Crystal structures and properties of two hydrated conglomerate forms of the heart-rate-lowering agent ivabradine hydro­chloride

Ivabradine hydro­chloride (IVA-HCl) (systematic name: {[3,4-di­methoxybi­cyclo­[4.2.0]octa-1(6),2,4-trien-7-yl]meth­yl}[3-(7,8-dimeth­oxy-2-oxo-2,3,4,5-tetra­hydro-1H-3-benzazepin-3-yl)prop­yl]methyl­aza­nium), is a novel medication used for the symptomatic management of stable angina pectoris. In many recent patents, it has been claimed to exist in a very large number of polymorphic, hydrated and solvated phases, although no detailed analysis of the structural features of these forms has been published to date. Here, we have successfully crystallized the tetra­hydrate form of IVA-HCl (form β), C₂₇H₃₇N₂O₅⁺·Cl⁻·4H₂O, and elucidated its structure for the first time. Simultaneously, a new crystal form of IVA-HCl, i.e. the hemihydrate (form II), C₂₇H₃₇N₂O₅⁺·Cl⁻·0.5H₂O, was discovered. Its crystal structure was also accurately determined and compared to that of the tetra­hydrate form. While the tetra­hydrate form of IVA-HCl crystallized in the ortho­rhom­bic space group P2₁2₁2₁, the new form (hemihydrate) was solved in the monoclinic space group P2₁. Detailed conformational and packing com­parisons between the two forms have allowed us to understand the role of water in the crystal assembly of this hydro­chloride salt. The stabilities of the two forms were compared theoretically by calculating the binding energy of the water in the crystal lattice using differential scanning calorimetry (DSC). The stability experiments show that the tetra­hydrate is stable under high-humidity conditions, while the hemihydrate is stable under high-temperature conditions.

Computing details

For both structures, data collection: CrysAlis PRO (Agilent, 2009); cell refinement: CrysAlis PRO (Agilent, 2009); data reduction: CrysAlis PRO (Agilent, 2009); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

{[3,4-Dimethoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-yl]methyl}[3-(7,8-dimethoxy-2-oxo-2,3,4,5-tetrahydro-1H-3-benzazepin-3-yl)propyl]methylazanium hemihydrate (1123_iva)

Crystal data

2C27H37N2O5^+·2Cl^−·H2O	F(000) = 1100
Mr = 1028.08	Dx = 1.258 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 5.4874 (1) Å	Cell parameters from 13189 reflections
b = 43.4767 (7) Å	θ = 67.5–3.0°
c = 11.4892 (2) Å	µ = 1.58 mm^−1
β = 98.144 (2)°	T = 296 K
V = 2713.38 (8) Å^3	Chunk, colorless
Z = 2	0.38 × 0.22 × 0.19 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	9744 independent reflections
Radiation source: fine-focus sealed tube	8864 reflections with I > 2σ(I)
Detector resolution: 10.3592 pixels mm^-1	Rint = 0.035
ω scans	θmax = 67.6°, θmin = 3.9°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −5→6
Tmin = 0.545, Tmax = 0.744	k = −51→51
30111 measured reflections	l = −13→13

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0475P)^2 + 0.3577P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.096	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.28 e Å^−3
9744 reflections	Δρmin = −0.17 e Å^−3
650 parameters	Absolute structure: Flack x determined using 3869 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.019 (7)
Primary atom site location: dual

