#------------------------------------------------------------------------------
#$Date: 2016-03-25 09:17:47 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179718 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/20/7002029.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_7002029
loop_
_publ_author_name
'Lemke, Jessica'
'Pinto, Antonio'
'Niehoff, Philip'
'Vasylyeva, Vera'
'Metzler-Nolte, Nils'
_publ_section_title
;
 Synthesis, structural characterisation and anti-proliferative activity
 of NHC gold amino acid and peptide conjugates
;
_journal_issue                   35
_journal_name_full               'Dalton Transactions'
_journal_page_first              7063
_journal_paper_doi               10.1039/b906140a
_journal_year                    2009
_chemical_formula_sum            'C19 H25 Au Br3 N3 O3'
_chemical_formula_weight         780.12
_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                 92.894(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.452(4)
_cell_length_b                   9.212(4)
_cell_length_c                   15.756(7)
_cell_measurement_temperature    293(2)
_cell_volume                     1225.2(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0740
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6721
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    10.919
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    2.115
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_refine_diff_density_max         1.496
_refine_diff_density_min         -2.035
_refine_diff_density_rms         0.259
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3852
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0594
_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)+(0.1187P)²+1.1391P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1618
_reflns_number_gt                3550
_reflns_number_total             3852
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b906140a.txt
_cod_data_source_block           081016t
_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        1225.2(9)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7002029
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.65971(6) 0.19551(5) 0.68419(3) 0.0270(2) Uani 1 1 d . . .
Br2 Br 0.7493(2) -0.0463(2) 0.65112(11) 0.0398(4) Uani 1 1 d . . .
Br1 Br 0.43750(18) 0.0957(3) 0.75858(11) 0.0456(5) Uani 1 1 d . . .
Br3 Br 0.5783(3) 0.4400(3) 0.71400(14) 0.0544(5) Uani 1 1 d . . .
N3 N 0.9862(15) 0.3391(14) 0.9019(8) 0.024(3) Uani 1 1 d . . .
H3A H 0.9962 0.2497 0.9169 0.029 Uiso 1 1 calc R . .
N2 N 0.9910(13) 0.2855(13) 0.6728(7) 0.021(2) Uani 1 1 d . . .
C1 C 0.8539(19) 0.2733(18) 0.6292(10) 0.029(3) Uani 1 1 d . . .
O1 O 0.9877(17) 0.5023(12) 0.7904(7) 0.040(3) Uani 1 1 d . . .
C16 C 0.627(2) 0.061(2) 1.0873(14) 0.049(5) Uani 1 1 d . . .
H16A H 0.5972 -0.0285 1.1090 0.059 Uiso 1 1 calc R . .
C15 C 0.5996(19) 0.087(2) 1.0026(13) 0.040(4) Uani 1 1 d . . .
H15A H 0.5506 0.0183 0.9671 0.048 Uiso 1 1 calc R . .
C9 C 0.9942(16) 0.3795(16) 0.8183(9) 0.024(3) Uani 1 1 d . . .
C10 C 0.9606(18) 0.4511(16) 0.9636(9) 0.019(3) Uani 1 1 d . . .
H10A H 0.9883 0.5440 0.9380 0.023 Uiso 1 1 calc R . .
C2 C 1.028(2) 0.3633(19) 0.5448(11) 0.036(4) Uani 1 1 d . . .
H2A H 1.0733 0.4015 0.4971 0.043 Uiso 1 1 calc R . .
C3 C 1.104(2) 0.3407(17) 0.6215(9) 0.028(3) Uani 1 1 d . . .
H3B H 1.2104 0.3586 0.6364 0.033 Uiso 1 1 calc R . .
C14 C 0.6463(18) 0.2191(19) 0.9712(10) 0.033(4) Uani 1 1 d . . .
H14A H 0.6252 0.2393 0.9139 0.039 Uiso 1 1 calc R . .
C17 C 0.6973(19) 0.161(2) 1.1420(11) 0.039(4) Uani 1 1 d . . .
H17A H 0.7086 0.1412 1.1999 0.047 Uiso 1 1 calc R . .
N1 N 0.8755(15) 0.3210(14) 0.5495(8) 0.030(3) Uani 1 1 d . . .
C8 C 1.0222(18) 0.2466(16) 0.7628(9) 0.025(3) Uani 1 1 d . . .
H8A H 1.1308 0.2137 0.7718 0.030 Uiso 1 1 calc R . .
H8B H 0.9525 0.1683 0.7782 0.030 Uiso 1 1 calc R . .
C12 C 0.7811(16) 0.4599(17) 0.9859(10) 0.028(3) Uani 1 1 d . . .
H12A H 0.7684 0.5368 1.0270 0.034 Uiso 1 1 calc R . .
H12B H 0.7175 0.4845 0.9349 0.034 Uiso 1 1 calc R . .
C18 C 0.7506(18) 0.290(2) 1.1107(10) 0.032(4) Uani 1 1 d . . .
H18A H 0.8040 0.3559 1.1464 0.039 Uiso 1 1 calc R . .
C4 C 0.756(2) 0.344(2) 0.4755(11) 0.042(4) Uani 1 1 d . . .
C7 C 0.608(3) 0.254(3) 0.4843(14) 0.074(8) Uani 1 1 d . . .
H7A H 0.5356 0.2710 0.4363 0.111 Uiso 1 1 calc R . .
