An experimental and theoretical study on the regioselective synthesis of a new class of spiropyrrolothiazoles with quinoxalines motifs via 1,3-dipolar cycloaddition reaction. An evaluation of DFT methods
Hamzehloueian, Mahshid; Sarrafi, Yaghoub; Aghaei, Zahra; RSC Adv.  (2015) –; doi:10.1039/C5RA14071D

data_7221979
_publ_section_title
;
 An experimental and theoretical study on the regioselective synthesis of
 a new class of spiropyrrolothiazoles with quinoxalines motifs via
 1,3-dipolar cycloaddition reaction. An evaluation of DFT methods
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA14071D
_journal_year                    2015
_chemical_formula_sum            'C27 H22 N4 O3 S'
_chemical_formula_weight         482.56
_chemical_melting_point          231
_chemical_name_systematic
'6'-(4-methoxyphenyl)-7'-nitro-3',6',7',7a'-tetrahydro-1'H-spiro[indeno[1,2-b]quinoxaline-11,5'-pyrrolo[1,2-c]thiazole] '
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-06-25 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                94.706(11)
_cell_angle_beta                 104.718(11)
_cell_angle_gamma                117.139(10)
_cell_formula_units_Z            2
_cell_length_a                   10.1308(14)
_cell_length_b                   10.1837(13)
_cell_length_c                   13.2866(18)
_cell_measurement_reflns_used    10490
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.36
_cell_volume                     1148.2(3)
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_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  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10490
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.36
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4969
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0686P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1166
_reflns_number_gt                3296
_reflns_number_total             4969
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra14071d2.cif
_cod_data_source_block           f:\solution\d149\khd149
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'None' changed to 'none'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C27 H22 N4 O3 S1'
_cod_database_code               7221979