Stereoretentive formylation of (S)-proline: new application of the self-regeneration of stereo-centres (SRS) principle via chelation to cobalt(iii).
Temizsoy, Mehmet; Sethi, Waqas; Reinholdt, Anders; Schau-Magnussen, Magnus; Bendix, Jesper; Hammershøi, Anders; Dalton transactions (Cambridge, England : 2003) 44 (2015) 18438–18446; doi:10.1039/c5dt02674a

data_7036687
_publ_section_title
;
 Stereoretentive formylation of (S)-proline: new application of the
 self-regeneration of stereo-centres (SRS) principle via chelation to
 cobalt(iii).
;
_journal_issue                   42
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              18438
_journal_page_last               18446
_journal_paper_doi               10.1039/c5dt02674a
_journal_volume                  44
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H28 Co N5 O3, 2(Cl), 2(H2 O)'
_chemical_formula_sum            'C12 H32 Cl2 Co N5 O5'
_chemical_formula_weight         456.25
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-01-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-09-04 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9450(3)
_cell_length_b                   12.4236(4)
_cell_length_c                   17.4130(6)
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    122.4
_cell_measurement_theta_max      30.332
_cell_measurement_theta_min      2.560
_cell_volume                     1935.09(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      122.4
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30215
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         2.560
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.196
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0870 before and 0.0657 after correction.
The Ratio of minimum to maximum transmission is 0.9020.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear reddish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 1976 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.006(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         5425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0284P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0556
_refine_ls_wR_factor_ref         0.0585
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4854
_reflns_number_total             5425
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5dt02674a1.cif
_cod_data_source_block           mo_d8v990_0m-a
_cod_depositor_comments
'Adding full bibliography for 7036685--7036687.cif.'
_cod_database_code               7036687
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.787
_shelx_estimated_absorpt_t_min   0.381
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5C,H5D), O4(H4E,H4F)
2.b Ternary CH refined with riding coordinates:
 N5(H5)
2.c Secondary CH2 refined with riding coordinates:
 N4(H4A,H4B), N2(H2A,H2B), N3(H3A,H3B), C6(H6A,H6B), C5(H5A,H5B), C1(H1A,H1B),
 C2(H2C,H2D), C3(H3C,H3D), C4(H4C,H4D), C12(H12A,H12B), C11(H11A,H11B),
 C10(H10A,H10B), C9(H9A,H9B)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              78753
_olex2_submission_special_instructions 'No special instructions were received'