#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:08:22 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178770 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/24/4102474.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_4102474
loop_
_publ_author_name
'Scott R. Daly'
'Brian J. Bellott'
'Do Young Kim'
'Gregory S. Girolami'
_publ_contact_author_address
;Department of Chemistry, Box 4-6
University of Illinois at Urbana-Champaign
600 South Mathews
Urbana, IL 61801
;
_publ_contact_author_email       girolami@scs.illinois.edu
_publ_contact_author_fax         '(217) 333-2685'
_publ_contact_author_name        'Gregory S. Girolami'
_publ_contact_author_phone       ' (217) 333-2729'
_publ_section_title
;
 Synthesis of the Long-Sought Unsubstituted Aminodiboranate
 Na(H3B-NH2-BH3) and Its N-Alkyl Analogs
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7254
_journal_page_last               7255
_journal_paper_doi               10.1021/ja1016427
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C8 H22 B2 N Na O2'
_chemical_formula_weight         208.88
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.583(4)
_cell_angle_beta                 101.318(4)
_cell_angle_gamma                101.330(4)
_cell_formula_units_Z            2
_cell_length_a                   7.781(2)
_cell_length_b                   9.048(3)
_cell_length_c                   10.230(3)
_cell_measurement_reflns_used    828
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.24
_cell_volume                     627.5(3)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0701
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7712
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.98012
_exptl_absorpt_correction_T_min  0.93371
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   XPREP/SHELXTL
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0525
_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)+(0.0907P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1586
_reflns_number_gt                1599
_reflns_number_total             2923
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1016427_si_002_1.cif
_cod_data_source_block           f93d_face
_cod_database_code               4102474
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Na1 Na 0.09483(11) 1.14755(9) 0.70878(8) 0.0354(3) Uani 1 1 d .
B1 B 0.1941(4) 0.8901(3) 0.5484(3) 0.0339(6) Uani 1 1 d .
H11 H 0.296(3) 0.963(3) 0.661(2) 0.041(6) Uiso 1 1 d .
H12 H 0.197(3) 0.973(2) 0.486(2) 0.028(5) Uiso 1 1 d .
H13 H 0.054(3) 0.861(2) 0.558(2) 0.033(5) Uiso 1 1 d .
B2 B 0.0944(4) 0.6225(3) 0.3035(3) 0.0366(6) Uani 1 1 d .
H21 H 0.110(3) 0.694(3) 0.235(2) 0.041(6) Uiso 1 1 d .
H22 H -0.045(3) 0.609(3) 0.318(2) 0.048(6) Uiso 1 1 d .
H23 H 0.112(3) 0.500(3) 0.249(2) 0.051(6) Uiso 1 1 d .
N1 N 0.2394(2) 0.72390(19) 0.46284(17) 0.0296(4) Uani 1 1 d .
C1 C 0.2445(3) 0.6224(3) 0.5496(2) 0.0406(6) Uani 1 1 d .
H1A H 0.2296 0.5052 0.4853 0.049 Uiso 1 1 calc R
H1B H 0.1457 0.6260 0.5977 0.049 Uiso 1 1 calc R
C2 C 0.4333(3) 0.7021(3) 0.6645(3) 0.0524(7) Uani 1 1 d .
H2A H 0.4256 0.7816 0.7588 0.063 Uiso 1 1 calc R
H2B H 0.4828 0.6161 0.6821 0.063 Uiso 1 1 calc R
C3 C 0.5547(3) 0.7924(3) 0.5996(3) 0.0478(6) Uani 1 1 d .
H3A H 0.6014 0.9133 0.6635 0.057 Uiso 1 1 calc R
H3B H 0.6603 0.7483 0.5881 0.057 Uiso 1 1 calc R
C4 C 0.4306(3) 0.7584(3) 0.4517(2) 0.0364(5) Uani 1 1 d .
H4A H 0.4611 0.8561 0.4291 0.044 Uiso 1 1 calc R
H4B H 0.4443 0.6614 0.3730 0.044 Uiso 1 1 calc R
O1 O 0.3573(2) 1.36449(18) 0.88662(16) 0.0450(4) Uani 1 1 d .
C11 C 0.3238(4) 1.5002(4) 0.9952(3) 0.0739(9) Uani 1 1 d .
