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_7036686
_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 unk
_chemical_formula_moiety         'C12 H28 Co N5 O4, 2(Cl), 2(H2 O)'
_chemical_formula_sum            'C12 H32 Cl2 Co N5 O6'
_chemical_formula_weight         472.26
_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_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             2015-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.06 svn.r3119 for OlexSys, GUI svn.r4979)
;
_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                   9.6314(6)
_cell_length_b                   13.5664(6)
_cell_length_c                   14.7998(8)
_cell_measurement_reflns_used    7952
_cell_measurement_temperature    122.4
_cell_measurement_theta_max      29.435
_cell_measurement_theta_min      2.523
_cell_volume                     1933.79(18)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      122.4
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.9967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14308
_diffrn_reflns_theta_full        27.1011
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    1.203
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.6220
_exptl_crystal_description       prism
_exptl_crystal_F_000             994.9990
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.6303
_refine_diff_density_min         -0.3700
_refine_diff_density_rms         0.0745
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.010(13)
_refine_ls_d_res_high            0.7801
_refine_ls_d_res_low             10.0006
_refine_ls_goodness_of_fit_ref   1.0134
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4259
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.0129
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0269
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0207P)^2^+1.4765P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0617
_refine_ls_wR_factor_ref         0.0662
_reflns_Friedel_coverage         0.993
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              17
_reflns_limit_k_min              -17
_reflns_limit_l_max              18
_reflns_limit_l_min              -18
_reflns_number_gt                3991
_reflns_number_total             4259
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5dt02674a1.cif
_cod_data_source_block           mo_D8V958_0m-1
_cod_depositor_comments
'Adding full bibliography for 7036685--7036687.cif.'
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               7036686
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O5-H5c
 0.87 with sigma of 0.02
 O5-H5d
 0.87 with sigma of 0.02
 H3-O3
 0.84 with sigma of 0.02
 O4-H4
 0.84 with sigma of 0.02
3.a Free rotating group:
 O6(H6c,H6d)
3.b Ternary CH refined with riding coordinates:
 C9(H9)
3.c Secondary CH2 refined with riding coordinates:
 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)
;
_olex2_submission_special_instructions 'No special instructions were received'