#------------------------------------------------------------------------------
#$Date: 2024-06-28 11:32:51 +0200 (Fri 28 de Jun de 2024) $
#$Revision: 292638 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/46/7244658.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_7244658
loop_
_publ_author_name
'Maganti, Lakshmi Haritha Bharathi'
'Ramesh, Deepthi'
'Vijayakumar, Balaji Gowrivel'
'Khan, Mohd Imran K.'
'Dhayalan, Arunkumar'
'Kamalraja, Jayabal'
'Kannan, Tharanikkarasu'
_publ_section_title
;
 Acetylene containing 2-(2-hydrazinyl)thiazole derivatives: design,
 synthesis, and in vitro and in silico evaluation of antimycobacterial
 activity against Mycobacterium tuberculosis
;
_journal_issue                   14
_journal_name_full               'RSC Advances'
_journal_page_first              8771
_journal_page_last               8782
_journal_paper_doi               10.1039/D2RA00928E
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C11 H11 N3 O S'
_chemical_formula_sum            'C11 H11 N3 O S'
_chemical_formula_weight         233.29
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc26fjmt
_audit_creation_date             2020-10-15
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_audit_update_record
;
2020-10-16 deposited with the CCDC.	2022-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                95.201(5)
_cell_angle_beta                 95.934(5)
_cell_angle_gamma                107.575(5)
_cell_formula_units_Z            4
_cell_length_a                   8.6009(5)
_cell_length_b                   10.6365(7)
_cell_length_c                   13.6233(9)
_cell_measurement_reflns_used    4261
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.3789
_cell_measurement_theta_min      3.1174
_cell_volume                     1171.97(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.9975
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -17.00   24.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.8710  -99.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega  -19.00    9.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.8710  -99.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega   26.00   65.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   80.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000  -60.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega   -6.00   90.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   37.0000 -150.0000 96

#__ type_ start__ end____ width___ exp.time_
  6 omega  -49.00   45.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835  -37.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
  7 omega  -93.00  -32.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.8710  178.0000  120.0000 61

#__ type_ start__ end____ width___ exp.time_
  8 omega   -2.00   23.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   32.00   96.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835 -178.0000   60.0000 64
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0659723000
_diffrn_orient_matrix_UB_12      0.0251355000
_diffrn_orient_matrix_UB_13      -0.0274043000
_diffrn_orient_matrix_UB_21      0.0514223000
_diffrn_orient_matrix_UB_22      0.0332202000
_diffrn_orient_matrix_UB_23      0.0447613000
_diffrn_orient_matrix_UB_31      0.0251285000
_diffrn_orient_matrix_UB_32      -0.0569201000
_diffrn_orient_matrix_UB_33      0.0056156000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12789
_diffrn_reflns_theta_full        29.44
_diffrn_reflns_theta_max         29.44
_diffrn_reflns_theta_min         3.12
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0435
_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)+(0.0475P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                3591
_reflns_number_total             5520
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ra00928e2.cif
_cod_data_source_block           4
_cod_depositor_comments
;

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C22 H22 N6 O2 S2'
_cod_original_formula_weight         466.58
_cod_original_formula_moiety         '2(C11 H11 N3 O S)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1171.95(12)
_cod_database_code               7244658
_chemical_oxdiff_formula         'C15 H16 O2 N2'
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C29(H29A,H29B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N6(H6), C9(H9), C13(H13), C19(H19), C20(H20), C24(H24), C26(H26),
 C27(H27), C28(H28), C30(H30), C31(H31)
2.c X=CH2 refined with riding coordinates:
 N11(H11A,H11B), N14(H14A,H14B)
2.d :
 C25(H25), C32(H32)
;
_olex2_date_sample_data_collection 1566597833.08
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.47214(5) 0.82581(4) -0.02329(4) 0.04222(14) Uani 1 d . . .
S2 S -0.04954(6) -0.26846(5) 1.01660(4) 0.04921(15) Uani 1 d . . .
N3 N 0.52509(17) 0.55091(13) 0.13471(11) 0.0377(3) Uani 1 d . . .
N4 N 0.11550(16) -0.11195(13) 0.89897(11) 0.0380(3) Uani 1 d . . .
