electronic papers (organic compounds)
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 OO distances in the range 2.486 (9)-2.830 (5) Å; other distances are NO = 2.860 (5), NCl = 3.134 (4) and OCl = 3.303 (4) Å.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100010490/qd0001sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010490/qd0001Isup2.hkl |
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−·3.5H2O | Dx = 1.228 Mg m−3 |
Mr = 847.46 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 14.409 (2) Å | θ = 20.0–30.0° |
b = 16.489 (3) Å | µ = 1.30 mm−1 |
c = 19.267 (3) Å | T = 293 K |
V = 4577.6 (13) Å3 | Block, colourless |
Z = 4 | 0.50 × 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 tube | Rint = 0.062 |
Graphite monochromator | θmax = 68.0°, θmin = 5.0° |
ω–2θ scans | h = 0→17 |
Absorption correction: empirical (using intensity measurements) ψ scan (3 reflections; North et al., 1968) | k = 0→19 |
Tmin = 0.56, Tmax = 0.66 | l = −23→23 |
8735 measured reflections | 3 standard reflections every 200 reflections |
8291 independent reflections | intensity decay: 12.6% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: geom and difference maps |
R[F2 > 2σ(F2)] = 0.058 | H-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 reflections | Δρmax = 0.20 e Å−3 |
532 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.01 (3) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | 0.25061 (11) | 0.87642 (10) | −0.04179 (7) | 0.0837 (4) | |
O1 | 0.55650 (18) | 0.60759 (17) | 0.34796 (16) | 0.0475 (7) | |
O2 | 0.4746 (2) | 0.5024 (2) | 0.38923 (18) | 0.0618 (9) | |
O3 | 0.23968 (18) | 0.63278 (17) | 0.31443 (14) | 0.0427 (7) | |
O4 | 0.1304 (2) | 0.53247 (17) | 0.34298 (16) | 0.0492 (7) | |
O5 | 0.0660 (2) | 0.71118 (18) | 0.26086 (18) | 0.0577 (8) | |
O6 | −0.0778 (2) | 0.6117 (2) | 0.25741 (18) | 0.0659 (10) | |
H6 | −0.1188 | 0.5777 | 0.2621 | 0.099* | |
O7 | 0.27955 (19) | 0.58293 (17) | 0.12528 (15) | 0.0467 (7) | |
O8 | 0.13238 (19) | 0.54420 (17) | 0.10599 (15) | 0.0471 (7) | |
O9 | 0.2349 (4) | 0.7438 (2) | 0.0862 (3) | 0.1074 (17) | |
H9 | 0.2632 | 0.7642 | 0.0537 | 0.161* | |
O10 | 0.4043 (2) | 0.42754 (18) | 0.21812 (16) | 0.0554 (8) | |
O11 | 0.5730 (3) | 0.3296 (2) | 0.1690 (2) | 0.0791 (12) | |
O12 | 0.6457 (3) | 0.40473 (19) | 0.28939 (18) | 0.0640 (9) | |
H12 | 0.6314 | 0.3646 | 0.2667 | 0.096* | |
O13 | 0.77492 (19) | 0.5218 (2) | 0.28931 (18) | 0.0590 (9) | |
H13 | 0.7778 | 0.4770 | 0.3076 | 0.089* | |
N1 | 0.0855 (3) | 0.7581 (2) | −0.01075 (19) | 0.0543 (10) | |
H1 | 0.1353 | 0.7913 | −0.0047 | 0.065* | |
C1 | 0.4783 (3) | 0.5701 (3) | 0.3690 (2) | 0.0436 (10) | |
C2 | 0.3962 (3) | 0.6274 (3) | 0.3636 (2) | 0.0452 (10) | |
H2 | 0.4183 | 0.6787 | 0.3438 | 0.054* | |
C3 | 0.3265 (3) | 0.5898 (3) | 0.3124 (2) | 0.0392 (10) | |
H3 | 0.3157 | 0.5331 | 0.3255 | 0.047* | |
C4 | 0.3626 (3) | 0.5926 (2) | 0.2380 (2) | 0.0414 (10) | |
H4 | 0.4245 | 0.5680 | 0.2393 | 0.050* | |
C5 | 0.3046 (3) | 0.5394 (2) | 0.1877 (2) | 0.0405 (9) | |
H5 | 0.2477 | 0.5222 | 0.2114 | 0.049* | |
