Bromide-Mediatedortho-Deprotonation in the Synthesis of Chiral, Nonracemic Ferrocene Derivatives
Steurer, Marianne; Wang, Yaping; Mereiter, Kurt; Weissensteiner, Walter; Organometallics 26 (2007) 3850–; doi:10.1021/om7003282

data_4073442
_publ_section_title
;
 Bromide-Mediatedortho-Deprotonation in the Synthesis of Chiral,
 Nonracemic Ferrocene Derivatives
;
_journal_issue                   15
_journal_name_full               Organometallics
_journal_page_first              3850
_journal_paper_doi               10.1021/om7003282
_journal_volume                  26
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H21 Fe N O'
_chemical_formula_sum            'C15 H21 Fe N O'
_chemical_formula_weight         287.18
_chemical_name_common            'compound (R,S~p~)-8'
_chemical_name_systematic
; 
(R,S~p~)-3-[1-(N,N-Dimethylamino)ethyl]-1-hydroxymethyl-ferrocene
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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                   6.2478(4)
_cell_length_b                   10.4688(6)
_cell_length_c                   20.7139(12)
_cell_measurement_reflns_used    6415
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.96
_cell_measurement_theta_min      3.41
_cell_volume                     1354.83(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT, SADABS, XPREP'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0143
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17488
_diffrn_reflns_theta_full        29.98
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         3.41
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.101
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'program SADABS V2.10'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.007(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         3921
_refine_ls_number_restraints     115
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_gt           0.0202
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0309P)^2^+0.2060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0530
_refine_ls_wR_factor_ref         0.0533
_reflns_number_gt                3841
_reflns_number_total             3921
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om7003282-file003.cif
_cod_data_source_block           8-1085
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4073442