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#$Date: 2023-05-17 10:04:19 +0300 (Wed, 17 May 2023) $
#$Revision: 283815 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/72/8107213.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_8107213
loop_
_publ_author_name
'Radulović, Niko S.'
'Sejmanović, Dragana M.'
'Ristić, Milenko N.'
'Dekić, Vidoslav S.'
'Krüger, Biljana'
'Kahlenberg, Volker'
'Rodić, Marko V.'
_publ_section_title
;
 The crystal structure of
 3-(1-(2-((5-methylthiophen-2-yl)methylene)hydrazinyl)ethylidene)chroman-2,4-dione,
 C17H14N2O3S
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              775
_journal_page_last               777
_journal_paper_doi               10.1515/ncrs-2022-0225
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C17 H14 N2 O3 S'
_chemical_formula_sum            'C17 H14 N2 O3 S'
_chemical_formula_weight         326.36
_chemical_melting_point          463
_chemical_name_common
; 3-(1-(2-((5-Methylthiophen-2-yl)methylene)hydrazinyl)ethylidene)chroman-2,4-
dione
;
_chemical_name_systematic
; 1-[-1-(4-Hydroxy-2-oxo-2H-chromen-3-yl)ethylidene]-2-(4-methoxybenziylidene)
hydrazine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   .
_cell_angle_alpha                90
_cell_angle_beta                 92.245(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8966(5)
_cell_length_b                   9.4360(4)
_cell_length_c                   16.7115(7)
_cell_measurement_reflns_used    14477
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.3430
_cell_measurement_theta_min      3.0820
_cell_volume                     1559.39(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'ShelXle (Hübschle, 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3575
_diffrn_detector_type            'Ruby (Oxford Diffraction)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -18.00  43.00   1.00   20.00    --    9.94 -77.00-120.00   61
  2  ω    -40.00  61.00   1.00   20.00    --  -11.66  57.00-120.00  101
  3  ω    -84.00  16.00   1.00   20.00    --  -11.66 -57.00  90.00  100
  4  ω    -18.00  83.00   1.00   20.00    --    9.94  57.00 -60.00  101
  5  ω      1.00  51.00   1.00   20.00    --    9.94 -99.00   0.00   50
  6  ω    -23.00  39.00   1.00   20.00    --    9.94  77.00  60.00   62
  7  ω    -18.00  43.00   1.00   20.00    --    9.94 -77.00 120.00   61
  8  ω    -64.00  34.00   1.00   20.00    --    9.94 -38.00   0.00   98
  9  ω   -100.00 -38.00   1.00   20.00    --  -11.66-179.00   0.00   62
 10  ω    -18.00  54.00   1.00   20.00    --    9.94  57.00  30.00   72
 11  ω    -44.00  39.00   1.00   20.00    --  -11.66  77.00 150.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Gemini R ultra (Oxford Diffraction)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0355816000
_diffrn_orient_matrix_UB_12      -0.0642634000
_diffrn_orient_matrix_UB_13      -0.0055982000
_diffrn_orient_matrix_UB_21      0.0622821000
_diffrn_orient_matrix_UB_22      0.0368012000
_diffrn_orient_matrix_UB_23      0.0049364000
_diffrn_orient_matrix_UB_31      0.0002852000
_diffrn_orient_matrix_UB_32      -0.0128980000
_diffrn_orient_matrix_UB_33      0.0418131000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            32946
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.439
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type
'Enhance (Mo) X-ray Source (Oxford Diffraction)'
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       irregular
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.528
_exptl_crystal_size_mid          0.462
_exptl_crystal_size_min          0.255
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.033(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0358
_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/[σ²(Fo²)+(0.0572P)²+0.3038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1013
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2792
_reflns_number_total             3188
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0225_suppl.cif
_cod_data_source_block           VD35N_4119S_s3_2_m_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107213
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_oxdiff_exptl_absorpt_empirical_full_min 0.961
_oxdiff_exptl_absorpt_empirical_full_max 1.033
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_theta     26.32
_reflns_odcompleteness_iscentric 1
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.87812(4) 0.67596(4) 0.36715(2) 0.04671(14) Uani 1 1 d . . . . .
O1 O 0.43999(11) 0.06147(11) 0.66941(5) 0.0505(3) Uani 1 1 d . . . . .
O2 O 0.60654(13) 0.20437(14) 0.69839(6) 0.0685(4) Uani 1 1 d . . . . .
O3 O 0.39687(11) 0.20110(12) 0.43885(6) 0.0552(3) Uani 1 1 d . . . . .
N1 N 0.59360(12) 0.36706(13) 0.46404(7) 0.0429(3) Uani 1 1 d . . . . .
H1 H 0.5290(18) 0.3197(18) 0.4343(11) 0.065(5) Uiso 1 1 d . . . . .
N2 N 0.67878(12) 0.46785(12) 0.43386(7) 0.0444(3) Uani 1 1 d . . . . .
