#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/11/27/7112723.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_7112723
loop_
_publ_author_name
'Medda, Federico'
'Joseph, Thomas L.'
'Pirrie, Lisa'
'Higgins, Maureen'
'Slawin, Alexandra M. Z.'
'Lain, Sonia'
'Verma, Chandra'
'Westwood, Nicholas J.'
_publ_section_title
;
 N1-Benzyl substituted cambinol analogues as isozyme selective inhibitors
 of the sirtuin family of protein deacetylases
;
_journal_issue                   7
_journal_name_full               MedChemComm
_journal_page_first              611
_journal_paper_doi               10.1039/c1md00023c
_journal_volume                  2
_journal_year                    2011
_chemical_formula_moiety         'C29 H24 N2 O2 S'
_chemical_formula_sum            'C29 H24 N2 O2 S'
_chemical_formula_weight         464.56
_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                78.20(3)
_cell_angle_beta                 67.70(2)
_cell_angle_gamma                87.07(3)
_cell_formula_units_Z            2
_cell_length_a                   10.002(2)
_cell_length_b                   10.640(3)
_cell_length_c                   12.1261(18)
_cell_measurement_reflns_used    4141
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.8
_cell_measurement_theta_min      2.0
_cell_volume                     1168.2(5)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_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      93(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7503
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4122
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0425
_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)+(0.0612P)²+0.1497P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                3376
_reflns_number_total             4122
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1md00023c.txt
_cod_data_source_block           4iv
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7112723
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
N1 N 0.69611(15) 0.25548(12) 0.17883(11) 0.0184(3) Uani 1 1 d .
C2 C 0.76383(19) 0.21811(16) 0.06891(14) 0.0199(4) Uani 1 1 d .
S2 S 0.73693(5) 0.28348(5) -0.05709(4) 0.03001(16) Uani 1 1 d .
N3 N 0.85781(16) 0.12102(13) 0.06870(12) 0.0195(3) Uani 1 1 d D
H3N H 0.908(2) 0.0922(18) -0.0035(15) 0.042(6) Uiso 1 1 d D
C4 C 0.89558(18) 0.06047(15) 0.16433(14) 0.0183(4) Uani 1 1 d .
O4 O 0.98632(14) -0.02380(11) 0.14864(10) 0.0262(3) Uani 1 1 d .
C5 C 0.82147(18) 0.10335(15) 0.27861(14) 0.0172(4) Uani 1 1 d .
C6 C 0.72328(18) 0.19671(15) 0.28298(14) 0.0171(4) Uani 1 1 d .
C1' C 0.63411(19) 0.24038(15) 0.39831(14) 0.0179(4) Uani 1 1 d .
C2' C 0.5024(2) 0.17716(17) 0.47254(15) 0.0251(4) Uani 1 1 d .
H2'A H 0.4707 0.1072 0.4500 0.030 Uiso 1 1 calc R
C3' C 0.4174(2) 0.21638(18) 0.57948(16) 0.0295(5) Uani 1 1 d .
H3'A H 0.3270 0.1739 0.6294 0.035 Uiso 1 1 calc R
C4' C 0.4639(2) 0.31701(17) 0.61361(15) 0.0272(5) Uani 1 1 d .
H4'A H 0.4061 0.3430 0.6873 0.033 Uiso 1 1 calc R
C5' C 0.5950(2) 0.37985(17) 0.53987(15) 0.0244(4) Uani 1 1 d .
H5'A H 0.6267 0.4490 0.5634 0.029 Uiso 1 1 calc R
C6' C 0.68026(19) 0.34281(16) 0.43213(15) 0.0221(4) Uani 1 1 d .
H6'A H 0.7695 0.3869 0.3816 0.027 Uiso 1 1 calc R
C1" C 0.85934(19) 0.03523(15) 0.38513(14) 0.0204(4) Uani 1 1 d .
H1"A H 0.9481 -0.0133 0.3527 0.024 Uiso 1 1 calc R
H1"B H 0.7807 -0.0285 0.4374 0.024 Uiso 1 1 calc R
C1"A C 0.88376(19) 0.11671(15) 0.46524(14) 0.0189(4) Uani 1 1 d .
C2" C 0.79983(19) 0.09459(15) 0.58887(14) 0.0190(4) Uani 1 1 d .
O2" O 0.69349(14) -0.00017(11) 0.63145(10) 0.0271(3) Uani 1 1 d .
C3" C 0.8224(2) 0.16618(16) 0.66614(15) 0.0232(4) Uani 1 1 d .
