Crystal structures and Hirshfeld surface analysis of 2-(adamantan-1-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole and 2-(adamantan-1-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole
Al-Wahaibi, Lamya H.; Alsfouk, Aisha; El-Emam, Ali A.; Blacque, Olivier; Acta Crystallographica Section E 75 (2019) 611–615; doi:10.1107/S2056989019004651

data_2242904
_publ_section_title
;
 Crystal structures and Hirshfeld surface analysis of
 2-(adamantan-1-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole and
 2-(adamantan-1-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              611
_journal_page_last               615
_journal_paper_doi               10.1107/S2056989019004651
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C18 H19 F N2 O'
_chemical_formula_moiety         'C18 H19 F N2 O'
_chemical_formula_sum            'C18 H19 F N2 O'
_chemical_formula_weight         298.35
_chemical_name_systematic
' 2-(Adamantan-1-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.556(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.2525(4)
_cell_length_b                   7.07855(16)
_cell_length_c                   11.2207(2)
_cell_measurement_reflns_used    7588
_cell_measurement_temperature    160.0(10)
_cell_measurement_theta_max      78.5
_cell_measurement_theta_min      4.9
_cell_volume                     1433.59(5)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2019)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2019)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2019)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2008)
;
_computing_publication_material
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
ShelXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
ShelXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      160.0(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13058
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.487
_diffrn_reflns_theta_min         4.900
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2019)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.382
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.229
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0798
_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^)+(0.0572P)^2^+6.0123P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2309
_refine_ls_wR_factor_ref         0.2331
_reflns_number_gt                2578
_reflns_number_total             2903
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            su5492sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1433.59(6)
_cod_database_code               2242904
_cod_database_fobs_code          2242904
_shelx_estimated_absorpt_t_min   0.873
_shelx_estimated_absorpt_t_max   0.988
_shelx_hkl_checksum              46550
_shelx_res_checksum              99722