#------------------------------------------------------------------------------
#$Date: 2025-08-20 18:06:18 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301834 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/04/4120420.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_4120420
loop_
_publ_author_name
'Weiwei Zi'
'F. Dean Toste'
_publ_section_title
;
 Gold(I)-Catalyzed Enantioselective Carboalkoxylation of Alkynes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12600
_journal_page_last               12603
_journal_paper_doi               10.1021/ja407150h
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H12 O2'
_chemical_formula_weight         212.24
_chemical_name_common            ZW03183
_chemical_name_systematic
; 
 toste79 
;
_space_group.centring_type       P
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3759(11)
_cell_length_b                   10.6746(14)
_cell_length_c                   11.5652(15)
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      5.64
_cell_volume                     1034.0(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2013
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_refln_scan_rate          5
_diffrn_refln_scan_width         1.0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15454
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.311
_diffrn_reflns_theta_min         5.640
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
; 
 Flack x determined using 770 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0245
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0406P)²+0.1676P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0658
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                1868
_reflns_number_total             1885
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja407150h_si_002.cif
_cod_data_source_block           toste79
_cod_depositor_comments
;
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_database_code               4120420
#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. 
;
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.986
_shelxl_version_number           2013-4
#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, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.90462(18) 0.87197(14) 0.38293(13) 0.0180(3) Uani 1 1 d . .
H1 H 0.8948 0.8946 0.2993 0.022 Uiso 1 1 calc R U
C2 C 1.02403(18) 0.95707(15) 0.44160(12) 0.0176(3) Uani 1 1 d . .
C3 C 1.18925(18) 0.96362(15) 0.41770(13) 0.0192(3) Uani 1 1 d . .
H3 H 1.2363 0.9105 0.3613 0.023 Uiso 1 1 calc R U
C4 C 1.27968(18) 1.04803(15) 0.47748(13) 0.0197(3) Uani 1 1 d . .
H4 H 1.3908 1.0531 0.4618 0.024 Uiso 1 1 calc R U
C5 C 1.21220(18) 1.12882(14) 0.56277(12) 0.0184(3) Uani 1 1 d . .
C6 C 1.30704(18) 1.21623(15) 0.62381(13) 0.0202(3) Uani 1 1 d . .
H6 H 1.4185 1.2204 0.6091 0.024 Uiso 1 1 calc R U
C7 C 1.24041(19) 1.29507(15) 0.70398(13) 0.0218(3) Uani 1 1 d . .
H7 H 1.3053 1.3542 0.7434 0.026 Uiso 1 1 calc R U
C8 C 1.0756(2) 1.28829(16) 0.72784(13) 0.0234(3) Uani 1 1 d . .
H8 H 1.0300 1.3430 0.7836 0.028 Uiso 1 1 calc R U
C9 C 0.98014(19) 1.20347(15) 0.67143(13) 0.0212(3) Uani 1 1 d . .
H9 H 0.8694 1.1996 0.6888 0.025 Uiso 1 1 calc R U
C10 C 1.04551(17) 1.12196(14) 0.58763(13) 0.0178(3) Uani 1 1 d . .
C11 C 0.95444(18) 1.03248(14) 0.52384(12) 0.0180(3) Uani 1 1 d . .
C12 C 0.78144(18) 1.00437(15) 0.53043(12) 0.0193(3) Uani 1 1 d . .
C13 C 0.74688(18) 0.89878(15) 0.44611(13) 0.0223(3) Uani 1 1 d . .
H13A H 0.6632 0.9242 0.3904 0.027 Uiso 1 1 calc R U
H13B H 0.7099 0.8233 0.4880 0.027 Uiso 1 1 calc R U
C14 C 0.87667(19) 0.66249(15) 0.32096(14) 0.0214(3) Uani 1 1 d . .
H14A H 0.7641 0.6595 0.3438 0.032 Uiso 1 1 calc R U
H14B H 0.9234 0.5787 0.3277 0.032 Uiso 1 1 calc R U
H14C H 0.8849 0.6913 0.2407 0.032 Uiso 1 1 calc R U
O1 O 0.96018(13) 0.74669(10) 0.39438(9) 0.0200(3) Uani 1 1 d . .
O2 O 0.68241(12) 1.05532(11) 0.59193(10) 0.0248(3) 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 0.0181 0.0091 '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 0.0492 0.0322 '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
O1 C1 C2 107.86(12)
O1 C1 C13 114.34(13)
C2 C1 C13 104.10(12)
O1 C1 H1 110.1
C2 C1 H1 110.1
C13 C1 H1 110.1
C11 C2 C3 121.42(15)
C11 C2 C1 112.43(13)
C3 C2 C1 126.15(14)
C4 C3 C2 118.49(14)
C4 C3 H3 120.8
C2 C3 H3 120.8
C3 C4 C5 121.95(13)
C3 C4 H4 119.0
C5 C4 H4 119.0
C6 C5 C4 121.42(13)
C6 C5 C10 118.86(14)
C4 C5 C10 119.72(14)
C7 C6 C5 120.93(14)
C7 C6 H6 119.5
C5 C6 H6 119.5
C6 C7 C8 119.97(15)
C6 C7 H7 120.0
C8 C7 H7 120.0
C9 C8 C7 120.73(15)
C9 C8 H8 119.6
C7 C8 H8 119.6
C8 C9 C10 120.44(14)
C8 C9 H9 119.8
C10 C9 H9 119.8
C9 C10 C5 119.06(14)
C9 C10 C11 124.01(13)
C5 C10 C11 116.92(14)
C2 C11 C10 121.49(14)
C2 C11 C12 109.35(14)
C10 C11 C12 129.15(14)
O2 C12 C11 127.18(15)
O2 C12 C13 125.14(14)
C11 C12 C13 107.69(13)
C12 C13 C1 106.24(12)
C12 C13 H13A 110.5
C1 C13 H13A 110.5
C12 C13 H13B 110.5
C1 C13 H13B 110.5
H13A C13 H13B 108.7
O1 C14 H14A 109.5
O1 C14 H14B 109.5
H14A C14 H14B 109.5
O1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C14 O1 C1 112.22(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.4222(18)
C1 C2 1.512(2)
C1 C13 1.537(2)
C1 H1 1.0000
C2 C11 1.376(2)
C2 C3 1.413(2)
C3 C4 1.365(2)
C3 H3 0.9500
C4 C5 1.427(2)
C4 H4 0.9500
C5 C6 1.414(2)
C5 C10 1.427(2)
C6 C7 1.371(2)
C6 H6 0.9500
C7 C8 1.410(2)
C7 H7 0.9500
C8 C9 1.373(2)
C8 H8 0.9500
C9 C10 1.413(2)
C9 H9 0.9500
C10 C11 1.428(2)
C11 C12 1.482(2)
C12 O2 1.2206(19)
C12 C13 1.518(2)
C13 H13A 0.9900
C13 H13B 0.9900
C14 O1 1.4206(18)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139122410
