#------------------------------------------------------------------------------
#$Date: 2016-03-23 14:55:18 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179312 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/09/4320961.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_4320961
loop_
_publ_author_name
'David M. Schubert'
'Mandana Z. Visi'
'Carolyn B. Knobler'
_publ_contact_author
;
Schubert, D. M.,
US Borax Inc.
26877 Tourney Road, Valencia, CA 91355-1847, USA
;
_publ_contact_author_fax         661-287-6014
_publ_contact_author_phone       661-287-6074
_publ_section_title
;
 Guanidinium and Imidazolium Borates Containing the First Examples of an
 Isolated Nonaborate Oxoanion: [B₉O₁₂(OH)₆]³
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2250
_journal_page_last               2251
_journal_paper_doi               10.1021/ic000217u
_journal_volume                  39
_journal_year                    2000
_chemical_formula_sum            'C9 H21 B9 N6 O18'
_chemical_formula_weight         598.61
_chemical_name_common
;
imidazolium nonaborate
;
_chemical_name_systematic
;
[C₃H₅N₂]₃ [B₉O₁₂(OH)₆
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 91.170(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.622(3)
_cell_length_b                   9.3324(15)
_cell_length_c                   15.570(3)
_cell_measurement_temperature    373(2)
_cell_volume                     2414.8(7)
_computing_cell_refinement       'Bruker SMART 1000'
_computing_data_collection       'Bruker SMART 1000'
_computing_data_reduction        'Bruker SMART 1000'
_computing_molecular_graphics    ORTEP
_computing_publication_material  'Bruker SMART 1000 and UCLA programs'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      373(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker SMART 1000'
_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  0.1032
_diffrn_reflns_av_sigmaI/netI    0.1445
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15207
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.23
_exptl_absorpt_coefficient_mu    0.146
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          1.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.00230(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.819
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.819
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0500
_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)+(0.0124P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0873
_reflns_number_gt                2863
_reflns_number_total             5756
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic000217u_1.cif
_cod_data_source_block           compound2
_cod_original_sg_symbol_H-M      'P 1 21/a 1'
_cod_database_code               4320961
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.05052(9) 0.98535(17) 0.38380(10) 0.0194(4) Uani 1 1 d . . .
H1 H -0.0793 0.9173 0.3962 0.029 Uiso 1 1 calc R . .
B1 B 0.02786(17) 0.9539(3) 0.40509(17) 0.0137(6) Uani 1 1 d . . .
O2 O 0.08458(9) 1.05731(17) 0.39327(10) 0.0134(4) Uani 1 1 d . . .
B3 B 0.17177(16) 1.0199(3) 0.39354(17) 0.0123(6) Uani 1 1 d . . .
O4 O 0.18447(9) 0.90053(17) 0.45688(9) 0.0140(4) Uani 1 1 d . . .
B5 B 0.12617(17) 0.8004(3) 0.47039(18) 0.0148(7) Uani 1 1 d . . .
O5 O 0.13993(9) 0.67716(18) 0.51426(10) 0.0194(4) Uani 1 1 d . . .
H5 H 0.1881 0.6701 0.5259 0.029 Uiso 1 1 calc R . .
O6 O 0.04798(9) 0.82092(18) 0.43777(10) 0.0160(4) Uani 1 1 d . . .
O7 O 0.19622(9) 0.97680(17) 0.30916(10) 0.0126(4) Uani 1 1 d . . .
B8 B 0.25275(17) 1.0583(3) 0.25820(18) 0.0118(6) Uani 1 1 d . . .
O9 O 0.31247(9) 1.13319(17) 0.31312(10) 0.0133(4) Uani 1 1 d . . .
B10 B 0.29091(16) 1.1788(3) 0.39108(18) 0.0117(6) Uani 1 1 d . . .
O10 O 0.34292(9) 1.26704(17) 0.43765(10) 0.0160(4) Uani 1 1 d . . .
H10 H 0.3204 1.2961 0.4807 0.024 Uiso 1 1 calc R . .
O11 O 0.21759(9) 1.14510(17) 0.42549(10) 0.0133(4) Uani 1 1 d . . .
O21 O 0.53811(9) 0.95988(18) 0.10462(10) 0.0202(4) Uani 1 1 d . . .
H21 H 0.5674 0.8953 0.0881 0.030 Uiso 1 1 calc R . .
B21 B 0.45979(18) 0.9224(3) 0.09055(18) 0.0161(7) Uani 1 1 d . . .
O22 O 0.40226(9) 1.02218(17) 0.10796(10) 0.0151(4) Uani 1 1 d . . .
