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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619004819/qf3025sup1.cif
Contains datablocks 1123_iva, i-518, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619004819/qf30251123_ivasup2.hkl
Contains datablock 1123_iva

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619004819/qf3025i-518sup3.hkl
Contains datablock i-518

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619004819/qf3025sup4.pdf
Morphology predictions and fully labelled ellipsoid plots

CCDC references: 1908842; 1908841

Computing details top

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) top
Crystal data top
2C27H37N2O5+·2Cl·H2OF(000) = 1100
Mr = 1028.08Dx = 1.258 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
a = 5.4874 (1) ÅCell parameters from 13189 reflections
b = 43.4767 (7) Åθ = 67.5–3.0°
c = 11.4892 (2) ŵ = 1.58 mm1
β = 98.144 (2)°T = 296 K
V = 2713.38 (8) Å3Chunk, colorless
Z = 20.38 × 0.22 × 0.19 mm
Data collection top
Oxford Diffraction Xcalibur Atlas Gemini ultra
diffractometer
9744 independent reflections
Radiation source: fine-focus sealed tube8864 reflections with I > 2σ(I)
Detector resolution: 10.3592 pixels mm-1Rint = 0.035
ω scansθmax = 67.6°, θmin = 3.9°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 56
Tmin = 0.545, Tmax = 0.744k = 5151
30111 measured reflectionsl = 1313
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH-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 = 1.04Δρmax = 0.28 e Å3
9744 reflectionsΔρmin = 0.17 e Å3
650 parametersAbsolute structure: Flack x determined using 3869 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute 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
xyzUiso*/Ueq
Cl1A0.06631 (16)0.71114 (3)0.61783 (8)0.0634 (2)
Cl1B0.33759 (18)0.77834 (3)0.11157 (8)0.0663 (3)
O1A0.7874 (6)0.54551 (6)0.8390 (3)0.0713 (8)
O2A1.0237 (5)0.57884 (6)0.7110 (3)0.0699 (8)
O3A0.4428 (5)0.82055 (6)0.5716 (2)0.0619 (7)
O4A0.6928 (5)0.96952 (6)0.5521 (3)0.0681 (7)
O5A1.0510 (5)0.96837 (6)0.7267 (2)0.0588 (6)
O1B0.1002 (6)0.97049 (6)0.2456 (3)0.0734 (8)
O2B0.3470 (6)0.93905 (6)0.1156 (3)0.0702 (8)
O3B0.0848 (6)0.68306 (6)0.1384 (2)0.0651 (7)
O4B0.3930 (5)0.53529 (6)0.1536 (3)0.0709 (8)
O5B0.7572 (5)0.53932 (6)0.3228 (3)0.0611 (7)
O60.1418 (7)0.81133 (11)0.0228 (3)0.1031 (12)
H6A0.2844550.8133550.0543910.155*
H6B0.0127350.8073550.0481110.155*
N1A0.3583 (5)0.71549 (6)0.8201 (2)0.0415 (5)
H1A0.2289000.7198190.7541960.050*
N1B0.0225 (5)0.79109 (6)0.3388 (2)0.0416 (6)
H1B0.0956230.7858060.2694890.050*
N2A0.5582 (5)0.82578 (6)0.7663 (2)0.0442 (6)
N2B0.2646 (6)0.68159 (6)0.3273 (3)0.0539 (7)
C1A0.6165 (6)0.66897 (7)0.9012 (3)0.0451 (7)
H1AA0.7405570.6829240.9419160.054*
C2A0.4866 (7)0.64836 (8)0.9876 (3)0.0518 (8)
H2AA0.5441590.6519261.0702720.062*
H2AB0.3082300.6484310.9715450.062*
C3A0.6077 (6)0.62108 (8)0.9351 (3)0.0479 (7)
C4A0.6211 (7)0.58929 (8)0.9340 (3)0.0552 (9)
H4A0.5408410.5771670.9834140.066*
C5A0.7618 (7)0.57651 (8)0.8544 (4)0.0537 (8)
C6A0.8870 (6)0.59502 (8)0.7819 (3)0.0513 (8)
C7A0.8685 (6)0.62681 (8)0.7834 (3)0.0507 (8)
H7A0.9476940.6392190.7344900.061*
C8A0.7247 (6)0.63904 (8)0.8621 (3)0.0467 (7)
C9A0.6216 (10)0.52578 (10)0.8877 (6)0.0863 (15)
H9AA0.6492910.5273970.9718820.129*
H9AB0.6480960.5049210.8651070.129*
H9AC0.4553200.5316910.8590410.129*
C10A1.1917 (8)0.59546 (11)0.6539 (4)0.0687 (11)
H10A1.1034880.6091970.5975390.103*
H10B1.2873430.5814270.6143040.103*
H10C1.2991450.6070970.7107640.103*
C11A0.4549 (6)0.68395 (7)0.7984 (3)0.0457 (7)
H11A0.5485430.6852560.7329810.055*
H11B0.3155500.6705390.7744330.055*
C12A0.2398 (7)0.71743 (9)0.9286 (3)0.0546 (8)
H12A0.1226010.7010440.9288440.082*
H12B0.1570250.7368440.9304560.082*
H12C0.3631300.7156640.9963500.082*
C13A0.5495 (6)0.73994 (7)0.8174 (3)0.0451 (7)
H13A0.6501400.7348780.7571190.054*
H13B0.6559020.7401960.8923890.054*
C14A0.4417 (6)0.77147 (7)0.7933 (3)0.0436 (7)
H14A0.3598780.7780210.8586220.052*
H14B0.3206940.7709900.7230470.052*
C15A0.6458 (6)0.79396 (7)0.7766 (3)0.0453 (7)
H15A0.7758020.7923580.8430020.054*
H15B0.7148180.7884480.7062850.054*
C16A0.4614 (6)0.83649 (7)0.6612 (3)0.0446 (7)
C17A0.3699 (6)0.86941 (8)0.6562 (3)0.0507 (8)
H17A0.2513030.8714490.7107860.061*
H17B0.2830510.8731680.5779210.061*
C18A0.5631 (6)0.89439 (7)0.6840 (3)0.0412 (7)
C19A0.5444 (6)0.91978 (8)0.6073 (3)0.0491 (8)
H19A0.4196710.9200920.5434130.059*
C20A0.7051 (6)0.94411 (8)0.6241 (3)0.0479 (7)
C21A0.8982 (6)0.94349 (7)0.7176 (3)0.0454 (7)
C22A0.9158 (6)0.91884 (7)0.7935 (3)0.0431 (7)
H22A1.0419070.9186250.8567900.052*
C23A0.7502 (6)0.89394 (7)0.7791 (3)0.0389 (6)
C24A0.7929 (6)0.86848 (7)0.8698 (3)0.0449 (7)
H24A0.9411480.8575250.8575660.054*
H24B0.8242050.8779170.9469950.054*
C25A0.5887 (6)0.84513 (7)0.8712 (3)0.0453 (7)
H25A0.6254110.8322200.9403370.054*
H25B0.4355290.8558210.8765010.054*
C26A0.4705 (10)0.97889 (16)0.4987 (7)0.122 (3)
H26A0.4211140.9664220.4304360.183*
H26B0.4802271.0000150.4753950.183*
H26C0.3518560.9769170.5521170.183*
C27A1.2529 (7)0.96835 (9)0.8181 (4)0.0610 (9)
H27A1.1935710.9674790.8926740.091*
H27B1.3474300.9867880.8137110.091*
H27C1.3548370.9507610.8097650.091*
C1B0.0749 (6)0.84631 (8)0.2808 (3)0.0504 (8)
H1BA0.1992380.8384660.2182170.060*
C2B0.1962 (7)0.86542 (8)0.3749 (4)0.0558 (9)
H2BA0.3747440.8652690.3627420.067*
H2BB0.1308700.8607570.4559340.067*
C3B0.0824 (7)0.89355 (8)0.3255 (3)0.0520 (8)
C4B0.0674 (7)0.92527 (8)0.3312 (4)0.0570 (9)
H4B0.1471750.9365770.3832200.068*
C5B0.0731 (7)0.93928 (8)0.2551 (3)0.0555 (8)
C6B0.2039 (7)0.92169 (8)0.1807 (3)0.0525 (8)
C7B0.1805 (7)0.89027 (9)0.1737 (3)0.0532 (8)
H7B0.2603400.8786080.1227360.064*
C8B0.0310 (6)0.87701 (8)0.2470 (3)0.0485 (8)
C9B0.0676 (10)0.98942 (10)0.2963 (5)0.0809 (13)
H9BA0.2329460.9827960.2696540.121*
H9BB0.0482381.0103990.2731550.121*
H9BC0.0349210.9878780.3804300.121*
C10B0.5159 (8)0.92311 (11)0.0570 (4)0.0705 (11)
H10D0.6170850.9102010.1118860.106*
H10E0.6178390.9375780.0231390.106*
H10F0.4283280.9106510.0040860.106*
C11B0.1210 (6)0.82255 (7)0.3189 (3)0.0455 (7)
H11C0.2293310.8211590.2593410.055*
H11D0.2188270.8294770.3911270.055*
C12B0.1105 (6)0.79002 (8)0.4425 (3)0.0527 (8)
H12D0.1640020.7693480.4539060.079*
H12E0.2510150.8033860.4297270.079*
H12F0.0026070.7966240.5111050.079*
C13B0.2266 (6)0.76792 (7)0.3480 (3)0.0476 (8)
