#------------------------------------------------------------------------------
#$Date: 2021-07-29 08:06:50 +0300 (Thu, 29 Jul 2021) $
#$Revision: 267814 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/32/7243284.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_7243284
loop_
_publ_author_name
'Tantawy, Ahmed H.'
'Meng, Xiang-Gao'
'Marzouk, Adel A.'
'Fouad, Ali'
'Abdelazeem, Ahmed H.'
'Youssif, Bahaa G. M.'
'Jiang, Hong'
'Wang, Man-Qun'
_publ_section_title
;
 Structure-based design, synthesis, and biological evaluation of novel
 piperine--resveratrol hybrids as antiproliferative agents targeting
 SIRT-2
;
_journal_issue                   41
_journal_name_full               'RSC Advances'
_journal_page_first              25738
_journal_page_last               25751
_journal_paper_doi               10.1039/D1RA04061H
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C20 H18 N2 O5'
_chemical_formula_sum            'C20 H18 N2 O5'
_chemical_formula_weight         366.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-05-30
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2020-06-12 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.874(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1988(7)
_cell_length_b                   4.8105(2)
_cell_length_c                   22.1672(8)
_cell_measurement_reflns_used    2380
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      64.10
_cell_measurement_theta_min      4.10
_cell_volume                     1788.03(13)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14927
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        65.921
_diffrn_reflns_theta_max         65.921
_diffrn_reflns_theta_min         2.635
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.6313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1274 before and 0.0607 after correction. The Ra '
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0671P)²+0.2630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1575
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2352
_reflns_number_total             3069
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra04061h3.cif
_cod_data_source_block           cu_190528e_0m
_cod_database_code               7243284
_shelx_shelxl_version_number     2014/7
_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   0.922
_shelx_estimated_absorpt_t_min   0.908
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All N(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H) groups 
2.a Secondary CH2 refined with riding coordinates: 
 C20(H20A,H20B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C2(H2), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), 
 C15(H15), C16(H16), C19(H19), N2(H2A) 
2.c Idealised Me refined as rotating group: 
 C7(H7A,H7B,H7C) 
2.d Idealised tetrahedral OH refined as rotating group: 
 O2(H2B) 
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.35046(13) -0.0588(4) 0.02034(10) 0.0447(5) Uani 1 1 d . . . . .
C2 C 0.40926(13) 0.1462(4) 0.04431(10) 0.0465(5) Uani 1 1 d . . . . .
H2 H 0.4244 0.2484 0.0154 0.056 Uiso 1 1 calc R . . . .
C3 C 0.44484(13) 0.1971(5) 0.11054(10) 0.0489(6) Uani 1 1 d . . . . .
C4 C 0.42036(14) 0.0507(5) 0.15411(11) 0.0525(6) Uani 1 1 d . . . . .
C5 C 0.36294(15) -0.1505(5) 0.13104(12) 0.0609(7) Uani 1 1 d . . . . .
H5 H 0.3467 -0.2482 0.1599 0.073 Uiso 1 1 calc R . . . .
C6 C 0.32912(14) -0.2085(5) 0.06451(11) 0.0548(6) Uani 1 1 d . . . . .
H6 H 0.2915 -0.3499 0.0493 0.066 Uiso 1 1 calc R . . . .
C7 C 0.54046(15) 0.5202(6) 0.10291(14) 0.0691(7) Uani 1 1 d . . . . .
H7A H 0.5011 0.6334 0.0707 0.104 Uiso 1 1 calc GR . . . .
H7B H 0.5611 0.3864 0.0814 0.104 Uiso 1 1 calc GR . . . .
H7C H 0.5831 0.6357 0.1308 0.104 Uiso 1 1 calc GR . . . .
C8 C 0.31287(13) -0.1229(5) -0.04891(10) 0.0457(5) Uani 1 1 d . . . . .
H8 H 0.2920 -0.2998 -0.0617 0.055 Uiso 1 1 calc R . . . .
C9 C 0.24917(13) 0.1389(4) -0.20754(10) 0.0436(5) Uani 1 1 d . . . . .
C10 C 0.21373(14) 0.0028(5) -0.27161(11) 0.0484(6) Uani 1 1 d . . . . .
H10 H 0.2004 -0.1844 -0.2731 0.058 Uiso 1 1 calc R . . . .
C11 C 0.19976(13) 0.1351(5) -0.32771(10) 0.0477(6) Uani 1 1 d . . . . .
H11 H 0.2151 0.3205 -0.3255 0.057 Uiso 1 1 calc R . . . .
C12 C 0.16284(13) 0.0127(5) -0.39112(10) 0.0489(6) Uani 1 1 d . . . . .
H12 H 0.1408 -0.1637 -0.3938 0.059 Uiso 1 1 calc R . . . .
