#------------------------------------------------------------------------------
#$Date: 2018-01-30 16:30:45 +0200 (Tue, 30 Jan 2018) $
#$Revision: 205898 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/14/2101402.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2101402
loop_
_publ_author_name
'Karle, J. M.'
'Lin, Ai. J.'
_publ_section_title
;
 Correlation of the crystal structures of diastereomeric artemisinin
 derivatives with their proton NMR spectra in CDCl₃
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              1063
_journal_page_last               1068
_journal_paper_doi               10.1107/S0108768195005581
_journal_volume                  51
_journal_year                    1995
_chemical_formula_sum            'C26 H35 N O9'
_chemical_formula_weight         505.6
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_cell_angle_alpha                90.0
_cell_angle_beta                 91.51(2)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   12.392(2)
_cell_length_b                   10.639(2)
_cell_length_c                   20.081(2)
_cell_volume                     2646.5(7)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.54184
_exptl_absorpt_coefficient_mu    0.80
_exptl_crystal_density_diffrn    1.269
_cod_data_source_file            cr0493.cif
_cod_data_source_block           cr0493b
_cod_original_formula_sum        'C26 H35 N1 O9'
_cod_database_code               2101402
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
O(1A) .5684(4) .1166 .9728(2) .065(2)
O(2A) .5758(4) .2491(7) .9515(3) .068(2)
C(3A) .5289(7) .2592(12) .8875(5) .073(4)
C(4A) .4188(8) .1974(12) .8807(5) .084(4)
C(5A) .4179(7) .0638(12) .8549(4) .083(4)
C(5aA) .4900(7) -.0279(10) .8944(4) .065(4)
C(6A) .5040(8) -.1507(12) .8553(4) .079(4)
C(7A) .5754(8) -.2407(11) .8924(4) .082(4)
C(8A) .6838(8) -.1838(11) .9113(4) .077(4)
C(8aA) .6727(8) -.0677(11) .9536(4) .070(4)
C(9A) .7761(7) -.0034(11) .9779(4) .071(4)
C(10A) .8311(8) .0658(11) .9221(4) .075(4)
O(11A) .7597(5) .1481(8) .8877(3) .066(2)
C(12A) .6581(7) .1021(11) .8652(4) .065(4)
C(12aA) .5962(7) .0302(10) .9199(3) .055(3)
O(13A) .5995(4) .2060(8) .8397(2) .069(2)
C(14A) .5261(8) .4001(11) .8741(5) .097(5)
C(15A) .3955(8) -.2122(12) .8377(5) .110(5)
C(16A) .8542(9) -.0888(13) 1.0170(5) .106(5)
O(17A) .8767(4) -.0257(8) .8786(2) .068(2)
C(18A) .9610(6) .0197(11) .8368(4) .069(3)
C(19A) .9179(6) .0614(11) .7698(4) .061(3)
C(20A) .8380(7) -.0106(10) .7359(4) .063(3)
