Validation of experimental charge densities: refinement of the macrolide antibiotic roxithromycin

Multipole refinements of larger organic molecules have so far been limited to a few exceptional cases. We report an investigation of the detailed experimental electron-density distribution (EDD) of roxithromycin, a macrolide antibiotic consisting of 134 atoms. Although the experimental multipole refinement on high-resolution synchrotron data converged smoothly, validation of the electron density by calculation of an `experiment minus invariom' difference density revealed conformational disorder of the H atoms. Hydrogen disorder is shown to affect the EDD, the electrostatic potential and atomic properties as defined by Bader's quantum theory of atoms in molecules. A procedure to obtain the electron density distribution in the presence of disorder is proposed.

Computing details

Program(s) used to refine structure: Koritsanszky et al., (2003); molecular graphics: Koritsanszky et al., (2003); software used to prepare material for publication: Koritsanszky et al., (2003).

(roxi)

Crystal data

C41H76N2O15·0.88(H2O)	F(000) = 1859.10
Mr = 852.96	Dx = 1.212 Mg m^−3
Orthorhombic, P212121	Synchrotron radiation, λ = 0.5600 Å
Hall symbol: P 2ac 2ab	Cell parameters from 474571 reflections
a = 11.624 (2) Å	θ = 0–38.5°
b = 16.748 (3) Å	µ = 0.06 mm^−1
c = 24.018 (5) Å	T = 100 K
V = 4675.8 (15) Å^3	Rectangle, colorless
Z = 4.0	0.50 × 0.35 × 0.30 mm

Data collection

Huber Kappa diffractometer with marCCD 165 detector	Rint = 0.0
φ scans with two different ω settings	θmax = 38.5°, θmin = 1.2°
474571 measured reflections	h = 0→25
28457 independent reflections	k = 0→37
26324 reflections with F > 3(σ)F	l = 0→53

Refinement

Refinement on F	850 parameters
Least-squares matrix: full	0 restraints
R[F^2 > 2σ(F^2)] = 0.020	w1 = 1/[s^2(Fo)]
wR(F^2) = 0.017	(Δ/σ)max < 0.001
S = 3.59	Δρmax = 0.20 e Å^−3
26324 reflections	Δρmin = −0.20 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O(14)	0.54781 (2)	0.451840 (10)	0.710460 (10)	0.018
O(21)	0.72755 (3)	0.46816 (2)	0.67631 (2)	0.021
O(22)	0.82148 (4)	0.28208 (2)	0.689690 (10)	0.018
O(23)	0.57637 (5)	0.33448 (2)	0.57041 (2)	0.021
O(24)	0.36993 (5)	0.36052 (2)	0.60274 (2)	0.023
O(25)	0.82793 (4)	0.15660 (3)	0.57624 (2)	0.024
O(26)	0.93743 (3)	0.26978 (3)	0.554790 (10)	0.028
O(27)	1.02473 (4)	0.35743 (3)	0.65183 (2)	0.039
O(5)	0.81014 (2)	0.206120 (10)	0.831520 (10)	0.016
O(58)	0.99248 (2)	0.176890 (10)	0.856990 (10)	0.018
O(59)	0.73423 (4)	0.19262 (2)	0.94128 (2)	0.022
O(3)	0.83631 (2)	0.432440 (10)	0.844530 (10)	0.018
O(38)	1.03346 (2)	0.44401 (2)	0.822140 (10)	0.02
O(39)	1.17361 (4)	0.35767 (3)	0.945200 (10)	0.022
O(40)	0.93967 (2)	0.37991 (2)	0.950350 (10)	0.02
O(80)	0.78943 (4)	0.40293 (3)	0.56831 (3)	0.028	0.884
N(2)	0.88506 (4)	0.09917 (2)	1.016770 (10)	0.018
N(1)	0.71803 (4)	0.19441 (2)	0.58030 (2)	0.021
C(1)	0.66092 (3)	0.46565 (2)	0.71503 (2)	0.017
C(2)	0.69573 (3)	0.47986 (2)	0.775100 (10)	0.018
C(3)	0.78794 (3)	0.41692 (2)	0.790850 (10)	0.016
