Simultaneous Construction of Planar and Central Chiralities as Well as Unprecedented Axial Chirality on and around a Ferrocene Backbone.
Li, Hongjie; Jia, Peijing; Qian, Naixin; Li, Shasha; Jiao, Peng; The Journal of organic chemistry 84 (2019) 2817–2828; doi:10.1021/acs.joc.8b03221

data_4033715
_publ_section_title
;
 Simultaneous Construction of Planar and Central Chiralities as Well as
 Unprecedented Axial Chirality on and around a Ferrocene Backbone.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2817
_journal_page_last               2828
_journal_paper_doi               10.1021/acs.joc.8b03221
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H23 Fe N O'
_chemical_formula_sum            'C24 H23 Fe N O'
_chemical_formula_weight         397.30
_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'
_symmetry_Int_Tables_number      4
_audit_creation_date             2018-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.540(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5422(4)
_cell_length_b                   7.9944(2)
_cell_length_c                   11.1408(4)
_cell_measurement_reflns_used    4116
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.6590
_cell_measurement_theta_min      3.6540
_cell_volume                     938.59(5)
_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 0.9978
_diffrn_measured_fraction_theta_max 0.8222
_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    -15.00  30.00   1.00    2.34    --  -11.20 -99.00 -60.00   45
  2  \w     45.00 101.00   1.00    2.34    --   12.45 178.00  90.00   56
  3  \w    -12.00  79.00   1.00    2.34    --   12.45  37.00-120.00   91
  4  \w     10.00  44.00   1.00    2.34    --   12.45 -77.00  90.00   34
  5  \w    -58.00  23.00   1.00    2.34    --   12.45 -37.00  60.00   81
;
_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      0.0236616000
_diffrn_orient_matrix_UB_12      -0.0289412000
_diffrn_orient_matrix_UB_13      -0.0552353000
_diffrn_orient_matrix_UB_21      0.0611629000
_diffrn_orient_matrix_UB_22      0.0306684000
_diffrn_orient_matrix_UB_23      0.0165430000
_diffrn_orient_matrix_UB_31      0.0152382000
_diffrn_orient_matrix_UB_32      -0.0780961000
_diffrn_orient_matrix_UB_33      0.0269572000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7651
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         29.70
_diffrn_reflns_theta_min         3.66
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89186
_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 brown'
_exptl_crystal_density_diffrn    1.4057
_exptl_crystal_description       block
_exptl_crystal_F_000             416.8512
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.3262
_refine_diff_density_min         -0.2733
_refine_diff_density_rms         0.0629
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.028(14)
_refine_ls_d_res_high            0.7173
_refine_ls_d_res_low             5.5684
_refine_ls_goodness_of_fit_ref   1.0400
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4385
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0400
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0267P)^2^+0.1955P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0724
_reflns_Friedel_coverage         0.773
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              13
_reflns_limit_l_min              -14
_reflns_number_gt                4102
_reflns_number_total             4385
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo8b03221_si_014.cif
_cod_data_source_block           20180718b
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               4033715
_chemical_oxdiff_formula         C1H1N1O1Fe1
_reflns_odcompleteness_completeness 99.66
_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
2.a Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C4(H4a,H4b), C3(H3a,H3b), C12(H12a,H12b)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C24(H24), C27(H27), C6(H6), C18(H18), C19(H19), C25(H25),
 C26(H26), C23(H23), C22(H22), C20(H20), C21(H21)
;
_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 1.240
_oxdiff_exptl_absorpt_empirical_full_min 0.805