#------------------------------------------------------------------------------
#$Date: 2016-08-11 15:44:09 +0300 (Thu, 11 Aug 2016) $
#$Revision: 185753 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/91/7119121.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_7119121
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         'C34 H25 B O'
_chemical_formula_sum            'C34 H25 B O'
_chemical_formula_weight         460.35
_chemical_name_common            Pentaphenyl-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                86.4386(15)
_cell_angle_beta                 70.8147(14)
_cell_angle_gamma                85.0255(14)
_cell_formula_units_Z            2
_cell_length_a                   9.7747(5)
_cell_length_b                   11.2285(5)
_cell_length_c                   12.0790(6)
_cell_measurement_reflns_used    9022
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.233
_cell_measurement_theta_min      2.348
_cell_volume                     1246.59(11)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0508
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28438
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_min         2.348
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       prism
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.154
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         6434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0541P)²+0.2336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1190
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4380
_reflns_number_total             6434
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc02040b2.cif
_cod_data_source_block           9
_cod_database_code               7119121
_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   0.982
_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 0.86464(9) 0.15380(8) 0.02416(8) 0.0270(2) Uani 1 1 d . . . . .
B1 B 0.99592(15) 0.19955(13) -0.04034(13) 0.0236(3) Uani 1 1 d . . . . .
C1 C 1.06777(13) 0.26879(11) 0.02587(11) 0.0239(3) Uani 1 1 d . . . . .
C2 C 0.99460(13) 0.28575(11) 0.14402(11) 0.0234(3) Uani 1 1 d . . . . .
C3 C 0.85363(13) 0.23975(11) 0.20231(11) 0.0235(3) Uani 1 1 d . . . . .
C4 C 0.79591(13) 0.17084(12) 0.14042(11) 0.0256(3) Uani 1 1 d . . . . .
C11 C 1.21192(13) 0.32072(12) -0.02886(11) 0.0245(3) Uani 1 1 d . . . . .
C12 C 1.33798(14) 0.24762(13) -0.07631(11) 0.0281(3) Uani 1 1 d . . . . .
H12 H 1.3322 0.1637 -0.0776 0.034 Uiso 1 1 calc R U . . .
C13 C 1.47195(15) 0.29605(14) -0.12175(12) 0.0340(3) Uani 1 1 d . . . . .
H13 H 1.5571 0.2449 -0.1529 0.041 Uiso 1 1 calc R U . . .
C14 C 1.48257(16) 0.41836(15) -0.12204(12) 0.0372(4) Uani 1 1 d . . . . .
H14 H 1.5746 0.4511 -0.1525 0.045 Uiso 1 1 calc R U . . .
C15 C 1.35797(16) 0.49214(14) -0.07754(12) 0.0359(3) Uani 1 1 d . . . . .
H15 H 1.3642 0.5762 -0.0785 0.043 Uiso 1 1 calc R U . . .
C16 C 1.22379(15) 0.44412(12) -0.03145(12) 0.0301(3) Uani 1 1 d . . . . .
H16 H 1.1389 0.4958 -0.0013 0.036 Uiso 1 1 calc R U . . .
C21 C 1.06268(13) 0.34740(12) 0.21764(11) 0.0239(3) Uani 1 1 d . . . . .
C22 C 1.18249(13) 0.28989(12) 0.24110(12) 0.0276(3) Uani 1 1 d . . . . .
H22 H 1.2217 0.2150 0.2077 0.033 Uiso 1 1 calc R U . . .
C23 C 1.24533(15) 0.34058(14) 0.31270(12) 0.0337(3) Uani 1 1 d . . . . .
H23 H 1.3264 0.3000 0.3290 0.040 Uiso 1 1 calc R U . . .
C24 C 1.18978(16) 0.45024(14) 0.36032(13) 0.0371(4) Uani 1 1 d . . . . .
H24 H 1.2322 0.4851 0.4098 0.045 Uiso 1 1 calc R U . . .
C25 C 1.07241(16) 0.50907(14) 0.33586(13) 0.0373(4) Uani 1 1 d . . . . .