Special details

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

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

	x	y	z	Uiso*/Ueq
Cl1A	−0.06631 (16)	0.71114 (3)	0.61783 (8)	0.0634 (2)
Cl1B	−0.33759 (18)	0.77834 (3)	0.11157 (8)	0.0663 (3)
O1A	0.7874 (6)	0.54551 (6)	0.8390 (3)	0.0713 (8)
O2A	1.0237 (5)	0.57884 (6)	0.7110 (3)	0.0699 (8)
O3A	0.4428 (5)	0.82055 (6)	0.5716 (2)	0.0619 (7)
O4A	0.6928 (5)	0.96952 (6)	0.5521 (3)	0.0681 (7)
O5A	1.0510 (5)	0.96837 (6)	0.7267 (2)	0.0588 (6)
O1B	0.1002 (6)	0.97049 (6)	0.2456 (3)	0.0734 (8)
O2B	0.3470 (6)	0.93905 (6)	0.1156 (3)	0.0702 (8)
O3B	0.0848 (6)	0.68306 (6)	0.1384 (2)	0.0651 (7)
O4B	0.3930 (5)	0.53529 (6)	0.1536 (3)	0.0709 (8)
O5B	0.7572 (5)	0.53932 (6)	0.3228 (3)	0.0611 (7)
O6	0.1418 (7)	0.81133 (11)	0.0228 (3)	0.1031 (12)
H6A	0.284455	0.813355	0.054391	0.155*
H6B	0.012735	0.807355	0.048111	0.155*
N1A	0.3583 (5)	0.71549 (6)	0.8201 (2)	0.0415 (5)
H1A	0.228900	0.719819	0.754196	0.050*
N1B	0.0225 (5)	0.79109 (6)	0.3388 (2)	0.0416 (6)
H1B	−0.095623	0.785806	0.269489	0.050*
N2A	0.5582 (5)	0.82578 (6)	0.7663 (2)	0.0442 (6)
N2B	0.2646 (6)	0.68159 (6)	0.3273 (3)	0.0539 (7)
C1A	0.6165 (6)	0.66897 (7)	0.9012 (3)	0.0451 (7)
H1AA	0.740557	0.682924	0.941916	0.054*
C2A	0.4866 (7)	0.64836 (8)	0.9876 (3)	0.0518 (8)
H2AA	0.544159	0.651926	1.070272	0.062*
H2AB	0.308230	0.648431	0.971545	0.062*
C3A	0.6077 (6)	0.62108 (8)	0.9351 (3)	0.0479 (7)
C4A	0.6211 (7)	0.58929 (8)	0.9340 (3)	0.0552 (9)
H4A	0.540841	0.577167	0.983414	0.066*
C5A	0.7618 (7)	0.57651 (8)	0.8544 (4)	0.0537 (8)
C6A	0.8870 (6)	0.59502 (8)	0.7819 (3)	0.0513 (8)
C7A	0.8685 (6)	0.62681 (8)	0.7834 (3)	0.0507 (8)
H7A	0.947694	0.639219	0.734490	0.061*
C8A	0.7247 (6)	0.63904 (8)	0.8621 (3)	0.0467 (7)
C9A	0.6216 (10)	0.52578 (10)	0.8877 (6)	0.0863 (15)
H9AA	0.649291	0.527397	0.971882	0.129*
H9AB	0.648096	0.504921	0.865107	0.129*
H9AC	0.455320	0.531691	0.859041	0.129*
C10A	1.1917 (8)	0.59546 (11)	0.6539 (4)	0.0687 (11)
H10A	1.103488	0.609197	0.597539	0.103*
H10B	1.287343	0.581427	0.614304	0.103*
H10C	1.299145	0.607097	0.710764	0.103*
C11A	0.4549 (6)	0.68395 (7)	0.7984 (3)	0.0457 (7)
H11A	0.548543	0.685256	0.732981	0.055*
H11B	0.315550	0.670539	0.774433	0.055*
C12A	0.2398 (7)	0.71743 (9)	0.9286 (3)	0.0546 (8)
H12A	0.122601	0.701044	0.928844	0.082*
H12B	0.157025	0.736844	0.930456	0.082*
H12C	0.363130	0.715664	0.996350	0.082*
C13A	0.5495 (6)	0.73994 (7)	0.8174 (3)	0.0451 (7)
H13A	0.650140	0.734878	0.757119	0.054*
H13B	0.655902	0.740196	0.892389	0.054*
C14A	0.4417 (6)	0.77147 (7)	0.7933 (3)	0.0436 (7)
H14A	0.359878	0.778021	0.858622	0.052*
H14B	0.320694	0.770990	0.723047	0.052*
C15A	0.6458 (6)	0.79396 (7)	0.7766 (3)	0.0453 (7)
H15A	0.775802	0.792358	0.843002	0.054*
H15B	0.714818	0.788448	0.706285	0.054*
C16A	0.4614 (6)	0.83649 (7)	0.6612 (3)	0.0446 (7)
C17A	0.3699 (6)	0.86941 (8)	0.6562 (3)	0.0507 (8)
H17A	0.251303	0.871449	0.710786	0.061*
H17B	0.283051	0.873168	0.577921	0.061*
C18A	0.5631 (6)	0.89439 (7)	0.6840 (3)	0.0412 (7)
C19A	0.5444 (6)	0.91978 (8)	0.6073 (3)	0.0491 (8)
H19A	0.419671	0.920092	0.543413	0.059*
C20A	0.7051 (6)	0.94411 (8)	0.6241 (3)	0.0479 (7)
C21A	0.8982 (6)	0.94349 (7)	0.7176 (3)	0.0454 (7)
C22A	0.9158 (6)	0.91884 (7)	0.7935 (3)	0.0431 (7)
H22A	1.041907	0.918625	0.856790	0.052*
C23A	0.7502 (6)	0.89394 (7)	0.7791 (3)	0.0389 (6)
C24A	0.7929 (6)	0.86848 (7)	0.8698 (3)	0.0449 (7)
H24A	0.941148	0.857525	0.857566	0.054*
H24B	0.824205	0.877917	0.946995	0.054*
C25A	0.5887 (6)	0.84513 (7)	0.8712 (3)	0.0453 (7)
H25A	0.625411	0.832220	0.940337	0.054*
H25B	0.435529	0.855821	0.876501	0.054*
C26A	0.4705 (10)	0.97889 (16)	0.4987 (7)	0.122 (3)
H26A	0.421114	0.966422	0.430436	0.183*
H26B	0.480227	1.000015	0.475395	0.183*
H26C	0.351856	0.976917	0.552117	0.183*
C27A	1.2529 (7)	0.96835 (9)	0.8181 (4)	0.0610 (9)
H27A	1.193571	0.967479	0.892674	0.091*
H27B	1.347430	0.986788	0.813711	0.091*
H27C	1.354837	0.950761	0.809765	0.091*
C1B	−0.0749 (6)	0.84631 (8)	0.2808 (3)	0.0504 (8)
H1BA	−0.199238	0.838466	0.218217	0.060*
C2B	−0.1962 (7)	0.86542 (8)	0.3749 (4)	0.0558 (9)
H2BA	−0.374744	0.865269	0.362742	0.067*
H2BB	−0.130870	0.860757	0.455934	0.067*
C3B	−0.0824 (7)	0.89355 (8)	0.3255 (3)	0.0520 (8)
C4B	−0.0674 (7)	0.92527 (8)	0.3312 (4)	0.0570 (9)
H4B	−0.147175	0.936577	0.383220	0.068*
C5B	0.0731 (7)	0.93928 (8)	0.2551 (3)	0.0555 (8)
C6B	0.2039 (7)	0.92169 (8)	0.1807 (3)	0.0525 (8)
C7B	0.1805 (7)	0.89027 (9)	0.1737 (3)	0.0532 (8)
H7B	0.260340	0.878608	0.122736	0.064*
C8B	0.0310 (6)	0.87701 (8)	0.2470 (3)	0.0485 (8)
C9B	−0.0676 (10)	0.98942 (10)	0.2963 (5)	0.0809 (13)
H9BA	−0.232946	0.982796	0.269654	0.121*
H9BB	−0.048238	1.010399	0.273155	0.121*
H9BC	−0.034921	0.987878	0.380430	0.121*
C10B	0.5159 (8)	0.92311 (11)	0.0570 (4)	0.0705 (11)
H10D	0.617085	0.910201	0.111886	0.106*
H10E	0.617839	0.937578	0.023139	0.106*
H10F	0.428328	0.910651	−0.004086	0.106*
C11B	0.1210 (6)	0.82255 (7)	0.3189 (3)	0.0455 (7)
H11C	0.229331	0.821159	0.259341	0.055*
H11D	0.218827	0.829477	0.391127	0.055*
C12B	−0.1105 (6)	0.79002 (8)	0.4425 (3)	0.0527 (8)
H12D	−0.164002	0.769348	0.453906	0.079*
H12E	−0.251015	0.803386	0.429727	0.079*
H12F	−0.002607	0.796624	0.511105	0.079*
C13B	0.2266 (6)	0.76792 (7)	0.3480 (3)	0.0476 (8)
H13C	0.330994	0.770467	0.422921	0.057*
H13D	0.326326	0.771698	0.286222	0.057*
C14B	0.1323 (7)	0.73538 (8)	0.3382 (3)	0.0512 (8)
H14C	0.004241	0.733603	0.271076	0.061*
H14D	0.062093	0.729989	0.408309	0.061*
C15B	0.3438 (7)	0.71339 (8)	0.3234 (4)	0.0577 (9)
H15C	0.401388	0.717368	0.248842	0.069*
H15D	0.479713	0.716992	0.385670	0.069*
C16B	0.1363 (6)	0.66877 (8)	0.2308 (3)	0.0478 (8)
C17B	0.0556 (7)	0.63583 (8)	0.2399 (4)	0.0573 (9)
H17C	−0.038466	0.630040	0.165240	0.069*
H17D	−0.054838	0.634830	0.298673	0.069*
C18B	0.2565 (6)	0.61206 (7)	0.2711 (3)	0.0453 (7)
C19B	0.2375 (7)	0.58551 (8)	0.2004 (3)	0.0522 (8)
H19B	0.108078	0.584002	0.138948	0.063*
C20B	0.4031 (6)	0.56177 (8)	0.2189 (3)	0.0490 (8)
C21B	0.5999 (6)	0.56404 (7)	0.3103 (3)	0.0467 (7)
C22B	0.6197 (6)	0.58972 (7)	0.3803 (3)	0.0466 (7)
H22B	0.749473	0.590975	0.441676	0.056*
C23B	0.4509 (6)	0.61426 (7)	0.3628 (3)	0.0440 (7)
C24B	0.5004 (7)	0.64116 (8)	0.4456 (3)	0.0512 (8)
H24C	0.651102	0.651039	0.430269	0.061*
H24D	0.529528	0.633236	0.525269	0.061*
C25B	0.3011 (8)	0.66548 (9)	0.4397 (3)	0.0576 (9)
H25C	0.147696	0.655816	0.452326	0.069*
H25D	0.345166	0.680269	0.502359	0.069*
C26B	0.1662 (10)	0.52758 (13)	0.0870 (6)	0.0916 (16)
H26D	0.038366	0.528721	0.135944	0.137*
H26E	0.174428	0.507043	0.057111	0.137*
H26F	0.130802	0.541700	0.022634	0.137*
C27B	0.9554 (8)	0.54023 (9)	0.4151 (4)	0.0632 (10)
H27D	1.060743	0.557255	0.403529	0.095*
H27E	1.047182	0.521414	0.416121	0.095*
H27F	0.893304	0.542643	0.488604	0.095*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1A	0.0554 (5)	0.0906 (7)	0.0457 (4)	0.0072 (5)	0.0127 (3)	−0.0021 (5)
Cl1B	0.0656 (5)	0.0776 (6)	0.0509 (5)	−0.0074 (5)	−0.0087 (4)	−0.0018 (4)
O1A	0.0868 (19)	0.0395 (14)	0.093 (2)	0.0034 (12)	0.0313 (16)	−0.0024 (13)
O2A	0.0726 (17)	0.0581 (16)	0.086 (2)	−0.0078 (13)	0.0367 (15)	−0.0194 (14)
O3A	0.0849 (18)	0.0532 (15)	0.0439 (13)	−0.0062 (13)	−0.0035 (12)	−0.0064 (11)
O4A	0.0705 (16)	0.0526 (15)	0.0778 (18)	−0.0026 (12)	−0.0007 (13)	0.0313 (14)
O5A	0.0625 (14)	0.0408 (13)	0.0699 (16)	−0.0140 (11)	−0.0017 (12)	0.0130 (12)
O1B	0.102 (2)	0.0376 (14)	0.087 (2)	−0.0021 (13)	0.0355 (17)	0.0028 (13)
O2B	0.0855 (18)	0.0573 (16)	0.0739 (19)	0.0062 (14)	0.0322 (15)	0.0146 (14)
O3B	0.0894 (19)	0.0554 (16)	0.0517 (15)	0.0149 (13)	0.0135 (13)	0.0076 (12)
O4B	0.0740 (17)	0.0508 (15)	0.083 (2)	0.0069 (13)	−0.0076 (14)	−0.0224 (14)
O5B	0.0636 (15)	0.0398 (13)	0.0764 (18)	0.0161 (11)	−0.0023 (13)	−0.0075 (12)
O6	0.084 (2)	0.140 (3)	0.088 (2)	0.023 (2)	0.0230 (18)	0.024 (2)
N1A	0.0444 (13)	0.0325 (13)	0.0478 (14)	−0.0032 (10)	0.0076 (11)	0.0012 (11)
N1B	0.0426 (13)	0.0379 (13)	0.0427 (14)	0.0010 (10)	0.0003 (11)	−0.0021 (11)
N2A	0.0593 (16)	0.0319 (13)	0.0406 (14)	−0.0074 (11)	0.0047 (12)	−0.0004 (11)
N2B	0.0737 (19)	0.0375 (15)	0.0517 (17)	0.0113 (13)	0.0135 (14)	0.0058 (12)
C1A	0.0430 (16)	0.0367 (16)	0.0545 (19)	−0.0028 (12)	0.0036 (13)	−0.0042 (14)
C2A	0.0561 (19)	0.0450 (18)	0.055 (2)	0.0075 (14)	0.0102 (16)	0.0016 (15)
C3A	0.0508 (18)	0.0444 (18)	0.0483 (19)	0.0030 (14)	0.0067 (14)	0.0038 (15)
C4A	0.066 (2)	0.0436 (19)	0.058 (2)	0.0048 (16)	0.0168 (17)	0.0090 (16)
C5A	0.060 (2)	0.0395 (18)	0.062 (2)	0.0038 (15)	0.0095 (17)	−0.0013 (16)
C6A	0.0472 (18)	0.051 (2)	0.057 (2)	−0.0037 (14)	0.0098 (15)	−0.0097 (16)
C7A	0.0444 (17)	0.0494 (19)	0.059 (2)	−0.0094 (14)	0.0101 (15)	−0.0023 (16)
C8A	0.0427 (16)	0.0409 (17)	0.056 (2)	−0.0013 (13)	0.0053 (14)	−0.0019 (15)
C9A	0.099 (4)	0.044 (2)	0.122 (4)	−0.005 (2)	0.033 (3)	−0.003 (2)
C10A	0.058 (2)	0.085 (3)	0.067 (3)	−0.009 (2)	0.0200 (18)	−0.013 (2)
C11A	0.0524 (18)	0.0324 (15)	0.0513 (19)	−0.0047 (13)	0.0043 (14)	−0.0021 (13)
C12A	0.0539 (18)	0.053 (2)	0.062 (2)	−0.0019 (15)	0.0239 (16)	0.0081 (17)
C13A	0.0461 (17)	0.0366 (16)	0.055 (2)	−0.0056 (12)	0.0142 (14)	−0.0004 (14)
C14A	0.0490 (17)	0.0369 (16)	0.0454 (17)	−0.0029 (13)	0.0088 (13)	0.0005 (13)
C15A	0.0528 (18)	0.0351 (16)	0.0478 (18)	−0.0046 (13)	0.0065 (14)	−0.0003 (14)
C16A	0.0478 (17)	0.0397 (17)	0.0443 (18)	−0.0105 (13)	−0.0002 (13)	−0.0016 (14)
C17A	0.0456 (17)	0.0455 (19)	0.057 (2)	−0.0042 (14)	−0.0055 (15)	0.0054 (15)
C18A	0.0438 (16)	0.0319 (15)	0.0469 (17)	0.0006 (12)	0.0034 (13)	−0.0006 (13)
C19A	0.0494 (17)	0.0431 (18)	0.0513 (19)	0.0024 (14)	−0.0047 (14)	0.0056 (15)
C20A	0.0570 (19)	0.0372 (17)	0.0498 (19)	0.0018 (14)	0.0085 (15)	0.0091 (14)
C21A	0.0475 (17)	0.0343 (16)	0.0542 (19)	−0.0034 (13)	0.0064 (14)	0.0018 (14)
C22A	0.0452 (16)	0.0354 (16)	0.0472 (17)	−0.0051 (12)	0.0014 (13)	0.0032 (13)
C23A	0.0442 (15)	0.0315 (15)	0.0413 (16)	−0.0009 (12)	0.0070 (12)	−0.0004 (12)
C24A	0.0534 (18)	0.0380 (16)	0.0422 (17)	−0.0056 (13)	0.0031 (14)	0.0018 (13)
C25A	0.0583 (19)	0.0395 (17)	0.0392 (17)	−0.0062 (14)	0.0106 (14)	0.0002 (13)
C26A	0.082 (3)	0.115 (5)	0.171 (7)	0.028 (3)	0.023 (4)	0.098 (5)
C27A	0.061 (2)	0.0463 (19)	0.072 (2)	−0.0138 (16)	−0.0023 (18)	0.0035 (18)
C1B	0.0547 (19)	0.0398 (17)	0.053 (2)	−0.0016 (14)	−0.0055 (15)	0.0024 (14)
C2B	0.055 (2)	0.0447 (19)	0.068 (2)	−0.0021 (15)	0.0097 (17)	0.0042 (17)
C3B	0.0576 (19)	0.0445 (19)	0.053 (2)	0.0002 (15)	0.0058 (15)	0.0034 (15)
C4B	0.070 (2)	0.0424 (19)	0.062 (2)	−0.0007 (16)	0.0215 (18)	−0.0017 (16)
C5B	0.067 (2)	0.044 (2)	0.056 (2)	0.0006 (16)	0.0109 (17)	−0.0007 (16)
C6B	0.060 (2)	0.050 (2)	0.0478 (19)	0.0021 (15)	0.0086 (15)	0.0065 (15)
C7B	0.066 (2)	0.052 (2)	0.0418 (18)	0.0102 (16)	0.0073 (15)	0.0038 (15)
C8B	0.0581 (19)	0.0407 (17)	0.0443 (18)	0.0030 (14)	−0.0011 (14)	0.0006 (14)
C9B	0.101 (3)	0.043 (2)	0.104 (4)	0.008 (2)	0.032 (3)	0.006 (2)
C10B	0.065 (2)	0.085 (3)	0.063 (2)	0.009 (2)	0.0135 (19)	0.014 (2)
C11B	0.0527 (18)	0.0382 (17)	0.0442 (17)	−0.0066 (13)	0.0021 (14)	0.0003 (13)
C12B	0.0520 (18)	0.0480 (19)	0.060 (2)	−0.0010 (14)	0.0150 (15)	−0.0001 (16)
C13B	0.0473 (17)	0.0421 (18)	0.054 (2)	0.0056 (13)	0.0085 (14)	0.0017 (14)
C14B	0.0572 (19)	0.0407 (18)	0.058 (2)	0.0034 (14)	0.0159 (16)	0.0049 (15)
C15B	0.067 (2)	0.0389 (18)	0.068 (2)	0.0075 (16)	0.0115 (17)	0.0006 (17)
C16B	0.0528 (18)	0.0431 (18)	0.050 (2)	0.0121 (14)	0.0165 (15)	0.0036 (15)
C17B	0.0490 (19)	0.047 (2)	0.075 (3)	0.0065 (15)	0.0080 (17)	0.0049 (18)
C18B	0.0448 (16)	0.0381 (17)	0.0541 (19)	0.0017 (13)	0.0104 (14)	0.0056 (14)
C19B	0.0516 (19)	0.0463 (19)	0.057 (2)	−0.0012 (14)	0.0017 (15)	−0.0017 (16)
C20B	0.0567 (19)	0.0372 (17)	0.0534 (19)	0.0017 (14)	0.0086 (15)	−0.0026 (15)
C21B	0.0495 (17)	0.0373 (17)	0.0543 (19)	0.0037 (13)	0.0111 (14)	0.0022 (15)
C22B	0.0484 (18)	0.0391 (17)	0.0517 (19)	0.0037 (13)	0.0057 (14)	−0.0001 (14)
C23B	0.0480 (17)	0.0371 (16)	0.0489 (18)	0.0020 (13)	0.0135 (14)	0.0045 (13)
C24B	0.061 (2)	0.0436 (18)	0.0484 (19)	0.0083 (15)	0.0075 (15)	−0.0011 (15)
C25B	0.080 (2)	0.051 (2)	0.0449 (19)	0.0202 (18)	0.0198 (17)	0.0045 (15)
C26B	0.084 (3)	0.079 (3)	0.110 (4)	−0.016 (2)	0.007 (3)	−0.039 (3)
C27B	0.065 (2)	0.048 (2)	0.073 (3)	0.0175 (17)	−0.0018 (19)	0.0018 (18)

Geometric parameters (Å, º)