H3"A H 0.7640 0.1490 0.7505 0.028 Uiso 1 1 calc R
C4" C 0.9277(2) 0.26003(16) 0.62028(15) 0.0232(4) Uani 1 1 d .
H4"A H 0.9423 0.3075 0.6734 0.028 Uiso 1 1 calc R
C4"A C 1.01606(19) 0.28809(16) 0.49474(15) 0.0214(4) Uani 1 1 d .
C5" C 1.1232(2) 0.38833(18) 0.44490(16) 0.0286(5) Uani 1 1 d .
H5"A H 1.1395 0.4355 0.4974 0.034 Uiso 1 1 calc R
C6" C 1.2032(2) 0.41832(19) 0.32313(17) 0.0313(5) Uani 1 1 d .
H6"A H 1.2718 0.4880 0.2908 0.038 Uiso 1 1 calc R
C7" C 1.1832(2) 0.34529(18) 0.24590(16) 0.0296(5) Uani 1 1 d .
H7"A H 1.2393 0.3656 0.1611 0.036 Uiso 1 1 calc R
C8" C 1.08444(19) 0.24564(17) 0.29108(15) 0.0234(4) Uani 1 1 d .
H8"A H 1.0753 0.1960 0.2374 0.028 Uiso 1 1 calc R
C8"A C 0.99469(18) 0.21435(15) 0.41691(14) 0.0191(4) Uani 1 1 d .
C9" C 0.6039(2) -0.0232(2) 0.75818(16) 0.0391(6) Uani 1 1 d .
H9"1 H 0.6644 -0.0446 0.8064 0.059 Uiso 1 1 calc R
H9"2 H 0.5358 -0.0950 0.7771 0.059 Uiso 1 1 calc R
H9"3 H 0.5500 0.0540 0.7778 0.059 Uiso 1 1 calc R
C1'" C 0.59369(18) 0.36089(15) 0.18307(15) 0.0194(4) Uani 1 1 d .
H1'A H 0.5263 0.3560 0.2684 0.023 Uiso 1 1 calc R
H1'B H 0.5358 0.3487 0.1353 0.023 Uiso 1 1 calc R
C1A C 0.66566(19) 0.49309(16) 0.13432(14) 0.0201(4) Uani 1 1 d .
C2'" C 0.8030(2) 0.51977(17) 0.12941(15) 0.0257(4) Uani 1 1 d .
H2'B H 0.8591 0.4519 0.1517 0.031 Uiso 1 1 calc R
C3'" C 0.8585(2) 0.64558(18) 0.09186(17) 0.0317(5) Uani 1 1 d .
H3'B H 0.9518 0.6634 0.0894 0.038 Uiso 1 1 calc R
C4'" C 0.7780(2) 0.74421(18) 0.05829(16) 0.0313(5) Uani 1 1 d .
H4'B H 0.8154 0.8301 0.0336 0.038 Uiso 1 1 calc R
C5'" C 0.6424(2) 0.71799(17) 0.06055(15) 0.0289(5) Uani 1 1 d .
H5'B H 0.5876 0.7857 0.0362 0.035 Uiso 1 1 calc R
C6'" C 0.5870(2) 0.59300(16) 0.09828(14) 0.0234(4) Uani 1 1 d .
H6'B H 0.4942 0.5755 0.0995 0.028 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 0.0033 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 N1 C6 121.85(15)
C2 N1 C1'" 117.15(14)
C6 N1 C1'" 120.99(13)
N3 C2 N1 115.33(15)
N3 C2 S2 120.42(12)
N1 C2 S2 124.25(14)
C2 N3 C4 127.21(14)
C2 N3 H3N 119.4(14)
C4 N3 H3N 113.3(14)
O4 C4 N3 119.49(15)
O4 C4 C5 125.05(16)
N3 C4 C5 115.46(15)
C6 C5 C4 118.74(16)
C6 C5 C1" 125.30(15)
C4 C5 C1" 115.93(15)
C5 C6 N1 121.32(14)
C5 C6 C1' 122.58(15)
N1 C6 C1' 116.07(15)
C2' C1' C6' 119.74(15)
C2' C1' C6 118.95(14)
C6' C1' C6 121.31(14)
C3' C2' C1' 120.00(16)
C3' C2' H2'A 120.0
C1' C2' H2'A 120.0
C4' C3' C2' 120.25(17)
C4' C3' H3'A 119.9