C(4)	0.73397 (3)	0.33276 (2)	0.791930 (10)	0.015
C(5)	0.82798 (3)	0.26657 (2)	0.789930 (10)	0.015
C(6)	0.83069 (3)	0.22342 (2)	0.732510 (10)	0.016
C(7)	0.72499 (3)	0.16889 (2)	0.727950 (10)	0.017
C(8)	0.70734 (3)	0.12533 (2)	0.672190 (10)	0.018
C(9)	0.66564 (3)	0.17957 (2)	0.625950 (10)	0.017
C(10)	0.54753 (3)	0.21879 (2)	0.631480 (10)	0.018
C(11)	0.55881 (3)	0.31046 (2)	0.626890 (10)	0.017
C(12)	0.45310 (3)	0.35977 (2)	0.646570 (10)	0.018
C(13)	0.49525 (3)	0.44685 (2)	0.655480 (10)	0.017
C(50)	0.88595 (3)	0.20741 (2)	0.876400 (10)	0.015
C(51)	0.83658 (3)	0.15480 (2)	0.922870 (10)	0.016
C(52)	0.92698 (3)	0.14783 (2)	0.969320 (10)	0.016
C(53)	1.04257 (3)	0.12006 (2)	0.945640 (10)	0.019
C(54)	1.08041 (3)	0.17556 (2)	0.898970 (10)	0.018
C(55)	1.18988 (3)	0.14750 (2)	0.87088 (2)	0.025
C(56)	0.87875 (3)	0.01328 (2)	1.00502 (2)	0.023
C(57)	0.95562 (3)	0.11326 (2)	1.066360 (10)	0.025
C(30)	0.93564 (3)	0.48168 (2)	0.844830 (10)	0.018
C(31)	0.95546 (3)	0.51115 (2)	0.904050 (10)	0.02
C(32)	1.01054 (3)	0.44883 (2)	0.942730 (10)	0.018
C(33)	1.11872 (3)	0.41769 (2)	0.913070 (10)	0.018
C(34)	1.08795 (3)	0.38401 (2)	0.855790 (10)	0.018
C(35)	1.19281 (3)	0.35773 (2)	0.82308 (2)	0.025
C(36)	1.04265 (4)	0.48612 (2)	0.998630 (10)	0.025
C(37)	0.83221 (4)	0.39222 (3)	0.97671 (2)	0.028
C(60)	0.73213 (3)	0.56769 (2)	0.78015 (2)	0.025
C(61)	0.64992 (3)	0.32232 (2)	0.840310 (10)	0.021
C(62)	0.94240 (3)	0.17613 (2)	0.726470 (10)	0.022
C(63)	0.61902 (4)	0.05790 (2)	0.680830 (10)	0.024
C(64)	0.46125 (3)	0.18208 (2)	0.59039 (2)	0.025
C(65)	0.39330 (3)	0.32713 (2)	0.69809 (2)	0.024
C(66)	0.40249 (3)	0.51086 (2)	0.653430 (10)	0.021
C(67)	0.45365 (4)	0.59470 (2)	0.65527 (2)	0.026
C(68)	0.88935 (4)	0.19837 (3)	0.53493 (2)	0.026
C(69)	1.04699 (4)	0.26014 (3)	0.57998 (2)	0.038
C(70)	1.08605 (4)	0.33953 (4)	0.60278 (2)	0.04
C(71)	1.05306 (5)	0.43393 (4)	0.67328 (2)	0.042
H(22)	0.89723	0.30325	0.68323	0.029
H(23)	0.65684	0.34662	0.56453	0.03
H(24)	0.42005	0.36655	0.57117	0.032
H(59)	0.7077	0.16766	0.97494	0.032
H(39)	1.25008	0.37389	0.95565	0.036
H(2)	0.61988	0.46825	0.80095	0.03
H(3)	0.85635	0.42007	0.75939	0.029
H(4)	0.68628	0.32813	0.75268	0.026
H(5)	0.91398	0.29186	0.79671	0.028
H(7A)	0.64798	0.20325	0.73848	0.031
H(7B)	0.73051	0.12381	0.76079	0.033
H(8)	0.78891	0.09776	0.65979	0.032
H(10)	0.51745	0.2064	0.67386	0.03
H(11)	0.63241	0.32834	0.65268	0.031
H(13)	0.55954	0.46262	0.62384	0.03
H(50)	0.89814	0.26893	0.89139	0.031
H(51)	0.81881	0.09678	0.90337	0.033
H(52)	0.93807	0.20776	0.98728	0.029
H(53A)	1.10689	0.11656	0.97873	0.037
H(53B)	1.03635	0.06011	0.92785	0.036
H(54)	1.0836	0.23615	0.9164	0.03
H(55A)	1.2106	0.18397	0.83449	0.047
H(55B)	1.17473	0.08653	0.85633	0.048
H(55C)	1.26596	0.15121	0.89755	0.05
H(56A)	0.83285	−0.01462	1.03951	0.046
H(56B)	0.96356	−0.01403	1.0012	0.046
H(56C)	0.82738	0.00348	0.96768	0.044
H(57A)	1.04063	0.0863	1.06218	0.047
H(57B)	0.91956	0.07969	1.10109	0.048
H(57C)	0.97492	0.17625	1.07301	0.046
H(30)	0.91509	0.52955	0.81504	0.038
H(31A)	0.87391	0.53136	0.92184	0.038
