Asymmetric synthesis of chiral trifluoromethylated heliotridane via highly catalytic asymmetric Friedel–Crafts alkylation with β-trifluoromethylated acrylates and pyrroles
Huang, Yiyong; Suzuki, Satoru; Liu, Guokai; Tokunaga, Etsuko; Shiro, Motoo; Shibata, Norio; New Journal of Chemistry 35 (2011) 2614–; doi:10.1039/c1nj20550a

data_7052787
_publ_section_title
;
 Asymmetric synthesis of chiral trifluoromethylated heliotridane via
 highly catalytic asymmetric Friedel--Crafts alkylation with
 \b-trifluoromethylated acrylates and pyrroles
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2614
_journal_paper_doi               10.1039/c1nj20550a
_journal_volume                  35
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H17 F3 N2 O3 '
_chemical_formula_sum            'C18 H17 F3 N2 O3'
_chemical_formula_weight         366.34
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.0681(9)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   10.77497(19)
_cell_length_b                   6.30036(11)
_cell_length_c                   12.5202(7)
_cell_measurement_reflns_used    15209
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      4.1
_cell_volume                     849.40(5)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      93.1
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16058
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_exptl_absorpt_coefficient_mu    1.033
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             380.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.13
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1272 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2971
_refine_ls_R_factor_gt           0.0243
_refine_ls_shift/su_max          0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0329P)^2^+0.2077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0617
_reflns_number_gt                2914
_reflns_number_total             2971
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c1nj20550a.txt
_cod_data_source_block           '_FC-164'
_cod_original_cell_volume        849.39(5)
_cod_original_formula_sum        'C18 H17 F3 N2 O3 '
_cod_database_code               7052787