C2' C3' H3'A 119.9
C3' C4' C5' 119.78(16)
C3' C4' H4'A 120.1
C5' C4' H4'A 120.1
C6' C5' C4' 120.66(16)
C6' C5' H5'A 119.7
C4' C5' H5'A 119.7
C5' C6' C1' 119.56(16)
C5' C6' H6'A 120.2
C1' C6' H6'A 120.2
C5 C1" C1"A 117.76(13)
C5 C1" H1"A 107.9
C1"A C1" H1"A 107.9
C5 C1" H1"B 107.9
C1"A C1" H1"B 107.9
H1"A C1" H1"B 107.2
C2" C1"A C8"A 118.63(15)
C2" C1"A C1" 120.08(14)
C8"A C1"A C1" 121.27(14)
O2" C2" C1"A 116.63(15)
O2" C2" C3" 121.92(14)
C1"A C2" C3" 121.44(15)
C2" O2" C9" 117.69(14)
C4" C3" C2" 120.15(15)
C4" C3" H3"A 119.9
C2" C3" H3"A 119.9
C3" C4" C4"A 121.12(16)
C3" C4" H4"A 119.4
C4"A C4" H4"A 119.4
C4" C4"A C5" 121.79(16)
C4" C4"A C8"A 118.72(15)
C5" C4"A C8"A 119.49(15)
C6" C5" C4"A 121.32(17)
C6" C5" H5"A 119.3
C4"A C5" H5"A 119.3
C5" C6" C7" 119.41(17)
C5" C6" H6"A 120.3
C7" C6" H6"A 120.3
C8" C7" C6" 120.87(16)
C8" C7" H7"A 119.6
C6" C7" H7"A 119.6
C7" C8" C8"A 121.50(16)
C7" C8" H8"A 119.3
C8"A C8" H8"A 119.3
C4"A C8"A C8" 117.32(15)
C4"A C8"A C1"A 119.93(14)
C8" C8"A C1"A 122.72(15)
O2" C9" H9"1 109.5
O2" C9" H9"2 109.5
H9"1 C9" H9"2 109.5
O2" C9" H9"3 109.5
H9"1 C9" H9"3 109.5
H9"2 C9" H9"3 109.5
N1 C1'" C1A 113.80(14)
N1 C1'" H1'A 108.8
C1A C1'" H1'A 108.8
N1 C1'" H1'B 108.8
C1A C1'" H1'B 108.8
H1'A C1'" H1'B 107.7
C6'" C1A C2'" 119.01(16)
C6'" C1A C1'" 117.62(16)
C2'" C1A C1'" 123.29(17)
C3'" C2'" C1A 120.26(19)
C3'" C2'" H2'B 119.9
C1A C2'" H2'B 119.9
C4'" C3'" C2'" 120.04(19)
C4'" C3'" H3'B 120.0
C2'" C3'" H3'B 120.0
C3'" C4'" C5'" 120.00(18)
C3'" C4'" H4'B 120.0
C5'" C4'" H4'B 120.0
C6'" C5'" C4'" 119.97(19)
C6'" C5'" H5'B 120.0
C4'" C5'" H5'B 120.0
C5'" C6'" C1A 120.69(18)
C5'" C6'" H6'B 119.7
C1A C6'" H6'B 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.378(2)
N1 C6 1.407(2)
N1 C1'" 1.475(2)
C2 N3 1.360(2)
C2 S2 1.6580(18)
N3 C4 1.380(2)
N3 H3N 0.935(15)
C4 O4 1.233(2)
C4 C5 1.457(2)
C5 C6 1.355(2)
C5 C1" 1.516(2)
C6 C1' 1.498(2)
C1' C2' 1.393(2)
C1' C6' 1.395(2)
C2' C3' 1.388(2)
C2' H2'A 0.9500
C3' C4' 1.382(3)
C3' H3'A 0.9500
C4' C5' 1.386(3)
C4' H4'A 0.9500
C5' C6' 1.386(2)
C5' H5'A 0.9500
C6' H6'A 0.9500
C1" C1"A 1.517(2)
C1" H1"A 0.9900
C1" H1"B 0.9900
C1"A C2" 1.389(2)
C1"A C8"A 1.424(2)
C2" O2" 1.376(2)
C2" C3" 1.407(2)
O2" C9" 1.431(2)
C3" C4" 1.361(2)
C3" H3"A 0.9500
C4" C4"A 1.417(2)
C4" H4"A 0.9500
C4"A C5" 1.419(2)
C4"A C8"A 1.423(2)
C5" C6" 1.364(3)
C5" H5"A 0.9500
C6" C7" 1.406(3)
C6" H6"A 0.9500
C7" C8" 1.364(3)
C7" H7"A 0.9500
