Dehydrogenative ester synthesis from enol ethers and water with a ruthenium complex catalyzing two reactions in synergy
Kar, Sayan; Luo, Jie; Rauch, Michael; Diskin-Posner, Yael; Ben-David, Yehoshoa; Milstein, David; Green Chemistry 24 (2022) 1481–1487; doi:10.1039/D1GC04574A

data_7244383
_publ_section_title
;
 Dehydrogenative ester synthesis from enol ethers and water with a
 ruthenium complex catalyzing two reactions in synergy
;
_journal_issue                   4
_journal_name_full               'Green Chemistry'
_journal_page_first              1481
_journal_page_last               1487
_journal_paper_doi               10.1039/D1GC04574A
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C40 H33 N O P2 Ru, C6 H6'
_chemical_formula_sum            'C46 H39 N O P2 Ru'
_chemical_formula_weight         784.79
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-04-25 deposited with the CCDC.	2022-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.1120(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7847(2)
_cell_length_b                   19.6339(3)
_cell_length_c                   14.6880(2)
_cell_measurement_reflns_used    54279
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      35.3290
_cell_measurement_theta_min      1.7340
_cell_volume                     3686.19(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_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    -26.00  53.00   0.25    2.00    --  -28.90  19.00  30.00  316
  2  \w     71.00 102.00   0.25    2.00    --   27.81  74.00  57.00  124
  3  \w     64.00  90.00   0.25    2.00    --   27.81 178.00 -30.00  104
  4  \w     65.00 110.00   0.25    2.00    --   27.81 178.00 -90.00  180
  5  \w     63.00 111.00   0.25    2.00    --   27.81 178.00  30.00  192
  6  \w      8.00  65.00   0.25    2.00    --   27.81  74.00  57.00  228
  7  \w    -22.00  53.00   0.25    2.00    --  -28.90  19.00  90.00  300
  8  \w     27.00  65.00   0.25    2.00    --   27.81 -74.00 -70.00  152
  9  \w     47.00  78.00   0.25    2.00    --   27.81 -99.00-150.00  124
 10  \w     60.00 108.00   0.25    2.00    --   27.81-178.00-180.00  192
 11  \w     70.00  98.00   0.25    2.00    --   27.81-178.00-150.00  112
 12  \w     -2.00  41.00   0.25    2.00    --   27.81 -99.00-150.00  172
 13  \w    -38.00 -12.00   0.25    2.00    --   27.81 -74.00 -70.00  104
 14  \w    -33.00   7.00   0.25    2.00    --  -28.90  74.00  57.00  160
 15  \w    -62.00 -10.00   0.25    2.00    --   27.81 -19.00 -30.00  208
 16  \w    -10.00  53.00   0.25    2.00    --  -28.90  19.00-150.00  252
 17  \w    -90.00 -34.00   0.25    2.00    --  -28.90 -74.00 -70.00  224
 18  \w   -109.00  13.00   0.25    2.00    --  -28.90 -77.00 -90.00  488
 19  \w     -2.00  80.00   0.25    2.00    --   27.81 -99.00 120.00  328
 20  \w    -61.00  40.00   0.25    2.00    --  -28.90  57.00 150.00  404
 21  \w   -110.00   2.00   0.25    2.00    --  -28.90 -57.00 -60.00  448
 22  \w   -110.00 -43.00   0.25    2.00    --  -28.90-178.00  60.00  268
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0209007000
_diffrn_orient_matrix_UB_12      0.0294717000
_diffrn_orient_matrix_UB_13      0.0208097000
_diffrn_orient_matrix_UB_21      -0.0464078000
_diffrn_orient_matrix_UB_22      -0.0034695000
_diffrn_orient_matrix_UB_23      -0.0268359000
_diffrn_orient_matrix_UB_31      -0.0221232000
_diffrn_orient_matrix_UB_32      -0.0206067000
_diffrn_orient_matrix_UB_33      0.0343344000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            143025
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.141
_diffrn_reflns_theta_min         1.732
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.550
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.644
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       prism
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.181
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     464
_refine_ls_number_reflns         14072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0327P)^2^+1.2984P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0775
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11853
_reflns_number_total             14072
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc04574a2.cif
_cod_data_source_block           m2275a
_cod_depositor_comments          'Adding full bibliography for 7244383.cif.'
_cod_database_code               7244383
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C40 H33 N Ru P2 O'
_chemical_oxdiff_usercomment     Sayan
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.07
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C1(H1A,H1B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C23(H23), C36(H36), C24(H24), C44(H44), C41(H41), C38(H38),
 C27(H27), C17(H17), C32(H32), C11(H11), C19(H19), C25(H25), C13(H13), C45(H45),
  C12(H12), C5(H5), C37(H37), C33(H33), C18(H18), C39(H39), C29(H29), C26(H26),
 C35(H35), C20(H20), C31(H31), C30(H30), C42(H42), C4(H4), C46(H46), C43(H43),
 C3(H3)
;
_shelx_res_checksum              39091
_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 1.177
_oxdiff_exptl_absorpt_empirical_full_min 0.852