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_4033708
_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 H27 Fe N O'
_chemical_formula_sum            'C24 H27 Fe N O'
_chemical_formula_weight         401.31
_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             2018-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3286(4)
_cell_length_b                   11.5424(5)
_cell_length_c                   17.6325(8)
_cell_measurement_reflns_used    4036
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      27.6810
_cell_measurement_theta_min      3.8800
_cell_volume                     1898.57(14)
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.874
_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     44.00  91.00   1.00    7.84    --   12.45-178.00   0.00   47
  2  \w    -52.00  71.00   1.00    7.84    --   12.45   0.00  90.00  123
;
_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      -0.0414339000
_diffrn_orient_matrix_UB_12      -0.0101788000
_diffrn_orient_matrix_UB_13      0.0330954000
_diffrn_orient_matrix_UB_21      0.0592668000
_diffrn_orient_matrix_UB_22      -0.0282269000
_diffrn_orient_matrix_UB_23      0.0170502000
_diffrn_orient_matrix_UB_31      0.0234260000
_diffrn_orient_matrix_UB_32      0.0536589000
_diffrn_orient_matrix_UB_33      0.0152326000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8724
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.771
_diffrn_reflns_theta_min         3.530
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95743
_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    1.404
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1522 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4530
_refine_ls_number_restraints     419
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0251P)^2^+0.3518P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0768
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.786
_reflns_number_gt                4143
_reflns_number_total             4530
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03221_si_007.cif
_cod_data_source_block           20180718a
_cod_database_code               4033708
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C1H1N1O1Fe1
_reflns_odcompleteness_completeness 99.51
_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 C(H,H,H,H) groups, All O(H) groups
2. Restrained distances
 C24A-C23A = C25-C24 = C25A-C24A = C26-C25 = C26A-C25A = C27-C26 = C27A-C26A =
 C27-C23 = C24-C23 = C27A-C23A
 1.42 with sigma of 0.02
 C11-C12 \\sim C11-C12A
 with sigma of 0.02
 C12-C13 \\sim C12A-C13A
 with sigma of 0.02
 C11-C13 \\sim C11-C13A
 with sigma of 0.04
 C2-C12 \\sim C2-C12A
 with sigma of 0.04
 C2-C13 \\sim C2-C13A
 with sigma of 0.02
 C12A-C11 \\sim C12-C11
 with sigma of 0.02
 C2-C3 \\sim C2-C3A
 with sigma of 0.02
 C4-C3 \\sim C4A-C3A
 with sigma of 0.02
 C5-C3 \\sim C5-C3A
 with sigma of 0.04
 C2-C4 \\sim C2-C4A
 with sigma of 0.04
 C5-C4 \\sim C5-C4A
 with sigma of 0.02
 C3A-C2 \\sim C3-C2
 with sigma of 0.02
 N10-C2 \\sim N10-C2A
 with sigma of 0.02
 C9-C2 \\sim C9-C2A
 with sigma of 0.02
 C2-C13 \\sim C2A-C13
 with sigma of 0.02
 C2-C3 \\sim C2A-C3
 with sigma of 0.02
 C2-C13A \\sim C2A-C13A
 with sigma of 0.02
 C2-C3A \\sim C2A-C3A
 with sigma of 0.02
 C9-C2A \\sim C9-C2
 with sigma of 0.02
 C2A-C13A \\sim C2-C13
 with sigma of 0.02
 C3A-C2A \\sim C3-C2
 with sigma of 0.02
 N10-C2A \\sim N10-C2
 with sigma of 0.02
 C23-C24 \\sim C23A-C24A
 with sigma of 0.02
 C23-C27 \\sim C23A-C27A
 with sigma of 0.02
 C24-C25 \\sim C24A-C25A
 with sigma of 0.02
 C27-C26 \\sim C27A-C26A
 with sigma of 0.02
 C25-C26 \\sim C25A-C26A
 with sigma of 0.02
 Fe1-C23 \\sim Fe1-C23A
 with sigma of 0.04
 Fe1-C24 \\sim Fe1-C24A
 with sigma of 0.04
 Fe1-C27 \\sim Fe1-C27A
 with sigma of 0.04
 Fe1-C25 \\sim Fe1-C25A
 with sigma of 0.04
 Fe1-C26 \\sim Fe1-C26A
 with sigma of 0.04
 C23-C25 \\sim C23A-C25A
 with sigma of 0.04
 C23-C26 \\sim C23A-C26A
 with sigma of 0.04
 C24-C27 \\sim C24A-C27A
 with sigma of 0.04
 C24-C26 \\sim C24A-C26A
 with sigma of 0.04
 C27-C25 \\sim C27A-C25A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.02
4. Others
 Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C13A)=Sof(H13C)=
 Sof(H13D)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C2A)=1-
 FVAR(1)
 Sof(H11A)=Sof(H11B)=Sof(C2)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C12)=Sof(H12A)=
 Sof(H12B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C3)=Sof(H3A)=Sof(H3B)=FVAR(1)
 Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=Sof(C25A)=Sof(H25A)=Sof(C26A)=
 Sof(H26A)=Sof(C27A)=Sof(H27A)=1-FVAR(2)
 Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=Sof(C27)=Sof(H27)=Sof(C25)=Sof(H25)=
 Sof(C26)=Sof(H26)=FVAR(2)
5.a Riding coordinates:
 O16(H16)
5.b Ternary CH refined with riding coordinates:
 C14(H14)
5.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C11(H11C,H11D), C15(H15A,H15B), C4(H4A,H4B), C12(H12A,H12B),
 C13(H13A,H13B), C3(H3A,H3B), C12A(H12C,H12D), C13A(H13C,H13D), C4A(H4AA,H4AB),
 C3A(H3AA,H3AB)
5.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C23(H23), C24(H24), C8(H8), C20(H20), C21(H21), C7(H7), C22(H22),
 C18(H18), C19(H19), C27(H27), C25(H25), C26(H26), C23A(H23A), C24A(H24A),
 C25A(H25A), C26A(H26A), C27A(H27A)
;
_shelx_res_checksum              87503
_shelx_hkl_checksum              5031
_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 1.142
_oxdiff_exptl_absorpt_empirical_full_min 0.780