#------------------------------------------------------------------------------
#$Date: 2008-04-03 11:11:48 +0100 (Thu, 03 Apr 2008) $
#$Revision: 326 $
#$URL: svn://www.crystallography.net/cod/cif/2/2100909.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2100909
loop_
_publ_author_name
'Larsen, S.'
'de Diego, H. L.'
'Kozma, D.'
_publ_section_title
;
 Optical resolution through diastereomeric salt formation: the crystal
 structures of cinchoninium (<i>R</i>)-mandelate and cinchoninium
 (<i>S</i>)-mandelate at low temperature
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              310
_journal_page_last               316
_journal_volume                  49
_journal_year                    1993
_chemical_formula_moiety         'C19 H23 N2 O1,C8 H7 O3'
_chemical_formula_sum            'C27 H30 N2 O4'
_chemical_formula_weight         446.55
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2y1'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_beta                 99.068(7)
_cell_formula_units_Z            2
_cell_length_a                   11.2478(10)
_cell_length_b                   7.0880(6)
_cell_length_c                   14.684(2)
_cell_volume                     1156.0(4)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.5418
_exptl_absorpt_coefficient_mu    0.657
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             476
_[local]_cod_data_source_file    ab0286.cif
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
C(1) .53810(10) .2776(3) -.01600(10) .0166(4)
O(1) .53510(10) .250 .06792(8) .0200(3)
O(2) .45400(10) .2338(2) -.08014(8) .0203(3)
C(2) .65180(10) .3680(3) -.04340(10) .0176(4)
O(3) .71060(10) .4875(2) .02742(8) .0195(3)
C(3) .7419(2) .2183(3) -.06160(10) .0174(4)
C(4) .7199(2) .0255(3) -.05540(10) .0237(4)
C(5) .8079(2) -.1053(3) -.06760(10) .0275(4)
C(6) .9193(2) -.0461(3) -.08540(10) .0267(4)
C(7) .9416(2) .1456(3) -.09260(10) .0284(4)
C(8) .8538(2) .2764(3) -.08070(10) .0252(4)
C(9) .51770(10) .5339(3) .66800(10) .0160(4)
C(10) .60450(10) .6730(3) .65330(10) .0175(4)
C(11) .6299(2) .8369(3) .70920(10) .0209(4)
C(12) .7125(2) .9675(3) .69030(10) .0250(4)
C(13) .7734(2) .9418(3) .61380(10) .0274(5)
C(14) .7531(2) .7846(3) .56010(10) .0250(4)
C(15) .6694(2) .6459(3) .57870(10) .0201(4)
N(1) .65560(10) .4889(3) .52330(10) .0231(4)
C(16) .5780(2) .3609(3) .54190(10) .0231(4)
C(17) .5067(3) .3777(3) .61260(10) .0195(4)
C(18) .43800(10) .5595(3) .74170(10) .0148(4)
O(4) .37950(10) .3882(2) .75797(8) .0182(3)
C(19) .34400(10) .7138(3) .70960(10) .0158(4)
C(20) .2432(2) .6530(3) .63200(10) .0185(4)
C(21) .1265(2) .7523(3) .64580(10) .0209(4)
C(22) .1542(2) .9616(3) .66550(10) .0245(4)
C(23) .2329(2) .9794(3) .76130(10) .0213(4)
N(2) .28560(10) .7884(2) .78879(9) .0158(3)
C(24) .1866(2) .6614(3) .81020(10) .0198(4)
C(25) .0796(2) .6682(3) .73030(10) .0222(4)
C(26) .0237(2) .4777(4) .7117(2) .0386(5)
C(27) -.0929(2) .4458(4) .7130(2) .0560(6)
H2 .622(2) .440(4) -.1040(10) ?
H3 .655(2) .564(4) .0430(10) ?
H4 .636(2) -.020(4) -.0460(10) ?
H5 .790(2) -.245(4) -.0550(10) ?
H6 .986(2) -.137(4) -.0900(10) ?
H7 1.021(2) .193(4) -.1070(10) ?
H8 .865(2) .410(4) -.0840(10) ?
H11 .588(2) .851(4) .7660(10) ?
H12 .732(2) 1.073(4) .7300(10) ?
H13 .835(2) 1.049(4) .5990(10) ?
H14 .792(2) .764(4) .5060(10) ?
H16 .571(2) .250(4) .4980(10) ?
H17 .448(2) .280(4) .6190(10) ?
H18 .488(2) .601(4) .8020(10) ?
HO4 .415(2) .345(4) .8150(10) ?
H19 .384(2) .824(4) .6900(10) ?
