#------------------------------------------------------------------------------
#$Date: 2023-03-13 12:35:11 +0200 (Mon, 13 Mar 2023) $
#$Revision: 281844 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106932.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_8106932
loop_
_publ_author_name
'Li, Ping'
'Fan, Cai-Hong'
'Ge, Jun-Feng'
_publ_section_title
;
 Crystal structure of 1-propyl-3-methylimidazolium pentaborate,
 [C7H13N2][B5O6(OH)4]
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              537
_journal_page_last               539
_journal_paper_doi               10.1515/ncrs-2015-0178
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C7 H17 B5 N2 O10'
_chemical_formula_weight         343.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90.367(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5108(17)
_cell_length_b                   15.659(3)
_cell_length_c                   10.356(2)
_cell_measurement_reflns_used    2903
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.01
_cell_measurement_theta_min      2.36
_cell_volume                     1542.3(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL(Bruker, 2001)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7736
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.141
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_correction_T_min  0.9702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       columnar
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.301
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         2714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.301
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0402
_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)+(0.0200P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0893
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2195
_reflns_number_total             2714
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2015-0178_suppl.cif
_cod_data_source_block           A
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_cell_volume        1542.2(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8106932
_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.
;
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.985
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_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
B1 B 0.9548(2) 0.09463(13) 0.09825(19) 0.0284(4) Uani 1 1 d . . . . .
B2 B 0.8691(2) 0.20215(13) -0.0434(2) 0.0312(5) Uani 1 1 d . . . . .
B3 B 0.70515(19) 0.13355(13) 0.10981(18) 0.0272(4) Uani 1 1 d . . . . .
B4 B 0.4506(2) 0.10330(13) 0.10516(19) 0.0301(4) Uani 1 1 d . . . . .
B5 B 0.5365(2) 0.20327(13) 0.2593(2) 0.0317(5) Uani 1 1 d . . . . .
C0AA C 0.1938(3) 0.1586(2) 0.7669(2) 0.0756(8) Uani 1 1 d . . . . .
H0A1 H 0.2187 0.2178 0.7592 0.113 Uiso 0.5 1 calc R U P . .
H0A2 H 0.2603 0.1303 0.8224 0.113 Uiso 0.5 1 calc R U P . .
H0A3 H 0.1014 0.1539 0.8030 0.113 Uiso 0.5 1 calc R U P . .
H0A4 H 0.1683 0.1169 0.8305 0.113 Uiso 0.5 1 calc R U P . .
H0A5 H 0.1266 0.2043 0.7673 0.113 Uiso 0.5 1 calc R U P . .
H0A6 H 0.2856 0.1808 0.7867 0.113 Uiso 0.5 1 calc R U P . .
C1AA C 0.2022(3) 0.15988(15) 0.5239(2) 0.0616(6) Uani 1 1 d . . . . .
H1AA H 0.2079 0.2186 0.5117 0.074 Uiso 1 1 calc R U . . .
C3 C 0.1991(3) 0.10063(15) 0.4316(2) 0.0642(7) Uani 1 1 d . . . . .
H3 H 0.2028 0.1105 0.3431 0.077 Uiso 1 1 calc R U . . .
C4 C 0.1881(2) 0.03616(15) 0.6162(2) 0.0503(6) Uani 1 1 d . . . . .
H4 H 0.1827 -0.0063 0.6788 0.060 Uiso 1 1 calc R U . . .
N1 N 0.19540(17) 0.11870(12) 0.63928(16) 0.0461(4) Uani 1 1 d . . . . .
N2 N 0.18945(18) 0.02302(11) 0.49028(17) 0.0499(5) Uani 1 1 d . . . . .
O1 O 1.06179(14) 0.04518(9) 0.14271(13) 0.0398(3) Uani 1 1 d . . . . .
O2 O 0.98105(12) 0.15937(8) 0.01173(12) 0.0365(3) Uani 1 1 d . . . . .
O3 O 0.82385(11) 0.07900(7) 0.14128(11) 0.0308(3) Uani 1 1 d . . . . .
O4 O 0.73692(11) 0.19006(8) 0.00027(11) 0.0316(3) Uani 1 1 d . . . . .
