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The absolute configuration was determined for the title compound, C38H70NO13+·Cl-·3.5H2O. The cation contains a 14-membered macrocyclic lactone and two sugars, namely cladinose and desos­amine. The six-membered rings of the sugars adopt chair conformations. The structure is stabilized by strong hydrogen bonds, with O...O distances in the range 2.486 (9)-2.830 (5) Å; other distances are N...O = 2.860 (5), N...Cl = 3.134 (4) and O...Cl = 3.303 (4) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100010490/qd0001sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010490/qd0001Isup2.hkl
Contains datablock I

CCDC reference: 150735

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: TEXSAN (Molecular Structure Corporation, 1994); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXTL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXTL97.

6-O-Methylerythromycin A Hydrochloride 3.5 Hydrate top
Crystal data top
C38H70NO13+·Cl·3.5H2ODx = 1.228 Mg m3
Mr = 847.46Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 14.409 (2) Åθ = 20.0–30.0°
b = 16.489 (3) ŵ = 1.30 mm1
c = 19.267 (3) ÅT = 293 K
V = 4577.6 (13) Å3Block, colourless
Z = 40.50 × 0.38 × 0.35 mm
F(000) = 1844
Data collection top
Enraf-Nonius CAD-4
diffractometer
5541 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.062
Graphite monochromatorθmax = 68.0°, θmin = 5.0°
ω–2θ scansh = 017
Absorption correction: empirical (using intensity measurements)
ψ scan (3 reflections; North et al., 1968)
k = 019
Tmin = 0.56, Tmax = 0.66l = 2323
8735 measured reflections3 standard reflections every 200 reflections
8291 independent reflections intensity decay: 12.6%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: geom and difference maps
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.150 w = 1/[σ2(Fo2) + (0.047P)2 + 3.56P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
8291 reflectionsΔρmax = 0.20 e Å3
532 parametersΔρmin = 0.25 e Å3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (3)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.25061 (11)0.87642 (10)0.04179 (7)0.0837 (4)
O10.55650 (18)0.60759 (17)0.34796 (16)0.0475 (7)
O20.4746 (2)0.5024 (2)0.38923 (18)0.0618 (9)
O30.23968 (18)0.63278 (17)0.31443 (14)0.0427 (7)
O40.1304 (2)0.53247 (17)0.34298 (16)0.0492 (7)
O50.0660 (2)0.71118 (18)0.26086 (18)0.0577 (8)
