Pd(II)-Catalyzed, Picolinamide-Assisted, Z-Selective γ-Arylation of Allylamines To Construct Z-Cinnamylamines.
Parella, Ramarao; Babu, Srinivasarao Arulananda; The Journal of organic chemistry 82 (2017) 6550–6567; doi:10.1021/acs.joc.7b00535

data_4037488
_publ_section_title
;
 Pd(II)-Catalyzed, Picolinamide-Assisted, Z-Selective \g-Arylation of
 Allylamines To Construct Z-Cinnamylamines.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6550
_journal_page_last               6567
_journal_paper_doi               10.1021/acs.joc.7b00535
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C16 H16 N2 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
????
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.8868(11)
_cell_length_b                   15.861(2)
_cell_length_c                   18.9570(19)
_cell_measurement_reflns_used    5278
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     2972.7(6)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_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      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.017602
_diffrn_orient_matrix_UB_12      -0.026791
_diffrn_orient_matrix_UB_13      0.095931
_diffrn_orient_matrix_UB_21      0.013594
_diffrn_orient_matrix_UB_22      -0.058603
_diffrn_orient_matrix_UB_23      -0.018861
_diffrn_orient_matrix_UB_31      0.050685
_diffrn_orient_matrix_UB_32      0.013534
_diffrn_orient_matrix_UB_33      -0.005520
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30321
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         3.243
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BLESSING 1995'
_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    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0786
_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^)+(0.0653P)^2^+0.6435P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1664
_refine_ls_wR_factor_ref         0.1878
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2317
_reflns_number_total             3398
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00535_si_002.cif
_cod_data_source_block           pr-3398_rt
_cod_original_cell_volume        2972.8(6)
_cod_database_code               4037488
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{O3A, O3B}
{O4A, O4B}
3. Uiso/Uaniso restraints and constraints
Uanis(O3A) = Uanis(O3B)
Uanis(O4A) = Uanis(O4B)
Uanis(C16B) = Uanis(C16A) = Uanis(C15A) = Uanis(C15B)
4. Others
 Sof(O3B)=Sof(C16B)=Sof(H16A)=Sof(H16B)=Sof(O4B)=Sof(C15B)=Sof(H15C)=Sof(H15D)=
 1-FVAR(1)
 Sof(O4A)=Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(C16A)=Sof(H16C)=Sof(H16D)=Sof(O3A)=
 FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C15A(H15A,H15B), C16B(H16A,H16B), C16A(H16C,H16D), C15B(H15C,H15D)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C0AA(H0AA), C7(H7), C8(H8), C10(H10), C13(H13), C14(H14)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'