H4 H 0.1987 -0.1354 0.9206 0.046 Uiso 1 calc . . R
N5 N 0.12907(16) -0.02562(13) 0.82887(10) 0.0367(3) Uani 1 d . . .
N6 N 0.55593(16) 0.65345(13) 0.07797(10) 0.0386(3) Uani 1 d . . .
H6 H 0.6554 0.6941 0.0692 0.046 Uiso 1 calc . . R
O7 O 0.90873(16) 0.43986(14) 0.23054(11) 0.0595(4) Uani 1 d . . .
O8 O 0.57597(15) 0.12636(13) 0.75310(10) 0.0530(3) Uani 1 d . . .
C9 C 0.2707(2) 0.01888(15) 0.80272(13) 0.0357(4) Uani 1 d . . .
H9 H 0.3573 -0.0072 0.8311 0.043 Uiso 1 calc . . R
C10 C 0.2986(2) 0.11072(16) 0.72843(13) 0.0359(4) Uani 1 d . . .
N11 N -0.14899(17) -0.11743(15) 0.89806(12) 0.0529(4) Uani 1 d . . .
H11A H -0.1336 -0.0622 0.8549 0.064 Uiso 1 calc . . R
H11B H -0.2436 -0.1453 0.9181 0.064 Uiso 1 calc . . R
C12 C -0.0281(2) -0.15912(15) 0.93324(13) 0.0358(4) Uani 1 d . . .
C13 C 0.6512(2) 0.52572(16) 0.17401(13) 0.0391(4) Uani 1 d . . .
H13 H 0.7554 0.5743 0.1618 0.047 Uiso 1 calc . . R
N14 N 0.28149(17) 0.61637(14) 0.04474(12) 0.0494(4) Uani 1 d . . .
H14A H 0.2673 0.5480 0.0761 0.059 Uiso 1 calc . . R
H14B H 0.1977 0.6363 0.0190 0.059 Uiso 1 calc . . R
C15 C 0.6336(2) 0.42126(15) 0.23801(13) 0.0363(4) Uani 1 d . . .
C16 C 0.7659(2) 0.37765(16) 0.26683(13) 0.0399(4) Uani 1 d . . .
C17 C 0.4561(2) 0.16479(16) 0.70311(13) 0.0391(4) Uani 1 d . . .
C18 C 1.1202(2) 0.45878(19) 0.36488(17) 0.0505(5) Uani 1 d . . .
C19 C 0.1723(2) 0.14887(18) 0.68239(15) 0.0499(5) Uani 1 d . . .
H19 H 0.0664 0.1141 0.6983 0.060 Uiso 1 calc . . R
C20 C 0.4828(2) 0.25187(17) 0.63279(15) 0.0502(5) Uani 1 d . . .
H20 H 0.5875 0.2859 0.6150 0.060 Uiso 1 calc . . R
C21 C 0.7467(2) 0.1024(2) 0.63025(18) 0.0532(5) Uani 1 d . . .
C22 C 1.0531(2) 0.4075(2) 0.26168(16) 0.0588(6) Uani 1 d . . .
H22A H 1.1358 0.4435 0.2196 0.071 Uiso 1 calc . . R
H22B H 1.0276 0.3116 0.2530 0.071 Uiso 1 calc . . R
C23 C 0.4314(2) 0.69056(15) 0.03603(13) 0.0353(4) Uani 1 d . . .
C24 C 0.5984(3) 0.21842(18) 0.35542(15) 0.0568(5) Uani 1 d . . .
H24 H 0.5864 0.1496 0.3944 0.068 Uiso 1 calc . . R
C25 C 0.7550(3) 0.0469(2) 0.5553(2) 0.0709(7) Uani 1 d . . .
H25 H 0.7616 0.0021 0.4948 0.085 Uiso 1 calc . . R
C26 C 0.3546(3) 0.28795(19) 0.58931(16) 0.0574(5) Uani 1 d . . .
H26 H 0.3732 0.3477 0.5428 0.069 Uiso 1 calc . . R
C27 C 0.2000(3) 0.2371(2) 0.61356(16) 0.0609(6) Uani 1 d . . .
H27 H 0.1136 0.2621 0.5836 0.073 Uiso 1 calc . . R
C28 C 0.4851(2) 0.36048(19) 0.27012(15) 0.0522(5) Uani 1 d . . .
