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_4036372
_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         'C31 H33 Fe N O2, 0.5(C5 H12)'
_chemical_formula_sum            'C33.5 H39 Fe N O2'
_chemical_formula_weight         543.50
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 97.2543(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.65882(8)
_cell_length_b                   10.60526(9)
_cell_length_c                   27.9871(2)
_cell_measurement_reflns_used    50693
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.2080
_cell_measurement_theta_min      3.3240
_cell_volume                     2843.89(4)
_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 0.996
_diffrn_measured_fraction_theta_max 0.954
_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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            99503
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         29.56
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.861
_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            'clear red'
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1156
_exptl_crystal_size_max          0.3587
_exptl_crystal_size_mid          0.3386
_exptl_crystal_size_min          0.2592
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     705
_refine_ls_number_reflns         14673
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0270
_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^)+(0.0294P)^2^+0.8342P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0646
_reflns_number_gt                13840
_reflns_number_total             14673
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo5b01766_si_001.cif
_cod_data_source_block           gui64(R~p~-6)
_cod_depositor_comments
;

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C67 H78 Fe2 N2 O4'
_cod_original_formula_weight         1087.01
_cod_original_formula_moiety         '2 (C31 H33 Fe N O2), C5 H12'
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4036372