#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:55:43 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179084 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/46/4304645.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_4304645
loop_
_publ_author_name
'Manoja K. Samantaray'
'Keliang Pang'
'Mobin M. Shaikh'
'Prasenjit Ghosh'
_publ_section_title
;
From Large 12-Membered Macrometallacycles to Ionic (NHC)2M+Cl- Type
Complexes of Gold and Silver by Modulation of the N-Substituent of
Amido-Functionalized N-Heterocyclic Carbene (NHC) Ligands
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4153
_journal_page_last               4165
_journal_paper_doi               10.1021/ic702186g
_journal_volume                  47
_journal_year                    2008
_chemical_formula_sum            'C20 H28 Au N3 O'
_chemical_formula_weight         523.42
_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                 98.704(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.840(2)
_cell_length_b                   9.1945(18)
_cell_length_c                   21.0125(12)
_cell_measurement_reflns_used    10703
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.1400
_cell_measurement_theta_min      2.9855
_cell_volume                     2070.2(6)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 15.9948
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19877
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    7.118
_exptl_absorpt_correction_T_max  0.2692
_exptl_absorpt_correction_T_min  0.1896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         2.786
_refine_diff_density_min         -1.516
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    RIDING
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         6004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0287
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0298P)²+3.1823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0640
_reflns_number_gt                4623
_reflns_number_total             6004
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic702186g-file008.cif
_cod_data_source_block           pg057
_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_cell_volume        2070.1(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4304645
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.949668(12) -0.135077(14) -0.073507(7) 0.02228(5) Uani 1 1 d . . .
O1 O 0.6954(2) 0.0337(3) 0.11834(14) 0.0314(6) Uani 1 1 d . . .
N1 N 0.6685(3) -0.1533(3) -0.09228(15) 0.0253(7) Uani 1 1 d . . .
N2 N 0.7449(3) -0.1368(3) 0.00774(14) 0.0211(6) Uani 1 1 d . . .
N3 N 0.8737(3) 0.1412(3) 0.09548(14) 0.0202(6) Uani 1 1 d . . .
C1 C 0.7779(3) -0.1392(4) -0.05204(17) 0.0209(7) Uani 1 1 d . . .
C2 C 0.6169(3) -0.1479(4) 0.00474(19) 0.0271(8) Uani 1 1 d . . .
H2 H 0.5727 -0.1471 0.0394 0.032 Uiso 1 1 calc R . .
C3 C 0.5683(3) -0.1601(4) -0.0582(2) 0.0291(8) Uani 1 1 d . . .
H3 H 0.4845 -0.1708 -0.0753 0.035 Uiso 1 1 calc R . .
C4 C 0.6559(4) -0.1584(5) -0.16301(19) 0.0347(9) Uani 1 1 d . . .
H4 H 0.7389 -0.1455 -0.1753 0.042 Uiso 1 1 calc R . .
C5 C 0.6064(8) -0.3057(8) -0.1871(3) 0.089(3) Uani 1 1 d . . .
H5A H 0.6653 -0.3798 -0.1708 0.134 Uiso 1 1 calc R . .
H5B H 0.5944 -0.3068 -0.2333 0.134 Uiso 1 1 calc R . .
H5C H 0.5282 -0.3240 -0.1723 0.134 Uiso 1 1 calc R . .
C6 C 0.5733(5) -0.0330(8) -0.1914(3) 0.071(2) Uani 1 1 d . . .
H6A H 0.4925 -0.0413 -0.1782 0.106 Uiso 1 1 calc R . .
H6B H 0.5645 -0.0364 -0.2376 0.106 Uiso 1 1 calc R . .
H6C H 0.6108 0.0577 -0.1764 0.106 Uiso 1 1 calc R . .
C7 C 0.8316(3) -0.1149(4) 0.06795(17) 0.0235(7) Uani 1 1 d . . .
H7A H 0.9169 -0.1102 0.0592 0.028 Uiso 1 1 calc R . .
H7B H 0.8252 -0.1949 0.0974 0.028 Uiso 1 1 calc R . .
C8 C 0.7953(3) 0.0296(4) 0.09773(17) 0.0228(7) Uani 1 1 d . . .
C9 C 0.8274(3) 0.2797(4) 0.11432(18) 0.0238(7) Uani 1 1 d . . .
C10 C 0.8404(4) 0.3180(5) 0.1794(2) 0.0335(9) Uani 1 1 d . . .
C11 C 0.9053(5) 0.2186(6) 0.2316(2) 0.0531(14) Uani 1 1 d . . .
H11 H 0.9386 0.1356 0.2104 0.064 Uiso 1 1 calc R . .
C12 C 0.8127(10) 0.1595(10) 0.2735(4) 0.123(4) Uani 1 1 d . . .
H12A H 0.7483 0.1057 0.2471 0.184 Uiso 1 1 calc R . .
