#------------------------------------------------------------------------------
#$Date: 2016-03-24 17:15:54 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179683 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/05/7000539.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_7000539
loop_
_publ_author_name
'Shishkov, Igor V.'
'Rominger, Frank'
'Hofmann, Peter'
_publ_section_title
;
 Reversible substrate binding at copper centers in neutral copper(i)
 carbene complexes derived from
 bis(3-tert-butylimidazole-2-ylidene)methane
;
_journal_issue                   8
_journal_name_full               'Dalton Transactions'
_journal_page_first              1428
_journal_paper_doi               10.1039/b813790k
_journal_year                    2009
_chemical_formula_sum            'C20 H35 Br2 Cu2 N5'
_chemical_formula_weight         632.43
_chemical_name_common            'in paper 7'
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 98.9950(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.65390(10)
_cell_length_b                   12.1517(2)
_cell_length_c                   22.0186(3)
_cell_measurement_temperature    200(2)
_cell_volume                     2551.26(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            26001
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    4.815
_exptl_absorpt_correction_T_max  0.5521
_exptl_absorpt_correction_T_min  0.4172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         5858
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0336
_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)+(0.0352P)²+1.3689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0823
_reflns_number_gt                4177
_reflns_number_total             5858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b813790k.txt
_cod_data_source_block           ivsh20
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7000539
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.91436(4) 0.65676(3) 0.159571(18) 0.03133(11) Uani 1 1 d . . .
Cu2 Cu 0.94425(4) 0.74905(3) 0.043791(19) 0.03377(12) Uani 1 1 d . . .
Br1 Br 0.94096(4) 0.85693(3) 0.139288(16) 0.04041(11) Uani 1 1 d . . .
Br2 Br 0.71311(4) 0.74343(3) -0.015565(15) 0.03419(10) Uani 1 1 d . . .
C1 C 1.0705(3) 0.5607(2) 0.18262(13) 0.0249(7) Uani 1 1 d . . .
N2 N 1.1238(3) 0.4948(2) 0.14157(11) 0.0255(6) Uani 1 1 d . . .
C3 C 1.2274(4) 0.4263(3) 0.16953(15) 0.0330(8) Uani 1 1 d . . .
H3 H 1.2789 0.3740 0.1500 0.040 Uiso 1 1 calc R . .
C4 C 1.2415(4) 0.4477(3) 0.22979(14) 0.0330(8) Uani 1 1 d . . .
H4 H 1.3045 0.4127 0.2614 0.040 Uiso 1 1 calc R . .
N5 N 1.1466(3) 0.5307(2) 0.23740(11) 0.0246(6) Uani 1 1 d . . .
C6 C 1.1330(4) 0.5765(3) 0.29967(14) 0.0314(8) Uani 1 1 d . . .
C7 C 1.0395(4) 0.6762(3) 0.29376(15) 0.0377(8) Uani 1 1 d . . .
H7A H 1.0759 0.7310 0.2677 0.056 Uiso 1 1 calc R . .
H7B H 1.0374 0.7076 0.3346 0.056 Uiso 1 1 calc R . .
H7C H 0.9444 0.6549 0.2752 0.056 Uiso 1 1 calc R . .
C8 C 1.0702(6) 0.4866(4) 0.33519(19) 0.0722(15) Uani 1 1 d . . .
H8A H 0.9819 0.4610 0.3112 0.108 Uiso 1 1 calc R . .
H8B H 1.0521 0.5161 0.3746 0.108 Uiso 1 1 calc R . .
H8C H 1.1360 0.4249 0.3426 0.108 Uiso 1 1 calc R . .
C9 C 1.2790(4) 0.6077(4) 0.33152(18) 0.0571(12) Uani 1 1 d . . .
H9A H 1.3388 0.5421 0.3362 0.086 Uiso 1 1 calc R . .
H9B H 1.2730 0.6387 0.3721 0.086 Uiso 1 1 calc R . .
H9C H 1.3194 0.6626 0.3067 0.086 Uiso 1 1 calc R . .
C10 C 1.0795(3) 0.5008(3) 0.07550(13) 0.0278(7) Uani 1 1 d . . .
H10A H 0.9795 0.5225 0.0671 0.033 Uiso 1 1 calc R . .
H10B H 1.0880 0.4269 0.0575 0.033 Uiso 1 1 calc R . .
C11 C 1.1157(3) 0.6824(3) 0.02828(13) 0.0276(7) Uani 1 1 d . . .
N12 N 1.1614(3) 0.5787(2) 0.04572(11) 0.0245(6) Uani 1 1 d . . .
C13 C 1.2918(3) 0.5576(3) 0.03013(15) 0.0339(8) Uani 1 1 d . . .
H13 H 1.3446 0.4917 0.0376 0.041 Uiso 1 1 calc R . .
C14 C 1.3291(3) 0.6487(3) 0.00229(15) 0.0368(8) Uani 1 1 d . . .
H14 H 1.4139 0.6595 -0.0137 0.044 Uiso 1 1 calc R . .
N15 N 1.2217(3) 0.7237(2) 0.00122(12) 0.0302(6) Uani 1 1 d . A .
