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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/44/7104419.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_7104419
loop_
_publ_author_name
'Wan, Jie-Ping'
'Pan, Yuan-Jiang'
_publ_section_title
;
 Chemo-/regioselective synthesis of 6-unsubstituted
 dihydropyrimidinones, 1,3-thiazines and chromones via novel variants
 of Biginelli reaction.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2768
_journal_page_last               2770
_journal_paper_doi               10.1039/b901112a
_journal_volume                  34
_journal_year                    2009
_chemical_formula_sum            'C17 H13 Cl N2 O S'
_chemical_formula_weight         328.81
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                   21.147(4)
_cell_length_b                   8.3692(17)
_cell_length_c                   18.124(4)
_cell_measurement_temperature    293(2)
_cell_volume                     3207.6(11)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            28828
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.31(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         7269
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0399
_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/[σ²(Fo²)+(0.0679P)²+0.0035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1345
_reflns_number_gt                4766
_reflns_number_total             7269
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B901112A.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 

2018-03-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_original_formula_sum        'C136 H104 Cl8 N16 O8 S8'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     2630.51
_cod_database_code               7104419
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.39965(16) 0.9143(4) 0.5795(2) 0.0537(8) Uani 1 1 d . . .
H1A H 0.4303 0.8513 0.5569 0.064 Uiso 1 1 calc R . .
C2 C 0.4174(2) 1.0205(4) 0.6345(2) 0.0674(11) Uani 1 1 d . . .
H2A H 0.4596 1.0287 0.6487 0.081 Uiso 1 1 calc R . .
C3 C 0.3720(2) 1.1134(4) 0.6676(2) 0.0686(11) Uani 1 1 d . . .
C4 C 0.3107(2) 1.1054(5) 0.6465(2) 0.0744(12) Uani 1 1 d . . .
H4A H 0.2807 1.1716 0.6683 0.089 Uiso 1 1 calc R . .
C5 C 0.29256(18) 0.9969(4) 0.5916(2) 0.0597(9) Uani 1 1 d . . .
H5A H 0.2503 0.9897 0.5778 0.072 Uiso 1 1 calc R . .
C6 C 0.33720(14) 0.9000(3) 0.55750(17) 0.0430(7) Uani 1 1 d . . .
C7 C 0.31849(14) 0.7775(3) 0.49920(17) 0.0396(6) Uani 1 1 d . . .
H7A H 0.3569 0.7433 0.4734 0.047 Uiso 1 1 calc R . .
C8 C 0.23106(14) 0.5798(4) 0.52472(18) 0.0435(7) Uani 1 1 d . . .
C9 C 0.21491(13) 0.7863(4) 0.43520(19) 0.0467(7) Uani 1 1 d . . .
H9A H 0.1881 0.8304 0.4000 0.056 Uiso 1 1 calc R . .
C10 C 0.27337(12) 0.8468(3) 0.44293(17) 0.0404(6) Uani 1 1 d . . .
C11 C 0.29768(13) 0.9694(3) 0.39412(17) 0.0414(7) Uani 1 1 d . . .
C12 C 0.25186(14) 1.0710(3) 0.35089(17) 0.0424(7) Uani 1 1 d . . .
C13 C 0.20493(17) 1.1522(4) 0.3873(2) 0.0615(9) Uani 1 1 d . . .
H13A H 0.1988 1.1375 0.4376 0.074 Uiso 1 1 calc R . .
C14 C 0.1665(2) 1.2571(5) 0.3476(3) 0.0799(13) Uani 1 1 d . . .
H14A H 0.1359 1.3170 0.3720 0.096 Uiso 1 1 calc R . .
C15 C 0.1736(2) 1.2719(5) 0.2734(3) 0.0860(14) Uani 1 1 d . . .
H15A H 0.1468 1.3385 0.2467 0.103 Uiso 1 1 calc R . .
C16 C 0.2197(2) 1.1895(6) 0.2383(3) 0.0862(14) Uani 1 1 d . . .
H16A H 0.2243 1.1999 0.1875 0.103 Uiso 1 1 calc R . .
C17 C 0.25994(19) 1.0905(4) 0.2765(2) 0.0659(10) Uani 1 1 d . . .