H11A H 0.3091 1.4724 1.0781 0.089 Uiso 1 1 calc R
H11B H 0.2079 1.5170 0.9518 0.089 Uiso 1 1 calc R
C12 C 0.5259(4) 1.3448(3) 0.9491(3) 0.0573(7) Uani 1 1 d .
H12A H 0.5535 1.2543 0.8738 0.069 Uiso 1 1 calc R
H12B H 0.5156 1.3131 1.0307 0.069 Uiso 1 1 calc R
O2 O 0.0173(2) 1.04560(18) 0.88390(16) 0.0461(4) Uani 1 1 d .
C21 C 0.0139(5) 0.8836(3) 0.8758(3) 0.0727(9) Uani 1 1 d .
H21A H -0.1132 0.8091 0.8257 0.087 Uiso 1 1 calc R
H21B H 0.0917 0.8392 0.8144 0.087 Uiso 1 1 calc R
C22 C -0.0749(4) 1.1208(3) 0.9872(3) 0.0625(8) Uani 1 1 d .
H22A H -0.0566 1.2381 1.0026 0.075 Uiso 1 1 calc R
H22B H -0.2081 1.0628 0.9447 0.075 Uiso 1 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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
O1 Na1 O2 93.58(7) . .
O1 Na1 B1 110.45(8) . .
O2 Na1 B1 97.85(7) . .
O1 Na1 B2 91.23(7) . 2_576
O2 Na1 B2 108.86(7) . 2_576
B1 Na1 B2 144.47(8) . 2_576
O1 Na1 B1 135.68(7) . 2_576
O2 Na1 B1 120.85(8) . 2_576
B1 Na1 B1 92.80(8) . 2_576
B2 Na1 B1 53.57(7) 2_576 2_576
O1 Na1 Na1 141.73(5) . 2_576
O2 Na1 Na1 118.99(5) . 2_576
B1 Na1 Na1 49.63(6) . 2_576
B2 Na1 Na1 96.00(6) 2_576 2_576
B1 Na1 Na1 43.17(5) 2_576 2_576
O1 Na1 H11 88.1(5) . .
O2 Na1 H11 88.7(5) . .
B1 Na1 H11 24.9(5) . .
B2 Na1 H11 162.5(5) 2_576 .
B1 Na1 H11 117.2(5) 2_576 .
Na1 Na1 H11 74.2(5) 2_576 .
O1 Na1 H12 108.3(4) . .
O2 Na1 H12 122.8(4) . .
B1 Na1 H12 25.1(4) . .
B2 Na1 H12 122.3(4) 2_576 .
B1 Na1 H12 77.5(4) 2_576 .
Na1 Na1 H12 38.2(4) 2_576 .
H11 Na1 H12 42.3(6) . .
O1 Na1 H13 131.7(5) . .
O2 Na1 H13 84.4(5) . .
B1 Na1 H13 24.4(5) . .
B2 Na1 H13 135.0(5) 2_576 .
B1 Na1 H13 82.4(5) 2_576 .
Na1 Na1 H13 43.5(5) 2_576 .
H11 Na1 H13 43.8(7) . .
H12 Na1 H13 41.6(6) . .
N1 B1 Na1 172.45(16) . .
N1 B1 Na1 94.71(12) . 2_576
Na1 B1 Na1 87.20(8) . 2_576
N1 B1 H11 110.4(11) . .
Na1 B1 H11 68.9(10) . .
Na1 B1 H11 153.8(10) 2_576 .
N1 B1 H12 111.5(9) . .
Na1 B1 H12 75.4(9) . .
Na1 B1 H12 52.5(9) 2_576 .
H11 B1 H12 108.6(14) . .
N1 B1 H13 109.9(10) . .
Na1 B1 H13 64.2(10) . .
Na1 B1 H13 65.9(10) 2_576 .
H11 B1 H13 110.2(15) . .
H12 B1 H13 106.1(14) . .
N1 B2 Na1 101.09(13) . 2_576
N1 B2 H21 110.1(11) . .
Na1 B2 H21 55.9(10) 2_576 .
N1 B2 H22 107.7(12) . .
Na1 B2 H22 58.2(11) 2_576 .
H21 B2 H22 108.0(16) . .