H25 H 1.0353 0.5851 0.3676 0.045 Uiso 1 1 calc R U . . .
C26 C 1.00838(15) 0.45791(12) 0.26518(12) 0.0299(3) Uani 1 1 d . . . . .
H26 H 0.9272 0.4986 0.2493 0.036 Uiso 1 1 calc R U . . .
C31 C 0.76845(13) 0.26895(11) 0.32623(11) 0.0244(3) Uani 1 1 d . . . . .
C32 C 0.82038(15) 0.23895(12) 0.42015(12) 0.0291(3) Uani 1 1 d . . . . .
H32 H 0.9143 0.1996 0.4058 0.035 Uiso 1 1 calc R U . . .
C33 C 0.73650(16) 0.26590(13) 0.53374(12) 0.0329(3) Uani 1 1 d . . . . .
H33 H 0.7733 0.2452 0.5966 0.039 Uiso 1 1 calc R U . . .
C34 C 0.59951(16) 0.32278(13) 0.55607(13) 0.0349(3) Uani 1 1 d . . . . .
H34 H 0.5416 0.3404 0.6342 0.042 Uiso 1 1 calc R U . . .
C35 C 0.54710(15) 0.35397(13) 0.46387(12) 0.0318(3) Uani 1 1 d . . . . .
H35 H 0.4531 0.3933 0.4789 0.038 Uiso 1 1 calc R U . . .
C36 C 0.63105(14) 0.32805(12) 0.35012(12) 0.0274(3) Uani 1 1 d . . . . .
H36 H 0.5946 0.3508 0.2875 0.033 Uiso 1 1 calc R U . . .
C41 C 0.65921(13) 0.10758(11) 0.18562(11) 0.0248(3) Uani 1 1 d . . . . .
C42 C 0.61942(15) 0.04798(12) 0.29522(12) 0.0312(3) Uani 1 1 d . . . . .
H42 H 0.6795 0.0482 0.3431 0.037 Uiso 1 1 calc R U . . .
C43 C 0.49296(16) -0.01152(13) 0.33471(13) 0.0347(3) Uani 1 1 d . . . . .
H43 H 0.4665 -0.0515 0.4096 0.042 Uiso 1 1 calc R U . . .
C44 C 0.40489(15) -0.01286(13) 0.26525(13) 0.0333(3) Uani 1 1 d . . . . .
H44 H 0.3177 -0.0530 0.2928 0.040 Uiso 1 1 calc R U . . .
C45 C 0.44451(14) 0.04452(13) 0.15565(13) 0.0314(3) Uani 1 1 d . . . . .
H45 H 0.3847 0.0430 0.1077 0.038 Uiso 1 1 calc R U . . .
C46 C 0.57086(14) 0.10414(12) 0.11557(12) 0.0281(3) Uani 1 1 d . . . . .
H46 H 0.5976 0.1429 0.0401 0.034 Uiso 1 1 calc R U . . .
C51 C 1.04255(14) 0.17114(12) -0.17353(12) 0.0272(3) Uani 1 1 d . . . . .
C52 C 0.97246(15) 0.08509(14) -0.21000(13) 0.0358(3) Uani 1 1 d . . . . .
H52 H 0.9002 0.0425 -0.1528 0.043 Uiso 1 1 calc R U . . .
C53 C 1.00567(16) 0.06044(15) -0.32744(14) 0.0409(4) Uani 1 1 d . . . . .
H53 H 0.9566 0.0014 -0.3496 0.049 Uiso 1 1 calc R U . . .
C54 C 1.10993(16) 0.12151(15) -0.41221(13) 0.0404(4) Uani 1 1 d . . . . .
H54 H 1.1321 0.1053 -0.4927 0.048 Uiso 1 1 calc R U . . .
C55 C 1.18170(16) 0.20629(15) -0.37916(13) 0.0390(4) Uani 1 1 d . . . . .
H55 H 1.2540 0.2482 -0.4371 0.047 Uiso 1 1 calc R U . . .
C56 C 1.14884(15) 0.23059(13) -0.26178(12) 0.0317(3) Uani 1 1 d . . . . .
