Dicatharanthinium (2R,3R)-tartrate trihydrate

The title salt, bis­(methyl 3,4-didehydro­ibogamin-6-ium-18-carboxyl­ate) (2R,3R)-tartrate trihydrate, 2C₂₁H₂₅N₂O₂⁺·C₄H₄O₆²⁻·3H₂O, contains two catharanthinium cations, a (2R,3R)-tartrate anion and three water solvent mol­ecules. The cation contains an indole ring system with a planar conformation and a seven-membered nitro­gen-containing ring with a distorted chair conformation. A network of O—H...O and N—H...O inter­molecular hydrogen bonds stabil­izes the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.063
• wR factor = 0.136
• Data-to-parameter ratio = 7.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.87
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.23 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.59 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.63 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.22 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.24
           From the CIF: _reflns_number_total               4516
           Count of symmetry unique reflns         4522
           Completeness (_total/calc)             99.87%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

bis(methyl 3,4-didehydroibogamin-6-ium-18-carboxylate) (2R,3R)-tartrate trihydrate

Crystal data

2C21H25N2O2^+·C4H4O6^2^−·3H2O	F(000) = 1872
Mr = 876.98	Dx = 1.303 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3507 reflections
a = 10.1147 (4) Å	θ = 2.2–24.1°
b = 18.8215 (8) Å	µ = 0.10 mm^−1
c = 23.4907 (9) Å	T = 293 K
V = 4472.0 (3) Å^3	Block, colourless
Z = 4	0.31 × 0.27 × 0.23 mm

Data collection

Bruker APEX area-detector diffractometer	4516 independent reflections
Radiation source: fine-focus sealed tube	3899 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
φ and ω scans	θmax = 25.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→7
Tmin = 0.965, Tmax = 0.971	k = −22→22
24131 measured reflections	l = −27→28

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.063	H-atom parameters constrained
wR(F^2) = 0.136	w = 1/[σ^2(Fo^2) + (0.0524P)^2 + 1.3486P] where P = (Fo^2 + 2Fc^2)/3
S = 1.19	(Δ/σ)max = 0.001
4516 reflections	Δρmax = 0.20 e Å^−3
574 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Absolute structure: Flack (1983), 4259 Friedel pairs
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.3682 (3)	0.45885 (16)	0.76909 (14)	0.0578 (9)
O2	0.5866 (4)	0.45307 (19)	0.77919 (16)	0.0693 (10)
O3	0.6744 (3)	0.35034 (15)	0.24612 (14)	0.0491 (8)
O4	0.4609 (4)	0.32414 (19)	0.24807 (17)	0.0719 (10)
O5	0.5745 (3)	0.47244 (19)	0.64360 (14)	0.0615 (10)
O6	0.6957 (3)	0.44833 (18)	0.56744 (13)	0.0541 (8)
O7	0.3487 (3)	0.4562 (2)	0.59025 (16)	0.0680 (10)
H7	0.3650	0.4544	0.6244	0.102*
O8	0.4447 (6)	0.3184 (2)	0.58989 (19)	0.0962 (15)
H8	0.3717	0.2994	0.5900	0.144*
O9	0.2565 (4)	0.30656 (19)	0.51319 (16)	0.0728 (11)