O1A—C5A	1.369 (4)	C19A—C20A	1.373 (5)
O1A—C9A	1.422 (6)	C20A—C21A	1.398 (5)
O2A—C6A	1.376 (4)	C21A—C22A	1.377 (5)
O2A—C10A	1.405 (5)	C22A—H22A	0.9300
O3A—C16A	1.233 (4)	C22A—C23A	1.408 (4)
O4A—C20A	1.376 (4)	C23A—C24A	1.516 (4)
O4A—C26A	1.349 (6)	C24A—H24A	0.9700
O5A—C21A	1.363 (4)	C24A—H24B	0.9700
O5A—C27A	1.414 (5)	C24A—C25A	1.513 (5)
O1B—C5B	1.371 (5)	C25A—H25A	0.9700
O1B—C9B	1.420 (5)	C25A—H25B	0.9700
O2B—C6B	1.382 (5)	C26A—H26A	0.9600
O2B—C10B	1.404 (5)	C26A—H26B	0.9600
O3B—C16B	1.228 (4)	C26A—H26C	0.9600
O4B—C20B	1.371 (4)	C27A—H27A	0.9600
O4B—C26B	1.406 (6)	C27A—H27B	0.9600
O5B—C21B	1.373 (4)	C27A—H27C	0.9600
O5B—C27B	1.408 (5)	C1B—H1BA	0.9800
O6—H6A	0.8195	C1B—C2B	1.583 (6)
O6—H6B	0.8214	C1B—C8B	1.528 (5)
N1A—H1A	0.9800	C1B—C11B	1.510 (5)
N1A—C11A	1.504 (4)	C2B—H2BA	0.9700
N1A—C12A	1.488 (4)	C2B—H2BB	0.9700
N1A—C13A	1.497 (4)	C2B—C3B	1.519 (5)
N1B—H1B	0.9800	C3B—C4B	1.382 (5)
N1B—C11B	1.500 (4)	C3B—C8B	1.369 (5)
N1B—C12B	1.484 (4)	C4B—H4B	0.9300
N1B—C13B	1.499 (4)	C4B—C5B	1.386 (5)
N2A—C15A	1.464 (4)	C5B—C6B	1.416 (5)
N2A—C16A	1.333 (4)	C6B—C7B	1.373 (5)
N2A—C25A	1.460 (4)	C7B—H7B	0.9300
N2B—C15B	1.452 (5)	C7B—C8B	1.382 (5)
N2B—C16B	1.347 (5)	C9B—H9BA	0.9600
N2B—C25B	1.458 (5)	C9B—H9BB	0.9600
C1A—H1AA	0.9800	C9B—H9BC	0.9600
C1A—C2A	1.580 (5)	C10B—H10D	0.9600
C1A—C8A	1.524 (5)	C10B—H10E	0.9600
C1A—C11A	1.519 (5)	C10B—H10F	0.9600
C2A—H2AA	0.9700	C11B—H11C	0.9700
C2A—H2AB	0.9700	C11B—H11D	0.9700
C2A—C3A	1.525 (5)	C12B—H12D	0.9600
C3A—C4A	1.384 (5)	C12B—H12E	0.9600
C3A—C8A	1.371 (5)	C12B—H12F	0.9600
C4A—H4A	0.9300	C13B—H13C	0.9700
C4A—C5A	1.394 (5)	C13B—H13D	0.9700
C5A—C6A	1.405 (5)	C13B—C14B	1.505 (5)
C6A—C7A	1.386 (5)	C14B—H14C	0.9700
C7A—H7A	0.9300	C14B—H14D	0.9700
C7A—C8A	1.387 (5)	C14B—C15B	1.531 (5)
C9A—H9AA	0.9600	C15B—H15C	0.9700
C9A—H9AB	0.9600	C15B—H15D	0.9700
C9A—H9AC	0.9600	C16B—C17B	1.507 (5)
C10A—H10A	0.9600	C17B—H17C	0.9700
C10A—H10B	0.9600	C17B—H17D	0.9700
C10A—H10C	0.9600	C17B—C18B	1.516 (5)
C11A—H11A	0.9700	C18B—C19B	1.407 (5)
C11A—H11B	0.9700	C18B—C23B	1.392 (5)
C12A—H12A	0.9600	C19B—H19B	0.9300
C12A—H12B	0.9600	C19B—C20B	1.372 (5)
C12A—H12C	0.9600	C20B—C21B	1.399 (5)
C13A—H13A	0.9700	C21B—C22B	1.371 (5)
C13A—H13B	0.9700	C22B—H22B	0.9300
C13A—C14A	1.503 (5)	C22B—C23B	1.408 (5)
C14A—H14A	0.9700	C23B—C24B	1.508 (5)
C14A—H14B	0.9700	C24B—H24C	0.9700
C14A—C15A	1.519 (4)	C24B—H24D	0.9700
C15A—H15A	0.9700	C24B—C25B	1.516 (5)
C15A—H15B	0.9700	C25B—H25C	0.9700
C16A—C17A	1.515 (5)	C25B—H25D	0.9700
C17A—H17A	0.9700	C26B—H26D	0.9600
C17A—H17B	0.9700	C26B—H26E	0.9600
C17A—C18A	1.519 (4)	C26B—H26F	0.9600
C18A—C19A	1.407 (5)	C27B—H27D	0.9600
C18A—C23A	1.390 (4)	C27B—H27E	0.9600
C19A—H19A	0.9300	C27B—H27F	0.9600
C5A—O1A—C9A	117.4 (3)	H25A—C25A—H25B	107.9
C6A—O2A—C10A	117.5 (3)	O4A—C26A—H26A	109.5
C26A—O4A—C20A	118.7 (3)	O4A—C26A—H26B	109.5
C21A—O5A—C27A	117.7 (3)	O4A—C26A—H26C	109.5
C5B—O1B—C9B	117.2 (3)	H26A—C26A—H26B	109.5
C6B—O2B—C10B	117.0 (3)	H26A—C26A—H26C	109.5
C20B—O4B—C26B	117.5 (3)	H26B—C26A—H26C	109.5
C21B—O5B—C27B	117.6 (3)	O5A—C27A—H27A	109.5
H6A—O6—H6B	133.1	O5A—C27A—H27B	109.5
C11A—N1A—H1A	106.3	O5A—C27A—H27C	109.5
C12A—N1A—H1A	106.3	H27A—C27A—H27B	109.5
C12A—N1A—C11A	113.4 (3)	H27A—C27A—H27C	109.5
C12A—N1A—C13A	111.6 (3)	H27B—C27A—H27C	109.5
C13A—N1A—H1A	106.3	C2B—C1B—H1BA	111.6
C13A—N1A—C11A	112.3 (2)	C8B—C1B—H1BA	111.6
C11B—N1B—H1B	107.5	C8B—C1B—C2B	85.8 (3)
C12B—N1B—H1B	107.5	C11B—C1B—H1BA	111.6
C12B—N1B—C11B	112.3 (3)	C11B—C1B—C2B	120.8 (3)
C12B—N1B—C13B	111.7 (3)	C11B—C1B—C8B	113.0 (3)
C13B—N1B—H1B	107.5	C1B—C2B—H2BA	114.3
C13B—N1B—C11B	110.0 (2)	C1B—C2B—H2BB	114.3
C16A—N2A—C15A	119.2 (3)	H2BA—C2B—H2BB	111.4
C16A—N2A—C25A	122.1 (3)	C3B—C2B—C1B	86.1 (3)
C25A—N2A—C15A	118.7 (3)	C3B—C2B—H2BA	114.3
C15B—N2B—C25B	118.7 (3)	C3B—C2B—H2BB	114.3
C16B—N2B—C15B	119.5 (3)	C4B—C3B—C2B	144.1 (4)
C16B—N2B—C25B	121.4 (3)	C8B—C3B—C2B	94.2 (3)
C2A—C1A—H1AA	113.3	C8B—C3B—C4B	121.7 (4)
C8A—C1A—H1AA	113.3	C3B—C4B—H4B	121.8
C8A—C1A—C2A	86.0 (2)	C3B—C4B—C5B	116.3 (4)
C11A—C1A—H1AA	113.3	C5B—C4B—H4B	121.8
C11A—C1A—C2A	117.8 (3)	O1B—C5B—C4B	124.2 (3)
C11A—C1A—C8A	110.2 (3)	O1B—C5B—C6B	114.6 (3)
C1A—C2A—H2AA	114.3	C4B—C5B—C6B	121.2 (3)
C1A—C2A—H2AB	114.3	O2B—C6B—C5B	114.0 (3)
H2AA—C2A—H2AB	111.4	C7B—C6B—O2B	124.6 (3)
C3A—C2A—C1A	86.1 (3)	C7B—C6B—C5B	121.4 (3)
C3A—C2A—H2AA	114.3	C6B—C7B—H7B	122.0
C3A—C2A—H2AB	114.3	C6B—C7B—C8B	116.0 (3)
C4A—C3A—C2A	143.8 (3)	C8B—C7B—H7B	122.0
C8A—C3A—C2A	93.8 (3)	C3B—C8B—C1B	93.8 (3)
C8A—C3A—C4A	122.2 (3)	C3B—C8B—C7B	123.1 (3)
C3A—C4A—H4A	122.0	C7B—C8B—C1B	143.0 (3)
C3A—C4A—C5A	116.1 (3)	O1B—C9B—H9BA	109.5
C5A—C4A—H4A	122.0	O1B—C9B—H9BB	109.5
O1A—C5A—C4A	123.6 (3)	O1B—C9B—H9BC	109.5
O1A—C5A—C6A	114.8 (3)	H9BA—C9B—H9BB	109.5
C4A—C5A—C6A	121.6 (3)	H9BA—C9B—H9BC	109.5
O2A—C6A—C5A	114.3 (3)	H9BB—C9B—H9BC	109.5
O2A—C6A—C7A	124.3 (3)	O2B—C10B—H10D	109.5
C7A—C6A—C5A	121.4 (3)	O2B—C10B—H10E	109.5
C6A—C7A—H7A	122.0	O2B—C10B—H10F	109.5
C8A—C7A—C6A	116.1 (3)	H10D—C10B—H10E	109.5
C8A—C7A—H7A	122.0	H10D—C10B—H10F	109.5
C3A—C8A—C1A	94.0 (3)	H10E—C10B—H10F	109.5
C3A—C8A—C7A	122.7 (3)	N1B—C11B—C1B	114.2 (3)
C7A—C8A—C1A	143.2 (3)	N1B—C11B—H11C	108.7
O1A—C9A—H9AA	109.5	N1B—C11B—H11D	108.7
O1A—C9A—H9AB	109.5	C1B—C11B—H11C	108.7
O1A—C9A—H9AC	109.5	C1B—C11B—H11D	108.7
H9AA—C9A—H9AB	109.5	H11C—C11B—H11D	107.6
H9AA—C9A—H9AC	109.5	N1B—C12B—H12D	109.5
H9AB—C9A—H9AC	109.5	N1B—C12B—H12E	109.5
O2A—C10A—H10A	109.5	N1B—C12B—H12F	109.5
O2A—C10A—H10B	109.5	H12D—C12B—H12E	109.5
O2A—C10A—H10C	109.5	H12D—C12B—H12F	109.5
H10A—C10A—H10B	109.5	H12E—C12B—H12F	109.5
H10A—C10A—H10C	109.5	N1B—C13B—H13C	109.1
H10B—C10A—H10C	109.5	N1B—C13B—H13D	109.1
N1A—C11A—C1A	116.3 (3)	N1B—C13B—C14B	112.4 (3)
N1A—C11A—H11A	108.2	H13C—C13B—H13D	107.9
N1A—C11A—H11B	108.2	C14B—C13B—H13C	109.1
C1A—C11A—H11A	108.2	C14B—C13B—H13D	109.1
C1A—C11A—H11B	108.2	C13B—C14B—H14C	109.7
H11A—C11A—H11B	107.4	C13B—C14B—H14D	109.7
N1A—C12A—H12A	109.5	C13B—C14B—C15B	109.7 (3)
N1A—C12A—H12B	109.5	H14C—C14B—H14D	108.2
N1A—C12A—H12C	109.5	C15B—C14B—H14C	109.7
H12A—C12A—H12B	109.5	C15B—C14B—H14D	109.7
H12A—C12A—H12C	109.5	N2B—C15B—C14B	110.9 (3)
H12B—C12A—H12C	109.5	N2B—C15B—H15C	109.5
N1A—C13A—H13A	109.0	N2B—C15B—H15D	109.5
N1A—C13A—H13B	109.0	C14B—C15B—H15C	109.5
N1A—C13A—C14A	113.1 (3)	C14B—C15B—H15D	109.5
H13A—C13A—H13B	107.8	H15C—C15B—H15D	108.1
C14A—C13A—H13A	109.0	O3B—C16B—N2B	122.1 (3)
C14A—C13A—H13B	109.0	O3B—C16B—C17B	120.5 (3)
