Chiral Calcium Phosphate Catalyzed Asymmetric Alkenylation Reaction of Arylglyoxals with 3-Vinylindoles.
Li, Xiao-Yun; Yuan, Wen-Qiang; Tang, Sheng; Huang, Yi-Wei; Xue, Jia-Hui; Fu, Li Na; Guo, Qi-Xiang; Organic letters 19 (2017) 1120–1123; doi:10.1021/acs.orglett.7b00143

data_1545285
_publ_section_title
;
 Chiral Calcium Phosphate Catalyzed Asymmetric Alkenylation Reaction of
 Arylglyoxals with 3-Vinylindoles.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1120
_journal_page_last               1123
_journal_paper_doi               10.1021/acs.orglett.7b00143
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C25 H21 N O2'
_chemical_formula_sum            'C25 H21 N O2'
_chemical_formula_weight         367.43
_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             2016-11-15
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.75219(16)
_cell_length_b                   11.3668(2)
_cell_length_c                   19.7080(4)
_cell_measurement_reflns_used    5257
_cell_measurement_temperature    290.47(10)
_cell_measurement_theta_max      72.9480
_cell_measurement_theta_min      4.4780
_cell_volume                     1960.64(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.47(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_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   -104.00 -20.00   1.00    1.00    --  -37.03 -57.00  90.00   84
  2  \w    -30.00  54.00   1.00    1.00    --   37.03 -57.00 150.00   84
  3  \w      1.00  76.00   1.00    1.00    --   37.03 -99.00 120.00   75
  4  \w     24.00  91.00   1.00    1.00    --   37.03-126.00 -90.00   67
  5  \w     20.00 104.00   1.00    1.00    --   37.03  57.00  90.00   84
  6  \w     41.00 109.00   1.00   30.00    --  110.47 -95.00-150.00   68
  7  \w     41.00 109.00   1.00   30.00    --  110.47 -95.00   0.00   68
  8  \w     42.00 128.00   1.00   30.00    --  110.47 -45.00-150.00   86
  9  \w     41.00 178.00   1.00   30.00    --  110.47   0.00 150.00  137
 10  \w   -106.00 -18.00   1.00    1.00    --  -37.03 -38.00 -60.00   88
 11  \w   -106.00 -18.00   1.00    1.00    --  -37.03 -38.00-150.00   88
 12  \w    -32.00  56.00   1.00    1.00    --   37.03 -38.00 -60.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0011889000
_diffrn_orient_matrix_UB_12      0.1215634000
_diffrn_orient_matrix_UB_13      -0.0345327000
_diffrn_orient_matrix_UB_21      0.0483670000
_diffrn_orient_matrix_UB_22      -0.0575162000
_diffrn_orient_matrix_UB_23      -0.0674337000
_diffrn_orient_matrix_UB_31      -0.1693152000
_diffrn_orient_matrix_UB_32      -0.0173250000
_diffrn_orient_matrix_UB_33      -0.0189740000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8352
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.968
_diffrn_reflns_theta_min         4.487
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1185 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.04(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3538
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0641P)^2^+0.2449P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.609
_reflns_Friedel_fraction_full    0.844
_reflns_Friedel_fraction_max     0.801
_reflns_number_gt                3244
_reflns_number_total             3538
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00143_si_003.cif
_cod_data_source_block           gqx-20161115-3
_cod_depositor_comments
'Adding full bibliography for 1545285--1545286.cif.'
_cod_original_cell_volume        1960.64(7)
_cod_database_code               1545285
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C1 H1 N1 O1'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O2) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C5(H5), C6(H6), C15(H15), C16(H16), C17(H17),
 C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
3.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              45386
_shelx_hkl_checksum              38674
_olex2_date_sample_data_collection 2016-11-15
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.070
_oxdiff_exptl_absorpt_empirical_full_min 0.437