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

data_7123233
_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         'C16 H16 N2'
_chemical_formula_sum            'C16 H16 N2'
_chemical_formula_weight         236.31
_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     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                 97.7197(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6991(2)
_cell_length_b                   7.55240(18)
_cell_length_c                   14.8701(3)
_cell_measurement_reflns_used    7375
_cell_measurement_temperature    294.5(3)
_cell_measurement_theta_max      76.2210
_cell_measurement_theta_min      4.4940
_cell_volume                     1301.96(5)
_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      294.5(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.972
_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    -68.00   1.00   0.50    1.00    --    0.00 -23.00 150.00  138
  2  \w     -1.00  68.00   0.50    1.00    --    0.00  23.00 -44.00  138
  3  \w    101.00 170.00   0.50    4.00    --  102.08  23.00 -44.00  138
  4  \w     34.00 104.00   0.50    4.00    --  102.08 -23.00 150.00  140
  5  \w    -10.00  61.00   0.50    1.00    --    0.00  57.00  60.00  142
  6  \w     -1.00  65.00   0.50    1.00    --    0.00  37.00-180.00  132
  7  \w     39.00 105.00   0.50    4.00    --  102.08 -45.00-150.00  132
  8  \w    100.00 165.00   0.50    4.00    --  102.08  45.00-180.00  130
  9  \w     39.00 105.00   0.50    4.00    --  102.08 -45.00  60.00  132
 10  \w     39.00 105.00   0.50    4.00    --  102.08 -45.00-120.00  132
 11  \w     39.00 105.00   0.50    4.00    --  102.08 -45.00 -60.00  132
 12  \w     39.00 118.00   0.50    4.00    --  102.08-125.00  30.00  158
 13  \w    101.00 169.00   0.50    4.00    --  102.08  30.00  90.00  136
 14  \w    100.00 165.00   0.50    4.00    --  102.08  45.00   0.00  130
 15  \w     39.00 105.00   0.50    4.00    --  102.08 -45.00   0.00  132
 16  \w     39.00 118.00   0.50    4.00    --  102.08-125.00-150.00  158
 17  \w    -10.00  61.00   0.50    1.00    --    0.00  57.00   0.00  142
 18  \w    -22.00  62.00   0.50    1.00    --    0.00  77.00  90.00  168
 19  \w    -22.00  62.00   0.50    1.00    --    0.00  77.00-120.00  168
 20  \w    101.00 126.00   0.50    4.00    --  102.08  30.00-120.00   50
;
_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      -0.0997752000
_diffrn_orient_matrix_UB_12      0.0291508000
_diffrn_orient_matrix_UB_13      0.0562530000
_diffrn_orient_matrix_UB_21      0.0875212000
_diffrn_orient_matrix_UB_22      0.0477605000
_diffrn_orient_matrix_UB_23      0.0833792000
_diffrn_orient_matrix_UB_31      -0.0064906000
_diffrn_orient_matrix_UB_32      0.1961363000
_diffrn_orient_matrix_UB_33      -0.0286030000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9610
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.452
_diffrn_reflns_theta_min         4.525
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.551
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77490
_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 yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0267(18)
_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   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0733P)^2^+0.1593P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1293
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2434
_reflns_number_total             2656
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01383k2.cif
_cod_data_source_block           cg_jk_aceto_azine
_cod_depositor_comments
;

2025-03-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '4(C16 H16 N2)'
_cod_original_formula_sum        'C64 H64 N8'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     945.23
_cod_database_code               7123233
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C64 H64 N8 '
_diffrn_oxdiff_ac3_digest_frames
;
01b654acec4f894e63cb5bbcc4f236798e00035f68f
;
_diffrn_oxdiff_ac3_digest_hkl
;
01a6605530738b7b8c06134a40d28a2e754336
;
_reflns_odcompleteness_completeness 99.76
_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:
 C007(H007), C008(H008), C009(H009), C00B(H00D), C00C(H00E), C00E(H00I),
 C00F(H00J), C00G(H00K), C00H(H00L), C00I(H00M)
2.b Idealised Me refined as rotating group:
 C00A(H00A,H00B,H00C), C00D(H00F,H00G,H00H)
;
_shelx_res_checksum              76332
_shelx_hkl_checksum              44339
_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 4.668
_oxdiff_exptl_absorpt_empirical_full_min 0.405