#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/16/2001650.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_2001650
loop_
_publ_author_name
'Mori, K.'
'Masuda, Y.'
'Kashino, S.'
_publ_section_title
;
 (+)-(R)- and racemic forms of 2,2'-dihydroxy-1,1'-binaphthyl
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1224
_journal_page_last               1227
_journal_paper_doi               10.1107/S0108270193000083
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.33
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_atom_type_scat_source           'IntTabIV Table 2.2B'
_cell_angle_alpha                90.
_cell_angle_beta                 90.
_cell_angle_gamma                120.00(10)
_cell_formula_units_Z            3
_cell_length_a                   10.808(2)
_cell_length_b                   10.808(2)
_cell_length_c                   10.8830(10)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    295
_cell_measurement_theta_max      20
_cell_measurement_theta_min      19
_cell_volume                     1101.0(12)
_diffrn_measurement_device       'Rigaku AFC-5'
_diffrn_measurement_method
;ω-2θ scans; width 1.2 + 0.15tanθ)° in ω; rate 4° min⁻¹
in ω; background counts 4 s on each side of every scan
;
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.02
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1266
_diffrn_reflns_theta_max         60.0
_diffrn_standards_decay_%        1.2
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      1.30
_exptl_crystal_density_method    'flotation in aq. KI'
_exptl_crystal_description       'Prism elongated along c'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.09
_refine_diff_density_min         -0.13
_refine_ls_goodness_of_fit_obs   1.357
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     258
_refine_ls_number_reflns         1077
_refine_ls_R_factor_obs          0.03
_refine_ls_shift/esd_max         0.05
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F)-0.0017|Fₒ|+0.009|Fₒ|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.039
_reflns_number_observed          1077
_reflns_number_total             1091
_reflns_observed_criterion       F>1.0\s(F)
_cod_data_source_file            oh1012.cif
_cod_data_source_block           oh1012_structure_1_of_2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '
1/[\s^2^(F)-0.0017|F~o~|+0.009|F~o~|^2^]' 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^(F)-0.0017|F~o~|+0.009|F~o~|^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1101.0(4)
_cod_database_code               2001650
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O(1) .4028(2) .2926(2) .5348(2)
O(2) .5488(2) .2585(2) .8018(2)
C(1) .3997(2) .4035(2) .7263(2)
C(2) .3311(2) .3150(2) .6274(2)
C(3) .1810(3) .2431(3) .6169(3)
C(4) .1017(2) .2608(3) .7033(3)
C(5) .0834(3) .3741(3) .8953(3)
C(6) .1477(3) .4660(3) .9899(3)
C(7) .2967(3) .5395(3) 1.0015(2)
C(8) .3794(2) .5200(2) .9167(2)
C(9) .3167(2) .4253(2) .8164(2)
C(10) .1655(2) .3527(2) .8052(2)
C(11) .5588(2) .4762(2) .7343(2)
C(12) .6243(3) .4007(3) .7708(2)
C(13) .7743(3) .4660(4) .7752(3)
C(14) .8571(3) .6036(4) .7397(3)
C(15) .8792(3) .8290(3) .6520(3)
C(16) .8161(3) .9024(3) .6122(3)
C(17) .6688(3) .8411(3) .6165(3)
C(18) .5856(3) .7040(3) .6566(2)
C(19) .6447(2) .6211(3) .6971(2)
