#------------------------------------------------------------------------------
#$Date: 2021-12-19 00:54:45 +0200 (Sun, 19 Dec 2021) $
#$Revision: 271516 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/94/7129422.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_7129422
loop_
_publ_author_name
'Vogler, Daniel'
'Haas, Lea'
'Wolf, Nina'
'Kaifer, Elisabeth'
'Himmel, Hans-Jörg'
_publ_section_title
;
 Derivatization of an especially electron-rich diborane
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06359F
_journal_year                    2022
_chemical_formula_moiety         'C14 H24 B2 Br2 N6, C2 H4 Cl4'
_chemical_formula_sum            'C16 H28 B2 Br2 Cl4 N6'
_chemical_formula_weight         627.68
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-05 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.646(2)
_cell_length_b                   12.3273(11)
_cell_length_c                   8.5158(7)
_cell_measurement_reflns_used    8246
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.44
_cell_volume                     2377.3(4)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       'APEX3 v2018.7-2 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PhotonIII detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker, D8-Venture, dual Source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23126
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.313
_diffrn_reflns_theta_min         2.442
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms 3.0'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.877
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0970 before and 0.0781 after correction. The Ratio of minimum to maximum transmission is 0.8219. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_description       plank
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.986
_refine_diff_density_min         -1.116
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         3090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0324
_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)+(0.0105P)²+3.3923P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0668
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2489
_reflns_number_total             3090
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06359f2.cif
_cod_data_source_block           mo_dv122_0ma
_cod_database_code               7129422
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Others
 Fixed Sof: H10A(0.5) H10B(0.5) H9A(0.5) H9B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
 C10(H10A,H10B), C9(H9A,H9B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.59575(2) 0.41618(2) 0.27672(3) 0.01602(7) Uani 1 1 d . . . . .
Cl3 Cl 0.42207(4) 0.250000 0.22022(12) 0.0266(2) Uani 1 2 d S T P . .
Cl4 Cl 0.42317(6) 0.250000 0.56023(14) 0.0750(6) Uani 1 2 d S T P . .
N1 N 0.58774(9) 0.34228(17) 0.6055(2) 0.0131(4) Uani 1 1 d . . . . .
N3 N 0.69257(9) 0.34232(17) 0.4853(2) 0.0128(4) Uani 1 1 d . . . . .
C1 C 0.56866(12) 0.4482(2) 0.6641(3) 0.0171(5) Uani 1 1 d . . . . .
H1A H 0.531304 0.469385 0.612087 0.021 Uiso 1 1 calc R . . . .
H1B H 0.598886 0.503471 0.638579 0.021 Uiso 1 1 calc R . . . .
C2 C 0.55948(12) 0.4440(2) 0.8411(3) 0.0183(6) Uani 1 1 d . . . . .
H2A H 0.597852 0.433126 0.894542 0.022 Uiso 1 1 calc R . . . .
H2B H 0.542385 0.513337 0.878179 0.022 Uiso 1 1 calc R . . . .
C3 C 0.51819(12) 0.3514(2) 0.8803(3) 0.0183(5) Uani 1 1 d . . . . .
H3A H 0.515709 0.343015 0.995676 0.022 Uiso 1 1 calc R . . . .
H3B H 0.478140 0.368280 0.840497 0.022 Uiso 1 1 calc R . . . .
N2 N 0.53881(13) 0.250000 0.8103(3) 0.0135(6) Uani 1 2 d S T P . .
C4 C 0.57007(15) 0.250000 0.6757(4) 0.0129(7) Uani 1 2 d S T P . .
C5 C 0.71912(12) 0.4478(2) 0.5186(3) 0.0199(6) Uani 1 1 d . . . . .
H5A H 0.710568 0.468707 0.628543 0.024 Uiso 1 1 calc R . . . .
H5B H 0.701659 0.503404 0.448694 0.024 Uiso 1 1 calc R . . . .
C6 C 0.78540(12) 0.4437(2) 0.4937(3) 0.0227(6) Uani 1 1 d . . . . .
H6A H 0.794155 0.433306 0.380790 0.027 Uiso 1 1 calc R . . . .
H6B H 0.803456 0.512901 0.527764 0.027 Uiso 1 1 calc R . . . .
C7 C 0.81104(12) 0.3512(2) 0.5872(3) 0.0215(6) Uani 1 1 d . . . . .