O5 O 0.89917(15) 0.25517(10) -0.14213(15) 0.0511(4) Uani 1 1 d . . . . .
O6 O 0.58317(11) 0.08042(7) 0.07407(11) 0.0310(3) Uani 1 1 d . . . . .
O7 O 0.33682(12) 0.06244(9) 0.05514(14) 0.0420(4) Uani 1 1 d . . . . .
O8 O 0.42454(12) 0.16755(8) 0.19227(12) 0.0380(3) Uani 1 1 d . . . . .
O9 O 0.50463(15) 0.25463(10) 0.35911(14) 0.0473(4) Uani 1 1 d . . . . .
O10 O 0.67022(11) 0.18543(8) 0.22451(11) 0.0327(3) Uani 1 1 d . . . . .
H7 H 0.359(3) 0.0214(16) 0.012(2) 0.065(8) Uiso 1 1 d . . . . .
H1 H 1.136(3) 0.0569(15) 0.110(2) 0.058(7) Uiso 1 1 d . . . . .
H9 H 0.577(3) 0.2718(17) 0.398(3) 0.083(9) Uiso 1 1 d . . . . .
H5 H 0.832(3) 0.2728(16) -0.177(2) 0.071(8) Uiso 1 1 d . . . . .
C3AA C 0.3193(6) -0.1016(3) 0.4212(6) 0.0698(11) Uani 0.5 1 d . . P A 1
H3AA H 0.3099 -0.1615 0.3989 0.084 Uiso 0.5 1 calc R U P A 1
H3AB H 0.3551 -0.0973 0.5089 0.084 Uiso 0.5 1 calc R U P A 1
C5 C 0.1753(6) -0.0552(4) 0.4083(6) 0.0574(9) Uiso 0.5 1 d . U P A 1
H5A H 0.1564 -0.0400 0.3191 0.069 Uiso 0.5 1 calc R U P A 1
H5B H 0.0997 -0.0913 0.4390 0.069 Uiso 0.5 1 calc R U P A 1
C4AA C 0.2938(6) -0.0829(3) 0.3359(6) 0.0698(11) Uani 0.5 1 d . . P A 2
H4AA H 0.2797 -0.1403 0.3032 0.084 Uiso 0.5 1 calc R U P A 2
H4AB H 0.2746 -0.0433 0.2659 0.084 Uiso 0.5 1 calc R U P A 2
C1 C 0.4383(7) -0.0734(5) 0.3764(7) 0.0879(14) Uiso 0.5 1 d . U P A 2
H1A H 0.4991 -0.0844 0.3046 0.132 Uiso 0.5 1 calc R U P A 2
H1B H 0.4535 -0.0163 0.4072 0.132 Uiso 0.5 1 calc R U P A 2
H1C H 0.4586 -0.1133 0.4445 0.132 Uiso 0.5 1 calc R U P A 2
C5A C 0.1900(6) -0.0665(4) 0.4450(5) 0.0574(9) Uiso 0.5 1 d . U P A 2
H5A1 H 0.0962 -0.0814 0.4155 0.069 Uiso 0.5 1 calc R U P A 2
H5A2 H 0.2134 -0.1035 0.5172 0.069 Uiso 0.5 1 calc R U P A 2
C2 C 0.4221(8) -0.0544(4) 0.3230(6) 0.0879(14) Uiso 0.5 1 d . U P A 1
H2A H 0.3786 -0.0517 0.2392 0.132 Uiso 0.5 1 calc R U P A 1
H2B H 0.5088 -0.0856 0.3174 0.132 Uiso 0.5 1 calc R U P A 1
H2C H 0.4409 0.0024 0.3533 0.132 Uiso 0.5 1 calc R U P A 1
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
O3 B1 O1 118.47(16) . .
O3 B1 O2 121.37(15) . .
O1 B1 O2 120.16(16) . .
O5 B2 O4 122.83(16) . .
O5 B2 O2 116.46(16) . .
O4 B2 O2 120.71(16) . .
O3 B3 O4 111.33(14) . .
O3 B3 O6 109.54(14) . .
O4 B3 O6 108.13(13) . .
O3 B3 O10 108.75(13) . .
O4 B3 O10 109.71(14) . .
