Structure and absolute configuration of nebivolol: (±)-(<i>R</i>*{<i>S</i>*[<i>S</i>*-(<i>S</i>*)]})-α,α'-[iminobis(methylene)]bis(6-fluoro-3,4-dihydro-2<i>H</i>-1-benzopyran-2-methanol) (nebivolol) hydrochloride (I) and (+)-(<i>S</i>{<i>R</i>[<i>R</i>-(<i>R</i>)]})-nebivolol hydrobromide dihydrate (II)
Peeters, O. M.; Blaton, N. M.; De Ranter, C. J.; Acta Crystallographica Section C 49 (1993) 2154–2157; doi:10.1107/S0108270193006687

data_2001181
_publ_section_title
;Structure and absolute configuration of nebivolol:
 (+-)-(<i>R</i>*{<i>S</i>*[<i>S</i>*-(<i>S</i>*)]})-\a,\a'-[iminobis(methylene)]bis(6-fluoro-3,4-dihydro-2<i>H</i>-1-benzopyran-2-methanol)
 (nebivolol) hydrochloride (I) and
 (+)-(<i>S</i>{<i>R</i>[<i>R</i>-(<i>R</i>)]})-nebivolol hydrobromide
 dihydrate (II)
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2154
_journal_page_last               2157
_journal_paper_doi               10.1107/S0108270193006687
_journal_volume                  49
_journal_year                    1993
_chemical_formula_analytical     'C22 H26 F2 NO4 ^+^. Cl ^-^'
_chemical_formula_moiety         'C22 H27 Cl1 F2 N1 O4'
_chemical_formula_sum            'C22 H27 Cl F2 N O4'
_chemical_formula_weight         442.91
_chemical_name_systematic
;
(^+^~-~)-(R^*^{S^*^[S^*^-(S^*^)]})-\a,\a'-[Iminobis(methylene-6-fluoro-
3,4-dihydro-2H-1-benzopyran-2-methanol] Hydrochloride
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                81.37(9)
_cell_angle_beta                 85.29(9)
_cell_angle_gamma                68.61(9)
_cell_formula_units_Z            2
_cell_length_a                   8.110(9)
_cell_length_b                   9.070(10)
_cell_length_c                   15.61(2)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293
_cell_measurement_theta_max      50
_cell_measurement_theta_min      40
_cell_volume                     1057(2)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe & Cie, 1985)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1985)'
_computing_molecular_graphics    'PLUTO (Motherwell & Clegg, 1978)'
_computing_publication_material  'PARST (Nardelli, 1983a)'
_computing_structure_refinement
'NRCVAX (Gabe, Le Page, Charland, Lee & White, 1989)'
_computing_structure_solution    'MULTAN80 (Main et al., 1980)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Stoe Stadi-4 four-circle diffractometer  '
_diffrn_measurement_method       2\q/\w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  .0150
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3812
_diffrn_reflns_theta_max         64.48
_diffrn_standards_decay_%        .6
_diffrn_standards_interval_time  60
_diffrn_standards_number         4
_exptl_absorpt_coefficient_mu    2.014
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       needle
_exptl_crystal_F_000             466
_exptl_crystal_size_max          .50
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .10
_refine_diff_density_max         .25
_refine_diff_density_min         -.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.10
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         1858
_refine_ls_R_factor_all          .0935
_refine_ls_R_factor_obs          .0464
_refine_ls_shift/esd_max         .013
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/(\s^2^(F) + 0.00300F^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .0900
_refine_ls_wR_factor_obs         .0699
_reflns_number_observed          1858
_reflns_number_total             3109
_reflns_observed_criterion       '> 3.0 sigma(I)'
_cod_data_source_file            na1052.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic ' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic ' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/(\s^2^(F) + 0.00300F^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) +
0.00300F^2^)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P -1       '
_cod_original_formula_sum        'C22 H27 Cl1 F2 N1 O4'
_cod_database_code               2001181