C6 | 0.3560 (3) | 0.4635 (3) | 0.1608 (2) | 0.0430 (10) | |
C7 | 0.4333 (3) | 0.4885 (3) | 0.1105 (2) | 0.0469 (11) | |
H7A | 0.4686 | 0.5321 | 0.1316 | 0.056* | |
H7B | 0.4049 | 0.5098 | 0.0687 | 0.056* | |
C8 | 0.5013 (3) | 0.4204 (3) | 0.0896 (2) | 0.0532 (12) | |
H8 | 0.4648 | 0.3719 | 0.0788 | 0.064* | |
C9 | 0.5687 (4) | 0.3988 (3) | 0.1467 (3) | 0.0555 (12) | |
C10 | 0.6362 (3) | 0.4622 (3) | 0.1721 (2) | 0.0509 (11) | |
H10 | 0.6222 | 0.5132 | 0.1481 | 0.061* | |
C11 | 0.6237 (3) | 0.4763 (3) | 0.2508 (2) | 0.0479 (11) | |
H11 | 0.5580 | 0.4885 | 0.2589 | 0.058* | |
C12 | 0.6802 (3) | 0.5453 (3) | 0.2825 (2) | 0.0472 (11) | |
C13 | 0.6450 (3) | 0.5657 (3) | 0.3558 (2) | 0.0495 (11) | |
H13A | 0.6354 | 0.5154 | 0.3819 | 0.059* | |
C14 | 0.7063 (3) | 0.6221 (4) | 0.3974 (3) | 0.0694 (15) | |
H14A | 0.7667 | 0.5969 | 0.4029 | 0.083* | |
H14B | 0.7151 | 0.6717 | 0.3712 | 0.083* | |
C15 | 0.6699 (4) | 0.6436 (5) | 0.4675 (3) | 0.102 (2) | |
H15A | 0.6124 | 0.6725 | 0.4627 | 0.153* | |
H15B | 0.7142 | 0.6771 | 0.4912 | 0.153* | |
H15C | 0.6596 | 0.5949 | 0.4938 | 0.153* | |
C16 | 0.3631 (3) | 0.6439 (4) | 0.4380 (3) | 0.0772 (18) | |
H16A | 0.3407 | 0.5944 | 0.4583 | 0.116* | |
H16B | 0.3140 | 0.6833 | 0.4372 | 0.116* | |
H16C | 0.4138 | 0.6644 | 0.4651 | 0.116* | |
C17 | 0.1752 (3) | 0.6043 (3) | 0.3643 (2) | 0.0444 (10) | |
H17 | 0.2098 | 0.5920 | 0.4068 | 0.053* | |
C18 | 0.1080 (3) | 0.6718 (3) | 0.3807 (2) | 0.0535 (12) | |
H18A | 0.1428 | 0.7219 | 0.3856 | 0.064* | |
H18B | 0.0790 | 0.6603 | 0.4250 | 0.064* | |
C19 | 0.0320 (3) | 0.6850 (3) | 0.3269 (2) | 0.0506 (12) | |
C20 | −0.0115 (3) | 0.6029 (3) | 0.3116 (2) | 0.0498 (11) | |
H20 | −0.0431 | 0.5833 | 0.3534 | 0.060* | |
C21 | 0.0602 (3) | 0.5412 (3) | 0.2897 (2) | 0.0478 (11) | |
H21 | 0.0897 | 0.5591 | 0.2465 | 0.057* | |
C22 | −0.0414 (4) | 0.7430 (3) | 0.3550 (3) | 0.0789 (17) | |
H22A | −0.0129 | 0.7939 | 0.3663 | 0.118* | |
H22B | −0.0689 | 0.7202 | 0.3960 | 0.118* | |
H22C | −0.0885 | 0.7513 | 0.3205 | 0.118* | |
C23 | 0.1196 (4) | 0.7839 (3) | 0.2608 (3) | 0.0789 (18) | |
H23A | 0.0887 | 0.8244 | 0.2881 | 0.118* | |
H23B | 0.1263 | 0.8031 | 0.2140 | 0.118* | |
H23C | 0.1797 | 0.7731 | 0.2801 | 0.118* | |
C24 | 0.0213 (4) | 0.4574 (3) | 0.2797 (3) | 0.0706 (15) | |
H24A | 0.0689 | 0.4222 | 0.2621 | 0.106* | |
H24B | −0.0292 | 0.4594 | 0.2472 | 0.106* | |
H24C | −0.0007 | 0.4369 | 0.3234 | 0.106* | |
C25 | 0.3768 (4) | 0.6790 (3) | 0.2114 (2) | 0.0562 (13) | |
H25A | 0.3193 | 0.7083 | 0.2145 | 0.084* | |
H25B | 0.3969 | 0.6774 | 0.1639 | 0.084* | |
H25C | 0.4230 | 0.7057 | 0.2391 | 0.084* | |
C26 | 0.1886 (3) | 0.6116 (3) | 0.1213 (2) | 0.0443 (10) | |
H26 | 0.1698 | 0.6367 | 0.1652 | 0.053* | |
C27 | 0.1875 (3) | 0.6733 (3) | 0.0630 (3) | 0.0523 (12) | |
H27 | 0.2170 | 0.6512 | 0.0212 | 0.063* | |
C28 | 0.0882 (3) | 0.6968 (3) | 0.0485 (2) | 0.0464 (11) | |
H28 | 0.0641 | 0.7238 | 0.0901 | 0.056* | |
C29 | 0.0293 (3) | 0.6238 (3) | 0.0354 (2) | 0.0541 (12) | |
H29A | 0.0500 | 0.5965 | −0.0064 | 0.065* | |