C13 C 0.15768(13) 0.1340(5) -0.44697(11) 0.0492(6) Uani 1 1 d . . . . .
H13 H 0.1789 0.3119 -0.4437 0.059 Uiso 1 1 calc R . . . .
C14 C 0.12194(13) 0.0142(5) -0.51255(10) 0.0458(5) Uani 1 1 d . . . . .
C15 C 0.14739(14) 0.1054(5) -0.56074(11) 0.0543(6) Uani 1 1 d . . . . .
H15 H 0.1843 0.2492 -0.5509 0.065 Uiso 1 1 calc R . . . .
C16 C 0.11978(15) -0.0101(5) -0.62272(12) 0.0591(6) Uani 1 1 d . . . . .
H16 H 0.1387 0.0480 -0.6540 0.071 Uiso 1 1 calc R . . . .
C17 C 0.06331(14) -0.2136(5) -0.63579(11) 0.0517(6) Uani 1 1 d . . . . .
C18 C 0.03554(13) -0.3008(5) -0.58953(10) 0.0469(5) Uani 1 1 d . . . . .
C19 C 0.06363(13) -0.1959(5) -0.52779(10) 0.0461(5) Uani 1 1 d . . . . .
H19 H 0.0450 -0.2603 -0.4968 0.055 Uiso 1 1 calc R . . . .
C20 C -0.03308(16) -0.5247(6) -0.68314(12) 0.0612(7) Uani 1 1 d . . . . .
H20A H -0.0856 -0.4555 -0.7105 0.073 Uiso 1 1 calc R . . . .
H20B H -0.0292 -0.7169 -0.6948 0.073 Uiso 1 1 calc R . . . .
N1 N 0.30761(11) 0.0563(4) -0.09272(8) 0.0450(5) Uani 1 1 d . . . . .
N2 N 0.27210(11) -0.0397(4) -0.15635(8) 0.0475(5) Uani 1 1 d . . . . .
H2A H 0.2645 -0.2152 -0.1635 0.057 Uiso 1 1 calc R . . . .
O1 O 0.50512(11) 0.3803(4) 0.14094(8) 0.0695(6) Uani 1 1 d . . . . .
O2 O 0.45540(13) 0.0990(4) 0.21964(8) 0.0734(6) Uani 1 1 d . . . . .
H2B H 0.4798 0.2466 0.2262 0.110 Uiso 1 1 calc GR . . . .
O3 O 0.25559(11) 0.3921(3) -0.20059(7) 0.0596(5) Uani 1 1 d . . . . .
O4 O 0.02702(11) -0.3619(4) -0.69268(8) 0.0714(5) Uani 1 1 d . . . . .
O5 O -0.02112(10) -0.5052(4) -0.61582(8) 0.0621(5) 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 0.0181 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'
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
C2 C1 C8 121.87(19) . . ?
C6 C1 C2 118.7(2) . . ?
C6 C1 C8 119.4(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 120.1(2) . . ?
O1 C3 C2 126.6(2) . . ?
O1 C3 C4 113.23(19) . . ?
C5 C4 C3 119.9(2) . . ?
O2 C4 C3 120.5(2) . . ?
O2 C4 C5 119.5(2) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.9(2) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 121.0(2) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
C1 C8 H8 119.1 . . ?
N1 C8 C1 121.9(2) . . ?
N1 C8 H8 119.1 . . ?
N2 C9 C10 113.89(19) . . ?
O3 C9 C10 123.3(2) . . ?
O3 C9 N2 122.77(19) . . ?
C9 C10 H10 118.5 . . ?
C11 C10 C9 123.0(2) . . ?
C11 C10 H10 118.5 . . ?
C10 C11 H11 117.7 . . ?
C10 C11 C12 124.6(2) . . ?
C12 C11 H11 117.7 . . ?
C11 C12 H12 117.7 . . ?
C13 C12 C11 124.6(2) . . ?
C13 C12 H12 117.7 . . ?
C12 C13 H13 116.8 . . ?
C12 C13 C14 126.3(2) . . ?
C14 C13 H13 116.8 . . ?
C15 C14 C13 119.2(2) . . ?
C15 C14 C19 119.1(2) . . ?
C19 C14 C13 121.63(19) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 C14 122.4(2) . . ?
C16 C15 H15 118.8 . . ?
C15 C16 H16 121.6 . . ?
C17 C16 C15 116.8(2) . . ?
C17 C16 H16 121.6 . . ?
C16 C17 C18 121.7(2) . . ?
C16 C17 O4 128.3(2) . . ?
C18 C17 O4 110.0(2) . . ?
C17 C18 O5 109.51(19) . . ?
C19 C18 C17 122.4(2) . . ?
