Crystal structure of {tetraaqua-bis(1-(4-hydroxy-2-oxotetrahydrofuran-3-yl)-2-((4aS,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethane-1-sulfonato-k2O,O') calcium(II)}-{triaqua-bis(1-(4-hydroxy-2-oxotetrahydrofuran-3-yl)-2-((4aS,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethane-1-sulfonato-k2O,O') calcium(II)} – water – acetone (1/1/8/2)

Ying-Jie Chang; Yuan-Min Ding; Lin-Yuan Zhu; Hong-Min Liu; Wen Li

doi:10.1515/ncrs-2020-0382

Article Open Access

Crystal structure of {tetraaqua-bis(1-(4-hydroxy-2-oxotetrahydrofuran-3-yl)-2-((4aS,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethane-1-sulfonato-k²O,O') calcium(II)}-{triaqua-bis(1-(4-hydroxy-2-oxotetrahydrofuran-3-yl)-2-((4aS,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethane-1-sulfonato-k²O,O') calcium(II)} – water – acetone (1/1/8/2)

Ying-Jie Chang , Yuan-Min Ding , Lin-Yuan Zhu , Hong-Min Liu and Wen Li

Published/Copyright: November 5, 2020

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From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 236 Issue 1

Abstract

C₄₃H₇₈CaO₂₂S₂, monoclinic, P2₁ (no. 4), a = 18.2539(3) Å, b = 15.3118(3) Å, c = 18.3718(4) Å, β = 91.2637(17)°, Z = 4, V = 5133.65(18) Å³, R_gt(F) = 0.0544, wR_ref(F²) = 0.1622, T = 293(2) K.

CCDC no.: 1881394

Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.


Crystal:	Colourless
Size:	0.22 × 0.16 × 0.13 mm
Wavelength:	Cu Kα radiation (1.54184 Å)
μ:	2.48 mm^-1
Diffractometer, scan mode:	Xcalibur, ω
θ_max, completeness:	70.9°, >99%
N(hkl)_measured, N(hkl)_unique, R_int:	25633, 15314, 0.027
Criterion for I_obs, N(hkl)_gt:	I_obs > 2 σ(I_obs), 12706
N(param)_refined:	1271
Programs:	Bruker [1], SHELX [2], [3]

Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²).

