#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/85/7218589.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7218589
loop_
_publ_author_name
'Sarkar, Satavisha'
'Das, Deb K.'
'Khan, Abu T.'
_publ_section_title
;
 Synthesis of fully-substituted pyridines and dihydropyridines in a highly
 chemoselective manner utilizing a multicomponent reaction (MCR) strategy
;
_journal_issue                   96
_journal_name_full               'RSC Adv.'
_journal_page_first              53752
_journal_paper_doi               10.1039/C4RA08237K
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C19 H19 N5, C2 H6 O S'
_chemical_formula_sum            'C21 H25 N5 O S'
_chemical_formula_weight         395.53
_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                84.207(2)
_cell_angle_beta                 72.287(2)
_cell_angle_gamma                75.180(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5845(3)
_cell_length_b                   10.8223(3)
_cell_length_c                   12.5073(4)
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.62
_cell_measurement_theta_min      2.43
_cell_volume                     1069.73(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13065
_diffrn_reflns_theta_full        28.42
_diffrn_reflns_theta_max         28.42
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'needle shape'
_exptl_crystal_F_000             420.0
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.109
_refine_diff_density_min         -1.204
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.005(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0772
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1324P)²+0.7180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2353
_refine_ls_wR_factor_ref         0.2513
_reflns_number_gt                3420
_reflns_number_total             5294
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra08237k2.cif
_cod_data_source_block           4a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 
;
_cod_database_code               7218589
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C9 C 0.6218(3) 0.4809(2) 0.1958(2) 0.0342(5) Uani 1 1 d .
C12 C 0.4749(3) 0.6232(2) 0.3869(2) 0.0330(5) Uani 1 1 d .
C10 C 0.6976(3) 0.5758(2) 0.2165(2) 0.0356(6) Uani 1 1 d .
C11 C 0.6249(3) 0.6459(2) 0.3147(2) 0.0329(5) Uani 1 1 d .
N5 N 0.6971(3) 0.4102(2) 0.1034(2) 0.0453(6) Uani 1 1 d .
C3 C 0.7040(3) 0.7434(2) 0.3375(2) 0.0349(5) Uani 1 1 d .
C1 C 0.3927(3) 0.6875(3) 0.4911(2) 0.0383(6) Uani 1 1 d .
C2 C 0.8385(4) 0.6060(3) 0.1321(3) 0.0473(7) Uani 1 1 d .
C14 C 0.6442(4) 0.3043(3) 0.0736(2) 0.0454(7) Uani 1 1 d .
H14 H 0.5256 0.3114 0.1155 0.054 Uiso 1 1 calc R
C4 C 0.6140(4) 0.8693(3) 0.3556(2) 0.0447(7) Uani 1 1 d .
H4 H 0.5011 0.8919 0.3575 0.054 Uiso 1 1 calc R
C8 C 0.8725(4) 0.7102(3) 0.3372(2) 0.0445(7) Uani 1 1 d .
H8 H 0.9342 0.6259 0.3262 0.053 Uiso 1 1 calc R
C7 C 0.9476(4) 0.8033(3) 0.3533(3) 0.0564(8) Uani 1 1 d .
H7 H 1.0596 0.7813 0.3535 0.068 Uiso 1 1 calc R
C5 C 0.6904(4) 0.9620(3) 0.3708(3) 0.0546(8) Uani 1 1 d .
H5 H 0.6292 1.0464 0.3822 0.066 Uiso 1 1 calc R
C6 C 0.8567(5) 0.9289(3) 0.3691(3) 0.0590(9) Uani 1 1 d .
H6 H 0.9082 0.9912 0.3786 0.071 Uiso 1 1 calc R
C17 C 0.7125(5) 0.0759(4) -0.0571(4) 0.0744(11) Uani 1 1 d .
H17A H 0.8296 0.0667 -0.1002 0.089 Uiso 1 1 calc R
H17B H 0.6735 0.0072 -0.0768 0.089 Uiso 1 1 calc R
C16 C 0.6113(6) 0.2013(4) -0.0869(4) 0.0774(12) Uani 1 1 d .
H16A H 0.6285 0.2070 -0.1674 0.093 Uiso 1 1 calc R
H16B H 0.4928 0.2062 -0.0505 0.093 Uiso 1 1 calc R
C15 C 0.6594(5) 0.3128(4) -0.0515(3) 0.0617(9) Uani 1 1 d .
H15A H 0.5867 0.3922 -0.0682 0.074 Uiso 1 1 calc R
H15B H 0.7744 0.3134 -0.0941 0.074 Uiso 1 1 calc R
C19 C 0.7452(5) 0.1778(3) 0.1044(3) 0.0645(9) Uani 1 1 d .
