#------------------------------------------------------------------------------
#$Date: 2016-03-21 12:17:54 +0100 (lun 21 de mar de 2016) $
#$Revision: 178697 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/08/4080875.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_4080875
loop_
_publ_author_name
'Reeds, Jonathan P.'
'Whitwood, Adrian C.'
'Healy, Mark P.'
'Fairlamb, Ian J. S.'
_publ_section_title
;
 Synthesis and Reactivity of N-Heterocyclic Carbene Gold(I) and Gold(III)
 Imidate Complexes and Their Catalytic Activity in 1,5-Enyne
 Cycloisomerization
;
_journal_issue                   10
_journal_name_full               Organometallics
_journal_page_first              3108
_journal_paper_doi               10.1021/om400310z
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C19 H24 Au Br2 N3 O2'
_chemical_formula_sum            'C19 H24 Au Br2 N3 O2'
_chemical_formula_weight         683.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.8674(17)
_cell_length_b                   13.3922(11)
_cell_length_c                   8.3251(7)
_cell_measurement_reflns_used    8183
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.55
_cell_volume                     2215.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20843
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    10.267
_exptl_absorpt_correction_T_max  0.735
_exptl_absorpt_correction_T_min  0.382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.03; (Sheldrick)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.049
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.581
_refine_diff_density_min         -2.380
_refine_diff_density_rms         0.202
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2847
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0319
_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)+(0.0294P)²+6.3064P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0871
_reflns_number_gt                2631
_reflns_number_total             2847
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400310z_si_002.cif
_cod_data_source_block           ijf0806a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.3.1 from 2005-06-27.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               4080875
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
Au1 Au 0.271878(10) 0.2500 0.03284(2) 0.01314(9) Uani 1 2 d S
Br1 Br 0.26649(3) 0.2500 -0.25910(6) 0.02111(14) Uani 1 2 d S
Br2 Br 0.27896(3) 0.2500 0.32436(6) 0.02094(14) Uani 1 2 d S
C1 C 0.1713(3) 0.2500 0.0429(6) 0.0187(12) Uani 1 2 d S
C2 C 0.0640(2) 0.2002(4) 0.0542(6) 0.0300(10) Uani 1 1 d .
H2 H 0.0253 0.1585 0.0578 0.036 Uiso 1 1 calc R
C3 C 0.1468(2) 0.0580(3) 0.0297(5) 0.0197(8) Uani 1 1 d .
C4 C 0.2195(3) 0.0343(4) 0.0622(9) 0.0467(16) Uani 1 1 d .
H4A H 0.2479 0.0685 -0.0168 0.070 Uiso 1 1 calc R
H4B H 0.2266 -0.0380 0.0542 0.070 Uiso 1 1 calc R
H4C H 0.2315 0.0569 0.1705 0.070 Uiso 1 1 calc R
C5 C 0.1300(3) 0.0296(4) -0.1422(6) 0.0421(13) Uani 1 1 d .
H5A H 0.1572 0.0697 -0.2162 0.063 Uiso 1 1 calc R
H5B H 0.0821 0.0421 -0.1625 0.063 Uiso 1 1 calc R
H5C H 0.1397 -0.0414 -0.1589 0.063 Uiso 1 1 calc R
C6 C 0.1034(3) -0.0004(4) 0.1458(8) 0.0488(16) Uani 1 1 d .
H6A H 0.1131 -0.0719 0.1349 0.073 Uiso 1 1 calc R
H6B H 0.0558 0.0118 0.1218 0.073 Uiso 1 1 calc R
H6C H 0.1132 0.0210 0.2559 0.073 Uiso 1 1 calc R
C7 C 0.4128(2) 0.1645(3) 0.0162(4) 0.0169(8) Uani 1 1 d .
C8 C 0.4844(2) 0.1976(3) 0.0078(4) 0.0174(8) Uani 1 1 d .
C9 C 0.5434(2) 0.1443(3) 0.0017(5) 0.0220(8) Uani 1 1 d .
H9 H 0.5433 0.0734 0.0003 0.026 Uiso 1 1 calc R
C10 C 0.6037(2) 0.1982(3) -0.0025(5) 0.0252(9) Uani 1 1 d .
H10 H 0.6453 0.1633 -0.0054 0.030 Uiso 1 1 calc R
N1 N 0.13003(19) 0.1683(3) 0.0480(4) 0.0202(7) Uani 1 1 d .
N2 N 0.3732(3) 0.2500 0.0218(5) 0.0184(10) Uani 1 2 d S
O1 O 0.39131(16) 0.0795(2) 0.0200(4) 0.0231(6) 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'
O O 0.0106 0.0060 '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'
Au Au -2.0133 8.8022 '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
C1 Au1 N2 179.79(19) . .