O60.0778 (2)0.6117 (2)0.25741 (18)0.0659 (10)
H60.11880.57770.26210.099*
O70.27955 (19)0.58293 (17)0.12528 (15)0.0467 (7)
O80.13238 (19)0.54420 (17)0.10599 (15)0.0471 (7)
O90.2349 (4)0.7438 (2)0.0862 (3)0.1074 (17)
H90.26320.76420.05370.161*
O100.4043 (2)0.42754 (18)0.21812 (16)0.0554 (8)
O110.5730 (3)0.3296 (2)0.1690 (2)0.0791 (12)
O120.6457 (3)0.40473 (19)0.28939 (18)0.0640 (9)
H120.63140.36460.26670.096*
O130.77492 (19)0.5218 (2)0.28931 (18)0.0590 (9)
H130.77780.47700.30760.089*
N10.0855 (3)0.7581 (2)0.01075 (19)0.0543 (10)
H10.13530.79130.00470.065*
C10.4783 (3)0.5701 (3)0.3690 (2)0.0436 (10)
C20.3962 (3)0.6274 (3)0.3636 (2)0.0452 (10)
H20.41830.67870.34380.054*
C30.3265 (3)0.5898 (3)0.3124 (2)0.0392 (10)
H30.31570.53310.32550.047*
C40.3626 (3)0.5926 (2)0.2380 (2)0.0414 (10)
H40.42450.56800.23930.050*
C50.3046 (3)0.5394 (2)0.1877 (2)0.0405 (9)
H50.24770.52220.21140.049*
C60.3560 (3)0.4635 (3)0.1608 (2)0.0430 (10)
C70.4333 (3)0.4885 (3)0.1105 (2)0.0469 (11)
H7A0.46860.53210.13160.056*
H7B0.40490.50980.06870.056*
C80.5013 (3)0.4204 (3)0.0896 (2)0.0532 (12)
H80.46480.37190.07880.064*
C90.5687 (4)0.3988 (3)0.1467 (3)0.0555 (12)
C100.6362 (3)0.4622 (3)0.1721 (2)0.0509 (11)
H100.62220.51320.14810.061*
C110.6237 (3)0.4763 (3)0.2508 (2)0.0479 (11)
H110.55800.48850.25890.058*
C120.6802 (3)0.5453 (3)0.2825 (2)0.0472 (11)
C130.6450 (3)0.5657 (3)0.3558 (2)0.0495 (11)
H13A0.63540.51540.38190.059*
C140.7063 (3)0.6221 (4)0.3974 (3)0.0694 (15)
H14A0.76670.59690.40290.083*
H14B0.71510.67170.37120.083*
C150.6699 (4)0.6436 (5)0.4675 (3)0.102 (2)
H15A0.61240.67250.46270.153*
H15B0.71420.67710.49120.153*
H15C0.65960.59490.49380.153*
C160.3631 (3)0.6439 (4)0.4380 (3)0.0772 (18)
H16A0.34070.59440.45830.116*
H16B0.31400.68330.43720.116*
H16C0.41380.66440.46510.116*
C170.1752 (3)0.6043 (3)0.3643 (2)0.0444 (10)
H170.20980.59200.40680.053*
C180.1080 (3)0.6718 (3)0.3807 (2)0.0535 (12)
H18A0.14280.72190.38560.064*
H18B0.07900.66030.42500.064*
C190.0320 (3)0.6850 (3)0.3269 (2)0.0506 (12)
C200.0115 (3)0.6029 (3)0.3116 (2)0.0498 (11)
H200.04310.58330.35340.060*
C210.0602 (3)0.5412 (3)0.2897 (2)0.0478 (11)
H210.08970.55910.24650.057*
C220.0414 (4)0.7430 (3)0.3550 (3)0.0789 (17)
H22A0.01290.79390.36630.118*
H22B0.06890.72020.39600.118*
H22C0.08850.75130.32050.118*
C230.1196 (4)0.7839 (3)0.2608 (3)0.0789 (18)
H23A0.08870.82440.28810.118*
H23B0.12630.80310.21400.118*
