#------------------------------------------------------------------------------
#$Date: 2019-09-23 18:29:49 +0300 (Mon, 23 Sep 2019) $
#$Revision: 218755 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/33/4063346.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_4063346
loop_
_publ_author_name
'Sabiah, Shahulhameed'
'Lee, Chen-Shiang'
'Hwang, Wen-Shu'
'Lin, Ivan J. B.'
_publ_section_title
;
 Facile C---N Bond Cleavage Promoted by Cuprous Oxide:
 Formation of C---C-Coupled Biimidazole from Its Methylene-Bridged Congener
;
_journal_coden_ASTM              ORGND7
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              290
_journal_page_last               293
_journal_paper_doi               10.1021/om9010406
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C16 H20 Cl4 Cu2 N8'
_chemical_formula_weight         593.28
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 113.3380(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.0805(6)
_cell_length_b                   10.8127(4)
_cell_length_c                   14.4679(6)
_cell_measurement_temperature    296(2)
_cell_volume                     2309.77(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13866
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    2.325
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.220
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0247
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0410P)²+1.3978P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0762
_reflns_number_gt                1971
_reflns_number_total             2152
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om9010406_si_002.cif
_cod_data_source_block           714906
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

 Updated bibliographic information.

 Antanas Vaitkus,
 2019-09-23
;
_cod_original_cell_volume        2309.77(15)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4063346
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Cu1 Cu 1.0000 0.42148(3) 0.2500 0.03170(12) Uani 1 2 d S . .
Cu2 Cu 1.0000 0.08912(3) 0.2500 0.03430(13) Uani 1 2 d S . .
Cl3 Cl 0.88703(4) 0.49980(6) 0.11440(4) 0.05002(17) Uani 1 1 d . . .
Cl4 Cl 1.11525(5) 0.01080(7) 0.21954(5) 0.0627(2) Uani 1 1 d . . .
C8 C 0.96100(15) 0.22316(18) 0.06039(16) 0.0347(4) Uani 1 1 d . . .
N4 N 1.07564(10) 0.36086(15) 0.17965(12) 0.0324(4) Uani 1 1 d . . .
C7 C 1.04967(14) 0.28327(19) 0.10242(16) 0.0342(4) Uani 1 1 d . . .
N3 N 0.92949(11) 0.15019(15) 0.11323(12) 0.0336(4) Uani 1 1 d . . .
C6 C 0.84226(14) 0.1204(2) 0.04988(17) 0.0422(5) Uani 1 1 d . . .
H6A H 0.8030 0.0706 0.0664 0.051 Uiso 1 1 calc R . .
N2 N 1.11784(15) 0.26275(16) 0.07264(17) 0.0432(5) Uani 1 1 d . . .
C5 C 1.16425(14) 0.3898(2) 0.19988(17) 0.0393(5) Uani 1 1 d . . .
H5A H 1.2005 0.4424 0.2507 0.047 Uiso 1 1 calc R . .
N1 N 0.89767(15) 0.23935(15) -0.03313(15) 0.0429(5) Uani 1 1 d . . .
C4 C 1.19019(15) 0.3297(2) 0.13411(19) 0.0474(5) Uani 1 1 d . . .
H4A H 1.2469 0.3334 0.1313 0.057 Uiso 1 1 calc R . .
C3 C 0.82297(16) 0.1748(2) -0.04004(18) 0.0485(6) Uani 1 1 d . . .
H3A H 0.7687 0.1693 -0.0963 0.058 Uiso 1 1 calc R . .
C2 C 1.1175(2) 0.1762(3) -0.0051(2) 0.0659(8) Uani 1 1 d . . .
H2A H 1.0582 0.1405 -0.0375 0.099 Uiso 1 1 calc R . .
H2B H 1.1609 0.1118 0.0251 0.099 Uiso 1 1 calc R . .
H2C H 1.1330 0.2193 -0.0541 0.099 Uiso 1 1 calc R . .
