Formation of 1-(thiazol-2-yl)-4,5-dihydropyrazoles from simple precursors: synthesis, spectroscopic characterization and the structures of an intermediate and two products
Mahesha, Ninganayaka; Yathirajan, Hemmige S.; Nagma Banu, Holalagudu A.; Kalluraya, Balakrishna; Rathore, Ravindranath S.; Glidewell, Christopher; Acta Crystallographica Section E 77 (2021) –; doi:10.1107/S2056989021009312

data_2243915
_publ_section_title
;
 Formation of 1-(thiazol-2-yl)-4,5-dihydropyrazoles from simple
 precursors: synthesis, spectroscopic characterization and the structures
 of an intermediate and two products
;
_journal_coeditor_code           ZL5017
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989021009312
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C29 H25 N3 O2 S'
_chemical_formula_moiety         'C29 H25 N3 O2 S'
_chemical_formula_sum            'C29 H25 N3 O2 S'
_chemical_formula_weight         479.58
_chemical_name_systematic
(<i>RS</i>)-5-(4-Methoxyphenyl)-1-[4-(4-methylphenyl)thiazol-2-yl]-3-[4-(prop-2-ynyloxy)phenyl]-4,5-dihydro-1<i>H</i>-pyrazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 116.401(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.5634(17)
_cell_length_b                   17.7250(19)
_cell_length_c                   9.4032(11)
_cell_measurement_reflns_used    5580
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.628
_cell_measurement_theta_min      2.470
_cell_volume                     2472.7(5)
_computing_cell_refinement
;
APEX3 and SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT and XPREP (Bruker, 2016)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
<i>SHELXL2014</i> (Sheldrick, 2015b) and PLATON (Spek,
2020)
;
_computing_structure_refinement
;
<i>SHELXL2014</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2014/5</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            40416
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.628
_diffrn_reflns_theta_min         3.337
_diffrn_source
'INCOATEC high brilliance microfocus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.166
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1613 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5578
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0501P)^2^+0.6209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1214
_reflns_number_gt                3802
_reflns_number_total             5578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            zl5017sup1.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2243915
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.976
_shelx_hkl_checksum              77571
_shelx_res_checksum              64180
_shelxl_version_number           2.014
_cod_database_fobs_code 2243915