H7A H 0.853729 0.344308 0.564133 0.026 Uiso 1 1 calc R . . . .
H7B H 0.806468 0.365994 0.700782 0.026 Uiso 1 1 calc R . . . .
N4 N 0.78095(13) 0.250000 0.5472(4) 0.0162(6) Uani 1 2 d S T P . .
C8 C 0.72333(15) 0.250000 0.5069(4) 0.0126(7) Uani 1 2 d S T P . .
C10 C 0.46578(17) 0.250000 0.3925(5) 0.0262(9) Uani 1 2 d S T P . .
H10A H 0.491500 0.185065 0.392549 0.031 Uiso 0.5 1 calc R . . . .
H10B H 0.491500 0.314935 0.392549 0.031 Uiso 0.5 1 calc R . . . .
B1 B 0.62655(12) 0.3195(2) 0.4626(3) 0.0115(5) Uani 1 1 d . . . . .
Cl1 Cl 0.78626(5) 0.250000 1.12192(12) 0.0303(2) Uani 1 2 d S T P . .
Cl2 Cl 0.69391(5) 0.250000 0.88567(12) 0.0315(3) Uani 1 2 d S T P . .
C9 C 0.70957(17) 0.250000 1.0891(4) 0.0207(8) Uani 1 2 d S T P . .
H9A H 0.691799 0.315002 1.138359 0.025 Uiso 0.5 1 calc R . . . .
H9B H 0.691799 0.184998 1.138359 0.025 Uiso 0.5 1 calc R . . . .
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 B1 127.3(2) . . ?
C4 N1 C1 121.0(2) . . ?
C4 N1 B1 111.7(2) . . ?
C5 N3 B1 126.1(2) . . ?
C8 N3 C5 120.9(2) . . ?
C8 N3 B1 111.5(2) . . ?
N1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
N1 C1 C2 110.4(2) . . ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 C1 109.2(2) . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
N2 C3 C2 111.0(2) . . ?
N2 C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
C3 N2 C3 117.6(3) . 7_565 ?
C4 N2 C3 120.96(14) . 7_565 ?
C4 N2 C3 120.96(14) . . ?
N1 C4 N1 115.4(3) 7_565 . ?
N1 C4 N2 122.30(15) . . ?
N1 C4 N2 122.30(15) 7_565 . ?
N3 C5 H5A 109.6 . . ?
N3 C5 H5B 109.6 . . ?
N3 C5 C6 110.5(2) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 C5 109.5(2) . . ?
C7 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.2 . . ?
N4 C7 C6 110.1(2) . . ?
N4 C7 H7A 109.6 . . ?
N4 C7 H7B 109.6 . . ?
C7 N4 C7 117.2(3) . 7_565 ?
C8 N4 C7 120.68(15) . 7_565 ?
C8 N4 C7 120.68(15) . . ?
N3 C8 N3 115.3(3) 7_565 . ?
N3 C8 N4 122.34(16) . . ?
N3 C8 N4 122.34(16) 7_565 . ?
Cl3 C10 H10A 109.2 . . ?
Cl3 C10 H10B 109.2 . . ?
Cl4 C10 Cl3 112.0(2) . . ?
Cl4 C10 H10A 109.2 . . ?
Cl4 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N1 B1 Br1 107.73(16) . . ?
N1 B1 N3 115.3(2) . . ?
N1 B1 B1 100.62(13) . 7_565 ?
N3 B1 Br1 108.32(17) . . ?
N3 B1 B1 100.59(13) . 7_565 ?
B1 B1 Br1 124.58(8) 7_565 . ?
Cl1 C9 Cl2 110.7(2) . . ?
Cl1 C9 H9A 109.5 . . ?
Cl1 C9 H9B 109.5 . . ?
Cl2 C9 H9A 109.5 . . ?
Cl2 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 B1 2.101(3) . ?
Cl3 C10 1.770(4) . ?
Cl4 C10 1.724(4) . ?
N1 C1 1.463(3) . ?
N1 C4 1.346(3) . ?
N1 B1 1.527(3) . ?
N3 C5 1.461(3) . ?
N3 C8 1.347(3) . ?
N3 B1 1.534(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.523(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.512(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 N2 1.462(3) . ?
N2 C4 1.347(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.517(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.507(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N4 1.461(3) . ?
N4 C8 1.349(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
B1 B1 1.712(6) 7_565 ?
Cl1 C9 1.759(4) . ?
Cl2 C9 1.768(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