O10	0.3480 (4)	0.3837 (2)	0.45464 (14)	0.0660 (10)
O11	0.5807 (5)	0.3453 (2)	0.39256 (18)	0.0979 (15)
H11C	0.5162	0.3571	0.4137	0.117*
H11D	0.5862	0.2997	0.3924	0.117*
O12	0.5626 (5)	0.2019 (2)	0.40689 (19)	0.1014 (15)
H12C	0.6302	0.1933	0.4276	0.122*
H12D	0.4954	0.2059	0.4292	0.122*
O13	0.3322 (5)	0.1732 (2)	0.46546 (18)	0.0968 (14)
H13C	0.2796	0.1412	0.4566	0.116*
H13D	0.2956	0.2081	0.4808	0.116*
N1	0.4561 (3)	0.58769 (17)	0.70097 (13)	0.0382 (8)
H1A	0.4769	0.5453	0.6907	0.046*
N2	0.3528 (4)	0.63147 (19)	0.88301 (14)	0.0437 (9)
H2	0.2927	0.6234	0.9111	0.052*
N3	0.5565 (4)	0.4658 (2)	0.32544 (15)	0.0470 (9)
H3A	0.5599	0.4217	0.3347	0.056*
N4	0.6074 (3)	0.52817 (19)	0.14354 (15)	0.0439 (9)
H4	0.6681	0.5295	0.1150	0.053*
C1	0.4288 (4)	0.6429 (2)	0.66484 (17)	0.0396 (10)
C2	0.4235 (5)	0.6457 (3)	0.60557 (19)	0.0535 (13)
H2a	0.4383	0.6056	0.5834	0.064*
C3	0.3958 (6)	0.7100 (3)	0.5814 (2)	0.0661 (15)
H3	0.3938	0.7133	0.5419	0.079*
C4	0.3707 (6)	0.7696 (3)	0.6130 (2)	0.0663 (15)
H4a	0.3531	0.8123	0.5945	0.080*
C5	0.3712 (5)	0.7675 (3)	0.6718 (2)	0.0560 (13)
H5	0.3525	0.8079	0.6931	0.067*
C6	0.4006 (4)	0.7026 (2)	0.69840 (18)	0.0418 (10)
C7	0.4102 (4)	0.6807 (2)	0.75691 (17)	0.0392 (10)
C8	0.4451 (4)	0.6110 (2)	0.75638 (15)	0.0348 (9)
C9	0.4720 (4)	0.5612 (2)	0.80615 (16)	0.0371 (9)
C10	0.3576 (4)	0.5617 (2)	0.85065 (17)	0.0387 (10)
H10	0.2727	0.5526	0.8319	0.046*
C11	0.2992 (5)	0.6951 (2)	0.85246 (19)	0.0523 (12)
H11A	0.2796	0.7314	0.8805	0.063*
H11B	0.2163	0.6817	0.8347	0.063*
C12	0.3867 (6)	0.7274 (2)	0.80754 (19)	0.0562 (13)
H12A	0.3469	0.7714	0.7947	0.067*
H12B	0.4713	0.7390	0.8246	0.067*
C13	0.6008 (4)	0.5812 (3)	0.83906 (18)	0.0470 (11)
H13A	0.6696	0.5469	0.8307	0.056*
H13B	0.6314	0.6277	0.8270	0.056*
C14	0.5724 (5)	0.5820 (3)	0.90313 (19)	0.0514 (12)
H14	0.6547	0.5873	0.9248	0.062*
C15	0.4803 (5)	0.6440 (3)	0.91459 (18)	0.0544 (13)
H15A	0.4631	0.6478	0.9551	0.065*
H15B	0.5207	0.6879	0.9018	0.065*
C16	0.5003 (5)	0.5158 (3)	0.92071 (18)	0.0533 (12)
H16	0.5339	0.4847	0.9478	0.064*
C17	0.3854 (5)	0.5049 (2)	0.89492 (18)	0.0480 (11)
C18	0.2846 (6)	0.4481 (3)	0.9060 (2)	0.0679 (15)
H18A	0.1990	0.4705	0.9109	0.082*
H18B	0.2791	0.4178	0.8727	0.082*
C19	0.3118 (9)	0.4025 (4)	0.9569 (3)	0.112 (3)
H19A	0.3011	0.4302	0.9910	0.167*
H19B	0.4007	0.3848	0.9550	0.167*
H19C	0.2510	0.3633	0.9575	0.167*
C20	0.4856 (5)	0.4848 (2)	0.78370 (17)	0.0430 (11)
C21	0.3698 (7)	0.3861 (3)	0.7489 (3)	0.086 (2)
H21A	0.3927	0.3549	0.7797	0.130*
H21B	0.4339	0.3814	0.7190	0.130*
H21C	0.2839	0.3737	0.7346	0.130*
C22	0.5660 (5)	0.5221 (3)	0.36256 (19)	0.0492 (11)
C23	0.5883 (5)	0.5219 (3)	0.4209 (2)	0.0645 (15)
H23	0.6010	0.4800	0.4412	0.077*
C24	0.5906 (6)	0.5877 (4)	0.4471 (2)	0.0721 (17)
H24	0.6044	0.5899	0.4862	0.087*
C25	0.5729 (6)	0.6504 (3)	0.4171 (2)	0.0725 (16)
H25	0.5731	0.6933	0.4366	0.087*
