#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:03:03 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178833 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/87/4108786.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_4108786
loop_
_publ_author_name
'Peter F. Kaiser'
'Jonathan M. White'
'Craig A. Hutton'
_publ_section_title
;
 Enantioselective Preparation of a Stable Boronate Complex Stereogenic
 Only at Boron
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16450
_journal_page_last               16451
_journal_paper_doi               10.1021/ja8044629
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C25 H18 B N O3'
_chemical_formula_weight         391.21
_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
_cell_angle_alpha                99.372(10)
_cell_angle_beta                 95.847(9)
_cell_angle_gamma                98.583(12)
_cell_formula_units_Z            2
_cell_length_a                   5.936(3)
_cell_length_b                   10.222(5)
_cell_length_c                   16.668(9)
_cell_measurement_reflns_used    720
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      20.96
_cell_measurement_theta_min      2.50
_cell_volume                     978.4(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_av_sigmaI/netI    0.1297
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4521
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.25
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       rod
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.845
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.845
_refine_ls_R_factor_all          0.1157
_refine_ls_R_factor_gt           0.0592
_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)+(0.0434P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1370
_reflns_number_gt                1781
_reflns_number_total             3333
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8044629_si_002.cif
_cod_data_source_block           jmwpk2
_cod_original_cell_volume        978.3(8)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4108786
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
C1 C -0.1085(6) 0.5213(3) 0.26363(19) 0.0316(8) Uani 1 1 d .
C2 C 0.0364(5) 0.4263(3) 0.26766(18) 0.0305(8) Uani 1 1 d .
C3 C 0.0401(6) 0.3543(3) 0.33512(19) 0.0318(8) Uani 1 1 d .
C4 C 0.2015(6) 0.2699(3) 0.3514(2) 0.0386(9) Uani 1 1 d .
H4 H 0.3088 0.2527 0.3141 0.046 Uiso 1 1 calc R
C5 C 0.2048(6) 0.2131(3) 0.4197(2) 0.0447(9) Uani 1 1 d .
H5 H 0.3164 0.1579 0.4294 0.054 Uiso 1 1 calc R
C6 C 0.0477(7) 0.2337(4) 0.4765(2) 0.0493(10) Uani 1 1 d .
H6 H 0.0509 0.1922 0.5235 0.059 Uiso 1 1 calc R
C7 C -0.1081(6) 0.3141(3) 0.4623(2) 0.0435(9) Uani 1 1 d .
H7 H -0.2144 0.3287 0.5004 0.052 Uiso 1 1 calc R
C8 C -0.1181(6) 0.3762(3) 0.3939(2) 0.0356(8) Uani 1 1 d .
C9 C -0.2762(6) 0.4652(3) 0.3811(2) 0.0396(9) Uani 1 1 d .
H9 H -0.3883 0.4752 0.4175 0.047 Uiso 1 1 calc R
C10 C -0.2731(6) 0.5354(3) 0.3198(2) 0.0398(9) Uani 1 1 d .
H10 H -0.3805 0.5944 0.3137 0.048 Uiso 1 1 calc R
C11 C 0.2038(6) 0.2632(3) 0.16403(18) 0.0317(8) Uani 1 1 d .
C12 C 0.4062(6) 0.2413(3) 0.13139(19) 0.0373(9) Uani 1 1 d .
H12 H 0.5285 0.3141 0.1346 0.045 Uiso 1 1 calc R
C13 C 0.4271(6) 0.1119(3) 0.0942(2) 0.0440(9) Uani 1 1 d .
H13 H 0.5627 0.0969 0.0709 0.053 Uiso 1 1 calc R
C14 C 0.2520(7) 0.0062(3) 0.0911(2) 0.0474(10) Uani 1 1 d .
H14 H 0.2679 -0.0818 0.0662 0.057 Uiso 1 1 calc R
C15 C 0.0522(7) 0.0267(3) 0.1242(2) 0.0460(10) Uani 1 1 d .
H15 H -0.0692 -0.0465 0.1215 0.055 Uiso 1 1 calc R
C16 C 0.0312(6) 0.1554(3) 0.1614(2) 0.0380(9) Uani 1 1 d .
H16 H -0.1038 0.1694 0.1853 0.046 Uiso 1 1 calc R
C17 C 0.3041(6) 0.7490(3) 0.24878(19) 0.0334(8) Uani 1 1 d .
C18 C 0.5101(6) 0.8101(3) 0.2287(2) 0.0441(10) Uani 1 1 d .
H18 H 0.5434 0.7880 0.1741 0.053 Uiso 1 1 calc R
C19 C 0.6711(7) 0.9026(4) 0.2853(2) 0.0544(11) Uani 1 1 d .
H19 H 0.8115 0.9418 0.2696 0.065 Uiso 1 1 calc R
C20 C 0.6216(7) 0.9363(4) 0.3651(2) 0.0556(11) Uani 1 1 d .
