#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/11/27/7112728.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_7112728
loop_
_publ_author_name
'Nakhi, Ali'
'Prasad, Bagineni'
'Reddy, Uppender'
'Rao, Raja Mohan'
'Sandra, Sandhya'
'Kapavarapu, Ravikumar'
'Rambabu, D.'
'Rama Krishna, G.'
'Reddy, C. Malla'
'Ravada, Kishore'
'Misra, Parimal'
'Iqbal, Javed'
'Pal, Manojit'
_publ_section_title
;
 A new route to indoles via in situ desilylation--Sonogashira strategy:
 identification of novel small molecules as potential anti-tuberculosis
 agents
;
_journal_issue                   10
_journal_name_full               MedChemComm
_journal_page_first              1006
_journal_paper_doi               10.1039/c1md00148e
_journal_volume                  2
_journal_year                    2011
_chemical_formula_moiety         'C25 H24 N2 O5 S2'
_chemical_formula_sum            'C25 H24 N2 O5 S2'
_chemical_formula_weight         496.58
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.590(4)
_cell_angle_beta                 91.371(4)
_cell_angle_gamma                108.406(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2712(4)
_cell_length_b                   12.0103(6)
_cell_length_c                   13.3107(6)
_cell_measurement_reflns_used    5109
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.9329
_cell_measurement_theta_min      2.9220
_cell_volume                     1237.00(11)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8168
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.9702
_exptl_absorpt_correction_T_min  0.9417
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4219
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0429
_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)+(0.0451P)²+0.6516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1130
_reflns_number_gt                3536
_reflns_number_total             4219
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1md00148e.txt
_cod_data_source_block           tri
_cod_original_cell_volume        1237.00(10)
_cod_original_sg_symbol_H-M      'P - 1'
_cod_database_code               7112728
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.7351(3) 0.69975(19) 0.10489(15) 0.0337(5) Uani 1 1 d .
C2 C 0.6450(3) 0.6178(2) 0.15870(17) 0.0422(5) Uani 1 1 d .
H2 H 0.5434 0.5574 0.1353 0.051 Uiso 1 1 calc R
C3 C 0.7306(3) 0.6385(2) 0.25792(16) 0.0382(5) Uani 1 1 d .
C4 C 0.8769(3) 0.73698(19) 0.26236(15) 0.0349(5) Uani 1 1 d .
C5 C 0.6953(3) 0.5810(2) 0.34286(18) 0.0494(6) Uani 1 1 d .
H5 H 0.6005 0.5131 0.3393 0.059 Uiso 1 1 calc R
C6 C 0.7998(3) 0.6243(2) 0.43174(18) 0.0505(6) Uani 1 1 d .
C7 C 0.9445(3) 0.7255(2) 0.43492(17) 0.0467(6) Uani 1 1 d .
C8 C 0.9860(3) 0.7817(2) 0.35033(17) 0.0427(5) Uani 1 1 d .
H8 H 1.0839 0.8472 0.3527 0.051 Uiso 1 1 calc R
C9 C 1.0565(4) 0.7815(3) 0.53120(19) 0.0577(7) Uani 1 1 d .
C10 C 1.2449(4) 0.8142(2) 0.52835(19) 0.0519(6) Uani 1 1 d .
C11 C 1.3208(4) 0.7613(3) 0.4524(2) 0.0627(8) Uani 1 1 d .
H11 H 1.2534 0.7065 0.3986 0.075 Uiso 1 1 calc R
C12 C 1.4959(5) 0.7895(3) 0.4562(3) 0.0850(10) Uani 1 1 d .
H12 H 1.5464 0.7533 0.4052 0.102 Uiso 1 1 calc R
C13 C 1.5963(5) 0.8709(4) 0.5351(3) 0.0884(11) Uani 1 1 d .
H13 H 1.7144 0.8891 0.5376 0.106 Uiso 1 1 calc R
C14 C 1.5235(5) 0.9247(3) 0.6094(3) 0.0813(10) Uani 1 1 d .
H14 H 1.5921 0.9806 0.6621 0.098 Uiso 1 1 calc R
C15 C 1.3499(4) 0.8971(3) 0.6070(2) 0.0676(8) Uani 1 1 d .
H15 H 1.3012 0.9340 0.6585 0.081 Uiso 1 1 calc R
C16 C 0.7568(5) 0.5610(3) 0.5228(2) 0.0866(11) Uani 1 1 d .
H16A H 0.7056 0.6048 0.5712 0.130 Uiso 1 1 calc R
H16B H 0.8593 0.5559 0.5542 0.130 Uiso 1 1 calc R
H16C H 0.6781 0.4824 0.5007 0.130 Uiso 1 1 calc R
C17 C 0.9759(4) 1.0097(2) 0.1638(2) 0.0696(8) Uani 1 1 d .
H17A H 1.0622 1.0786 0.1483 0.104 Uiso 1 1 calc R
H17B H 0.9588 1.0212 0.2352 0.104 Uiso 1 1 calc R
H17C H 0.8709 0.9981 0.1250 0.104 Uiso 1 1 calc R
C18 C 0.6896(3) 0.71705(19) 0.00140(15) 0.0337(5) Uani 1 1 d .
C19 C 0.5914(3) 0.7899(2) -0.01054(17) 0.0406(5) Uani 1 1 d .
H19 H 0.5591 0.8288 0.0474 0.049 Uiso 1 1 calc R
C20 C 0.5397(3) 0.8069(2) -0.10529(18) 0.0431(5) Uani 1 1 d .
C21 C 0.5899(3) 0.7480(2) -0.18984(18) 0.0461(6) Uani 1 1 d .
H21 H 0.5592 0.7590 -0.2544 0.055 Uiso 1 1 calc R
C22 C 0.6847(3) 0.6731(2) -0.18092(17) 0.0451(6) Uani 1 1 d .