H13C0.3309940.7704670.4229210.057*
H13D0.3263260.7716980.2862220.057*
C14B0.1323 (7)0.73538 (8)0.3382 (3)0.0512 (8)
H14C0.0042410.7336030.2710760.061*
H14D0.0620930.7299890.4083090.061*
C15B0.3438 (7)0.71339 (8)0.3234 (4)0.0577 (9)
H15C0.4013880.7173680.2488420.069*
H15D0.4797130.7169920.3856700.069*
C16B0.1363 (6)0.66877 (8)0.2308 (3)0.0478 (8)
C17B0.0556 (7)0.63583 (8)0.2399 (4)0.0573 (9)
H17C0.0384660.6300400.1652400.069*
H17D0.0548380.6348300.2986730.069*
C18B0.2565 (6)0.61206 (7)0.2711 (3)0.0453 (7)
C19B0.2375 (7)0.58551 (8)0.2004 (3)0.0522 (8)
H19B0.1080780.5840020.1389480.063*
C20B0.4031 (6)0.56177 (8)0.2189 (3)0.0490 (8)
C21B0.5999 (6)0.56404 (7)0.3103 (3)0.0467 (7)
C22B0.6197 (6)0.58972 (7)0.3803 (3)0.0466 (7)
H22B0.7494730.5909750.4416760.056*
C23B0.4509 (6)0.61426 (7)0.3628 (3)0.0440 (7)
C24B0.5004 (7)0.64116 (8)0.4456 (3)0.0512 (8)
H24C0.6511020.6510390.4302690.061*
H24D0.5295280.6332360.5252690.061*
C25B0.3011 (8)0.66548 (9)0.4397 (3)0.0576 (9)
H25C0.1476960.6558160.4523260.069*
H25D0.3451660.6802690.5023590.069*
C26B0.1662 (10)0.52758 (13)0.0870 (6)0.0916 (16)
H26D0.0383660.5287210.1359440.137*
H26E0.1744280.5070430.0571110.137*
H26F0.1308020.5417000.0226340.137*
C27B0.9554 (8)0.54023 (9)0.4151 (4)0.0632 (10)
H27D1.0607430.5572550.4035290.095*
H27E1.0471820.5214140.4161210.095*
H27F0.8933040.5426430.4886040.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0554 (5)0.0906 (7)0.0457 (4)0.0072 (5)0.0127 (3)0.0021 (5)
Cl1B0.0656 (5)0.0776 (6)0.0509 (5)0.0074 (5)0.0087 (4)0.0018 (4)
O1A0.0868 (19)0.0395 (14)0.093 (2)0.0034 (12)0.0313 (16)0.0024 (13)
O2A0.0726 (17)0.0581 (16)0.086 (2)0.0078 (13)0.0367 (15)0.0194 (14)
O3A0.0849 (18)0.0532 (15)0.0439 (13)0.0062 (13)0.0035 (12)0.0064 (11)
O4A0.0705 (16)0.0526 (15)0.0778 (18)0.0026 (12)0.0007 (13)0.0313 (14)
O5A0.0625 (14)0.0408 (13)0.0699 (16)0.0140 (11)0.0017 (12)0.0130 (12)
O1B0.102 (2)0.0376 (14)0.087 (2)0.0021 (13)0.0355 (17)0.0028 (13)
O2B0.0855 (18)0.0573 (16)0.0739 (19)0.0062 (14)0.0322 (15)0.0146 (14)
O3B0.0894 (19)0.0554 (16)0.0517 (15)0.0149 (13)0.0135 (13)0.0076 (12)
O4B0.0740 (17)0.0508 (15)0.083 (2)0.0069 (13)0.0076 (14)0.0224 (14)
O5B0.0636 (15)0.0398 (13)0.0764 (18)0.0161 (11)0.0023 (13)0.0075 (12)
O60.084 (2)0.140 (3)0.088 (2)0.023 (2)0.0230 (18)0.024 (2)
N1A0.0444 (13)0.0325 (13)0.0478 (14)0.0032 (10)0.0076 (11)0.0012 (11)
N1B0.0426 (13)0.0379 (13)0.0427 (14)0.0010 (10)0.0003 (11)0.0021 (11)
N2A0.0593 (16)0.0319 (13)0.0406 (14)0.0074 (11)0.0047 (12)0.0004 (11)
N2B0.0737 (19)0.0375 (15)0.0517 (17)0.0113 (13)0.0135 (14)0.0058 (12)
C1A0.0430 (16)0.0367 (16)0.0545 (19)0.0028 (12)0.0036 (13)0.0042 (14)
C2A0.0561 (19)0.0450 (18)0.055 (2)0.0075 (14)0.0102 (16)0.0016 (15)
C3A0.0508 (18)0.0444 (18)0.0483 (19)0.0030 (14)0.0067 (14)0.0038 (15)
C4A0.066 (2)0.0436 (19)0.058 (2)0.0048 (16)0.0168 (17)0.0090 (16)
C5A0.060 (2)0.0395 (18)0.062 (2)0.0038 (15)0.0095 (17)0.0013 (16)
C6A0.0472 (18)0.051 (2)0.057 (2)0.0037 (14)0.0098 (15)0.0097 (16)
C7A0.0444 (17)0.0494 (19)0.059 (2)0.0094 (14)0.0101 (15)0.0023 (16)
C8A0.0427 (16)0.0409 (17)0.056 (2)0.0013 (13)0.0053 (14)0.0019 (15)
C9A0.099 (4)0.044 (2)0.122 (4)0.005 (2)0.033 (3)0.003 (2)
C10A0.058 (2)0.085 (3)0.067 (3)0.009 (2)0.0200 (18)0.013 (2)
C11A0.0524 (18)0.0324 (15)0.0513 (19)0.0047 (13)0.0043 (14)0.0021 (13)
C12A0.0539 (18)0.053 (2)0.062 (2)0.0019 (15)0.0239 (16)0.0081 (17)
C13A0.0461 (17)0.0366 (16)0.055 (2)0.0056 (12)0.0142 (14)0.0004 (14)
C14A0.0490 (17)0.0369 (16)0.0454 (17)0.0029 (13)0.0088 (13)0.0005 (13)
C15A0.0528 (18)0.0351 (16)0.0478 (18)0.0046 (13)0.0065 (14)0.0003 (14)
C16A0.0478 (17)0.0397 (17)0.0443 (18)0.0105 (13)0.0002 (13)0.0016 (14)
C17A0.0456 (17)0.0455 (19)0.057 (2)0.0042 (14)0.0055 (15)0.0054 (15)
C18A0.0438 (16)0.0319 (15)0.0469 (17)0.0006 (12)0.0034 (13)0.0006 (13)
C19A0.0494 (17)0.0431 (18)0.0513 (19)0.0024 (14)0.0047 (14)0.0056 (15)
C20A0.0570 (19)0.0372 (17)0.0498 (19)0.0018 (14)0.0085 (15)0.0091 (14)
C21A0.0475 (17)0.0343 (16)0.0542 (19)0.0034 (13)0.0064 (14)0.0018 (14)
C22A0.0452 (16)0.0354 (16)0.0472 (17)0.0051 (12)0.0014 (13)0.0032 (13)
C23A0.0442 (15)0.0315 (15)0.0413 (16)0.0009 (12)0.0070 (12)0.0004 (12)
C24A0.0534 (18)0.0380 (16)0.0422 (17)0.0056 (13)0.0031 (14)0.0018 (13)
C25A0.0583 (19)0.0395 (17)0.0392 (17)0.0062 (14)0.0106 (14)0.0002 (13)
C26A0.082 (3)0.115 (5)0.171 (7)0.028 (3)0.023 (4)0.098 (5)
C27A0.061 (2)0.0463 (19)0.072 (2)0.0138 (16)0.0023 (18)0.0035 (18)
C1B0.0547 (19)0.0398 (17)0.053 (2)0.0016 (14)0.0055 (15)0.0024 (14)
C2B0.055 (2)0.0447 (19)0.068 (2)0.0021 (15)0.0097 (17)0.0042 (17)
C3B0.0576 (19)0.0445 (19)0.053 (2)0.0002 (15)0.0058 (15)0.0034 (15)
C4B0.070 (2)0.0424 (19)0.062 (2)0.0007 (16)0.0215 (18)0.0017 (16)
C5B0.067 (2)0.044 (2)0.056 (2)0.0006 (16)0.0109 (17)0.0007 (16)
C6B0.060 (2)0.050 (2)0.0478 (19)0.0021 (15)0.0086 (15)0.0065 (15)
C7B0.066 (2)0.052 (2)0.0418 (18)0.0102 (16)0.0073 (15)0.0038 (15)
C8B0.0581 (19)0.0407 (17)0.0443 (18)0.0030 (14)0.0011 (14)0.0006 (14)
C9B0.101 (3)0.043 (2)0.104 (4)0.008 (2)0.032 (3)0.006 (2)
C10B0.065 (2)0.085 (3)0.063 (2)0.009 (2)0.0135 (19)0.014 (2)
C11B0.0527 (18)0.0382 (17)0.0442 (17)0.0066 (13)0.0021 (14)0.0003 (13)
C12B0.0520 (18)0.0480 (19)0.060 (2)0.0010 (14)0.0150 (15)0.0001 (16)
C13B0.0473 (17)0.0421 (18)0.054 (2)0.0056 (13)0.0085 (14)0.0017 (14)
C14B0.0572 (19)0.0407 (18)0.058 (2)0.0034 (14)0.0159 (16)0.0049 (15)
C15B0.067 (2)0.0389 (18)0.068 (2)0.0075 (16)0.0115 (17)0.0006 (17)
C16B0.0528 (18)0.0431 (18)0.050 (2)0.0121 (14)0.0165 (15)0.0036 (15)
C17B0.0490 (19)0.047 (2)0.075 (3)0.0065 (15)0.0080 (17)0.0049 (18)
C18B0.0448 (16)0.0381 (17)0.0541 (19)0.0017 (13)0.0104 (14)0.0056 (14)
C19B0.0516 (19)0.0463 (19)0.057 (2)0.0012 (14)0.0017 (15)0.0017 (16)
C20B0.0567 (19)0.0372 (17)0.0534 (19)0.0017 (14)0.0086 (15)0.0026 (15)
C21B0.0495 (17)0.0373 (17)0.0543 (19)0.0037 (13)0.0111 (14)0.0022 (15)
C22B0.0484 (18)0.0391 (17)0.0517 (19)0.0037 (13)0.0057 (14)0.0001 (14)
C23B0.0480 (17)0.0371 (16)0.0489 (18)0.0020 (13)0.0135 (14)0.0045 (13)
C24B0.061 (2)0.0436 (18)0.0484 (19)0.0083 (15)0.0075 (15)0.0011 (15)
C25B0.080 (2)0.051 (2)0.0449 (19)0.0202 (18)0.0198 (17)0.0045 (15)
C26B0.084 (3)0.079 (3)0.110 (4)0.016 (2)0.007 (3)0.039 (3)
C27B0.065 (2)0.048 (2)0.073 (3)0.0175 (17)0.0018 (19)0.0018 (18)
Geometric parameters (Å, º) top
O1A—C5A1.369 (4)C19A—C20A1.373 (5)
