#------------------------------------------------------------------------------
#$Date: 2016-08-11 15:44:09 +0300 (Thu, 11 Aug 2016) $
#$Revision: 185753 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/91/7119122.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_7119122
loop_
_publ_author_name
'Sam Yruegas'
'Dayna C. Patterson'
'Caleb D. Martin'
_publ_section_title
;
 Oxygen insertion into boroles as a route to 1,2-oxaborines
;
_journal_name_full               Chem.Commun.
_journal_page_first              6658
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C40 H29 B O'
_chemical_formula_sum            'C40 H29 B O'
_chemical_formula_weight         536.44
_chemical_name_common            Biphenyl-1,2-oxaborine
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-03-04 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                91.8608(17)
_cell_angle_beta                 94.7506(15)
_cell_angle_gamma                113.4778(15)
_cell_formula_units_Z            2
_cell_length_a                   10.5923(5)
_cell_length_b                   11.7946(7)
_cell_length_c                   12.5909(7)
_cell_measurement_reflns_used    9011
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.986
_cell_measurement_theta_min      2.403
_cell_volume                     1434.13(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26298
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.191
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       prism
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0434
_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)+(0.0643P)²+0.3468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1281
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4417
_reflns_number_total             5856
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc02040b2.cif
_cod_data_source_block           9Ph
_cod_database_code               7119122
_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   0.983
_shelx_estimated_absorpt_t_max   0.989
_shelxl_version_number           2013-4
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
O1 O 0.21959(10) 0.47094(9) 0.47286(8) 0.0233(2) Uani 1 1 d . . . . .
B1 B 0.10660(18) 0.35877(15) 0.45718(14) 0.0234(4) Uani 1 1 d . . . . .
C1 C 0.09235(15) 0.28005(13) 0.35456(12) 0.0237(3) Uani 1 1 d . . . . .
C2 C 0.20168(15) 0.32085(13) 0.29297(12) 0.0233(3) Uani 1 1 d . . . . .
C3 C 0.31979(15) 0.43748(13) 0.32055(12) 0.0231(3) Uani 1 1 d . . . . .
C4 C 0.32194(15) 0.51091(14) 0.40761(12) 0.0226(3) Uani 1 1 d . . . . .
C11 C -0.03232(16) 0.16348(14) 0.32211(11) 0.0252(3) Uani 1 1 d . . . . .
C12 C -0.16134(17) 0.16782(15) 0.29996(13) 0.0313(4) Uani 1 1 d . . . . .
H12 H -0.1691 0.2452 0.3057 0.038 Uiso 1 1 calc R U . . .
C13 C -0.27868(17) 0.06057(16) 0.26956(13) 0.0352(4) Uani 1 1 d . . . . .
H13 H -0.3656 0.0654 0.2540 0.042 Uiso 1 1 calc R U . . .
C14 C -0.26973(18) -0.05286(16) 0.26188(13) 0.0360(4) Uani 1 1 d . . . . .
H14 H -0.3502 -0.1261 0.2411 0.043 Uiso 1 1 calc R U . . .
C15 C -0.14267(18) -0.05916(15) 0.28464(13) 0.0335(4) Uani 1 1 d . . . . .
H15 H -0.1359 -0.1371 0.2800 0.040 Uiso 1 1 calc R U . . .
C16 C -0.02564(17) 0.04767(15) 0.31403(13) 0.0294(4) Uani 1 1 d . . . . .
H16 H 0.0611 0.0422 0.3290 0.035 Uiso 1 1 calc R U . . .
C21 C 0.19912(16) 0.24781(14) 0.19242(12) 0.0265(3) Uani 1 1 d . . . . .
C22 C 0.11495(18) 0.24753(16) 0.10196(13) 0.0354(4) Uani 1 1 d . . . . .
H22 H 0.0621 0.2963 0.1032 0.042 Uiso 1 1 calc R U . . .
C23 C 0.1073(2) 0.17661(18) 0.00967(15) 0.0475(5) Uani 1 1 d . . . . .
H23 H 0.0499 0.1776 -0.0521 0.057 Uiso 1 1 calc R U . . .
C24 C 0.1827(2) 0.10482(18) 0.00726(16) 0.0504(5) Uani 1 1 d . . . . .
H24 H 0.1768 0.0558 -0.0558 0.060 Uiso 1 1 calc R U . . .
C25 C 0.2667(2) 0.10441(17) 0.09674(16) 0.0473(5) Uani 1 1 d . . . . .
H25 H 0.3189 0.0550 0.0952 0.057 Uiso 1 1 calc R U . . .
C26 C 0.27558(19) 0.17598(16) 0.18928(14) 0.0370(4) Uani 1 1 d . . . . .
H26 H 0.3342 0.1757 0.2505 0.044 Uiso 1 1 calc R U . . .
