The stereoselective formation of highly substituted CF3-dihydropyrans as versatile building blocks
Bjarke S. Donslund; Alicia Monleon; Jesper Larsen; Lise Ibsen; Karl Anker Jorgensen; Chem.Commun. 51 (2015) 13666–; doi:10.1039/C5cc04874E

data_7117676
_publ_section_title
;
 The stereoselective formation of highly substituted CF3-dihydropyrans as
 versatile building blocks
;
_journal_name_full               Chem.Commun.
_journal_page_first              13666
_journal_paper_doi               10.1039/C5cc04874E
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H22 Br F3 O4'
_chemical_formula_sum            'C28 H22 Br F3 O4'
_chemical_formula_weight         559.36
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-06-07 deposited with the CCDC.
2015-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.557(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6758(14)
_cell_length_b                   9.3185(8)
_cell_length_c                   25.405(3)
_cell_measurement_reflns_used    2508
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      22.4060
_cell_measurement_theta_min      2.6860
_cell_volume                     2492.3(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_details
;
  1 omega   35.00   81.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6399  178.0000  -60.0000 46

  2 omega  -20.00   60.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6399  -99.0000  150.0000 80

  3 omega   -9.00   94.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6399   38.0000   60.0000 103

  4 omega  -12.00   92.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6399   57.0000  -30.0000 104

  5 omega  -45.00  -14.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8118   38.0000   30.0000 31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0089953000
_diffrn_orient_matrix_UB_12      -0.0156030000
_diffrn_orient_matrix_UB_13      0.0277022000
_diffrn_orient_matrix_UB_21      -0.0270202000
_diffrn_orient_matrix_UB_22      -0.0689249000
_diffrn_orient_matrix_UB_23      -0.0057214000
_diffrn_orient_matrix_UB_31      0.0610916000
_diffrn_orient_matrix_UB_32      -0.0281891000
_diffrn_orient_matrix_UB_33      -0.0013777000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_av_unetI/netI     0.2652
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            25880
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.042
_diffrn_reflns_theta_min         2.219
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.705
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_F_000             1136
_refine_diff_density_max         1.431
_refine_diff_density_min         -1.114
_refine_diff_density_rms         0.127
_refine_ls_abs_structure_details
;
 Flack x determined using 1153 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     641
_refine_ls_number_reflns         14583
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.2437
_refine_ls_R_factor_gt           0.1093
_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^)+(0.0850P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2150
_refine_ls_wR_factor_ref         0.2913
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.769
_reflns_number_gt                5639
_reflns_number_total             14583
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc04874e2.cif
_cod_data_source_block           exp_2547
_cod_database_code               7117676
_chemical_oxdiff_formula         C28H22BrF3O4
_reflns_odcompleteness_completeness 99.01
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00M(H00M), C00P(H00P), C00U(H00U), C00V(H00V), C016(H016), C017(H017),
 C01G(H01J), C01L(H01N)
2.b Secondary CH2 refined with riding coordinates:
 C018(H01A,H01B), C01C(H01C,H01D), C01O(H01O,H01P), C020(H02A,H02B)
2.c Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00I(H00I), C00L(H00L), C00O(H00O), C00Q(H00Q), C00T(H00T),
 C00W(H00W), C00Z(H00Z), C012(H012), C013(H013), C015(H015), C019(H019),
 C01A(H01H), C01E(H01I), C01J(H01K), C01K(H01L), C01M(H01M), C01T(H01T),
 C01U(H01U), C01W(H01W), C01X(H01X), C01Y(H01Y)
2.d Idealised Me refined as rotating group:
 C01P(H01E,H01F,H01G), C01V(H01Q,H01R,H01S)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'