#------------------------------------------------------------------------------
#$Date: 2025-01-06 14:25:19 +0200 (Mon, 06 Jan 2025) $
#$Revision: 297110 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/74/7717432.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_7717432
loop_
_publ_author_name
'Gonçalves, Ana C R'
'Libardi, Silvia H.'
'Borges, Júlio C'
'Oliveira, Ronaldo J.'
'Gotzmann, Carla'
'Blacque, Olivier'
'de Albuquerque, Sergio'
'Lopes, Carla D.'
'Alberto, Roger'
'Maia, Pedro I. S.'
_publ_section_title
;
 Rhenium(I) and technetium(I) complexes with megazol derivatives: towards
 the development of a theranostic platform for Chagas disease.
;
_journal_issue                   48
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              19153
_journal_page_last               19165
_journal_paper_doi               10.1039/d4dt02714k
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C7 H8 N6 O2 S'
_chemical_formula_sum            'C7 H8 N6 O2 S'
_chemical_formula_weight         240.25
_chemical_name_common            LH,Me
_chemical_name_systematic
N-methyl-5-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-amine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-26
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-06-28 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.371(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.67495(16)
_cell_length_b                   9.4303(2)
_cell_length_c                   18.9778(5)
_cell_measurement_reflns_used    5353
_cell_measurement_temperature    159.99(10)
_cell_measurement_theta_max      78.4010
_cell_measurement_theta_min      4.6720
_cell_volume                     1011.17(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      159.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     42.00 128.00   0.50    0.60    --   51.31  38.00  30.00  172
  2  ω     76.00 162.00   0.50    2.40    --   90.00  57.00 -80.46  172
  3  ω     94.00 178.00   0.50    2.40    --  107.75  58.00-102.59  168
  4  ω     98.00 178.00   0.50    2.40    --  107.75  15.00 120.00  160
  5  ω     34.00  88.00   0.50    2.40    --  107.75 -53.00 123.90  108
  6  ω     33.00  82.00   0.50    2.40    --  107.75 -49.00  69.22   98
  7  ω     34.00  84.00   0.50    2.40    --  107.75 -51.00 -29.00  100
  8  ω     30.00  69.00   0.50    2.40    --  107.75 -30.00 -60.00   78
  9  ω     36.00 102.00   0.50    2.40    --  107.75 -59.00-125.76  132
 10  ω     35.00  91.00   0.50    2.40    --  107.75 -55.00 -91.61  112
 11  ω     30.00  69.00   0.50    2.40    --  107.75 -30.00-180.00   78
 12  ω     30.00  69.00   0.50    2.40    --  107.75 -30.00-150.00   78
 13  ω     32.00  77.00   0.50    2.40    --  107.75 -45.00 -90.00   90
 14  ω     30.00  69.00   0.50    2.40    --  107.75 -30.00   0.00   78
 15  ω     35.00  91.00   0.50    2.40    --  107.75 -55.00  25.27  112
 16  ω     30.00  69.00   0.50    2.40    --  107.75 -30.00  90.00   78
 17  ω     30.00  69.00   0.50    2.40    --  107.75 -30.00 150.00   78
 18  ω     28.00 117.00   0.50    2.40    --  107.75 -15.00  90.00  178
 19  ω     40.00 126.00   0.50    0.60    --   54.00  59.00 113.21  172
 20  ω     55.00 141.00   0.50    0.60    --   70.00  60.00-153.54  172
 21  ω    -65.00  21.00   0.50    0.60    --  -51.31  57.00 -30.00  172
 22  ω   -124.00 -37.00   0.50    0.60    --  -51.31 -57.00-180.00  174
 23  ω   -124.00 -37.00   0.50    0.60    --  -51.31 -57.00 -60.00  174
 24  ω   -146.00 -60.00   0.50    2.40    --  -74.00 -59.00-111.65  172
 25  ω   -158.00-113.00   0.50    2.40    --  -86.25 -58.00  41.90   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2403646000
_diffrn_orient_matrix_UB_12      -0.0423210000
_diffrn_orient_matrix_UB_13      -0.0254188000
_diffrn_orient_matrix_UB_21      -0.0225163000
_diffrn_orient_matrix_UB_22      0.1209071000
_diffrn_orient_matrix_UB_23      -0.0548281000
_diffrn_orient_matrix_UB_31      0.1269005000
_diffrn_orient_matrix_UB_32      0.1013448000
_diffrn_orient_matrix_UB_33      0.0547097000
_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  0.0344
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9328
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.484
_diffrn_reflns_theta_min         4.681
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.868
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0606P)²+0.8433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1162
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1862
_reflns_number_total             2026
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02714k2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7717431--7717436.cif.'
