Synthesis and Crystal Structure of 4-(Bis(4-hydroxy-2-oxo-2<i>H</i>-chromen-3-yl)methyl)benzoic Acid
DOCHEV, Stefan; ROLLER, Alexander; MILUNOVIC, Miljan; MANOLOV, Ilia; X-ray Structure Analysis Online 33 (2017) 53–; doi:10.2116/xraystruct.33.53

data_1551574
_publ_section_title
;
 Synthesis and Crystal Structure of
 4-(Bis(4-hydroxy-2-oxo-2&lt;i&gt;H&lt;/i&gt;-chromen-3-yl)methyl)benzoic
 Acid
;
_journal_issue                   0
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              53
_journal_paper_doi               10.2116/xraystruct.33.53
_journal_volume                  33
_journal_year                    2017
_chemical_formula_moiety         'C26 H16 O8, C4 H8 O'
_chemical_formula_sum            'C30 H24 O9'
_chemical_formula_weight         528.49
_chemical_name_systematic
'4-(Bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)benzoic acid'
_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'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-15
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.890(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.676(2)
_cell_length_b                   10.017(2)
_cell_length_c                   24.438(6)
_cell_measurement_reflns_used    1585
_cell_measurement_temperature    130.0
_cell_measurement_theta_max      21.733
_cell_measurement_theta_min      2.651
_cell_volume                     2566.4(9)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       APEX2
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130.0
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0779
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11248
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.360
_diffrn_reflns_theta_min         2.203
_diffrn_source                   'sealed tube'
_diffrn_source_type              'INCOATEC microfocus'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.0784 before and 0.0404 after correction. 
The Ratio of minimum to maximum transmission is 0.8408. 
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_recrystallization_method
'slow solvent evaporation from tetrahydrofuran/water solution'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         4648
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0609
_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^)+(0.0607P)^2^+0.9450P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1579
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2766
_reflns_number_total             4648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            33_53_1.txt
_cod_data_source_block           stdo001_thf_h2o_p21n
_cod_original_cell_volume        2566.4(10)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1551574
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.975