C(21A) .8073(6) .0174(11) .6720(4) .063(3)
C(22A) .8545(8) .1201(12) .6418(4) .067(4)
C(23A) .9283(7) .1936(11) .6740(5) .076(4)
C(24A) .9594(7) .1651(12) .7374(5) .072(4)
N(25A) .8212(7) .1484(12) .5718(4) .083(4)
O(26A) .8563(7) .2414(10) .5468(3) .117(3)
O(27A) .7654(7) .0749(12) .5423(3) .134(4)
C(28A) 1.0351(7) -.0930(12) .8276(4) .088(4)
C(29A) 1.0844(11) -.1431(18) .8926(7) .112(7)
O(30A) 1.0784(7) -.2545(12) .9070(4) .140(4)
O(31A) 1.1265(6) -.0604(11) .9282(4) .105(4)
C(32A) 1.1751(12) -.1018(16) .9920(7) .141(8)
C(33A) 1.1919(15) -.0134(18) 1.0336(7) .231(12)
O(1B) .4494(4) .1900(9) .2864(3) .078(2)
O(2B) .4539(5) .3181(9) .3143(3) .088(3)
C(3B) .4954(8) .3109(13) .3797(6) .085(5)
C(4B) .5982(7) .2309(13) .3864(5) .096(5)
C(5B) .5772(8) .0939(13) .4052(5) .092(5)
C(5aB) .4986(7) .0199(12) .3585(4) .072(4)
C(6B) .4668(8) -.1024(12) .3907(5) .082(4)
C(7B) .3937(7) -.1764(11) .3414(5) .084(4)
C(8B) .2936(7) -.1009(11) .3217(5) .081(4)
C(8aB) .3247(7) .0241(11) .2904(4) .068(4)
C(9B) .2280(7) .1057(12) .2685(4) .076(4)
C(10B) .1802(7) .1724(11) .3266(4) .071(4)
O(11B) .2560(5) .2406(9) .3644(3) .069(2)
C(12B) .3474(7) .1709(11) .3889(4) .073(4)
C(12aB) .4040(6) .1013(11) .3328(4) .061(3)
O(13B) .4133(4) .2593(8) .4221(3) .074(2)
C(14B) .5109(9) .4436(13) .4011(6) .118(6)
C(15B) .5652(8) -.1816(14) .4113(5) .119(5)
C(16B) .1432(8) .0381(14) .2263(4) .112(5)
O(17B) .1214(4) .0862(8) .3661(2) .062(2)
C(18B) .0528(6) .1473(11) .4137(4) .071(4)
C(19B) .0998(6) .1328(12) .4838(4) .060(4)
C(20B) .1325(6) .2362(11) .5201(5) .070(4)
C(21B) .1702(7) .2264(13) .5845(5) .079(4)
C(22B) .1786(6) .1083(13) .6122(4) .065(4)
C(23B) .1496(7) .0024(12) .5777(5) .080(4)
C(24B) .1093(7) .0159(12) .5140(5) .083(4)
N(25B) .2195(7) .0953(15) .6816(4) .090(5)
O(26B) .2363(7) .1904(12) .7138(4) .131(4)
O(27B) .2332(7) -.0095(13) .7027(4) .128(4)
C(28B) -.0565(6) .0853(12) .4048(4) .074(4)
C(29B) -.1053(9) .1188(18) .3369(5) .094(5)
O(30B) -.0968(7) .2205(12) .3110(4) .129(4)
O(31B) -.1571(6) .0244(11) .3093(3) .113(4)
C(32B) -.2104(14) .0465(19) .2446(7) .223(11)
C(33B) -.1999(15) -.0213(17) .2003(6) .228(12)
H(4AA) .3752 .2474 .8506 .080
H(4AB) .3873 .1972 .9238 .080
H(5AA) .3451 .0332 .8558 .080
H(5AB) .4415 .0650 .8097 .080
H(5aA) .4536 -.0485 .9346 .080
H(6A) .5379 -.1290 .8144 .080
H(7AA) .5403 -.2659 .9324 .080
H(7AB) .5868 -.3130 .8649 .080
H(8AA) .7203 -.1617 .8713 .080
H(8AB) .7258 -.2449 .9357 .080
H(8aA) .6422 -.1009 .9934 .080