H20 H 0.7279 0.9997 0.4044 0.067 Uiso 1 1 calc R
C21 C 0.4193(7) 0.8780(4) 0.3870(2) 0.0551(11) Uani 1 1 d .
H21 H 0.3873 0.8998 0.4418 0.066 Uiso 1 1 calc R
C22 C 0.2607(6) 0.7874(3) 0.3298(2) 0.0423(9) Uani 1 1 d .
H22 H 0.1193 0.7503 0.3458 0.051 Uiso 1 1 calc R
C23 C 0.1672(5) 0.4009(3) 0.19722(18) 0.0263(7) Uani 1 1 d .
C24 C 0.2071(6) 0.6072(3) 0.0465(2) 0.0358(8) Uani 1 1 d .
C25 C 0.3031(6) 0.4968(3) 0.08044(18) 0.0366(9) Uani 1 1 d .
H25A H 0.2452 0.4085 0.0446 0.044 Uiso 1 1 calc R
H25B H 0.4732 0.5135 0.0863 0.044 Uiso 1 1 calc R
N1 N 0.2208(4) 0.5015(2) 0.16066(15) 0.0293(6) Uani 1 1 d .
O1 O -0.0995(4) 0.6029(2) 0.20830(13) 0.0353(6) Uani 1 1 d .
O2 O 0.1051(4) 0.6793(2) 0.10155(12) 0.0371(6) Uani 1 1 d .
O3 O 0.2193(4) 0.6294(2) -0.02184(14) 0.0466(7) Uani 1 1 d .
B1 B 0.1290(7) 0.6392(4) 0.1831(2) 0.0333(9) Uani 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 0.0033 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'
N N 0.0061 0.0033 '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
O1 C1 C2 122.3(3)
O1 C1 C10 117.3(3)
C2 C1 C10 120.3(3)
C1 C2 C3 119.6(3)
C1 C2 C23 115.8(3)
C3 C2 C23 124.4(3)
C4 C3 C8 116.9(3)
C4 C3 C2 124.3(3)
C8 C3 C2 118.7(3)
C5 C4 C3 120.9(3)
C4 C5 C6 121.9(4)
C7 C6 C5 118.3(4)
C6 C7 C8 122.4(3)
C7 C8 C9 122.0(3)
C7 C8 C3 119.6(3)
C9 C8 C3 118.3(3)
C10 C9 C8 122.6(3)
C9 C10 C1 120.0(3)
C16 C11 C12 119.3(3)
C16 C11 C23 119.5(3)
C12 C11 C23 121.1(3)
C13 C12 C11 119.7(3)
C14 C13 C12 120.1(3)
C13 C14 C15 120.6(3)
C14 C15 C16 119.4(3)
C11 C16 C15 120.9(3)
C18 C17 C22 116.3(3)
C18 C17 B1 121.3(3)
C22 C17 B1 122.3(3)
C17 C18 C19 122.9(3)
C20 C19 C18 118.7(4)
C21 C20 C19 119.9(3)
C20 C21 C22 120.6(4)
C21 C22 C17 121.6(3)
N1 C23 C2 116.2(3)
N1 C23 C11 122.2(3)
C2 C23 C11 121.0(3)
O3 C24 O2 123.4(3)
O3 C24 C25 124.9(3)
O2 C24 C25 111.6(3)
N1 C25 C24 103.9(2)
C23 N1 C25 127.0(3)
C23 N1 B1 122.2(3)
C25 N1 B1 108.1(2)
C1 O1 B1 115.2(3)
C24 O2 B1 113.2(3)
O1 B1 O2 110.0(3)
O1 B1 N1 105.6(3)
O2 B1 N1 100.4(2)
O1 B1 C17 114.7(3)
O2 B1 C17 111.8(3)
N1 B1 C17 113.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.340(4)
C1 C2 1.395(4)
C1 C10 1.427(4)
C2 C3 1.440(4)
C2 C23 1.481(4)
C3 C4 1.417(4)
C3 C8 1.439(4)
C4 C5 1.359(4)
C5 C6 1.408(5)
C6 C7 1.354(5)
C7 C8 1.393(5)
C8 C9 1.425(5)
C9 C10 1.342(5)
C11 C16 1.380(4)
C11 C12 1.401(4)
C11 C23 1.482(4)
C12 C13 1.395(4)
C13 C14 1.373(5)
C14 C15 1.387(4)
C15 C16 1.389(4)
C17 C18 1.386(5)
C17 C22 1.404(4)
C17 B1 1.600(5)
C18 C19 1.398(5)
C19 C20 1.392(5)
C20 C21 1.370(5)
C21 C22 1.387(5)
C23 N1 1.294(4)
C24 O3 1.203(4)
C24 O2 1.334(4)
C24 C25 1.502(4)
C25 N1 1.466(4)
N1 B1 1.587(4)
O1 B1 1.473(4)
O2 B1 1.481(4)
