Three-Component One-Pot Approach to Highly Efficient and Sustainable Synthesis of the Functionalized Quinolones via Linear/Branched Domino Protocols, Key Synthetic Methods for the Floxacin of Quinolone Drugs.
Bai, Hairui; Liu, Fujun; Wang, Xiaojing; Wang, Ping; Huang, Chao; ACS omega 3 (2018) 11233–11251; doi:10.1021/acsomega.8b01378

data_4516088
_publ_section_title
;
 Three-Component One-Pot Approach to Highly Efficient and Sustainable
 Synthesis of the Functionalized Quinolones via Linear/Branched Domino
 Protocols, Key Synthetic Methods for the Floxacin of Quinolone Drugs.
;
_journal_issue                   9
_journal_name_full               'ACS omega'
_journal_page_first              11233
_journal_page_last               11251
_journal_paper_doi               10.1021/acsomega.8b01378
_journal_volume                  3
_journal_year                    2018
_chemical_formula_moiety         'C14 H15 N O2'
_chemical_formula_sum            'C14 H15 N O2'
_chemical_formula_weight         229.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-10
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.395(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.6496(17)
_cell_length_b                   9.9333(13)
_cell_length_c                   19.755(3)
_cell_measurement_reflns_used    2532
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.644
_cell_measurement_theta_min      2.713
_cell_volume                     2441.5(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14358
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.713
_diffrn_reflns_theta_min         2.933
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0662 before and 0.0419 after correction.
The Ratio of minimum to maximum transmission is 0.8605.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         5567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0568P)^2^+0.2804P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1408
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3060
_reflns_number_total             5567
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b01378_si_001.cif
_cod_data_source_block           bhr6a_0m
_cod_database_code               4516088
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), N2(H2), C22(H22),
 C25(H25), C26(H26), C27(H27), C28(H28)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C19(H19A,H19B,H19C),
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              7493
_shelx_hkl_checksum              8221
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'