Probing Through-Space Polar-π Interactions in 2,6-Diarylphenols.
Bosmans, Vera; Poater, Jordi; Hammink, Roel; Tinnemans, Paul; Bickelhaupt, F. Matthias; Mecinović, Jasmin; The Journal of organic chemistry 84 (2019) 3632–3637; doi:10.1021/acs.joc.8b03147

data_4033893
_publ_section_title
;
 Probing Through-Space Polar-\p Interactions in 2,6-Diarylphenols.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3632
_journal_page_last               3637
_journal_paper_doi               10.1021/acs.joc.8b03147
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H12 F2 O'
_chemical_formula_sum            'C18 H12 F2 O'
_chemical_formula_weight         282.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 97.3063(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1063(4)
_cell_length_b                   14.9181(5)
_cell_length_c                   7.0214(2)
_cell_measurement_reflns_used    8118
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.1
_cell_measurement_theta_min      3.1
_cell_volume                     1361.69(7)
_computing_cell_refinement       Peakref
_computing_data_collection       Apex3
_computing_data_reduction        SAINT,SADABS-2014/5
_computing_molecular_graphics    'PLATON, Shelxle'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'Bruker D8 Quest Apex3'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_detector       Photon100
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            21909
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.572
_diffrn_reflns_theta_min         2.731
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.7112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.464
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.177
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 3132 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.47(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         9401
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0423
_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/[\s^2^(Fo^2^)+(0.0651P)^2^+0.0760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1109
_reflns_Friedel_coverage         0.913
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.907
_reflns_number_gt                7644
_reflns_number_total             9401
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03147_si_001.cif
_cod_data_source_block           p1831a
_cod_original_cell_volume        1361.68(7)
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               4033893
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.982
_shelx_res_checksum              29713
_shelx_hkl_checksum              18098