C8" C8"A 1.424(2)
C8" H8"A 0.9500
C9" H9"1 0.9800
C9" H9"2 0.9800
C9" H9"3 0.9800
C1'" C1A 1.512(2)
C1'" H1'A 0.9900
C1'" H1'B 0.9900
C1A C6'" 1.388(3)
C1A C2'" 1.394(3)
C2'" C3'" 1.393(3)
C2'" H2'B 0.9500
C3'" C4'" 1.380(3)
C3'" H3'B 0.9500
C4'" C5'" 1.387(3)
C4'" H4'B 0.9500
C5'" C6'" 1.385(2)
C5'" H5'B 0.9500
C6'" H6'B 0.9500
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
N3 H3N O4 0.935(15) 1.943(16) 2.8772(19) 177.1(19) 2_755
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
C6 N1 C2 N3 0.1(2)
C1'" N1 C2 N3 179.76(13)
C6 N1 C2 S2 -179.88(12)
C1'" N1 C2 S2 -0.2(2)
N1 C2 N3 C4 -2.6(2)
S2 C2 N3 C4 177.40(13)
C2 N3 C4 O4 -177.75(15)
C2 N3 C4 C5 2.5(2)
O4 C4 C5 C6 -179.63(15)
N3 C4 C5 C6 0.1(2)
O4 C4 C5 C1" -1.2(2)
N3 C4 C5 C1" 178.54(13)
C4 C5 C6 N1 -2.4(2)
C1" C5 C6 N1 179.41(14)
C4 C5 C6 C1' 175.51(14)
C1" C5 C6 C1' -2.7(2)
C2 N1 C6 C5 2.3(2)
C1'" N1 C6 C5 -177.34(14)
C2 N1 C6 C1' -175.68(14)
C1'" N1 C6 C1' 4.7(2)
C5 C6 C1' C2' -88.4(2)
N1 C6 C1' C2' 89.54(19)
C5 C6 C1' C6' 91.8(2)
N1 C6 C1' C6' -90.2(2)
C6' C1' C2' C3' 0.2(3)
C6 C1' C2' C3' -179.61(18)
C1' C2' C3' C4' -0.8(3)
C2' C3' C4' C5' 0.8(3)
C3' C4' C5' C6' 0.0(3)
C4' C5' C6' C1' -0.6(3)
C2' C1' C6' C5' 0.6(3)
C6 C1' C6' C5' -179.66(17)
C6 C5 C1" C1"A -45.3(2)
C4 C5 C1" C1"A 136.46(15)
C5 C1" C1"A C2" 121.57(18)
C5 C1" C1"A C8"A -60.2(2)
C8"A C1"A C2" O2" 179.68(15)
C1" C1"A C2" O2" -2.0(2)
C8"A C1"A C2" C3" 0.0(3)
C1" C1"A C2" C3" 178.27(16)
C1"A C2" O2" C9" -178.93(17)
C3" C2" O2" C9" 0.8(3)
O2" C2" C3" C4" -179.32(17)
C1"A C2" C3" C4" 0.4(3)
C2" C3" C4" C4"A 0.3(3)
C3" C4" C4"A C5" 177.95(18)
C3" C4" C4"A C8"A -1.2(3)
C4" C4"A C5" C6" -177.03(19)
C8"A C4"A C5" C6" 2.1(3)
C4"A C5" C6" C7" -2.5(3)
C5" C6" C7" C8" 0.4(3)
C6" C7" C8" C8"A 2.1(3)
C4" C4"A C8"A C8" 179.52(17)
C5" C4"A C8"A C8" 0.3(3)
C4" C4"A C8"A C1"A 1.5(3)
C5" C4"A C8"A C1"A -177.64(17)
C7" C8" C8"A C4"A -2.4(3)
C7" C8" C8"A C1"A 175.50(18)
C2" C1"A C8"A C4"A -0.9(3)
C1" C1"A C8"A C4"A -179.21(15)
C2" C1"A C8"A C8" -178.80(17)
C1" C1"A C8"A C8" 2.9(3)
C2 N1 C1'" C1A -80.41(18)
C6 N1 C1'" C1A 99.28(17)
N1 C1'" C1A C6'" 159.81(14)
N1 C1'" C1A C2'" -23.3(2)
C6'" C1A C2'" C3'" 1.7(2)
C1'" C1A C2'" C3'" -175.19(15)
C1A C2'" C3'" C4'" -0.6(3)
C2'" C3'" C4'" C5'" -0.8(3)
C3'" C4'" C5'" C6'" 1.0(3)
C4'" C5'" C6'" C1A 0.1(2)
C2'" C1A C6'" C5'" -1.5(2)
C1'" C1A C6'" C5'" 175.59(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 90666421
