#------------------------------------------------------------------------------
#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/64/4126450.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_4126450
loop_
_publ_author_name
'García-Morales, Cristina'
'Ranieri, Beatrice'
'Escofet, Imma'
'López-Suarez, Laura'
'Obradors, Carla'
'Konovalov, Andrey I.'
'Echavarren, Antonio M.'
_publ_section_title
;
 Enantioselective Synthesis of Cyclobutenes by Intermolecular [2+2]
 Cycloaddition with Non-C2 Symmetric Digold Catalysts.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b07651
_journal_year                    2017
_chemical_formula_sum            'C28 H24 F2'
_chemical_formula_weight         398.47
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.5997(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.1418(14)
_cell_length_b                   5.7036(3)
_cell_length_c                   15.8393(10)
_cell_measurement_reflns_used    3288
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      2.63
_cell_volume                     2048.0(2)
_computing_cell_refinement       'Bruker APEX2 v2014.9-0'
_computing_data_collection       'Bruker APEX2 v2014.9-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.653
_diffrn_reflns_theta_min         1.797
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_current           0.6
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Bruker APEX DUO'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       Plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0710
_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)+(0.0238P)²+8.0798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.1551
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2223
_reflns_number_total             2882
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b07651_si_008.cif
_cod_data_source_block           mo_CG30531_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/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/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4126450
_shelx_shelxl_version_number     2014/7
_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   0.987
_shelx_estimated_absorpt_t_max   0.999
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C1 C 0.20190(9) 0.1989(5) 0.59057(14) 0.0214(5) Uani 1 1 d . .
C2 C 0.22051(10) 0.3873(5) 0.64244(15) 0.0214(5) Uani 1 1 d . .
H2 H 0.1939 0.5086 0.6500 0.026 Uiso 1 1 calc R U
C3 C 0.27949(10) 0.3962(4) 0.68370(14) 0.0175(4) Uani 1 1 d . .
H3 H 0.2933 0.5251 0.7202 0.021 Uiso 1 1 calc R U
C4 C 0.31876(9) 0.2190(4) 0.67244(13) 0.0142(4) Uani 1 1 d . .
C5 C 0.29787(10) 0.0314(4) 0.61912(14) 0.0196(5) Uani 1 1 d . .
H5 H 0.3242 -0.0904 0.6108 0.024 Uiso 1 1 calc R U
C6 C 0.23859(10) 0.0195(5) 0.57751(15) 0.0226(5) Uani 1 1 d . .
H6 H 0.2242 -0.1091 0.5412 0.027 Uiso 1 1 calc R U
C7 C 0.38377(9) 0.2397(4) 0.71400(13) 0.0141(4) Uani 1 1 d . .
C8 C 0.39809(9) 0.3365(4) 0.80696(14) 0.0164(4) Uani 1 1 d . .
H8 H 0.3896 0.4782 0.8335 0.020 Uiso 1 1 calc R U
C9 C 0.42889(9) 0.1287(4) 0.83643(14) 0.0144(4) Uani 1 1 d . .
C10 C 0.41545(10) 0.0126(4) 0.75386(14) 0.0187(5) Uani 1 1 d . .
H10A H 0.3888 -0.1239 0.7523 0.022 Uiso 1 1 calc R U
H10B H 0.4507 -0.0289 0.7306 0.022 Uiso 1 1 calc R U
C11 C 0.41705(10) 0.3655(5) 0.65292(14) 0.0208(5) Uani 1 1 d . .
H11A H 0.4146 0.2726 0.6003 0.031 Uiso 1 1 calc R U
H11B H 0.4585 0.3844 0.6812 0.031 Uiso 1 1 calc R U
H11C H 0.3994 0.5200 0.6382 0.031 Uiso 1 1 calc R U
C12 C 0.46426(9) 0.0606(4) 0.92020(13) 0.0140(4) Uani 1 1 d . .
C13 C 0.46774(9) 0.2069(4) 0.99189(14) 0.0161(4) Uani 1 1 d . .