Atom	x	y	z	U_iso*/U_eq
C1	0.1185 (3)	0.3018 (3)	0.7137 (3)	0.0319 (10)
H1A	0.0834	0.2837	0.6762	0.038*
H1B	0.1625	0.2671	0.7083	0.038*
C1"	0.6199 (3)	0.5511 (3)	0.2148 (3)	0.0326 (10)
H1"A	0.5870	0.5296	0.1768	0.039*
H1"B	0.6662	0.5206	0.2106	0.039*
C1′	−0.1129 (2)	0.2983 (3)	1.2771 (2)	0.0309 (10)
H1′A	−0.0771	0.2789	1.3134	0.037*
H1′B	−0.1571	0.2643	1.2832	0.037*
C1A	0.3838 (3)	0.5465 (3)	0.7801 (2)	0.0312 (10)
H1AA	0.4216	0.5291	0.8151	0.037*
H1AB	0.3407	0.5113	0.7888	0.037*
C2	0.0864 (3)	0.2838 (3)	0.7888 (3)	0.0396 (11)
H2A	0.0738	0.2224	0.7926	0.048*
H2B	0.1227	0.2971	0.8265	0.048*
C2"	0.5876 (3)	0.5312 (3)	0.2889 (3)	0.0395 (11)
H2"A	0.5795	0.4688	0.2932	0.047*
H2"B	0.6222	0.5485	0.3271	0.047*
C2′	−0.0830 (3)	0.2809 (3)	1.2010 (3)	0.0382 (11)
H2′A	−0.0718	0.2193	1.1961	0.046*
H2′B	−0.1200	0.2959	1.1644	0.046*
C2A	0.4103 (3)	0.5281 (4)	0.7036 (3)	0.0429 (12)
H2AA	0.4226	0.4666	0.6993	0.051*
H2AB	0.3714	0.5410	0.6684	0.051*
C3	0.0185 (3)	0.3389 (4)	0.8001 (2)	0.0357 (11)
H3	−0.0167	0.3253	0.7606	0.043*
C3"	0.5160 (3)	0.5788 (4)	0.2988 (2)	0.0361 (11)
H3"	0.4825	0.5612	0.2592	0.043*
C3′	−0.0144 (3)	0.3341 (4)	1.1884 (2)	0.0358 (11)
H3′	0.0219	0.3181	1.2261	0.043*
C3A	0.4771 (3)	0.5829 (4)	0.6870 (2)	0.0410 (12)
H3A	0.5152	0.5686	0.7235	0.049*
C4	0.0339 (3)	0.4375 (3)	0.7977 (2)	0.0342 (10)
C4"	0.5241 (3)	0.6787 (3)	0.2957 (3)	0.0363 (11)
C4′	−0.0270 (2)	0.4330 (3)	1.1931 (2)	0.0324 (10)
C4A	0.4630 (3)	0.6813 (4)	0.6916 (2)	0.0356 (11)
C5	0.0685 (2)	0.4548 (3)	0.7212 (2)	0.0286 (9)
H5	0.0307	0.4357	0.6860	0.034*
C5"	0.5599 (2)	0.6993 (3)	0.2204 (2)	0.0310 (10)
H5"	0.5244	0.6776	0.1839	0.037*
C5′	−0.0607 (2)	0.4507 (3)	1.2700 (2)	0.0288 (9)
H5′	−0.0226	0.4313	1.3048	0.035*
C5A	0.4329 (2)	0.6991 (3)	0.7696 (2)	0.0298 (9)
H5A	0.4724	0.6799	0.8028	0.036*
C6	0.0795 (3)	0.5522 (3)	0.7042 (3)	0.0389 (11)
H6A	0.1185	0.5754	0.7352	0.047*
H6B	0.0349	0.5840	0.7144	0.047*
C6"	0.5655 (3)	0.7978 (3)	0.2050 (3)	0.0432 (12)
H6"A	0.6022	0.8236	0.2373	0.052*
H6"B	0.5188	0.8255	0.2144	0.052*
C6′	−0.0705 (3)	0.5474 (3)	1.2871 (3)	0.0387 (11)
H6′A	−0.1101	0.5710	1.2570	0.046*
H6′B	−0.0260	0.5788	1.2757	0.046*
C6A	0.4237 (3)	0.7963 (3)	0.7866 (3)	0.0406 (11)
H6AA	0.3830	0.8198	0.7579	0.049*
H6AB	0.4677	0.8276	0.7734	0.049*
C7	0.0989 (3)	0.5650 (4)	0.6239 (3)	0.0432 (12)
H7A	0.0577	0.5480	0.5928	0.052*
H7B	0.1093	0.6262	0.6149	0.052*
C7"	0.5863 (3)	0.8134 (4)	0.1251 (3)	0.0432 (12)
