Chain-length-dependent reactivity of alkenyl phosphates in ruthenium-catalyzed cross-metathesis
Pontavatchai, Apicha; Schwedtmann, Kevin; Royla, Philipp; Schwedtmann, Kai; Khamnaen, Tossapol; Schwarzenbolz, Uwe; Henle, Thomas; Somsook, Ekasith; Weigand, Jan J.; Chemical Communications  (2026) –; doi:10.1039/D5CC05790F

data_7135286
_publ_section_title
;
 Chain-length-dependent reactivity of alkenyl phosphates in
 ruthenium-catalyzed cross-metathesis
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D5CC05790F
_journal_year                    2026
_chemical_formula_moiety         'C40 H59 Cl2 N2 P Ru'
_chemical_formula_sum            'C40 H59 Cl2 N2 P Ru'
_chemical_formula_weight         770.83
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-18
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2025-10-07 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.8900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.21890(10)
_cell_length_b                   18.29290(10)
_cell_length_c                   17.88730(10)
_cell_measurement_reflns_used    29798
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.5380
_cell_measurement_theta_min      3.4980
_cell_volume                     3881.24(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.132a 64-bit (release 05-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5700
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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   -113.00 -15.00   0.50    1.00    --  -38.50 -32.00  -7.00  196
  2  \w    -37.00 -12.00   0.50    1.00    --  -38.50  32.00 151.00   50
  3  \w     -7.00  18.00   0.50    1.00    --   42.75 -32.00  -7.00   50
  4  \w     21.00 117.00   0.50    1.00    --   42.75  32.00 151.00  192
  5  \w    102.00 139.00   0.50    4.00    --  111.00  32.00 151.00   74
  6  \w     74.00 101.00   0.50    4.00    --  111.00 -32.00  -7.00   54
  7  \w    -61.00 -33.00   0.50    1.00    --  -38.50 125.00  90.00   56
  8  \w      7.00  34.00   0.50    1.00    --   42.75 -99.00-120.00   54
  9  \w    -30.00  63.00   0.50    1.00    --   42.75 -38.00-150.00  186
 10  \w    -23.00   6.00   0.50    1.00    --   42.75 -38.00 -30.00   58
 11  \w     32.00  62.00   0.50    1.00    --   42.75 -38.00 -30.00   60
 12  \w     37.00  90.00   0.50    1.00    --   42.75-125.00-180.00  106
 13  \w     32.00  96.00   0.50    1.00    --   42.75-125.00 -30.00  128
 14  \w    120.00 177.00   0.50    4.00    --  111.00  61.00   0.00  114
 15  \w     80.00 107.00   0.50    4.00    --  111.00 -94.00 -90.00   54
 16  \w     30.00 105.00   0.50    4.00    --  111.00 -94.00 -30.00  150
 17  \w     32.00  81.00   0.50    4.00    --  111.00 -15.00 -90.00   98
 18  \w     54.00 112.00   0.50    4.00    --  111.00-125.00-150.00  116
 19  \w    104.00 152.00   0.50    4.00    --  111.00  77.00  90.00   96
 20  \w     88.00 151.00   0.50    4.00    --  111.00  30.00-180.00  126
 21  \w     37.00  67.00   0.50    4.00    --  111.00 -94.00 -90.00   60
 22  \w     86.00 112.00   0.50    4.00    --  111.00-125.00  30.00   52
 23  \w     97.00 129.00   0.50    4.00    --  111.00 -77.00  60.00   64
 24  \w     53.00 135.00   0.50    4.00    --  111.00 -61.00  30.00  164
 25  \w     84.00 112.00   0.50    4.00    --  111.00 -61.00-150.00   56
 26  \w     47.00 107.00   0.50    4.00    --  111.00 -99.00  36.78  120
 27  \w     44.00  72.00   0.50    4.00    --  111.00-125.00 150.00   56
 28  \w     43.00  68.00   0.50    4.00    --  111.00 -61.00-150.00   50
 29  \w     81.00 107.00   0.50    4.00    --  111.00 -94.00  90.00   52
 30  \w    104.00 176.00   0.50    4.00    --  111.00  77.00  60.00  144
 31  \w    106.00 156.00   0.50    4.00    --  111.00 -15.00 -90.00  100
 32  \w     47.00  90.00   0.50    4.00    --  111.00 -61.00-180.00   86
 33  \w    109.00 134.00   0.50    4.00    --  111.00 -61.00-180.00   50
 34  \w     31.00 107.00   0.50    4.00    --  111.00 -94.00  60.00  152
 35  \w     78.00 107.00   0.50    4.00    --  111.00 -94.00-180.00   58
 36  \w     39.00  75.00   0.50    4.00    --  111.00 -94.00   0.00   72
 37  \w    140.00 178.00   0.50    4.00    --  111.00  77.00  30.00   76
 38  \w     79.00 104.00   0.50    4.00    --  111.00 -94.00-150.00   50
 39  \w     87.00 150.00   0.50    4.00    --  111.00  45.00  30.00  126
 40  \w     76.00 112.00   0.50    4.00    --  111.00-125.00 -60.00   72
 41  \w    121.00 154.00   0.50    4.00    --  111.00  77.00-120.00   66
 42  \w     81.00 106.00   0.50    4.00    --  111.00 -94.00 150.00   50
 43  \w     30.00  64.00   0.50    4.00    --  111.00 -94.00-150.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0401436000
_diffrn_orient_matrix_UB_12      -0.0108615000
_diffrn_orient_matrix_UB_13      0.0745919000
_diffrn_orient_matrix_UB_21      0.1152393000
_diffrn_orient_matrix_UB_22      -0.0332970000
_diffrn_orient_matrix_UB_23      0.0393122000
_diffrn_orient_matrix_UB_31      0.0444954000
_diffrn_orient_matrix_UB_32      0.0765654000
_diffrn_orient_matrix_UB_33      0.0276399000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            46671
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.686
_diffrn_reflns_theta_min         3.509
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.137
_exptl_absorpt_correction_T_max  0.706
_exptl_absorpt_correction_T_min  0.404
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       plate
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         8128
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0255
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0412P)^2^+0.9359P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0675
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7729
_reflns_number_total             8128
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05790f3.cif
_cod_data_source_block           jjw1807
_cod_database_code               7135286
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C40H59Cl2N2PRu
_shelx_estimated_absorpt_t_max   0.684
_shelx_estimated_absorpt_t_min   0.360
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C23(H23), C29(H29), C35(H35)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B),
 C27(H27A,H27B), C28(H28A,H28B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B),
  C33(H33A,H33B), C34(H34A,H34B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,
 H38B), C39(H39A,H39B), C40(H40A,H40B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C16(H16), C18(H18)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              77361
_shelx_hkl_checksum              58941
_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 2.787
_oxdiff_exptl_absorpt_empirical_full_min 0.431