O1A—C9A1.422 (6)C20A—C21A1.398 (5)
O2A—C6A1.376 (4)C21A—C22A1.377 (5)
O2A—C10A1.405 (5)C22A—H22A0.9300
O3A—C16A1.233 (4)C22A—C23A1.408 (4)
O4A—C20A1.376 (4)C23A—C24A1.516 (4)
O4A—C26A1.349 (6)C24A—H24A0.9700
O5A—C21A1.363 (4)C24A—H24B0.9700
O5A—C27A1.414 (5)C24A—C25A1.513 (5)
O1B—C5B1.371 (5)C25A—H25A0.9700
O1B—C9B1.420 (5)C25A—H25B0.9700
O2B—C6B1.382 (5)C26A—H26A0.9600
O2B—C10B1.404 (5)C26A—H26B0.9600
O3B—C16B1.228 (4)C26A—H26C0.9600
O4B—C20B1.371 (4)C27A—H27A0.9600
O4B—C26B1.406 (6)C27A—H27B0.9600
O5B—C21B1.373 (4)C27A—H27C0.9600
O5B—C27B1.408 (5)C1B—H1BA0.9800
O6—H6A0.8195C1B—C2B1.583 (6)
O6—H6B0.8214C1B—C8B1.528 (5)
N1A—H1A0.9800C1B—C11B1.510 (5)
N1A—C11A1.504 (4)C2B—H2BA0.9700
N1A—C12A1.488 (4)C2B—H2BB0.9700
N1A—C13A1.497 (4)C2B—C3B1.519 (5)
N1B—H1B0.9800C3B—C4B1.382 (5)
N1B—C11B1.500 (4)C3B—C8B1.369 (5)
N1B—C12B1.484 (4)C4B—H4B0.9300
N1B—C13B1.499 (4)C4B—C5B1.386 (5)
N2A—C15A1.464 (4)C5B—C6B1.416 (5)
N2A—C16A1.333 (4)C6B—C7B1.373 (5)
N2A—C25A1.460 (4)C7B—H7B0.9300
N2B—C15B1.452 (5)C7B—C8B1.382 (5)
N2B—C16B1.347 (5)C9B—H9BA0.9600
N2B—C25B1.458 (5)C9B—H9BB0.9600
C1A—H1AA0.9800C9B—H9BC0.9600
C1A—C2A1.580 (5)C10B—H10D0.9600
C1A—C8A1.524 (5)C10B—H10E0.9600
C1A—C11A1.519 (5)C10B—H10F0.9600
C2A—H2AA0.9700C11B—H11C0.9700
C2A—H2AB0.9700C11B—H11D0.9700
C2A—C3A1.525 (5)C12B—H12D0.9600
C3A—C4A1.384 (5)C12B—H12E0.9600
C3A—C8A1.371 (5)C12B—H12F0.9600
C4A—H4A0.9300C13B—H13C0.9700
C4A—C5A1.394 (5)C13B—H13D0.9700
C5A—C6A1.405 (5)C13B—C14B1.505 (5)
C6A—C7A1.386 (5)C14B—H14C0.9700
C7A—H7A0.9300C14B—H14D0.9700
C7A—C8A1.387 (5)C14B—C15B1.531 (5)
C9A—H9AA0.9600C15B—H15C0.9700
C9A—H9AB0.9600C15B—H15D0.9700
C9A—H9AC0.9600C16B—C17B1.507 (5)
C10A—H10A0.9600C17B—H17C0.9700
C10A—H10B0.9600C17B—H17D0.9700
C10A—H10C0.9600C17B—C18B1.516 (5)
C11A—H11A0.9700C18B—C19B1.407 (5)
C11A—H11B0.9700C18B—C23B1.392 (5)
C12A—H12A0.9600C19B—H19B0.9300
C12A—H12B0.9600C19B—C20B1.372 (5)
C12A—H12C0.9600C20B—C21B1.399 (5)
C13A—H13A0.9700C21B—C22B1.371 (5)
C13A—H13B0.9700C22B—H22B0.9300
C13A—C14A1.503 (5)C22B—C23B1.408 (5)
C14A—H14A0.9700C23B—C24B1.508 (5)
C14A—H14B0.9700C24B—H24C0.9700
C14A—C15A1.519 (4)C24B—H24D0.9700
C15A—H15A0.9700C24B—C25B1.516 (5)
C15A—H15B0.9700C25B—H25C0.9700
C16A—C17A1.515 (5)C25B—H25D0.9700
C17A—H17A0.9700C26B—H26D0.9600
C17A—H17B0.9700C26B—H26E0.9600
C17A—C18A1.519 (4)C26B—H26F0.9600
C18A—C19A1.407 (5)C27B—H27D0.9600
C18A—C23A1.390 (4)C27B—H27E0.9600
C19A—H19A0.9300C27B—H27F0.9600
C5A—O1A—C9A117.4 (3)H25A—C25A—H25B107.9
C6A—O2A—C10A117.5 (3)O4A—C26A—H26A109.5
C26A—O4A—C20A118.7 (3)O4A—C26A—H26B109.5
C21A—O5A—C27A117.7 (3)O4A—C26A—H26C109.5
C5B—O1B—C9B117.2 (3)H26A—C26A—H26B109.5
C6B—O2B—C10B117.0 (3)H26A—C26A—H26C109.5
C20B—O4B—C26B117.5 (3)H26B—C26A—H26C109.5
C21B—O5B—C27B117.6 (3)O5A—C27A—H27A109.5
H6A—O6—H6B133.1O5A—C27A—H27B109.5
C11A—N1A—H1A106.3O5A—C27A—H27C109.5
C12A—N1A—H1A106.3H27A—C27A—H27B109.5
C12A—N1A—C11A113.4 (3)H27A—C27A—H27C109.5
C12A—N1A—C13A111.6 (3)H27B—C27A—H27C109.5
C13A—N1A—H1A106.3C2B—C1B—H1BA111.6
C13A—N1A—C11A112.3 (2)C8B—C1B—H1BA111.6
C11B—N1B—H1B107.5C8B—C1B—C2B85.8 (3)
C12B—N1B—H1B107.5C11B—C1B—H1BA111.6
C12B—N1B—C11B112.3 (3)C11B—C1B—C2B120.8 (3)
C12B—N1B—C13B111.7 (3)C11B—C1B—C8B113.0 (3)
C13B—N1B—H1B107.5C1B—C2B—H2BA114.3
C13B—N1B—C11B110.0 (2)C1B—C2B—H2BB114.3
C16A—N2A—C15A119.2 (3)H2BA—C2B—H2BB111.4
C16A—N2A—C25A122.1 (3)C3B—C2B—C1B86.1 (3)
C25A—N2A—C15A118.7 (3)C3B—C2B—H2BA114.3
C15B—N2B—C25B118.7 (3)C3B—C2B—H2BB114.3
C16B—N2B—C15B119.5 (3)C4B—C3B—C2B144.1 (4)
C16B—N2B—C25B121.4 (3)C8B—C3B—C2B94.2 (3)
C2A—C1A—H1AA113.3C8B—C3B—C4B121.7 (4)
C8A—C1A—H1AA113.3C3B—C4B—H4B121.8
C8A—C1A—C2A86.0 (2)C3B—C4B—C5B116.3 (4)
C11A—C1A—H1AA113.3C5B—C4B—H4B121.8
C11A—C1A—C2A117.8 (3)O1B—C5B—C4B124.2 (3)
C11A—C1A—C8A110.2 (3)O1B—C5B—C6B114.6 (3)
C1A—C2A—H2AA114.3C4B—C5B—C6B121.2 (3)
C1A—C2A—H2AB114.3O2B—C6B—C5B114.0 (3)
H2AA—C2A—H2AB111.4C7B—C6B—O2B124.6 (3)
C3A—C2A—C1A86.1 (3)C7B—C6B—C5B121.4 (3)
C3A—C2A—H2AA114.3C6B—C7B—H7B122.0
C3A—C2A—H2AB114.3C6B—C7B—C8B116.0 (3)
C4A—C3A—C2A143.8 (3)C8B—C7B—H7B122.0
C8A—C3A—C2A93.8 (3)C3B—C8B—C1B93.8 (3)
C8A—C3A—C4A122.2 (3)C3B—C8B—C7B123.1 (3)
C3A—C4A—H4A122.0C7B—C8B—C1B143.0 (3)
C3A—C4A—C5A116.1 (3)O1B—C9B—H9BA109.5
C5A—C4A—H4A122.0O1B—C9B—H9BB109.5
O1A—C5A—C4A123.6 (3)O1B—C9B—H9BC109.5
O1A—C5A—C6A114.8 (3)H9BA—C9B—H9BB109.5
C4A—C5A—C6A121.6 (3)H9BA—C9B—H9BC109.5
O2A—C6A—C5A114.3 (3)H9BB—C9B—H9BC109.5
O2A—C6A—C7A124.3 (3)O2B—C10B—H10D109.5
C7A—C6A—C5A121.4 (3)O2B—C10B—H10E109.5
C6A—C7A—H7A122.0O2B—C10B—H10F109.5
C8A—C7A—C6A116.1 (3)H10D—C10B—H10E109.5
C8A—C7A—H7A122.0H10D—C10B—H10F109.5
C3A—C8A—C1A94.0 (3)H10E—C10B—H10F109.5
C3A—C8A—C7A122.7 (3)N1B—C11B—C1B114.2 (3)
C7A—C8A—C1A143.2 (3)N1B—C11B—H11C108.7
O1A—C9A—H9AA109.5N1B—C11B—H11D108.7
O1A—C9A—H9AB109.5C1B—C11B—H11C108.7
O1A—C9A—H9AC109.5C1B—C11B—H11D108.7
H9AA—C9A—H9AB109.5H11C—C11B—H11D107.6
H9AA—C9A—H9AC109.5N1B—C12B—H12D109.5
H9AB—C9A—H9AC109.5N1B—C12B—H12E109.5
O2A—C10A—H10A109.5N1B—C12B—H12F109.5
O2A—C10A—H10B109.5H12D—C12B—H12E109.5
O2A—C10A—H10C109.5H12D—C12B—H12F109.5
H10A—C10A—H10B109.5H12E—C12B—H12F109.5
H10A—C10A—H10C109.5N1B—C13B—H13C109.1
H10B—C10A—H10C109.5N1B—C13B—H13D109.1
N1A—C11A—C1A116.3 (3)N1B—C13B—C14B112.4 (3)
N1A—C11A—H11A108.2H13C—C13B—H13D107.9
N1A—C11A—H11B108.2C14B—C13B—H13C109.1
C1A—C11A—H11A108.2C14B—C13B—H13D109.1
C1A—C11A—H11B108.2C13B—C14B—H14C109.7
H11A—C11A—H11B107.4C13B—C14B—H14D109.7
N1A—C12A—H12A109.5C13B—C14B—C15B109.7 (3)
N1A—C12A—H12B109.5H14C—C14B—H14D108.2
N1A—C12A—H12C109.5C15B—C14B—H14C109.7
H12A—C12A—H12B109.5C15B—C14B—H14D109.7
H12A—C12A—H12C109.5N2B—C15B—C14B110.9 (3)
H12B—C12A—H12C109.5N2B—C15B—H15C109.5
N1A—C13A—H13A109.0N2B—C15B—H15D109.5
N1A—C13A—H13B109.0C14B—C15B—H15C109.5
N1A—C13A—C14A113.1 (3)C14B—C15B—H15D109.5
H13A—C13A—H13B107.8H15C—C15B—H15D108.1
C14A—C13A—H13A109.0O3B—C16B—N2B122.1 (3)
C14A—C13A—H13B109.0O3B—C16B—C17B120.5 (3)
C13A—C14A—H14A109.8N2B—C16B—C17B117.4 (3)
C13A—C14A—H14B109.8C16B—C17B—H17C108.1
C13A—C14A—C15A109.4 (3)C16B—C17B—H17D108.1
H14A—C14A—H14B108.2C16B—C17B—C18B117.0 (3)
C15A—C14A—H14A109.8H17C—C17B—H17D107.3
C15A—C14A—H14B109.8C18B—C17B—H17C108.1
N2A—C15A—C14A112.3 (3)C18B—C17B—H17D108.1
N2A—C15A—H15A109.2C19B—C18B—C17B115.5 (3)
N2A—C15A—H15B109.2C23B—C18B—C17B125.8 (3)
C14A—C15A—H15A109.2C23B—C18B—C19B118.6 (3)
C14A—C15A—H15B109.2C18B—C19B—H19B118.8
H15A—C15A—H15B107.9C20B—C19B—C18B122.3 (3)