H17A H 0.2923 1.0373 0.2520 0.079 Uiso 1 1 calc R . .
C18 C 0.35667(15) 0.4030(4) 0.4001(2) 0.0521(8) Uani 1 1 d . . .
H18A H 0.3276 0.3323 0.4206 0.062 Uiso 1 1 calc R . .
C19 C 0.33872(18) 0.4965(4) 0.3408(2) 0.0599(9) Uani 1 1 d . . .
H19A H 0.2982 0.4881 0.3212 0.072 Uiso 1 1 calc R . .
C20 C 0.38155(18) 0.6017(4) 0.3115(2) 0.0569(9) Uani 1 1 d . . .
C21 C 0.4411(2) 0.6203(4) 0.3407(2) 0.0617(9) Uani 1 1 d . . .
H21A H 0.4691 0.6953 0.3215 0.074 Uiso 1 1 calc R . .
C22 C 0.45849(15) 0.5229(4) 0.40019(19) 0.0525(8) Uani 1 1 d . . .
H22A H 0.4988 0.5331 0.4203 0.063 Uiso 1 1 calc R . .
C23 C 0.41729(12) 0.4124(3) 0.42966(17) 0.0391(6) Uani 1 1 d . . .
C24 C 0.43637(13) 0.2982(3) 0.49132(17) 0.0404(6) Uani 1 1 d . . .
H24A H 0.3979 0.2664 0.5176 0.048 Uiso 1 1 calc R . .
C25 C 0.52105(13) 0.0917(3) 0.46927(18) 0.0432(7) Uani 1 1 d . . .
C26 C 0.53891(14) 0.3019(4) 0.55684(18) 0.0470(7) Uani 1 1 d . . .
H26A H 0.5660 0.3470 0.5915 0.056 Uiso 1 1 calc R . .
C27 C 0.48139(13) 0.3677(4) 0.54694(17) 0.0411(7) Uani 1 1 d . . .
C28 C 0.45722(14) 0.4939(3) 0.59463(16) 0.0422(7) Uani 1 1 d . . .
C29 C 0.49901(15) 0.5958(3) 0.64111(18) 0.0446(7) Uani 1 1 d . . .
C30 C 0.55607(17) 0.6563(4) 0.6158(2) 0.0635(9) Uani 1 1 d . . .
H30A H 0.5714 0.6266 0.5697 0.076 Uiso 1 1 calc R . .
C31 C 0.5903(2) 0.7621(5) 0.6598(3) 0.0873(15) Uani 1 1 d . . .
H31A H 0.6286 0.8028 0.6430 0.105 Uiso 1 1 calc R . .
C32 C 0.5677(2) 0.8061(5) 0.7276(3) 0.0770(11) Uani 1 1 d . . .
H32A H 0.5906 0.8773 0.7567 0.092 Uiso 1 1 calc R . .
C33 C 0.5120(2) 0.7463(4) 0.7527(2) 0.0673(11) Uani 1 1 d . . .
H33A H 0.4972 0.7757 0.7991 0.081 Uiso 1 1 calc R . .
C34 C 0.47708(18) 0.6418(4) 0.7098(2) 0.0557(8) Uani 1 1 d . . .
Cl1 Cl 0.39402(9) 1.24235(15) 0.73873(8) 0.1199(6) Uani 1 1 d . . .
Cl2 Cl 0.36044(6) 0.71882(13) 0.23557(6) 0.0856(3) Uani 1 1 d . . .
H34A H 0.4349(17) 0.610(4) 0.728(2) 0.058(9) Uiso 1 1 d . . .
N1 N 0.28925(11) 0.6356(3) 0.53334(15) 0.0452(6) Uani 1 1 d . . .
H1B H 0.3098 0.5883 0.5574 0.054 Uiso 1 1 d R . .
N2 N 0.19333(11) 0.6620(3) 0.47731(17) 0.0579(8) Uani 1 1 d . . .
H2B H 0.1601 0.6325 0.4743 0.070 Uiso 1 1 d R . .
N3 N 0.55908(11) 0.1722(3) 0.51819(16) 0.0549(7) Uani 1 1 d . . .
