#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/98/2009863.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_2009863
loop_
_publ_author_name
'Stomberg, R.'
'Li, S.'
'Lundquist, K.'
_publ_section_title
;
 threo-3-Fluoro-2-hydroxy-1,3-diphenyl-1-propanone and
 (1RS,2RS,3RS)-3-fluoro-1,3-diphenyl-1,2-propanediol
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1145
_journal_page_last               1148
_journal_paper_doi               10.1107/S0108270193012478
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C15 H15 F1 O2'
_chemical_formula_sum            'C15 H15 F O2'
_chemical_formula_weight         246.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 95.470(10)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   5.325(2)
_cell_length_b                   9.900(3)
_cell_length_c                   23.778(2)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    296
_cell_measurement_theta_max      37.3
_cell_measurement_theta_min      29.0
_cell_volume                     1247.8(6)
_diffrn_measurement_device       'Syntex P2₁'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            2378
_diffrn_reflns_theta_max         62.6
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.76
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.14
_refine_ls_goodness_of_fit_obs   1.94
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     223
_refine_ls_number_reflns         1333
_refine_ls_R_factor_obs          0.038
_refine_ls_shift/esd_max         0.02
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = [σ²(Fₒ) + 0.03(Fₒ)²]⁻¹'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.047
_reflns_number_observed          1333
_reflns_number_total             2125
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            ha1075.cif
_cod_data_source_block           ha1075_structure_2_of_2
_cod_depositor_comments
;
 Changing the space group from '-P 1' to '-P 2yn' after consulting the
 original publication. All related space group information was changed
 accordingly.

 Antanas Vaitkus,
 2017-07-04

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '[\s^2^(F~o~) +
0.03(F~o~)^2^]^-1^' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = [\s^2^(F~o~) + 0.03(F~o~)^2^]^-1^'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1247.9(7)
_cod_original_sg_symbol_Hall     '-P 2yn'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C15 H15 F1 O2'
_cod_database_code               2009863
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x+1/2,-y+1/2,z+1/2
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
C(1) -.2370(4) .2621(3) .66130(10)
C(2) -.0203(5) .1945(3) .68270(10)
C(3) .1057(6) .2335(4) .73350(10)
C(4) .0211(7) .3399(4) .76320(10)
C(5) -.1908(7) .4078(4) .74230(10)
C(6) -.3214(6) .3690(3) .69170(10)
C(7) -.3770(5) .2239(3) .60580(10)
C(8) -.2451(4) .2611(3) .55440(10)
C(9) -.3964(4) .2259(3) .49850(10)
C(10) -.2490(4) .2570(2) .44910(10)
C(11) -.2310(5) .3881(3) .42930(10)
C(12) -.0834(5) .4175(3) .38610(10)
C(13) .0518(5) .3175(3) .36260(10)
C(14) .0359(6) .1878(3) .38180(10)
C(15) -.1147(5) .1565(3) .42410(10)
F -.4176(3) .0835(2) .60468(7)
O(1) -.0093(3) .1964(2) .55913(8)
O(2) -.6249(3) .3031(2) .49705(8)
H(2) .050(5) .124(3) .6600(10)