H23C0.17970.77310.28010.118*
C240.0213 (4)0.4574 (3)0.2797 (3)0.0706 (15)
H24A0.06890.42220.26210.106*
H24B0.02920.45940.24720.106*
H24C0.00070.43690.32340.106*
C250.3768 (4)0.6790 (3)0.2114 (2)0.0562 (13)
H25A0.31930.70830.21450.084*
H25B0.39690.67740.16390.084*
H25C0.42300.70570.23910.084*
C260.1886 (3)0.6116 (3)0.1213 (2)0.0443 (10)
H260.16980.63670.16520.053*
C270.1875 (3)0.6733 (3)0.0630 (3)0.0523 (12)
H270.21700.65120.02120.063*
C280.0882 (3)0.6968 (3)0.0485 (2)0.0464 (11)
H280.06410.72380.09010.056*
C290.0293 (3)0.6238 (3)0.0354 (2)0.0541 (12)
H29A0.05000.59650.00640.065*
H29B0.03480.64000.02900.065*
C300.0368 (3)0.5666 (3)0.0969 (2)0.0471 (11)
H300.01350.59320.13890.056*
C310.0947 (4)0.7225 (4)0.0815 (2)0.0742 (16)
H31A0.03990.69210.09240.111*
H31B0.14780.68740.08280.111*
H31C0.10250.76530.11480.111*
C320.0014 (4)0.8109 (3)0.0067 (3)0.0803 (18)
H32A0.00120.84800.04510.120*
H32B0.00230.84080.03610.120*
H32C0.05330.77770.00850.120*
C330.0156 (3)0.4895 (3)0.0842 (3)0.0666 (14)
H33A0.00760.46380.04310.100*
H33B0.08030.50160.07840.100*
H33C0.00780.45380.12320.100*
C340.2885 (3)0.4059 (3)0.1252 (3)0.0660 (15)
H34A0.31910.35530.11590.099*
H34B0.26790.42950.08230.099*
H34C0.23610.39660.15490.099*
C350.3594 (5)0.3714 (4)0.2612 (3)0.108 (2)
H35A0.29620.38790.26810.163*
H35B0.39070.36910.30510.163*
H35C0.36070.31890.23980.163*
C360.5544 (4)0.4450 (4)0.0240 (2)0.0729 (16)
H36A0.58940.49340.03300.109*
H36B0.51120.45480.01300.109*
H36C0.59590.40210.01090.109*
C370.7349 (4)0.4357 (4)0.1514 (3)0.0835 (18)
H37A0.74940.38510.17350.125*
H37B0.77860.47630.16590.125*
H37C0.73810.42930.10190.125*
C380.6798 (3)0.6209 (3)0.2365 (3)0.0599 (13)
H38A0.71530.66310.25830.090*
H38B0.61710.63910.23000.090*
H38C0.70670.60810.19230.090*
O140.3813 (3)0.7691 (3)0.1486 (2)0.0993 (14)
O150.1859 (3)0.3791 (3)0.4090 (3)0.1119 (16)
O160.1777 (3)0.9109 (3)0.1089 (2)0.0964 (13)
O170.3762 (5)0.8302 (5)0.0820 (4)0.090 (2)0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0881 (10)0.0997 (11)0.0634 (8)0.0169 (9)0.0078 (8)0.0186 (8)
O10.0307 (15)0.0522 (17)0.0595 (18)0.0041 (14)0.0042 (14)0.0062 (15)
O20.0428 (18)0.064 (2)0.079 (2)0.0029 (16)0.0019 (17)0.0277 (19)
O30.0302 (15)0.0475 (16)0.0503 (16)0.0025 (13)0.0007 (13)0.0045 (14)
O40.0412 (17)0.0476 (17)0.0589 (18)0.0045 (14)0.0063 (15)0.0087 (14)
O50.052 (2)0.0515 (18)0.070 (2)0.0066 (16)0.0039 (17)0.0098 (16)
