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_7229602
_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_absolute_configuration ad
_chemical_formula_moiety         'C24 H15 F9 N2'
_chemical_formula_sum            'C24 H15 F9 N2'
_chemical_formula_weight         502.38
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_Hall           'P 4cw'
_space_group_name_H-M_alt        'P 43'
_symmetry_space_group_name_Hall  'P 4cw'
_symmetry_space_group_name_H-M   'P 43'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-03
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-09-22 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            4
_cell_length_a                   10.9162(2)
_cell_length_b                   10.9162(2)
_cell_length_c                   19.1285(4)
_cell_measurement_reflns_used    15549
_cell_measurement_temperature    150
_cell_measurement_theta_max      68.1110
_cell_measurement_theta_min      2.3190
_cell_volume                     2279.42(8)
_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_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     69.67 257.67   1.00   15.00    --   99.46  73.87 157.22  188
  2  \w    -81.29 105.71   1.00   15.00    --  -51.50  73.87 -25.89  187
  3  \w     74.39 262.39   1.00   15.00    --  104.18  73.87 -82.86  188
  4  \w     82.65 270.65   1.00   15.00    --  112.44  73.87  61.96  188
  5  \f   -249.79  -9.60   1.00   15.00  73.16 102.95  73.87    --   240
  6  \w   -104.82  82.18   1.00   15.00    --  -75.03  73.87  -7.40  187
  7  \w    -34.43 152.57   1.00   15.00    --   -4.63  73.87-102.66  187
  8  \w     74.96 261.96   1.00   15.00    --  104.75  73.87 -11.33  187
  9  \w     64.79 252.79   1.00   15.00    --   94.58  73.87-112.72  188
 10  \f   -117.29  32.83   1.00   15.00 115.04 -43.16  73.87    --   150
 11  \w   -108.77  78.23   1.00   15.00    --  -78.98  73.87-144.46  187
 12  \w     70.76 257.76   1.00   15.00    --  100.55  73.87  77.69  187
 13  \w     73.15 261.15   1.00   15.00    --  102.94  73.87  23.67  188
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0241048000
_diffrn_orient_matrix_UB_12      -0.1279407000
_diffrn_orient_matrix_UB_13      0.0307480000
_diffrn_orient_matrix_UB_21      -0.1147004000
_diffrn_orient_matrix_UB_22      0.0126475000
_diffrn_orient_matrix_UB_23      0.0463971000
_diffrn_orient_matrix_UB_31      -0.0788696000
_diffrn_orient_matrix_UB_32      -0.0578475000
_diffrn_orient_matrix_UB_33      -0.0582107000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26788
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.244
_diffrn_reflns_theta_min         4.050
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.228
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50267
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.132
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4163
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0635P)^2^+1.5107P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1271
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3911
_reflns_number_total             4163
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra11827a2.cif
_cod_data_source_block           s4860x
_cod_original_cell_volume        2279.42(10)
_cod_database_code               7229602
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.855
_shelx_estimated_absorpt_t_min   0.746
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.0(3)
 -0.0(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3. Others
 1*[Sof(F1)+Sof(F2)+Sof(F3)]+1*[Sof(F4)+Sof(F5)+Sof(F6)]+1*[Sof(F7)+Sof(F8)+
 Sof(F9)]=1 with esd of 0.0001
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(2)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(3)
4.a Riding coordinates:
 N1(H1)
4.b Ternary CH refined with riding coordinates:
 C9(H9), C7(H7)
4.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C5(H5), C4(H4), C23(H23), C18(H18), C16(H16), C24(H24),
 C19(H19), C15(H15), C22(H22), C21(H21)
;
_shelx_res_checksum              70199
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.299
_oxdiff_exptl_absorpt_empirical_full_min 0.536