#------------------------------------------------------------------------------
#$Date: 2019-11-02 07:05:05 +0200 (Sat, 02 Nov 2019) $
#$Revision: 220891 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/76/4127698.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4127698
loop_
_publ_author_name
'Oeschger, Raphael J.'
'Larsen, Matthew A.'
'Bismuto, Alessandro'
'Hartwig, John F.'
_publ_section_title
;
 Origin of the Difference in Reactivity between Ir Catalysts for the
 Borylation of C-H Bonds.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16479
_journal_page_last               16485
_journal_paper_doi               10.1021/jacs.9b08920
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C30 H46 B2 N2 O4'
_chemical_formula_sum            'C30 H46 B2 N2 O4'
_chemical_formula_weight         520.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0153(3)
_cell_length_b                   11.1661(3)
_cell_length_c                   19.0586(5)
_cell_measurement_reflns_used    6098
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.4980
_cell_measurement_theta_min      5.5690
_cell_volume                     2982.60(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13276
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         4.640
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_description       needle
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0560
_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/[σ²(Fo²)+(0.0988P)²+1.3956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1595
_refine_ls_wR_factor_ref         0.1665
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2285
_reflns_number_total             2726
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b08920_si_002.cif
_cod_data_source_block           RO001_Hartwig
_cod_database_code               4127698
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.882
_shelx_estimated_absorpt_t_max   0.966
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.3517(2) 0.7742(2) 0.82271(12) 0.0477(6) Uani 1 1 d . .
H1A H 0.2820 0.7743 0.8183 0.072 Uiso 1 1 calc R U
H1B H 0.3697 0.8048 0.8690 0.072 Uiso 1 1 calc R U
H1C H 0.3756 0.6922 0.8172 0.072 Uiso 1 1 calc R U
C2 C 0.39442(15) 0.85299(18) 0.76655(10) 0.0340(5) Uani 1 1 d . .
C3 C 0.36147(16) 0.98086(19) 0.77545(11) 0.0377(5) Uani 1 1 d . .
H3A H 0.3807 1.0279 0.7344 0.057 Uiso 1 1 calc R U
H3B H 0.3905 1.0150 0.8177 0.057 Uiso 1 1 calc R U
H3C H 0.2918 0.9826 0.7800 0.057 Uiso 1 1 calc R U
C4 C 0.50486(15) 0.83742(18) 0.75673(10) 0.0339(5) Uani 1 1 d . .
C5 C 0.5585(2) 0.8021(2) 0.82271(12) 0.0509(7) Uani 1 1 d . .
H5A H 0.5338 0.7256 0.8401 0.076 Uiso 1 1 calc R U
H5B H 0.5496 0.8639 0.8586 0.076 Uiso 1 1 calc R U
H5C H 0.6265 0.7941 0.8120 0.076 Uiso 1 1 calc R U
C6 C 0.55208(15) 0.9439(2) 0.72286(12) 0.0388(5) Uani 1 1 d . .
H6A H 0.6184 0.9241 0.7115 0.058 Uiso 1 1 calc R U
H6B H 0.5507 1.0120 0.7553 0.058 Uiso 1 1 calc R U
H6C H 0.5179 0.9649 0.6797 0.058 Uiso 1 1 calc R U
C7 C 0.40525(13) 0.65484(16) 0.60539(9) 0.0245(4) Uani 1 1 d . .
C8 C 0.45891(12) 0.53041(15) 0.51771(9) 0.0223(4) Uani 1 1 d . .
C9 C 0.36583(13) 0.51268(16) 0.49268(9) 0.0237(4) Uani 1 1 d . .
H9 H 0.3551 0.4622 0.4534 0.028 Uiso 1 1 calc R U
C10 C 0.28945(12) 0.56873(16) 0.52519(9) 0.0236(4) Uani 1 1 d . .
C11 C 0.31167(12) 0.64223(16) 0.58235(9) 0.0256(4) Uani 1 1 d . .
H11 H 0.2620 0.6842 0.6058 0.031 Uiso 1 1 calc R U
C12 C 0.18555(12) 0.55086(16) 0.50253(9) 0.0258(4) Uani 1 1 d . .
C13 C 0.12855(14) 0.5054(2) 0.56542(11) 0.0345(5) Uani 1 1 d . .
H13A H 0.1568 0.4305 0.5825 0.052 Uiso 1 1 calc R U
H13B H 0.0623 0.4909 0.5512 0.052 Uiso 1 1 calc R U
H13C H 0.1300 0.5654 0.6029 0.052 Uiso 1 1 calc R U
C14 C 0.14392(14) 0.67054(18) 0.47763(12) 0.0360(5) Uani 1 1 d . .
