Synthesis of (Z)-4-Hydroxytamoxifen and (Z)-2-[4-[1-(p-Hydroxyphenyl)-2-phenyl]-1butenyl]phenoxyacetic Acid
Anastasia Detsi; Maria Koufaki; Theodora Calogeropoulou; Journal of Organic Chemistry 67 (2002) 4608–4611; doi:10.1021/jo0255328

data_4022222
_publ_section_title
;
 Synthesis of (Z)-4-Hydroxytamoxifen and
 (Z)-2-[4-[1-(p-Hydroxyphenyl)-2-phenyl]-1butenyl]phenoxyacetic Acid
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4608
_journal_page_last               4611
_journal_paper_doi               10.1021/jo0255328
_journal_volume                  67
_journal_year                    2002
_chemical_formula_sum            'C36 H25 F7 O2'
_chemical_formula_weight         622.56
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 91.65(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.57(1)
_cell_length_b                   15.58(1)
_cell_length_c                   24.91(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      11.6
_cell_measurement_theta_min      5.2
_cell_volume                     6045(7)
_computing_cell_refinement
'Program LEAST (UCLA Crystallographic package, C.E.Strouse 1994)'
_computing_data_collection
'Program COLLECT (UCLA Crystallographic package, C.E.Strouse 1994)'
_computing_data_reduction
'Program REDUCE (UCLA Crystallographic package, C.E.Strouse 1994)'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      298
_diffrn_measurement_device       'Crystal Logic Dual Goniometer'
_diffrn_measurement_method       'theta-2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            3727
_diffrn_reflns_theta_max         23.48
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        -2.9
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.113
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      1.35
_exptl_crystal_density_method    'floating method'
_exptl_crystal_description       parallelipiped
_exptl_crystal_F_000             2560
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.064
_refine_ls_goodness_of_fit_obs   1.160
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         3668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_restrained_S_obs      1.160
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_obs          0.0642
_refine_ls_shift/esd_max         0.056
_refine_ls_shift/esd_mean        0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+10.0293P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2000
_refine_ls_wR_factor_obs         0.1683
_reflns_number_observed          2367
_reflns_number_total             3668
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            jo0255328_s1.cif
_cod_data_source_block           shel93
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+10.0293P] 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^)+(0.0679P)^2^+10.0293P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               4022222