#------------------------------------------------------------------------------
#$Date: 2019-11-26 06:45:13 +0200 (Tue, 26 Nov 2019) $
#$Revision: 242855 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/30/4133002.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_4133002
loop_
_publ_author_name
'Liu, Siyuan'
'Légaré, Marc-André'
'Hofmann, Alexander'
'Braunschweig, Holger'
_publ_section_title
;
 A Boradiselenirane and a Boraditellurirane: Isolable Heavy Analogs of
 Dioxiranes and Dithiiranes.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11223
_journal_page_last               11226
_journal_paper_doi               10.1021/jacs.8b07829
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C9 H17 B N2 Se'
_chemical_formula_sum            'C9 H17 B N2 Se'
_chemical_formula_weight         243.01
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 108.23(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.404(7)
_cell_length_b                   7.679(4)
_cell_length_c                   12.800(7)
_cell_measurement_reflns_used    1888
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.77
_cell_measurement_theta_min      2.76
_cell_volume                     1158.0(11)
_computing_cell_refinement       'Saint+ ver. V8.38A (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.38A (Bruker AXS)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11282
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         1.996
_diffrn_source                   'rotating-anode (Nonius FR-591)'
_exptl_absorpt_coefficient_mu    3.202
_exptl_absorpt_correction_T_max  0.5867
_exptl_absorpt_correction_T_min  0.3044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.144
_refine_diff_density_max         0.844
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0877
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1823
_reflns_number_total             2281
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b07829_si_006.cif
_cod_data_source_block           AlHo067_a
_cod_original_cell_volume        1157.9(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4133002
_shelx_shelxl_version_number     2016/6
_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   0.287
_shelx_estimated_absorpt_t_max   0.656
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Se1 Se 0.60496(3) 0.90994(4) 0.68703(3) 0.01699(13) Uani 1 1 d . .
B1 B 0.4827(3) 0.7963(4) 0.7145(3) 0.0153(8) Uani 1 1 d . .
C1_1 C 0.4184(3) 0.8489(4) 0.7991(3) 0.0166(7) Uani 1 1 d . .
C2_1 C 0.4568(3) 1.0267(4) 0.8521(3) 0.0205(8) Uani 1 1 d . .
H2A_1 H 0.438024 1.117103 0.795264 0.031 Uiso 1 1 calc R U
H2B_1 H 0.538997 1.025071 0.888703 0.031 Uiso 1 1 calc R U
H2C_1 H 0.417899 1.051477 0.906374 0.031 Uiso 1 1 calc R U
C3_1 C 0.2894(3) 0.8568(4) 0.7416(3) 0.0218(8) Uani 1 1 d . .
H3A_1 H 0.272719 0.943337 0.682404 0.033 Uiso 1 1 calc R U
H3B_1 H 0.251241 0.889737 0.795084 0.033 Uiso 1 1 calc R U
H3C_1 H 0.262197 0.742259 0.710640 0.033 Uiso 1 1 calc R U
C4_1 C 0.4402(3) 0.7099(4) 0.8906(3) 0.0209(8) Uani 1 1 d . .
H4A_1 H 0.414571 0.595971 0.857634 0.031 Uiso 1 1 calc R U
H4B_1 H 0.398406 0.740641 0.941493 0.031 Uiso 1 1 calc R U
H4C_1 H 0.521634 0.704796 0.930837 0.031 Uiso 1 1 calc R U
C1_2 C 0.4424(3) 0.6224(4) 0.6434(3) 0.0141(7) Uani 1 1 d . .
N1_2 N 0.3628(2) 0.6092(3) 0.5446(2) 0.0167(6) Uani 1 1 d . .
C2_2 C 0.3583(3) 0.4408(4) 0.5044(3) 0.0220(8) Uani 1 1 d . .
H2_2 H 0.309617 0.398899 0.436093 0.026 Uiso 1 1 calc R U
N2_2 N 0.4874(2) 0.4613(3) 0.6666(2) 0.0174(6) Uani 1 1 d . .
C3_2 C 0.4361(3) 0.3483(4) 0.5810(3) 0.0202(8) Uani 1 1 d . .
H3_2 H 0.452867 0.228135 0.577206 0.024 Uiso 1 1 calc R U
C4_2 C 0.2965(3) 0.7545(4) 0.4829(3) 0.0242(8) Uani 1 1 d . .
H4A_2 H 0.266324 0.723090 0.404925 0.036 Uiso 1 1 calc R U
H4B_2 H 0.345195 0.857365 0.491078 0.036 Uiso 1 1 calc R U
H4C_2 H 0.233497 0.780354 0.511327 0.036 Uiso 1 1 calc R U
C5_2 C 0.5834(3) 0.4171(4) 0.7626(3) 0.0230(8) Uani 1 1 d . .
