Effect of remote aryl substituents on the conformational equilibria of 2,2-diaryl-1,3-dioxanes: importance of electrostatic interactions.
Bailey, William F.; Lambert, Kyle M.; Wiberg, Kenneth B.; Mercado, Brandon Q.; The Journal of organic chemistry 80 (2015) 4108–4115; doi:10.1021/acs.joc.5b00422

data_4036184
_publ_section_title
;
 Effect of remote aryl substituents on the conformational equilibria of
 2,2-diaryl-1,3-dioxanes: importance of electrostatic interactions.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4108
_journal_page_last               4115
_journal_paper_doi               10.1021/acs.joc.5b00422
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H19 N O4'
_chemical_formula_sum            'C18 H19 N O4'
_chemical_formula_weight         313.34
_chemical_name_common            'compound 2'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 106.570(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7461(2)
_cell_length_b                   13.7554(3)
_cell_length_c                   8.0544(6)
_cell_measurement_reflns_used    11968
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      66.5
_cell_measurement_theta_min      3.2
_cell_volume                     822.56(7)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1060
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            28960
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         66.554
_diffrn_reflns_theta_min         5.731
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
; 
 Flack x determined using 1026 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.07(13)
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2859
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0615
_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^)+(0.1219P)^2^+0.1587P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1639
_refine_ls_wR_factor_ref         0.1909
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                2417
_reflns_number_total             2859
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00422_si_002.cif
_cod_data_source_block           007_13129
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4036184
_shelx_estimated_absorpt_t_min   0.917
_shelx_estimated_absorpt_t_max   0.978
_shelxl_version_number           2013-3
_shelx_res_checksum              24107
_shelx_hkl_checksum              92170