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_4034414
_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         'C40 H54 N O2 P, 0.5(H2 O)'
_chemical_formula_sum            'C40 H55 N O2.5 P'
_chemical_formula_weight         620.81
_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   mixed
_atom_sites_solution_primary     iterative
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.3937(2)
_cell_length_b                   18.5331(3)
_cell_length_c                   38.2687(6)
_cell_measurement_reflns_used    12641
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.6350
_cell_measurement_theta_min      4.1910
_cell_volume                     7371.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6254
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.978
_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    -93.00 -17.00   1.00    3.29    --  -41.49 125.00 -30.00   76
  2  \w   -115.00 -13.00   1.00    3.29    --  -41.49 -57.00-150.00  102
  3  \w      1.00  42.00   1.00    3.29    --   41.49 -99.00 150.00   41
  4  \w     44.00  70.00   1.00   13.17    --  104.69 -45.00  30.00   26
  5  \w     97.00 148.00   1.00   13.17    --  104.69 125.00-180.00   51
  6  \w    107.00 133.00   1.00   13.17    --  104.69 125.00   0.00   26
  7  \w     32.00 121.00   1.00   13.17    --  104.69 -45.00-150.00   89
  8  \w    144.00 171.00   1.00   13.17    --  104.69 125.00   0.00   27
  9  \w     77.00 165.00   1.00   13.17    --  104.69  77.00   0.00   88
 10  \w     87.00 169.00   1.00   13.17    --  104.69  30.00  90.00   82
;
_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      0.1474721000
_diffrn_orient_matrix_UB_12      -0.0051070000
_diffrn_orient_matrix_UB_13      -0.0030369000
_diffrn_orient_matrix_UB_21      0.0012710000
_diffrn_orient_matrix_UB_22      0.0687909000
_diffrn_orient_matrix_UB_23      -0.0226285000
_diffrn_orient_matrix_UB_31      0.0145869000
_diffrn_orient_matrix_UB_32      0.0463829000
_diffrn_orient_matrix_UB_33      0.0331662000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            26803
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.100
_diffrn_reflns_theta_min         4.207
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.916
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_description       block
_exptl_crystal_F_000             2696
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.999
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 5531 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     829
_refine_ls_number_reflns         14040
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0627P)^2^+6.2123P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1335
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                13276
_reflns_number_total             14040
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            11d.cif
_cod_data_source_block           zjx20180921
_cod_depositor_comments
;

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C40 H54 N O2 P), H2 O'
_cod_original_formula_sum        'C80 H110 N2 O5 P2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1241.63
_cod_database_code               4034414
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         ' C1 N1 O1 P1 H1'
_reflns_odcompleteness_completeness 99.75
_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, All O(H,H) groups
2.a Free rotating group:
 O89(H89A,H89B)
2.b Secondary CH2 refined with riding coordinates:
 C57(H57A,H57B), C48(H48A,H48B), C5(H5A,H5B), C49(H49A,H49B), C58(H58A,H58B),
 C4(H4A,H4B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), N56(H56), N12(H12), C36(H36), C22(H22), C80(H80), C64(H64),
 C78(H78), C34(H34), C76(H76), C18(H18), C66(H66), C62(H62), C9(H9), C7(H7),
 C8(H8), C32(H32), C53(H53), C51(H51), C52(H52)
2.d Idealised Me refined as rotating group:
 C82(H82A,H82B,H82C), C83(H83A,H83B,H83C), C24(H24A,H24B,H24C), C86(H86A,H86B,
 H86C), C28(H28A,H28B,H28C), C42(H42A,H42B,H42C), C29(H29A,H29B,H29C), C87(H87A,
 H87B,H87C), C25(H25A,H25B,H25C), C43(H43A,H43B,H43C), C84(H84A,H84B,H84C),
 C26(H26A,H26B,H26C), C68(H68A,H68B,H68C), C30(H30A,H30B,H30C), C88(H88A,H88B,
 H88C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C44(H44A,H44B,H44C), C40(H40A,
 H40B,H40C), C72(H72A,H72B,H72C), C73(H73A,H73B,H73C), C74(H74A,H74B,H74C),
 C69(H69A,H69B,H69C), C70(H70A,H70B,H70C)
;
_shelx_res_checksum              43140
_shelx_hkl_checksum              37706
_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 1.614
_oxdiff_exptl_absorpt_empirical_full_min 0.642