An Efficient Route to 2-Substituted N-(1-Amino-3-methylpyrrol)amides by Ring-Opening Cyclization of Benzylidene- and Alkylidenecyclopropylcarbaldehydes with Hydrazides
Xiang-Ying Tang; Min Shi; Journal of Organic Chemistry 74 (2009) 5983–5986; doi:10.1021/jo900730t

data_4024740
_publ_section_title
;
An Efficient Route to 2-Substituted N-(1-Amino-3-methylpyrrol)amides by
Ring-Opening Cyclization of Benzylidene- and
Alkylidenecyclopropylcarbaldehydes with Hydrazides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5983
_journal_page_last               5986
_journal_paper_doi               10.1021/jo900730t
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C19 H13 Cl N2 O2'
_chemical_formula_weight         336.76
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.694(2)
_cell_angle_beta                 97.449(2)
_cell_angle_gamma                100.456(2)
_cell_formula_units_Z            2
_cell_length_a                   5.9212(8)
_cell_length_b                   9.7223(13)
_cell_length_c                   14.6666(19)
_cell_measurement_reflns_used    2573
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.382
_cell_measurement_theta_min      5.482
_cell_volume                     814.75(19)
_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 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.1050
_diffrn_reflns_av_sigmaI/netI    0.0725
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4487
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78385
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.152
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.037(6)
_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   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0872P)^2^+0.1453P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1575
_reflns_number_gt                2783
_reflns_number_total             3138
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900730t_si_001.cif
_cod_data_source_block           cd28568
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024740