O3A—C16A—N2A122.3 (3)C20B—C19B—H19B118.8
O3A—C16A—C17A120.8 (3)O4B—C20B—C19B124.9 (3)
N2A—C16A—C17A116.9 (3)O4B—C20B—C21B115.9 (3)
C16A—C17A—H17A108.1C19B—C20B—C21B119.1 (3)
C16A—C17A—H17B108.1O5B—C21B—C20B115.5 (3)
C16A—C17A—C18A116.7 (3)C22B—C21B—O5B125.4 (3)
H17A—C17A—H17B107.3C22B—C21B—C20B119.1 (3)
C18A—C17A—H17A108.1C21B—C22B—H22B118.8
C18A—C17A—H17B108.1C21B—C22B—C23B122.5 (3)
C19A—C18A—C17A116.3 (3)C23B—C22B—H22B118.8
C23A—C18A—C17A124.8 (3)C18B—C23B—C22B118.3 (3)
C23A—C18A—C19A118.9 (3)C18B—C23B—C24B125.5 (3)
C18A—C19A—H19A119.1C22B—C23B—C24B116.2 (3)
C20A—C19A—C18A121.9 (3)C23B—C24B—H24C108.1
C20A—C19A—H19A119.1C23B—C24B—H24D108.1
O4A—C20A—C21A116.4 (3)C23B—C24B—C25B116.7 (3)
C19A—C20A—O4A123.9 (3)H24C—C24B—H24D107.3
C19A—C20A—C21A119.7 (3)C25B—C24B—H24C108.1
O5A—C21A—C20A115.8 (3)C25B—C24B—H24D108.1
O5A—C21A—C22A125.6 (3)N2B—C25B—C24B112.5 (3)
C22A—C21A—C20A118.6 (3)N2B—C25B—H25C109.1
C21A—C22A—H22A118.7N2B—C25B—H25D109.1
C21A—C22A—C23A122.5 (3)C24B—C25B—H25C109.1
C23A—C22A—H22A118.7C24B—C25B—H25D109.1
C18A—C23A—C22A118.3 (3)H25C—C25B—H25D107.8
C18A—C23A—C24A125.2 (3)O4B—C26B—H26D109.5
C22A—C23A—C24A116.5 (3)O4B—C26B—H26E109.5
C23A—C24A—H24A108.0O4B—C26B—H26F109.5
C23A—C24A—H24B108.0H26D—C26B—H26E109.5
H24A—C24A—H24B107.3H26D—C26B—H26F109.5
C25A—C24A—C23A117.0 (3)H26E—C26B—H26F109.5
C25A—C24A—H24A108.0O5B—C27B—H27D109.5
C25A—C24A—H24B108.0O5B—C27B—H27E109.5
N2A—C25A—C24A112.1 (3)O5B—C27B—H27F109.5
N2A—C25A—H25A109.2H27D—C27B—H27E109.5
N2A—C25A—H25B109.2H27D—C27B—H27F109.5
C24A—C25A—H25A109.2H27E—C27B—H27F109.5
C24A—C25A—H25B109.2
O1A—C5A—C6A—O2A2.7 (5)C23A—C18A—C19A—C20A0.2 (5)
O1A—C5A—C6A—C7A176.8 (3)C23A—C24A—C25A—N2A68.2 (4)
O2A—C6A—C7A—C8A179.1 (3)C25A—N2A—C15A—C14A96.0 (3)
O3A—C16A—C17A—C18A114.6 (4)C25A—N2A—C16A—O3A177.5 (3)
O4A—C20A—C21A—O5A0.5 (5)C25A—N2A—C16A—C17A3.4 (5)
O4A—C20A—C21A—C22A178.8 (3)C26A—O4A—C20A—C19A31.5 (7)
O5A—C21A—C22A—C23A179.6 (3)C26A—O4A—C20A—C21A150.0 (5)
O1B—C5B—C6B—O2B3.2 (5)C27A—O5A—C21A—C20A178.3 (3)
O1B—C5B—C6B—C7B175.0 (4)C27A—O5A—C21A—C22A3.5 (5)
O2B—C6B—C7B—C8B179.2 (3)C1B—C2B—C3B—C4B174.9 (6)
O3B—C16B—C17B—C18B120.5 (4)C1B—C2B—C3B—C8B2.2 (3)
O4B—C20B—C21B—O5B0.1 (5)C2B—C1B—C8B—C3B2.2 (3)
O4B—C20B—C21B—C22B179.1 (3)C2B—C1B—C8B—C7B177.7 (5)
O5B—C21B—C22B—C23B179.8 (3)C2B—C1B—C11B—N1B87.7 (4)
N1A—C13A—C14A—C15A172.8 (3)C2B—C3B—C4B—C5B178.1 (5)
N1B—C13B—C14B—C15B168.7 (3)C2B—C3B—C8B—C1B2.3 (3)
N2A—C16A—C17A—C18A66.3 (4)C2B—C3B—C8B—C7B177.6 (3)
N2B—C16B—C17B—C18B59.8 (5)C3B—C4B—C5B—O1B177.3 (4)
C1A—C2A—C3A—C4A173.9 (5)C3B—C4B—C5B—C6B3.3 (6)
C1A—C2A—C3A—C8A1.3 (3)C4B—C3B—C8B—C1B175.7 (4)
C2A—C1A—C8A—C3A1.3 (3)C4B—C3B—C8B—C7B4.3 (6)
C2A—C1A—C8A—C7A176.4 (5)C4B—C5B—C6B—O2B176.2 (4)
C2A—C1A—C11A—N1A90.4 (3)C4B—C5B—C6B—C7B5.6 (6)
C2A—C3A—C4A—C5A174.6 (5)C5B—C6B—C7B—C8B2.7 (5)
C2A—C3A—C8A—C1A1.3 (3)C6B—C7B—C8B—C1B178.0 (4)
C2A—C3A—C8A—C7A177.8 (3)C6B—C7B—C8B—C3B2.1 (5)
C3A—C4A—C5A—O1A177.7 (4)C8B—C1B—C2B—C3B2.0 (3)
C3A—C4A—C5A—C6A1.5 (6)C8B—C1B—C11B—N1B173.0 (3)
C4A—C3A—C8A—C1A175.3 (3)C8B—C3B—C4B—C5B1.4 (6)
C4A—C3A—C8A—C7A1.2 (6)C9B—O1B—C5B—C4B14.8 (6)
C4A—C5A—C6A—O2A178.1 (4)C9B—O1B—C5B—C6B165.9 (4)
C4A—C5A—C6A—C7A2.5 (6)C10B—O2B—C6B—C5B168.5 (4)
C5A—C6A—C7A—C8A1.5 (5)C10B—O2B—C6B—C7B13.3 (6)
C6A—C7A—C8A—C1A173.9 (4)C11B—N1B—C13B—C14B165.9 (3)
C6A—C7A—C8A—C3A0.3 (5)C11B—C1B—C2B—C3B116.3 (3)
C8A—C1A—C2A—C3A1.2 (2)C11B—C1B—C8B—C3B124.0 (3)
C8A—C1A—C11A—N1A173.3 (3)C11B—C1B—C8B—C7B55.9 (6)
C8A—C3A—C4A—C5A0.3 (6)C12B—N1B—C11B—C1B68.3 (4)
C9A—O1A—C5A—C4A13.9 (6)C12B—N1B—C13B—C14B68.7 (4)
C9A—O1A—C5A—C6A165.3 (4)C13B—N1B—C11B—C1B166.7 (3)
C10A—O2A—C6A—C5A167.6 (4)C13B—C14B—C15B—N2B173.4 (3)
C10A—O2A—C6A—C7A12.9 (6)C15B—N2B—C16B—O3B0.5 (5)
C11A—N1A—C13A—C14A158.4 (3)C15B—N2B—C16B—C17B179.2 (3)
C11A—C1A—C2A—C3A109.6 (3)C15B—N2B—C25B—C24B109.1 (4)
C11A—C1A—C8A—C3A116.9 (3)C16B—N2B—C15B—C14B79.9 (4)
C11A—C1A—C8A—C7A58.2 (6)C16B—N2B—C25B—C24B78.2 (4)
C12A—N1A—C11A—C1A50.2 (4)C16B—C17B—C18B—C19B132.4 (4)
C12A—N1A—C13A—C14A73.0 (4)C16B—C17B—C18B—C23B48.5 (5)
C13A—N1A—C11A—C1A77.4 (3)C17B—C18B—C19B—C20B179.0 (3)
C13A—C14A—C15A—N2A173.4 (3)C17B—C18B—C23B—C22B179.1 (3)
C15A—N2A—C16A—O3A0.1 (5)C17B—C18B—C23B—C24B1.8 (5)
C15A—N2A—C16A—C17A179.0 (3)C18B—C19B—C20B—O4B179.5 (3)
C15A—N2A—C25A—C24A105.7 (3)C18B—C19B—C20B—C21B0.7 (6)
C16A—N2A—C15A—C14A86.3 (4)C18B—C23B—C24B—C25B9.7 (5)
C16A—N2A—C25A—C24A72.0 (4)C19B—C18B—C23B—C22B0.0 (5)
C16A—C17A—C18A—C19A134.4 (3)C19B—C18B—C23B—C24B179.1 (3)
C16A—C17A—C18A—C23A46.6 (5)C19B—C20B—C21B—O5B180.0 (3)
C17A—C18A—C19A—C20A178.8 (3)C19B—C20B—C21B—C22B1.1 (5)
C17A—C18A—C23A—C22A179.9 (3)C20B—C21B—C22B—C23B0.9 (5)
C17A—C18A—C23A—C24A0.4 (5)C21B—C22B—C23B—C18B0.4 (5)
C18A—C19A—C20A—O4A179.5 (3)C21B—C22B—C23B—C24B178.8 (3)
C18A—C19A—C20A—C21A2.1 (5)C22B—C23B—C24B—C25B171.2 (3)
C18A—C23A—C24A—C25A12.9 (5)C23B—C18B—C19B—C20B0.2 (5)
C19A—C18A—C23A—C22A0.9 (5)C23B—C24B—C25B—N2B65.1 (4)
C19A—C18A—C23A—C24A179.4 (3)C25B—N2B—C15B—C14B92.9 (4)
C19A—C20A—C21A—O5A179.1 (3)C25B—N2B—C16B—O3B173.2 (3)
C19A—C20A—C21A—C22A2.6 (5)C25B—N2B—C16B—C17B6.5 (5)
C20A—C21A—C22A—C23A1.5 (5)C26B—O4B—C20B—C19B19.5 (6)
C21A—C22A—C23A—C18A0.3 (5)C26B—O4B—C20B—C21B160.7 (4)
C21A—C22A—C23A—C24A180.0 (3)C27B—O5B—C21B—C20B178.7 (3)
C22A—C23A—C24A—C25A167.4 (3)C27B—O5B—C21B—C22B0.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6A···Cl1Bi0.822.583.230 (4)137
O6—H6B···Cl1B0.822.493.283 (4)162
N1A—H1A···Cl1A0.982.123.055 (3)158
N1B—H1B···Cl1B0.982.123.093 (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) top
Crystal data top
C27H37N2O5+·Cl·4H2ODx = 1.253 Mg m3
Mr = 577.10Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 32894 reflections
a = 8.6747 (2) Åθ = 3.0–27.5°
b = 18.2437 (5) ŵ = 0.18 mm1
c = 38.6507 (9) ÅT = 296 K
V = 6116.8 (3) Å3Needle, colourless
Z = 80.3 × 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 tube7143 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1Rint = 0.058
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1110
Tmin = 0.949, Tmax = 0.983k = 2323
55596 measured reflectionsl = 5050
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH 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 = 0.96Δρmax = 0.17 e Å3
13936 reflectionsΔρmin = 0.19 e Å3
715 parametersAbsolute structure: Flack x determined using 2366 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