C26	0.5554 (5)	0.6503 (3)	0.3598 (2)	0.0603 (13)
H26	0.5458	0.6927	0.3399	0.072*
C27	0.5521 (5)	0.5845 (2)	0.33090 (19)	0.0490 (11)
C28	0.5382 (5)	0.5640 (2)	0.27290 (19)	0.0469 (11)
C29	0.5405 (4)	0.4917 (2)	0.27130 (17)	0.0408 (10)
C30	0.5272 (4)	0.4432 (2)	0.22010 (17)	0.0385 (10)
C31	0.6341 (4)	0.4578 (2)	0.17369 (17)	0.0384 (10)
H31	0.7228	0.4578	0.1905	0.046*
C32	0.6326 (5)	0.5950 (2)	0.17673 (18)	0.0462 (11)
H32A	0.6360	0.6343	0.1501	0.055*
H32B	0.7193	0.5911	0.1942	0.055*
C33	0.5341 (5)	0.6133 (2)	0.22282 (19)	0.0526 (12)
H33A	0.5511	0.6613	0.2359	0.063*
H33B	0.4458	0.6125	0.2067	0.063*
C34	0.3900 (4)	0.4495 (3)	0.19057 (19)	0.0467 (11)
H34A	0.3367	0.4081	0.1994	0.056*
H34B	0.3442	0.4913	0.2044	0.056*
C35	0.4100 (4)	0.4549 (3)	0.1258 (2)	0.0521 (12)
H35	0.3251	0.4510	0.1059	0.062*
C36	0.4750 (5)	0.5261 (3)	0.1129 (2)	0.0536 (12)
H36A	0.4882	0.5312	0.0722	0.064*
H36B	0.4191	0.5647	0.1259	0.064*
C37	0.5031 (5)	0.3985 (3)	0.10604 (19)	0.0514 (12)
H37	0.4784	0.3638	0.0799	0.062*
C38	0.6232 (4)	0.4013 (2)	0.12833 (17)	0.0404 (10)
C39	0.7423 (5)	0.3585 (3)	0.1123 (2)	0.0555 (12)
H39A	0.7779	0.3368	0.1465	0.067*
H39B	0.8091	0.3905	0.0975	0.067*
C40	0.7186 (7)	0.3008 (3)	0.0690 (3)	0.099 (2)
H40A	0.6774	0.3209	0.0359	0.148*
H40B	0.6619	0.2652	0.0851	0.148*
H40C	0.8015	0.2797	0.0585	0.148*
C41	0.5465 (5)	0.3657 (2)	0.23959 (17)	0.0430 (10)
C42	0.7054 (6)	0.2780 (2)	0.2601 (3)	0.0717 (16)
H42A	0.6647	0.2469	0.2329	0.107*
H42B	0.6727	0.2673	0.2975	0.107*
H42C	0.7995	0.2715	0.2592	0.107*
C43	0.5877 (5)	0.4544 (2)	0.59328 (19)	0.0439 (11)
C44	0.4625 (5)	0.4389 (2)	0.55925 (18)	0.0443 (11)
H44	0.4641	0.4682	0.5248	0.053*
C45	0.4570 (5)	0.3613 (2)	0.54129 (19)	0.0529 (12)
H45	0.5401	0.3492	0.5221	0.063*
C46	0.3437 (5)	0.3497 (2)	0.4996 (2)	0.0508 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.056 (2)	0.0410 (18)	0.076 (2)	0.0002 (16)	−0.0134 (19)	−0.0084 (16)
O2	0.059 (2)	0.060 (2)	0.088 (3)	0.0206 (19)	−0.002 (2)	−0.011 (2)
O3	0.0429 (18)	0.0370 (16)	0.067 (2)	0.0001 (14)	−0.0106 (17)	0.0034 (15)
O4	0.052 (2)	0.060 (2)	0.104 (3)	−0.0178 (19)	0.004 (2)	0.020 (2)
O5	0.057 (2)	0.077 (2)	0.0513 (19)	0.0153 (18)	−0.0081 (17)	−0.0320 (18)
O6	0.0448 (19)	0.067 (2)	0.0510 (18)	0.0053 (17)	−0.0065 (16)	−0.0172 (16)
O7	0.045 (2)	0.082 (3)	0.077 (2)	0.0162 (19)	−0.0015 (19)	−0.025 (2)
O8	0.136 (4)	0.060 (2)	0.092 (3)	−0.004 (3)	−0.054 (3)	0.023 (2)
O9	0.074 (3)	0.065 (2)	0.079 (2)	−0.017 (2)	−0.004 (2)	−0.003 (2)
O10	0.066 (2)	0.084 (2)	0.0489 (19)	−0.012 (2)	−0.0166 (18)	0.0023 (19)
O11	0.122 (4)	0.078 (3)	0.093 (3)	0.002 (3)	0.035 (3)	0.025 (2)
O12	0.123 (4)	0.073 (3)	0.108 (3)	−0.005 (3)	−0.038 (3)	0.003 (2)
O13	0.091 (3)	0.076 (3)	0.123 (3)	−0.015 (3)	−0.018 (3)	−0.028 (3)
N1	0.042 (2)	0.0342 (18)	0.0387 (18)	0.0033 (17)	0.0041 (17)	−0.0054 (15)
