#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:48:43 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281345 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/83/1568342.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_1568342
loop_
_publ_author_name
'Tendera, Lukas'
'Fantuzzi, Felipe'
'Marder, Todd B.'
'Radius, Udo'
_publ_section_title
;
 Nickel boryl complexes and nickel-catalyzed alkyne borylation.
;
_journal_issue                   8
_journal_name_full               'Chemical science'
_journal_page_first              2215
_journal_page_last               2228
_journal_paper_doi               10.1039/d2sc04690c
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C21 H16 B2 O4'
_chemical_formula_sum            'C21 H16 B2 O4'
_chemical_formula_weight         353.96
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-08-20 deposited with the CCDC.	2023-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                100.552(2)
_cell_angle_beta                 97.420(2)
_cell_angle_gamma                93.988(2)
_cell_formula_units_Z            2
_cell_length_a                   6.35850(10)
_cell_length_b                   8.8436(2)
_cell_length_c                   16.0653(4)
_cell_measurement_reflns_used    8649
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      77.2360
_cell_measurement_theta_min      2.8530
_cell_volume                     876.64(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_molecular_graphics    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      99.9(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18064
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.490
_diffrn_reflns_theta_min         2.828
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.540
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.49a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.096
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0419
_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)+(0.0661P)²+0.1901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1173
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3159
_reflns_number_total             3562
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04690c2.cif
_cod_data_source_block           compound_7
_cod_depositor_comments
'Adding full bibliography for 1568336--1568351.cif.'
_cod_database_code               1568342
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.54141(13) 0.52931(10) 0.67656(6) 0.0258(2) Uani 1 1 d . . . . .
B1 B 0.2196(2) 0.76616(17) 0.84686(9) 0.0277(3) Uani 1 1 d . . . . .
O002 O 0.27229(14) 0.67810(10) 0.64446(6) 0.0254(2) Uani 1 1 d . . . . .
B2 B 0.3436(2) 0.57280(15) 0.69362(9) 0.0236(3) Uani 1 1 d . . . . .
O003 O 0.41894(14) 0.82481(10) 0.83320(6) 0.0288(2) Uani 1 1 d . . . . .
O004 O 0.12036(15) 0.87839(10) 0.89536(6) 0.0301(2) Uani 1 1 d . . . . .
C005 C 0.2003(2) 0.50378(14) 0.75218(8) 0.0248(3) Uani 1 1 d . . . . .
C006 C 0.1344(2) 0.33407(14) 0.72535(8) 0.0248(3) Uani 1 1 d . . . . .
C007 C 0.5924(2) 0.60841(14) 0.61358(8) 0.0248(3) Uani 1 1 d . . . . .
C008 C 0.4305(2) 0.69885(14) 0.59489(8) 0.0248(3) Uani 1 1 d . . . . .
C009 C 0.4439(2) 0.97746(14) 0.87607(8) 0.0266(3) Uani 1 1 d . . . . .
C00A C 0.2884(2) 0.22888(14) 0.72528(8) 0.0267(3) Uani 1 1 d . . . . .
H00A H 0.431423 0.264894 0.741665 0.032 Uiso 1 1 calc R U . . .
C00B C 0.1293(2) 0.59444(15) 0.81800(9) 0.0283(3) Uani 1 1 d . . . . .
C00C C 0.2301(2) 0.07099(15) 0.70098(8) 0.0290(3) Uani 1 1 d . . . . .
H00C H 0.334338 0.002292 0.701738 0.035 Uiso 1 1 calc R U . . .
C00D C 0.2631(2) 1.00979(15) 0.91303(9) 0.0288(3) Uani 1 1 d . . . . .
C00E C -0.0795(2) 0.27672(15) 0.69914(9) 0.0302(3) Uani 1 1 d . . . . .
H00E H -0.184352 0.344908 0.698284 0.036 Uiso 1 1 calc R U . . .
C00F C 0.4345(2) 0.78867(15) 0.53349(9) 0.0304(3) Uani 1 1 d . . . . .
H00F H 0.324959 0.849069 0.521050 0.037 Uiso 1 1 calc R U . . .