C13A—C14A—H14A	109.8	N2B—C16B—C17B	117.4 (3)
C13A—C14A—H14B	109.8	C16B—C17B—H17C	108.1
C13A—C14A—C15A	109.4 (3)	C16B—C17B—H17D	108.1
H14A—C14A—H14B	108.2	C16B—C17B—C18B	117.0 (3)
C15A—C14A—H14A	109.8	H17C—C17B—H17D	107.3
C15A—C14A—H14B	109.8	C18B—C17B—H17C	108.1
N2A—C15A—C14A	112.3 (3)	C18B—C17B—H17D	108.1
N2A—C15A—H15A	109.2	C19B—C18B—C17B	115.5 (3)
N2A—C15A—H15B	109.2	C23B—C18B—C17B	125.8 (3)
C14A—C15A—H15A	109.2	C23B—C18B—C19B	118.6 (3)
C14A—C15A—H15B	109.2	C18B—C19B—H19B	118.8
H15A—C15A—H15B	107.9	C20B—C19B—C18B	122.3 (3)
O3A—C16A—N2A	122.3 (3)	C20B—C19B—H19B	118.8
O3A—C16A—C17A	120.8 (3)	O4B—C20B—C19B	124.9 (3)
N2A—C16A—C17A	116.9 (3)	O4B—C20B—C21B	115.9 (3)
C16A—C17A—H17A	108.1	C19B—C20B—C21B	119.1 (3)
C16A—C17A—H17B	108.1	O5B—C21B—C20B	115.5 (3)
C16A—C17A—C18A	116.7 (3)	C22B—C21B—O5B	125.4 (3)
H17A—C17A—H17B	107.3	C22B—C21B—C20B	119.1 (3)
C18A—C17A—H17A	108.1	C21B—C22B—H22B	118.8
C18A—C17A—H17B	108.1	C21B—C22B—C23B	122.5 (3)
C19A—C18A—C17A	116.3 (3)	C23B—C22B—H22B	118.8
C23A—C18A—C17A	124.8 (3)	C18B—C23B—C22B	118.3 (3)
C23A—C18A—C19A	118.9 (3)	C18B—C23B—C24B	125.5 (3)
C18A—C19A—H19A	119.1	C22B—C23B—C24B	116.2 (3)
C20A—C19A—C18A	121.9 (3)	C23B—C24B—H24C	108.1
C20A—C19A—H19A	119.1	C23B—C24B—H24D	108.1
O4A—C20A—C21A	116.4 (3)	C23B—C24B—C25B	116.7 (3)
C19A—C20A—O4A	123.9 (3)	H24C—C24B—H24D	107.3
C19A—C20A—C21A	119.7 (3)	C25B—C24B—H24C	108.1
O5A—C21A—C20A	115.8 (3)	C25B—C24B—H24D	108.1
O5A—C21A—C22A	125.6 (3)	N2B—C25B—C24B	112.5 (3)
C22A—C21A—C20A	118.6 (3)	N2B—C25B—H25C	109.1
C21A—C22A—H22A	118.7	N2B—C25B—H25D	109.1
C21A—C22A—C23A	122.5 (3)	C24B—C25B—H25C	109.1
C23A—C22A—H22A	118.7	C24B—C25B—H25D	109.1
C18A—C23A—C22A	118.3 (3)	H25C—C25B—H25D	107.8
C18A—C23A—C24A	125.2 (3)	O4B—C26B—H26D	109.5
C22A—C23A—C24A	116.5 (3)	O4B—C26B—H26E	109.5
C23A—C24A—H24A	108.0	O4B—C26B—H26F	109.5
C23A—C24A—H24B	108.0	H26D—C26B—H26E	109.5
H24A—C24A—H24B	107.3	H26D—C26B—H26F	109.5
C25A—C24A—C23A	117.0 (3)	H26E—C26B—H26F	109.5
C25A—C24A—H24A	108.0	O5B—C27B—H27D	109.5
C25A—C24A—H24B	108.0	O5B—C27B—H27E	109.5
N2A—C25A—C24A	112.1 (3)	O5B—C27B—H27F	109.5
N2A—C25A—H25A	109.2	H27D—C27B—H27E	109.5
N2A—C25A—H25B	109.2	H27D—C27B—H27F	109.5
C24A—C25A—H25A	109.2	H27E—C27B—H27F	109.5
C24A—C25A—H25B	109.2
O1A—C5A—C6A—O2A	−2.7 (5)	C23A—C18A—C19A—C20A	−0.2 (5)
O1A—C5A—C6A—C7A	176.8 (3)	C23A—C24A—C25A—N2A	68.2 (4)
O2A—C6A—C7A—C8A	−179.1 (3)	C25A—N2A—C15A—C14A	96.0 (3)
O3A—C16A—C17A—C18A	−114.6 (4)	C25A—N2A—C16A—O3A	177.5 (3)
O4A—C20A—C21A—O5A	0.5 (5)	C25A—N2A—C16A—C17A	−3.4 (5)
O4A—C20A—C21A—C22A	178.8 (3)	C26A—O4A—C20A—C19A	31.5 (7)
O5A—C21A—C22A—C23A	179.6 (3)	C26A—O4A—C20A—C21A	−150.0 (5)
O1B—C5B—C6B—O2B	3.2 (5)	C27A—O5A—C21A—C20A	−178.3 (3)
O1B—C5B—C6B—C7B	−175.0 (4)	C27A—O5A—C21A—C22A	3.5 (5)
O2B—C6B—C7B—C8B	179.2 (3)	C1B—C2B—C3B—C4B	174.9 (6)
O3B—C16B—C17B—C18B	120.5 (4)	C1B—C2B—C3B—C8B	−2.2 (3)
O4B—C20B—C21B—O5B	−0.1 (5)	C2B—C1B—C8B—C3B	−2.2 (3)
O4B—C20B—C21B—C22B	−179.1 (3)	C2B—C1B—C8B—C7B	177.7 (5)
O5B—C21B—C22B—C23B	−179.8 (3)	C2B—C1B—C11B—N1B	87.7 (4)
N1A—C13A—C14A—C15A	−172.8 (3)	C2B—C3B—C4B—C5B	−178.1 (5)
N1B—C13B—C14B—C15B	168.7 (3)	C2B—C3B—C8B—C1B	2.3 (3)
N2A—C16A—C17A—C18A	66.3 (4)	C2B—C3B—C8B—C7B	−177.6 (3)
N2B—C16B—C17B—C18B	−59.8 (5)	C3B—C4B—C5B—O1B	177.3 (4)
C1A—C2A—C3A—C4A	−173.9 (5)	C3B—C4B—C5B—C6B	−3.3 (6)
C1A—C2A—C3A—C8A	1.3 (3)	C4B—C3B—C8B—C1B	−175.7 (4)
C2A—C1A—C8A—C3A	1.3 (3)	C4B—C3B—C8B—C7B	4.3 (6)
C2A—C1A—C8A—C7A	176.4 (5)	C4B—C5B—C6B—O2B	−176.2 (4)
C2A—C1A—C11A—N1A	90.4 (3)	C4B—C5B—C6B—C7B	5.6 (6)
C2A—C3A—C4A—C5A	174.6 (5)	C5B—C6B—C7B—C8B	−2.7 (5)
C2A—C3A—C8A—C1A	−1.3 (3)	C6B—C7B—C8B—C1B	178.0 (4)
C2A—C3A—C8A—C7A	−177.8 (3)	C6B—C7B—C8B—C3B	−2.1 (5)
C3A—C4A—C5A—O1A	−177.7 (4)	C8B—C1B—C2B—C3B	2.0 (3)
C3A—C4A—C5A—C6A	1.5 (6)	C8B—C1B—C11B—N1B	−173.0 (3)
C4A—C3A—C8A—C1A	175.3 (3)	C8B—C3B—C4B—C5B	−1.4 (6)
C4A—C3A—C8A—C7A	−1.2 (6)	C9B—O1B—C5B—C4B	−14.8 (6)
C4A—C5A—C6A—O2A	178.1 (4)	C9B—O1B—C5B—C6B	165.9 (4)
C4A—C5A—C6A—C7A	−2.5 (6)	C10B—O2B—C6B—C5B	168.5 (4)
C5A—C6A—C7A—C8A	1.5 (5)	C10B—O2B—C6B—C7B	−13.3 (6)
C6A—C7A—C8A—C1A	−173.9 (4)	C11B—N1B—C13B—C14B	−165.9 (3)
C6A—C7A—C8A—C3A	0.3 (5)	C11B—C1B—C2B—C3B	116.3 (3)
C8A—C1A—C2A—C3A	−1.2 (2)	C11B—C1B—C8B—C3B	−124.0 (3)
C8A—C1A—C11A—N1A	−173.3 (3)	C11B—C1B—C8B—C7B	55.9 (6)
C8A—C3A—C4A—C5A	0.3 (6)	C12B—N1B—C11B—C1B	−68.3 (4)
C9A—O1A—C5A—C4A	13.9 (6)	C12B—N1B—C13B—C14B	68.7 (4)
C9A—O1A—C5A—C6A	−165.3 (4)	C13B—N1B—C11B—C1B	166.7 (3)
C10A—O2A—C6A—C5A	−167.6 (4)	C13B—C14B—C15B—N2B	173.4 (3)
C10A—O2A—C6A—C7A	12.9 (6)	C15B—N2B—C16B—O3B	0.5 (5)
C11A—N1A—C13A—C14A	158.4 (3)	C15B—N2B—C16B—C17B	−179.2 (3)
C11A—C1A—C2A—C3A	109.6 (3)	C15B—N2B—C25B—C24B	−109.1 (4)
C11A—C1A—C8A—C3A	−116.9 (3)	C16B—N2B—C15B—C14B	79.9 (4)
C11A—C1A—C8A—C7A	58.2 (6)	C16B—N2B—C25B—C24B	78.2 (4)
C12A—N1A—C11A—C1A	−50.2 (4)	C16B—C17B—C18B—C19B	−132.4 (4)
C12A—N1A—C13A—C14A	−73.0 (4)	C16B—C17B—C18B—C23B	48.5 (5)
C13A—N1A—C11A—C1A	77.4 (3)	C17B—C18B—C19B—C20B	−179.0 (3)
C13A—C14A—C15A—N2A	−173.4 (3)	C17B—C18B—C23B—C22B	179.1 (3)
C15A—N2A—C16A—O3A	−0.1 (5)	C17B—C18B—C23B—C24B	−1.8 (5)
C15A—N2A—C16A—C17A	179.0 (3)	C18B—C19B—C20B—O4B	179.5 (3)
C15A—N2A—C25A—C24A	105.7 (3)	C18B—C19B—C20B—C21B	−0.7 (6)
C16A—N2A—C15A—C14A	−86.3 (4)	C18B—C23B—C24B—C25B	9.7 (5)
C16A—N2A—C25A—C24A	−72.0 (4)	C19B—C18B—C23B—C22B	0.0 (5)
C16A—C17A—C18A—C19A	134.4 (3)	C19B—C18B—C23B—C24B	179.1 (3)
C16A—C17A—C18A—C23A	−46.6 (5)	C19B—C20B—C21B—O5B	−180.0 (3)
C17A—C18A—C19A—C20A	178.8 (3)	C19B—C20B—C21B—C22B	1.1 (5)
C17A—C18A—C23A—C22A	−179.9 (3)	C20B—C21B—C22B—C23B	−0.9 (5)
C17A—C18A—C23A—C24A	0.4 (5)	C21B—C22B—C23B—C18B	0.4 (5)
C18A—C19A—C20A—O4A	−179.5 (3)	C21B—C22B—C23B—C24B	−178.8 (3)
C18A—C19A—C20A—C21A	2.1 (5)	C22B—C23B—C24B—C25B	−171.2 (3)
C18A—C23A—C24A—C25A	−12.9 (5)	C23B—C18B—C19B—C20B	0.2 (5)
C19A—C18A—C23A—C22A	−0.9 (5)	C23B—C24B—C25B—N2B	−65.1 (4)
C19A—C18A—C23A—C24A	179.4 (3)	C25B—N2B—C15B—C14B	−92.9 (4)
C19A—C20A—C21A—O5A	179.1 (3)	C25B—N2B—C16B—O3B	173.2 (3)
C19A—C20A—C21A—C22A	−2.6 (5)	C25B—N2B—C16B—C17B	−6.5 (5)
C20A—C21A—C22A—C23A	1.5 (5)	C26B—O4B—C20B—C19B	−19.5 (6)
C21A—C22A—C23A—C18A	0.3 (5)	C26B—O4B—C20B—C21B	160.7 (4)
C21A—C22A—C23A—C24A	−180.0 (3)	C27B—O5B—C21B—C20B	−178.7 (3)
C22A—C23A—C24A—C25A	167.4 (3)	C27B—O5B—C21B—C22B	0.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···Cl1B^i	0.82	2.58	3.230 (4)	137
O6—H6B···Cl1B	0.82	2.49	3.283 (4)	162
N1A—H1A···Cl1A	0.98	2.12	3.055 (3)	158
N1B—H1B···Cl1B	0.98	2.12	3.093 (3)	174