N2	0.043 (2)	0.056 (2)	0.0323 (17)	−0.0074 (18)	0.0102 (17)	−0.0039 (16)
N3	0.046 (2)	0.047 (2)	0.048 (2)	−0.0016 (19)	0.0104 (19)	−0.0005 (17)
N4	0.037 (2)	0.052 (2)	0.0428 (19)	0.0053 (18)	0.0051 (17)	0.0068 (17)
C1	0.030 (2)	0.050 (3)	0.039 (2)	0.003 (2)	0.0034 (19)	−0.002 (2)
C2	0.048 (3)	0.072 (3)	0.041 (2)	0.006 (3)	0.001 (2)	−0.002 (2)
C3	0.061 (4)	0.090 (4)	0.047 (3)	0.009 (3)	0.000 (3)	0.019 (3)
C4	0.067 (4)	0.069 (4)	0.063 (3)	0.017 (3)	0.004 (3)	0.028 (3)
C5	0.055 (3)	0.050 (3)	0.063 (3)	0.005 (3)	0.003 (3)	0.005 (2)
C6	0.034 (2)	0.047 (3)	0.044 (2)	−0.003 (2)	0.003 (2)	0.007 (2)
C7	0.038 (2)	0.039 (2)	0.040 (2)	0.0002 (19)	0.006 (2)	−0.0033 (19)
C8	0.030 (2)	0.043 (2)	0.031 (2)	−0.0043 (19)	0.0031 (18)	−0.0017 (17)
C9	0.033 (2)	0.040 (2)	0.038 (2)	−0.0012 (19)	0.002 (2)	−0.0040 (18)
C10	0.032 (2)	0.046 (2)	0.038 (2)	−0.0073 (19)	0.000 (2)	0.0001 (19)
C11	0.067 (3)	0.048 (3)	0.042 (2)	0.013 (2)	0.011 (3)	−0.005 (2)
C12	0.080 (4)	0.039 (2)	0.050 (3)	0.006 (3)	0.010 (3)	−0.006 (2)
C13	0.035 (2)	0.055 (3)	0.051 (3)	−0.007 (2)	0.001 (2)	0.004 (2)
C14	0.046 (3)	0.066 (3)	0.042 (2)	−0.012 (2)	−0.012 (2)	−0.003 (2)
C15	0.057 (3)	0.071 (3)	0.036 (2)	−0.018 (3)	0.001 (2)	−0.008 (2)
C16	0.052 (3)	0.068 (3)	0.040 (2)	0.002 (3)	−0.005 (2)	0.008 (2)
C17	0.047 (3)	0.054 (3)	0.043 (2)	−0.008 (2)	0.002 (2)	0.010 (2)
C18	0.068 (4)	0.067 (3)	0.068 (3)	−0.026 (3)	0.004 (3)	0.011 (3)
C19	0.126 (6)	0.099 (5)	0.110 (5)	−0.042 (5)	−0.001 (5)	0.055 (4)
C20	0.049 (3)	0.043 (2)	0.037 (2)	0.001 (2)	−0.002 (2)	0.0044 (19)
C21	0.099 (5)	0.042 (3)	0.118 (5)	−0.003 (3)	−0.033 (5)	−0.009 (3)
C22	0.040 (3)	0.064 (3)	0.044 (2)	−0.004 (2)	0.011 (2)	−0.006 (2)
C23	0.065 (3)	0.077 (4)	0.052 (3)	−0.009 (3)	0.012 (3)	−0.002 (3)
C24	0.068 (4)	0.105 (5)	0.043 (3)	−0.013 (4)	0.010 (3)	−0.015 (3)
C25	0.073 (4)	0.077 (4)	0.067 (4)	−0.013 (3)	0.014 (3)	−0.029 (3)
C26	0.058 (3)	0.061 (3)	0.062 (3)	−0.007 (3)	0.015 (3)	−0.013 (3)
C27	0.038 (3)	0.057 (3)	0.052 (3)	0.000 (2)	0.015 (2)	−0.009 (2)
C28	0.040 (2)	0.043 (3)	0.057 (3)	0.003 (2)	0.009 (2)	−0.003 (2)
C29	0.034 (2)	0.047 (3)	0.042 (2)	−0.002 (2)	0.007 (2)	0.000 (2)
C30	0.025 (2)	0.044 (2)	0.046 (2)	−0.0011 (19)	0.0068 (19)	0.0007 (19)
C31	0.029 (2)	0.042 (2)	0.044 (2)	0.0032 (19)	0.0014 (19)	0.0012 (19)
C32	0.049 (3)	0.039 (2)	0.051 (3)	0.001 (2)	0.002 (2)	0.002 (2)
C33	0.054 (3)	0.042 (3)	0.062 (3)	0.007 (2)	0.003 (3)	−0.002 (2)
C34	0.031 (2)	0.046 (3)	0.063 (3)	0.001 (2)	−0.001 (2)	−0.001 (2)
C35	0.033 (2)	0.061 (3)	0.062 (3)	0.001 (2)	−0.016 (2)	0.000 (2)
C36	0.046 (3)	0.059 (3)	0.056 (3)	0.006 (2)	−0.008 (2)	0.004 (2)
C37	0.049 (3)	0.054 (3)	0.050 (3)	0.001 (2)	−0.008 (2)	−0.010 (2)
C38	0.038 (2)	0.050 (3)	0.034 (2)	−0.003 (2)	0.004 (2)	0.0010 (19)
C39	0.048 (3)	0.057 (3)	0.062 (3)	0.005 (2)	0.010 (3)	−0.008 (2)
C40	0.083 (5)	0.078 (4)	0.135 (6)	−0.001 (4)	0.019 (5)	−0.060 (4)
