#------------------------------------------------------------------------------
#$Date: 2016-03-21 11:13:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178684 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/95/4079552.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_4079552
loop_
_publ_author_name
'Sato, Tetsuo'
'Hirose, Yoichi'
'Yoshioka, Daisuke'
'Oi, Shuichi'
_publ_section_title
;
 N-Heterocyclic Carbenes with aN-2,4-Dinitrophenyl Substituent: Comparison
 with PPh3and IPr
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              6995
_journal_paper_doi               10.1021/om300814f
_journal_volume                  31
_journal_year                    2012
_chemical_formula_sum            'C18 H14 Au Cl N6 O9'
_chemical_formula_weight         690.77
_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                 113.251(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.772(2)
_cell_length_b                   9.0891(15)
_cell_length_c                   17.990(3)
_cell_measurement_reflns_used    6617
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      2.33
_cell_volume                     2219.2(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11940
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    6.814
_exptl_absorpt_correction_T_max  0.9350
_exptl_absorpt_correction_T_min  0.6004
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
 SADABS (Sheldrick, 1997)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.068
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.192
_refine_diff_density_min         -1.294
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0259
_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)+(0.0145P)²+9.6443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0606
_reflns_number_gt                4275
_reflns_number_total             4947
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om300814f_si_007.cif
_cod_data_source_block           ydkr
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4079552
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
Au1 Au 0.066035(10) 0.499436(16) 0.444014(8) 0.01327(5) Uani 1 1 d .
Cl1 Cl 0.00840(7) 0.26930(9) 0.39472(5) 0.01553(17) Uani 1 1 d .
O1 O 0.3613(3) 0.7835(4) 0.5136(2) 0.0353(8) Uani 1 1 d .
O2 O 0.4480(3) 0.5861(4) 0.5255(2) 0.0382(8) Uani 1 1 d .
O3 O 0.5463(2) 0.3510(4) 0.7840(2) 0.0440(9) Uani 1 1 d .
O4 O 0.4359(3) 0.3019(5) 0.8294(3) 0.0559(12) Uani 1 1 d .
O5 O 0.1593(2) 0.8719(4) 0.3317(2) 0.0380(8) Uani 1 1 d .
O6 O 0.0959(2) 1.0696(4) 0.26309(19) 0.0312(7) Uani 1 1 d .
O7 O -0.2584(3) 1.0528(5) 0.1267(2) 0.0454(9) Uani 1 1 d .
O8 O -0.3414(3) 0.9915(6) 0.1959(3) 0.0664(15) Uani 1 1 d .
O9 O 0.3073(4) 0.2945(5) 0.0829(3) 0.0613(14) Uani 1 1 d .
N1 N 0.1993(2) 0.7351(4) 0.54639(19) 0.0178(7) Uani 1 1 d .
N2 N 0.0813(2) 0.8302(4) 0.44641(18) 0.0164(7) Uani 1 1 d .
N3 N 0.3899(3) 0.6618(4) 0.5418(2) 0.0251(8) Uani 1 1 d .
N4 N 0.4639(3) 0.3623(4) 0.7825(2) 0.0313(9) Uani 1 1 d .
N5 N 0.0914(3) 0.9601(4) 0.3012(2) 0.0224(7) Uani 1 1 d .
N6 N -0.2657(3) 0.9993(5) 0.1849(3) 0.0335(9) Uani 1 1 d .
C1 C 0.1177(3) 0.6988(4) 0.4803(2) 0.0147(7) Uani 1 1 d .
C2 C 0.1373(3) 0.9471(5) 0.4914(2) 0.0224(8) Uani 1 1 d .
H2 H 0.1256 1.0489 0.4797 0.027 Uiso 1 1 calc R
C3 C 0.2112(3) 0.8870(4) 0.5546(2) 0.0221(8) Uani 1 1 d .
H3 H 0.2618 0.9383 0.5968 0.027 Uiso 1 1 calc R
C4 C 0.2649(3) 0.6339(4) 0.6024(2) 0.0196(8) Uani 1 1 d .
C5 C 0.3558(3) 0.6005(4) 0.6019(2) 0.0199(8) Uani 1 1 d .
C6 C 0.4210(3) 0.5088(4) 0.6599(3) 0.0223(8) Uani 1 1 d .
H6 H 0.4830 0.4840 0.6591 0.027 Uiso 1 1 calc R
C7 C 0.3927(3) 0.4556(5) 0.7183(3) 0.0228(9) Uani 1 1 d .
C8 C 0.3024(3) 0.4828(5) 0.7207(3) 0.0246(9) Uani 1 1 d .
H8 H 0.2849 0.4400 0.7614 0.029 Uiso 1 1 calc R
C9 C 0.2374(3) 0.5745(5) 0.6620(3) 0.0231(9) Uani 1 1 d .
H9 H 0.1748 0.5967 0.6625 0.028 Uiso 1 1 calc R
C10 C -0.0056(3) 0.8538(4) 0.3752(2) 0.0148(7) Uani 1 1 d .