H7B H 0.5581 0.2809 0.5355 0.111 Uiso 1 1 calc R . .
H7C H 0.6356 0.1531 0.4867 0.111 Uiso 1 1 calc R . .
C6 C 0.833(3) 0.294(3) 0.3952(13) 0.068(7) Uani 1 1 d . . .
H6A H 0.7600 0.3070 0.3471 0.102 Uiso 1 1 calc R . .
H6B H 0.8601 0.1929 0.4006 0.102 Uiso 1 1 calc R . .
H6C H 0.9269 0.3496 0.3874 0.102 Uiso 1 1 calc R . .
C5 C 0.721(4) 0.507(3) 0.4758(18) 0.089(10) Uani 1 1 d . . .
H5A H 0.6466 0.5295 0.4298 0.134 Uiso 1 1 calc R . .
H5B H 0.8176 0.5595 0.4690 0.134 Uiso 1 1 calc R . .
H5C H 0.6775 0.5330 0.5287 0.134 Uiso 1 1 calc R . .
O2 O 1.1471(12) 0.3165(11) 1.0500(6) 0.029(2) Uani 1 1 d . . .
C13 C 0.7226(18) 0.3216(16) 1.0210(9) 0.026(3) Uani 1 1 d . . .
O3 O 1.0574(14) 0.5240(12) 1.1015(7) 0.032(3) Uani 1 1 d . . .
C11 C 1.062(2) 0.4349(16) 1.0463(10) 0.023(3) Uani 1 1 d . . .
C19 C 1.241(2) 0.294(2) 1.1304(13) 0.045(5) Uani 1 1 d . . .
H19A H 1.2993 0.2047 1.1273 0.067 Uiso 1 1 calc R . .
H19B H 1.1713 0.2888 1.1765 0.067 Uiso 1 1 calc R . .
H19C H 1.3134 0.3732 1.1396 0.067 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'
Br Br -0.2901 2.4595 '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 Br3 89.9(5) . . ?
C1 Au1 Br2 88.0(5) . . ?
Br3 Au1 Br2 177.84(7) . . ?
C1 Au1 Br1 176.1(4) . . ?
Br3 Au1 Br1 91.39(8) . . ?
Br2 Au1 Br1 90.76(7) . . ?
C9 N3 C10 118.0(13) . . ?
C1 N2 C3 110.1(13) . . ?
C1 N2 C8 126.1(13) . . ?
C3 N2 C8 123.8(12) . . ?
N2 C1 N1 107.4(14) . . ?
N2 C1 Au1 121.1(11) . . ?
N1 C1 Au1 131.5(12) . . ?
C15 C16 C17 122.6(18) . . ?
C16 C15 C14 118.2(17) . . ?
O1 C9 N3 126.5(14) . . ?
O1 C9 C8 123.0(13) . . ?
N3 C9 C8 110.4(12) . . ?
N3 C10 C11 114.1(11) . . ?
N3 C10 C12 111.5(12) . . ?
C11 C10 C12 108.6(11) . . ?
N1 C2 C3 108.6(14) . . ?
C2 C3 N2 105.4(14) . . ?
C13 C14 C15 122.5(15) . . ?
C16 C17 C18 119.6(17) . . ?
C2 N1 C1 108.5(14) . . ?
C2 N1 C4 121.2(14) . . ?
C1 N1 C4 130.0(14) . . ?
N2 C8 C9 109.3(11) . . ?
C13 C12 C10 112.4(13) . . ?
C17 C18 C13 119.0(16) . . ?
C7 C4 C6 107.3(18) . . ?
C7 C4 C5 112(2) . . ?
C6 C4 C5 113(2) . . ?
C7 C4 N1 111.9(14) . . ?
C6 C4 N1 107.3(15) . . ?
C5 C4 N1 105.0(17) . . ?
C11 O2 C19 115.4(12) . . ?
C14 C13 C18 118.0(14) . . ?
C14 C13 C12 122.3(14) . . ?
C18 C13 C12 119.7(14) . . ?
O3 C11 O2 125.3(15) . . ?
O3 C11 C10 120.9(14) . . ?
O2 C11 C10 113.8(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 C1 2.025(17) . ?
Au1 Br3 2.408(2) . ?
Au1 Br2 2.418(2) . ?
Au1 Br1 2.4431(18) . ?
N3 C9 1.374(19) . ?
N3 C10 1.442(19) . ?
N2 C1 1.32(2) . ?
N2 C3 1.381(19) . ?
N2 C8 1.474(19) . ?
C1 N1 1.35(2) . ?
O1 C9 1.214(18) . ?
C16 C15 1.37(3) . ?
C16 C17 1.38(3) . ?
C15 C14 1.38(3) . ?
C9 C8 1.53(2) . ?
C10 C11 1.531(19) . ?
C10 C12 1.58(2) . ?
C2 N1 1.35(2) . ?
C2 C3 1.36(2) . ?
C14 C13 1.37(2) . ?
C17 C18 1.37(3) . ?
N1 C4 1.52(2) . ?
C12 C13 1.48(2) . ?
C18 C13 1.45(2) . ?
C4 C7 1.52(3) . ?
C4 C6 1.53(3) . ?
C4 C5 1.52(3) . ?
O2 C11 1.31(2) . ?
O2 C19 1.475(18) . ?
O3 C11 1.197(19) . ?
