#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:01:31 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180244 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/30/7113062.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_7113062
loop_
_publ_author_name
'Hirsch-Weil, Dimitri'
'Abboud, Khalil A.'
'Hong, Sukwon'
_publ_section_title
;
 Isoquinoline-based chiral monodentate N-heterocyclic carbenes.
;
_journal_issue                   40
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7525
_journal_page_last               7527
_journal_paper_doi               10.1039/c0cc02211j
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C27 H32 Au Cl N2'
_chemical_formula_weight         616.96
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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-97
_audit_update_record
;
2010-02-02 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4129(6)
_cell_length_b                   16.7290(11)
_cell_length_c                   17.6201(12)
_cell_measurement_reflns_used    283
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.0
_cell_volume                     2774.6(3)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2 (Bruker, 2008)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL (Bruker, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω 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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            43949
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    5.413
_exptl_absorpt_correction_T_max  0.5441
_exptl_absorpt_correction_T_min  0.3165
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
'based on measured indexed crystal faces, Bruker SHELXTL v6.12 (Bruker 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_platon_squeeze_details
;
;
_refine_diff_density_max         1.156
_refine_diff_density_min         -1.026
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.009(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.849
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         6356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.849
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0201
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0363P)²+6.6738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0562
_refine_ls_wR_factor_ref         0.0569
_reflns_number_gt                6106
_reflns_number_total             6356
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c0cc02211j.txt
_cod_data_source_block           dhw10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7113062
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
Au1 Au 0.548866(14) 0.540477(8) 0.382068(8) 0.02132(4) Uani 1 1 d .
Cl1 Cl 0.70495(11) 0.61338(7) 0.31106(6) 0.0317(2) Uani 1 1 d .
N1 N 0.2738(3) 0.4622(2) 0.42499(18) 0.0222(6) Uani 1 1 d .
N2 N 0.4276(3) 0.44694(19) 0.51300(17) 0.0201(6) Uani 1 1 d .
C1 C 0.4101(4) 0.4787(2) 0.4433(2) 0.0204(8) Uani 1 1 d .
C2 C 0.2042(4) 0.4812(2) 0.3527(2) 0.0239(8) Uani 1 1 d .
H2A H 0.2503 0.5299 0.3308 0.029 Uiso 1 1 calc R
C3 C 0.0487(4) 0.5018(2) 0.3727(3) 0.0305(9) Uani 1 1 d .
H3A H 0.0464 0.5497 0.4057 0.037 Uiso 1 1 calc R
H3B H -0.0044 0.5142 0.3257 0.037 Uiso 1 1 calc R
C4 C -0.0198(4) 0.4339(2) 0.4122(2) 0.0203(8) Uani 1 1 d .
C5 C -0.1556(4) 0.4069(2) 0.3950(2) 0.0244(8) Uani 1 1 d .
H5A H -0.2100 0.4339 0.3575 0.029 Uiso 1 1 calc R
C6 C -0.2138(4) 0.3399(3) 0.4323(2) 0.0253(8) Uani 1 1 d .
H6A H -0.3065 0.3217 0.4196 0.030 Uiso 1 1 calc R
C7 C -0.1363(4) 0.3008(2) 0.4872(2) 0.0232(8) Uani 1 1 d .
H7A H -0.1764 0.2563 0.5130 0.028 Uiso 1 1 calc R
C8 C 0.0000(4) 0.3260(2) 0.5051(2) 0.0203(7) Uani 1 1 d .
H8A H 0.0535 0.2980 0.5423 0.024 Uiso 1 1 calc R
C9 C 0.0592(4) 0.3926(2) 0.4688(2) 0.0193(7) Uani 1 1 d .
C10 C 0.2051(4) 0.4203(2) 0.4828(2) 0.0198(7) Uani 1 1 d .
C11 C 0.3022(4) 0.4132(2) 0.5406(2) 0.0205(7) Uani 1 1 d .
C12 C 0.2999(4) 0.3831(2) 0.6188(2) 0.0213(7) Uani 1 1 d .
C13 C 0.1744(4) 0.3759(2) 0.6611(2) 0.0216(8) Uani 1 1 d .
H13A H 0.0862 0.3916 0.6395 0.026 Uiso 1 1 calc R
C14 C 0.1787(5) 0.3461(3) 0.7338(2) 0.0273(9) Uani 1 1 d .
H14A H 0.0932 0.3408 0.7621 0.033 Uiso 1 1 calc R
C15 C 0.3085(5) 0.3237(2) 0.7664(2) 0.0286(9) Uani 1 1 d .
H15A H 0.3109 0.3020 0.8162 0.034 Uiso 1 1 calc R
C16 C 0.4334(5) 0.3333(2) 0.7256(2) 0.0253(8) Uani 1 1 d .
H16A H 0.5217 0.3198 0.7484 0.030 Uiso 1 1 calc R
C17 C 0.4309(4) 0.3623(2) 0.6522(2) 0.0210(7) Uani 1 1 d .
