#------------------------------------------------------------------------------
#$Date: 2016-03-23 23:40:49 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179511 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/08/4340861.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_4340861
loop_
_publ_author_name
'Hailmann, Michael'
'Konieczka, Szymon Z.'
'Himmelspach, Alexander'
'Löblein, Jochen'
'Reiss, Guido J.'
'Finze, Maik'
_publ_section_title
;
 Carba-closo-dodecaborate Anions with Two Functional Groups:
 [1-R-12-HC≡C-closo-1-CB11H10](-) (R = CN, NC, CO2H, C(O)NH2,
 NHC(O)H).
;
_journal_issue                   17
_journal_name_full               'Inorganic chemistry'
_journal_page_first              9385
_journal_page_last               9399
_journal_paper_doi               10.1021/ic501526g
_journal_volume                  53
_journal_year                    2014
_chemical_formula_moiety         'C4 H11 B11 N, C8 H20 N'
_chemical_formula_sum            'C12 H31 B11 N2'
_chemical_formula_weight         322.30
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_Hall           '-P 2c 2b'
_space_group_name_H-M_alt        'P b c m'
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_space_group_name_H-M   'P b c m'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7742(5)
_cell_length_b                   11.6626(5)
_cell_length_c                   13.5228(5)
_cell_measurement_reflns_used    9780
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.7935
_cell_measurement_theta_min      2.3645
_cell_volume                     2014.63(14)
_computing_cell_refinement       'Saint+ ver. 7.68A (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2010.3 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. 7.68A (Bruker AXS)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  helios
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20051
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.594
_exptl_absorpt_coefficient_mu    0.053
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.063
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2070
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0805P)²+0.5298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                1867
_reflns_number_total             2070
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic501526g_si_002.cif
_cod_data_source_block           '[Et4N][1-NC-12-HCC-closo-1-CB11H10]'
_cod_depositor_comments
'Adding full bibliography for 4340857--4340862.cif.'
_cod_database_code               4340861
#BEGIN Tags that were not found in dictionaries:
_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.
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
N1 N -0.08643(13) 0.83493(14) 0.2500 0.0322(4) Uani 1 2 d S T P
H1 H 0.1770(15) 0.9706(17) 0.2500 0.023(5) Uiso 1 2 d S . P
H1AA H 0.6110(19) 0.566(2) 0.2500 0.047(7) Uiso 1 2 d S . P
C2 C 0.00096(14) 0.81290(14) 0.2500 0.0235(4) Uani 1 2 d S T P
H2 H 0.1441(11) 0.8371(12) 0.0823(12) 0.031(4) Uiso 1 1 d . . .
C1 C 0.11032(13) 0.77974(14) 0.2500 0.0193(4) Uani 1 2 d S T P
B1 B 0.20460(15) 0.88438(16) 0.2500 0.0219(4) Uani 1 2 d S T P
B2 B 0.18030(10) 0.79823(12) 0.14247(9) 0.0209(3) Uani 1 1 d . . .
B3 B 0.14041(11) 0.65850(11) 0.18381(10) 0.0220(3) Uani 1 1 d . . .
H3 H 0.0760(13) 0.6163(14) 0.1458(12) 0.041(4) Uiso 1 1 d . . .
B4 B 0.30985(11) 0.82176(12) 0.18368(10) 0.0229(3) Uani 1 1 d . . .
H4 H 0.3610(12) 0.8727(13) 0.1410(11) 0.036(4) Uiso 1 1 d . . .
B5 B 0.26978(11) 0.68231(11) 0.14258(10) 0.0221(3) Uani 1 1 d . . .
H5B H 0.1701(11) 0.2900(12) 0.6077(11) 0.022(3) Uiso 1 1 d . . .
H5A H 0.2526(11) 0.3845(13) 0.5910(11) 0.033(4) Uiso 1 1 d . . .
H5 H 0.3025(11) 0.6473(13) 0.0745(12) 0.034(4) Uiso 1 1 d . . .
B6 B 0.24508(15) 0.59642(16) 0.2500 0.0221(4) Uani 1 2 d S T P
H6C H 0.1579(15) 0.4452(15) 0.4475(14) 0.051(5) Uiso 1 1 d . . .