H7"A	0.5470	0.7935	0.0929	0.052*
H7"B	0.5934	0.8754	0.1169	0.052*
C7′	−0.0877 (3)	0.5606 (4)	1.3674 (3)	0.0428 (12)
H7′A	−0.0460	0.5429	1.3975	0.051*
H7′B	−0.0972	0.6219	1.3766	0.051*
C7A	0.4095 (3)	0.8096 (4)	0.8680 (3)	0.0452 (13)
H7AA	0.4524	0.7921	0.8964	0.054*
H7AB	0.4003	0.8709	0.8774	0.054*
C8	0.1648 (3)	0.5107 (3)	0.6059 (2)	0.0331 (10)
C8"	0.6555 (3)	0.7649 (3)	0.1089 (2)	0.0344 (10)
C8′	−0.1537 (3)	0.5073 (3)	1.3864 (2)	0.0316 (9)
C8A	0.3448 (3)	0.7565 (3)	0.8899 (2)	0.0334 (10)
C9	0.1524 (2)	0.4139 (3)	0.6189 (2)	0.0258 (8)
H9	0.1074	0.3980	0.5921	0.031*
C9"	0.6483 (2)	0.6672 (3)	0.1210 (2)	0.0267 (9)
H9"	0.6041	0.6490	0.0937	0.032*
C9′	−0.1419 (2)	0.4104 (3)	1.3739 (2)	0.0266 (9)
H9′	−0.0958	0.3950	1.3989	0.032*
C9A	0.3551 (2)	0.6598 (3)	0.8769 (2)	0.0246 (8)
H9AA	0.4015	0.6434	0.9011	0.030*
C10	0.1374 (2)	0.3989 (3)	0.7024 (2)	0.0253 (9)
C10"	0.6325 (2)	0.6496 (3)	0.2037 (2)	0.0257 (9)
C10′	−0.1301 (2)	0.3953 (3)	1.2901 (2)	0.0246 (8)
C10A	0.3648 (2)	0.6436 (3)	0.7925 (2)	0.0257 (9)
C11	0.2138 (2)	0.3555 (3)	0.5897 (2)	0.0336 (10)
H11A	0.2604	0.3746	0.6106	0.040*
H11B	0.2056	0.2959	0.6054	0.040*
C11"	0.7115 (2)	0.6126 (3)	0.0911 (2)	0.0338 (10)
H11E	0.7049	0.5520	0.1049	0.041*
H11F	0.7573	0.6328	0.1127	0.041*
C11′	−0.2015 (2)	0.3523 (3)	1.4063 (2)	0.0303 (9)
H11C	−0.1944	0.2925	1.3906	0.036*
H11D	−0.2492	0.3714	1.3882	0.036*
C11A	0.2948 (2)	0.6020 (3)	0.9101 (2)	0.0310 (9)
H11G	0.2473	0.6218	0.8922	0.037*
H11H	0.3014	0.5422	0.8940	0.037*
C12	0.2179 (2)	0.3576 (3)	0.5063 (2)	0.0320 (10)
H12	0.2224	0.4190	0.4919	0.038*
C12"	0.7156 (2)	0.6188 (3)	0.0076 (2)	0.0317 (10)
H12"	0.7200	0.6806	−0.0054	0.038*
C12′	−0.1999 (2)	0.3559 (3)	1.4902 (2)	0.0299 (9)
H12′	−0.1897	0.4165	1.5041	0.036*
C12A	0.2964 (2)	0.6045 (3)	0.9938 (2)	0.0299 (9)
H12A	0.3078	0.6646	1.0083	0.036*
C13	0.1501 (3)	0.3217 (4)	0.4679 (2)	0.0386 (11)
C13"	0.6494 (2)	0.5829 (4)	−0.0319 (2)	0.0348 (11)
C13′	−0.1414 (3)	0.3005 (4)	1.5257 (3)	0.0415 (12)
C13A	0.3531 (3)	0.5471 (4)	1.0289 (3)	0.0357 (11)
C14	0.1208 (3)	0.2437 (5)	0.4696 (3)	0.0563 (15)
H14	0.1396	0.1969	0.4963	0.068*
C14"	0.6164 (3)	0.5071 (5)	−0.0270 (3)	0.0503 (14)
H14"	0.6312	0.4621	0.0040	0.060*
C14′	−0.1386 (4)	0.2157 (5)	1.5393 (3)	0.0597 (16)
H14′	−0.1745	0.1758	1.5250	0.072*
C14A	0.3521 (3)	0.4620 (4)	1.0451 (3)	0.0520 (14)
H14A	0.3133	0.4244	1.0345	0.062*
C15	0.0541 (4)	0.2406 (6)	0.4235 (4)	0.069 (2)