C00G C 0.7683(2) 0.60171(15) 0.57191(9) 0.0303(3) Uani 1 1 d . . . . .
H00G H 0.876409 0.540300 0.584494 0.036 Uiso 1 1 calc R U . . .
C00H C 0.6145(2) 1.08592(16) 0.88405(9) 0.0330(3) Uani 1 1 d . . . . .
H00H H 0.736112 1.063559 0.859420 0.040 Uiso 1 1 calc R U . . .
C00I C 0.0187(2) 0.01517(15) 0.67570(9) 0.0315(3) Uani 1 1 d . . . . .
H00I H -0.019697 -0.090614 0.659690 0.038 Uiso 1 1 calc R U . . .
C00J C 0.7750(2) 0.69255(16) 0.50954(9) 0.0339(3) Uani 1 1 d . . . . .
H00J H 0.891056 0.691971 0.479728 0.041 Uiso 1 1 calc R U . . .
C00K C 0.5940(2) 1.23249(16) 0.93165(9) 0.0351(3) Uani 1 1 d . . . . .
H00K H 0.704678 1.310230 0.938571 0.042 Uiso 1 1 calc R U . . .
C00L C 0.4125(3) 1.26426(16) 0.96866(10) 0.0364(3) Uani 1 1 d . . . . .
H00L H 0.405007 1.362716 0.999970 0.044 Uiso 1 1 calc R U . . .
C00M C 0.6129(2) 0.78356(16) 0.49102(9) 0.0338(3) Uani 1 1 d . . . . .
H00M H 0.623255 0.842759 0.449212 0.041 Uiso 1 1 calc R U . . .
C00N C -0.1361(2) 0.11868(16) 0.67442(9) 0.0339(3) Uani 1 1 d . . . . .
H00N H -0.278518 0.081851 0.656902 0.041 Uiso 1 1 calc R U . . .
C00O C -0.0279(2) 0.53533(16) 0.87045(10) 0.0360(3) Uani 1 1 d . . . . .
H00B H -0.033570 0.424712 0.861771 0.054 Uiso 1 1 calc R U . . .
H00D H -0.166565 0.565151 0.852919 0.054 Uiso 1 1 calc R U . . .
H00O H 0.016668 0.578619 0.929956 0.054 Uiso 1 1 calc R U . . .
C00P C 0.2408(2) 1.15260(16) 0.96022(10) 0.0347(3) Uani 1 1 d . . . . .
H00P H 0.118909 1.173457 0.984960 0.042 Uiso 1 1 calc R U . . .
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'
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B2 O001 C007 105.14(10) . . ?
O004 B1 O003 111.24(11) . . ?
O004 B1 C00B 124.33(12) . . ?
O003 B1 C00B 124.25(12) . . ?
C008 O002 B2 105.16(10) . . ?
O001 B2 O002 111.36(11) . . ?
O001 B2 C005 126.52(11) . . ?
O002 B2 C005 121.82(11) . . ?
C009 O003 B1 105.16(10) . . ?
C00D O004 B1 105.23(10) . . ?
C00B C005 C006 123.18(11) . . ?
C00B C005 B2 121.61(11) . . ?
C006 C005 B2 115.01(10) . . ?
C00A C006 C00E 118.44(12) . . ?
C00A C006 C005 119.90(11) . . ?
C00E C006 C005 121.66(11) . . ?
C00G C007 C008 122.26(12) . . ?
C00G C007 O001 128.69(12) . . ?
C008 C007 O001 109.03(10) . . ?
C00F C008 C007 122.38(12) . . ?
C00F C008 O002 128.28(12) . . ?
C007 C008 O002 109.31(11) . . ?
C00H C009 C00D 122.33(13) . . ?
C00H C009 O003 128.69(12) . . ?
C00D C009 O003 108.98(11) . . ?
C00C C00A C006 120.68(12) . . ?
C00C C00A H00A 119.7 . . ?
C006 C00A H00A 119.7 . . ?
C005 C00B C00O 123.38(12) . . ?
C005 C00B B1 120.09(12) . . ?
C00O C00B B1 116.42(11) . . ?
