A comparison of the structures of some 2- and 3-substituted chromone derivatives: a structural study on the importance of the secondary carboxamide backbone for the inhibitory activity of MAO-B.
Gomes, Ligia R.; Low, John Nicolson; Cagide, Fernando; Gaspar, Alexandra; Borges, Fernanda; Acta crystallographica. Section E, Crystallographic communications 71 (2015) 1270–1277; doi:10.1107/S2056989015017958

data_2311311
_publ_section_title
;
 A comparison of the structures of some 2- and 3-substituted chromone
 derivatives: a structural study on the importance of the secondary
 carboxamide backbone for the inhibitory activity of MAO-B.
;
_journal_issue                   'Pt 11'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1270
_journal_page_last               1277
_journal_paper_doi               10.1107/S2056989015017958
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C14 H13 N O3'
_chemical_formula_moiety         'C14 H13 N O3'
_chemical_formula_sum            'C14 H13 N O3'
_chemical_formula_weight         243.25
_chemical_name_systematic
;
3-(Pyrrolidine-1-carbonyl)-4<i>H</i>-chromen-4-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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.430(3)
_cell_length_b                   11.963(6)
_cell_length_c                   12.648(6)
_cell_measurement_reflns_used    4253
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.2
_cell_measurement_theta_min      2.3
_cell_volume                     1124.2(9)
_computing_cell_refinement
;
<i>CrystalClear-SM Expert</i> (Rigaku, 2012)
;
_computing_data_collection
;
<i>CrystalClear-SM Expert</i> (Rigaku, 2012)
;
_computing_data_reduction
;
<i>CrystalClear-SM Expert</i> (Rigaku, 2012)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2006)
;
_computing_publication_material
;
Oscail (McArdle <i>et al.</i>,  2004),
SHELXL-2014/17 (Sheldrick, 2015) and
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
Oscail (McArdle <i>et al.</i>,  2004),
<i>ShelXle</i> (H\"ubschle <i>et al.</i>,  2011) and
SHELXL-2014/17 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2015),
PLATON (Spek, 2009),
<i>Flipper 25</i> (Oszl\'anyi & S\"ut\>o, 2004) and
Olex2 (Dolomanov <i>et al</i>., 2009).
;
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7547
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.287
_diffrn_reflns_theta_min         2.343
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_correction_T_min  0.9779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>CrystalClear-SM Expert</i>; Rigaku, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       lath
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.440
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 946 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al</i>., 2013)
;
_refine_ls_abs_structure_Flack   -0.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0686
_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^)+(0.0459P)^2^+1.1472P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1483
_refine_ls_wR_factor_ref         0.1521
_reflns_number_gt                3066
_reflns_number_total             3294
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lh5791sup1.cif
_cod_data_source_block           3
_cod_database_code               2311311
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.997
_shelx_hkl_checksum              17900
_shelx_res_checksum              83615