2 (3)
C20—C14—H14	120.2 (9)	C37—C36—H36	120.4
C16—C15—C20	117.92 (11)	C35—C36—H36	120.4
C16—C15—C28	120.84 (11)	C36—C37—C38	121.9 (2)
C20—C15—C28	121.13 (11)	C36—C37—H37	125.3 (19)
C15—C16—O8	122.23 (11)	C38—C37—H37	112.7 (19)
C15—C16—C17	123.49 (11)	C37—C38—C39	118.8 (2)
O8—C16—C17	114.28 (11)	C37—C38—H38	120.6
O7—C17—C18	123.99 (11)	C39—C38—H38	120.6
O7—C17—C16	116.41 (11)	C34—C39—C38	119.1 (2)
C18—C17—C16	119.59 (11)	C34—C39—H39	114.5 (11)
C17—C18—C27	116.73 (11)	C38—C39—H39	126.2 (11)
C17—C18—C19	118.41 (11)	N2—C40—C41	109.12 (10)
C27—C18—C19	124.85 (11)	N2—C40—H40B	109.1 (10)
C11—C19—C20	116.73 (10)	C41—C40—H40B	110.6 (10)
C11—C19—C18	123.47 (11)	N2—C40—H40A	108.2 (10)
C20—C19—C18	119.79 (10)	C41—C40—H40A	110.7 (10)
C14—C20—C19	118.94 (10)	H40B—C40—H40A	109.0 (14)
C14—C20—C15	120.42 (11)	C40—C41—C42	112.03 (11)
C19—C20—C15	120.62 (11)	C40—C41—H41B	108.1 (9)
C3—C21—H21C	110.2 (11)	C42—C41—H41B	110.2 (9)
C3—C21—H21B	111.7 (11)	C40—C41—H41A	108.6 (10)
H21C—C21—H21B	105.5 (15)	C42—C41—H41A	109.4 (10)
C3—C21—H21A	111.5 (11)	H41B—C41—H41A	108.5 (13)
H21C—C21—H21A	107.4 (15)	C43—C42—C41	114.88 (11)
H21B—C21—H21A	110.3 (15)	C43—C42—H42B	108.8 (10)
N1—C22—C8	124.29 (11)	C41—C42—H42B	108.0 (10)
N1—C22—H22A	115.1 (9)	C43—C42—H42A	109.5 (10)
C8—C22—H22A	120.6 (9)	C41—C42—H42A	108.3 (10)
C5—C23—C24	109.71 (13)	H42B—C42—H42A	107.1 (14)
C5—C23—C25	115.26 (12)	C48—C43—C44	118.12 (12)
C24—C23—C25	110.91 (13)	C48—C43—C42	122.33 (12)
C5—C23—H23	108.7 (10)	C44—C43—C42	119.53 (12)
C24—C23—H23	105.8 (10)	C45—C44—C43	120.89 (14)
C25—C23—H23	105.9 (10)	C45—C44—H44	118.8 (11)
C23—C24—H24C	111.3 (13)	C43—C44—H44	120.3 (11)
C23—C24—H24B	109.7 (13)	C46—C45—C44	120.23 (14)
H24C—C24—H24B	108.0 (19)	C46—C45—H45	119.9 (12)
C23—C24—H24A	109.8 (12)	C44—C45—H45	119.9 (12)
H24C—C24—H24A	108.8 (18)	C47—C46—C45	119.70 (13)
H24B—C24—H24A	109.2 (18)	C47—C46—H46	117.3 (11)
C23—C25—H25C	110.2 (12)	C45—C46—H46	123.0 (11)
C23—C25—H25B	112.3 (12)	C46—C47—C48	120.11 (14)
H25C—C25—H25B	105.7 (17)	C46—C47—H47	120.9 (11)
C23—C25—H25A	112.9 (12)	C48—C47—H47	119.0 (11)
H25C—C25—H25A	106.9 (17)	C47—C48—C43	120.93 (13)
H25B—C25—H25A	108.5 (17)	C47—C48—H48	118.8 (10)
C13—C26—H26C	111.6 (11)	C43—C48—H48	120.2 (10)
O1—C1—C2—C3	176.20 (11)	O7—C17—C18—C27	−0.14 (19)
C9—C1—C2—C3	−3.68 (18)	C16—C17—C18—C27	−178.98 (11)
O1—C1—C2—C12	−4.88 (17)	O7—C17—C18—C19	−179.37 (12)
C9—C1—C2—C12	175.25 (11)	C16—C17—C18—C19	1.78 (18)
C1—C2—C3—C4	0.86 (18)	O5—C11—C19—C20	−178.19 (10)
C12—C2—C3—C4	−178.05 (11)	C12—C11—C19—C20	2.78 (18)
C1—C2—C3—C21	−178.83 (11)	O5—C11—C19—C18	2.61 (17)
C12—C2—C3—C21	2.26 (18)	C12—C11—C19—C18	−176.43 (11)
C2—C3—C4—C10	1.27 (19)	C17—C18—C19—C11	177.14 (12)
C21—C3—C4—C10	−179.03 (12)	C27—C18—C19—C11	−2.02 (19)
C10—C5—C6—O4	175.05 (11)	C17—C18—C19—C20	−2.04 (17)
C23—C5—C6—O4	−0.82 (19)	C27—C18—C19—C20	178.79 (11)
C10—C5—C6—C7	−3.38 (19)	C13—C14—C20—C19	−0.61 (19)
C23—C5—C6—C7	−179.25 (12)	C13—C14—C20—C15	178.13 (12)
C5—C6—C7—O3	179.74 (12)	C11—C19—C20—C14	−1.44 (17)
