Ruthenium(ii)-catalysed direct synthesis of ketazines using secondary alcohols
Kishore, Jugal; Thiyagarajan, Subramanian; Gunanathan, Chidambaram; Chemical Communications  (2019) –; doi:10.1039/C9CC01383K

data_7123235
_publ_section_title
;
 Ruthenium(ii)-catalysed direct synthesis of ketazines using secondary
 alcohols
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01383K
_journal_year                    2019
_chemical_formula_moiety         '2(C24 H20 N2)'
_chemical_formula_sum            'C48 H40 N4'
_chemical_formula_weight         672.84
_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
_audit_creation_date             2019-03-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-03-20 deposited with the CCDC.    2019-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.656(3)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   18.8305(5)
_cell_length_b                   5.31570(13)
_cell_length_c                   9.2092(2)
_cell_measurement_reflns_used    5505
_cell_measurement_temperature    298.21(10)
_cell_measurement_theta_max      76.1770
_cell_measurement_theta_min      4.8600
_cell_volume                     905.92(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_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      air
_diffrn_ambient_temperature      298.21(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_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    -61.00 -12.00   0.50    1.15    --    0.00 143.00  33.00   98
  2  \w    -51.00  -4.00   0.50    1.15    --    0.00 127.00-136.00   94
  3  \w     39.00 119.00   0.50    4.62    --  102.08-127.00 148.00  160
  4  \w     41.00 131.00   0.50    4.62    --  102.08-143.00 -21.00  180
  5  \w     84.00 163.00   0.50    4.62    --  102.08 143.00  33.00  158
  6  \w     93.00 165.00   0.50    4.62    --  102.08 127.00-136.00  144
  7  \w     -1.00  65.00   0.50    1.15    --    0.00  37.00 -90.00  132
  8  \w     -1.00  65.00   0.50    1.15    --    0.00  37.00-150.00  132
  9  \w     36.00 103.00   0.50    4.62    --  102.08 -30.00  60.00  134
 10  \w    100.00 170.00   0.50    4.62    --  102.08  15.00-120.00  140
 11  \w     94.00 166.00   0.50    4.62    --  102.08 125.00   0.00  144
 12  \w     40.00 114.00   0.50    4.62    --  102.08 -61.00  30.00  148
 13  \w     91.00 164.00   0.50    4.62    --  102.08  61.00 150.00  146
 14  \w     40.00 114.00   0.50    4.62    --  102.08 -61.00 -30.00  148
 15  \w    100.00 165.00   0.50    4.62    --  102.08  45.00  30.00  130
 16  \w     94.00 166.00   0.50    4.62    --  102.08 125.00 -90.00  144
 17  \w    100.00 165.00   0.50    4.62    --  102.08  45.00 150.00  130
 18  \w     -1.00  47.00   0.50    1.15    --    0.00  37.00 -30.00   96
 19  \w     -1.00  67.00   0.50    1.15    --    0.00  19.00 150.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0825508000
_diffrn_orient_matrix_UB_12      0.0187003000
_diffrn_orient_matrix_UB_13      -0.0496540000
_diffrn_orient_matrix_UB_21      -0.0093611000
_diffrn_orient_matrix_UB_22      -0.2440768000
_diffrn_orient_matrix_UB_23      0.0847284000
_diffrn_orient_matrix_UB_31      -0.0049191000
_diffrn_orient_matrix_UB_32      0.1551491000
_diffrn_orient_matrix_UB_33      0.1390903000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6917
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.402
_diffrn_reflns_theta_min         4.779
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.556
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.108
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0760P)^2^+0.0750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1481
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1652
_reflns_number_total             1849
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01383k2.cif
_cod_data_source_block           cg_jk_170f
_cod_database_code               7123235
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C24H20N2
_diffrn_oxdiff_ac3_digest_frames
;
01924910355360586530ce25c95f3d67760003171aa
;
_diffrn_oxdiff_ac3_digest_hkl
;
0132bc2fb5f7dfb3f88f1afa33dc9d85791872
;
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C007(H007), C008(H008), C009(H009), C00A(H00A), C00C(H00E),
 C00D(H00F)
2.b Idealised Me refined as rotating group:
 C00B(H00B,H00C,H00D)
;
_shelx_res_checksum              48974
_shelx_hkl_checksum              15006
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.518
_oxdiff_exptl_absorpt_empirical_full_min 0.356