Construction of a 1,2-diazetidine core based on a multicomponent reaction of <i>N</i>,<i>N</i>'-(2,3-dimethylbutane-2,3-diyl)bis(hydroxylamine), arylglyoxals, and Meldrum's acid.
Bakuleva, Nadezhda A.; Lichitskii, Boris V.; Komogortsev, Andrey N.; Tretyakov, Evgeny V.; Organic & biomolecular chemistry 23 (2025) 4997–5005; doi:10.1039/d5ob00545k

data_7160523
_publ_section_title
;
 Construction of a 1,2-diazetidine core based on a multicomponent reaction
 of <i>N</i>,<i>N</i>'-(2,3-dimethylbutane-2,3-diyl)bis(hydroxylamine),
 arylglyoxals, and Meldrum's acid.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4997
_journal_page_last               5005
_journal_paper_doi               10.1039/d5ob00545k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         '2(C20 H23 Br N2 O5), C2 H3 N '
_chemical_formula_sum            'C42 H49 Br2 N5 O10'
_chemical_formula_weight         943.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-08-06
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2025-03-11 deposited with the CCDC.	2025-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.3633(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.74413(6)
_cell_length_b                   8.52595(5)
_cell_length_c                   38.0051(2)
_cell_measurement_reflns_used    21202
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.4620
_cell_measurement_theta_min      2.3270
_cell_volume                     4129.39(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.129a 64-bit (release 29-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_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    -51.00 -20.00   0.50    0.32    --  -98.00  45.00   0.00   62
  2  \w    -43.00  39.00   0.50    0.08    --  -40.71  38.00 -30.00  164
  3  \w    -43.00  39.00   0.50    0.08    --  -40.71  38.00 -30.00  164
  4  \w    -27.00  42.00   0.50    0.08    --  -40.71  19.00-180.00  138
  5  \w     61.00 151.00   0.50    0.32    --  119.50-178.00  30.00  180
  6  \w     61.00 151.00   0.50    0.32    --  119.50-178.00  90.00  180
  7  \w     27.00  90.00   0.50    0.08    --   40.71-115.00 108.00  126
  8  \w     45.00 109.00   0.50    0.32    --  119.50-115.00 108.00  128
  9  \w     44.00 108.00   0.50    0.32    --  119.50-111.00 120.00  128
 10  \w     44.00 108.00   0.50    0.32    --  119.50-111.00 150.00  128
 11  \w     58.00 146.00   0.50    0.32    --  119.50-172.00 -33.00  176
 12  \w     41.00 105.00   0.50    0.32    --  119.50 -95.00 120.00  128
 13  \w     61.00 151.00   0.50    0.32    --  119.50-178.00 -60.00  180
 14  \w     61.00 151.00   0.50    0.32    --  119.50-178.00-180.00  180
 15  \w     44.00 108.00   0.50    0.32    --  119.50-111.00-180.00  128
 16  \w     46.00 105.00   0.50    0.32    --  119.50 -77.00-180.00  118
 17  \w     46.00 105.00   0.50    0.32    --  119.50 -77.00 -90.00  118
 18  \w     46.00 105.00   0.50    0.32    --  119.50 -77.00  60.00  118
 19  \w     46.00 105.00   0.50    0.32    --  119.50 -77.00 120.00  118
 20  \w    -42.00  27.00   0.50    0.08    --   40.71 -19.00   0.00  138
 21  \w     87.00 178.00   0.50    0.32    --  119.50  77.00-120.00  182
 22  \w     93.00 178.00   0.50    0.32    --  119.50  61.00 -90.00  170
 23  \w     93.00 178.00   0.50    0.32    --  119.50  61.00 -30.00  170
 24  \w     93.00 178.00   0.50    0.32    --  119.50  45.00   0.00  170
 25  \w     87.00 178.00   0.50    0.32    --  119.50  30.00  90.00  182
 26  \w     87.00 178.00   0.50    0.32    --  119.50  77.00  90.00  182
 27  \w     63.00 123.00   0.50    0.08    --   40.71 178.00 150.00  120
 28  \w     63.00 146.00   0.50    0.32    --  119.50 178.00  60.00  166
 29  \w     63.00 146.00   0.50    0.32    --  119.50 178.00 -90.00  166
 30  \w     66.00 149.00   0.50    0.32    --  119.50 172.00 -20.00  166
 31  \w     63.00 146.00   0.50    0.32    --  119.50 178.00 -60.00  166
 32  \w     63.00 146.00   0.50    0.32    --  119.50 178.00-120.00  166
 33  \w     63.00 146.00   0.50    0.32    --  119.50 178.00-150.00  166
 34  \w    103.00 178.00   0.50    0.32    --  119.50 111.00-150.00  150
 35  \w    101.00 178.00   0.50    0.32    --  119.50 115.00-162.00  154
 36  \w    103.00 178.00   0.50    0.32    --  119.50 111.00 120.00  150
 37  \w    103.00 178.00   0.50    0.32    --  119.50 111.00 150.00  150
 38  \w     -1.00  27.00   0.50    0.08    --   40.71  98.00 110.98   56
 39  \w   -173.00 -80.00   0.50    0.32    --  -98.00-115.00 108.00  186
 40  \w   -121.00 -44.00   0.50    0.08    --  -40.71-172.00 -33.00  154
 41  \w   -119.00 -36.00   0.50    0.32    --  -98.00 172.00 -20.00  166
 42  \w    -83.00  -6.00   0.50    0.08    --  -40.71 115.00-162.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0162299000
_diffrn_orient_matrix_UB_12      -0.1584927000
_diffrn_orient_matrix_UB_13      -0.0187138000
_diffrn_orient_matrix_UB_21      0.0127228000
_diffrn_orient_matrix_UB_22      0.0813232000
_diffrn_orient_matrix_UB_23      -0.0359172000
_diffrn_orient_matrix_UB_31      0.1191325000
_diffrn_orient_matrix_UB_32      -0.0302656000
_diffrn_orient_matrix_UB_33      0.0015732000
_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  0.0302
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            32584
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.065
_diffrn_reflns_theta_min         2.325
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.033
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.473
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_description       prism
_exptl_crystal_F_000             1944
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.00022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0248
_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^)+(0.0312P)^2^+5.0658P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0632
_refine_ls_wR_factor_ref         0.0638
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4342
_reflns_number_total             4467
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00545k2.cif
_cod_data_source_block           NB-358-2
_cod_depositor_comments          'Adding full bibliography for 7160523.cif.'
_cod_database_code               7160523
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C21H23BrN3O5
_chemical_oxdiff_usercomment     NB-358-2
_shelx_estimated_absorpt_t_max   0.816
_shelx_estimated_absorpt_t_min   0.542
_reflns_odcompleteness_completeness 98.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C27(0.5) H27A(0.5) H27B(0.5) H27C(0.5) N25(0.5) C26(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18)
3.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              6542
_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 1.190
_oxdiff_exptl_absorpt_empirical_full_min 0.871