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.
Supporting information
CCDC references: 1908842; 1908841
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-1
H-3-benzazepin-3-yl)propyl]methylazanium hemihydrate (1123_iva)
top
Crystal data top
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) Å3 | Chunk, colorless |
Z = 2 | 0.38 × 0.22 × 0.19 mm |
Data collection top
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 top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0475P)2 + 0.3577P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6A···Cl1Bi | 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-1
H-3-benzazepin-3-yl)propyl]{[3,4-dimethoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-yl]methyl}methylazanium
tetrahydrate (i-518)
top
Crystal data top
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) Å3 | Needle, colourless |
Z = 8 | 0.3 × 0.12 × 0.1 mm |
F(000) = 2480 | |
Data collection top
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 top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0468P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O3Ai | 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···O14i | 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···O23ii | 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···O3Biii | 0.82 | 1.90 | 2.706 (4) | 166 |
O24—H24E···Cl1iii | 0.82 | 2.40 | 3.172 (4) | 158 |
O24—H24F···O23iv | 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. |
Thermophysical data for the hemihydrate and tetrahydrate topSolid form | Hemihydrate | Tetrahydrate |
Desolvation onset temperature (°C) | 152.6 | 59.3 |
Desolvation enthalpy change ΔHS,exp (J g-1) | 60.2 | 318.5 |
Calcd weight loss (ΔmS%) | 1.8 | 12.5 |
Obsd weight loss in TGA (ΔmS%) | 1.7 | 12.5 |
Calculated binding energy (kJ mol-1) | 63.7 | 45.8 |
Heat of vaporization of the pure solvate ΔHPS (kJ mol-1) | 40.7 | 40.7 |
Boiling point of pure solvent (°C) | 100 | 100 |