#------------------------------------------------------------------------------
#$Date: 2016-03-22 13:53:46 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178981 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/04/4120421.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_4120421
loop_
_publ_author_name
'Eric R. Abbey'
'Ashley N. Lamm'
'Andrew W. Baggett'
'Lev N. Zakharov'
'Shih-Yuan Liu'
_publ_section_title
;
 Protecting Group-Free Synthesis of 1,2-Azaborines: A Simple Approach to
 the Construction of BN-Benzenoids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12908
_journal_page_last               12913
_journal_paper_doi               10.1021/ja4073436
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C12 H12 B N O2'
_chemical_formula_weight         213.04
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXLTL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.083(2)
_cell_length_b                   18.098(3)
_cell_length_c                   7.4267(11)
_cell_measurement_reflns_used    1462
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.28
_cell_measurement_theta_min      2.38
_cell_volume                     2296.1(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex 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  0.0543
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13541
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_correction_T_min  0.9789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0431
_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)+(0.0407P)²+0.4584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                1400
_reflns_number_total             2024
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4073436_si_002.cif
_cod_data_source_block           liu127a
_cod_original_cell_volume        2296.2(6)
_cod_database_code               4120421
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
O1 O 0.06809(8) 0.33013(6) 0.52472(17) 0.0386(4) Uani 1 1 d
O2 O -0.00700(8) 0.42417(7) 0.61800(18) 0.0445(4) Uani 1 1 d
N1 N 0.10706(9) 0.44076(9) 0.3459(2) 0.0314(4) Uani 1 1 d
B1 B 0.10964(12) 0.36417(12) 0.3814(3) 0.0308(5) Uani 1 1 d
C1 C 0.14862(12) 0.47159(12) 0.2077(3) 0.0383(5) Uani 1 1 d
C2 C 0.19447(12) 0.43018(12) 0.1001(3) 0.0442(6) Uani 1 1 d
C3 C 0.19983(12) 0.35277(12) 0.1271(3) 0.0419(5) Uani 1 1 d
C4 C 0.16047(11) 0.31842(12) 0.2611(3) 0.0370(5) Uani 1 1 d
C5 C 0.01517(11) 0.36133(11) 0.6333(2) 0.0350(5) Uani 1 1 d
C6 C -0.01187(17) 0.30744(13) 0.7744(3) 0.0503(6) Uani 1 1 d
C7 C -0.06671(12) 0.33846(10) 0.9126(2) 0.0341(5) Uani 1 1 d
C8 C -0.14438(13) 0.31675(12) 0.9198(3) 0.0433(6) Uani 1 1 d
C9 C -0.19420(14) 0.34502(13) 1.0488(3) 0.0505(6) Uani 1 1 d
C10 C -0.16703(14) 0.39487(13) 1.1731(3) 0.0492(6) Uani 1 1 d
C11 C -0.08986(14) 0.41635(12) 1.1682(3) 0.0455(6) Uani 1 1 d
C12 C -0.03995(12) 0.38862(11) 1.0392(3) 0.0381(5) Uani 1 1 d
