#------------------------------------------------------------------------------
#$Date: 2017-12-11 01:28:22 +0200 (Mon, 11 Dec 2017) $
#$Revision: 204147 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/33/1503374.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_1503374
loop_
_publ_author_name
'González, Ana Z'
'Toste, F. Dean'
_publ_section_title
;
 Gold(I)-catalyzed enantioselective [4 + 2]-cycloaddition of
 allene-dienes.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              200
_journal_page_last               203
_journal_paper_doi               10.1021/ol902622b
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C93 H81 Au Cl O9 P'
_chemical_formula_weight         1605.96
_chemical_name_common            toste06
_chemical_name_systematic
;
 toste06
;
_space_group.centring_type       P
_space_group_IT_number           173
_space_group.IT_number           173
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            2
_cell_length_a                   15.923(2)
_cell_length_b                   15.923(2)
_cell_length_c                   18.741(3)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    288(2)
_cell_measurement_theta_max      22.35
_cell_measurement_theta_min      2.56
_cell_volume                     4115.0(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      288(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       'φ and 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  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_refln_scan_rate          30
_diffrn_refln_scan_width         0.5
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33929
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    1.896
_exptl_absorpt_correction_T_max  0.8631
_exptl_absorpt_correction_T_min  0.7641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1644
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.657
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.015(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5044
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1094P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1626
_reflns_number_gt                3800
_reflns_number_total             5044
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902622b_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Hexagonal' changed to 'hexagonal'
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 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_original_cell_volume        4114.9(10)
_cod_original_sg_symbol_H-M      P6(3)
_cod_database_code               1503374
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, 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
C1 C 0.5167(4) 0.8059(4) 0.6326(4) 0.0540(14) Uani 1 1 d .
C2 C 0.5064(5) 0.8796(5) 0.6015(5) 0.0704(19) Uani 1 1 d .
H2 H 0.4455 0.8707 0.5905 0.085 Uiso 1 1 calc R
C3 C 0.5886(6) 0.9653(5) 0.5879(5) 0.078(2) Uani 1 1 d .
H3 H 0.5835 1.0161 0.5682 0.094 Uiso 1 1 calc R
C4 C 0.6784(5) 0.9783(5) 0.6025(5) 0.0700(19) Uani 1 1 d .
C5 C 0.7666(6) 1.0688(5) 0.5877(6) 0.085(2) Uani 1 1 d .
H5 H 0.7631 1.1195 0.5662 0.102 Uiso 1 1 calc R
C6 C 0.8534(6) 1.0797(6) 0.6048(6) 0.092(3) Uani 1 1 d .
H6 H 0.9093 1.1380 0.5944 0.111 Uiso 1 1 calc R
C7 C 0.8616(5) 1.0081(6) 0.6369(6) 0.086(3) Uani 1 1 d .
H7 H 0.9229 1.0183 0.6480 0.103 Uiso 1 1 calc R
C8 C 0.7818(5) 0.9211(5) 0.6534(5) 0.0711(19) Uani 1 1 d .
H8 H 0.7891 0.8732 0.6761 0.085 Uiso 1 1 calc R
C9 C 0.6883(5) 0.9041(5) 0.6357(4) 0.0548(15) Uani 1 1 d .
C10 C 0.6039(4) 0.8146(4) 0.6496(4) 0.0514(13) Uani 1 1 d .
C11 C 0.6066(4) 0.7293(4) 0.6804(4) 0.0535(15) Uani 1 1 d .
C12 C 0.5720(4) 0.6930(4) 0.7494(4) 0.0578(15) Uani 1 1 d .
C13 C 0.5365(5) 0.7378(6) 0.7963(4) 0.077(2) Uani 1 1 d .
H13 H 0.5376 0.7943 0.7822 0.092 Uiso 1 1 calc R
C14 C 0.5006(9) 0.6989(9) 0.8622(5) 0.108(3) Uani 1 1 d .
H14 H 0.4764 0.7286 0.8920 0.130 Uiso 1 1 calc R
C15 C 0.5000(8) 0.6156(9) 0.8847(6) 0.110(3) Uani 1 1 d .