C2 C 0.52581(15) 0.16768(15) 0.64641(8) 0.0452(3) Uani 1 1 d . . . . .
C3 C 0.51281(13) 0.22073(14) 0.56514(7) 0.0391(3) Uani 1 1 d . . . . .
C4 C 0.41183(13) 0.16285(14) 0.51051(7) 0.0401(3) Uani 1 1 d . . . . .
C4' C 0.32269(13) 0.05342(14) 0.54086(8) 0.0405(3) Uani 1 1 d . . . . .
C5 C 0.21898(15) -0.00668(17) 0.49305(9) 0.0500(3) Uani 1 1 d . . . . .
H5 H 0.204646 0.024035 0.439251 0.060 Uiso 1 1 calc R U . . .
C6 C 0.13748(16) -0.11000(18) 0.52334(10) 0.0573(4) Uani 1 1 d . . . . .
H6 H 0.066792 -0.150188 0.490601 0.069 Uiso 1 1 calc R U . . .
C7 C 0.15857(17) -0.15553(18) 0.60176(11) 0.0592(4) Uani 1 1 d . . . . .
H7 H 0.102092 -0.227134 0.622364 0.071 Uiso 1 1 calc R U . . .
C8 C 0.26002(17) -0.09842(17) 0.64997(10) 0.0566(4) Uani 1 1 d . . . . .
H8 H 0.274617 -0.130236 0.703544 0.068 Uiso 1 1 calc R U . . .
C8' C 0.34080(14) 0.00667(14) 0.61892(8) 0.0433(3) Uani 1 1 d . . . . .
C9 C 0.60231(14) 0.32835(14) 0.54005(8) 0.0415(3) Uani 1 1 d . . . . .
C10 C 0.70383(18) 0.40300(19) 0.59326(10) 0.0635(4) Uani 1 1 d . . . . .
H10A H 0.777992 0.337998 0.607877 0.095 Uiso 1 1 calc R U . . .
H10B H 0.660589 0.434974 0.641838 0.095 Uiso 1 1 calc R U . . .
H10C H 0.739597 0.485039 0.565023 0.095 Uiso 1 1 calc R U . . .
C11 C 0.65823(14) 0.49418(15) 0.35937(8) 0.0431(3) Uani 1 1 d . . . . .
H11 H 0.588580 0.445543 0.329849 0.052 Uiso 1 1 calc R U . . .
C12 C 0.73950(13) 0.59656(14) 0.32004(8) 0.0412(3) Uani 1 1 d . . . . .
C13 C 0.72116(15) 0.64599(16) 0.24346(8) 0.0480(3) Uani 1 1 d . . . . .
H13 H 0.650260 0.615188 0.207619 0.058 Uiso 1 1 calc R U . . .
C14 C 0.81824(16) 0.74708(16) 0.22345(9) 0.0512(4) Uani 1 1 d . . . . .
H14 H 0.819254 0.791784 0.172536 0.061 Uiso 1 1 calc R U . . .
C15 C 0.91036(15) 0.77500(16) 0.28349(9) 0.0475(3) Uani 1 1 d . . . . .
C16 C 1.02682(18) 0.8761(2) 0.28408(11) 0.0647(4) Uani 1 1 d . . . . .
H16A H 1.020505 0.935234 0.235864 0.097 Uiso 1 1 calc R U . . .
H16B H 1.111840 0.822800 0.285089 0.097 Uiso 1 1 calc R U . . .
H16C H 1.024386 0.936586 0.331686 0.097 Uiso 1 1 calc R U . . .
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'
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
C15 S1 C12 91.98(7) . .
C8' O1 C2 122.49(11) . .
C9 N1 N2 121.62(12) . .
C9 N1 H1 114.0(11) . .
N2 N1 H1 124.4(11) . .
C11 N2 N1 114.46(12) . .
O2 C2 O1 113.93(12) . .
O2 C2 C3 127.39(14) . .
O1 C2 C3 118.67(12) . .
C9 C3 C4 120.71(11) . .
C9 C3 C2 119.34(12) . .
C4 C3 C2 119.94(13) . .
O3 C4 C3 123.46(13) . .
O3 C4 C4' 118.97(12) . .
C3 C4 C4' 117.57(11) . .
C8' C4' C5 118.41(13) . .
C8' C4' C4 119.69(12) . .
C5 C4' C4 121.90(12) . .
C6 C5 C4' 120.41(14) . .
C6 C5 H5 119.8 . .
C4' C5 H5 119.8 . .
C5 C6 C7 119.92(15) . .
C5 C6 H6 120.0 . .
C7 C6 H6 120.0 . .
C8 C7 C6 120.83(15) . .
C8 C7 H7 119.6 . .
C6 C7 H7 119.6 . .
C7 C8 C8' 118.70(15) . .
C7 C8 H8 120.7 . .
C8' C8 H8 120.7 . .