C00I C00C C00A 120.57(12) . . ?
C00I C00C H00C 119.7 . . ?
C00A C00C H00C 119.7 . . ?
C00P C00D C009 122.55(13) . . ?
C00P C00D O004 128.07(13) . . ?
C009 C00D O004 109.37(11) . . ?
C00N C00E C006 120.46(12) . . ?
C00N C00E H00E 119.8 . . ?
C006 C00E H00E 119.8 . . ?
C008 C00F C00M 115.93(13) . . ?
C008 C00F H00F 122.0 . . ?
C00M C00F H00F 122.0 . . ?
C007 C00G C00J 116.09(13) . . ?
C007 C00G H00G 122.0 . . ?
C00J C00G H00G 122.0 . . ?
C009 C00H C00K 115.86(13) . . ?
C009 C00H H00H 122.1 . . ?
C00K C00H H00H 122.1 . . ?
C00C C00I C00N 119.37(12) . . ?
C00C C00I H00I 120.3 . . ?
C00N C00I H00I 120.3 . . ?
C00M C00J C00G 121.61(13) . . ?
C00M C00J H00J 119.2 . . ?
C00G C00J H00J 119.2 . . ?
C00L C00K C00H 121.59(13) . . ?
C00L C00K H00K 119.2 . . ?
C00H C00K H00K 119.2 . . ?
C00K C00L C00P 121.85(13) . . ?
C00K C00L H00L 119.1 . . ?
C00P C00L H00L 119.1 . . ?
C00J C00M C00F 121.73(13) . . ?
C00J C00M H00M 119.1 . . ?
C00F C00M H00M 119.1 . . ?
C00E C00N C00I 120.47(13) . . ?
C00E C00N H00N 119.8 . . ?
C00I C00N H00N 119.8 . . ?
C00B C00O H00B 109.5 . . ?
C00B C00O H00D 109.5 . . ?
H00B C00O H00D 109.5 . . ?
C00B C00O H00O 109.5 . . ?
H00B C00O H00O 109.5 . . ?
H00D C00O H00O 109.5 . . ?
C00D C00P C00L 115.82(13) . . ?
C00D C00P H00P 122.1 . . ?
C00L C00P H00P 122.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 B2 1.3869(16) . ?
O001 C007 1.3894(15) . ?
B1 O004 1.3862(17) . ?
B1 O003 1.3948(18) . ?
B1 C00B 1.5502(19) . ?
O002 C008 1.3839(15) . ?
O002 B2 1.3898(16) . ?
B2 C005 1.5628(18) . ?
O003 C009 1.3869(15) . ?
O004 C00D 1.3857(16) . ?
C005 C00B 1.3519(18) . ?
C005 C006 1.4975(17) . ?
C006 C00A 1.3966(17) . ?
C006 C00E 1.4009(18) . ?
C007 C00G 1.3749(18) . ?
C007 C008 1.3826(18) . ?
C008 C00F 1.3767(18) . ?
C009 C00H 1.3740(19) . ?
C009 C00D 1.3844(19) . ?
C00A C00C 1.3893(18) . ?
C00A H00A 0.9300 . ?
C00B C00O 1.5128(18) . ?
C00C C00I 1.382(2) . ?
C00C H00C 0.9300 . ?
C00D C00P 1.3754(19) . ?
C00E C00N 1.3894(19) . ?
C00E H00E 0.9300 . ?
C00F C00M 1.397(2) . ?
C00F H00F 0.9300 . ?
C00G C00J 1.397(2) . ?
C00G H00G 0.9300 . ?
C00H C00K 1.403(2) . ?
C00H H00H 0.9300 . ?
C00I C00N 1.391(2) . ?
C00I H00I 0.9300 . ?
C00J C00M 1.387(2) . ?
C00J H00J 0.9300 . ?
C00K C00L 1.388(2) . ?
C00K H00K 0.9300 . ?
C00L C00P 1.396(2) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00O H00B 0.9600 . ?
C00O H00D 0.9600 . ?
C00O H00O 0.9600 . ?
C00P H00P 0.9300 . ?