C19 C18 O5 128.1(2) . . ?
C14 C19 H19 121.2 . . ?
C18 C19 C14 117.5(2) . . ?
C18 C19 H19 121.2 . . ?
H20A C20 H20B 108.5 . . ?
O4 C20 H20A 110.2 . . ?
O4 C20 H20B 110.2 . . ?
O5 C20 H20A 110.2 . . ?
O5 C20 H20B 110.2 . . ?
O5 C20 O4 107.78(19) . . ?
C8 N1 N2 114.73(18) . . ?
C9 N2 N1 120.85(18) . . ?
C9 N2 H2A 119.6 . . ?
N1 N2 H2A 119.6 . . ?
C3 O1 C7 118.55(18) . . ?
C4 O2 H2B 109.5 . . ?
C17 O4 C20 105.78(18) . . ?
C18 O5 C20 105.92(17) . . ?
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
C1 C2 1.399(3) . ?
C1 C6 1.387(3) . ?
C1 C8 1.450(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(3) . ?
C3 C4 1.401(3) . ?
C3 O1 1.363(3) . ?
C4 C5 1.369(3) . ?
C4 O2 1.360(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(3) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C7 O1 1.414(3) . ?
C8 H8 0.9300 . ?
C8 N1 1.274(3) . ?
C9 C10 1.466(3) . ?
C9 N2 1.353(3) . ?
C9 O3 1.228(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.331(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.428(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.339(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.461(3) . ?
C14 C15 1.390(3) . ?
C14 C19 1.408(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.366(3) . ?
C17 C18 1.373(3) . ?
C17 O4 1.374(3) . ?
C18 C19 1.358(3) . ?
C18 O5 1.379(3) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 O4 1.426(3) . ?
C20 O5 1.425(3) . ?
N1 N2 1.383(2) . ?
N2 H2A 0.8600 . ?
O2 H2B 0.8200 . ?
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
N2 H2A O3 0.86 2.04 2.880(2) 164.6 1_545
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
C1 C2 C3 C4 -2.3(3) . . . . ?
C1 C2 C3 O1 176.8(2) . . . . ?
C1 C8 N1 N2 178.29(18) . . . . ?
C2 C1 C6 C5 2.4(3) . . . . ?
C2 C1 C8 N1 -26.3(3) . . . . ?
C2 C3 C4 C5 2.4(4) . . . . ?
C2 C3 C4 O2 179.7(2) . . . . ?
C2 C3 O1 C7 -5.4(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C3 O1 C7 173.7(2) . . . . ?
C4 C5 C6 C1 -2.3(4) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C6 C1 C8 N1 155.2(2) . . . . ?
C8 C1 C2 C3 -178.6(2) . . . . ?
C8 C1 C6 C5 -179.1(2) . . . . ?
C8 N1 N2 C9 167.5(2) . . . . ?
C9 C10 C11 C12 -177.7(2) . . . . ?
C10 C9 N2 N1 179.08(18) . . . . ?
C10 C11 C12 C13 -171.3(2) . . . . ?
C11 C12 C13 C14 178.7(2) . . . . ?
C12 C13 C14 C15 -154.5(2) . . . . ?
C12 C13 C14 C19 24.0(4) . . . . ?
C13 C14 C15 C16 176.0(2) . . . . ?
C13 C14 C19 C18 -178.0(2) . . . . ?
C14 C15 C16 C17 2.4(4) . . . . ?
C15 C14 C19 C18 0.5(3) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C15 C16 C17 O4 -179.3(2) . . . . ?
C16 C17 C18 C19 -1.6(4) . . . . ?
C16 C17 C18 O5 179.6(2) . . . . ?
C16 C17 O4 C20 -173.7(3) . . . . ?
C17 C18 C19 C14 1.5(3) . . . . ?
C17 C18 O5 C20 -5.2(2) . . . . ?
C18 C17 O4 C20 7.2(3) . . . . ?
C19 C14 C15 C16 -2.5(3) . . . . ?
C19 C18 O5 C20 176.0(2) . . . . ?
N2 C9 C10 C11 -168.4(2) . . . . ?
O1 C3 C4 C5 -176.8(2) . . . . ?
O1 C3 C4 O2 0.6(3) . . . . ?
O2 C4 C5 C6 -177.5(2) . . . . ?
O3 C9 C10 C11 13.5(4) . . . . ?
O3 C9 N2 N1 -2.8(3) . . . . ?
O4 C17 C18 C19 177.5(2) . . . . ?
O4 C17 C18 O5 -1.3(3) . . . . ?
O4 C20 O5 C18 9.6(2) . . . . ?
O5 C18 C19 C14 -179.9(2) . . . . ?
O5 C20 O4 C17 -10.3(3) . . . . ?
