#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:15:57 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179016 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/14/4121478.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_4121478
loop_
_publ_author_name
'Obligacion, Jennifer V.'
'Semproni, Scott P.'
'Chirik, Paul J.'
_publ_section_title
;
 Cobalt-catalyzed C-h borylation.
;
_journal_issue                   11
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4133
_journal_page_last               4136
_journal_paper_doi               10.1021/ja500712z
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C25 H49 B Co N O2 P2'
_chemical_formula_weight         527.33
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0403(4)
_cell_length_b                   33.7265(8)
_cell_length_c                   8.0786(2)
_cell_measurement_reflns_used    7742
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.58
_cell_measurement_theta_min      4.21
_cell_volume                     3008.07(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP3 (Farraguia, 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacavazzo, 1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11832
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    5.620
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.046
_platon_squeeze_details
;
The unit cell contained a molecule of disordered diethyl
ether solvate which was treated as a diffuse contribution
to the overall scattering through the use of PLATON/SQUEEZE.
;
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0586P)²+3.1273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1093
_reflns_number_gt                2449
_reflns_number_total             2606
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ja500712z_si_002.cif
_cod_data_source_block           sps147
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               4121478
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.3150(2) 0.05985(7) 0.0867(3) 0.0200(5) Uani 1 1 d .
H1A H 0.2339 0.0484 0.1083 0.024 Uiso 1 1 calc R
H1B H 0.3297 0.0590 -0.0341 0.024 Uiso 1 1 calc R
C2 C 0.4103(2) 0.03559(7) 0.1750(3) 0.0181(5) Uani 1 1 d .
C3 C 0.4078(2) -0.00553(7) 0.1744(3) 0.0224(5) Uani 1 1 d .
H3 H 0.3430 -0.0192 0.1222 0.027 Uiso 1 1 calc R
C4 C 0.5000 -0.02646(10) 0.2500 0.0232(8) Uani 1 2 d S
H4 H 0.5000 -0.0546 0.2500 0.028 Uiso 1 2 calc SR
C5 C 0.1905(2) 0.11365(7) 0.3081(3) 0.0199(5) Uani 1 1 d .
H5 H 0.1147 0.1064 0.2474 0.024 Uiso 1 1 calc R
C6 C 0.1750(2) 0.15539(8) 0.3787(3) 0.0289(6) Uani 1 1 d .
H6A H 0.1090 0.1554 0.4599 0.043 Uiso 1 1 calc R
H6B H 0.1556 0.1739 0.2888 0.043 Uiso 1 1 calc R
H6C H 0.2504 0.1637 0.4326 0.043 Uiso 1 1 calc R
C7 C 0.2097(2) 0.08347(7) 0.4473(3) 0.0251(5) Uani 1 1 d .
H7A H 0.2850 0.0896 0.5063 0.038 Uiso 1 1 calc R
H7B H 0.2151 0.0568 0.4000 0.038 Uiso 1 1 calc R
H7C H 0.1414 0.0847 0.5246 0.038 Uiso 1 1 calc R
C8 C 0.2576(2) 0.13930(7) -0.0215(3) 0.0226(5) Uani 1 1 d .
H8 H 0.2355 0.1664 0.0183 0.027 Uiso 1 1 calc R
C9 C 0.1424(3) 0.12078(8) -0.0933(3) 0.0329(6) Uani 1 1 d .
H9A H 0.1108 0.1378 -0.1817 0.049 Uiso 1 1 calc R
H9B H 0.0815 0.1182 -0.0057 0.049 Uiso 1 1 calc R
H9C H 0.1613 0.0945 -0.1384 0.049 Uiso 1 1 calc R
C10 C 0.3528(2) 0.14454(8) -0.1575(3) 0.0266(6) Uani 1 1 d .
