#------------------------------------------------------------------------------
#$Date: 2019-11-23 13:57:29 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233529 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/89/4348989.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_4348989
loop_
_publ_author_name
'Hohloch, Stephan'
'Suntrup, Lisa'
'Sarkar, Biprajit'
_publ_section_title
;
 Exploring potential cooperative effects in dicopper(i)-di-mesoionic
 carbene complexes: applications in click catalysis
;
_journal_issue                   1
_journal_name_full               'Inorganic Chemistry Frontiers'
_journal_page_first              67
_journal_paper_doi               10.1039/C5QI00163C
_journal_volume                  3
_journal_year                    2016
_chemical_formula_sum            'C42 H44 B2 Cl4 Cu2 F8 N12'
_chemical_formula_weight         1159.39
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_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
_audit_update_record
;
2013-08-07 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.151(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.220(4)
_cell_length_b                   13.993(3)
_cell_length_c                   17.774(3)
_cell_measurement_reflns_used    4796
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      1.78
_cell_volume                     4922.1(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Smart AXS'
_diffrn_measurement_method       '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  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24229
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    1.158
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2352
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5627
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0264
_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)+(0.0309P)²+6.3949P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0673
_reflns_number_gt                4796
_reflns_number_total             5627
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5qi00163c2.cif
_cod_data_source_block           sar243m
_cod_original_cell_volume        4921.9(15)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4348989
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
C6 C 0.19514(8) 0.23724(12) 0.34011(10) 0.0216(3) Uani 1 1 d .
C5 C 0.20263(8) 0.13388(12) 0.32050(11) 0.0255(4) Uani 1 1 d .
H5A H 0.2148 0.1305 0.2729 0.031 Uiso 1 1 calc R
H5B H 0.2388 0.1048 0.3650 0.031 Uiso 1 1 calc R
C8 C 0.19733(10) 0.40440(14) 0.30914(15) 0.0429(6) Uani 1 1 d .
H8 H 0.2016 0.4525 0.2752 0.051 Uiso 1 1 calc R
C7 C 0.20207(9) 0.30898(13) 0.28961(12) 0.0297(4) Uani 1 1 d .
H7 H 0.2099 0.2933 0.2429 0.036 Uiso 1 1 calc R
C12 C 0.00860(8) 0.33681(11) 0.02646(9) 0.0182(3) Uani 1 1 d .
H12A H -0.0080 0.3757 -0.0219 0.022 Uiso 1 1 calc R
H12B H -0.0169 0.2777 0.0161 0.022 Uiso 1 1 calc R
C14 C 0.10367(9) 0.22151(13) 0.04434(11) 0.0269(4) Uani 1 1 d .
H14 H 0.0722 0.1721 0.0318 0.032 Uiso 1 1 calc R
C13 C 0.08265(8) 0.31496(11) 0.04620(9) 0.0187(3) Uani 1 1 d .
C16 C 0.21880(9) 0.27368(15) 0.08000(11) 0.0337(4) Uani 1 1 d .
H16 H 0.2641 0.2600 0.0908 0.040 Uiso 1 1 calc R
C15 C 0.17191(10) 0.20121(15) 0.06123(12) 0.0352(4) Uani 1 1 d .
H15 H 0.1857 0.1384 0.0598 0.042 Uiso 1 1 calc R
C30 C -0.05792(8) 0.59429(11) 0.15857(10) 0.0204(3) Uani 1 1 d .
H30A H -0.0228 0.6416 0.1720 0.031 Uiso 1 1 calc R
H30C H -0.0766 0.5918 0.2003 0.031 Uiso 1 1 calc R
H30B H -0.0928 0.6108 0.1083 0.031 Uiso 1 1 calc R
C11 C 0.18292(9) 0.26191(14) 0.40923(12) 0.0302(4) Uani 1 1 d .
H11 H 0.1777 0.2142 0.4430 0.036 Uiso 1 1 calc R
C29 C 0.06526(9) -0.13137(12) 0.33617(11) 0.0262(4) Uani 1 1 d .
H29A H 0.0673 -0.1784 0.2977 0.039 Uiso 1 1 calc R
H29C H 0.0209 -0.1313 0.3390 0.039 Uiso 1 1 calc R
H29B H 0.0981 -0.1464 0.3883 0.039 Uiso 1 1 calc R
C17 C 0.19822(9) 0.36750(14) 0.08284(11) 0.0289(4) Uani 1 1 d .
H17 H 0.2299 0.4166 0.0958 0.035 Uiso 1 1 calc R
C18 C 0.13050(8) 0.38819(12) 0.06640(10) 0.0237(3) Uani 1 1 d .
H18 H 0.1170 0.4510 0.0689 0.028 Uiso 1 1 calc R
C10 C 0.17840(10) 0.35718(16) 0.42838(14) 0.0422(5) Uani 1 1 d .
H10 H 0.1701 0.3733 0.4747 0.051 Uiso 1 1 calc R
C9 C 0.18626(10) 0.42768(15) 0.37862(16) 0.0461(6) Uani 1 1 d .
H9 H 0.1841 0.4915 0.3920 0.055 Uiso 1 1 calc R
F3 F 0.35145(5) 0.18454(8) 0.38287(7) 0.0329(2) Uani 1 1 d .
F4 F 0.32518(6) 0.18214(11) 0.24688(7) 0.0524(4) Uani 1 1 d .
B1 B 0.37613(9) 0.17118(14) 0.32091(12) 0.0244(4) Uani 1 1 d .
F2 F 0.42806(6) 0.23708(8) 0.32952(8) 0.0394(3) Uani 1 1 d .
F1 F 0.40263(5) 0.07946(7) 0.32645(7) 0.0320(2) Uani 1 1 d .