C41	0.044 (3)	0.045 (3)	0.040 (2)	−0.007 (2)	0.006 (2)	−0.0017 (19)
C42	0.077 (4)	0.043 (3)	0.095 (4)	0.008 (3)	−0.020 (4)	0.001 (3)
C43	0.045 (3)	0.042 (2)	0.045 (3)	0.011 (2)	−0.004 (2)	−0.015 (2)
C44	0.044 (3)	0.044 (2)	0.046 (2)	0.010 (2)	−0.003 (2)	−0.002 (2)
C45	0.059 (3)	0.045 (3)	0.054 (3)	0.014 (3)	−0.019 (3)	−0.009 (2)
C46	0.058 (3)	0.042 (3)	0.053 (3)	0.000 (2)	−0.003 (3)	−0.010 (2)

Geometric parameters (Å, º)

O1—C20	1.328 (6)	C15—H15A	0.9700
O1—C21	1.449 (6)	C15—H15B	0.9700
O2—C20	1.188 (6)	C16—C17	1.327 (7)
O3—C41	1.335 (5)	C16—H16	0.9300
O3—C42	1.434 (5)	C17—C18	1.501 (7)
O4—C41	1.183 (5)	C18—C19	1.498 (8)
O5—C43	1.237 (5)	C18—H18A	0.9700
O6—C43	1.255 (5)	C18—H18B	0.9700
O7—C44	1.401 (5)	C19—H19A	0.9600
O7—H7	0.8200	C19—H19B	0.9600
O8—C45	1.403 (6)	C19—H19C	0.9600
O8—H8	0.8200	C21—H21A	0.9600
O9—C46	1.241 (6)	C21—H21B	0.9600
O10—C46	1.235 (6)	C21—H21C	0.9600
O11—H11C	0.8488	C22—C23	1.390 (7)
O11—H11D	0.8606	C22—C27	1.397 (6)
O12—H12C	0.8546	C23—C24	1.382 (8)
O12—H12D	0.8618	C23—H23	0.9300
O13—H13C	0.8296	C24—C25	1.386 (8)
O13—H13D	0.8365	C24—H24	0.9300
N1—C1	1.369 (5)	C25—C26	1.358 (7)
N1—C8	1.378 (5)	C25—H25	0.9300
N1—H1A	0.8600	C26—C27	1.412 (6)
N2—C11	1.497 (6)	C26—H26	0.9300
N2—C15	1.506 (6)	C27—C28	1.423 (6)
N2—C10	1.518 (5)	C28—C29	1.361 (6)
N2—H2	0.9100	C28—C33	1.499 (6)
N3—C29	1.371 (5)	C29—C30	1.517 (6)
N3—C22	1.375 (6)	C30—C41	1.541 (6)
N3—H3A	0.8600	C30—C34	1.556 (6)
N4—C32	1.501 (5)	C30—C31	1.560 (6)
N4—C36	1.521 (6)	C31—C38	1.510 (6)
N4—C31	1.525 (5)	C31—H31	0.9800
N4—H4	0.9100	C32—C33	1.512 (6)
C1—C2	1.395 (6)	C32—H32A	0.9700
C1—C6	1.403 (6)	C32—H32B	0.9700
C2—C3	1.365 (7)	C33—H33A	0.9700
C2—H2a	0.9300	C33—H33B	0.9700
C3—C4	1.370 (8)	C34—C35	1.538 (6)
C3—H3	0.9300	C34—H34A	0.9700
C4—C5	1.382 (7)	C34—H34B	0.9700
C4—H4a	0.9300	C35—C37	1.494 (6)
C5—C6	1.404 (6)	C35—C36	1.522 (7)
C5—H5	0.9300	C35—H35	0.9800
C6—C7	1.438 (6)	C36—H36A	0.9700
C7—C8	1.359 (6)	C36—H36B	0.9700
C7—C12	1.497 (6)	C37—C38	1.324 (6)
C8—C9	1.523 (5)	C37—H37	0.9300
C9—C20	1.538 (6)	C38—C39	1.498 (6)
C9—C10	1.560 (6)	C39—C40	1.507 (7)
C9—C13	1.561 (6)	C39—H39A	0.9700
C10—C17	1.518 (6)	C39—H39B	0.9700
C10—H10	0.9800	C40—H40A	0.9600
C11—C12	1.505 (6)	C40—H40B	0.9600
C11—H11A	0.9700	C40—H40C	0.9600
C11—H11B	0.9700	C42—H42A	0.9600
C12—H12A	0.9700	C42—H42B	0.9600
C12—H12B	0.9700	C42—H42C	0.9600
C13—C14	1.532 (6)	C43—C44	1.525 (6)
C13—H13A	0.9700	C44—C45	1.522 (6)
C13—H13B	0.9700	C44—H44	0.9800
C14—C16	1.502 (7)	C45—C46	1.523 (7)
C14—C15	1.517 (7)	C45—H45	0.9800
C14—H14	0.9800
C20—O1—C21	114.9 (4)	O1—C21—H21C	109.5
C41—O3—C42	116.3 (4)	H21A—C21—H21C	109.5
C44—O7—H7	109.5	H21B—C21—H21C	109.5
C45—O8—H8	109.5	N3—C22—C23	129.5 (5)
H11C—O11—H11D	108.2	N3—C22—C27	107.6 (4)
H12C—O12—H12D	107.6	C23—C22—C27	122.9 (5)
H13C—O13—H13D	113.2	C24—C23—C22	116.1 (5)
C1—N1—C8	109.1 (3)	C24—C23—H23	122.0