H(31B)	1.01195	0.56336	0.90334	0.037
H(33)	1.1739	0.46998	0.90605	0.031
H(34)	1.02766	0.334	0.86058	0.03
H(35A)	1.2531	0.40619	0.81412	0.048
H(35B)	1.17094	0.33028	0.78317	0.049
H(35C)	1.23773	0.31537	0.85007	0.046
H(36A)	1.06227	0.43998	1.02939	0.048
H(36B)	0.9672	0.5157	1.01633	0.049
H(36C)	1.11217	0.52885	0.99118	0.047
H(37A)	0.79126	0.33351	0.97932	0.05
H(37B)	0.77429	0.42771	0.95061	0.046
H(37C)	0.84082	0.41252	1.01982	0.052
H(60A)	0.65586	0.60214	0.76861	0.044
H(60B)	0.80901	0.58227	0.75596	0.043
H(60C)	0.74823	0.57956	0.82424	0.044
H(61A)	0.58368	0.36851	0.83747	0.038
H(61B)	0.69087	0.3267	0.88118	0.038
H(61C)	0.60621	0.2645	0.84135	0.038
H(62A)	1.01826	0.21462	0.72848	0.04
H(62B)	0.94477	0.14921	0.68501	0.041
H(62C)	0.95237	0.13032	0.75854	0.04
H(63A)	0.60411	0.02925	0.64056	0.045
H(63B)	0.53908	0.08354	0.69679	0.043
H(63C)	0.65472	0.01666	0.71164	0.044
H(64A)	0.46488	0.11713	0.59451	0.045
H(64B)	0.48597	0.19445	0.5473	0.043
H(64C)	0.37478	0.20526	0.59817	0.044
H(65A)	0.35506	0.26979	0.68668	0.042
H(65B)	0.33119	0.37169	0.71247	0.042
H(65C)	0.45326	0.32055	0.73286	0.039
H(66A)	0.33856	0.50455	0.68653	0.038
H(66B)	0.35508	0.50415	0.61436	0.038
H(67A)	0.5215	0.60314	0.62427	0.044
H(67B)	0.49661	0.60509	0.69513	0.044
H(67C)	0.38699	0.63937	0.64741	0.048
H(68A)	0.83188	0.21411	0.50098	0.042
H(68B)	0.95584	0.15529	0.52436	0.047
H(69A)	1.10734	0.24642	0.54624	0.054
H(69B)	1.04906	0.21425	0.61248	0.051
H(70A)	1.17993	0.33836	0.60702	0.06
H(70B)	1.07043	0.39018	0.57491	0.052
H(71A)	1.01381	0.4478	0.71354	0.064
H(71B)	1.01944	0.47882	0.64448	0.06
H(71C)	1.14653	0.43999	0.66907	0.068
H(80A)	0.84486	0.36038	0.56855	0.039	0.884
H(80B)	0.78089	0.42473	0.60506	0.042	0.884

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(14)	0.01840 (9)	0.02085 (10)	0.01512 (8)	0.00202 (8)	−0.00188 (7)	−0.00020 (7)
O(21)	0.02080 (10)	0.0243 (2)	0.01800 (10)	−0.00240 (10)	0.00020 (10)	0.00150 (10)
O(22)	0.01960 (10)	0.02000 (10)	0.01530 (10)	−0.00060 (10)	0.00030 (10)	0.00370 (10)
O(23)	0.0233 (2)	0.0223 (2)	0.01670 (10)	0.00270 (10)	0.00180 (10)	0.00120 (10)
O(24)	0.0190 (2)	0.0269 (2)	0.0234 (2)	0.00190 (10)	−0.00530 (10)	−0.00320 (10)
O(25)	0.0287 (2)	0.02440 (10)	0.01880 (10)	0.00870 (10)	0.00700 (10)	0.00320 (10)
O(26)	0.0284 (2)	0.0295 (2)	0.0253 (2)	0.0046 (2)	0.00420 (10)	0.00390 (10)
O(27)	0.0339 (2)	0.0490 (2)	0.0344 (2)	−0.0170 (2)	0.0064 (2)	0.0071 (3)
O(5)	0.01856 (9)	0.01575 (8)	0.01371 (7)	−0.00109 (7)	−0.00235 (6)	0.00181 (6)
O(58)	0.01831 (9)	0.02044 (10)	0.01480 (8)	0.00202 (8)	−0.00035 (6)	0.00032 (7)
O(59)	0.01820 (10)	0.02750 (10)	0.01920 (10)	0.00310 (10)	0.00130 (10)	0.00600 (10)
O(3)	0.01995 (9)	0.01754 (9)	0.01529 (8)	−0.00270 (8)	−0.00320 (7)	0.00017 (7)
O(38)	0.02130 (10)	0.02280 (10)	0.01580 (10)	−0.00310 (10)	−0.00140 (10)	0.00270 (10)
O(39)	0.02400 (10)	0.02000 (10)	0.02230 (10)	−0.00150 (10)	−0.00570 (10)	0.00330 (10)
O(40)	0.02270 (10)	0.01980 (10)	0.01860 (10)	−0.00300 (10)	0.00170 (10)	−0.00060 (10)
O(80)	0.0273 (2)	0.0284 (2)	0.0277 (2)	0.0001 (2)	0.0032 (2)	0.0008 (2)
