2-(6-Bromopyridin-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and (6-bromopyridin-3-yl)boronic acid, new bifunctional building blocks for combinatorial chemistry
Sopková-de Oliveira Santos, Jana; Lancelot, Jean-Charles; Bouillon, Alexandre; Rault, Sylvain; Acta Crystallographica Section C 59 (2003) o111–o113; doi:10.1107/S0108270103000908

data_2013131
_publ_section_title
;
 2-(6-Bromopyridin-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and
 (6-bromopyridin-3-yl)boronic acid, new bifunctional building blocks
 for combinatorial chemistry
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o111
_journal_page_last               o113
_journal_paper_doi               10.1107/S0108270103000908
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C5 H5 B Br N O2'
_chemical_formula_sum            'C5 H5 B Br N O2'
_chemical_formula_weight         201.82
_chemical_melting_point          471
_chemical_name_systematic
;
(6-bromopyridin-3-yl)boronic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 96.574(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4991(9)
_cell_length_b                   6.9178(5)
_cell_length_c                   13.8251(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      18
_cell_volume                     712.49(13)
_computing_cell_refinement       'CAD-4-PC Software (Enraf-Nonius, 1996)'
_computing_data_collection       'CAD-4-PC Software (Enraf-Nonius, 1996)'
_computing_data_reduction        'JANA98 (Pet\<r\'i\<cek & Du\<sek, 1998)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_av_sigmaI/netI    0.044
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2150
_diffrn_reflns_theta_full        29.97
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         2.73
_diffrn_standards_decay_%        2.4
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.699
_exptl_absorpt_correction_T_max  0.381
_exptl_absorpt_correction_T_min  0.073
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   '(JANA98; Pet\<r\'i\<cek & Du\<sek, 1998 )'
_exptl_crystal_colour            'dark white Grey'
_exptl_crystal_density_diffrn    1.881
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.62
_refine_diff_density_min         -0.83
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         2071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.099
_refine_ls_R_factor_gt           0.049
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0712P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.111
_refine_ls_wR_factor_ref         0.129
_reflns_number_gt                1326
_reflns_number_total             2071
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fa1004.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'YES' changed to 'yes' according
to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (3 times).

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 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Gaussian'
changed to 'gaussian' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

'_geom_bond_publ_flag'
value 'YES' changed to 'yes' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (3
times).

'_geom_angle_publ_flag' value 'YES' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (3
times).

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

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2013131
_cod_database_fobs_code          2013131