A cooperative electron-deficient phosphine/olefin ligand system for the site-selective mechanochemical Suzuki-Miyaura cross-coupling of 2,4-dibromoaryl ethers.
Gao, Yunpeng; Jiang, Julong; Maeda, Satoshi; Kubota, Koji; Ito, Hajime; Chemical science 16 (2025) 15964–15976; doi:10.1039/d5sc01669j

data_1575238
_publ_section_title
;
 A cooperative electron-deficient phosphine/olefin ligand system for the
 site-selective mechanochemical Suzuki-Miyaura cross-coupling of
 2,4-dibromoaryl ethers.
;
_journal_issue                   35
_journal_name_full               'Chemical science'
_journal_page_first              15964
_journal_page_last               15976
_journal_paper_doi               10.1039/d5sc01669j
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C17 H13 Br O'
_chemical_formula_sum            'C17 H13 Br O'
_chemical_formula_weight         313.18
_chemical_name_systematic        2-(5-bromo-2-methoxyphenyl)naphthalene
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-10-06 deposited with the CCDC.	2025-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.47480(10)
_cell_length_b                   9.6162(2)
_cell_length_c                   21.7688(3)
_cell_measurement_reflns_used    3415
_cell_measurement_temperature    123
_cell_measurement_theta_max      76.5130
_cell_measurement_theta_min      6.0200
_cell_volume                     1355.39(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.921
_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    -84.00 -41.00   0.50    0.50    --    5.00   0.00-180.00   86
  2  \w    -89.00  34.00   0.50    0.50    --  -45.39   9.00  60.00  246
  3  \w   -137.00-102.00   0.50    0.50    -- -109.60   9.00   0.00   70
  4  \w    -63.00 -21.00   0.50    0.50    -- -109.60  46.00  90.00   84
  5  \w   -116.00 -75.00   0.50    0.50    -- -109.60  46.00  90.00   82
  6  \w    -83.00 -33.00   0.50    0.50    -- -109.60   9.00   0.00  100
  7  \w    -95.00 -26.00   0.50    0.50    -- -109.60  18.00 150.00  138
  8  \w   -197.00-106.00   0.50    0.50    -- -109.60  18.00 150.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0402363000
_diffrn_orient_matrix_UB_12      -0.0427090000
_diffrn_orient_matrix_UB_13      0.0672027000
_diffrn_orient_matrix_UB_21      -0.1456106000
_diffrn_orient_matrix_UB_22      0.1256634000
_diffrn_orient_matrix_UB_23      0.0079203000
_diffrn_orient_matrix_UB_31      -0.1837377000
_diffrn_orient_matrix_UB_32      -0.0897252000
_diffrn_orient_matrix_UB_33      -0.0207875000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4112
_diffrn_reflns_point_group_measured_fraction_full 0.886
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.606
_diffrn_reflns_theta_min         5.028
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    4.026
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane/DCM'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0281
_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^)+(0.0274P)^2^+2.1407P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0807
_reflns_Friedel_coverage         0.565
_reflns_Friedel_fraction_full    0.802
_reflns_Friedel_fraction_max     0.738
_reflns_number_gt                2399
_reflns_number_total             2413
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01669j2.cif
_cod_data_source_block           gyp847_auto
_cod_depositor_comments
'Adding full bibliography for 1575237--1575240.cif.'
_cod_database_code               1575238
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H O Br'
_shelx_estimated_absorpt_t_max   0.296
_shelx_estimated_absorpt_t_min   0.296
_diffrn_oxdiff_digest_frames
;
01fcd7773d9a6b9703700eca92fd2b2f10000321341
;
_diffrn_oxdiff_digest_hkl
;
01a92cfefd9bdaa01c17277c30dd07c321f5b3
;
_reflns_odcompleteness_completeness 94.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C003(H003), C004(H004), C00A(H00A), C00B(H00B), C00E(H00F), C00F(H00G),
 C00G(H00H), C00H(H00I), C00I(H00J), C00J(H00K)
2.b Idealised Me refined as rotating group:
 C00C(H00C,H00D,H00E)
;
_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 1.473
_oxdiff_exptl_absorpt_empirical_full_min 0.662