Base-selective access to highly functionalized heterocycles from multicomponent Ugi adducts
González-Saiz, Beatriz; Pertejo, Pablo; Peña-Calleja, Pablo; Mielczarek, Marcin; Hermosilla, Tomás; Carreira-Barral, Israel; de Miguel, Olivia; Rodríguez-Vidal, Francisco; Quesada, Roberto; García-Valverde, María; Green Chemistry 24 (2022) 7988–7995; doi:10.1039/D2GC02896D

data_7245577
_publ_section_title
;
 Base-selective access to highly functionalized heterocycles from
 multicomponent Ugi adducts
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              7988
_journal_page_last               7995
_journal_paper_doi               10.1039/D2GC02896D
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C H Cl3, C30 H28 F N3 O5'
_chemical_formula_sum            'C31 H29 Cl3 F N3 O5'
_chemical_formula_weight         648.92
_chemical_name_systematic        7jdiast2
_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             2022-05-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-07-28 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                108.53(4)
_cell_angle_beta                 96.84(7)
_cell_angle_gamma                106.91(5)
_cell_formula_units_Z            2
_cell_length_a                   9.940(16)
_cell_length_b                   10.793(10)
_cell_length_c                   16.25(2)
_cell_measurement_reflns_used    6451
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      66.076
_cell_measurement_theta_min      2.953
_cell_volume                     1538(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      230(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29480
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.666
_diffrn_reflns_theta_max         66.666
_diffrn_reflns_theta_min         2.949
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    3.129
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1243 before and 0.0889 after correction.
The Ratio of minimum to maximum transmission is 0.6647.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform, hexane'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0025(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0657
_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^)+(0.0915P)^2^+1.9055P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1647
_refine_ls_wR_factor_ref         0.2160
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3218
_reflns_number_total             5392
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc02896d2.cif
_cod_data_source_block           7jdiast2
_cod_depositor_comments
'Adding full bibliography for 7245575--7245579.cif.'
_cod_database_code               7245577
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.745
_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:
 C9(H9), C7(H7), C19(H19), C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C23(H23A,H23B), C24(H24A,H24B), C22(H22A,H22B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C13(H13), C30(H30), C26(H26), C17(H17), C5(H5), C4(H4),
 C2(H2A), C14(H14), C29(H29), C27(H27), C3(H3A), C28(H28), C16(H16)
;
_shelx_res_checksum              89912
_olex2_submission_special_instructions 'No special instructions were received'