Palladium-catalyzed synthesis of β-hydroxy compounds via a strained 6,4-palladacycle from directed C–H activation of anilines and C–O insertion of epoxides
Thombal, Raju S.; Feoktistova, Taisiia; González-Montiel, Gisela A.; Cheong, Paul H.-Y.; Lee, Yong Rok; Chemical Science 11 (2020) 7260–7265; doi:10.1039/D0SC01462A

data_1558389
_publ_section_title
;
 Palladium-catalyzed synthesis of \b-hydroxy compounds via a strained
 6,4-palladacycle from directed C--H activation of anilines and C--O
 insertion of epoxides
;
_journal_issue                   27
_journal_name_full               'Chemical Science'
_journal_page_first              7260
_journal_page_last               7265
_journal_paper_doi               10.1039/D0SC01462A
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration ab
_chemical_formula_moiety         'C17 H19 N O3'
_chemical_formula_sum            'C17 H19 N O3'
_chemical_formula_weight         285.33
_chemical_melting_point          390
_chemical_name_systematic
(S)-N-(2-(2-hydroxy-3-phenoxypropyl)phenyl)acetamide
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-02-01 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
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_cell_length_a                   10.2060(4)
_cell_length_b                   11.8825(5)
_cell_length_c                   12.7337(5)
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      28.16
_cell_measurement_theta_min      2.56
_cell_volume                     1544.25(11)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            50079
_diffrn_reflns_point_group_measured_fraction_full 0.997
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.293
_diffrn_reflns_theta_min         2.558
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       Block
_exptl_crystal_F_000             608
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane/Ethyl acetate'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
; 
 Flack x determined using 1244 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0577P)^2^+0.2713P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3171
_reflns_number_total             3821
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01462a2.cif
_cod_data_source_block           RST-463(S)
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1558389.cif.

 Adding full bibliography for 1558389.cif.
;
_cod_database_code               1558389
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              60162