Environmentally benign and diastereoselective synthesis of 2,4,5-trisubstituted-2-imidazolines
Le Phuong, Hai Anh; Cseri, Levente; Whitehead, George F. S.; Garforth, Arthur; Budd, Peter; Szekely, Gyorgy; RSC Advances 7 (2017) 53278–; doi:10.1039/C7RA11827A

data_7229604
_publ_section_title
;
 Environmentally benign and diastereoselective synthesis of
 2,4,5-trisubstituted-2-imidazolines
;
_journal_issue                   84
_journal_name_full               'RSC Advances'
_journal_page_first              53278
_journal_paper_doi               10.1039/C7RA11827A
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C24 H15 F9 N2'
_chemical_formula_sum            'C24 H15 F9 N2'
_chemical_formula_weight         502.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-10-25 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.08130(17)
_cell_length_b                   20.6490(4)
_cell_length_c                   21.8088(4)
_cell_measurement_reflns_used    5818
_cell_measurement_temperature    150.03(10)
_cell_measurement_theta_max      67.9120
_cell_measurement_theta_min      4.0380
_cell_volume                     4539.91(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.03(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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     69.00  95.00   1.00    2.00    --   55.00  57.00 129.00   26
  2  \w     31.00  56.00   1.00    2.00    --   55.00  57.00 129.00   25
  3  \w    -33.00  -7.00   1.00    2.00    --   55.00  49.00-104.00   26
  4  \w    -22.00   3.00   1.00    2.00    --   55.00  59.00  16.00   25
  5  \w     86.00 111.00   1.00    5.00    --  110.00  59.00  16.00   25
  6  \w     86.00 111.00   1.00    5.00    --  110.00  49.00-104.00   25
  7  \w    174.00 199.00   1.00    5.00    --  110.00  59.00  16.00   25
  8  \w     99.00 124.00   1.00    5.00    --  110.00  57.00 129.00   25
  9  \w    -71.00 -19.00   1.00    1.00    --    0.00  60.00-180.00   52
 10  \w     33.00  83.00   1.00    1.00    --    0.00  60.00-180.00   50
 11  \w    -24.00   1.00   1.00    1.00    --    0.00  59.00  16.00   25
 12  \w    -24.00   1.00   1.00    1.00    --    0.00  49.00-104.00   25
 13  \w    -33.00 142.00   1.00    2.00    --   55.00  29.00  60.00  175
 14  \w    -32.00  24.00   1.00    2.00    --   55.00  57.00 -90.00   56
 15  \w     55.00  80.00   1.00    2.00    --   55.00  59.00  16.00   25
 16  \w     47.00  75.00   1.00    2.00    --   55.00  57.00 -90.00   28
 17  \w     57.00 198.00   1.00    5.00    --  110.00  48.00-150.00  141
 18  \w     22.00  52.00   1.00    5.00    --  110.00  10.00 -60.00   30
 19  \w    173.00 199.00   1.00    5.00    --  110.00  60.00   0.00   26
 20  \w    106.00 186.00   1.00    5.00    --  110.00  10.00  60.00   80
 21  \w     21.00 121.00   1.00    5.00    --  110.00  60.00   0.00  100
 22  \w     58.00  84.00   1.00    5.00    --  110.00  10.00 -60.00   26
 23  \w     42.00  80.00   1.00    5.00    --  110.00  10.00  60.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0365385000
_diffrn_orient_matrix_UB_12      -0.0477326000
_diffrn_orient_matrix_UB_13      0.0515977000
_diffrn_orient_matrix_UB_21      0.1263812000
_diffrn_orient_matrix_UB_22      -0.0394334000
_diffrn_orient_matrix_UB_23      -0.0135549000
_diffrn_orient_matrix_UB_31      0.0777506000
_diffrn_orient_matrix_UB_32      0.0416254000
_diffrn_orient_matrix_UB_33      0.0463030000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16281
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.235
_diffrn_reflns_theta_min         4.054
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.233
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.30c (Rigaku Oxford Diffraction, 2017)
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    1.470
_exptl_crystal_description       plate
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.740
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         4146
_refine_ls_number_restraints     418
_refine_ls_restrained_S_all      1.321
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0705
_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^)+(0.0946P)^2^+6.1064P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1874
_refine_ls_wR_factor_ref         0.1952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3579
_reflns_number_total             4146
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra11827a2.cif
_cod_data_source_block           s4980l
_cod_original_cell_volume        4539.89(14)
_cod_database_code               7229604
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.842
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F5-C14 = F5A-C14 = F4-C14 = F4A-C14 = F6-C14 = F6A-C14
 1.35 with sigma of 0.01
 F5A-F4A = F4A-F6 = F6-F5A
 2.36 with sigma of 0.01
 F5-F4 = F4-F6A = F6A-F5
 2.36 with sigma of 0.01
 F8-F9 = F9-F7 = F7-F8
 2.36 with sigma of 0.01
 F8A-F9A = F9A-F7A = F7A-F8A
 2.36 with sigma of 0.01
 F8-C22 = F9-C22 = F7-C22 = F8A-C22A = F9A-C22A = F7A-C22A
 1.35 with sigma of 0.01
 F2-C1 = F1A-C1 = F1-C1 = F3A-C1 = F3-C1 = F2A-C1
 1.35 with sigma of 0.01
 C22A-C21 \\sim C22-C21
 with sigma of 0.01
3. Rigid bond restraints
 F5, F5A, F4, F4A, F6A, F6, C14
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 F7, F9, F8, C22, F7A, F8A, F9A, C22A
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 F3, F1, C1, F2, F2A, F1A, F3A, F2B, F3B, F1B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
F5 \\sim F5A \\sim F4 \\sim F4A \\sim F6A \\sim F6 \\sim C14: within 2A with
sigma of 0.02 and sigma for terminal atoms of 0.01
F7 \\sim F9 \\sim F8 \\sim C22 \\sim F7A \\sim F8A \\sim F9A \\sim C22A: within
2A with sigma of 0.02 and sigma for terminal atoms of 0.01
F3 \\sim F1 \\sim C1 \\sim F2 \\sim F2A \\sim F1A \\sim F3A \\sim F2B \\sim F3B
\\sim F1B: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.01
5. Others
 1*[Sof(F2A)+Sof(F1A)+Sof(F3A)]+1*[Sof(F3)+Sof(F1)+Sof(F2)]+1*[Sof(F3B)+
 Sof(F2B)+Sof(F1B)]=1 with esd of 0.0001
 Sof(F7A)=Sof(F8A)=Sof(F9A)=Sof(C22A)=1-FVAR(1)
 Sof(F7)=Sof(F9)=Sof(F8)=Sof(C22)=FVAR(1)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(2)
 Sof(F5)=Sof(F6)=Sof(F4)=FVAR(2)
 Sof(F2A)=Sof(F1A)=Sof(F3A)=FVAR(3)
 Sof(F3)=Sof(F1)=Sof(F2)=FVAR(4)
 Sof(F3B)=Sof(F2B)=Sof(F1B)=FVAR(5)
6.a Ternary CH refined with riding coordinates:
 C17(H17), C9(H9)
6.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C6(H6), C23(H23), C11(H11), C19(H19), C4(H4), C7(H7), C16(H16),
 C12(H12), C3(H3), C20(H20), C15(H15)
;
_shelx_res_checksum              83063
_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 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.759