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_7243649
_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 F5 N3 O'
_chemical_formula_weight         381.31
_chemical_name_common            Fluxapyroxad
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.8826(6)
_cell_length_b                   9.2515(5)
_cell_length_c                   28.4963(12)
_cell_measurement_reflns_used    7606
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      66.56
_cell_measurement_theta_min      5.89
_cell_volume                     3396.3(3)
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.153.0 (STOE, 2018)'
_computing_data_reduction        'X-Area Integrate 1.74.2.0 (STOE, 2018)'
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_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'STOE Stadivari'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            10749
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        66.676
_diffrn_reflns_theta_max         66.676
_diffrn_reflns_theta_min         6.090
_diffrn_source                   'Genix3D Cu HF'
_exptl_absorpt_coefficient_mu    1.163
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'STOE X-AREA LANA'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       needle
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_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         2929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0477P)^2^+1.3541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1728
_reflns_number_total             2929
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc02602j2.cif
_cod_data_source_block           po2
_cod_database_code               7243649
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.883
_shelx_estimated_absorpt_t_max   0.973
_exptl_absorpt_special_details   'X-Area LANA 1.70.0.0 (STOE, 2017)'
_shelx_res_checksum              48473