#------------------------------------------------------------------------------
#$Date: 2016-03-21 11:01:58 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178677 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/88/4078839.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_4078839
loop_
_publ_author_name
'Sivaram, Haresh'
'Tan, Jackie'
'Huynh, Han Vinh'
_publ_section_title
;
 Syntheses, Characterizations, and a Preliminary Comparative Cytotoxicity
 Study of Gold(I) and Gold(III) Complexes Bearing Benzimidazole- and
 Pyrazole-Derived N-Heterocyclic Carbenes
;
_journal_issue                   16
_journal_name_full               Organometallics
_journal_page_first              5875
_journal_paper_doi               10.1021/om300444c
_journal_volume                  31
_journal_year                    2012
_chemical_formula_sum            'C24 H34 Au F6 N4 P'
_chemical_formula_weight         720.49
_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                 102.706(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6027(13)
_cell_length_b                   13.8516(16)
_cell_length_c                   18.185(2)
_cell_measurement_reflns_used    954
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.46
_cell_volume                     2605.3(5)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18346
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    5.772
_exptl_absorpt_correction_T_max  0.4305
_exptl_absorpt_correction_T_min  0.2906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.837
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.983
_refine_diff_density_min         -1.146
_refine_diff_density_rms         0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0349
_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)+(0.0505P)²+3.0924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                5214
_reflns_number_total             5976
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om300444c_si_002.cif
_cod_data_source_block           '[Au(FPyr)(iPr2-bimy)]PF6(5)'
_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 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4078839
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 0.449680(17) 0.644300(13) 0.049059(10) 0.01560(8) Uani 1 1 d .
N1 N 0.3806(4) 0.4730(3) 0.1343(2) 0.0165(9) Uani 1 1 d .
N2 N 0.5908(4) 0.4835(3) 0.1502(2) 0.0177(9) Uani 1 1 d .
N3 N 0.2895(4) 0.7971(3) -0.0427(2) 0.0196(9) Uani 1 1 d .
N4 N 0.2937(5) 0.8796(3) -0.0841(3) 0.0223(10) Uani 1 1 d .
C1 C 0.4784(5) 0.5255(4) 0.1154(3) 0.0174(10) Uani 1 1 d .
C2 C 0.4326(5) 0.3979(4) 0.1828(3) 0.0189(10) Uani 1 1 d .
C3 C 0.3743(6) 0.3300(4) 0.2218(3) 0.0215(11) Uani 1 1 d .
H3 H 0.2831 0.3265 0.2156 0.026 Uiso 1 1 calc R
C4 C 0.4571(6) 0.2679(4) 0.2702(3) 0.0275(12) Uani 1 1 d .
H4 H 0.4218 0.2220 0.2989 0.033 Uiso 1 1 calc R
C5 C 0.5915(6) 0.2721(4) 0.2774(3) 0.0261(12) Uani 1 1 d .
H5 H 0.6446 0.2274 0.3098 0.031 Uiso 1 1 calc R
C6 C 0.6498(6) 0.3396(4) 0.2385(3) 0.0232(12) Uani 1 1 d .
H6 H 0.7408 0.3417 0.2433 0.028 Uiso 1 1 calc R
C7 C 0.5669(5) 0.4038(4) 0.1920(3) 0.0176(10) Uani 1 1 d .
C8 C 0.2411(5) 0.4968(4) 0.1087(3) 0.0174(10) Uani 1 1 d .
H8 H 0.2352 0.5536 0.0741 0.021 Uiso 1 1 calc R
C9 C 0.1834(6) 0.5276(4) 0.1744(3) 0.0274(12) Uani 1 1 d .
H9A H 0.1722 0.4709 0.2045 0.041 Uiso 1 1 calc R
H9B H 0.0992 0.5581 0.1551 0.041 Uiso 1 1 calc R
H9C H 0.2414 0.5738 0.2059 0.041 Uiso 1 1 calc R
C10 C 0.1671(5) 0.4148(4) 0.0631(3) 0.0267(12) Uani 1 1 d .
H10A H 0.2093 0.3971 0.0222 0.040 Uiso 1 1 calc R
H10B H 0.0782 0.4355 0.0419 0.040 Uiso 1 1 calc R
H10C H 0.1661 0.3588 0.0960 0.040 Uiso 1 1 calc R
C11 C 0.7177(5) 0.5245(4) 0.1500(3) 0.0181(10) Uani 1 1 d .