7 restraintsAbsolute 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
xyzUiso*/Ueq
Cl10.61033 (12)0.47173 (6)0.42178 (4)0.0999 (4)
Cl20.41813 (13)0.54721 (6)0.57885 (4)0.0947 (4)
O1A0.6412 (3)0.87639 (14)0.28869 (7)0.0726 (7)
O2A0.8773 (3)0.82923 (15)0.32083 (7)0.0730 (8)
O3A0.0837 (3)0.62870 (14)0.40461 (6)0.0687 (7)
O4A0.2588 (3)0.64185 (15)0.26145 (7)0.0714 (8)
O5A0.4908 (3)0.56182 (14)0.27999 (6)0.0633 (7)
N1A0.4527 (3)0.61379 (15)0.44549 (7)0.0484 (7)
H1A0.4949330.5678890.4363370.058*
N2A0.0208 (3)0.51664 (14)0.41408 (7)0.0460 (7)
O110.4198 (3)0.77188 (13)0.54417 (6)0.0711 (7)
H11E0.4057540.8050260.5582280.107*
H11F0.4245240.7900750.5247780.107*
O120.6567 (3)0.67652 (16)0.56147 (7)0.0862 (9)
H12G0.5998530.7060640.5515510.129*
H12H0.6075730.6388940.5658410.129*
O130.4072 (3)0.83916 (17)0.48195 (8)0.0946 (9)
H13E0.4893170.8322570.4718170.142*
H13F0.3356870.8320170.4684070.142*
O140.2006 (3)0.66100 (18)0.54256 (9)0.1008 (11)
H14E0.2609260.6953660.5405690.151*
H14F0.2375460.6216660.5486390.151*
C1A0.4913 (4)0.66664 (18)0.38552 (8)0.0482 (8)
H1AA0.5081860.6160840.3778370.058*
C2A0.3433 (4)0.70032 (18)0.36840 (9)0.0532 (9)
H2AA0.2832070.6657110.3549440.064*
H2AB0.2786910.7279590.3841890.064*
C3A0.4532 (4)0.74717 (18)0.34703 (8)0.0468 (8)
C4A0.4622 (4)0.79966 (19)0.32122 (9)0.0523 (9)
H4A0.3749990.8167320.3097830.063*
C5A0.6085 (4)0.82530 (19)0.31340 (9)0.0522 (9)
C6A0.7391 (4)0.79873 (19)0.33130 (10)0.0514 (9)
C7A0.7275 (4)0.74544 (19)0.35628 (9)0.0528 (9)
H7A0.8135240.7271940.3677660.063*
C8A0.5805 (4)0.72059 (17)0.36329 (8)0.0469 (8)
C9A0.5153 (5)0.9042 (3)0.26888 (11)0.0855 (13)
H9AA0.4690440.8649220.2560070.128*
H9AB0.5521510.9409910.2531800.128*
H9AC0.4401090.9252940.2841300.128*
C10A1.0098 (4)0.8103 (2)0.34018 (11)0.0762 (12)
H10A0.9940310.8229060.3640330.114*
H10B1.0973170.8365100.3313750.114*
H10C1.0279620.7585180.3382750.114*
C11A0.5187 (4)0.67440 (18)0.42392 (8)0.0521 (8)
H11A0.6288790.6767790.4280030.063*
H11B0.4744220.7204680.4315730.063*
C12A0.5068 (5)0.6199 (2)0.48184 (9)0.0769 (12)
H12A0.6174410.6206810.4822680.115*
H12B0.4701850.5786370.4948770.115*
H12C0.4677360.6643200.4918540.115*
C13A0.2807 (4)0.60841 (19)0.44244 (9)0.0508 (9)
H13A0.2528910.6069200.4181400.061*
H13B0.2345950.6519890.4524160.061*
C14A0.2152 (4)0.54150 (19)0.46028 (9)0.0510 (9)
H14A0.2242300.5474910.4851330.061*
H14B0.2746650.4986910.4536840.061*
C15A0.0461 (4)0.52925 (19)0.45085 (8)0.0493 (9)
H15A0.0076600.4873670.4636880.059*
H15B0.0130450.5717960.4579540.059*
C16A0.0463 (4)0.5673 (2)0.39390 (9)0.0509 (9)
C17A0.0683 (4)0.5484 (2)0.35611 (9)0.0576 (9)
H17A0.1355380.5845400.3455710.069*
H17B0.1187030.5010460.3543730.069*
C18A0.0828 (4)0.54584 (17)0.33620 (8)0.0464 (8)
C19A0.0985 (4)0.59186 (18)0.30734 (9)0.0539 (9)
H19A0.0144570.6198620.3003640.065*
C20A0.2328 (4)0.59693 (19)0.28917 (9)0.0517 (9)
C21A0.3583 (4)0.55391 (19)0.29940 (9)0.0496 (8)
C22A0.3446 (4)0.50895 (18)0.32752 (9)0.0493 (8)
H22A0.4293190.4812350.3343500.059*
C23A0.2074 (4)0.50325 (17)0.34638 (9)0.0463 (8)
C24A0.2106 (4)0.45134 (18)0.37689 (8)0.0502 (9)
H24A0.2959990.4655910.3916450.060*
H24B0.2335060.4027110.3681400.060*
C25A0.0682 (4)0.44566 (18)0.39935 (9)0.0520 (9)
H25A0.0158420.4260310.3856410.062*
H25B0.0882500.4115560.4180750.062*
C26A0.1473 (6)0.6973 (3)0.25430 (10)0.0860 (14)
H26A0.0535580.6747960.2464240.129*
H26B0.1860660.7294670.2366910.129*
H26C0.1271390.7248150.2749720.129*
C27A0.6277 (4)0.5313 (3)0.29376 (11)0.0814 (13)
H27A0.6439120.5496260.3167510.122*
H27B0.7135310.5445810.2793980.122*
H27C0.6185090.4788390.2944750.122*
O1B0.3760 (3)0.12954 (15)0.71476 (7)0.0744 (8)
O2B0.1448 (3)0.16137 (15)0.67729 (7)0.0751 (8)
O3B1.0957 (3)0.36746 (16)0.59195 (7)0.0764 (8)
O4B0.7429 (3)0.35039 (15)0.73160 (7)0.0751 (8)
O5B0.5245 (3)0.43911 (16)0.71391 (6)0.0712 (7)
N1B0.5606 (3)0.40080 (15)0.56155 (7)0.0514 (7)
H1B0.5294000.4522750.5634290.062*
N2B1.0089 (3)0.48330 (16)0.58399 (7)0.0533 (7)
C1B0.5426 (4)0.28530 (18)0.59855 (9)0.0514 (8)
H1BA0.5492020.2571250.5770170.062*
C2B0.6853 (4)0.2711 (2)0.62305 (10)0.0601 (10)
H2BA0.7635930.2394500.6131590.072*
H2BB0.7302210.3152140.6327490.072*
C3B0.5737 (4)0.23229 (18)0.64690 (9)0.0513 (9)
C4B0.5585 (4)0.1929 (2)0.67748 (10)0.0586 (10)
H4B0.6428670.1829510.6915520.070*
C5B0.4114 (4)0.1693 (2)0.68604 (9)0.0552 (9)
C6B0.2837 (4)0.1852 (2)0.66471 (10)0.0559 (10)
C7B0.3010 (4)0.22418 (19)0.63406 (10)0.0579 (10)
H7B0.2177500.2350480.6197940.069*
C8B0.4495 (4)0.24577 (17)0.62607 (9)0.0495 (8)
C9B0.4984 (6)0.1051 (3)0.73629 (11)0.0959 (15)
H9BA0.5681930.0755980.7229800.144*
H9BB0.4571570.0765110.7549780.144*
H9BC0.5523930.1467090.7454720.144*
C10B0.0120 (4)0.1801 (2)0.65774 (12)0.0793 (13)
H10D0.0073580.2323740.6549620.119*
H10E0.0786000.1634690.6696290.119*
H10F0.0175490.1572410.6354120.119*
C11B0.4912 (4)0.36233 (18)0.59245 (9)0.0541 (9)
H11C0.5148820.3908490.6129600.065*
H11D0.3800180.3622700.5897790.065*
C12B0.4965 (4)0.3740 (2)0.52816 (10)0.0784 (12)
H12D0.5401820.4016540.5094420.118*
H12E0.3865790.3798990.5281820.118*
H12F0.5215320.3230720.5253110.118*
C13B0.7332 (3)0.4006 (2)0.56251 (10)0.0548 (9)
H13C0.7707110.3537070.5542220.066*
H13D0.7674120.4064910.5862430.066*
C14B0.8021 (4)0.4617 (2)0.54045 (9)0.0538 (9)
H14C0.7489750.5072830.5453580.065*
H14D0.7868910.4502700.5161720.065*
C15B0.9743 (4)0.4712 (2)0.54755 (9)0.0580 (10)
H15C1.0285500.4278230.5397110.070*
H15D1.0121720.5125830.5342510.070*
C16B1.0673 (4)0.4291 (2)0.60334 (10)0.0595 (10)
C17B1.0917 (4)0.4453 (2)0.64106 (10)0.0662 (10)
H17C1.1454240.4916700.6434890.079*
H17D1.1555910.4073320.6512120.079*
C18B0.9387 (4)0.4490 (2)0.66026 (9)0.0523 (9)
C19B0.9156 (4)0.4003 (2)0.68770 (9)0.0574 (10)
H19B0.9952490.3691520.6942830.069*
C20B0.7781 (4)0.3975 (2)0.70511 (10)0.0595 (10)
C21B0.6580 (4)0.4447 (2)0.69532 (9)0.0575 (9)
C22B0.6808 (4)0.49246 (19)0.66838 (9)0.0528 (9)
H22B0.6004550.5231810.6617880.063*
C23B0.8210 (4)0.49658 (18)0.65047 (9)0.0505 (9)
C24B0.8290 (4)0.55344 (19)0.62200 (9)0.0575 (10)
H24C0.8185430.6013870.6325900.069*
H24D0.7404350.5464700.6070430.069*
C25B0.9723 (4)0.5545 (2)0.59941 (10)0.0613 (10)
H25C0.9577160.5900600.5810260.074*
H25D1.0592610.5705640.6132540.074*
C26B0.8556 (6)0.2969 (2)0.74068 (12)0.0859 (14)
H26D0.8771880.2665520.7209790.129*
H26E0.8171710.2670960.7592360.129*
H26F0.9484830.3210660.7479410.129*
