#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:39:25 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178718 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/29/4082976.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_4082976
loop_
_publ_author_name
'Lake, Benjamin R. M.'
'Willans, Charlotte E.'
_publ_section_title
;
 Remarkable Stability of Copper(II)--N-Heterocyclic Carbene Complexes Void
 of an Anionic Tether
;
_journal_issue                   8
_journal_name_full               Organometallics
_journal_page_first              2027
_journal_paper_doi               10.1021/om500178e
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C34 H34 Br2 Cu2 N6'
_chemical_formula_sum            'C34 H34 Br2 Cu2 N6'
_chemical_formula_weight         813.57
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 104.0190(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.7104(5)
_cell_length_b                   11.0398(6)
_cell_length_c                   15.3078(8)
_cell_measurement_reflns_used    4803
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.945
_cell_measurement_theta_min      2.2985
_cell_volume                     1592.13(15)
_computing_cell_refinement
;
APEX 2 software, Bruker Nonius 2004
;
_computing_data_collection
;
APEX 2 software, Bruker Nonius 2004
;
_computing_data_reduction
;
SAINT - Bruker Integration program embedded in
APEX 2 software, Bruker Nonius 2004
;
_computing_molecular_graphics    'ORTEP-III Version 1.08 (Farrugia, 2005)'
_computing_publication_material
;
enCIFer: A program for viewing, editing and visualising CIFs.
F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler,
J. Applied Cryst., 37, 331-334, 2004
;
_computing_structure_refinement
;
SHELXS-97 (Sheldrick, G. M.    Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, G. M.    Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean
;
120 microns
;
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'ApexII camera'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator
;
Mach3 kappa-type 4-circle goniostat.
;
_diffrn_radiation_source
;
Bruker Nonius FR591 rotating anode generator
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14966
_diffrn_reflns_theta_full        31.64
_diffrn_reflns_theta_max         31.64
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.880
_exptl_absorpt_correction_T_max  0.7729
_exptl_absorpt_correction_T_min  0.3437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
See Sheldrick, G. M. (2002). SADABS.
 University of Gottingen, Germany. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         5099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0285
_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)+(0.0306P)²+0.1450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0672
_reflns_number_gt                4033
_reflns_number_total             5099
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om500178e_si_002.cif
_cod_data_source_block           Complex3f
_cod_depositor_comments
'Adding full bibliography for 4082971--4082988.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4082976
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
Br1 Br 0.75499(2) -0.089063(18) 0.814711(13) 0.02068(6) Uani 1 1 d .
Cu1 Cu 0.87474(2) 0.010756(18) 0.952518(15) 0.01331(6) Uani 1 1 d .
N1 N 1.22139(17) 0.03269(13) 0.94722(10) 0.0137(3) Uani 1 1 d .
N2 N 1.06540(17) 0.19243(13) 0.89162(11) 0.0156(3) Uani 1 1 d .
N3 N 0.89078(18) 0.27237(14) 0.93284(11) 0.0171(3) Uani 1 1 d .
C1 C 1.3331(2) -0.03720(16) 0.94099(13) 0.0152(4) Uani 1 1 d .
H1 H 1.3688 -0.0938 0.9878 0.018 Uiso 1 1 calc R
C2 C 1.3978(2) -0.03051(17) 0.87006(13) 0.0186(4) Uani 1 1 d .
H2 H 1.4783 -0.0790 0.8693 0.022 Uiso 1 1 calc R
C3 C 1.3426(2) 0.04843(18) 0.80028(14) 0.0204(4) Uani 1 1 d .
H3 H 1.3828 0.0525 0.7496 0.024 Uiso 1 1 calc R
C4 C 1.2288(2) 0.12144(18) 0.80449(13) 0.0186(4) Uani 1 1 d .
H4 H 1.1894 0.1765 0.7573 0.022 Uiso 1 1 calc R
C5 C 1.1736(2) 0.11170(16) 0.88025(13) 0.0139(3) Uani 1 1 d .
C6 C 0.9587(2) 0.16413(15) 0.93327(12) 0.0139(3) Uani 1 1 d .
C7 C 1.0600(2) 0.31357(17) 0.86439(15) 0.0219(4) Uani 1 1 d .
H7 H 1.1217 0.3528 0.8337 0.026 Uiso 1 1 calc R
C8 C 0.9501(2) 0.36321(17) 0.89038(15) 0.0233(4) Uani 1 1 d .
