Hydrogen bonding between aromatic H and F groups leading to a stripe structure withR- andS-columns: the crystal structure of (2,7-dimethoxynaphthalen-1-yl)(3-fluorophenyl)methanone and comparison with its 1-aroylnaphthalene analogues
Mohri, Saki; Ohisa, Shinji; Isozaki, Katsuhiro; Yonezawa, Noriyuki; Okamoto, Akiko; Acta Crystallographica Section C Structural Chemistry 71 (2015) –; doi:10.1107/S2053229615005720

data_2019922
_publ_section_title
;
 Hydrogen bonding between aromatic H and F groups leading to a stripe
 structure withR- andS-columns: the crystal structure of
 (2,7-dimethoxynaphthalen-1-yl)(3-fluorophenyl)methanone and comparison
 with its 1-aroylnaphthalene analogues
;
_journal_coeditor_code           YF3082
_journal_issue                   5
_journal_name_full
'Acta Crystallographica Section C Structural Chemistry'
_journal_paper_doi               10.1107/S2053229615005720
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C19 H15 F O3'
_chemical_formula_moiety         'C19 H15 F O3'
_chemical_formula_sum            'C19 H15 F O3'
_chemical_formula_weight         310.31
_chemical_name_systematic
;
(2,7-Dimethoxynaphthalen-1-yl)(3-fluorophenyl)methanone
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.6710(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0057(2)
_cell_length_b                   7.64555(14)
_cell_length_c                   18.6746(3)
_cell_measurement_reflns_used    20127
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      4.13
_cell_volume                     1526.85(5)
_computing_cell_refinement
;
PROCESS-AUTO (Rigaku, 1998)
;
_computing_data_collection
;
PROCESS-AUTO (Rigaku, 1998)
;
_computing_data_reduction
;
CrystalStructure (Rigaku, 2010)
;
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SIR2004 (Burla <i>et al.</i>,  2007)
;
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23103
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         4.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_T_max  0.7624
_exptl_absorpt_correction_T_min  0.5601
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.136
_refine_ls_extinction_coef       0.0090(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL97 (Sheldrick, 2008)
;
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0576P)^2^+0.1828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1005
_reflns_number_gt                2335
_reflns_number_total             2785
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            yf3082sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2019922
_cod_database_fobs_code          2019922