H29B | −0.0348 | 0.6400 | 0.0290 | 0.065* | |
C30 | 0.0368 (3) | 0.5666 (3) | 0.0969 (2) | 0.0471 (11) | |
H30 | 0.0135 | 0.5932 | 0.1389 | 0.056* | |
C31 | 0.0947 (4) | 0.7225 (4) | −0.0815 (2) | 0.0742 (16) | |
H31A | 0.0399 | 0.6921 | −0.0924 | 0.111* | |
H31B | 0.1478 | 0.6874 | −0.0828 | 0.111* | |
H31C | 0.1025 | 0.7653 | −0.1148 | 0.111* | |
C32 | 0.0014 (4) | 0.8109 (3) | −0.0067 (3) | 0.0803 (18) | |
H32A | 0.0012 | 0.8480 | −0.0451 | 0.120* | |
H32B | 0.0023 | 0.8408 | 0.0361 | 0.120* | |
H32C | −0.0533 | 0.7777 | −0.0085 | 0.120* | |
C33 | −0.0156 (3) | 0.4895 (3) | 0.0842 (3) | 0.0666 (14) | |
H33A | 0.0076 | 0.4638 | 0.0431 | 0.100* | |
H33B | −0.0803 | 0.5016 | 0.0784 | 0.100* | |
H33C | −0.0078 | 0.4538 | 0.1232 | 0.100* | |
C34 | 0.2885 (3) | 0.4059 (3) | 0.1252 (3) | 0.0660 (15) | |
H34A | 0.3191 | 0.3553 | 0.1159 | 0.099* | |
H34B | 0.2679 | 0.4295 | 0.0823 | 0.099* | |
H34C | 0.2361 | 0.3966 | 0.1549 | 0.099* | |
C35 | 0.3594 (5) | 0.3714 (4) | 0.2612 (3) | 0.108 (2) | |
H35A | 0.2962 | 0.3879 | 0.2681 | 0.163* | |
H35B | 0.3907 | 0.3691 | 0.3051 | 0.163* | |
H35C | 0.3607 | 0.3189 | 0.2398 | 0.163* | |
C36 | 0.5544 (4) | 0.4450 (4) | 0.0240 (2) | 0.0729 (16) | |
H36A | 0.5894 | 0.4934 | 0.0330 | 0.109* | |
H36B | 0.5112 | 0.4548 | −0.0130 | 0.109* | |
H36C | 0.5959 | 0.4021 | 0.0109 | 0.109* | |
C37 | 0.7349 (4) | 0.4357 (4) | 0.1514 (3) | 0.0835 (18) | |
H37A | 0.7494 | 0.3851 | 0.1735 | 0.125* | |
H37B | 0.7786 | 0.4763 | 0.1659 | 0.125* | |
H37C | 0.7381 | 0.4293 | 0.1019 | 0.125* | |
C38 | 0.6798 (3) | 0.6209 (3) | 0.2365 (3) | 0.0599 (13) | |
H38A | 0.7153 | 0.6631 | 0.2583 | 0.090* | |
H38B | 0.6171 | 0.6391 | 0.2300 | 0.090* | |
H38C | 0.7067 | 0.6081 | 0.1923 | 0.090* | |
O14 | 0.3813 (3) | 0.7691 (3) | −0.1486 (2) | 0.0993 (14) | |
O15 | 0.1859 (3) | 0.3791 (3) | 0.4090 (3) | 0.1119 (16) | |
O16 | 0.1777 (3) | 0.9109 (3) | 0.1089 (2) | 0.0964 (13) | |
O17 | 0.3762 (5) | 0.8302 (5) | 0.0820 (4) | 0.090 (2) | 0.50 |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0881 (10) | 0.0997 (11) | 0.0634 (8) | −0.0169 (9) | 0.0078 (8) | 0.0186 (8) |
O1 | 0.0307 (15) | 0.0522 (17) | 0.0595 (18) | −0.0041 (14) | −0.0042 (14) | 0.0062 (15) |
O2 | 0.0428 (18) | 0.064 (2) | 0.079 (2) | −0.0029 (16) | 0.0019 (17) | 0.0277 (19) |
O3 | 0.0302 (15) | 0.0475 (16) | 0.0503 (16) | 0.0025 (13) | 0.0007 (13) | 0.0045 (14) |
O4 | 0.0412 (17) | 0.0476 (17) | 0.0589 (18) | −0.0045 (14) | −0.0063 (15) | 0.0087 (14) |
O5 | 0.052 (2) | 0.0515 (18) | 0.070 (2) | −0.0066 (16) | 0.0039 (17) | 0.0098 (16) |
O6 | 0.0378 (19) | 0.087 (3) | 0.073 (2) | −0.0110 (17) | −0.0182 (17) | 0.022 (2) |
O7 | 0.0384 (16) | 0.0559 (18) | 0.0459 (17) | 0.0019 (14) | −0.0075 (13) | 0.0068 (14) |
O8 | 0.0398 (16) | 0.0429 (15) | 0.0586 (18) | 0.0010 (14) | −0.0104 (14) | −0.0011 (14) |
O9 | 0.120 (4) | 0.065 (2) | 0.137 (4) | −0.040 (3) | −0.074 (3) | 0.047 (3) |
O10 | 0.056 (2) | 0.0550 (18) | 0.0552 (19) | 0.0042 (16) | −0.0058 (16) | 0.0174 (15) |
O11 | 0.098 (3) | 0.0432 (19) | 0.097 (3) | 0.018 (2) | −0.010 (2) | 0.0025 (19) |