H15A	0.0594	0.1995	0.3838	0.083*
H15B	0.0119	0.2242	0.4517	0.083*
C15"	0.5523 (3)	0.5030 (6)	−0.0779 (4)	0.0650 (19)
H15E	0.5577	0.4563	−0.1130	0.078*
H15F	0.5073	0.4941	−0.0517	0.078*
C15′	−0.0705 (4)	0.1931 (7)	1.5804 (5)	0.095 (3)
H15C	−0.0816	0.1699	1.6280	0.114*
H15D	−0.0420	0.1504	1.5542	0.114*
C15A	0.4218 (4)	0.4364 (6)	1.0822 (4)	0.077 (2)
H15G	0.4129	0.4143	1.1306	0.092*
H15H	0.4469	0.3919	1.0546	0.092*
C16	0.1040 (4)	0.3769 (6)	0.4219 (4)	0.073 (2)
C16"	0.6087 (4)	0.6348 (6)	−0.0861 (4)	0.070 (2)
C16′	−0.0736 (4)	0.3380 (6)	1.5559 (4)	0.071 (2)
C16A	0.4243 (3)	0.5808 (5)	1.0549 (3)	0.0564 (16)
C17	0.2271 (3)	0.5462 (4)	0.5866 (3)	0.0444 (13)
H17A	0.2314	0.6067	0.5837	0.053*
H17B	0.2669	0.5109	0.5759	0.053*
C17"	0.7168 (3)	0.8051 (4)	0.0924 (3)	0.0481 (13)
H17E	0.7183	0.8658	0.0905	0.058*
H17F	0.7586	0.7728	0.0827	0.058*
C17′	−0.2156 (3)	0.5431 (4)	1.4072 (3)	0.0458 (13)
H17C	−0.2195	0.6035	1.4104	0.055*
H17D	−0.2553	0.5079	1.4185	0.055*
C17A	0.2842 (3)	0.7938 (4)	0.9125 (3)	0.0464 (13)
H17G	0.2810	0.8543	0.9149	0.056*
H17H	0.2446	0.7595	0.9259	0.056*
C18	−0.0390 (3)	0.4863 (5)	0.8016 (3)	0.0560 (16)
H18A	−0.0667	0.4772	0.7573	0.084*
H18B	−0.0297	0.5475	0.8080	0.084*
H18C	−0.0662	0.4647	0.8420	0.084*
C18"	0.4472 (3)	0.7177 (5)	0.2960 (3)	0.065 (2)
H18G	0.4203	0.6927	0.3352	0.098*
H18H	0.4225	0.7051	0.2506	0.098*
H18I	0.4505	0.7798	0.3025	0.098*
C18′	0.0481 (3)	0.4777 (5)	1.1904 (3)	0.0536 (15)
H18D	0.0416	0.5386	1.1797	0.080*
H18E	0.0767	0.4511	1.1532	0.080*
H18F	0.0730	0.4715	1.2367	0.080*
C18A	0.5369 (3)	0.7292 (5)	0.6843 (3)	0.0592 (17)
H18J	0.5621	0.7069	0.6430	0.089*
H18K	0.5663	0.7201	0.7276	0.089*
H18L	0.5281	0.7906	0.6779	0.089*
C19	0.0853 (3)	0.4683 (4)	0.8602 (3)	0.0408 (12)
H19A	0.1275	0.4299	0.8633	0.049*
H19B	0.1027	0.5266	0.8495	0.049*
C19"	0.5699 (3)	0.7154 (4)	0.3598 (3)	0.0464 (13)
H19E	0.6138	0.6802	0.3662	0.056*
H19F	0.5851	0.7744	0.3481	0.056*
C19′	−0.0761 (3)	0.4670 (3)	1.1313 (2)	0.0365 (10)
H19C	−0.1186	0.4293	1.1261	0.044*
H19D	−0.0933	0.5250	1.1437	0.044*
C19A	0.4102 (3)	0.7129 (4)	0.6309 (2)	0.0394 (11)
H19G	0.3677	0.6748	0.6287	0.047*
H19H	0.3934	0.7713	0.6424	0.047*
C20	0.2071 (2)	0.4226 (3)	0.7465 (2)	0.0331 (10)
H20A	0.2491	0.3989	0.7230	0.050*
H20B	0.2042	0.3987	0.7947	0.050*
H20C	0.2116	0.4850	0.7495	0.050*
C20"	0.6996 (3)	0.6786 (4)	0.2493 (2)	0.0362 (11)
H20G	0.6944	0.6596	0.2987	0.054*