H15 H 0.4732 0.5888 0.9288 0.132 Uiso 1 1 calc R
C16 C 0.5370(7) 0.5732(8) 0.8445(6) 0.100(3) Uani 1 1 d .
H16 H 0.5406 0.5205 0.8621 0.121 Uiso 1 1 calc R
C17 C 0.5714(5) 0.6089(6) 0.7740(5) 0.077(2) Uani 1 1 d .
C18 C 0.6101(6) 0.5638(6) 0.7282(6) 0.087(3) Uani 1 1 d .
H18 H 0.6110 0.5089 0.7441 0.105 Uiso 1 1 calc R
C19 C 0.6449(5) 0.5992(5) 0.6632(5) 0.073(2) Uani 1 1 d .
H19 H 0.6704 0.5698 0.6344 0.088 Uiso 1 1 calc R
C20 C 0.6421(5) 0.6815(5) 0.6393(4) 0.0590(16) Uani 1 1 d .
C21 C 0.6460(6) 0.6772(6) 0.5135(5) 0.089(3) Uani 1 1 d .
C22 C 0.6820(7) 0.7410(7) 0.4481(5) 0.075(2) Uani 1 1 d .
C23 C 0.7768(9) 0.8335(8) 0.4621(6) 0.112(3) Uani 1 1 d .
H23A H 0.8260 0.8178 0.4761 0.135 Uiso 1 1 calc R
H23B H 0.7686 0.8693 0.5007 0.135 Uiso 1 1 calc R
C24 C 0.8094(11) 0.8965(9) 0.3935(6) 0.128(4) Uani 1 1 d .
H24 H 0.8711 0.9560 0.4022 0.154 Uiso 1 1 calc R
C25 C 0.733(2) 0.9217(17) 0.3757(14) 0.192(9) Uani 1 1 d .
H25A H 0.7299 0.9628 0.4127 0.230 Uiso 1 1 calc R
H25B H 0.7483 0.9570 0.3309 0.230 Uiso 1 1 calc R
C26 C 0.6444(18) 0.838(2) 0.3702(14) 0.187(9) Uani 1 1 d .
H26 H 0.5950 0.8557 0.3602 0.224 Uiso 1 1 calc R
C27 C 0.6473(15) 0.7772(17) 0.3063(11) 0.183(9) Uani 1 1 d .
H27A H 0.5847 0.7189 0.3008 0.219 Uiso 1 1 calc R
H27B H 0.6620 0.8147 0.2626 0.219 Uiso 1 1 calc R
C28 C 0.7260(15) 0.7499(11) 0.3206(8) 0.150(6) Uani 1 1 d .
H28 H 0.7313 0.7139 0.2800 0.180 Uiso 1 1 calc R
C29 C 0.6955(10) 0.6877(9) 0.3872(6) 0.113(4) Uani 1 1 d .
H29A H 0.6352 0.6279 0.3782 0.136 Uiso 1 1 calc R
H29B H 0.7446 0.6711 0.3995 0.136 Uiso 1 1 calc R
C30 C 0.6119(10) 0.7713(13) 0.4342(8) 0.136(5) Uani 1 1 d .
H30A H 0.6064 0.8050 0.4755 0.163 Uiso 1 1 calc R
H30B H 0.5488 0.7150 0.4250 0.163 Uiso 1 1 calc R
C31 C 0.8214(11) 0.8406(13) 0.3339(8) 0.145(5) Uani 1 1 d .
H31A H 0.8702 0.8239 0.3466 0.175 Uiso 1 1 calc R
H31B H 0.8425 0.8800 0.2910 0.175 Uiso 1 1 calc R
O1 O 0.4340(3) 0.7158(3) 0.6492(3) 0.0583(10) Uani 1 1 d .
O2 O 0.6824(3) 0.7241(4) 0.5734(3) 0.0635(12) Uani 1 1 d .
O3 O 0.5854(9) 0.5903(6) 0.5139(4) 0.181(5) Uani 1 1 d .
P1 P 0.3333 0.6667 0.6097(2) 0.0494(8) Uani 1 3 d S
Cl1 Cl 0.3333 0.6667 0.3727(4) 0.150(3) Uani 1 3 d S
Au1 Au 0.3333 0.6667 0.49344(4) 0.0790(2) Uani 1 3 d S
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'
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C10 C1 C2 123.8(6) . .
