Regioselective routes to orthogonally-substituted aromatic MIDA boronates.
Close, Adam J.; Kemmitt, Paul; Mark Roe, S.; Spencer, John; Organic & biomolecular chemistry 14 (2016) 6751–6756; doi:10.1039/c6ob01141a

data_7155161
_publ_section_title
;
 Regioselective routes to orthogonally-substituted aromatic MIDA
 boronates.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6751
_journal_page_last               6756
_journal_paper_doi               10.1039/c6ob01141a
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C8 H9 B Br N O3'
_chemical_formula_sum            'C8 H9 B Br N O3'
_chemical_formula_weight         257.88
_chemical_name_systematic        '(5-acetamido-2-bromophenyl)boronic acid'
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-04-18 deposited with the CCDC.
2016-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.957(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2445(3)
_cell_length_b                   10.6254(5)
_cell_length_c                   12.4110(6)
_cell_measurement_reflns_used    1796
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      71.1780
_cell_measurement_theta_min      7.1020
_cell_volume                     955.21(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w   -109.00 -57.00   1.00   12.13    --  -36.75-178.00  60.00   52
  2  \w     35.00 109.00   1.00   12.13    --   36.75 178.00-180.00   74
  3  \w     20.00 104.00   1.00   12.13    --   36.75  57.00 150.00   84
  4  \w     38.00  84.00   1.00   48.49    --  107.00 -95.00 120.00   46
  5  \w     38.00  84.00   1.00   48.49    --  107.00 -95.00 150.00   46
  6  \w     39.00  77.00   1.00   48.49    --  107.00 -45.00   0.00   38
  7  \w     39.00  77.00   1.00   48.49    --  107.00 -45.00 -30.00   38
  8  \w     37.00  69.00   1.00   48.49    --  107.00 -30.00 -90.00   32
  9  \w     37.00  69.00   1.00   48.49    --  107.00 -30.00 -60.00   32
 10  \w     40.00 125.00   1.00   48.49    --  107.00 -61.00-180.00   85
 11  \w   -109.00 -57.00   1.00   12.13    --  -36.75-178.00-150.00   52
 12  \w     20.00 104.00   1.00   12.13    --   36.75  57.00-120.00   84
 13  \w     10.00 104.00   1.00   12.13    --   36.75  77.00 -30.00   94
 14  \w     86.00 125.00   1.00   48.49    --  107.00  30.00-120.00   39
 15  \w     38.00 176.00   1.00   48.49    --  107.00   0.00  30.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1616622000
_diffrn_orient_matrix_UB_12      0.0860719000
_diffrn_orient_matrix_UB_13      -0.0344879000
_diffrn_orient_matrix_UB_21      0.1119879000
_diffrn_orient_matrix_UB_22      0.0468941000
_diffrn_orient_matrix_UB_23      -0.0964012000
_diffrn_orient_matrix_UB_31      -0.0809636000
_diffrn_orient_matrix_UB_32      -0.1067715000
_diffrn_orient_matrix_UB_33      -0.0702943000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3908
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.233
_diffrn_reflns_theta_min         5.481
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.717
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_description       irregular
_exptl_crystal_F_000             512
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0721P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1512
_reflns_number_total             1737
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01141a3.cif
_cod_data_source_block           10br01
_cod_depositor_comments
'Adding full bibliography for 7155160--7155162.cif.'
_cod_database_code               7155161
_chemical_oxdiff_formula         'c12 N2 O5 Br B H14'
_reflns_odcompleteness_completeness 95.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C8(H8)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 1425642948.52
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.404
_oxdiff_exptl_absorpt_empirical_full_min 0.783
_solvent_exptl_crystal_recrystallization_method 'MeCN and water'