Acid-promoted rapid solvent-free access to substituted 1,4-dihydropyridines from β-ketothioamides
Li, Ming; Sun, Ke-Na; Wen, Li-Rong; RSC Adv.  (2016) –; doi:10.1039/C5RA26931H

data_7224272
_publ_section_title
;
 Acid-promoted rapid solvent-free access to substituted
 1,4-dihydropyridines from \b-ketothioamides
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA26931H
_journal_year                    2016
_chemical_formula_moiety         'C31 H22 Cl N3 S, C4 H8 O2'
_chemical_formula_sum            'C35 H30 Cl N3 O2 S'
_chemical_formula_weight         592.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/cc13v57c
_audit_creation_date             2014-12-08
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2014-12-08 deposited with the CCDC.
2016-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                94.687(6)
_cell_angle_beta                 109.956(7)
_cell_angle_gamma                92.579(4)
_cell_formula_units_Z            2
_cell_length_a                   9.394(3)
_cell_length_b                   13.133(4)
_cell_length_c                   13.181(5)
_cell_measurement_reflns_used    5082
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4785
_cell_measurement_theta_min      1.6526
_cell_volume                     1518.8(9)
_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 0.989
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0309
_diffrn_orient_matrix_UB_12      0.0086
_diffrn_orient_matrix_UB_13      0.1090
_diffrn_orient_matrix_UB_21      0.0750
_diffrn_orient_matrix_UB_22      0.0027
_diffrn_orient_matrix_UB_23      -0.0153
_diffrn_orient_matrix_UB_31      0.0099
_diffrn_orient_matrix_UB_32      0.0779
_diffrn_orient_matrix_UB_33      0.0204
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14983
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.451
_diffrn_reflns_theta_min         1.653
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       plate
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.098
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         6801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0971
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0804P)^2^+3.7828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2392
_refine_ls_wR_factor_ref         0.2448
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6128
_reflns_number_total             6801
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra26931h2.cif
_cod_data_source_block           mx3440
_cod_original_cell_volume        1518.7(9)
_cod_database_code               7224272
_shelxl_version_number           2013-4
_diffrn_number_total             6804
_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(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C27(H27), C28(H28),
  C29(H29), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C35(H35A,H35B,H35C)
;
_shelx_res_checksum              59765