#------------------------------------------------------------------------------
#$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/14/2101401.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_2101401
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 CDCl~3~
;
_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            'C24 H31 N O9'
_chemical_formula_weight         477.5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_cell_angle_alpha                90.0
_cell_angle_beta                 114.32(2)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   26.555(3)
_cell_length_b                   8.7370(10)
_cell_length_c                   11.4940(10)
_cell_volume                     2430.1(6)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.54184
_exptl_absorpt_coefficient_mu    0.84
_exptl_crystal_density_diffrn    1.305
_cod_data_source_file            cr0493.cif
_cod_data_source_block           cr0493a
_cod_original_cell_volume        2430.0(5)
_cod_original_formula_sum        'C24 H31 N1 O9'
_cod_database_code               2101401
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
O(1) .58400(10) .7511 .6544(3) .0560(10)
O(2) .6250(2) .6494(6) .7428(3) .075(2)
C(3) .6719(2) .7347(9) .8126(5) .076(2)
C(4) .6589(2) .8803(9) .8696(5) .082(3)
C(5) .6521(2) 1.0205(8) .7879(5) .081(3)
C(5a) .6083(2) 1.0113(7) .6494(5) .061(2)
C(6) .6128(3) 1.1442(8) .5673(7) .100(4)
C(7) .5727(3) 1.1301(9) .4312(7) .109(4)
C(8) .5765(2) .9783(8) .3727(5) .082(3)
C(8a) .5662(2) .8458(7) .4485(4) .058(2)
C(9) .5654(2) .6852(8) .3971(4) .064(2)
C(10) .6225(2) .6310(7) .4166(3) .052(2)
O(11) .66130(10) .6513(5) .5456(2) .0560(10)
C(12) .6632(2) .7963(7) .6032(4) .051(2)
C(12a) .6068(2) .8530(6) .5893(4) .044(2)
O(13) .69980(10) .7740(6) .7312(2) .078(2)
C(14) .7098(3) .6248(12) .91296(5) .136(4)
C(15) .6069(5) 1.2967(9) .6247(9) .151(7)
C(16) .5244(2) .6641(12) .2577(5) .115(3)
O(17) .64030(10) .7070(5) .3315(2) .0460(10)
C(18) .6796(2) .6215(7) .3026(3) .048(2)
C(19) .6509(2) .4922(7) .21110(4) .049(2)
C(20) .6062(2) .5231(8) .0967(4) .072(2)
C(21) .5788(2) .4029(9) .0171(5) .084(3)
C(22) .5955(2) .2556(9) .0540(5) .071(2)
C(23) .6395(2) .2248(8) .1625(5) .086(3)
C(24) .6671(2) .3434(8) .2416(5) .068(2)
N(25) .5633(3) .1279(11) -.0293(7) .118(4)
O(26) .5258(3) .1604(11) -.1307(6) .198(4)
O(27) .5776(3) -.0015(9) .0081(7) .147(4)
C(28) .7061(2) .7356(7) .2469(4) .058(2)
C(29) .7427(2) .8476(8) .3451(4) .064(2)
O(30) .7624(2) .8274(7) .4564(3) .113(2)
O(31) .7527(2) .9697(7) .2920(3) .107(2)
H(4A) .6886 .8983 .9515 .080
H(4B) .6252 .8643 .8800 .080
H(5A) .6424 1.1043 .8286 .080
H(5B) .6871 1.0410 .7850 .080
H(5a) .5730 1.0232 .6525 .080
H(6) .6489 1.1400 .5672 .080
H(7A) .5360 1.1413 .4268 .080
H(7B) .5798 1.2104 .3830 .080
H(8A) .5492 .9748 .2861 .080
H(8B) .6126 .9676 .3738 .080
H(8a) .5289 .8629 .4386 .080
H(9) .5524 .6219 .4472 .080
H(10) .6203 .5233 .3985 .080
H(12) .6753 .8753 .5625 .080
H(14A) .7435 .6765 .9650 .080
