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_7157202
_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         'C16 H16 F3 N O S'
_chemical_formula_sum            'C16 H16 F3 N O S'
_chemical_formula_weight         327.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-23 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.57(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.153(4)
_cell_length_b                   15.177(5)
_cell_length_c                   7.937(2)
_cell_measurement_reflns_used    2321
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.7880
_cell_measurement_theta_min      3.6700
_cell_volume                     1518.6(8)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.841
_diffrn_measurement_details
;
  1 omega  -27.00   38.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       14.1634  -38.0000 -120.0000 65

  2 omega  -22.00    3.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       14.1634   77.0000 -180.0000 25

  3 omega   22.00   97.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       14.1634   77.0000 -180.0000 75

  4 omega  -10.00   26.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7103  -99.0000   60.0000 36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0070603000
_diffrn_orient_matrix_UB_12      -0.0389217000
_diffrn_orient_matrix_UB_13      0.0518727000
_diffrn_orient_matrix_UB_21      -0.0076974000
_diffrn_orient_matrix_UB_22      -0.0258331000
_diffrn_orient_matrix_UB_23      -0.0767036000
_diffrn_orient_matrix_UB_31      0.0553520000
_diffrn_orient_matrix_UB_32      0.0012360000
_diffrn_orient_matrix_UB_33      0.0096203000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.841
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7255
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.423
_diffrn_reflns_theta_min         3.232
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67108
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.135(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3526
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0543P)^2^+0.1001P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1271
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2418
_reflns_number_total             3526
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02120e2.cif
_cod_data_source_block           psu-1012(b-344)
_cod_database_code               7157202
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C H N O S F'
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.877
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S1-C8 \\sim S1A-C8
 with sigma of 0.02
 S1-C11 \\sim S1A-C11A
 with sigma of 0.02
 C8-C9 \\sim C8-C9A
 with sigma of 0.02
 C9-C10 \\sim C9A-C10A
 with sigma of 0.02
 C10-C11 \\sim C10A-C11A
 with sigma of 0.02
 S1-C10 \\sim S1A-C10A
 with sigma of 0.04
 C8-C10 \\sim C8-C10A
 with sigma of 0.04
 C8-C11 \\sim C8-C11A
 with sigma of 0.04
 C9-C11 \\sim C9A-C11A
 with sigma of 0.04
 F1-C12 \\sim F1A-C12
 with sigma of 0.02
 F2-C12 \\sim F2A-C12
 with sigma of 0.02
 F3-C12 \\sim F3A-C12
 with sigma of 0.02
3. Rigid bond restraints
 F1, F1A, F2, F2A, F3, F3A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
F1 \\sim F1A \\sim F2 \\sim F2A \\sim F3 \\sim F3A: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
5. Others
 Sof(S1A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=1-FVAR(1)
 Sof(S1)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(2)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C9(H9), C9A(H9A), C10(H10), C10A(H10A), C11(H11), C11A(H11A)
6.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              4311
_olex2_submission_special_instructions 'No special instructions were received'