C18 C 0.5639(4) 0.3718(2) 0.6057(2) 0.0247(8) Uani 1 1 d .
H18A H 0.5746 0.3250 0.5717 0.030 Uiso 1 1 calc R
H18B H 0.6473 0.3733 0.6398 0.030 Uiso 1 1 calc R
C19 C 0.5598(4) 0.4492(2) 0.5574(2) 0.0221(7) Uani 1 1 d .
H19A H 0.6417 0.4480 0.5213 0.027 Uiso 1 1 calc R
C20 C 0.2108(5) 0.4141(3) 0.2938(3) 0.0311(10) Uani 1 1 d .
H20A H 0.1634 0.4334 0.2471 0.037 Uiso 1 1 calc R
H20B H 0.1541 0.3686 0.3132 0.037 Uiso 1 1 calc R
C21 C 0.3576(5) 0.3822(3) 0.2715(2) 0.0320(9) Uani 1 1 d .
H21A H 0.4274 0.4272 0.2734 0.038 Uiso 1 1 calc R
C22 C 0.4081(5) 0.3155(3) 0.3263(3) 0.0384(11) Uani 1 1 d .
H22A H 0.4113 0.3364 0.3782 0.058 Uiso 1 1 calc R
H22B H 0.5031 0.2974 0.3114 0.058 Uiso 1 1 calc R
H22C H 0.3418 0.2704 0.3241 0.058 Uiso 1 1 calc R
C23 C 0.3541(7) 0.3481(4) 0.1895(3) 0.0470(13) Uani 1 1 d .
H23A H 0.4486 0.3281 0.1759 0.071 Uiso 1 1 calc R
H23B H 0.3263 0.3905 0.1541 0.071 Uiso 1 1 calc R
H23C H 0.2852 0.3043 0.1869 0.071 Uiso 1 1 calc R
C24 C 0.5689(4) 0.5264(2) 0.6039(2) 0.0213(8) Uani 1 1 d .
H24A H 0.4852 0.5293 0.6377 0.026 Uiso 1 1 calc R
H24B H 0.5639 0.5724 0.5686 0.026 Uiso 1 1 calc R
C25 C 0.7033(5) 0.5347(3) 0.6522(2) 0.0305(8) Uani 1 1 d .
H25A H 0.6998 0.4941 0.6938 0.037 Uiso 1 1 calc R
C26 C 0.7084(6) 0.6178(3) 0.6878(3) 0.0390(11) Uani 1 1 d .
H26A H 0.6226 0.6265 0.7182 0.059 Uiso 1 1 calc R
H26B H 0.7137 0.6582 0.6477 0.059 Uiso 1 1 calc R
H26C H 0.7923 0.6221 0.7205 0.059 Uiso 1 1 calc R
C27 C 0.8384(5) 0.5204(3) 0.6049(3) 0.0432(13) Uani 1 1 d .
H27A H 0.9222 0.5259 0.6374 0.065 Uiso 1 1 calc R
H27B H 0.8431 0.5598 0.5638 0.065 Uiso 1 1 calc R
H27C H 0.8358 0.4664 0.5833 0.065 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'
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
C1 Au1 Cl1 178.86(11)
C1 N1 C10 111.6(3)
C1 N1 C2 125.9(3)
C10 N1 C2 122.4(3)
C1 N2 C11 111.9(3)
C1 N2 C19 125.3(3)
C11 N2 C19 122.7(3)
N2 C1 N1 104.6(3)
N2 C1 Au1 128.4(3)
N1 C1 Au1 126.9(3)
N1 C2 C20 114.3(3)
N1 C2 C3 105.9(3)
C20 C2 C3 110.9(3)
N1 C2 H2A 108.5
C20 C2 H2A 108.5
C3 C2 H2A 108.5
C4 C3 C2 110.4(3)
C4 C3 H3A 109.6
C2 C3 H3A 109.6
C4 C3 H3B 109.6
C2 C3 H3B 109.6
H3A C3 H3B 108.1
C5 C4 C9 118.4(3)
C5 C4 C3 123.2(4)
C9 C4 C3 118.4(3)
C4 C5 C6 120.9(4)
C4 C5 H5A 119.5
C6 C5 H5A 119.5
C7 C6 C5 119.9(4)
C7 C6 H6A 120.0
C5 C6 H6A 120.0
C6 C7 C8 120.4(4)
C6 C7 H7A 119.8
C8 C7 H7A 119.8
C7 C8 C9 120.4(4)
C7 C8 H8A 119.8
C9 C8 H8A 119.8
C8 C9 C4 119.9(4)
C8 C9 C10 123.1(3)
C4 C9 C10 116.9(3)
C11 C10 N1 106.0(3)
C11 C10 C9 136.0(4)
N1 C10 C9 117.9(3)
C10 C11 N2 105.6(3)
C10 C11 C12 135.7(4)
N2 C11 C12 118.6(3)
C13 C12 C17 119.7(4)
C13 C12 C11 122.7(3)
C17 C12 C11 117.6(3)
C14 C13 C12 120.1(4)
C14 C13 H13A 120.0