H20H	0.7034	0.7411	0.2481	0.054*
H20I	0.7430	0.6533	0.2296	0.054*
C20′	−0.2000 (2)	0.4209 (3)	1.2474 (2)	0.0329 (10)
H20D	−0.2026	0.4833	1.2433	0.049*
H20E	−0.2421	0.3999	1.2726	0.049*
H20F	−0.1991	0.3954	1.1997	0.049*
C20A	0.2934 (2)	0.6685 (3)	0.7525 (2)	0.0318 (10)
H20J	0.2916	0.6410	0.7055	0.048*
H20K	0.2913	0.7307	0.7466	0.048*
H20L	0.2525	0.6493	0.7803	0.048*
Ca1	0.00043 (6)	0.34412 (7)	0.99371 (6)	0.0317 (2)
Ca1A	0.49034 (5)	0.58920 (7)	0.49181 (5)	0.0345 (2)
O1	−0.0148 (2)	0.3157 (3)	0.86785 (19)	0.0495 (10)
H1	−0.051 (3)	0.282 (4)	0.8592 (13)	0.074*
O1"	0.4842 (2)	0.5523 (3)	0.36639 (19)	0.0494 (10)
H1"	0.450 (3)	0.515 (4)	0.3584 (14)	0.074*
O1′	0.0151 (2)	0.3109 (3)	1.11907 (19)	0.0498 (10)
H1′	0.050 (3)	0.275 (4)	1.1256 (13)	0.075*
O1A	0.5044 (2)	0.5585 (3)	0.61679 (19)	0.0596 (13)
H1AC	0.542 (3)	0.525 (4)	0.6229 (13)	0.089*
O2	0.0489 (2)	0.4688 (3)	0.92948 (18)	0.0449 (9)
H2	0.065 (3)	0.514 (2)	0.9527 (14)	0.067*
O2"	0.5310 (2)	0.7165 (3)	0.42693 (19)	0.0491 (9)
H2"	0.533 (3)	0.7685 (12)	0.444 (2)	0.074*
O2′	−0.0390 (2)	0.4708 (2)	1.06272 (17)	0.0389 (8)
H2′	−0.050 (3)	0.5197 (15)	1.0433 (15)	0.058*
O2A	0.4443 (2)	0.7138 (3)	0.56072 (18)	0.0442 (9)
H2AC	0.427 (3)	0.758 (2)	0.5383 (14)	0.066*
O3	0.0469 (3)	0.3288 (5)	0.3965 (3)	0.096 (2)
O3"	0.5527 (3)	0.5872 (5)	−0.1130 (3)	0.0843 (17)
O3′	−0.0325 (3)	0.2736 (6)	1.5865 (3)	0.101 (2)
O3A	0.4638 (3)	0.5151 (5)	1.0855 (3)	0.0828 (18)
O4	0.1095 (4)	0.4524 (5)	0.4072 (4)	0.127 (3)
O4"	0.6209 (4)	0.7075 (5)	−0.1064 (4)	0.116 (3)
O4′	−0.0538 (3)	0.4126 (5)	1.5550 (4)	0.110 (2)
O4A	0.4481 (3)	0.6530 (5)	1.0514 (3)	0.093 (2)
O5	0.2895 (2)	0.2110 (3)	0.4973 (2)	0.0547 (10)
O5"	0.7888 (2)	0.4726 (3)	−0.0010 (2)	0.0497 (9)
O5′	−0.3022 (2)	0.2396 (3)	1.5038 (2)	0.0514 (10)
O5A	0.1884 (2)	0.4931 (3)	1.0031 (2)	0.0532 (10)
O6	0.2979 (2)	0.3132 (3)	0.3967 (2)	0.0514 (10)
O6"	0.7939 (2)	0.5735 (3)	−0.10293 (19)	0.0487 (9)
O6′	−0.2805 (2)	0.3379 (3)	1.60480 (19)	0.0498 (10)
O6A	0.2139 (2)	0.5863 (3)	1.10723 (19)	0.0510 (10)
O7	0.3607 (2)	0.3415 (3)	0.5112 (2)	0.0551 (11)
O7"	0.85846 (19)	0.6054 (3)	0.0098 (2)	0.0519 (10)
O7′	−0.3406 (2)	0.3889 (3)	1.4940 (2)	0.0554 (11)
O7A	0.1583 (2)	0.6459 (3)	0.9971 (2)	0.0583 (12)
O8	0.1273 (2)	0.3110 (5)	1.0020 (3)	0.088 (2)
H8A	0.1373	0.2552	1.0085	0.132*
H8B	0.1534	0.3414	1.0407	0.132*
O8A	0.3616 (2)	0.5747 (4)	0.4684 (3)	0.0828 (17)
H8AA	0.3758	0.5252	0.4821	0.124*