C10 C1 O1 115.9(5) . .
C2 C1 O1 120.3(5) . .
C3 C2 C1 117.6(6) . .
C3 C2 H2 121.2 . .
C1 C2 H2 121.2 . .
C2 C3 C4 121.6(7) . .
C2 C3 H3 119.2 . .
C4 C3 H3 119.2 . .
C3 C4 C9 120.5(6) . .
C3 C4 C5 122.2(7) . .
C9 C4 C5 117.3(7) . .
C6 C5 C4 120.4(8) . .
C6 C5 H5 119.8 . .
C4 C5 H5 119.8 . .
C5 C6 C7 121.6(7) . .
C5 C6 H6 119.2 . .
C7 C6 H6 119.2 . .
C6 C7 C8 121.5(8) . .
C6 C7 H7 119.2 . .
C8 C7 H7 119.2 . .
C7 C8 C9 119.8(8) . .
C7 C8 H8 120.1 . .
C9 C8 H8 120.1 . .
C10 C9 C4 118.5(6) . .
C10 C9 C8 122.1(6) . .
C4 C9 C8 119.4(6) . .
C1 C10 C9 117.9(6) . .
C1 C10 C11 119.2(5) . .
C9 C10 C11 122.8(5) . .
C20 C11 C12 117.8(6) . .
C20 C11 C10 119.2(6) . .
C12 C11 C10 122.9(6) . .
C11 C12 C17 120.3(7) . .
C11 C12 C13 122.3(6) . .
C17 C12 C13 117.4(7) . .
C14 C13 C12 120.9(9) . .
C14 C13 H13 119.5 . .
C12 C13 H13 119.5 . .
C13 C14 C15 120.4(11) . .
C13 C14 H14 119.8 . .
C15 C14 H14 119.8 . .
C16 C15 C14 121.4(10) . .
C16 C15 H15 119.3 . .
C14 C15 H15 119.3 . .
C15 C16 C17 120.0(9) . .
C15 C16 H16 120.0 . .
C17 C16 H16 120.0 . .
C12 C17 C16 119.8(9) . .
C12 C17 C18 118.5(7) . .
C16 C17 C18 121.7(8) . .
C19 C18 C17 121.4(7) . .
C19 C18 H18 119.3 . .
C17 C18 H18 119.3 . .
C18 C19 C20 118.8(8) . .
C18 C19 H19 120.6 . .
C20 C19 H19 120.6 . .
C11 C20 O2 115.9(6) . .
C11 C20 C19 123.1(7) . .
O2 C20 C19 120.8(6) . .
O3 C21 O2 120.6(8) . .
O3 C21 C22 125.7(8) . .
O2 C21 C22 113.6(7) . .
C30 C22 C29 113.9(11) . .
C30 C22 C21 106.0(8) . .
C29 C22 C21 110.5(8) . .
C30 C22 C23 105.5(10) . .
C29 C22 C23 109.0(9) . .
C21 C22 C23 111.9(8) . .
C22 C23 C24 109.5(9) . .
C22 C23 H23A 109.8 . .
C24 C23 H23A 109.8 . .
C22 C23 H23B 109.8 . .
C24 C23 H23B 109.8 . .
H23A C23 H23B 108.2 . .
C31 C24 C25 110.8(15) . .
C31 C24 C23 109.5(12) . .
C25 C24 C23 107.7(14) . .
C31 C24 H24 109.6 . .
C25 C24 H24 109.6 . .
C23 C24 H24 109.6 . .
C26 C25 C24 109.2(15) . .
C26 C25 H25A 109.8 . .
C24 C25 H25A 109.8 . .
C26 C25 H25B 109.8 . .
C24 C25 H25B 109.8 . .
H25A C25 H25B 108.3 . .
C25 C26 C30 117(2) . .
C25 C26 C27 109(2) . .
C30 C26 C27 106(2) . .
C25 C26 H26 108.1 . .
C30 C26 H26 108.1 . .
C27 C26 H26 108.1 . .
C28 C27 C26 108.8(12) . .
