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_7157199
_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         'C11 H9 F3 O2 S'
_chemical_formula_sum            'C11 H9 F3 O2 S'
_chemical_formula_weight         262.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-01-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-24 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.53(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.470(2)
_cell_length_b                   13.267(3)
_cell_length_c                   9.675(2)
_cell_measurement_reflns_used    1939
_cell_measurement_temperature    295
_cell_measurement_theta_max      28.7160
_cell_measurement_theta_min      3.7170
_cell_volume                     1086.8(4)
_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 0.998
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_details
;
  1 omega  -95.00  -14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7103  -19.0000    0.0000 81

  2 omega   -1.00   26.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7103  -19.0000    0.0000 27

  3 omega  -12.00   21.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7103  -99.0000   60.0000 33

  4 omega  -82.00  -52.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.2416  -38.0000 -120.0000 30

  5 omega  -30.00    8.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.2416  -38.0000 -120.0000 38

  6 omega  -98.00  -64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.2416  -19.0000  -30.0000 34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0779981000
_diffrn_orient_matrix_UB_12      0.0138010000
_diffrn_orient_matrix_UB_13      -0.0205835000
_diffrn_orient_matrix_UB_21      -0.0211953000
_diffrn_orient_matrix_UB_22      0.0024807000
_diffrn_orient_matrix_UB_23      0.0702983000
_diffrn_orient_matrix_UB_31      0.0222662000
_diffrn_orient_matrix_UB_32      0.0515954000
_diffrn_orient_matrix_UB_33      0.0019613000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6252
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.420
_diffrn_reflns_theta_min         3.509
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58867
_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 light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2635
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0556P)^2^+0.3586P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1221
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2093
_reflns_number_total             2635
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02120e2.cif
_cod_data_source_block           psu-831(r-44-r)
_cod_database_code               7157199
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C12 H12 N1 O3 S1 F3'
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.841
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C11(H11)
;
_shelx_res_checksum              62336
_olex2_submission_special_instructions 'No special instructions were received'