Preparation of aromatic γ-hydroxyketones by means of Heck coupling of aryl halides and 2,3-dihydrofuran, catalyzed by a palladium(ii) glycine complex under microwave irradiation
Jiménez-Cruz, Juan C.; Guzmán-Mejía, Ramón; Juaristi, Eusebio; Sánchez-Antonio, Omar; García-Revilla, Marco A.; González-Campos, J. Betzabe; Aviña-Verduzco, Judit; New Journal of Chemistry 44 (2020) 13382–13392; doi:10.1039/D0NJ02630A

data_7059813
_publ_section_title
;
 Preparation of aromatic \g-hydroxyketones by means of Heck coupling of
 aryl halides and 2,3-dihydrofuran, catalyzed by a palladium(ii) glycine
 complex under microwave irradiation
;
_journal_issue                   31
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13382
_journal_page_last               13392
_journal_paper_doi               10.1039/D0NJ02630A
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C18 H20 O4'
_chemical_formula_sum            'C18 H20 O4'
_chemical_formula_weight         300.34
_chemical_name_systematic        4-hydroxy-1,4-bis(4-methoxyphenyl)butan-1-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-23 deposited with the CCDC.	2020-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.648(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1124(5)
_cell_length_b                   5.2113(2)
_cell_length_c                   13.3792(6)
_cell_measurement_reflns_used    9358
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      62.29
_cell_measurement_theta_min      3.31
_cell_volume                     773.22(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      273.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18860
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        62.540
_diffrn_reflns_theta_max         62.540
_diffrn_reflns_theta_min         3.310
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.5665
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1304 before and 0.0977 after correction. The Ratio of minimum to maximum transmission is 0.7531. The \l/2 correction factor is Not present.'
_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    1.290
_exptl_crystal_description       ROMBO
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 817 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(14)
_refine_ls_extinction_coef       0.008(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   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2456
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0713P)^2^+0.1608P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1434
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2127
_reflns_number_total             2456
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj02630a2.cif
_cod_data_source_block           jav_jc_11_0m
_cod_depositor_comments
;Adding full bibliography for 7059813--7059814.cif.

 Adding full bibliography for 7059813--7059814.cif.
;
_cod_database_code               7059813
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.809
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00B,H00C), C00K(H00D,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C006(H006), C007(H007), C00A(H00A), C00E(H00E), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J)
2.d Idealised Me refined as rotating group:
 C00L(H00K,H00L,H00M), C00M(H00N,H00O,H00P)
2.e Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_res_checksum              59122
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
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;