O60.0378 (19)0.087 (3)0.073 (2)0.0110 (17)0.0182 (17)0.022 (2)
O70.0384 (16)0.0559 (18)0.0459 (17)0.0019 (14)0.0075 (13)0.0068 (14)
O80.0398 (16)0.0429 (15)0.0586 (18)0.0010 (14)0.0104 (14)0.0011 (14)
O90.120 (4)0.065 (2)0.137 (4)0.040 (3)0.074 (3)0.047 (3)
O100.056 (2)0.0550 (18)0.0552 (19)0.0042 (16)0.0058 (16)0.0174 (15)
O110.098 (3)0.0432 (19)0.097 (3)0.018 (2)0.010 (2)0.0025 (19)
O120.068 (2)0.0556 (19)0.068 (2)0.0017 (19)0.0076 (19)0.0177 (17)
O130.0250 (16)0.076 (2)0.076 (2)0.0042 (15)0.0017 (15)0.0205 (19)
N10.055 (2)0.055 (2)0.053 (2)0.0082 (19)0.007 (2)0.0029 (19)
C10.030 (2)0.057 (3)0.044 (2)0.005 (2)0.0015 (19)0.003 (2)
C20.032 (2)0.055 (3)0.048 (2)0.002 (2)0.0043 (19)0.007 (2)
C30.026 (2)0.046 (2)0.046 (2)0.0020 (18)0.0025 (18)0.001 (2)
C40.038 (2)0.043 (2)0.043 (2)0.0023 (19)0.005 (2)0.0031 (18)
C50.040 (2)0.041 (2)0.041 (2)0.0023 (19)0.0064 (19)0.0050 (19)
C60.041 (2)0.045 (2)0.043 (2)0.003 (2)0.003 (2)0.0055 (19)
C70.054 (3)0.046 (2)0.041 (2)0.005 (2)0.003 (2)0.0004 (19)
C80.060 (3)0.048 (3)0.051 (3)0.004 (2)0.003 (2)0.007 (2)
C90.064 (3)0.045 (3)0.057 (3)0.014 (2)0.008 (2)0.003 (2)
C100.044 (3)0.056 (3)0.053 (3)0.013 (2)0.005 (2)0.006 (2)
C110.034 (2)0.053 (3)0.056 (3)0.003 (2)0.000 (2)0.011 (2)
C120.025 (2)0.058 (3)0.059 (3)0.008 (2)0.002 (2)0.011 (2)
C130.030 (2)0.062 (3)0.056 (3)0.001 (2)0.004 (2)0.006 (2)
C140.040 (3)0.100 (4)0.068 (3)0.016 (3)0.010 (2)0.009 (3)
C150.075 (4)0.159 (7)0.072 (4)0.040 (4)0.005 (3)0.022 (4)
C160.041 (3)0.130 (5)0.061 (3)0.001 (3)0.007 (3)0.040 (3)
C170.038 (2)0.056 (3)0.039 (2)0.006 (2)0.0025 (19)0.001 (2)
C180.038 (3)0.068 (3)0.054 (3)0.001 (2)0.001 (2)0.011 (2)
C190.041 (3)0.053 (3)0.057 (3)0.002 (2)0.005 (2)0.003 (2)
C200.034 (2)0.062 (3)0.053 (3)0.001 (2)0.002 (2)0.011 (2)
C210.048 (3)0.051 (2)0.044 (2)0.011 (2)0.009 (2)0.007 (2)
C220.051 (3)0.075 (4)0.110 (5)0.013 (3)0.013 (3)0.013 (3)
C230.062 (4)0.045 (3)0.129 (5)0.007 (3)0.009 (4)0.015 (3)
C240.070 (4)0.056 (3)0.086 (4)0.022 (3)0.009 (3)0.001 (3)
C250.061 (3)0.053 (3)0.055 (3)0.021 (2)0.000 (2)0.003 (2)
C260.038 (2)0.042 (2)0.052 (3)0.003 (2)0.009 (2)0.000 (2)
C270.046 (3)0.049 (3)0.061 (3)0.004 (2)0.013 (2)0.007 (2)
C280.049 (3)0.050 (3)0.040 (2)0.009 (2)0.004 (2)0.003 (2)
C290.042 (3)0.069 (3)0.051 (3)0.007 (2)0.004 (2)0.005 (2)
C300.031 (2)0.057 (3)0.053 (3)0.003 (2)0.008 (2)0.003 (2)
C310.091 (4)0.087 (4)0.044 (3)0.002 (3)0.000 (3)0.005 (3)
