#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/56/1505682.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_1505682
loop_
_publ_author_name
'Gunatilleke, Shamila S.'
'Barrios, Amy M.'
_publ_section_title
;
 Inhibition of lysosomal cysteine proteases by a series of Au(I)
 complexes: a detailed mechanistic investigation.
;
_journal_issue                   13
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              3933
_journal_page_last               3937
_journal_paper_doi               10.1021/jm060158f
_journal_volume                  49
_journal_year                    2006
_chemical_formula_sum            'C27 H25 Au N O5 P S'
_chemical_formula_weight         703.48
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.208(3)
_cell_angle_beta                 112.512(3)
_cell_angle_gamma                104.970(3)
_cell_formula_units_Z            2
_cell_length_a                   10.2180(19)
_cell_length_b                   12.489(2)
_cell_length_c                   12.620(2)
_cell_measurement_reflns_used    4015
_cell_measurement_temperature    128(2)
_cell_measurement_theta_max      27.24
_cell_measurement_theta_min      2.20
_cell_volume                     1302.0(4)
_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      128(2)
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0608
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7934
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.93
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    5.830
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method
'Recrystallized from ethanol and dichloromethane'
_refine_diff_density_max         2.214
_refine_diff_density_min         -1.133
_refine_diff_density_rms         0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0397P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0897
_reflns_number_gt                4672
_reflns_number_total             5579
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jm060158fsi20060213_011931.cif
_cod_data_source_block           shaum
_cod_original_cell_volume        1301.9(4)
_cod_database_code               1505682
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Au1 Au 0.92786(3) 0.92064(2) 0.73449(2) 0.02844(9) Uani 1 1 d .
S1 S 1.16129(18) 0.97953(16) 0.73580(15) 0.0335(4) Uani 1 1 d .
P1 P 0.71019(17) 0.86757(14) 0.75108(14) 0.0250(3) Uani 1 1 d .
O1 O 1.1140(7) 1.4090(5) 0.5252(5) 0.0611(15) Uani 1 1 d .
O2 O 1.3341(7) 1.4133(5) 0.5471(5) 0.0653(16) Uani 1 1 d .
O3 O 0.7236(5) 1.2709(4) 1.1442(4) 0.0435(12) Uani 1 1 d .
O4 O 0.1227(5) 0.6564(4) 0.2619(4) 0.0410(11) Uani 1 1 d .
O5 O 0.6918(6) 0.4920(4) 0.9587(4) 0.0445(12) Uani 1 1 d .
N1 N 1.2221(8) 1.3739(6) 0.5555(5) 0.0435(14) Uani 1 1 d .
C1 C 1.1707(7) 1.0939(6) 0.6830(6) 0.0347(15) Uani 1 1 d .
C2 C 1.0466(8) 1.1262(7) 0.6308(6) 0.0416(17) Uani 1 1 d .
H2 H 0.9492 1.0818 0.6216 0.050 Uiso 1 1 calc R
C3 C 1.0606(8) 1.2207(7) 0.5921(6) 0.0422(17) Uani 1 1 d .
H3 H 0.9771 1.2439 0.5607 0.051 Uiso 1 1 calc R
C4 C 1.2016(8) 1.2789(6) 0.6014(6) 0.0349(15) Uani 1 1 d .
C5 C 1.3280(8) 1.2541(7) 0.6557(7) 0.0482(19) Uani 1 1 d .
H5 H 1.4253 1.2999 0.6656 0.058 Uiso 1 1 calc R
C6 C 1.3121(8) 1.1627(7) 0.6954(7) 0.0491(19) Uani 1 1 d .
H6 H 1.3996 1.1454 0.7326 0.059 Uiso 1 1 calc R
C7 C 0.7133(6) 0.9972(5) 0.8614(5) 0.0242(12) Uani 1 1 d .
C8 C 0.5784(6) 1.0062(5) 0.8573(6) 0.0289(13) Uani 1 1 d .
H8 H 0.4800 0.9468 0.7884 0.035 Uiso 1 1 calc R
C9 C 0.5856(7) 1.0998(6) 0.9516(6) 0.0303(14) Uani 1 1 d .
H9 H 0.4926 1.1054 0.9467 0.036 Uiso 1 1 calc R
C10 C 0.7294(7) 1.1864(6) 1.0542(6) 0.0325(14) Uani 1 1 d .
C11 C 0.8640(7) 1.1824(5) 1.0571(5) 0.0317(14) Uani 1 1 d .
H11 H 0.9622 1.2440 1.1242 0.038 Uiso 1 1 calc R
C12 C 0.8559(7) 1.0879(6) 0.9613(5) 0.0290(14) Uani 1 1 d .
H12 H 0.9492 1.0852 0.9642 0.035 Uiso 1 1 calc R
C13 C 0.8673(9) 1.3521(8) 1.2572(7) 0.061(2) Uani 1 1 d .
H13A H 0.9168 1.3044 1.2944 0.092 Uiso 1 1 calc R
H13B H 0.8477 1.4046 1.3178 0.092 Uiso 1 1 calc R
H13C H 0.9361 1.4029 1.2369 0.092 Uiso 1 1 calc R
C14 C 0.5291(6) 0.8059(5) 0.6053(5) 0.0231(12) Uani 1 1 d .
C15 C 0.3987(7) 0.7088(6) 0.5744(6) 0.0345(15) Uani 1 1 d .
H15 H 0.4013 0.6740 0.6327 0.041 Uiso 1 1 calc R
C16 C 0.2639(7) 0.6614(6) 0.4594(6) 0.0355(15) Uani 1 1 d .
H16 H 0.1754 0.5941 0.4395 0.043 Uiso 1 1 calc R
C17 C 0.2572(7) 0.7113(6) 0.3736(5) 0.0283(13) Uani 1 1 d .
