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_4034410
_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_formula_moiety         'C13 H15 Br O4'
_chemical_formula_sum            'C13 H15 Br O4'
_chemical_formula_weight         315.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.621(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7187(9)
_cell_length_b                   5.5986(5)
_cell_length_c                   23.953(3)
_cell_measurement_reflns_used    1692
_cell_measurement_temperature    199.96(10)
_cell_measurement_theta_max      25.5700
_cell_measurement_theta_min      4.0230
_cell_volume                     1285.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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      199.96(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.844
_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    -10.00  54.00   2.00   10.00    --   12.61  37.00 -90.00   32
  2  \w      5.00  87.00   2.00   10.00    --   12.61  37.00-180.00   41
  3  \w     -9.00  21.00   2.00   10.00    --  -11.04 -77.00  30.00   15
  4  \w    -28.00  18.00   2.00   10.00    --   12.61  19.00-180.00   23
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0730714000
_diffrn_orient_matrix_UB_12      -0.0027966000
_diffrn_orient_matrix_UB_13      -0.0097278000
_diffrn_orient_matrix_UB_21      -0.0119370000
_diffrn_orient_matrix_UB_22      0.0320675000
_diffrn_orient_matrix_UB_23      0.0274324000
_diffrn_orient_matrix_UB_31      0.0015094000
_diffrn_orient_matrix_UB_32      0.1225046000
_diffrn_orient_matrix_UB_33      -0.0073935000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0745
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            7012
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.732
_diffrn_reflns_theta_min         3.451
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.203
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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    1.629
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0344P)^2^+0.3776P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2244
_reflns_number_total             3087
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            2b.cif
_cod_data_source_block           20170317a
_cod_database_code               4034410
_chemical_oxdiff_formula         c1h1Br1O1
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C7(H7)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              9471
_shelx_hkl_checksum              67690
_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 1.367
_oxdiff_exptl_absorpt_empirical_full_min 0.771