H8AB	0.3506	0.5806	0.4212	0.124*
O9	−0.0060 (2)	0.1870 (3)	0.9931 (3)	0.0615 (12)
H9A	0.0242	0.1531	1.0316	0.092*
H9B	−0.0582	0.1580	0.9878	0.092*
O9A	0.4922 (3)	0.4324 (3)	0.4928 (3)	0.0651 (12)
H9AB	0.5341	0.4083	0.4717	0.098*
H9AC	0.4526	0.4073	0.4673	0.098*
O10	−0.12636 (19)	0.3260 (3)	0.9881 (3)	0.0545 (10)
H10A	−0.1449	0.3688	0.9655	0.082*
H10B	−0.1399	0.2696	0.9941	0.082*
O10A	0.61798 (18)	0.5681 (3)	0.4985 (2)	0.0475 (9)
H10C	0.6453	0.6058	0.4674	0.071*
H10D	0.6335	0.5102	0.4853	0.071*
S1	0.29810 (6)	0.30140 (9)	0.47466 (7)	0.0347 (3)
S1"	0.79544 (6)	0.56290 (10)	−0.02483 (6)	0.0328 (3)
S1′	−0.28769 (6)	0.32806 (9)	1.52647 (6)	0.0330 (3)
S1A	0.20726 (6)	0.57929 (10)	1.02853 (6)	0.0358 (3)
C21	0.7993 (5)	0.6146 (5)	0.6792 (4)	0.074 (2)
C22	0.7951 (6)	0.5534 (7)	0.6155 (5)	0.110 (4)
H22A	0.7720	0.4999	0.6299	0.165*
H22B	0.8436	0.5412	0.5992	0.165*
H22C	0.7669	0.5798	0.5767	0.165*
C23	0.7288 (5)	0.6368 (7)	0.7128 (5)	0.100 (3)
H23A	0.7212	0.6988	0.7102	0.150*
H23B	0.7299	0.6187	0.7628	0.150*
H23C	0.6896	0.6074	0.6872	0.150*
O11	0.8569 (4)	0.6453 (5)	0.7008 (3)	0.097 (2)
C21A	0.6926 (4)	0.3687 (5)	0.8209 (4)	0.0679 (18)
C22A	0.7650 (5)	0.3973 (6)	0.7937 (5)	0.088 (2)
H22D	0.7675	0.3852	0.7425	0.131*
H22E	0.8034	0.3662	0.8192	0.131*
H22F	0.7709	0.4589	0.8017	0.131*
C23A	0.6926 (6)	0.3011 (7)	0.8801 (5)	0.105 (3)
H23D	0.6434	0.2923	0.8961	0.157*
H23E	0.7228	0.3206	0.9203	0.157*
H23F	0.7115	0.2471	0.8617	0.157*
O11A	0.6358 (3)	0.3990 (5)	0.7973 (3)	0.096 (2)
O14	0.2371 (5)	0.5421 (5)	0.3628 (4)	0.133 (3)
H14B	0.1965	0.5325	0.3832	0.199*
H14C	0.2450	0.5175	0.3192	0.199*
O19	0.6069 (4)	0.4479 (5)	0.6579 (3)	0.117 (3)
H19I	0.6489	0.4437	0.6392	0.175*
H19J	0.6053	0.4191	0.7037	0.175*
O15	0.2159 (4)	0.7090 (5)	0.2986 (3)	0.113 (2)
H15I	0.2252	0.6640	0.3271	0.169*
H15J	0.2438	0.7470	0.3335	0.169*
O16	0.2711 (4)	0.4682 (5)	0.2127 (4)	0.125 (3)
H16A	0.2493	0.5097	0.1904	0.187*
H16B	0.2659	0.4280	0.1792	0.187*
O12	0.8746 (3)	0.7059 (5)	0.8383 (3)	0.0848 (18)
H12B	0.8579	0.7120	0.7951	0.127*
H12C	0.8478	0.6664	0.8566	0.127*
O17	0.2466 (4)	0.3092 (5)	0.1245 (4)	0.122 (3)
H17I	0.2346	0.2942	0.1656	0.183*
H17J	0.2794	0.2718	0.1148	0.183*
O13	0.3789 (4)	0.4407 (5)	0.3225 (4)	0.117 (3)
H13A	0.3527	0.4550	0.2856	0.175*
H13B	0.3559	0.3986	0.3416	0.175*
O18	0.1169 (3)	0.7024 (4)	0.1821 (3)	0.0770 (15)
H18M	0.1336	0.7078	0.2254	0.115*
H18N	0.1502	0.6665	0.1705	0.115*

