#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:08:22 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178770 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/24/4102477.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_4102477
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            'C6 H20 B2 N Na O2'
_chemical_formula_weight         182.84
_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                106.786(4)
_cell_angle_beta                 98.357(2)
_cell_angle_gamma                110.880(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9953(12)
_cell_length_b                   8.9580(13)
_cell_length_c                   9.566(2)
_cell_measurement_reflns_used    1880
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.71
_cell_measurement_theta_min      2.31
_cell_volume                     588.79(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker TWINABS'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4486
_diffrn_reflns_theta_full        25.71
_diffrn_reflns_theta_max         25.71
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.745262
_exptl_absorpt_correction_T_min  0.659471
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   TWINABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.031
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2245
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0994P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1751
_reflns_number_gt                1357
_reflns_number_total             2245
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1016427_si_002_4.cif
_cod_data_source_block           f94d_abs
_cod_original_cell_volume        588.78(18)
_cod_database_code               4102477
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.07001(12) 0.65053(10) 0.20505(10) 0.0618(4) Uani 1 1 d . . .
B1 B -0.1629(4) 0.6084(3) -0.0684(3) 0.0632(8) Uani 1 1 d D . .
H11 H -0.009(2) 0.644(3) -0.053(2) 0.065(6) Uiso 1 1 d D . .
H12 H -0.218(3) 0.524(3) -0.003(2) 0.067(7) Uiso 1 1 d D . .
H13 H -0.239(3) 0.536(3) -0.193(2) 0.083(8) Uiso 1 1 d D . .
B2 B -0.0503(5) 0.8983(3) 0.1610(3) 0.0674(9) Uani 1 1 d D A .
H21 H 0.097(2) 0.922(3) 0.161(3) 0.068(7) Uiso 1 1 d D . .
H22 H -0.094(3) 0.831(3) 0.242(3) 0.096(9) Uiso 1 1 d D . .
H23 H -0.062(3) 1.025(3) 0.199(3) 0.077(7) Uiso 1 1 d D . .
N1 N -0.1836(3) 0.7818(2) -0.0050(2) 0.0576(6) Uani 1 1 d D . .
H1 H -0.146(3) 0.839(3) -0.059(3) 0.052(6) Uiso 1 1 d . . .
C1A C -0.3838(13) 0.7517(17) -0.0326(18) 0.062(4) Uani 0.494(7) 1 d PD A 1
H1A1 H -0.4362 0.6873 0.0308 0.074 Uiso 0.494(7) 1 calc PR A 1
H1A2 H -0.4467 0.6732 -0.1398 0.074 Uiso 0.494(7) 1 calc PR A 1
C2A C -0.4458(8) 0.8990(8) -0.0064(7) 0.078(2) Uani 0.494(7) 1 d PD A 1
H2AA H -0.3730 0.9885 0.0937 0.117 Uiso 0.494(7) 1 calc PR A 1
H2AB H -0.5784 0.8548 -0.0110 0.117 Uiso 0.494(7) 1 calc PR A 1
H2AC H -0.4255 0.9477 -0.0853 0.117 Uiso 0.494(7) 1 calc PR A 1
C1B C -0.3736(13) 0.755(2) 0.0016(16) 0.071(4) Uani 0.506(7) 1 d PD A 2
H1C H -0.3774 0.8652 0.0573 0.086 Uiso 0.506(7) 1 calc PR A 2
H1D H -0.4209 0.6738 0.0530 0.086 Uiso 0.506(7) 1 calc PR A 2
C2B C -0.4874(9) 0.6822(9) -0.1613(10) 0.088(2) Uani 0.506(7) 1 d PD A 2
H2BA H -0.4215 0.7495 -0.2166 0.132 Uiso 0.506(7) 1 calc PR A 2
H2BB H -0.6084 0.6872 -0.1654 0.132 Uiso 0.506(7) 1 calc PR A 2
H2BC H -0.5065 0.5625 -0.2079 0.132 Uiso 0.506(7) 1 calc PR A 2
O1 O 0.3356(3) 0.8613(2) 0.4036(2) 0.0852(6) Uani 1 1 d D . .
C11 C 0.3406(5) 1.0210(4) 0.4927(5) 0.1312(16) Uani 1 1 d . . .
H11A H 0.3451 1.0901 0.4279 0.157 Uiso 1 1 calc R . .
H11B H 0.2220 0.9977 0.5208 0.157 Uiso 1 1 calc R . .
C12A C 0.5182(7) 0.8825(8) 0.3792(7) 0.070(2) Uani 0.511(10) 1 d PD . 1
H12A H 0.5185 0.7678 0.3374 0.084 Uiso 0.511(10) 1 calc PR . 1
H12B H 0.5388 0.9370 0.3029 0.084 Uiso 0.511(10) 1 calc PR . 1
C12B C 0.4988(8) 0.8387(6) 0.4724(10) 0.078(3) Uani 0.489(10) 1 d PD . 2
H12C H 0.4826 0.8155 0.5658 0.093 Uiso 0.489(10) 1 calc PR . 2
H12D H 0.5059 0.7380 0.4004 0.093 Uiso 0.489(10) 1 calc PR . 2
O2 O -0.0633(3) 0.5272(2) 0.3685(2) 0.0770(6) Uani 1 1 d . . .