C11 C -0.0021(3) 0.9289(4) 0.3090(2) 0.0156(7) Uani 1 1 d .
C12 C -0.0872(3) 0.9762(4) 0.2463(2) 0.0172(8) Uani 1 1 d .
H12 H -0.0843 1.0307 0.2022 0.021 Uiso 1 1 calc R
C13 C -0.1753(3) 0.9416(5) 0.2500(2) 0.0194(8) Uani 1 1 d .
C14 C -0.1827(3) 0.8589(5) 0.3123(2) 0.0219(8) Uani 1 1 d .
H14 H -0.2451 0.8324 0.3118 0.026 Uiso 1 1 calc R
C15 C -0.0962(3) 0.8162(4) 0.3752(2) 0.0202(8) Uani 1 1 d .
H15 H -0.0993 0.7604 0.4188 0.024 Uiso 1 1 calc R
C16 C 0.3565(5) 0.3102(6) 0.0436(4) 0.0426(13) Uani 1 1 d .
C17 C 0.3124(5) 0.3009(8) -0.0458(4) 0.0583(17) Uani 1 1 d .
H17 H 0.2457 0.2600 -0.0637 0.088 Uiso 1 1 calc R
H17A H 0.3530 0.2370 -0.0640 0.088 Uiso 1 1 calc R
H17B H 0.3092 0.3994 -0.0688 0.088 Uiso 1 1 calc R
C18 C 0.4628(6) 0.3406(7) 0.0822(4) 0.0620(19) Uani 1 1 d .
H18 H 0.4830 0.3468 0.1409 0.093 Uiso 1 1 calc R
H18A H 0.4770 0.4341 0.0618 0.093 Uiso 1 1 calc R
H18B H 0.4992 0.2612 0.0694 0.093 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'
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'
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'
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
C1 Au1 Cl1 176.35(10) .
C1 Au1 Au1 92.27(11) 3_566
Cl1 Au1 Au1 91.15(2) 3_566
C1 N1 C3 111.4(3) .
C1 N1 C4 125.7(3) .
C3 N1 C4 122.9(3) .
C1 N2 C2 111.9(3) .
C1 N2 C10 126.5(3) .
C2 N2 C10 121.6(3) .
O1 N3 O2 124.8(4) .
O1 N3 C5 119.0(4) .
O2 N3 C5 116.1(4) .
O4 N4 O3 124.3(4) .
O4 N4 C7 118.1(4) .
O3 N4 C7 117.6(4) .
O6 N5 O5 124.4(4) .
O6 N5 C11 118.0(3) .
O5 N5 C11 117.6(3) .
O7 N6 O8 125.0(4) .
O7 N6 C13 118.1(4) .
O8 N6 C13 116.9(4) .
N2 C1 N1 103.8(3) .
N2 C1 Au1 128.9(3) .
N1 C1 Au1 127.3(3) .
C3 C2 N2 106.3(4) .
C3 C2 H2 126.9 .
N2 C2 H2 126.9 .
C2 C3 N1 106.7(3) .
C2 C3 H3 126.7 .
N1 C3 H3 126.7 .
C5 C4 C9 119.9(4) .
C5 C4 N1 121.9(4) .
C9 C4 N1 118.1(4) .
C4 C5 C6 121.0(4) .
C4 C5 N3 122.6(4) .
C6 C5 N3 116.4(4) .
C7 C6 C5 117.5(4) .
C7 C6 H6 121.3 .
C5 C6 H6 121.3 .
C6 C7 C8 123.9(4) .
C6 C7 N4 117.6(4) .
C8 C7 N4 118.5(4) .
C7 C8 C9 118.2(4) .
C7 C8 H8 120.9 .
C9 C8 H8 120.9 .
C8 C9 C4 119.5(4) .
C8 C9 H9 120.2 .
C4 C9 H9 120.2 .
C15 C10 C11 119.0(3) .
C15 C10 N2 119.4(3) .
C11 C10 N2 121.2(3) .
C12 C11 C10 121.5(4) .
C12 C11 N5 116.5(3) .
C10 C11 N5 122.0(3) .
C13 C12 C11 117.6(4) .
C13 C12 H12 121.2 .
C11 C12 H12 121.2 .
C12 C13 C14 123.0(4) .
C12 C13 N6 117.3(4) .
C14 C13 N6 119.7(4) .
C15 C14 C13 118.0(4) .
C15 C14 H14 121.0 .
C13 C14 H14 121.0 .
C10 C15 C14 120.7(4) .
C10 C15 H15 119.6 .
C14 C15 H15 119.6 .
O9 C16 C18 121.6(6) .
O9 C16 C17 121.5(6) .
C18 C16 C17 116.9(5) .
C16 C17 H17 109.5 .
C16 C17 H17A 109.5 .
H17 C17 H17A 109.5 .
C16 C17 H17B 109.5 .
H17 C17 H17B 109.5 .
H17A C17 H17B 109.5 .
C16 C18 H18 109.5 .
C16 C18 H18A 109.5 .
H18 C18 H18A 109.5 .
C16 C18 H18B 109.5 .
