l-Proline-catalyzed synthesis of highly functionalized multisubstituted 1,4-dihydropyridines
Jiang, Huanfeng; Mai, Ronghuan; Cao, Hua; Zhu, Qiuhua; Liu, Xiaohang; Organic & Biomolecular Chemistry 7 (2009) 4943–4953; doi:10.1039/b914659h

data_7150774
_publ_section_title
;
 l-Proline-catalyzed synthesis of highly functionalized
 multisubstituted 1,4-dihydropyridines
;
_journal_issue                   23
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              4943
_journal_page_last               4953
_journal_paper_doi               10.1039/b914659h
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C22 H20 Cl N O2'
_chemical_formula_sum            'C22 H20 Cl N O2'
_chemical_formula_weight         365.84
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.530(3)
_cell_length_b                   14.759(3)
_cell_length_c                   14.559(3)
_cell_measurement_reflns_used    4520
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      1.36
_cell_volume                     3766.8(13)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       \w
_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  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26778
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         3.03
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.768
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3357
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0663
_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^)+(0.1303P)^2^+0.2046P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2090
_refine_ls_wR_factor_ref         0.2385
_reflns_number_gt                1942
_reflns_number_total             3357
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b914659h.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_Hall     '-P 2ac 2ab '
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7150774