H(9A) .7535 .0581 1.0096 .080
H(10A) .8875 .1182 .9405 .080
H(12A) .6677 .0402 .8311 .080
H(14A) .4946 .4153 .8307 .080
H(14B) .5982 .4329 .8762 .080
H(14C) .4836 .4408 .9071 .080
H(15A) .3504 -.1533 .8138 .080
H(15B) .3610 -.2371 .8779 .080
H(15C) .4070 -.2848 .8104 .080
H(16A) .8163 -.1307 1.0517 .080
H(16B) .9117 -.0392 1.0363 .080
H(16C) .8837 -.1502 .9875 .080
H(18A) .9965 .0911 .8568 .080
H(20A) .8050 -.0799 .7582 .080
H(21A) .7544 -.0328 .6484 .080
H(23A) .9583 .2653 .6521 .080
H(24A) 1.0112 .2176 .7604 .080
H(28A) 1.0926 -.0684 .7993 .080
H(28B) .9940 -.1592 .8066 .080
H(32A) 1.2429 -.1416 .9833 .080
H(32B) 1.1274 -.1616 1.0116 .080
H(33A) 1.2235 -.0473 1.0739 .080
H(33B) 1.1248 .0269 1.0433 .080
H(33C) 1.2403 .0469 1.0150 .080
H(4BA) .6445 .2676 .4201 .080
H(4BB) .6338 .2322 .3445 .080
H(5BA) .6453 .0507 .4059 .080
H(5BB) .5481 .0932 .4490 .080
H(5aB) .5352 -.0028 .3187 .080
H(6B) .4289 -.0836 .4306 .080
H(7BA) .3720 -.2535 .3619 .080
H(7BB) .4335 -.1949 .3021 .080
H(8BA) .2506 -.1483 .2902 .080
H(8BB) .2525 -.0850 .3607 .080
H(8aB) .3608 -.0013 .2509 .080
H(9B) .2569 .1679 .2393 .080
H(10B) .1308 .2342 .3089 .080
H(12B) .3274 .1049 .4187 .080
H(14D) .5395 .4455 .4459 .080
H(14E) .4428 .4867 .3990 .080
H(14F) .5604 .4844 .3721 .080
H(15D) .6102 -.1349 .4420 .080
H(15E) .6054 -.2021 .3725 .080
H(15F) .5417 -.2576 .4322 .080
H(16D) .1771 -.0031 .1899 .080
H(16E) .0913 .0978 .2093 .080
H(16F) .1075 -.0231 .2531 .080
H(18B) .0470 .2363 .4065 .080
H(20B) .1286 .3177 .4997 .080
H(21B) .1904 .2999 .6096 .080
H(23B) .1573 -.0793 .5975 .080
H(24B) .0870 -.0576 .4895 .080
H(28C) -.0484 -.0043 .4081 .080
H(28D) -.1033 .1142 .4390 .080
H(32C) -.1872 .1278 .2301 .080
H(32D) -.2864 .0486 .2527 .080
H(33D) -.2414 .0087 .1625 .080
H(33E) -.2242 -.1039 .2120 .080
H(33F) -.1250 -.0246 .1894 .080
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O(2A) O(1A) C(12aA) 111.9(5)
O(2A) C(3A) C(4A) 113.6(8)
C(4A) C(3A) O(13A) 109.4(8)
C(4A) C(3A) C(14A) 113.2(9)
C(3A) C(4A) C(5A) 115.9(9)
C(5A) C(5aA) C(6A) 110.4(7)
C(6A) C(5aA) C(12aA) 114.0(7)
C(5aA) C(6A) C(15A) 111.8(8)
C(6A) C(7A) C(8A) 112.3(9)
C(8A) C(8aA) C(9A) 117.4(8)
C(9A) C(8aA) C(12aA) 109.7(9)
C(8aA) C(9A) C(16A) 114.4(9)
C(9A) C(10A) O(11A) 112.0(8)
O(11A) C(10A) O(17A) 111.9(6)
O(11A) C(12A) C(12aA) 113.3(6)
C(12aA) C(12A) O(13A) 112.5(7)
O(1A) C(12aA) C(8aA) 105.1(5)
O(1A) C(12aA) C(12A) 109.6(7)
C(8aA) C(12aA) C(12A) 109.3(7)
C(10A) O(17A) C(18A) 115.5(8)
