#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/18/2101873.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_2101873
loop_
_publ_author_name
'Gjerløv, A.'
'Larsen, S.'
_publ_section_title
;
 A Study of Diastereomeric Mandelate Salts of Cinchonidine and the
 Relation to Their Quasidiastereomeric Analogues
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              708
_journal_page_last               718
_journal_paper_doi               10.1107/S0108768197003480
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety
;
'C~19H~23~N~2~O^+^C~8~H~7~O~3~^-^
;
_chemical_formula_sum            'C27 H30 N2 O4'
_chemical_formula_weight         446.53
_chemical_name_systematic
;
cinchonidinium (R)-mandelate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 100.67(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.410(3)
_cell_length_b                   32.808(11)
_cell_length_c                   11.222(2)
_cell_measurement_reflns_used    18
_cell_measurement_temperature    122.0(10)
_cell_measurement_theta_max      30.18
_cell_measurement_theta_min      16.23
_cell_volume                     2319.2(14)
_computing_cell_refinement       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'DREADD (Blessing, 1987)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
;
SHELXL-93 (Sheldrick, 1995) and local programs'
;
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1995)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      122.0(10)
_diffrn_measurement_device       'Enraf Nonius CAD4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10960
_diffrn_reflns_theta_max         75.03
_diffrn_reflns_theta_min         2.69
_diffrn_standards_decay_%        7.7
_diffrn_standards_interval_time  166.7
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   'integration by crystal shape'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    none
_exptl_crystal_description       needle
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.243
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.029
_refine_ls_goodness_of_fit_obs   1.027
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     775
_refine_ls_number_reflns         9153
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_restrained_S_obs      1.027
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_obs          0.0380
_refine_ls_shift/esd_max         0.005
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0761P)²+0.2265P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1007
_refine_ls_wR_factor_obs         0.0991
_reflns_number_observed          8951
_reflns_number_total             9154
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ab0369.cif
_cod_data_source_block           R
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0761P)^2^+0.2265P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0761P)^2^+0.2265P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2319.2(13)
_cod_original_sg_symbol_Hall     'P 2y1'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2101873
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
O4A 0.4411(2) 0.22863(4) 0.15799(10) 0.0236(2) Uani d 1 O
H4O_1 0.412(4) 0.2052(7) 0.193(2) 0.030 Uiso d 1 H
N1A 0.7113(2) 0.35760(4) 0.37576(13) 0.0268(3) Uani d 1 N
N2A 0.8311(2) 0.20179(4) 0.04372(12) 0.0211(3) Uani d 1 N
H2_1 0.899(4) 0.1866(7) 0.111(2) 0.030 Uiso d 1 H
