Ru(II)-catalyzed P(III)-assisted C8-alkylation of naphthphosphines
Ma, Wen-Tao; Huang, Mao-Gui; Fuyue, Liuting; Wang, Zhong-Hui; Tao, Jun-Yang; Li, Jia-Wei; Liu, Yue-Jin; Zeng, Ming-Hua; Chemical Communications  (2022) –; doi:10.1039/D2CC02161G

data_7130155
_publ_section_title
;
 Ru(II)-catalyzed P(III)-assisted C8-alkylation of naphthphosphines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02161G
_journal_year                    2022
_chemical_formula_moiety         'C27 H25 O2 P'
_chemical_formula_sum            'C27 H25 O2 P'
_chemical_formula_weight         412.47
_chemical_name_systematic
'ethyl 3-(8-(diphenylphosphaneyl)naphthalen-1-yl)propanoate'
_chemical_properties_physical    Air-sensitive,Oxygen-sensitive
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-05
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-03-05 deposited with the CCDC.	2022-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                68.499(3)
_cell_angle_beta                 79.973(3)
_cell_angle_gamma                73.741(3)
_cell_formula_units_Z            2
_cell_length_a                   9.3822(3)
_cell_length_b                   10.1224(4)
_cell_length_c                   13.1212(4)
_cell_measurement_reflns_used    8550
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.3550
_cell_measurement_theta_min      3.6050
_cell_volume                     1109.47(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.953
_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     77.00 123.00   0.50    0.05    --  112.45 150.00-149.00   92
  2  \w    105.00 147.00   0.50    0.05    --  112.45 111.00 -90.00   84
  3  \w    150.00 177.00   0.50    0.05    --  112.45 111.00 -90.00   54
  4  \w    102.00 176.00   0.50    0.05    --  112.45 111.00 150.00  148
  5  \w    103.00 129.00   0.50    0.05    --  112.45 122.00  48.00   52
  6  \w    -49.00 -24.00   0.50    0.05    --    0.00 122.00  48.00   50
  7  \w    -75.00 -50.00   0.50    0.05    --  -37.97 122.00  48.00   50
  8  \w   -125.00 -36.00   0.50    0.05    --  -98.50 178.00-120.00  178
  9  \w    -87.00 -16.00   0.50    0.05    --  -98.50 111.00-180.00  142
 10  \w    -94.00 -68.00   0.50    0.05    --  -37.97 150.00-149.00   52
 11  \w    -74.00 -49.00   0.50    0.05    --    0.00 150.00-149.00   50
 12  \w    -55.00 -26.00   0.50    0.05    --  -98.50 150.00-149.00   58
 13  \w    -91.00 -59.00   0.50    0.05    --  -98.50 150.00-149.00   64
 14  \w    -87.00 -25.00   0.50    0.05    --  -98.50 111.00  30.00  124
 15  \w    -58.00 -19.00   0.50    0.05    --  -98.50 111.00 120.00   78
 16  \w   -177.00-129.00   0.50    0.05    --  -98.50 -45.00 -30.00   96
 17  \w     34.00 100.00   0.50    0.05    --  112.45-111.00   0.00  132
 18  \w     81.00 114.00   0.50    0.05    --  112.45-111.00 -90.00   66
 19  \w     32.00  74.00   0.50    0.05    --  112.45-111.00 -90.00   84
 20  \w     38.00  64.00   0.50    0.05    --  112.45 -94.00-150.00   52
 21  \w     81.00 106.00   0.50    0.05    --  112.45 -94.00-150.00   50
 22  \w     36.00  85.00   0.50    0.05    --  112.45-122.00 -32.00   98
 23  \w     94.00 119.00   0.50    0.05    --  112.45-122.00 -32.00   50
 24  \w     62.00 105.00   0.50    0.05    --  112.45 -94.00  90.00   86
 25  \w     83.00 130.00   0.50    0.05    --  112.45-150.00 165.00   94
 26  \w     40.00  65.00   0.50    0.05    --   37.97-122.00 -32.00   50
 27  \w     76.00 105.00   0.50    0.05    --   37.97-150.00 165.00   58
 28  \w     49.00  84.00   0.50    0.05    --   37.97 -99.00-180.00   70
 29  \w     -4.00  44.00   0.50    0.05    --   37.97 -99.00-180.00   96