N(2)	0.01960 (10)	0.01900 (10)	0.01560 (10)	0.00010 (10)	−0.00090 (10)	0.00300 (10)
N(1)	0.02560 (10)	0.02240 (10)	0.01470 (10)	0.00600 (10)	0.00290 (10)	0.00150 (10)
C(1)	0.01830 (10)	0.01540 (10)	0.01580 (10)	0.00030 (10)	−0.00180 (10)	0.00090 (10)
C(2)	0.02090 (10)	0.01500 (10)	0.01680 (10)	0.00120 (10)	−0.00290 (10)	−0.00060 (10)
C(3)	0.01770 (10)	0.01440 (10)	0.01470 (10)	−0.00040 (10)	−0.00180 (10)	0.00030 (10)
C(4)	0.01650 (10)	0.01410 (10)	0.01540 (10)	0.00000 (10)	−0.00090 (10)	−0.00010 (10)
C(5)	0.01620 (10)	0.01460 (10)	0.01390 (10)	0.00010 (10)	−0.00080 (10)	0.00090 (10)
C(6)	0.01750 (10)	0.01590 (10)	0.01360 (10)	0.00100 (10)	0.00080 (10)	0.00090 (10)
C(7)	0.02110 (10)	0.01560 (10)	0.01340 (10)	−0.00100 (10)	0.00080 (10)	−0.00060 (10)
C(8)	0.02430 (10)	0.01510 (10)	0.01410 (10)	0.00160 (10)	0.00010 (10)	−0.00080 (10)
C(9)	0.02180 (10)	0.01690 (10)	0.01350 (10)	0.00210 (10)	0.00030 (10)	−0.00060 (10)
C(10)	0.01980 (10)	0.01820 (10)	0.01680 (10)	0.00050 (10)	−0.00060 (10)	−0.00030 (10)
C(11)	0.01760 (10)	0.01750 (10)	0.01580 (10)	0.00130 (10)	−0.00020 (10)	−0.00040 (10)
C(12)	0.01700 (10)	0.01970 (10)	0.01630 (10)	0.00150 (10)	−0.00020 (10)	−0.00050 (10)
C(13)	0.01780 (10)	0.01900 (10)	0.01490 (10)	0.00310 (10)	−0.00150 (10)	−0.00010 (10)
C(50)	0.01710 (10)	0.01540 (10)	0.01360 (10)	0.00010 (10)	−0.00120 (10)	0.00070 (10)
C(51)	0.01740 (10)	0.01660 (10)	0.01490 (10)	−0.00070 (10)	−0.00180 (10)	0.00180 (10)
C(52)	0.01760 (10)	0.01630 (10)	0.01440 (10)	0.00010 (10)	−0.00150 (10)	0.00140 (10)
C(53)	0.01820 (10)	0.02030 (10)	0.01810 (10)	0.00220 (10)	−0.00080 (10)	0.00330 (10)
C(54)	0.01720 (10)	0.01910 (10)	0.01700 (10)	0.00100 (10)	−0.00010 (10)	0.00120 (10)
C(55)	0.02010 (10)	0.0306 (2)	0.02470 (10)	0.00550 (10)	0.00410 (10)	0.00350 (10)
C(56)	0.0270 (2)	0.01800 (10)	0.02500 (10)	0.00020 (10)	0.00080 (10)	0.00460 (10)
C(57)	0.02680 (10)	0.0318 (2)	0.01670 (10)	−0.00270 (10)	−0.00440 (10)	0.00470 (10)
C(30)	0.02120 (10)	0.01640 (10)	0.01780 (10)	−0.00300 (10)	−0.00420 (10)	0.00150 (10)
C(31)	0.02390 (10)	0.01650 (10)	0.02010 (10)	−0.00120 (10)	−0.00510 (10)	−0.00190 (10)
C(32)	0.02180 (10)	0.01780 (10)	0.01580 (10)	−0.00180 (10)	−0.00240 (10)	−0.00130 (10)
C(33)	0.01980 (10)	0.01760 (10)	0.01690 (10)	−0.00250 (10)	−0.00300 (10)	0.00100 (10)
C(34)	0.01940 (10)	0.01880 (10)	0.01610 (10)	−0.00280 (10)	−0.00050 (10)	0.00030 (10)
C(35)	0.02370 (10)	0.0284 (2)	0.02320 (10)	−0.00090 (10)	0.00390 (10)	−0.00180 (10)
C(36)	0.0317 (2)	0.02460 (10)	0.01780 (10)	−0.00110 (10)	−0.00500 (10)	−0.00430 (10)
C(37)	0.0285 (2)	0.0293 (2)	0.02520 (10)	−0.00400 (10)	0.00730 (10)	−0.00320 (10)
C(60)	0.0308 (2)	0.01460 (10)	0.02860 (10)	0.00130 (10)	−0.00880 (10)	−0.00200 (10)
C(61)	0.02120 (10)	0.01870 (10)	0.02330 (10)	0.00100 (10)	0.00580 (10)	0.00190 (10)
C(62)	0.02120 (10)	0.02500 (10)	0.01900 (10)	0.00630 (10)	0.00140 (10)	−0.00010 (10)
C(63)	0.0358 (2)	0.01610 (10)	0.02030 (10)	−0.00430 (10)	−0.00200 (10)	−0.00120 (10)
C(64)	0.0268 (2)	0.02260 (10)	0.02640 (10)	−0.00190 (10)	−0.00710 (10)	−0.00230 (10)
