A one-pot route to N-acyl ureas: a formal four-component hydrolytic reaction involving aminonitrones and isocyanide dibromides
Il’in, Mikhail V.; Lesnikova, Liana A.; Bolotin, Dmitrii S.; Novikov, Alexander S.; Suslonov, Vitalii V.; Kukushkin, Vadim Yu.; New Journal of Chemistry 44 (2020) 1253–1262; doi:10.1039/C9NJ05445F

data_7059176
_publ_section_title
;
 A one-pot route to N-acyl ureas: a formal four-component hydrolytic
 reaction involving aminonitrones and isocyanide dibromides
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1253
_journal_page_last               1262
_journal_paper_doi               10.1039/C9NJ05445F
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C15 H17 F3 N2 O2'
_chemical_formula_sum            'C15 H17 F3 N2 O2'
_chemical_formula_weight         314.30
_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     iterative
_audit_creation_date             2019-07-05
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_audit_update_record
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2019-07-05 deposited with the CCDC.	2019-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                100.531(9)
_cell_angle_beta                 94.646(14)
_cell_angle_gamma                100.547(15)
_cell_formula_units_Z            2
_cell_length_a                   5.1066(12)
_cell_length_b                   11.5568(13)
_cell_length_c                   12.7664(13)
_cell_measurement_reflns_used    1953
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.1860
_cell_measurement_theta_min      3.2840
_cell_volume                     723.1(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -69.00  -42.00   1.0000   14.3600
omega____ theta____ kappa____ phi______ frames
    -      -25.5873 -178.0000    0.0000 27

  2 omega   20.00   61.00   1.0000   14.3600
omega____ theta____ kappa____ phi______ frames
    -       26.6811  -99.0000  -30.0000 41

  3 omega   52.00   97.00   1.0000   14.3600
omega____ theta____ kappa____ phi______ frames
    -       26.6811 -178.0000 -120.0000 45

  4 omega  -21.00   69.00   1.0000   14.3600
omega____ theta____ kappa____ phi______ frames
    -       26.6811  -99.0000   60.0000 90

  5 omega   40.00   69.00   1.0000   14.3600
omega____ theta____ kappa____ phi______ frames
    -       26.6811  -99.0000 -150.0000 29

  6 omega  -38.00   39.00   1.0000   14.3600
omega____ theta____ kappa____ phi______ frames
    -       26.6811  -57.0000 -180.0000 77

  7 omega  -17.00  100.00   1.0000   14.3600
omega____ theta____ kappa____ phi______ frames
    -       26.6811   19.0000    0.0000 117

  8 omega  -47.00  -22.00   1.0000   14.3600
omega____ theta____ kappa____ phi______ frames
    -      -25.5873  -38.0000   60.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
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_diffrn_orient_matrix_UB_11      -0.1223654000
_diffrn_orient_matrix_UB_12      -0.0417240000
_diffrn_orient_matrix_UB_13      -0.0031574000
_diffrn_orient_matrix_UB_21      0.0725814000
_diffrn_orient_matrix_UB_22      -0.0445789000
_diffrn_orient_matrix_UB_23      0.0095302000
_diffrn_orient_matrix_UB_31      -0.0021268000
_diffrn_orient_matrix_UB_32      0.0182900000
_diffrn_orient_matrix_UB_33      0.0560195000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6124
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         3.269
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0631P)^2^+0.0776P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1328
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_reflns_number_gt                2644
_reflns_number_total             3326
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj05445f2.cif
_cod_data_source_block           3
_cod_depositor_comments
;Adding full bibliography for 7059176--7059177.cif.

 Adding full bibliography for 7059176--7059177.cif.
;
_cod_database_code               7059176
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         ' O4 C30 N4 F6'
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.976
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B), C7(H7A,H7B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C10(H10), C14(H14), C12(H12), C13(H13)
;
_shelx_res_checksum              6466
_olex2_submission_special_instructions 'No special instructions were received'