Aza-Claisen rearrangement as a key step in synthesis of specialised anilines used in the production of efficient ethenolysis catalysts
Sytniczuk, Adrian; Struzik, Filip; Purohit, Vishal; Grela, Karol; Kajetanowicz, Anna; Catalysis Science & Technology 13 (2023) 3682–3688; doi:10.1039/D3CY00395G

data_1569260
_publ_section_title
;
 Aza-Claisen rearrangement as a key step in synthesis of specialised
 anilines used in the production of efficient ethenolysis catalysts
;
_journal_issue                   12
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              3682
_journal_page_last               3688
_journal_paper_doi               10.1039/D3CY00395G
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C35 H45 Cl2 N O Ru, C H Cl3'
_chemical_formula_sum            'C36 H46 Cl5 N O Ru'
_chemical_formula_weight         787.06
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-05-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-14 deposited with the CCDC.	2023-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.265(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7816(3)
_cell_length_b                   16.0450(5)
_cell_length_c                   21.2485(7)
_cell_measurement_reflns_used    26103
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.7380
_cell_measurement_theta_min      2.4920
_cell_volume                     3617.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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    -39.00  41.00   1.00    5.00    --   10.32 -77.00 120.00   80
  2  \w    -42.00  43.00   1.00    5.00    --   10.32 -77.00-120.00   85
  3  \w    -14.00  85.00   1.00    5.00    --   10.32  38.00-180.00   99
  4  \w    -12.00  85.00   1.00    5.00    --   10.32  38.00  60.00   97
  5  \w    -53.00  33.00   1.00    5.00    --   10.32 -38.00   0.00   86
  6  \w    -18.00  71.00   1.00    5.00    --   10.32  57.00 -60.00   89
  7  \w    -86.00 -61.00   1.00    5.00    --  -11.10 153.00 -48.05   25
  8  \w    -78.00 -36.00   1.00    5.00    --  -11.10 142.00  62.47   42
  9  \w    -87.00 -43.00   1.00    5.00    --  -11.10 154.00-170.48   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0188399000
_diffrn_orient_matrix_UB_12      0.0206139000
_diffrn_orient_matrix_UB_13      -0.0263149000
_diffrn_orient_matrix_UB_21      0.0064790000
_diffrn_orient_matrix_UB_22      -0.0390266000
_diffrn_orient_matrix_UB_23      -0.0146999000
_diffrn_orient_matrix_UB_31      -0.0638273000
_diffrn_orient_matrix_UB_32      0.0021062000
_diffrn_orient_matrix_UB_33      -0.0155923000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            60338
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.301
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       plate
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.025
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         7380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0300
_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^)+(0.0278P)^2^+4.7727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0736
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6453
_reflns_number_total             7380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cy00395g2.cif
_cod_data_source_block           2021_03_15_dt_as_1560_k
_cod_depositor_comments          'Adding full bibliography for 1569260.cif.'
_cod_original_cell_volume        3616.9(2)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1569260
_shelx_shelxl_version_number     2016/4
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C33(H33), C36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C11(H11A,H11B), C3(H3A,H3B), C15(H15A,H15B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C32(H32), C9(H9), C7(H7), C25(H25), C21(H21), C29(H29), C31(H31),
 C8(H8), C24(H24), C30(H30), C23(H23), C22(H22)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C34(H34A,H34B,
 H34C), C35(H35A,H35B,H35C), C16(H16A,H16B,H16C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              75108
_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 1.280
_oxdiff_exptl_absorpt_empirical_full_min 0.636