Crystal structure, Hirshfeld surface analysis and energy frameworks of 1-[(<i>E</i>)-2-(2-fluoro-phen-yl)diazan-1-yl-idene]naphthalen-2(1<i>H</i>)-one.
Akkache, Hibet Errahmane Meroua; Hamdouni, Noudjoud; Boudjada, Ali; Medjroubi, Mohamed Larbi; Mili, Assia; Jeannin, Olivier; Acta crystallographica. Section E, Crystallographic communications 80 (2024) 137–142; doi:10.1107/S2056989024000227

data_2023006
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and energy frameworks of
 1-[(<i>E</i>)-2-(2-fluoro-phen-yl)diazan-1-yl-idene]naphthalen-2(1<i>H</i>)-one.
;
_journal_coeditor_code           EE2002
_journal_issue                   'Pt 2'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              137
_journal_page_last               142
_journal_paper_doi               10.1107/S2056989024000227
_journal_volume                  80
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_compound_source        organic
_chemical_formula_iupac          'C16 H11 F N2 O'
_chemical_formula_moiety         'C16 H11 F N2 O'
_chemical_formula_sum            'C16 H11 F N2 O'
_chemical_formula_weight         266.27
_chemical_name_systematic
;
1-[(<i>E</i>)-2-(2-Fluorophenyl)diazan-1-ylidene]naphthalen-2(1<i>H</i>)-one
;
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.612(3)
_cell_length_b                   7.2392(8)
_cell_length_c                   7.2122(7)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.94
_cell_volume                     1232.8(2)
_computing_cell_refinement
;
APEX3 (Bruker, 2015)
;
_computing_data_collection
;
APEX3 (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012),
Mercury (Macrae <i>et al.</i>,  2020), OLEX2 (Dolomanov <i>et al.</i>,
 2009)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 2012)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2018/2</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'D8 VENTURE Bruker AXS'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5289
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.943
_diffrn_source                   'Enraf--Nonius FR590'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange-red
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.23
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1169 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2803
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+0.1870P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1094
_reflns_number_gt                2700
_reflns_number_total             2803
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ee2002sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2023006.cif.'
_cod_database_code               2023006
_cod_database_fobs_code          2023006
_shelx_hkl_checksum              41922
_shelx_res_checksum              7430