Discovery of the first A1 adenosine receptor ligand based on chromone scaffold
Borges, Fernanda; Cagide-Fagín, Fernando; Reis, Joana; Gaspar, Alexandra; Chavarria, Daniel; Klotz, Karl-Norbert; Vilar, Santiago; Gomes, Lígia R.; Kachler, Sonja; Hripcsak, George; Low, John; RSC Adv.  (2016) –; doi:10.1039/C6RA02347A

data_7225088
_publ_section_title
;
 Discovery of the first A1 adenosine receptor ligand based on chromone
 scaffold
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA02347A
_journal_year                    2016
_chemical_formula_moiety         'C16 H10 N2 O5'
_chemical_formula_sum            'C16 H10 N2 O5'
_chemical_formula_weight         310.26
_chemical_name_systematic
;
<i>N</i>-(2-nitrophenyl)-4-oxo-4<i>H</i>-chromone-3-carboxamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/cc13dyyd
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-04-21 deposited with the CCDC.
2016-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.065(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.104(9)
_cell_length_b                   12.692(8)
_cell_length_c                   7.340(5)
_cell_measurement_reflns_used    3262
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.3
_cell_measurement_theta_min      2.2
_cell_volume                     1293.7(15)
_computing_cell_refinement
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_data_collection
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_molecular_graphics    ' Mercury (Macrae et al, 2006)'
_computing_publication_material
;
Oscail (McArdle et al., 2004),
SHELXL-2014/6 (Sheldrick, 2015)
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
Oscail (McArdle et al., 2004),
ShelXle (H\"ubschle et al., 2011)
SHELXL-2014/6 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2015)
PLATON (Spek, 2009)
Flipper 25 (Oszl\'anyi & S\"ut\>o, 2004)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
scan:
 Number of images: 140
            Slice: -110.0000 - 30.0000
      Image width: 1.0000
         Exp time: 150.0000
    Rotation axis: Omega
            Omega: 0.0000
            Kappa: -15.0000
              Phi: 135.0000
              XTD: 45.0143
           2theta: -19.9329
scan:
 Number of images: 80
            Slice: -90.0000 - -10.0000
      Image width: 1.0000
         Exp time: 150.0000
    Rotation axis: Omega
            Omega: 0.0000
            Kappa: -70.0000
              Phi: 135.0000
              XTD: 45.0143
           2theta: -19.9329
scan:
 Number of images: 44
            Slice: -99.0000 - -55.0000
      Image width: 1.0000
         Exp time: 150.0000
    Rotation axis: Omega
            Omega: 0.0000
            Kappa: -15.0000
              Phi: 45.0000
              XTD: 45.0143
           2theta: -19.9329
scan:
 Number of images: 38
            Slice: -48.0000 - -10.0000
      Image width: 1.0000
         Exp time: 150.0000
    Rotation axis: Omega
            Omega: 0.0000
            Kappa: 70.0000
              Phi: 180.0000
              XTD: 45.0143
           2theta: -19.9329

;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Mitegen
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.131149
_diffrn_orient_matrix_UB_12      -0.017938
_diffrn_orient_matrix_UB_13      -0.040271
_diffrn_orient_matrix_UB_21      -0.018824
_diffrn_orient_matrix_UB_22      -0.024832
_diffrn_orient_matrix_UB_23      0.072363
_diffrn_orient_matrix_UB_31      -0.026876
_diffrn_orient_matrix_UB_32      0.065026
_diffrn_orient_matrix_UB_33      0.015323
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8466
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.934
_diffrn_reflns_transf_matrix_11  -0.131149
_diffrn_reflns_transf_matrix_12  -0.017938
_diffrn_reflns_transf_matrix_13  -0.040271
_diffrn_reflns_transf_matrix_21  -0.018824
_diffrn_reflns_transf_matrix_22  -0.024832
_diffrn_reflns_transf_matrix_23  0.072363
_diffrn_reflns_transf_matrix_31  -0.026876
_diffrn_reflns_transf_matrix_32  0.065026
_diffrn_reflns_transf_matrix_33  0.015323
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.9988
_exptl_absorpt_correction_T_min  0.9892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2012)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_description       rod
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0766
_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^)+(0.0365P)^2^+1.6526P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1525
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2215
_reflns_number_total             2947
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra02347a2.cif
_cod_data_source_block           2b
_cod_database_code               7225088
_publcif_datablock.id            {99e6e887-6bb1-4d5a-b944-911d1f7b80ed}
_shelx_estimated_absorpt_t_min   0.989
_shelx_estimated_absorpt_t_max   0.999
_shelxl_version_number           2014/6
_shelx_res_checksum              30262