H5A_2 H 0.610050 0.299490 0.753785 0.035 Uiso 1 1 calc R U
H5B_2 H 0.559655 0.421228 0.828766 0.035 Uiso 1 1 calc R U
H5C_2 H 0.644987 0.500690 0.769839 0.035 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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 -2.00 0.0720
1.00 0.00 2.00 0.0510
0.00 -2.00 1.00 0.2270
0.00 2.00 -1.00 0.2240
-1.00 -1.00 -2.00 0.1960
1.00 1.00 2.00 0.1300
0.00 1.00 -1.00 0.1960
0.00 -1.00 1.00 0.1870
1.00 1.00 -2.00 0.1500
1.00 0.00 -2.00 0.0530
-1.00 0.00 2.00 0.0880
1.00 0.00 -1.00 0.0510
-1.00 0.00 1.00 0.0920
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1_1 B1 C1_2 117.7(3)
C1_1 B1 Se1 128.2(2)
C1_2 B1 Se1 114.0(3)
C2_1 C1_1 C3_1 108.0(3)
C2_1 C1_1 C4_1 108.8(3)
C3_1 C1_1 C4_1 107.4(3)
C2_1 C1_1 B1 112.1(3)
C3_1 C1_1 B1 110.7(3)
C4_1 C1_1 B1 109.6(3)
C1_1 C2_1 H2A_1 109.5
C1_1 C2_1 H2B_1 109.5
H2A_1 C2_1 H2B_1 109.5
C1_1 C2_1 H2C_1 109.5
H2A_1 C2_1 H2C_1 109.5
H2B_1 C2_1 H2C_1 109.5
C1_1 C3_1 H3A_1 109.5
C1_1 C3_1 H3B_1 109.5
H3A_1 C3_1 H3B_1 109.5
C1_1 C3_1 H3C_1 109.5
H3A_1 C3_1 H3C_1 109.5
H3B_1 C3_1 H3C_1 109.5
C1_1 C4_1 H4A_1 109.5
C1_1 C4_1 H4B_1 109.5
H4A_1 C4_1 H4B_1 109.5
C1_1 C4_1 H4C_1 109.5
H4A_1 C4_1 H4C_1 109.5
H4B_1 C4_1 H4C_1 109.5
N1_2 C1_2 N2_2 105.6(3)
N1_2 C1_2 B1 127.1(3)
N2_2 C1_2 B1 127.1(3)
C1_2 N1_2 C2_2 110.6(3)
C1_2 N1_2 C4_2 125.1(3)
C2_2 N1_2 C4_2 124.1(3)
C3_2 C2_2 N1_2 106.6(3)
C3_2 C2_2 H2_2 126.7
N1_2 C2_2 H2_2 126.7
C1_2 N2_2 C3_2 110.1(3)
C1_2 N2_2 C5_2 124.8(3)
C3_2 N2_2 C5_2 124.9(3)
C2_2 C3_2 N2_2 107.0(3)
C2_2 C3_2 H3_2 126.5
N2_2 C3_2 H3_2 126.5
N1_2 C4_2 H4A_2 109.5
N1_2 C4_2 H4B_2 109.5
H4A_2 C4_2 H4B_2 109.5
N1_2 C4_2 H4C_2 109.5
H4A_2 C4_2 H4C_2 109.5
H4B_2 C4_2 H4C_2 109.5
N2_2 C5_2 H5A_2 109.5
N2_2 C5_2 H5B_2 109.5
H5A_2 C5_2 H5B_2 109.5
N2_2 C5_2 H5C_2 109.5
H5A_2 C5_2 H5C_2 109.5
H5B_2 C5_2 H5C_2 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se1 B1 1.876(4)
B1 C1_1 1.585(5)
B1 C1_2 1.605(4)
C1_1 C2_1 1.533(4)
C1_1 C3_1 1.538(5)
C1_1 C4_1 1.545(4)
C2_1 H2A_1 0.9800
C2_1 H2B_1 0.9800
C2_1 H2C_1 0.9800
C3_1 H3A_1 0.9800
C3_1 H3B_1 0.9800
C3_1 H3C_1 0.9800
C4_1 H4A_1 0.9800
C4_1 H4B_1 0.9800
C4_1 H4C_1 0.9800
C1_2 N1_2 1.343(4)
C1_2 N2_2 1.352(4)
N1_2 C2_2 1.386(4)
N1_2 C4_2 1.462(4)
C2_2 C3_2 1.344(5)
C2_2 H2_2 0.9500
N2_2 C3_2 1.387(4)
N2_2 C5_2 1.458(4)
C3_2 H3_2 0.9500
C4_2 H4A_2 0.9800
C4_2 H4B_2 0.9800
C4_2 H4C_2 0.9800
C5_2 H5A_2 0.9800
C5_2 H5B_2 0.9800
C5_2 H5C_2 0.9800
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_2 B1 C1_1 C2_1 -173.9(3)
Se1 B1 C1_1 C2_1 7.4(4)
C1_2 B1 C1_1 C3_1 -53.2(4)
Se1 B1 C1_1 C3_1 128.1(3)
C1_2 B1 C1_1 C4_1 65.1(4)
Se1 B1 C1_1 C4_1 -113.5(3)
C1_1 B1 C1_2 N1_2 90.3(4)
Se1 B1 C1_2 N1_2 -90.9(4)
C1_1 B1 C1_2 N2_2 -95.2(4)
Se1 B1 C1_2 N2_2 83.6(4)
N2_2 C1_2 N1_2 C2_2 -0.8(4)
B1 C1_2 N1_2 C2_2 174.7(3)
N2_2 C1_2 N1_2 C4_2 -175.9(3)
B1 C1_2 N1_2 C4_2 -0.4(5)
C1_2 N1_2 C2_2 C3_2 0.6(4)
C4_2 N1_2 C2_2 C3_2 175.8(3)
N1_2 C1_2 N2_2 C3_2 0.6(4)
B1 C1_2 N2_2 C3_2 -174.8(3)
N1_2 C1_2 N2_2 C5_2 175.1(3)
B1 C1_2 N2_2 C5_2 -0.4(5)
N1_2 C2_2 C3_2 N2_2 -0.2(4)
C1_2 N2_2 C3_2 C2_2 -0.3(4)
C5_2 N2_2 C3_2 C2_2 -174.7(3)
