#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:52:50 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178538 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/44/4064470.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_4064470
loop_
_publ_author_name
'Carcedo, Cristina'
'Knight, James C.'
'Pope, Simon J. A.'
'Fallis, Ian A.'
'Dervisi, Athanasia'
_publ_section_title
;
 Chiral Silver and Gold Rings: Synthesis and Structural, Spectroscopic,
 and Photophysical Properties of Ag and Au Metallamacrocycles of Bridging
 NHC Ligands
;
_journal_issue                   9
_journal_name_full               Organometallics
_journal_page_first              2553
_journal_paper_doi               10.1021/om200125w
_journal_volume                  30
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C14 H18 Au2 Cl2 N4 O2'
_chemical_formula_sum            'C14 H18 Au2 Cl2 N4 O2'
_chemical_formula_weight         739.16
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 114.071(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.3312(3)
_cell_length_b                   12.6030(4)
_cell_length_c                   9.4992(4)
_cell_measurement_reflns_used    1776
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     910.67(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius, 2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5974
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    16.399
_exptl_absorpt_correction_T_max  0.7351
_exptl_absorpt_correction_T_min  0.0508
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.696
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.848
_refine_diff_density_min         -1.292
_refine_diff_density_rms         0.283
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.018(16)
_refine_ls_extinction_coef       0.0016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3742
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0371
_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)+(0.0238P)²+10.6469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0853
_reflns_number_gt                3436
_reflns_number_total             3742
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om200125w_si_002.cif
_cod_data_source_block           ad1001a
_cod_original_cell_volume        910.66(6)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4064470
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
C1 C 0.7695(18) 0.4892(10) 0.7937(15) 0.029(3) Uani 1 1 d .
H1A H 0.8868 0.4800 0.7949 0.044 Uiso 1 1 calc R
H1B H 0.6803 0.4765 0.6893 0.044 Uiso 1 1 calc R
H1C H 0.7533 0.4387 0.8652 0.044 Uiso 1 1 calc R
C2 C 0.6073(13) 0.6591(10) 0.7668(13) 0.022(3) Uani 1 1 d .
C3 C 0.8748(15) 0.6478(14) 0.9673(15) 0.034(3) Uani 1 1 d .
H3 H 0.9864 0.6220 1.0363 0.041 Uiso 1 1 calc R
C4 C 0.8025(15) 0.7417(11) 0.9716(15) 0.029(3) Uani 1 1 d .
H4 H 0.8563 0.7955 1.0461 0.035 Uiso 1 1 calc R
C5 C 0.5313(15) 0.8432(10) 0.8252(16) 0.024(3) Uani 1 1 d .
H5 H 0.5719 0.8877 0.9206 0.028 Uiso 1 1 calc R
C6 C 0.5357(17) 0.9108(10) 0.6886(16) 0.030(3) Uani 1 1 d .
H6A H 0.6281 0.9660 0.7271 0.036 Uiso 1 1 calc R
H6B H 0.5588 0.8652 0.6140 0.036 Uiso 1 1 calc R
C7 C 0.2462(15) 0.8754(9) 0.6152(15) 0.019(3) Uani 1 1 d .
H7 H 0.2218 0.8246 0.5280 0.023 Uiso 1 1 calc R
C8 C 0.3408(17) 0.8251(10) 0.7690(17) 0.029(3) Uani 1 1 d .
H8 H 0.3188 0.7470 0.7578 0.035 Uiso 1 1 calc R
C9 C 0.1362(16) 0.9467(9) 0.7917(14) 0.023(3) Uani 1 1 d .
H9A H 0.1894 1.0182 0.8176 0.028 Uiso 1 1 calc R
H9B H 0.0347 0.9429 0.8204 0.028 Uiso 1 1 calc R
C10 C 0.0777(15) 0.9236(9) 0.6180(14) 0.020(2) Uani 1 1 d .
H10 H 0.0474 0.9913 0.5578 0.024 Uiso 1 1 calc R
C11 C -0.0746(17) 0.7526(10) 0.6216(15) 0.025(3) Uani 1 1 d .
H11 H 0.0007 0.7297 0.7223 0.030 Uiso 1 1 calc R
C12 C -0.1938(17) 0.8526(10) 0.4096(15) 0.024(3) Uani 1 1 d .
C13 C -0.2091(16) 0.6979(10) 0.5173(15) 0.024(3) Uani 1 1 d .
H13 H -0.2466 0.6288 0.5301 0.029 Uiso 1 1 calc R
C14 C -0.4329(17) 0.7291(11) 0.2514(16) 0.031(3) Uani 1 1 d .
H14A H -0.5279 0.7051 0.2794 0.047 Uiso 1 1 calc R
H14B H -0.3994 0.6714 0.1997 0.047 Uiso 1 1 calc R
H14C H -0.4731 0.7901 0.1818 0.047 Uiso 1 1 calc R
N1 N 0.7518(13) 0.5960(8) 0.8402(11) 0.024(2) Uani 1 1 d U
N2 N 0.6416(13) 0.7487(8) 0.8544(12) 0.022(2) Uani 1 1 d .
N3 N -0.0668(14) 0.8482(8) 0.5543(12) 0.023(2) Uani 1 1 d .
N4 N -0.2812(14) 0.7600(8) 0.3906(12) 0.022(2) Uani 1 1 d .
