Rational design of 5-HT6R ligands using a bioisosteric strategy: Synthesis, biological evaluation and molecular modelling
Staroń, Jakub; Warszycki, Dawid; Kalinowska-Tłuścik, Justyna; Satała, Grzegorz; Bojarski, AJ; RSC Adv.  (2015) –; doi:10.1039/C5RA00054H

data_7219750
_publ_section_title
;
 Rational design of 5-HT6R ligands using a bioisosteric strategy:
 Synthesis, biological evaluation and molecular modelling
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA00054H
_journal_year                    2015
_chemical_formula_moiety         'C18 H22 N4 O2'
_chemical_formula_sum            'C18 H22 N4 O2'
_chemical_formula_weight         326.39
_chemical_name_common            'Compound 172'
_chemical_name_systematic
;
N-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-01-29T22:33:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2014-04-05 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.000
_cell_angle_beta                 108.015(2)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   14.8320(4)
_cell_length_b                   4.8941(2)
_cell_length_c                   23.9340(7)
_cell_measurement_reflns_used    4493
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.7
_cell_measurement_theta_min      0.998
_cell_volume                     1652.18(10)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.0150412
_diffrn_orient_matrix_UB_12      0.1265995
_diffrn_orient_matrix_UB_13      -0.0344553
_diffrn_orient_matrix_UB_21      0.0181049
_diffrn_orient_matrix_UB_22      0.1597043
_diffrn_orient_matrix_UB_23      0.0272518
_diffrn_orient_matrix_UB_31      0.0669035
_diffrn_orient_matrix_UB_32      -0.0147275
_diffrn_orient_matrix_UB_33      -0.0006677
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            10299
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.682
_diffrn_reflns_theta_min         2.624
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        DENZO-SMN; Otwinowski & Minor, 1997
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0564P)^2^+0.4300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1199
_reflns_number_gt                3068
_reflns_number_total             4234
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra00054h2.cif
_cod_data_source_block           dks-172
_cod_original_cell_volume        1652.15(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7219750