Primary Amides to Amines or Nitriles: Dual Role by a Single Catalyst
Mandal, Swadhin K.; Das, Hari Sankar; Das, Shyamal; Dey, Kartick; Singh, Bhagat; Koottanil Haridasan, Rahul; Das, Arpan; Ahmed, Jasimuddin; Chemical Communications  (2019) –; doi:10.1039/C9CC05856G

data_7124112
_publ_section_title
;
 Primary Amides to Amines or Nitriles: Dual Role by a Single Catalyst
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05856G
_journal_year                    2019
_chemical_formula_moiety         'C31 H25 Mn N3 O3, Cl O4'
_chemical_formula_sum            'C31 H25 Cl Mn N3 O7'
_chemical_formula_weight         641.93
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-09 deposited with the CCDC.    2019-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.719(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1071(11)
_cell_length_b                   15.4146(7)
_cell_length_c                   14.1647(10)
_cell_measurement_reflns_used    5787
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      24.9960
_cell_measurement_theta_min      2.8020
_cell_volume                     2701.3(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
  1 omega -113.00   19.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.7617  -77.0000   30.0000 132

  2 omega  -60.00   72.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1679  -77.0000  120.0000 132

  3 omega  -11.00   57.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1679   57.0000 -150.0000 68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0285886000
_diffrn_orient_matrix_UB_12      0.0040281000
_diffrn_orient_matrix_UB_13      0.0294565000
_diffrn_orient_matrix_UB_21      -0.0488109000
_diffrn_orient_matrix_UB_22      0.0063178000
_diffrn_orient_matrix_UB_23      -0.0487256000
_diffrn_orient_matrix_UB_31      -0.0092549000
_diffrn_orient_matrix_UB_32      -0.0454404000
_diffrn_orient_matrix_UB_33      -0.0041585000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10772
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.643
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear blackish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       block
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.198
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         4707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0718P)^2^+2.9806P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1280
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4284
_reflns_number_total             4707
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05856g2.cif
_cod_data_source_block           mn_ag
_cod_database_code               7124112
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O Mn Ag Cl'
_reflns_odcompleteness_completeness 91.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C29(H29A,H29B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C25(H25)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              94213
_olex2_date_sample_data_collection 2018-06-09
_olex2_submission_special_instructions 'No special instructions were received'