Synthesis of 3,3'-carbonyl-bis(chromones) and their activity as mammalian alkaline phosphatase inhibitors.
Miliutina, Mariia; Ejaz, Syeda Abida; Iaroshenko, Viktor O.; Villinger, Alexander; Iqbal, Jamshed; Langer, Peter; Organic & biomolecular chemistry 14 (2015) 495–502; doi:10.1039/c5ob01350j

data_7154861
_publ_section_title
;
 Synthesis of 3,3'-carbonyl-bis(chromones) and their activity as mammalian
 alkaline phosphatase inhibitors.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              495
_journal_page_last               502
_journal_paper_doi               10.1039/c5ob01350j
_journal_volume                  14
_journal_year                    2015
_chemical_formula_moiety         'C21 H14 O7'
_chemical_formula_sum            'C21 H14 O7'
_chemical_formula_weight         378.32
_chemical_name_systematic
;
3,3'-carbonylbis(6-methoxy-4<i>H</i>-chromen-4-one)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-06-08 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                74.281(2)
_cell_angle_beta                 81.211(2)
_cell_angle_gamma                68.824(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9459(3)
_cell_length_b                   8.6534(4)
_cell_length_c                   14.8426(7)
_cell_measurement_reflns_used    8275
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.60
_cell_volume                     799.27(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Apex Kappa II-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  0.0268
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20387
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_min         2.654
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0493P)^2^+0.2363P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1057
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3472
_reflns_number_total             4243
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01350j2.cif
_cod_data_source_block           ah_mm2931
_cod_database_code               7154861
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           2013-4
_shelx_res_checksum              24240