#------------------------------------------------------------------------------
#$Date: 2015-08-05 22:19:24 +0300 (Wed, 05 Aug 2015) $
#$Revision: 152860 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/39/4123949.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_4123949
loop_
_publ_author_name
'Brown, Alec N.'
'Li, Bo'
'Liu, Shih-Yuan'
_publ_section_title
;
 Negishi Cross-Coupling Is Compatible with a Reactive B-Cl Bond:
 Development of a Versatile Late-Stage Functionalization of 1,2-Azaborines
 and Its Application to the Synthesis of New BN Isosteres of Naphthalene
 and Indenyl.
;
_journal_issue                   28
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8932
_journal_page_last               8935
_journal_paper_doi               10.1021/jacs.5b05879
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C8 H8 B N'
_chemical_formula_sum            'C8 H8 B N'
_chemical_formula_weight         128.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 107.059(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1542(6)
_cell_length_b                   5.7395(4)
_cell_length_c                   7.7590(5)
_cell_measurement_reflns_used    2001
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.49
_cell_measurement_theta_min      5.68
_cell_volume                     347.15(4)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_laue_measured_fraction_full 0.981
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3226
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.487
_diffrn_reflns_theta_min         5.675
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\uS'
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G.M. (2013). SADABS. Bruker AXS Inc. Madison, WI USA.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             136
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       na
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     62
_refine_ls_number_reflns         616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0566
_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)+(0.0929P)²+0.1717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1641
_reflns_Friedel_coverage         0.000
_reflns_number_gt                511
_reflns_number_total             616
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b05879_si_003.cif
_cod_data_source_block           C8H8BN
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4123948--4123949.cif.
;
_cod_database_code               4123949
_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   0.938
_shelx_estimated_absorpt_t_max   0.984
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6285(3) 0.2507(3) 0.4400(3) 0.0424(7) Uani 0.5 1 d P A 1
B1 B 0.4838(3) 0.3876(4) 0.4497(3) 0.0329(6) Uani 0.5 1 d P A 1
C1 C 0.6285(3) 0.2507(3) 0.4400(3) 0.0424(7) Uani 0.5 1 d P A 2
C2 C 0.4838(3) 0.3876(4) 0.4497(3) 0.0329(6) Uani 0.5 1 d P A 2
C3 C 0.7870(3) 0.3221(4) 0.5226(3) 0.0448(7) Uani 1 1 d . . .
C4 C 0.8243(3) 0.5287(4) 0.6204(3) 0.0424(7) Uani 1 1 d . . .
C5 C 0.6967(3) 0.6800(4) 0.6397(3) 0.0456(7) Uani 1 1 d . . .
H1 H 0.720(4) 0.812(7) 0.702(4) 0.073(10) Uiso 1 1 d . . .
H2 H 0.616(3) 0.089(5) 0.373(4) 0.061(8) Uiso 1 1 d . . .
H3 H 0.948(3) 0.558(5) 0.676(4) 0.053(7) Uiso 1 1 d . . .
H4 H 0.880(4) 0.216(5) 0.515(4) 0.059(8) 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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C3 N1 B1 120.2(2) . .
C3 N1 H2 116.9(15) . .
B1 N1 H2 122.8(15) . .
N1 B1 C5 123.4(2) . 3_666
N1 B1 C2 118.6(2) . 3_666
C5 B1 C2 118.0(3) 3_666 3_666
C3 C1 C2 120.2(2) . .
C3 C1 H2 116.9(15) . .
C2 C1 H2 122.8(15) . .
C1 C2 C5 123.4(2) . 3_666
C1 C2 B1 118.6(2) . 3_666
C5 C2 B1 118.0(3) 3_666 3_666
C1 C3 C4 123.5(2) . .
C1 C3 H4 115.9(17) . .
C4 C3 H4 120.6(17) . .
C3 C4 C5 122.5(2) . .
C3 C4 H3 114.3(15) . .
C5 C4 H3 123.1(16) . .
C4 C5 B1 117.1(2) . 3_666
C4 C5 H1 122.7(19) . .
B1 C5 H1 120.2(19) 3_666 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C3 1.328(3) .
N1 B1 1.438(3) .
N1 H2 1.06(3) .
B1 C5 1.483(3) 3_666
B1 C2 1.492(4) 3_666
C1 C3 1.328(3) .
C1 C2 1.438(3) .
C1 H2 1.06(3) .
C2 C5 1.483(3) 3_666
C3 C4 1.392(3) .
C3 H4 0.99(3) .
C4 C5 1.397(3) .
C4 H3 0.99(3) .
C5 C2 1.483(3) 3_666
C5 H1 0.89(4) .
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
_geom_torsion_site_symmetry_4
C3 C1 C2 C5 179.6(2) 3_666
C3 C1 C2 B1 1.4(3) 3_666
C2 C1 C3 C4 -0.5(3) .
N1 C3 C4 C5 -0.2(3) .
C3 C4 C5 B1 -0.1(3) 3_666