C1 Au1 Br2 90.92(14) . .
N2 Au1 Br2 89.29(13) . .
C1 Au1 Br1 89.88(14) . .
N2 Au1 Br1 89.91(13) . .
Br2 Au1 Br1 179.20(2) . .
N1 C1 N1 106.3(5) 7_565 .
N1 C1 Au1 126.9(3) 7_565 .
N1 C1 Au1 126.9(3) . .
C2 C2 N1 108.0(3) 7_565 .
C2 C2 H2 126.0 7_565 .
N1 C2 H2 126.0 . .
C4 C3 C6 108.9(5) . .
C4 C3 C5 109.2(4) . .
C6 C3 C5 110.3(4) . .
C4 C3 N1 113.4(4) . .
C6 C3 N1 108.2(4) . .
C5 C3 N1 106.8(3) . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C3 C5 H5A 109.5 . .
C3 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C3 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C3 C6 H6A 109.5 . .
C3 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C3 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
O1 C7 N2 124.8(4) . .
O1 C7 C8 127.9(4) . .
N2 C7 C8 107.3(4) . .
C9 C8 C8 121.3(2) . 7_565
C9 C8 C7 131.4(4) . .
C8 C8 C7 107.3(2) 7_565 .
C8 C9 C10 117.6(4) . .
C8 C9 H9 121.2 . .
C10 C9 H9 121.2 . .
C10 C10 C9 121.1(2) 7_565 .
C10 C10 H10 119.5 7_565 .
C9 C10 H10 119.5 . .
C1 N1 C2 108.8(4) . .
C1 N1 C3 129.9(4) . .
C2 N1 C3 120.8(4) . .
C7 N2 C7 110.9(5) 7_565 .
C7 N2 Au1 124.5(3) 7_565 .
C7 N2 Au1 124.5(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Au1 C1 2.001(6) .
Au1 N2 2.016(5) .
Au1 Br2 2.4310(6) .
Au1 Br1 2.4328(6) .
C1 N1 1.367(5) 7_565
C1 N1 1.367(5) .
C2 C2 1.333(10) 7_565
C2 N1 1.381(6) .
C2 H2 0.9500 .
C3 C4 1.504(7) .
C3 C6 1.514(6) .
C3 C5 1.518(6) .
C3 N1 1.522(5) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 O1 1.217(5) .
C7 N2 1.389(5) .
C7 C8 1.491(6) .
C8 C9 1.374(6) .
C8 C8 1.403(8) 7_565
C9 C10 1.398(6) .
C9 H9 0.9500 .
C10 C10 1.388(9) 7_565
C10 H10 0.9500 .
N2 C7 1.389(5) 7_565
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
_geom_torsion_site_symmetry_4
Br2 Au1 C1 N1 89.5(4) . 7_565
Br1 Au1 C1 N1 -90.5(4) . 7_565
Br2 Au1 C1 N1 -89.5(4) . .
Br1 Au1 C1 N1 90.5(4) . .
O1 C7 C8 C9 0.3(7) . .
N2 C7 C8 C9 179.3(4) . .
O1 C7 C8 C8 -179.3(3) . 7_565
N2 C7 C8 C8 -0.4(3) . 7_565
C8 C8 C9 C10 0.8(5) 7_565 .
C7 C8 C9 C10 -178.8(4) . .
C8 C9 C10 C10 -0.8(5) . 7_565
N1 C1 N1 C2 0.8(6) 7_565 .
Au1 C1 N1 C2 -180.0(4) . .
N1 C1 N1 C3 173.3(2) 7_565 .
Au1 C1 N1 C3 -7.4(7) . .
C2 C2 N1 C1 -0.5(3) 7_565 .
C2 C2 N1 C3 -173.9(3) 7_565 .
C4 C3 N1 C1 21.2(6) . .
C6 C3 N1 C1 142.1(5) . .
C5 C3 N1 C1 -99.2(5) . .
C4 C3 N1 C2 -167.0(5) . .
C6 C3 N1 C2 -46.1(5) . .
C5 C3 N1 C2 72.6(5) . .
O1 C7 N2 C7 179.6(2) . 7_565
C8 C7 N2 C7 0.6(5) . 7_565
O1 C7 N2 Au1 -1.3(6) . .
C8 C7 N2 Au1 179.6(3) . .
Br2 Au1 N2 C7 -90.5(4) . 7_565
Br1 Au1 N2 C7 89.5(4) . 7_565
Br2 Au1 N2 C7 90.5(4) . .
Br1 Au1 N2 C7 -89.5(4) . .