C16 C 1.2203(3) 0.8342(3) -0.03009(15) 0.0364(8) Uani 1 1 d DU . .
C17 C 1.2029(17) 0.8142(8) -0.0973(3) 0.109(6) Uani 0.592(13) 1 d PDU A 1
H17A H 1.2770 0.7646 -0.1065 0.163 Uiso 0.592(13) 1 calc PR A 1
H17B H 1.2091 0.8843 -0.1188 0.163 Uiso 0.592(13) 1 calc PR A 1
H17C H 1.1111 0.7806 -0.1112 0.163 Uiso 0.592(13) 1 calc PR A 1
C18 C 1.3629(8) 0.8909(7) -0.0116(6) 0.078(4) Uani 0.592(13) 1 d PDU A 1
H18A H 1.3782 0.9055 0.0327 0.118 Uiso 0.592(13) 1 calc PR A 1
H18B H 1.3639 0.9606 -0.0340 0.118 Uiso 0.592(13) 1 calc PR A 1
H18C H 1.4376 0.8430 -0.0218 0.118 Uiso 0.592(13) 1 calc PR A 1
C19 C 1.1143(10) 0.9124(6) -0.0099(5) 0.079(5) Uani 0.592(13) 1 d PDU A 1
H19A H 1.1372 0.9250 0.0345 0.118 Uiso 0.592(13) 1 calc PR A 1
H19B H 1.0203 0.8804 -0.0195 0.118 Uiso 0.592(13) 1 calc PR A 1
H19C H 1.1168 0.9826 -0.0317 0.118 Uiso 0.592(13) 1 calc PR A 1
C17B C 1.261(2) 0.9112(9) 0.0183(5) 0.099(9) Uani 0.408(13) 1 d PDU A 2
H17D H 1.3557 0.8943 0.0389 0.148 Uiso 0.408(13) 1 calc PR A 2
H17E H 1.1952 0.9065 0.0481 0.148 Uiso 0.408(13) 1 calc PR A 2
H17F H 1.2583 0.9858 0.0013 0.148 Uiso 0.408(13) 1 calc PR A 2
C18B C 1.0741(9) 0.8484(12) -0.0663(7) 0.080(7) Uani 0.408(13) 1 d PDU A 2
H18D H 1.0583 0.7932 -0.0990 0.120 Uiso 0.408(13) 1 calc PR A 2
H18E H 1.0652 0.9222 -0.0844 0.120 Uiso 0.408(13) 1 calc PR A 2
H18F H 1.0045 0.8390 -0.0387 0.120 Uiso 0.408(13) 1 calc PR A 2
C19B C 1.3187(13) 0.8274(12) -0.0770(6) 0.070(5) Uani 0.408(13) 1 d PDU A 2
H19D H 1.2847 0.7715 -0.1079 0.104 Uiso 0.408(13) 1 calc PR A 2
H19E H 1.4127 0.8072 -0.0564 0.104 Uiso 0.408(13) 1 calc PR A 2
H19F H 1.3225 0.8989 -0.0972 0.104 Uiso 0.408(13) 1 calc PR A 2
N21 N 0.7039(3) 0.6398(3) 0.13265(14) 0.0363(7) Uani 1 1 d . . .
H21 H 0.695(3) 0.652(3) 0.0948(16) 0.034(10) Uiso 1 1 d . . .
C22 C 0.6144(4) 0.7222(3) 0.15602(19) 0.0502(10) Uani 1 1 d . . .
H22A H 0.5167 0.7141 0.1348 0.060 Uiso 1 1 calc R . .
H22B H 0.6472 0.7970 0.1476 0.060 Uiso 1 1 calc R . .
C23 C 0.6191(4) 0.7074(4) 0.22434(19) 0.0534(11) Uani 1 1 d . . .
H23A H 0.5561 0.7615 0.2396 0.064 Uiso 1 1 calc R . .
H23B H 0.7156 0.7207 0.2458 0.064 Uiso 1 1 calc R . .
C24 C 0.5737(5) 0.5917(4) 0.2381(2) 0.0653(13) Uani 1 1 d . . .
H24A H 0.5864 0.5806 0.2831 0.078 Uiso 1 1 calc R . .
H24B H 0.4729 0.5823 0.2217 0.078 Uiso 1 1 calc R . .
C25 C 0.6578(5) 0.5066(3) 0.20958(19) 0.0600(12) Uani 1 1 d . . .
H25A H 0.7565 0.5087 0.2302 0.072 Uiso 1 1 calc R . .
H25B H 0.6200 0.4324 0.2158 0.072 Uiso 1 1 calc R . .
C26 C 0.6523(4) 0.5273(3) 0.14211(18) 0.0529(11) Uani 1 1 d . . .
H26A H 0.7112 0.4727 0.1246 0.064 Uiso 1 1 calc R . .
H26B H 0.5547 0.5195 0.1207 0.064 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
_geom_angle_publ_flag
C1 Cu1 N21 136.47(13) . . ?
C1 Cu1 Br1 122.98(9) . . ?
N21 Cu1 Br1 99.94(9) . . ?
