#------------------------------------------------------------------------------
#$Date: 2019-11-24 09:11:57 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237421 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/82/4088261.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_4088261
loop_
_publ_author_name
'Chang, Mu-Chieh'
'Otten, Edwin'
_publ_section_title
;
 Intramolecular Hydride Transfer Reactions in (Formazanate)Boron Dihydride
 Complexes
;
_journal_issue                   4
_journal_name_full               Organometallics
_journal_page_first              534
_journal_paper_doi               10.1021/acs.organomet.5b00968
_journal_volume                  35
_journal_year                    2016
_chemical_formula_sum            'C16 H17 B N3 O'
_chemical_formula_weight         278.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 113.0854(13)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.2629(5)
_cell_length_b                   19.8344(9)
_cell_length_c                   14.5639(8)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.415
_cell_measurement_theta_min      2.963
_cell_volume                     3258.7(3)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            69661
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.440
_diffrn_reflns_theta_min         2.963
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick,1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         4090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0490
_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)+(0.0863P)²+4.2507P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1548
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3678
_reflns_number_total             4090
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om5b00968_si_001.cif
_cod_data_source_block           mo_molan323_0ma_sq
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4088261
_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   0.974
_shelx_estimated_absorpt_t_max   0.980
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
N1 N 0.60900(9) 0.34511(5) 0.13885(8) 0.0135(2) Uani 1 1 d . . .
H100 H 0.5576(18) 0.4931(11) 0.1912(14) 0.027(5) Uiso 1 1 d . . .
N2 N 0.65335(10) 0.38775(5) 0.08493(8) 0.0136(2) Uani 1 1 d . . .
N3 N 0.57516(10) 0.45247(5) 0.17123(8) 0.0134(2) Uani 1 1 d . . .
C8 C 0.66914(11) 0.50801(6) 0.06422(9) 0.0130(2) Uani 1 1 d . . .
C7 C 0.63273(11) 0.44923(6) 0.10645(9) 0.0127(2) Uani 1 1 d . . .
C12 C 0.77666(12) 0.55311(7) -0.03064(10) 0.0186(3) Uani 1 1 d . . .
H12 H 0.8262 0.5458 -0.0661 0.022 Uiso 1 1 calc R U .
C13 C 0.74294(12) 0.49864(7) 0.01218(10) 0.0171(3) Uani 1 1 d . . .
H13 H 0.7701 0.4547 0.0062 0.021 Uiso 1 1 calc R U .
C9 C 0.63124(11) 0.57314(7) 0.07283(10) 0.0156(3) Uani 1 1 d . . .
H9 H 0.5815 0.5804 0.1081 0.019 Uiso 1 1 calc R U .
C10 C 0.66581(12) 0.62754(7) 0.02998(10) 0.0169(3) Uani 1 1 d . . .
H10 H 0.6392 0.6716 0.0365 0.020 Uiso 1 1 calc R U .
C11 C 0.73883(12) 0.61856(7) -0.02235(10) 0.0161(3) Uani 1 1 d . . .
C5 C 0.62030(12) 0.18198(7) 0.01839(10) 0.0192(3) Uani 1 1 d . . .
H5 H 0.6311 0.1657 -0.0388 0.023 Uiso 1 1 calc R U .
C2 C 0.59693(13) 0.22967(7) 0.18877(11) 0.0190(3) Uani 1 1 d . . .
H2 H 0.5918 0.2456 0.2485 0.023 Uiso 1 1 calc R U .
C4 C 0.60129(12) 0.13660(7) 0.08311(11) 0.0203(3) Uani 1 1 d . . .
H4 H 0.5952 0.0897 0.0689 0.024 Uiso 1 1 calc R U .
C1 C 0.61010(11) 0.27539(6) 0.12098(9) 0.0137(2) Uani 1 1 d . . .
C6 C 0.62380(11) 0.25123(7) 0.03611(10) 0.0164(3) Uani 1 1 d . . .
H6 H 0.6355 0.2818 -0.0094 0.020 Uiso 1 1 calc R U .
