#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:34:00 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179851 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/47/7014713.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_7014713
loop_
_publ_author_name
'Kunz, Peter C.'
'Wetzel, Corinna'
'Kögel, Susanne'
'Kassack, Matthias U.'
'Spingler, Bernhard'
_publ_section_title
;
 [(C3H4N2)2Au]Cl--a bis protic gold(I)-NHC.
;
_journal_issue                   1
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              35
_journal_page_last               37
_journal_paper_doi               10.1039/c0dt01089h
_journal_volume                  40
_journal_year                    2011
_chemical_formula_sum            'C16 H27 Au Cl N4 O4'
_chemical_formula_weight         571.83
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.996(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4555(3)
_cell_length_b                   13.2831(8)
_cell_length_c                   22.2966(7)
_cell_measurement_reflns_used    5436
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      32.6802
_cell_measurement_theta_min      2.7470
_cell_volume                     2191.64(17)
_computing_cell_refinement       'CrysAlisPro (Oxford, 2007)'
_computing_data_collection       'CrysAlisPro (Oxford, 2007)'
_computing_data_reduction        'CrysAlisPro (Oxford, 2007)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean 10.4498
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Xcalibur Ruby CCD'
_diffrn_measurement_method       'ο oscillation scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12129
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    6.860
_exptl_absorpt_correction_T_max  0.7710
_exptl_absorpt_correction_T_min  0.3810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1116
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         3.249
_refine_diff_density_min         -2.426
_refine_diff_density_rms         0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4842
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.198
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0360P)²+21.8672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1290
_reflns_number_gt                3851
_reflns_number_total             4842
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0DT01089H.TXT
_cod_data_source_block           kp170410
_cod_original_cell_volume        2191.64(18)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7014713
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.86871(5) 0.22013(3) 0.841378(15) 0.03117(13) Uani 1 1 d . . .
C1 C 0.9091(12) 0.1997(8) 0.7548(4) 0.029(2) Uani 1 1 d . . .
C2 C 1.0538(13) 0.1873(9) 0.6724(4) 0.036(3) Uani 1 1 d . . .
H2 H 1.1490 0.1836 0.6478 0.043 Uiso 1 1 calc R . .
C3 C 0.8762(13) 0.1839(9) 0.6532(4) 0.037(3) Uani 1 1 d . . .
H3 H 0.8214 0.1773 0.6127 0.045 Uiso 1 1 calc R . .
C4 C 0.8260(12) 0.2424(8) 0.9272(4) 0.030(2) Uani 1 1 d . . .
C5 C 0.6788(13) 0.2628(9) 1.0095(4) 0.039(3) Uani 1 1 d . . .
H5 H 0.5814 0.2673 1.0332 0.047 Uiso 1 1 calc R . .
C6 C 0.8559(13) 0.2694(10) 1.0295(4) 0.043(3) Uani 1 1 d . . .
H6 H 0.9083 0.2799 1.0700 0.051 Uiso 1 1 calc R . .
C7 C 0.5913(12) 0.1843(8) 0.7049(4) 0.031(2) Uani 1 1 d . . .
H7A H 0.5609 0.1872 0.7473 0.038 Uiso 1 1 calc R . .
C8 C 0.5227(17) 0.3584(10) 0.6941(6) 0.057(4) Uani 1 1 d . . .
H8A H 0.6513 0.3788 0.6975 0.069 Uiso 1 1 calc R . .
H8B H 0.4842 0.3601 0.7351 0.069 Uiso 1 1 calc R . .
C9 C 0.4113(19) 0.4298(10) 0.6541(7) 0.068(4) Uani 1 1 d . . .
H9A H 0.4516 0.4292 0.6139 0.103 Uiso 1 1 calc R . .
H9B H 0.4246 0.4978 0.6711 0.103 Uiso 1 1 calc R . .
H9C H 0.2841 0.4096 0.6509 0.103 Uiso 1 1 calc R . .