C9A 0.6785(3) 0.27997(5) 0.26234(13) 0.0201(3) Uani d 1 C
C10A 0.8700(3) 0.29134(5) 0.34190(14) 0.0209(3) Uani d 1 C
C11A 1.0524(3) 0.26607(5) 0.36922(14) 0.0232(3) Uani d 1 C
H11_1 1.045(4) 0.2378(7) 0.337(2) 0.030 Uiso d 1 H
C12A 1.2322(3) 0.27922(6) 0.4445(2) 0.0281(3) Uani d 1 C
H12_1 1.361(4) 0.2600(7) 0.461(2) 0.030 Uiso d 1 H
C13A 1.2394(3) 0.31850(6) 0.4976(2) 0.0289(4) Uani d 1 C
H13_1 1.360(4) 0.3280(7) 0.556(2) 0.030 Uiso d 1 H
C14A 1.0656(3) 0.34326(5) 0.47463(15) 0.0277(3) Uani d 1 C
H14_1 1.065(4) 0.3696(7) 0.514(2) 0.030 Uiso d 1 H
C15A 0.8778(3) 0.33075(5) 0.39679(14) 0.0237(3) Uani d 1 C
C16A 0.5388(3) 0.34555(5) 0.30125(15) 0.0263(3) Uani d 1 C
H16_1 0.422(4) 0.3665(7) 0.286(2) 0.030 Uiso d 1 H
C17A 0.5149(3) 0.30733(5) 0.24239(14) 0.0236(3) Uani d 1 C
H17_1 0.378(4) 0.3003(7) 0.189(2) 0.030 Uiso d 1 H
C18A 0.6576(2) 0.23905(5) 0.19738(13) 0.0190(3) Uani d 1 C
H18_1 0.724(4) 0.2179(7) 0.251(2) 0.030 Uiso d 1 H
C19A 0.7714(2) 0.24291(4) 0.08804(13) 0.0190(3) Uani d 1 C
H19_1 0.909(4) 0.2559(7) 0.117(2) 0.030 Uiso d 1 H
C20A 0.6454(3) 0.26658(5) -0.02063(14) 0.0230(3) Uani d 1 C
H201_1 0.709(4) 0.2943(7) -0.017(2) 0.030 Uiso d 1 H
H202_1 0.501(4) 0.2699(7) -0.007(2) 0.030 Uiso d 1 H
C21A 0.6542(3) 0.24302(5) -0.13755(14) 0.0233(3) Uani d 1 C
H21_1 0.579(4) 0.2588(7) -0.211(2) 0.030 Uiso d 1 H
C22A 0.5400(3) 0.20213(6) -0.1336(2) 0.0276(3) Uani d 1 C
H221_1 0.546(4) 0.1883(7) -0.209(2) 0.030 Uiso d 1 H
H222_1 0.395(4) 0.2067(7) -0.131(2) 0.030 Uiso d 1 H
C23A 0.6450(3) 0.17779(5) -0.0214(2) 0.0263(3) Uani d 1 C
H231_1 0.704(4) 0.1521(7) -0.041(2) 0.030 Uiso d 1 H
H232_1 0.545(4) 0.1725(7) 0.036(2) 0.030 Uiso d 1 H
C24A 0.9872(3) 0.20801(5) -0.03895(15) 0.0243(3) Uani d 1 C
H241_1 1.025(4) 0.1817(7) -0.062(2) 0.030 Uiso d 1 H
H242_1 1.105(4) 0.2198(7) 0.007(2) 0.030 Uiso d 1 H
C25A 0.8854(3) 0.23419(5) -0.14937(15) 0.0245(3) Uani d 1 C
H25_1 0.877(4) 0.2169(7) -0.225(2) 0.030 Uiso d 1 H
C26A 1.0085(3) 0.27244(6) -0.1591(2) 0.0318(4) Uani d 1 C
H26_1 1.040(4) 0.2898(7) -0.090(2) 0.030 Uiso d 1 H
C27A 1.0744(5) 0.28351(9) -0.2582(2) 0.0607(8) Uani d 1 C
H271_1 1.148(4) 0.3088(7) -0.266(2) 0.030 Uiso d 1 H
H272_1 1.044(4) 0.2694(7) -0.325(2) 0.030 Uiso d 1 H
O4B 0.0289(2) 0.48126(4) 0.30277(10) 0.0233(2) Uani d 1 O
H4O_2 -0.045(4) 0.4990(7) 0.244(2) 0.030 Uiso d 1 H
N1B 0.1093(2) 0.35899(4) 0.04548(13) 0.0283(3) Uani d 1 N
N2B 0.4908(2) 0.50434(4) 0.41613(12) 0.0204(3) Uani d 1 N
H2_2 0.522(4) 0.5210(7) 0.355(2) 0.030 Uiso d 1 H
C9B 0.1794(2) 0.43246(5) 0.18060(13) 0.0202(3) Uani d 1 C
C10B 0.3098(3) 0.42263(5) 0.09425(14) 0.0219(3) Uani d 1 C
C11B 0.4781(3) 0.44751(5) 0.0705(2) 0.0264(3) Uani d 1 C
H11_2 0.507(4) 0.4725(7) 0.114(2) 0.030 Uiso d 1 H
C12B 0.5943(3) 0.43641(6) -0.0156(2) 0.0335(4) Uani d 1 C
H12_2 0.702(4) 0.4543(7) -0.031(2) 0.030 Uiso d 1 H
C13B 0.5507(3) 0.39971(7) -0.0807(2) 0.0355(4) Uani d 1 C
H13_2 0.634(4) 0.3921(7) -0.139(2) 0.030 Uiso d 1 H
C14B 0.3910(3) 0.37469(6) -0.0584(2) 0.0327(4) Uani d 1 C
H14_2 0.354(4) 0.3481(7) -0.101(2) 0.030 Uiso d 1 H
C15B 0.2665(3) 0.38554(5) 0.02851(14) 0.0252(3) Uani d 1 C
C16B -0.0066(3) 0.36954(5) 0.1259(2) 0.0275(3) Uani d 1 C
H16_2 -0.118(4) 0.3523(7) 0.133(2) 0.030 Uiso d 1 H
C17B 0.0216(3) 0.40577(5) 0.19479(14) 0.0235(3) Uani d 1 C
H17_2 -0.074(4) 0.4119(7) 0.248(2) 0.030 Uiso d 1 H
C18B 0.2129(2) 0.47126(5) 0.25676(13) 0.0199(3) Uani d 1 C