B23 B 0.31537(17) 0.9859(3) 0.11257(18) 0.0135(6) Uani 1 1 d . . .
O24 O 0.29944(9) 0.85382(17) 0.06103(10) 0.0140(4) Uani 1 1 d . . .
B25 B 0.35868(17) 0.7595(3) 0.04080(18) 0.0148(7) Uani 1 1 d . . .
O25 O 0.34270(10) 0.63294(18) 0.00039(10) 0.0189(4) Uani 1 1 d . . .
H25 H 0.2942 0.6260 -0.0091 0.028 Uiso 1 1 calc R . .
O26 O 0.43897(9) 0.78714(18) 0.06153(10) 0.0170(4) Uani 1 1 d . . .
O27 O 0.29314(9) 0.95720(17) 0.20099(10) 0.0128(4) Uani 1 1 d . . .
O29 O 0.20768(9) 1.16919(17) 0.20683(10) 0.0132(4) Uani 1 1 d . . .
B30 B 0.21762(16) 1.1859(3) 0.12151(18) 0.0137(6) Uani 1 1 d . . .
O30 O 0.17493(9) 1.29579(18) 0.08313(10) 0.0169(4) Uani 1 1 d . . .
H30 H 0.1885 1.3041 0.0331 0.025 Uiso 1 1 calc R . .
O31 O 0.26937(9) 1.10486(17) 0.07404(10) 0.0140(4) Uani 1 1 d . . .
N1A N 0.56568(12) 0.4107(2) 0.19417(13) 0.0189(5) Uani 1 1 d . . .
H1A H 0.6064 0.4373 0.2252 0.023 Uiso 1 1 calc R . .
C2A C 0.53705(15) 0.2792(3) 0.18935(16) 0.0204(6) Uani 1 1 d . . .
H2A H 0.5579 0.1998 0.2183 0.024 Uiso 1 1 calc R . .
N3A N 0.47367(12) 0.2790(2) 0.13644(13) 0.0209(5) Uani 1 1 d . . .
H3A H 0.4443 0.2058 0.1235 0.025 Uiso 1 1 calc R . .
C4A C 0.46282(15) 0.4158(3) 0.10569(16) 0.0205(6) Uani 1 1 d . . .
H4A H 0.4230 0.4458 0.0669 0.025 Uiso 1 1 calc R . .
C5A C 0.52032(15) 0.4982(3) 0.14208(16) 0.0202(6) Uani 1 1 d . . .
H5A H 0.5278 0.5959 0.1335 0.024 Uiso 1 1 calc R . .
N1B N 1.02090(12) 0.3213(2) 0.36732(13) 0.0176(5) Uani 1 1 d . . .
H1B H 1.0514 0.2527 0.3854 0.021 Uiso 1 1 calc R . .
C2B C 0.96043(14) 0.3076(3) 0.31143(15) 0.0167(6) Uani 1 1 d . . .
H2B H 0.9433 0.2226 0.2858 0.020 Uiso 1 1 calc R . .
N3B N 0.92854(12) 0.4356(2) 0.29820(12) 0.0174(5) Uani 1 1 d . . .
H3B H 0.8887 0.4543 0.2639 0.021 Uiso 1 1 calc R . .
C4B C 0.96952(14) 0.5340(3) 0.34830(15) 0.0183(6) Uani 1 1 d . . .
H4B H 0.9592 0.6317 0.3515 0.022 Uiso 1 1 calc R . .
C5B C 1.02743(15) 0.4617(3) 0.39189(16) 0.0187(6) Uani 1 1 d . . .
H5B H 1.0646 0.4999 0.4310 0.022 Uiso 1 1 calc R . .
N1C N 0.24895(12) 0.6851(2) 0.23691(13) 0.0181(5) Uani 1 1 d . . .
H1C H 0.2575 0.7673 0.2139 0.022 Uiso 1 1 calc R . .
C2C C 0.23090(15) 0.5649(3) 0.19453(17) 0.0190(6) Uani 1 1 d . . .
H2C H 0.2254 0.5554 0.1352 0.023 Uiso 1 1 calc R . .
N3C N 0.22210(12) 0.4607(2) 0.25201(13) 0.0194(5) Uani 1 1 d . . .
H3C H 0.2103 0.3730 0.2404 0.023 Uiso 1 1 calc R . .
C4C C 0.23493(15) 0.5164(3) 0.33301(17) 0.0209(6) Uani 1 1 d . . .
H4C H 0.2325 0.4669 0.3847 0.025 Uiso 1 1 calc R . .
C5C C 0.25169(15) 0.6561(3) 0.32299(17) 0.0200(6) Uani 1 1 d . . .
