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_7155386
_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_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H23 F3 O4'
_chemical_formula_sum            'C22 H23 F3 O4'
_chemical_formula_weight         408.4
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2016-10-19T13:07:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-10-19 deposited with the CCDC.
2016-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                91.588(5)
_cell_angle_beta                 107.369(4)
_cell_angle_gamma                115.303(13)
_cell_formula_units_Z            2
_cell_length_a                   8.8528(7)
_cell_length_b                   10.3504(8)
_cell_length_c                   14.1556(11)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.95
_cell_measurement_theta_min      2.21
_cell_measurement_wavelength     0.71073
_cell_volume                     1100.9(2)
_computing_cell_refinement       'SAINT V7.68A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2016/5 (Sheldrick, 2016)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.063
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            49415
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.029
_diffrn_reflns_theta_min         1.532
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.1
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_platon_squeeze_details
;
TITL shelx     P -1         R = 0.20
CELL    8.8528   10.3504   14.1556     91.59    107.37    115.30
SPGR P-1
C101 0.555 1.002 0.490 !      10.31 eA-3
C102 0.428 0.127 0.389 !       8.19 eA-3
C103 0.546 0.088 0.420 !       7.14 eA-3
C104 0.710 0.156 0.388 !       6.58 eA-3
C105 0.559 0.167 0.406 !       5.88 eA-3
Q106 0.594 1.000 0.422 !       0.95 eA-3
Q107 0.671 0.230 0.344 !       0.85 eA-3
C108 0.463 0.037 0.433 !       0.75 eA-3
Q109 0.813 0.184 0.048 !       0.74 eA-3
Q110 0.846 0.819 0.406 !       0.72 eA-3
Q111 0.215 0.412 0.063 !       0.70 eA-3
C112 0.796 0.176 0.451 !       0.69 eA-3
Q113 0.910 0.337 0.284 !       0.69 eA-3
Q114 0.095 0.759 0.190 !       0.68 eA-3
Q115 0.816 0.225 0.013 !       0.66 eA-3
Q116 0.885 0.622 0.387 !       0.64 eA-3
Q117 0.247 0.993 0.021 !       0.63 eA-3
Q118 0.380 0.833 0.225 !       0.63 eA-3
Q119 0.897 0.753 0.356 !       0.62 eA-3
Q120 0.848 0.052 0.179 !       0.62 eA-3
Q121 0.250 0.947 0.067 !       0.62 eA-3
Q122 0.668 0.287 0.165 !       0.62 eA-3
Q123 0.118 0.349 0.091 !       0.61 eA-3
Q124 0.250 0.288 0.483 !       0.61 eA-3
Q125 0.849 0.415 0.096 !       0.60 eA-3
Q126 0.789 0.563 0.457 !       0.60 eA-3
Q127 0.973 0.248 0.124 !       0.58 eA-3
Q128 0.906 0.496 0.133 !       0.58 eA-3
Q129 0.815 0.914 0.160 !       0.57 eA-3
Q130 0.189 0.346 0.499 !       0.57 eA-3
Q131 0.316 0.908 0.158 !       0.57 eA-3
Q132 0.147 0.283 0.177 !       0.57 eA-3
Q133 0.399 0.469 0.123 !       0.56 eA-3
Q134 0.782 0.934 0.086 !       0.56 eA-3
Q135 0.965 0.374 0.250 !       0.56 eA-3
Q136 0.869 0.287 0.136 !       0.54 eA-3
Q137 0.855 0.370 0.147 !       0.53 eA-3
Q138 0.057 0.255 0.131 !       0.53 eA-3
Q139 0.780 0.754 0.472 !       0.52 eA-3
Q140 0.405 0.778 0.264 !       0.52 eA-3
Q141 0.123 0.343 0.046 !       0.51 eA-3
Q142 0.168 0.777 0.193 !       0.51 eA-3
Q143 0.877 0.159 0.152 !       0.50 eA-3
;
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     263
_refine_ls_number_reflns         6433
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+0.2780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1211
_reflns_Friedel_coverage         0
_reflns_number_gt                5362
_reflns_number_total             6433
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02333a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7155386--7155387.cif.'
_cod_database_code               7155386
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.99
_shelx_shelxl_version_number     2016/5
_shelx_res_checksum              3566
_shelx_hkl_checksum              47210
_platon_squeeze_void_probe_radius 1.20
_shelx_fab_checksum              88373