O12 | 0.068 (2) | 0.0556 (19) | 0.068 (2) | −0.0017 (19) | −0.0076 (19) | 0.0177 (17) |
O13 | 0.0250 (16) | 0.076 (2) | 0.076 (2) | 0.0042 (15) | −0.0017 (15) | 0.0205 (19) |
N1 | 0.055 (2) | 0.055 (2) | 0.053 (2) | 0.0082 (19) | −0.007 (2) | 0.0029 (19) |
C1 | 0.030 (2) | 0.057 (3) | 0.044 (2) | −0.005 (2) | −0.0015 (19) | 0.003 (2) |
C2 | 0.032 (2) | 0.055 (3) | 0.048 (2) | 0.002 (2) | −0.0043 (19) | −0.007 (2) |
C3 | 0.026 (2) | 0.046 (2) | 0.046 (2) | 0.0020 (18) | −0.0025 (18) | −0.001 (2) |
C4 | 0.038 (2) | 0.043 (2) | 0.043 (2) | −0.0023 (19) | −0.005 (2) | −0.0031 (18) |
C5 | 0.040 (2) | 0.041 (2) | 0.041 (2) | −0.0023 (19) | −0.0064 (19) | 0.0050 (19) |
C6 | 0.041 (2) | 0.045 (2) | 0.043 (2) | −0.003 (2) | −0.003 (2) | 0.0055 (19) |
C7 | 0.054 (3) | 0.046 (2) | 0.041 (2) | 0.005 (2) | −0.003 (2) | 0.0004 (19) |
C8 | 0.060 (3) | 0.048 (3) | 0.051 (3) | 0.004 (2) | 0.003 (2) | −0.007 (2) |
C9 | 0.064 (3) | 0.045 (3) | 0.057 (3) | 0.014 (2) | 0.008 (2) | −0.003 (2) |
C10 | 0.044 (3) | 0.056 (3) | 0.053 (3) | 0.013 (2) | 0.005 (2) | 0.006 (2) |
C11 | 0.034 (2) | 0.053 (3) | 0.056 (3) | 0.003 (2) | 0.000 (2) | 0.011 (2) |
C12 | 0.025 (2) | 0.058 (3) | 0.059 (3) | 0.008 (2) | −0.002 (2) | 0.011 (2) |
C13 | 0.030 (2) | 0.062 (3) | 0.056 (3) | −0.001 (2) | −0.004 (2) | 0.006 (2) |
C14 | 0.040 (3) | 0.100 (4) | 0.068 (3) | −0.016 (3) | −0.010 (2) | −0.009 (3) |
C15 | 0.075 (4) | 0.159 (7) | 0.072 (4) | −0.040 (4) | −0.005 (3) | −0.022 (4) |
C16 | 0.041 (3) | 0.130 (5) | 0.061 (3) | −0.001 (3) | −0.007 (3) | −0.040 (3) |
C17 | 0.038 (2) | 0.056 (3) | 0.039 (2) | −0.006 (2) | −0.0025 (19) | −0.001 (2) |
C18 | 0.038 (3) | 0.068 (3) | 0.054 (3) | 0.001 (2) | 0.001 (2) | −0.011 (2) |
C19 | 0.041 (3) | 0.053 (3) | 0.057 (3) | 0.002 (2) | 0.005 (2) | −0.003 (2) |
C20 | 0.034 (2) | 0.062 (3) | 0.053 (3) | 0.001 (2) | −0.002 (2) | 0.011 (2) |
C21 | 0.048 (3) | 0.051 (2) | 0.044 (2) | −0.011 (2) | −0.009 (2) | 0.007 (2) |
C22 | 0.051 (3) | 0.075 (4) | 0.110 (5) | 0.013 (3) | 0.013 (3) | −0.013 (3) |
C23 | 0.062 (4) | 0.045 (3) | 0.129 (5) | −0.007 (3) | 0.009 (4) | 0.015 (3) |
C24 | 0.070 (4) | 0.056 (3) | 0.086 (4) | −0.022 (3) | −0.009 (3) | −0.001 (3) |
C25 | 0.061 (3) | 0.053 (3) | 0.055 (3) | −0.021 (2) | 0.000 (2) | −0.003 (2) |
C26 | 0.038 (2) | 0.042 (2) | 0.052 (3) | 0.003 (2) | −0.009 (2) | 0.000 (2) |
C27 | 0.046 (3) | 0.049 (3) | 0.061 (3) | −0.004 (2) | −0.013 (2) | 0.007 (2) |
C28 | 0.049 (3) | 0.050 (3) | 0.040 (2) | 0.009 (2) | −0.004 (2) | 0.003 (2) |
C29 | 0.042 (3) | 0.069 (3) | 0.051 (3) | 0.007 (2) | −0.004 (2) | 0.005 (2) |
C30 | 0.031 (2) | 0.057 (3) | 0.053 (3) | 0.003 (2) | −0.008 (2) | 0.003 (2) |
C31 | 0.091 (4) | 0.087 (4) | 0.044 (3) | 0.002 (3) | 0.000 (3) | 0.005 (3) |
C32 | 0.075 (4) | 0.070 (4) | 0.096 (4) | 0.035 (3) | −0.006 (3) | 0.018 (3) |
C33 | 0.049 (3) | 0.074 (4) | 0.076 (4) | −0.015 (3) | −0.010 (3) | 0.005 (3) |
C34 | 0.061 (3) | 0.052 (3) | 0.085 (4) | −0.013 (2) | −0.007 (3) | −0.014 (3) |
C35 | 0.136 (6) | 0.094 (5) | 0.095 (5) | −0.028 (5) | −0.010 (5) | 0.052 (4) |
