Recurrent π–π stacking motifs in three new 4,5-dihydropyrazolyl–thiazole–coumarin hybrids: X-ray characterization, Hirshfeld surface analysis and DFT calculations
Madni, Murtaza; Ahmed, Muhammad Naeem; Hafeez, Muhammad; Ashfaq, Muhammad; Tahir, Muhammad Nawaz; Gil, Diego M.; Galmés, Bartomeu; Hameed, Shahid; Frontera, Antonio; New Journal of Chemistry 44 (2020) 14592–14603; doi:10.1039/D0NJ02931A

data_7059838
_publ_section_title
;
 Recurrent \p--\p stacking motifs in three new
 4,5-dihydropyrazolyl--thiazole--coumarin hybrids: X-ray characterization,
 Hirshfeld surface analysis and DFT calculations
;
_journal_issue                   34
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14592
_journal_page_last               14603
_journal_paper_doi               10.1039/D0NJ02931A
_journal_volume                  44
_journal_year                    2020
_chemical_formula_iupac          'C27 H17 Cl2 N3 O2 S'
_chemical_formula_moiety         'C27 H17 Cl2 N3 O2 S'
_chemical_formula_sum            'C27 H17 Cl2 N3 O2 S'
_chemical_formula_weight         518.40
_chemical_name_systematic
;
3-[2-(3,5-Di(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-1,3-thiazol-4-yl]-2H
-1-benzopyran-2-one
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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
;
2020-05-19 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                71.363(2)
_cell_angle_beta                 73.094(3)
_cell_angle_gamma                82.970(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6740(6)
_cell_length_b                   11.8234(8)
_cell_length_c                   12.4070(7)
_cell_measurement_reflns_used    4265
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.271
_cell_measurement_theta_min      1.798
_cell_volume                     1152.98(13)
_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 7.76
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0252
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18290
_diffrn_reflns_theta_full        27.271
_diffrn_reflns_theta_max         27.271
_diffrn_reflns_theta_min         1.798
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.405
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0491P)^2^+0.4013P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1074
_reflns_number_gt                4265
_reflns_number_total             5105
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d0nj02931a2.cif
_cod_data_source_block           A14
_cod_depositor_comments
;Adding full bibliography for 7059836--7059838.cif.

 Adding full bibliography for 7059836--7059838.cif.
;
_cod_database_code               7059838
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.861
_shelx_estimated_absorpt_t_max   0.909
_shelx_res_checksum              85504