#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/47/7154727.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_7154727
loop_
_publ_author_name
'Zhu, Jianan'
'Wei, Ying'
'Lin, Dongqing'
'Ou, Changjin'
'Xie, Linghai'
'Zhao, Yu'
'Huang, Wei'
_publ_section_title
;
 One-pot synthesis of benzoxaborole derivatives from the
 palladium-catalyzed cross-coupling reaction of alkoxydiboron with
 unprotected o-bromobenzylalcohols.
;
_journal_issue                   46
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              11362
_journal_page_last               11368
_journal_paper_doi               10.1039/c5ob01781e
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         '2(C19 H13 B O2), C7 H8'
_chemical_formula_sum            'C45 H34 B2 O4'
_chemical_formula_weight         660.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-12-15 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                107.793(3)
_cell_angle_beta                 92.053(3)
_cell_angle_gamma                114.166(3)
_cell_formula_units_Z            1
_cell_length_a                   8.5900(6)
_cell_length_b                   9.4711(7)
_cell_length_c                   12.6798(10)
_cell_measurement_reflns_used    1952
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.85
_cell_measurement_theta_min      3.43
_cell_volume                     880.65(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_sigmaI/netI    0.1024
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7132
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.9839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             346
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.042(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3040
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0531
_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)+(0.0452P)²+0.1019P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1261
_reflns_number_gt                1676
_reflns_number_total             3040
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01781e2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154727.cif.
;
_cod_original_cell_volume        880.65(11)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7154727
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3330(3) 0.2637(3) 0.1922(2) 0.0298(6) Uani 1 1 d . . .
C2 C 0.3186(3) 0.2151(3) 0.2962(2) 0.0299(6) Uani 1 1 d . . .
C3 C 0.4351(4) 0.3024(4) 0.3989(2) 0.0375(7) Uani 1 1 d . . .
H3 H 0.5337 0.4041 0.4105 0.045 Uiso 1 1 calc R . .
C4 C 0.4013(4) 0.2348(4) 0.4834(2) 0.0476(8) Uani 1 1 d . . .
H4 H 0.4789 0.2904 0.5539 0.057 Uiso 1 1 calc R . .
C5 C 0.2566(4) 0.0878(4) 0.4666(3) 0.0498(8) Uani 1 1 d . . .
H5 H 0.2367 0.0436 0.5254 0.060 Uiso 1 1 calc R . .
C6 C 0.1408(4) 0.0047(4) 0.3656(2) 0.0410(8) Uani 1 1 d . . .
H6 H 0.0405 -0.0951 0.3554 0.049 Uiso 1 1 calc R . .
C7 C 0.1722(3) 0.0684(3) 0.2784(2) 0.0318(7) Uani 1 1 d . . .
B1 B 0.0793(4) 0.0149(4) 0.1571(3) 0.0339(8) Uani 1 1 d . . .
C9 C 0.5898(3) 0.4375(3) 0.1407(2) 0.0337(7) Uani 1 1 d . . .
C10 C 0.4989(3) 0.2810(3) 0.1468(2) 0.0312(7) Uani 1 1 d . . .
C11 C 0.5650(4) 0.1658(4) 0.1175(2) 0.0398(7) Uani 1 1 d . . .
H11 H 0.5041 0.0594 0.1225 0.048 Uiso 1 1 calc R . .
C12 C 0.7226(4) 0.2101(4) 0.0806(2) 0.0479(8) Uani 1 1 d . . .
H12 H 0.7696 0.1327 0.0596 0.058 Uiso 1 1 calc R . .
C13 C 0.8117(4) 0.3646(4) 0.0740(2) 0.0481(8) Uani 1 1 d . . .
H13 H 0.9191 0.3921 0.0482 0.058 Uiso 1 1 calc R . .
C14 C 0.7468(4) 0.4808(4) 0.1046(2) 0.0414(8) Uani 1 1 d . . .