H19A H 0.7264 0.1723 0.1851 0.077 Uiso 1 1 calc R
H19B H 0.8640 0.1730 0.0691 0.077 Uiso 1 1 calc R
C18 C 0.6987(7) 0.0648(4) 0.0681(4) 0.0846(13) Uani 1 1 d .
H18A H 0.5845 0.0624 0.1111 0.102 Uiso 1 1 calc R
H18B H 0.7733 -0.0143 0.0835 0.102 Uiso 1 1 calc R
N3 N 0.4748(3) 0.4632(2) 0.26384(17) 0.0351(5) Uani 1 1 d .
N4 N 0.2536(3) 0.5141(3) 0.4218(2) 0.0468(6) Uani 1 1 d .
N2 N 0.3229(3) 0.7348(3) 0.5752(2) 0.0561(7) Uani 1 1 d .
N1 N 0.9481(4) 0.6284(3) 0.0611(3) 0.0730(10) Uani 1 1 d .
S1 S 0.07957(12) 0.24245(10) 0.34454(11) 0.0778(4) Uani 1 1 d .
C20 C 0.2936(5) 0.1867(4) 0.3329(4) 0.0780(12) Uani 1 1 d .
H20A H 0.3540 0.2466 0.2885 0.117 Uiso 1 1 calc R
H20B H 0.3351 0.1053 0.2974 0.117 Uiso 1 1 calc R
H20C H 0.3093 0.1775 0.4063 0.117 Uiso 1 1 calc R
C21 C 0.0956(9) 0.2731(7) 0.2017(5) 0.155(4) Uani 1 1 d .
H21A H -0.0144 0.3095 0.1931 0.233 Uiso 1 1 calc R
H21B H 0.1439 0.1945 0.1619 0.233 Uiso 1 1 calc R
H21C H 0.1661 0.3318 0.1720 0.233 Uiso 1 1 calc R
O1 O 0.0266(3) 0.3711(2) 0.3910(2) 0.0625(7) Uani 1 1 d .
C22 C 0.4010(3) 0.5328(2) 0.3568(2) 0.0332(5) Uani 1 1 d .
H4A H 0.206(4) 0.548(3) 0.476(3) 0.042(8) Uiso 1 1 d .
H4B H 0.207(4) 0.468(3) 0.403(3) 0.050(9) Uiso 1 1 d .
H5N H 0.788(5) 0.413(3) 0.064(3) 0.049(9) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N3 C9 N5 118.9(2)
N3 C9 C10 121.8(2)
N5 C9 C10 119.3(2)
C11 C12 C22 119.3(2)
C11 C12 C1 121.9(2)
C22 C12 C1 118.9(2)
C11 C10 C9 119.9(2)
C11 C10 C2 120.4(2)
C9 C10 C2 119.6(2)
C10 C11 C12 117.5(2)
C10 C11 C3 120.2(2)
C12 C11 C3 122.3(2)
C9 N5 C14 126.4(2)
C4 C3 C8 119.1(2)
C4 C3 C11 120.6(2)
C8 C3 C11 120.3(2)
N2 C1 C12 176.9(3)
N1 C2 C10 176.7(3)
N5 C14 C19 111.2(3)
N5 C14 C15 109.7(3)
C19 C14 C15 110.9(2)
C5 C4 C3 120.7(3)
C7 C8 C3 119.8(3)
C6 C7 C8 120.3(3)
C6 C5 C4 119.9(3)
C5 C6 C7 120.3(3)
C16 C17 C18 111.6(3)
C15 C16 C17 111.8(3)
C16 C15 C14 111.4(3)
C14 C19 C18 112.3(3)
C19 C18 C17 110.8(3)
C22 N3 C9 118.8(2)
O1 S1 C20 106.94(19)
O1 S1 C21 103.2(3)
C20 S1 C21 98.5(3)
N3 C22 N4 117.2(2)
N3 C22 C12 122.5(2)
N4 C22 C12 120.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C9 N3 1.339(3)
C9 N5 1.345(3)
C9 C10 1.430(4)
C12 C11 1.395(3)
C12 C22 1.428(3)
C12 C1 1.432(3)
C10 C11 1.398(3)
C10 C2 1.427(4)
C11 C3 1.483(3)
N5 C14 1.454(4)
C3 C4 1.387(4)
C3 C8 1.397(4)
C1 N2 1.139(3)
C2 N1 1.139(4)
C14 C19 1.504(5)
C14 C15 1.525(4)
C4 C5 1.387(4)
C8 C7 1.387(4)
C7 C6 1.383(5)
C5 C6 1.374(5)
C17 C16 1.492(6)
C17 C18 1.528(6)
C16 C15 1.516(5)
C19 C18 1.527(5)
N3 C22 1.343(3)
N4 C22 1.333(3)
S1 O1 1.470(2)
S1 C20 1.746(4)
S1 C21 1.753(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199404