_cod_original_cell_volume        1011.17(5)
_cod_database_code               7717432
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C7 H8 N6 O2 S'
_chemical_oxdiff_usercomment     LB3
_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   0.894
_shelx_estimated_absorpt_t_min   0.490
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C7(H7A,H7B,H7C)
;
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.555
_oxdiff_exptl_absorpt_empirical_full_min 0.570
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
S1 S 1.02105(9) 0.78322(5) 0.51178(3) 0.02715(18) Uani 1 1 d . . . . .
O2 O 0.1534(3) 0.7770(2) 0.74949(10) 0.0457(5) Uani 1 1 d . . . . .
O1 O 0.3910(3) 0.6097(2) 0.79061(10) 0.0464(5) Uani 1 1 d . . . . .
N1 N 0.3336(3) 0.7044(2) 0.74772(10) 0.0321(4) Uani 1 1 d . . . . .
N2 N 0.6652(3) 0.65184(18) 0.67552(9) 0.0260(4) Uani 1 1 d . . . . .
N3 N 0.6320(3) 0.84006(18) 0.60285(9) 0.0278(4) Uani 1 1 d . . . . .
N4 N 1.0818(3) 0.56600(18) 0.59354(9) 0.0263(4) Uani 1 1 d . . . . .
N5 N 1.2547(3) 0.55537(18) 0.54831(9) 0.0268(4) Uani 1 1 d . . . . .
N6 N 1.3977(3) 0.6753(2) 0.45275(10) 0.0287(4) Uani 1 1 d . . . . .
H6 H 1.502(5) 0.616(3) 0.4535(15) 0.043(8) Uiso 1 1 d . . . . .
C1 C 0.4788(4) 0.7343(2) 0.69263(11) 0.0271(4) Uani 1 1 d . . . . .
C2 C 0.4606(4) 0.8481(2) 0.64767(11) 0.0289(4) Uani 1 1 d . . . . .
H2 H 0.345532 0.921197 0.647897 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7510(4) 0.7205(2) 0.62055(11) 0.0244(4) Uani 1 1 d . . . . .
C3 C 0.7510(4) 0.5173(2) 0.70759(13) 0.0365(5) Uani 1 1 d . . . . .
H3A H 0.868932 0.475742 0.679131 0.055 Uiso 1 1 calc R U . . .
H3B H 0.617966 0.451494 0.709297 0.055 Uiso 1 1 calc R U . . .
H3C H 0.823382 0.534855 0.755730 0.055 Uiso 1 1 calc R U . . .
C5 C 0.9474(3) 0.6769(2) 0.58157(10) 0.0245(4) Uani 1 1 d . . . . .
C6 C 1.2471(4) 0.6620(2) 0.50222(11) 0.0257(4) Uani 1 1 d . . . . .
C7 C 1.4075(5) 0.8035(3) 0.41097(13) 0.0386(5) Uani 1 1 d . . . . .
H7A H 1.532125 0.794319 0.378829 0.058 Uiso 1 1 calc R U . . .
H7B H 1.442344 0.884692 0.442496 0.058 Uiso 1 1 calc R U . . .
H7C H 1.254778 0.818296 0.383356 0.058 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 0.0181 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -1 0.0206
0 -1 1 0.0186
0 0 1 0.0297
0 0 -1 0.0167
-3 -2 -4 0.1129
2 0 -1 0.1338
0 1 1 0.0238
0 -1 -1 0.0148
2 -4 -7 0.0754
2 3 7 0.0936
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 S1 C5 86.14(9) . . ?
O2 N1 C1 116.74(19) . . ?
O1 N1 O2 123.60(19) . . ?
O1 N1 C1 119.67(19) . . ?
C1 N2 C3 128.48(18) . . ?
C4 N2 C1 104.54(17) . . ?
C4 N2 C3 126.96(18) . . ?
C4 N3 C2 105.32(17) . . ?
C5 N4 N5 113.12(17) . . ?
C6 N5 N4 112.10(16) . . ?
C6 N6 H6 116(2) . . ?
C6 N6 C7 121.58(19) . . ?
C7 N6 H6 121(2) . . ?
N2 C1 N1 125.03(19) . . ?
C2 C1 N1 126.9(2) . . ?
C2 C1 N2 108.11(18) . . ?
N3 C2 C1 109.36(18) . . ?
N3 C2 H2 125.3 . . ?
C1 C2 H2 125.3 . . ?