H6B H 0.0691(14) 0.3539(16) 0.4704(13) 0.047(5) Uiso 1 1 d . . .
H6A H 0.0911(13) 0.4531(15) 0.5463(13) 0.047(5) Uiso 1 1 d . . .
H6 H 0.2597(16) 0.5031(19) 0.2500 0.035(6) Uiso 1 2 d S . P
B7 B 0.35023(15) 0.69668(16) 0.2500 0.0210(4) Uani 1 2 d S T P
H7B H 0.2906(11) 0.3479(12) 0.3830(11) 0.023(3) Uiso 1 1 d . . .
H7A H 0.3723(11) 0.2541(13) 0.3874(11) 0.028(4) Uiso 1 1 d . . .
C3 C 0.46392(14) 0.64893(15) 0.2500 0.0248(4) Uani 1 2 d S T P
C4 C 0.54729(15) 0.60366(17) 0.2500 0.0291(4) Uani 1 2 d S T P
N2 N 0.26907(10) 0.2500 0.5000 0.0182(3) Uani 1 2 d S T P
C5 C 0.20189(9) 0.33315(10) 0.55890(9) 0.0209(3) Uani 1 1 d . . .
C6 C 0.12377(10) 0.40139(12) 0.49925(10) 0.0296(3) Uani 1 1 d . . .
C7 C 0.33608(10) 0.31318(10) 0.42463(9) 0.0241(3) Uani 1 1 d . . .
C8 C 0.41270(11) 0.39870(12) 0.46687(12) 0.0329(3) Uani 1 1 d . . .
H8C H 0.4481(14) 0.4329(16) 0.4102(15) 0.053(5) Uiso 1 1 d . . .
H8A H 0.3790(14) 0.4591(16) 0.5053(14) 0.054(5) Uiso 1 1 d . . .
H8B H 0.4645(13) 0.3625(16) 0.5096(14) 0.045(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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C2 C1 177.48(19) . .
C2 C1 B1 119.14(14) . .
C2 C1 B3 115.81(11) . 6_556
B1 C1 B3 115.40(11) . 6_556
C2 C1 B3 115.82(11) . .
B1 C1 B3 115.40(11) . .
B3 C1 B3 62.84(11) 6_556 .
C2 C1 B2 117.86(7) . .
B1 C1 B2 62.99(7) . .
B3 C1 B2 115.31(11) 6_556 .
B3 C1 B2 63.02(7) . .
C2 C1 B2 117.86(7) . 6_556
B1 C1 B2 62.99(7) . 6_556
B3 C1 B2 63.02(7) 6_556 6_556
B3 C1 B2 115.31(11) . 6_556
B2 C1 B2 115.38(13) . 6_556
C1 B1 B4 103.85(11) . 6_556
C1 B1 B4 103.85(11) . .
B4 B1 B4 60.75(11) 6_556 .
C1 B1 B2 58.66(7) . 6_556
B4 B1 B2 59.39(7) 6_556 6_556
B4 B1 B2 108.08(11) . 6_556
C1 B1 B2 58.66(7) . .
B4 B1 B2 108.08(11) 6_556 .
B4 B1 B2 59.39(7) . .
B2 B1 B2 108.25(13) 6_556 .
C1 B2 B4 103.85(9) . .
C1 B2 B5 103.83(10) . .
B4 B2 B5 60.91(8) . .
C1 B2 B1 58.35(8) . .
B4 B2 B1 59.71(9) . .
B5 B2 B1 108.37(10) . .
C1 B2 B3 58.40(8) . .
B4 B2 B3 107.95(9) . .
B5 B2 B3 59.35(7) . .
B1 B2 B3 107.75(9) . .
C1 B3 B6 104.07(9) . .
C1 B3 B5 104.16(10) . .
B6 B3 B5 61.03(8) . .
C1 B3 B3 58.58(5) . 6_556
B6 B3 B3 59.52(5) . 6_556
B5 B3 B3 108.41(6) . 6_556
C1 B3 B2 58.58(7) . .
B6 B3 B2 108.37(10) . .