H(14B) .7181 .5392 .8712 .080
H(14C) .6919 .5893 .9650 .080
H(15A) .6333 1.3019 .7120 .080
H(15B) .5703 1.3055 .6209 .080
H(15C) .6135 1.3789 .5773 .080
H(16A) .4886 .6990 .2471 .080
H(16B) .5225 .5577 .2354 .080
H(16C) .5366 .7222 .2032 .080
H(18) .7071 .5733 .3765 .080
H(20) .5943 .6266 .0730 .080
H(21) .5484 .4227 -.0633 .080
H(23) .6516 .1211 .1848 .080
H(24) .6983 .3214 .3200 .080
H(28A) .7281 .6811 .2118 .080
H(28B) .6776 .7914 .1802 .080
H(31) .784(3) 1.060(9) .374(6) .12(2)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O(2) O(1) C(12a) 112.8(3)
O(2) C(3) C(4) 112.7(5)
C(4) C(3) O(13) 110.1(6)
C(4) C(3) C(14) 113.4(5)
C(3) C(4) C(5) 113.4(5)
C(5) C(5a) C(6) 112.4(5)
C(6) C(5a) C(12a) 113.5(5)
C(5a) C(6) C(15) 110.4(7)
C(6) C(7) C(8) 112.9(6)
C(8) C(8a) C(9) 116.8(5)
C(9) C(8a) C(12a) 109.9(4)
C(8a) C(9) C(16) 114.1(5)
C(9) C(10) O(11) 111.5(4)
O(11) C(10) O(17) 110.9(4)
O(11) C(12) C(12a) 113.4(4)
C(12a) C(12) O(13) 112.4(4)
O(1) C(12a) C(8a) 105.0(3)
O(1) C(12a) C(12) 110.4(4)
C(8a) C(12a) C(12) 109.4(4)
C(10) O(17) C(18) 113.5(4)
O(17) C(18) C(28) 105.5(4)
C(18) C(19) C(20) 120.1(5)
C(20) C(19) C(24) 118.9(5)
C(20) C(21) C(22) 119.5(5)
C(21) C(22) N(25) 118.5(5)
C(22) C(23) C(24) 119.2(6)
C(22) N(25) O(26) 117.9(9)
O(26) N(25) O(27) 124.8(9)
C(28) C(29) O(30) 125.2(6)
O(30) C(29) O(31) 122.9(6)
O(1) O(2) C(3) 108.2(4)
O(2) C(3) O(13) 109.2(4)
O(2) C(3) C(14) 104.8(6)
O(13) C(3) C(14) 106.4(5)
C(4) C(5) C(5a) 116.6(5)
C(5) C(5a) C(12a) 112.3(4)
C(5a) C(6) C(7) 112.4(6)
C(7) C(6) C(15) 111.7(6)
C(7) C(8) C(8a) 110.3(6)
C(8) C(8a) C(12a) 110.8(4)
C(8a) C(9) C(10) 112.3(4)
C(10) C(9) C(16) 110.7(5)
C(9) C(10) O(17) 110.5(4)
C(10) O(11) C(12) 117.9(4)
O(11) C(12) O(13) 104.0(4)
O(1) C(12a) C(5a) 105.1(4)
C(5a) C(12a) C(8a) 112.8(4)
C(5a) C(12a) C(12) 113.7(4)
C(3) O(13) C(12) 113.1(3)
O(17) C(18) C(19) 110.2(3)
C(19) C(18) C(28) 112.7(4)
C(18) C(19) C(24) 120.9(3)
C(19) C(20) C(21) 119.3(6)
C(21) C(22) C(23) 121.6(6)
C(23) C(22) N(25) 119.9(7)
C(19) C(24) C(23) 121.4(4)
C(22) N(25) O(27) 117.2(6)
C(18) C(28) C(29) 112.4(4)
C(28) C(29) O(31) 111.8(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O(1) O(2) 1.447(4)
O(2) C(3) 1.388(7)
C(3) O(13) 1.452(8)
C(4) C(5) 1.508(10)
C(5a) C(6) 1.532(10)
C(6) C(7) 1.491(9)
C(7) C(8) 1.510(11)
C(8a) C(9) 1.519(9)
C(9) C(10) 1.515(7)
C(10) O(11) 1.426(4)
O(11) C(12) 1.421(7)
C(12) O(13) 1.403(4)
C(18) C(19) 1.517(7)
C(19) C(20) 1.387(5)
C(20) C(21) 1.385(9)
C(22) C(23) 1.339(7)
C(23) C(24) 1.374(9)
N(25) O(27) 1.214(12)
C(29) O(30) 1.179(6)
O(1) C(12a) 1.446(6)
C(3) C(4) 1.533(10)
C(3) C(14) 1.518(10)
C(5) C(5a) 1.538(6)
C(5a) C(12a) 1.539(8)
C(6) C(15) 1.523(12)
C(8) C(8a) 1.540(9)
C(8a) C(12a) 1.533(5)
C(9) C(16) 1.533(6)
C(10) O(17) 1.415(6)
C(12) C(12a) 1.523(6)
O(17) C(18) 1.429(6)
C(18) C(28) 1.508(8)
C(19) C(24) 1.369(9)
C(21) C(22) 1.371(11)
C(22) N(25) 1.489(11)
N(25) O(26) 1.215(9)
C(28) C(29) 1.508(7)
C(29) O(31) 1.310(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102002596