#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:27:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178652 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/63/4076385.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_4076385
loop_
_publ_author_name
'Yao, Zi-Jian'
'Jin, Guo-Xin'
_publ_section_title
;
 Synthesis, Reactivity, and Structural Transformation of Mono- and
 Binuclear Carboranylamidinate-Based 3d Metal Complexes and
 Metallacarborane Derivatives
;
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              1767
_journal_paper_doi               10.1021/om2011358
_journal_volume                  31
_journal_year                    2012
_chemical_formula_sum            'C18 H50 B20 Cu N4'
_chemical_formula_weight         602.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 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                 101.544(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.682(9)
_cell_length_b                   8.324(5)
_cell_length_c                   15.107(10)
_cell_measurement_reflns_used    747
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.325
_cell_measurement_theta_min      2.752
_cell_volume                     1685.7(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0795
_diffrn_reflns_av_sigmaI/netI    0.1316
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7898
_diffrn_reflns_theta_full        27.01
_diffrn_reflns_theta_max         27.01
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        4.96
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  0.9423
_exptl_absorpt_correction_T_min  0.9065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             630
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         3.411
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3635
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.912
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0763
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0970P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1709
_refine_ls_wR_factor_ref         0.1820
_reflns_number_gt                2090
_reflns_number_total             3635
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om2011358_si_001.cif
_cod_data_source_block           5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2/n
_cod_database_code               4076385
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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
Cu1 Cu 0.7500 0.59998(9) 0.7500 0.0279(3) Uani 1 2 d S
N1 N 0.7883(2) 0.5429(4) 0.6322(2) 0.0289(8) Uani 1 1 d .
N2 N 0.8794(3) 0.6559(5) 0.5279(3) 0.0375(10) Uani 1 1 d .
H2 H 0.926(4) 0.722(6) 0.526(3) 0.053(16) Uiso 1 1 d .
B3 B 0.9912(3) 0.5889(7) 0.7670(3) 0.0349(12) Uani 1 1 d .
H3 H 0.9923 0.4570 0.7624 0.042 Uiso 1 1 calc R
B4 B 0.9917(4) 0.6908(7) 0.8692(4) 0.0405(13) Uani 1 1 d .
H4 H 0.9939 0.6245 0.9325 0.049 Uiso 1 1 calc R
B5 B 0.9228(4) 0.8685(6) 0.8455(4) 0.0385(13) Uani 1 1 d .
H5 H 0.8797 0.9176 0.8935 0.046 Uiso 1 1 calc R
B6 B 0.8780(4) 0.8823(6) 0.7297(3) 0.0331(11) Uani 1 1 d .
H6 H 0.8057 0.9383 0.7012 0.040 Uiso 1 1 calc R
B7 B 0.9827(4) 0.8964(7) 0.6756(4) 0.0354(12) Uani 1 1 d .
H7 H 0.9785 0.9618 0.6117 0.043 Uiso 1 1 calc R
B8 B 1.0528(4) 0.7185(7) 0.6986(4) 0.0380(13) Uani 1 1 d .
H8 H 1.0939 0.6693 0.6491 0.046 Uiso 1 1 calc R
B9 B 1.0969(4) 0.7034(8) 0.8163(4) 0.0456(15) Uani 1 1 d .
H9 H 1.1684 0.6447 0.8448 0.055 Uiso 1 1 calc R
B10 B 1.0543(4) 0.8758(7) 0.8670(4) 0.0425(14) Uani 1 1 d .
H10 H 1.0979 0.9300 0.9289 0.051 Uiso 1 1 calc R
B11 B 0.9840(4) 0.9966(7) 0.7793(4) 0.0414(14) Uani 1 1 d .
H11 H 0.9819 1.1284 0.7836 0.050 Uiso 1 1 calc R
B12 B 1.0924(4) 0.8912(7) 0.7612(4) 0.0422(13) Uani 1 1 d .
H12 H 1.1609 0.9547 0.7543 0.051 Uiso 1 1 calc R
C1 C 0.8888(3) 0.6980(5) 0.7837(3) 0.0295(10) Uani 1 1 d .
C2 C 0.9259(3) 0.7187(5) 0.6868(3) 0.0284(10) Uani 1 1 d .
C3 C 0.8570(3) 0.6319(5) 0.6101(3) 0.0285(10) Uani 1 1 d .
C4 C 0.7390(3) 0.4110(5) 0.5720(3) 0.0322(10) Uani 1 1 d .
H4A H 0.7030 0.4575 0.5151 0.039 Uiso 1 1 calc R
C5 C 0.6659(3) 0.3225(6) 0.6174(3) 0.0430(12) Uani 1 1 d .
H5A H 0.6999 0.2835 0.6751 0.065 Uiso 1 1 calc R
H5B H 0.6379 0.2337 0.5803 0.065 Uiso 1 1 calc R
H5C H 0.6135 0.3944 0.6255 0.065 Uiso 1 1 calc R
C6 C 0.8165(4) 0.2924(6) 0.5518(4) 0.0497(13) Uani 1 1 d .
