#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:23:55 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178948 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/77/4117740.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_4117740
loop_
_publ_author_name
'Xiangcheng Pan'
'Emmanuel Lacôte'
'Jacques Lalevée'
'Dennis P. Curran'
_publ_section_title
;
 Polarity Reversal Catalysis in Radical Reductions of Halides by
 N-Heterocyclic Carbene Boranes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5669
_journal_page_last               5674
_journal_paper_doi               10.1021/ja300416f
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C4 H10 B N3'
_chemical_formula_sum            'C4 H10 B N3'
_chemical_formula_weight         110.96
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.463(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4755(11)
_cell_length_b                   4.6745(5)
_cell_length_c                   12.6976(13)
_cell_measurement_reflns_used    1533
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      24.45
_cell_measurement_theta_min      3.26
_cell_volume                     669.80(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       '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    0.0512
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7448
_diffrn_reflns_theta_full        31.00
_diffrn_reflns_theta_max         32.24
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.100
_exptl_crystal_description       columnar
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         2211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0571
_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)+(0.0780P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1626
_reflns_number_gt                1286
_reflns_number_total             2211
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja300416f_si_001.cif
_cod_data_source_block           xpan425s
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4117740
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
B B 0.28709(17) -0.1670(3) 0.61064(12) 0.0518(4) Uani 1 1 d
H1A H 0.2144(13) -0.147(3) 0.5376(13) 0.065(4) Uiso 1 1 d
H1B H 0.3081(13) -0.391(4) 0.6295(13) 0.072(5) Uiso 1 1 d
H1C H 0.3714(17) -0.062(4) 0.5949(14) 0.079(5) Uiso 1 1 d
N1 N 0.15490(10) 0.1608(2) 0.71312(9) 0.0494(3) Uani 1 1 d
C1 C 0.24707(11) -0.0122(2) 0.71015(9) 0.0422(3) Uani 1 1 d
N2 N 0.30388(10) -0.0223(2) 0.81368(8) 0.0477(3) Uani 1 1 d
C2 C 0.24332(15) 0.1450(4) 0.87295(12) 0.0601(4) Uani 1 1 d
H2 H 0.2720(14) 0.167(4) 0.9500(15) 0.074(5) Uiso 1 1 d
N3 N 0.15183(13) 0.2617(3) 0.81483(11) 0.0638(4) Uani 1 1 d
C3 C 0.06442(18) 0.2538(5) 0.62513(16) 0.0670(5) Uani 1 1 d
H3A H -0.003(2) 0.175(5) 0.6279(18) 0.113(8) Uiso 1 1 d
H3B H 0.0796(19) 0.198(5) 0.5559(19) 0.110(8) Uiso 1 1 d
H3C H 0.057(2) 0.458(6) 0.625(2) 0.132(9) Uiso 1 1 d
C4 C 0.41177(16) -0.1841(4) 0.85405(14) 0.0636(5) Uani 1 1 d
H4A H 0.4189(17) -0.236(4) 0.9296(18) 0.101(7) Uiso 1 1 d
H4B H 0.4069(18) -0.359(6) 0.816(2) 0.108(8) Uiso 1 1 d
H4C H 0.483(2) -0.067(5) 0.8557(17) 0.114(7) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
B 0.0645(11) 0.0500(9) 0.0437(8) -0.0044(7) 0.0173(7) -0.0050(8)
N1 0.0515(7) 0.0513(6) 0.0480(6) -0.0003(5) 0.0161(5) -0.0020(5)
C1 0.0493(7) 0.0401(6) 0.0387(6) 0.0021(5) 0.0122(5) -0.0078(5)
N2 0.0542(7) 0.0541(6) 0.0366(5) 0.0012(5) 0.0134(5) -0.0045(5)
C2 0.0698(10) 0.0705(9) 0.0435(8) -0.0091(7) 0.0198(7) -0.0050(8)
N3 0.0724(9) 0.0676(8) 0.0577(8) -0.0109(6) 0.0285(7) 0.0030(7)
C3 0.0546(10) 0.0758(12) 0.0703(12) 0.0110(9) 0.0105(8) 0.0050(9)
C4 0.0609(10) 0.0793(12) 0.0498(9) 0.0134(8) 0.0077(7) 0.0040(8)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 B H1A 109.7(8)
C1 B H1B 110.2(9)
H1A B H1B 110.9(11)
C1 B H1C 108.8(9)
H1A B H1C 110.2(11)
H1B B H1C 106.9(12)
C1 N1 N3 112.78(12)
C1 N1 C3 128.33(13)
N3 N1 C3 118.87(14)
N1 C1 N2 103.70(11)
N1 C1 B 129.78(12)
N2 C1 B 126.49(12)
C1 N2 C2 108.17(12)
C1 N2 C4 125.77(12)
C2 N2 C4 126.06(13)
N3 C2 N2 111.79(14)
N3 C2 H2 128.2(10)
N2 C2 H2 120.0(10)
C2 N3 N1 103.56(13)
N1 C3 H3A 111.4(15)
N1 C3 H3B 113.6(12)
H3A C3 H3B 104(2)
N1 C3 H3C 110.8(15)
H3A C3 H3C 110(2)
H3B C3 H3C 107(2)
N2 C4 H4A 112.7(12)
N2 C4 H4B 107.5(13)
H4A C4 H4B 105.8(18)
N2 C4 H4C 111.8(13)
H4A C4 H4C 101.3(16)
H4B C4 H4C 118(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B C1 1.594(2)
B H1A 1.133(15)
B H1B 1.090(19)
B H1C 1.134(19)
N1 C1 1.3374(17)
N1 N3 1.3813(17)
N1 C3 1.447(2)
C1 N2 1.3580(15)
N2 C2 1.3605(19)
N2 C4 1.462(2)
C2 N3 1.289(2)
C2 H2 0.979(18)
C3 H3A 0.87(3)
C3 H3B 0.96(3)
C3 H3C 0.96(3)
C4 H4A 0.98(2)
C4 H4B 0.94(3)
C4 H4C 0.98(3)