H10A H 0.3749 0.1185 -0.2025 0.040 Uiso 1 1 calc R
H10B H 0.4249 0.1573 -0.1111 0.040 Uiso 1 1 calc R
H10C H 0.3195 0.1611 -0.2461 0.040 Uiso 1 1 calc R
C11 C 0.5506(2) 0.23785(7) 0.3165(3) 0.0245(5) Uani 1 1 d .
C12 C 0.6570(3) 0.26555(8) 0.2812(4) 0.0342(7) Uani 1 1 d .
H12A H 0.7164 0.2635 0.3709 0.051 Uiso 1 1 calc R
H12B H 0.6277 0.2929 0.2738 0.051 Uiso 1 1 calc R
H12C H 0.6952 0.2580 0.1763 0.051 Uiso 1 1 calc R
C13 C 0.5035(3) 0.24470(8) 0.4921(4) 0.0323(6) Uani 1 1 d .
H13A H 0.4356 0.2267 0.5139 0.048 Uiso 1 1 calc R
H13B H 0.4761 0.2722 0.5032 0.048 Uiso 1 1 calc R
H13C H 0.5686 0.2396 0.5717 0.048 Uiso 1 1 calc R
N1 N 0.5000 0.05622(8) 0.2500 0.0157(6) Uani 1 2 d S
Co1 Co 0.5000 0.115993(14) 0.2500 0.01327(17) Uani 1 2 d S
P1 P 0.31926(5) 0.111789(16) 0.15960(7) 0.01588(17) Uani 1 1 d .
B1 B 0.5000 0.17310(11) 0.2500 0.0194(8) Uani 1 2 d S
O1 O 0.59404(15) 0.19731(5) 0.3085(2) 0.0222(4) Uani 1 1 d .
H1 H 0.553(4) 0.1225(10) 0.082(5) 0.057(10) Uiso 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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
C2 C1 P1 110.16(15) . .
C2 C1 H1A 109.6 . .
P1 C1 H1A 109.6 . .
C2 C1 H1B 109.6 . .
P1 C1 H1B 109.6 . .
H1A C1 H1B 108.1 . .
N1 C2 C3 122.0(2) . .
N1 C2 C1 116.3(2) . .
C3 C2 C1 121.7(2) . .
C4 C3 C2 119.6(2) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C3 C4 C3 118.5(3) . 4_655
C3 C4 H4 120.7 . .
C3 C4 H4 120.7 4_655 .
C6 C5 C7 110.7(2) . .
C6 C5 P1 110.92(17) . .
C7 C5 P1 110.17(16) . .
C6 C5 H5 108.3 . .
C7 C5 H5 108.3 . .
P1 C5 H5 108.3 . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C5 C7 H7A 109.5 . .
C5 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C5 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C10 C8 C9 110.2(2) . .
C10 C8 P1 111.78(16) . .
C9 C8 P1 113.46(18) . .
C10 C8 H8 107.0 . .
C9 C8 H8 107.0 . .
P1 C8 H8 107.0 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C8 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C8 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
O1 C11 C13 107.2(2) . .
O1 C11 C12 108.3(2) . .
C13 C11 C12 110.0(2) . .
O1 C11 C11 101.96(13) . 4_655
C13 C11 C11 113.5(3) . 4_655
C12 C11 C11 115.1(2) . 4_655
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C11 C13 H13A 109.5 . .
C11 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C11 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C2 N1 C2 118.1(3) . 4_655
C2 N1 Co1 120.94(14) . .
C2 N1 Co1 120.94(14) 4_655 .
B1 Co1 N1 180.0 . .
B1 Co1 P1 93.817(19) . .
N1 Co1 P1 86.183(19) . .
B1 Co1 P1 93.817(19) . 4_655
N1 Co1 P1 86.183(19) . 4_655
P1 Co1 P1 172.37(4) . 4_655
B1 Co1 H1 81.6(13) . .
N1 Co1 H1 98.4(13) . .
P1 Co1 H1 93.7(15) . .
P1 Co1 H1 87.4(15) 4_655 .
C1 P1 C8 102.28(11) . .