H6A H 0.8583 0.3446 0.5165 0.075 Uiso 1 1 calc R
H6B H 0.7834 0.2028 0.5186 0.075 Uiso 1 1 calc R
H6C H 0.8567 0.2551 0.6075 0.075 Uiso 1 1 calc R
C7 C 0.8123(3) 0.6540(6) 0.4386(3) 0.0395(11) Uani 1 1 d .
H7A H 0.7907 0.5432 0.4240 0.047 Uiso 1 1 calc R
C8 C 0.8729(4) 0.7101(8) 0.3707(3) 0.0574(15) Uani 1 1 d .
H8A H 0.8907 0.8209 0.3817 0.086 Uiso 1 1 calc R
H8B H 0.8340 0.6986 0.3107 0.086 Uiso 1 1 calc R
H8C H 0.9323 0.6464 0.3768 0.086 Uiso 1 1 calc R
C9 C 0.7210(4) 0.7569(7) 0.4380(4) 0.0634(17) Uani 1 1 d .
H9A H 0.6870 0.7201 0.4839 0.095 Uiso 1 1 calc R
H9B H 0.6770 0.7493 0.3800 0.095 Uiso 1 1 calc R
H9C H 0.7409 0.8667 0.4496 0.095 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'
Cu Cu 0.3201 1.2651 '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 Cu1 N1 152.6(2) 2_656 .
N1 Cu1 C1 105.59(15) 2_656 .
N1 Cu1 C1 85.46(15) . .
N1 Cu1 C1 85.46(15) 2_656 2_656
N1 Cu1 C1 105.59(15) . 2_656
C1 Cu1 C1 132.8(3) . 2_656
C3 N1 C4 121.7(3) . .
C3 N1 Cu1 115.1(3) . .
C4 N1 Cu1 123.1(3) . .
C3 N2 C7 128.7(4) . .
C1 B3 C2 57.0(2) . .
C1 B3 B4 58.7(3) . .
C2 B3 B4 102.9(4) . .
C1 B3 B9 105.9(4) . .
C2 B3 B9 102.9(4) . .
B4 B3 B9 60.7(3) . .
C1 B3 B8 104.6(4) . .
C2 B3 B8 57.6(3) . .
B4 B3 B8 107.0(4) . .
B9 B3 B8 59.0(3) . .
C1 B4 B5 59.2(3) . .
C1 B4 B3 59.8(3) . .
B5 B4 B3 108.7(4) . .
C1 B4 B10 106.5(4) . .
B5 B4 B10 60.2(3) . .
B3 B4 B10 108.7(4) . .
C1 B4 B9 106.0(4) . .
B5 B4 B9 108.0(4) . .
B3 B4 B9 59.8(3) . .
B10 B4 B9 60.1(3) . .
C1 B5 B6 60.2(3) . .
C1 B5 B4 59.2(3) . .
B6 B5 B4 109.1(4) . .
C1 B5 B10 106.5(4) . .
B6 B5 B10 108.9(4) . .
B4 B5 B10 60.3(3) . .
C1 B5 B11 107.2(4) . .
B6 B5 B11 60.4(3) . .
B4 B5 B11 109.0(4) . .
B10 B5 B11 60.4(3) . .
C2 B6 C1 57.6(3) . .
C2 B6 B5 104.2(4) . .
C1 B6 B5 59.1(3) . .
C2 B6 B11 104.3(4) . .
C1 B6 B11 106.9(4) . .
B5 B6 B11 61.0(3) . .
C2 B6 B7 58.1(3) . .
C1 B6 B7 105.8(3) . .
B5 B6 B7 108.1(4) . .
B11 B6 B7 59.7(3) . .
C2 B7 B8 59.3(3) . .
C2 B7 B11 104.2(3) . .
B8 B7 B11 108.3(4) . .
C2 B7 B12 104.1(4) . .
B8 B7 B12 59.2(3) . .
B11 B7 B12 60.7(3) . .
C2 B7 B6 58.1(3) . .
B8 B7 B6 108.0(4) . .
B11 B7 B6 59.6(3) . .
B12 B7 B6 107.7(4) . .
C2 B8 B12 104.7(4) . .
C2 B8 B7 58.5(3) . .
B12 B8 B7 60.8(3) . .
C2 B8 B9 103.9(4) . .
B12 B8 B9 60.4(3) . .
B7 B8 B9 108.7(4) . .
C2 B8 B3 58.8(3) . .
B12 B8 B3 108.0(4) . .
B7 B8 B3 108.4(4) . .
B9 B8 B3 59.2(3) . .
B8 B9 B12 59.3(3) . .
B8 B9 B3 61.8(3) . .
B12 B9 B3 109.3(4) . .
B8 B9 B10 107.5(4) . .
B12 B9 B10 60.3(3) . .