C10 C 0.5779(19) 0.0059(12) 0.7088(7) 0.074(5) Uani 1 1 d . . .
H10 H 0.6850 -0.0302 0.7037 0.089 Uiso 1 1 calc R . .
C11 C 0.453(3) -0.0248(13) 0.7478(8) 0.099(6) Uani 1 1 d . . .
H11C H 0.4396 0.0286 0.7773 0.148 Uiso 1 1 calc R . .
H11B H 0.4967 -0.0863 0.7690 0.148 Uiso 1 1 calc R . .
H11A H 0.3357 -0.0380 0.7241 0.148 Uiso 1 1 calc R . .
C12 C 1.1445(14) 0.2665(10) 0.9783(4) 0.044(3) Uani 1 1 d . . .
H12A H 1.1798 0.2539 0.9371 0.052 Uiso 1 1 calc R . .
C13 C 1.176(2) 0.4419(14) 0.9592(9) 0.098(7) Uani 1 1 d . . .
H13B H 1.0630 0.4296 0.9322 0.118 Uiso 1 1 calc R . .
H13A H 1.1583 0.5031 0.9832 0.118 Uiso 1 1 calc R . .
C14 C 1.317(2) 0.4607(13) 0.9232(8) 0.097(6) Uani 1 1 d . . .
H14C H 1.4325 0.4668 0.9493 0.145 Uiso 1 1 calc R . .
H14B H 1.2924 0.5233 0.9005 0.145 Uiso 1 1 calc R . .
H14A H 1.3245 0.4048 0.8949 0.145 Uiso 1 1 calc R . .
C15 C 1.216(2) 0.0975(11) 1.0021(8) 0.082(5) Uani 1 1 d . . .
H15A H 1.2675 0.0886 0.9635 0.099 Uiso 1 1 calc R . .
H15B H 1.0881 0.0763 0.9960 0.099 Uiso 1 1 calc R . .
C16 C 1.319(2) 0.0345(13) 1.0505(10) 0.110(8) Uani 1 1 d . . .
H16C H 1.2609 0.0386 1.0875 0.165 Uiso 1 1 calc R . .
H16B H 1.4436 0.0594 1.0586 0.165 Uiso 1 1 calc R . .
H16A H 1.3206 -0.0357 1.0370 0.165 Uiso 1 1 calc R . .
N1 N 0.7895(10) 0.1919(7) 0.7039(3) 0.0304(18) Uani 1 1 d U . .
N2 N 1.0722(10) 0.1968(6) 0.7333(3) 0.0312(17) Uani 1 1 d U . .
H2A H 1.1769 0.2007 0.7562 0.037 Uiso 1 1 calc R . .
N3 N 0.9497(10) 0.2574(7) 0.9779(4) 0.0337(19) Uani 1 1 d U . .
N4 N 0.6659(10) 0.2480(6) 0.9468(3) 0.0312(17) Uani 1 1 d U . .
H4A H 0.5627 0.2429 0.9232 0.037 Uiso 1 1 calc R . .
O1 O 0.5036(9) 0.2593(5) 0.6706(3) 0.0302(16) Uani 1 1 d . . .
O2 O 0.5244(10) 0.0993(7) 0.6771(4) 0.051(2) Uani 1 1 d . . .
O3 O 1.2085(10) 0.3576(7) 1.0000(4) 0.057(2) Uani 1 1 d . . .
O4 O 1.2288(10) 0.1981(7) 1.0198(3) 0.048(2) Uani 1 1 d . . .
Cl1 Cl 0.3648(3) 0.2068(3) 0.84309(12) 0.0564(9) 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'
Cl Cl 0.1484 0.1585 '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
C4 Au1 C1 179.1(4) . . ?
N1 C1 N2 103.1(7) . . ?
N1 C1 Au1 130.8(7) . . ?
N2 C1 Au1 126.0(6) . . ?
C3 C2 N2 107.3(8) . . ?
C3 C2 H2 126.3 . . ?
N2 C2 H2 126.3 . . ?