C27B0.3919 (5)0.4730 (3)0.70011 (11)0.0889 (14)
H27D0.4074270.5250720.6991870.133*
H27E0.3047320.4623000.7145480.133*
H27F0.3733310.4547140.6771950.133*
O210.3803 (3)0.34166 (16)0.44309 (8)0.0894 (9)
H21A0.4227320.3809040.4383180.134*
H21B0.4439220.3096540.4473080.134*
O220.1170 (3)0.33620 (18)0.48238 (7)0.1011 (10)
H22C0.1796400.3280820.4668670.152*
H22D0.0324500.3404920.4732170.152*
O230.1092 (4)0.26197 (14)0.54282 (7)0.0865 (9)
H23A0.0972060.2856990.5250030.130*
H23B0.0892960.2946890.5567030.130*
O240.1792 (4)0.3540 (2)0.45942 (9)0.0974 (10)
H24E0.2250430.3781220.4446800.18 (3)*
H24F0.2050230.3106520.4599400.18 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0587 (6)0.0590 (6)0.1819 (13)0.0061 (5)0.0032 (7)0.0043 (7)
Cl20.0665 (6)0.0591 (6)0.1585 (12)0.0101 (5)0.0028 (7)0.0132 (7)
O1A0.0695 (17)0.0770 (18)0.0713 (17)0.0007 (15)0.0032 (15)0.0328 (15)
O2A0.0505 (15)0.0872 (19)0.0811 (19)0.0057 (15)0.0023 (14)0.0243 (16)
O3A0.0811 (18)0.0557 (15)0.0692 (17)0.0203 (15)0.0093 (15)0.0041 (14)
O4A0.0798 (18)0.0730 (18)0.0615 (16)0.0025 (15)0.0141 (14)0.0251 (14)
O5A0.0599 (15)0.0744 (18)0.0555 (15)0.0020 (14)0.0021 (13)0.0102 (13)
N1A0.0468 (15)0.0479 (16)0.0506 (16)0.0084 (13)0.0064 (14)0.0037 (14)
N2A0.0444 (15)0.0428 (15)0.0508 (17)0.0011 (13)0.0027 (14)0.0002 (14)
O110.0883 (19)0.0548 (15)0.0704 (17)0.0001 (15)0.0044 (16)0.0011 (13)
O120.0722 (17)0.090 (2)0.096 (2)0.0041 (16)0.0032 (17)0.0143 (17)
O130.0728 (18)0.120 (2)0.091 (2)0.0044 (19)0.0002 (17)0.0185 (19)
O140.0699 (18)0.086 (2)0.147 (3)0.0026 (17)0.0136 (19)0.026 (2)
C1A0.0527 (19)0.0412 (18)0.0508 (19)0.0012 (16)0.0016 (16)0.0002 (16)
C2A0.0468 (18)0.054 (2)0.059 (2)0.0089 (17)0.0047 (17)0.0004 (18)
C3A0.0415 (18)0.050 (2)0.049 (2)0.0031 (16)0.0028 (16)0.0022 (17)
C4A0.050 (2)0.057 (2)0.050 (2)0.0067 (18)0.0065 (18)0.0034 (18)
C5A0.059 (2)0.049 (2)0.049 (2)0.0018 (19)0.0017 (18)0.0086 (18)
C6A0.0463 (19)0.052 (2)0.056 (2)0.0013 (17)0.0029 (17)0.0066 (18)
C7A0.0464 (19)0.057 (2)0.055 (2)0.0062 (17)0.0011 (17)0.0148 (18)
C8A0.0485 (19)0.0432 (18)0.0490 (19)0.0036 (16)0.0020 (17)0.0053 (16)
C9A0.093 (3)0.087 (3)0.076 (3)0.012 (3)0.014 (3)0.036 (2)
C10A0.045 (2)0.089 (3)0.094 (3)0.007 (2)0.004 (2)0.010 (3)
C11A0.0492 (18)0.051 (2)0.056 (2)0.0135 (16)0.0038 (17)0.0060 (17)
C12A0.078 (3)0.104 (3)0.049 (2)0.019 (3)0.018 (2)0.007 (2)
C13A0.0443 (18)0.052 (2)0.056 (2)0.0051 (16)0.0041 (17)0.0052 (18)
C14A0.0496 (19)0.053 (2)0.051 (2)0.0030 (17)0.0044 (17)0.0056 (17)
C15A0.0456 (18)0.052 (2)0.050 (2)0.0047 (16)0.0060 (17)0.0067 (17)
C16A0.0393 (18)0.053 (2)0.061 (2)0.0020 (17)0.0046 (17)0.0019 (19)
C17A0.053 (2)0.059 (2)0.061 (2)0.0013 (18)0.0159 (19)0.0007 (19)
C18A0.0433 (18)0.0459 (18)0.050 (2)0.0043 (16)0.0123 (16)0.0047 (17)
C19A0.054 (2)0.050 (2)0.058 (2)0.0010 (18)0.0229 (19)0.0032 (18)
C20A0.062 (2)0.048 (2)0.045 (2)0.0089 (19)0.0171 (19)0.0062 (17)
C21A0.053 (2)0.049 (2)0.047 (2)0.0044 (18)0.0023 (18)0.0014 (18)
C22A0.0505 (19)0.045 (2)0.052 (2)0.0010 (16)0.0091 (18)0.0031 (18)
C23A0.0498 (19)0.0399 (18)0.049 (2)0.0003 (16)0.0087 (17)0.0006 (16)
C24A0.058 (2)0.0401 (18)0.052 (2)0.0038 (17)0.0012 (17)0.0016 (17)
C25A0.055 (2)0.0422 (19)0.058 (2)0.0021 (17)0.0037 (18)0.0020 (17)
C26A0.110 (4)0.071 (3)0.077 (3)0.012 (3)0.016 (3)0.023 (2)
C27A0.051 (2)0.121 (4)0.072 (3)0.003 (3)0.004 (2)0.017 (3)
O1B0.0738 (18)0.091 (2)0.0583 (16)0.0002 (16)0.0055 (15)0.0222 (16)
O2B0.0514 (15)0.088 (2)0.0860 (19)0.0096 (15)0.0033 (14)0.0244 (16)
O3B0.0670 (17)0.0774 (19)0.085 (2)0.0206 (16)0.0020 (16)0.0048 (16)
O4B0.0831 (19)0.0733 (18)0.0690 (18)0.0031 (16)0.0130 (15)0.0238 (16)
O5B0.0617 (16)0.089 (2)0.0634 (16)0.0041 (15)0.0027 (14)0.0136 (15)
N1B0.0456 (16)0.0486 (16)0.0600 (18)0.0038 (14)0.0078 (14)0.0046 (14)
N2B0.0450 (15)0.0594 (18)0.0555 (18)0.0052 (14)0.0004 (14)0.0053 (16)
C1B0.0498 (19)0.048 (2)0.057 (2)0.0002 (16)0.0035 (18)0.0019 (17)
C2B0.0444 (19)0.061 (2)0.075 (3)0.0059 (17)0.0026 (19)0.002 (2)
C3B0.0458 (19)0.051 (2)0.057 (2)0.0056 (17)0.0029 (18)0.0021 (18)
C4B0.053 (2)0.068 (2)0.054 (2)0.010 (2)0.0091 (19)0.002 (2)
C5B0.059 (2)0.058 (2)0.049 (2)0.004 (2)0.0015 (18)0.0013 (19)
C6B0.0430 (19)0.058 (2)0.066 (3)0.0057 (18)0.0054 (19)0.004 (2)
C7B0.049 (2)0.060 (2)0.064 (2)0.0048 (18)0.0102 (19)0.008 (2)
C8B0.049 (2)0.0405 (18)0.059 (2)0.0024 (16)0.0079 (18)0.0006 (17)
C9B0.104 (3)0.119 (4)0.065 (3)0.018 (3)0.011 (3)0.030 (3)
C10B0.051 (2)0.084 (3)0.103 (3)0.011 (2)0.004 (2)0.008 (3)
C11B0.0442 (18)0.051 (2)0.067 (2)0.0025 (16)0.0034 (18)0.0058 (18)
C12B0.071 (3)0.096 (3)0.069 (3)0.020 (2)0.020 (2)0.004 (2)
C13B0.0425 (19)0.055 (2)0.067 (2)0.0007 (17)0.0068 (17)0.0014 (19)
C14B0.052 (2)0.061 (2)0.049 (2)0.0032 (18)0.0019 (17)0.0037 (18)
C15B0.051 (2)0.069 (3)0.055 (2)0.0053 (19)0.0054 (18)0.003 (2)
C16B0.0382 (19)0.070 (3)0.070 (3)0.0006 (19)0.0002 (19)0.005 (2)
C17B0.047 (2)0.079 (3)0.072 (3)0.002 (2)0.0168 (19)0.003 (2)
C18B0.0479 (19)0.057 (2)0.052 (2)0.0023 (18)0.0118 (18)0.0020 (19)
C19B0.055 (2)0.058 (2)0.059 (2)0.002 (2)0.020 (2)0.0044 (19)
C20B0.068 (2)0.054 (2)0.057 (2)0.004 (2)0.018 (2)0.008 (2)
C21B0.060 (2)0.063 (2)0.050 (2)0.006 (2)0.0099 (19)0.002 (2)
C22B0.053 (2)0.057 (2)0.048 (2)0.0048 (18)0.0073 (17)0.0030 (18)
C23B0.059 (2)0.047 (2)0.046 (2)0.0049 (17)0.0069 (18)0.0031 (17)
C24B0.070 (2)0.048 (2)0.055 (2)0.0001 (18)0.0016 (19)0.0024 (18)
C25B0.066 (2)0.055 (2)0.063 (2)0.013 (2)0.004 (2)0.0021 (19)
C26B0.102 (3)0.069 (3)0.087 (3)0.000 (3)0.025 (3)0.024 (3)
C27B0.055 (2)0.129 (4)0.083 (3)0.002 (3)0.013 (2)0.018 (3)
O210.0700 (18)0.087 (2)0.111 (2)0.0013 (16)0.0024 (17)0.0170 (18)
O220.0787 (19)0.137 (3)0.087 (2)0.010 (2)0.0001 (17)0.032 (2)
O230.113 (2)0.0636 (17)0.0832 (19)0.0014 (17)0.0038 (18)0.0093 (14)
O240.080 (2)0.101 (3)0.112 (3)0.0048 (19)0.016 (2)0.015 (2)
Geometric parameters (Å, º) top
O1A—C5A1.364 (4)O1B—C5B1.361 (4)
O1A—C9A1.426 (4)O1B—C9B1.420 (5)
O2A—C6A1.382 (4)O2B—C6B1.370 (4)
O2A—C10A1.414 (4)O2B—C10B1.419 (4)
O3A—C16A1.238 (4)O3B—C16B1.233 (4)
O4A—C20A1.368 (4)O4B—C20B1.371 (4)
O4A—C26A1.426 (5)O4B—C26B1.425 (5)
O5A—C21A1.380 (4)O5B—C21B1.367 (4)
O5A—C27A1.416 (4)O5B—C27B1.411 (4)
N1A—H1A0.9800N1B—H1B0.9800
N1A—C11A1.498 (4)N1B—C11B1.511 (4)
N1A—C12A1.485 (4)N1B—C12B1.488 (4)
N1A—C13A1.500 (4)N1B—C13B1.498 (4)
N2A—C15A1.456 (4)N2B—C15B1.457 (4)
N2A—C16A1.342 (4)N2B—C16B1.338 (5)
