#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151628.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_7151628
loop_
_publ_author_name
'Bhurruth-Alcor, Yushma'
'Røst, Therese'
'Jorgensen, Michael R.'
'Kontogiorgis, Christos'
'Skorve, Jon'
'Cooper, Robert G.'
'Sheridan, Joseph M.'
'Hamilton, William D. O.'
'Heal, Jonathan R.'
'Berge, Rolf K.'
'Miller, Andrew D.'
_publ_section_title
;
 Synthesis of novel PPARα/γ dual agonists as potential drugs for the
 treatment of the metabolic syndrome and diabetes type II designed
 using a new de novo design program PROTOBUILD.
;
_journal_issue                   4
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1169
_journal_page_last               1188
_journal_paper_doi               10.1039/C0OB00146E
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C22 H16 N2 O2 S'
_chemical_formula_sum            'C22 H16 N2 O2 S'
_chemical_formula_weight         372.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.888(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8591(3)
_cell_length_b                   10.0425(3)
_cell_length_c                   17.0542(4)
_cell_measurement_reflns_used    4785
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.8460
_cell_measurement_theta_min      3.7750
_cell_volume                     1826.32(9)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 15.9863
_diffrn_measured_fraction_theta_full 0.875
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_device_type  'OD Xcalibur 3'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0621
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12993
_diffrn_reflns_theta_full        28.96
_diffrn_reflns_theta_max         28.96
_diffrn_reflns_theta_min         3.79
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
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)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4231
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0542P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1155
_reflns_number_gt                2710
_reflns_number_total             4231
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0OB00146E.TXT
_cod_data_source_block           Compound_25
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7151628
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.58850(12) 0.94935(14) 0.89361(8) 0.0372(3) Uani 1 1 d . A .
C2 C 0.69146(15) 0.9818(2) 0.95585(10) 0.0409(4) Uani 1 1 d . . .
C3 C 0.66789(15) 1.0993(2) 0.98703(10) 0.0451(5) Uani 1 1 d . . .
H3A H 0.7210 1.1425 1.0302 0.054 Uiso 1 1 calc R . .
C4 C 0.55142(15) 1.14953(19) 0.94562(10) 0.0398(4) Uani 1 1 d . . .
C5 C 0.48547(17) 1.2660(2) 0.95259(11) 0.0454(5) Uani 1 1 d . . .
H5A H 0.5168 1.3297 0.9926 0.054 Uiso 1 1 calc R . .
C6 C 0.37405(18) 1.28779(19) 0.90068(11) 0.0456(5) Uani 1 1 d . . .
C7 C 0.32607(16) 1.1936(2) 0.84183(11) 0.0438(4) Uani 1 1 d . . .
H7A H 0.2488 1.2108 0.8067 0.053 Uiso 1 1 calc R . .
C8 C 0.38902(15) 1.0772(2) 0.83434(10) 0.0419(4) Uani 1 1 d . . .
H8A H 0.3564 1.0134 0.7947 0.050 Uiso 1 1 calc R . .
C9 C 0.50191(15) 1.05544(18) 0.88659(9) 0.0363(4) Uani 1 1 d . . .
S10 S 0.56610(4) 0.80969(5) 0.83901(3) 0.04155(16) Uani 1 1 d D . .
O11 O 0.64141(13) 0.70998(14) 0.88334(8) 0.0609(4) Uani 1 1 d . A .
O12 O 0.43393(11) 0.79307(13) 0.81821(8) 0.0532(4) Uani 1 1 d . A .