N2 C4 C5 127.17(18) . . ?
N3 C4 N2 112.67(18) . . ?
N3 C4 C5 120.15(18) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N4 C5 S1 114.62(15) . . ?
N4 C5 C4 127.08(19) . . ?
C4 C5 S1 118.29(15) . . ?
N5 C6 S1 114.01(15) . . ?
N5 C6 N6 123.39(19) . . ?
N6 C6 S1 122.60(16) . . ?
N6 C7 H7A 109.5 . . ?
N6 C7 H7B 109.5 . . ?
N6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
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
S1 C5 1.743(2) . ?
S1 C6 1.740(2) . ?
O2 N1 1.233(3) . ?
O1 N1 1.232(3) . ?
N1 C1 1.419(3) . ?
N2 C1 1.376(3) . ?
N2 C4 1.356(3) . ?
N2 C3 1.471(3) . ?
N3 C2 1.353(3) . ?
N3 C4 1.341(3) . ?
N4 N5 1.367(2) . ?
N4 C5 1.302(3) . ?
N5 C6 1.331(3) . ?
N6 H6 0.82(3) . ?
N6 C6 1.333(3) . ?
N6 C7 1.450(3) . ?
C1 C2 1.368(3) . ?
C2 H2 0.9500 . ?
C4 C5 1.454(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
N6 H6 N5_$1 0.82(3) 2.12(3) 2.938(3) 174(3) 3_866
C2 H2 O1_$2 0.95 2.57 3.446(3) 153.1 2_556
C3 H3A N4 0.98 2.28 3.030(3) 132.7 .
C3 H3B O2_$3 0.98 2.43 3.379(3) 162.1 2_546
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
_geom_torsion_publ_flag
O2 N1 C1 N2 -169.6(2) . . . . ?
O2 N1 C1 C2 10.6(3) . . . . ?
O1 N1 C1 N2 10.4(3) . . . . ?
O1 N1 C1 C2 -169.4(2) . . . . ?
N1 C1 C2 N3 179.44(19) . . . . ?
N2 C1 C2 N3 -0.4(2) . . . . ?
N2 C4 C5 S1 179.14(16) . . . . ?
N2 C4 C5 N4 -2.2(3) . . . . ?
N3 C4 C5 S1 -0.3(3) . . . . ?
N3 C4 C5 N4 178.35(19) . . . . ?
N4 N5 C6 S1 -0.4(2) . . . . ?
N4 N5 C6 N6 179.91(19) . . . . ?
N5 N4 C5 S1 -0.1(2) . . . . ?
N5 N4 C5 C4 -178.88(19) . . . . ?
C1 N2 C4 N3 0.5(2) . . . . ?
C1 N2 C4 C5 -179.01(19) . . . . ?
C2 N3 C4 N2 -0.8(2) . . . . ?
C2 N3 C4 C5 178.79(18) . . . . ?
C4 N2 C1 N1 -179.90(19) . . . . ?
C4 N2 C1 C2 0.0(2) . . . . ?
C4 N3 C2 C1 0.7(2) . . . . ?
C3 N2 C1 N1 1.6(3) . . . . ?
C3 N2 C1 C2 -178.5(2) . . . . ?
C3 N2 C4 N3 179.03(19) . . . . ?
C3 N2 C4 C5 -0.5(3) . . . . ?
C5 S1 C6 N5 0.23(16) . . . . ?
C5 S1 C6 N6 179.96(19) . . . . ?
C5 N4 N5 C6 0.3(2) . . . . ?
C6 S1 C5 N4 -0.05(16) . . . . ?
C6 S1 C5 C4 178.81(17) . . . . ?
C7 N6 C6 S1 10.2(3) . . . . ?
C7 N6 C6 N5 -170.1(2) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0001 0.9997 -1.0005 -0.0169 0.1757 0.0466
-0.0001 -0.9997 1.0005 0.0169 -0.1757 -0.0466
-0.0001 0.0005 1.0003 -0.0255 -0.0548 0.0548
0.0001 -0.0005 -1.0003 0.0255 0.0548 -0.0548
-2.9991 -2.0077 -4.0031 -0.5341 0.0443 -0.8031
1.9999 0.0032 -0.9990 0.5060 0.0101 0.1994
-0.0002 1.0007 1.0002 -0.0678 0.0662 0.1561
0.0002 -1.0007 -1.0002 0.0678 -0.0662 -0.1561
2.0007 -4.0005 -7.0006 0.8282 -0.1449 -0.5345
1.9988 3.0076 7.0034 0.1751 -0.0654 0.9416