O(17A) C(18A) C(28A) 104.8(9)
C(18A) C(19A) C(20A) 120.0(9)
C(20A) C(19A) C(24A) 118.1(8)
C(20A) C(21A) C(22A) 118.2(9)
C(21A) C(22A) N(25A) 117.6(9)
C(22A) C(23A) C(24A) 119.4(10)
C(22A) N(25A) O(26A) 118.0(9)
O(26A) N(25A) O(27A) 123.3(9)
C(28A) C(29A) O(30A) 121.2(13)
O(30A) C(29A) O(31A) 125.3(13)
O(31A) C(32A) C(33A) 114.0(14)
O(1B) O(2B) C(3B) 108.4(8)
O(2B) C(3B) O(13B) 108.9(8)
O(2B) C(3B) C(14B) 105.1(10)
O(13B) C(3B) C(14B) 106.1(9)
C(4B) C(5B) C(5aB) 116.3(8)
C(5B) C(5aB) C(12aB) 112.3(10)
C(5aB) C(6B) C(7B) 108.7(8)
C(7B) C(6B) C(15B) 110.0(10)
C(7B) C(8B) C(8aB) 110.8(8)
C(8B) C(8aB) C(12aB) 113.9(7)
C(8aB) C(9B) C(10B) 111.5(7)
C(10B) C(9B) C(16B) 112.2(7)
C(9B) C(10B) O(17B) 110.2(9)
C(10B) O(11B) C(12B) 115.7(9)
O(11B) C(12B) O(13B) 105.2(9)
O(1B) C(12aB) C(5aB) 106.1(7)
C(5aB) C(12aB) C(8aB) 111.0(9)
C(5aB) C(12aB) C(12B) 112.7(7)
C(3B) O(13B) C(12B) 112.6(7)
O(17B) C(18B) C(19B) 110.4(7)
C(19B) C(18B) C(28B) 112.7(7)
C(18B) C(19B) C(24B) 121.5(10)
C(19B) C(20B) C(21B) 122.0(11)
C(21B) C(22B) C(23B) 122.1(9)
C(23B) C(22B) N(25B) 118.7(12)
O(1A) O(2A) C(3A) 108.2(7)
O(2A) C(3A) O(13A) 109.8(7)
O(2A) C(3A) C(14A) 104.1(8)
O(13A) C(3A) C(14A) 106.4(8)
C(4A) C(5A) C(5aA) 115.0(8)
C(5A) C(5aA) C(12aA) 113.7(9)
C(5aA) C(6A) C(7A) 111.3(8)
C(7A) C(6A) C(15A) 110.3(10)
C(7A) C(8A) C(8aA) 112.0(8)
C(8A) C(8aA) C(12aA) 111.6(7)
C(8aA) C(9A) C(10A) 111.9(7)
C(10A) C(9A) C(16A) 112.1(8)
C(9A) C(10A) O(17A) 108.2(9)
C(10A) O(11A) C(12A) 118.9(8)
O(11A) C(12A) O(13A) 106.9(8)
O(1A) C(12aA) C(5aA) 106.3(6)
C(5aA) C(12aA) C(8aA) 112.6(8)
C(5aA) C(12aA) C(12A) 113.4(6)
C(3A) O(13A) C(12A) 112.6(7)
O(17A) C(18A) C(19A) 112.0(6)
C(19A) C(18A) C(28A) 108.9(7)
C(18A) C(19A) C(24A) 121.8(8)
C(19A) C(20A) C(21A) 120.7(9)
C(21A) C(22A) C(23A) 122.3(9)
C(23A) C(22A) N(25A) 120.1(10)
C(19A) C(24A) C(23A) 121.3(9)
C(22A) N(25A) O(27A) 118.6(11)
C(18A) C(28A) C(29A) 113.6(9)
C(28A) C(29A) O(31A) 113.5(15)
C(29A) O(31A) C(32A) 116.5(13)
O(2B) O(1B) C(12aB) 111.6(6)
O(2B) C(3B) C(4B) 113.3(9)
C(4B) C(3B) O(13B) 109.4(10)
C(4B) C(3B) C(14B) 113.6(9)
C(3B) C(4B) C(5B) 113.8(8)
C(5B) C(5aB) C(6B) 110.2(8)
C(6B) C(5aB) C(12aB) 115.1(8)
C(5aB) C(6B) C(15B) 112.0(8)
C(6B) C(7B) C(8B) 111.0(9)
C(8B) C(8aB) C(9B) 114.1(7)
C(9B) C(8aB) C(12aB) 110.0(9)
C(8aB) C(9B) C(16B) 114.6(10)
C(9B) C(10B) O(11B) 113.3(7)
O(11B) C(10B) O(17B) 112.2(6)
O(11B) C(12B) C(12aB) 111.9(7)
C(12aB) C(12B) O(13B) 113.6(7)
O(1B) C(12aB) C(8aB) 104.3(6)
O(1B) C(12aB) C(12B) 110.5(9)
