IMDAV reaction between phenylmaleic anhydride and thienyl(furyl)allylamines: synthesis and molecular structure of (3a<i>SR</i>,4<i>RS</i>,4a<i>RS</i>,7a<i>SR</i>)-5-oxothieno- and (3a<i>SR</i>,4<i>SR</i>,4a<i>RS</i>,7a<i>SR</i>)-5-oxofuro[2,3-<i>f</i>]isoindole-4-carboxylic acids
Toze, Flavien A. A.; Nadirova, Maryana A.; Mertsalov, Dmitriy F.; Sokolova, Julya S.; Dorovatovskii, Pavel V.; Khrustalev, Victor N.; Acta Crystallographica Section E 74 (2018) 1400–1404; doi:10.1107/S2056989018012239

data_2242625
_publ_section_title
;
 IMDAV reaction between phenylmaleic anhydride and
 thienyl(furyl)allylamines: synthesis and molecular structure of
 (3a<i>SR</i>,4<i>RS</i>,4a<i>RS</i>,7a<i>SR</i>)-5-oxothieno- and
 (3a<i>SR</i>,4<i>SR</i>,4a<i>RS</i>,7a<i>SR</i>)-5-oxofuro[2,3-<i>f</i>]isoindole-4-carboxylic
 acids
;
_journal_coeditor_code           YK2117
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1400
_journal_page_last               1404
_journal_paper_doi               10.1107/S2056989018012239
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C24 H21 N O3 S'
_chemical_formula_moiety         'C24 H21 N O3 S'
_chemical_formula_sum            'C24 H21 N O3 S'
_chemical_formula_weight         403.48
_chemical_name_systematic
'(3a<i>SR</i>,4<i>RS</i>,4a<i>RS</i>,7a<i>SR</i>)-5-Oxothieno[2,3-<i>f</i>]isoindole-4-carboxylic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 111.92(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.572(3)
_cell_length_b                   8.7989(18)
_cell_length_c                   16.982(3)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.0
_cell_measurement_theta_min      3.6
_cell_volume                     2020.0(8)
_computing_cell_refinement
;
<i>iMosflm</i> (Battye <i>et al.</i>,  2011)
;
_computing_data_collection
;
<i>MarCCD</i> (Doyle, 2011)
;
_computing_data_reduction
;
<i>iMosflm</i> (Battye <i>et al.</i>,  2011)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.96260
_diffrn_reflns_av_R_equivalents  0.1008
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12006
_diffrn_reflns_theta_full        35.279
_diffrn_reflns_theta_max         38.408
_diffrn_reflns_theta_min         3.592
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SCALA; Evans, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.831
_refine_ls_extinction_coef       0.027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.0820
_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^)+(0.08P)^2^+4P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1923
_refine_ls_wR_factor_ref         0.2444
_reflns_number_gt                2888
_reflns_number_total             4140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yk2117sup1.cif
_cod_data_source_block           I
_cod_database_code               2242625
_cod_database_fobs_code          2242625
_shelx_estimated_absorpt_t_min   0.936
_shelx_estimated_absorpt_t_max   0.957
_shelx_hkl_checksum              19473
_shelx_res_checksum              63109
_shelxl_version_number           2014/6