H5C H 0.2631 0.7214 0.3667 0.024 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'
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 B1 O1 118.2(2) . .
O2 B1 O6 121.5(2) . .
O1 B1 O6 120.3(2) . .
B1 O2 B3 120.6(2) . .
O7 B3 O11 112.1(2) . .
O7 B3 O2 110.81(19) . .
O11 B3 O2 108.1(2) . .
O7 B3 O4 110.7(2) . .
O11 B3 O4 107.56(18) . .
O2 B3 O4 107.43(19) . .
B5 O4 B3 121.24(19) . .
O5 B5 O4 123.0(2) . .
O5 B5 O6 116.4(2) . .
O4 B5 O6 120.5(2) . .
B1 O6 B5 118.2(2) . .
B3 O7 B8 123.24(19) . .
O7 B8 O27 107.6(2) . .
O7 B8 O9 111.5(2) . .
O27 B8 O9 110.2(2) . .
O7 B8 O29 109.28(19) . .
O27 B8 O29 110.5(2) . .
O9 B8 O29 107.79(19) . .
B10 O9 B8 119.1(2) . .
O9 B10 O11 122.3(2) . .
O9 B10 O10 119.1(2) . .
O11 B10 O10 118.6(2) . .
B10 O11 B3 120.3(2) . .
O21 B21 O22 117.6(2) . .
O21 B21 O26 121.3(3) . .
O22 B21 O26 121.0(2) . .
B21 O22 B23 122.6(2) . .
O27 B23 O31 112.6(2) . .
O27 B23 O22 110.66(19) . .
O31 B23 O22 107.8(2) . .
O27 B23 O24 108.1(2) . .
O31 B23 O24 108.63(19) . .
O22 B23 O24 108.9(2) . .
B25 O24 B23 122.5(2) . .
O25 B25 O24 122.1(2) . .
O25 B25 O26 116.4(2) . .
O24 B25 O26 121.4(2) . .
B21 O26 B25 118.5(2) . .
B23 O27 B8 125.61(19) . .
B30 O29 B8 122.3(2) . .
O29 B30 O31 123.8(2) . .
O29 B30 O30 116.1(2) . .
O31 B30 O30 120.0(2) . .
B30 O31 B23 121.5(2) . .
C2A N1A C5A 109.2(2) . .
N1A C2A N3A 108.6(2) . .
C2A N3A C4A 108.2(2) . .
C5A C4A N3A 107.3(2) . .
C4A C5A N1A 106.7(2) . .
C2B N1B C5B 109.3(2) . .
N3B C2B N1B 108.2(2) . .
C2B N3B C4B 108.8(2) . .
C5B C4B N3B 107.0(2) . .
C4B C5B N1B 106.6(2) . .
C2C N1C C5C 108.8(2) . .
N3C C2C N1C 108.0(2) . .
C2C N3C C4C 108.8(2) . .
C5C C4C N3C 106.8(2) . .
C4C C5C N1C 107.6(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 B1 1.370(3) .
B1 O2 1.364(3) .
B1 O6 1.380(3) .
O2 B3 1.491(3) .
B3 O7 1.440(3) .
B3 O11 1.475(3) .
B3 O4 1.500(3) .
O4 B5 1.366(3) .
B5 O5 1.355(3) .
B5 O6 1.399(3) .
O7 B8 1.456(3) .
B8 O27 1.469(3) .
B8 O9 1.473(3) .
B8 O29 1.499(3) .
O9 B10 1.342(3) .
B10 O11 1.378(3) .
B10 O10 1.387(3) .
O21 B21 1.361(3) .
B21 O22 1.366(3) .
B21 O26 1.382(3) .
O22 B23 1.487(3) .
B23 O27 1.458(3) .
B23 O31 1.469(3) .
B23 O24 1.492(3) .
O24 B25 1.362(3) .
B25 O25 1.362(3) .
B25 O26 1.391(3) .
O29 B30 1.351(3) .
B30 O31 1.373(3) .
B30 O30 1.376(3) .
N1A C2A 1.318(3) .
N1A C5A 1.366(3) .
C2A N3A 1.324(3) .
N3A C4A 1.374(3) .
C4A C5A 1.343(3) .
N1B C2B 1.322(3) .
N1B C5B 1.369(3) .
C2B N3B 1.321(3) .
N3B C4B 1.376(3) .
C4B C5B 1.347(3) .
N1C C2C 1.332(3) .
N1C C5C 1.367(3) .
C2C N3C 1.331(3) .
N3C C4C 1.377(3) .
C4C C5C 1.343(3) .