C31 C 0.43743(15) 0.47858(14) 0.25273(12) 0.0240(3) Uani 1 1 d . . . . .
C32 C 0.54254(17) 0.43669(16) 0.27026(13) 0.0319(4) Uani 1 1 d . . . . .
H32 H 0.5369 0.3795 0.3230 0.038 Uiso 1 1 calc R U . . .
C33 C 0.65505(18) 0.47767(17) 0.21153(14) 0.0388(4) Uani 1 1 d . . . . .
H33 H 0.7266 0.4489 0.2244 0.047 Uiso 1 1 calc R U . . .
C34 C 0.66389(19) 0.56023(18) 0.13430(15) 0.0435(5) Uani 1 1 d . . . . .
H34 H 0.7415 0.5886 0.0943 0.052 Uiso 1 1 calc R U . . .
C35 C 0.5598(2) 0.60131(17) 0.11545(15) 0.0422(4) Uani 1 1 d . . . . .
H35 H 0.5656 0.6578 0.0621 0.051 Uiso 1 1 calc R U . . .
C36 C 0.44645(17) 0.56045(15) 0.17413(13) 0.0318(4) Uani 1 1 d . . . . .
H36 H 0.3747 0.5887 0.1604 0.038 Uiso 1 1 calc R U . . .
C41 C 0.42371(15) 0.63734(13) 0.44426(11) 0.0234(3) Uani 1 1 d . . . . .
C42 C 0.56646(16) 0.67594(14) 0.44296(12) 0.0271(3) Uani 1 1 d . . . . .
H42 H 0.6026 0.6207 0.4150 0.032 Uiso 1 1 calc R U . . .
C43 C 0.65541(17) 0.79439(15) 0.48230(13) 0.0317(4) Uani 1 1 d . . . . .
H43 H 0.7524 0.8195 0.4817 0.038 Uiso 1 1 calc R U . . .
C44 C 0.60503(18) 0.87642(15) 0.52231(13) 0.0351(4) Uani 1 1 d . . . . .
H44 H 0.6669 0.9579 0.5484 0.042 Uiso 1 1 calc R U . . .
C45 C 0.46376(18) 0.83937(15) 0.52422(13) 0.0336(4) Uani 1 1 d . . . . .
H45 H 0.4285 0.8957 0.5516 0.040 Uiso 1 1 calc R U . . .
C46 C 0.37384(17) 0.72084(14) 0.48649(12) 0.0278(3) Uani 1 1 d . . . . .
H46 H 0.2772 0.6957 0.4892 0.033 Uiso 1 1 calc R U . . .
C51 C 0.01578(15) 0.33011(13) 0.55314(12) 0.0226(3) Uani 1 1 d . . . . .
C52 C 0.01990(15) 0.42793(14) 0.62180(12) 0.0241(3) Uani 1 1 d . . . . .
H52 H 0.0736 0.5107 0.6063 0.029 Uiso 1 1 calc R U . . .
C53 C -0.05140(15) 0.40812(14) 0.71120(12) 0.0245(3) Uani 1 1 d . . . . .
H53 H -0.0476 0.4769 0.7548 0.029 Uiso 1 1 calc R U . . .
C54 C -0.12915(15) 0.28779(14) 0.73818(12) 0.0229(3) Uani 1 1 d . . . . .
C55 C -0.13380(16) 0.18919(14) 0.67129(12) 0.0259(3) Uani 1 1 d . . . . .
H55 H -0.1851 0.1066 0.6884 0.031 Uiso 1 1 calc R U . . .
C56 C -0.06474(16) 0.20986(14) 0.58037(12) 0.0252(3) Uani 1 1 d . . . . .
H56 H -0.0721 0.1409 0.5353 0.030 Uiso 1 1 calc R U . . .
C61 C -0.20407(16) 0.26589(14) 0.83513(12) 0.0258(3) Uani 1 1 d . . . . .
C62 C -0.14152(17) 0.33666(16) 0.93099(13) 0.0340(4) Uani 1 1 d . . . . .
H62 H -0.0497 0.3981 0.9343 0.041 Uiso 1 1 calc R U . . .
C63 C -0.21145(19) 0.31837(19) 1.02111(14) 0.0426(5) Uani 1 1 d . . . . .
H63 H -0.1677 0.3677 1.0855 0.051 Uiso 1 1 calc R U . . .
C64 C -0.34454(19) 0.22883(18) 1.01811(14) 0.0394(4) Uani 1 1 d . . . . .
H64 H -0.3921 0.2159 1.0803 0.047 Uiso 1 1 calc R U . . .
C65 C -0.40828(18) 0.15790(16) 0.92374(14) 0.0339(4) Uani 1 1 d . . . . .
H65 H -0.5003 0.0969 0.9208 0.041 Uiso 1 1 calc R U . . .