C36 | 0.074 (4) | 0.094 (4) | 0.051 (3) | 0.013 (3) | 0.011 (3) | −0.011 (3) |
C37 | 0.052 (3) | 0.116 (5) | 0.082 (4) | 0.023 (3) | 0.013 (3) | 0.001 (4) |
C38 | 0.051 (3) | 0.060 (3) | 0.068 (3) | −0.003 (3) | 0.000 (3) | 0.016 (3) |
O14 | 0.109 (3) | 0.085 (3) | 0.103 (3) | −0.012 (3) | 0.001 (3) | 0.017 (2) |
O15 | 0.108 (3) | 0.092 (3) | 0.135 (4) | −0.004 (3) | −0.047 (3) | 0.023 (3) |
O16 | 0.108 (3) | 0.102 (3) | 0.080 (3) | −0.020 (3) | −0.002 (3) | −0.020 (2) |
O17 | 0.073 (5) | 0.094 (6) | 0.103 (6) | 0.006 (5) | 0.006 (5) | 0.002 (5) |
Geometric parameters (Å, º) top
O1—C1 | 1.348 (5) | C15—H15C | 0.9600 |
O1—C13 | 1.458 (5) | C16—H16A | 0.9600 |
O2—C1 | 1.184 (5) | C16—H16B | 0.9600 |
O3—C17 | 1.416 (5) | C16—H16C | 0.9600 |
O3—C3 | 1.438 (5) | C17—C18 | 1.509 (6) |
O4—C17 | 1.410 (5) | C17—H17 | 0.9800 |
O4—C21 | 1.448 (5) | C18—C19 | 1.523 (6) |
O5—C23 | 1.426 (5) | C18—H18A | 0.9700 |
O5—C19 | 1.431 (5) | C18—H18B | 0.9700 |
O6—C20 | 1.422 (5) | C19—C20 | 1.520 (6) |
O6—H6 | 0.8200 | C19—C22 | 1.525 (6) |
O7—C26 | 1.396 (5) | C20—C21 | 1.512 (6) |
O7—C5 | 1.446 (5) | C20—H20 | 0.9800 |
O8—C26 | 1.407 (5) | C21—C24 | 1.504 (6) |
O8—C30 | 1.437 (5) | C21—H21 | 0.9800 |
O9—C27 | 1.421 (5) | C22—H22A | 0.9600 |
O9—H9 | 0.8200 | C22—H22B | 0.9600 |
O10—C35 | 1.400 (6) | C22—H22C | 0.9600 |
O10—C6 | 1.434 (5) | C23—H23A | 0.9600 |
O11—C9 | 1.220 (5) | C23—H23B | 0.9600 |
O12—C11 | 1.431 (5) | C23—H23C | 0.9600 |
O12—H12 | 0.8200 | C24—H24A | 0.9600 |
O13—C12 | 1.424 (5) | C24—H24B | 0.9600 |
O13—H13 | 0.8200 | C24—H24C | 0.9600 |
N1—C31 | 1.490 (6) | C25—H25A | 0.9600 |
N1—C32 | 1.493 (6) | C25—H25B | 0.9600 |
N1—C28 | 1.525 (5) | C25—H25C | 0.9600 |
N1—H1 | 0.9100 | C26—C27 | 1.516 (6) |
C1—C2 | 1.517 (6) | C26—H26 | 0.9800 |
C2—C16 | 1.536 (6) | C27—C28 | 1.509 (6) |
C2—C3 | 1.538 (5) | C27—H27 | 0.9800 |
C2—H2 | 0.9800 | C28—C29 | 1.495 (6) |
C3—C4 | 1.526 (6) | C28—H28 | 0.9800 |
C3—H3 | 0.9800 | C29—C30 | 1.517 (6) |
C4—C25 | 1.528 (6) | C29—H29A | 0.9700 |
C4—C5 | 1.552 (5) | C29—H29B | 0.9700 |
C4—H4 | 0.9800 | C30—C33 | 1.498 (6) |
C5—C6 | 1.544 (6) | C30—H30 | 0.9800 |
C5—H5 | 0.9800 | C31—H31A | 0.9600 |
C6—C34 | 1.522 (6) | C31—H31B | 0.9600 |
C6—C7 | 1.534 (6) | C31—H31C | 0.9600 |
C7—C8 | 1.544 (6) | C32—H32A | 0.9600 |
C7—H7A | 0.9700 | C32—H32B | 0.9600 |
C7—H7B | 0.9700 | C32—H32C | 0.9600 |
C8—C9 | 1.509 (7) | C33—H33A | 0.9600 |
C8—C36 | 1.533 (6) | C33—H33B | 0.9600 |
C8—H8 | 0.9800 | C33—H33C | 0.9600 |
C9—C10 | 1.509 (7) | C34—H34A | 0.9600 |
C10—C37 | 1.540 (6) | C34—H34B | 0.9600 |
C10—C11 | 1.545 (6) | C34—H34C | 0.9600 |
C10—H10 | 0.9800 | C35—H35A | 0.9600 |
C11—C12 | 1.526 (6) | C35—H35B | 0.9600 |
C11—H11 | 0.9800 | C35—H35C | 0.9600 |
C12—C38 | 1.531 (6) | C36—H36A | 0.9600 |
C12—C13 | 1.538 (6) | C36—H36B | 0.9600 |
C13—C14 | 1.512 (6) | C36—H36C | 0.9600 |
C13—H13A | 0.9800 | C37—H37A | 0.9600 |
C14—C15 | 1.492 (7) | C37—H37B | 0.9600 |
C14—H14A | 0.9700 | C37—H37C | 0.9600 |
C14—H14B | 0.9700 | C38—H38A | 0.9600 |
C15—H15A | 0.9600 | C38—H38B | 0.9600 |
