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_7219752
_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         'C20 H24 N4 O2'
_chemical_formula_sum            'C20 H24 N4 O2'
_chemical_formula_weight         352.43
_chemical_name_systematic
;
2-[5-(4-methylpiperazin-1-yl)-2-nitrophenyl]-1,2,3,4-tetrahydroisoquinoline
;
_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   geom
_audit_creation_date             2014-02-04T22:50:33-00:00
_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
_cell_angle_beta                 100.828(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_c                   16.1976(3)
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_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      71.0969
_cell_measurement_theta_min      3.0701
_cell_volume                     1762.75(6)
_computing_cell_refinement
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
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_computing_data_collection
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.3756
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_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0657472
_diffrn_orient_matrix_UB_12      -0.1573153
_diffrn_orient_matrix_UB_13      -0.0265129
_diffrn_orient_matrix_UB_21      -0.0844911
_diffrn_orient_matrix_UB_22      0.1240914
_diffrn_orient_matrix_UB_23      -0.0065819
_diffrn_orient_matrix_UB_31      0.0037463
_diffrn_orient_matrix_UB_32      0.0361355
_diffrn_orient_matrix_UB_33      -0.0928963
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0497
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_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23634
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.236
_diffrn_reflns_theta_min         3.073
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.25738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.199
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_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         3397
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.763
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.6023P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1062
_reflns_number_gt                2901
_reflns_number_total             3397
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra00054h2.cif
_cod_data_source_block           new
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7219752