O6 B3 O10 109.36(13) . .
O6 B4 O7 121.80(17) . .
O6 B4 O8 121.48(16) . .
O7 B4 O8 116.69(16) . .
O9 B5 O10 122.99(16) . .
O9 B5 O8 116.76(16) . .
O10 B5 O8 120.24(16) . .
N1 C0AA H0A1 109.5 . .
N1 C0AA H0A2 109.5 . .
H0A1 C0AA H0A2 109.5 . .
N1 C0AA H0A3 109.5 . .
H0A1 C0AA H0A3 109.5 . .
H0A2 C0AA H0A3 109.5 . .
N1 C0AA H0A4 109.5 . .
H0A1 C0AA H0A4 141.1 . .
H0A2 C0AA H0A4 56.3 . .
H0A3 C0AA H0A4 56.3 . .
N1 C0AA H0A5 109.5 . .
H0A1 C0AA H0A5 56.3 . .
H0A2 C0AA H0A5 141.1 . .
H0A3 C0AA H0A5 56.3 . .
H0A4 C0AA H0A5 109.5 . .
N1 C0AA H0A6 109.5 . .
H0A1 C0AA H0A6 56.3 . .
H0A2 C0AA H0A6 56.3 . .
H0A3 C0AA H0A6 141.1 . .
H0A4 C0AA H0A6 109.5 . .
H0A5 C0AA H0A6 109.5 . .
C3 C1AA N1 107.4(2) . .
C3 C1AA H1AA 126.3 . .
N1 C1AA H1AA 126.3 . .
C1AA C3 N2 107.6(2) . .
C1AA C3 H3 126.2 . .
N2 C3 H3 126.2 . .
N1 C4 N2 109.36(18) . .
N1 C4 H4 125.3 . .
N2 C4 H4 125.3 . .
C4 N1 C1AA 108.00(19) . .
C4 N1 C0AA 125.7(2) . .
C1AA N1 C0AA 126.3(2) . .
C4 N2 C3 107.63(19) . .
C4 N2 C5A 117.5(3) . .
C3 N2 C5A 134.8(3) . .
C4 N2 C5 133.4(3) . .
C3 N2 C5 118.9(3) . .
B1 O1 H1 112.5(16) . .
B1 O2 B2 118.97(14) . .
B1 O3 B3 122.55(14) . .
B2 O4 B3 122.56(14) . .
B2 O5 H5 112.9(19) . .
B4 O6 B3 121.67(14) . .
B4 O7 H7 111.9(17) . .
B4 O8 B5 118.91(14) . .
B5 O9 H9 111.7(19) . .
B5 O10 B3 122.94(13) . .
C5 C3AA C2 105.8(5) . .
C5 C3AA H3AA 110.6 . .
C2 C3AA H3AA 110.6 . .
C5 C3AA H3AB 110.6 . .
C2 C3AA H3AB 110.6 . .
H3AA C3AA H3AB 108.7 . .
N2 C5 C3AA 104.9(4) . .
N2 C5 H5A 110.8 . .
C3AA C5 H5A 110.8 . .
N2 C5 H5B 110.8 . .
C3AA C5 H5B 110.8 . .
H5A C5 H5B 108.8 . .
C1 C4AA C5A 112.8(5) . .
C1 C4AA H4AA 109.0 . .
C5A C4AA H4AA 109.0 . .
C1 C4AA H4AB 109.0 . .
C5A C4AA H4AB 109.0 . .
H4AA C4AA H4AB 107.8 . .
C4AA C1 H1A 109.5 . .
C4AA C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C4AA C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N2 C5A C4AA 113.5(4) . .
N2 C5A H5A1 108.9 . .
C4AA C5A H5A1 108.9 . .
N2 C5A H5A2 108.9 . .
C4AA C5A H5A2 108.9 . .
H5A1 C5A H5A2 107.7 . .
C3AA C2 H2A 109.5 . .
C3AA C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C3AA C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 O3 1.348(2) .
B1 O1 1.357(2) .
B1 O2 1.377(2) .
B2 O5 1.349(2) .
B2 O4 1.352(2) .
B2 O2 1.379(2) .
B3 O3 1.451(2) .