C320.075 (4)0.070 (4)0.096 (4)0.035 (3)0.006 (3)0.018 (3)
C330.049 (3)0.074 (4)0.076 (4)0.015 (3)0.010 (3)0.005 (3)
C340.061 (3)0.052 (3)0.085 (4)0.013 (2)0.007 (3)0.014 (3)
C350.136 (6)0.094 (5)0.095 (5)0.028 (5)0.010 (5)0.052 (4)
C360.074 (4)0.094 (4)0.051 (3)0.013 (3)0.011 (3)0.011 (3)
C370.052 (3)0.116 (5)0.082 (4)0.023 (3)0.013 (3)0.001 (4)
C380.051 (3)0.060 (3)0.068 (3)0.003 (3)0.000 (3)0.016 (3)
O140.109 (3)0.085 (3)0.103 (3)0.012 (3)0.001 (3)0.017 (2)
O150.108 (3)0.092 (3)0.135 (4)0.004 (3)0.047 (3)0.023 (3)
O160.108 (3)0.102 (3)0.080 (3)0.020 (3)0.002 (3)0.020 (2)
O170.073 (5)0.094 (6)0.103 (6)0.006 (5)0.006 (5)0.002 (5)
Geometric parameters (Å, º) top
O1—C11.348 (5)C15—H15C0.9600
O1—C131.458 (5)C16—H16A0.9600
O2—C11.184 (5)C16—H16B0.9600
O3—C171.416 (5)C16—H16C0.9600
O3—C31.438 (5)C17—C181.509 (6)
O4—C171.410 (5)C17—H170.9800
O4—C211.448 (5)C18—C191.523 (6)
O5—C231.426 (5)C18—H18A0.9700
O5—C191.431 (5)C18—H18B0.9700
O6—C201.422 (5)C19—C201.520 (6)
O6—H60.8200C19—C221.525 (6)
O7—C261.396 (5)C20—C211.512 (6)
O7—C51.446 (5)C20—H200.9800
O8—C261.407 (5)C21—C241.504 (6)
O8—C301.437 (5)C21—H210.9800
O9—C271.421 (5)C22—H22A0.9600
O9—H90.8200C22—H22B0.9600
O10—C351.400 (6)C22—H22C0.9600
O10—C61.434 (5)C23—H23A0.9600
O11—C91.220 (5)C23—H23B0.9600
O12—C111.431 (5)C23—H23C0.9600
O12—H120.8200C24—H24A0.9600
O13—C121.424 (5)C24—H24B0.9600
O13—H130.8200C24—H24C0.9600
N1—C311.490 (6)C25—H25A0.9600
N1—C321.493 (6)C25—H25B0.9600
N1—C281.525 (5)C25—H25C0.9600
N1—H10.9100C26—C271.516 (6)
C1—C21.517 (6)C26—H260.9800
C2—C161.536 (6)C27—C281.509 (6)
C2—C31.538 (5)C27—H270.9800
C2—H20.9800C28—C291.495 (6)
C3—C41.526 (6)C28—H280.9800
C3—H30.9800C29—C301.517 (6)
C4—C251.528 (6)C29—H29A0.9700
C4—C51.552 (5)C29—H29B0.9700
C4—H40.9800C30—C331.498 (6)
C5—C61.544 (6)C30—H300.9800
C5—H50.9800C31—H31A0.9600
C6—C341.522 (6)C31—H31B0.9600
C6—C71.534 (6)C31—H31C0.9600
C7—C81.544 (6)C32—H32A0.9600
C7—H7A0.9700C32—H32B0.9600
C7—H7B0.9700C32—H32C0.9600
C8—C91.509 (7)C33—H33A0.9600
C8—C361.533 (6)C33—H33B0.9600
C8—H80.9800C33—H33C0.9600
C9—C101.509 (7)C34—H34A0.9600
C10—C371.540 (6)C34—H34B0.9600
C10—C111.545 (6)C34—H34C0.9600
C10—H100.9800C35—H35A0.9600
C11—C121.526 (6)C35—H35B0.9600
C11—H110.9800C35—H35C0.9600
C12—C381.531 (6)C36—H36A0.9600
C12—C131.538 (6)C36—H36B0.9600
C13—C141.512 (6)C36—H36C0.9600
C13—H13A0.9800C37—H37A0.9600
C14—C151.492 (7)C37—H37B0.9600
C14—H14A0.9700C37—H37C0.9600
