Synthesis of meta-Substituted Anilines via Three-Component Reaction of Acetone, Amines, and 1,3-Diketones
Galeev, Andrew R.; Mokrushin, Ivan G.; Dmitriev, Maksim V.; Mashevskaya, Irina V.; Maslivets, Andrey N.; Rubin, Michael; Organic & Biomolecular Chemistry  (2019) –; doi:10.1039/C9OB02120E

data_7157201
_publ_section_title
;
 Synthesis of meta-Substituted Anilines via Three-Component Reaction of
 Acetone, Amines, and 1,3-Diketones
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/C9OB02120E
_journal_year                    2019
_chemical_formula_moiety         'C20 H17 N O3'
_chemical_formula_sum            'C20 H17 N O3'
_chemical_formula_weight         319.35
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2019-03-24 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                82.664(14)
_cell_angle_beta                 79.063(17)
_cell_angle_gamma                76.170(16)
_cell_formula_units_Z            2
_cell_length_a                   7.6883(17)
_cell_length_b                   9.4591(15)
_cell_length_c                   11.7328(19)
_cell_measurement_reflns_used    1861
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.8870
_cell_measurement_theta_min      4.0570
_cell_volume                     810.4(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      295.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measurement_details
;
  1 omega   -4.00   94.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -       14.0072   77.0000  -60.0000 98

  2 omega  -22.00   86.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -       14.0072   77.0000   90.0000 108

  3 omega  -45.00   57.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.5541   77.0000 -180.0000 102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0563322000
_diffrn_orient_matrix_UB_12      -0.0152984000
_diffrn_orient_matrix_UB_13      -0.0542870000
_diffrn_orient_matrix_UB_21      -0.0003181000
_diffrn_orient_matrix_UB_22      0.0753626000
_diffrn_orient_matrix_UB_23      -0.0130852000
_diffrn_orient_matrix_UB_31      0.0781495000
_diffrn_orient_matrix_UB_32      -0.0097441000
_diffrn_orient_matrix_UB_33      0.0264836000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6254
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.439
_diffrn_reflns_theta_min         2.964
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0592
_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^)+(0.0892P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1545
_refine_ls_wR_factor_ref         0.1868
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2429
_reflns_number_total             3760
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02120e2.cif
_cod_data_source_block           psu-345(md-356)
_cod_database_code               7157201
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C17(H17), C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              31422
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'