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_7117677
_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         'C24 H22 Br F3 O3'
_chemical_formula_sum            'C24 H22 Br F3 O3'
_chemical_formula_weight         495.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-06-08 deposited with the CCDC.
2015-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.671(3)
_cell_length_b                   10.892(3)
_cell_length_c                   21.822(6)
_cell_measurement_reflns_used    1690
_cell_measurement_temperature    295.03(10)
_cell_measurement_theta_max      21.9050
_cell_measurement_theta_min      2.7480
_cell_volume                     2298.7(11)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.03(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_details
;
  1 omega  -16.00   86.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       10.3194   77.0000 -150.0000 102

  2 omega  -29.00   26.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4132   57.0000   30.0000 55
;
_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      -0.0359223000
_diffrn_orient_matrix_UB_12      -0.0535025000
_diffrn_orient_matrix_UB_13      -0.0094839000
_diffrn_orient_matrix_UB_21      -0.0620848000
_diffrn_orient_matrix_UB_22      0.0345230000
_diffrn_orient_matrix_UB_23      -0.0029075000
_diffrn_orient_matrix_UB_31      0.0168489000
_diffrn_orient_matrix_UB_32      0.0132777000
_diffrn_orient_matrix_UB_33      -0.0308678000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.1533
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10758
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.652
_diffrn_reflns_theta_min         2.303
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_type              'Agilent Mova'
_exptl_absorpt_coefficient_mu    1.834
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12958
_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.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             1008
_refine_diff_density_max         0.926
_refine_diff_density_min         -0.920
_refine_diff_density_rms         0.118
_refine_ls_abs_structure_details
;
 Flack x determined using 755 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         5412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1616
_refine_ls_R_factor_gt           0.0803
_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^)+(0.0590P)^2^+3.6410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.1943
_reflns_Friedel_coverage         0.694
_reflns_friedel_fraction_full    1.000
_reflns_friedel_fraction_max     0.782
_reflns_number_gt                2918
_reflns_number_total             5412
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc04874e2.cif
_cod_data_source_block           exp_2423
_cod_original_cell_volume        2298.6(12)
_cod_database_code               7117677
_chemical_oxdiff_formula         C22H17F3O3Br
_reflns_odcompleteness_completeness 99.82
_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:
 C0AA(H0AA), C14(H14), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C13(H13), C17(H17), C18(H18), C19(H19), C24(H24), C26(H26),
 C3(H3), C4(H4), C1AA(H1AA), C9(H9)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'