Preparation and Application of Amino Phosphine Ligands Bearing Spiro[indane-1,2'-pyrrolidine] Backbone.
Li, Shasha; Zhang, Jinxia; Li, Hongjie; Feng, Lifei; Jiao, Peng; The Journal of organic chemistry 84 (2019) 9460–9473; doi:10.1021/acs.joc.9b00875

data_4034415
_publ_section_title
;
 Preparation and Application of Amino Phosphine Ligands Bearing
 Spiro[indane-1,2'-pyrrolidine] Backbone.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9460
_journal_page_last               9473
_journal_paper_doi               10.1021/acs.joc.9b00875
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C24 H22 N O2 P'
_chemical_formula_sum            'C24 H22 N O2 P'
_chemical_formula_weight         387.42
_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_Int_Tables_number      19
_audit_creation_date             2018-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3691(2)
_cell_length_b                   9.9458(2)
_cell_length_c                   22.7743(5)
_cell_measurement_reflns_used    3867
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.9470
_cell_measurement_theta_min      3.8530
_cell_volume                     1895.67(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9843
_diffrn_measured_fraction_theta_max 0.9835
_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   -118.00 -15.00   1.00    1.00    --  -41.49 -77.00   0.00  103
  2  \w    -58.00 -11.00   1.00    1.00    --  -41.49 125.00  30.00   47
  3  \w   -111.00 -26.00   1.00    1.00    --  -41.49 -37.00-120.00   85
  4  \w    -23.00  14.00   1.00    1.00    --   41.49 -37.00 120.00   37
  5  \w     23.00  98.00   1.00    1.00    --   41.49-125.00-150.00   75
  6  \w     32.00  66.00   1.00    1.00    --   41.49 -37.00 120.00   34
  7  \w     78.00 177.00   1.00    1.00    --  107.19  61.00 150.00   99
  8  \w    127.00 162.00   1.00    1.00    --  107.19  61.00   0.00   35
  9  \w     99.00 164.00   1.00    1.00    --  107.19 125.00 -60.00   65
 10  \w     25.00 102.00   1.00    1.00    --  107.19 -94.00  60.00   77
 11  \w     42.00 130.00   1.00    1.00    --  107.19 -61.00 -90.00   88
 12  \w     78.00 104.00   1.00    1.00    --  107.19  61.00   0.00   26
 13  \w     93.00 120.00   1.00    1.00    --  107.19-125.00   0.00   27
 14  \w     80.00 131.00   1.00    1.00    --  107.19  30.00  30.00   51
 15  \w     65.00 108.00   1.00    1.00    --  107.19 -94.00 120.00   43
 16  \w     93.00 161.00   1.00    1.00    --  107.19  45.00 -60.00   68
 17  \w    135.00 175.00   1.00    1.00    --  107.19  30.00  30.00   40
 18  \w     33.00 107.00   1.00    1.00    --  107.19 -94.00-120.00   74
 19  \w     53.00 114.00   1.00    1.00    --  107.19 -30.00-180.00   61
 20  \w    115.00 140.00   1.00    1.00    --  107.19 -77.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0665049000
_diffrn_orient_matrix_UB_12      -0.1093078000
_diffrn_orient_matrix_UB_13      -0.0412558000
_diffrn_orient_matrix_UB_21      0.0036702000
_diffrn_orient_matrix_UB_22      -0.1003567000
_diffrn_orient_matrix_UB_23      0.0514927000
_diffrn_orient_matrix_UB_31      -0.1716378000
_diffrn_orient_matrix_UB_32      -0.0443506000
_diffrn_orient_matrix_UB_33      -0.0148871000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1195
_diffrn_reflns_av_unetI/netI     0.0958
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13047
_diffrn_reflns_theta_full        73.3491
_diffrn_reflns_theta_max         73.35
_diffrn_reflns_theta_min         3.88
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.442
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.3574
_exptl_crystal_description       plate
_exptl_crystal_F_000             819.5028
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.3497
_refine_diff_density_min         -0.5033
_refine_diff_density_rms         0.0751
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_d_res_high            0.8047
_refine_ls_d_res_low             11.3872
_refine_ls_goodness_of_fit_ref   1.0070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    40
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0070
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0364P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1182
_reflns_Friedel_coverage         0.971
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              28
_reflns_limit_l_min              -27
_reflns_number_gt                3371
_reflns_number_total             3755
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            11a.cif
_cod_data_source_block           LSS171026-1
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               4034415
_chemical_oxdiff_formula         C1H1O1N1P1
_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, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C4(H4a,H4b), C14(H14a,H14b), C5(H5a,H5b)
2.b Aromatic/amide H refined with riding coordinates:
 N12(H12), C9(H9), C18(H18), C27(H27), C26(H26), C25(H25), C28(H28), C7(H7),
 C21(H21), C24(H24), C22(H22), C8(H8), C19(H19), C20(H20)
;
_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 4.428
_oxdiff_exptl_absorpt_empirical_full_min 0.330