C13 C 0.6292(3) 0.8375(3) 0.75531(15) 0.0417(11) Uani 0.702(10) 1 d PGD A 1
C14 C 0.5651(5) 0.9162(4) 0.69387(19) 0.0688(14) Uani 0.702(10) 1 d PGD A 1
H14A H 0.4858 0.9530 0.6977 0.083 Uiso 0.702(10) 1 calc PR A 1
C15 C 0.6168(7) 0.9410(3) 0.6267(2) 0.090(2) Uani 0.702(10) 1 d PG A 1
H15A H 0.5730 0.9948 0.5847 0.108 Uiso 0.702(10) 1 calc PR A 1
C16 C 0.7327(6) 0.8872(3) 0.6211(2) 0.0712(17) Uani 0.702(10) 1 d PG A 1
H16A H 0.7681 0.9041 0.5752 0.085 Uiso 0.702(10) 1 calc PR A 1
C17 C 0.7969(3) 0.8085(5) 0.6825(2) 0.0609(15) Uani 0.702(10) 1 d PG A 1
H17A H 0.8761 0.7716 0.6786 0.073 Uiso 0.702(10) 1 calc PR A 1
C18 C 0.7451(2) 0.7836(5) 0.74963(14) 0.0498(11) Uani 0.702(10) 1 d PGD A 1
H18A H 0.7889 0.7298 0.7916 0.060 Uiso 0.702(10) 1 calc PR A 1
C13' C 0.6106(5) 0.8552(9) 0.7478(3) 0.030(2) Uiso 0.298(10) 1 d PGD A 2
C14' C 0.5194(5) 0.9033(8) 0.6859(4) 0.041(2) Uiso 0.298(10) 1 d PGD A 2
H14B H 0.4359 0.9157 0.6939 0.049 Uiso 0.298(10) 1 calc PR A 2
C15' C 0.5505(6) 0.9333(7) 0.6125(3) 0.049(2) Uiso 0.298(10) 1 d PG A 2
H15B H 0.4882 0.9663 0.5702 0.058 Uiso 0.298(10) 1 calc PR A 2
C16' C 0.6727(6) 0.9152(7) 0.6009(3) 0.044(2) Uiso 0.298(10) 1 d PG A 2
H16B H 0.6939 0.9357 0.5507 0.053 Uiso 0.298(10) 1 calc PR A 2
C17' C 0.7638(5) 0.8670(8) 0.6628(3) 0.035(2) Uiso 0.298(10) 1 d PG A 2
H17B H 0.8474 0.8546 0.6549 0.042 Uiso 0.298(10) 1 calc PR A 2
C18' C 0.7328(5) 0.8370(8) 0.7362(3) 0.045(2) Uiso 0.298(10) 1 d PGD A 2
H18B H 0.7951 0.8041 0.7785 0.054 Uiso 0.298(10) 1 calc PR A 2
C19 C 0.80761(16) 0.8994(2) 0.97983(10) 0.0490(5) Uani 1 1 d . . .
H19A H 0.7822 0.8060 0.9864 0.059 Uiso 1 1 calc R . .
H19B H 0.8525 0.9310 1.0325 0.059 Uiso 1 1 calc R . .
C20 C 0.89827(15) 0.90162(18) 0.92215(10) 0.0381(4) Uani 1 1 d . . .
C21 C 0.90877(16) 1.01031(18) 0.87401(11) 0.0417(4) Uani 1 1 d . . .
H21A H 0.8576 1.0863 0.8764 0.050 Uiso 1 1 calc R . .
C22 C 0.99268(16) 1.00966(19) 0.82253(11) 0.0447(5) Uani 1 1 d . . .
H22A H 0.9986 1.0849 0.7897 0.054 Uiso 1 1 calc R . .
C23 C 1.06792(16) 0.9005(2) 0.81846(11) 0.0473(5) Uani 1 1 d . . .
H23A H 1.1249 0.9000 0.7825 0.057 Uiso 1 1 calc R . .
C24 C 1.06037(17) 0.7934(2) 0.86628(13) 0.0509(5) Uani 1 1 d . . .
H24A H 1.1125 0.7181 0.8638 0.061 Uiso 1 1 calc R . .
C25 C 0.97669(17) 0.79392(19) 0.91863(12) 0.0475(5) Uani 1 1 d . . .
H25A H 0.9732 0.7194 0.9525 0.057 Uiso 1 1 calc R . .
C26 C 0.3051(2) 1.4086(2) 0.90767(13) 0.0599(6) Uani 1 1 d . . .