H18_2 0.254(4) 0.4946(7) 0.207(2) 0.030 Uiso d 1 H
C19B 0.4006(2) 0.46453(5) 0.36328(13) 0.0200(3) Uani d 1 C
H19_2 0.516(4) 0.4512(7) 0.330(2) 0.030 Uiso d 1 H
C20B 0.3461(3) 0.43816(5) 0.46719(14) 0.0223(3) Uani d 1 C
H201_2 0.419(4) 0.4117(7) 0.468(2) 0.030 Uiso d 1 H
H202_2 0.200(4) 0.4340(7) 0.457(2) 0.030 Uiso d 1 H
C21B 0.4198(2) 0.45965(5) 0.58882(14) 0.0225(3) Uani d 1 C
H21_2 0.393(4) 0.4421(7) 0.659(2) 0.030 Uiso d 1 H
C22B 0.3003(3) 0.49997(5) 0.5890(2) 0.0269(3) Uani d 1 C
H221_2 0.347(4) 0.5157(7) 0.668(2) 0.030 Uiso d 1 H
H222_2 0.148(4) 0.4936(7) 0.577(2) 0.030 Uiso d 1 H
C23B 0.3430(3) 0.52675(5) 0.4835(2) 0.0237(3) Uani d 1 C
H231_2 0.410(4) 0.5513(7) 0.511(2) 0.030 Uiso d 1 H
H232_2 0.209(4) 0.5346(7) 0.427(2) 0.030 Uiso d 1 H
C24B 0.6975(2) 0.49602(5) 0.50102(15) 0.0233(3) Uani d 1 C
H241_2 0.757(4) 0.5231(7) 0.530(2) 0.030 Uiso d 1 H
H242_2 0.793(4) 0.4826(7) 0.449(2) 0.030 Uiso d 1 H
C25B 0.6593(2) 0.46938(5) 0.60854(14) 0.0224(3) Uani d 1 C
H25_2 0.695(4) 0.4849(7) 0.685(2) 0.030 Uiso d 1 H
C26B 0.7959(3) 0.43158(6) 0.6219(2) 0.0276(3) Uani d 1 C
H26_2 0.774(4) 0.4135(7) 0.553(2) 0.030 Uiso d 1 H
C27B 0.9434(3) 0.42382(7) 0.7185(2) 0.0386(4) Uani d 1 C
H271_2 0.968(4) 0.4419(7) 0.784(2) 0.030 Uiso d 1 H
H272_2 1.025(4) 0.3989(8) 0.728(2) 0.030 Uiso d 1 H
O1A 0.3819(2) 0.15654(4) 0.26121(12) 0.0309(3) Uani d 1 O
O2A 0.0433(2) 0.17436(4) 0.25104(10) 0.0249(2) Uani d 1 O
O3A 0.3388(2) 0.08458(4) 0.34974(13) 0.0306(3) Uani d 1 O
H3O_3 0.429(4) 0.0981(7) 0.323(2) 0.030 Uiso d 1 H
C1A 0.1958(2) 0.14980(5) 0.27276(13) 0.0209(3) Uani d 1 C
C2A 0.1489(3) 0.10713(5) 0.32049(14) 0.0224(3) Uani d 1 C
H2_3 0.096(4) 0.1128(7) 0.395(2) 0.030 Uiso d 1 H
C3A -0.0173(3) 0.08477(5) 0.22980(14) 0.0216(3) Uani d 1 C
C4A -0.2266(3) 0.09872(5) 0.2072(2) 0.0261(3) Uani d 1 C
H4_3 -0.263(4) 0.1232(7) 0.251(2) 0.030 Uiso d 1 H
C5A -0.3791(3) 0.07947(6) 0.1213(2) 0.0311(4) Uani d 1 C
H5_3 -0.528(4) 0.0892(7) 0.106(2) 0.030 Uiso d 1 H
C6A -0.3259(3) 0.04579(6) 0.0590(2) 0.0348(4) Uani d 1 C
H6_3 -0.442(4) 0.0325(7) -0.001(2) 0.030 Uiso d 1 H
C7A -0.1184(3) 0.03143(5) 0.0821(2) 0.0333(4) Uani d 1 C
H7_3 -0.088(4) 0.0092(7) 0.030(2) 0.030 Uiso d 1 H
C8A 0.0356(3) 0.05103(5) 0.1664(2) 0.0267(3) Uani d 1 C
H8_3 0.171(4) 0.0413(7) 0.180(2) 0.030 Uiso d 1 H
O1B 0.1782(2) 0.03520(4) 0.85158(11) 0.0288(3) Uani d 1 O
O2B 0.3772(2) 0.06011(4) 0.72375(12) 0.0318(3) Uani d 1 O
O3B 0.1203(2) 0.10775(4) 0.94186(11) 0.0307(3) Uani d 1 O
H3O_4 0.101(4) 0.0842(8) 0.954(2) 0.030 Uiso d 1 H
C1B 0.2571(2) 0.06338(5) 0.79960(14) 0.0229(3) Uani d 1 C
C2B 0.1997(3) 0.10715(5) 0.83200(14) 0.0229(3) Uani d 1 C
H2_4 0.328(4) 0.1236(7) 0.842(2) 0.030 Uiso d 1 H
C3B 0.0377(3) 0.12522(5) 0.72889(14) 0.0221(3) Uani d 1 C
C4B 0.0988(3) 0.15309(5) 0.64803(15) 0.0255(3) Uani d 1 C
H4_4 0.239(4) 0.1618(7) 0.658(2) 0.030 Uiso d 1 H
C5B -0.0501(3) 0.16901(6) 0.5533(2) 0.0326(4) Uani d 1 C
H5_4 -0.004(4) 0.1892(7) 0.496(2) 0.030 Uiso d 1 H
C6B -0.2606(3) 0.15683(6) 0.5374(2) 0.0341(4) Uani d 1 C
H6_4 -0.365(4) 0.1678(7) 0.468(2) 0.030 Uiso d 1 H
C7B -0.3223(3) 0.12901(6) 0.6177(2) 0.0317(4) Uani d 1 C
H7_4 -0.467(4) 0.1206(7) 0.611(2) 0.030 Uiso d 1 H
C8B -0.1739(3) 0.11337(5) 0.7131(2) 0.0263(3) Uani d 1 C
H8_4 -0.214(4) 0.0942(7) 0.771(2) 0.030 Uiso d 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
H4O_1 O4A C18A . . 110.0(15) ?
