#------------------------------------------------------------------------------
#$Date: 2019-11-24 09:11:57 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237421 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/82/4088260.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_4088260
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            'C20 H19 B N4'
_chemical_formula_weight         326.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 94.7599(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.14730(10)
_cell_length_b                   20.9249(7)
_cell_length_c                   19.0650(6)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      3.895
_cell_volume                     1648.79(9)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16573
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         3.761
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  ?\0.7455
_exptl_absorpt_correction_T_min  0.6987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick,1996)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1371 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3350
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0325
_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)+(0.0496P)²+0.6185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0846
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    0.855
_reflns_Friedel_fraction_max     0.832
_reflns_number_gt                3193
_reflns_number_total             3350
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om5b00968_si_001.cif
_cod_data_source_block           mo_molan309_0m
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4088260
_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   0.9350
_shelx_estimated_absorpt_t_max   0.9980
_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'
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
N1 N 0.6399(4) 0.19628(8) 0.36864(9) 0.0142(4) Uani 1 1 d . .
H101 H 0.578(5) 0.1988(10) 0.2531(11) 0.008(5) Uiso 1 1 d . .
N3 N 0.7261(4) 0.32452(8) 0.35864(10) 0.0155(3) Uani 1 1 d . .
N4 N 0.6191(4) 0.29339(8) 0.30216(9) 0.0144(3) Uani 1 1 d . .
N2 N 0.7478(4) 0.22847(8) 0.42482(9) 0.0147(4) Uani 1 1 d . .
H100 H 0.990(6) 0.2210(12) 0.2938(13) 0.018(6) Uiso 1 1 d . .
C8 C 1.0210(5) 0.32320(9) 0.47329(11) 0.0148(4) Uani 1 1 d . .
C7 C 0.8426(5) 0.28917(9) 0.41404(11) 0.0146(4) Uani 1 1 d . .
C10 C 1.2267(5) 0.42125(10) 0.52754(12) 0.0191(4) Uani 1 1 d . .
H10 H 1.2446 0.4655 0.5260 0.023 Uiso 1 1 calc R U
C1 C 0.4637(4) 0.13978(9) 0.38139(11) 0.0137(4) Uani 1 1 d . .
C15 C 0.4412(5) 0.33023(10) 0.24950(11) 0.0154(4) Uani 1 1 d . .
C11 C 1.3677(5) 0.38838(10) 0.58549(11) 0.0168(4) Uani 1 1 d . .
C13 C 1.1607(5) 0.29008(10) 0.53177(12) 0.0181(4) Uani 1 1 d . .
H13 H 1.1380 0.2459 0.5341 0.022 Uiso 1 1 calc R U
C9 C 1.0594(5) 0.38949(10) 0.47170(11) 0.0175(4) Uani 1 1 d . .
H9 H 0.9723 0.4126 0.4330 0.021 Uiso 1 1 calc R U
C12 C 1.3333(5) 0.32225(10) 0.58661(11) 0.0190(4) Uani 1 1 d . .
H12 H 1.4274 0.2992 0.6247 0.023 Uiso 1 1 calc R U
C4 C 0.1232(5) 0.02816(10) 0.40510(12) 0.0191(4) Uani 1 1 d . .
H4 H 0.0090 -0.0091 0.4129 0.023 Uiso 1 1 calc R U
C14 C 1.5531(5) 0.42267(11) 0.64587(12) 0.0235(5) Uani 1 1 d . .
H14A H 1.7715 0.4071 0.6511 0.035 Uiso 1 1 calc R U
H14B H 1.4512 0.4150 0.6885 0.035 Uiso 1 1 calc R U
H14C H 1.5545 0.4677 0.6364 0.035 Uiso 1 1 calc R U
C6 C 0.3448(5) 0.12897(10) 0.44658(11) 0.0174(4) Uani 1 1 d . .
H6 H 0.3781 0.1592 0.4822 0.021 Uiso 1 1 calc R U
C5 C 0.1762(5) 0.07310(10) 0.45833(11) 0.0194(4) Uani 1 1 d . .
