Experimental and Theoretical Studies on Constitutional Isomers of 2,6-Dihydroxynaphthalene Carbaldehydes. Effects of Resonance-Assisted Hydrogen Bonding on the Electronic Absorption Spectra
Hirohiko Houjou; Takatoshi Motoyama; Seisaku Banno; Isao Yoshikawa; Koji Araki; Journal of Organic Chemistry 74 (2009) 520–529; doi:10.1021/jo802345f

data_4024276
_publ_section_title
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Experimental and Theoretical Studies on Constitutional Isomers of
2,6-Dihydroxynaphthalene Carbaldehydes. Effects of Resonance-Assisted
Hydrogen Bonding on the Electronic Absorption Spectra
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              520
_journal_page_last               529
_journal_paper_doi               10.1021/jo802345f
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C12 H8 O4'
_chemical_formula_sum            'C12 H8 O4'
_chemical_formula_weight         216.18
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.870(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.3980(2)
_cell_length_b                   12.2080(6)
_cell_length_c                   8.6590(5)
_cell_measurement_reflns_used    4150
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      73.44
_cell_measurement_theta_min      6.37
_cell_volume                     453.23(4)
_computing_cell_refinement       Scalepack
_computing_data_collection       'MacScience Xpress'
_computing_data_reduction        'Denzo and Scalepack'
_computing_molecular_graphics    maXus
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.847
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measurement_device_type  'MacScience DIPLabo'
_diffrn_measurement_method       IP
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4150
_diffrn_reflns_theta_full        73.44
_diffrn_reflns_theta_max         73.44
_diffrn_reflns_theta_min         6.37
_exptl_absorpt_coefficient_mu    1.015
_exptl_absorpt_correction_T_max  0.8542
_exptl_absorpt_correction_T_min  0.6998
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0619
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1111P)^2^+0.2455P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1798
_refine_ls_wR_factor_ref         0.1810
_reflns_number_gt                747
_reflns_number_total             781
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802345f_si_002.cif
_cod_data_source_block           070723
_cod_depositor_comments
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The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
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_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4024276