H11 H 0.7033 0.5841 0.1183 0.022 Uiso 1 1 calc R
C12 C 0.7875(5) 0.5548(4) 0.2293(3) 0.0240(11) Uani 1 1 d .
H12A H 0.7374 0.6051 0.2478 0.036 Uiso 1 1 calc R
H12B H 0.8734 0.5800 0.2279 0.036 Uiso 1 1 calc R
H12C H 0.7966 0.4989 0.2630 0.036 Uiso 1 1 calc R
C13 C 0.7985(5) 0.4547(4) 0.1134(3) 0.0243(12) Uani 1 1 d .
H13A H 0.8227 0.3984 0.1462 0.036 Uiso 1 1 calc R
H13B H 0.8768 0.4876 0.1063 0.036 Uiso 1 1 calc R
H13C H 0.7475 0.4335 0.0644 0.036 Uiso 1 1 calc R
C14 C 0.4118(5) 0.7631(4) -0.0171(3) 0.0182(10) Uani 1 1 d .
C15 C 0.1720(5) 0.7738(4) -0.0160(3) 0.0232(11) Uani 1 1 d .
H15A H 0.1765 0.8055 0.0333 0.028 Uiso 1 1 calc R
H15B H 0.1682 0.7032 -0.0084 0.028 Uiso 1 1 calc R
C16 C 0.0493(5) 0.8060(4) -0.0707(3) 0.0252(12) Uani 1 1 d .
H16A H -0.0262 0.7970 -0.0476 0.030 Uiso 1 1 calc R
H16B H 0.0357 0.7668 -0.1173 0.030 Uiso 1 1 calc R
C17 C 0.0630(6) 0.9126(5) -0.0894(4) 0.0339(15) Uani 1 1 d .
H17A H -0.0180 0.9358 -0.1227 0.041 Uiso 1 1 calc R
H17B H 0.0790 0.9513 -0.0425 0.041 Uiso 1 1 calc R
C18 C 0.1751(6) 0.9249(5) -0.1286(4) 0.0324(14) Uani 1 1 d .
H18A H 0.1525 0.8949 -0.1792 0.039 Uiso 1 1 calc R
H18B H 0.1908 0.9945 -0.1351 0.039 Uiso 1 1 calc R
C19 C 0.4160(5) 0.8957(4) -0.0870(3) 0.0171(10) Uani 1 1 d .
C20 C 0.4624(6) 0.9764(4) -0.1290(3) 0.0297(13) Uani 1 1 d .
H20A H 0.4205 1.0376 -0.1195 0.036 Uiso 1 1 calc R
H20B H 0.4398 0.9632 -0.1838 0.036 Uiso 1 1 calc R
C21 C 0.6090(7) 0.9850(5) -0.1020(5) 0.0444(18) Uani 1 1 d .
H21A H 0.6427 1.0202 -0.1410 0.053 Uiso 1 1 calc R
H21B H 0.6272 1.0251 -0.0558 0.053 Uiso 1 1 calc R
C22 C 0.6815(6) 0.8949(6) -0.0856(4) 0.0444(18) Uani 1 1 d .
H22A H 0.7729 0.9113 -0.0634 0.053 Uiso 1 1 calc R
H22B H 0.6794 0.8613 -0.1339 0.053 Uiso 1 1 calc R
C23 C 0.6354(6) 0.8252(4) -0.0331(4) 0.0290(13) Uani 1 1 d .
H23A H 0.6653 0.7592 -0.0416 0.035 Uiso 1 1 calc R
H23B H 0.6738 0.8432 0.0198 0.035 Uiso 1 1 calc R
C24 C 0.4909(5) 0.8254(4) -0.0451(3) 0.0171(10) Uani 1 1 d .
P1 P 0.95733(14) 0.70700(11) 0.65568(8) 0.0236(3) Uani 1 1 d .
F1 F 1.0001(5) 0.7672(3) 0.7315(2) 0.0595(13) Uani 1 1 d .
F2 F 0.9948(6) 0.6116(3) 0.7031(2) 0.0661(15) Uani 1 1 d .
F3 F 0.9204(5) 0.6481(3) 0.5794(2) 0.0488(11) Uani 1 1 d .