C(20) .7964(2) .6857(3) .6973(2)
H(2) .500(3) .359(4) .538(3)
H(3) .139(4) .191(4) .543(4)
H(4) -.003(3) .212(3) .704(3)
H(5) -.024(3) .317(3) .885(3)
H(6) .090(4) .479(4) 1.055(4)
H(7) .335(3) .597(3) 1.080(3)
H(8) .483(2) .571(3) .924(3)
H(12) .464(3) .238(3) .807(3)
H(13) .819(3) .411(3) .800(2)
H(14) .960(3) .646(3) .734(3)
H(15) .981(3) .869(3) .650(3)
H(16) .879(4) .998(4) .576(4)
H(17) .627(3) .905(3) .583(3)
H(18) .481(3) .662(3) .658(3)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(2) C(1) C(9) 119.0(2) yes
C(2) C(1) C(11) 119.1(2) yes
C(9) C(1) C(11) 121.8(2) yes
O(1) C(2) C(1) 122.8(3) yes
O(1) C(2) C(3) 116.2(3) yes
C(1) C(2) C(3) 121.0(3) yes
C(2) C(3) C(4) 120.2(3) yes
C(3) C(4) C(10) 121.6(3) yes
C(6) C(5) C(10) 120.7(3) yes
C(5) C(6) C(7) 120.5(3) yes
C(6) C(7) C(8) 120.3(3) yes
C(7) C(8) C(9) 121.1(3) yes
C(1) C(9) C(8) 122.4(2) yes
C(1) C(9) C(10) 119.6(2) yes
C(8) C(9) C(10) 117.9(2) yes
C(4) C(10) C(5) 122.1(2) yes
C(4) C(10) C(9) 118.5(2) yes
C(5) C(10) C(9) 119.5(2) yes
C(1) C(11) C(12) 120.1(3) yes
C(1) C(11) C(19) 120.6(3) yes
C(12) C(11) C(19) 119.2(3) yes
O(2) C(12) C(11) 122.6(3) yes
O(2) C(12) C(13) 116.3(3) yes
C(11) C(12) C(13) 121.1(3) yes
C(12) C(13) C(14) 120.2(4) yes
C(13) C(14) C(20) 121.5(4) yes
C(16) C(15) C(20) 121.2(4) yes
C(15) C(16) C(17) 120.4(4) yes
C(16) C(17) C(18) 120.3(3) yes
C(17) C(18) C(19) 122.0(3) yes
C(11) C(19) C(18) 122.4(3) yes
C(11) C(19) C(20) 119.8(3) yes
C(18) C(19) C(20) 117.8(3) yes
C(14) C(20) C(15) 123.6(3) yes
C(14) C(20) C(19) 118.2(3) yes
C(15) C(20) C(19) 118.2(3) yes
C(2) O(1) H(2) 111(3) yes
C(12) O(2) H(12) 106(2) yes
C(2) C(3) H(3) 118(2) yes
C(4) C(3) H(3) 121(2) yes
C(3) C(4) H(4) 125(2) yes
C(10) C(4) H(4) 114(2) yes
C(6) C(5) H(5) 123(2) yes
C(10) C(5) H(5) 116(2) yes
C(5) C(6) H(6) 121(2) yes
C(7) C(6) H(6) 119(2) yes
C(6) C(7) H(7) 115(2) yes
C(8) C(7) H(7) 124(2) yes
C(7) C(8) H(8) 121(2) yes
C(9) C(8) H(8) 118(2) yes
C(12) C(13) H(13) 120(2) yes
C(14) C(13) H(13) 120(2) yes
C(13) C(14) H(14) 121(2) yes
C(20) C(14) H(14) 117(2) yes
C(16) C(15) H(15) 122(2) yes
C(20) C(15) H(15) 117(2) yes
C(15) C(16) H(16) 117(3) yes
C(17) C(16) H(16) 122(3) yes
C(16) C(17) H(17) 116(2) yes
C(18) C(17) H(17) 124(2) yes
C(17) C(18) H(18) 119(2) yes
C(19) C(18) H(18) 119(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(2) 1.365(4) yes
O(2) C(12) 1.374(4) yes
C(1) C(2) 1.383(4) yes
C(1) C(9) 1.426(3) yes
C(1) C(11) 1.494(4) yes
C(2) C(3) 1.411(4) yes
C(3) C(4) 1.349(4) yes
C(4) C(10) 1.417(4) yes
C(5) C(6) 1.356(4) yes
C(5) C(10) 1.417(4) yes
C(6) C(7) 1.400(4) yes
C(7) C(8) 1.373(4) yes
C(8) C(9) 1.416(4) yes
C(9) C(10) 1.421(3) yes
C(11) C(12) 1.380(4) yes
C(11) C(19) 1.422(4) yes
C(12) C(13) 1.408(5) yes
C(13) C(14) 1.353(6) yes
C(14) C(20) 1.419(5) yes
C(15) C(16) 1.350(6) yes
C(15) C(20) 1.434(5) yes
C(16) C(17) 1.386(5) yes
C(17) C(18) 1.365(4) yes
C(18) C(19) 1.406(4) yes
C(19) C(20) 1.425(4) yes
O(1) H(2) .93(4) yes
O(2) H(12) .83(3) yes
C(3) H(3) .95(4) yes
C(4) H(4) .98(3) yes
C(5) H(5) 1.01(3) yes
C(6) H(6) 1.00(4) yes
C(7) H(7) 1.01(3) yes
C(8) H(8) .97(3) yes
C(13) H(13) .97(3) yes
C(14) H(14) .97(3) yes
C(15) H(15) .96(4) yes
C(16) H(16) .99(5) yes
C(17) H(17) 1.05(3) yes
C(18) H(18) .98(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11762
