Chiral Spiro Phosphoric Acid-Catalyzed Friedel–Crafts Conjugate Addition/Enantioselective Protonation Reactions
Li, Yi-Pan; Li, Zi-Qi; Zhou, Biying; Li, Mao-Lin; Xue, Xiao-Song; Zhu, Shou-Fei; Zhou, Qi-Lin; ACS Catalysis 9 (2019) 6522–; doi:10.1021/acscatal.9b01502

data_4514790
_publ_section_title
;
 Chiral Spiro Phosphoric Acid-Catalyzed Friedel--Crafts Conjugate
 Addition/Enantioselective Protonation Reactions
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              6522
_journal_paper_doi               10.1021/acscatal.9b01502
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H17 N O'
_chemical_formula_sum            'C19 H17 N O'
_chemical_formula_weight         275.33
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.9500(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.36780(10)
_cell_length_b                   6.94080(10)
_cell_length_c                   11.28290(10)
_cell_measurement_reflns_used    10620
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      78.6330
_cell_measurement_theta_min      3.9180
_cell_volume                     731.872(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.3a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.3a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.3a (Rigaku OD, 2015)'
_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      294.15
_diffrn_detector                 PILT
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.968
_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   -125.00 -28.00   1.00    5.00    --  -35.00 -72.00   0.00   97
  2  \w   -114.00 -21.00   1.00    5.00    --  -35.00 -72.00 -72.00   93
  3  \w    -50.00  40.00   1.00    5.00    --  -35.00  72.00  36.00   90
  4  \w   -114.00 -21.00   1.00    5.00    --  -35.00 -72.00  36.00   93
  5  \w    -50.00  40.00   1.00    5.00    --  -35.00  43.00   0.00   90
  6  \w   -115.00 -25.00   1.00    5.00    --  -35.00 -44.00 108.00   90
  7  \w   -117.00 -27.00   1.00    5.00    --  -35.00 -44.00-180.00   90
  8  \w   -115.00 -25.00   1.00    5.00    --  -35.00 -72.00 -36.00   90
  9  \w   -125.00 -32.00   1.00    5.00    -- -110.00  43.00-144.00   93
 10  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -44.00  72.00   91
 11  \w   -125.00 -32.00   1.00    5.00    -- -110.00  72.00 108.00   93
 12  \w   -200.00-110.00   1.00    5.00    -- -110.00 -15.00   0.00   90
 13  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -44.00 108.00   91
 14  \w   -123.00 -33.00   1.00    5.00    -- -110.00  72.00  36.00   90
 15  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -44.00 -36.00   90
 16  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -44.00  36.00   91
 17  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -44.00   0.00   90
 18  \w   -115.00 -25.00   1.00    5.00    -- -110.00  72.00  72.00   90
 19  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -72.00   0.00   91
 20  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -44.00 -72.00   90
 21  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -72.00  72.00   91
 22  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -72.00 -72.00   90
 23  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -72.00  36.00   91
 24  \w   -125.00 -33.00   1.00    5.00    -- -110.00  72.00   0.00   92
 25  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -72.00 144.00   91
 26  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -15.00-108.00   90
 27  \w   -200.00-110.00   1.00    5.00    -- -110.00 -15.00 -72.00   90
 28  \w   -200.00-110.00   1.00    5.00    -- -110.00 -15.00  36.00   90
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Xtalab P200'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1101469000
_diffrn_orient_matrix_UB_12      0.0105589000
_diffrn_orient_matrix_UB_13      0.0950938000
_diffrn_orient_matrix_UB_21      0.1225592000
_diffrn_orient_matrix_UB_22      -0.0004947000
_diffrn_orient_matrix_UB_23      0.0983411000
_diffrn_orient_matrix_UB_31      0.0054217000
_diffrn_orient_matrix_UB_32      0.2216684000
_diffrn_orient_matrix_UB_33      -0.0042351000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0092
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12277
_diffrn_reflns_point_group_measured_fraction_full 0.861
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.162
_diffrn_reflns_theta_min         3.927
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.3a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       prism
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.095
_refine_diff_density_min         -0.092
_refine_diff_density_rms         0.020
_refine_ls_abs_structure_details
;
 Flack x determined using 950 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(7)
_refine_ls_extinction_coef       0.028(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2641
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0271
_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^)+(0.0430P)^2^+0.0450P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0747
_reflns_Friedel_coverage         0.591
_reflns_Friedel_fraction_full    0.716
_reflns_Friedel_fraction_max     0.677
_reflns_number_gt                2605
_reflns_number_total             2641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01502_si_004.cif
_cod_data_source_block           p20170927a
_cod_database_code               4514790
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.910
_shelx_estimated_absorpt_t_min   0.860
_reflns_odcompleteness_completeness 96.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.92
_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:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              91323
_shelx_hkl_checksum              99182
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.219
_oxdiff_exptl_absorpt_empirical_full_min 0.817