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_7219753
_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         'C21 H26 N4 O2'
_chemical_formula_sum            'C21 H26 N4 O2'
_chemical_formula_weight         366.46
_chemical_name_common            'Compound 182'
_chemical_name_systematic
;
2-[5-(4-methylpiperazin-1-yl)-2-nitrophenyl]-2,3,4,5-tetrahydro-1H-2-benzazepine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-02-04T23:04:34-00:00
_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                105.049(2)
_cell_angle_beta                 92.969(2)
_cell_angle_gamma                114.7100(10)
_cell_formula_units_Z            2
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_cell_length_b                   10.1771(2)
_cell_length_c                   11.0759(2)
_cell_measurement_reflns_used    3942
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     927.62(4)
_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 0.994
_diffrn_measured_fraction_theta_max 0.987
_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      0.0757067
_diffrn_orient_matrix_UB_12      0.0763788
_diffrn_orient_matrix_UB_13      -0.0355495
_diffrn_orient_matrix_UB_21      0.0875016
_diffrn_orient_matrix_UB_22      -0.0163094
_diffrn_orient_matrix_UB_23      0.0360787
_diffrn_orient_matrix_UB_31      -0.0195535
_diffrn_orient_matrix_UB_32      -0.0827285
_diffrn_orient_matrix_UB_33      -0.0804825
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0107
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7289
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.448
_diffrn_reflns_theta_min         2.788
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.958
_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       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0550P)^2^+0.3576P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.098
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                3928
_reflns_number_total             4191
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra00054h2.cif
_cod_data_source_block           dks-182
_cod_original_cell_volume        927.62(3)
_cod_database_code               7219753