Synthesis of 2-carboxyaniline-substituted maleimides from 2'-nitrochalcones.
Aksenov, Nicolai A.; Aksenov, Dmitrii A.; Ganusenko, Daniil D.; Kurenkov, Igor A.; Leontiev, Alexander V.; Aksenov, Alexander V.; Organic & biomolecular chemistry 21 (2023) 3156–3166; doi:10.1039/d3ob00197k

data_7159246
_publ_section_title
;
 Synthesis of 2-carboxyaniline-substituted maleimides from
 2'-nitrochalcones.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3156
_journal_page_last               3166
_journal_paper_doi               10.1039/d3ob00197k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C2 H6 O S, C17 H12 N2 O4'
_chemical_formula_sum            'C19 H18 N2 O5 S'
_chemical_formula_weight         386.41
_chemical_name_systematic
'2-((2,5-dioxo-4-phenyl-2,5-dihydro-1H-pyrrol-3-yl)amino)benzoic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-01-17 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.2150(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.71100(10)
_cell_length_b                   8.91200(10)
_cell_length_c                   20.7791(2)
_cell_measurement_reflns_used    12661
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.9490
_cell_measurement_theta_min      2.1610
_cell_volume                     1775.11(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -87.00  -6.00   1.00    1.00    --  -40.82 125.00-180.00   81
  2  \w   -115.00 -16.00   1.00    1.00    --  -40.82 -38.00-180.00   99
  3  \w   -115.00 -16.00   1.00    1.00    --  -40.82 -38.00 -90.00   99
  4  \w      6.00  82.00   1.00    1.00    --   40.82 -99.00 150.00   76
  5  \w    -31.00  69.00   1.00    1.00    --   40.82 -57.00-180.00  100
  6  \w     36.00 109.00   1.00    1.00    --  112.00-111.00  30.00   73
  7  \w     40.00 141.00   1.00    1.00    --  112.00 -61.00 -90.00  101
  8  \w     37.00 137.00   1.00    1.00    --  112.00 -33.00 172.92  100
  9  \w     36.00 109.00   1.00    1.00    --  112.00-111.00   0.00   73
 10  \w    103.00 178.00   1.00    1.00    --  112.00  77.00 -60.00   75
 11  \w    103.00 178.00   1.00    1.00    --  112.00  77.00 120.00   75
 12  \w     36.00 140.00   1.00    1.00    --  112.00 -30.00 -60.00  104
 13  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00  90.00   76
 14  \w    104.00 178.00   1.00    1.00    --  112.00 111.00-180.00   74
 15  \w     83.00 178.00   1.00    1.00    --  112.00  61.00-120.00   95
 16  \w     86.00 178.00   1.00    1.00    --  112.00  45.00-180.00   92
 17  \w     36.00 109.00   1.00    1.00    --  112.00-111.00 -30.00   73
 18  \w    103.00 178.00   1.00    1.00    --  112.00  77.00 -30.00   75
 19  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00  30.00   76
 20  \w     61.00 146.00   1.00    1.00    --  112.00 178.00 150.00   85
 21  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00  60.00   76
 22  \w     81.00 120.00   1.00    1.00    --  112.00   0.00-180.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1534084000
_diffrn_orient_matrix_UB_12      -0.0358563000
_diffrn_orient_matrix_UB_13      -0.0043683000
_diffrn_orient_matrix_UB_21      0.0351926000
_diffrn_orient_matrix_UB_22      0.0005172000
_diffrn_orient_matrix_UB_23      0.0749748000
_diffrn_orient_matrix_UB_31      -0.0324948000
_diffrn_orient_matrix_UB_32      -0.1690981000
_diffrn_orient_matrix_UB_33      0.0011494000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19149
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.132
_diffrn_reflns_theta_min         4.311
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    1.928
_exptl_absorpt_correction_T_max  0.790
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_preparation       'Prepared from nitrochalcone'
_exptl_crystal_recrystallization_method
'Crystallized by slow evaporation of saturated solution in EtOAc.'
_exptl_crystal_size_max          0.339
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0526P)^2^+1.5336P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1059
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3576
_reflns_number_total             3715
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00197k2.cif
_cod_data_source_block           anna_ros845_yellow_2
_cod_depositor_comments          'Adding full bibliography for 7159246.cif.'
_cod_database_code               7159246
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C19 H18 N2 O5 S'
_shelx_estimated_absorpt_t_max   0.761
_shelx_estimated_absorpt_t_min   0.561
_reflns_odcompleteness_completeness 98.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     76.86
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C17(H17), C9(H9), C10(H10), C11(H11), C16(H16), C15(H15), C14(H14),
 C13(H13)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              19061
_olex2_exptl_crystal_mounting_method
'Mounted on the glass stick by acrylic glue'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.196
_oxdiff_exptl_absorpt_empirical_full_min 0.846