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_7229605
_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         '3(I), 2.5(O), C30 H42 N5'
_chemical_formula_sum            'C30 H44 I3 N5 O2.5'
_chemical_formula_weight         895.72
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-22
_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                 91.647(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.1338(3)
_cell_length_b                   30.1549(9)
_cell_length_c                   18.5852(5)
_cell_measurement_reflns_used    13411
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      26.1980
_cell_measurement_theta_min      1.9540
_cell_volume                     7917.8(4)
_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      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_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     67.00 106.00   1.00   30.00    --   17.50  43.00   0.00   39
  2  \w    -71.00  42.00   1.00   30.00    --   17.50  60.00  90.00  113
  3  \w    -68.00  89.00   1.00   30.00    --   17.50  43.00-180.00  157
  4  \w    -46.00 -20.00   1.00   30.00    --   17.50  60.00-120.00   26
  5  \w    -71.00 -44.00   1.00   30.00    --   17.50  43.00   0.00   27
;
_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      0.0125841000
_diffrn_orient_matrix_UB_12      0.0104882000
_diffrn_orient_matrix_UB_13      -0.0325203000
_diffrn_orient_matrix_UB_21      0.0089246000
_diffrn_orient_matrix_UB_22      -0.0210169000
_diffrn_orient_matrix_UB_23      -0.0155432000
_diffrn_orient_matrix_UB_31      -0.0477779000
_diffrn_orient_matrix_UB_32      -0.0011564000
_diffrn_orient_matrix_UB_33      -0.0126139000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            51690
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.435
_diffrn_reflns_theta_min         2.239
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.401
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.30c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
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    1.503
_exptl_crystal_description       needle
_exptl_crystal_F_000             3505
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.690
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     808
_refine_ls_number_reflns         16200
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0843P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1507
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10348
_reflns_number_total             16200
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra11827a2.cif
_cod_data_source_block           s4935l
_cod_original_formula_sum        'C30 H44 I3 N5 O2.50'
_cod_database_code               7229605
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C30H44I3N5O2.5
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.558
_reflns_odcompleteness_completeness 99.83
_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. Restrained distances
 N15-H15 \\sim N50_$1-H50_$1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(I77) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O83) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 1*[Sof(I75)]+1*[Sof(I76)]+1*[Sof(I81)]+1*[Sof(I78)]+1*[Sof(I77)]+1*[Sof(I79)]+
 1*[Sof(I80)]=2 with esd of 0.001
5.a Ternary CH refined with riding coordinates:
 C49(H49), C48(H48), C14(H14), C13(H13)
5.b Aromatic/amide H refined with riding coordinates:
 C42(H42), C44(H44), C45(H45), C63(H63), C62(H62), C65(H65), C52(H52),
 C56(H56), C53(H53), C66(H66), C41(H41), C55(H55), C17(H17), C30(H30), C18(H18),
  C28(H28), C9(H9), C10(H10), C7(H7), C6(H6), C31(H31), C21(H21), C27(H27),
 C20(H20)
5.c Idealised Me refined as rotating group:
 C69(H69A,H69B,H69C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,
 H38C), C68(H68A,H68B,H68C), C60(H60A,H60B,H60C), C70(H70A,H70B,H70C), C58(H58A,
 H58B,H58C), C59(H59A,H59B,H59C), C1(H1A,H1B,H1C), C24(H24A,H24B,H24C),
 C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C3(H3A,H3B,H3C), C34(H34A,H34B,H34C),
  C23(H23A,H23B,H23C), C2(H2A,H2B,H2C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              11050
_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 2.349
_oxdiff_exptl_absorpt_empirical_full_min 0.406