Symmetry code: (i) x+1, y, z.

[3-(7,8-Dimethoxy-2-oxo-2,3,4,5-tetrahydro-1H-3-benzazepin-3-yl)propyl]{[3,4-dimethoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-yl]methyl}methylazanium tetrahydrate (i-518)

Crystal data

C27H37N2O5^+·Cl^−·4H2O	Dx = 1.253 Mg m^−3
Mr = 577.10	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 32894 reflections
a = 8.6747 (2) Å	θ = 3.0–27.5°
b = 18.2437 (5) Å	µ = 0.18 mm^−1
c = 38.6507 (9) Å	T = 296 K
V = 6116.8 (3) Å^3	Needle, colourless
Z = 8	0.3 × 0.12 × 0.1 mm
F(000) = 2480

Data collection

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	13936 independent reflections
Radiation source: fine-focus sealed tube	7143 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.058
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→10
Tmin = 0.949, Tmax = 0.983	k = −23→23
55596 measured reflections	l = −50→50

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.0468P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.106	(Δ/σ)max = 0.001
S = 0.96	Δρmax = 0.17 e Å^−3
13936 reflections	Δρmin = −0.19 e Å^−3
715 parameters	Absolute structure: Flack x determined using 2366 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
7 restraints	Absolute structure parameter: −0.01 (3)
Primary atom site location: dual

Special details

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

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

	x	y	z	Uiso*/Ueq
Cl1	0.61033 (12)	0.47173 (6)	0.42178 (4)	0.0999 (4)
Cl2	0.41813 (13)	0.54721 (6)	0.57885 (4)	0.0947 (4)
O1A	0.6412 (3)	0.87639 (14)	0.28869 (7)	0.0726 (7)
O2A	0.8773 (3)	0.82923 (15)	0.32083 (7)	0.0730 (8)
O3A	−0.0837 (3)	0.62870 (14)	0.40461 (6)	0.0687 (7)
O4A	0.2588 (3)	0.64185 (15)	0.26145 (7)	0.0714 (8)
O5A	0.4908 (3)	0.56182 (14)	0.27999 (6)	0.0633 (7)
N1A	0.4527 (3)	0.61379 (15)	0.44549 (7)	0.0484 (7)
H1A	0.494933	0.567889	0.436337	0.058*
N2A	0.0208 (3)	0.51664 (14)	0.41408 (7)	0.0460 (7)
O11	0.4198 (3)	0.77188 (13)	0.54417 (6)	0.0711 (7)
H11E	0.405754	0.805026	0.558228	0.107*
H11F	0.424524	0.790075	0.524778	0.107*
O12	0.6567 (3)	0.67652 (16)	0.56147 (7)	0.0862 (9)
H12G	0.599853	0.706064	0.551551	0.129*
H12H	0.607573	0.638894	0.565841	0.129*
O13	0.4072 (3)	0.83916 (17)	0.48195 (8)	0.0946 (9)
H13E	0.489317	0.832257	0.471817	0.142*
H13F	0.335687	0.832017	0.468407	0.142*
O14	0.2006 (3)	0.66100 (18)	0.54256 (9)	0.1008 (11)
H14E	0.260926	0.695366	0.540569	0.151*
H14F	0.237546	0.621666	0.548639	0.151*
C1A	0.4913 (4)	0.66664 (18)	0.38552 (8)	0.0482 (8)
H1AA	0.508186	0.616084	0.377837	0.058*
C2A	0.3433 (4)	0.70032 (18)	0.36840 (9)	0.0532 (9)
H2AA	0.283207	0.665711	0.354944	0.064*
H2AB	0.278691	0.727959	0.384189	0.064*
C3A	0.4532 (4)	0.74717 (18)	0.34703 (8)	0.0468 (8)
C4A	0.4622 (4)	0.79966 (19)	0.32122 (9)	0.0523 (9)
H4A	0.374999	0.816732	0.309783	0.063*
C5A	0.6085 (4)	0.82530 (19)	0.31340 (9)	0.0522 (9)
C6A	0.7391 (4)	0.79873 (19)	0.33130 (10)	0.0514 (9)
C7A	0.7275 (4)	0.74544 (19)	0.35628 (9)	0.0528 (9)
H7A	0.813524	0.727194	0.367766	0.063*
C8A	0.5805 (4)	0.72059 (17)	0.36329 (8)	0.0469 (8)
C9A	0.5153 (5)	0.9042 (3)	0.26888 (11)	0.0855 (13)
H9AA	0.469044	0.864922	0.256007	0.128*
H9AB	0.552151	0.940991	0.253180	0.128*
H9AC	0.440109	0.925294	0.284130	0.128*
C10A	1.0098 (4)	0.8103 (2)	0.34018 (11)	0.0762 (12)
H10A	0.994031	0.822906	0.364033	0.114*
H10B	1.097317	0.836510	0.331375	0.114*
H10C	1.027962	0.758518	0.338275	0.114*
C11A	0.5187 (4)	0.67440 (18)	0.42392 (8)	0.0521 (8)
H11A	0.628879	0.676779	0.428003	0.063*
H11B	0.474422	0.720468	0.431573	0.063*
C12A	0.5068 (5)	0.6199 (2)	0.48184 (9)	0.0769 (12)
H12A	0.617441	0.620681	0.482268	0.115*
H12B	0.470185	0.578637	0.494877	0.115*
H12C	0.467736	0.664320	0.491854	0.115*
C13A	0.2807 (4)	0.60841 (19)	0.44244 (9)	0.0508 (9)
H13A	0.252891	0.606920	0.418140	0.061*
H13B	0.234595	0.651989	0.452416	0.061*
C14A	0.2152 (4)	0.54150 (19)	0.46028 (9)	0.0510 (9)
H14A	0.224230	0.547491	0.485133	0.061*
H14B	0.274665	0.498691	0.453684	0.061*
C15A	0.0461 (4)	0.52925 (19)	0.45085 (8)	0.0493 (9)
H15A	0.007660	0.487367	0.463688	0.059*
H15B	−0.013045	0.571796	0.457954	0.059*
C16A	−0.0463 (4)	0.5673 (2)	0.39390 (9)	0.0509 (9)
C17A	−0.0683 (4)	0.5484 (2)	0.35611 (9)	0.0576 (9)
H17A	−0.135538	0.584540	0.345571	0.069*
H17B	−0.118703	0.501046	0.354373	0.069*
C18A	0.0828 (4)	0.54584 (17)	0.33620 (8)	0.0464 (8)
C19A	0.0985 (4)	0.59186 (18)	0.30734 (9)	0.0539 (9)
H19A	0.014457	0.619862	0.300364	0.065*
C20A	0.2328 (4)	0.59693 (19)	0.28917 (9)	0.0517 (9)
C21A	0.3583 (4)	0.55391 (19)	0.29940 (9)	0.0496 (8)
C22A	0.3446 (4)	0.50895 (18)	0.32752 (9)	0.0493 (8)
H22A	0.429319	0.481235	0.334350	0.059*
C23A	0.2074 (4)	0.50325 (17)	0.34638 (9)	0.0463 (8)
C24A	0.2106 (4)	0.45134 (18)	0.37689 (8)	0.0502 (9)
H24A	0.295999	0.465591	0.391645	0.060*
H24B	0.233506	0.402711	0.368140	0.060*
C25A	0.0682 (4)	0.44566 (18)	0.39935 (9)	0.0520 (9)
H25A	−0.015842	0.426031	0.385641	0.062*
H25B	0.088250	0.411556	0.418075	0.062*
C26A	0.1473 (6)	0.6973 (3)	0.25430 (10)	0.0860 (14)
H26A	0.053558	0.674796	0.246424	0.129*
H26B	0.186066	0.729467	0.236691	0.129*
H26C	0.127139	0.724815	0.274972	0.129*
C27A	0.6277 (4)	0.5313 (3)	0.29376 (11)	0.0814 (13)
H27A	0.643912	0.549626	0.316751	0.122*
H27B	0.713531	0.544581	0.279398	0.122*
H27C	0.618509	0.478839	0.294475	0.122*
O1B	0.3760 (3)	0.12954 (15)	0.71476 (7)	0.0744 (8)
O2B	0.1448 (3)	0.16137 (15)	0.67729 (7)	0.0751 (8)
O3B	1.0957 (3)	0.36746 (16)	0.59195 (7)	0.0764 (8)
O4B	0.7429 (3)	0.35039 (15)	0.73160 (7)	0.0751 (8)
O5B	0.5245 (3)	0.43911 (16)	0.71391 (6)	0.0712 (7)
N1B	0.5606 (3)	0.40080 (15)	0.56155 (7)	0.0514 (7)
H1B	0.529400	0.452275	0.563429	0.062*
N2B	1.0089 (3)	0.48330 (16)	0.58399 (7)	0.0533 (7)
C1B	0.5426 (4)	0.28530 (18)	0.59855 (9)	0.0514 (8)
H1BA	0.549202	0.257125	0.577017	0.062*
C2B	0.6853 (4)	0.2711 (2)	0.62305 (10)	0.0601 (10)
H2BA	0.763593	0.239450	0.613159	0.072*
H2BB	0.730221	0.315214	0.632749	0.072*
C3B	0.5737 (4)	0.23229 (18)	0.64690 (9)	0.0513 (9)
C4B	0.5585 (4)	0.1929 (2)	0.67748 (10)	0.0586 (10)
H4B	0.642867	0.182951	0.691552	0.070*
C5B	0.4114 (4)	0.1693 (2)	0.68604 (9)	0.0552 (9)
C6B	0.2837 (4)	0.1852 (2)	0.66471 (10)	0.0559 (10)
C7B	0.3010 (4)	0.22418 (19)	0.63406 (10)	0.0579 (10)
H7B	0.217750	0.235048	0.619794	0.069*
C8B	0.4495 (4)	0.24577 (17)	0.62607 (9)	0.0495 (8)
C9B	0.4984 (6)	0.1051 (3)	0.73629 (11)	0.0959 (15)
H9BA	0.568193	0.075598	0.722980	0.144*
H9BB	0.457157	0.076511	0.754978	0.144*
H9BC	0.552393	0.146709	0.745472	0.144*
C10B	0.0120 (4)	0.1801 (2)	0.65774 (12)	0.0793 (13)
H10D	0.007358	0.232374	0.654962	0.119*
H10E	−0.078600	0.163469	0.669629	0.119*
H10F	0.017549	0.157241	0.635412	0.119*
C11B	0.4912 (4)	0.36233 (18)	0.59245 (9)	0.0541 (9)
H11C	0.514882	0.390849	0.612960	0.065*
H11D	0.380018	0.362270	0.589779	0.065*
C12B	0.4965 (4)	0.3740 (2)	0.52816 (10)	0.0784 (12)
H12D	0.540182	0.401654	0.509442	0.118*
H12E	0.386579	0.379899	0.528182	0.118*
H12F	0.521532	0.323072	0.525311	0.118*
C13B	0.7332 (3)	0.4006 (2)	0.56251 (10)	0.0548 (9)
H13C	0.770711	0.353707	0.554222	0.066*
H13D	0.767412	0.406491	0.586243	0.066*
C14B	0.8021 (4)	0.4617 (2)	0.54045 (9)	0.0538 (9)
H14C	0.748975	0.507283	0.545358	0.065*
H14D	0.786891	0.450270	0.516172	0.065*
C15B	0.9743 (4)	0.4712 (2)	0.54755 (9)	0.0580 (10)
H15C	1.028550	0.427823	0.539711	0.070*
H15D	1.012172	0.512583	0.534251	0.070*
C16B	1.0673 (4)	0.4291 (2)	0.60334 (10)	0.0595 (10)
