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_7036685
_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_formula_moiety         '2(I), C10 H26 Co N5 O4, H2 O'
_chemical_formula_sum            'C10 H28 Co I2 N5 O5'
_chemical_formula_weight         611.10
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-01-22
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_audit_update_record
;
2015-09-04 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.732(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.619(3)
_cell_length_b                   9.0014(10)
_cell_length_c                   22.283(3)
_cell_measurement_reflns_used    9405
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.148
_cell_measurement_theta_min      2.487
_cell_volume                     3838.2(9)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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      298
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            35223
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.148
_diffrn_reflns_theta_min         2.487
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.140
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0826 before and 0.0551 after correction.
The Ratio of minimum to maximum transmission is 0.7090.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.115
_exptl_crystal_description       rod
_exptl_crystal_F_000             2368
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.310
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         6799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0550
_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^)+(0.0372P)^2^+58.8173P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1443
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5152
_reflns_number_total             6799
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {afcb7822-4d7c-43fb-b39e-7ae7f02b3f51}
_cod_data_source_file            c5dt02674a1.cif
_cod_data_source_block           mo_scan_0m_p21_n
_cod_depositor_comments
'Adding full bibliography for 7036685--7036687.cif.'
_cod_original_cell_volume        3838.1(8)
_cod_database_code               7036685
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.733
_shelx_estimated_absorpt_t_min   0.491
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1S(H1SA,H1SB), O2S(H2SA,H2SB)
2.b Ternary CH refined with riding coordinates:
 C9(H9), C109(H109)
2.c Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B), N5(H5A,H5B), N102(H10D,H10E),
 N103(H10F,H10G), N104(H10H,H10I), N105(H10J,H10K), C1(H1A,H1B), C2(H2C,H2D),
 C3(H3C,H3D), C4(H4C,H4D), C5(H5C,H5D), C6(H6A,H6B), C102(H10L,H10M), C101(H10N,
 H10O), C103(H10P,H10Q), C104(H10R,H10S), C105(H10T,H10U), C106(H10V,H10W)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C110(H11A,H11B,H11C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O104(H104), O103(H103)
;
_shelx_res_checksum              69434
_olex2_submission_special_instructions 'No special instructions were received'