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_4034412
_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         'C12 H13 N O'
_chemical_formula_sum            'C12 H13 N O'
_chemical_formula_weight         187.23
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-10-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.39581(12)
_cell_length_b                   9.46599(17)
_cell_length_c                   13.8475(2)
_cell_measurement_reflns_used    3316
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.8290
_cell_measurement_theta_min      4.6200
_cell_volume                     969.44(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_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     24.00  84.00   1.00    1.00    --   41.49-125.00 -90.00   60
  2  \w     26.00  93.00   1.00    1.00    --   41.49-125.00 -30.00   67
  3  \w     46.00  72.00   1.00    1.00    --  107.19 -94.00 -60.00   26
  4  \w     78.00 109.00   1.00    1.00    --  107.19 -94.00 -60.00   31
  5  \w     35.00 115.00   1.00    1.00    --  107.19-125.00-120.00   80
  6  \w     82.00 148.00   1.00    1.00    --  107.19  45.00-120.00   66
  7  \w    139.00 175.00   1.00    1.00    --  107.19  77.00  90.00   36
  8  \w     91.00 117.00   1.00    1.00    --  107.19  77.00  90.00   26
  9  \w   -112.00 -75.00   1.00    1.00    --  -41.49 -57.00 -60.00   37
 10  \w    -62.00  -5.00   1.00    1.00    --  -41.74  77.00 120.00   57
 11  \w    104.00 135.00   1.00    1.00    --  107.19 125.00 150.00   31
 12  \w    150.00 177.00   1.00    1.00    --  107.19 125.00 150.00   27
 13  \w     95.00 140.00   1.00    1.00    --  107.19 125.00  60.00   45
 14  \w     99.00 159.00   1.00    1.00    --  107.19 125.00-120.00   60
 15  \w     80.00 108.00   1.00    1.00    --  107.19-125.00 150.00   28
;
_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      0.1305640000
_diffrn_orient_matrix_UB_12      -0.1259460000
_diffrn_orient_matrix_UB_13      -0.0112760000
_diffrn_orient_matrix_UB_21      0.0034937000
_diffrn_orient_matrix_UB_22      0.0233959000
_diffrn_orient_matrix_UB_23      -0.1100843000
_diffrn_orient_matrix_UB_31      0.1622886000
_diffrn_orient_matrix_UB_32      0.1003515000
_diffrn_orient_matrix_UB_33      0.0115077000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3893
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.011
_diffrn_reflns_theta_min         5.662
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.6a (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    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 751 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0312
_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^)+(0.0473P)^2^+0.1617P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0811
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                1872
_reflns_number_total             1884
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            6a.cif
_cod_data_source_block           20161012c
_cod_database_code               4034412
_chemical_oxdiff_formula         c1h1n1o1
_reflns_odcompleteness_completeness 99.90
_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:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C10(H10), C11(H11), C12(H12)
;
_shelx_res_checksum              55538
_shelx_hkl_checksum              44925
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.165
_oxdiff_exptl_absorpt_empirical_full_min 0.842