H5 H 0.0987 0.0658 0.5020 0.023 Uiso 1 1 calc R U
C3 C 0.2411(5) 0.03892(10) 0.34028(12) 0.0200(4) Uani 1 1 d . .
H3 H 0.2046 0.0088 0.3046 0.024 Uiso 1 1 calc R U
C19 C 0.1504(6) 0.42580(11) 0.21292(13) 0.0226(5) Uani 1 1 d . .
H19 H 0.0610 0.4650 0.2237 0.027 Uiso 1 1 calc R U
C20 C 0.3040(5) 0.38877(10) 0.26619(11) 0.0179(4) Uani 1 1 d . .
H20 H 0.3156 0.4028 0.3126 0.021 Uiso 1 1 calc R U
C16 C 0.4177(5) 0.30866(10) 0.18038(12) 0.0201(4) Uani 1 1 d . .
H16 H 0.5055 0.2694 0.1694 0.024 Uiso 1 1 calc R U
C2 C 0.4137(5) 0.09434(10) 0.32793(11) 0.0177(4) Uani 1 1 d . .
H2 H 0.4949 0.1010 0.2845 0.021 Uiso 1 1 calc R U
C18 C 0.1297(6) 0.40452(11) 0.14366(13) 0.0237(5) Uani 1 1 d . .
H18 H 0.0272 0.4295 0.1081 0.028 Uiso 1 1 calc R U
C17 C 0.2618(6) 0.34618(11) 0.12773(12) 0.0243(5) Uani 1 1 d . .
H17 H 0.2464 0.3319 0.0814 0.029 Uiso 1 1 calc R U
B1 B 0.7228(6) 0.22186(11) 0.29493(12) 0.0164(5) 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'
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
N2 N1 C1 115.63(17)
N2 N1 B1 118.10(16)
C1 N1 B1 126.25(17)
N4 N3 C7 116.67(16)
N3 N4 C15 115.67(16)
N3 N4 B1 118.21(16)
C15 N4 B1 125.85(16)
N1 N2 C7 116.27(17)
C9 C8 C13 117.98(19)
C9 C8 C7 120.78(18)
C13 C8 C7 121.22(17)
N3 C7 N2 123.10(17)
N3 C7 C8 117.30(16)
N2 C7 C8 118.01(18)
C11 C10 C9 121.52(18)
C6 C1 C2 119.89(18)
C6 C1 N1 120.86(17)
C2 C1 N1 119.25(18)
C16 C15 C20 120.18(18)
C16 C15 N4 119.02(18)
C20 C15 N4 120.74(18)
C10 C11 C12 117.89(19)
C10 C11 C14 121.66(19)
C12 C11 C14 120.45(19)
C12 C13 C8 120.89(18)
C10 C9 C8 120.57(19)
C13 C12 C11 121.12(19)
C3 C4 C5 119.76(19)
C5 C6 C1 120.04(19)
C4 C5 C6 120.2(2)
C4 C3 C2 120.70(19)
C18 C19 C20 120.3(2)
C19 C20 C15 119.5(2)
C15 C16 C17 119.57(19)
C3 C2 C1 119.38(19)
C17 C18 C19 119.8(2)
C18 C17 C16 120.6(2)
N4 B1 N1 99.51(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.312(2)
N1 C1 1.421(2)
N1 B1 1.568(3)
N3 N4 1.304(2)
N3 C7 1.346(3)
N4 C15 1.423(2)
N4 B1 1.566(3)
N2 C7 1.350(3)
C8 C9 1.397(3)
C8 C13 1.397(3)
C8 C7 1.480(3)
C10 C11 1.389(3)
C10 C9 1.391(3)
C1 C6 1.393(3)
C1 C2 1.397(3)
C15 C16 1.389(3)
C15 C20 1.398(3)
C11 C12 1.391(3)
C11 C14 1.511(3)
C13 C12 1.391(3)
C4 C3 1.385(3)
C4 C5 1.388(3)
C6 C5 1.390(3)
C3 C2 1.393(3)
C19 C18 1.389(3)
C19 C20 1.389(3)
C16 C17 1.391(3)
C18 C17 1.382(3)
