Crystal engineering with 1,3,4-oxadiazole derivatives: on the importance of CH⋯N and CH⋯π interactions
Ahmed, Muhammad Naeem; Akhtar, Maheen; Andleeb, Hina; Bashir, Muhammad Adnan; Ibrahim, Mahmoud A. A.; Sidhom, Peter A.; Arshad, Ifzan; Tahir, Muhammad Nawaz; Gil, Diego M.; Gomila, Rosa M.; Frontera, Antonio; CrystEngComm 25 (2023) 6710–6718; doi:10.1039/D3CE00944K

data_7247701
_publ_section_title
;
 Crystal engineering with 1,3,4-oxadiazole derivatives: on the importance
 of CH&#x22EF;N and CH&#x22EF;\p interactions
;
_journal_issue                   48
_journal_name_full               CrystEngComm
_journal_page_first              6710
_journal_page_last               6718
_journal_paper_doi               10.1039/D3CE00944K
_journal_volume                  25
_journal_year                    2023
_chemical_formula_iupac          'C22 H26 N2 O4 S'
_chemical_formula_moiety         'C22 H26 N2 O4 S'
_chemical_formula_sum            'C22 H26 N2 O4 S'
_chemical_formula_weight         414.51
_chemical_name_systematic
2-[(4-Tertbutylphenylmethyl)sulfanyl]-5-(3,4,5-trimethoxyphenyl)-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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2023-10-06 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.9360(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.40660(10)
_cell_length_b                   24.9033(2)
_cell_length_c                   8.87920(10)
_cell_measurement_reflns_used    4266
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      77.005
_cell_measurement_theta_min      4.290
_cell_volume                     2279.08(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL-2019/2  (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.16
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            31041
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.975
_diffrn_reflns_theta_min         4.290
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.497
_exptl_absorpt_correction_T_max  0.615
_exptl_absorpt_correction_T_min  0.545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correctionusing spherical harmonics,
implimented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0015(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4391
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0771P)^2^+0.4386P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1372
_reflns_number_gt                4023
_reflns_number_total             4391
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d3ce00944k2.cif
_cod_data_source_block           9_AUTO
_cod_depositor_comments
'Adding full bibliography for 7247700--7247701.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7247701
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.615
_shelx_estimated_absorpt_t_max   0.774
_shelx_res_checksum              12855