C2 C3 N1 106.3(8) . . ?
C2 C3 H3 126.9 . . ?
N1 C3 H3 126.9 . . ?
N4 C4 N3 105.0(8) . . ?
N4 C4 Au1 125.5(7) . . ?
N3 C4 Au1 129.5(7) . . ?
C6 C5 N4 106.5(8) . . ?
C6 C5 H5 126.7 . . ?
N4 C5 H5 126.7 . . ?
C5 C6 N3 106.5(8) . . ?
C5 C6 H6 126.7 . . ?
N3 C6 H6 126.7 . . ?
O2 C7 O1 103.2(7) . . ?
O2 C7 N1 111.3(8) . . ?
O1 C7 N1 110.5(8) . . ?
O2 C7 H7A 110.6 . . ?
O1 C7 H7A 110.6 . . ?
N1 C7 H7A 110.6 . . ?
O1 C8 C9 110.3(10) . . ?
O1 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
O1 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 O2 112.5(13) . . ?
C11 C10 H10 123.8 . . ?
O2 C10 H10 123.8 . . ?
C10 C11 H11C 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11C C11 H11B 109.5 . . ?
C10 C11 H11A 109.5 . . ?
H11C C11 H11A 109.5 . . ?
H11B C11 H11A 109.5 . . ?
O3 C12 O4 103.5(8) . . ?
O3 C12 N3 112.4(9) . . ?
O4 C12 N3 108.6(9) . . ?
O3 C12 H12A 110.7 . . ?
O4 C12 H12A 110.7 . . ?
N3 C12 H12A 110.7 . . ?
C14 C13 O3 114.5(13) . . ?
C14 C13 H13B 108.6 . . ?
O3 C13 H13B 108.6 . . ?
C14 C13 H13A 108.6 . . ?
O3 C13 H13A 108.6 . . ?
H13B C13 H13A 107.6 . . ?
C13 C14 H14C 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14C C14 H14B 109.5 . . ?
C13 C14 H14A 109.5 . . ?
H14C C14 H14A 109.5 . . ?
H14B C14 H14A 109.5 . . ?
O4 C15 C16 108.7(14) . . ?
O4 C15 H15A 110.0 . . ?
C16 C15 H15A 110.0 . . ?
O4 C15 H15B 110.0 . . ?
C16 C15 H15B 110.0 . . ?
H15A C15 H15B 108.3 . . ?
C15 C16 H16C 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16C C16 H16B 109.5 . . ?
C15 C16 H16A 109.5 . . ?
H16C C16 H16A 109.5 . . ?
H16B C16 H16A 109.5 . . ?
C1 N1 C3 111.5(8) . . ?
C1 N1 C7 123.2(8) . . ?
C3 N1 C7 125.1(7) . . ?
C2 N2 C1 111.8(7) . . ?
C2 N2 H2A 124.1 . . ?
C1 N2 H2A 124.1 . . ?
C4 N3 C6 109.4(8) . . ?
C4 N3 C12 125.6(8) . . ?
C6 N3 C12 124.9(8) . . ?
C4 N4 C5 112.5(8) . . ?
C4 N4 H4A 123.7 . . ?
C5 N4 H4A 123.7 . . ?
C7 O1 C8 116.7(8) . . ?
C7 O2 C10 115.1(9) . . ?
C12 O3 C13 116.1(12) . . ?
C12 O4 C15 115.4(11) . . ?
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 C4 1.999(10) . ?
Au1 C1 2.007(9) . ?
C1 N1 1.359(10) . ?
C1 N2 1.361(12) . ?
C2 C3 1.341(13) . ?
C2 N2 1.355(12) . ?
C2 H2 0.9500 . ?
C3 N1 1.373(12) . ?
C3 H3 0.9500 . ?
C4 N4 1.323(12) . ?
C4 N3 1.384(11) . ?
C5 C6 1.344(13) . ?
C5 N4 1.402(12) . ?
C5 H5 0.9500 . ?
C6 N3 1.426(13) . ?