C(8aB) C(12aB) C(12B) 111.7(7)
C(10B) O(17B) C(18B) 113.3(8)
O(17B) C(18B) C(28B) 105.4(7)
C(18B) C(19B) C(20B) 120.7(10)
C(20B) C(19B) C(24B) 117.7(8)
C(20B) C(21B) C(22B) 118.2(11)
C(21B) C(22B) N(25B) 119.2(11)
C(22B) C(23B) C(24B) 118.2(11)
C(19B) C(24B) C(23B) 121.8(11)
C(22B) N(25B) O(27B) 117.5(12)
C(18B) C(28B) C(29B) 109.7(9)
C(28B) C(29B) O(31B) 112.3(14)
C(29B) O(31B) C(32B) 117.3(12)
C(22B) N(25B) O(26B) 118.3(13)
O(26B) N(25B) O(27B) 124.3(10)
C(28B) C(29B) O(30B) 124.1(13)
O(30B) C(29B) O(31B) 123.6(10)
O(31B) C(32B) C(33B) 121.8(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O(1A) O(2A) 1.477(7)
O(2A) C(3A) 1.401(11)
C(3A) O(13A) 1.433(11)
C(4A) C(5A) 1.513(17)
C(5aA) C(6A) 1.538(16)
C(6A) C(7A) 1.490(15)
C(7A) C(8A) 1.513(14)
C(8aA) C(9A) 1.521(14)
C(9A) C(10A) 1.516(13)
C(10A) O(11A) 1.414(12)
O(11A) C(12A) 1.413(11)
C(12A) O(13A) 1.411(13)
C(18A) C(19A) 1.503(12)
C(19A) C(20A) 1.411(13)
C(20A) C(21A) 1.363(12)
C(22A) C(23A) 1.355(15)
C(23A) C(24A) 1.355(14)
N(25A) O(27A) 1.191(15)
C(29A) O(30A) 1.22(2)
O(31A) C(32A) 1.468(16)
O(1B) O(2B) 1.474(13)
O(2B) C(3B) 1.401(13)
C(3B) O(13B) 1.451(13)
C(4B) C(5B) 1.53(2)
C(5aB) C(6B) 1.510(17)
C(6B) C(7B) 1.541(14)
C(7B) C(8B) 1.521(14)
C(8aB) C(9B) 1.534(14)
C(9B) C(10B) 1.501(13)
C(10B) O(11B) 1.394(12)
O(11B) C(12B) 1.430(12)
C(12B) O(13B) 1.403(12)
C(18B) C(19B) 1.517(11)
C(19B) C(20B) 1.375(16)
C(20B) C(21B) 1.367(14)
C(22B) C(23B) 1.366(17)
C(23B) C(24B) 1.368(14)
N(25B) O(27B) 1.20(2)
C(29B) O(30B) 1.21(2)
O(31B) C(32B) 1.461(17)
O(1A) C(12aA) 1.453(9)
C(3A) C(4A) 1.517(14)
C(3A) C(14A) 1.523(17)
C(5A) C(5aA) 1.530(14)
C(5aA) C(12aA) 1.530(12)
C(6A) C(15A) 1.528(14)
C(8A) C(8aA) 1.508(15)
C(8aA) C(12aA) 1.552(13)
C(9A) C(16A) 1.530(15)
C(10A) O(17A) 1.434(12)
C(12A) C(12aA) 1.558(12)
O(17A) C(18A) 1.440(10)
C(18A) C(28A) 1.525(16)
C(19A) C(24A) 1.386(15)
C(21A) C(22A) 1.386(15)
C(22A) N(25A) 1.487(13)
N(25A) O(26A) 1.195(15)
C(28A) C(29A) 1.522(17)
C(29A) O(31A) 1.24(2)
C(32A) C(33A) 1.27(2)
O(1B) C(12aB) 1.450(12)
C(3B) C(4B) 1.535(16)
C(3B) C(14B) 1.487(19)
C(5B) C(5aB) 1.549(14)
C(5aB) C(12aB) 1.536(13)
C(6B) C(15B) 1.530(16)
C(8B) C(8aB) 1.524(16)
C(8aB) C(12aB) 1.525(13)
C(9B) C(16B) 1.514(14)
C(10B) O(17B) 1.426(12)
C(12B) C(12aB) 1.533(13)
O(17B) C(18B) 1.450(10)
C(18B) C(28B) 1.513(12)
C(19B) C(24B) 1.387(17)
C(21B) C(22B) 1.377(19)
C(22B) N(25B) 1.477(12)
N(25B) O(26B) 1.215(18)
C(28B) C(29B) 1.519(14)
C(29B) O(31B) 1.307(19)
C(32B) C(33B) 1.16(2)