C17B	1.0917 (4)	0.4453 (2)	0.64106 (10)	0.0662 (10)
H17C	1.145424	0.491670	0.643489	0.079*
H17D	1.155591	0.407332	0.651212	0.079*
C18B	0.9387 (4)	0.4490 (2)	0.66026 (9)	0.0523 (9)
C19B	0.9156 (4)	0.4003 (2)	0.68770 (9)	0.0574 (10)
H19B	0.995249	0.369152	0.694283	0.069*
C20B	0.7781 (4)	0.3975 (2)	0.70511 (10)	0.0595 (10)
C21B	0.6580 (4)	0.4447 (2)	0.69532 (9)	0.0575 (9)
C22B	0.6808 (4)	0.49246 (19)	0.66838 (9)	0.0528 (9)
H22B	0.600455	0.523181	0.661788	0.063*
C23B	0.8210 (4)	0.49658 (18)	0.65047 (9)	0.0505 (9)
C24B	0.8290 (4)	0.55344 (19)	0.62200 (9)	0.0575 (10)
H24C	0.818543	0.601387	0.632590	0.069*
H24D	0.740435	0.546470	0.607043	0.069*
C25B	0.9723 (4)	0.5545 (2)	0.59941 (10)	0.0613 (10)
H25C	0.957716	0.590060	0.581026	0.074*
H25D	1.059261	0.570564	0.613254	0.074*
C26B	0.8556 (6)	0.2969 (2)	0.74068 (12)	0.0859 (14)
H26D	0.877188	0.266552	0.720979	0.129*
H26E	0.817171	0.267096	0.759236	0.129*
H26F	0.948483	0.321066	0.747941	0.129*
C27B	0.3919 (5)	0.4730 (3)	0.70011 (11)	0.0889 (14)
H27D	0.407427	0.525072	0.699187	0.133*
H27E	0.304732	0.462300	0.714548	0.133*
H27F	0.373331	0.454714	0.677195	0.133*
O21	0.3803 (3)	0.34166 (16)	0.44309 (8)	0.0894 (9)
H21A	0.422732	0.380904	0.438318	0.134*
H21B	0.443922	0.309654	0.447308	0.134*
O22	0.1170 (3)	0.33620 (18)	0.48238 (7)	0.1011 (10)
H22C	0.179640	0.328082	0.466867	0.152*
H22D	0.032450	0.340492	0.473217	0.152*
O23	0.1092 (4)	0.26197 (14)	0.54282 (7)	0.0865 (9)
H23A	0.097206	0.285699	0.525003	0.130*
H23B	0.089296	0.294689	0.556703	0.130*
O24	−0.1792 (4)	0.3540 (2)	0.45942 (9)	0.0974 (10)
H24E	−0.225043	0.378122	0.444680	0.18 (3)*
H24F	−0.205023	0.310652	0.459940	0.18 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0587 (6)	0.0590 (6)	0.1819 (13)	0.0061 (5)	0.0032 (7)	0.0043 (7)
Cl2	0.0665 (6)	0.0591 (6)	0.1585 (12)	0.0101 (5)	0.0028 (7)	0.0132 (7)
O1A	0.0695 (17)	0.0770 (18)	0.0713 (17)	0.0007 (15)	−0.0032 (15)	0.0328 (15)
O2A	0.0505 (15)	0.0872 (19)	0.0811 (19)	−0.0057 (15)	0.0023 (14)	0.0243 (16)
O3A	0.0811 (18)	0.0557 (15)	0.0692 (17)	0.0203 (15)	−0.0093 (15)	−0.0041 (14)
O4A	0.0798 (18)	0.0730 (18)	0.0615 (16)	−0.0025 (15)	−0.0141 (14)	0.0251 (14)
O5A	0.0599 (15)	0.0744 (18)	0.0555 (15)	−0.0020 (14)	−0.0021 (13)	0.0102 (13)
N1A	0.0468 (15)	0.0479 (16)	0.0506 (16)	−0.0084 (13)	−0.0064 (14)	0.0037 (14)
N2A	0.0444 (15)	0.0428 (15)	0.0508 (17)	−0.0011 (13)	−0.0027 (14)	−0.0002 (14)
O11	0.0883 (19)	0.0548 (15)	0.0704 (17)	0.0001 (15)	0.0044 (16)	0.0011 (13)
O12	0.0722 (17)	0.090 (2)	0.096 (2)	0.0041 (16)	−0.0032 (17)	0.0143 (17)
O13	0.0728 (18)	0.120 (2)	0.091 (2)	0.0044 (19)	0.0002 (17)	0.0185 (19)
O14	0.0699 (18)	0.086 (2)	0.147 (3)	0.0026 (17)	−0.0136 (19)	0.026 (2)
C1A	0.0527 (19)	0.0412 (18)	0.0508 (19)	−0.0012 (16)	−0.0016 (16)	−0.0002 (16)
C2A	0.0468 (18)	0.054 (2)	0.059 (2)	−0.0089 (17)	−0.0047 (17)	−0.0004 (18)
C3A	0.0415 (18)	0.050 (2)	0.049 (2)	−0.0031 (16)	0.0028 (16)	−0.0022 (17)
C4A	0.050 (2)	0.057 (2)	0.050 (2)	0.0067 (18)	−0.0065 (18)	0.0034 (18)
C5A	0.059 (2)	0.049 (2)	0.049 (2)	0.0018 (19)	0.0017 (18)	0.0086 (18)
C6A	0.0463 (19)	0.052 (2)	0.056 (2)	−0.0013 (17)	0.0029 (17)	0.0066 (18)
C7A	0.0464 (19)	0.057 (2)	0.055 (2)	0.0062 (17)	−0.0011 (17)	0.0148 (18)
C8A	0.0485 (19)	0.0432 (18)	0.0490 (19)	−0.0036 (16)	−0.0020 (17)	0.0053 (16)
C9A	0.093 (3)	0.087 (3)	0.076 (3)	0.012 (3)	−0.014 (3)	0.036 (2)
C10A	0.045 (2)	0.089 (3)	0.094 (3)	−0.007 (2)	−0.004 (2)	0.010 (3)
C11A	0.0492 (18)	0.051 (2)	0.056 (2)	−0.0135 (16)	−0.0038 (17)	0.0060 (17)
C12A	0.078 (3)	0.104 (3)	0.049 (2)	−0.019 (3)	−0.018 (2)	0.007 (2)
C13A	0.0443 (18)	0.052 (2)	0.056 (2)	−0.0051 (16)	−0.0041 (17)	0.0052 (18)
C14A	0.0496 (19)	0.053 (2)	0.051 (2)	−0.0030 (17)	−0.0044 (17)	0.0056 (17)
C15A	0.0456 (18)	0.052 (2)	0.050 (2)	−0.0047 (16)	0.0060 (17)	0.0067 (17)
C16A	0.0393 (18)	0.053 (2)	0.061 (2)	−0.0020 (17)	−0.0046 (17)	−0.0019 (19)
C17A	0.053 (2)	0.059 (2)	0.061 (2)	−0.0013 (18)	−0.0159 (19)	−0.0007 (19)
C18A	0.0433 (18)	0.0459 (18)	0.050 (2)	−0.0043 (16)	−0.0123 (16)	−0.0047 (17)
C19A	0.054 (2)	0.050 (2)	0.058 (2)	−0.0010 (18)	−0.0229 (19)	0.0032 (18)
C20A	0.062 (2)	0.048 (2)	0.045 (2)	−0.0089 (19)	−0.0171 (19)	0.0062 (17)
C21A	0.053 (2)	0.049 (2)	0.047 (2)	−0.0044 (18)	−0.0023 (18)	0.0014 (18)
C22A	0.0505 (19)	0.045 (2)	0.052 (2)	0.0010 (16)	−0.0091 (18)	−0.0031 (18)
C23A	0.0498 (19)	0.0399 (18)	0.049 (2)	−0.0003 (16)	−0.0087 (17)	0.0006 (16)
C24A	0.058 (2)	0.0401 (18)	0.052 (2)	0.0038 (17)	−0.0012 (17)	0.0016 (17)
C25A	0.055 (2)	0.0422 (19)	0.058 (2)	−0.0021 (17)	−0.0037 (18)	0.0020 (17)
C26A	0.110 (4)	0.071 (3)	0.077 (3)	0.012 (3)	−0.016 (3)	0.023 (2)
C27A	0.051 (2)	0.121 (4)	0.072 (3)	−0.003 (3)	−0.004 (2)	0.017 (3)
O1B	0.0738 (18)	0.091 (2)	0.0583 (16)	0.0002 (16)	−0.0055 (15)	0.0222 (16)
O2B	0.0514 (15)	0.088 (2)	0.0860 (19)	−0.0096 (15)	−0.0033 (14)	0.0244 (16)
O3B	0.0670 (17)	0.0774 (19)	0.085 (2)	0.0206 (16)	−0.0020 (16)	−0.0048 (16)
O4B	0.0831 (19)	0.0733 (18)	0.0690 (18)	−0.0031 (16)	−0.0130 (15)	0.0238 (16)
O5B	0.0617 (16)	0.089 (2)	0.0634 (16)	0.0041 (15)	0.0027 (14)	0.0136 (15)
N1B	0.0456 (16)	0.0486 (16)	0.0600 (18)	−0.0038 (14)	−0.0078 (14)	0.0046 (14)
N2B	0.0450 (15)	0.0594 (18)	0.0555 (18)	−0.0052 (14)	0.0004 (14)	0.0053 (16)
C1B	0.0498 (19)	0.048 (2)	0.057 (2)	−0.0002 (16)	−0.0035 (18)	0.0019 (17)
C2B	0.0444 (19)	0.061 (2)	0.075 (3)	0.0059 (17)	−0.0026 (19)	0.002 (2)
C3B	0.0458 (19)	0.051 (2)	0.057 (2)	0.0056 (17)	−0.0029 (18)	−0.0021 (18)
C4B	0.053 (2)	0.068 (2)	0.054 (2)	0.010 (2)	−0.0091 (19)	−0.002 (2)
C5B	0.059 (2)	0.058 (2)	0.049 (2)	0.004 (2)	−0.0015 (18)	−0.0013 (19)
C6B	0.0430 (19)	0.058 (2)	0.066 (3)	−0.0057 (18)	−0.0054 (19)	0.004 (2)
C7B	0.049 (2)	0.060 (2)	0.064 (2)	−0.0048 (18)	−0.0102 (19)	0.008 (2)
C8B	0.049 (2)	0.0405 (18)	0.059 (2)	−0.0024 (16)	−0.0079 (18)	0.0006 (17)
C9B	0.104 (3)	0.119 (4)	0.065 (3)	0.018 (3)	−0.011 (3)	0.030 (3)
C10B	0.051 (2)	0.084 (3)	0.103 (3)	−0.011 (2)	−0.004 (2)	0.008 (3)
C11B	0.0442 (18)	0.051 (2)	0.067 (2)	−0.0025 (16)	0.0034 (18)	0.0058 (18)
C12B	0.071 (3)	0.096 (3)	0.069 (3)	−0.020 (2)	−0.020 (2)	0.004 (2)
C13B	0.0425 (19)	0.055 (2)	0.067 (2)	0.0007 (17)	−0.0068 (17)	0.0014 (19)
C14B	0.052 (2)	0.061 (2)	0.049 (2)	−0.0032 (18)	0.0019 (17)	0.0037 (18)
C15B	0.051 (2)	0.069 (3)	0.055 (2)	−0.0053 (19)	0.0054 (18)	0.003 (2)
C16B	0.0382 (19)	0.070 (3)	0.070 (3)	0.0006 (19)	0.0002 (19)	0.005 (2)
C17B	0.047 (2)	0.079 (3)	0.072 (3)	−0.002 (2)	−0.0168 (19)	0.003 (2)
C18B	0.0479 (19)	0.057 (2)	0.052 (2)	−0.0023 (18)	−0.0118 (18)	−0.0020 (19)
C19B	0.055 (2)	0.058 (2)	0.059 (2)	−0.002 (2)	−0.020 (2)	0.0044 (19)
C20B	0.068 (2)	0.054 (2)	0.057 (2)	−0.004 (2)	−0.018 (2)	0.008 (2)
C21B	0.060 (2)	0.063 (2)	0.050 (2)	−0.006 (2)	−0.0099 (19)	−0.002 (2)
C22B	0.053 (2)	0.057 (2)	0.048 (2)	0.0048 (18)	−0.0073 (17)	0.0030 (18)
C23B	0.059 (2)	0.047 (2)	0.046 (2)	−0.0049 (17)	−0.0069 (18)	−0.0031 (17)
C24B	0.070 (2)	0.048 (2)	0.055 (2)	0.0001 (18)	−0.0016 (19)	0.0024 (18)
C25B	0.066 (2)	0.055 (2)	0.063 (2)	−0.013 (2)	−0.004 (2)	0.0021 (19)
C26B	0.102 (3)	0.069 (3)	0.087 (3)	0.000 (3)	−0.025 (3)	0.024 (3)
C27B	0.055 (2)	0.129 (4)	0.083 (3)	−0.002 (3)	−0.013 (2)	0.018 (3)
O21	0.0700 (18)	0.087 (2)	0.111 (2)	0.0013 (16)	−0.0024 (17)	0.0170 (18)
O22	0.0787 (19)	0.137 (3)	0.087 (2)	0.010 (2)	0.0001 (17)	0.032 (2)
O23	0.113 (2)	0.0636 (17)	0.0832 (19)	0.0014 (17)	0.0038 (18)	0.0093 (14)
O24	0.080 (2)	0.101 (3)	0.112 (3)	−0.0048 (19)	−0.016 (2)	0.015 (2)