H13 H 0.4456 0.3483 0.9867 0.019 Uiso 1 1 calc R U
C14 C 0.49691(9) -0.1479(4) 0.92968(14) 0.0165(4) Uani 1 1 d . .
H14 H 0.4948 -0.2499 0.8818 0.020 Uiso 1 1 calc R U
F1 F 0.14417(6) 0.1877(3) 0.54982(10) 0.0330(4) 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'
F F 0.0171 0.0103 '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
F1 C1 C2 118.7(2) .
F1 C1 C6 118.1(2) .
C2 C1 C6 123.1(2) .
C1 C2 C3 118.1(2) .
C2 C3 C4 121.1(2) .
C5 C4 C3 118.7(2) .
C5 C4 C7 121.1(2) .
C3 C4 C7 120.1(2) .
C4 C5 C6 120.8(2) .
C1 C6 C5 118.1(2) .
C4 C7 C11 110.03(17) .
C4 C7 C8 116.37(17) .
C11 C7 C8 113.34(19) .
C4 C7 C10 117.04(19) .
C11 C7 C10 112.97(18) .
C8 C7 C10 85.27(16) .
C9 C8 C7 90.72(18) .
C8 C9 C10 94.76(18) .
C8 C9 C12 132.4(2) .
C10 C9 C12 132.7(2) .
C9 C10 C7 89.07(18) .
C13 C12 C14 118.54(19) .
C13 C12 C9 120.5(2) .
C14 C12 C9 120.9(2) .
C14 C13 C12 120.7(2) 5_657
C13 C14 C12 120.8(2) 5_657
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 F1 1.363(2) .
C1 C2 1.369(4) .
C1 C6 1.371(4) .
C2 C3 1.391(3) .
C3 C4 1.394(3) .
C4 C5 1.388(3) .
C4 C7 1.521(3) .
C5 C6 1.399(3) .
C7 C11 1.531(3) .
C7 C8 1.545(3) .
C7 C10 1.558(3) .
C8 C9 1.413(3) .
C9 C10 1.443(3) .
C9 C12 1.464(3) .
C12 C13 1.398(3) .
C12 C14 1.400(3) .
C13 C14 1.385(3) 5_657
C14 C13 1.385(3) 5_657
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
F1 C1 C2 C3 179.9(2) .
C6 C1 C2 C3 0.0(4) .
C1 C2 C3 C4 0.3(3) .
C2 C3 C4 C5 -0.2(3) .
C2 C3 C4 C7 176.4(2) .
C3 C4 C5 C6 -0.1(3) .
C7 C4 C5 C6 -176.6(2) .
F1 C1 C6 C5 179.8(2) .
C2 C1 C6 C5 -0.3(4) .
C4 C5 C6 C1 0.3(3) .
C5 C4 C7 C11 87.0(3) .
C3 C4 C7 C11 -89.5(2) .
C5 C4 C7 C8 -142.4(2) .
C3 C4 C7 C8 41.2(3) .
C5 C4 C7 C10 -43.8(3) .
C3 C4 C7 C10 139.8(2) .
C4 C7 C8 C9 121.0(2) .
C11 C7 C8 C9 -109.9(2) .
C10 C7 C8 C9 3.12(16) .
C7 C8 C9 C10 -3.37(17) .
C7 C8 C9 C12 174.1(2) .
C8 C9 C10 C7 3.34(17) .
C12 C9 C10 C7 -174.1(2) .
C4 C7 C10 C9 -120.32(19) .
C11 C7 C10 C9 110.32(19) .
C8 C7 C10 C9 -3.05(16) .
C8 C9 C12 C13 6.2(4) .
C10 C9 C12 C13 -177.2(2) .
C8 C9 C12 C14 -171.5(2) .
C10 C9 C12 C14 5.0(4) .
C14 C12 C13 C14 0.5(4) 5_657
C9 C12 C13 C14 -177.3(2) 5_657
C13 C12 C14 C13 -0.5(4) 5_657
C9 C12 C14 C13 177.3(2) 5_657
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139125579