F4 F 0.9208(6) 0.8036(3) 0.6094(3) 0.0786(18) Uani 1 1 d .
F5 F 1.1016(4) 0.7181(6) 0.6458(3) 0.091(2) Uani 1 1 d .
F6 F 0.8143(4) 0.7002(6) 0.6656(3) 0.086(2) 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'
F F 0.0171 0.0103 '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'
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
C1 Au1 C14 177.2(2)
C1 N1 C2 109.8(4)
C1 N1 C8 124.0(4)
C2 N1 C8 126.2(4)
C1 N2 C7 110.4(4)
C1 N2 C11 123.3(4)
C7 N2 C11 125.9(4)
C14 N3 N4 109.4(4)
C14 N3 C15 128.6(4)
N4 N3 C15 119.7(4)
C19 N4 N3 108.1(4)
C19 N4 C18 128.9(5)
N3 N4 C18 121.8(4)
N2 C1 N1 107.0(4)
N2 C1 Au1 129.1(4)
N1 C1 Au1 123.9(4)
N1 C2 C7 106.4(4)
N1 C2 C3 131.5(5)
C7 C2 C3 122.1(5)
C4 C3 C2 116.5(5)
C3 C4 C5 121.2(5)
C6 C5 C4 122.3(5)
C5 C6 C7 116.3(5)
N2 C7 C6 131.9(5)
N2 C7 C2 106.5(4)
C6 C7 C2 121.5(5)
N1 C8 C10 111.3(4)
N1 C8 C9 111.2(4)
C10 C8 C9 112.9(5)
N2 C11 C12 111.1(4)
N2 C11 C13 111.0(4)
C12 C11 C13 112.4(4)
N3 C14 C24 105.5(4)
N3 C14 Au1 122.3(4)
C24 C14 Au1 132.2(4)
N3 C15 C16 112.7(4)
C15 C16 C17 108.6(4)
C18 C17 C16 109.5(5)
N4 C18 C17 110.7(5)
N4 C19 C24 108.0(4)
N4 C19 C20 125.4(5)
C24 C19 C20 126.6(5)
C19 C20 C21 108.7(5)
C22 C21 C20 116.8(6)
C21 C22 C23 116.4(6)
C24 C23 C22 111.6(5)
C19 C24 C14 109.0(5)
C19 C24 C23 121.9(5)
C14 C24 C23 129.1(5)
F6 P1 F2 91.1(3)
F6 P1 F3 90.6(3)
F2 P1 F3 91.8(2)
F6 P1 F4 89.0(4)
F2 P1 F4 179.0(3)
F3 P1 F4 89.2(2)
F6 P1 F5 177.9(4)
F2 P1 F5 90.6(3)
F3 P1 F5 90.5(3)
F4 P1 F5 89.3(4)
F6 P1 F1 91.7(3)
F2 P1 F1 88.6(2)
F3 P1 F1 177.6(3)
F4 P1 F1 90.5(2)
F5 P1 F1 87.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Au1 C1 2.024(5)
Au1 C14 2.026(5)
N1 C1 1.371(6)
N1 C2 1.397(6)
N1 C8 1.486(6)
N2 C1 1.352(6)
N2 C7 1.394(6)
N2 C11 1.461(6)
N3 C14 1.362(7)
N3 N4 1.375(6)
N3 C15 1.469(7)
N4 C19 1.329(7)
N4 C18 1.476(7)
C2 C7 1.399(7)
C2 C3 1.401(7)
C3 C4 1.395(8)
C4 C5 1.403(8)
C5 C6 1.396(8)
C6 C7 1.398(7)
C8 C10 1.518(7)
C8 C9 1.520(7)
C11 C12 1.528(7)
C11 C13 1.537(7)
C14 C24 1.377(7)
C15 C16 1.520(7)
C16 C17 1.529(9)
C17 C18 1.524(8)
C19 C24 1.376(7)
C19 C20 1.495(7)
C20 C21 1.528(9)
C21 C22 1.461(10)
C22 C23 1.514(9)
C23 C24 1.500(8)
P1 F6 1.568(5)
P1 F2 1.581(4)
P1 F3 1.582(4)
P1 F4 1.583(4)
P1 F5 1.586(5)
P1 F1 1.590(4)
