Development of subnanomolar-affinity serotonin 5-HT<sub>4</sub> receptor ligands based on quinoline structures.
Castriconi, Federica; Paolino, Marco; Grisci, Giorgio; Francini, Cinzia Maria; Reale, Annalisa; Giuliani, Germano; Anzini, Maurizio; Giorgi, Gianluca; Mennuni, Laura; Sabatini, Chiara; Lanza, Marco; Caselli, Gianfranco; Cappelli, Andrea; MedChemComm 9 (2018) 1466–1471; doi:10.1039/c8md00233a

data_7121917
_publ_section_title
;
 Development of subnanomolar-affinity serotonin 5-HT<sub>4</sub> receptor
 ligands based on quinoline structures.
;
_journal_issue                   9
_journal_name_full               MedChemComm
_journal_page_first              1466
_journal_page_last               1471
_journal_paper_doi               10.1039/c8md00233a
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C18 H22 Cl N3 O'
_chemical_formula_sum            'C18 H22 Cl N3 O'
_chemical_formula_weight         331.83
_chemical_name_systematic
;
4-chloro-N-(3-(piperidin-1-yl)propyl)quinoline-2-carboxamide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2018-05-02 deposited with the CCDC.
2018-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   37.512(5)
_cell_length_b                   7.280(5)
_cell_length_c                   12.978(5)
_cell_measurement_reflns_used    22101
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      2.9
_cell_volume                     3544(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_av_unetI/netI     0.3501
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15689
_diffrn_reflns_point_group_measured_fraction_full 0.862
_diffrn_reflns_point_group_measured_fraction_max 0.744
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         29.143
_diffrn_reflns_theta_min         2.679
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98342
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       needle
_exptl_crystal_F_000             1408
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 399 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.586
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         7097
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.586
_refine_ls_R_factor_all          0.2630
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0095P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0396
_refine_ls_wR_factor_ref         0.0560
_reflns_Friedel_coverage         0.594
_reflns_Friedel_fraction_full    0.711
_reflns_Friedel_fraction_max     0.579
_reflns_number_gt                1553
_reflns_number_total             7097
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8md00233a2.cif
_cod_data_source_block           VC1400
_cod_depositor_comments
'Adding full bibliography for 7121917--7121918.cif.'
_cod_database_code               7121917
_shelx_shelxl_version_number     2018/1
_exptl_absorpt_special_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_shelx_res_checksum              68452