 30  \w   -170.00 -80.00   0.50    0.05    --  -98.50 -94.00 -90.00  180
 31  \w   -148.00-123.00   0.50    0.05    --  -98.50-122.00 -32.00   50
 32  \w   -119.00 -75.00   0.50    0.05    --  -37.97-122.00 -32.00   88
 33  \w   -107.00 -58.00   0.50    0.05    --  -37.97-150.00 165.00   98
 34  \w   -128.00-103.00   0.50    0.05    --  -98.50-150.00 165.00   50
 35  \w   -165.00-124.00   0.50    0.05    --  -98.50 -61.00  30.00   82
 36  \w    -87.00  -8.00   0.50    0.05    --  -37.97 -57.00-180.00  158
 37  \w      9.00 111.00   0.50    0.05    --   37.97  57.00  90.00  204
 38  \w    119.00 178.00   0.50    0.05    --  112.45  61.00 -30.00  118
 39  \w     36.00  67.00   0.50    0.05    --  112.45 -77.00 120.00   62
 40  \w   -113.00 -12.00   0.50    0.05    --  -37.97 -77.00 -30.00  202
 41  \w   -173.00 -55.00   0.50    0.05    --  -98.50 -30.00 -90.00  236
 42  \w    -98.00 -68.00   0.50    0.05    --  -98.50 -45.00 -30.00   60
 43  \w   -109.00 -66.00   0.50    0.05    --  -98.50 -61.00  30.00   86
 44  \w     80.00 134.00   0.50    0.05    --  112.45 -77.00 120.00  108
 45  \w    -58.00 -32.00   0.50    0.05    --  -98.50 122.00  48.00   52
 46  \w    141.00 167.00   0.50    0.05    --  112.45  61.00 -60.00   52
 47  \w    110.00 136.00   0.50    0.05    --  112.45  61.00 -60.00   52
 48  \w    112.00 137.00   0.50    0.05    --  112.45 122.00  48.00   50
 49  \w   -119.00 -94.00   0.50    0.05    --  -37.97-122.00 -32.00   50
 50  \w   -104.00 -79.00   0.50    0.05    --  -98.50-150.00 165.00   50
 51  \w    -48.00  -9.00   0.50    0.05    --  -37.97 -57.00  90.00   78
 52  \w    -74.00  -4.00   0.50    0.05    --  -37.97 -77.00  60.00  140
 53  \w   -115.00 -89.00   0.50    0.05    --  -37.97 -77.00  60.00   52
 54  \w   -105.00 -79.00   0.50    0.05    --  -37.97 -57.00-120.00   52
 55  \w    -65.00  -8.00   0.50    0.05    --  -37.97 -57.00-120.00  114
 56  \w    -75.00 -46.00   0.50    0.05    --  -37.97 178.00 -90.00   58
 57  \w   -124.00 -82.00   0.50    0.05    --  -37.97 178.00 -90.00   84
 58  \w    -91.00 -65.00   0.50    0.05    --  -37.97 -57.00  90.00   52
 59  \w     75.00 105.00   0.50    0.05    --   37.97  77.00 -90.00   60
 60  \w     61.00 110.00   0.50    0.05    --   37.97 178.00  90.00   98
 61  \w     -8.00  28.00   0.50    0.05    --   37.97  95.00  15.75   72
 62  \w     32.00  58.00   0.50    0.05    --   37.97  57.00-180.00   52
 63  \w      0.00  53.00   0.50    0.05    --   37.97  77.00 -90.00  106
 64  \w     64.00 112.00   0.50    0.05    --   37.97  57.00-180.00   96
 65  \w     62.00 110.00   0.50    0.05    --   37.97 178.00 -30.00   96
 66  \w   -164.00 -60.00   0.50    0.05    --  -98.50 -77.00-150.00  208
 67  \w   -166.00-140.00   0.50    0.05    --  -98.50 -74.00 -72.27   52
 68  \w   -124.00 -63.00   0.50    0.05    --  -98.50 -70.00 107.70  122
 69  \w    -96.00 -60.00   0.50    0.05    --  -98.50 -77.00   0.00   72
 70  \w   -142.00 -65.00   0.50    0.05    --  -98.50 -66.00  57.22  154
 71  \w   -171.00-145.00   0.50    0.05    --  -98.50 -74.00-107.82   52
 72  \w   -100.00 -60.00   0.50    0.05    --  -98.50 -77.00-120.00   80
 73  \w   -168.00-143.00   0.50    0.05    --  -98.50 -75.00 169.16   50
 74  \w   -163.00-137.00   0.50    0.05    --  -98.50 -70.00 107.70   52
 75  \w   -109.00 -60.00   0.50    0.05    --  -98.50 -78.00 109.77   98
 76  \w    -86.00 -60.00   0.50    0.05    --  -98.50 -77.00 -90.00   52
 77  \w   -141.00 -60.00   0.50    0.05    --  -98.50 -79.00  85.38  162
 78  \w    -88.00 -58.00   0.50    0.05    --  -98.50 -83.00 -48.77   60