C14—H14B0.9700C38—H38A0.9600
C15—H15A0.9600C38—H38B0.9600
C15—H15B0.9600C38—H38C0.9600
C1—O1—C13118.9 (3)O5—C19—C18113.7 (4)
C17—O3—C3115.2 (3)C20—C19—C18107.6 (4)
C17—O4—C21116.3 (3)O5—C19—C22111.3 (4)
C23—O5—C19116.2 (4)C20—C19—C22110.0 (4)
C20—O6—H6109.5C18—C19—C22110.3 (4)
C26—O7—C5116.6 (3)O6—C20—C21108.9 (4)
C26—O8—C30112.0 (3)O6—C20—C19109.2 (4)
C27—O9—H9109.5C21—C20—C19111.8 (4)
C35—O10—C6120.4 (4)O6—C20—H20109.0
C11—O12—H12109.5C21—C20—H20109.0
C12—O13—H13109.5C19—C20—H20109.0
C31—N1—C32110.5 (4)O4—C21—C24105.1 (4)
C31—N1—C28114.9 (4)O4—C21—C20110.3 (3)
C32—N1—C28111.6 (4)C24—C21—C20113.5 (4)
C31—N1—H1106.4O4—C21—H21109.3
C32—N1—H1106.4C24—C21—H21109.3
C28—N1—H1106.4C20—C21—H21109.3
O2—C1—O1124.7 (4)C19—C22—H22A109.5
O2—C1—C2125.1 (4)C19—C22—H22B109.5
O1—C1—C2110.2 (4)H22A—C22—H22B109.5
C1—C2—C16106.8 (4)C19—C22—H22C109.5
C1—C2—C3107.6 (3)H22A—C22—H22C109.5
C16—C2—C3117.8 (4)H22B—C22—H22C109.5
C1—C2—H2108.1O5—C23—H23A109.5
C16—C2—H2108.1O5—C23—H23B109.5
C3—C2—H2108.1H23A—C23—H23B109.5
O3—C3—C4107.9 (3)O5—C23—H23C109.5
O3—C3—C2110.6 (3)H23A—C23—H23C109.5
C4—C3—C2111.5 (3)H23B—C23—H23C109.5
O3—C3—H3108.9C21—C24—H24A109.5
C4—C3—H3108.9C21—C24—H24B109.5
C2—C3—H3108.9H24A—C24—H24B109.5
C3—C4—C25112.9 (3)C21—C24—H24C109.5
C3—C4—C5112.7 (3)H24A—C24—H24C109.5
C25—C4—C5113.0 (3)H24B—C24—H24C109.5
C3—C4—H4105.8C4—C25—H25A109.5
C25—C4—H4105.8C4—C25—H25B109.5
C5—C4—H4105.8H25A—C25—H25B109.5
O7—C5—C6104.0 (3)C4—C25—H25C109.5
O7—C5—C4111.9 (3)H25A—C25—H25C109.5
C6—C5—C4114.2 (3)H25B—C25—H25C109.5
O7—C5—H5108.9O7—C26—O8106.5 (3)
C6—C5—H5108.9O7—C26—C27106.1 (4)
C4—C5—H5108.9O8—C26—C27111.7 (3)
O10—C6—C34113.5 (4)O7—C26—H26110.8
O10—C6—C7104.2 (3)O8—C26—H26110.8
C34—C6—C7110.3 (4)C27—C26—H26110.8
O10—C6—C5108.0 (3)O9—C27—C28107.7 (4)
C34—C6—C5110.5 (4)O9—C27—C26108.1 (4)
C7—C6—C5110.1 (3)C28—C27—C26108.6 (4)
C6—C7—C8115.5 (4)O9—C27—H27110.8
C6—C7—H7A108.4C28—C27—H27110.8
C8—C7—H7A108.4C26—C27—H27110.8
C6—C7—H7B108.4C29—C28—C27111.2 (4)
C8—C7—H7B108.4C29—C28—N1113.2 (4)
H7A—C7—H7B107.5C27—C28—N1109.5 (4)
C9—C8—C36110.1 (4)C29—C28—H28107.6
C9—C8—C7112.9 (4)C27—C28—H28107.6
C36—C8—C7109.8 (4)N1—C28—H28107.6
C9—C8—H8108.0C28—C29—C30109.2 (4)
C36—C8—H8108.0C28—C29—H29A109.8
C7—C8—H8108.0C30—C29—H29A109.8
O11—C9—C10120.1 (5)C28—C29—H29B109.8
O11—C9—C8120.6 (5)C30—C29—H29B109.8
C10—C9—C8119.1 (4)H29A—C29—H29B108.3
C9—C10—C37108.4 (4)O8—C30—C33106.6 (4)
