#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/82/2018259.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2018259
loop_
_publ_author_name
'Batsanov, Andrei S.'
'Bramham, George'
'Norman, Nicholas C.'
'Russell, Christopher A.'
_publ_section_title
;
 A variable-temperature study of
 1,2-bis(dimethylamino)-1,2-bis(2,6-dimethylanilino)diborane
;
_journal_coeditor_code           MX3055
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o394
_journal_page_last               o396
_journal_paper_doi               10.1107/S0108270111039230
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H32 B2 N4'
_chemical_formula_moiety         'C20 H32 B2 N4'
_chemical_formula_sum            'C20 H32 B2 N4'
_chemical_formula_weight         350.12
_chemical_name_systematic
;
1,2-bis(dimethylamino)-1,2-bis(2,6-dimethylanilino)diborane
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 98.06(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.4957(11)
_cell_length_b                   9.6327(10)
_cell_length_c                   10.5554(11)
_cell_measurement_reflns_used    4810
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.90
_cell_measurement_theta_min      2.56
_cell_volume                     1056.6(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'OLEX2 (Version 1.1-β+++; Dolomanov et al., 2009)'
_computing_publication_material
'OLEX2 (Version 1.1-β+++; Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXTL (Version 6.12; Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Version 6.12; Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens SMART 1000 CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10983
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.11
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.100
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2436
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0428
_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)+(0.0582P)²+0.1935P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1280
_reflns_number_gt                1779
_reflns_number_total             2436
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            mx3055.cif
_cod_data_source_block           a-I
_cod_original_cell_volume        1056.63(19)
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_database_code               2018259
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.11688(10) 0.21137(13) 0.12955(11) 0.0417(3) Uani d D 1 1 . .
H H1N 0.0336(12) 0.2042(16) 0.1103(14) 0.050 Uiso d D 1 1 . .
N N2 0.08526(12) 0.42128(13) 0.24982(12) 0.0509(3) Uani d . 1 1 . .
C C1 0.17641(11) 0.09284(14) 0.08258(11) 0.0351(3) Uani d . 1 1 . .
C C2 0.13404(11) -0.03951(14) 0.11391(11) 0.0363(3) Uani d . 1 1 . .
C C3 0.18564(12) -0.15600(15) 0.06326(12) 0.0427(3) Uani d . 1 1 . .
H H3 0.1572 -0.2430 0.0846 0.051 Uiso d R 1 1 . .
C C4 0.27814(13) -0.14390(18) -0.01784(13) 0.0486(4) Uani d . 1 1 . .
H H4 0.3133 -0.2279 -0.0517 0.058 Uiso d R 1 1 . .
C C5 0.31867(13) -0.01409(18) -0.04859(12) 0.0486(4) Uani d . 1 1 . .
H H5 0.3823 -0.0122 -0.1044 0.058 Uiso d R 1 1 . .
C C6 0.26890(12) 0.10617(16) -0.00077(12) 0.0424(3) Uani d . 1 1 . .
C C7 0.03494(12) -0.05473(16) 0.20282(12) 0.0433(3) Uani d . 1 1 . .
H H7A 0.0167 -0.1534 0.2140 0.065 Uiso d R 1 1 . .
H H7B -0.0443 -0.0070 0.1664 0.065 Uiso d R 1 1 . .
H H7C 0.0677 -0.0137 0.2860 0.065 Uiso d R 1 1 . .
C C8 0.31144(16) 0.24532(19) -0.04330(15) 0.0611(4) Uani d . 1 1 . .
H H8A 0.3816 0.2805 0.0196 0.092 Uiso d R 1 1 . .
H H8B 0.2389 0.3103 -0.0506 0.092 Uiso d R 1 1 . .
H H8C 0.3416 0.2360 -0.1266 0.092 Uiso d R 1 1 . .
C C9 0.12520(17) 0.53273(16) 0.33939(17) 0.0592(4) Uani d . 1 1 . .
H H9A 0.2166 0.5218 0.3727 0.089 Uiso d R 1 1 . .
H H9B 0.0743 0.5296 0.4104 0.089 Uiso d R 1 1 . .
H H9C 0.1118 0.6222 0.2953 0.089 Uiso d R 1 1 . .
C C10 -0.05069(17) 0.4308(2) 0.1985(2) 0.0774(6) Uani d . 1 1 . .