C66 C -0.33793(17) 0.17586(15) 0.83377(13) 0.0311(4) Uani 1 1 d . . . . .
H66 H -0.3819 0.1257 0.7698 0.037 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 0.0033 0.0016 '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 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C4 O1 B1 124.47(12) . .
O1 B1 C1 116.79(14) . .
O1 B1 C51 113.00(13) . .
C1 B1 C51 130.13(14) . .
C2 C1 C11 120.99(13) . .
C2 C1 B1 116.76(13) . .
C11 C1 B1 122.24(13) . .
C1 C2 C3 121.43(13) . .
C1 C2 C21 120.69(13) . .
C3 C2 C21 117.84(13) . .
C4 C3 C2 119.72(13) . .
C4 C3 C31 120.12(13) . .
C2 C3 C31 120.15(13) . .
O1 C4 C3 120.34(13) . .
O1 C4 C41 110.74(12) . .
C3 C4 C41 128.92(13) . .
C12 C11 C16 117.73(14) . .
C12 C11 C1 119.93(14) . .
C16 C11 C1 122.33(14) . .
C13 C12 C11 120.92(15) . .
C14 C13 C12 120.40(16) . .
C13 C14 C15 119.50(15) . .
C16 C15 C14 120.13(16) . .
C15 C16 C11 121.31(16) . .
C22 C21 C26 118.99(15) . .
C22 C21 C2 119.84(14) . .
C26 C21 C2 121.12(15) . .
C21 C22 C23 120.53(17) . .
C24 C23 C22 120.22(19) . .
C23 C24 C25 119.73(17) . .
C24 C25 C26 120.31(18) . .
C21 C26 C25 120.21(18) . .
C36 C31 C32 118.86(14) . .
C36 C31 C3 121.53(14) . .
C32 C31 C3 119.59(14) . .
C33 C32 C31 120.48(16) . .
C34 C33 C32 120.25(16) . .
C35 C34 C33 119.80(16) . .
C34 C35 C36 120.25(17) . .
C31 C36 C35 120.36(16) . .
C42 C41 C46 118.45(14) . .
C42 C41 C4 123.64(13) . .
C46 C41 C4 117.85(13) . .
C43 C42 C41 120.24(15) . .
C44 C43 C42 120.81(15) . .
C43 C44 C45 119.58(15) . .
C46 C45 C44 120.23(15) . .
C45 C46 C41 120.68(15) . .
C52 C51 C56 116.31(13) . .
C52 C51 B1 119.67(13) . .
C56 C51 B1 123.87(13) . .
C53 C52 C51 122.30(14) . .
C52 C53 C54 120.65(14) . .
C55 C54 C53 117.92(13) . .
C55 C54 C61 121.17(13) . .
C53 C54 C61 120.91(13) . .
C56 C55 C54 121.07(14) . .
C55 C56 C51 121.72(14) . .
C66 C61 C62 117.91(14) . .
C66 C61 C54 121.58(14) . .
C62 C61 C54 120.51(14) . .
C63 C62 C61 120.88(16) . .
C64 C63 C62 120.38(17) . .
C63 C64 C65 119.55(16) . .
C66 C65 C64 120.01(16) . .
C65 C66 C61 121.26(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.3558(17) .
O1 B1 1.380(2) .
B1 C1 1.527(2) .
B1 C51 1.568(2) .
C1 C2 1.379(2) .
C1 C11 1.493(2) .
C2 C3 1.450(2) .
C2 C21 1.500(2) .
C3 C4 1.368(2) .
C3 C31 1.496(2) .
C4 C41 1.480(2) .
C11 C12 1.393(2) .
C11 C16 1.396(2) .
C12 C13 1.389(2) .
C13 C14 1.379(3) .
C14 C15 1.384(2) .
C15 C16 1.382(2) .
C21 C22 1.386(2) .
C21 C26 1.387(2) .
C22 C23 1.387(2) .
C23 C24 1.377(3) .
C24 C25 1.378(3) .
C25 C26 1.391(2) .
C31 C36 1.387(2) .
C31 C32 1.392(2) .
C32 C33 1.382(2) .
C33 C34 1.381(3) .
C34 C35 1.377(3) .
C35 C36 1.389(2) .
C41 C42 1.396(2) .
C41 C46 1.399(2) .
C42 C43 1.383(2) .
C43 C44 1.378(2) .
C44 C45 1.384(2) .
C45 C46 1.381(2) .
C51 C52 1.403(2) .
C51 C56 1.405(2) .
C52 C53 1.382(2) .
C53 C54 1.398(2) .
C54 C55 1.396(2) .
C54 C61 1.485(2) .
C55 C56 1.386(2) .
C61 C66 1.390(2) .
C61 C62 1.398(2) .
C62 C63 1.382(2) .
C63 C64 1.381(3) .
C64 C65 1.386(2) .
C65 C66 1.383(2) .
