#------------------------------------------------------------------------------
#$Date: 2019-11-17 12:18:32 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229830 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/64/7046476.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_7046476
loop_
_publ_author_name
'Nahra, Fady'
'Van Hecke, Kristof'
'Kennedy, Alan R.'
'Nelson, David J.'
_publ_section_title
;
 Coinage metal complexes of selenoureas derived from N-heterocyclic
 carbenes.
;
_journal_issue                   31
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10671
_journal_page_last               10684
_journal_paper_doi               10.1039/c8dt01506f
_journal_volume                  47
_journal_year                    2018
_chemical_formula_sum            'C42 H48 Cl2 Cu2 N4 Se2'
_chemical_formula_weight         964.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-04-16 deposited with the CCDC.
2018-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.387(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3880(12)
_cell_length_b                   19.011(3)
_cell_length_c                   13.4119(19)
_cell_measurement_reflns_used    5114
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.5458
_cell_measurement_theta_min      3.0446
_cell_volume                     2121.0(5)
_computing_cell_refinement       CrysalisPro
_computing_data_collection       CrysalisPro
_computing_data_reduction        CrysalisPro
_computing_publication_material  SHELXL-2014
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur E
;
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        27.000
_diffrn_reflns_theta_max         29.611
_diffrn_reflns_theta_min         3.051
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.879
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         5355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0398
_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)+(0.0308P)²+0.4469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0895
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4025
_reflns_number_total             5355
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8dt01506f2.cif
_cod_data_source_block           nelson_cuse_imu
_cod_depositor_comments
'Adding full bibliography for 7046473--7046483.cif.'
_cod_database_code               7046476
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 1.0000 0.0000 0.0000 0.02807(13) Uani 1 2 d S . P
Cu2 Cu 0.5000 0.0000 0.5000 0.04630(17) Uani 1 2 d S . P
Se1 Se 0.79473(3) 0.07413(2) 0.01863(2) 0.03073(9) Uani 1 1 d . . .
Cl1 Cl 0.55585(11) 0.10256(5) 0.55046(7) 0.0577(2) Uani 1 1 d . . .
N1 N 0.6841(2) 0.11400(11) 0.20218(16) 0.0250(5) Uani 1 1 d . . .
N2 N 0.7912(3) 0.01008(11) 0.21765(16) 0.0240(5) Uani 1 1 d . . .
C1 C 0.7588(3) 0.06405(13) 0.15240(19) 0.0227(5) Uani 1 1 d . . .
C2 C 0.6677(3) 0.09053(15) 0.2987(2) 0.0332(7) Uani 1 1 d . . .
H2 H 0.6185 0.1150 0.3484 0.040 Uiso 1 1 calc R U .
C3 C 0.7353(3) 0.02648(15) 0.3077(2) 0.0324(7) Uani 1 1 d . . .
H3 H 0.7434 -0.0026 0.3658 0.039 Uiso 1 1 calc R U .
C4 C 0.6352(3) 0.18181(13) 0.16067(19) 0.0235(6) Uani 1 1 d . . .
C5 C 0.4740(3) 0.19181(14) 0.12263(19) 0.0258(6) Uani 1 1 d . . .
C6 C 0.4332(3) 0.25685(14) 0.0792(2) 0.0286(6) Uani 1 1 d . . .
H6 H 0.3239 0.2658 0.0541 0.034 Uiso 1 1 calc R U .
C7 C 0.5467(3) 0.30929(14) 0.0711(2) 0.0278(6) Uani 1 1 d . . .
C8 C 0.7044(3) 0.29702(14) 0.1106(2) 0.0300(6) Uani 1 1 d . . .
H8 H 0.7820 0.3329 0.1065 0.036 Uiso 1 1 calc R U .
C9 C 0.7528(3) 0.23341(14) 0.1566(2) 0.0286(6) Uani 1 1 d . . .
C10 C 0.3511(3) 0.13530(15) 0.1288(2) 0.0367(7) Uani 1 1 d . . .
H10A H 0.2494 0.1493 0.0896 0.055 Uiso 1 1 calc R U .
H10B H 0.3348 0.1282 0.1991 0.055 Uiso 1 1 calc R U .
H10C H 0.3889 0.0914 0.1016 0.055 Uiso 1 1 calc R U .
C11 C 0.4999(4) 0.37789(16) 0.0188(2) 0.0413(8) Uani 1 1 d . . .
H11A H 0.3842 0.3777 -0.0045 0.062 Uiso 0.5 1 calc R U P
H11B H 0.5254 0.4169 0.0659 0.062 Uiso 0.5 1 calc R U P
H11C H 0.5595 0.3836 -0.0389 0.062 Uiso 0.5 1 calc R U P
H11D H 0.5952 0.4078 0.0195 0.062 Uiso 0.5 1 calc R U P
H11E H 0.4541 0.3686 -0.0509 0.062 Uiso 0.5 1 calc R U P
H11F H 0.4199 0.4019 0.0539 0.062 Uiso 0.5 1 calc R U P
C12 C 0.9258(3) 0.22223(17) 0.1998(3) 0.0469(9) Uani 1 1 d . . .
