Ruthenium-catalyzed three-component tandem remote C-H functionalization of naphthalenes: modular and concise synthesis of multifunctional naphthalenes.
Huang, Mao-Gui; Fu, Yue-Liu-Ting; Li, Jia-Wei; Liu, Yue-Jin; Chemical science 16 (2025) 1957–1965; doi:10.1039/d4sc06846g

data_1573570
_publ_section_title
;
 Ruthenium-catalyzed three-component tandem remote C-H functionalization
 of naphthalenes: modular and concise synthesis of multifunctional
 naphthalenes.
;
_journal_issue                   4
_journal_name_full               'Chemical science'
_journal_page_first              1957
_journal_page_last               1965
_journal_paper_doi               10.1039/d4sc06846g
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C31 H29 F2 O4 P'
_chemical_formula_sum            'C31 H29 F2 O4 P'
_chemical_formula_weight         534.51
_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             2020-12-26
_audit_creation_method
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2024-07-08 deposited with the CCDC.	2024-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                99.3100(10)
_cell_angle_beta                 98.0540(10)
_cell_angle_gamma                100.6190(10)
_cell_formula_units_Z            2
_cell_length_a                   9.62340(10)
_cell_length_b                   10.49270(10)
_cell_length_c                   14.0802(2)
_cell_measurement_reflns_used    17430
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.8670
_cell_measurement_theta_min      3.2010
_cell_volume                     1357.67(3)
_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 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.964
_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    -56.00 -27.00   0.50    0.39    --  -43.30  42.00-103.00   58
  2  \w     -8.00  32.00   0.50    0.39    --  -43.30  42.00-103.00   80
  3  \w     94.00 120.00   0.50    0.39    --   43.30  42.00-103.00   52
  4  \w     85.00 111.00   0.50    0.39    --   43.30  57.00 -30.00   52
  5  \w     91.00 117.00   0.50    0.39    --   43.30  77.00 -30.00   52
  6  \w     64.00  90.00   0.50    0.39    --   43.30  77.00  60.00   52
  7  \w     28.00  65.00   0.50    0.39    --   43.30  77.00 -30.00   74
  8  \w     22.00  69.00   0.50    0.39    --   43.30  42.00-103.00   94
  9  \w     22.00  48.00   0.50    0.39    --   43.30  57.00 -30.00   52
 10  \w     14.00  51.00   0.50    0.39    --   43.30  77.00  60.00   74
 11  \w     88.00 174.00   0.50    1.56    --  109.88  61.00  90.00  172
 12  \w     94.00 170.00   0.50    1.56    --  109.88  61.00  30.00  152
 13  \w     90.00 168.00   0.50    1.56    --  109.88  42.00-103.00  156
 14  \w    113.00 176.00   0.50    1.56    --  109.88 125.00-120.00  126
 15  \w     93.00 174.00   0.50    1.56    --  109.88 125.00 -30.00  162
 16  \w     95.00 171.00   0.50    1.56    --  109.88 125.00  30.00  152
 17  \w     83.00 164.00   0.50    1.56    --  109.88  77.00 120.00  162
 18  \w     61.00 168.00   0.50    1.56    --  109.88  15.00   0.00  214
 19  \w     74.00 107.00   0.50    1.56    --  109.88 -94.00 120.00   66
 20  \w     44.00  79.00   0.50    0.39    --   43.30 -99.00   0.00   70
 21  \w     32.00  97.00   0.50    0.39    --   43.30-125.00 -30.00  130