B3 O4 1.472(2) .
B3 O6 1.473(2) .
B3 O10 1.479(2) .
B4 O6 1.352(2) .
B4 O7 1.357(2) .
B4 O8 1.375(2) .
B5 O9 1.346(2) .
B5 O10 1.354(2) .
B5 O8 1.385(2) .
C0AA N1 1.462(3) .
C0AA H0A1 0.9600 .
C0AA H0A2 0.9600 .
C0AA H0A3 0.9600 .
C0AA H0A4 0.9600 .
C0AA H0A5 0.9600 .
C0AA H0A6 0.9600 .
C1AA C3 1.333(3) .
C1AA N1 1.360(3) .
C1AA H1AA 0.9300 .
C3 N2 1.362(3) .
C3 H3 0.9300 .
C4 N1 1.316(3) .
C4 N2 1.320(3) .
C4 H4 0.9300 .
N2 C5A 1.477(6) .
N2 C5 1.496(6) .
O1 H1 0.81(2) .
O5 H5 0.78(3) .
O7 H7 0.81(2) .
O9 H9 0.84(3) .
C3AA C5 1.555(8) .
C3AA C2 1.596(9) .
C3AA H3AA 0.9700 .
C3AA H3AB 0.9700 .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C4AA C1 1.442(9) .
C4AA C5A 1.527(8) .
C4AA H4AA 0.9700 .
C4AA H4AB 0.9700 .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C5A H5A1 0.9700 .
C5A H5A2 0.9700 .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N1 C1AA C3 N2 0.4(3) . . . .
N2 C4 N1 C1AA -0.2(2) . . . .
N2 C4 N1 C0AA 178.77(19) . . . .
C3 C1AA N1 C4 -0.1(3) . . . .
C3 C1AA N1 C0AA -179.1(2) . . . .
N1 C4 N2 C3 0.4(2) . . . .
N1 C4 N2 C5A 176.6(3) . . . .
N1 C4 N2 C5 -175.8(3) . . . .
C1AA C3 N2 C4 -0.5(3) . . . .
C1AA C3 N2 C5A -175.8(4) . . . .
C1AA C3 N2 C5 176.3(3) . . . .
O3 B1 O2 B2 -7.8(3) . . . .
O1 B1 O2 B2 172.53(17) . . . .
O5 B2 O2 B1 -169.71(17) . . . .
O4 B2 O2 B1 9.8(3) . . . .
O1 B1 O3 B3 173.60(15) . . . .
O2 B1 O3 B3 -6.0(3) . . . .
O4 B3 O3 B1 16.1(2) . . . .
O6 B3 O3 B1 135.60(16) . . . .
O10 B3 O3 B1 -104.94(17) . . . .
O5 B2 O4 B3 -178.65(17) . . . .
O2 B2 O4 B3 1.8(3) . . . .
O3 B3 O4 B2 -14.0(2) . . . .
O6 B3 O4 B2 -134.37(16) . . . .
O10 B3 O4 B2 106.44(18) . . . .
O7 B4 O6 B3 169.16(16) . . . .
O8 B4 O6 B3 -12.9(3) . . . .
O3 B3 O6 B4 144.44(16) . . . .
O4 B3 O6 B4 -94.07(18) . . . .
O10 B3 O6 B4 25.4(2) . . . .
O6 B4 O8 B5 -6.8(3) . . . .
O7 B4 O8 B5 171.24(16) . . . .
O9 B5 O8 B4 -168.54(17) . . . .
O10 B5 O8 B4 10.8(3) . . . .
O9 B5 O10 B3 -175.91(17) . . . .
O8 B5 O10 B3 4.8(3) . . . .
O3 B3 O10 B5 -141.05(16) . . . .
O4 B3 O10 B5 96.97(18) . . . .
O6 B3 O10 B5 -21.5(2) . . . .
C4 N2 C5 C3AA -75.6(5) . . . .
C3 N2 C5 C3AA 108.5(4) . . . .
C2 C3AA C5 N2 -81.3(5) . . . .
C4 N2 C5A C4AA -135.9(4) . . . .
C3 N2 C5A C4AA 39.0(6) . . . .
C1 C4AA C5A N2 66.4(6) . . . .
