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_4033719
_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 O2, 0.5(H2 O)'
_chemical_formula_sum            'C24 H26 Fe N O2.5'
_chemical_formula_weight         424.31
_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
_audit_creation_date             2018-08-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 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                   8.58910(10)
_cell_length_b                   15.2073(2)
_cell_length_c                   30.3650(5)
_cell_measurement_reflns_used    12705
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.9530
_cell_measurement_theta_min      4.0770
_cell_volume                     3966.19(10)
_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)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.995
_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    -66.00  27.00   1.00    1.00    --  -41.49  37.00 -30.00   93
  2  \w      6.00  33.00   1.00    1.00    --  -41.49  37.00-150.00   27
  3  \w    -82.00  22.00   1.00    1.00    --  -41.49  19.00-150.00  104
  4  \w   -113.00 -77.00   1.00    1.00    --  -41.49 -37.00  30.00   36
  5  \w   -118.00 -11.00   1.00    1.00    --  -41.49 -77.00-180.00  107
  6  \w     35.00 118.00   1.00    4.00    --  107.19-125.00 120.00   83
  7  \w    141.00 178.00   1.00    4.00    --  107.19  77.00   0.00   37
  8  \w     32.00 137.00   1.00    4.00    --  107.19 -77.00  90.00  105
  9  \w     43.00 140.00   1.00    4.00    --  107.19 -77.00-120.00   97
 10  \w     79.00 105.00   1.00    4.00    --  107.19 -94.00   0.00   26
 11  \w     37.00 135.00   1.00    4.00    --  107.19 -30.00  60.00   98
 12  \w     94.00 169.00   1.00    4.00    --  107.19  30.00  30.00   75
 13  \w     95.00 174.00   1.00    4.00    --  107.19  30.00-150.00   79
 14  \w     43.00  68.00   1.00    4.00    --  107.19 -94.00   0.00   25
 15  \w     82.00 128.00   1.00    4.00    --  107.19  30.00   0.00   46
 16  \w     83.00 109.00   1.00    4.00    --  107.19 -94.00-180.00   26
 17  \w     94.00 142.00   1.00    4.00    --  107.19 125.00  90.00   48
 18  \w    100.00 125.00   1.00    4.00    --  107.19  83.00-127.00   25
 19  \w     65.00 151.00   1.00    4.00    --  107.19   0.00 -30.00   86
;
_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      0.0521855000
_diffrn_orient_matrix_UB_12      -0.0879251000
_diffrn_orient_matrix_UB_13      0.0204343000
_diffrn_orient_matrix_UB_21      -0.1181062000
_diffrn_orient_matrix_UB_22      0.0126099000
_diffrn_orient_matrix_UB_23      0.0376371000
_diffrn_orient_matrix_UB_31      -0.1245927000
_diffrn_orient_matrix_UB_32      -0.0486584000
_diffrn_orient_matrix_UB_33      -0.0271889000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            29002
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.274
_diffrn_reflns_theta_min         4.115
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.275
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47294
_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 pale brown'
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       block
_exptl_crystal_F_000             1784
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.956
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 2669 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         7898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0453P)^2^+2.9075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                7085
_reflns_number_total             7898
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03221_si_006.cif
_cod_data_source_block           20171116e
_cod_original_formula_sum        'C24 H26 Fe N O2.50'
_cod_database_code               4033719
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C1H1N1O1Fe1
_reflns_odcompleteness_completeness 99.90
_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
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O2AA(H2AA,H2AB)
2.b Ternary CH refined with riding coordinates:
 C3AA(H3AB), C5BA(H5BA)
2.c Secondary CH2 refined with riding coordinates:
 C7AA(H7AA,H7AB), C8AA(H8AA,H8AB), C6BA(H6BA,H6BB), C7BA(H7BA,H7BB), C2CA(H2CA,
 H2CB), C3CA(H3CA,H3CB), C0DA(H0DA,H0DB), C1DA(H1DA,H1DB), C7DA(H7DA,H7DB),
 C0EA(H0EA,H0EB)
2.d Aromatic/amide H refined with riding coordinates:
 C0AA(H0AA), C4AA(H4AB), C5AA(H5AA), C0BA(H0BA), C2BA(H2BA), C3BA(H3BA),
 C4BA(H4BA), C8BA(H8BA), C9BA(H9BA), C4CA(H4CA), C6CA(H6CA), C7CA(H7CA),
 C8CA(H8CA), C9CA(H9CA), C2DA(H2DA), C5DA(H5DA), C6DA(H6DA), C8DA(H8DA),
 C9DA(H9DA), C1EA(H1EA), C2EA(H2EA), C3EA(H3EA), C4EA(H4EA), C5EA(H5EA),
 C6EA(H6EA), C7EA(H7EA)
2.e Idealised tetrahedral OH refined as rotating group:
 O4AA(H4AA), O3AA(H3AA)
;
_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 1.655
_oxdiff_exptl_absorpt_empirical_full_min 0.608