C(65)	0.02450 (10)	0.02550 (10)	0.02270 (10)	0.00020 (10)	0.00690 (10)	0.00070 (10)
C(66)	0.02120 (10)	0.02200 (10)	0.02020 (10)	0.00640 (10)	−0.00260 (10)	−0.00110 (10)
C(67)	0.0298 (2)	0.02060 (10)	0.0279 (2)	0.00600 (10)	−0.00290 (10)	−0.00120 (10)
C(68)	0.0320 (2)	0.0276 (2)	0.01840 (10)	0.0066 (2)	0.00860 (10)	0.00210 (10)
C(69)	0.0257 (2)	0.0442 (3)	0.0447 (2)	0.0041 (2)	0.0045 (2)	0.0048 (2)
C(70)	0.0258 (2)	0.0520 (3)	0.0418 (2)	−0.0096 (2)	0.0064 (2)	0.0082 (2)
C(71)	0.0371 (2)	0.0505 (3)	0.0371 (2)	−0.0159 (2)	−0.0005 (2)	0.0068 (2)
H(22)	0.0225	0.0342	0.029	−0.0014	0.0028	0.0063
H(23)	0.0278	0.037	0.0251	0.0008	0.0009	0.0029
H(24)	0.0299	0.0399	0.0258	0.0019	−0.0011	−0.0003
H(59)	0.0306	0.0382	0.0283	0.0038	0.0052	0.0104
H(39)	0.0311	0.0344	0.0413	−0.0031	−0.0115	0.0048
H(2)	0.0296	0.0315	0.0282	0.0009	0.0035	−0.0002
H(3)	0.0271	0.0312	0.0276	−0.0025	0.004	0.0028
H(4)	0.0277	0.0302	0.0212	−0.0009	−0.0029	0
H(5)	0.023	0.0306	0.0301	−0.0036	−0.0011	0.0011
H(7A)	0.0276	0.0314	0.0347	0.0032	0.0019	−0.0047
H(7B)	0.0442	0.0272	0.0269	−0.0029	−0.0032	0.0065
H(8)	0.0354	0.0315	0.0295	0.0082	0.0014	−0.0027
H(10)	0.0334	0.0332	0.0233	−0.003	0.002	0.0012
H(11)	0.0284	0.0328	0.0321	−0.0003	−0.0068	−0.003
H(13)	0.0307	0.033	0.0266	0.0007	0.0033	0.0027
H(50)	0.0416	0.0222	0.0304	−0.0013	0.0028	−0.0015
H(51)	0.0417	0.0263	0.0323	−0.0045	−0.007	−0.0033
H(52)	0.0364	0.0234	0.0269	−0.002	−0.0013	−0.0042
H(53A)	0.0296	0.0492	0.031	0.0012	−0.0077	0.0077
H(53B)	0.0422	0.0258	0.0388	0.0023	0.0046	−0.003
H(54)	0.0334	0.0267	0.0303	−0.0032	−0.0019	−0.0022
H(55A)	0.0428	0.0562	0.0411	0.0091	0.0128	0.018
H(55B)	0.0458	0.0397	0.0585	0.0063	0.0119	−0.0058
H(55C)	0.0284	0.0766	0.0464	0.0076	−0.0049	0.005
H(56A)	0.0587	0.0386	0.0415	−0.0066	0.012	0.0127
H(56B)	0.0383	0.0358	0.0638	0.0084	0.0015	0.0041
H(56C)	0.056	0.035	0.0399	−0.0038	−0.0152	0.0015
H(57A)	0.0353	0.0641	0.0406	0.0093	−0.0069	0.0025
H(57B)	0.0521	0.0616	0.029	−0.0123	−0.0016	0.0171
H(57C)	0.0615	0.0387	0.0375	−0.0088	−0.0123	0.0007
H(30)	0.0483	0.0311	0.0342	0	−0.0117	0.0084
H(31A)	0.033	0.0403	0.0403	0.006	−0.0002	−0.0057
H(31B)	0.0409	0.0274	0.0421	−0.0106	−0.0097	0.0014
H(33)	0.0312	0.027	0.0358	−0.0089	−0.0038	0.0034
H(34)	0.0304	0.0264	0.0323	−0.0072	0.0005	−0.0011
H(35A)	0.0396	0.0465	0.0575	−0.011	0.0145	0.001
H(35B)	0.0446	0.0666	0.035	−0.0007	0.0029	−0.017
H(35C)	0.0415	0.0505	0.0454	0.0122	0.0029	0.008
H(36A)	0.0727	0.0423	0.0299	0.0011	−0.0117	0.0034
H(36B)	0.0482	0.0584	0.0407	0.009	−0.001	−0.0184
H(36C)	0.0524	0.0458	0.0413	−0.0172	−0.0066	−0.0061
H(37A)	0.0481	0.0393	0.0613	−0.0119	0.0174	−0.0006
H(37B)	0.0388	0.055	0.0454	0.0077	0.0042	0.0054
H(37C)	0.0539	0.0709	0.031	−0.0025	0.0086	−0.0119
H(60A)	0.0432	0.0306	0.0567	0.0077	−0.0145	0.0012
H(60B)	0.0452	0.0343	0.0504	−0.0079	0.007	0.001
H(60C)	0.0667	0.0346	0.0295	−0.0043	−0.0117	−0.0025
H(61A)	0.0366	0.0388	0.0388	0.0139	0.0076	0.0061
H(61B)	0.0371	0.0545	0.0219	−0.0028	−0.0033	−0.0008
H(61C)	0.0441	0.0302	0.0384	−0.0116	0.011	−0.0029
