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_4514789
_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         'C18 H15 N O2'
_chemical_formula_sum            'C18 H15 N O2'
_chemical_formula_weight         277.31
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-02-22
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.98144(12)
_cell_length_b                   9.10592(11)
_cell_length_c                   35.9259(4)
_cell_measurement_reflns_used    15474
_cell_measurement_temperature    294
_cell_measurement_theta_max      78.6040
_cell_measurement_theta_min      2.4840
_cell_volume                     2938.17(6)
_computing_cell_refinement
;
CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_reduction
;
CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)
;
_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_temperature      294
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.814
_diffrn_detector_type            'Rigaku Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_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    -50.00  40.00   1.00    5.00    --  -35.00  43.00 -72.00   90
  2  \w    -50.00  55.00   1.00    5.00    --  -35.00  43.00   0.00  105
  3  \w    -50.00  40.00   1.00    5.00    --  -35.00  43.00 108.00   90
  4  \w   -125.00 -32.00   1.00    5.00    -- -110.00  72.00 -72.00   93
  5  \w   -195.00-105.00   1.00    5.00    -- -110.00 -44.00 144.00   90
  6  \w   -191.00 -96.00   1.00    5.00    -- -110.00 -72.00-144.00   95
  7  \w   -187.00 -96.00   1.00    5.00    -- -110.00 -72.00 -36.00   91
  8  \w   -125.00 -31.00   1.00    5.00    -- -110.00  43.00 108.00   94
  9  \w   -200.00-110.00   1.00    5.00    -- -110.00 -44.00-108.00   90
 10  \w   -115.00 -25.00   1.00    5.00    -- -110.00  72.00   0.00   90
 11  \w   -200.00-110.00   1.00    5.00    -- -110.00 -72.00   0.00   90
 12  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -72.00-180.00   90
 13  \w   -200.00-110.00   1.00    5.00    -- -110.00 -15.00 108.00   90
 14  \w   -191.00-101.00   1.00    5.00    -- -110.00 -15.00-180.00   90
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLab P200'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0745810000
_diffrn_orient_matrix_UB_12      0.0766472000
_diffrn_orient_matrix_UB_13      0.0333990000
_diffrn_orient_matrix_UB_21      0.1215140000
_diffrn_orient_matrix_UB_22      -0.0612535000
_diffrn_orient_matrix_UB_23      0.0259890000
_diffrn_orient_matrix_UB_31      0.0953876000
_diffrn_orient_matrix_UB_32      0.1377138000
_diffrn_orient_matrix_UB_33      -0.0070317000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            25565
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.339
_diffrn_reflns_theta_min         2.460
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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    1.254
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 2468 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_coef       0.0057(5)
_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   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         6278
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0560P)^2^+0.1960P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0943
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                5990
_reflns_number_total             6278
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01502_si_003.cif
_cod_data_source_block           p20170222a
_cod_database_code               4514789
_chemical_oxdiff_formula         C18H15NO2
_shelx_estimated_absorpt_t_max   0.880
_shelx_estimated_absorpt_t_min   0.828
_reflns_odcompleteness_completeness 98.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     79.09
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C18(H18A,H18B), C27(H27A,H27B), C36(H36A,H36B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C19(H19), C23(H23), C24(H24), C25(H25), C26(H26), C31(H31), C32(H32),
  C33(H33), C34(H34)
;
_shelx_res_checksum              6811
_shelx_hkl_checksum              13340
_shelx_shelxl_version_number     2014/7
_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 1.447
_oxdiff_exptl_absorpt_empirical_full_min 0.829