H14 H 0.8091 0.5877 0.1007 0.050 Uiso 1 1 calc R . .
C15 C 0.4890(3) 0.5316(3) 0.1791(2) 0.0324(7) Uani 1 1 d . . .
C16 C 0.3396(3) 0.4317(3) 0.2083(2) 0.0311(7) Uani 1 1 d . . .
C17 C 0.2203(4) 0.4886(4) 0.2476(2) 0.0397(7) Uani 1 1 d . . .
H17 H 0.1181 0.4199 0.2671 0.048 Uiso 1 1 calc R . .
C18 C 0.2545(4) 0.6498(4) 0.2576(3) 0.0485(8) Uani 1 1 d . . .
H18 H 0.1742 0.6914 0.2839 0.058 Uiso 1 1 calc R . .
C19 C 0.4041(4) 0.7500(4) 0.2296(3) 0.0493(8) Uani 1 1 d . . .
H19 H 0.4251 0.8595 0.2372 0.059 Uiso 1 1 calc R . .
C20 C 0.5238(4) 0.6930(4) 0.1905(2) 0.0424(8) Uani 1 1 d . . .
H20 H 0.6268 0.7623 0.1720 0.051 Uiso 1 1 calc R . .
C21 C 0.0942(5) 0.6580(6) 0.5756(3) 0.0735(10) Uani 0.50 1 d PDU A 1
C24 C 0.1908(10) 0.8152(9) 0.6464(6) 0.069(2) Uani 0.50 1 d PDU A 1
H24A H 0.1587 0.8901 0.6222 0.103 Uiso 0.50 1 calc PR A 1
H24B H 0.3141 0.8452 0.6451 0.103 Uiso 0.50 1 calc PR A 1
H24C H 0.1697 0.8242 0.7231 0.103 Uiso 0.50 1 calc PR A 1
C21' C 0.0942(5) 0.6580(6) 0.5756(3) 0.0735(10) Uani 0.50 1 d PU A 2
H21A H 0.1590 0.7670 0.6283 0.088 Uiso 0.50 1 calc PR A 2
C22 C -0.0208(5) 0.6291(6) 0.4834(3) 0.0756(11) Uani 1 1 d DU . .
H22A H -0.0343 0.7183 0.4720 0.091 Uiso 1 1 calc R A 1
C23 C 0.1139(5) 0.5272(6) 0.5904(3) 0.0721(11) Uani 1 1 d DU . .
H23A H 0.1938 0.5470 0.6532 0.087 Uiso 1 1 calc R A 1
O1 O 0.1778(2) 0.1308(2) 0.11032(14) 0.0329(5) Uani 1 1 d . . .
O2 O -0.0699(2) -0.1176(2) 0.09973(16) 0.0433(6) Uani 1 1 d D . .
H2 H -0.104(4) -0.122(4) 0.0359(17) 0.052 Uiso 1 1 d D . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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'
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
O1 C1 C2 103.5(2) .
O1 C1 C16 110.91(19) .
C2 C1 C16 115.6(2) .
O1 C1 C10 111.7(2) .
C2 C1 C10 114.3(2) .
C16 C1 C10 101.2(2) .
C7 C2 C3 122.2(2) .
C7 C2 C1 111.7(2) .
C3 C2 C1 126.2(2) .
C4 C3 C2 117.4(3) .
C4 C3 H3 121.3 .
C2 C3 H3 121.3 .
C5 C4 C3 121.1(3) .
C5 C4 H4 119.5 .
C3 C4 H4 119.5 .
C6 C5 C4 120.9(3) .
C6 C5 H5 119.5 .
C4 C5 H5 119.5 .
C5 C6 C7 119.4(3) .
C5 C6 H6 120.3 .
C7 C6 H6 120.3 .
C2 C7 C6 119.0(3) .
C2 C7 B1 105.7(2) .
C6 C7 B1 135.3(3) .