B3 B9 B10 107.8(4) . .
B8 B9 B4 108.1(4) . .
B12 B9 B4 107.9(4) . .
B3 B9 B4 59.4(3) . .
B10 B9 B4 59.4(3) . .
B5 B10 B4 59.5(3) . .
B5 B10 B9 107.6(4) . .
B4 B10 B9 60.4(3) . .
B5 B10 B12 107.9(4) . .
B4 B10 B12 108.0(4) . .
B9 B10 B12 59.5(3) . .
B5 B10 B11 60.3(3) . .
B4 B10 B11 108.3(4) . .
B9 B10 B11 108.1(4) . .
B12 B10 B11 60.3(3) . .
B6 B11 B7 60.7(3) . .
B6 B11 B5 58.6(3) . .
B7 B11 B5 107.0(4) . .
B6 B11 B10 106.6(4) . .
B7 B11 B10 107.4(4) . .
B5 B11 B10 59.3(3) . .
B6 B11 B12 107.8(4) . .
B7 B11 B12 59.8(3) . .
B5 B11 B12 106.8(4) . .
B10 B11 B12 59.8(3) . .
B8 B12 B9 60.4(3) . .
B8 B12 B7 60.0(3) . .
B9 B12 B7 108.1(4) . .
B8 B12 B10 108.2(4) . .
B9 B12 B10 60.2(3) . .
B7 B12 B10 107.4(4) . .
B8 B12 B11 108.0(4) . .
B9 B12 B11 108.3(4) . .
B7 B12 B11 59.6(3) . .
B10 B12 B11 59.9(3) . .
C2 C1 B4 108.7(3) . .
C2 C1 B5 107.4(3) . .
B4 C1 B5 61.6(3) . .
C2 C1 B6 60.1(3) . .
B4 C1 B6 111.6(4) . .
B5 C1 B6 60.7(3) . .
C2 C1 B3 61.6(3) . .
B4 C1 B3 61.6(3) . .
B5 C1 B3 112.1(4) . .
B6 C1 B3 113.1(3) . .
C2 C1 Cu1 104.9(3) . .
B4 C1 Cu1 139.5(3) . .
B5 C1 Cu1 127.3(3) . .
B6 C1 Cu1 104.5(3) . .
B3 C1 Cu1 119.7(3) . .
C3 C2 C1 111.9(3) . .
C3 C2 B6 116.4(3) . .
C1 C2 B6 62.2(3) . .
C3 C2 B7 124.4(4) . .
C1 C2 B7 114.1(3) . .
B6 C2 B7 63.7(3) . .
C3 C2 B8 122.7(4) . .
C1 C2 B8 113.2(3) . .
B6 C2 B8 115.1(4) . .
B7 C2 B8 62.3(3) . .
C3 C2 B3 113.0(4) . .
C1 C2 B3 61.5(3) . .
B6 C2 B3 114.8(3) . .
B7 C2 B3 115.6(3) . .
B8 C2 B3 63.6(3) . .
N1 C3 N2 129.2(4) . .
N1 C3 C2 116.6(4) . .
N2 C3 C2 114.2(4) . .
N1 C4 C5 109.8(3) . .
N1 C4 C6 110.5(4) . .
C5 C4 C6 109.0(4) . .
N2 C7 C9 111.2(4) . .
N2 C7 C8 106.9(4) . .
C9 C7 C8 112.6(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 2.010(4) 2_656
Cu1 N1 2.010(4) .
Cu1 C1 2.036(4) .
Cu1 C1 2.036(4) 2_656
N1 C3 1.293(5) .
N1 C4 1.498(5) .
N2 C3 1.352(5) .
N2 C7 1.473(6) .
B3 C1 1.730(7) .
B3 C2 1.732(7) .
B3 B4 1.761(8) .
B3 B9 1.768(8) .
B3 B8 1.815(7) .
B4 C1 1.710(7) .
B4 B5 1.752(8) .
B4 B10 1.766(8) .
B4 B9 1.784(8) .
B5 C1 1.712(7) .
B5 B6 1.739(8) .
B5 B10 1.765(8) .
B5 B11 1.782(8) .
B6 C2 1.695(7) .
B6 C1 1.730(7) .
B6 B11 1.771(7) .
B6 B7 1.790(7) .
B7 C2 1.696(7) .
B7 B8 1.760(8) .
B7 B11 1.772(8) .
B7 B12 1.775(7) .
B8 C2 1.710(6) .
B8 B12 1.746(8) .
B8 B9 1.766(8) .
B9 B12 1.766(8) .
B9 B10 1.779(9) .
B10 B12 1.782(8) .
B10 B11 1.784(8) .
B11 B12 1.791(8) .
C1 C2 1.651(6) .
C2 C3 1.521(6) .
C4 C5 1.512(6) .
C4 C6 1.524(6) .
C7 C9 1.513(7) .
C7 C8 1.515(6) .