H4O_1 O4A O1A . . 4.3(15) ?
C18A O4A O1A . . 106.59(9) ?
H4O_1 O4A H4O_1 . . 0.(5) ?
C18A O4A H4O_1 . . 110.0(15) ?
O1A O4A H4O_1 . . 4.3(15) ?
C16A N1A C15A . . 116.87(14) ?
H2_1 N2A C24A . . 107.8(14) ?
H2_1 N2A C23A . . 108.9(14) ?
C24A N2A C23A . . 109.36(12) yes
H2_1 N2A C19A . . 108.3(14) ?
C24A N2A C19A . . 108.71(12) yes
C23A N2A C19A . . 113.68(12) yes
H2_1 N2A O2A . 1_655 11.7(14) ?
C24A N2A O2A . 1_655 107.41(10) ?
C23A N2A O2A . 1_655 119.06(10) ?
C19A N2A O2A . 1_655 97.78(9) ?
H2_1 N2A H2_1 . . 0.(4) ?
C24A N2A H2_1 . . 107.8(14) ?
C23A N2A H2_1 . . 108.9(14) ?
C19A N2A H2_1 . . 108.3(14) ?
O2A N2A H2_1 1_655 . 11.7(14) ?
C17A C9A C10A . . 118.40(14) ?
C17A C9A C18A . . 120.25(14) yes
C10A C9A C18A . . 121.32(14) yes
C11A C10A C9A . . 124.12(14) ?
C11A C10A C15A . . 118.25(15) ?
C9A C10A C15A . . 117.63(15) ?
C12A C11A C10A . . 121.1(2) ?
C12A C11A H11_1 . . 119.8(14) ?
C10A C11A H11_1 . . 119.0(14) ?
C11A C12A C13A . . 120.3(2) ?
C11A C12A H12_1 . . 118.4(13) ?
C13A C12A H12_1 . . 121.3(13) ?
C14A C13A C12A . . 120.0(2) ?
C14A C13A H13_1 . . 117.5(14) ?
C12A C13A H13_1 . . 122.3(14) ?
C13A C14A C15A . . 121.1(2) ?
C13A C14A H14_1 . . 121.2(14) ?
C15A C14A H14_1 . . 117.6(14) ?
N1A C15A C14A . . 117.9(2) ?
N1A C15A C10A . . 122.9(2) ?
C14A C15A C10A . . 119.2(2) ?
N1A C16A C17A . . 124.6(2) ?
N1A C16A H16_1 . . 114.4(13) ?
C17A C16A H16_1 . . 121.0(13) ?
C9A C17A C16A . . 119.5(2) ?
C9A C17A H17_1 . . 120.7(13) ?
C16A C17A H17_1 . . 119.8(13) ?
O4A C18A C9A . . 110.90(12) yes
O4A C18A C19A . . 110.54(12) yes
C9A C18A C19A . . 107.18(12) yes
O4A C18A H18_1 . . 108.5(14) ?
C9A C18A H18_1 . . 110.1(13) ?
C19A C18A H18_1 . . 109.7(13) ?
N2A C19A C20A . . 108.46(12) yes
N2A C19A C18A . . 111.96(12) yes
C20A C19A C18A . . 114.48(13) yes
N2A C19A H19_1 . . 103.2(14) ?
C20A C19A H19_1 . . 110.7(14) ?
C18A C19A H19_1 . . 107.4(13) ?
C21A C20A C19A . . 109.03(12) ?
C21A C20A H201_1 . . 115.0(13) ?
C19A C20A H201_1 . . 105.9(13) ?
C21A C20A H202_1 . . 112.5(14) ?
C19A C20A H202_1 . . 107.6(14) ?
H201_1 C20A H202_1 . . 106.3(19) ?
C20A C21A C22A . . 108.86(14) ?
C20A C21A C25A . . 110.93(13) ?
C22A C21A C25A . . 108.07(14) ?
C20A C21A H21_1 . . 110.7(13) ?
C22A C21A H21_1 . . 108.1(13) ?
C25A C21A H21_1 . . 110.1(13) ?
C21A C22A C23A . . 109.84(13) ?
C21A C22A H221_1 . . 106.8(14) ?
C23A C22A H221_1 . . 113.1(14) ?
C21A C22A H222_1 . . 109.9(14) ?
C23A C22A H222_1 . . 109.9(13) ?
H221_1 C22A H222_1 . . 107.2(19) ?
N2A C23A C22A . . 108.30(13) ?
N2A C23A H231_1 . . 105.1(13) ?
C22A C23A H231_1 . . 113.3(13) ?
N2A C23A H232_1 . . 108.9(13) ?
C22A C23A H232_1 . . 112.3(13) ?
H231_1 C23A H232_1 . . 108.6(18) ?