C15—H15B | 0.9600 | C38—H38C | 0.9600 |
C1—O1—C13 | 118.9 (3) | O5—C19—C18 | 113.7 (4) |
C17—O3—C3 | 115.2 (3) | C20—C19—C18 | 107.6 (4) |
C17—O4—C21 | 116.3 (3) | O5—C19—C22 | 111.3 (4) |
C23—O5—C19 | 116.2 (4) | C20—C19—C22 | 110.0 (4) |
C20—O6—H6 | 109.5 | C18—C19—C22 | 110.3 (4) |
C26—O7—C5 | 116.6 (3) | O6—C20—C21 | 108.9 (4) |
C26—O8—C30 | 112.0 (3) | O6—C20—C19 | 109.2 (4) |
C27—O9—H9 | 109.5 | C21—C20—C19 | 111.8 (4) |
C35—O10—C6 | 120.4 (4) | O6—C20—H20 | 109.0 |
C11—O12—H12 | 109.5 | C21—C20—H20 | 109.0 |
C12—O13—H13 | 109.5 | C19—C20—H20 | 109.0 |
C31—N1—C32 | 110.5 (4) | O4—C21—C24 | 105.1 (4) |
C31—N1—C28 | 114.9 (4) | O4—C21—C20 | 110.3 (3) |
C32—N1—C28 | 111.6 (4) | C24—C21—C20 | 113.5 (4) |
C31—N1—H1 | 106.4 | O4—C21—H21 | 109.3 |
C32—N1—H1 | 106.4 | C24—C21—H21 | 109.3 |
C28—N1—H1 | 106.4 | C20—C21—H21 | 109.3 |
O2—C1—O1 | 124.7 (4) | C19—C22—H22A | 109.5 |
O2—C1—C2 | 125.1 (4) | C19—C22—H22B | 109.5 |
O1—C1—C2 | 110.2 (4) | H22A—C22—H22B | 109.5 |
C1—C2—C16 | 106.8 (4) | C19—C22—H22C | 109.5 |
C1—C2—C3 | 107.6 (3) | H22A—C22—H22C | 109.5 |
C16—C2—C3 | 117.8 (4) | H22B—C22—H22C | 109.5 |
C1—C2—H2 | 108.1 | O5—C23—H23A | 109.5 |
C16—C2—H2 | 108.1 | O5—C23—H23B | 109.5 |
C3—C2—H2 | 108.1 | H23A—C23—H23B | 109.5 |
O3—C3—C4 | 107.9 (3) | O5—C23—H23C | 109.5 |
O3—C3—C2 | 110.6 (3) | H23A—C23—H23C | 109.5 |
C4—C3—C2 | 111.5 (3) | H23B—C23—H23C | 109.5 |
O3—C3—H3 | 108.9 | C21—C24—H24A | 109.5 |
C4—C3—H3 | 108.9 | C21—C24—H24B | 109.5 |
C2—C3—H3 | 108.9 | H24A—C24—H24B | 109.5 |
C3—C4—C25 | 112.9 (3) | C21—C24—H24C | 109.5 |
C3—C4—C5 | 112.7 (3) | H24A—C24—H24C | 109.5 |
C25—C4—C5 | 113.0 (3) | H24B—C24—H24C | 109.5 |
C3—C4—H4 | 105.8 | C4—C25—H25A | 109.5 |
C25—C4—H4 | 105.8 | C4—C25—H25B | 109.5 |
C5—C4—H4 | 105.8 | H25A—C25—H25B | 109.5 |
O7—C5—C6 | 104.0 (3) | C4—C25—H25C | 109.5 |
O7—C5—C4 | 111.9 (3) | H25A—C25—H25C | 109.5 |
C6—C5—C4 | 114.2 (3) | H25B—C25—H25C | 109.5 |
O7—C5—H5 | 108.9 | O7—C26—O8 | 106.5 (3) |
C6—C5—H5 | 108.9 | O7—C26—C27 | 106.1 (4) |
C4—C5—H5 | 108.9 | O8—C26—C27 | 111.7 (3) |
O10—C6—C34 | 113.5 (4) | O7—C26—H26 | 110.8 |
O10—C6—C7 | 104.2 (3) | O8—C26—H26 | 110.8 |
C34—C6—C7 | 110.3 (4) | C27—C26—H26 | 110.8 |
O10—C6—C5 | 108.0 (3) | O9—C27—C28 | 107.7 (4) |
C34—C6—C5 | 110.5 (4) | O9—C27—C26 | 108.1 (4) |
C7—C6—C5 | 110.1 (3) | C28—C27—C26 | 108.6 (4) |
C6—C7—C8 | 115.5 (4) | O9—C27—H27 | 110.8 |
C6—C7—H7A | 108.4 | C28—C27—H27 | 110.8 |
C8—C7—H7A | 108.4 | C26—C27—H27 | 110.8 |
C6—C7—H7B | 108.4 | C29—C28—C27 | 111.2 (4) |
C8—C7—H7B | 108.4 | C29—C28—N1 | 113.2 (4) |
H7A—C7—H7B | 107.5 | C27—C28—N1 | 109.5 (4) |
C9—C8—C36 | 110.1 (4) | C29—C28—H28 | 107.6 |
C9—C8—C7 | 112.9 (4) | C27—C28—H28 | 107.6 |
C36—C8—C7 | 109.8 (4) | N1—C28—H28 | 107.6 |
C9—C8—H8 | 108.0 | C28—C29—C30 | 109.2 (4) |
C36—C8—H8 | 108.0 | C28—C29—H29A | 109.8 |
C7—C8—H8 | 108.0 | C30—C29—H29A | 109.8 |
O11—C9—C10 | 120.1 (5) | C28—C29—H29B | 109.8 |
O11—C9—C8 | 120.6 (5) | C30—C29—H29B | 109.8 |
C10—C9—C8 | 119.1 (4) | H29A—C29—H29B | 108.3 |
C9—C10—C37 | 108.4 (4) | O8—C30—C33 | 106.6 (4) |