H(62A)	0.0282	0.0386	0.0536	−0.0015	0.0021	−0.0004
H(62B)	0.0447	0.0518	0.0258	0.014	−0.0009	−0.0097
H(62C)	0.0448	0.0403	0.0343	0.012	0.0045	0.0138
H(63A)	0.065	0.0411	0.0302	−0.0107	−0.0055	−0.0096
H(63B)	0.0396	0.0347	0.0536	−0.0019	0.0061	−0.004
H(63C)	0.055	0.0344	0.0428	−0.0034	−0.0135	0.0118
H(64A)	0.0581	0.0273	0.0491	−0.0028	−0.0161	−0.0011
H(64B)	0.0513	0.0534	0.0256	−0.0079	−0.0028	−0.0004
H(64C)	0.0323	0.0511	0.0474	0.0035	−0.0057	−0.0117
H(65A)	0.0457	0.039	0.0401	−0.0145	0.0024	−0.0055
H(65B)	0.0375	0.0441	0.0441	0.0125	0.0107	0.0004
H(65C)	0.0292	0.0566	0.03	−0.0035	−0.0058	0.0056
H(66A)	0.0369	0.0425	0.0359	0.0082	0.0062	−0.0013
H(66B)	0.0423	0.0406	0.0317	0.0076	−0.0123	−0.003
H(67A)	0.0517	0.0392	0.0425	0.0001	0.0085	−0.0012
H(67B)	0.0597	0.0399	0.0334	0.0007	−0.0168	−0.0005
H(67C)	0.0469	0.0359	0.0601	0.0169	−0.0127	0.0005
H(68A)	0.0488	0.044	0.0324	0.0048	0.0016	0.0086
H(68B)	0.0453	0.0436	0.051	0.0149	0.0175	0.0043
H(69A)	0.0397	0.0669	0.0558	0.0052	0.0171	0.0048
H(69B)	0.0442	0.0581	0.0515	0.0014	0.0001	0.0173
H(70A)	0.0328	0.079	0.067	−0.0053	0.0022	0.0082
H(70B)	0.0523	0.0551	0.0483	−0.0029	0.0057	0.0106
H(71A)	0.0742	0.0732	0.0458	−0.0324	0.0129	−0.0046
H(71B)	0.0697	0.0586	0.0522	−0.0162	−0.0053	0.007
H(71C)	0.045	0.0837	0.0757	−0.0259	0.0018	0.0018
H(80A)	0.04	0.0378	0.0405	0.006	0.0054	0.0016
H(80B)	0.0484	0.0393	0.0376	−0.0029	0.0091	−0.0056

Geometric parameters (Å, º)

O(14)—C(1)	1.3395 (5)	C(55)—H(55C)	1.0937
O(21)—C(1)	1.2110 (6)	C(56)—H(56A)	1.0907
O(22)—C(6)	1.4264 (5)	C(56)—H(56B)	1.0906
O(22)—H(22)	0.9618	C(56)—H(56C)	1.0899
O(23)—C(11)	1.4297 (5)	C(57)—H(57A)	1.0910
O(23)—H(23)	0.9676	C(57)—H(57B)	1.0898
O(24)—C(12)	1.4294 (6)	C(57)—H(57C)	1.0904
O(24)—H(24)	0.9616	C(30)—C(31)	1.5230 (5)
O(25)—C(68)	1.4084 (6)	C(30)—H(30)	1.1008
O(26)—C(68)	1.4036 (7)	C(31)—C(32)	1.5369 (5)
O(26)—C(69)	1.4192 (7)	C(31)—H(31A)	1.0936
O(27)—C(70)	1.4093 (7)	C(31)—H(31B)	1.0936
O(27)—C(71)	1.4197 (8)	C(32)—C(33)	1.5364 (5)
O(5)—C(50)	1.3923 (4)	C(32)—C(36)	1.5270 (5)
O(58)—C(50)	1.4183 (4)	C(33)—C(34)	1.5295 (4)
O(59)—C(51)	1.4186 (6)	C(33)—H(33)	1.0984
O(59)—H(59)	0.9610	C(34)—C(35)	1.5154 (5)
O(3)—C(30)	1.4190 (4)	C(34)—H(34)	1.0982
O(38)—C(30)	1.4100 (4)	C(35)—H(35A)	1.0937
O(39)—C(33)	1.4189 (6)	C(35)—H(35B)	1.0931
O(39)—H(39)	0.9627	C(35)—H(35C)	1.0937
O(40)—C(32)	1.4300 (4)	C(36)—H(36A)	1.0932
O(40)—C(37)	1.4155 (5)	C(36)—H(36B)	1.0933
O(80)—H(80A)	0.9608	C(36)—H(36C)	1.0942
O(80)—H(80B)	0.9604	C(37)—H(37A)	1.0942
N(2)—C(56)	1.4677 (5)	C(37)—H(37B)	1.0952
N(2)—C(57)	1.4653 (5)	C(37)—H(37C)	1.0945
N(1)—C(9)	1.2785 (5)	C(60)—H(60A)	1.0935
C(1)—C(2)	1.5171 (5)	C(60)—H(60B)	1.0936
C(2)—C(60)	1.5354 (5)	C(60)—H(60C)	1.0934
C(2)—H(2)	1.0958	C(61)—H(61A)	1.0936
C(3)—H(3)	1.0982	C(61)—H(61B)	1.0934
C(4)—C(61)	1.5282 (4)	C(61)—H(61C)	1.0938
C(4)—H(4)	1.0963	C(62)—H(62A)	1.0934
C(5)—H(5)	1.0978	C(62)—H(62B)	1.0935
C(6)—C(7)	1.5349 (4)	C(62)—H(62C)	1.0933
C(6)—C(62)	1.5279 (4)	C(63)—H(63A)	1.0934
C(7)—C(8)	1.5386 (4)	C(63)—H(63B)	1.0931
