Synthesis of Ferrocene Oxazoline N,O ligands and Their Application in Asymmetric Ethyl- and Phenylzinc Additions to Aldehydes.
Nottingham, Chris; Benson, Robert; Müller-Bunz, Helge; Guiry, Patrick J.; The Journal of organic chemistry 80 (2015) 10163–10176; doi:10.1021/acs.joc.5b01766

data_4036374
_publ_section_title
;
 Synthesis of Ferrocene Oxazoline N,O ligands and Their Application in
 Asymmetric Ethyl- and Phenylzinc Additions to Aldehydes.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10163
_journal_page_last               10176
_journal_paper_doi               10.1021/acs.joc.5b01766
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C72 H88 Fe4 Li4 N4 O8, 0.5(C5 H12)'
_chemical_formula_sum            'C74.5 H94 Fe4 Li4 N4 O8'
_chemical_formula_weight         1424.69
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.2354(2)
_cell_length_b                   25.5309(3)
_cell_length_c                   16.9029(2)
_cell_measurement_reflns_used    26036
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.6010
_cell_measurement_theta_min      3.3950
_cell_volume                     7437.87(15)
_computing_cell_refinement
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_data_collection
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_data_reduction
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3196
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            63393
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         29.60
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2996
_exptl_crystal_size_max          0.3338
_exptl_crystal_size_mid          0.2650
_exptl_crystal_size_min          0.0960
_platon_squeeze_details
; 
 PLATON: A.L. Spek, J. Appl. Cryst. 36 (2003), 7-13 
 PLATON version from 27.07.2012 
;
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.005(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         9480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0320P)^2^+5.1851P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0730
_reflns_number_gt                8765
_reflns_number_total             9480
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo5b01766_si_001.cif
_cod_data_source_block           gui67sqz(18)
_cod_depositor_comments
;

2021-05-03
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C149 H188 Fe8 Li8 N8 O16'
_cod_original_formula_weight         2849.39
_cod_original_formula_moiety         '2 (C72 H88 Fe4 Li4 N4 O8), C5 H12'
_cod_original_formula_units_Z            2
_cod_database_code               4036374