H12A H 0.9314 0.2089 0.2708 0.070 Uiso 1 1 calc R U .
H12B H 0.9863 0.2658 0.1941 0.070 Uiso 1 1 calc R U .
H12C H 0.9722 0.1847 0.1626 0.070 Uiso 1 1 calc R U .
C13 C 0.8782(3) -0.05362(13) 0.19884(18) 0.0227(5) Uani 1 1 d . . .
C14 C 1.0438(3) -0.05490(14) 0.22514(19) 0.0245(6) Uani 1 1 d . . .
C15 C 1.1237(3) -0.11715(14) 0.2069(2) 0.0266(6) Uani 1 1 d . . .
H15 H 1.2368 -0.1197 0.2252 0.032 Uiso 1 1 calc R U .
C16 C 1.0437(3) -0.17536(14) 0.16298(19) 0.0270(6) Uani 1 1 d . . .
C17 C 0.8782(3) -0.17173(14) 0.1401(2) 0.0300(6) Uani 1 1 d . . .
H17 H 0.8219 -0.2117 0.1112 0.036 Uiso 1 1 calc R U .
C18 C 0.7911(3) -0.11136(14) 0.1580(2) 0.0267(6) Uani 1 1 d . . .
C19 C 1.1330(3) 0.00795(15) 0.2717(2) 0.0369(7) Uani 1 1 d . . .
H19A H 1.1139 0.0484 0.2264 0.055 Uiso 1 1 calc R U .
H19B H 1.2484 -0.0024 0.2829 0.055 Uiso 1 1 calc R U .
H19C H 1.0950 0.0189 0.3360 0.055 Uiso 1 1 calc R U .
C20 C 1.1362(4) -0.24009(15) 0.1388(2) 0.0380(7) Uani 1 1 d . . .
H20A H 1.2126 -0.2275 0.0923 0.057 Uiso 1 1 calc R U .
H20B H 1.0611 -0.2756 0.1075 0.057 Uiso 1 1 calc R U .
H20C H 1.1948 -0.2591 0.2008 0.057 Uiso 1 1 calc R U .
C21 C 0.6095(3) -0.10869(17) 0.1362(3) 0.0421(8) Uani 1 1 d . . .
H21A H 0.5636 -0.1049 0.1996 0.063 Uiso 1 1 calc R U .
H21B H 0.5701 -0.1517 0.1010 0.063 Uiso 1 1 calc R U .
H21C H 0.5774 -0.0677 0.0940 0.063 Uiso 1 1 calc R U .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
Se1 Cu1 Se1 180.0 . 3_755
Cl1 Cu2 Cl1 180.00(5) 3_656 .
C1 Se1 Cu1 105.15(8) . .
C1 N1 C2 109.9(2) . .
C1 N1 C4 124.1(2) . .
C2 N1 C4 126.0(2) . .
C1 N2 C3 109.3(2) . .
C1 N2 C13 125.7(2) . .
C3 N2 C13 124.9(2) . .
N2 C1 N1 106.2(2) . .
N2 C1 Se1 130.95(19) . .
N1 C1 Se1 122.82(18) . .
C3 C2 N1 106.5(2) . .
C3 C2 H2 126.8 . .
N1 C2 H2 126.8 . .
C2 C3 N2 108.2(2) . .
C2 C3 H3 125.9 . .
N2 C3 H3 125.9 . .
C5 C4 C9 123.1(2) . .
C5 C4 N1 118.5(2) . .
C9 C4 N1 118.3(2) . .
C6 C5 C4 116.7(2) . .
C6 C5 C10 121.8(2) . .
C4 C5 C10 121.5(2) . .
C5 C6 C7 122.3(2) . .
C5 C6 H6 118.8 . .
C7 C6 H6 118.8 . .
C8 C7 C6 118.7(2) . .
C8 C7 C11 120.3(3) . .
C6 C7 C11 121.0(2) . .
C7 C8 C9 121.8(3) . .
C7 C8 H8 119.1 . .
C9 C8 H8 119.1 . .
C8 C9 C4 117.3(2) . .
C8 C9 C12 120.3(3) . .
C4 C9 C12 122.4(3) . .
C5 C10 H10A 109.5 . .
C5 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C5 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C7 C11 H11A 109.5 . .
C7 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C7 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C7 C11 H11D 109.5 . .
H11A C11 H11D 141.1 . .
H11B C11 H11D 56.3 . .
H11C C11 H11D 56.3 . .
C7 C11 H11E 109.5 . .
H11A C11 H11E 56.3 . .
H11B C11 H11E 141.1 . .
H11C C11 H11E 56.3 . .
H11D C11 H11E 109.5 . .
C7 C11 H11F 109.5 . .
H11A C11 H11F 56.3 . .
H11B C11 H11F 56.3 . .
H11C C11 H11F 141.1 . .
H11D C11 H11F 109.5 . .
H11E C11 H11F 109.5 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C14 C13 C18 122.9(2) . .
