#------------------------------------------------------------------------------
#$Date: 2022-10-07 04:10:41 +0300 (Fri, 07 Oct 2022) $
#$Revision: 278457 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/17/7061713.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_7061713
loop_
_publ_author_name
Pragya,
'Saini, Vaishali'
'Rangan, Krishnan'
'Khungar, Bharti'
_publ_section_title
;
 A pyrazinium-based fluorescent chemosensor for the selective detection of
 2,4,6-trinitrophenol in an aqueous medium
;
_journal_issue                   35
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16907
_journal_page_last               16913
_journal_paper_doi               10.1039/D2NJ02999E
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C19 H15 N2 S2, C6 H2 N3 O7'
_chemical_formula_sum            'C25 H17 N5 O7 S2'
_chemical_formula_weight         563.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-01
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-04-22 deposited with the CCDC.	2022-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.423(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.0779(3)
_cell_length_b                   20.0433(3)
_cell_length_c                   14.3377(3)
_cell_measurement_reflns_used    9226
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      79.1970
_cell_measurement_theta_min      4.0780
_cell_volume                     4836.20(16)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     64.00  89.00   0.50    5.91    --    0.00  37.00 120.00   50
  2  ω    -18.00  68.00   0.50    5.91    --    0.00  37.00   0.00  172
  3  ω      4.00  30.00   0.50    5.91    --    0.00  77.00-120.00   52
  4  ω     29.00  86.00   0.50    5.91    --    0.00  77.00   0.00  114
  5  ω     -6.00  34.00   0.50    5.91    --    0.00  37.00 120.00   80
  6  ω     33.00 134.00   0.50   23.64    --  107.20 -15.00 -90.00  202
  7  ω     19.00 138.00   0.50   23.64    --  107.20 -82.00 -90.00  238
  8  ω     94.00 153.00   0.50   23.64    --  107.20  45.00  60.00  118
  9  ω     96.00 122.00   0.50   23.64    --  107.20 -61.00 -60.00   52
 10  ω     41.00  67.00   0.50   23.64    --  107.20 -61.00 -60.00   52
 11  ω     20.00 126.00   0.50   23.64    --  107.20 -30.00  60.00  212
 12  ω     47.00  97.00   0.50   23.64    --  107.20 -77.00-180.00  100
 13  ω     18.00 124.00   0.50   23.64    --  107.20 -61.00 -90.00  212
 14  ω     50.00  76.00   0.50   23.64    --  107.20 -15.00  30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0212849000
_diffrn_orient_matrix_UB_12      0.0647764000
_diffrn_orient_matrix_UB_13      0.0423376000
_diffrn_orient_matrix_UB_21      -0.0671498000
_diffrn_orient_matrix_UB_22      -0.0368272000
_diffrn_orient_matrix_UB_23      0.0208213000
_diffrn_orient_matrix_UB_31      0.0585319000
_diffrn_orient_matrix_UB_32      -0.0188494000
_diffrn_orient_matrix_UB_33      0.1053030000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14206
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.838
_diffrn_reflns_theta_min         4.047
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.513
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_description       block
_exptl_crystal_F_000             2320
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0473
_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)+(0.0907P)²+3.2475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1418
_refine_ls_wR_factor_ref         0.1451
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4587
_reflns_number_total             5121
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj02999e2.cif
_cod_data_source_block           exp_845_bk_s2_autored
_cod_depositor_comments
'Adding full bibliography for 7061712--7061713.cif.'
_cod_database_code               7061713
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C25 H17 N5 O7 S2'
_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.
;
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.704
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C6(H6), C10(H10), C2(H2), C3(H3), C22(H22), C19(H19), C15(H15),
 C18(H18), C11(H11), C7(H7), C16(H16), C12(H12), C17(H17), C8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.393
_oxdiff_exptl_absorpt_empirical_full_min 0.554
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
S2 S 0.63563(2) 0.46581(2) 0.73458(3) 0.02747(15) Uani 1 1 d . . . . .
S1 S 0.47313(3) 0.64920(3) 0.59500(4) 0.03286(16) Uani 1 1 d . . . . .
O1 O 0.14690(8) 0.41760(8) 0.51957(10) 0.0365(3) Uani 1 1 d . . . . .
O5 O -0.18109(8) 0.49352(8) 0.20144(10) 0.0363(3) Uani 1 1 d . . . . .
O4 O -0.13072(9) 0.59244(7) 0.23711(11) 0.0369(3) Uani 1 1 d . . . . .
N2 N 0.34867(8) 0.41871(8) 0.50646(11) 0.0234(3) Uani 1 1 d . . . . .
N1 N 0.47259(8) 0.50306(8) 0.60026(10) 0.0230(3) Uani 1 1 d . . . . .
N4 N -0.12691(9) 0.53172(8) 0.25004(11) 0.0270(3) Uani 1 1 d . . . . .
O6 O 0.09059(11) 0.31738(8) 0.36492(12) 0.0476(4) Uani 1 1 d . . . . .
N3 N 0.13550(9) 0.56460(9) 0.50345(12) 0.0309(4) Uani 1 1 d . . . . .
