Phase-transfer catalyzed Michael/ammonolysis cascade reactions of enaminones and olefinic azlactones: a new approach to structurally diverse quinoline-2,5-diones
Chen, Lin; Liang, Wei; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00096B

data_7158623
_publ_section_title
;
 Phase-transfer catalyzed Michael/ammonolysis cascade reactions of
 enaminones and olefinic azlactones: a new approach to structurally
 diverse quinoline-2,5-diones
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00096B
_journal_year                    2022
_chemical_formula_moiety         'C31 H29 Br N2 O3'
_chemical_formula_sum            'C31 H29 Br N2 O3'
_chemical_formula_weight         557.47
_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             2021-08-08
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-08-15 deposited with the CCDC.	2022-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                87.802(5)
_cell_angle_beta                 88.240(4)
_cell_angle_gamma                81.951(5)
_cell_formula_units_Z            4
_cell_length_a                   10.5937(6)
_cell_length_b                   15.3406(11)
_cell_length_c                   16.5661(7)
_cell_measurement_reflns_used    4376
_cell_measurement_temperature    250.01(10)
_cell_measurement_theta_max      24.6030
_cell_measurement_theta_min      2.4760
_cell_volume                     2662.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (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      250.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -59.00  37.00   1.00    5.00    --   11.90 -57.00 -30.00   96
  2  \w    -15.00  83.00   1.00    5.00    --   11.90  57.00 120.00   98
  3  \w     37.00  63.00   1.00    5.00    --   11.90 178.00 -60.00   26
  4  \w    -14.00  79.00   1.00    5.00    --   11.90  77.00-120.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0281520000
_diffrn_orient_matrix_UB_12      0.0151598000
_diffrn_orient_matrix_UB_13      -0.0371723000
_diffrn_orient_matrix_UB_21      0.0117304000
_diffrn_orient_matrix_UB_22      -0.0434242000
_diffrn_orient_matrix_UB_23      -0.0143780000
_diffrn_orient_matrix_UB_31      -0.0603780000
_diffrn_orient_matrix_UB_32      -0.0082282000
_diffrn_orient_matrix_UB_33      0.0157684000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19181
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.942
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.579
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (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    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.175
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     683
_refine_ls_number_reflns         9378
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1175
_refine_ls_R_factor_gt           0.0621
_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^)+(0.0666P)^2^+0.9671P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1585
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5817
_reflns_number_total             9378
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00096b2.cif
_cod_data_source_block           duibr
_cod_database_code               7158623
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.833
_shelx_estimated_absorpt_t_min   0.809
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 O3, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 O7, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Others
 Sof(O7)=1-FVAR(1)
 Sof(O3)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C48(H48), C49(H49)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C34(H34A,H34B), C36(H36A,H36B)
4.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C11(H11), C12(H12), C14(H14), C15(H15), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C26(H26), C27(H27), C29(H29), C30(H30), N4(H4), C41(H41),
 C42(H42), C44(H44), C45(H45), C51(H51), C52(H52), C54(H54), C55(H55), C58(H58),
  C59(H59), C60(H60), C61(H61), C62(H62)
4.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C31(H31A,H31B,H31C), C38(H38A,H38B,
 H38C), C39(H39A,H39B,H39C), C46(H46A,H46B,H46C)
;
_shelx_res_checksum              2909
_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 1.599
_oxdiff_exptl_absorpt_empirical_full_min 0.734