H28 H 0.3951 0.3887 0.2517 0.063 Uiso 1 calc . . R
C29 C 0.7373(2) 0.1699(2) 0.72638(15) 0.0550(5) Uani 1 d . . .
H29A H 0.8139 0.1531 0.7770 0.066 Uiso 1 calc . . R
H29B H 0.7696 0.2650 0.7238 0.066 Uiso 1 calc . . R
C30 C 0.7483(2) 0.27715(18) 0.32591(15) 0.0503(5) Uani 1 d . . .
H30 H 0.8379 0.2492 0.3458 0.060 Uiso 1 calc . . R
C31 C 0.4667(3) 0.2599(2) 0.32826(16) 0.0603(6) Uani 1 d . . .
H31 H 0.3655 0.2204 0.3490 0.072 Uiso 1 calc . . R
C32 C 1.1729(3) 0.5000(2) 0.44638(19) 0.0679(6) Uani 1 d . . .
H32 H 1.2155 0.5334 0.5124 0.082 Uiso 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 0.0033 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
_geom_angle_publ_flag
C13 N3 N6 115.64(14) . . ?
C12 N4 N5 119.41(14) . . ?
C9 N5 N4 115.80(14) . . ?
C23 N6 N3 120.17(14) . . ?
C16 O7 C22 118.70(15) . . ?
C17 O8 C29 118.37(14) . . ?
N5 C9 C10 120.29(15) . . ?
C17 C10 C9 120.34(15) . . ?
C19 C10 C9 121.66(15) . . ?
C19 C10 C17 117.99(16) . . ?
N4 C12 S2 120.33(13) . . ?
N11 C12 S2 122.71(13) . . ?
N11 C12 N4 116.96(16) . . ?
N3 C13 C15 120.42(16) . . ?
C16 C15 C13 120.51(16) . . ?
C28 C15 C13 121.56(16) . . ?
C28 C15 C16 117.91(16) . . ?
O7 C16 C15 115.03(15) . . ?
O7 C16 C30 124.48(16) . . ?
C30 C16 C15 120.48(17) . . ?
O8 C17 C10 115.18(15) . . ?
O8 C17 C20 124.37(16) . . ?
C20 C17 C10 120.45(17) . . ?
C32 C18 C22 179.5(2) . . ?
C27 C19 C10 121.31(18) . . ?
C26 C20 C17 119.79(18) . . ?
C25 C21 C29 178.5(2) . . ?
O7 C22 C18 112.78(16) . . ?
N6 C23 S1 119.67(12) . . ?
N14 C23 S1 123.69(13) . . ?
N14 C23 N6 116.64(15) . . ?
C31 C24 C30 120.72(18) . . ?
C27 C26 C20 120.69(18) . . ?
C26 C27 C19 119.76(19) . . ?
C31 C28 C15 121.84(18) . . ?
O8 C29 C21 111.78(16) . . ?
C24 C30 C16 119.83(18) . . ?
C24 C31 C28 119.2(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
S1 C23 1.6764(17) . ?
S2 C12 1.6821(18) . ?
N3 N6 1.3703(18) . ?
N3 C13 1.271(2) . ?
N4 N5 1.3733(18) . ?
N4 C12 1.335(2) . ?
N5 C9 1.268(2) . ?
N6 C23 1.341(2) . ?
O7 C16 1.373(2) . ?
O7 C22 1.420(2) . ?
O8 C17 1.361(2) . ?
O8 C29 1.421(2) . ?
C9 C10 1.457(2) . ?
C10 C17 1.396(2) . ?
C10 C19 1.382(2) . ?
N11 C12 1.312(2) . ?
C13 C15 1.456(2) . ?
N14 C23 1.317(2) . ?
C15 C16 1.387(2) . ?
C15 C28 1.381(2) . ?
C16 C30 1.377(2) . ?
C17 C20 1.381(2) . ?
C18 C22 1.453(3) . ?
C18 C32 1.148(3) . ?
C19 C27 1.374(3) . ?
C20 C26 1.370(3) . ?
C21 C25 1.152(3) . ?
C21 C29 1.457(3) . ?
C24 C30 1.371(3) . ?
C24 C31 1.364(3) . ?
C26 C27 1.363(3) . ?
C28 C31 1.369(3) . ?
