#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:24:27 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179894 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/90/7019013.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_7019013
loop_
_publ_author_name
'Gómez-Suárez, Adrián'
'Ramón, Rubén S'
'Slawin, Alexandra M. Z.'
'Nolan, Steven P.'
_publ_section_title
;
 Synthetic routes to [Au(NHC)(OH)] (NHC = N-heterocyclic carbene)
 complexes.
;
_journal_issue                   18
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5461
_journal_page_last               5463
_journal_paper_doi               10.1039/c2dt30294b
_journal_volume                  41
_journal_year                    2012
_chemical_formula_moiety         'C27 H39 Au N2 O,C5 H12'
_chemical_formula_sum            'C32 H51 Au N2 O'
_chemical_formula_weight         676.71
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 115.108(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.426(7)
_cell_length_b                   9.336(2)
_cell_length_c                   16.544(5)
_cell_measurement_reflns_used    5783
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      2.4
_cell_volume                     3136.5(15)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_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      93(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9206
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.32
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    4.715
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.383
_refine_diff_density_min         -1.221
_refine_diff_density_rms         0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2845
_refine_ls_number_restraints     133
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0548P)²+20.8866P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                2746
_reflns_number_total             2845
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt30294b.txt
_cod_data_source_block           4
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3136.5(16)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7019013
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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 0.0000 0.02324(3) 0.2500 0.02168(15) Uani 1 2 d SU
O1 O 0.0000 -0.1930(8) 0.2500 0.0400(16) Uani 1 2 d SDU
H1O H -0.0476(11) -0.203(16) 0.230(9) 0.048 Uiso 0.50 1 d PD
C1 C 0.0000 0.2349(9) 0.2500 0.0200(17) Uani 1 2 d SU
N2 N 0.0076(2) 0.3176(5) 0.1892(3) 0.0205(10) Uani 1 1 d U
C3 C 0.0130(3) 0.4705(6) 0.2138(4) 0.0245(14) Uani 1 1 d U
H3A H -0.0146 0.5310 0.1623 0.029 Uiso 1 1 calc R
H3B H 0.0592 0.5040 0.2379 0.029 Uiso 1 1 calc R
C4 C 0.0267(3) 0.2673(6) 0.1208(4) 0.0229(12) Uani 1 1 d U
C5 C 0.0906(3) 0.2222(7) 0.1429(4) 0.0272(13) Uani 1 1 d U
C6 C 0.1057(4) 0.1787(8) 0.0727(5) 0.0388(16) Uani 1 1 d U
H6A H 0.1496 0.1518 0.0852 0.047 Uiso 1 1 calc R