N2A C24A C25A . . 109.86(13) ?
N2A C24A H241_1 . . 106.4(14) ?
C25A C24A H241_1 . . 112.1(14) ?
N2A C24A H242_1 . . 106.4(14) ?
C25A C24A H242_1 . . 113.5(14) ?
H241_1 C24A H242_1 . . 108.(2) ?
C26A C25A C21A . . 112.17(14) ?
C26A C25A C24A . . 111.93(14) ?
C21A C25A C24A . . 107.77(13) ?
C26A C25A H25_1 . . 110.8(13) ?
C21A C25A H25_1 . . 106.0(13) ?
C24A C25A H25_1 . . 107.8(13) ?
C27A C26A C25A . . 123.4(2) yes
C27A C26A H26_1 . . 118.3(14) ?
C25A C26A H26_1 . . 118.3(14) ?
C26A C27A H271_1 . . 123.6(14) ?
C26A C27A H272_1 . . 121.9(16) ?
H271_1 C27A H272_1 . . 114.(2) ?
H4O_2 O4B C18B . . 103.3(14) ?
H4O_2 O4B O1B . 2_556 4.0(14) ?
C18B O4B O1B . 2_556 105.49(9) ?
H4O_2 O4B H4O_2 . . 0.(5) ?
C18B O4B H4O_2 . . 103.3(14) ?
O1B O4B H4O_2 2_556 . 4.0(14) ?
C16B N1B C15B . . 116.78(14) ?
H2_2 N2B C19B . . 109.9(14) ?
H2_2 N2B C24B . . 106.9(14) ?
C19B N2B C24B . . 108.70(12) yes
H2_2 N2B C23B . . 108.8(14) ?
C19B N2B C23B . . 112.91(12) yes
C24B N2B C23B . . 109.39(12) yes
H2_2 N2B O2B . 2_656 11.0(14) ?
C19B N2B O2B . 2_656 120.49(10) ?
C24B N2B O2B . 2_656 99.21(9) ?
C23B N2B O2B . 2_656 105.03(10) ?
H2_2 N2B H2_2 . . 0.(4) ?
C19B N2B H2_2 . . 109.9(14) ?
C24B N2B H2_2 . . 106.9(14) ?
C23B N2B H2_2 . . 108.8(14) ?
O2B N2B H2_2 2_656 . 11.0(14) ?
C17B C9B C10B . . 118.16(14) ?
C17B C9B C18B . . 119.93(14) yes
C10B C9B C18B . . 121.91(14) yes
C11B C10B C15B . . 118.51(15) ?
C11B C10B C9B . . 123.98(15) ?
C15B C10B C9B . . 117.51(14) ?
C12B C11B C10B . . 120.7(2) ?
C12B C11B H11_2 . . 120.4(14) ?
C10B C11B H11_2 . . 118.9(14) ?
C11B C12B C13B . . 120.7(2) ?
C11B C12B H12_2 . . 118.3(14) ?
C13B C12B H12_2 . . 121.0(14) ?
C14B C13B C12B . . 120.0(2) ?
C14B C13B H13_2 . . 120.0(14) ?
C12B C13B H13_2 . . 120.0(14) ?
C13B C14B C15B . . 120.7(2) ?
C13B C14B H14_2 . . 123.6(13) ?
C15B C14B H14_2 . . 115.7(13) ?
N1B C15B C14B . . 117.3(2) ?
N1B C15B C10B . . 123.28(15) ?
C14B C15B C10B . . 119.4(2) ?
N1B C16B C17B . . 124.4(2) ?
N1B C16B H16_2 . . 115.8(14) ?
C17B C16B H16_2 . . 119.7(14) ?
C9B C17B C16B . . 119.9(2) ?
C9B C17B H17_2 . . 120.8(14) ?
C16B C17B H17_2 . . 119.3(14) ?
O4B C18B C9B . . 110.99(12) yes
O4B C18B C19B . . 109.50(12) yes
C9B C18B C19B . . 108.81(12) yes
O4B C18B H18_2 . . 110.2(13) ?
C9B C18B H18_2 . . 110.4(13) ?
C19B C18B H18_2 . . 106.8(13) ?
N2B C19B C20B . . 108.24(12) yes
N2B C19B C18B . . 111.58(12) yes
C20B C19B C18B . . 114.27(12) yes
N2B C19B H19_2 . . 105.8(14) ?
C20B C19B H19_2 . . 108.9(14) ?
C18B C19B H19_2 . . 107.7(13) ?
C21B C20B C19B . . 109.86(13) ?
C21B C20B H201_2 . . 109.1(13) ?
C19B C20B H201_2 . . 109.1(13) ?
C21B C20B H202_2 . . 108.4(14) ?
C19B C20B H202_2 . . 110.6(14) ?
H201_2 C20B H202_2 . . 110.(2) ?
C22B C21B C20B . . 109.10(13) ?
C22B C21B C25B . . 107.82(13) ?
C20B C21B C25B . . 110.96(13) ?
C22B C21B H21_2 . . 109.6(13) ?
C20B C21B H21_2 . . 111.1(13) ?