H8 H 0.9188 0.4448 0.8815 0.028 Uiso 1 1 calc R
C9 C 0.7633(2) 0.29275(15) 0.96445(13) 0.0149(4) Uani 1 1 d .
C10 C 0.6334(2) 0.28796(16) 0.90190(13) 0.0159(4) Uani 1 1 d .
C11 C 0.5107(2) 0.31348(16) 0.93185(13) 0.0167(4) Uani 1 1 d .
H11 H 0.4206 0.3111 0.8902 0.020 Uiso 1 1 calc R
C12 C 0.5190(2) 0.34235(16) 1.02218(13) 0.0183(4) Uani 1 1 d .
C13 C 0.6516(2) 0.34720(16) 1.08149(13) 0.0195(4) Uani 1 1 d .
H13 H 0.6578 0.3688 1.1424 0.023 Uiso 1 1 calc R
C14 C 0.7768(2) 0.32160(16) 1.05525(13) 0.0181(4) Uani 1 1 d .
C15 C 0.6224(2) 0.25319(18) 0.80487(13) 0.0197(4) Uani 1 1 d .
H15A H 0.6943 0.2972 0.7823 0.030 Uiso 1 1 calc R
H15B H 0.5277 0.2741 0.7684 0.030 Uiso 1 1 calc R
H15C H 0.6379 0.1658 0.8010 0.030 Uiso 1 1 calc R
C16 C 0.3855(2) 0.36714(19) 1.05317(15) 0.0241(4) Uani 1 1 d .
H16A H 0.3568 0.2935 1.0798 0.036 Uiso 1 1 calc R
H16B H 0.3095 0.3920 1.0016 0.036 Uiso 1 1 calc R
H16C H 0.4035 0.4320 1.0982 0.036 Uiso 1 1 calc R
C17 C 0.9176(3) 0.32125(19) 1.12275(15) 0.0267(4) Uani 1 1 d .
H17A H 0.9115 0.3710 1.1747 0.040 Uiso 1 1 calc R
H17B H 0.9904 0.3545 1.0950 0.040 Uiso 1 1 calc R
H17C H 0.9429 0.2380 1.1426 0.040 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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C6 Cu1 N1 127.47(7) . 3_757
C6 Cu1 Br1 113.48(6) . .
N1 Cu1 Br1 109.83(5) 3_757 .
C6 Cu1 Cu1 77.69(6) . 3_757
N1 Cu1 Cu1 95.59(5) 3_757 3_757
Br1 Cu1 Cu1 130.780(14) . 3_757
C5 N1 C1 116.87(15) . .
C5 N1 Cu1 126.33(12) . 3_757
C1 N1 Cu1 116.12(12) . 3_757
C6 N2 C7 112.16(15) . .
C6 N2 C5 125.17(15) . .
C7 N2 C5 122.61(15) . .
C6 N3 C8 112.24(15) . .
C6 N3 C9 125.77(14) . .
C8 N3 C9 121.76(15) . .
N1 C1 C2 123.35(18) . .
N1 C1 H1 118.3 . .
C2 C1 H1 118.3 . .
C1 C2 C3 118.43(18) . .
C1 C2 H2 120.8 . .
C3 C2 H2 120.8 . .
C4 C3 C2 119.75(16) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
C3 C4 C5 117.82(18) . .
C3 C4 H4 121.1 . .
C5 C4 H4 121.1 . .
N1 C5 C4 123.68(17) . .
N1 C5 N2 116.36(15) . .
C4 C5 N2 119.88(17) . .
N3 C6 N2 102.48(14) . .
N3 C6 Cu1 123.14(13) . .
N2 C6 Cu1 131.43(13) . .
C8 C7 N2 106.07(16) . .
C8 C7 H7 127.0 . .
N2 C7 H7 127.0 . .
C7 C8 N3 107.02(17) . .
C7 C8 H8 126.5 . .
N3 C8 H8 126.5 . .
C10 C9 C14 122.97(17) . .
C10 C9 N3 118.05(16) . .
C14 C9 N3 118.92(18) . .
C9 C10 C11 117.93(17) . .
C9 C10 C15 121.57(16) . .
C11 C10 C15 120.49(19) . .
C12 C11 C10 121.11(19) . .
C12 C11 H11 119.4 . .
C10 C11 H11 119.4 . .
C13 C12 C11 118.52(17) . .
C13 C12 C16 121.32(18) . .
C11 C12 C16 120.2(2) . .
C12 C13 C14 122.60(18) . .
C12 C13 H13 118.7 . .
C14 C13 H13 118.7 . .
C13 C14 C9 116.87(19) . .