N26 N 0.2505(2) 1.5037(2) 0.91303(15) 0.0878(7) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C2 107.88(14) . . ?
C9 N1 S10 124.08(11) . . ?
C2 N1 S10 128.00(12) . . ?
C3 C2 N1 108.35(15) . . ?
C3 C2 C19 126.30(16) . . ?
N1 C2 C19 125.32(16) . . ?
C2 C3 C4 109.55(16) . . ?
C5 C4 C9 119.48(16) . . ?
C5 C4 C3 133.01(17) . . ?
C9 C4 C3 107.50(16) . . ?
C6 C5 C4 118.96(17) . . ?
C5 C6 C7 121.00(18) . . ?
C5 C6 C26 119.20(19) . . ?
C7 C6 C26 119.79(18) . . ?
C8 C7 C6 121.05(17) . . ?
C7 C8 C9 117.94(17) . . ?
C8 C9 C4 121.56(17) . . ?
C8 C9 N1 131.74(16) . . ?
C4 C9 N1 106.68(15) . . ?
O11 S10 O12 120.25(9) . . ?
O11 S10 N1 106.64(8) . . ?
O12 S10 N1 105.70(7) . . ?
O11 S10 C13 106.10(13) . . ?
O12 S10 C13 110.72(13) . . ?
N1 S10 C13 106.66(12) . . ?
O11 S10 C13' 115.1(2) . . ?
O12 S10 C13' 103.9(2) . . ?
N1 S10 C13' 103.7(3) . . ?
C13 S10 C13' 9.0(2) . . ?
C14 C13 C18 120.0 . . ?
C14 C13 S10 119.80(13) . . ?
C18 C13 S10 120.19(13) . . ?
C15 C14 C13 120.0 . . ?
C14 C15 C16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C16 C17 C18 120.0 . . ?
C17 C18 C13 120.0 . . ?
C14' C13' C18' 120.0 . . ?
C14' C13' S10 118.8(3) . . ?
C18' C13' S10 121.1(3) . . ?
C13' C14' C15' 120.0 . . ?
C16' C15' C14' 120.0 . . ?
C17' C16' C15' 120.0 . . ?
C18' C17' C16' 120.0 . . ?
C17' C18' C13' 120.0 . . ?
C2 C19 C20 115.51(14) . . ?
C21 C20 C25 118.04(16) . . ?
C21 C20 C19 122.17(16) . . ?
C25 C20 C19 119.76(16) . . ?
C22 C21 C20 120.82(17) . . ?
C23 C22 C21 120.37(18) . . ?
C24 C23 C22 119.70(17) . . ?
C23 C24 C25 120.15(17) . . ?
C20 C25 C24 120.89(18) . . ?
N26 C26 C6 179.8(3) . . ?
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
N1 C9 1.411(2) . ?
N1 C2 1.426(2) . ?
N1 S10 1.6757(14) . ?
C2 C3 1.339(3) . ?
C2 C19 1.499(2) . ?
C3 C4 1.419(2) . ?
C4 C5 1.388(3) . ?
C4 C9 1.411(2) . ?
C5 C6 1.375(3) . ?
C6 C7 1.406(3) . ?
C6 C26 1.442(3) . ?
C7 C8 1.372(2) . ?
C8 C9 1.390(2) . ?
S10 O11 1.4175(14) . ?
S10 O12 1.4217(13) . ?
S10 C13 1.7187(15) . ?
S10 C13' 1.774(4) . ?
C13 C14 1.3900 . ?
C13 C18 1.3900 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C13' C14' 1.3900 . ?
C13' C18' 1.3900 . ?
C14' C15' 1.3900 . ?
C15' C16' 1.3900 . ?
C16' C17' 1.3900 . ?
C17' C18' 1.3900 . ?
C19 C20 1.518(2) . ?
C20 C21 1.383(2) . ?
C20 C25 1.385(2) . ?
C21 C22 1.380(2) . ?
C22 C23 1.376(3) . ?
C23 C24 1.362(3) . ?
C24 C25 1.389(3) . ?
C26 N26 1.137(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 53309435