C12 C13 H13A 120.0
C13 C14 C15 120.3(4)
C13 C14 H14A 119.8
C15 C14 H14A 119.8
C16 C15 C14 119.7(4)
C16 C15 H15A 120.1
C14 C15 H15A 120.1
C15 C16 C17 120.7(4)
C15 C16 H16A 119.6
C17 C16 H16A 119.6
C16 C17 C12 119.5(4)
C16 C17 C18 122.2(4)
C12 C17 C18 118.3(3)
C17 C18 C19 111.4(3)
C17 C18 H18A 109.3
C19 C18 H18A 109.3
C17 C18 H18B 109.3
C19 C18 H18B 109.3
H18A C18 H18B 108.0
N2 C19 C24 110.7(3)
N2 C19 C18 106.9(3)
C24 C19 C18 114.2(3)
N2 C19 H19A 108.3
C24 C19 H19A 108.3
C18 C19 H19A 108.3
C2 C20 C21 117.7(4)
C2 C20 H20A 107.9
C21 C20 H20A 107.9
C2 C20 H20B 107.9
C21 C20 H20B 107.9
H20A C20 H20B 107.2
C22 C21 C20 111.5(4)
C22 C21 C23 108.8(4)
C20 C21 C23 110.3(4)
C22 C21 H21A 108.7
C20 C21 H21A 108.7
C23 C21 H21A 108.7
C21 C22 H22A 109.5
C21 C22 H22B 109.5
H22A C22 H22B 109.5
C21 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
C21 C23 H23A 109.5
C21 C23 H23B 109.5
H23A C23 H23B 109.5
C21 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
C19 C24 C25 114.9(3)
C19 C24 H24A 108.6
C25 C24 H24A 108.6
C19 C24 H24B 108.6
C25 C24 H24B 108.6
H24A C24 H24B 107.5
C26 C25 C24 109.7(4)
C26 C25 C27 109.8(4)
C24 C25 C27 111.5(4)
C26 C25 H25A 108.6
C24 C25 H25A 108.6
C27 C25 H25A 108.6
C25 C26 H26A 109.5
C25 C26 H26B 109.5
H26A C26 H26B 109.5
C25 C26 H26C 109.5
H26A C26 H26C 109.5
H26B C26 H26C 109.5
C25 C27 H27A 109.5
C25 C27 H27B 109.5
H27A C27 H27B 109.5
C25 C27 H27C 109.5
H27A C27 H27C 109.5
H27B C27 H27C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Au1 C1 1.985(4)
Au1 Cl1 2.2829(10)
N1 C1 1.352(5)
N1 C10 1.395(5)
N1 C2 1.467(5)
N2 C1 1.348(5)
N2 C11 1.396(5)
N2 C19 1.470(5)
C2 C20 1.531(7)
C2 C3 1.544(6)
C2 H2A 1.0000
C3 C4 1.479(5)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.390(5)
C4 C9 1.423(5)
C5 C6 1.411(6)
C5 H5A 0.9500
C6 C7 1.377(6)
C6 H6A 0.9500
C7 C8 1.387(6)
C7 H7A 0.9500
C8 C9 1.400(5)
C8 H8A 0.9500
C9 C10 1.470(6)
C10 C11 1.373(6)
C11 C12 1.468(6)
C12 C13 1.402(5)
C12 C17 1.410(5)
C13 C14 1.375(6)
C13 H13A 0.9500
C14 C15 1.402(6)
C14 H14A 0.9500
C15 C16 1.388(6)
C15 H15A 0.9500
C16 C17 1.382(5)
C16 H16A 0.9500
C17 C18 1.505(6)
C18 C19 1.550(5)
C18 H18A 0.9900
C18 H18B 0.9900
C19 C24 1.531(5)
C19 H19A 1.0000
C20 C21 1.533(7)
C20 H20A 0.9900
C20 H20B 0.9900
C21 C22 1.551(7)
C21 C23 1.553(7)
C21 H21A 1.0000
C22 H22A 0.9800
C22 H22B 0.9800
C22 H22C 0.9800
C23 H23A 0.9800
C23 H23B 0.9800
C23 H23C 0.9800
C24 C25 1.531(5)
C24 H24A 0.9900
C24 H24B 0.9900
C25 C26 1.526(7)
C25 C27 1.540(7)
C25 H25A 1.0000
C26 H26A 0.9800
C26 H26B 0.9800
C26 H26C 0.9800
C27 H27A 0.9800
C27 H27B 0.9800
C27 H27C 0.9800
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.053 0.250 0.000 230 74 ' '
2 0.008 0.750 0.500 230 74 ' '