H(3) .251(6) .187(3) .7490(10)
H(4) .117(7) .365(4) .799(2)
H(5) -.252(6) .476(3) .7620(10)
H(6) -.479(5) .409(3) .6780(10)
H(7) -.550(5) .266(2) .6030(10)
H(8) -.218(4) .359(2) .5550(10)
H(9) -.441(4) .131(2) .4990(10)
H(11) -.319(4) .456(3) .4460(10)
H(12) -.084(5) .508(3) .3730(10)
H(13) .160(5) .337(3) .3340(10)
H(14) .129(5) .118(3) .3670(10)
H(15) -.129(5) .072(3) .4380(10)
H(17) .092(6) .231(3) .5370(10)
H(18) -.700(7) .288(4) .465(2)
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(7) 121.7(3) yes
C(1) C(7) C(8) 114.8(2) yes
C(1) C(7) F 109.1(2) yes
C(8) C(7) F 107.9(2) yes
C(7) C(8) C(9) 113.6(2) yes
C(7) C(8) O(1) 107.7(2) yes
C(9) C(8) O(1) 111.0(2) yes
C(8) C(9) C(10) 111.1(2) yes
C(8) C(9) O(2) 105.9(2) yes
C(10) C(9) O(2) 112.1(2) yes
C(9) C(10) C(11) 121.0(2) yes
C(2) C(1) C(6) 118.7(3) yes
C(6) C(1) C(7) 119.6(2) yes
C(1) C(2) C(3) 120.2(3) yes
C(2) C(3) C(4) 120.7(3) yes
C(3) C(4) C(5) 119.5(3) yes
C(4) C(5) C(6) 120.5(3) yes
C(1) C(6) C(5) 120.3(3) yes
C(9) C(10) C(15) 120.9(2) yes
C(11) C(10) C(15) 118.0(2) yes
C(10) C(11) C(12) 120.8(3) yes
C(11) C(12) C(13) 120.5(3) yes
C(12) C(13) C(14) 119.2(3) yes
C(13) C(14) C(15) 120.9(3) yes
C(10) C(15) C(14) 120.6(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C(1) C(2) 1.388(4) yes
C(1) C(6) 1.380(4) yes
C(1) C(7) 1.502(3) yes
C(2) C(3) 1.380(4) yes
C(3) C(4) 1.369(5) yes
C(4) C(5) 1.365(5) yes
C(5) C(6) 1.387(4) yes
C(7) C(8) 1.512(3) yes
C(7) F 1.407(3) yes
C(8) C(9) 1.528(3) yes
C(8) O(1) 1.405(3) yes
C(9) C(10) 1.505(3) yes
C(9) O(2) 1.435(3) yes
C(10) C(11) 1.387(3) yes
C(10) C(15) 1.392(4) yes
C(11) C(12) 1.382(4) yes
C(12) C(13) 1.374(4) yes
C(13) C(14) 1.369(4) yes
C(14) C(15) 1.380(4) yes
C(2) H(2) 0.98(3) no
C(3) H(3) 0.94(3) no
C(4) H(4) 0.98(4) no
C(5) H(5) 0.90(3) no
C(6) H(6) 0.95(3) no
C(7) H(7) 1.01(2) no
C(8) H(8) 0.98(2) no
C(9) H(9) 0.97(2) no
C(11) H(11) 0.92(2) no
C(12) H(12) 0.95(3) no
C(13) H(13) 0.96(3) no
C(14) H(14) 0.94(3) no
C(15) H(15) 0.91(3) no
O(1) H(17) 0.87(3) no
O(2) H(18) 0.85(4) no
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
C(1) C(7) C(8) C(9) -177.8(2) yes
C(1) C(7) C(8) O(1) 58.7(3) yes
C(1) C(7) C(8) H(C8) -59.0(10) no
C(2) C(1) C(7) C(8) -71.7(3) yes
C(6) C(1) C(7) C(8) 106.8(3) yes
C(2) C(1) C(7) F 49.6(3) yes
C(6) C(1) C(7) F -131.9(3) yes
C(2) C(1) C(7) H(C7) 165.0(10) no
C(2) C(1) C(7) H(C7) -17.0(10) no
C(7) C(8) C(9) C(10) -176.4(2) yes
C(7) C(8) C(9) O(2) 61.6(3) yes
C(7) C(8) C(9) H(C9) -54.0(10) no
C(7) C(8) O(1) H(O1) -163(2) no
C(8) C(9) C(10) C(11) -79.1(3) yes
C(8) C(9) C(10) C(15) 97.2(3) yes
C(8) C(9) O(2) H(O2) 175(3) no
C(9) C(8) C(7) F 60.2(3) yes
C(9) C(8) C(7) H(C7) -54.0(10) no
C(9) C(8) O(1) H(O1) 72(2) no
C(10) C(9) C(8) O(1) -54.8(3) yes
C(10) C(9) C(8) H(C8) 64.0(10) no
C(10) C(9) O(2) H(O2) 53(3) no
C(11) C(10) C(9) O(2) 39.3(3) yes
C(15) C(10) C(9) O(2) -144.5(2) yes
C(11) C(10) C(9) H(C9) 160.0(10) no
F C(7) C(8) O(1) -63.2(2) yes
F C(7) C(8) H(C8) 179.0(10) no
O(1) C(8) C(7) H(C7) -178.0(10) no
O(1) C(8) C(9) O(2) -176.8(2) yes
O(1) C(8) C(9) H(C9) 67.0(10) no
O(2) C(9) C(8) H(C8) -58.0(10) no
H(C7) C(7) C(8) H(C8) 65(2) no
C(C8) C(8) C(9) H(C9) -174(2) no
H(C8) C(8) O(1) H(01) -46(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139057218
