Tridentate P,N,N-ligand promoted copper-catalyzed [3+2] cycloaddition of propargylic esters with β-enamino esters: synthesis of highly functionalized pyrroles
Li, Qing; Hou, Chuan-Jin; Hui, Yun-Ze; Liu, Yan-Jun; Yang, Rui-Feng; Hu, Xiang-Ping; RSC Adv.  (2015) –; doi:10.1039/C5RA19304D

data_7222441
_publ_section_title
;
 Tridentate P,N,N-ligand promoted copper-catalyzed [3+2] cycloaddition of
 propargylic esters with \b-enamino esters: synthesis of highly
 functionalized pyrroles
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA19304D
_journal_year                    2015
_chemical_formula_moiety         'C26 H23 N O4 S'
_chemical_formula_sum            'C26 H23 N O4 S'
_chemical_formula_weight         445.51
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-10-16
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2015-06-19 deposited with the CCDC.
2015-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.524(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9973(18)
_cell_length_b                   19.663(3)
_cell_length_c                   11.499(2)
_cell_measurement_reflns_used    6125
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4823
_cell_measurement_theta_min      1.8215
_cell_volume                     2197.8(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0303
_diffrn_orient_matrix_UB_12      -0.0834
_diffrn_orient_matrix_UB_13      -0.0520
_diffrn_orient_matrix_UB_21      -0.0343
_diffrn_orient_matrix_UB_22      -0.0101
_diffrn_orient_matrix_UB_23      0.0362
_diffrn_orient_matrix_UB_31      -0.0650
_diffrn_orient_matrix_UB_32      0.0309
_diffrn_orient_matrix_UB_33      -0.0531
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14109
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         2.759
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.341
_exptl_crystal_size_min          0.261
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0479P)^2^+1.1642P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1284
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4673
_reflns_number_total             4993
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra19304d2.cif
_cod_data_source_block           sa3664
_cod_original_cell_volume        2197.7(7)
_cod_database_code               7222441
_shelxl_version_number           2013-4
_diffrn_number_total             5153
_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:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
2.c X=CH2 refined with riding coordinates:
 C26(H26A,H26B)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              43234
_shelx_hkl_checksum              22156