B5 B3 B2 59.59(7) . .
B3 B3 B2 108.13(6) 6_556 .
B2 B4 B1 60.89(8) . .
B2 B4 B7 107.54(10) . .
B1 B4 B7 107.51(9) . .
B2 B4 B5 59.62(7) . .
B1 B4 B5 108.28(10) . .
B7 B4 B5 59.87(7) . .
B2 B4 B4 108.37(6) . 6_556
B1 B4 B4 59.62(5) . 6_556
B7 B4 B4 59.90(5) . 6_556
B5 B4 B4 108.05(6) . 6_556
B3 B5 B2 61.06(8) . .
B3 B5 B7 107.23(9) . .
B2 B5 B7 107.48(10) . .
B3 B5 B6 59.44(8) . .
B2 B5 B6 108.29(10) . .
B7 B5 B6 59.66(9) . .
B3 B5 B4 108.17(9) . .
B2 B5 B4 59.47(7) . .
B7 B5 B4 59.93(8) . .
B6 B5 B4 107.81(9) . .
B3 B6 B3 60.97(11) . 6_556
B3 B6 B7 107.59(11) . .
B3 B6 B7 107.59(11) 6_556 .
B3 B6 B5 59.53(7) . .
B3 B6 B5 108.37(11) 6_556 .
B7 B6 B5 60.02(7) . .
B3 B6 B5 108.37(11) . 6_556
B3 B6 B5 59.53(7) 6_556 6_556
B7 B6 B5 60.02(7) . 6_556
B5 B6 B5 108.27(13) . 6_556
C3 B7 B6 117.98(14) . .
C3 B7 B5 120.22(8) . .
B6 B7 B5 60.31(7) . .
C3 B7 B5 120.22(8) . 6_556
B6 B7 B5 60.31(7) . 6_556
B5 B7 B5 108.73(13) . 6_556
C3 B7 B4 124.15(12) . 6_556
B6 B7 B4 108.54(11) . 6_556
B5 B7 B4 108.55(11) . 6_556
B5 B7 B4 60.20(7) 6_556 6_556
C3 B7 B4 124.15(12) . .
B6 B7 B4 108.54(11) . .
B5 B7 B4 60.20(7) . .
B5 B7 B4 108.55(11) 6_556 .
B4 B7 B4 60.19(11) 6_556 .
C4 C3 B7 174.61(18) . .
C5 N2 C5 111.27(12) 4_556 .
C5 N2 C7 111.08(7) 4_556 4_556
C5 N2 C7 106.00(7) . 4_556
C5 N2 C7 106.00(7) 4_556 .
C5 N2 C7 111.08(7) . .
C7 N2 C7 111.52(12) 4_556 .
C6 C5 N2 115.42(9) . .
C8 C7 N2 115.55(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.146(2) .
C2 C1 1.450(2) .
C1 B1 1.715(2) .
C1 B3 1.7169(18) 6_556
C1 B3 1.7169(18) .
C1 B2 1.7204(15) .
C1 B2 1.7204(15) 6_556
B1 B4 1.774(2) 6_556
B1 B4 1.774(2) .
B1 B2 1.7945(17) 6_556
B1 B2 1.7945(17) .
B2 B4 1.7677(19) .
B2 B5 1.7704(19) .
B2 B3 1.7965(19) .
B3 B6 1.764(2) .
B3 B5 1.766(2) .
B3 B3 1.790(3) 6_556
B4 B7 1.788(2) .
B4 B5 1.7934(19) .
B4 B4 1.794(3) 6_556
B5 B7 1.7873(17) .
B5 B6 1.7925(17) .
B6 B3 1.764(2) 6_556
B6 B7 1.781(3) .
B6 B5 1.7925(17) 6_556
B7 C3 1.555(3) .
B7 B5 1.7873(17) 6_556
B7 B4 1.788(2) 6_556
C3 C4 1.189(3) .
N2 C5 1.5203(13) 4_556
N2 C5 1.5203(13) .
N2 C7 1.5214(13) 4_556
N2 C7 1.5214(13) .
C5 C6 1.5099(17) .
C7 C8 1.5096(18) .