C18 C 0.3840(7) 0.8123(6) 0.4049(6) 0.0352(15) Uani 1 1 d .
H18 H 0.3792 0.8500 0.3486 0.042 Uiso 1 1 calc R
C19 C 0.5196(7) 0.8581(6) 0.5207(6) 0.0336(14) Uani 1 1 d .
H19 H 0.6073 0.9268 0.5418 0.040 Uiso 1 1 calc R
C20 C 0.1186(8) 0.6995(8) 0.1674(6) 0.052(2) Uani 1 1 d .
H20A H 0.1308 0.7847 0.1976 0.077 Uiso 1 1 calc R
H20B H 0.0187 0.6488 0.0894 0.077 Uiso 1 1 calc R
H20C H 0.2033 0.6947 0.1505 0.077 Uiso 1 1 calc R
C21 C 0.6980(6) 0.7543(5) 0.8151(5) 0.0244(12) Uani 1 1 d .
C22 C 0.6918(7) 0.6416(6) 0.7502(6) 0.0314(14) Uani 1 1 d .
H22 H 0.6886 0.6225 0.6707 0.038 Uiso 1 1 calc R
C23 C 0.6903(7) 0.5568(6) 0.8017(6) 0.0349(15) Uani 1 1 d .
H23 H 0.6856 0.4796 0.7569 0.042 Uiso 1 1 calc R
C24 C 0.6957(7) 0.5840(6) 0.9181(6) 0.0346(15) Uani 1 1 d .
C25 C 0.7044(7) 0.6950(6) 0.9827(6) 0.0328(14) Uani 1 1 d .
H25 H 0.7103 0.7145 1.0633 0.039 Uiso 1 1 calc R
C26 C 0.7046(7) 0.7805(6) 0.9316(5) 0.0297(13) Uani 1 1 d .
H26 H 0.7093 0.8574 0.9770 0.036 Uiso 1 1 calc R
C27 C 0.7036(9) 0.5171(7) 1.0812(7) 0.055(2) Uani 1 1 d .
H27A H 0.8049 0.5835 1.1466 0.082 Uiso 1 1 calc R
H27B H 0.6934 0.4434 1.0966 0.082 Uiso 1 1 calc R
H27C H 0.6206 0.5413 1.0839 0.082 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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
P1 Au1 S1 175.13(6)
C1 S1 Au1 106.2(2)
C7 P1 C14 106.9(3)
C7 P1 C21 105.3(3)
C14 P1 C21 106.6(3)
C7 P1 Au1 110.59(19)
C14 P1 Au1 115.63(18)
C21 P1 Au1 111.18(18)
C10 O3 C13 116.8(6)
C17 O4 C20 117.2(5)
C24 O5 C27 117.5(5)
O2 N1 O1 123.1(7)
O2 N1 C4 120.8(7)
O1 N1 C4 116.1(6)
C6 C1 C2 116.5(6)
C6 C1 S1 118.8(5)
C2 C1 S1 124.7(5)
C3 C2 C1 122.7(6)
C4 C3 C2 116.8(6)
C5 C4 C3 122.8(6)
C5 C4 N1 117.3(6)
C3 C4 N1 119.9(6)
C6 C5 C4 119.1(6)
C5 C6 C1 122.0(7)
C12 C7 C8 118.1(5)
C12 C7 P1 119.0(4)
C8 C7 P1 122.7(4)
C9 C8 C7 121.1(5)
C8 C9 C10 120.0(6)
O3 C10 C11 124.8(6)
O3 C10 C9 115.4(6)
C11 C10 C9 119.8(6)
C10 C11 C12 119.8(5)
C11 C12 C7 121.1(6)
C15 C14 C19 118.1(5)
C15 C14 P1 122.8(4)
C19 C14 P1 119.0(4)
C14 C15 C16 121.0(6)
C17 C16 C15 120.5(6)
O4 C17 C18 124.0(5)
O4 C17 C16 116.4(5)
C18 C17 C16 119.6(5)
C17 C18 C19 119.1(6)
C14 C19 C18 121.6(6)
C26 C21 C22 118.9(6)
C26 C21 P1 121.4(5)
C22 C21 P1 119.6(4)
C21 C22 C23 119.9(6)
C22 C23 C24 120.4(6)
C25 C24 O5 125.2(6)
C25 C24 C23 119.7(6)
O5 C24 C23 115.1(6)
C24 C25 C26 120.3(6)
C21 C26 C25 120.6(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Au1 P1 2.2588(15)
Au1 S1 2.2993(16)
S1 C1 1.733(7)
P1 C7 1.800(6)
P1 C14 1.808(6)
P1 C21 1.815(6)
O1 N1 1.256(8)
O2 N1 1.181(8)
O3 C10 1.350(7)
O3 C13 1.428(8)
O4 C17 1.354(7)
O4 C20 1.430(8)
O5 C24 1.379(7)
O5 C27 1.439(8)
N1 C4 1.462(9)
C1 C6 1.400(9)
C1 C2 1.407(9)
C2 C3 1.393(10)
C3 C4 1.378(9)
C4 C5 1.371(9)
C5 C6 1.366(10)
C7 C12 1.393(8)
C7 C8 1.394(8)
C8 C9 1.379(8)
C9 C10 1.395(8)
C10 C11 1.377(9)
C11 C12 1.391(8)
C14 C15 1.379(8)
C14 C19 1.384(8)
C15 C16 1.386(8)
C16 C17 1.382(8)
C17 C18 1.382(8)
C18 C19 1.398(8)
C21 C26 1.384(8)
C21 C22 1.388(8)
C22 C23 1.388(9)
C23 C24 1.389(9)
C24 C25 1.358(9)
C25 C26 1.393(8)
