Pd-catalysed [3+2]-Cycloaddition towards the generation of bioactive bis-heterocycles/Identification of COX-2 inhibitors via in silico analysis
Sathish, Elagandhula; Ansari, Arshad J.; Joshi, Gaurav; Pandit, Akansha; Shukla, Monika; Kumari, Neha; Sharon, Ashoke; Verma, Ved Prakash; Sawant, Devesh M.; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00467D

data_7158696
_publ_section_title
;
 Pd-catalysed [3+2]-Cycloaddition towards the generation of bioactive
 bis-heterocycles/Identification of COX-2 inhibitors via in silico
 analysis
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00467D
_journal_year                    2022
_chemical_formula_moiety         'C18 H14 Cl N O4'
_chemical_formula_sum            'C18 H14 Cl N O4'
_chemical_formula_weight         343.75
_chemical_name_systematic
(S)-4-((R)-3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl)-4-phenyl-1,3-dioxolan-2-one
_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
_audit_creation_date             2022-02-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-02-09 deposited with the CCDC.	2022-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                110.956(10)
_cell_angle_beta                 90.069(10)
_cell_angle_gamma                90.054(10)
_cell_formula_units_Z            2
_cell_length_a                   8.777(4)
_cell_length_b                   9.470(4)
_cell_length_c                   10.205(4)
_cell_measurement_reflns_used    4755
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.411
_cell_measurement_theta_min      2.6666
_cell_volume                     792.1(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku oxford diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18576
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.411
_diffrn_reflns_theta_min         2.520
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1804 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_coef       0.0155(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         6086
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0187P)^2^+0.4234P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0958
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_full    0.909
_reflns_Friedel_fraction_max     0.886
_reflns_number_gt                4755
_reflns_number_total             6086
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00467d2.cif
_cod_data_source_block           t_a
_cod_database_code               7158696
_publcif_datablock.id            {609c82c1-1688-4f7b-a22a-b36b7e094314}
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.925
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C40(H40)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C41(H41A,H41B), C47(H47A,H47B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C19(H19), C20(H20), C21(H21), C22(H22),
 C23(H23), C32(H32), C33(H33), C35(H35), C36(H36), C49(H49), C50(H50), C51(H51),
  C52(H52), C53(H53)
;
_shelx_res_checksum              85269
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
;
;