Two distinct protocols for the synthesis of unsymmetrical 3,4-disubstituted maleimides based on transition-metal catalysts.
Bandehali-Naeini, Farzaneh; Tanbakouchian, Zahra; Farajinia-Lehi, Noushin; Mayer, Nicolas; Shiri, Morteza; Breugst, Martin; Organic & biomolecular chemistry 22 (2024) 380–387; doi:10.1039/d3ob01620j

data_7159707
_publ_section_title
;
 Two distinct protocols for the synthesis of unsymmetrical
 3,4-disubstituted maleimides based on transition-metal catalysts.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              380
_journal_page_last               387
_journal_paper_doi               10.1039/d3ob01620j
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C24 H21 Br N2 O2'
_chemical_formula_sum            'C24 H21 Br N2 O2'
_chemical_formula_weight         449.35
_chemical_name_systematic
3-(2-bromophenyl)-1-cyclohexyl-4-(1H-indol-2-yl)-1H-pyrrole-2,5-dione
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-08 deposited with the CCDC.	2023-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.102(5)
_cell_angle_beta                 111.664(5)
_cell_angle_gamma                113.639(6)
_cell_formula_units_Z            4
_cell_length_a                   12.1123(7)
_cell_length_b                   13.4106(9)
_cell_length_c                   15.0272(7)
_cell_measurement_reflns_used    7916
_cell_measurement_temperature    153(70)
_cell_measurement_theta_max      25.9130
_cell_measurement_theta_min      3.6330
_cell_volume                     2045.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      153(70)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.855
_diffrn_measured_fraction_theta_max 0.750
_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    -73.00  12.00   1.00   32.78    --    1.07 -40.00 121.00   85
  2  \w    -13.00  75.00   1.00   32.78    --    1.07  40.00 -84.00   88
  3  \w      3.00  40.00   1.00   32.78    --    1.07 -99.00-120.00   37
  4  \w    -10.00  15.00   1.00   32.78    --    1.07 -99.00-150.00   25
  5  \w    -14.00  38.00   1.00   32.78    --   -1.93 -99.00 -30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0691524000
_diffrn_orient_matrix_UB_12      -0.0313647000
_diffrn_orient_matrix_UB_13      -0.0244009000
_diffrn_orient_matrix_UB_21      -0.0076839000
_diffrn_orient_matrix_UB_22      0.0494830000
_diffrn_orient_matrix_UB_23      -0.0072114000
_diffrn_orient_matrix_UB_31      0.0063986000
_diffrn_orient_matrix_UB_32      -0.0027616000
_diffrn_orient_matrix_UB_33      -0.0448828000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1047
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_Laue_measured_fraction_full 0.855
_diffrn_reflns_Laue_measured_fraction_max 0.750
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15127
_diffrn_reflns_point_group_measured_fraction_full 0.855
_diffrn_reflns_point_group_measured_fraction_max 0.750
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.591
_diffrn_reflns_theta_min         3.330
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.032
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       irregular
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.896
_refine_diff_density_min         -1.696
_refine_diff_density_rms         0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         6435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.205
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0752
_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^)+(0.1929P)^2^+0.4819P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2439
_refine_ls_wR_factor_ref         0.2830
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5146
_reflns_number_total             6435
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01620j3.cif
_cod_data_source_block           exp_72
_cod_depositor_comments
;
          Adding full bibliography for 7159707.cif.

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C10.67 H9.33 Br0.44 N0.89 O0.89'
_cod_original_formula_weight         199.71
_cod_original_formula_moiety         '0.44(C24 H21 Br N2 O2)'
_cod_original_formula_units_Z            9
_cod_original_cell_volume        2045.7(2)
_cod_database_code               7159707
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     21.92
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C00V(H00V), C01C(H01P)
2.b Secondary CH2 refined with riding coordinates:
 C011(H01A,H01B), C012(H01C,H01D), C013(H01E,H01F), C018(H01M,H01N), C01A(H01G,
 H01H), C01G(H01R,H01S), C01H(H01T,H01U), C01I(H01J,H01K), C01K(H01V,H01W),
 C01L(H01X,H01Y)
2.c Aromatic/amide H refined with riding coordinates:
 N007(H007), N008(H008), C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O),
 C00P(H00P), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C014(H014),
 C015(H015), C017(H017), C019(H019), C01B(H01O), C01D(H01Q), C01E(H01I),
 C01J(H01L), C01M(H01Z)
;
_shelx_res_checksum              69694
_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 1.825
_oxdiff_exptl_absorpt_empirical_full_min 0.666