H56 H 1.1996 0.2890 -0.2406 0.038 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 124.41(10) . .
O1 B1 C1 116.69(12) . .
O1 B1 C51 112.39(11) . .
C1 B1 C51 130.91(12) . .
C2 C1 C11 118.54(11) . .
C2 C1 B1 117.61(11) . .
C11 C1 B1 123.84(11) . .
C1 C2 C3 121.55(11) . .
C1 C2 C21 120.83(11) . .
C3 C2 C21 117.55(11) . .
C4 C3 C2 118.92(11) . .
C4 C3 C31 119.76(11) . .
C2 C3 C31 121.29(11) . .
O1 C4 C3 120.60(11) . .
O1 C4 C41 111.84(10) . .
C3 C4 C41 127.56(12) . .
C12 C11 C16 118.16(12) . .
C12 C11 C1 121.12(12) . .
C16 C11 C1 120.70(12) . .
C13 C12 C11 120.69(13) . .
C14 C13 C12 120.58(14) . .
C15 C14 C13 119.31(13) . .
C14 C15 C16 120.35(14) . .
C15 C16 C11 120.89(13) . .
C26 C21 C22 118.95(12) . .
C26 C21 C2 122.49(11) . .
C22 C21 C2 118.54(11) . .
C23 C22 C21 120.77(13) . .
C24 C23 C22 119.81(13) . .
C25 C24 C23 119.85(13) . .
C24 C25 C26 120.42(14) . .
C25 C26 C21 120.17(13) . .
C36 C31 C32 118.18(12) . .
C36 C31 C3 118.99(12) . .
C32 C31 C3 122.83(11) . .
C33 C32 C31 120.78(13) . .
C34 C33 C32 120.27(13) . .
C33 C34 C35 119.62(13) . .
C36 C35 C34 120.29(13) . .
C35 C36 C31 120.85(13) . .
C42 C41 C46 118.89(12) . .
C42 C41 C4 121.47(12) . .
C46 C41 C4 119.60(12) . .
C43 C42 C41 120.47(13) . .
C42 C43 C44 120.18(14) . .
C45 C44 C43 119.79(13) . .
C46 C45 C44 120.33(13) . .
C45 C46 C41 120.32(13) . .
C52 C51 C56 116.57(13) . .
C52 C51 B1 119.69(12) . .
C56 C51 B1 123.70(12) . .
C53 C52 C51 121.80(14) . .
C54 C53 C52 120.13(14) . .
C55 C54 C53 119.53(14) . .
C54 C55 C56 120.32(14) . .
C55 C56 C51 121.65(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.3605(15) .
O1 B1 1.3875(17) .
B1 C1 1.5094(19) .
B1 C51 1.567(2) .
C1 C2 1.3870(18) .
C1 C11 1.4983(17) .
C2 C3 1.4498(17) .
C2 C21 1.5027(17) .
C3 C4 1.3786(18) .
C3 C31 1.4952(18) .
C4 C41 1.4917(18) .
C11 C12 1.3926(18) .
C11 C16 1.3979(19) .
C12 C13 1.3877(19) .
C13 C14 1.386(2) .
C14 C15 1.382(2) .
C15 C16 1.3879(19) .
C21 C26 1.3875(18) .
C21 C22 1.3904(18) .
C22 C23 1.3857(19) .
C23 C24 1.381(2) .
C24 C25 1.381(2) .
C25 C26 1.3874(19) .
C31 C36 1.3936(18) .
C31 C32 1.3999(19) .
C32 C33 1.3840(19) .
C33 C34 1.382(2) .
C34 C35 1.386(2) .
C35 C36 1.3831(19) .
C41 C42 1.3959(19) .
C41 C46 1.3976(18) .
C42 C43 1.3848(19) .
C43 C44 1.387(2) .
C44 C45 1.385(2) .
C45 C46 1.3849(18) .
C51 C52 1.4011(19) .
C51 C56 1.4020(19) .
C52 C53 1.387(2) .
C53 C54 1.380(2) .
C54 C55 1.380(2) .
C55 C56 1.386(2) .