C1—N1—H1A	125.4	C22—C23—H23	122.0
C8—N1—H1A	125.4	C23—C24—C25	122.3 (5)
C11—N2—C15	114.9 (4)	C23—C24—H24	118.9
C11—N2—C10	117.6 (3)	C25—C24—H24	118.9
C15—N2—C10	110.7 (3)	C26—C25—C24	121.4 (5)
C11—N2—H2	103.9	C26—C25—H25	119.3
C15—N2—H2	103.9	C24—C25—H25	119.3
C10—N2—H2	103.9	C25—C26—C27	118.7 (5)
C29—N3—C22	108.8 (4)	C25—C26—H26	120.7
C29—N3—H3A	125.6	C27—C26—H26	120.7
C22—N3—H3A	125.6	C22—C27—C26	118.6 (4)
C32—N4—C36	114.7 (3)	C22—C27—C28	107.0 (4)
C32—N4—C31	117.1 (3)	C26—C27—C28	134.4 (5)
C36—N4—C31	110.7 (3)	C29—C28—C27	107.2 (4)
C32—N4—H4	104.2	C29—C28—C33	126.7 (4)
C36—N4—H4	104.2	C27—C28—C33	125.9 (4)
C31—N4—H4	104.2	C28—C29—N3	109.4 (4)
N1—C1—C2	131.0 (4)	C28—C29—C30	128.5 (4)
N1—C1—C6	107.5 (3)	N3—C29—C30	122.1 (4)
C2—C1—C6	121.5 (4)	C29—C30—C41	108.9 (3)
C3—C2—C1	117.2 (5)	C29—C30—C34	112.7 (3)
C3—C2—H2a	121.4	C41—C30—C34	108.5 (4)
C1—C2—H2a	121.4	C29—C30—C31	112.7 (3)
C2—C3—C4	122.6 (5)	C41—C30—C31	106.7 (3)
C2—C3—H3	118.7	C34—C30—C31	107.0 (3)
C4—C3—H3	118.7	C38—C31—N4	105.7 (3)
C3—C4—C5	121.1 (5)	C38—C31—C30	108.5 (3)
C3—C4—H4a	119.4	N4—C31—C30	110.8 (3)
C5—C4—H4a	119.4	C38—C31—H31	110.6
C4—C5—C6	118.1 (5)	N4—C31—H31	110.6
C4—C5—H5	120.9	C30—C31—H31	110.6
C6—C5—H5	120.9	N4—C32—C33	116.8 (4)
C1—C6—C5	119.4 (4)	N4—C32—H32A	108.1
C1—C6—C7	107.1 (4)	C33—C32—H32A	108.1
C5—C6—C7	133.6 (4)	N4—C32—H32B	108.1
C8—C7—C6	106.6 (4)	C33—C32—H32B	108.1
C8—C7—C12	127.9 (4)	H32A—C32—H32B	107.3
C6—C7—C12	125.5 (4)	C28—C33—C32	113.7 (4)
C7—C8—N1	109.7 (3)	C28—C33—H33A	108.8
C7—C8—C9	129.3 (3)	C32—C33—H33A	108.8
N1—C8—C9	121.0 (3)	C28—C33—H33B	108.8
C8—C9—C20	109.2 (3)	C32—C33—H33B	108.8
C8—C9—C10	112.2 (3)	H33A—C33—H33B	107.7
C20—C9—C10	107.5 (3)	C35—C34—C30	109.2 (3)
C8—C9—C13	112.4 (3)	C35—C34—H34A	109.8
C20—C9—C13	108.7 (4)	C30—C34—H34A	109.8
C10—C9—C13	106.6 (3)	C35—C34—H34B	109.8
C17—C10—N2	105.8 (3)	C30—C34—H34B	109.8
C17—C10—C9	108.5 (3)	H34A—C34—H34B	108.3
N2—C10—C9	111.4 (3)	C37—C35—C36	106.9 (4)
C17—C10—H10	110.4	C37—C35—C34	110.0 (4)
N2—C10—H10	110.4	C36—C35—C34	108.2 (4)
C9—C10—H10	110.4	C37—C35—H35	110.5
N2—C11—C12	116.5 (4)	C36—C35—H35	110.5
N2—C11—H11A	108.2	C34—C35—H35	110.5
C12—C11—H11A	108.2	N4—C36—C35	108.0 (4)
N2—C11—H11B	108.2	N4—C36—H36A	110.1
C12—C11—H11B	108.2	C35—C36—H36A	110.1
H11A—C11—H11B	107.3	N4—C36—H36B	110.1
C7—C12—C11	114.4 (4)	C35—C36—H36B	110.1
C7—C12—H12A	108.7	H36A—C36—H36B	108.4
C11—C12—H12A	108.7	C38—C37—C35	115.3 (4)
C7—C12—H12B	108.7	C38—C37—H37	122.4
C11—C12—H12B	108.7	C35—C37—H37	122.4
H12A—C12—H12B	107.6	C37—C38—C39	128.1 (4)
C14—C13—C9	109.4 (4)	C37—C38—C31	112.0 (4)
C14—C13—H13A	109.8	C39—C38—C31	119.8 (4)
C9—C13—H13A	109.8	C38—C39—C40	115.4 (5)
C14—C13—H13B	109.8	C38—C39—H39A	108.4
C9—C13—H13B	109.8	C40—C39—H39A	108.4
H13A—C13—H13B	108.2	C38—C39—H39B	108.4
C16—C14—C15	106.9 (4)	C40—C39—H39B	108.4
C16—C14—C13	110.7 (4)	H39A—C39—H39B	107.5
