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_2001182
_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 +. Br1 -. 2H2 O1'
_chemical_formula_moiety         'C22 H30 Br1 F2 N1 O6'
_chemical_formula_sum            'C22 H30 Br F2 N O6'
_chemical_formula_weight         522.38
_chemical_name_systematic
;
(+)-(S{R[R-(R)]})-\a,\a'-[Iminobis(methylene-6-fluoro-3,4-dihydro
-2H-1-benzopyran-2-methanol)]
Hydrobromide Dihydrate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.841(4)
_cell_length_b                   14.617(7)
_cell_length_c                   33.460(10)
_cell_measurement_reflns_used    28
_cell_measurement_temperature    293
_cell_measurement_theta_max      46
_cell_measurement_theta_min      16
_cell_volume                     2368(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    'DIRDIF92 (Beurskens et al., 1992)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Stoe STADI4 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  .050
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            6139
_diffrn_reflns_reduction_process
;
Decay and Lp corrected intensities were averaged, except for Friedel
pairs.
;
_diffrn_reflns_theta_max         59.18
_diffrn_standards_decay_%        9.1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.835
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       needle
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          .38
_exptl_crystal_size_mid          .06
_exptl_crystal_size_min          .04
_refine_diff_density_max         .54
_refine_diff_density_min         -.57
_refine_ls_abs_structure_details
;
The Bijvoet coefficient was 0.84(1) for the 101 most significant
Bijvoet pairs. With more stringent selection parameters it becomes 1.
;
_refine_ls_extinction_method     'none                                    '
_refine_ls_goodness_of_fit_obs   1.53
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         1088
_refine_ls_R_factor_all          .1867
_refine_ls_R_factor_obs          .0658
_refine_ls_shift/esd_max         .092
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/(\s^2^(F) + 0.00200F^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .1214
_refine_ls_wR_factor_obs         .0833
_reflns_number_observed          1088
_reflns_number_total             2840
_cod_data_source_file            na1052.cif
_cod_data_source_block           2
_cod_depositor_comments
;
 Updating space group information and adding the symmetry operation list.

 Antanas Vaitkus,
 2018-06-18

 Marking attached hydrogen atoms.

 Antanas Vaitkus,
 2017-03-27

The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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) + 0.00200F^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) +
0.00200F^2^)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2368.(2)
_cod_original_sg_symbol_H-M      'P 21 21 21   '
_cod_original_formula_sum        'C22 H30 Br1 F2 N1 O6'
_cod_database_code               2001182