H12B H 0.7761 0.2391 0.2936 0.184 Uiso 1 1 calc R . .
H12C H 0.8557 0.0968 0.3060 0.184 Uiso 1 1 calc R . .
C13 C 1.0117(10) 0.2923(8) 0.2714(5) 0.153(5) Uani 1 1 d . . .
H13A H 1.0701 0.3246 0.2444 0.230 Uiso 1 1 calc R . .
H13B H 1.0522 0.2255 0.3030 0.230 Uiso 1 1 calc R . .
H13C H 0.9817 0.3744 0.2927 0.230 Uiso 1 1 calc R . .
C14 C 0.7894(5) 0.4498(5) 0.1952(2) 0.0468(12) Uani 1 1 d . . .
H14 H 0.7965 0.4766 0.2382 0.056 Uiso 1 1 calc R . .
C15 C 0.7290(5) 0.5412(5) 0.1493(3) 0.0445(12) Uani 1 1 d . . .
H15 H 0.6954 0.6284 0.1612 0.053 Uiso 1 1 calc R . .
C16 C 0.7182(4) 0.5032(5) 0.0855(2) 0.0416(11) Uani 1 1 d . . .
H16 H 0.6764 0.5649 0.0544 0.050 Uiso 1 1 calc R . .
C17 C 0.7693(4) 0.3732(4) 0.0664(2) 0.0344(9) Uani 1 1 d . . .
C18 C 0.7624(7) 0.3350(6) -0.0048(3) 0.0671(19) Uani 1 1 d . . .
H18 H 0.7825 0.2313 -0.0070 0.081 Uiso 1 1 calc R . .
C19 C 0.8480(9) 0.4103(16) -0.0363(3) 0.181(7) Uani 1 1 d . . .
H19A H 0.8476 0.3699 -0.0785 0.271 Uiso 1 1 calc R . .
H19B H 0.9301 0.4016 -0.0120 0.271 Uiso 1 1 calc R . .
H19C H 0.8250 0.5112 -0.0401 0.271 Uiso 1 1 calc R . .
C20 C 0.6391(9) 0.3550(17) -0.0418(4) 0.243(11) Uani 1 1 d . . .
H20A H 0.6437 0.4243 -0.0755 0.364 Uiso 1 1 calc R . .
H20B H 0.5830 0.3901 -0.0140 0.364 Uiso 1 1 calc R . .
H20C H 0.6092 0.2638 -0.0603 0.364 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'
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
_geom_angle_publ_flag
C1 Au1 N3 177.32(12) . 3_755 ?
C1 N1 C3 111.2(3) . . ?
C1 N1 C4 124.9(3) . . ?
C3 N1 C4 123.9(3) . . ?
C1 N2 C2 111.1(3) . . ?
C1 N2 C7 125.1(3) . . ?
C2 N2 C7 123.7(3) . . ?
C8 N3 C9 114.6(3) . . ?
C8 N3 Au1 127.7(2) . 3_755 ?
C9 N3 Au1 117.6(2) . 3_755 ?
N1 C1 N2 104.6(3) . . ?
N1 C1 Au1 128.6(3) . . ?
N2 C1 Au1 126.7(2) . . ?
C3 C2 N2 106.9(3) . . ?
C3 C2 H2 126.6 . . ?
N2 C2 H2 126.6 . . ?
C2 C3 N1 106.3(3) . . ?
C2 C3 H3 126.8 . . ?
N1 C3 H3 126.8 . . ?
N1 C4 C5 109.9(4) . . ?
N1 C4 C6 109.3(4) . . ?
C5 C4 C6 112.8(5) . . ?
N1 C4 H4 108.2 . . ?
C5 C4 H4 108.2 . . ?
C6 C4 H4 108.2 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 C8 107.3(3) . . ?
N2 C7 H7A 110.3 . . ?
C8 C7 H7A 110.3 . . ?
N2 C7 H7B 110.3 . . ?
C8 C7 H7B 110.3 . . ?
H7A C7 H7B 108.5 . . ?
O1 C8 N3 126.1(3) . . ?
O1 C8 C7 117.5(3) . . ?
N3 C8 C7 116.3(3) . . ?
C10 C9 C17 121.1(4) . . ?
C10 C9 N3 120.1(3) . . ?
C17 C9 N3 118.8(3) . . ?
C14 C10 C9 117.8(4) . . ?
C14 C10 C11 120.7(4) . . ?
C9 C10 C11 121.5(4) . . ?
C13 C11 C10 111.7(5) . . ?
C13 C11 C12 111.0(7) . . ?
C10 C11 C12 110.9(5) . . ?
C13 C11 H11 107.7 . . ?
C10 C11 H11 107.7 . . ?
C12 C11 H11 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C10 122.1(4) . . ?
C15 C14 H14 119.0 . . ?
C10 C14 H14 119.0 . . ?
C14 C15 C16 119.5(4) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 121.1(4) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C9 C17 C16 118.3(4) . . ?
