#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:27:03 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179481 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/78/4337839.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_4337839
loop_
_publ_author_name
'Messori, Luigi'
'Marchetti, Lorella'
'Massai, Lara'
'Scaletti, Federica'
'Guerri, Annalisa'
'Landini, Ida'
'Nobili, Stefania'
'Perrone, Gabriele'
'Mini, Enrico'
'Leoni, Piero'
'Pasquali, Marco'
'Gabbiani, Chiara'
_publ_section_title
;
 Chemistry and biology of two novel gold(i) carbene complexes as
 prospective anticancer agents.
;
_journal_issue                   5
_journal_name_full               'Inorganic chemistry'
_journal_page_first              2396
_journal_page_last               2403
_journal_paper_doi               10.1021/ic401731a
_journal_volume                  53
_journal_year                    2014
_chemical_formula_moiety         'C8 H14 Au Cl N2'
_chemical_formula_sum            'C8 H14 Au Cl N2'
_chemical_formula_weight         370.63
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2009(6)
_cell_length_b                   10.6215(7)
_cell_length_c                   12.1355(9)
_cell_measurement_temperature    120(2)
_cell_volume                     1057.07(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 16.4547
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_av_unetI/netI     0.1051
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3998
_diffrn_reflns_point_group_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.742
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.325
_diffrn_reflns_theta_min         4.572
_exptl_absorpt_coefficient_mu    14.121
_exptl_absorpt_correction_T_max  0.8683
_exptl_absorpt_correction_T_min  0.3468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.329
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         3.588
_refine_diff_density_min         -5.530
_refine_diff_density_rms         0.495
_refine_ls_abs_structure_details
;
 Flack x determined using 570 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.10(5)
_refine_ls_extinction_coef       0.0050(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         2154
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0709
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0906P)²+7.1774P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1793
_refine_ls_wR_factor_ref         0.1863
_reflns_Friedel_coverage         0.522
_reflns_Friedel_fraction_full    0.822
_reflns_Friedel_fraction_max     0.602
_reflns_number_gt                1911
_reflns_number_total             2154
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic401731a_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4337839
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2012-9
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Au1 Au 0.74326(9) 0.70383(6) 0.12552(6) 0.0176(4) Uani 1 1 d . .
Cl1 Cl 0.7287(7) 0.8695(4) 0.0061(4) 0.0233(11) Uani 1 1 d . .
C1 C 0.754(3) 0.5657(15) 0.2307(17) 0.016(4) Uiso 1 1 d . .
N2 N 0.891(2) 0.5290(18) 0.2894(18) 0.021(4) Uiso 1 1 d . .
N1 N 0.642(2) 0.4795(17) 0.2613(19) 0.023(4) Uiso 1 1 d . .
C4 C 0.854(3) 0.424(2) 0.351(2) 0.027(3) Uiso 1 1 d . .
H4 H 0.9287 0.3779 0.3952 0.032 Uiso 1 1 calc R U
C3 C 0.696(3) 0.396(2) 0.339(2) 0.027(3) Uiso 1 1 d . .
H3 H 0.6351 0.3328 0.3759 0.032 Uiso 1 1 calc R U
C5 C 1.042(5) 0.598(4) 0.289(4) 0.083(7) Uiso 1 1 d D .
H5A H 1.0666 0.6252 0.2129 0.100 Uiso 1 1 calc R U
H5B H 1.1311 0.5411 0.3132 0.100 Uiso 1 1 calc R U
C2 C 0.477(4) 0.486(3) 0.225(3) 0.046(8) Uiso 1 1 d . .
H2A H 0.4438 0.5738 0.2174 0.069 Uiso 1 1 calc R U
H2B H 0.4062 0.4440 0.2794 0.069 Uiso 1 1 calc R U
H2C H 0.4661 0.4429 0.1539 0.069 Uiso 1 1 calc R U
C7 C 1.016(5) 0.697(3) 0.489(3) 0.083(7) Uiso 1 1 d D .
H7A H 1.1117 0.6499 0.5167 0.100 Uiso 1 1 calc R U
H7B H 0.9191 0.6437 0.5007 0.100 Uiso 1 1 calc R U
C6 C 1.038(5) 0.715(3) 0.366(3) 0.083(7) Uiso 1 1 d D .
H6A H 1.1407 0.7618 0.3541 0.100 Uiso 1 1 calc R U
H6B H 0.9481 0.7698 0.3396 0.100 Uiso 1 1 calc R U
C8 C 0.997(5) 0.815(4) 0.560(4) 0.083(7) Uiso 1 1 d D .
H8A H 1.0278 0.7952 0.6360 0.125 Uiso 1 1 calc R U
H8B H 0.8833 0.8427 0.5578 0.125 Uiso 1 1 calc R U
H8C H 1.0678 0.8816 0.5314 0.125 Uiso 1 1 calc R U
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 Au1 Cl1 178.4(6)
N1 C1 N2 102.5(17)
N1 C1 Au1 131.3(16)
N2 C1 Au1 126.0(14)
C4 N2 C1 109.2(17)
C4 N2 C5 127(3)
C1 N2 C5 124(3)
C1 N1 C3 114.3(19)
C1 N1 C2 122(2)
C3 N1 C2 123(2)
C3 C4 N2 109(2)
C3 C4 H4 125.3
N2 C4 H4 125.3
C4 C3 N1 104(2)
C4 C3 H3 127.9
N1 C3 H3 127.9
N2 C5 C6 113(3)
N2 C5 H5A 109.1
C6 C5 H5A 109.1
N2 C5 H5B 109.1
C6 C5 H5B 109.1
H5A C5 H5B 107.8
N1 C2 H2A 109.5
N1 C2 H2B 109.5
H2A C2 H2B 109.5
N1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
C6 C7 C8 118(3)
C6 C7 H7A 107.8
C8 C7 H7A 107.8
C6 C7 H7B 107.8
C8 C7 H7B 107.8
H7A C7 H7B 107.2
C7 C6 C5 120(3)
C7 C6 H6A 107.4
C5 C6 H6A 107.4
C7 C6 H6B 107.4
C5 C6 H6B 107.4
H6A C6 H6B 107.0
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Au1 C1 1.947(18)
Au1 Cl1 2.282(4)
C1 N1 1.35(3)
C1 N2 1.38(3)
N2 C4 1.38(3)
N2 C5 1.44(4)
N1 C3 1.37(3)
N1 C2 1.43(4)
C4 C3 1.33(3)
C4 H4 0.9500
C3 H3 0.9500
C5 C6 1.55(2)
C5 H5A 0.9900
C5 H5B 0.9900
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
C7 C6 1.52(2)
C7 C8 1.52(2)
C7 H7A 0.9900
C7 H7B 0.9900
C6 H6A 0.9900
C6 H6B 0.9900
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