Geometric parameters (Å, º)

O1A—C5A	1.364 (4)	O1B—C5B	1.361 (4)
O1A—C9A	1.426 (4)	O1B—C9B	1.420 (5)
O2A—C6A	1.382 (4)	O2B—C6B	1.370 (4)
O2A—C10A	1.414 (4)	O2B—C10B	1.419 (4)
O3A—C16A	1.238 (4)	O3B—C16B	1.233 (4)
O4A—C20A	1.368 (4)	O4B—C20B	1.371 (4)
O4A—C26A	1.426 (5)	O4B—C26B	1.425 (5)
O5A—C21A	1.380 (4)	O5B—C21B	1.367 (4)
O5A—C27A	1.416 (4)	O5B—C27B	1.411 (4)
N1A—H1A	0.9800	N1B—H1B	0.9800
N1A—C11A	1.498 (4)	N1B—C11B	1.511 (4)
N1A—C12A	1.485 (4)	N1B—C12B	1.488 (4)
N1A—C13A	1.500 (4)	N1B—C13B	1.498 (4)
N2A—C15A	1.456 (4)	N2B—C15B	1.457 (4)
N2A—C16A	1.342 (4)	N2B—C16B	1.338 (5)
N2A—C25A	1.473 (4)	N2B—C25B	1.465 (5)
O11—H11E	0.8222	C1B—H1BA	0.9800
O11—H11F	0.8207	C1B—C2B	1.580 (5)
O12—H12G	0.8248	C1B—C8B	1.518 (5)
O12—H12H	0.8253	C1B—C11B	1.493 (5)
O13—H13E	0.8223	C2B—H2BA	0.9700
O13—H13F	0.8222	C2B—H2BB	0.9700
O14—H14E	0.8205	C2B—C3B	1.512 (5)
O14—H14F	0.8203	C3B—C4B	1.389 (5)
C1A—H1AA	0.9800	C3B—C8B	1.368 (4)
C1A—C2A	1.570 (4)	C4B—H4B	0.9300
C1A—C8A	1.518 (4)	C4B—C5B	1.387 (5)
C1A—C11A	1.510 (4)	C5B—C6B	1.411 (5)
C2A—H2AA	0.9700	C6B—C7B	1.390 (5)
C2A—H2AB	0.9700	C7B—H7B	0.9300
C2A—C3A	1.524 (4)	C7B—C8B	1.382 (5)
C3A—C4A	1.385 (5)	C9B—H9BA	0.9600
C3A—C8A	1.360 (4)	C9B—H9BB	0.9600
C4A—H4A	0.9300	C9B—H9BC	0.9600
C4A—C5A	1.386 (5)	C10B—H10D	0.9600
C5A—C6A	1.413 (5)	C10B—H10E	0.9600
C6A—C7A	1.374 (5)	C10B—H10F	0.9600
C7A—H7A	0.9300	C11B—H11C	0.9700
C7A—C8A	1.381 (4)	C11B—H11D	0.9700
C9A—H9AA	0.9600	C12B—H12D	0.9600
C9A—H9AB	0.9600	C12B—H12E	0.9600
C9A—H9AC	0.9600	C12B—H12F	0.9600
C10A—H10A	0.9600	C13B—H13C	0.9700
C10A—H10B	0.9600	C13B—H13D	0.9700
C10A—H10C	0.9600	C13B—C14B	1.525 (5)
C11A—H11A	0.9700	C14B—H14C	0.9700
C11A—H11B	0.9700	C14B—H14D	0.9700
C12A—H12A	0.9600	C14B—C15B	1.529 (5)
C12A—H12B	0.9600	C15B—H15C	0.9700
C12A—H12C	0.9600	C15B—H15D	0.9700
C13A—H13A	0.9700	C16B—C17B	1.503 (5)
C13A—H13B	0.9700	C17B—H17C	0.9700
C13A—C14A	1.513 (5)	C17B—H17D	0.9700
C14A—H14A	0.9700	C17B—C18B	1.522 (5)
C14A—H14B	0.9700	C18B—C19B	1.398 (5)
C14A—C15A	1.528 (4)	C18B—C23B	1.392 (5)
C15A—H15A	0.9700	C19B—H19B	0.9300
C15A—H15B	0.9700	C19B—C20B	1.371 (5)
C16A—C17A	1.513 (5)	C20B—C21B	1.404 (5)
C17A—H17A	0.9700	C21B—C22B	1.372 (5)
C17A—H17B	0.9700	C22B—H22B	0.9300
C17A—C18A	1.521 (5)	C22B—C23B	1.401 (5)
C18A—C19A	1.403 (5)	C23B—C24B	1.514 (5)
C18A—C23A	1.389 (4)	C24B—H24C	0.9700
C19A—H19A	0.9300	C24B—H24D	0.9700
C19A—C20A	1.364 (5)	C24B—C25B	1.519 (5)
C20A—C21A	1.399 (5)	C25B—H25C	0.9700
C21A—C22A	1.367 (5)	C25B—H25D	0.9700
C22A—H22A	0.9300	C26B—H26D	0.9600
C22A—C23A	1.400 (4)	C26B—H26E	0.9600
C23A—C24A	1.513 (4)	C26B—H26F	0.9600
C24A—H24A	0.9700	C27B—H27D	0.9600
C24A—H24B	0.9700	C27B—H27E	0.9600
C24A—C25A	1.513 (4)	C27B—H27F	0.9600
C25A—H25A	0.9700	O21—H21A	0.8257
C25A—H25B	0.9700	O21—H21B	0.8198
C26A—H26A	0.9600	O22—H22C	0.8226
C26A—H26B	0.9600	O22—H22D	0.8181
C26A—H26C	0.9600	O23—H23A	0.8202
C27A—H27A	0.9600	O23—H23B	0.8210
C27A—H27B	0.9600	O24—H24E	0.8226
C27A—H27C	0.9600	O24—H24F	0.8214
C5A—O1A—C9A	117.4 (3)	C5B—O1B—C9B	118.5 (3)
C6A—O2A—C10A	116.8 (3)	C6B—O2B—C10B	116.6 (3)
C20A—O4A—C26A	117.7 (3)	C20B—O4B—C26B	117.4 (3)
C21A—O5A—C27A	116.9 (3)	C21B—O5B—C27B	117.4 (3)
C11A—N1A—H1A	106.7	C11B—N1B—H1B	106.0
C11A—N1A—C13A	112.6 (3)	C12B—N1B—H1B	106.0
C12A—N1A—H1A	106.7	C12B—N1B—C11B	112.6 (3)
C12A—N1A—C11A	110.5 (3)	C12B—N1B—C13B	113.2 (3)
C12A—N1A—C13A	113.2 (3)	C13B—N1B—H1B	106.0
C13A—N1A—H1A	106.7	C13B—N1B—C11B	112.2 (3)
C15A—N2A—C25A	118.3 (3)	C15B—N2B—C25B	118.8 (3)
C16A—N2A—C15A	121.6 (3)	C16B—N2B—C15B	120.4 (3)
C16A—N2A—C25A	120.1 (3)	C16B—N2B—C25B	120.7 (3)
H11E—O11—H11F	108.3	C2B—C1B—H1BA	112.2
H12G—O12—H12H	109.3	C8B—C1B—H1BA	112.2
H13E—O13—H13F	109.0	C8B—C1B—C2B	85.3 (2)
H14E—O14—H14F	116.5	C11B—C1B—H1BA	112.2
C2A—C1A—H1AA	111.3	C11B—C1B—C2B	118.9 (3)
C8A—C1A—H1AA	111.3	C11B—C1B—C8B	113.5 (3)
C8A—C1A—C2A	85.7 (2)	C1B—C2B—H2BA	114.2
C11A—C1A—H1AA	111.3	C1B—C2B—H2BB	114.2
C11A—C1A—C2A	120.4 (3)	H2BA—C2B—H2BB	111.4
C11A—C1A—C8A	114.6 (3)	C3B—C2B—C1B	86.6 (2)
C1A—C2A—H2AA	114.3	C3B—C2B—H2BA	114.2
C1A—C2A—H2AB	114.3	C3B—C2B—H2BB	114.2
H2AA—C2A—H2AB	111.4	C4B—C3B—C2B	145.2 (3)
C3A—C2A—C1A	86.3 (2)	C8B—C3B—C2B	93.5 (3)
C3A—C2A—H2AA	114.3	C8B—C3B—C4B	121.2 (3)
C3A—C2A—H2AB	114.3	C3B—C4B—H4B	121.6
C4A—C3A—C2A	144.4 (3)	C5B—C4B—C3B	116.8 (3)
C8A—C3A—C2A	93.3 (3)	C5B—C4B—H4B	121.6
C8A—C3A—C4A	122.3 (3)	O1B—C5B—C4B	124.6 (3)
C3A—C4A—H4A	121.9	O1B—C5B—C6B	114.2 (3)
C3A—C4A—C5A	116.2 (3)	C4B—C5B—C6B	121.3 (3)
C5A—C4A—H4A	121.9	O2B—C6B—C5B	114.7 (3)
O1A—C5A—C4A	125.0 (3)	O2B—C6B—C7B	124.0 (3)
O1A—C5A—C6A	114.2 (3)	C7B—C6B—C5B	121.2 (3)
C4A—C5A—C6A	120.8 (3)	C6B—C7B—H7B	122.0
O2A—C6A—C5A	114.4 (3)	C8B—C7B—C6B	115.9 (3)
C7A—C6A—O2A	123.7 (3)	C8B—C7B—H7B	122.0
C7A—C6A—C5A	121.9 (3)	C3B—C8B—C1B	94.5 (3)
C6A—C7A—H7A	122.0	C3B—C8B—C7B	123.5 (3)
C6A—C7A—C8A	116.0 (3)	C7B—C8B—C1B	142.0 (3)
C8A—C7A—H7A	122.0	O1B—C9B—H9BA	109.5
C3A—C8A—C1A	94.6 (3)	O1B—C9B—H9BB	109.5
C3A—C8A—C7A	122.8 (3)	O1B—C9B—H9BC	109.5
C7A—C8A—C1A	142.6 (3)	H9BA—C9B—H9BB	109.5
O1A—C9A—H9AA	109.5	H9BA—C9B—H9BC	109.5
O1A—C9A—H9AB	109.5	H9BB—C9B—H9BC	109.5
O1A—C9A—H9AC	109.5	O2B—C10B—H10D	109.5
H9AA—C9A—H9AB	109.5	O2B—C10B—H10E	109.5
H9AA—C9A—H9AC	109.5	O2B—C10B—H10F	109.5
H9AB—C9A—H9AC	109.5	H10D—C10B—H10E	109.5
O2A—C10A—H10A	109.5	H10D—C10B—H10F	109.5
O2A—C10A—H10B	109.5	H10E—C10B—H10F	109.5
O2A—C10A—H10C	109.5	N1B—C11B—H11C	108.2
H10A—C10A—H10B	109.5	N1B—C11B—H11D	108.2
H10A—C10A—H10C	109.5	C1B—C11B—N1B	116.3 (3)
H10B—C10A—H10C	109.5	C1B—C11B—H11C	108.2
N1A—C11A—C1A	114.7 (3)	C1B—C11B—H11D	108.2
N1A—C11A—H11A	108.6	H11C—C11B—H11D	107.4
N1A—C11A—H11B	108.6	N1B—C12B—H12D	109.5
C1A—C11A—H11A	108.6	N1B—C12B—H12E	109.5
C1A—C11A—H11B	108.6	N1B—C12B—H12F	109.5
H11A—C11A—H11B	107.6	H12D—C12B—H12E	109.5
N1A—C12A—H12A	109.5	H12D—C12B—H12F	109.5
N1A—C12A—H12B	109.5	H12E—C12B—H12F	109.5
N1A—C12A—H12C	109.5	N1B—C13B—H13C	109.2
H12A—C12A—H12B	109.5	N1B—C13B—H13D	109.2
H12A—C12A—H12C	109.5	N1B—C13B—C14B	112.1 (3)
H12B—C12A—H12C	109.5	H13C—C13B—H13D	107.9
N1A—C13A—H13A	109.0	C14B—C13B—H13C	109.2
N1A—C13A—H13B	109.0	C14B—C13B—H13D	109.2
N1A—C13A—C14A	113.0 (3)	C13B—C14B—H14C	109.3
H13A—C13A—H13B	107.8	C13B—C14B—H14D	109.3
C14A—C13A—H13A	109.0	C13B—C14B—C15B	111.5 (3)
C14A—C13A—H13B	109.0	H14C—C14B—H14D	108.0
C13A—C14A—H14A	109.3	C15B—C14B—H14C	109.3
C13A—C14A—H14B	109.3	C15B—C14B—H14D	109.3
C13A—C14A—C15A	111.7 (3)	N2B—C15B—C14B	113.1 (3)
H14A—C14A—H14B	107.9	N2B—C15B—H15C	109.0
C15A—C14A—H14A	109.3	N2B—C15B—H15D	109.0
C15A—C14A—H14B	109.3	C14B—C15B—H15C	109.0
N2A—C15A—C14A	113.6 (3)	C14B—C15B—H15D	109.0
N2A—C15A—H15A	108.8	H15C—C15B—H15D	107.8
N2A—C15A—H15B	108.8	O3B—C16B—N2B	123.4 (4)
C14A—C15A—H15A	108.8	O3B—C16B—C17B	119.8 (4)
C14A—C15A—H15B	108.8	N2B—C16B—C17B	116.8 (4)
H15A—C15A—H15B	107.7	C16B—C17B—H17C	109.4
O3A—C16A—N2A	122.9 (3)	C16B—C17B—H17D	109.4
O3A—C16A—C17A	119.7 (3)	C16B—C17B—C18B	111.0 (3)
N2A—C16A—C17A	117.3 (3)	H17C—C17B—H17D	108.0
C16A—C17A—H17A	109.0	C18B—C17B—H17C	109.4