C21 C -0.0605(5) 0.6293(3) 0.5154(4) 0.0815(9) Uani 1 1 d . . .
H21A H -0.1825 0.5774 0.5347 0.098 Uiso 1 1 calc R . .
H21B H -0.0397 0.7461 0.5185 0.098 Uiso 1 1 calc R . .
C22 C -0.0886(5) 0.3592(3) 0.3652(3) 0.0802(9) Uani 1 1 d . . .
H22A H -0.0872 0.2896 0.2644 0.096 Uiso 1 1 calc R . .
H22B H -0.2112 0.3011 0.3811 0.096 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
O2 Na1 O1 92.71(8) . .
O2 Na1 B1 95.45(8) . 2_565
O1 Na1 B1 106.69(9) . 2_565
O2 Na1 B1 119.18(9) . .
O1 Na1 B1 140.48(8) . .
B1 Na1 B1 93.69(10) 2_565 .
O2 Na1 B2 113.28(8) . .
O1 Na1 B2 92.39(9) . .
B1 Na1 B2 144.79(9) 2_565 .
B1 Na1 B2 55.18(8) . .
O2 Na1 Na1 115.53(6) . 2_565
O1 Na1 Na1 141.27(6) . 2_565
B1 Na1 Na1 47.97(7) 2_565 2_565
B1 Na1 Na1 45.72(6) . 2_565
B2 Na1 Na1 99.28(7) . 2_565
O2 Na1 H11 140.6(4) . .
O1 Na1 H11 125.7(4) . .
B1 Na1 H11 82.5(5) 2_565 .
B1 Na1 H11 23.4(3) . .
B2 Na1 H11 62.4(5) . .
Na1 Na1 H11 39.1(5) 2_565 .
O2 Na1 H12 96.5(3) . .
O1 Na1 H12 159.6(5) . .
B1 Na1 H12 90.5(5) 2_565 .
B1 Na1 H12 23.4(3) . .
B2 Na1 H12 67.2(5) . .
Na1 Na1 H12 47.4(5) 2_565 .
H11 Na1 H12 44.4(6) . .
O2 Na1 H21 131.7(4) . .
O1 Na1 H21 78.1(5) . .
B1 Na1 H21 132.7(4) 2_565 .
B1 Na1 H21 63.5(5) . .
B2 Na1 H21 23.4(3) . .
Na1 Na1 H21 98.9(5) 2_565 .
H11 Na1 H21 59.9(8) . .
H12 Na1 H21 82.2(7) . .
O2 Na1 H22 90.1(3) . .
O1 Na1 H22 92.3(6) . .
B1 Na1 H22 159.9(6) 2_565 .
B1 Na1 H22 66.9(6) . .
B2 Na1 H22 23.3(3) . .
Na1 Na1 H22 112.4(6) 2_565 .
H11 Na1 H22 81.0(7) . .
H12 Na1 H22 69.6(9) . .
H21 Na1 H22 44.1(6) . .
N1 B1 Na1 166.99(18) . 2_565
N1 B1 Na1 96.27(15) . .
Na1 B1 Na1 86.31(10) 2_565 .
N1 B1 H11 106.7(11) . .
Na1 B1 H11 63.9(11) 2_565 .
Na1 B1 H11 58.8(10) . .
N1 B1 H12 110.4(12) . .
Na1 B1 H12 81.9(12) 2_565 .
Na1 B1 H12 59.8(10) . .
H11 B1 H12 109.9(13) . .
N1 B1 H13 111.7(13) . .
Na1 B1 H13 66.1(13) 2_565 .
Na1 B1 H13 152.0(13) . .
H11 B1 H13 109.0(10) . .
H12 B1 H13 109.2(10) . .
N1 B2 Na1 96.00(13) . .
N1 B2 H21 109.3(12) . .
Na1 B2 H21 63.3(10) . .
N1 B2 H22 109.3(14) . .
Na1 B2 H22 57.0(11) . .
H21 B2 H22 110.3(14) . .
N1 B2 H23 109.6(12) . .
Na1 B2 H23 154.1(12) . .
H21 B2 H23 109.7(10) . .
H22 B2 H23 108.6(11) . .
C1B N1 C1A 12.2(12) . .
C1B N1 B1 112.8(6) . .
C1A N1 B1 111.4(5) . .
C1B N1 B2 107.1(6) . .
C1A N1 B2 117.6(6) . .
B1 N1 B2 111.9(2) . .
C1B N1 H1 112.2(17) . .
C1A N1 H1 102.2(17) . .