 22  \w     34.00 101.00   0.50    1.56    --  109.88 -42.00 103.00  134
 23  \w     37.00 103.00   0.50    1.56    --  109.88 -94.00   0.00  132
 24  \w     93.00 120.00   0.50    1.56    --  109.88-125.00   0.00   54
 25  \w     53.00  94.00   0.50    1.56    --  109.88 -94.00-120.00   82
 26  \w     42.00  67.00   0.50    1.56    --  109.88-125.00   0.00   50
 27  \w     42.00  89.00   0.50    1.56    --  109.88 -94.00 -30.00   94
 28  \w     36.00  98.00   0.50    1.56    --  109.88 -94.00  60.00  124
 29  \w     36.00  68.00   0.50    1.56    --  109.88 -94.00 120.00   64
 30  \w     -3.00  33.00   0.50    0.39    --   43.30 -99.00   0.00   72
 31  \w    -33.00  58.00   0.50    0.39    --   43.30 -42.00 103.00  182
 32  \w    -67.00 -16.00   0.50    0.39    --  -43.30 -77.00 120.00  102
 33  \w    -81.00 -16.00   0.50    0.39    --  -43.30 -77.00  60.00  130
 34  \w    -64.00 -15.00   0.50    0.39    --  -43.30 -77.00 -30.00   98
 35  \w    -65.00 -14.00   0.50    0.39    --  -43.30 -77.00-120.00  102
 36  \w    -52.00 -16.00   0.50    0.39    --  -43.30 -77.00-180.00   72
 37  \w    -83.00 -26.00   0.50    0.39    --  -43.30 -37.00-120.00  114
 38  \w    -91.00 -63.00   0.50    1.56    --  -90.25 -73.00 -18.94   56
 39  \w    -85.00 -59.00   0.50    1.56    --  -90.25 -83.00  27.10   52
 40  \w    -89.00 -61.00   0.50    1.56    --  -90.25 -77.00  60.00   56
 41  \w    -87.00 -61.00   0.50    1.56    --  -90.25 -77.00 114.21   52
 42  \w    -87.00 -61.00   0.50    1.56    --  -90.25 -77.00 150.00   52
 43  \w    -86.00 -61.00   0.50    1.56    --  -90.25 -78.00  86.79   50
 44  \w    -92.00 -59.00   0.50    1.56    --  -90.25 -81.00  58.60   66
 45  \w    -87.00 -61.00   0.50    1.56    --  -90.25 -77.00   0.00   52
 46  \w    -91.00 -61.00   0.50    1.56    --  -90.25 -77.00 -30.00   60
 47  \w    -86.00 -60.00   0.50    1.56    --  -90.25 -79.00 -77.28   52
 48  \w    -99.00 -60.00   0.50    1.56    --  -90.25 -82.00-131.20   78
 49  \w    -89.00 -64.00   0.50    1.56    --  -90.25 -77.00-150.00   50
 50  \w    -90.00 -61.00   0.50    1.56    --  -90.25 -77.00-180.00   58
 51  \w   -102.00 -63.00   0.50    1.56    --  -90.25 -72.00-167.87   78
 52  \w   -101.00 -63.00   0.50    1.56    --  -90.25 -73.00-121.56   76
 53  \w   -115.00 -68.00   0.50    0.39    --  -43.30 -77.00-120.00   94
 54  \w   -115.00 -62.00   0.50    1.56    --  -90.25 -76.00 -50.30  106
 55  \w   -115.00 -89.00   0.50    0.39    --  -43.30 -77.00  60.00   52
 56  \w   -103.00 -25.00   0.50    0.39    --  -43.30 -42.00 103.00  156
 57  \w    -92.00 -67.00   0.50    1.56    --  -90.25 -61.00 140.39   50
 58  \w   -103.00 -64.00   0.50    1.56    --  -90.25 -71.00 133.60   78
 59  \w   -108.00 -59.00   0.50    1.56    --  -90.25 -83.00  46.62   98
 60  \w    -96.00 -63.00   0.50    1.56    --  -90.25 -76.00  76.10   66
 61  \w   -101.00 -64.00   0.50    1.56    --  -90.25 -70.00  87.57   74
 62  \w   -110.00 -61.00   0.50    1.56    --  -90.25 -79.00  27.86   98
 63  \w   -109.00 -61.00   0.50    1.56    --  -90.25 -77.00 -60.00   96
 64  \w   -114.00 -63.00   0.50    1.56    --  -90.25 -77.00 -90.00  102
 65  \w   -116.00 -61.00   0.50    1.56    --  -90.25 -78.00-102.23  110