C16A—C17A—H17B	109.0	C18B—C17B—H17D	109.4
C16A—C17A—C18A	112.7 (3)	C19B—C18B—C17B	117.8 (3)
H17A—C17A—H17B	107.8	C23B—C18B—C17B	122.3 (3)
C18A—C17A—H17A	109.0	C23B—C18B—C19B	119.8 (3)
C18A—C17A—H17B	109.0	C18B—C19B—H19B	119.3
C19A—C18A—C17A	117.9 (3)	C20B—C19B—C18B	121.4 (3)
C23A—C18A—C17A	123.0 (3)	C20B—C19B—H19B	119.3
C23A—C18A—C19A	119.0 (3)	O4B—C20B—C19B	125.7 (4)
C18A—C19A—H19A	118.9	O4B—C20B—C21B	114.9 (3)
C20A—C19A—C18A	122.2 (3)	C19B—C20B—C21B	119.4 (3)
C20A—C19A—H19A	118.9	O5B—C21B—C20B	116.2 (3)
O4A—C20A—C21A	115.4 (3)	O5B—C21B—C22B	124.6 (3)
C19A—C20A—O4A	125.8 (3)	C22B—C21B—C20B	119.2 (4)
C19A—C20A—C21A	118.8 (3)	C21B—C22B—H22B	118.9
O5A—C21A—C20A	115.8 (3)	C21B—C22B—C23B	122.3 (3)
C22A—C21A—O5A	124.6 (3)	C23B—C22B—H22B	118.9
C22A—C21A—C20A	119.6 (3)	C18B—C23B—C22B	118.0 (3)
C21A—C22A—H22A	118.9	C18B—C23B—C24B	126.2 (3)
C21A—C22A—C23A	122.2 (3)	C22B—C23B—C24B	115.8 (3)
C23A—C22A—H22A	118.9	C23B—C24B—H24C	107.9
C18A—C23A—C22A	118.2 (3)	C23B—C24B—H24D	107.9
C18A—C23A—C24A	125.8 (3)	C23B—C24B—C25B	117.7 (3)
C22A—C23A—C24A	115.9 (3)	H24C—C24B—H24D	107.2
C23A—C24A—H24A	107.7	C25B—C24B—H24C	107.9
C23A—C24A—H24B	107.7	C25B—C24B—H24D	107.9
C23A—C24A—C25A	118.4 (3)	N2B—C25B—C24B	113.6 (3)
H24A—C24A—H24B	107.1	N2B—C25B—H25C	108.9
C25A—C24A—H24A	107.7	N2B—C25B—H25D	108.9
C25A—C24A—H24B	107.7	C24B—C25B—H25C	108.9
N2A—C25A—C24A	112.9 (3)	C24B—C25B—H25D	108.9
N2A—C25A—H25A	109.0	H25C—C25B—H25D	107.7
N2A—C25A—H25B	109.0	O4B—C26B—H26D	109.5
C24A—C25A—H25A	109.0	O4B—C26B—H26E	109.5
C24A—C25A—H25B	109.0	O4B—C26B—H26F	109.5
H25A—C25A—H25B	107.8	H26D—C26B—H26E	109.5
O4A—C26A—H26A	109.5	H26D—C26B—H26F	109.5
O4A—C26A—H26B	109.5	H26E—C26B—H26F	109.5
O4A—C26A—H26C	109.5	O5B—C27B—H27D	109.5
H26A—C26A—H26B	109.5	O5B—C27B—H27E	109.5
H26A—C26A—H26C	109.5	O5B—C27B—H27F	109.5
H26B—C26A—H26C	109.5	H27D—C27B—H27E	109.5
O5A—C27A—H27A	109.5	H27D—C27B—H27F	109.5
O5A—C27A—H27B	109.5	H27E—C27B—H27F	109.5
O5A—C27A—H27C	109.5	H21A—O21—H21B	111.2
H27A—C27A—H27B	109.5	H22C—O22—H22D	107.1
H27A—C27A—H27C	109.5	H23A—O23—H23B	97.9
H27B—C27A—H27C	109.5	H24E—O24—H24F	113.6
O1A—C5A—C6A—O2A	0.3 (5)	O1B—C5B—C6B—O2B	3.2 (5)
O1A—C5A—C6A—C7A	−178.0 (3)	O1B—C5B—C6B—C7B	−178.8 (3)
O2A—C6A—C7A—C8A	−179.4 (3)	O2B—C6B—C7B—C8B	177.9 (3)
O3A—C16A—C17A—C18A	106.7 (4)	O3B—C16B—C17B—C18B	−105.1 (4)
O4A—C20A—C21A—O5A	−0.7 (5)	O4B—C20B—C21B—O5B	1.8 (5)
O4A—C20A—C21A—C22A	178.0 (3)	O4B—C20B—C21B—C22B	−178.3 (3)
O5A—C21A—C22A—C23A	179.7 (3)	O5B—C21B—C22B—C23B	179.1 (3)
N1A—C13A—C14A—C15A	−168.8 (3)	N1B—C13B—C14B—C15B	168.0 (3)
N2A—C16A—C17A—C18A	−70.2 (4)	N2B—C16B—C17B—C18B	72.4 (4)
C1A—C2A—C3A—C4A	178.1 (5)	C1B—C2B—C3B—C4B	177.3 (5)
C1A—C2A—C3A—C8A	−3.1 (3)	C1B—C2B—C3B—C8B	−1.1 (3)
C2A—C1A—C8A—C3A	−3.1 (3)	C2B—C1B—C8B—C3B	−1.1 (3)
C2A—C1A—C8A—C7A	177.0 (5)	C2B—C1B—C8B—C7B	178.8 (5)
C2A—C1A—C11A—N1A	90.0 (4)	C2B—C1B—C11B—N1B	91.8 (4)
C2A—C3A—C4A—C5A	177.0 (4)	C2B—C3B—C4B—C5B	−179.2 (5)
C2A—C3A—C8A—C1A	3.2 (3)	C2B—C3B—C8B—C1B	1.2 (3)
C2A—C3A—C8A—C7A	−176.9 (4)	C2B—C3B—C8B—C7B	−178.7 (3)
C3A—C4A—C5A—O1A	179.5 (3)	C3B—C4B—C5B—O1B	179.3 (3)
C3A—C4A—C5A—C6A	−0.3 (5)	C3B—C4B—C5B—C6B	−0.6 (5)
C4A—C3A—C8A—C1A	−177.6 (3)	C4B—C3B—C8B—C1B	−177.8 (3)
C4A—C3A—C8A—C7A	2.3 (5)	C4B—C3B—C8B—C7B	2.3 (5)
C4A—C5A—C6A—O2A	−179.9 (3)	C4B—C5B—C6B—O2B	−177.0 (4)
C4A—C5A—C6A—C7A	1.9 (6)	C4B—C5B—C6B—C7B	1.1 (6)
C5A—C6A—C7A—C8A	−1.3 (5)	C5B—C6B—C7B—C8B	0.0 (5)
C6A—C7A—C8A—C1A	179.1 (4)	C6B—C7B—C8B—C1B	178.5 (4)
C6A—C7A—C8A—C3A	−0.7 (5)	C6B—C7B—C8B—C3B	−1.7 (5)
C8A—C1A—C2A—C3A	2.7 (2)	C8B—C1B—C2B—C3B	1.0 (2)
C8A—C1A—C11A—N1A	−170.1 (3)	C8B—C1B—C11B—N1B	−170.3 (3)
C8A—C3A—C4A—C5A	−1.7 (5)	C8B—C3B—C4B—C5B	−1.1 (5)
C9A—O1A—C5A—C4A	−1.6 (5)	C9B—O1B—C5B—C4B	−5.3 (6)
C9A—O1A—C5A—C6A	178.3 (3)	C9B—O1B—C5B—C6B	174.5 (4)
C10A—O2A—C6A—C5A	173.8 (3)	C10B—O2B—C6B—C5B	176.3 (4)
C10A—O2A—C6A—C7A	−8.0 (5)	C10B—O2B—C6B—C7B	−1.8 (6)
C11A—N1A—C13A—C14A	172.4 (3)	C11B—N1B—C13B—C14B	−158.1 (3)
C11A—C1A—C2A—C3A	118.8 (3)	C11B—C1B—C2B—C3B	115.3 (3)
C11A—C1A—C8A—C3A	−124.6 (3)	C11B—C1B—C8B—C3B	−120.7 (3)
C11A—C1A—C8A—C7A	55.5 (6)	C11B—C1B—C8B—C7B	59.2 (6)
C12A—N1A—C11A—C1A	170.9 (3)	C12B—N1B—C11B—C1B	73.8 (4)
C12A—N1A—C13A—C14A	−61.4 (4)	C12B—N1B—C13B—C14B	73.1 (4)
C13A—N1A—C11A—C1A	−61.5 (4)	C13B—N1B—C11B—C1B	−55.4 (4)
C13A—C14A—C15A—N2A	61.3 (4)	C13B—C14B—C15B—N2B	−54.8 (4)
C15A—N2A—C16A—O3A	3.7 (5)	C15B—N2B—C16B—O3B	0.5 (5)
C15A—N2A—C16A—C17A	−179.5 (3)	C15B—N2B—C16B—C17B	−176.9 (3)
C15A—N2A—C25A—C24A	−107.3 (3)	C15B—N2B—C25B—C24B	103.8 (3)
C16A—N2A—C15A—C14A	−108.2 (4)	C16B—N2B—C15B—C14B	103.6 (4)
C16A—N2A—C25A—C24A	73.8 (4)	C16B—N2B—C25B—C24B	−73.4 (4)
C16A—C17A—C18A—C19A	−122.5 (3)	C16B—C17B—C18B—C19B	120.9 (4)
C16A—C17A—C18A—C23A	53.9 (4)	C16B—C17B—C18B—C23B	−56.4 (5)
C17A—C18A—C19A—C20A	175.8 (3)	C17B—C18B—C19B—C20B	−176.5 (3)
C17A—C18A—C23A—C22A	−175.6 (3)	C17B—C18B—C23B—C22B	175.9 (3)
C17A—C18A—C23A—C24A	3.1 (5)	C17B—C18B—C23B—C24B	−4.3 (5)
C18A—C19A—C20A—O4A	−178.0 (3)	C18B—C19B—C20B—O4B	178.1 (3)
C18A—C19A—C20A—C21A	1.0 (5)	C18B—C19B—C20B—C21B	−0.3 (6)
C18A—C23A—C24A—C25A	−1.7 (5)	C18B—C23B—C24B—C25B	6.4 (5)
C19A—C18A—C23A—C22A	0.8 (5)	C19B—C18B—C23B—C22B	−1.3 (5)
C19A—C18A—C23A—C24A	179.5 (3)	C19B—C18B—C23B—C24B	178.5 (3)
C19A—C20A—C21A—O5A	−179.8 (3)	C19B—C20B—C21B—O5B	−179.7 (3)
C19A—C20A—C21A—C22A	−1.1 (5)	C19B—C20B—C21B—C22B	0.3 (5)
C20A—C21A—C22A—C23A	1.1 (5)	C20B—C21B—C22B—C23B	−0.9 (5)
C21A—C22A—C23A—C18A	−1.0 (5)	C21B—C22B—C23B—C18B	1.3 (5)
C21A—C22A—C23A—C24A	−179.8 (3)	C21B—C22B—C23B—C24B	−178.5 (3)
C22A—C23A—C24A—C25A	177.0 (3)	C22B—C23B—C24B—C25B	−173.7 (3)
C23A—C18A—C19A—C20A	−0.8 (5)	C23B—C18B—C19B—C20B	0.8 (5)
C23A—C24A—C25A—N2A	−57.2 (4)	C23B—C24B—C25B—N2B	53.0 (4)
C25A—N2A—C15A—C14A	72.9 (4)	C25B—N2B—C15B—C14B	−73.6 (4)
C25A—N2A—C16A—O3A	−177.5 (3)	C25B—N2B—C16B—O3B	177.7 (3)
C25A—N2A—C16A—C17A	−0.7 (4)	C25B—N2B—C16B—C17B	0.3 (5)
C26A—O4A—C20A—C19A	11.6 (5)	C26B—O4B—C20B—C19B	−3.7 (5)
C26A—O4A—C20A—C21A	−167.5 (3)	C26B—O4B—C20B—C21B	174.7 (3)
C27A—O5A—C21A—C20A	167.2 (3)	C27B—O5B—C21B—C20B	−166.0 (4)
C27A—O5A—C21A—C22A	−11.5 (5)	C27B—O5B—C21B—C22B	14.1 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···Cl1	0.98	2.10	3.070 (3)	172
O11—H11E···O3A^i	0.82	1.88	2.685 (4)	166
O11—H11F···O13	0.82	1.89	2.702 (4)	171
O12—H12G···O11	0.82	1.99	2.774 (4)	158
O12—H12H···Cl2	0.83	2.40	3.209 (3)	168
O13—H13E···O14^i	0.82	1.92	2.715 (4)	163
O14—H14E···O11	0.82	1.97	2.777 (4)	169
O14—H14F···Cl2	0.82	2.38	3.137 (3)	154
N1B—H1B···Cl2	0.98	2.07	3.018 (3)	162
O21—H21A···Cl1	0.83	2.41	3.208 (3)	163
O21—H21B···O23^ii	0.82	1.98	2.795 (4)	176
O22—H22C···O21	0.82	1.98	2.745 (4)	154
O22—H22D···O24	0.82	1.93	2.738 (4)	170
O23—H23A···O22	0.82	1.90	2.701 (4)	167
O23—H23B···O3B^iii	0.82	1.90	2.706 (4)	166
O24—H24E···Cl1^iii	0.82	2.40	3.172 (4)	158
O24—H24F···O23^iv	0.82	2.09	2.801 (5)	145

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) x+1/2, −y+1/2, −z+1; (iii) x−1, y, z; (iv) x−1/2, −y+1/2, −z+1.