C25B C21B H21_2 . . 108.3(13) ?
C21B C22B C23B . . 109.44(13) ?
C21B C22B H221_2 . . 111.9(13) ?
C23B C22B H221_2 . . 108.4(13) ?
C21B C22B H222_2 . . 107.4(14) ?
C23B C22B H222_2 . . 109.1(13) ?
H221_2 C22B H222_2 . . 110.5(18) ?
N2B C23B C22B . . 108.96(13) ?
N2B C23B H231_2 . . 106.9(14) ?
C22B C23B H231_2 . . 111.9(14) ?
N2B C23B H232_2 . . 110.4(13) ?
C22B C23B H232_2 . . 112.5(13) ?
H231_2 C23B H232_2 . . 106.1(19) ?
N2B C24B C25B . . 110.39(12) ?
N2B C24B H241_2 . . 106.6(13) ?
C25B C24B H241_2 . . 110.7(13) ?
N2B C24B H242_2 . . 105.6(13) ?
C25B C24B H242_2 . . 113.5(13) ?
H241_2 C24B H242_2 . . 109.7(18) ?
C26B C25B C21B . . 112.79(13) ?
C26B C25B C24B . . 111.67(13) ?
C21B C25B C24B . . 107.59(12) ?
C26B C25B H25_2 . . 107.5(13) ?
C21B C25B H25_2 . . 107.1(14) ?
C24B C25B H25_2 . . 110.0(13) ?
C27B C26B C25B . . 123.5(2) yes
C27B C26B H26_2 . . 121.1(14) ?
C25B C26B H26_2 . . 115.3(14) ?
C26B C27B H271_2 . . 121.0(14) ?
C26B C27B H272_2 . . 122.9(14) ?
H271_2 C27B H272_2 . . 116.(2) ?
C1A O1A H4O_1 . . 112.4(7) ?
C1A O1A H3O_3 . . 83.2(7) ?
H4O_1 O1A H3O_3 . . 163.6(10) ?
C1A O1A O3A . . 68.05(9) ?
H4O_1 O1A O3A . . 177.3(7) ?
H3O_3 O1A O3A . . 15.3(7) ?
C1A O1A O4A . . 114.56(10) ?
H4O_1 O1A O4A . . 2.2(7) ?
H3O_3 O1A O4A . . 161.4(7) ?
O3A O1A O4A . . 175.94(7) ?
H3O_3 O3A C2A . . 105.3(16) ?
H3O_3 O3A O1A . . 40.7(16) ?
C2A O3A O1A . . 65.31(9) ?
H3O_3 O3A H3O_3 . . 0.(5) ?
C2A O3A H3O_3 . . 105.3(16) ?
O1A O3A H3O_3 . . 40.7(16) ?
O1A C1A O2A . . 126.38(15) yes
O1A C1A C2A . . 116.65(14) yes
O2A C1A C2A . . 116.97(14) yes
O3A C2A C3A . . 111.75(14) yes
O3A C2A C1A . . 109.89(13) yes
C3A C2A C1A . . 111.22(12) yes
O3A C2A H2_3 . . 108.8(14) ?
C3A C2A H2_3 . . 110.7(14) ?
C1A C2A H2_3 . . 104.2(13) ?
C8A C3A C4A . . 119.0(2) yes
C8A C3A C2A . . 121.31(15) yes
C4A C3A C2A . . 119.65(15) yes
C5A C4A C3A . . 120.4(2) yes
C5A C4A H4_3 . . 120.9(13) ?
C3A C4A H4_3 . . 118.7(13) ?
C6A C5A C4A . . 120.4(2) yes
C6A C5A H5_3 . . 119.5(14) ?
C4A C5A H5_3 . . 120.1(14) ?
C5A C6A C7A . . 119.5(2) yes
C5A C6A H6_3 . . 117.6(13) ?
C7A C6A H6_3 . . 122.9(13) ?
C6A C7A C8A . . 120.3(2) yes
C6A C7A H7_3 . . 115.5(14) ?
C8A C7A H7_3 . . 123.9(14) ?
C3A C8A C7A . . 120.4(2) yes
C3A C8A H8_3 . . 120.4(15) ?
C7A C8A H8_3 . . 119.2(15) ?
C1B O1B H3O_4 . . 81.1(7) ?
C1B O1B O3B . . 67.03(10) ?
H3O_4 O1B O3B . . 14.2(7) ?
H3O_4 O3B C2B . . 103.3(17) ?
H3O_4 O3B O1B . . 39.8(17) ?
C2B O3B O1B . . 63.60(8) ?
H3O_4 O3B H3O_4 . . 0.(5) ?
C2B O3B H3O_4 . . 103.3(17) ?
O1B O3B H3O_4 . . 39.8(17) ?
O1B C1B O2B . . 127.4(2) yes
O1B C1B C2B . . 116.37(14) yes
O2B C1B C2B . . 116.28(14) yes
O3B C2B C3B . . 110.51(13) yes
O3B C2B C1B . . 110.94(13) yes
C3B C2B C1B . . 109.99(12) yes
O3B C2B H2_4 . . 108.8(14) ?
