Silyl Phosphorus and Nitrogen Donor Chelates for Homogeneous Ortho Borylation Catalysis.
Ghaffari, Behnaz; Preshlock, Sean M.; Plattner, Donald L.; Staples, Richard J.; Maligres, Peter E.; Krska, Shane W.; Maleczka, Jr, Robert E; Smith, 3rd, Milton R; Journal of the American Chemical Society 136 (2014) 14345–; doi:10.1021/ja506229s

data_4122723
_publ_section_title
;
 Silyl Phosphorus and Nitrogen Donor Chelates for Homogeneous Ortho
 Borylation Catalysis.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14345
_journal_paper_doi               10.1021/ja506229s
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C16 H23 B O6'
_chemical_formula_sum            'C16 H23 B O6'
_chemical_formula_weight         322.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-11-04
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 118.6010(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.4123(4)
_cell_length_b                   9.0701(2)
_cell_length_c                   18.5703(3)
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.121
_cell_measurement_theta_min      2.710
_cell_volume                     3462.24(12)
_computing_cell_refinement       'APEX2 (BRUKER, V2012.10-0, 2012)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      172.99
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15915
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.114
_diffrn_reflns_theta_min         4.302
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0494 before and 0.0401 after correction. The Ratio of minimum to maximum transmission is 0.9014. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       Chunk
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.427
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.194
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0663
_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^)+(0.1027P)^2^+5.8014P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1903
_refine_ls_wR_factor_ref         0.1943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3053
_reflns_number_total             3362
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja506229s_si_003.cif
_cod_data_source_block           mrs913
_cod_depositor_comments
'Adding full bibliography for 4122723--4122724.cif.'
_cod_database_code               4122723
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.865
_shelx_estimated_absorpt_t_min   0.735
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C14(H14A,
 H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_contact_crystallographer_email  staples@chemistry.msu.com
_contact_crystallographer_name   'Richard Staples'