C1 C 0.9038(2) 0.3187(3) -0.1119(2) 0.0695(8) Uani 1 1 d . . .
H1A H 0.9632 0.3547 -0.0889 0.104 Uiso 1 1 calc R . .
H1B H 0.8594 0.3832 -0.1272 0.104 Uiso 1 1 calc R . .
H1C H 0.8930 0.2704 -0.1712 0.104 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
N4 Cu1 N4 141.37(9) 2_755 . ?
N4 Cu1 Cl3 97.17(5) 2_755 2_755 ?
N4 Cu1 Cl3 97.17(5) . 2_755 ?
N4 Cu1 Cl3 97.17(5) 2_755 . ?
N4 Cu1 Cl3 97.17(5) . . ?
Cl3 Cu1 Cl3 135.69(4) 2_755 . ?
N3 Cu2 N3 140.72(9) 2_755 . ?
N3 Cu2 Cl4 96.98(5) 2_755 2_755 ?
N3 Cu2 Cl4 97.66(5) . 2_755 ?
N3 Cu2 Cl4 97.66(5) 2_755 . ?
N3 Cu2 Cl4 96.98(5) . . ?
Cl4 Cu2 Cl4 135.46(4) 2_755 . ?
N3 C8 N1 110.27(19) . . ?
N3 C8 C7 123.72(19) . . ?
N1 C8 C7 125.9(2) . . ?
C7 N4 C5 106.15(17) . . ?
C7 N4 Cu1 126.14(14) . . ?
C5 N4 Cu1 127.71(14) . . ?
N4 C7 N2 110.46(19) . . ?
N4 C7 C8 124.17(18) . . ?
N2 C7 C8 125.27(19) . . ?
C8 N3 C6 106.02(18) . . ?
C8 N3 Cu2 125.37(14) . . ?
C6 N3 Cu2 128.42(15) . . ?
C3 C6 N3 109.0(2) . . ?
C3 C6 H6A 125.5 . . ?
N3 C6 H6A 125.5 . . ?
C7 N2 C4 107.30(19) . . ?
C7 N2 C2 126.6(2) . . ?
C4 N2 C2 125.9(2) . . ?
C4 C5 N4 108.96(19) . . ?
C4 C5 H5A 125.5 . . ?
N4 C5 H5A 125.5 . . ?
C8 N1 C3 107.6(2) . . ?
C8 N1 C1 127.1(2) . . ?
C3 N1 C1 125.1(2) . . ?
C5 C4 N2 107.13(19) . . ?
C5 C4 H4A 126.4 . . ?
N2 C4 H4A 126.4 . . ?
C6 C3 N1 107.15(19) . . ?
C6 C3 H3A 126.4 . . ?
N1 C3 H3A 126.4 . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N4 1.9815(16) 2_755 ?
Cu1 N4 1.9815(16) . ?
Cu1 Cl3 2.2456(5) 2_755 ?
Cu1 Cl3 2.2456(5) . ?
Cu2 N3 1.9645(17) 2_755 ?
Cu2 N3 1.9645(17) . ?
Cu2 Cl4 2.2346(6) 2_755 ?
Cu2 Cl4 2.2346(6) . ?
C8 N3 1.331(3) . ?
C8 N1 1.344(3) . ?
C8 C7 1.462(3) . ?
N4 C7 1.326(3) . ?
N4 C5 1.372(3) . ?
C7 N2 1.346(3) . ?
N3 C6 1.376(3) . ?
C6 C3 1.347(3) . ?
C6 H6A 0.9300 . ?
N2 C4 1.360(3) . ?
N2 C2 1.462(3) . ?
C5 C4 1.348(3) . ?
C5 H5A 0.9300 . ?
N1 C3 1.358(3) . ?
N1 C1 1.461(3) . ?
C4 H4A 0.9300 . ?
C3 H3A 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