C3B C2B H2_4 . . 108.3(14) ?
C1B C2B H2_4 . . 108.2(14) ?
C8B C3B C4B . . 119.0(2) yes
C8B C3B C2B . . 119.95(15) yes
C4B C3B C2B . . 120.99(15) yes
C5B C4B C3B . . 120.5(2) yes
C5B C4B H4_4 . . 119.3(14) ?
C3B C4B H4_4 . . 120.2(14) ?
C6B C5B C4B . . 120.2(2) yes
C6B C5B H5_4 . . 120.1(14) ?
C4B C5B H5_4 . . 119.7(14) ?
C5B C6B C7B . . 119.5(2) yes
C5B C6B H6_4 . . 119.4(14) ?
C7B C6B H6_4 . . 121.1(14) ?
C6B C7B C8B . . 120.3(2) yes
C6B C7B H7_4 . . 121.8(14) ?
C8B C7B H7_4 . . 117.9(14) ?
C3B C8B C7B . . 120.4(2) yes
C3B C8B H8_4 . . 117.9(14) ?
C7B C8B H8_4 . . 121.6(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O4A H4O_1 . 0.90(2) ?
O4A C18A . 1.418(2) yes
O4A O1A . 2.691(2) ?
O4A H4O_1 . 0.90(2) ?
N1A C16A . 1.318(2) ?
N1A C15A . 1.370(2) ?
N2A H2_1 . 0.94(2) ?
N2A C24A . 1.499(2) yes
N2A C23A . 1.501(2) yes
N2A C19A . 1.511(2) yes
N2A O2A 1_655 2.627(2) ?
N2A H2_1 . 0.94(2) ?
C9A C17A . 1.367(2) ?
C9A C10A . 1.427(2) ?
C9A C18A . 1.522(2) yes
C10A C11A . 1.420(2) ?
C10A C15A . 1.429(2) ?
C11A C12A . 1.367(2) ?
C11A H11_1 . 0.99(2) ?
C12A C13A . 1.417(3) ?
C12A H12_1 . 1.03(2) ?
C13A C14A . 1.364(3) ?
C13A H13_1 . 0.97(2) ?
C14A C15A . 1.411(2) ?
C14A H14_1 . 0.97(2) ?
C16A C17A . 1.412(2) ?
C16A H16_1 . 1.01(2) ?
C17A H17_1 . 0.99(2) ?
C18A C19A . 1.544(2) yes
C18A H18_1 . 0.97(2) ?
C19A C20A . 1.542(2) ?
C19A H19_1 . 0.98(2) ?
C20A C21A . 1.533(2) ?
C20A H201_1 . 0.99(2) ?
C20A H202_1 . 0.97(3) ?
C21A C22A . 1.533(2) ?
C21A C25A . 1.539(2) ?
C21A H21_1 . 1.02(2) ?
C22A C23A . 1.537(2) ?
C22A H221_1 . 0.97(2) ?
C22A H222_1 . 0.95(2) ?
C23A H231_1 . 0.97(2) ?
C23A H232_1 . 1.00(2) ?
C24A C25A . 1.549(2) ?
C24A H241_1 . 0.95(2) ?
C24A H242_1 . 0.92(2) ?
C25A C26A . 1.497(2) yes
C25A H25_1 . 1.01(2) ?
C26A C27A . 1.311(3) yes
C26A H26_1 . 0.96(2) ?
C27A H271_1 . 0.97(2) ?
C27A H272_1 . 0.87(2) ?
O4B H4O_2 . 0.94(2) ?
O4B C18B . 1.411(2) yes
O4B O1B 2_556 2.654(2) ?
O4B H4O_2 . 0.94(2) ?
N1B C16B . 1.317(2) ?
N1B C15B . 1.372(2) ?
N2B H2_2 . 0.93(2) ?
N2B C19B . 1.505(2) yes
N2B C24B . 1.507(2) yes
N2B C23B . 1.509(2) yes
N2B O2B 2_656 2.649(2) ?
N2B H2_2 . 0.93(2) ?
C9B C17B . 1.369(2) ?
C9B C10B . 1.429(2) ?
C9B C18B . 1.526(2) yes
C10B C11B . 1.416(2) ?
C10B C15B . 1.423(2) ?
C11B C12B . 1.374(2) ?
C11B H11_2 . 0.95(2) ?
C12B C13B . 1.409(3) ?
C12B H12_2 . 0.94(2) ?
C13B C14B . 1.371(3) ?
C13B H13_2 . 0.95(2) ?
C14B C15B . 1.415(2) ?
C14B H14_2 . 1.00(2) ?
C16B C17B . 1.411(2) ?
C16B H16_2 . 0.92(2) ?
C17B H17_2 . 0.95(2) ?
C18B C19B . 1.547(2) yes
C18B H18_2 . 1.01(2) ?
C19B C20B . 1.543(2) ?
C19B H19_2 . 0.99(2) ?
C20B C21B . 1.531(2) ?
C20B H201_2 . 0.99(2) ?
C20B H202_2 . 0.93(2) ?