H2O .237(2) .510(4) .6320(10) ?
H20' .265(2) .680(4) .5710(10) ?
H21 .064(2) .737(4) .5910(10) ?
H22 .077(2) 1.039(4) .6640(10) ?
H22' .197(2) 1.010(4) .6210(10) ?
H23 .187(2) 1.016(4) .8090(10) ?
H23' .302(2) 1.066(4) .7600(10) ?
HN2 .347(2) .793(4) .8440(10) ?
H24 .220(2) .537(4) .8230(10) ?
H24' .165(2) .701(4) .8700(10) ?
H25 .020(2) .765(4) .7500(10) ?
H26 .081(2) .379(4) .6940(10) ?
H27 -.147(2) .317(4) .7020(10) ?
H27' -.082(2) .422(4) .6620(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C(9) C(10) 1.427(2)
C(9) C(17) 1.369(2)
C(9) C(18) 1.520(2)
C(10) C(11) 1.425(2)
C(10) C(15) 1.422(2)
C(11) C(12) 1.371(2)
C(12) C(13) 1.416(2)
C(13) C(14) 1.363(3)
C(14) C(15) 1.418(2)
C(15) N(1) 1.373(2)
N(1) C(16) 1.317(2)
C(16) C(17) 1.412(2)
C(18) O(4) 1.419(2)
C(18) C(19) 1.542(2)
C(19) C(20) 1.537(2)
C(19) N(2) 1.519(2)
C(20) C(21) 1.530(2)
C(21) C(22) 1.534(2)
C(21) C(25) 1.543(2)
C(22) C(23) 1.545(2)
C(23) N(2) 1.507(2)
N(2) C(24) 1.503(2)
C(24) C(25) 1.544(2)
C(25) C(26) 1.497(3)
C(26) C(27) 1.334(3)
O(1) C(1) 1.254(2)
O(2) C(1) 1.264(2)
C(1) C(2) 1.540(2)
C(2) O(3) 1.421(2)
C(2) C(3) 1.520(2)
C(3) C(4) 1.394(2)
C(3) C(8) 1.395(2)
C(4) C(5) 1.389(3)
C(5) C(6) 1.385(3)
C(6) C(7) 1.389(3)
C(7) C(8) 1.386(3)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(10) C(9) C(17) 117.97(14)
C(10) C(9) C(18) 121.25(14)
C(17) C(9) C(18) 120.77(14)
C(9) C(10) C(11) 123.80(14)
C(9) C(10) C(15) 118.0(2)
C(11) C(10) C(15) 118.23(14)
C(10) C(11) C(12) 121.0(2)
C(11) C(12) C(13) 120.1(2)
C(12) C(13) C(14) 120.4(2)
C(13) C(14) C(15) 120.7(2)
C(10) C(15) C(14) 119.5(2)
C(10) C(15) N(1) 122.9(2)
C(14) C(15) N(1) 117.61(14)
C(15) N(1) C(16) 116.83(13)
N(1) C(16) O(17) 124.5(2)
C(9) C(17) C(16) 119.8(2)
C(9) C(18) O(4) 111.04(13)
C(9) C(18) C(19) 108.63(12)
O(1) C(1) O(2) 124.14(14)
O(1) C(1) C(2) 118.30(13)
O(2) C(1) C(2) 117.56(13)
C(1) C(2) O(3) 111.53(12)
C(1) C(2) C(3) 111.05(13)
O(3) C(2) C(3) 107.32(12)
C(2) C(3) C(4) 122.87(14)
C(2) C(3) C(8) 118.5(2)
C(4) C(3) C(8) 118.5(2)
C(3) C(4) C(5) 120.6(2)
O(4) C(18) C(19) 110.13(12)
C(18) C(19) C(20) 114.73(13)
C(18) C(19) N(2) 111.79(12)
C(20) C(19) N(2) 107.87(11)
C(19) C(20) C(21) 108.75(13)
C(20) C(21) C(22) 108.49(14)
C(20) C(21) C(25) 109.76(14)
C(22) C(21) C(25) 107.83(14)
C(21) C(22) C(23) 108.73(14)
C(22) C(23) N(2) 108.37(14)
C(19) N(2) C(23) 107.88(12)
C(19) N(2) C(24) 112.12(12)
C(23) N(2) C(24) 108.74(12)
N(2) C(24) C(25) 109.65(13)
C(21) C(25) C(24) 107.40(12)
C(21) C(25) C(26) 112.9(2)
C(24) C(25) C(26) 111.4(2)
C(25) C(26) C(27) 122.4(2)