O1 O 0.2622(13) 0.8670(8) 0.8700(11) 0.029(2) Uani 1 1 d .
O2 O 0.3657(11) 0.9580(8) 0.6186(9) 0.0257(19) Uani 1 1 d .
Au1 Au 0.40051(5) 0.63233(4) 0.57341(5) 0.02237(13) Uani 1 1 d .
Au2 Au -0.23497(6) 0.96527(4) 0.25428(5) 0.02227(13) Uani 1 1 d .
Cl1 Cl 0.1655(4) 0.6290(4) 0.3407(3) 0.0324(6) Uani 1 1 d .
Cl2 Cl -0.2757(4) 1.0812(3) 0.0578(4) 0.0288(7) 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'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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_3
N1 C1 H1A 109.5 .
N1 C1 H1B 109.5 .
H1A C1 H1B 109.5 .
N1 C1 H1C 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
N2 C2 N1 104.4(9) .
N2 C2 Au1 126.7(8) .
N1 C2 Au1 128.8(9) .
C4 C3 N1 105.2(11) .
C4 C3 H3 127.4 .
N1 C3 H3 127.4 .
C3 C4 N2 109.9(12) .
C3 C4 H4 125.0 .
N2 C4 H4 125.0 .
N2 C5 C8 116.5(11) .
N2 C5 C6 112.1(10) .
C8 C5 C6 99.8(10) .
N2 C5 H5 109.4 .
C8 C5 H5 109.4 .
C6 C5 H5 109.4 .
O2 C6 C5 105.0(10) .
O2 C6 H6A 110.7 .
C5 C6 H6A 110.7 .
O2 C6 H6B 110.7 .
C5 C6 H6B 110.7 .
H6A C6 H6B 108.8 .
O2 C7 C8 101.7(9) .
O2 C7 C10 110.1(10) .
C8 C7 C10 105.8(10) .
O2 C7 H7 112.8 .
C8 C7 H7 112.8 .
C10 C7 H7 112.8 .
O1 C8 C5 114.3(12) .
O1 C8 C7 106.9(10) .
C5 C8 C7 110.6(10) .
O1 C8 H8 108.3 .
C5 C8 H8 108.3 .
C7 C8 H8 108.3 .
O1 C9 C10 105.6(9) .
O1 C9 H9A 110.6 .
C10 C9 H9A 110.6 .
O1 C9 H9B 110.6 .
C10 C9 H9B 110.6 .
H9A C9 H9B 108.7 .
N3 C10 C7 109.9(10) .
N3 C10 C9 114.5(10) .
C7 C10 C9 101.5(9) .
N3 C10 H10 110.2 .
C7 C10 H10 110.2 .
C9 C10 H10 110.2 .
C13 C11 N3 106.8(11) .
C13 C11 H11 126.6 .
N3 C11 H11 126.6 .
N4 C12 N3 104.8(11) .
N4 C12 Au2 127.1(10) .
N3 C12 Au2 128.0(10) .
C11 C13 N4 107.1(11) .
C11 C13 H13 126.5 .
N4 C13 H13 126.5 .
N4 C14 H14A 109.5 .
N4 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
N4 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
C2 N1 C3 110.7(11) .
C2 N1 C1 124.3(10) .
C3 N1 C1 125.0(11) .
C4 N2 C2 109.8(10) .
C4 N2 C5 123.1(11) .
C2 N2 C5 126.9(10) .
C12 N3 C11 110.0(11) .
C12 N3 C10 124.5(11) .
C11 N3 C10 124.4(10) .
C12 N4 C13 111.2(11) .
C12 N4 C14 124.9(11) .
C13 N4 C14 123.9(10) .
C9 O1 C8 110.1(9) .
C6 O2 C7 104.9(9) .
C2 Au1 Cl1 170.8(4) .
C2 Au1 Au2 91.7(3) 2_546
Cl1 Au1 Au2 95.85(10) 2_546
C12 Au2 Cl2 173.4(4) .
C12 Au2 Au1 93.9(4) 2_556
Cl2 Au2 Au1 92.54(9) 2_556
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.443(16) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 N2 1.362(16) .
C2 N1 1.372(14) .
C2 Au1 1.969(10) .
C3 C4 1.34(2) .
C3 N1 1.387(17) .
C3 H3 0.9500 .
C4 N2 1.352(15) .
C4 H4 0.9500 .
C5 N2 1.459(15) .
C5 C8 1.471(17) .
C5 C6 1.566(18) .
C5 H5 1.0000 .
C6 O2 1.426(15) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 O2 1.432(14) .
C7 C8 1.489(18) .
C7 C10 1.540(16) .
C7 H7 1.0000 .
C8 O1 1.462(18) .
C8 H8 1.0000 .
C9 O1 1.424(15) .
C9 C10 1.545(17) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 N3 1.457(16) .
C10 H10 1.0000 .
C11 C13 1.344(18) .
C11 N3 1.378(15) .
C11 H11 0.9500 .
C12 N4 1.349(17) .
C12 N3 1.351(17) .
C12 Au2 1.974(13) .
C13 N4 1.353(16) .
C13 H13 0.9500 .
C14 N4 1.460(16) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
Au1 Cl1 2.278(3) .
Au1 Au2 3.2948(7) 2_546
Au2 Cl2 2.285(3) .
Au2 Au1 3.2948(7) 2_556