B1 N1 H1 107.6(15) . .
B2 N1 H1 105.0(16) . .
N1 C1A C2A 122.6(9) . .
N1 C1A H1A1 106.7 . .
C2A C1A H1A1 106.7 . .
N1 C1A H1A2 106.7 . .
C2A C1A H1A2 106.7 . .
H1A1 C1A H1A2 106.6 . .
N1 C1B C2B 105.2(8) . .
N1 C1B H1C 110.7 . .
C2B C1B H1C 110.7 . .
N1 C1B H1D 110.7 . .
C2B C1B H1D 110.7 . .
H1C C1B H1D 108.8 . .
C1B C2B H2BA 109.5 . .
C1B C2B H2BB 109.5 . .
H2BA C2B H2BB 109.5 . .
C1B C2B H2BC 109.5 . .
H2BA C2B H2BC 109.5 . .
H2BB C2B H2BC 109.5 . .
C11 O1 C12A 111.0(3) . .
C11 O1 C12B 110.2(3) . .
C12A O1 C12B 43.1(3) . .
C11 O1 Na1 121.82(19) . .
C12A O1 Na1 117.2(2) . .
C12B O1 Na1 127.0(2) . .
C12A C11 C12B 47.3(3) 2_676 2_676
C12A C11 O1 117.1(4) 2_676 .
C12B C11 O1 116.4(4) 2_676 .
C12A C11 H11A 108.0 2_676 .
C12B C11 H11A 63.5 2_676 .
O1 C11 H11A 108.0 . .
C12A C11 H11B 108.0 2_676 .
C12B C11 H11B 135.4 2_676 .
O1 C11 H11B 108.0 . .
H11A C11 H11B 107.3 . .
C11 C12A O1 112.9(4) 2_676 .
C11 C12A H12A 109.0 2_676 .
O1 C12A H12A 109.0 . .
C11 C12A H12B 109.0 2_676 .
O1 C12A H12B 109.0 . .
H12A C12A H12B 107.8 . .
C11 C12B O1 111.9(5) 2_676 .
C11 C12B H12C 109.2 2_676 .
O1 C12B H12C 109.2 . .
C11 C12B H12D 109.2 2_676 .
O1 C12B H12D 109.2 . .
H12C C12B H12D 107.9 . .
C21 O2 C22 109.55(18) . .
C21 O2 Na1 121.97(14) . .
C22 O2 Na1 124.32(14) . .
O2 C21 C22 110.6(2) . 2_566
O2 C21 H21A 109.5 . .
C22 C21 H21A 109.5 2_566 .
O2 C21 H21B 109.5 . .
C22 C21 H21B 109.5 2_566 .
H21A C21 H21B 108.1 . .
O2 C22 C21 110.7(2) . 2_566
O2 C22 H22A 109.5 . .
C21 C22 H22A 109.5 2_566 .
O2 C22 H22B 109.5 . .
C21 C22 H22B 109.5 2_566 .
H22A C22 H22B 108.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Na1 O2 2.3333(18) .
Na1 O1 2.362(2) .
Na1 B1 2.720(3) 2_565
Na1 B1 2.822(4) .
Na1 B2 2.823(3) .
Na1 Na1 3.7916(18) 2_565
Na1 H11 2.436(19) .
Na1 H12 2.46(2) .
Na1 H21 2.53(2) .
Na1 H22 2.40(2) .
B1 N1 1.573(3) .
B1 Na1 2.720(3) 2_565
B1 H11 1.130(13) .
B1 H12 1.128(14) .
B1 H13 1.13(2) .
B2 N1 1.582(4) .
B2 H21 1.125(13) .
B2 H22 1.132(14) .
B2 H23 1.13(2) .
N1 C1B 1.465(9) .
N1 C1A 1.494(8) .
N1 H1 0.84(2) .
C1A C2A 1.537(10) .
C1A H1A1 0.9900 .
C1A H1A2 0.9900 .
C2A H2AA 0.9800 .
C2A H2AB 0.9800 .
C2A H2AC 0.9800 .
C1B C2B 1.503(10) .
C1B H1C 0.9900 .
C1B H1D 0.9900 .
C2B H2BA 0.9800 .
C2B H2BB 0.9800 .
C2B H2BC 0.9800 .
O1 C11 1.421(3) .
O1 C12A 1.466(5) .
O1 C12B 1.480(6) .
C11 C12A 1.347(6) 2_676
C11 C12B 1.350(6) 2_676
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12A C11 1.347(6) 2_676
C12A H12A 0.9900 .
C12A H12B 0.9900 .
C12B C11 1.350(6) 2_676
C12B H12C 0.9900 .
C12B H12D 0.9900 .
O2 C21 1.430(3) .
O2 C22 1.435(3) .
C21 C22 1.478(4) 2_566
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C21 1.478(4) 2_566
C22 H22A 0.9900 .
C22 H22B 0.9900 .