C28 C27 H27A 109.9 . .
C26 C27 H27A 109.9 . .
C28 C27 H27B 109.9 . .
C26 C27 H27B 109.9 . .
H27A C27 H27B 108.3 . .
C31 C28 C29 109.3(14) . .
C31 C28 C27 109.3(14) . .
C29 C28 C27 106.7(13) . .
C31 C28 H28 110.5 . .
C29 C28 H28 110.5 . .
C27 C28 H28 110.5 . .
C22 C29 C28 110.3(10) . .
C22 C29 H29A 109.6 . .
C28 C29 H29A 109.6 . .
C22 C29 H29B 109.6 . .
C28 C29 H29B 109.6 . .
H29A C29 H29B 108.1 . .
C22 C30 C26 109.1(12) . .
C22 C30 H30A 109.9 . .
C26 C30 H30A 109.9 . .
C22 C30 H30B 109.9 . .
C26 C30 H30B 109.9 . .
H30A C30 H30B 108.3 . .
C24 C31 C28 109.1(11) . .
C24 C31 H31A 109.9 . .
C28 C31 H31A 109.9 . .
C24 C31 H31B 109.9 . .
C28 C31 H31B 109.9 . .
H31A C31 H31B 108.3 . .
C1 O1 P1 126.9(4) . .
C21 O2 C20 120.9(6) . .
O1 P1 O1 99.6(3) 2_665 .
O1 P1 O1 99.6(3) 2_665 3_565
O1 P1 O1 99.6(3) . 3_565
O1 P1 Au1 118.1(2) 2_665 .
O1 P1 Au1 118.1(2) . .
O1 P1 Au1 118.1(2) 3_565 .
P1 Au1 Cl1 180.000(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C10 1.362(9) .
C1 C2 1.392(9) .
C1 O1 1.415(7) .
C2 C3 1.362(10) .
C2 H2 0.9300 .
C3 C4 1.367(11) .
C3 H3 0.9300 .
C4 C9 1.412(11) .
C4 C5 1.450(11) .
C5 C6 1.342(14) .
C5 H5 0.9300 .
C6 C7 1.351(14) .
C6 H6 0.9300 .
C7 C8 1.368(11) .
C7 H7 0.9300 .
C8 C9 1.412(10) .
C8 H8 0.9300 .
C9 C10 1.410(9) .
C10 C11 1.496(9) .
C11 C20 1.388(9) .
C11 C12 1.410(10) .
C12 C17 1.412(10) .
C12 C13 1.416(11) .
C13 C14 1.372(12) .
C13 H13 0.9300 .
C14 C15 1.388(17) .
C14 H14 0.9300 .
C15 C16 1.328(16) .
C15 H15 0.9300 .
C16 C17 1.435(13) .
C16 H16 0.9300 .
C17 C18 1.441(13) .
C18 C19 1.341(13) .
C18 H18 0.9300 .
C19 C20 1.407(10) .
C19 H19 0.9300 .
C20 O2 1.401(9) .
C21 O3 1.229(11) .
C21 O2 1.313(10) .
C21 C22 1.509(12) .
C22 C30 1.443(16) .
C22 C29 1.502(14) .
C22 C23 1.514(15) .
C23 C24 1.552(15) .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
C24 C31 1.50(2) .
C24 C25 1.50(3) .
C24 H24 0.9800 .
C25 C26 1.38(3) .
C25 H25A 0.9700 .
C25 H25B 0.9700 .
C26 C30 1.51(2) .
C26 C27 1.55(3) .
C26 H26 0.9800 .
C27 C28 1.54(3) .
C27 H27A 0.9700 .
C27 H27B 0.9700 .
C28 C31 1.50(2) .
C28 C29 1.51(2) .
C28 H28 0.9800 .
C29 H29A 0.9700 .
C29 H29B 0.9700 .
C30 H30A 0.9700 .
C30 H30B 0.9700 .
C31 H31A 0.9700 .
C31 H31B 0.9700 .
O1 P1 1.573(4) .
P1 O1 1.573(4) 2_665
P1 O1 1.573(5) 3_565
P1 Au1 2.179(4) .
Cl1 Au1 2.263(8) .
