#------------------------------------------------------------------------------
#$Date: 2025-08-20 20:34:49 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301835 $
#$URL: svn://www.crystallography.net/cod/cif/4/13/43/4134377.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_4134377
loop_
_publ_author_name
'Lanke, Veeranjaneyulu'
'Marek, Ilan'
_publ_section_title
;
 Nucleophilic Substitution at Quaternary Carbon Stereocenters.
;
_journal_issue                   12
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5543
_journal_page_last               5548
_journal_paper_doi               10.1021/jacs.0c01133
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C30 H44 F2 O4'
_chemical_formula_sum            'C30 H44 F2 O4'
_chemical_formula_weight         506.65
_chemical_name_common            'Marek155b (Veeru)'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                108.412(2)
_cell_angle_beta                 94.7640(10)
_cell_angle_gamma                104.611(3)
_cell_formula_units_Z            1
_cell_length_a                   5.893(4)
_cell_length_b                   9.976(7)
_cell_length_c                   13.552(6)
_cell_measurement_reflns_used    2572
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.280
_cell_measurement_theta_min      1.609
_cell_volume                     719.9(8)
_computing_cell_refinement       'APEX2 v2010.7-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2010.7.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 95
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'APEX2 (Bruker AXS)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1118
_diffrn_reflns_av_unetI/netI     0.1264
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5957
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.280
_diffrn_reflns_theta_min         1.609
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_description       block
_exptl_crystal_F_000             274
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0510
_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)+(0.0227P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1332
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1726
_reflns_number_total             2572
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c01133_si_003.cif
_cod_data_source_block           Marek155b
_cod_depositor_comments
'Adding full bibliography for 4134376--4134377.cif.'
_cod_original_cell_volume        720.0(8)
_cod_database_code               4134377
_shelx_shelxl_version_number     2018/3
_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   0.980
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.4946(2) 0.54046(13) 0.85999(9) 0.0461(4) Uani 1 1 d . . . . .
O1 O 0.7490(3) 0.60576(17) 0.65040(13) 0.0491(4) Uani 1 1 d . . . . .
O2 O 0.3541(3) 0.52215(14) 0.64197(11) 0.0372(4) Uani 1 1 d . . . . .
C1 C 0.3609(5) 0.7800(2) 0.7057(2) 0.0515(6) Uani 1 1 d . . . . .
H1A H 0.323604 0.857216 0.683027 0.077 Uiso 1 1 calc R U . . .
H1B H 0.527703 0.814345 0.740969 0.077 Uiso 1 1 calc R U . . .
H1C H 0.257024 0.757878 0.754876 0.077 Uiso 1 1 calc R U . . .
C2 C 0.3219(4) 0.6430(2) 0.61115(18) 0.0433(6) Uani 1 1 d . . . . .
H2A H 0.158445 0.614637 0.571192 0.052 Uiso 1 1 calc R U . . .
H2B H 0.435471 0.663485 0.564121 0.052 Uiso 1 1 calc R U . . .
C3 C 0.5782(4) 0.5191(2) 0.66212(15) 0.0340(5) Uani 1 1 d . . . . .
C4 C 0.5872(4) 0.3936(2) 0.70120(15) 0.0327(5) Uani 1 1 d . . . . .
H4 H 0.424850 0.320469 0.679916 0.039 Uiso 1 1 calc R U . . .
C5 C 0.7587(4) 0.3161(2) 0.64998(15) 0.0339(5) Uani 1 1 d . . . . .
H5 H 0.907180 0.374953 0.643677 0.041 Uiso 1 1 calc R U . . .
C6 C 0.7144(4) 0.1715(2) 0.61353(15) 0.0333(5) Uani 1 1 d . . . . .
H6 H 0.569587 0.115710 0.625243 0.040 Uiso 1 1 calc R U . . .
C7 C 0.8637(4) 0.0865(2) 0.55670(14) 0.0290(5) Uani 1 1 d . . . . .
C8 C 0.8340(4) -0.0586(2) 0.55211(15) 0.0343(5) Uani 1 1 d . . . . .
H8 H 0.719221 -0.100650 0.587593 0.041 Uiso 1 1 calc R U . . .
C9 C 0.9665(4) -0.1427(2) 0.49755(15) 0.0327(5) Uani 1 1 d . . . . .
H9 H 0.942175 -0.240899 0.496729 0.039 Uiso 1 1 calc R U . . .