 66  \w   -129.00-103.00   0.50    1.56    --  -90.25 -73.00 -18.94   52
 67  \w   -142.00-117.00   0.50    1.56    --  -90.25 -83.00  27.10   50
 68  \w   -122.00 -96.00   0.50    1.56    --  -90.25 -42.00 103.00   52
 69  \w    -89.00 -64.00   0.50    1.56    --  -90.25 -69.00 116.02   50
 70  \w   -155.00-130.00   0.50    1.56    --  -90.25 -71.00 133.60   50
 71  \w   -160.00-135.00   0.50    1.56    --  -90.25 -78.00  86.79   50
 72  \w   -139.00-114.00   0.50    1.56    --  -90.25 -81.00  58.60   50
 73  \w   -163.00-124.00   0.50    1.56    --  -90.25 -79.00  27.86   78
 74  \w   -162.00-136.00   0.50    1.56    --  -90.25 -77.00 114.21   52
 75  \w   -162.00 -99.00   0.50    1.56    --  -90.25 -77.00   0.00  126
 76  \w   -146.00-120.00   0.50    1.56    --  -90.25 -77.00 -90.00   52
 77  \w   -147.00-116.00   0.50    1.56    --  -90.25 -82.00-131.20   62
 78  \w   -151.00-125.00   0.50    1.56    --  -90.25 -77.00-150.00   52
 79  \w   -158.00-116.00   0.50    1.56    --  -90.25 -73.00-121.56   84
 80  \w   -155.00-107.00   0.50    1.56    --  -90.25 -77.00-180.00   96
 81  \w   -164.00-113.00   0.50    1.56    --  -90.25 -79.00 -77.28  102
 82  \w    -93.00 -68.00   0.50    1.56    --  -90.25  42.00-103.00   50
 83  \w     88.00 172.00   0.50    1.56    --  109.88  77.00-180.00  168
;
_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      -0.1257805000
_diffrn_orient_matrix_UB_12      0.0333252000
_diffrn_orient_matrix_UB_13      -0.0649641000
_diffrn_orient_matrix_UB_21      0.0881692000
_diffrn_orient_matrix_UB_22      0.1408700000
_diffrn_orient_matrix_UB_23      0.0081777000
_diffrn_orient_matrix_UB_31      0.0614296000
_diffrn_orient_matrix_UB_32      -0.0471227000
_diffrn_orient_matrix_UB_33      -0.0916245000
_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  0.0332
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30872
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.090
_diffrn_reflns_theta_min         3.231
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.311
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77475
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0457P)^2^+0.2786P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4840
_reflns_number_total             5457
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06846g2.cif
_cod_data_source_block           fuyue-2-100
_cod_depositor_comments          'Adding full bibliography for 1573570.cif.'
_cod_database_code               1573570
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O P F'
_shelx_estimated_absorpt_t_max   0.780
_shelx_estimated_absorpt_t_min   0.780
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C00L(H00B,H00C), C00Z(H00R,H00U)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00G(H00G), C00H(H00H), C00J(H00J), C00K(H00K), C00M(H00M),
 C00N(H00N), C00P(H00P), C00Q(H00Q), C00S(H00S), C00T(H00T), C00V(H00V),
 C00W(H00W), C00X(H00X), C010(H010), C011(H011)
2.c Idealised Me refined as rotating group:
 C00O(H00D,H00E,H00F), C00U(H00I,H00L,H00O), C012(H01A,H01B,H01C)
;
_shelx_res_checksum              33155
_shelx_hkl_checksum              36797
_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 1.295
_oxdiff_exptl_absorpt_empirical_full_min 0.848