Source of material

Andrographolide calcium bisulfite crude product was provided by Jiangsu Jiuxu Pharmaceutical Com. Ltd. To begin with, the raw materials were dissolved in mixture of absolute water and acetone and then slow evaporation at room temperature for 3 days. Finally, we obtained the crystals of the title compound.

Experimental details

All hydrogen atmos were located in calculated positions and refined as riding atoms. The hydrogen atoms of tertiary and secondary carbons for isotropic displacement factors U_iso(H) were set to 1.2 times U_eq(C), 1.5 times U_eq(C) of methyl hydrogen atoms and 1.5 times U_eq(O).

Comment

Andrographolide, a diterpenoid lactone, can be obtained from the extract of traditional herb Andrographis paniculata with extraordinary efficacy for treating various diseases including diarrhea, hepatic protection, rheumatoid arthritis, upperrespiratory tract infection, cancer and so on [4], [5], [6], [7], and the Andrographolide’s contribution of these effects had been proved by pharmacological researches [8]. Furthermore, Andrographolide is a neuroprotection regulator in central nervous system (CNS) [9]. Andrographolide has been identified an anti-inflammatory, anti-bacteria and anti-virus drug, however, which blocks its excellent clinically application prospect for extremely poor water solubility and low bioavailability. Given inadequacies of Andrographolide, researchers improved its solubility by introducing hydrophilic sodium bisulfite group, resulting in Andrographolide sodium bisulfite (ASB). In a recent study, we found Andrographolide calcium bisulfite (ACB) which is a related impurity of ASB.

The asymmetric unit contains four andrographolide bisulfite anions, two calcium cations, two molecules of acetone and 14 molecules of water. Ca1 adopts a distorted polyhedron geometry by coordinating to four oxygen atoms of hydroxyl from a pair of organic ligands and four oxygen atoms of four water ligands (see the figure). In contrast Ca1a is sevenfold coordinated by four hydroxy groups of two organic ligands and three water ligands.

The organic ligand andrographolide calcium bisulfite consists of two fused cyclohexanes adopting chair conformations and a nearly planar five-membered lactonic ring. Ca–O distances are in the range of those observed in reported Ca(II) complexes [10], [11]. The O–S distances coincided with the normal ranges. And bond angles around the central Ca (II) ion vary from 71.47 (13)° to 164.85 (19)°. The Flack parameter (absolute configuration) was determined to 0.003(7), thus the configuration at atoms C3, C4, C5, C9, C10 and C12 are in R, R, S, R, S and R, respectively.

Corresponding author: Wen Li, School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001, People’s Republic of China; Henan Province Collaborative Innovation Center of New Drug Research and Safety Evaluation, Zhengzhou, People’s Republic of China; Ministry of Education, Key Laboratory of Advanced Drug Preparation Technologies, Zhengzhou, People’s Republic of China; and Key Laboratory of Henan Province for Drug Quality and Evaluation, Zhengzhou, People’s Republic of China, E-mail: liwen@zzu.edu.cn

Funding source: Science and Technology Bureau of Henan Province for the Cooperation Research Project Fund

Award Identifier / Grant number: 152107000041

Acknowledgments

The Analysis and Testing Center of Zhengzhou University is acknowledged for the single crystal X-ray diffraction facility.

Research funding: This work was supported by the Science and Technology Bureau of Henan Province for the Cooperation Research Project Fund (No. 152107000041 for WL) and Jiangsu Jiuxu Pharmaceutical Com. Ltd.
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2020-07-22

Accepted: 2020-09-16

Published Online: 2020-11-05

Published in Print: 2021-01-26

This work is licensed under the Creative Commons Attribution 4.0 International License.

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