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#$Date: 2025-08-21 00:40:30 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301839 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/11/4331184.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_4331184
loop_
_publ_author_name
'Adam C. Malcolm'
'Kyle J. Sabourin'
'Robert McDonald'
'Michael J. Ferguson'
'Eric Rivard'
_publ_contact_author_address
;
Department of Chemistry
University of Alberta
Edmonton
AB T6G 2G2
CANADA
;
_publ_contact_author_email       ERIVARD@UALBERTA.CA
_publ_contact_author_name        'E. Rivard'
_publ_section_title
;
 Donor-Acceptor Complexation and Dehydrogenation Chemistry of Aminoboranes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              12905
_journal_page_last               12916
_journal_paper_doi               10.1021/ic3018997
_journal_volume                  51
_journal_year                    2012
_chemical_formula_moiety         'C9 H21 B2 N3'
_chemical_formula_sum            'C9 H21 B2 N3'
_chemical_formula_weight         192.91
_chemical_name_common            7
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4065(6)
_cell_length_b                   10.0395(8)
_cell_length_c                   14.3963(11)
_cell_measurement_reflns_used    2254
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.70
_cell_measurement_theta_min      2.47
_cell_volume                     1215.01(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXD (Schneider & Sheldrick, 2002)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10623
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.9812
_exptl_absorpt_correction_T_min  0.9770
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.055
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.6(19)
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2782
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0386P)²+0.1196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0886
_reflns_number_gt                2418
_reflns_number_total             2782
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic3018997_si_002_4.cif
_cod_data_source_block           riv11d4
_cod_database_code               4331184
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.15568(12) 0.49584(10) 0.25796(7) 0.0296(2) Uani 1 1 d .
N2 N 0.28538(13) 0.34062(11) 0.13452(7) 0.0293(3) Uani 1 1 d .
N3 N 0.26325(13) -0.03093(11) 0.00571(8) 0.0333(3) Uani 1 1 d .
C1 C 0.17334(19) 0.63168(14) 0.29718(11) 0.0417(4) Uani 1 1 d .
H1A H 0.1684 0.6974 0.2469 0.050 Uiso 1 1 calc R
H1B H 0.2760 0.6388 0.3290 0.050 Uiso 1 1 calc R
H1C H 0.0872 0.6486 0.3415 0.050 Uiso 1 1 calc R
C2 C -0.00301(16) 0.48861(15) 0.21372(10) 0.0393(3) Uani 1 1 d .
H2A H -0.0096 0.5548 0.1638 0.047 Uiso 1 1 calc R
H2B H -0.0853 0.5069 0.2602 0.047 Uiso 1 1 calc R
H2C H -0.0191 0.3994 0.1878 0.047 Uiso 1 1 calc R
C3 C 0.36309(16) 0.23369(13) 0.16927(9) 0.0306(3) Uani 1 1 d .
H3 H 0.4227 0.2448 0.2248 0.037 Uiso 1 1 calc R
C4 C 0.36063(16) 0.11071(13) 0.12894(9) 0.0305(3) Uani 1 1 d .
H4 H 0.4197 0.0398 0.1557 0.037 Uiso 1 1 calc R
C5 C 0.27050(15) 0.08830(13) 0.04746(9) 0.0280(3) Uani 1 1 d .
C6 C 0.18965(16) 0.20082(13) 0.01220(9) 0.0328(3) Uani 1 1 d .
H6 H 0.1261 0.1925 -0.0421 0.039 Uiso 1 1 calc R
C7 C 0.20193(17) 0.32102(14) 0.05524(9) 0.0333(3) Uani 1 1 d .
H7 H 0.1491 0.3952 0.0282 0.040 Uiso 1 1 calc R
C8 C 0.3416(2) -0.14718(15) 0.04545(12) 0.0502(4) Uani 1 1 d .
H8A H 0.4538 -0.1265 0.0572 0.060 Uiso 1 1 calc R
H8B H 0.3342 -0.2219 0.0019 0.060 Uiso 1 1 calc R
H8C H 0.2896 -0.1712 0.1040 0.060 Uiso 1 1 calc R
C9 C 0.15528(17) -0.05308(15) -0.07181(10) 0.0393(3) Uani 1 1 d .