H3B H 0.5988 0.1246 0.5278 0.066 Uiso 1 1 d R . .
N4 N 0.46438(11) 0.1523(3) 0.45792(14) 0.0419(6) Uani 1 1 d . . .
H4B H 0.4331 0.1018 0.4298 0.050 Uiso 1 1 d R . .
O1 O 0.35491(9) 0.9932(3) 0.38865(14) 0.0531(6) Uani 1 1 d . . .
O2 O 0.39947(10) 0.5168(3) 0.59676(13) 0.0557(6) Uani 1 1 d . . .
S1 S 0.20497(4) 0.41793(10) 0.56990(5) 0.0564(2) Uani 1 1 d . . .
S2 S 0.54638(4) -0.07478(10) 0.42683(6) 0.0600(3) Uani 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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 121.4(4) . . ?
C6 C1 H1A 119.3 . . ?
C2 C1 H1A 119.3 . . ?
C3 C2 C1 119.2(4) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 Cl1 119.7(4) . . ?
C2 C3 Cl1 119.2(3) . . ?
C3 C4 C5 119.7(4) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
C1 C6 C5 118.0(3) . . ?
C1 C6 C7 120.3(3) . . ?
C5 C6 C7 121.6(3) . . ?
N1 C7 C10 109.1(2) . . ?
N1 C7 C6 111.1(3) . . ?
C10 C7 C6 111.9(2) . . ?
N1 C7 H7A 108.2 . . ?
C10 C7 H7A 108.2 . . ?
C6 C7 H7A 108.2 . . ?
N1 C8 N2 116.2(3) . . ?
N1 C8 S1 122.2(2) . . ?
N2 C8 S1 121.6(2) . . ?
C10 C9 N2 122.4(3) . . ?
C10 C9 H9A 118.8 . . ?
N2 C9 H9A 118.8 . . ?
C9 C10 C11 122.0(3) . . ?
C9 C10 C7 120.4(3) . . ?
C11 C10 C7 117.4(2) . . ?
O1 C11 C10 120.9(3) . . ?
O1 C11 C12 119.9(3) . . ?
C10 C11 C12 119.2(2) . . ?
C17 C12 C13 120.3(3) . . ?
C17 C12 C11 119.9(3) . . ?
C13 C12 C11 119.6(3) . . ?
C12 C13 C14 119.0(4) . . ?
C12 C13 H13A 120.5 . . ?
C14 C13 H13A 120.5 . . ?
C15 C14 C13 120.2(4) . . ?
C15 C14 H14A 119.9 . . ?
C13 C14 H14A 119.9 . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C15 C16 C17 121.2(5) . . ?
C15 C16 H16A 119.4 . . ?
C17 C16 H16A 119.4 . . ?
C12 C17 C16 119.4(4) . . ?
C12 C17 H17A 120.3 . . ?
C16 C17 H17A 120.3 . . ?
C19 C18 C23 121.3(3) . . ?
C19 C18 H18A 119.3 . . ?
C23 C18 H18A 119.3 . . ?
C20 C19 C18 118.9(3) . . ?
C20 C19 H19A 120.5 . . ?
C18 C19 H19A 120.5 . . ?
C19 C20 C21 121.9(3) . . ?
C19 C20 Cl2 119.8(3) . . ?
C21 C20 Cl2 118.3(3) . . ?
C20 C21 C22 118.1(3) . . ?
C20 C21 H21A 121.0 . . ?
C22 C21 H21A 121.0 . . ?
C23 C22 C21 121.5(3) . . ?
C23 C22 H22A 119.2 . . ?
C21 C22 H22A 119.2 . . ?
C22 C23 C18 118.1(3) . . ?
C22 C23 C24 122.5(3) . . ?
C18 C23 C24 119.4(3) . . ?
N4 C24 C27 109.8(2) . . ?
N4 C24 C23 108.8(2) . . ?
C27 C24 C23 114.6(2) . . ?
N4 C24 H24A 107.8 . . ?
C27 C24 H24A 107.8 . . ?
C23 C24 H24A 107.8 . . ?
N4 C25 N3 116.4(3) . . ?
N4 C25 S2 122.6(2) . . ?
N3 C25 S2 121.0(2) . . ?
