Crystal engineering with pyrazolyl-thiazole derivatives: structure-directing role of π-stacking and σ-hole interactions
Ahmed, Muhammad Naeem; Madni, Murtaza; Anjum, Shaista; Andleeb, Saiqa; Hameed, Shahid; Khan, Abdul Majeed; Ashfaq, Muhammad; Tahir, Muhammad Nawaz; Gil, Diego M.; Frontera, Antonio; CrystEngComm 23 (2021) 3276–3287; doi:10.1039/D1CE00256B

data_7242370
_publ_section_title
;
 Crystal engineering with pyrazolyl-thiazole derivatives:
 structure-directing role of \p-stacking and \s-hole interactions
;
_journal_issue                   18
_journal_name_full               CrystEngComm
_journal_page_first              3276
_journal_page_last               3287
_journal_paper_doi               10.1039/D1CE00256B
_journal_volume                  23
_journal_year                    2021
_chemical_formula_iupac          'C21 H17 Br Cl N3 O2 S'
_chemical_formula_moiety         'C21 H17 Br Cl N3 O2 S'
_chemical_formula_sum            'C21 H17 Br Cl N3 O2 S'
_chemical_formula_weight         490.80
_chemical_name_systematic
;
Ethyl 2-[5-(4-bromophenyl)-3-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]-
1,3-thiazole-4-carboxylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-02-05 deposited with the CCDC.	2021-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                73.421(5)
_cell_angle_beta                 89.483(5)
_cell_angle_gamma                86.045(6)
_cell_formula_units_Z            1
_cell_length_a                   4.7441(4)
_cell_length_b                   9.5883(9)
_cell_length_c                   12.0770(11)
_cell_measurement_reflns_used    3367
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.502
_cell_measurement_theta_min      2.222
_cell_volume                     525.23(8)
_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-2018/3  (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.72
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8109
_diffrn_reflns_theta_full        27.502
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_min         2.222
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.206
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4306
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0336P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0766
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3367
_reflns_number_total             4306
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d1ce00256b2.cif
_cod_data_source_block           A31P
_cod_depositor_comments
'Adding full bibliography for 7242370--7242372.cif.'
_cod_database_code               7242370
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.472
_shelx_estimated_absorpt_t_max   0.719
_shelx_res_checksum              70589
_shelx_hkl_checksum              40128