C9 C17 C18 120.9(4) . . ?
C16 C17 C18 120.9(4) . . ?
C19 C18 C20 107.8(7) . . ?
C19 C18 C17 114.3(6) . . ?
C20 C18 C17 113.5(6) . . ?
C19 C18 H18 106.9 . . ?
C20 C18 H18 106.9 . . ?
C17 C18 H18 106.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
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
Au1 C1 1.982(3) . ?
Au1 N3 2.037(3) 3_755 ?
O1 C8 1.226(4) . ?
N1 C1 1.354(4) . ?
N1 C3 1.390(5) . ?
N1 C4 1.473(5) . ?
N2 C1 1.357(5) . ?
N2 C2 1.384(4) . ?
N2 C7 1.471(4) . ?
N3 C8 1.338(4) . ?
N3 C9 1.447(5) . ?
N3 Au1 2.037(3) 3_755 ?
C2 C3 1.352(6) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.515(7) . ?
C4 C6 1.525(7) . ?
C4 H4 0.9800 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.546(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C10 1.398(6) . ?
C9 C17 1.398(5) . ?
C10 C14 1.393(6) . ?
C10 C11 1.515(6) . ?
C11 C13 1.483(9) . ?
C11 C12 1.532(10) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.369(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.401(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.528(7) . ?
C18 C19 1.402(10) . ?
C18 C20 1.453(12) . ?
C18 H18 0.9800 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 N2 -0.2(4) . . . . ?
C4 N1 C1 N2 178.9(3) . . . . ?
C3 N1 C1 Au1 176.4(3) . . . . ?
C4 N1 C1 Au1 -4.6(5) . . . . ?
C2 N2 C1 N1 -0.5(4) . . . . ?
C7 N2 C1 N1 -176.5(3) . . . . ?
C2 N2 C1 Au1 -177.2(3) . . . . ?
C7 N2 C1 Au1 6.9(5) . . . . ?
N3 Au1 C1 N1 -85(3) 3_755 . . . ?
N3 Au1 C1 N2 91(3) 3_755 . . . ?
C1 N2 C2 C3 1.1(4) . . . . ?
C7 N2 C2 C3 177.1(3) . . . . ?
N2 C2 C3 N1 -1.1(4) . . . . ?
C1 N1 C3 C2 0.8(4) . . . . ?
C4 N1 C3 C2 -178.2(3) . . . . ?
C1 N1 C4 C5 115.5(5) . . . . ?
C3 N1 C4 C5 -65.6(6) . . . . ?
C1 N1 C4 C6 -120.2(4) . . . . ?
C3 N1 C4 C6 58.7(5) . . . . ?
C1 N2 C7 C8 115.6(4) . . . . ?
C2 N2 C7 C8 -59.9(4) . . . . ?
C9 N3 C8 O1 -5.7(5) . . . . ?
Au1 N3 C8 O1 170.8(3) 3_755 . . . ?
C9 N3 C8 C7 170.7(3) . . . . ?
Au1 N3 C8 C7 -12.8(5) 3_755 . . . ?
N2 C7 C8 O1 68.4(4) . . . . ?
N2 C7 C8 N3 -108.4(3) . . . . ?
C8 N3 C9 C10 84.2(4) . . . . ?
Au1 N3 C9 C10 -92.7(4) 3_755 . . . ?
C8 N3 C9 C17 -95.5(4) . . . . ?
Au1 N3 C9 C17 87.6(4) 3_755 . . . ?
C17 C9 C10 C14 2.4(6) . . . . ?
N3 C9 C10 C14 -177.3(4) . . . . ?
C17 C9 C10 C11 -178.9(4) . . . . ?
N3 C9 C10 C11 1.4(6) . . . . ?
C14 C10 C11 C13 -58.6(8) . . . . ?
C9 C10 C11 C13 122.8(7) . . . . ?
C14 C10 C11 C12 65.8(7) . . . . ?
C9 C10 C11 C12 -112.8(6) . . . . ?
C9 C10 C14 C15 -0.6(7) . . . . ?
C11 C10 C14 C15 -179.2(5) . . . . ?
C10 C14 C15 C16 -0.3(8) . . . . ?
C14 C15 C16 C17 -0.7(8) . . . . ?
C10 C9 C17 C16 -3.4(6) . . . . ?
N3 C9 C17 C16 176.3(4) . . . . ?
C10 C9 C17 C18 176.2(5) . . . . ?
N3 C9 C17 C18 -4.1(6) . . . . ?
C15 C16 C17 C9 2.5(7) . . . . ?
C15 C16 C17 C18 -177.1(5) . . . . ?
C9 C17 C18 C19 -102.9(8) . . . . ?
C16 C17 C18 C19 76.7(9) . . . . ?
C9 C17 C18 C20 132.9(7) . . . . ?
C16 C17 C18 C20 -47.5(9) . . . . ?