C6 H6 0.9500 . ?
C7 O2 1.352(13) . ?
C7 O1 1.372(12) . ?
C7 N1 1.484(11) . ?
C7 H7A 1.0000 . ?
C8 O1 1.417(14) . ?
C8 C9 1.486(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.41(2) . ?
C10 O2 1.459(16) . ?
C10 H10 0.9500 . ?
C11 H11C 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11A 0.9800 . ?
C12 O3 1.367(15) . ?
C12 O4 1.391(13) . ?
C12 N3 1.456(12) . ?
C12 H12A 1.0000 . ?
C13 C14 1.42(2) . ?
C13 O3 1.444(16) . ?
C13 H13B 0.9900 . ?
C13 H13A 0.9900 . ?
C14 H14C 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14A 0.9800 . ?
C15 O4 1.393(16) . ?
C15 C16 1.50(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16C 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16A 0.9800 . ?
N2 H2A 0.8800 . ?
N4 H4A 0.8800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4A Cl1 0.88 2.23 3.070(8) 160.4 .
N2 H2A Cl1 0.88 2.25 3.077(8) 156.4 1_655
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
C4 Au1 C1 N1 -53(27) . . . . ?
C4 Au1 C1 N2 123(26) . . . . ?
N2 C2 C3 N1 0.1(13) . . . . ?
C1 Au1 C4 N4 56(27) . . . . ?
C1 Au1 C4 N3 -123(26) . . . . ?
N4 C5 C6 N3 -0.5(13) . . . . ?
N2 C1 N1 C3 0.4(12) . . . . ?
Au1 C1 N1 C3 176.6(8) . . . . ?
N2 C1 N1 C7 175.5(9) . . . . ?
Au1 C1 N1 C7 -8.3(15) . . . . ?
C2 C3 N1 C1 -0.3(13) . . . . ?
C2 C3 N1 C7 -175.3(10) . . . . ?
O2 C7 N1 C1 -122.1(10) . . . . ?
O1 C7 N1 C1 123.9(10) . . . . ?
O2 C7 N1 C3 52.3(13) . . . . ?
O1 C7 N1 C3 -61.7(13) . . . . ?
C3 C2 N2 C1 0.1(13) . . . . ?
N1 C1 N2 C2 -0.3(12) . . . . ?
Au1 C1 N2 C2 -176.7(8) . . . . ?
N4 C4 N3 C6 1.7(12) . . . . ?
Au1 C4 N3 C6 -179.7(8) . . . . ?
N4 C4 N3 C12 -174.4(10) . . . . ?
Au1 C4 N3 C12 4.2(16) . . . . ?
C5 C6 N3 C4 -0.7(13) . . . . ?
C5 C6 N3 C12 175.4(11) . . . . ?
O3 C12 N3 C4 118.9(11) . . . . ?
O4 C12 N3 C4 -127.1(10) . . . . ?
O3 C12 N3 C6 -56.6(14) . . . . ?
O4 C12 N3 C6 57.3(15) . . . . ?
N3 C4 N4 C5 -2.1(12) . . . . ?
Au1 C4 N4 C5 179.3(8) . . . . ?
C6 C5 N4 C4 1.7(14) . . . . ?
O2 C7 O1 C8 169.9(9) . . . . ?
N1 C7 O1 C8 -71.1(11) . . . . ?
C9 C8 O1 C7 -176.5(10) . . . . ?
O1 C7 O2 C10 -172.5(9) . . . . ?
N1 C7 O2 C10 68.9(11) . . . . ?
C11 C10 O2 C7 92.2(16) . . . . ?
O4 C12 O3 C13 166.6(10) . . . . ?
N3 C12 O3 C13 -76.3(13) . . . . ?
C14 C13 O3 C12 -91.6(18) . . . . ?
O3 C12 O4 C15 -167.4(10) . . . . ?
N3 C12 O4 C15 72.9(13) . . . . ?
C16 C15 O4 C12 177.9(11) . . . . ?