O1 C8' C4' 121.60(13) . .
O1 C8' C8 116.67(13) . .
C4' C8' C8 121.73(14) . .
N1 C9 C3 117.59(12) . .
N1 C9 C10 117.36(13) . .
C3 C9 C10 125.04(12) . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N2 C11 C12 120.47(13) . .
N2 C11 H11 119.8 . .
C12 C11 H11 119.8 . .
C13 C12 C11 127.07(13) . .
C13 C12 S1 110.66(11) . .
C11 C12 S1 122.27(10) . .
C12 C13 C14 112.81(13) . .
C12 C13 H13 123.6 . .
C14 C13 H13 123.6 . .
C15 C14 C13 113.75(13) . .
C15 C14 H14 123.1 . .
C13 C14 H14 123.1 . .
C14 C15 C16 128.66(14) . .
C14 C15 S1 110.80(11) . .
C16 C15 S1 120.54(12) . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C15 1.7218(15) .
S1 C12 1.7257(14) .
O1 C8' 1.3704(17) .
O1 C2 1.3780(18) .
O2 C2 1.2076(17) .
O3 C4 1.2539(16) .
N1 C9 1.3212(17) .
N1 N2 1.3795(17) .
N1 H1 0.911(18) .
N2 C11 1.2779(17) .
C2 C3 1.4484(18) .
C3 C9 1.422(2) .
C3 C4 1.4350(18) .
C4 C4' 1.462(2) .
C4' C8' 1.3820(18) .
C4' C5 1.396(2) .
C5 C6 1.374(2) .
C5 H5 0.9500 .
C6 C7 1.387(2) .
C6 H6 0.9500 .
C7 C8 1.373(2) .
C7 H7 0.9500 .
C8 C8' 1.387(2) .
C8 H8 0.9500 .
C9 C10 1.492(2) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 C12 1.4330(19) .
C11 H11 0.9500 .
C12 C13 1.3676(19) .
C13 C14 1.404(2) .
C13 H13 0.9500 .
C14 C15 1.355(2) .
C14 H14 0.9500 .
C15 C16 1.496(2) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.911(18) 1.725(18) 2.5211(16) 144.2(16) . yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C9 N1 N2 C11 179.99(12) . . . .
C8' O1 C2 O2 179.44(13) . . . .
C8' O1 C2 C3 -1.63(19) . . . .
O2 C2 C3 C9 0.0(2) . . . .
O1 C2 C3 C9 -178.78(12) . . . .
O2 C2 C3 C4 178.90(15) . . . .
O1 C2 C3 C4 0.13(19) . . . .
C9 C3 C4 O3 0.7(2) . . . .
C2 C3 C4 O3 -178.23(13) . . . .
C9 C3 C4 C4' -179.46(11) . . . .
C2 C3 C4 C4' 1.64(18) . . . .
O3 C4 C4' C8' 177.83(12) . . . .
C3 C4 C4' C8' -2.05(18) . . . .
O3 C4 C4' C5 -1.9(2) . . . .
C3 C4 C4' C5 178.22(12) . . . .
C8' C4' C5 C6 -0.1(2) . . . .
C4 C4' C5 C6 179.61(13) . . . .
C4' C5 C6 C7 -0.3(2) . . . .
C5 C6 C7 C8 0.2(3) . . . .
C6 C7 C8 C8' 0.4(2) . . . .
C2 O1 C8' C4' 1.2(2) . . . .
C2 O1 C8' C8 -179.05(13) . . . .
C5 C4' C8' O1 -179.60(12) . . . .
C4 C4' C8' O1 0.67(19) . . . .
C5 C4' C8' C8 0.7(2) . . . .
C4 C4' C8' C8 -179.03(13) . . . .
C7 C8 C8' O1 179.43(13) . . . .
C7 C8 C8' C4' -0.9(2) . . . .
N2 N1 C9 C3 -178.21(11) . . . .
N2 N1 C9 C10 2.9(2) . . . .
C4 C3 C9 N1 -3.53(19) . . . .
C2 C3 C9 N1 175.38(12) . . . .
C4 C3 C9 C10 175.31(14) . . . .
C2 C3 C9 C10 -5.8(2) . . . .
N1 N2 C11 C12 -179.90(12) . . . .
N2 C11 C12 C13 -172.97(14) . . . .
N2 C11 C12 S1 6.56(19) . . . .
C15 S1 C12 C13 -0.01(11) . . . .
C15 S1 C12 C11 -179.62(12) . . . .
C11 C12 C13 C14 179.48(13) . . . .
S1 C12 C13 C14 -0.10(16) . . . .
C12 C13 C14 C15 0.2(2) . . . .
C13 C14 C15 C16 -179.65(16) . . . .
C13 C14 C15 S1 -0.20(17) . . . .
C12 S1 C15 C14 0.12(12) . . . .
C12 S1 C15 C16 179.62(13) . . . .