Cl10 Cl 0.06549(2) 0.08644(4) 0.46454(3) 0.03467(11) Uani 1 1 d .
Cl11 Cl 0.11351(3) 0.02248(4) 0.63153(3) 0.04181(13) Uani 1 1 d .
C100 C 0.12910(10) 0.09828(14) 0.56120(11) 0.0318(4) Uani 1 1 d .
H10A H 0.1726 0.0827 0.5581 0.038 Uiso 1 1 calc R
H10B H 0.1308 0.1640 0.5791 0.038 Uiso 1 1 calc R
Cu1 Cu 0.049364(9) 0.233456(13) 0.215011(11) 0.01489(6) Uani 1 1 d .
N4 N -0.02908(6) 0.47454(9) 0.08004(8) 0.0176(3) Uani 1 1 d .
N2 N -0.02967(6) 0.50060(9) 0.15114(8) 0.0164(3) Uani 1 1 d .
N1 N 0.07976(7) -0.03683(9) 0.31100(8) 0.0190(3) Uani 1 1 d .
C2 C 0.01630(7) 0.35549(11) 0.17094(9) 0.0161(3) Uani 1 1 d .
N6 N -0.00140(6) 0.38793(9) 0.09370(8) 0.0160(3) Uani 1 1 d .
N3 N 0.14345(7) -0.00791(10) 0.33634(9) 0.0221(3) Uani 1 1 d .
N5 N 0.13921(7) 0.07988(9) 0.30576(8) 0.0196(3) Uani 1 1 d .
C4 C -0.00199(7) 0.43230(10) 0.20811(9) 0.0158(3) Uani 1 1 d .
C1 C 0.07564(7) 0.11032(11) 0.26097(9) 0.0172(3) Uani 1 1 d .
C3 C 0.03684(7) 0.03150(11) 0.26545(9) 0.0167(3) Uani 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'
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'
Cl Cl 0.1484 0.1585 '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'
F F 0.0171 0.0103 '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_3
C11 C6 C7 119.30(17) .
C11 C6 C5 120.78(16) .
C7 C6 C5 119.90(17) .
N5 C5 C6 111.40(13) .
C9 C8 C7 120.1(2) .
C6 C7 C8 119.9(2) .
N6 C12 C13 110.60(12) .
C13 C14 C15 120.26(17) .
C14 C13 C18 119.25(15) .
C14 C13 C12 120.10(15) .
C18 C13 C12 120.65(15) .
C15 C16 C17 119.73(17) .
C16 C15 C14 120.35(18) .
C6 C11 C10 120.51(19) .
C18 C17 C16 120.25(17) .
C17 C18 C13 120.15(16) .
C9 C10 C11 119.8(2) .
C10 C9 C8 120.45(19) .
F4 B1 F1 109.17(16) .
F4 B1 F3 110.55(15) .
F1 B1 F3 109.01(15) .
F4 B1 F2 110.26(16) .
F1 B1 F2 108.52(14) .
F3 B1 F2 109.30(15) .
Cl11 C100 Cl10 111.12(10) .
C1 Cu1 C2 175.18(6) .
C1 Cu1 Cu1 87.68(5) 2
C2 Cu1 Cu1 87.65(5) 2
N2 N4 N6 103.49(12) .
N4 N2 C4 111.56(12) .
N4 N2 C30 118.60(12) .
C4 N2 C30 129.84(13) .
N3 N1 C3 111.59(13) .
N3 N1 C29 118.25(13) .
C3 N1 C29 130.13(13) .
N6 C2 C4 101.45(13) .
N6 C2 Cu1 129.76(11) .
C4 C2 Cu1 128.56(11) .
N4 N6 C2 115.47(13) .
N4 N6 C12 118.55(12) .
C2 N6 C12 125.97(13) .
N1 N3 N5 103.45(12) .
N3 N5 C1 115.65(13) .
N3 N5 C5 118.32(13) .
C1 N5 C5 126.00(13) .
N2 C4 C2 108.01(13) .
N2 C4 C4 127.50(11) 2
C2 C4 C4 124.19(10) 2
N5 C1 C3 101.51(13) .
N5 C1 Cu1 127.48(11) .
C3 C1 Cu1 130.75(11) .
N1 C3 C1 107.82(13) .
N1 C3 C3 128.17(11) 2
C1 C3 C3 123.57(10) 2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C6 C11 1.388(3) .
C6 C7 1.389(2) .
C6 C5 1.510(2) .
C5 N5 1.482(2) .
C8 C9 1.377(4) .
C8 C7 1.392(3) .
C12 N6 1.472(2) .
C12 C13 1.513(2) .
C14 C13 1.386(2) .
C14 C15 1.398(3) .
C13 C18 1.395(2) .
C16 C15 1.375(3) .
C16 C17 1.390(3) .
C30 N2 1.4671(19) .
C11 C10 1.388(3) .
C29 N1 1.464(2) .
C17 C18 1.390(2) .
C10 C9 1.375(4) .
F3 B1 1.392(2) .
F4 B1 1.377(2) .
B1 F1 1.390(2) .
B1 F2 1.402(2) .
Cl10 C100 1.7685(19) .
Cl11 C100 1.7595(19) .
Cu1 C1 1.9021(16) .
Cu1 C2 1.9039(15) .
Cu1 Cu1 2.7958(5) 2
N4 N2 1.3195(18) .
N4 N6 1.3302(18) .
N2 C4 1.3619(19) .
N1 N3 1.3243(19) .
N1 C3 1.3664(19) .
C2 N6 1.3637(19) .
C2 C4 1.388(2) .
N3 N5 1.3330(19) .
N5 C1 1.3639(19) .
C4 C4 1.461(3) 2
C1 C3 1.396(2) .
C3 C3 1.458(3) 2
