Bifunctional squaramide catalyzed stereoselective Mannich reaction of α-azido ketones with isatin-derived ketimines.
Karahan, Seda; Tanyeli, Cihangir; Organic & biomolecular chemistry 18 (2020) 479–487; doi:10.1039/c9ob02208b

data_7157257
_publ_section_title
;
 Bifunctional squaramide catalyzed stereoselective Mannich reaction of
 \a-azido ketones with isatin-derived ketimines.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              479
_journal_page_last               487
_journal_paper_doi               10.1039/c9ob02208b
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C23 H23 N5 O5'
_chemical_formula_sum            'C23 H23 N5 O5'
_chemical_formula_weight         449.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-05-30 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                74.014(5)
_cell_angle_beta                 74.695(5)
_cell_angle_gamma                72.702(5)
_cell_formula_units_Z            2
_cell_length_a                   10.2450(2)
_cell_length_b                   10.9607(2)
_cell_length_c                   11.1338(7)
_cell_measurement_reflns_used    29145
_cell_measurement_temperature    295
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      3.07
_cell_volume                     1124.73(9)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9969
_diffrn_measurement_device_type  'Rigaku RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            29145
_diffrn_reflns_theta_full        28.2574
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.096
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.3271
_exptl_crystal_description       block
_exptl_crystal_F_000             472.2417
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.76
_exptl_crystal_size_min          0.55
_refine_diff_density_max         0.3754
_refine_diff_density_min         -0.4439
_refine_diff_density_rms         0.1277
_refine_ls_d_res_high            0.7506
_refine_ls_d_res_low             6.6456
_refine_ls_goodness_of_fit_ref   1.0697
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    37
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5552
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0697
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0588
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0973P)^2^+0.1929P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1599
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                4872
_reflns_number_total             5552
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9ob02208b2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 7157257.cif.'
_cod_database_code               7157257
_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.a Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C16(H16), C15(H15), C14(H14), C13(H13), N2(H2)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C23(H23a,H23b,H23c), C22(H22a,H22b,H22c), C21(H21a,H21b,H21c)
;
_olex2_submission_original_sample_id Seda
_olex2_submission_special_instructions 'No special instructions were received'