Diastereoselective synthesis of trifluoromethylated 1,3-dioxanes by intramolecular oxa-Michael reaction.
Becerra-Figueroa, Liliana; Brun, Elodie; Mathieson, Michael; Farrugia, Louis J.; Wilson, Claire; Prunet, Joëlle; Gamba-Sánchez, Diego; Organic & biomolecular chemistry 15 (2017) 301–305; doi:10.1039/c6ob02333a

data_7155387
_publ_section_title
;
 Diastereoselective synthesis of trifluoromethylated 1,3-dioxanes by
 intramolecular oxa-Michael reaction.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              301
_journal_page_last               305
_journal_paper_doi               10.1039/c6ob02333a
_journal_volume                  15
_journal_year                    2017
_chemical_formula_moiety         'C23 H24 F3 N O5'
_chemical_formula_sum            'C23 H24 F3 N O5'
_chemical_formula_weight         451.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-07
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-10-25 deposited with the CCDC.
2016-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.704(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.898(3)
_cell_length_b                   26.042(7)
_cell_length_c                   9.427(2)
_cell_measurement_reflns_used    2565
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.17
_cell_measurement_theta_min      2.29
_cell_volume                     2183.5(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1173
_diffrn_reflns_av_unetI/netI     0.1185
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12762
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.277
_diffrn_reflns_theta_max         25.277
_diffrn_reflns_theta_min         1.564
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1485 before and 0.1092 after correction.
The Ratio of minimum to maximum transmission is 0.6020.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       tablet
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0780
_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^)+(0.0890P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1768
_refine_ls_wR_factor_ref         0.1978
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2472
_reflns_number_total             3903
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02333a2.cif
_cod_data_source_block           2016gu0009_0m
_cod_depositor_comments
'Adding full bibliography for 7155386--7155387.cif.'
_cod_database_code               7155387
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.954
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6'(H6'), C2(H2), C4'(H4')
2.b Secondary CH2 refined with riding coordinates:
 C7'(H7'A,H7'B), C5'(H5'A,H5'B), C8'(H8'A,H8'B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C14(H14), C10(H10), C12(H12), C10'(H10'), C12'(H12'), C4(H4),
 C14'(H14'), C11'(H11'), C13(H13), C11(H11), C13'(H13')
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_shelx_res_checksum              62662
_shelx_hkl_checksum              19302
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'