O2 B1 O1 122.6(3) .
O2 B1 C7 129.2(3) .
O1 B1 C7 108.2(2) .
C14 C9 C10 120.7(3) .
C14 C9 C15 131.4(3) .
C10 C9 C15 107.9(2) .
C11 C10 C9 120.7(2) .
C11 C10 C1 128.0(2) .
C9 C10 C1 111.2(2) .
C12 C11 C10 118.2(3) .
C12 C11 H11 120.9 .
C10 C11 H11 120.9 .
C13 C12 C11 121.0(3) .
C13 C12 H12 119.5 .
C11 C12 H12 119.5 .
C12 C13 C14 120.9(3) .
C12 C13 H13 119.5 .
C14 C13 H13 119.5 .
C9 C14 C13 118.5(3) .
C9 C14 H14 120.8 .
C13 C14 H14 120.8 .
C16 C15 C20 120.7(2) .
C16 C15 C9 108.6(2) .
C20 C15 C9 130.7(3) .
C17 C16 C15 121.2(2) .
C17 C16 C1 127.8(2) .
C15 C16 C1 111.0(2) .
C16 C17 C18 118.1(3) .
C16 C17 H17 121.0 .
C18 C17 H17 121.0 .
C19 C18 C17 120.8(3) .
C19 C18 H18 119.6 .
C17 C18 H18 119.6 .
C18 C19 C20 121.1(3) .
C18 C19 H19 119.5 .
C20 C19 H19 119.5 .
C19 C20 C15 118.2(3) .
C19 C20 H20 120.9 .
C15 C20 H20 120.9 .
C24 C21 C23 121.4(5) .
C24 C21 C22 119.0(5) .
C23 C21 C22 119.5(4) .
C21 C24 H24A 109.5 .
C21 C24 H24B 109.5 .
H24A C24 H24B 109.5 .
C21 C24 H24C 109.5 .
H24A C24 H24C 109.5 .
H24B C24 H24C 109.5 .
C23 C22 C21 119.7(4) 2_566
C23 C22 H22A 120.2 2_566
C21 C22 H22A 120.2 .
C22 C23 C21 120.8(4) 2_566
C22 C23 H23A 119.6 2_566
C21 C23 H23A 119.6 .
B1 O1 C1 111.0(2) .
B1 O2 H2 116(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.473(3) .
C1 C2 1.518(3) .
C1 C16 1.518(3) .
C1 C10 1.522(3) .
C2 C7 1.386(4) .
C2 C3 1.397(4) .
C3 C4 1.391(4) .
C3 H3 0.9500 .
C4 C5 1.382(4) .
C4 H4 0.9500 .
C5 C6 1.378(4) .
C5 H5 0.9500 .
C6 C7 1.398(3) .
C6 H6 0.9500 .
C7 B1 1.538(4) .
B1 O2 1.344(4) .
B1 O1 1.394(3) .
C9 C14 1.379(4) .
C9 C10 1.393(4) .
C9 C15 1.476(4) .
C10 C11 1.388(4) .
C11 C12 1.388(4) .
C11 H11 0.9500 .
C12 C13 1.377(4) .
C12 H12 0.9500 .
C13 C14 1.390(4) .
C13 H13 0.9500 .
C14 H14 0.9500 .
C15 C16 1.390(4) .
C15 C20 1.391(4) .
C16 C17 1.383(3) .
C17 C18 1.395(4) .
C17 H17 0.9500 .
C18 C19 1.385(4) .
C18 H18 0.9500 .
C19 C20 1.386(4) .
C19 H19 0.9500 .
C20 H20 0.9500 .
C21 C24 1.352(7) .
C21 C23 1.383(5) .
C21 C22 1.384(5) .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C22 C23 1.355(5) 2_566
C22 H22A 0.9500 .
C23 C22 1.355(5) 2_566
C23 H23A 0.9500 .
O2 H2 0.833(17) .
