Asymmetric synthesis of polycyclic 3-fluoroalkylproline derivatives by intramolecular azomethine ylide cycloaddition
Rabasa-Alcañiz, Fernando; Hammerl, Daniel; Sánchez-Merino, Anabel; Tejero, Tomás; Merino, Pedro; Fustero, Santos; del Pozo, Carlos; Organic Chemistry Frontiers 6 (2019) 2916–; doi:10.1039/C9QO00525K

data_1554940
_publ_section_title
;
 Asymmetric synthesis of polycyclic 3-fluoroalkylproline derivatives by
 intramolecular azomethine ylide cycloaddition
;
_journal_issue                   16
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2916
_journal_paper_doi               10.1039/C9QO00525K
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H18 F3 N O3'
_chemical_formula_sum            'C22 H18 F3 N O3'
_chemical_formula_weight         401.37
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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     dual
_audit_creation_date             2019-01-11T15:08:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-02-25 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.69927(9)
_cell_length_b                   10.83500(9)
_cell_length_c                   16.94975(13)
_cell_measurement_reflns_used    8562
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.122
_cell_measurement_theta_min      4.077
_cell_volume                     1781.28(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -115.00 -29.00   0.50    1.00    --  -42.38 -38.00  90.00  172
  2  \w    -94.00  -2.00   0.50    1.00    --  -42.38 125.00  30.00  184
  3  \w     40.00  66.00   0.50    1.00    --  107.93-125.00  90.00   52
  4  \w     34.00  68.00   0.50    1.00    --  107.93 -30.00 -60.00   68
  5  \w     40.00  71.00   0.50    1.00    --  107.93 -45.00-120.00   62
  6  \w     35.00  60.00   0.50    1.00    --  107.93 -45.00 120.00   50
  7  \w     46.00 106.00   0.50    1.00    --  107.93-125.00-180.00  120
  8  \w     82.00 118.00   0.50    1.00    --  107.93-125.00  90.00   72
  9  \w     37.00  63.00   0.50    1.00    --  107.93 -45.00 -30.00   52
 10  \w     40.00  66.00   0.50    1.00    --  107.93 -30.00 -90.00   52
 11  \w     93.00 158.00   0.50    1.00    --  107.93 125.00 -60.00  130
 12  \w     48.00 131.00   0.50    1.00    --  107.93 -61.00   0.00  166
 13  \w     35.00  60.00   0.50    1.00    --  107.93 -45.00 -90.00   50
 14  \w   -119.00 -10.00   0.50    1.00    --  -42.38 -77.00   0.00  218
 15  \w   -116.00 -14.00   0.50    1.00    --  -42.38 -57.00-150.00  204
 16  \w    -30.00  71.00   0.50    1.00    --   42.38 -57.00-150.00  202
 17  \w     82.00 122.00   0.50    1.00    --  107.93  45.00  60.00   80
;
_diffrn_measurement_device       'four-circle\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.089612
_diffrn_orient_matrix_UB_12      -0.0546233
_diffrn_orient_matrix_UB_13      -0.0664491
_diffrn_orient_matrix_UB_21      -0.1277491
_diffrn_orient_matrix_UB_22      -0.0074476
_diffrn_orient_matrix_UB_23      -0.0538384
_diffrn_orient_matrix_UB_31      0.0299496
_diffrn_orient_matrix_UB_32      0.1310046
_diffrn_orient_matrix_UB_33      -0.0307687
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9754
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.989
_diffrn_reflns_theta_min         4.844
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.028
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.155
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.17
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 The Friedel pair coverage of the experiment is almost complete 
 (94%). Analysis of the absolute structure using likelihood methods
 (Hooft, Straver & Spek, 2008) was performed using PLATON
 (Spek, 2009). The resulting value was y=0.00(3)
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0383P)^2^+0.3395P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0691
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3230
_reflns_number_total             3288
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00525k2.cif
_cod_data_source_block           a20180355_fr1909
_cod_database_code               1554940