C15—C14—C13	107.3 (4)	C39—C40—H40A	109.5
C16—C14—H14	110.6	C39—C40—H40B	109.5
C15—C14—H14	110.6	H40A—C40—H40B	109.5
C13—C14—H14	110.6	C39—C40—H40C	109.5
N2—C15—C14	108.6 (4)	H40A—C40—H40C	109.5
N2—C15—H15A	110.0	H40B—C40—H40C	109.5
C14—C15—H15A	110.0	O4—C41—O3	123.2 (4)
N2—C15—H15B	110.0	O4—C41—C30	125.7 (4)
C14—C15—H15B	110.0	O3—C41—C30	111.2 (4)
H15A—C15—H15B	108.4	O3—C42—H42A	109.5
C17—C16—C14	115.4 (4)	O3—C42—H42B	109.5
C17—C16—H16	122.3	H42A—C42—H42B	109.5
C14—C16—H16	122.3	O3—C42—H42C	109.5
C16—C17—C18	128.8 (4)	H42A—C42—H42C	109.5
C16—C17—C10	111.5 (4)	H42B—C42—H42C	109.5
C18—C17—C10	119.6 (4)	O5—C43—O6	125.5 (4)
C19—C18—C17	114.9 (5)	O5—C43—C44	117.6 (4)
C19—C18—H18A	108.5	O6—C43—C44	116.8 (4)
C17—C18—H18A	108.5	O7—C44—C45	109.7 (4)
C19—C18—H18B	108.5	O7—C44—C43	111.4 (3)
C17—C18—H18B	108.5	C45—C44—C43	111.1 (4)
H18A—C18—H18B	107.5	O7—C44—H44	108.2
C18—C19—H19A	109.5	C45—C44—H44	108.2
C18—C19—H19B	109.5	C43—C44—H44	108.2
H19A—C19—H19B	109.5	O8—C45—C44	109.3 (4)
C18—C19—H19C	109.5	O8—C45—C46	112.0 (4)
H19A—C19—H19C	109.5	C44—C45—C46	110.1 (4)
H19B—C19—H19C	109.5	O8—C45—H45	108.5
O2—C20—O1	124.1 (4)	C44—C45—H45	108.5
O2—C20—C9	125.3 (4)	C46—C45—H45	108.5
O1—C20—C9	110.6 (4)	O10—C46—O9	125.7 (5)
O1—C21—H21A	109.5	O10—C46—C45	116.7 (5)
O1—C21—H21B	109.5	O9—C46—C45	117.6 (4)
H21A—C21—H21B	109.5
C8—N1—C1—C2	−178.2 (5)	C24—C25—C26—C27	1.6 (9)
C8—N1—C1—C6	0.3 (5)	N3—C22—C27—C26	178.6 (4)
N1—C1—C2—C3	−178.7 (5)	C23—C22—C27—C26	−2.6 (7)
C6—C1—C2—C3	3.0 (7)	N3—C22—C27—C28	−1.9 (5)
C1—C2—C3—C4	−1.5 (8)	C23—C22—C27—C28	176.8 (5)
C2—C3—C4—C5	−0.6 (9)	C25—C26—C27—C22	0.4 (8)
C3—C4—C5—C6	1.2 (9)	C25—C26—C27—C28	−178.8 (6)
N1—C1—C6—C5	178.9 (4)	C22—C27—C28—C29	1.6 (5)
C2—C1—C6—C5	−2.4 (7)	C26—C27—C28—C29	−179.2 (5)
N1—C1—C6—C7	−0.8 (5)	C22—C27—C28—C33	−173.5 (4)
C2—C1—C6—C7	177.8 (4)	C26—C27—C28—C33	5.7 (9)
C4—C5—C6—C1	0.3 (7)	C27—C28—C29—N3	−0.6 (5)
C4—C5—C6—C7	179.9 (5)	C33—C28—C29—N3	174.5 (5)
C1—C6—C7—C8	1.0 (5)	C27—C28—C29—C30	178.9 (4)
C5—C6—C7—C8	−178.7 (5)	C33—C28—C29—C30	−6.0 (8)
C1—C6—C7—C12	−179.4 (4)	C22—N3—C29—C28	−0.6 (5)
C5—C6—C7—C12	0.9 (8)	C22—N3—C29—C30	179.8 (4)
C6—C7—C8—N1	−0.8 (5)	C28—C29—C30—C41	175.9 (5)
C12—C7—C8—N1	179.6 (4)	N3—C29—C30—C41	−4.7 (5)
C6—C7—C8—C9	178.5 (4)	C28—C29—C30—C34	−63.7 (6)
C12—C7—C8—C9	−1.0 (8)	N3—C29—C30—C34	115.8 (4)
C1—N1—C8—C7	0.3 (5)	C28—C29—C30—C31	57.6 (6)
C1—N1—C8—C9	−179.1 (4)	N3—C29—C30—C31	−122.9 (4)
C7—C8—C9—C20	170.8 (4)	C32—N4—C31—C38	−170.7 (4)
N1—C8—C9—C20	−9.9 (5)	C36—N4—C31—C38	55.3 (4)
C7—C8—C9—C10	51.6 (6)	C32—N4—C31—C30	71.9 (4)
N1—C8—C9—C10	−129.1 (4)	C36—N4—C31—C30	−62.1 (4)
C7—C8—C9—C13	−68.5 (5)	C29—C30—C31—C38	173.0 (3)
N1—C8—C9—C13	110.8 (4)	C41—C30—C31—C38	53.6 (4)
C11—N2—C10—C17	−167.6 (4)	C34—C30—C31—C38	−62.5 (4)
C15—N2—C10—C17	57.6 (4)	C29—C30—C31—N4	−71.3 (4)
C11—N2—C10—C9	74.8 (5)	C41—C30—C31—N4	169.2 (3)
