#------------------------------------------------------------------------------
#$Date: 2019-11-23 13:57:29 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233529 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/89/4348987.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_4348987
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            'C24 H30 B2 F8 N6'
_chemical_formula_weight         576.16
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/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                 91.646(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.995(4)
_cell_length_b                   8.874(3)
_cell_length_c                   11.389(3)
_cell_measurement_reflns_used    1633
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.06
_cell_measurement_theta_min      1.57
_cell_volume                     1312.8(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9409
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2301
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0556
_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)+(0.1101P)²+1.0674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1608
_refine_ls_wR_factor_ref         0.1892
_reflns_number_gt                1633
_reflns_number_total             2301
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5qi00163c2.cif
_cod_data_source_block           sar282mm
_cod_original_cell_volume        1312.8(6)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4348987
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F2 F 0.16888(14) 0.9137(2) 0.13421(16) 0.0216(5) Uani 1 1 d .
F1 F 0.15018(16) 0.7913(2) 0.30727(17) 0.0299(6) Uani 1 1 d .
F3 F 0.16474(16) 1.0466(2) 0.30568(17) 0.0282(5) Uani 1 1 d .
F4 F 0.02008(15) 0.9336(3) 0.23260(18) 0.0314(6) Uani 1 1 d .
N5 N 0.20246(19) 0.4891(3) 0.1089(2) 0.0159(6) Uani 1 1 d .
N1 N 0.08727(19) 0.3445(3) 0.0469(2) 0.0144(6) Uani 1 1 d .
N3 N 0.1799(2) 0.3445(3) 0.0960(2) 0.0173(6) Uani 1 1 d .
C5 C 0.3014(2) 0.5277(4) 0.1636(3) 0.0172(7) Uani 1 1 d .
C1 C 0.1267(2) 0.5796(4) 0.0690(3) 0.0163(7) Uani 1 1 d .
H1 H 0.1261 0.6844 0.0695 0.020 Uiso 1 1 calc R
C29 C 0.0388(2) 0.1987(4) 0.0237(3) 0.0200(8) Uani 1 1 d .
H29A H 0.0845 0.1196 0.0495 0.030 Uiso 1 1 calc R
H29C H 0.0243 0.1885 -0.0590 0.030 Uiso 1 1 calc R
H29B H -0.0242 0.1922 0.0654 0.030 Uiso 1 1 calc R
C11 C 0.3519(3) 0.6383(5) -0.0313(3) 0.0286(9) Uani 1 1 d .
H11C H 0.2823 0.6111 -0.0525 0.043 Uiso 1 1 calc R
H11A H 0.3983 0.5857 -0.0810 0.043 Uiso 1 1 calc R
H11B H 0.3607 0.7449 -0.0409 0.043 Uiso 1 1 calc R
C10 C 0.3183(2) 0.4906(4) 0.2802(3) 0.0177(7) Uani 1 1 d .
C3 C 0.0503(2) 0.4861(4) 0.0273(3) 0.0140(7) Uani 1 1 d .
C8 C 0.4925(3) 0.5852(4) 0.2625(3) 0.0218(8) Uani 1 1 d .
C7 C 0.4698(3) 0.6244(4) 0.1470(3) 0.0237(8) Uani 1 1 d .
H7 H 0.5202 0.6711 0.1035 0.028 Uiso 1 1 calc R
C9 C 0.4154(2) 0.5195(4) 0.3274(3) 0.0198(8) Uani 1 1 d .
H8 H 0.4297 0.4941 0.4054 0.024 Uiso 1 1 calc R
C6 C 0.3743(2) 0.5963(4) 0.0941(3) 0.0207(8) Uani 1 1 d .
C13 C 0.2358(3) 0.4238(4) 0.3537(3) 0.0236(8) Uani 1 1 d .
H13A H 0.2628 0.4063 0.4319 0.035 Uiso 1 1 calc R
H13B H 0.2132 0.3300 0.3197 0.035 Uiso 1 1 calc R
H13C H 0.1788 0.4922 0.3565 0.035 Uiso 1 1 calc R
C12 C 0.5973(3) 0.6130(5) 0.3177(3) 0.0302(9) Uani 1 1 d .
H12C H 0.5983 0.5791 0.3977 0.045 Uiso 1 1 calc R
H12A H 0.6123 0.7189 0.3155 0.045 Uiso 1 1 calc R
H12B H 0.6481 0.5589 0.2749 0.045 Uiso 1 1 calc R
B1 B 0.1263(3) 0.9217(4) 0.2463(3) 0.0200(8) 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'
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
N3 N5 C1 112.7(3) .
N3 N5 C5 117.8(2) .
C1 N5 C5 129.5(3) .
N3 N1 C3 112.6(3) .
N3 N1 C29 117.6(3) .
C3 N1 C29 129.8(3) .
N1 N3 N5 104.2(2) .
C10 C5 C6 124.1(3) .
C10 C5 N5 118.0(3) .
C6 C5 N5 117.9(3) .
N5 C1 C3 105.8(3) .
C5 C10 C9 116.6(3) .
C5 C10 C13 122.4(3) .
C9 C10 C13 121.0(3) .
N1 C3 C1 104.7(3) .
N1 C3 C3 122.4(4) 3_565
C1 C3 C3 132.9(4) 3_565
C7 C8 C9 118.2(3) .
C7 C8 C12 121.4(3) .
C9 C8 C12 120.3(3) .
C8 C7 C6 122.1(3) .
C10 C9 C8 122.4(3) .
C7 C6 C5 116.5(3) .
C7 C6 C11 121.1(3) .
C5 C6 C11 122.3(3) .
F1 B1 F3 110.7(3) .
F1 B1 F4 109.2(3) .
F3 B1 F4 109.7(3) .
F1 B1 F2 109.0(3) .
F3 B1 F2 109.7(3) .
F4 B1 F2 108.5(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F2 B1 1.408(4) .
F1 B1 1.380(4) .
F3 B1 1.384(4) .
F4 B1 1.388(4) .
N5 N3 1.324(4) .
N5 C1 1.340(4) .
N5 C5 1.454(4) .
N1 N3 1.313(4) .
N1 C3 1.362(4) .
N1 C29 1.459(4) .
C5 C10 1.380(5) .
C5 C6 1.392(5) .
C1 C3 1.369(5) .
C11 C6 1.497(5) .
C10 C9 1.382(4) .
C10 C13 1.500(5) .
C3 C3 1.452(6) 3_565
C8 C7 1.385(5) .
C8 C9 1.390(5) .
C8 C12 1.503(5) .
C7 C6 1.386(5) .