C(7)—H(7A)	1.0938	C(63)—H(63C)	1.0940
C(7)—H(7B)	1.0937	C(64)—H(64A)	1.0931
C(8)—C(9)	1.5146 (4)	C(64)—H(64B)	1.0940
C(8)—H(8)	1.0959	C(64)—H(64C)	1.0935
C(9)—C(10)	1.5277 (5)	C(65)—H(65A)	1.0932
C(10)—C(64)	1.5355 (5)	C(65)—H(65B)	1.0943
C(10)—H(10)	1.0960	C(65)—H(65C)	1.0934
C(11)—H(11)	1.0978	C(66)—C(67)	1.5256 (6)
C(12)—C(65)	1.5208 (5)	C(66)—H(66A)	1.0933
C(13)—C(66)	1.5213 (4)	C(66)—H(66B)	1.0939
C(13)—H(13)	1.0980	C(67)—H(67A)	1.0938
C(50)—C(51)	1.5334 (4)	C(67)—H(67B)	1.0937
C(50)—H(50)	1.1006	C(67)—H(67C)	1.0934
C(51)—C(52)	1.5371 (4)	C(68)—H(68A)	1.0866
C(51)—H(51)	1.0983	C(68)—H(68B)	1.0874
C(52)—C(53)	1.5314 (5)	C(69)—C(70)	1.5079 (8)
C(52)—H(52)	1.1000	C(69)—H(69A)	1.0961
C(53)—C(54)	1.5212 (4)	C(69)—H(69B)	1.0958
C(53)—H(53A)	1.0928	C(70)—H(70A)	1.0961
C(53)—H(53B)	1.0936	C(70)—H(70B)	1.0957
C(54)—C(55)	1.5150 (5)	C(71)—H(71A)	1.0941
C(54)—H(54)	1.0983	C(71)—H(71B)	1.0939
C(55)—H(55A)	1.0931	C(71)—H(71C)	1.0958
C(55)—H(55B)	1.0934
C(6)—O(22)—H(22)	107.55	C(33)—C(32)—C(36)	110.27 (3)
C(11)—O(23)—H(23)	109.61	O(39)—C(33)—C(32)	110.88 (3)
C(12)—O(24)—H(24)	99.90	O(39)—C(33)—C(34)	109.46 (3)
C(68)—O(26)—C(69)	113.91 (5)	O(39)—C(33)—H(33)	112.69
C(70)—O(27)—C(71)	112.21 (5)	C(32)—C(33)—C(34)	110.54 (3)
C(51)—O(59)—H(59)	109.69	C(32)—C(33)—H(33)	106.17
C(33)—O(39)—H(39)	110.91	C(34)—C(33)—H(33)	107.01
C(32)—O(40)—C(37)	116.62 (3)	C(33)—C(34)—C(35)	112.67 (3)
H(80A)—O(80)—H(80B)	110.23	C(33)—C(34)—H(34)	109.65
C(56)—N(2)—C(57)	110.00 (3)	C(35)—C(34)—H(34)	110.25
O(14)—C(1)—O(21)	124.81 (3)	C(34)—C(35)—H(35A)	113.69
O(14)—C(1)—C(2)	111.52 (3)	C(34)—C(35)—H(35B)	112.94
O(21)—C(1)—C(2)	123.66 (3)	C(34)—C(35)—H(35C)	105.37
C(1)—C(2)—C(60)	107.39 (3)	H(35A)—C(35)—H(35B)	106.77
C(1)—C(2)—H(2)	107.24	H(35A)—C(35)—H(35C)	106.98
C(60)—C(2)—H(2)	110.30	H(35B)—C(35)—H(35C)	110.98
C(61)—C(4)—H(4)	108.81	C(32)—C(36)—H(36A)	110.86
O(22)—C(6)—C(7)	107.35 (3)	C(32)—C(36)—H(36B)	109.34
O(22)—C(6)—C(62)	110.63 (3)	C(32)—C(36)—H(36C)	107.72
C(7)—C(6)—C(62)	111.41 (3)	H(36A)—C(36)—H(36B)	102.99
C(6)—C(7)—C(8)	116.81 (3)	H(36A)—C(36)—H(36C)	114.75
C(6)—C(7)—H(7A)	109.00	H(36B)—C(36)—H(36C)	111.07
C(6)—C(7)—H(7B)	108.19	O(40)—C(37)—H(37A)	106.19
C(8)—C(7)—H(7A)	109.97	O(40)—C(37)—H(37B)	111.44
C(8)—C(7)—H(7B)	107.96	O(40)—C(37)—H(37C)	112.82
H(7A)—C(7)—H(7B)	104.14	H(37A)—C(37)—H(37B)	104.66
C(7)—C(8)—C(9)	113.37 (2)	H(37A)—C(37)—H(37C)	105.34
C(7)—C(8)—H(8)	108.73	H(37B)—C(37)—H(37C)	115.41
C(9)—C(8)—H(8)	109.29	C(2)—C(60)—H(60A)	105.19
N(1)—C(9)—C(8)	126.37 (3)	C(2)—C(60)—H(60B)	113.40
N(1)—C(9)—C(10)	114.77 (3)	C(2)—C(60)—H(60C)	107.34
C(8)—C(9)—C(10)	118.79 (3)	H(60A)—C(60)—H(60B)	114.20
C(9)—C(10)—C(64)	111.04 (3)	H(60A)—C(60)—H(60C)	106.76
C(9)—C(10)—H(10)	106.62	H(60B)—C(60)—H(60C)	109.51
C(64)—C(10)—H(10)	108.22	C(4)—C(61)—H(61A)	108.77
O(23)—C(11)—H(11)	110.33	C(4)—C(61)—H(61B)	113.37
O(24)—C(12)—C(65)	107.05 (3)	C(4)—C(61)—H(61C)	114.55
C(66)—C(13)—H(13)	106.88	H(61A)—C(61)—H(61B)	108.37
O(5)—C(50)—O(58)	107.01 (2)	H(61A)—C(61)—H(61C)	107.49
O(5)—C(50)—C(51)	108.52 (3)	H(61B)—C(61)—H(61C)	103.95
