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_4033717
_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 H25 Fe N O'
_chemical_formula_sum            'C24 H25 Fe N O'
_chemical_formula_weight         399.32
_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'
_symmetry_Int_Tables_number      19
_audit_creation_date             2018-06-08
_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            4
_cell_length_a                   9.1397(2)
_cell_length_b                   18.9143(5)
_cell_length_c                   10.8778(3)
_cell_measurement_reflns_used    9066
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.5480
_cell_measurement_theta_min      4.3000
_cell_volume                     1880.46(8)
_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      100.01(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 0.8679
_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    -16.00  25.00   1.00   11.11    --  -11.20 -99.00 -90.00   41
  2  \w      2.00  38.00   1.00   11.11    --   12.45 -77.00  30.00   36
  3  \w     35.00 101.00   1.00   11.11    --   12.45 178.00  30.00   66
  4  \w    -64.00 -38.00   1.00   11.11    --   12.45 -77.00  30.00   26
  5  \w      4.00  85.00   1.00   11.11    --   12.45  37.00  60.00   81
  6  \w     -9.00  89.00   1.00   11.11    --   12.45  77.00 120.00   98
;
_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      0.0773999000
_diffrn_orient_matrix_UB_12      0.0008183000
_diffrn_orient_matrix_UB_13      -0.0040242000
_diffrn_orient_matrix_UB_21      -0.0035598000
_diffrn_orient_matrix_UB_22      0.0337929000
_diffrn_orient_matrix_UB_23      -0.0281653000
_diffrn_orient_matrix_UB_31      0.0035785000
_diffrn_orient_matrix_UB_32      0.0162626000
_diffrn_orient_matrix_UB_33      0.0586935000
_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  0.0274
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17401
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         29.82
_diffrn_reflns_theta_min         3.62
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.815
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71202
_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    1.4104
_exptl_crystal_description       plate
_exptl_crystal_F_000             841.7019
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.2746
_refine_diff_density_min         -0.2303
_refine_diff_density_rms         0.0536
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.020(12)
_refine_ls_d_res_high            0.7146
_refine_ls_d_res_low             5.6251
_refine_ls_goodness_of_fit_ref   1.0350
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    45
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0350
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0274
_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^)+(0.0202P)^2^+0.9155P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0597
_refine_ls_wR_factor_ref         0.0613
_reflns_Friedel_coverage         0.809
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              26
_reflns_limit_k_min              -25
_reflns_limit_l_max              13
_reflns_limit_l_min              -14
_reflns_number_gt                4432
_reflns_number_total             4686
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo8b03221_si_009.cif
_cod_data_source_block           JQ180529-a
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               4033717
_chemical_oxdiff_formula         C1H1O1N1Fe1
_reflns_odcompleteness_completeness 99.55
_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 Ternary CH refined with riding coordinates:
 C5(H5), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21a,H21b), C7(H7a,H7b), C3(H3a,H3b), C22(H22a,H22b), C6(H6a,H6b)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C19(H19), C11(H11), C15(H15), C23(H23), C14(H14),
 C25(H25), C24(H24), C12(H12), C26(H26), C27(H27), C13(H13)
;
_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 1.316
_oxdiff_exptl_absorpt_empirical_full_min 0.719