Diversity oriented synthesis of 6-Nitro- and 6-Aminoquinolones and their activity as alkaline phosphatase inhibitors
Milyutina, Maria; Ivanov, Anton; Ejaz, Syeda; Iqbal, Jamshed; Villinger, Alexander; Iaroshenko, Victor O.; Langer, Peter; RSC Adv.  (2015) –; doi:10.1039/C5RA10948E

data_7221031
_publ_section_title
;
 Diversity oriented synthesis of 6-Nitro- and 6-Aminoquinolones and their
 activity as alkaline phosphatase inhibitors
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA10948E
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C24 H20 N2 O3'
_chemical_formula_sum            'C24 H20 N2 O3'
_chemical_formula_weight         384.42
_chemical_name_systematic
;
(<i>R</i>)-6-Nitro-1-(1-phenylethyl)-2-(4-tolyl)quinolin-4(1<i>H</i>)-one
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-05-29 deposited with the CCDC.
2015-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9322(10)
_cell_length_b                   13.6154(10)
_cell_length_c                   14.4052(15)
_cell_measurement_reflns_used    3063
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.64
_cell_measurement_theta_min      2.49
_cell_volume                     1948.0(3)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15463
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_min         3.628
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1083 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(7)
_refine_ls_extinction_coef       0.0048(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         5004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0342P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                3347
_reflns_number_total             5004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra10948e2.cif
_cod_data_source_block           is_mm115_118
_cod_database_code               7221031
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           2013-4
_shelx_res_checksum              64602