A tunable family of CAAC-ruthenium olefin metathesis catalysts modularly derived from a large-scale produced ibuprofen intermediate.
Sytniczuk, Adrian; Struzik, Filip; Grela, Karol; Kajetanowicz, Anna; Chemical science 14 (2023) 10744–10755; doi:10.1039/d3sc03849a

data_1569922
_publ_section_title
;
 A tunable family of CAAC-ruthenium olefin metathesis catalysts modularly
 derived from a large-scale produced ibuprofen intermediate.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              10744
_journal_page_last               10755
_journal_paper_doi               10.1039/d3sc03849a
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C37 H49 Cl2 N O Ru'
_chemical_formula_sum            'C37 H49 Cl2 N O Ru'
_chemical_formula_weight         695.74
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-26
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-07-26 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.9295(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.97514(11)
_cell_length_b                   11.89935(9)
_cell_length_c                   19.33172(15)
_cell_measurement_reflns_used    19989
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.0220
_cell_measurement_theta_min      3.4570
_cell_volume                     3403.05(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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      8.00  33.00   0.50    0.05    --    0.00-101.00 128.00   50
  2  \w    -41.00 -16.00   0.50    0.05    --    0.00 101.00-127.00   50
  3  \w     43.00  79.00   0.50    0.05    --    0.00  77.00  60.00   72
  4  \w     18.00  79.00   0.50    0.05    --    0.00  57.00-180.00  122
  5  \w    -38.00  11.00   0.50    0.05    --    0.00  77.00  60.00   98
  6  \w    -30.00   9.00   0.50    0.05    --    0.00  57.00-180.00   78
  7  \w    -48.00 -22.00   0.50    0.05    --  -54.00 101.00-127.00   52
  8  \w   -140.00 -85.00   0.50    0.05    --  -54.00-101.00 128.00  110
  9  \w    -86.00 -47.00   0.50    0.05    --  -54.00 125.00 -90.00   78
 10  \w   -135.00 -91.00   0.50    0.05    --  -54.00 -99.00  30.00   88
 11  \w   -129.00 -79.00   0.50    0.05    --  -54.00-125.00-180.00  100
 12  \w   -131.00 -87.00   0.50    0.05    --  -54.00 -99.00 -90.00   88
 13  \w   -137.00 -96.00   0.50    0.05    --  -54.00 -99.00 -30.00   82
 14  \w   -133.00 -21.00   0.50    0.05    --  -54.00 -57.00 -30.00  224
 15  \w   -139.00 -93.00   0.50    0.05    --  -54.00 -99.00  60.00   92
 16  \w   -140.00 -86.00   0.50    0.05    --  -54.00 -99.00-120.00  108
 17  \w    -77.00 -26.00   0.50    0.05    --  -54.00 125.00 -30.00  102
 18  \w     25.00 103.00   0.50    0.05    --   55.77-101.00 128.00  156
 19  \w     35.00  97.00   0.50    0.05    --   55.77-125.00 120.00  124
 20  \w     26.00 135.00   0.50    0.05    --   55.77  57.00 -90.00  218
 21  \w    107.00 178.00   0.50    0.20    --  111.55 101.00-127.00  142
 22  \w     72.00 107.00   0.50    0.20    --  111.55-101.00 128.00   70
 23  \w     72.00 133.00   0.50    0.20    --  111.55  45.00  30.00  122
 24  \w    120.00 155.00   0.50    0.20    --  111.55  61.00  90.00   70
 25  \w     81.00 117.00   0.50    0.20    --  111.55  61.00  60.00   72
 26  \w     29.00 103.00   0.50    0.20    --  111.55-111.00-120.00  148
 27  \w     30.00 103.00   0.50    0.20    --  111.55-111.00   0.00  146
 28  \w     43.00 146.00   0.50    0.20    --  111.55 -61.00  90.00  206
 29  \w     91.00 117.00   0.50    0.20    --  111.55 -61.00 -90.00   52
 30  \w     78.00 178.00   0.50    0.20    --  111.55  61.00 -90.00  200
 31  \w    109.00 165.00   0.50    0.20    --  111.55 111.00 -60.00  112
 32  \w     39.00 105.00   0.50    0.20    --  111.55-111.00  90.00  132
 33  \w     99.00 127.00   0.50    0.20    --  111.55 178.00  30.00   56
 34  \w     63.00 141.00   0.50    0.20    --  111.55 178.00 150.00  156
 35  \w    123.00 148.00   0.50    0.20    --  111.55 111.00 -30.00   50
 36  \w     27.00  84.00   0.50    0.20    --  111.55 -94.00 150.00  114
 37  \w     86.00 111.00   0.50    0.20    --  111.55  61.00 150.00   50
 38  \w    118.00 176.00   0.50    0.20    --  111.55  61.00 150.00  116
 39  \w    138.00 169.00   0.50    0.20    --  111.55  45.00  30.00   62
 40  \w    123.00 175.00   0.50    0.20    --  111.55  61.00  60.00  104
 41  \w     44.00 108.00   0.50    0.20    --  111.55-111.00 -90.00  128
 42  \w     34.00  59.00   0.50    0.20    --  111.55 -61.00 -90.00   50
 43  \w     70.00 141.00   0.50    0.20    --  111.55  77.00-180.00  142
 44  \w    146.00 171.00   0.50    0.20    --  111.55 111.00   0.00   50
 45  \w     72.00 178.00   0.50    0.20    --  111.55  45.00 -30.00  212
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0307406000
_diffrn_orient_matrix_UB_12      -0.1234746000
_diffrn_orient_matrix_UB_13      -0.0009545000
_diffrn_orient_matrix_UB_21      0.0189436000
_diffrn_orient_matrix_UB_22      -0.0004217000
_diffrn_orient_matrix_UB_23      0.0806673000
_diffrn_orient_matrix_UB_31      -0.0976327000
_diffrn_orient_matrix_UB_32      -0.0389431000
_diffrn_orient_matrix_UB_33      0.0019933000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            33773
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         4.378
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.385
_exptl_absorpt_correction_T_max  0.491
_exptl_absorpt_correction_T_min  0.242
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
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            'dark brown'
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.417
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.177
_refine_diff_density_max         0.986
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         6071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0366P)^2^+4.2219P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0770
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5857
_reflns_number_total             6071
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03849a2.cif
_cod_data_source_block           2023_05_19_dt_as_1665_n_auto
_cod_depositor_comments          'Adding full bibliography for 1569922.cif.'
_cod_database_code               1569922
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C37 H49 Cl2 N O Ru'
_chemical_oxdiff_usercomment     '100 k, BRONZE BLOCK'
_shelx_estimated_absorpt_t_max   0.449
_shelx_estimated_absorpt_t_min   0.212
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C12(H12), C35(H35)
1.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C11(H11A,H11B), C24(H24A,H24B), C26(H26A,H26B)
1.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C20(H20), C21(H21), C22(H22), C28(H28),
 C30(H30), C31(H31), C32(H32), C33(H33)
1.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C36(H36A,
 H36B,H36C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              16731
_shelx_hkl_checksum              22654
_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 1.409
_oxdiff_exptl_absorpt_empirical_full_min 0.674