C15—N2—C10—C9	−60.1 (4)	C34—C30—C31—N4	53.2 (4)
C8—C9—C10—C17	173.7 (3)	C36—N4—C32—C33	58.5 (5)
C20—C9—C10—C17	53.6 (4)	C31—N4—C32—C33	−73.7 (5)
C13—C9—C10—C17	−62.8 (4)	C29—C28—C33—C32	−47.1 (7)
C8—C9—C10—N2	−70.2 (4)	C27—C28—C33—C32	127.1 (5)
C20—C9—C10—N2	169.7 (3)	N4—C32—C33—C28	69.4 (5)
C13—C9—C10—N2	53.2 (4)	C29—C30—C34—C35	134.0 (4)
C15—N2—C11—C12	59.7 (5)	C41—C30—C34—C35	−105.3 (4)
C10—N2—C11—C12	−73.4 (5)	C31—C30—C34—C35	9.5 (5)
C8—C7—C12—C11	−47.5 (7)	C30—C34—C35—C37	48.3 (5)
C6—C7—C12—C11	133.0 (5)	C30—C34—C35—C36	−68.2 (5)
N2—C11—C12—C7	66.1 (6)	C32—N4—C36—C35	−131.9 (4)
C8—C9—C13—C14	132.4 (4)	C31—N4—C36—C35	3.3 (5)
C20—C9—C13—C14	−106.6 (4)	C37—C35—C36—N4	−58.2 (5)
C10—C9—C13—C14	9.0 (5)	C34—C35—C36—N4	60.2 (5)
C9—C13—C14—C16	48.3 (5)	C36—C35—C37—C38	56.5 (5)
C9—C13—C14—C15	−67.9 (5)	C34—C35—C37—C38	−60.8 (5)
C11—N2—C15—C14	−135.9 (4)	C35—C37—C38—C39	−172.0 (4)
C10—N2—C15—C14	0.3 (5)	C35—C37—C38—C31	5.6 (6)
C16—C14—C15—N2	−56.3 (4)	N4—C31—C38—C37	−62.4 (5)
C13—C14—C15—N2	62.4 (5)	C30—C31—C38—C37	56.5 (5)
C15—C14—C16—C17	57.7 (5)	N4—C31—C38—C39	115.4 (4)
C13—C14—C16—C17	−58.8 (6)	C30—C31—C38—C39	−125.7 (4)
C14—C16—C17—C18	−174.3 (5)	C37—C38—C39—C40	−5.8 (8)
C14—C16—C17—C10	2.9 (6)	C31—C38—C39—C40	176.7 (5)
N2—C10—C17—C16	−61.0 (5)	C42—O3—C41—O4	4.6 (7)
C9—C10—C17—C16	58.6 (5)	C42—O3—C41—C30	−175.5 (4)
N2—C10—C17—C18	116.5 (5)	C29—C30—C41—O4	100.6 (5)
C9—C10—C17—C18	−123.9 (5)	C34—C30—C41—O4	−22.5 (6)
C16—C17—C18—C19	6.9 (9)	C31—C30—C41—O4	−137.5 (5)
C10—C17—C18—C19	−170.1 (5)	C29—C30—C41—O3	−79.3 (4)
C21—O1—C20—O2	2.6 (7)	C34—C30—C41—O3	157.6 (3)
C21—O1—C20—C9	−178.3 (4)	C31—C30—C41—O3	42.6 (4)
C8—C9—C20—O2	105.4 (5)	O5—C43—C44—O7	7.0 (6)
C10—C9—C20—O2	−132.6 (5)	O6—C43—C44—O7	−172.4 (4)
C13—C9—C20—O2	−17.5 (6)	O5—C43—C44—C45	−115.6 (5)
C8—C9—C20—O1	−73.7 (4)	O6—C43—C44—C45	65.0 (5)
C10—C9—C20—O1	48.3 (4)	O7—C44—C45—O8	−57.8 (5)
C13—C9—C20—O1	163.3 (3)	C43—C44—C45—O8	65.8 (5)
C29—N3—C22—C23	−177.0 (5)	O7—C44—C45—C46	65.5 (5)
C29—N3—C22—C27	1.6 (5)	C43—C44—C45—C46	−170.9 (4)
N3—C22—C23—C24	−178.9 (5)	O8—C45—C46—O10	−177.9 (4)
C27—C22—C23—C24	2.7 (8)	C44—C45—C46—O10	60.3 (6)
C22—C23—C24—C25	−0.6 (9)	O8—C45—C46—O9	1.0 (6)
C23—C24—C25—C26	−1.5 (10)	C44—C45—C46—O9	−120.7 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5	0.86	2.02	2.821 (5)	155
N2—H2···O10^i	0.91	1.76	2.653 (5)	167
N3—H3A···O11	0.86	1.99	2.773 (5)	151
N4—H4···O6^ii	0.91	1.82	2.713 (4)	166
O7—H7···O5	0.82	2.19	2.623 (4)	113
O8—H8···O9	0.82	2.15	2.631 (7)	117
O11—H11C···O10	0.85	2.02	2.862 (6)	172
O11—H11D···O12	0.86	1.89	2.726 (5)	165
O12—H12C···O9^iii	0.85	1.89	2.720 (6)	164
O12—H12D···O13	0.86	1.96	2.760 (7)	155
O13—H13C···O6^iv	0.83	1.97	2.781 (5)	166
O13—H13D···O9	0.84	2.04	2.854 (5)	164

Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) −x+3/2, −y+1, z−1/2; (iii) x+1/2, −y+1/2, −z+1; (iv) x−1/2, −y+1/2, −z+1.