N1 B2 H23 110.7(12) . .
Na1 B2 H23 148.2(12) 2_576 .
H21 B2 H23 110.1(16) . .
H22 B2 H23 110.2(16) . .
C1 N1 C4 101.93(16) . .
C1 N1 B1 110.62(17) . .
C4 N1 B1 111.62(16) . .
C1 N1 B2 111.85(16) . .
C4 N1 B2 110.70(17) . .
B1 N1 B2 109.92(16) . .
N1 C1 C2 105.11(17) . .
N1 C1 H1A 110.7 . .
C2 C1 H1A 110.7 . .
N1 C1 H1B 110.7 . .
C2 C1 H1B 110.7 . .
H1A C1 H1B 108.8 . .
C3 C2 C1 105.42(19) . .
C3 C2 H2A 110.7 . .
C1 C2 H2A 110.7 . .
C3 C2 H2B 110.7 . .
C1 C2 H2B 110.7 . .
H2A C2 H2B 108.8 . .
C4 C3 C2 104.73(18) . .
C4 C3 H3A 110.8 . .
C2 C3 H3A 110.8 . .
C4 C3 H3B 110.8 . .
C2 C3 H3B 110.8 . .
H3A C3 H3B 108.9 . .
N1 C4 C3 106.17(18) . .
N1 C4 H4A 110.5 . .
C3 C4 H4A 110.5 . .
N1 C4 H4B 110.5 . .
C3 C4 H4B 110.5 . .
H4A C4 H4B 108.7 . .
C12 O1 C11 108.58(18) . .
C12 O1 Na1 126.15(13) . .
C11 O1 Na1 116.71(14) . .
O1 C11 C12 111.9(2) . 2_687
O1 C11 H11A 109.2 . .
C12 C11 H11A 109.2 2_687 .
O1 C11 H11B 109.2 . .
C12 C11 H11B 109.2 2_687 .
H11A C11 H11B 107.9 . .
O1 C12 C11 110.9(2) . 2_687
O1 C12 H12A 109.5 . .
C11 C12 H12A 109.5 2_687 .
O1 C12 H12B 109.5 . .
C11 C12 H12B 109.5 2_687 .
H12A C12 H12B 108.1 . .
C21 O2 C22 109.51(18) . .
C21 O2 Na1 124.83(14) . .
C22 O2 Na1 123.97(13) . .
C22 C21 O2 114.5(2) 2_577 .
C22 C21 H21A 108.6 2_577 .
O2 C21 H21A 108.6 . .
C22 C21 H21B 108.6 2_577 .
O2 C21 H21B 108.6 . .
H21A C21 H21B 107.6 . .
C21 C22 O2 113.6(2) 2_577 .
C21 C22 H22A 108.8 2_577 .
O2 C22 H22A 108.8 . .
C21 C22 H22B 108.8 2_577 .
O2 C22 H22B 108.8 . .
H22A C22 H22B 107.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Na1 O1 2.3816(17) .
Na1 O2 2.4179(17) .
Na1 B1 2.666(3) .
Na1 B2 2.799(3) 2_576
Na1 B1 2.968(3) 2_576
Na1 Na1 3.8912(18) 2_576
Na1 H11 2.49(2) .
Na1 H12 2.623(19) .
Na1 H13 2.401(19) .
B1 N1 1.585(3) .
B1 Na1 2.968(3) 2_576
B1 H11 1.13(2) .
B1 H12 1.149(19) .
B1 H13 1.10(2) .
B2 N1 1.594(3) .
B2 Na1 2.799(3) 2_576
B2 H21 1.12(2) .
B2 H22 1.11(2) .
B2 H23 1.09(2) .
N1 C1 1.494(2) .
N1 C4 1.495(3) .
C1 C2 1.531(3) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C3 1.530(3) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.512(3) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
O1 C12 1.417(3) .
O1 C11 1.430(3) .
C11 C12 1.472(4) 2_687
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C11 1.472(4) 2_687
C12 H12A 0.9900 .
C12 H12B 0.9900 .
O2 C21 1.432(3) .
O2 C22 1.433(3) .
C21 C22 1.407(4) 2_577
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C21 1.407(4) 2_577
C22 H22A 0.9900 .
C22 H22B 0.9900 .