H14A H 0.1484 0.7296 0.5155 0.054 Uiso 1 1 calc R U
H14B H 0.0768 0.6595 0.4646 0.054 Uiso 1 1 calc R U
H14C H 0.1799 0.6991 0.4368 0.054 Uiso 1 1 calc R U
C15 C 0.17669(14) 0.4587(2) 0.44384(11) 0.0346(5) Uani 1 1 d . .
H15A H 0.2126 0.4861 0.4028 0.052 Uiso 1 1 calc R U
H15B H 0.1094 0.4490 0.4312 0.052 Uiso 1 1 calc R U
H15C H 0.2024 0.3818 0.4598 0.052 Uiso 1 1 calc R U
B1 B 0.42633(15) 0.7349(2) 0.67142(11) 0.0288(5) Uani 1 1 d . .
N1 N 0.47916(10) 0.59863(13) 0.57342(7) 0.0233(4) Uani 1 1 d . .
O1 O 0.35747(10) 0.80677(12) 0.69961(7) 0.0327(4) Uani 1 1 d . .
O2 O 0.51119(10) 0.73927(13) 0.70604(7) 0.0343(4) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
C2 C1 H1A 109.5 .
C2 C1 H1B 109.5 .
H1A C1 H1B 109.5 .
C2 C1 H1C 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
O1 C2 C1 105.71(17) .
O1 C2 C3 108.75(17) .
C1 C2 C3 110.51(18) .
O1 C2 C4 101.84(14) .
C1 C2 C4 114.29(19) .
C3 C2 C4 114.83(17) .
C2 C3 H3A 109.5 .
C2 C3 H3B 109.5 .
H3A C3 H3B 109.5 .
C2 C3 H3C 109.5 .
H3A C3 H3C 109.5 .
H3B C3 H3C 109.5 .
O2 C4 C6 106.36(16) .
O2 C4 C5 108.82(16) .
C6 C4 C5 110.05(19) .
O2 C4 C2 102.80(15) .
C6 C4 C2 113.40(17) .
C5 C4 C2 114.74(18) .
C4 C5 H5A 109.5 .
C4 C5 H5B 109.5 .
H5A C5 H5B 109.5 .
C4 C5 H5C 109.5 .
H5A C5 H5C 109.5 .
H5B C5 H5C 109.5 .
C4 C6 H6A 109.5 .
C4 C6 H6B 109.5 .
H6A C6 H6B 109.5 .
C4 C6 H6C 109.5 .
H6A C6 H6C 109.5 .
H6B C6 H6C 109.5 .
N1 C7 C11 122.14(16) .
N1 C7 B1 118.66(16) .
C11 C7 B1 119.19(16) .
N1 C8 C9 123.21(16) .
N1 C8 C8 116.93(19) 5_666
C9 C8 C8 119.85(19) 5_666
C10 C9 C8 120.15(17) .
C10 C9 H9 119.9 .
C8 C9 H9 119.9 .
C9 C10 C11 116.17(16) .
C9 C10 C12 123.31(16) .
C11 C10 C12 120.50(15) .
C7 C11 C10 121.02(16) .
C7 C11 H11 119.5 .
C10 C11 H11 119.5 .
C15 C12 C13 107.97(16) .
C15 C12 C10 111.85(15) .
C13 C12 C10 108.61(14) .
C15 C12 C14 109.28(16) .
C13 C12 C14 109.50(16) .
C10 C12 C14 109.60(15) .
C12 C13 H13A 109.5 .
C12 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
C12 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
C12 C14 H14A 109.5 .
C12 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
C12 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
C12 C15 H15A 109.5 .
C12 C15 H15B 109.5 .
H15A C15 H15B 109.5 .
C12 C15 H15C 109.5 .
H15A C15 H15C 109.5 .
H15B C15 H15C 109.5 .
O2 B1 O1 113.94(18) .
O2 B1 C7 124.96(18) .
O1 B1 C7 121.10(17) .
C8 N1 C7 117.28(15) .
B1 O1 C2 107.38(15) .
B1 O2 C4 107.09(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.510(3) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 O1 1.470(2) .
C2 C3 1.510(3) .
C2 C4 1.569(3) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C4 O2 1.464(2) .
C4 C6 1.507(3) .
C4 C5 1.517(3) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 N1 1.356(2) .
C7 C11 1.390(2) .
C7 B1 1.572(3) .
C8 N1 1.337(2) .
C8 C9 1.403(3) .
C8 C8 1.498(3) 5_666
C9 C10 1.386(3) .
C9 H9 0.9500 .
C10 C11 1.399(3) .
C10 C12 1.532(2) .
C11 H11 0.9500 .
C12 C15 1.525(3) .
C12 C13 1.527(3) .
C12 C14 1.533(3) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
B1 O2 1.361(3) .
B1 O1 1.365(3) .