O4—C6—C7—O3	1.20 (16)	C18—C19—C20—C14	177.80 (11)
C5—C6—C7—C8	0.82 (19)	C11—C19—C20—C15	179.82 (11)
O4—C6—C7—C8	−177.72 (11)	C18—C19—C20—C15	−0.94 (17)
O3—C7—C8—C22	−1.10 (18)	C16—C15—C20—C14	−174.48 (12)
C6—C7—C8—C22	177.72 (11)	C28—C15—C20—C14	1.66 (19)
O3—C7—C8—C9	−177.83 (11)	C16—C15—C20—C19	4.24 (18)
C6—C7—C8—C9	1.00 (17)	C28—C15—C20—C19	−179.62 (12)
O1—C1—C9—C10	−175.73 (10)	C31—N1—C22—C8	−174.68 (12)
C2—C1—C9—C10	4.15 (17)	C7—C8—C22—N1	−1.80 (18)
O1—C1—C9—C8	5.88 (16)	C9—C8—C22—N1	174.71 (11)
C2—C1—C9—C8	−174.25 (11)	C6—C5—C23—C24	80.53 (16)
C22—C8—C9—C1	1.79 (18)	C10—C5—C23—C24	−95.23 (15)
C7—C8—C9—C1	178.24 (11)	C6—C5—C23—C25	−45.50 (18)
C22—C8—C9—C10	−176.56 (11)	C10—C5—C23—C25	138.75 (13)
C7—C8—C9—C10	−0.11 (16)	C40—N2—C27—C18	−179.68 (12)
C3—C4—C10—C9	−0.71 (18)	C17—C18—C27—N2	−0.41 (18)
C3—C4—C10—C5	178.34 (12)	C19—C18—C27—N2	178.77 (12)
C1—C9—C10—C4	−1.89 (16)	C16—C15—C28—C30	82.86 (16)
C8—C9—C10—C4	176.57 (10)	C20—C15—C28—C30	−93.16 (14)
C1—C9—C10—C5	179.06 (10)	C16—C15—C28—C29	−41.98 (19)
C8—C9—C10—C5	−2.48 (17)	C20—C15—C28—C29	142.00 (13)
C6—C5—C10—C4	−174.83 (11)	C22—N1—C31—C32	78.61 (17)
C23—C5—C10—C4	1.01 (18)	N1—C31—C32—C33	178.81 (14)
C6—C5—C10—C9	4.20 (17)	C31—C32—C33—C34	−59.9 (2)
C23—C5—C10—C9	−179.95 (11)	C32—C33—C34—C39	120.07 (19)
O5—C11—C12—C13	179.00 (11)	C32—C33—C34—C35	−59.0 (2)
C19—C11—C12—C13	−1.99 (18)	C39—C34—C35—C36	0.1 (3)
O5—C11—C12—C2	−2.52 (17)	C33—C34—C35—C36	179.16 (17)
C19—C11—C12—C2	176.49 (11)	C34—C35—C36—C37	0.3 (3)
C1—C2—C12—C11	88.34 (15)	C35—C36—C37—C38	−0.6 (3)
C3—C2—C12—C11	−92.76 (14)	C36—C37—C38—C39	0.6 (4)
C1—C2—C12—C13	−93.21 (15)	C35—C34—C39—C38	−0.1 (3)
C3—C2—C12—C13	85.69 (15)	C33—C34—C39—C38	−179.14 (17)
C11—C12—C13—C14	−0.18 (18)	C37—C38—C39—C34	−0.2 (3)
C2—C12—C13—C14	−178.64 (11)	C27—N2—C40—C41	−175.11 (12)
C11—C12—C13—C26	179.73 (12)	N2—C40—C41—C42	−177.77 (11)
C2—C12—C13—C26	1.28 (19)	C40—C41—C42—C43	179.66 (11)
C12—C13—C14—C20	1.5 (2)	C41—C42—C43—C48	−6.83 (19)
C26—C13—C14—C20	−178.45 (13)	C41—C42—C43—C44	174.53 (12)
C20—C15—C16—O8	175.44 (12)	C48—C43—C44—C45	−1.1 (2)
C28—C15—C16—O8	−0.7 (2)	C42—C43—C44—C45	177.59 (13)
C20—C15—C16—C17	−4.6 (2)	C43—C44—C45—C46	0.4 (2)
C28—C15—C16—C17	179.20 (12)	C44—C45—C46—C47	0.4 (2)
C15—C16—C17—O7	−177.25 (13)	C45—C46—C47—C48	−0.4 (2)
O8—C16—C17—O7	2.67 (18)	C46—C47—C48—C43	−0.3 (2)
C15—C16—C17—C18	1.7 (2)	C44—C43—C48—C47	1.1 (2)
O8—C16—C17—C18	−178.40 (12)	C42—C43—C48—C47	−177.60 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H101···O7^i	0.85 (2)	1.95 (2)	2.591 (1)	132 (2)
N1—H111···O3	0.93 (2)	1.77 (2)	2.535 (1)	137 (2)
O4—H104···O5^ii	0.85 (2)	2.48 (2)	3.217 (1)	146 (2)
O4—H104···O3	0.85 (2)	2.00 (2)	2.578 (1)	125 (2)
O5—H105···O3^ii	0.86 (2)	1.97 (2)	2.640 (1)	134 (2)
N2—H112···O7	0.91 (2)	1.77 (2)	2.517 (1)	138 (2)
O8—H108···O7	0.87 (2)	2.00 (2)	2.585 (1)	123 (2)
O8—H108···O1^iii	0.87 (2)	2.18 (2)	2.982 (1)	152 (2)

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