C14 C13 N2 118.6(2) . .
C18 C13 N2 118.4(2) . .
C13 C14 C15 117.2(2) . .
C13 C14 C19 121.3(2) . .
C15 C14 C19 121.5(2) . .
C16 C15 C14 122.3(2) . .
C16 C15 H15 118.9 . .
C14 C15 H15 118.9 . .
C17 C16 C15 118.1(2) . .
C17 C16 C20 121.4(3) . .
C15 C16 C20 120.5(2) . .
C16 C17 C18 122.3(3) . .
C16 C17 H17 118.9 . .
C18 C17 H17 118.9 . .
C13 C18 C17 117.1(2) . .
C13 C18 C21 120.9(3) . .
C17 C18 C21 122.0(3) . .
C14 C19 H19A 109.5 . .
C14 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C14 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C16 C20 H20A 109.5 . .
C16 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C16 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C18 C21 H21A 109.5 . .
C18 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C18 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Se1 2.2636(4) .
Cu1 Se1 2.2637(4) 3_755
Cu2 Cl1 2.0971(11) 3_656
Cu2 Cl1 2.0971(11) .
Se1 C1 1.867(3) .
N1 C1 1.359(3) .
N1 C2 1.393(3) .
N1 C4 1.443(3) .
N2 C1 1.353(3) .
N2 C3 1.387(3) .
N2 C13 1.452(3) .
C2 C3 1.342(4) .
C2 H2 0.9500 .
C3 H3 0.9500 .
C4 C5 1.395(3) .
C4 C9 1.398(4) .
C5 C6 1.391(4) .
C5 C10 1.498(4) .
C6 C7 1.392(4) .
C6 H6 0.9500 .
C7 C8 1.380(4) .
C7 C11 1.508(4) .
C8 C9 1.394(4) .
C8 H8 0.9500 .
C9 C12 1.506(4) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C11 H11D 0.9800 .
C11 H11E 0.9800 .
C11 H11F 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C14 1.389(3) .
C13 C18 1.391(4) .
C14 C15 1.397(4) .
C14 C19 1.502(4) .
C15 C16 1.386(4) .
C15 H15 0.9500 .
C16 C17 1.385(4) .
C16 C20 1.512(4) .
C17 C18 1.398(4) .
C17 H17 0.9500 .
C18 C21 1.514(4) .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C3 N2 C1 N1 0.5(3)
C13 N2 C1 N1 -176.6(2)
C3 N2 C1 Se1 -177.4(2)
C13 N2 C1 Se1 5.5(4)
C2 N1 C1 N2 -0.9(3)
C4 N1 C1 N2 177.2(2)
C2 N1 C1 Se1 177.21(18)
C4 N1 C1 Se1 -4.7(3)
Cu1 Se1 C1 N2 -24.3(3)
Cu1 Se1 C1 N1 158.09(19)
C1 N1 C2 C3 1.0(3)
C4 N1 C2 C3 -177.1(2)
N1 C2 C3 N2 -0.7(3)
C1 N2 C3 C2 0.1(3)
C13 N2 C3 C2 177.2(2)
C1 N1 C4 C5 100.6(3)
C2 N1 C4 C5 -81.6(3)
C1 N1 C4 C9 -76.7(3)
C2 N1 C4 C9 101.1(3)
C9 C4 C5 C6 0.0(4)
N1 C4 C5 C6 -177.2(2)
C9 C4 C5 C10 -179.7(3)
N1 C4 C5 C10 3.1(4)
C4 C5 C6 C7 1.6(4)
C10 C5 C6 C7 -178.6(3)
C5 C6 C7 C8 -2.2(4)
C5 C6 C7 C11 176.9(3)
C6 C7 C8 C9 1.1(4)
C11 C7 C8 C9 -178.0(3)
C7 C8 C9 C4 0.4(4)
C7 C8 C9 C12 -179.4(3)
C5 C4 C9 C8 -1.0(4)
N1 C4 C9 C8 176.2(2)
C5 C4 C9 C12 178.8(3)
N1 C4 C9 C12 -4.0(4)
C1 N2 C13 C14 90.8(3)
C3 N2 C13 C14 -85.8(3)
C1 N2 C13 C18 -91.1(3)
C3 N2 C13 C18 92.3(3)
C18 C13 C14 C15 1.4(4)
N2 C13 C14 C15 179.5(2)
C18 C13 C14 C19 -178.3(3)
N2 C13 C14 C19 -0.3(4)
C13 C14 C15 C16 1.0(4)
C19 C14 C15 C16 -179.2(3)
C14 C15 C16 C17 -2.3(4)
C14 C15 C16 C20 176.2(3)
C15 C16 C17 C18 1.3(4)
C20 C16 C17 C18 -177.3(3)
C14 C13 C18 C17 -2.4(4)
N2 C13 C18 C17 179.6(2)
C14 C13 C18 C21 176.4(3)
N2 C13 C18 C21 -1.6(4)
C16 C17 C18 C13 1.0(4)
C16 C17 C18 C21 -177.8(3)
