Accessing a Biologically Relevant Benzofuran Skeleton by a One-Pot Tandem Heck Alkynylation/Cyclization Reaction Using Well-Defined Palladium N-Heterocyclic Carbene Complexes.
Kumar, Anuj; Gangwar, Manoj Kumar; Prakasham, A. P.; Mhatre, Darshan; Kalita, Alok Ch; Ghosh, Prasenjit; Inorganic chemistry 55 (2016) 2882–2893; doi:10.1021/acs.inorgchem.5b02727

data_4347111
_publ_section_title
;
 Accessing a Biologically Relevant Benzofuran Skeleton by a One-Pot Tandem
 Heck Alkynylation/Cyclization Reaction Using Well-Defined Palladium
 N-Heterocyclic Carbene Complexes.
;
_journal_issue                   6
_journal_name_full               'Inorganic chemistry'
_journal_page_first              2882
_journal_page_last               2893
_journal_paper_doi               10.1021/acs.inorgchem.5b02727
_journal_volume                  55
_journal_year                    2016
_chemical_formula_moiety         'C12 H18 Br2 N4 Pd'
_chemical_formula_sum            'C12 H18 Br2 N4 Pd'
_chemical_formula_weight         484.52
_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             2016-02-02
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.10.28 svn.r3245 for OlexSys, GUI svn.r5128)
;
_cell_angle_alpha                90.184(12)
_cell_angle_beta                 93.046(14)
_cell_angle_gamma                91.594(9)
_cell_formula_units_Z            4
_cell_length_a                   9.223(5)
_cell_length_b                   12.844(6)
_cell_length_c                   13.910(7)
_cell_measurement_reflns_used    4148
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.1
_cell_measurement_theta_min      3.0
_cell_volume                     1644.8(14)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
scan:
	Number of images: 298
	           Slice: -110.0000 - 39.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: -36.0000
	             XTD: 44.9940
	          2theta: -19.9090
scan:
	Number of images: 223
	           Slice: -92.5000 - 19.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -36.0000
	             XTD: 44.9940
	          2theta: -19.9090
scan:
	Number of images: 169
	           Slice: -74.5000 - 10.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 108.0000
	             XTD: 44.9940
	          2theta: -19.9090
scan:
	Number of images: 89
	           Slice: -52.5000 - -8.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: -108.0000
	             XTD: 44.9940
	          2theta: -19.9090
scan:
	Number of images: 61
	           Slice: -59.0000 - -28.5000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: -36.0000
	             XTD: 44.9940
	          2theta: -19.9090
scan:
	Number of images: 60
	           Slice: -35.0000 - -5.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 36.0000
	             XTD: 44.9940
	          2theta: -19.9090
scan:
	Number of images: 241
	           Slice: -59.0000 - 61.5000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: -180.0000
	             XTD: 44.9940
	          2theta: -19.9090
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       XPlain
_diffrn_orient_matrix_UB_11      -0.054638
_diffrn_orient_matrix_UB_12      0.075368
_diffrn_orient_matrix_UB_13      -0.055980
_diffrn_orient_matrix_UB_21      -0.009076
_diffrn_orient_matrix_UB_22      -0.048309
_diffrn_orient_matrix_UB_23      -0.060417
_diffrn_orient_matrix_UB_31      -0.063646
_diffrn_orient_matrix_UB_32      -0.021230
_diffrn_orient_matrix_UB_33      0.026100
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17018
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.007
_diffrn_source                   MicroMax003_Mo
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    5.979
_exptl_absorpt_correction_T_max  0.585
_exptl_absorpt_correction_T_min  0.343
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.957
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.167
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.115
_refine_diff_density_max         1.716
_refine_diff_density_min         -1.444
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0300P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0869
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4154
_reflns_number_total             5767
_reflns_shell_number_unique_all  8746
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic5b02727_si_002.cif
_cod_data_source_block           PG-AK-12-64
_cod_database_code               4347111
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C20(H20A,H20B)
2.c Me refined with riding coordinates:
 C9(H9A,H9B,H9C), C21(H21A,H21B,H21C), C12(H12A,H12B,H12C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C11(H11A,H11B,H11C)
2.d Aromatic/amide H refined with riding coordinates:
 C14(H14), C16(H16), C17(H17), C5(H5), C18(H18), C1(H1), C6(H6), C15(H15),
 C3(H3), C4(H4), C13(H13), C2(H2)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'