C14 C 0.77660(13) 0.67721(7) -0.06863(11) 0.0218(3) Uani 1 1 d . . .
H14A H 0.7781 0.6633 -0.1327 0.033 Uiso 1 1 calc R U .
H14B H 0.8559 0.6920 -0.0239 0.033 Uiso 1 1 calc R U .
H14C H 0.7204 0.7144 -0.0794 0.033 Uiso 1 1 calc R U .
C3 C 0.59135(13) 0.16082(7) 0.16911(11) 0.0219(3) Uani 1 1 d . . .
H3 H 0.5806 0.1301 0.2149 0.026 Uiso 1 1 calc R U .
B1 B 0.55557(12) 0.38438(7) 0.19321(10) 0.0135(3) Uani 1 1 d . . .
O1 O 0.5000 0.35788(7) 0.2500 0.0158(3) Uani 1 2 d S T P
O2 O 1.0000 0.07553(7) 0.2500 0.0157(3) Uani 1 2 d S T P
C15 C 0.89857(12) 0.11805(7) 0.19572(10) 0.0192(3) Uani 1 1 d . . .
H15A H 0.8276 0.1024 0.2061 0.023 Uiso 1 1 calc R U .
H15B H 0.8811 0.1173 0.1234 0.023 Uiso 1 1 calc R U .
C16 C 0.93322(14) 0.18853(7) 0.23761(11) 0.0233(3) Uani 1 1 d . . .
H16A H 0.9165 0.1956 0.2981 0.028 Uiso 1 1 calc R U .
H16B H 0.8918 0.2234 0.1875 0.028 Uiso 1 1 calc R U .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 N1 C1 117.08(10) . .
N2 N1 B1 110.02(10) . .
C1 N1 B1 132.28(11) . .
C7 N2 N1 105.92(10) . .
C7 N3 B1 106.51(10) . .
C9 C8 C13 118.67(11) . .
C9 C8 C7 122.09(11) . .
C13 C8 C7 119.23(11) . .
N2 C7 N3 113.89(11) . .
N2 C7 C8 121.41(11) . .
N3 C7 C8 124.71(11) . .
C13 C12 C11 121.03(12) . .
C12 C13 C8 120.56(12) . .
C10 C9 C8 120.41(11) . .
C9 C10 C11 121.24(12) . .
C10 C11 C12 118.08(12) . .
C10 C11 C14 121.44(12) . .
C12 C11 C14 120.49(12) . .
C4 C5 C6 120.94(12) . .
C3 C2 C1 120.13(12) . .
C5 C4 C3 119.02(13) . .
C2 C1 C6 119.39(12) . .
C2 C1 N1 119.68(11) . .
C6 C1 N1 120.94(11) . .
C5 C6 C1 119.75(12) . .
C4 C3 C2 120.65(13) . .
O1 B1 N3 131.79(12) . .
O1 B1 N1 124.60(12) . .
N3 B1 N1 103.61(10) . .
B1 O1 B1 134.75(15) 2_655 .
C15 O2 C15 109.06(14) . 2_755
O2 C15 C16 105.71(11) . .
C15 C16 C16 101.51(9) . 2_755
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 N2 1.4010(14) .
N1 C1 1.4081(16) .
N1 B1 1.4386(16) .
N2 C7 1.3081(16) .
N3 C7 1.3839(15) .
N3 B1 1.4299(17) .
C8 C9 1.3951(17) .
C8 C13 1.4020(16) .
C8 C7 1.4671(17) .
C12 C13 1.3892(18) .
C12 C11 1.3995(18) .
C9 C10 1.3930(18) .
C10 C11 1.3963(17) .
C11 C14 1.5057(18) .
C5 C4 1.388(2) .
C5 C6 1.3951(18) .
C2 C3 1.3916(19) .
C2 C1 1.3958(18) .
C4 C3 1.3907(19) .
C1 C6 1.3959(17) .
B1 O1 1.3662(14) .
O1 B1 1.3661(14) 2_655
O2 C15 1.4533(15) .
O2 C15 1.4533(15) 2_755
C15 C16 1.518(2) .
C16 C16 1.533(3) 2_755
