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_7124113
_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         'C28 H18 Cl Mn N2 O2'
_chemical_formula_sum            'C28 H18 Cl Mn N2 O2'
_chemical_formula_weight         504.83
_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                 104.276(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0980(10)
_cell_length_b                   11.6602(7)
_cell_length_c                   18.3347(11)
_cell_measurement_reflns_used    2638
_cell_measurement_temperature    103(5)
_cell_measurement_theta_max      24.9730
_cell_measurement_theta_min      2.0800
_cell_volume                     2092.1(3)
_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      103(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega  -94.00  -58.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.7617  178.0000 -180.0000 36

  2 omega   -9.00   70.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1679  -99.0000  120.0000 79

  3 omega  -23.00   81.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1679   19.0000  -90.0000 104
;
_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      0.0247880000
_diffrn_orient_matrix_UB_12      0.0563420000
_diffrn_orient_matrix_UB_13      -0.0027507000
_diffrn_orient_matrix_UB_21      0.0648579000
_diffrn_orient_matrix_UB_22      -0.0225101000
_diffrn_orient_matrix_UB_23      -0.0006651000
_diffrn_orient_matrix_UB_31      -0.0207332000
_diffrn_orient_matrix_UB_32      -0.0034274000
_diffrn_orient_matrix_UB_33      -0.0398725000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_unetI/netI     0.0881
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5615
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.114
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10672
_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            'metallic dark brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.297
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0632
_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^)+(0.0917P)^2^+0.2591P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1575
_refine_ls_wR_factor_ref         0.1740
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2781
_reflns_number_total             3647
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05856g2.cif
_cod_data_source_block           mn_otbu
_cod_database_code               7124113
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O Mn'
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.858
_reflns_odcompleteness_completeness 91.38
_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
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C17(H17),
 C18(H18), C20(H20), C21(H21), C22(H22), C27(H27), C29(H29)
;
_shelx_res_checksum              80284
_olex2_date_sample_data_collection 2018-06-26
_olex2_submission_special_instructions 'No special instructions were received'