O(5)—C(50)—H(50)	110.44	C(6)—C(62)—H(62A)	112.06
O(58)—C(50)—C(51)	111.03 (2)	C(6)—C(62)—H(62B)	108.76
O(58)—C(50)—H(50)	109.42	C(6)—C(62)—H(62C)	112.76
C(51)—C(50)—H(50)	110.36	H(62A)—C(62)—H(62B)	105.24
O(59)—C(51)—C(50)	106.51 (3)	H(62A)—C(62)—H(62C)	107.29
O(59)—C(51)—C(52)	112.40 (3)	H(62B)—C(62)—H(62C)	110.47
O(59)—C(51)—H(51)	111.73	H(63A)—C(63)—H(63B)	110.36
C(50)—C(51)—C(52)	108.42 (3)	H(63A)—C(63)—H(63C)	112.42
C(50)—C(51)—H(51)	105.57	H(63B)—C(63)—H(63C)	109.46
C(52)—C(51)—H(51)	111.77	C(10)—C(64)—H(64A)	108.36
C(51)—C(52)—C(53)	110.69 (3)	C(10)—C(64)—H(64B)	111.15
C(51)—C(52)—H(52)	107.19	C(10)—C(64)—H(64C)	110.40
C(53)—C(52)—H(52)	108.66	H(64A)—C(64)—H(64B)	105.30
C(52)—C(53)—C(54)	109.98 (3)	H(64A)—C(64)—H(64C)	111.92
C(52)—C(53)—H(53A)	110.27	H(64B)—C(64)—H(64C)	109.62
C(52)—C(53)—H(53B)	111.47	C(12)—C(65)—H(65A)	107.32
C(54)—C(53)—H(53A)	111.78	C(12)—C(65)—H(65B)	108.26
C(54)—C(53)—H(53B)	106.99	C(12)—C(65)—H(65C)	111.49
H(53A)—C(53)—H(53B)	106.27	H(65A)—C(65)—H(65B)	114.21
C(53)—C(54)—C(55)	112.42 (3)	H(65A)—C(65)—H(65C)	111.22
C(53)—C(54)—H(54)	107.05	H(65B)—C(65)—H(65C)	104.37
C(55)—C(54)—H(54)	115.35	C(13)—C(66)—C(67)	111.80 (3)
C(54)—C(55)—H(55A)	111.57	C(13)—C(66)—H(66A)	112.96
C(54)—C(55)—H(55B)	107.26	C(13)—C(66)—H(66B)	108.21
C(54)—C(55)—H(55C)	113.63	C(67)—C(66)—H(66A)	109.44
H(55A)—C(55)—H(55B)	107.57	C(67)—C(66)—H(66B)	108.41
H(55A)—C(55)—H(55C)	104.96	H(66A)—C(66)—H(66B)	105.74
H(55B)—C(55)—H(55C)	111.74	C(66)—C(67)—H(67A)	112.35
N(2)—C(56)—H(56A)	107.35	C(66)—C(67)—H(67B)	110.47
N(2)—C(56)—H(56B)	112.47	C(66)—C(67)—H(67C)	110.39
N(2)—C(56)—H(56C)	109.47	H(67A)—C(67)—H(67B)	104.25
H(56A)—C(56)—H(56B)	109.05	H(67A)—C(67)—H(67C)	107.76
H(56A)—C(56)—H(56C)	107.00	H(67B)—C(67)—H(67C)	111.46
H(56B)—C(56)—H(56C)	111.28	O(25)—C(68)—O(26)	112.69 (4)
N(2)—C(57)—H(57A)	111.45	O(25)—C(68)—H(68A)	109.72
N(2)—C(57)—H(57B)	108.90	O(25)—C(68)—H(68B)	101.25
N(2)—C(57)—H(57C)	112.96	O(26)—C(68)—H(68A)	107.04
H(57A)—C(57)—H(57B)	101.85	O(26)—C(68)—H(68B)	111.21
H(57A)—C(57)—H(57C)	103.16	H(68A)—C(68)—H(68B)	115.01
H(57B)—C(57)—H(57C)	117.78	O(26)—C(69)—C(70)	108.95 (4)
O(3)—C(30)—O(38)	113.21 (3)	O(26)—C(69)—H(69A)	106.44
O(3)—C(30)—C(31)	108.43 (3)	O(26)—C(69)—H(69B)	113.78
O(3)—C(30)—H(30)	104.09	C(70)—C(69)—H(69A)	105.11
O(38)—C(30)—C(31)	112.58 (3)	C(70)—C(69)—H(69B)	110.68
O(38)—C(30)—H(30)	104.46	H(69A)—C(69)—H(69B)	111.44
C(31)—C(30)—H(30)	113.82	O(27)—C(70)—C(69)	109.80
C(30)—C(31)—C(32)	114.05 (3)	O(27)—C(70)—H(70A)	115.44
C(30)—C(31)—H(31A)	109.52	O(27)—C(70)—H(70B)	105.19
C(30)—C(31)—H(31B)	109.59	C(69)—C(70)—H(70A)	108.53
C(32)—C(31)—H(31A)	109.57	C(69)—C(70)—H(70B)	114.26
C(32)—C(31)—H(31B)	107.59	H(70A)—C(70)—H(70B)	103.63
H(31A)—C(31)—H(31B)	106.20	O(27)—C(71)—H(71A)	114.56
O(40)—C(32)—C(31)	112.68 (3)	O(27)—C(71)—H(71B)	107.93
O(40)—C(32)—C(33)	104.88 (3)	O(27)—C(71)—H(71C)	106.26
O(40)—C(32)—C(36)	111.00 (3)	H(71A)—C(71)—H(71B)	105.30
C(31)—C(32)—C(33)	106.93 (3)	H(71A)—C(71)—H(71C)	118.38
C(31)—C(32)—C(36)	110.83 (3)	H(71B)—C(71)—H(71C)	103.43