C9—C10—C11 | 110.3 (4) | O8—C30—C29 | 108.8 (4) |
C37—C10—C11 | 113.8 (4) | C33—C30—C29 | 111.4 (4) |
C9—C10—H10 | 108.1 | O8—C30—H30 | 110.0 |
C37—C10—H10 | 108.1 | C33—C30—H30 | 110.0 |
C11—C10—H10 | 108.1 | C29—C30—H30 | 110.0 |
O12—C11—C12 | 106.8 (3) | N1—C31—H31A | 109.5 |
O12—C11—C10 | 111.1 (4) | N1—C31—H31B | 109.5 |
C12—C11—C10 | 116.3 (4) | H31A—C31—H31B | 109.5 |
O12—C11—H11 | 107.4 | N1—C31—H31C | 109.5 |
C12—C11—H11 | 107.4 | H31A—C31—H31C | 109.5 |
C10—C11—H11 | 107.4 | H31B—C31—H31C | 109.5 |
O13—C12—C11 | 110.3 (4) | N1—C32—H32A | 109.5 |
O13—C12—C38 | 106.1 (4) | N1—C32—H32B | 109.5 |
C11—C12—C38 | 111.9 (4) | H32A—C32—H32B | 109.5 |
O13—C12—C13 | 106.9 (4) | N1—C32—H32C | 109.5 |
C11—C12—C13 | 110.8 (4) | H32A—C32—H32C | 109.5 |
C38—C12—C13 | 110.6 (4) | H32B—C32—H32C | 109.5 |
O1—C13—C14 | 106.0 (4) | C30—C33—H33A | 109.5 |
O1—C13—C12 | 107.3 (3) | C30—C33—H33B | 109.5 |
C14—C13—C12 | 115.4 (4) | H33A—C33—H33B | 109.5 |
O1—C13—H13A | 109.3 | C30—C33—H33C | 109.5 |
C14—C13—H13A | 109.3 | H33A—C33—H33C | 109.5 |
C12—C13—H13A | 109.3 | H33B—C33—H33C | 109.5 |
C15—C14—C13 | 114.8 (4) | C6—C34—H34A | 109.5 |
C15—C14—H14A | 108.6 | C6—C34—H34B | 109.5 |
C13—C14—H14A | 108.6 | H34A—C34—H34B | 109.5 |
C15—C14—H14B | 108.6 | C6—C34—H34C | 109.5 |
C13—C14—H14B | 108.6 | H34A—C34—H34C | 109.5 |
H14A—C14—H14B | 107.5 | H34B—C34—H34C | 109.5 |
C14—C15—H15A | 109.5 | O10—C35—H35A | 109.5 |
C14—C15—H15B | 109.5 | O10—C35—H35B | 109.5 |
H15A—C15—H15B | 109.5 | H35A—C35—H35B | 109.5 |
C14—C15—H15C | 109.5 | O10—C35—H35C | 109.5 |
H15A—C15—H15C | 109.5 | H35A—C35—H35C | 109.5 |
H15B—C15—H15C | 109.5 | H35B—C35—H35C | 109.5 |
C2—C16—H16A | 109.5 | C8—C36—H36A | 109.5 |
C2—C16—H16B | 109.5 | C8—C36—H36B | 109.5 |
H16A—C16—H16B | 109.5 | H36A—C36—H36B | 109.5 |
C2—C16—H16C | 109.5 | C8—C36—H36C | 109.5 |
H16A—C16—H16C | 109.5 | H36A—C36—H36C | 109.5 |
H16B—C16—H16C | 109.5 | H36B—C36—H36C | 109.5 |
O4—C17—O3 | 112.5 (3) | C10—C37—H37A | 109.5 |
O4—C17—C18 | 112.7 (3) | C10—C37—H37B | 109.5 |
O3—C17—C18 | 108.6 (3) | H37A—C37—H37B | 109.5 |
O4—C17—H17 | 107.6 | C10—C37—H37C | 109.5 |
O3—C17—H17 | 107.6 | H37A—C37—H37C | 109.5 |
C18—C17—H17 | 107.6 | H37B—C37—H37C | 109.5 |
C17—C18—C19 | 115.1 (4) | C12—C38—H38A | 109.5 |
C17—C18—H18A | 108.5 | C12—C38—H38B | 109.5 |
C19—C18—H18A | 108.5 | H38A—C38—H38B | 109.5 |
C17—C18—H18B | 108.5 | C12—C38—H38C | 109.5 |
C19—C18—H18B | 108.5 | H38A—C38—H38C | 109.5 |
H18A—C18—H18B | 107.5 | H38B—C38—H38C | 109.5 |
O5—C19—C20 | 103.7 (4) | ||
C13—O1—C1—O2 | −5.7 (6) | C1—O1—C13—C12 | 111.6 (4) |
C13—O1—C1—C2 | 173.7 (3) | O13—C12—C13—O1 | 166.9 (3) |
O2—C1—C2—C16 | 65.8 (6) | C11—C12—C13—O1 | −73.0 (4) |
O1—C1—C2—C16 | −113.6 (4) | C38—C12—C13—O1 | 51.7 (5) |
O2—C1—C2—C3 | −61.5 (6) | O13—C12—C13—C14 | 49.1 (5) |
O1—C1—C2—C3 | 119.1 (4) | C11—C12—C13—C14 | 169.2 (4) |
C17—O3—C3—C4 | 149.2 (3) | C38—C12—C13—C14 | −66.1 (5) |
C17—O3—C3—C2 | −88.5 (4) | O1—C13—C14—C15 | 59.6 (6) |
C1—C2—C3—O3 | 169.2 (3) | C12—C13—C14—C15 | 178.2 (5) |
