Directed, Regiocontrolled Hydroamination of Unactivated Alkenes via Protodepalladation.
Gurak, Jr, John A; Yang, Kin S.; Liu, Zhen; Engle, Keary M.; Journal of the American Chemical Society 138 (2016) 5805–5808; doi:10.1021/jacs.6b02718

data_4130362
_publ_section_title
;
 Directed, Regiocontrolled Hydroamination of Unactivated Alkenes via
 Protodepalladation.
;
_journal_issue                   18
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5805
_journal_page_last               5808
_journal_paper_doi               10.1021/jacs.6b02718
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C17 H15 N3 O3 Pd, 0.5(C4 H5 N O2), 0.25(O)'
_chemical_formula_sum            'C19 H17.5 N3.5 O4.25 Pd'
_chemical_formula_weight         469.26
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-15
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.8740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   25.7330(12)
_cell_length_b                   13.3912(5)
_cell_length_c                   21.1443(9)
_cell_measurement_reflns_used    9610
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.266
_cell_measurement_theta_min      2.396
_cell_volume                     7259.9(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            35578
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.295
_diffrn_reflns_theta_min         2.396
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.057
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_correction_T_min  0.2130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0510 before and 0.0468 after correction.
The Ratio of minimum to maximum transmission is 0.8108.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_description       block
_exptl_crystal_F_000             3776
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         2.572
_refine_diff_density_min         -1.008
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     569
_refine_ls_number_reflns         8994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0367P)^2^+33.5664P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7338
_reflns_number_total             8994
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b02718_si_003.cif
_cod_data_source_block           engle07_0m_a_sq
_cod_original_formula_sum        'C19 H17.50 N3.50 O4.25 Pd'
_cod_database_code               4130362
_shelx_estimated_absorpt_t_max   0.778
_shelx_estimated_absorpt_t_min   0.709
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Others
 Sof(O7')=Sof(O8')=Sof(N7')=Sof(H7')=Sof(C35')=Sof(C36')=Sof(H36C)=Sof(H36D)=
 Sof(C37')=Sof(H37C)=Sof(H37D)=Sof(C38')=1-FVAR(1)
 Sof(O7)=Sof(O8)=Sof(N7)=Sof(H7A)=Sof(C35)=Sof(C36)=Sof(H36A)=Sof(H36B)=
 Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(C38)=FVAR(1)
 Fixed Sof: O9'(0.5)
3.a Ternary CH refined with riding coordinates:
 C29(H29), C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C32(H32A,H32B), C33(H33A,H33B), C11(H11A,H11B), C15(H15A,
 H15B), C16(H16A,H16B), C36(H36A,H36B), C37(H37A,H37B), C36'(H36C,H36D),
 C37'(H37C,H37D)
3.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C1(H1), C2(H2),
 C3(H3), C5(H5), C6(H6), C7(H7), N7(H7A), N7'(H7')
3.d X=CH2 refined with riding coordinates:
 C30(H30A,H30B), C13(H13A,H13B)
;
_shelx_res_checksum              8896
_shelx_hkl_checksum              84771
_shelx_fab_checksum              11219
_shelx_shelxl_version_number     2014/7
_olex2_submission_original_sample_id AQ_H_Suc
_olex2_submission_special_instructions 'No special instructions were received'