C21B C22B . 1.529(2) ?
C21B C25B . 1.543(2) ?
C21B H21_2 . 1.01(2) ?
C22B C23B . 1.539(2) ?
C22B H221_2 . 1.02(2) ?
C22B H222_2 . 0.98(2) ?
C23B H231_2 . 0.94(2) ?
C23B H232_2 . 1.00(2) ?
C24B C25B . 1.546(2) ?
C24B H241_2 . 1.00(2) ?
C24B H242_2 . 1.02(2) ?
C25B C26B . 1.510(2) yes
C25B H25_2 . 0.99(2) ?
C26B C27B . 1.325(3) yes
C26B H26_2 . 0.97(2) ?
C27B H271_2 . 0.94(2) ?
C27B H272_2 . 0.96(3) ?
O1A C1A . 1.244(2) yes
O1A H3O_3 . 2.04(2) ?
O1A O3A . 2.596(2) ?
O2A C1A . 1.255(2) yes
O3A H3O_3 . 0.83(3) ?
O3A C2A . 1.410(2) yes
O3A H3O_3 . 0.83(3) ?
C1A C2A . 1.548(2) yes
C2A C3A . 1.519(2) yes
C2A H2_3 . 0.98(2) ?
C3A C8A . 1.391(2) yes
C3A C4A . 1.395(2) yes
C4A C5A . 1.391(2) yes
C4A H4_3 . 0.99(2) ?
C5A C6A . 1.384(3) yes
C5A H5_3 . 0.99(2) ?
C6A C7A . 1.390(3) yes
C6A H6_3 . 1.01(2) ?
C7A C8A . 1.392(3) yes
C7A H7_3 . 0.97(2) ?
C8A H8_3 . 0.91(3) ?
O1B C1B . 1.249(2) yes
O1B H3O_4 . 2.09(3) ?
O1B O3B . 2.640(2) ?
O2B C1B . 1.254(2) yes
O3B H3O_4 . 0.80(3) ?
O3B C2B . 1.419(2) yes
O3B H3O_4 . 0.80(3) ?
C1B C2B . 1.543(2) yes
C2B C3B . 1.524(2) yes
C2B H2_4 . 0.97(2) ?
C3B C8B . 1.391(2) yes
C3B C4B . 1.394(2) yes
C4B C5B . 1.392(2) yes
C4B H4_4 . 0.93(2) ?
C5B C6B . 1.387(3) yes
C5B H5_4 . 1.01(2) ?
C6B C7B . 1.391(3) yes
C6B H6_4 . 1.00(2) ?
C7B C8B . 1.392(3) yes
C7B H7_4 . 0.96(2) ?
C8B H8_4 . 0.98(2) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
O1A C1A C2A O3A 3.9(2) yes
O1A C1A C2A C3A -120.4(2) yes
C1A C2A C3A C4A -68.5(2) yes
O3A C2A C3A C4A 168.25(14) yes
C10A C9A C18A O4A 160.26(13) yes
C17A C9A C18A O4A -21.8(2) yes
C17A C9A C18A C19A 98.9(2) yes
C10A C9A C18A C19A -79.0(2) yes
C9A C18A C19A N2A 159.40(12) yes
C9A C18A C19A C20A -76.6(2) yes
O4A C18A C19A C20A 44.3(2) yes
O4A C18A C19A N2A -79.63(15) yes
C25A C21A N2A C24A -1.50(11) yes
C25A C21A N2A C19A 116.46(12) yes
C25A C21A N2A C23A -119.99(12) yes
C20A C21A N2A C19A -5.21(11) yes
C20A C21A N2A C23A 118.35(12) yes
C20A C21A N2A C24A -123.16(13) yes
C22A C21A N2A C23A -1.49(11) yes
C22A C21A N2A C24A 117.00(13) yes
C22A C21A N2A C19A -125.05(12) yes
C24A C25A C26A C27A 127.5(3) yes
O1B C1B C2B O3B 18.0(2) yes
O1B C1B C2B C3B -104.6(2) yes
C1B C2B C3B C4B -102.4(2) yes
O3B C2B C3B C4B 134.8(2) yes
C10B C9B C18B O4B 160.06(13) yes
C17B C9B C18B O4B -20.5(2) yes
C17B C9B C18B C19B 100.1(2) yes
C10B C9B C18B C19B -79.4(2) yes
C9B C18B C19B N2B 160.55(12) yes
C9B C18B C19B C20B -76.3(2) yes
O4B C18B C19B C20B 45.2(2) yes
O4B C18B C19B N2B -77.98(15) yes
C25B C21B N2B C24B 0.90(10) yes
C25B C21B N2B C19B 118.91(11) yes
C25B C21B N2B C23B -118.25(12) yes
C20B C21B N2B C19B -3.04(10) yes
C20B C21B N2B C23B 119.80(12) yes
C20B C21B N2B C24B -121.06(12) yes
C22B C21B N2B C23B -0.40(11) yes
C22B C21B N2B C24B 118.75(12) yes
C22B C21B N2B C19B -123.24(12) yes
C24B C25B C26B C27B 117.0(2) yes
