#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/04/2000441.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_2000441
loop_
_publ_author_name
'Karle, J. M.'
'Karle, I. L.'
_publ_section_title
;
 Structure of 9-epiquinine hydrochloride dihydrate versus
 antimalarial activity
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1975
_journal_page_last               1980
_journal_paper_doi               10.1107/S0108270192002373
_journal_volume                  48
_journal_year                    1992
_chemical_formula_moiety         'C20 H25 N2 O2,Cl,2(H2 O)'
_chemical_formula_sum            'C20 H29 Cl N2 O4'
_chemical_formula_weight         396.9
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.059(2)
_cell_length_b                   11.537(3)
_cell_length_c                   22.311(6)
_cell_volume                     2074.4(9)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.54178
_exptl_absorpt_coefficient_mu    1.858
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             848
_cod_data_source_file            cr0388.cif
_cod_data_source_block           cr0388a
_cod_original_cell_volume        2074.1(9)
_cod_database_code               2000441
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
N(1) 1.3428(6) .3765(4) 1.1323(2) .050(2)
C(2) 1.4645(9) .3174(6) 1.1723(3) .066(3)
C(3) 1.6031(9) .4016(7) 1.19080(10) .077(3)
C(4) 1.5759(10) .5146(7) 1.1545(4) .068(3)
C(5) 1.5699(11) .4870(8) 1.0880(4) .078(3)
C(6) 1.4252(9) .4084(6) 1.0741(3) .060(3)
C(7) 1.4119(8) .5686(6) 1.1727(3) .055(2)
C(8) 1.2732(8) .4798(5) 1.1643(3) .044(2)
C(9) 1.1196(8) .5254(5) 1.1320(3) .042(2)
C(10) 1.5867(14) .4101(11) 1.2586(4) .150(7)
C(11) 1.6871(18) .4591(10) 1.2931(5) .198(9)
O(12) 1.0033(5) .4328(4) 1.1262(2) .055(2)
N(13) .9014(8) .8224(5) 1.2220(3) .066(2)
C(14) .9784(11) .7390(8) 1.2504(3) .070(3)
C(15) 1.0505(9) .6416(6) 1.2249(3) .055(2)
C(16) 1.0397(8) .6257(5) 1.1638(3) .044(2)
C(17) .9486(7) .7106(5) 1.1305(3) .039(2)
C(18) .9146(8) .7015(5) 1.0687(3) .045(2)
C(19) .8355(9) .7880(6) 1.0399(3) .052(2)
C(20) .7828(9) .8892(7) 1.0697(3) .066(3)
C(21) .8089(9) .8979(6) 1.1298(3) .065(3)
C(22) .8880(9) .8097(6) 1.1618(3) .053(2)
O(23) .7944(7) .7874(4) .9795(2) .067(2)
C(24) .8181(11) .6813(7) .9468(3) .071(3)
Cl .9748(3) .3956(2) .98820(10) .0660(10)
O(W1) 1.1664(10) .1743(6) 1.0999(3) .091(3)
O(W2) .8156(8) .1990(6) 1.0728(3) .110(2)
H(1) 1.270(7) .333(5) 1.129(2) .052(17)
H(12) 1.004(8) .416(5) 1.094(2) .066(19)
H(2A) 1.4080 .2905 1.2076 ?
H(2B) 1.5125 .2527 1.1516 ?
H(3) 1.7152 .3791 1.1822 ?
H(4) 1.6664 .5665 1.1626 ?
H(5A) 1.6711 .4495 1.0762 ?
H(5B) 1.5576 .5582 1.0662 ?
H(6A) 1.4642 .3401 1.0540 ?
H(6B) 1.3473 .4483 1.0489 ?
H(7A) 1.4165 .5920 1.2140 ?
H(7B) 1.3904 .6351 1.1480 ?
H(8) 1.2342 .4595 1.2036 ?
H(9) 1.1541 .5536 1.0935 ?
H(14) .9857 .7459 1.2932 ?
H(15) 1.1066 .5858 1.2496 ?
H(18) .9490 .6337 1.0471 ?
H(20) .7291 .9506 1.0481 ?
H(21) .7725 .9662 1.1506 ?
H(24A) .7855 .6923 .9058 ?
H(24B) .7518 .6213 .9644 ?
H(24C) .9330 .6596 .9484 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(2) N(1) C(6) 109.6(5)
C(6) N(1) C(8) 112.4(5)
C(2) C(3) C(4) 106.8(5)
C(4) C(3) C(10) 116.9(7)
C(3) C(4) C(7) 109.2(6)
C(4) C(5) C(6) 110.6(6)
C(4) C(7) C(8) 109.2(6)
N(1) C(8) C(9) 110.6(5)
C(8) C(9) O(12) 108.6(5)
O(12) C(9) C(16) 109.8(5)
C(2) N(1) C(8) 108.9(5)
N(1) C(2) C(3) 110.5(5)
C(2) C(3) C(10) 104.1(6)
C(3) C(4) C(5) 109.8(5)
C(5) C(4) C(7) 108.7(6)
N(1) C(6) C(5) 108.1(5)
N(1) C(8) C(7) 108.5(5)
C(7) C(8) C(9) 114.9(5)
C(8) C(9) C(16) 112.9(5)
C(3) C(10) C(11) 125.8(10)
C(14) N(13) C(22) 116.0(6)
C(14) C(15) C(16) 119.1(6)
C(9) C(16) C(17) 120.1(5)
C(16) C(17) C(18) 123.8(5)
C(18) C(17) C(22) 118.2(5)
C(18) C(19) C(20) 122.1(6)
C(20) C(19) O(23) 113.0(6)
C(20) C(21) C(22) 121.4(7)
N(13) C(22) C(21) 117.7(6)
C(19) O(23) C(24) 117.7(5)
N(13) C(14) C(15) 126.6(7)
C(9) C(16) C(15) 122.9(6)
C(15) C(16) C(17) 117.0(5)
C(16) C(17) C(22) 118.0(5)
C(17) C(18) C(19) 120.2(6)
C(18) C(19) O(23) 124.9(6)
C(19) C(20) C(21) 118.6(7)
N(13) C(22) C(17) 123.0(6)
C(17) C(22) C(21) 119.3(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N(1) C(2) 1.491(9)
N(1) C(8) 1.499(8)
C(3) C(4) 1.550(11)
C(4) C(5) 1.518(11)
C(5) C(6) 1.509(11)
C(8) C(9) 1.526(9)
C(9) C(16) 1.502(9)
N(13) C(14) 1.309(10)
C(14) C(15) 1.386(11)
C(16) C(17) 1.433(8)
C(17) C(22) 1.426(9)
C(19) C(20) 1.409(10)
C(20) C(21) 1.361(10)
O(23) C(24) 1.437(9)
N(1) C(6) 1.504(8)
C(2) C(3) 1.536(10)
C(3) C(10) 1.522(9)
C(4) C(7) 1.517(10)
C(7) C(8) 1.528(9)
C(9) O(12) 1.427(7)
C(10) C(11) 1.252(16)
N(13) C(22) 1.355(9)
C(15) C(16) 1.379(8)
C(17) C(18) 1.409(8)
C(18) C(19) 1.347(9)
C(19) O(23) 1.389(8)
C(21) C(22) 1.397(10)