C1 Cu1 Cu2 107.03(9) . . ?
N21 Cu1 Cu2 90.89(8) . . ?
Br1 Cu1 Cu2 55.000(14) . . ?
C11 Cu2 Br2 130.08(9) . . ?
C11 Cu2 Br1 119.92(9) . . ?
Br2 Cu2 Br1 109.98(2) . . ?
C11 Cu2 Cu1 101.80(9) . . ?
Br2 Cu2 Cu1 105.113(18) . . ?
Br1 Cu2 Cu1 55.373(15) . . ?
Cu2 Br1 Cu1 69.627(16) . . ?
N5 C1 N2 102.9(2) . . ?
N5 C1 Cu1 133.9(2) . . ?
N2 C1 Cu1 123.0(2) . . ?
C1 N2 C3 112.5(2) . . ?
C1 N2 C10 123.4(3) . . ?
C3 N2 C10 124.1(3) . . ?
C4 C3 N2 106.4(3) . . ?
C3 C4 N5 107.1(3) . . ?
C1 N5 C4 111.2(2) . . ?
C1 N5 C6 126.7(3) . . ?
C4 N5 C6 122.1(2) . . ?
N5 C6 C7 110.8(2) . . ?
N5 C6 C9 107.8(3) . . ?
C7 C6 C9 109.8(3) . . ?
N5 C6 C8 107.6(3) . . ?
C7 C6 C8 109.9(3) . . ?
C9 C6 C8 110.9(3) . . ?
N2 C10 N12 112.9(2) . . ?
N15 C11 N12 103.4(3) . . ?
N15 C11 Cu2 130.7(2) . . ?
N12 C11 Cu2 125.9(2) . . ?
C11 N12 C13 111.5(3) . . ?
C11 N12 C10 123.5(3) . . ?
C13 N12 C10 124.9(3) . . ?
C14 C13 N12 106.3(3) . . ?
C13 C14 N15 107.4(3) . . ?
C11 N15 C14 111.4(3) . . ?
C11 N15 C16 125.2(3) . . ?
C14 N15 C16 123.3(3) . . ?
C17B C16 C17 145.9(7) . . ?
C17B C16 N15 105.1(5) . . ?
C17 C16 N15 107.6(4) . . ?
C17B C16 C19B 114.8(9) . . ?
C17 C16 C19B 45.1(6) . . ?
N15 C16 C19B 107.6(5) . . ?
C17B C16 C19 59.0(8) . . ?
C17 C16 C19 114.8(6) . . ?
N15 C16 C19 112.5(4) . . ?
C19B C16 C19 139.6(6) . . ?
C17B C16 C18B 116.1(9) . . ?
C17 C16 C18B 62.9(7) . . ?
N15 C16 C18B 106.4(4) . . ?
C19B C16 C18B 106.2(7) . . ?
C19 C16 C18B 57.8(7) . . ?
C17B C16 C18 51.7(7) . . ?
C17 C16 C18 107.1(7) . . ?
N15 C16 C18 109.6(4) . . ?
C19B C16 C18 64.7(6) . . ?
C19 C16 C18 105.0(6) . . ?
C18B C16 C18 144.0(6) . . ?
C22 N21 C26 110.5(3) . . ?
C22 N21 Cu1 116.4(3) . . ?
C26 N21 Cu1 113.3(2) . . ?
N21 C22 C23 109.9(3) . . ?
C22 C23 C24 110.2(4) . . ?
C25 C24 C23 111.2(3) . . ?
C26 C25 C24 111.0(4) . . ?
N21 C26 C25 109.5(3) . . ?
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 C1 1.912(3) . ?
Cu1 N21 2.036(3) . ?
Cu1 Br1 2.4936(6) . ?
Cu1 Cu2 2.8408(6) . ?
Cu2 C11 1.921(3) . ?
Cu2 Br2 2.4042(5) . ?
Cu2 Br1 2.4823(5) . ?
C1 N5 1.360(4) . ?
C1 N2 1.367(4) . ?
N2 C3 1.371(4) . ?
N2 C10 1.453(4) . ?
C3 C4 1.338(4) . ?
C4 N5 1.391(4) . ?
N5 C6 1.504(4) . ?
C6 C7 1.504(4) . ?
C6 C9 1.522(5) . ?
C6 C8 1.523(5) . ?
C10 N12 1.453(4) . ?
C11 N15 1.358(4) . ?
C11 N12 1.370(4) . ?
N12 C13 1.379(4) . ?
C13 C14 1.342(5) . ?
C14 N15 1.378(4) . ?
N15 C16 1.508(4) . ?
C16 C17B 1.427(9) . ?
C16 C17 1.484(8) . ?
C16 C19B 1.512(9) . ?
C16 C19 1.514(7) . ?
C16 C18B 1.518(8) . ?
C16 C18 1.537(7) . ?
N21 C22 1.467(5) . ?
N21 C26 1.481(5) . ?
C22 C23 1.509(6) . ?
C23 C24 1.517(6) . ?
C24 C25 1.511(6) . ?
C25 C26 1.500(6) . ?