C13 C14 C17 120.87(18) . .
C9 C14 C17 122.23(18) . .
C10 C15 H15A 109.5 . .
C10 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C10 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C12 C16 H16A 109.5 . .
C12 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C12 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C14 C17 H17A 109.5 . .
C14 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C14 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 Cu1 2.4141(3) .
Cu1 C6 1.9327(17) .
Cu1 N1 2.0375(14) 3_757
Cu1 Cu1 2.5247(5) 3_757
N1 C5 1.340(2) .
N1 C1 1.353(2) .
N1 Cu1 2.0374(14) 3_757
N2 C6 1.377(2) .
N2 C7 1.398(2) .
N2 C5 1.420(2) .
N3 C6 1.364(2) .
N3 C8 1.394(2) .
N3 C9 1.451(2) .
C1 C2 1.382(2) .
C1 H1 0.9500 .
C2 C3 1.382(3) .
C2 H2 0.9500 .
C3 C4 1.382(3) .
C3 H3 0.9500 .
C4 C5 1.395(2) .
C4 H4 0.9500 .
C7 C8 1.343(3) .
C7 H7 0.9500 .
C8 H8 0.9500 .
C9 C10 1.388(3) .
C9 C14 1.401(3) .
C10 C11 1.405(2) .
C10 C15 1.513(3) .
C11 C12 1.402(3) .
C11 H11 0.9500 .
C12 C13 1.385(3) .
C12 C16 1.510(3) .
C13 C14 1.399(3) .
C13 H13 0.9500 .
C14 C17 1.501(3) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 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
_geom_torsion_site_symmetry_1
C5 N1 C1 C2 -0.1(3) .
Cu1 N1 C1 C2 171.06(15) 3_757
N1 C1 C2 C3 -2.4(3) .
C1 C2 C3 C4 2.5(3) .
C2 C3 C4 C5 -0.2(3) .
C1 N1 C5 C4 2.6(3) .
Cu1 N1 C5 C4 -167.51(15) 3_757
C1 N1 C5 N2 -174.21(16) .
Cu1 N1 C5 N2 15.6(2) 3_757
C3 C4 C5 N1 -2.5(3) .
C3 C4 C5 N2 174.22(18) .
C6 N2 C5 N1 -35.3(3) .
C7 N2 C5 N1 141.69(19) .
C6 N2 C5 C4 147.70(19) .
C7 N2 C5 C4 -35.3(3) .
C8 N3 C6 N2 1.7(2) .
C9 N3 C6 N2 176.25(18) .
C8 N3 C6 Cu1 -160.85(15) .
C9 N3 C6 Cu1 13.7(3) .
C7 N2 C6 N3 -1.6(2) .
C5 N2 C6 N3 175.66(18) .
C7 N2 C6 Cu1 158.79(16) .
C5 N2 C6 Cu1 -23.9(3) .
N1 Cu1 C6 N3 -49.5(2) 3_757
Br1 Cu1 C6 N3 93.57(16) .
Cu1 Cu1 C6 N3 -137.08(17) 3_757
N1 Cu1 C6 N2 153.54(16) 3_757
Br1 Cu1 C6 N2 -63.4(2) .
Cu1 Cu1 C6 N2 65.92(18) 3_757
C6 N2 C7 C8 1.0(3) .
C5 N2 C7 C8 -176.4(2) .
N2 C7 C8 N3 0.1(3) .
C6 N3 C8 C7 -1.2(3) .
C9 N3 C8 C7 -176.0(2) .
C6 N3 C9 C10 -94.2(2) .
C8 N3 C9 C10 79.8(2) .
C6 N3 C9 C14 88.6(2) .
C8 N3 C9 C14 -97.3(2) .
C14 C9 C10 C11 0.1(3) .
N3 C9 C10 C11 -176.98(15) .
C14 C9 C10 C15 -178.33(17) .
N3 C9 C10 C15 4.6(2) .
C9 C10 C11 C12 -0.3(3) .
C15 C10 C11 C12 178.11(16) .
C10 C11 C12 C13 1.0(3) .
C10 C11 C12 C16 -178.84(17) .
C11 C12 C13 C14 -1.6(3) .
C16 C12 C13 C14 178.29(17) .
C12 C13 C14 C9 1.3(3) .
C12 C13 C14 C17 -176.62(18) .
C10 C9 C14 C13 -0.6(3) .
N3 C9 C14 C13 176.46(15) .
C10 C9 C14 C17 177.37(17) .
N3 C9 C14 C17 -5.6(3) .
