Palladium-catalyzed regiodivergent hydroaminocarbonylation of alkenes to primary amides with ammonium chloride.
Gao, Bao; Zhang, Guoying; Zhou, Xibing; Huang, Hanmin; Chemical science 9 (2018) 380–386; doi:10.1039/c7sc04054g

data_1547773
_publ_section_title
;
 Palladium-catalyzed regiodivergent hydroaminocarbonylation of alkenes to
 primary amides with ammonium chloride.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              380
_journal_page_last               386
_journal_paper_doi               10.1039/c7sc04054g
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C9 H10 Cl N O'
_chemical_formula_sum            'C9 H10 Cl N O'
_chemical_formula_weight         183.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-11-07 deposited with the CCDC.
2017-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.510(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.159(13)
_cell_length_b                   7.490(4)
_cell_length_c                   9.539(5)
_cell_measurement_reflns_used    1412
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.35
_cell_measurement_theta_min      3.13
_cell_volume                     1860.4(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SMART'
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4853
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         1.564
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_T_max  0.9313
_exptl_absorpt_correction_T_min  0.8994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_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    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0735
_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^)+(0.1764P)^2^+0.3762P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2312
_refine_ls_wR_factor_ref         0.2723
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1215
_reflns_number_total             1833
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc04054g2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1547772--1547775.cif.'
_cod_original_cell_volume        1860.4(16)
_cod_database_code               1547773
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.899
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Others
 Fixed Sof: C1(0.5) H1(0.5) C3(0.5) H3(0.5) C4(0.5) H4(0.5) C6(0.5) H6(0.5)
 C1'(0.5) H1'(0.5) C3'(0.5) H3'(0.5) C4'(0.5) H4'(0.5) C6'(0.5) H6'(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C6AA(H6AA,H6AB), C8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C1'(H1'), C3'(H3'), C4'(H4'), C6'(H6')
3.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'