Pd-Catalysed Suzuki‒Miyaura cross-coupling of aryl chlorides at low catalyst loadings in water for the synthesis of industrially important fungicides
Orecchia, Patrizio; Petkova, Desislava Slavcheva; Goetz, Roland; Rominger, Frank; Hashmi, A. Stephen K.; Schaub, Thomas; Green Chemistry  (2021) –; doi:10.1039/D1GC02602J

data_7243650
_publ_section_title
;
 Pd-Catalysed Suzuki--Miyaura cross-coupling of aryl chlorides at low
 catalyst loadings in water for the synthesis of industrially important
 fungicides
;
_journal_name_full               'Green Chemistry'
_journal_paper_doi               10.1039/D1GC02602J
_journal_year                    2021
_chemical_formula_sum            'C18 H12 Cl2 F3 N3 O'
_chemical_formula_weight         414.21
_chemical_name_common            Bixafen
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-27 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.0924(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   18.0476(11)
_cell_length_c                   8.6239(5)
_cell_measurement_reflns_used    2652
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.59
_cell_measurement_theta_min      2.76
_cell_volume                     1738.37(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17929
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         1.823
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    0.418
_exptl_absorpt_correction_T_max  0.9590
_exptl_absorpt_correction_T_min  0.9268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). <i>SADABS</i>. University of G\"ottingen, Germany.
;
_exptl_crystal_colour            colourless
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_exptl_crystal_description       plank
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_exptl_crystal_size_max          0.143
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_refine_diff_density_max         0.304
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_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0368P)^2^+1.9244P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1227
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_reflns_number_gt                2247
_reflns_number_total             3545
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc02602j2.cif
_cod_data_source_block           po3
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7243650
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.943
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              66735