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_7243648
_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 N2 O'
_chemical_formula_weight         343.20
_chemical_name_common            Boscalid
_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                 91.746(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.8126(13)
_cell_length_b                   11.5893(9)
_cell_length_c                   18.7010(15)
_cell_measurement_reflns_used    3484
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.05
_cell_measurement_theta_min      2.18
_cell_volume                     3208.9(5)
_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 1.000
_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  0.0851
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28243
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.406
_diffrn_reflns_theta_max         24.406
_diffrn_reflns_theta_min         2.068
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  0.9582
_exptl_absorpt_correction_T_min  0.9114
_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
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       plate
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         5283
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+1.7281P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1473
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3100
_reflns_number_total             5283
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc02602j2.cif
_cod_data_source_block           po1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7243648
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.930
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              93747