H1 H 0.1420(11) 0.5252(12) 0.192(3) 0.046(6) Uiso 1 1 d
H1N H 0.0749(12) 0.4698(11) 0.408(3) 0.048(6) Uiso 1 1 d
H2 H 0.2237(12) 0.4551(12) 0.001(3) 0.058(7) Uiso 1 1 d
H3 H 0.2335(12) 0.3269(10) 0.041(3) 0.047(6) Uiso 1 1 d
H4 H 0.1658(10) 0.2666(12) 0.275(3) 0.046(6) Uiso 1 1 d
H6A H -0.0372(14) 0.2677(15) 0.705(4) 0.094(10) Uiso 1 1 d
H6B H 0.0363(13) 0.2929(13) 0.833(3) 0.070(8) Uiso 1 1 d
H8 H -0.1636(12) 0.2839(12) 0.833(3) 0.061(7) Uiso 1 1 d
H9 H -0.2496(15) 0.3319(11) 1.056(3) 0.063(7) Uiso 1 1 d
H10 H -0.2031(13) 0.4147(12) 1.264(3) 0.067(7) Uiso 1 1 d
H11 H -0.0698(12) 0.4523(12) 1.255(3) 0.057(7) Uiso 1 1 d
H12 H 0.0152(12) 0.4048(10) 1.034(3) 0.047(6) 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 0.0033 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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 O1 B1 127.39(15)
C1 N1 B1 121.66(18)
C1 N1 H1N 118.1(13)
B1 N1 H1N 120.1(13)
N1 B1 O1 123.39(17)
N1 B1 C4 116.76(18)
O1 B1 C4 119.85(18)
C2 C1 N1 121.3(2)
C2 C1 H1 123.2(11)
N1 C1 H1 115.5(11)
C1 C2 C3 120.2(2)
C1 C2 H2 118.4(12)
C3 C2 H2 121.3(12)
C4 C3 C2 121.7(2)
C4 C3 H3 123.6(11)
C2 C3 H3 114.7(11)
C3 C4 B1 118.3(2)
C3 C4 H4 119.3(12)
B1 C4 H4 122.5(12)
O2 C5 O1 123.70(17)
O2 C5 C6 125.57(18)
O1 C5 C6 110.73(16)
C7 C6 C5 115.23(18)
C7 C6 H6A 110.9(16)
C5 C6 H6A 104.2(16)
C7 C6 H6B 109.0(14)
C5 C6 H6B 103.2(14)
H6A C6 H6B 114(2)
C12 C7 C8 118.46(19)
C12 C7 C6 120.3(2)
C8 C7 C6 121.3(2)
C9 C8 C7 120.8(2)
C9 C8 H8 119.8(13)
C7 C8 H8 119.3(13)
C10 C9 C8 120.2(2)
C10 C9 H9 116.8(13)
C8 C9 H9 123.0(13)
C9 C10 C11 119.5(2)
C9 C10 H10 119.4(14)
C11 C10 H10 121.0(14)
C10 C11 C12 120.6(2)
C10 C11 H11 120.4(13)
C12 C11 H11 119.0(13)
C11 C12 C7 120.4(2)
C11 C12 H12 120.5(12)
C7 C12 H12 119.0(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.337(2)
O1 B1 1.420(2)
O2 C5 1.204(2)
N1 C1 1.367(2)
N1 B1 1.412(3)
N1 H1N 0.89(2)
B1 C4 1.496(3)
C1 C2 1.347(3)
C1 H1 0.98(2)
C2 C3 1.418(3)
C2 H2 1.00(2)
C3 C4 1.353(3)
C3 H3 0.98(2)
C4 H4 0.95(2)
C5 C6 1.504(3)
C6 C7 1.499(3)
C6 H6A 0.98(3)
C6 H6B 0.97(2)
C7 C12 1.384(3)
C7 C8 1.385(3)
C8 C9 1.380(3)
C8 H8 0.94(2)
C9 C10 1.372(3)
C9 H9 0.98(2)
C10 C11 1.375(3)
C10 H10 0.98(2)
C11 C12 1.378(3)
C11 H11 0.98(2)
C12 H12 0.99(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O2 0.89(2) 2.25(2) 2.823(2) 121.9(16) .
N1 H1N O2 0.89(2) 2.25(2) 2.995(2) 140.8(17) 5_566
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
C1 N1 B1 O1 179.26(17)
C1 N1 B1 C4 0.4(3)
C5 O1 B1 N1 7.7(3)
C5 O1 B1 C4 -173.40(18)
B1 N1 C1 C2 -0.6(3)
N1 C1 C2 C3 0.8(3)
C1 C2 C3 C4 -0.8(3)
C2 C3 C4 B1 0.6(3)
N1 B1 C4 C3 -0.4(3)
O1 B1 C4 C3 -179.34(18)
B1 O1 C5 O2 3.1(3)
B1 O1 C5 C6 -176.87(19)
O2 C5 C6 C7 -4.6(4)
O1 C5 C6 C7 175.4(2)
C5 C6 C7 C12 -69.9(3)
C5 C6 C7 C8 111.5(2)
C12 C7 C8 C9 0.7(3)
C6 C7 C8 C9 179.29(19)
C7 C8 C9 C10 -0.5(3)
C8 C9 C10 C11 -0.1(3)
C9 C10 C11 C12 0.4(3)
C10 C11 C12 C7 -0.2(3)
C8 C7 C12 C11 -0.3(3)
C6 C7 C12 C11 -178.96(19)
