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_4033718
_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_formula_moiety         'C16 H17 Fe N O'
_chemical_formula_sum            'C16 H17 Fe N O'
_chemical_formula_weight         295.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-05-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.088(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.9629(7)
_cell_length_b                   21.9497(12)
_cell_length_c                   11.2186(7)
_cell_measurement_reflns_used    9743
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      29.6570
_cell_measurement_theta_min      4.3180
_cell_volume                     2551.1(3)
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_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 0.865
_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    -28.00  51.00   1.00   21.34    --   12.45 -92.00-152.81   79
  2  \w    -13.00  82.00   1.00   21.34    --   12.45  57.00  60.00   95
  3  \w    -18.00  88.00   1.00   21.34    --   12.45  77.00-180.00  106
  4  \w     -6.00  87.00   1.00   21.34    --   12.45  37.00 -30.00   93
  5  \w    -55.00  41.00   1.00   21.34    --   12.45 -57.00 -90.00   96
  6  \w    -18.00  53.00   1.00   21.34    --   12.45 -99.00 150.00   71
  7  \w    -28.00  52.00   1.00   21.34    --   14.00 -92.00  45.99   80
;
_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      -0.0141067000
_diffrn_orient_matrix_UB_12      0.0199524000
_diffrn_orient_matrix_UB_13      0.0434579000
_diffrn_orient_matrix_UB_21      -0.0474889000
_diffrn_orient_matrix_UB_22      0.0147132000
_diffrn_orient_matrix_UB_23      -0.0505268000
_diffrn_orient_matrix_UB_31      -0.0473764000
_diffrn_orient_matrix_UB_32      -0.0207069000
_diffrn_orient_matrix_UB_33      0.0060294000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1067
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20368
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.605
_diffrn_reflns_theta_min         3.383
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67465
_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 yellow'
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_description       needle
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.368
_refine_diff_density_min         -0.972
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0498
_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^)+(0.0748P)^2^+3.5952P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1362
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2950
_reflns_number_total             3412
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03221_si_003.cif
_cod_data_source_block           20180503i
_cod_database_code               4033718
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C1H1N1O1Fe1
_reflns_odcompleteness_completeness 99.78
_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, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 N10(H10), C15(H15), C4(H4), C6(H6), C16(H16), C17(H17), C5(H5), C19(H19),
 C18(H18)
;
_shelx_res_checksum              40645
_shelx_hkl_checksum              98168
_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 1.601
_oxdiff_exptl_absorpt_empirical_full_min 0.551