Clarithromycin hydro­chloride 3.5-hydrate

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.

Computing details

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

Crystal data

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) Å^3	Block, colourless
Z = 4	0.50 × 0.38 × 0.35 mm
F(000) = 1844

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: geom and difference maps
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.150	w = 1/[σ^2(Fo^2) + (0.047P)^2 + 3.56P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O13^i	0.82	1.86	2.660 (4)	164
O13—H13···O16^ii	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.