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_4034413
_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 ad
_chemical_formula_moiety         'C13 H15 N O2'
_chemical_formula_sum            'C13 H15 N O2'
_chemical_formula_weight         217.26
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-11-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.2490(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.00540(10)
_cell_length_b                   7.73140(10)
_cell_length_c                   8.68840(10)
_cell_measurement_reflns_used    6900
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.1090
_cell_measurement_theta_min      5.0980
_cell_volume                     535.496(11)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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      0.00  25.00   1.00    1.00    --   38.00  93.00-136.81   25
  2  \w    -62.00 -17.00   1.00    1.00    --  -41.49 -37.00  90.00   45
  3  \w    -45.00 -13.00   1.00    1.00    --  -41.49 -57.00   0.00   32
  4  \w   -106.00 -80.00   1.00    1.00    --  -41.49 -37.00  90.00   26
  5  \w    -61.00  32.00   1.00    1.00    --  -41.49  37.00-180.00   93
  6  \w    -94.00 -60.00   1.00    1.00    --  -41.49 -57.00   0.00   34
  7  \w     27.00  78.00   1.00    1.00    --   41.49  37.00-180.00   51
  8  \w     23.00  98.00   1.00    1.00    --   41.49-125.00 -30.00   75
  9  \w    -30.00  72.00   1.00    1.00    --   41.49 -77.00   0.00  102
 10  \w     17.00  42.00   1.00    1.00    --   50.00  80.00 -21.29   25
 11  \w     17.00  43.00   1.00    1.00    --   50.00  78.00 127.94   26
 12  \w     18.00  44.00   1.00    1.00    --   50.00  79.00  52.88   26
 13  \w     17.00  42.00   1.00    1.00    --   50.00  79.00 -86.70   25
 14  \w     96.00 123.00   1.00    1.00    --   54.00  77.00  99.82   27
 15  \w     22.00  53.00   1.00    1.00    --   54.00  77.00 -46.86   31
 16  \w     23.00  48.00   1.00    1.00    --   54.00  77.00  99.82   25
 17  \w     27.00  64.00   1.00    1.00    --   58.00  75.00-159.52   37
 18  \w     28.00  54.00   1.00    1.00    --   58.00  65.00 145.05   26
 19  \w     33.00  59.00   1.00    1.00    --   62.00  77.00  -7.50   26
 20  \w     35.00  60.00   1.00    1.00    --   66.00  76.00 150.33   25
 21  \w     38.00  64.00   1.00    1.00    --   66.00  64.00-139.22   26
 22  \w     39.00  65.00   1.00    1.00    --   70.00  75.00 136.06   26
 23  \w     38.00 144.00   1.00    1.00    --   70.00  76.00  17.90  106
 24  \w     42.00 111.00   1.00    1.00    --   74.00  77.00-135.33   69
 25  \w     57.00  85.00   1.00    1.00    --   86.00  62.00 -56.98   28
 26  \w     95.00 177.00   1.00    1.00    --  107.19 125.00-120.00   82
 27  \w     75.00 168.00   1.00    1.00    --  107.19  77.00  60.00   93
 28  \w     79.00 119.00   1.00    1.00    --  107.19  61.00 -30.00   40
 29  \w     25.00 106.00   1.00    1.00    --  107.19 -94.00-180.00   81
 30  \w     76.00 177.00   1.00    1.00    --  107.19  77.00-150.00  101
 31  \w     67.00 104.00   1.00    1.00    --  107.19 -94.00  30.00   37
 32  \w     78.00 129.00   1.00    1.00    --  107.19  61.00 -90.00   51
 33  \w     75.00 101.00   1.00    1.00    --  107.19  77.00 120.00   26
 34  \w     82.00 115.00   1.00    1.00    --  107.19  61.00  30.00   33
 35  \w     57.00 128.00   1.00    1.00    --  107.19 -61.00 -60.00   71
 36  \w     82.00 108.00   1.00    1.00    --  107.19  45.00 -90.00   26
 37  \w    117.00 144.00   1.00    1.00    --  107.19  77.00 -60.00   27
 38  \w    117.00 142.00   1.00    1.00    --  107.19  77.00  30.00   25
 39  \w     76.00 114.00   1.00    1.00    --  107.19  77.00 -60.00   38
 40  \w     76.00 149.00   1.00    1.00    --  107.19  77.00-180.00   73
 41  \w     77.00 107.00   1.00    1.00    --  107.19  77.00  30.00   30
 42  \w     78.00 104.00   1.00    1.00    --  107.19  61.00-180.00   26
 43  \w     79.00 109.00   1.00    1.00    --  107.19  61.00  60.00   30
 44  \w     75.00 176.00   1.00    1.00    --  107.19  77.00 -30.00  101
 45  \w     79.00 176.00   1.00    1.00    --  107.19  61.00 150.00   97
 46  \w    122.00 174.00   1.00    1.00    --  107.19  77.00   0.00   52
 47  \w     78.00 105.00   1.00    1.00    --  107.19  77.00   0.00   27
 48  \w     25.00 108.00   1.00    1.00    --  107.19 -94.00 -90.00   83
 49  \w     75.00 177.00   1.00    1.00    --  107.19  77.00  90.00  102
 50  \w     85.00 112.00   1.00    1.00    --  107.19  61.00   0.00   27
;
_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      0.1793286000
_diffrn_orient_matrix_UB_12      0.0296911000
_diffrn_orient_matrix_UB_13      -0.0451897000
_diffrn_orient_matrix_UB_21      0.0599045000
_diffrn_orient_matrix_UB_22      0.0388891000
_diffrn_orient_matrix_UB_23      0.1701376000
_diffrn_orient_matrix_UB_31      0.0397114000
_diffrn_orient_matrix_UB_32      -0.1931412000
_diffrn_orient_matrix_UB_33      0.0272800000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7770
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.863
_diffrn_reflns_theta_min         5.112
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62370
_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    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 864 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1979
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0269
_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^)+(0.0366P)^2^+0.1108P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0675
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                1961
_reflns_number_total             1979
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            8.cif
_cod_data_source_block           fjj20180815
_cod_database_code               4034413
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 N1 O1'
_shelx_estimated_absorpt_t_max   0.867
_shelx_estimated_absorpt_t_min   0.758
_reflns_odcompleteness_completeness 100.00
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C12(H12A,H12B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N10(H10), C6(H6), C5(H5), C7(H7)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              11528
_shelx_hkl_checksum              41556
_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 1.429
_oxdiff_exptl_absorpt_empirical_full_min 0.599