C27 C26 N3 122.7(3) . . ?
C27 C26 H26A 118.6 . . ?
N3 C26 H26A 118.6 . . ?
C26 C27 C28 122.3(3) . . ?
C26 C27 C24 120.2(3) . . ?
C28 C27 C24 117.1(2) . . ?
O2 C28 C27 118.5(3) . . ?
O2 C28 C29 118.7(3) . . ?
C27 C28 C29 122.8(3) . . ?
C34 C29 C30 119.2(3) . . ?
C34 C29 C28 118.0(3) . . ?
C30 C29 C28 122.6(3) . . ?
C29 C30 C31 119.7(4) . . ?
C29 C30 H30A 120.2 . . ?
C31 C30 H30A 120.2 . . ?
C32 C31 C30 120.2(4) . . ?
C32 C31 H31A 119.9 . . ?
C30 C31 H31A 119.9 . . ?
C33 C32 C31 120.2(4) . . ?
C33 C32 H32A 119.9 . . ?
C31 C32 H32A 119.9 . . ?
C32 C33 C34 120.5(4) . . ?
C32 C33 H33A 119.7 . . ?
C34 C33 H33A 119.7 . . ?
C29 C34 C33 120.2(4) . . ?
C29 C34 H34A 122(2) . . ?
C33 C34 H34A 118(2) . . ?
C8 N1 C7 128.6(2) . . ?
C8 N1 H1B 115.5 . . ?
C7 N1 H1B 115.9 . . ?
C8 N2 C9 122.8(2) . . ?
C8 N2 H2B 115.5 . . ?
C9 N2 H2B 121.6 . . ?
C26 N3 C25 122.7(2) . . ?
C26 N3 H3B 121.3 . . ?
C25 N3 H3B 115.6 . . ?
C25 N4 C24 128.0(2) . . ?
C25 N4 H4B 123.6 . . ?
C24 N4 H4B 108.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.385(4) . ?
C1 C2 1.388(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.373(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.355(6) . ?
C3 Cl1 1.744(4) . ?
C4 C5 1.400(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.389(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.525(4) . ?
C7 N1 1.475(4) . ?
C7 C10 1.512(4) . ?
C7 H7A 0.9800 . ?
C8 N1 1.326(4) . ?
C8 N2 1.360(4) . ?
C8 S1 1.676(3) . ?
C9 C10 1.343(4) . ?
C9 N2 1.368(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.449(4) . ?
C11 O1 1.231(3) . ?
C11 C12 1.509(4) . ?
C12 C17 1.369(5) . ?
C12 C13 1.372(5) . ?
C13 C14 1.396(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.359(7) . ?
C14 H14A 0.9300 . ?
C15 C16 1.354(7) . ?
C15 H15A 0.9300 . ?
C16 C17 1.374(5) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C19 1.382(5) . ?
C18 C23 1.392(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.371(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.375(5) . ?
C20 Cl2 1.747(4) . ?
C21 C22 1.401(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.379(4) . ?
C22 H22A 0.9300 . ?
C23 C24 1.525(4) . ?
C24 N4 1.486(4) . ?
C24 C27 1.503(4) . ?
C24 H24A 0.9800 . ?
C25 N4 1.317(4) . ?
C25 N3 1.374(4) . ?
C25 S2 1.679(3) . ?
C26 C27 1.347(4) . ?
C26 N3 1.360(4) . ?
C26 H26A 0.9300 . ?
C27 C28 1.458(4) . ?
C28 O2 1.237(3) . ?
C28 C29 1.489(4) . ?
C29 C34 1.383(5) . ?
C29 C30 1.387(5) . ?
C30 C31 1.394(5) . ?
C30 H30A 0.9300 . ?
C31 C32 1.370(7) . ?
C31 H31A 0.9300 . ?
C32 C33 1.359(6) . ?
C32 H32A 0.9300 . ?
C33 C34 1.384(5) . ?
C33 H33A 0.9300 . ?
C34 H34A 0.99(3) . ?
N1 H1B 0.7314 . ?
N2 H2B 0.7473 . ?
N3 H3B 0.9464 . ?
N4 H4B 0.9368 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139181019