 79  \w   -100.00 -58.00   0.50    0.05    --  -98.50 -83.00  -7.50   84
 80  \w    -93.00 -61.00   0.50    0.05    --  -98.50 -78.00 -30.92   64
 81  \w    -86.00 -61.00   0.50    0.05    --  -98.50 -74.00-107.82   50
 82  \w   -112.00 -60.00   0.50    0.05    --  -98.50 -79.00  26.23  104
 83  \w   -101.00 -61.00   0.50    0.05    --  -98.50 -76.00  40.15   80
 84  \w    -98.00 -64.00   0.50    0.05    --  -98.50 -71.00 147.15   68
 85  \w    -84.00 -59.00   0.50    0.05    --  -98.50 -80.00-168.56   50
 86  \w   -150.00-124.00   0.50    0.05    --  -98.50 -71.00 147.15   52
 87  \w   -134.00-101.00   0.50    0.05    --  -98.50 -77.00 137.38   66
 88  \w    -95.00 -60.00   0.50    0.05    --  -98.50 -77.00 137.38   70
 89  \w    -85.00 -60.00   0.50    0.05    --  -98.50 -79.00  60.52   50
 90  \w    -90.00 -64.00   0.50    0.05    --  -98.50 -71.00 -89.31   52
 91  \w   -142.00-117.00   0.50    0.05    --  -98.50 -61.00-180.00   50
 92  \w   -116.00 -67.00   0.50    0.05    --  -98.50 -61.00-180.00   98
 93  \w   -101.00 -60.00   0.50    0.05    --  -98.50 -77.00-134.78   82
 94  \w   -120.00 -62.00   0.50    0.05    --  -98.50 -74.00 -72.27  116
 95  \w    -95.00 -63.00   0.50    0.05    --  -98.50 -75.00 169.16   64
 96  \w    -85.00 -60.00   0.50    0.05    --  -98.50 -77.00  90.00   50
 97  \w   -139.00-108.00   0.50    0.05    --  -98.50 -74.00-107.82   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0091010000
_diffrn_orient_matrix_UB_12      0.0821942000
_diffrn_orient_matrix_UB_13      -0.1247974000
_diffrn_orient_matrix_UB_21      -0.0769153000
_diffrn_orient_matrix_UB_22      -0.1053872000
_diffrn_orient_matrix_UB_23      -0.0171672000
_diffrn_orient_matrix_UB_31      -0.1531172000
_diffrn_orient_matrix_UB_32      0.1023332000
_diffrn_orient_matrix_UB_33      0.0125609000
_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  0.0446
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22418
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.938
_diffrn_reflns_theta_min         3.632
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.250
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
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    1.235
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_refine_diff_density_max         0.822
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0545P)^2^+0.4157P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1089
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3937
_reflns_number_total             4302
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02161g2.cif
_cod_data_source_block           mwt-2-171-9
_cod_original_formula_sum        'C27 H25 O2 P1'
_cod_depositor_comments
;

2025-01-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         39.28
_cod_original_formula_moiety         '0.095(C27 H25 O2 P)'
_cod_original_formula_units_Z            21
_cod_database_code               7130155
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H P O'
_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 Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00D(H00D,H00E), C00T(H00U,H00V)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00E(H00F), C00F(H00G), C00G(H00H), C00H(H00I), C00I(H00J),
 C00J(H00K), C00K(H00L), C00L(H00M), C00M(H00N), C00N(H00O), C00O(H00P),
 C00P(H00Q), C00Q(H00R), C00R(H00S), C00S(H00T)
2.c Idealised Me refined as rotating group:
 C00U(H00W,H00X,H00Y)
;
_shelx_res_checksum              79983
_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 2.653
_oxdiff_exptl_absorpt_empirical_full_min 0.718