N2A—C25A1.473 (4)N2B—C25B1.465 (5)
O11—H11E0.8222C1B—H1BA0.9800
O11—H11F0.8207C1B—C2B1.580 (5)
O12—H12G0.8248C1B—C8B1.518 (5)
O12—H12H0.8253C1B—C11B1.493 (5)
O13—H13E0.8223C2B—H2BA0.9700
O13—H13F0.8222C2B—H2BB0.9700
O14—H14E0.8205C2B—C3B1.512 (5)
O14—H14F0.8203C3B—C4B1.389 (5)
C1A—H1AA0.9800C3B—C8B1.368 (4)
C1A—C2A1.570 (4)C4B—H4B0.9300
C1A—C8A1.518 (4)C4B—C5B1.387 (5)
C1A—C11A1.510 (4)C5B—C6B1.411 (5)
C2A—H2AA0.9700C6B—C7B1.390 (5)
C2A—H2AB0.9700C7B—H7B0.9300
C2A—C3A1.524 (4)C7B—C8B1.382 (5)
C3A—C4A1.385 (5)C9B—H9BA0.9600
C3A—C8A1.360 (4)C9B—H9BB0.9600
C4A—H4A0.9300C9B—H9BC0.9600
C4A—C5A1.386 (5)C10B—H10D0.9600
C5A—C6A1.413 (5)C10B—H10E0.9600
C6A—C7A1.374 (5)C10B—H10F0.9600
C7A—H7A0.9300C11B—H11C0.9700
C7A—C8A1.381 (4)C11B—H11D0.9700
C9A—H9AA0.9600C12B—H12D0.9600
C9A—H9AB0.9600C12B—H12E0.9600
C9A—H9AC0.9600C12B—H12F0.9600
C10A—H10A0.9600C13B—H13C0.9700
C10A—H10B0.9600C13B—H13D0.9700
C10A—H10C0.9600C13B—C14B1.525 (5)
C11A—H11A0.9700C14B—H14C0.9700
C11A—H11B0.9700C14B—H14D0.9700
C12A—H12A0.9600C14B—C15B1.529 (5)
C12A—H12B0.9600C15B—H15C0.9700
C12A—H12C0.9600C15B—H15D0.9700
C13A—H13A0.9700C16B—C17B1.503 (5)
C13A—H13B0.9700C17B—H17C0.9700
C13A—C14A1.513 (5)C17B—H17D0.9700
C14A—H14A0.9700C17B—C18B1.522 (5)
C14A—H14B0.9700C18B—C19B1.398 (5)
C14A—C15A1.528 (4)C18B—C23B1.392 (5)
C15A—H15A0.9700C19B—H19B0.9300
C15A—H15B0.9700C19B—C20B1.371 (5)
C16A—C17A1.513 (5)C20B—C21B1.404 (5)
C17A—H17A0.9700C21B—C22B1.372 (5)
C17A—H17B0.9700C22B—H22B0.9300
C17A—C18A1.521 (5)C22B—C23B1.401 (5)
C18A—C19A1.403 (5)C23B—C24B1.514 (5)
C18A—C23A1.389 (4)C24B—H24C0.9700
C19A—H19A0.9300C24B—H24D0.9700
C19A—C20A1.364 (5)C24B—C25B1.519 (5)
C20A—C21A1.399 (5)C25B—H25C0.9700
C21A—C22A1.367 (5)C25B—H25D0.9700
C22A—H22A0.9300C26B—H26D0.9600
C22A—C23A1.400 (4)C26B—H26E0.9600
C23A—C24A1.513 (4)C26B—H26F0.9600
C24A—H24A0.9700C27B—H27D0.9600
C24A—H24B0.9700C27B—H27E0.9600
C24A—C25A1.513 (4)C27B—H27F0.9600
C25A—H25A0.9700O21—H21A0.8257
C25A—H25B0.9700O21—H21B0.8198
C26A—H26A0.9600O22—H22C0.8226
C26A—H26B0.9600O22—H22D0.8181
C26A—H26C0.9600O23—H23A0.8202
C27A—H27A0.9600O23—H23B0.8210
C27A—H27B0.9600O24—H24E0.8226
C27A—H27C0.9600O24—H24F0.8214
C5A—O1A—C9A117.4 (3)C5B—O1B—C9B118.5 (3)
C6A—O2A—C10A116.8 (3)C6B—O2B—C10B116.6 (3)
C20A—O4A—C26A117.7 (3)C20B—O4B—C26B117.4 (3)
C21A—O5A—C27A116.9 (3)C21B—O5B—C27B117.4 (3)
C11A—N1A—H1A106.7C11B—N1B—H1B106.0
C11A—N1A—C13A112.6 (3)C12B—N1B—H1B106.0
C12A—N1A—H1A106.7C12B—N1B—C11B112.6 (3)
C12A—N1A—C11A110.5 (3)C12B—N1B—C13B113.2 (3)
C12A—N1A—C13A113.2 (3)C13B—N1B—H1B106.0
C13A—N1A—H1A106.7C13B—N1B—C11B112.2 (3)
C15A—N2A—C25A118.3 (3)C15B—N2B—C25B118.8 (3)
C16A—N2A—C15A121.6 (3)C16B—N2B—C15B120.4 (3)
C16A—N2A—C25A120.1 (3)C16B—N2B—C25B120.7 (3)
H11E—O11—H11F108.3C2B—C1B—H1BA112.2
H12G—O12—H12H109.3C8B—C1B—H1BA112.2
H13E—O13—H13F109.0C8B—C1B—C2B85.3 (2)
H14E—O14—H14F116.5C11B—C1B—H1BA112.2
C2A—C1A—H1AA111.3C11B—C1B—C2B118.9 (3)
C8A—C1A—H1AA111.3C11B—C1B—C8B113.5 (3)
C8A—C1A—C2A85.7 (2)C1B—C2B—H2BA114.2
C11A—C1A—H1AA111.3C1B—C2B—H2BB114.2
C11A—C1A—C2A120.4 (3)H2BA—C2B—H2BB111.4
C11A—C1A—C8A114.6 (3)C3B—C2B—C1B86.6 (2)
C1A—C2A—H2AA114.3C3B—C2B—H2BA114.2
C1A—C2A—H2AB114.3C3B—C2B—H2BB114.2
H2AA—C2A—H2AB111.4C4B—C3B—C2B145.2 (3)
C3A—C2A—C1A86.3 (2)C8B—C3B—C2B93.5 (3)
C3A—C2A—H2AA114.3C8B—C3B—C4B121.2 (3)
C3A—C2A—H2AB114.3C3B—C4B—H4B121.6
C4A—C3A—C2A144.4 (3)C5B—C4B—C3B116.8 (3)
C8A—C3A—C2A93.3 (3)C5B—C4B—H4B121.6
C8A—C3A—C4A122.3 (3)O1B—C5B—C4B124.6 (3)
C3A—C4A—H4A121.9O1B—C5B—C6B114.2 (3)
C3A—C4A—C5A116.2 (3)C4B—C5B—C6B121.3 (3)
C5A—C4A—H4A121.9O2B—C6B—C5B114.7 (3)
O1A—C5A—C4A125.0 (3)O2B—C6B—C7B124.0 (3)
O1A—C5A—C6A114.2 (3)C7B—C6B—C5B121.2 (3)
C4A—C5A—C6A120.8 (3)C6B—C7B—H7B122.0
O2A—C6A—C5A114.4 (3)C8B—C7B—C6B115.9 (3)
C7A—C6A—O2A123.7 (3)C8B—C7B—H7B122.0
C7A—C6A—C5A121.9 (3)C3B—C8B—C1B94.5 (3)
C6A—C7A—H7A122.0C3B—C8B—C7B123.5 (3)
C6A—C7A—C8A116.0 (3)C7B—C8B—C1B142.0 (3)
C8A—C7A—H7A122.0O1B—C9B—H9BA109.5
C3A—C8A—C1A94.6 (3)O1B—C9B—H9BB109.5
C3A—C8A—C7A122.8 (3)O1B—C9B—H9BC109.5
C7A—C8A—C1A142.6 (3)H9BA—C9B—H9BB109.5
O1A—C9A—H9AA109.5H9BA—C9B—H9BC109.5
O1A—C9A—H9AB109.5H9BB—C9B—H9BC109.5
O1A—C9A—H9AC109.5O2B—C10B—H10D109.5
H9AA—C9A—H9AB109.5O2B—C10B—H10E109.5
H9AA—C9A—H9AC109.5O2B—C10B—H10F109.5
H9AB—C9A—H9AC109.5H10D—C10B—H10E109.5
O2A—C10A—H10A109.5H10D—C10B—H10F109.5
O2A—C10A—H10B109.5H10E—C10B—H10F109.5
O2A—C10A—H10C109.5N1B—C11B—H11C108.2
H10A—C10A—H10B109.5N1B—C11B—H11D108.2
H10A—C10A—H10C109.5C1B—C11B—N1B116.3 (3)
H10B—C10A—H10C109.5C1B—C11B—H11C108.2
N1A—C11A—C1A114.7 (3)C1B—C11B—H11D108.2
N1A—C11A—H11A108.6H11C—C11B—H11D107.4
N1A—C11A—H11B108.6N1B—C12B—H12D109.5
C1A—C11A—H11A108.6N1B—C12B—H12E109.5
C1A—C11A—H11B108.6N1B—C12B—H12F109.5
H11A—C11A—H11B107.6H12D—C12B—H12E109.5
N1A—C12A—H12A109.5H12D—C12B—H12F109.5
N1A—C12A—H12B109.5H12E—C12B—H12F109.5
N1A—C12A—H12C109.5N1B—C13B—H13C109.2
H12A—C12A—H12B109.5N1B—C13B—H13D109.2
H12A—C12A—H12C109.5N1B—C13B—C14B112.1 (3)
H12B—C12A—H12C109.5H13C—C13B—H13D107.9
N1A—C13A—H13A109.0C14B—C13B—H13C109.2
N1A—C13A—H13B109.0C14B—C13B—H13D109.2
N1A—C13A—C14A113.0 (3)C13B—C14B—H14C109.3
H13A—C13A—H13B107.8C13B—C14B—H14D109.3
C14A—C13A—H13A109.0C13B—C14B—C15B111.5 (3)
C14A—C13A—H13B109.0H14C—C14B—H14D108.0
C13A—C14A—H14A109.3C15B—C14B—H14C109.3
C13A—C14A—H14B109.3C15B—C14B—H14D109.3
C13A—C14A—C15A111.7 (3)N2B—C15B—C14B113.1 (3)
H14A—C14A—H14B107.9N2B—C15B—H15C109.0
C15A—C14A—H14A109.3N2B—C15B—H15D109.0
C15A—C14A—H14B109.3C14B—C15B—H15C109.0
N2A—C15A—C14A113.6 (3)C14B—C15B—H15D109.0
N2A—C15A—H15A108.8H15C—C15B—H15D107.8
N2A—C15A—H15B108.8O3B—C16B—N2B123.4 (4)
C14A—C15A—H15A108.8O3B—C16B—C17B119.8 (4)
C14A—C15A—H15B108.8N2B—C16B—C17B116.8 (4)
H15A—C15A—H15B107.7C16B—C17B—H17C109.4
O3A—C16A—N2A122.9 (3)C16B—C17B—H17D109.4
O3A—C16A—C17A119.7 (3)C16B—C17B—C18B111.0 (3)
N2A—C16A—C17A117.3 (3)H17C—C17B—H17D108.0
C16A—C17A—H17A109.0C18B—C17B—H17C109.4
C16A—C17A—H17B109.0C18B—C17B—H17D109.4
C16A—C17A—C18A112.7 (3)C19B—C18B—C17B117.8 (3)
H17A—C17A—H17B107.8C23B—C18B—C17B122.3 (3)
C18A—C17A—H17A109.0C23B—C18B—C19B119.8 (3)
C18A—C17A—H17B109.0C18B—C19B—H19B119.3
C19A—C18A—C17A117.9 (3)C20B—C19B—C18B121.4 (3)
C23A—C18A—C17A123.0 (3)C20B—C19B—H19B119.3
C23A—C18A—C19A119.0 (3)O4B—C20B—C19B125.7 (4)
C18A—C19A—H19A118.9O4B—C20B—C21B114.9 (3)
C20A—C19A—C18A122.2 (3)C19B—C20B—C21B119.4 (3)
C20A—C19A—H19A118.9O5B—C21B—C20B116.2 (3)
O4A—C20A—C21A115.4 (3)O5B—C21B—C22B124.6 (3)
