Pd(OAc)2-Catalyzed, AgOAc-Promoted Z Selective Directed β-Arylation of Acrylamide Systems and Stereoselective Construction of Z-Cinnamamide Scaffolds.
Parella, Ramarao; Babu, Srinivasarao Arulananda; The Journal of organic chemistry 80 (2015) 12379–12396; doi:10.1021/acs.joc.5b02264

data_4036500
_publ_section_title
;
 Pd(OAc)2-Catalyzed, AgOAc-Promoted Z Selective Directed \b-Arylation of
 Acrylamide Systems and Stereoselective Construction of Z-Cinnamamide
 Scaffolds.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12379
_journal_page_last               12396
_journal_paper_doi               10.1021/acs.joc.5b02264
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C24 H17 N3 O3'
_chemical_formula_sum            'C24 H17 N3 O3'
_chemical_formula_weight         395.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                86.770(11)
_cell_angle_beta                 89.290(14)
_cell_angle_gamma                80.555(17)
_cell_formula_units_Z            4
_cell_length_a                   6.1038(9)
_cell_length_b                   16.2799(19)
_cell_length_c                   19.802(3)
_cell_measurement_reflns_used    3956
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1937.9(5)
_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 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 15.0000
	   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: 15.0000
	   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: 15.0000
	   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      0.092630
_diffrn_orient_matrix_UB_12      -0.136661
_diffrn_orient_matrix_UB_13      0.018100
_diffrn_orient_matrix_UB_21      -0.018678
_diffrn_orient_matrix_UB_22      -0.008063
_diffrn_orient_matrix_UB_23      -0.058953
_diffrn_orient_matrix_UB_31      0.041050
_diffrn_orient_matrix_UB_32      0.026213
_diffrn_orient_matrix_UB_33      -0.013645
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20791
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.541
_diffrn_reflns_theta_min         3.091
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessings, 1995'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.011(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         8910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.1731
_refine_ls_R_factor_gt           0.1155
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3524
_refine_ls_wR_factor_ref         0.4024
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3963
_reflns_number_total             8910
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02264_si_003.cif
_cod_data_source_block           pr2150rt
_cod_database_code               4036500
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N11(H11), N41(H41), C23(H23), C53(H53), C55(H55), C25(H25), C57(H57),
 C27(H27), C14(H14), C26(H26), C17(H17), C38(H38), C47(H47), C32(H32), C21(H21),
  C48(H48), C44(H44), C56(H56), C18(H18), C8(H8), C33(H33), C37(H37), C51(H51),
 C2(H2), C19(H19), C36(H36), C6(H6), C3(H3), C34(H34), C7(H7), C20(H20), C4(H4),
  C49(H49), C50(H50)
;
_olex2_submission_special_instructions 'No special instructions were received'