C16—C2—C3—O3 | 48.6 (5) | C21—O4—C17—O3 | −74.2 (4) |
C1—C2—C3—C4 | −70.7 (4) | C21—O4—C17—C18 | 48.9 (5) |
C16—C2—C3—C4 | 168.7 (4) | C3—O3—C17—O4 | −77.2 (4) |
O3—C3—C4—C25 | 58.8 (4) | C3—O3—C17—C18 | 157.4 (3) |
C2—C3—C4—C25 | −62.8 (5) | O4—C17—C18—C19 | −46.8 (5) |
O3—C3—C4—C5 | −70.6 (4) | O3—C17—C18—C19 | 78.5 (4) |
C2—C3—C4—C5 | 167.7 (3) | C23—O5—C19—C20 | −173.7 (4) |
C26—O7—C5—C6 | 133.6 (3) | C23—O5—C19—C18 | −57.1 (5) |
C26—O7—C5—C4 | −102.7 (4) | C23—O5—C19—C22 | 68.1 (5) |
C3—C4—C5—O7 | 131.5 (4) | C17—C18—C19—O5 | −64.8 (5) |
C25—C4—C5—O7 | 2.1 (5) | C17—C18—C19—C20 | 49.5 (5) |
C3—C4—C5—C6 | −110.6 (4) | C17—C18—C19—C22 | 169.4 (4) |
C25—C4—C5—C6 | 120.0 (4) | O5—C19—C20—O6 | −54.6 (4) |
C35—O10—C6—C34 | −35.8 (6) | C18—C19—C20—O6 | −175.3 (3) |
C35—O10—C6—C7 | −155.8 (5) | C22—C19—C20—O6 | 64.6 (5) |
C35—O10—C6—C5 | 87.1 (5) | O5—C19—C20—C21 | 65.9 (4) |
O7—C5—C6—O10 | 165.1 (3) | C18—C19—C20—C21 | −54.8 (5) |
C4—C5—C6—O10 | 42.9 (4) | C22—C19—C20—C21 | −174.9 (4) |
O7—C5—C6—C34 | −70.1 (4) | C17—O4—C21—C24 | −177.3 (4) |
C4—C5—C6—C34 | 167.7 (4) | C17—O4—C21—C20 | −54.7 (5) |
O7—C5—C6—C7 | 52.0 (4) | O6—C20—C21—O4 | 178.4 (3) |
C4—C5—C6—C7 | −70.2 (4) | C19—C20—C21—O4 | 57.7 (5) |
O10—C6—C7—C8 | 54.0 (5) | O6—C20—C21—C24 | −64.1 (5) |
C34—C6—C7—C8 | −68.1 (5) | C19—C20—C21—C24 | 175.2 (4) |
C5—C6—C7—C8 | 169.6 (4) | C5—O7—C26—O8 | −76.4 (4) |
C6—C7—C8—C9 | −74.4 (5) | C5—O7—C26—C27 | 164.5 (3) |
C6—C7—C8—C36 | 162.4 (4) | C30—O8—C26—O7 | −177.0 (3) |
C36—C8—C9—O11 | −114.6 (5) | C30—O8—C26—C27 | −61.6 (5) |
C7—C8—C9—O11 | 122.3 (5) | O7—C26—C27—O9 | −72.4 (5) |
C36—C8—C9—C10 | 60.4 (5) | O8—C26—C27—O9 | 172.0 (4) |
C7—C8—C9—C10 | −62.7 (5) | O7—C26—C27—C28 | 171.1 (4) |
O11—C9—C10—C37 | 62.5 (6) | O8—C26—C27—C28 | 55.5 (5) |
C8—C9—C10—C37 | −112.6 (5) | O9—C27—C28—C29 | −170.3 (4) |
O11—C9—C10—C11 | −62.7 (5) | C26—C27—C28—C29 | −53.5 (5) |
C8—C9—C10—C11 | 122.2 (4) | O9—C27—C28—N1 | 63.9 (5) |
C9—C10—C11—O12 | 63.8 (5) | C26—C27—C28—N1 | −179.3 (3) |
C37—C10—C11—O12 | −58.2 (5) | C31—N1—C28—C29 | −45.3 (5) |
C9—C10—C11—C12 | −173.8 (4) | C32—N1—C28—C29 | 81.5 (5) |
C37—C10—C11—C12 | 64.2 (5) | C31—N1—C28—C27 | 79.4 (5) |
O12—C11—C12—O13 | 49.5 (5) | C32—N1—C28—C27 | −153.8 (4) |
C10—C11—C12—O13 | −75.1 (5) | C27—C28—C29—C30 | 56.1 (5) |
O12—C11—C12—C38 | 167.4 (4) | N1—C28—C29—C30 | 179.9 (4) |
C10—C11—C12—C38 | 42.7 (5) | C26—O8—C30—C33 | −177.5 (4) |
O12—C11—C12—C13 | −68.7 (4) | C26—O8—C30—C29 | 62.3 (5) |
C10—C11—C12—C13 | 166.7 (3) | C28—C29—C30—O8 | −58.7 (5) |
C1—O1—C13—C14 | −124.6 (4) | C28—C29—C30—C33 | −176.0 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6···O13i | 0.82 | 1.86 | 2.660 (4) | 164 |
O13—H13···O16ii | 0.82 | 2.05 | 2.767 (5) | 146 |
O9—H9···O17 | 0.82 | 2.03 | 2.486 (9) | 114 |
O13—H13···O12 | 0.82 | 2.27 | 2.683 (5) | 111 |
O12—H12···O11 | 0.82 | 2.14 | 2.830 (5) | 142 |
O9—H9···Cl1 | 0.82 | 2.61 | 3.303 (4) | 143 |
N1—H1···O9 | 0.91 | 2.40 | 2.860 (5) | 112 |
N1—H1···Cl1 | 0.91 | 2.29 | 3.134 (4) | 154 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+1/2. |