Ring-opening cyclization of alkylidenecyclopropyl ketones with amines. An efficient synthesis of 2,3,4-trisubstituted pyrroles.
Lu, Lianghua; Chen, Guofei; Ma, Shengming; Organic letters 8 (2006) 835–838; doi:10.1021/ol052797a

data_1505842
_publ_section_title
;
 Ring-opening cyclization of alkylidenecyclopropyl ketones with amines. An
 efficient synthesis of 2,3,4-trisubstituted pyrroles.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              835
_journal_page_last               838
_journal_paper_doi               10.1021/ol052797a
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C23 H27 N O2 S'
_chemical_formula_weight         381.52
_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                 95.626(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9949(13)
_cell_length_b                   8.8953(11)
_cell_length_c                   21.764(3)
_cell_measurement_reflns_used    968
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35.478
_cell_measurement_theta_min      5.902
_cell_volume                     2118.3(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0969
_diffrn_reflns_av_sigmaI/netI    0.1462
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12112
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65390
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.416
_exptl_crystal_size_mid          0.304
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0140(9)
_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   0.800
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.800
_refine_ls_R_factor_all          0.1469
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0302P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1181
_reflns_number_gt                1800
_reflns_number_total             4588
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol052797asi20060119_074307.cif
_cod_data_source_block           cd25467
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2118.3(4)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1505842