Pd-catalyzed oxidative coupling of enamides and alkynes for synthesis of substituted pyrroles.
Zhao, Mi-Na; Ren, Zhi-Hui; Wang, Yao-Yu; Guan, Zheng-Hui; Organic letters 16 (2014) 608–611; doi:10.1021/ol403517p

data_1513403
_publ_section_title
;
 Pd-catalyzed oxidative coupling of enamides and alkynes for synthesis of
 substituted pyrroles.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              608
_journal_page_last               611
_journal_paper_doi               10.1021/ol403517p
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C21 H19 N O3'
_chemical_formula_weight         333.37
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.905(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.262(4)
_cell_length_b                   9.481(3)
_cell_length_c                   14.406(5)
_cell_measurement_reflns_used    2053
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.61
_cell_measurement_theta_min      2.32
_cell_volume                     1778.7(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8577
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_correction_T_min  0.9700
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0084(11)
_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   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.9656P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1177
_reflns_number_gt                2550
_reflns_number_total             3157
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403517p_si_002.cif
_cod_data_source_block           xb7110
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1513403