C19A—C20A—O4A125.8 (3)C22B—C21B—C20B119.2 (4)
C19A—C20A—C21A118.8 (3)C21B—C22B—H22B118.9
O5A—C21A—C20A115.8 (3)C21B—C22B—C23B122.3 (3)
C22A—C21A—O5A124.6 (3)C23B—C22B—H22B118.9
C22A—C21A—C20A119.6 (3)C18B—C23B—C22B118.0 (3)
C21A—C22A—H22A118.9C18B—C23B—C24B126.2 (3)
C21A—C22A—C23A122.2 (3)C22B—C23B—C24B115.8 (3)
C23A—C22A—H22A118.9C23B—C24B—H24C107.9
C18A—C23A—C22A118.2 (3)C23B—C24B—H24D107.9
C18A—C23A—C24A125.8 (3)C23B—C24B—C25B117.7 (3)
C22A—C23A—C24A115.9 (3)H24C—C24B—H24D107.2
C23A—C24A—H24A107.7C25B—C24B—H24C107.9
C23A—C24A—H24B107.7C25B—C24B—H24D107.9
C23A—C24A—C25A118.4 (3)N2B—C25B—C24B113.6 (3)
H24A—C24A—H24B107.1N2B—C25B—H25C108.9
C25A—C24A—H24A107.7N2B—C25B—H25D108.9
C25A—C24A—H24B107.7C24B—C25B—H25C108.9
N2A—C25A—C24A112.9 (3)C24B—C25B—H25D108.9
N2A—C25A—H25A109.0H25C—C25B—H25D107.7
N2A—C25A—H25B109.0O4B—C26B—H26D109.5
C24A—C25A—H25A109.0O4B—C26B—H26E109.5
C24A—C25A—H25B109.0O4B—C26B—H26F109.5
H25A—C25A—H25B107.8H26D—C26B—H26E109.5
O4A—C26A—H26A109.5H26D—C26B—H26F109.5
O4A—C26A—H26B109.5H26E—C26B—H26F109.5
O4A—C26A—H26C109.5O5B—C27B—H27D109.5
H26A—C26A—H26B109.5O5B—C27B—H27E109.5
H26A—C26A—H26C109.5O5B—C27B—H27F109.5
H26B—C26A—H26C109.5H27D—C27B—H27E109.5
O5A—C27A—H27A109.5H27D—C27B—H27F109.5
O5A—C27A—H27B109.5H27E—C27B—H27F109.5
O5A—C27A—H27C109.5H21A—O21—H21B111.2
H27A—C27A—H27B109.5H22C—O22—H22D107.1
H27A—C27A—H27C109.5H23A—O23—H23B97.9
H27B—C27A—H27C109.5H24E—O24—H24F113.6
O1A—C5A—C6A—O2A0.3 (5)O1B—C5B—C6B—O2B3.2 (5)
O1A—C5A—C6A—C7A178.0 (3)O1B—C5B—C6B—C7B178.8 (3)
O2A—C6A—C7A—C8A179.4 (3)O2B—C6B—C7B—C8B177.9 (3)
O3A—C16A—C17A—C18A106.7 (4)O3B—C16B—C17B—C18B105.1 (4)
O4A—C20A—C21A—O5A0.7 (5)O4B—C20B—C21B—O5B1.8 (5)
O4A—C20A—C21A—C22A178.0 (3)O4B—C20B—C21B—C22B178.3 (3)
O5A—C21A—C22A—C23A179.7 (3)O5B—C21B—C22B—C23B179.1 (3)
N1A—C13A—C14A—C15A168.8 (3)N1B—C13B—C14B—C15B168.0 (3)
N2A—C16A—C17A—C18A70.2 (4)N2B—C16B—C17B—C18B72.4 (4)
C1A—C2A—C3A—C4A178.1 (5)C1B—C2B—C3B—C4B177.3 (5)
C1A—C2A—C3A—C8A3.1 (3)C1B—C2B—C3B—C8B1.1 (3)
C2A—C1A—C8A—C3A3.1 (3)C2B—C1B—C8B—C3B1.1 (3)
C2A—C1A—C8A—C7A177.0 (5)C2B—C1B—C8B—C7B178.8 (5)
C2A—C1A—C11A—N1A90.0 (4)C2B—C1B—C11B—N1B91.8 (4)
C2A—C3A—C4A—C5A177.0 (4)C2B—C3B—C4B—C5B179.2 (5)
C2A—C3A—C8A—C1A3.2 (3)C2B—C3B—C8B—C1B1.2 (3)
C2A—C3A—C8A—C7A176.9 (4)C2B—C3B—C8B—C7B178.7 (3)
C3A—C4A—C5A—O1A179.5 (3)C3B—C4B—C5B—O1B179.3 (3)
C3A—C4A—C5A—C6A0.3 (5)C3B—C4B—C5B—C6B0.6 (5)
C4A—C3A—C8A—C1A177.6 (3)C4B—C3B—C8B—C1B177.8 (3)
C4A—C3A—C8A—C7A2.3 (5)C4B—C3B—C8B—C7B2.3 (5)
C4A—C5A—C6A—O2A179.9 (3)C4B—C5B—C6B—O2B177.0 (4)
C4A—C5A—C6A—C7A1.9 (6)C4B—C5B—C6B—C7B1.1 (6)
C5A—C6A—C7A—C8A1.3 (5)C5B—C6B—C7B—C8B0.0 (5)
C6A—C7A—C8A—C1A179.1 (4)C6B—C7B—C8B—C1B178.5 (4)
C6A—C7A—C8A—C3A0.7 (5)C6B—C7B—C8B—C3B1.7 (5)
C8A—C1A—C2A—C3A2.7 (2)C8B—C1B—C2B—C3B1.0 (2)
C8A—C1A—C11A—N1A170.1 (3)C8B—C1B—C11B—N1B170.3 (3)
C8A—C3A—C4A—C5A1.7 (5)C8B—C3B—C4B—C5B1.1 (5)
C9A—O1A—C5A—C4A1.6 (5)C9B—O1B—C5B—C4B5.3 (6)
C9A—O1A—C5A—C6A178.3 (3)C9B—O1B—C5B—C6B174.5 (4)
C10A—O2A—C6A—C5A173.8 (3)C10B—O2B—C6B—C5B176.3 (4)
C10A—O2A—C6A—C7A8.0 (5)C10B—O2B—C6B—C7B1.8 (6)
C11A—N1A—C13A—C14A172.4 (3)C11B—N1B—C13B—C14B158.1 (3)
C11A—C1A—C2A—C3A118.8 (3)C11B—C1B—C2B—C3B115.3 (3)
C11A—C1A—C8A—C3A124.6 (3)C11B—C1B—C8B—C3B120.7 (3)
C11A—C1A—C8A—C7A55.5 (6)C11B—C1B—C8B—C7B59.2 (6)
C12A—N1A—C11A—C1A170.9 (3)C12B—N1B—C11B—C1B73.8 (4)
C12A—N1A—C13A—C14A61.4 (4)C12B—N1B—C13B—C14B73.1 (4)
C13A—N1A—C11A—C1A61.5 (4)C13B—N1B—C11B—C1B55.4 (4)
C13A—C14A—C15A—N2A61.3 (4)C13B—C14B—C15B—N2B54.8 (4)
C15A—N2A—C16A—O3A3.7 (5)C15B—N2B—C16B—O3B0.5 (5)
C15A—N2A—C16A—C17A179.5 (3)C15B—N2B—C16B—C17B176.9 (3)
C15A—N2A—C25A—C24A107.3 (3)C15B—N2B—C25B—C24B103.8 (3)
C16A—N2A—C15A—C14A108.2 (4)C16B—N2B—C15B—C14B103.6 (4)
C16A—N2A—C25A—C24A73.8 (4)C16B—N2B—C25B—C24B73.4 (4)
C16A—C17A—C18A—C19A122.5 (3)C16B—C17B—C18B—C19B120.9 (4)
C16A—C17A—C18A—C23A53.9 (4)C16B—C17B—C18B—C23B56.4 (5)
C17A—C18A—C19A—C20A175.8 (3)C17B—C18B—C19B—C20B176.5 (3)
C17A—C18A—C23A—C22A175.6 (3)C17B—C18B—C23B—C22B175.9 (3)
C17A—C18A—C23A—C24A3.1 (5)C17B—C18B—C23B—C24B4.3 (5)
C18A—C19A—C20A—O4A178.0 (3)C18B—C19B—C20B—O4B178.1 (3)
C18A—C19A—C20A—C21A1.0 (5)C18B—C19B—C20B—C21B0.3 (6)
C18A—C23A—C24A—C25A1.7 (5)C18B—C23B—C24B—C25B6.4 (5)
C19A—C18A—C23A—C22A0.8 (5)C19B—C18B—C23B—C22B1.3 (5)
C19A—C18A—C23A—C24A179.5 (3)C19B—C18B—C23B—C24B178.5 (3)
C19A—C20A—C21A—O5A179.8 (3)C19B—C20B—C21B—O5B179.7 (3)
C19A—C20A—C21A—C22A1.1 (5)C19B—C20B—C21B—C22B0.3 (5)
C20A—C21A—C22A—C23A1.1 (5)C20B—C21B—C22B—C23B0.9 (5)
C21A—C22A—C23A—C18A1.0 (5)C21B—C22B—C23B—C18B1.3 (5)
C21A—C22A—C23A—C24A179.8 (3)C21B—C22B—C23B—C24B178.5 (3)
C22A—C23A—C24A—C25A177.0 (3)C22B—C23B—C24B—C25B173.7 (3)
C23A—C18A—C19A—C20A0.8 (5)C23B—C18B—C19B—C20B0.8 (5)
C23A—C24A—C25A—N2A57.2 (4)C23B—C24B—C25B—N2B53.0 (4)
C25A—N2A—C15A—C14A72.9 (4)C25B—N2B—C15B—C14B73.6 (4)
C25A—N2A—C16A—O3A177.5 (3)C25B—N2B—C16B—O3B177.7 (3)
C25A—N2A—C16A—C17A0.7 (4)C25B—N2B—C16B—C17B0.3 (5)
C26A—O4A—C20A—C19A11.6 (5)C26B—O4B—C20B—C19B3.7 (5)
C26A—O4A—C20A—C21A167.5 (3)C26B—O4B—C20B—C21B174.7 (3)
C27A—O5A—C21A—C20A167.2 (3)C27B—O5B—C21B—C20B166.0 (4)
C27A—O5A—C21A—C22A11.5 (5)C27B—O5B—C21B—C22B14.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···Cl10.982.103.070 (3)172
O11—H11E···O3Ai0.821.882.685 (4)166
O11—H11F···O130.821.892.702 (4)171
O12—H12G···O110.821.992.774 (4)158
O12—H12H···Cl20.832.403.209 (3)168
O13—H13E···O14i0.821.922.715 (4)163
O14—H14E···O110.821.972.777 (4)169
O14—H14F···Cl20.822.383.137 (3)154
N1B—H1B···Cl20.982.073.018 (3)162
O21—H21A···Cl10.832.413.208 (3)163
O21—H21B···O23ii0.821.982.795 (4)176
O22—H22C···O210.821.982.745 (4)154
O22—H22D···O240.821.932.738 (4)170
O23—H23A···O220.821.902.701 (4)167
O23—H23B···O3Biii0.821.902.706 (4)166
O24—H24E···Cl1iii0.822.403.172 (4)158
O24—H24F···O23iv0.822.092.801 (5)145
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x+1/2, y+1/2, z+1; (iii) x1, y, z; (iv) x1/2, y+1/2, z+1.
Thermophysical data for the hemihydrate and tetrahydrate top
Solid formHemihydrateTetrahydrate
Desolvation onset temperature (°C)152.659.3
Desolvation enthalpy change ΔHS,exp (J g-1)60.2318.5
Calcd weight loss (ΔmS%)1.812.5
Obsd weight loss in TGA (ΔmS%)1.712.5
Calculated binding energy (kJ mol-1)63.745.8
Heat of vaporization of the pure solvate ΔHPS (kJ mol-1)40.740.7
Boiling point of pure solvent (°C)100100
 

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