Three quinolone compounds featuring O···I halogen bonding
Bauer, Jurica; Milić, Dalibor; Modrić, Marina; Acta Crystallographica Section C 65 (2009) o512–o516; doi:10.1107/S0108270109036361

data_2017333
_publ_section_title
;
 Three quinolone compounds featuring O&#x00B7;&#x00B7;&#x00B7;I halogen
 bonding
;
_journal_coeditor_code           GA3130
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o512
_journal_page_last               o516
_journal_paper_doi               10.1107/S0108270109036361
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H14 I N O3'
_chemical_formula_moiety         'C14 H14 I N O3'
_chemical_formula_sum            'C14 H14 I N O3'
_chemical_formula_weight         371.05
_chemical_name_systematic
;
Ethyl 1-ethyl-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.326(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8169(3)
_cell_length_b                   8.0588(2)
_cell_length_c                   15.8422(4)
_cell_measurement_reflns_used    12268
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      31.8977
_cell_measurement_theta_min      3.9457
_cell_volume                     1380.61(6)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and Mercury (Macrae <i>et al.</i>,
2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) integrated in WinGX (Farrugia, 1999)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008) integrated in WinGX (Farrugia, 1999)
;
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21815
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         4.10
_exptl_absorpt_coefficient_mu    2.323
_exptl_absorpt_correction_T_max  0.498
_exptl_absorpt_correction_T_min  0.396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.741
_refine_diff_density_min         -0.694
_refine_ls_extinction_coef       0.0028(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         4010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0259
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0502P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0796
_reflns_number_gt                3045
_reflns_number_total             4010
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ga3130.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017333
_cod_database_fobs_code          2017333