C9—C10—C11110.3 (4)O8—C30—C29108.8 (4)
C37—C10—C11113.8 (4)C33—C30—C29111.4 (4)
C9—C10—H10108.1O8—C30—H30110.0
C37—C10—H10108.1C33—C30—H30110.0
C11—C10—H10108.1C29—C30—H30110.0
O12—C11—C12106.8 (3)N1—C31—H31A109.5
O12—C11—C10111.1 (4)N1—C31—H31B109.5
C12—C11—C10116.3 (4)H31A—C31—H31B109.5
O12—C11—H11107.4N1—C31—H31C109.5
C12—C11—H11107.4H31A—C31—H31C109.5
C10—C11—H11107.4H31B—C31—H31C109.5
O13—C12—C11110.3 (4)N1—C32—H32A109.5
O13—C12—C38106.1 (4)N1—C32—H32B109.5
C11—C12—C38111.9 (4)H32A—C32—H32B109.5
O13—C12—C13106.9 (4)N1—C32—H32C109.5
C11—C12—C13110.8 (4)H32A—C32—H32C109.5
C38—C12—C13110.6 (4)H32B—C32—H32C109.5
O1—C13—C14106.0 (4)C30—C33—H33A109.5
O1—C13—C12107.3 (3)C30—C33—H33B109.5
C14—C13—C12115.4 (4)H33A—C33—H33B109.5
O1—C13—H13A109.3C30—C33—H33C109.5
C14—C13—H13A109.3H33A—C33—H33C109.5
C12—C13—H13A109.3H33B—C33—H33C109.5
C15—C14—C13114.8 (4)C6—C34—H34A109.5
C15—C14—H14A108.6C6—C34—H34B109.5
C13—C14—H14A108.6H34A—C34—H34B109.5
C15—C14—H14B108.6C6—C34—H34C109.5
C13—C14—H14B108.6H34A—C34—H34C109.5
H14A—C14—H14B107.5H34B—C34—H34C109.5
C14—C15—H15A109.5O10—C35—H35A109.5
C14—C15—H15B109.5O10—C35—H35B109.5
H15A—C15—H15B109.5H35A—C35—H35B109.5
C14—C15—H15C109.5O10—C35—H35C109.5
H15A—C15—H15C109.5H35A—C35—H35C109.5
H15B—C15—H15C109.5H35B—C35—H35C109.5
C2—C16—H16A109.5C8—C36—H36A109.5
C2—C16—H16B109.5C8—C36—H36B109.5
H16A—C16—H16B109.5H36A—C36—H36B109.5
C2—C16—H16C109.5C8—C36—H36C109.5
H16A—C16—H16C109.5H36A—C36—H36C109.5
H16B—C16—H16C109.5H36B—C36—H36C109.5
O4—C17—O3112.5 (3)C10—C37—H37A109.5
O4—C17—C18112.7 (3)C10—C37—H37B109.5
O3—C17—C18108.6 (3)H37A—C37—H37B109.5
O4—C17—H17107.6C10—C37—H37C109.5
O3—C17—H17107.6H37A—C37—H37C109.5
C18—C17—H17107.6H37B—C37—H37C109.5
C17—C18—C19115.1 (4)C12—C38—H38A109.5
C17—C18—H18A108.5C12—C38—H38B109.5
C19—C18—H18A108.5H38A—C38—H38B109.5
C17—C18—H18B108.5C12—C38—H38C109.5
C19—C18—H18B108.5H38A—C38—H38C109.5
H18A—C18—H18B107.5H38B—C38—H38C109.5
O5—C19—C20103.7 (4)
C13—O1—C1—O25.7 (6)C1—O1—C13—C12111.6 (4)
C13—O1—C1—C2173.7 (3)O13—C12—C13—O1166.9 (3)
O2—C1—C2—C1665.8 (6)C11—C12—C13—O173.0 (4)
O1—C1—C2—C16113.6 (4)C38—C12—C13—O151.7 (5)
O2—C1—C2—C361.5 (6)O13—C12—C13—C1449.1 (5)
O1—C1—C2—C3119.1 (4)C11—C12—C13—C14169.2 (4)
C17—O3—C3—C4149.2 (3)C38—C12—C13—C1466.1 (5)
C17—O3—C3—C288.5 (4)O1—C13—C14—C1559.6 (6)
C1—C2—C3—O3169.2 (3)C12—C13—C14—C15178.2 (5)
C16—C2—C3—O348.6 (5)C21—O4—C17—O374.2 (4)
C1—C2—C3—C470.7 (4)C21—O4—C17—C1848.9 (5)