C7 C 0.0589(4) 0.1742(9) -0.0132(5) 0.0444(18) Uani 1 1 d U
H7A H 0.0701 0.1397 -0.0590 0.053 Uiso 1 1 calc R
C8 C -0.0044(3) 0.2193(8) -0.0341(5) 0.0364(16) Uani 1 1 d U
H8A H -0.0361 0.2183 -0.0945 0.044 Uiso 1 1 calc R
C9 C -0.0226(3) 0.2669(7) 0.0328(4) 0.0280(14) Uani 1 1 d U
C10 C 0.1444(3) 0.2229(8) 0.2385(4) 0.0324(15) Uani 1 1 d U
H10A H 0.1237 0.2557 0.2782 0.039 Uiso 1 1 calc R
C11 C 0.1992(4) 0.3268(10) 0.2503(6) 0.054(2) Uani 1 1 d U
H11A H 0.1806 0.4224 0.2309 0.081 Uiso 1 1 calc R
H11B H 0.2220 0.2953 0.2144 0.081 Uiso 1 1 calc R
H11C H 0.2304 0.3301 0.3134 0.081 Uiso 1 1 calc R
C12 C 0.1716(4) 0.0712(10) 0.2689(6) 0.052(2) Uani 1 1 d U
H12A H 0.2061 0.0750 0.3301 0.078 Uiso 1 1 calc R
H12B H 0.1901 0.0335 0.2291 0.078 Uiso 1 1 calc R
H12C H 0.1359 0.0085 0.2667 0.078 Uiso 1 1 calc R
C13 C -0.0917(3) 0.3139(8) 0.0113(5) 0.0360(16) Uani 1 1 d U
H13A H -0.0893 0.3780 0.0610 0.043 Uiso 1 1 calc R
C14 C -0.1226(5) 0.4017(11) -0.0750(6) 0.062(2) Uani 1 1 d U
H14A H -0.0937 0.4825 -0.0718 0.093 Uiso 1 1 calc R
H14B H -0.1656 0.4380 -0.0825 0.093 Uiso 1 1 calc R
H14C H -0.1281 0.3409 -0.1260 0.093 Uiso 1 1 calc R
C15 C -0.1364(4) 0.1858(9) 0.0088(5) 0.0460(18) Uani 1 1 d U
H15A H -0.1161 0.1322 0.0649 0.069 Uiso 1 1 calc R
H15B H -0.1418 0.1227 -0.0412 0.069 Uiso 1 1 calc R
H15C H -0.1796 0.2215 0.0011 0.069 Uiso 1 1 calc R
C21 C 0.3639(13) 0.195(3) 0.1884(18) 0.086(7) Uani 0.50 1 d PU
C22 C 0.3252(12) 0.210(3) 0.1291(18) 0.083(6) Uani 0.50 1 d PU
C23 C 0.2749(15) 0.291(4) 0.044(2) 0.084(8) Uani 0.50 1 d PU
C24 C 0.252(3) 0.323(5) 0.016(3) 0.149(16) Uani 0.50 1 d PU
C25 C 0.1731(13) 0.405(3) -0.0912(18) 0.095(7) Uani 0.50 1 d PU
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'
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 O1 180.000(1) . .
Au1 O1 H1O 96(9) . .
N2 C1 N2 109.4(7) 2 .
N2 C1 Au1 125.3(4) 2 .
N2 C1 Au1 125.3(4) . .
C1 N2 C4 125.2(5) . .
C1 N2 C3 111.9(5) . .
C4 N2 C3 120.9(5) . .
N2 C3 C3 101.6(3) . 2
N2 C3 H3A 111.4 . .
C3 C3 H3A 111.4 2 .
N2 C3 H3B 111.4 . .
C3 C3 H3B 111.4 2 .
H3A C3 H3B 109.3 . .
C5 C4 C9 122.9(5) . .
C5 C4 N2 120.5(5) . .
C9 C4 N2 116.6(5) . .
C4 C5 C6 117.1(6) . .
C4 C5 C10 123.1(6) . .
C6 C5 C10 119.8(6) . .
C7 C6 C5 121.5(7) . .
C7 C6 H6A 119.2 . .
C5 C6 H6A 119.2 . .
C6 C7 C8 120.6(7) . .
C6 C7 H7A 119.7 . .
C8 C7 H7A 119.7 . .
C7 C8 C9 120.8(7) . .
C7 C8 H8A 119.6 . .
C9 C8 H8A 119.6 . .
C4 C9 C8 117.0(6) . .
C4 C9 C13 121.6(6) . .
C8 C9 C13 121.5(6) . .
C11 C10 C5 112.2(6) . .
C11 C10 C12 111.1(6) . .
C5 C10 C12 111.3(6) . .
C11 C10 H10A 107.3 . .
C5 C10 H10A 107.3 . .
C12 C10 H10A 107.3 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C9 C13 C14 112.9(6) . .
C9 C13 C15 111.8(6) . .
C14 C13 C15 110.9(6) . .
C9 C13 H13A 106.9 . .
C14 C13 H13A 106.9 . .
C15 C13 H13A 106.9 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C22 C21 C25 45(2) . 7
C21 C22 C25 100(3) . 7
C21 C22 C23 159(3) . .