H9A H 0.1791 0.0105 -0.1215 0.047 Uiso 1 1 calc R
H9B H 0.0453 -0.0406 -0.0509 0.047 Uiso 1 1 calc R
H9C H 0.1688 -0.1441 -0.0952 0.047 Uiso 1 1 calc R
B1 B 0.29171(19) 0.48089(16) 0.18293(11) 0.0324(3) Uani 1 1 d .
H1BA H 0.4094(16) 0.4862(13) 0.2186(9) 0.031(4) Uiso 1 1 d .
H1BB H 0.2745(18) 0.5571(15) 0.1286(10) 0.040(4) Uiso 1 1 d .
B2 B 0.1644(2) 0.39017(18) 0.34119(12) 0.0398(4) Uani 1 1 d .
H2BA H 0.148(2) 0.2873(15) 0.3107(11) 0.049(4) Uiso 1 1 d .
H2BB H 0.0653(19) 0.4191(15) 0.3903(11) 0.046(4) Uiso 1 1 d .
H2BC H 0.287(2) 0.4030(17) 0.3715(12) 0.057(5) Uiso 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
C2 N1 C1 107.40(11)
C2 N1 B1 110.70(11)
C1 N1 B1 105.97(11)
C2 N1 B2 109.31(11)
C1 N1 B2 108.63(11)
B1 N1 B2 114.53(11)
C3 N2 C7 116.53(11)
C3 N2 B1 122.04(11)
C7 N2 B1 121.43(11)
C5 N3 C9 120.56(11)
C5 N3 C8 121.23(12)
C9 N3 C8 117.42(11)
N2 C3 C4 123.60(12)
C3 C4 C5 120.33(12)
N3 C5 C6 122.07(11)
N3 C5 C4 122.56(12)
C6 C5 C4 115.37(11)
C7 C6 C5 120.61(12)
N2 C7 C6 123.52(12)
N2 B1 N1 111.32(11)
N1 B1 H1BA 108.8(7)
N1 B1 H1BB 108.9(8)
N2 B1 H1BA 106.1(7)
N2 B1 H1BB 107.6(8)
H1BA B1 H1BB 114.1(11)
N1 B2 H2BA 108.0(8)
N1 B2 H2BB 105.3(8)
N1 B2 H2BC 104.8(9)
H2BA B2 H2BB 112.9(12)
H2BA B2 H2BC 111.3(12)
H2BB B2 H2BC 113.8(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.4800(17)
N1 C1 1.4835(16)
N1 B1 1.5801(18)
N1 B2 1.6020(19)
N2 C3 1.3527(16)
N2 C7 1.3540(17)
N2 B1 1.5722(19)
N3 C5 1.3408(16)
N3 C9 1.4556(17)
N3 C8 1.4573(18)
C3 C4 1.3645(18)
C4 C5 1.4144(17)
C5 C6 1.4127(17)
C6 C7 1.3604(19)
B1 H1BA 1.115(14)
B1 H1BB 1.104(15)
B2 H2BA 1.130(15)
B2 H2BB 1.130(16)
B2 H2BC 1.126(18)
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
C7 N2 C3 C4 -0.08(19)
B1 N2 C3 C4 -179.78(12)
N2 C3 C4 C5 -1.6(2)
C9 N3 C5 C6 -7.63(19)
C8 N3 C5 C6 -177.19(13)
C9 N3 C5 C4 173.11(12)
C8 N3 C5 C4 3.5(2)
C3 C4 C5 N3 -179.44(13)
C3 C4 C5 C6 1.25(18)
N3 C5 C6 C7 -178.73(12)
C4 C5 C6 C7 0.58(19)
C3 N2 C7 C6 2.05(19)
B1 N2 C7 C6 -178.25(13)
C5 C6 C7 N2 -2.3(2)
C3 N2 B1 N1 -88.48(15)
C7 N2 B1 N1 91.83(15)
C2 N1 B1 N2 -63.14(15)
C1 N1 B1 N2 -179.28(11)
B2 N1 B1 N2 60.99(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139138101