C16—C2—C3—C4168.7 (4)C3—O3—C17—O477.2 (4)
O3—C3—C4—C2558.8 (4)C3—O3—C17—C18157.4 (3)
C2—C3—C4—C2562.8 (5)O4—C17—C18—C1946.8 (5)
O3—C3—C4—C570.6 (4)O3—C17—C18—C1978.5 (4)
C2—C3—C4—C5167.7 (3)C23—O5—C19—C20173.7 (4)
C26—O7—C5—C6133.6 (3)C23—O5—C19—C1857.1 (5)
C26—O7—C5—C4102.7 (4)C23—O5—C19—C2268.1 (5)
C3—C4—C5—O7131.5 (4)C17—C18—C19—O564.8 (5)
C25—C4—C5—O72.1 (5)C17—C18—C19—C2049.5 (5)
C3—C4—C5—C6110.6 (4)C17—C18—C19—C22169.4 (4)
C25—C4—C5—C6120.0 (4)O5—C19—C20—O654.6 (4)
C35—O10—C6—C3435.8 (6)C18—C19—C20—O6175.3 (3)
C35—O10—C6—C7155.8 (5)C22—C19—C20—O664.6 (5)
C35—O10—C6—C587.1 (5)O5—C19—C20—C2165.9 (4)
O7—C5—C6—O10165.1 (3)C18—C19—C20—C2154.8 (5)
C4—C5—C6—O1042.9 (4)C22—C19—C20—C21174.9 (4)
O7—C5—C6—C3470.1 (4)C17—O4—C21—C24177.3 (4)
C4—C5—C6—C34167.7 (4)C17—O4—C21—C2054.7 (5)
O7—C5—C6—C752.0 (4)O6—C20—C21—O4178.4 (3)
C4—C5—C6—C770.2 (4)C19—C20—C21—O457.7 (5)
O10—C6—C7—C854.0 (5)O6—C20—C21—C2464.1 (5)
C34—C6—C7—C868.1 (5)C19—C20—C21—C24175.2 (4)
C5—C6—C7—C8169.6 (4)C5—O7—C26—O876.4 (4)
C6—C7—C8—C974.4 (5)C5—O7—C26—C27164.5 (3)
C6—C7—C8—C36162.4 (4)C30—O8—C26—O7177.0 (3)
C36—C8—C9—O11114.6 (5)C30—O8—C26—C2761.6 (5)
C7—C8—C9—O11122.3 (5)O7—C26—C27—O972.4 (5)
C36—C8—C9—C1060.4 (5)O8—C26—C27—O9172.0 (4)
C7—C8—C9—C1062.7 (5)O7—C26—C27—C28171.1 (4)
O11—C9—C10—C3762.5 (6)O8—C26—C27—C2855.5 (5)
C8—C9—C10—C37112.6 (5)O9—C27—C28—C29170.3 (4)
O11—C9—C10—C1162.7 (5)C26—C27—C28—C2953.5 (5)
C8—C9—C10—C11122.2 (4)O9—C27—C28—N163.9 (5)
C9—C10—C11—O1263.8 (5)C26—C27—C28—N1179.3 (3)
C37—C10—C11—O1258.2 (5)C31—N1—C28—C2945.3 (5)
C9—C10—C11—C12173.8 (4)C32—N1—C28—C2981.5 (5)
C37—C10—C11—C1264.2 (5)C31—N1—C28—C2779.4 (5)
O12—C11—C12—O1349.5 (5)C32—N1—C28—C27153.8 (4)
C10—C11—C12—O1375.1 (5)C27—C28—C29—C3056.1 (5)
O12—C11—C12—C38167.4 (4)N1—C28—C29—C30179.9 (4)
C10—C11—C12—C3842.7 (5)C26—O8—C30—C33177.5 (4)
O12—C11—C12—C1368.7 (4)C26—O8—C30—C2962.3 (5)
C10—C11—C12—C13166.7 (3)C28—C29—C30—O858.7 (5)
C1—O1—C13—C14124.6 (4)C28—C29—C30—C33176.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O13i0.821.862.660 (4)164
O13—H13···O16ii0.822.052.767 (5)146
O9—H9···O170.822.032.486 (9)114
O13—H13···O120.822.272.683 (5)111
O12—H12···O110.822.142.830 (5)142
O9—H9···Cl10.822.613.303 (4)143
N1—H1···O90.912.402.860 (5)112
N1—H1···Cl10.912.293.134 (4)154
Symmetry codes: (i) x1, y, z; (ii) x+1, y1/2, z+1/2.
 

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