Cobalt-catalyzed acceptorless dehydrogenative coupling of aminoalcohols with alcohols: direct access to pyrrole, pyridine and pyrazine derivatives.
Midya, Siba P.; Landge, Vinod G.; Sahoo, Manoj K.; Rana, Jagannath; Balaraman, Ekambaram; Chemical communications (Cambridge, England) 54 (2017) 90–93; doi:10.1039/c7cc07427a

data_7120920
_publ_section_title
;
 Cobalt-catalyzed acceptorless dehydrogenative coupling of aminoalcohols
 with alcohols: direct access to pyrrole, pyridine and pyrazine
 derivatives.
;
_journal_issue                   1
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              90
_journal_page_last               93
_journal_paper_doi               10.1039/c7cc07427a
_journal_volume                  54
_journal_year                    2017
_chemical_formula_moiety
'C16 H33 Cl4 Co2 N2 S4, 2(C16 H35.50 Cl4 Co2 N2 S4)'
_chemical_formula_sum            'C48 H104 Cl12 Co6 N6 S12'
_chemical_formula_weight         1929.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1p6x2w
_audit_creation_date             2017-06-16
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled Nov  7 2012 10:34:12, GUI svn.r4372)
;
_audit_update_record
;
2017-06-21 deposited with the CCDC.
2017-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.276(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   29.8732(14)
_cell_length_b                   7.1198(4)
_cell_length_c                   20.6123(11)
_cell_measurement_reflns_used    5857
_cell_measurement_temperature    149.97(15)
_cell_measurement_theta_max      28.8490
_cell_measurement_theta_min      3.4780
_cell_volume                     4162.9(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.97(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1640
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.8625
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -37.00  47.00   1.00   36.97    --   19.90 -37.00  60.00   84
  2  \w    -17.00   9.00   1.00   36.97    --   19.90 -99.00  60.00   26
  3  \w    -51.00  46.00   1.00   36.97    --   19.90 -37.00 -30.00   97
  4  \w    -17.00  23.00   1.00   36.97    --  -20.22  57.00-150.00   40
  5  \w    -41.00  -4.00   1.00   36.97    --  -20.22  57.00 -90.00   37
  6  \w    -37.00 -10.00   1.00   36.97    --  -20.22 -77.00-120.00   27
  7  \w    -24.00  11.00   1.00   36.97    --  -20.22 -77.00 -90.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0245627000
_diffrn_orient_matrix_UB_12      0.0182097000
_diffrn_orient_matrix_UB_13      -0.0126127000
_diffrn_orient_matrix_UB_21      0.0013386000
_diffrn_orient_matrix_UB_22      0.0058431000
_diffrn_orient_matrix_UB_23      -0.0336808000
_diffrn_orient_matrix_UB_31      -0.0044664000
_diffrn_orient_matrix_UB_32      -0.0978318000
_diffrn_orient_matrix_UB_33      -0.0043347000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            25358
_diffrn_reflns_theta_full        29.34
_diffrn_reflns_theta_max         29.34
_diffrn_reflns_theta_min         2.95
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.889
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       niddle
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         4.001
_refine_diff_density_min         -1.134
_refine_diff_density_rms         0.212
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         9858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.1044
_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^)+(0.0807P)^2^+78.6075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2496
_refine_ls_wR_factor_ref         0.2632
_reflns_number_gt                7627
_reflns_number_total             9858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc07427a2.cif
_cod_data_source_block           SNS-CoCl2-Dimer
_cod_depositor_comments          'Adding full bibliography for 7120920.cif.'
_cod_database_code               7120920
_chemical_oxdiff_formula         'C10 N10 S10 Cl10 H10 CO1'
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H2A,H2B} of C16B, H6 of N3, {H12A,H12B} of C18, {H11A,H11B} of C22, {H10A,
  H10B} of C19, H8 of N2, H7 of N1, {H13A,H13B} of C20, {H15A,H15B} of C10,
  {H16A,H16B} of C6, {H18A,H18B} of C21, {H17A,H17B} of C5, {H14A,H14B} of C24A,
   H7A of C24B, H4 of C16A, {H31A,H31B} of C2, {H19A,H19B} of C11, {H21A,H21B}
  of C14, {H20A,H20B} of C12, {H27A,H27B} of C4, {H25A,H25B} of C13, {H22A,
  H22B} of C3, H71 of C15, {H35A,H35B} of C7, H32 of C23
 At 1.5 times of:
  {H3A,H3B,H3C} of C1, {H30A,H30B,H30C} of C8, {H1A,H1B,H1C} of C17, {H53A,
  H53B,H53C} of C9
2. Others
 Fixed Sof: C16B(0.5) H2A(0.5) H2B(0.5) C24A(0.5) H14A(0.5) H14B(0.5)
 C24B(0.5) H7A(0.5) C16A(0.5) H4(0.5)
3.a Ternary CH refined with riding coordinates:
 N3(H6), N1(H7), N2(H8), C23(H32), C15(H71)
3.b Secondary CH2 refined with riding coordinates:
 C19(H10A,H10B), C22(H11A,H11B), C18(H12A,H12B), C20(H13A,H13B), C10(H15A,
 H15B), C6(H16A,H16B), C5(H17A,H17B), C21(H18A,H18B), C11(H19A,H19B), C12(H20A,
 H20B), C14(H21A,H21B), C3(H22A,H22B), C13(H25A,H25B), C4(H27A,H27B), C2(H31A,
 H31B), C7(H35A,H35B), C16B(H2A,H2B), C24A(H14A,H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C24B(H7A), C16A(H4)
3.d Idealised Me refined as rotating group:
 C8(H30A,H30B,H30C), C9(H53A,H53B,H53C), C17(H1A,H1B,H1C), C1(H3A,H3B,H3C)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.338
_oxdiff_exptl_absorpt_empirical_full_min 0.597