C1 P1 C5 102.57(10) . .
C8 P1 C5 102.16(11) . .
C1 P1 Co1 101.32(8) . .
C8 P1 Co1 125.38(8) . .
C5 P1 Co1 119.49(8) . .
O1 B1 O1 108.8(3) . 4_655
O1 B1 Co1 125.59(14) . .
O1 B1 Co1 125.59(14) 4_655 .
B1 O1 C11 108.6(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.512(3) .
C1 P1 1.849(2) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 N1 1.353(3) .
C2 C3 1.387(3) .
C3 C4 1.381(3) .
C3 H3 0.9500 .
C4 C3 1.381(3) 4_655
C4 H4 0.9500 .
C5 C6 1.528(3) .
C5 C7 1.531(3) .
C5 P1 1.861(2) .
C5 H5 1.0000 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C10 1.531(4) .
C8 C9 1.531(4) .
C8 P1 1.861(2) .
C8 H8 1.0000 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 O1 1.451(3) .
C11 C13 1.528(4) .
C11 C12 1.528(4) .
C11 C11 1.550(5) 4_655
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
N1 C2 1.353(3) 4_655
N1 Co1 2.016(3) .
Co1 B1 1.926(4) .
Co1 P1 2.1296(6) .
Co1 P1 2.1296(6) 4_655
Co1 H1 1.49(4) .
B1 O1 1.403(3) .
B1 O1 1.403(3) 4_655
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
P1 C1 C2 N1 -17.9(2) . .
P1 C1 C2 C3 164.04(18) . .
N1 C2 C3 C4 -1.0(3) . .
C1 C2 C3 C4 176.91(18) . .
C2 C3 C4 C3 0.48(15) . 4_655
C3 C2 N1 C2 0.51(15) . 4_655
C1 C2 N1 C2 -177.5(2) . 4_655
C3 C2 N1 Co1 -179.49(15) . .
C1 C2 N1 Co1 2.5(2) . .
C2 N1 Co1 P1 11.36(11) . .
C2 N1 Co1 P1 -168.64(11) 4_655 .
C2 N1 Co1 P1 -168.64(11) . 4_655
C2 N1 Co1 P1 11.36(11) 4_655 4_655
C2 C1 P1 C8 153.61(16) . .
C2 C1 P1 C5 -100.76(17) . .
C2 C1 P1 Co1 23.24(17) . .
C10 C8 P1 C1 -78.54(19) . .
C9 C8 P1 C1 46.8(2) . .
C10 C8 P1 C5 175.52(17) . .
C9 C8 P1 C5 -59.11(19) . .
C10 C8 P1 Co1 35.1(2) . .
C9 C8 P1 Co1 160.47(14) . .
C6 C5 P1 C1 -177.72(18) . .
C7 C5 P1 C1 59.30(18) . .
C6 C5 P1 C8 -72.01(19) . .
C7 C5 P1 C8 165.02(17) . .
C6 C5 P1 Co1 71.35(19) . .
C7 C5 P1 Co1 -51.63(18) . .
B1 Co1 P1 C1 162.78(8) . .
N1 Co1 P1 C1 -17.22(8) . .
B1 Co1 P1 C8 48.70(9) . .
N1 Co1 P1 C8 -131.30(9) . .
B1 Co1 P1 C5 -85.61(9) . .
N1 Co1 P1 C5 94.39(9) . .
P1 Co1 B1 O1 -4.37(8) 4_655 .
P1 Co1 B1 O1 -4.37(8) . 4_655
P1 Co1 B1 O1 175.63(8) 4_655 4_655
O1 B1 O1 C11 10.82(11) 4_655 .
Co1 B1 O1 C11 -169.18(11) . .
C13 C11 O1 B1 93.4(2) . .
C12 C11 O1 B1 -147.86(18) . .
C11 C11 O1 B1 -26.1(3) 4_655 .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.026 155 31 ' '
2 0.500 0.500 -0.021 155 31 ' '