H H10A -0.0921 0.3408 0.2075 0.116 Uiso d PR 0.50 1 A 1
H H10B -0.0597 0.4563 0.1078 0.116 Uiso d PR 0.50 1 A 1
H H10C -0.0918 0.5016 0.2457 0.116 Uiso d PR 0.50 1 A 1
H H10D -0.0655 0.5254 0.1656 0.116 Uiso d PR 0.50 1 A 2
H H10E -0.0806 0.3739 0.1232 0.116 Uiso d PR 0.50 1 A 2
H H10F -0.0941 0.4219 0.2744 0.116 Uiso d PR 0.50 1 A 2
B B1 0.16980(14) 0.31610(16) 0.21743(14) 0.0391(3) Uani d . 1 1 . .
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 0.0000 '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'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
0.00 -1.00 0.00 0.0200
0.00 1.00 0.00 0.0200
-1.00 0.00 1.00 0.1750
1.00 0.00 -1.00 0.1750
1.00 0.00 1.00 0.2650
-1.00 0.00 -1.00 0.2650
0.00 0.00 -1.00 0.2600
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C1 N1 B1 . 129.99(11)
C1 N1 H1N . 109.3(10)
B1 N1 H1N . 119.5(10)
B1 N2 C9 . 123.43(12)
B1 N2 C10 . 124.61(13)
C9 N2 C10 . 111.96(13)
C6 C1 C2 . 119.99(12)
C6 C1 N1 . 121.37(12)
C2 C1 N1 . 118.48(11)
C3 C2 C1 . 119.36(11)
C3 C2 C7 . 120.28(13)
C1 C2 C7 . 120.35(12)
C2 C3 C4 . 121.04(14)
C2 C3 H3 . 118.8
C4 C3 H3 . 120.2
C5 C4 C3 . 119.28(13)
C5 C4 H4 . 121.4
C3 C4 H4 . 119.3
C4 C5 C6 . 121.76(12)
C4 C5 H5 . 115.6
C6 C5 H5 . 122.7
C5 C6 C1 . 118.55(13)
C5 C6 C8 . 119.43(12)
C1 C6 C8 . 121.98(13)
C2 C7 H7A . 109.5
C2 C7 H7B . 109.4
H7A C7 H7B . 109.5
C2 C7 H7C . 109.5
H7A C7 H7C . 109.5
H7B C7 H7C . 109.5
C6 C8 H8A . 109.5
C6 C8 H8B . 109.5
H8A C8 H8B . 109.5
C6 C8 H8C . 109.5
H8A C8 H8C . 109.5
H8B C8 H8C . 109.5
N2 C9 H9A . 109.5
N2 C9 H9B . 109.6
H9A C9 H9B . 109.5
N2 C9 H9C . 109.3
H9A C9 H9C . 109.4
H9B C9 H9C . 109.5
N2 C10 H10A . 109.4
N2 C10 H10B . 109.6
H10A C10 H10B . 109.5
N2 C10 H10C . 109.4
H10A C10 H10C . 109.5
H10B C10 H10C . 109.5
N2 C10 H10D . 106.8
H10A C10 H10D . 143.7
H10B C10 H10D . 55.4
H10C C10 H10D . 58.2
N2 C10 H10E . 116.9
H10A C10 H10E . 59.2
H10B C10 H10E . 51.1
H10C C10 H10E . 133.5
H10D C10 H10E . 102.5
N2 C10 H10F . 103.5
H10A C10 H10F . 65.1
H10B C10 H10F . 146.0
H10C C10 H10F . 50.0
H10D C10 H10F . 107.6
H10E C10 H10F . 118.8
N2 B1 N1 . 117.45(12)
N2 B1 B1 2 120.76(10)
N1 B1 B1 2 121.80(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.4237(16) yes
N1 B1 . 1.4290(19) yes
N1 H1N . 0.871(12) ?
N2 B1 . 1.4197(19) yes
N2 C9 . 1.453(2) ?
N2 C10 . 1.456(2) ?
C1 C6 . 1.4043(17) ?
C1 C2 . 1.4049(18) ?
C2 C3 . 1.3855(18) ?
C2 C7 . 1.5026(17) ?
C3 C4 . 1.3864(19) ?
C3 H3 . 0.9283 ?
C4 C5 . 1.374(2) ?
C4 H4 . 0.9777 ?
C5 C6 . 1.394(2) ?
C5 H5 . 0.9512 ?
C6 C8 . 1.501(2) ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9801 ?
C7 H7C . 0.9800 ?
C8 H8A . 0.9803 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9798 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9801 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C10 H10D . 0.9800 ?
C10 H10E . 0.9800 ?
C10 H10F . 0.9800 ?
B1 B1 2 1.727(3) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N C3 3 0.871(12) 2.773(13) 3.5631(18) 151.6(13)
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_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
C6 C1 N1 B1 . . -69.21(18)
C1 N1 B1 B1 . 2 1.8(2)
N1 B1 B1 N1 2 2 -67.7(3)
N2 B1 B1 N2 2 3 173.69(16)
