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_4036501
_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         'C17 H12 F N3 O'
_chemical_formula_sum            'C17 H12 F N3 O'
_chemical_formula_weight         293.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
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_cell_length_a                   12.6317(13)
_cell_length_b                   15.1405(16)
_cell_length_c                   7.1160(8)
_cell_measurement_reflns_used    3063
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.5
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_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
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_computing_data_reduction
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CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
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_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 CCD
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_diffrn_measured_fraction_theta_full 0.998
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_diffrn_measurement_details
;
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 533
	           Slice: -69.0000 - 90.9000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             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      -0.140744
_diffrn_orient_matrix_UB_12      -0.007605
_diffrn_orient_matrix_UB_13      0.002384
_diffrn_orient_matrix_UB_21      0.003074
_diffrn_orient_matrix_UB_22      -0.040597
_diffrn_orient_matrix_UB_23      0.052008
_diffrn_orient_matrix_UB_31      -0.008809
_diffrn_orient_matrix_UB_32      0.061961
_diffrn_orient_matrix_UB_33      0.048887
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
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_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7422
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.140
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessings, 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    1.436
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.764
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.182
_refine_ls_R_factor_all          0.1627
_refine_ls_R_factor_gt           0.0940
_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          0.2348
_refine_ls_wR_factor_ref         0.3668
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1284
_reflns_number_total             2481
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02264_si_002.cif
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_cod_database_code               4036501
_shelxl_version_number           2014-3
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_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C16(H16), C17(H17)
;
_shelx_res_checksum              89374
_shelx_hkl_checksum              74228
_olex2_submission_special_instructions 'No special instructions were received'