C25 C22 C23 97(2) 7 .
C24 C23 C24 82(7) . 7
C24 C23 C23 60(6) . 7
C24 C23 C23 22(2) 7 7
C24 C23 C22 168(7) . .
C24 C23 C22 101(3) 7 .
C23 C23 C22 122(3) 7 .
C23 C24 C23 98(7) . 7
C23 C24 C24 74(7) . 7
C23 C24 C24 24(2) 7 7
C23 C24 C25 171(9) . .
C23 C24 C25 74(3) 7 .
C24 C24 C25 98(5) 7 .
C22 C25 C21 34.8(15) 7 7
C22 C25 C24 85(2) 7 .
C21 C25 C24 120(2) 7 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Au1 C1 1.976(8) .
Au1 O1 2.019(7) .
O1 H1O 0.9800(11) .
C1 N2 1.336(7) 2
C1 N2 1.336(7) .
N2 C4 1.448(7) .
N2 C3 1.476(7) .
C3 C3 1.537(13) 2
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.385(8) .
C4 C9 1.405(8) .
C5 C6 1.401(9) .
C5 C10 1.529(9) .
C6 C7 1.362(10) .
C6 H6A 0.9500 .
C7 C8 1.376(10) .
C7 H7A 0.9500 .
C8 C9 1.403(9) .
C8 H8A 0.9500 .
C9 C13 1.502(9) .
C10 C11 1.511(11) .
C10 C12 1.540(11) .
C10 H10A 1.0000 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C14 1.533(11) .
C13 C15 1.550(10) .
C13 H13A 1.0000 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C21 C22 1.01(3) .
C21 C25 1.73(4) 7
C22 C25 1.25(3) 7
C22 C23 1.58(4) .
C23 C24 0.60(5) .
C23 C24 1.41(4) 7
C23 C23 1.60(6) 7
C24 C23 1.41(4) 7
C24 C24 1.45(9) 7
C24 C25 2.05(6) .
C25 C22 1.25(3) 7
C25 C21 1.73(4) 7
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
O1 Au1 C1 N2 57(100) . 2
O1 Au1 C1 N2 -123(100) . .
N2 C1 N2 C4 170.4(6) 2 .
Au1 C1 N2 C4 -9.6(6) . .
N2 C1 N2 C3 6.7(3) 2 .
Au1 C1 N2 C3 -173.3(3) . .
C1 N2 C3 C3 -16.1(8) . 2
C4 N2 C3 C3 179.4(6) . 2
C1 N2 C4 C5 -71.9(7) . .
C3 N2 C4 C5 90.5(7) . .
C1 N2 C4 C9 108.0(6) . .
C3 N2 C4 C9 -89.7(7) . .
C9 C4 C5 C6 1.9(9) . .
N2 C4 C5 C6 -178.3(6) . .
C9 C4 C5 C10 179.8(6) . .
N2 C4 C5 C10 -0.4(9) . .
C4 C5 C6 C7 -3.1(10) . .
C10 C5 C6 C7 178.8(7) . .
C5 C6 C7 C8 3.2(12) . .
C6 C7 C8 C9 -1.9(12) . .
C5 C4 C9 C8 -0.7(9) . .
N2 C4 C9 C8 179.5(6) . .
C5 C4 C9 C13 178.8(6) . .
N2 C4 C9 C13 -1.0(9) . .
C7 C8 C9 C4 0.6(10) . .
C7 C8 C9 C13 -178.9(7) . .
C4 C5 C10 C11 -114.8(7) . .
C6 C5 C10 C11 63.1(9) . .
C4 C5 C10 C12 119.9(7) . .
C6 C5 C10 C12 -62.2(8) . .
C4 C9 C13 C14 140.4(7) . .
C8 C9 C13 C14 -40.1(9) . .
C4 C9 C13 C15 -93.7(8) . .
C8 C9 C13 C15 85.8(8) . .