H18 C18 H18B 109.5 .
H18A C18 H18B 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Au1 C1 1.975(4) .
Au1 Cl1 2.3000(9) .
Au1 Au1 3.3115(5) 3_566
O1 N3 1.221(5) .
O2 N3 1.222(5) .
O3 N4 1.211(5) .
O4 N4 1.208(5) .
O5 N5 1.230(5) .
O6 N5 1.225(5) .
O7 N6 1.197(5) .
O8 N6 1.211(6) .
O9 C16 1.206(6) .
N1 C1 1.358(5) .
N1 C3 1.393(5) .
N1 C4 1.424(5) .
N2 C1 1.352(5) .
N2 C2 1.393(5) .
N2 C10 1.427(5) .
N3 C5 1.471(5) .
N4 C7 1.483(5) .
N5 C11 1.471(5) .
N6 C13 1.482(5) .
C2 C3 1.342(6) .
C2 H2 0.9500 .
C3 H3 0.9500 .
C4 C5 1.381(6) .
C4 C9 1.396(6) .
C5 C6 1.385(6) .
C6 C7 1.364(6) .
C6 H6 0.9500 .
C7 C8 1.373(6) .
C8 C9 1.390(6) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C15 1.382(6) .
C10 C11 1.390(5) .
C11 C12 1.385(5) .
C12 C13 1.367(6) .
C12 H12 0.9500 .
C13 C14 1.389(6) .
C14 C15 1.386(6) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 C18 1.471(9) .
C16 C17 1.480(8) .
C17 H17 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C18 H18 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
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
C2 N2 C1 N1 -1.6(4) .
C10 N2 C1 N1 -179.3(3) .
C2 N2 C1 Au1 178.3(3) .
C10 N2 C1 Au1 0.6(6) .
C3 N1 C1 N2 2.0(4) .
C4 N1 C1 N2 -179.3(4) .
C3 N1 C1 Au1 -177.9(3) .
C4 N1 C1 Au1 0.8(6) .
Cl1 Au1 C1 N2 67.8(19) .
Au1 Au1 C1 N2 -91.6(3) 3_566
Cl1 Au1 C1 N1 -112.3(16) .
Au1 Au1 C1 N1 88.2(3) 3_566
C1 N2 C2 C3 0.6(5) .
C10 N2 C2 C3 178.4(4) .
N2 C2 C3 N1 0.6(5) .
C1 N1 C3 C2 -1.7(5) .
C4 N1 C3 C2 179.5(4) .
C1 N1 C4 C5 103.6(5) .
C3 N1 C4 C5 -77.8(5) .
C1 N1 C4 C9 -80.2(5) .
C3 N1 C4 C9 98.4(5) .
C9 C4 C5 C6 -0.2(6) .
N1 C4 C5 C6 176.0(4) .
C9 C4 C5 N3 -178.7(4) .
N1 C4 C5 N3 -2.5(6) .
O1 N3 C5 C4 30.3(6) .
O2 N3 C5 C4 -151.6(4) .
O1 N3 C5 C6 -148.3(4) .
O2 N3 C5 C6 29.9(5) .
C4 C5 C6 C7 -1.3(6) .
N3 C5 C6 C7 177.3(4) .
C5 C6 C7 C8 2.8(6) .
C5 C6 C7 N4 -177.6(4) .
O4 N4 C7 C6 -172.2(5) .
O3 N4 C7 C6 7.3(6) .
O4 N4 C7 C8 7.4(7) .
O3 N4 C7 C8 -173.0(4) .
C6 C7 C8 C9 -2.6(7) .
N4 C7 C8 C9 177.8(4) .
C7 C8 C9 C4 0.9(6) .
C5 C4 C9 C8 0.4(6) .
N1 C4 C9 C8 -175.9(4) .
C1 N2 C10 C15 64.9(5) .
C2 N2 C10 C15 -112.6(4) .
C1 N2 C10 C11 -122.5(4) .
C2 N2 C10 C11 60.1(5) .
C15 C10 C11 C12 4.9(6) .
N2 C10 C11 C12 -167.8(3) .
C15 C10 C11 N5 -174.0(4) .
N2 C10 C11 N5 13.3(6) .
O6 N5 C11 C12 29.6(5) .
O5 N5 C11 C12 -148.5(4) .
O6 N5 C11 C10 -151.4(4) .
O5 N5 C11 C10 30.5(6) .
C10 C11 C12 C13 -2.4(6) .
N5 C11 C12 C13 176.5(3) .
C11 C12 C13 C14 -1.7(6) .
C11 C12 C13 N6 176.8(4) .
O7 N6 C13 C12 11.3(6) .
O8 N6 C13 C12 -167.0(5) .
O7 N6 C13 C14 -170.1(4) .
O8 N6 C13 C14 11.6(7) .
C12 C13 C14 C15 3.2(6) .
N6 C13 C14 C15 -175.2(4) .
C11 C10 C15 C14 -3.2(6) .
N2 C10 C15 C14 169.6(4) .
C13 C14 C15 C10 -0.7(6) .