N5 N 0.03486(11) 0.33616(9) 0.38688(12) 0.0327(4) Uani 1 1 d . . . . .
O3 O 0.12382(11) 0.62353(9) 0.48772(16) 0.0582(5) Uani 1 1 d . . . . .
O7 O -0.01070(12) 0.29900(9) 0.40451(17) 0.0590(5) Uani 1 1 d . . . . .
O2 O 0.19692(10) 0.54296(10) 0.56535(15) 0.0604(5) Uani 1 1 d . . . . .
C4 C 0.48158(10) 0.43678(10) 0.61289(12) 0.0232(4) Uani 1 1 d . . . . .
C1 C 0.40170(10) 0.52730(9) 0.54260(12) 0.0238(4) Uani 1 1 d . . . . .
C24 C -0.04843(11) 0.43373(9) 0.32737(12) 0.0248(4) Uani 1 1 d . . . . .
H24 H -0.090700 0.405403 0.288922 0.030 Uiso 1 1 calc R . . . .
C6 C 0.32696(11) 0.63659(10) 0.47119(13) 0.0268(4) Uani 1 1 d . . . . .
H6 H 0.277291 0.618191 0.430146 0.032 Uiso 1 1 calc R . . . .
C23 C -0.05622(10) 0.50315(9) 0.32215(12) 0.0229(3) Uani 1 1 d . . . . .
C10 C 0.58149(10) 0.34589(10) 0.70049(13) 0.0264(4) Uani 1 1 d . . . . .
H10 H 0.547273 0.308672 0.676329 0.032 Uiso 1 1 calc R . . . .
C2 C 0.33749(10) 0.48464(10) 0.49382(12) 0.0244(4) Uani 1 1 d . . . . .
H2 H 0.287304 0.502175 0.452817 0.029 Uiso 1 1 calc R . . . .
C3 C 0.41900(10) 0.39309(9) 0.56489(12) 0.0238(4) Uani 1 1 d . . . . .
H3 H 0.426048 0.346209 0.573396 0.029 Uiso 1 1 calc R . . . .
C22 C 0.00488(11) 0.54446(9) 0.37949(12) 0.0240(4) Uani 1 1 d . . . . .
H22 H -0.001003 0.591533 0.373189 0.029 Uiso 1 1 calc R . . . .
C9 C 0.55866(10) 0.41142(9) 0.67714(12) 0.0232(4) Uani 1 1 d . . . . .
C14 C 0.30275(10) 0.32869(9) 0.38104(12) 0.0248(4) Uani 1 1 d . . . . .
C20 C 0.08832(10) 0.44615(10) 0.45846(12) 0.0257(4) Uani 1 1 d . . . . .
C5 C 0.39314(11) 0.59905(10) 0.53117(13) 0.0256(4) Uani 1 1 d . . . . .
C25 C 0.02225(11) 0.40830(9) 0.38984(13) 0.0250(4) Uani 1 1 d . . . . .
C21 C 0.07425(10) 0.51729(10) 0.44569(13) 0.0242(4) Uani 1 1 d . . . . .
C19 C 0.33462(11) 0.26552(10) 0.40876(13) 0.0280(4) Uani 1 1 d . . . . .
H19 H 0.341232 0.248577 0.473199 0.034 Uiso 1 1 calc R . . . .
C13 C 0.28175(10) 0.37160(10) 0.45385(14) 0.0279(4) Uani 1 1 d . . . . .
H13A H 0.232965 0.397370 0.417540 0.033 Uiso 1 1 calc R . . . .
H13B H 0.271061 0.342958 0.503767 0.033 Uiso 1 1 calc R . . . .
C15 C 0.29215(11) 0.35309(10) 0.28571(14) 0.0289(4) Uani 1 1 d . . . . .
H15 H 0.269740 0.396059 0.265878 0.035 Uiso 1 1 calc R . . . .
C18 C 0.35690(11) 0.22690(10) 0.34308(15) 0.0324(4) Uani 1 1 d . . . . .
H18 H 0.378757 0.183729 0.362593 0.039 Uiso 1 1 calc R . . . .
C11 C 0.66210(11) 0.34097(11) 0.76480(14) 0.0321(4) Uani 1 1 d . . . . .
H11 H 0.688219 0.299784 0.788461 0.039 Uiso 1 1 calc R . . . .
C7 C 0.34492(13) 0.70559(11) 0.48073(15) 0.0352(4) Uani 1 1 d . . . . .
H7 H 0.308024 0.739247 0.446397 0.042 Uiso 1 1 calc R . . . .
C16 C 0.31443(12) 0.31441(11) 0.22008(14) 0.0336(4) Uani 1 1 d . . . . .
H16 H 0.307294 0.330954 0.155267 0.040 Uiso 1 1 calc R . . . .
C12 C 0.69823(11) 0.40135(11) 0.78917(13) 0.0315(4) Uani 1 1 d . . . . .
H12 H 0.752202 0.407057 0.831739 0.038 Uiso 1 1 calc R . . . .
