Highly regioselective and diastereoselective synthesis of novel pyrazinoindolones <i>via</i> a base-mediated Ugi-<i>N</i>-alkylation sequence.
Tajik, Maryam; Shiri, Morteza; Hussain, Faiq H. S.; Lotfi Nosood, Yazdanbakhsh; Baeiszadeh, Behnaz; Amini, Zahra; Bikas, Rahman; Pyra, Anna; RSC advances 13 (2023) 16963–16969; doi:10.1039/d3ra02065g

data_7246993
_publ_section_title
;
 Highly regioselective and diastereoselective synthesis of novel
 pyrazinoindolones <i>via</i> a base-mediated Ugi-<i>N</i>-alkylation
 sequence.
;
_journal_issue                   25
_journal_name_full               'RSC advances'
_journal_page_first              16963
_journal_page_last               16969
_journal_paper_doi               10.1039/d3ra02065g
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C32 H32 Cl N3 O3'
_chemical_formula_sum            'C32 H32 Cl N3 O3'
_chemical_formula_weight         542.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-04-01 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.04(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.155(9)
_cell_length_b                   6.9777(18)
_cell_length_c                   30.372(14)
_cell_measurement_reflns_used    8663
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      50
_cell_measurement_theta_min      2
_cell_volume                     5458(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_av_unetI/netI     0.0787
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            32621
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         73.435
_diffrn_reflns_theta_min         2.059
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.549
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.548
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       needle
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.00066(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     742
_refine_ls_number_reflns         10338
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.1308
_refine_ls_R_factor_gt           0.0888
_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^)+(0.1738P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2463
_refine_ls_wR_factor_ref         0.2780
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6331
_reflns_number_total             10338
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra02065g2.cif
_cod_data_source_block           tmb2a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'direct methods' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_database_code               7246993
_shelx_estimated_absorpt_t_min   0.654
_shelx_estimated_absorpt_t_max   0.970
_oxdiff_exptl_absorpt_empirical_full_min 0.599
_oxdiff_exptl_absorpt_empirical_full_max 1.617
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelxl_version_number           2013-2
_shelx_res_checksum              10632