C10 C 0.6506(4) 0.4543(2) 0.82495(16) 0.0376(5) Uani 1 1 d . . . . .
C11 C 0.9008(4) 0.5572(3) 0.86780(19) 0.0511(6) Uani 1 1 d . . . . .
H11A H 0.922967 0.639915 0.841734 0.077 Uiso 1 1 calc R U . . .
H11B H 1.015581 0.503203 0.844256 0.077 Uiso 1 1 calc R U . . .
H11C H 0.926181 0.595150 0.945191 0.077 Uiso 1 1 calc R U . . .
C12 C 0.5945(4) 0.3307(2) 0.87020(17) 0.0451(6) Uani 1 1 d . . . . .
H12A H 0.638494 0.375619 0.948120 0.054 Uiso 1 1 calc R U . . .
H12B H 0.698244 0.267218 0.845790 0.054 Uiso 1 1 calc R U . . .
C13 C 0.3370(5) 0.2316(3) 0.84277(19) 0.0514(6) Uani 1 1 d . . . . .
H13A H 0.230258 0.294848 0.859927 0.062 Uiso 1 1 calc R U . . .
H13B H 0.297754 0.176342 0.765706 0.062 Uiso 1 1 calc R U . . .
C14 C 0.2882(5) 0.1226(3) 0.89991(19) 0.0570(7) Uani 1 1 d . . . . .
H14A H 0.321183 0.177501 0.976989 0.068 Uiso 1 1 calc R U . . .
H14B H 0.397863 0.061017 0.884682 0.068 Uiso 1 1 calc R U . . .
C15 C 0.0342(6) 0.0229(3) 0.8683(2) 0.0712(8) Uani 1 1 d . . . . .
H15A H 0.000145 -0.031478 0.791960 0.107 Uiso 1 1 calc R U . . .
H15B H -0.075102 0.082929 0.886276 0.107 Uiso 1 1 calc R U . . .
H15C H 0.012773 -0.047193 0.906057 0.107 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'
F F 0.0171 0.0103 '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'
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
_geom_angle_publ_flag
C3 O2 C2 116.58(16) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 C1 111.24(18) . . ?
O2 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
O2 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
O1 C3 O2 123.77(19) . . ?
O1 C3 C4 125.3(2) . . ?
O2 C3 C4 110.96(18) . . ?
C5 C4 C3 110.41(17) . . ?
C5 C4 C10 112.76(16) . . ?
C3 C4 C10 109.57(16) . . ?
C5 C4 H4 108.0 . . ?
C3 C4 H4 108.0 . . ?
C10 C4 H4 108.0 . . ?
C6 C5 C4 123.7(2) . . ?
C6 C5 H5 118.2 . . ?
C4 C5 H5 118.1 . . ?
C5 C6 C7 127.4(2) . . ?
C5 C6 H6 116.3 . . ?
C7 C6 H6 116.3 . . ?
C8 C7 C9 116.87(18) . 2_756 ?
C8 C7 C6 120.17(19) . . ?
C9 C7 C6 122.92(17) 2_756 . ?
C9 C8 C7 121.76(19) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C7 121.37(18) . 2_756 ?
C8 C9 H9 119.3 . . ?
C7 C9 H9 119.3 2_756 . ?
F1 C10 C11 106.37(18) . . ?
F1 C10 C12 106.14(18) . . ?
C11 C10 C12 112.62(18) . . ?
F1 C10 C4 105.64(15) . . ?
C11 C10 C4 113.53(19) . . ?
C12 C10 C4 111.83(17) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 C13 116.89(18) . . ?
C10 C12 H12A 108.1 . . ?
C13 C12 H12A 108.1 . . ?
C10 C12 H12B 108.1 . . ?
C13 C12 H12B 108.1 . . ?
H12A C12 H12B 107.3 . . ?
C14 C13 C12 114.0(2) . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 C15 112.7(2) . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C10 1.422(2) . ?
O1 C3 1.209(3) . ?
O2 C3 1.336(3) . ?
O2 C2 1.444(2) . ?
C1 C2 1.499(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.516(3) . ?
C4 C5 1.507(3) . ?
C4 C10 1.568(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.315(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.470(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(3) . ?
C7 C9 1.399(3) 2_756 ?
C8 C9 1.376(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.511(3) . ?
C10 C12 1.521(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.528(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.509(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.512(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168336268