C17 C 0.34723(12) 0.25141(11) 0.24899(15) 0.0339(4) Uani 1 1 d . . . . .
H17 H 0.362976 0.225223 0.204197 0.041 Uiso 1 1 calc R . . . .
C8 C 0.42057(14) 0.71883(11) 0.54420(16) 0.0365(4) Uani 1 1 d . . . . .
H8 H 0.441697 0.762664 0.558521 0.044 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C12 S2 C9 91.42(9) . . ?
C8 S1 C5 91.27(10) . . ?
C2 N2 C3 121.56(15) . . ?
C2 N2 C13 119.88(15) . . ?
C3 N2 C13 118.56(16) . . ?
C1 N1 C4 118.97(15) . . ?
O5 N4 C23 118.13(16) . . ?
O4 N4 O5 122.57(16) . . ?
O4 N4 C23 119.28(16) . . ?
O3 N3 O2 122.32(18) . . ?
O3 N3 C21 118.95(17) . . ?
O2 N3 C21 118.73(18) . . ?
O6 N5 C25 117.60(17) . . ?
O7 N5 O6 123.81(19) . . ?
O7 N5 C25 118.58(18) . . ?
N1 C4 C3 121.16(16) . . ?
N1 C4 C9 118.20(16) . . ?
C3 C4 C9 120.64(17) . . ?
N1 C1 C2 121.17(17) . . ?
N1 C1 C5 117.97(16) . . ?
C2 C1 C5 120.85(16) . . ?
C25 C24 C23 117.35(17) . . ?
C5 C6 C7 110.43(17) . . ?
C24 C23 N4 118.75(16) . . ?
C22 C23 N4 119.72(16) . . ?
C22 C23 C24 121.36(16) . . ?
C9 C10 C11 111.70(17) . . ?
N2 C2 C1 118.47(16) . . ?
N2 C3 C4 118.64(17) . . ?
C21 C22 C23 120.01(17) . . ?
C4 C9 S2 120.14(14) . . ?
C10 C9 S2 111.62(13) . . ?
C10 C9 C4 128.24(17) . . ?
C19 C14 C13 120.43(16) . . ?
C19 C14 C15 119.58(17) . . ?
C15 C14 C13 119.96(17) . . ?
O1 C20 C25 121.06(18) . . ?
O1 C20 C21 127.49(18) . . ?
C21 C20 C25 111.43(15) . . ?
C1 C5 S1 118.97(14) . . ?
C6 C5 S1 111.91(14) . . ?
C6 C5 C1 129.10(17) . . ?
C24 C25 N5 117.89(17) . . ?
C24 C25 C20 126.22(18) . . ?
C20 C25 N5 115.86(16) . . ?
C22 C21 N3 116.34(17) . . ?
C22 C21 C20 123.34(16) . . ?
C20 C21 N3 120.32(16) . . ?
C18 C19 C14 120.51(17) . . ?
N2 C13 C14 110.28(14) . . ?
C16 C15 C14 119.84(18) . . ?
C17 C18 C19 119.90(19) . . ?
C12 C11 C10 112.92(18) . . ?
C8 C7 C6 113.16(18) . . ?
C15 C16 C17 120.16(18) . . ?
C11 C12 S2 112.34(14) . . ?
C18 C17 C16 120.00(18) . . ?
C7 C8 S1 113.23(17) . . ?
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
S2 C9 1.7221(18) . ?
S2 C12 1.707(2) . ?
S1 C5 1.7240(19) . ?
S1 C8 1.696(2) . ?
O1 C20 1.241(2) . ?
O5 N4 1.238(2) . ?
O4 N4 1.229(2) . ?
N2 C2 1.339(2) . ?
N2 C3 1.343(2) . ?
N2 C13 1.502(2) . ?
N1 C4 1.343(3) . ?
N1 C1 1.337(2) . ?
N4 C23 1.437(2) . ?
O6 N5 1.220(2) . ?
N3 O3 1.206(2) . ?
N3 O2 1.220(2) . ?
N3 C21 1.463(2) . ?
N5 O7 1.204(2) . ?
N5 C25 1.467(3) . ?
C4 C3 1.397(2) . ?
C4 C9 1.453(2) . ?
C1 C2 1.405(2) . ?
C1 C5 1.449(3) . ?
C24 C23 1.398(3) . ?
C24 C25 1.363(2) . ?
C6 C5 1.409(3) . ?
C6 C7 1.416(3) . ?
C23 C22 1.385(2) . ?
C10 C9 1.381(3) . ?
C10 C11 1.415(2) . ?
C22 C21 1.379(2) . ?
C14 C19 1.388(3) . ?
C14 C13 1.504(2) . ?
C14 C15 1.397(2) . ?
C20 C25 1.453(2) . ?
C20 C21 1.448(3) . ?
C19 C18 1.388(3) . ?
C15 C16 1.388(3) . ?
C18 C17 1.385(3) . ?
C11 C12 1.359(3) . ?
C7 C8 1.364(3) . ?
C16 C17 1.392(3) . ?
