Ru(II)-catalyzed tunable cascade reaction via C-H/C-C bond cleavage.
Yang, Zi; Yue, Qi; Yang, Mengqi; Zhang, Hong; Cui, Xiuling; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01614

data_4038844
_publ_section_title
;
 Ru(II)-catalyzed tunable cascade reaction via C-H/C-C bond cleavage.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01614
_journal_year                    2020
_chemical_formula_moiety         'C21 H24 N2 O2'
_chemical_formula_sum            'C21 H24 N2 O2'
_chemical_formula_weight         336.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-08-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                113.729(9)
_cell_angle_beta                 92.491(6)
_cell_angle_gamma                101.392(7)
_cell_formula_units_Z            2
_cell_length_a                   8.7033(6)
_cell_length_b                   10.3399(10)
_cell_length_c                   11.7859(11)
_cell_measurement_reflns_used    2165
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7990
_cell_measurement_theta_min      4.2630
_cell_volume                     942.86(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.817
_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     -3.00  85.00   1.00    2.48    --   15.65  38.00  60.00   88
  2  \w     -6.00  22.00   1.00    2.48    --  -16.28 -99.00-120.00   28
  3  \w    -24.00  46.00   1.00    2.48    --   15.65 -99.00-120.00   70
  4  \w     -8.00  18.00   1.00    2.48    --  -16.28 -99.00   0.00   26
  5  \w    -56.00  37.00   1.00    2.48    --   15.65 -19.00-120.00   93
  6  \w    -67.00  -2.00   1.00    2.48    --  -16.28 -57.00  90.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0101066000
_diffrn_orient_matrix_UB_12      0.0720320000
_diffrn_orient_matrix_UB_13      0.0291857000
_diffrn_orient_matrix_UB_21      -0.0056868000
_diffrn_orient_matrix_UB_22      0.0032625000
_diffrn_orient_matrix_UB_23      -0.0589663000
_diffrn_orient_matrix_UB_31      -0.0831223000
_diffrn_orient_matrix_UB_32      -0.0272815000
_diffrn_orient_matrix_UB_33      -0.0086952000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.817
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7799
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.502
_diffrn_reflns_theta_min         3.515
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.062(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4303
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0487
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1426
_refine_ls_wR_factor_ref         0.1683
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3027
_reflns_number_total             4303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01614_si_002.cif
_cod_data_source_block           exp_5792
_cod_original_cell_volume        942.85(15)
_cod_database_code               4038844
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.989
_reflns_odcompleteness_completeness 99.71
_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, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2A
 0.8 with sigma of 0.02
 N2-H2B
 0.9 with sigma of 0.02
3.a Riding coordinates:
 O2(H2A,H2B)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_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 1.699
_oxdiff_exptl_absorpt_empirical_full_min 0.688