H22 H 0.7158 0.6342 -0.2393 0.054 Uiso 1 1 calc R
C23 C 0.7338(3) 0.65550(19) -0.08611(16) 0.0375(5) Uani 1 1 d .
C24 C 0.4340(4) 0.8873(3) -0.1164(2) 0.0616(7) Uani 1 1 d .
H24A H 0.3645 0.8881 -0.0597 0.092 Uiso 1 1 calc R
H24B H 0.3620 0.8583 -0.1786 0.092 Uiso 1 1 calc R
H24C H 0.5085 0.9666 -0.1178 0.092 Uiso 1 1 calc R
C25 C 1.0829(5) 0.6124(4) -0.1919(4) 0.1156(16) Uani 1 1 d .
H25A H 1.1331 0.5768 -0.2467 0.173 Uiso 1 1 calc R
H25B H 1.1654 0.6451 -0.1343 0.173 Uiso 1 1 calc R
H25C H 1.0478 0.6746 -0.2134 0.173 Uiso 1 1 calc R
N1 N 0.8224(3) 0.57477(19) -0.07225(15) 0.0522(6) Uani 1 1 d .
H1 H 0.8325 0.5613 -0.0111 0.063 Uiso 1 1 calc R
N2 N 0.8831(2) 0.77513(16) 0.16678(13) 0.0353(4) Uani 1 1 d .
O1 O 0.7886(3) 0.45805(18) -0.24525(14) 0.0751(6) Uani 1 1 d .
O2 O 0.9633(3) 0.42587(18) -0.10737(14) 0.0667(6) Uani 1 1 d .
O3 O 1.0435(2) 0.85885(17) 0.02552(12) 0.0571(5) Uani 1 1 d .
O4 O 1.1888(2) 0.89898(18) 0.19603(14) 0.0651(5) Uani 1 1 d .
O5 O 0.9918(3) 0.7992(3) 0.61136(15) 0.0968(9) Uani 1 1 d .
S1 S 0.90660(9) 0.50519(6) -0.15782(5) 0.04905(19) Uani 1 1 d .
S2 S 1.04116(7) 0.88500(5) 0.13269(4) 0.04104(17) 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'
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
C2 C1 N2 108.32(19)
C2 C1 C18 127.8(2)
N2 C1 C18 123.78(18)
C1 C2 C3 109.1(2)
C4 C3 C5 119.4(2)
C4 C3 C2 107.33(19)
C5 C3 C2 133.3(2)
C8 C4 C3 121.4(2)
C8 C4 N2 131.1(2)
C3 C4 N2 107.55(18)
C6 C5 C3 120.6(2)
C5 C6 C7 118.9(2)
C5 C6 C16 119.3(3)
C7 C6 C16 121.8(3)
C8 C7 C6 121.7(2)
C8 C7 C9 116.9(2)
C6 C7 C9 121.4(2)
C4 C8 C7 118.1(2)
O5 C9 C10 120.8(2)
O5 C9 C7 119.7(3)
C10 C9 C7 119.5(2)
C11 C10 C15 118.3(3)
C11 C10 C9 122.3(2)
C15 C10 C9 119.3(3)
C12 C11 C10 120.2(3)
C13 C12 C11 120.2(3)
C14 C13 C12 120.2(3)
C13 C14 C15 120.2(3)
C14 C15 C10 120.8(3)
C19 C18 C23 118.6(2)
C19 C18 C1 119.70(19)
C23 C18 C1 121.55(19)
C20 C19 C18 122.7(2)
C21 C20 C19 117.2(2)
C21 C20 C24 121.1(2)
C19 C20 C24 121.7(2)
C22 C21 C20 121.7(2)
C21 C22 C23 120.6(2)
C22 C23 C18 119.1(2)
C22 C23 N1 123.2(2)
C18 C23 N1 117.65(19)
C23 N1 S1 127.54(16)
C4 N2 C1 107.67(17)
C4 N2 S2 125.37(15)
C1 N2 S2 126.91(14)
O1 S1 O2 119.15(12)
O1 S1 N1 108.71(12)
O2 S1 N1 105.48(11)
O1 S1 C25 107.7(2)
O2 S1 C25 109.13(18)
N1 S1 C25 105.90(18)
O3 S2 O4 119.70(12)
O3 S2 N2 106.87(10)
O4 S2 N2 106.97(10)
O3 S2 C17 109.26(14)
O4 S2 C17 109.07(15)
N2 S2 C17 103.77(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.345(3)
C1 N2 1.423(3)
C1 C18 1.481(3)
C2 C3 1.433(3)
C3 C4 1.392(3)
C3 C5 1.401(3)
C4 C8 1.389(3)
C4 N2 1.412(3)
C5 C6 1.379(3)
C6 C7 1.405(4)
C6 C16 1.516(4)
C7 C8 1.393(3)
C7 C9 1.498(3)
C9 O5 1.225(3)
C9 C10 1.484(4)
C10 C11 1.382(4)
C10 C15 1.393(4)
C11 C12 1.378(4)
C12 C13 1.373(5)
C13 C14 1.356(5)
C14 C15 1.367(5)
C17 S2 1.744(3)
C18 C19 1.391(3)
C18 C23 1.404(3)
C19 C20 1.386(3)
C20 C21 1.382(3)
C20 C24 1.513(3)
C21 C22 1.382(3)
C22 C23 1.382(3)
C23 N1 1.417(3)
C25 S1 1.735(4)
N1 S1 1.6130(19)
N2 S2 1.6655(18)
O1 S1 1.424(2)
O2 S1 1.4270(19)
O3 S2 1.4161(17)
O4 S2 1.4174(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139184595
