Synthesis of Polysubstituted 2-Aminoimidazoles via Alkene-Diamination of Guanidine with Conjugated α-Bromoalkenones.
Guchhait, Sankar K.; Hura, Neha; Shah, Archana P.; The Journal of organic chemistry 82 (2017) 2745–2752; doi:10.1021/acs.joc.6b03021

data_4032182
_publ_section_title
;
 Synthesis of Polysubstituted 2-Aminoimidazoles via Alkene-Diamination of
 Guanidine with Conjugated \a-Bromoalkenones.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2745
_journal_page_last               2752
_journal_paper_doi               10.1021/acs.joc.6b03021
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C20 H21 N3 O5'
_chemical_formula_sum            'C20 H21 N3 O5'
_chemical_formula_weight         383.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                75.979(2)
_cell_angle_beta                 86.878(2)
_cell_angle_gamma                75.535(2)
_cell_formula_units_Z            4
_cell_length_a                   10.6227(2)
_cell_length_b                   11.7438(3)
_cell_length_c                   18.1448(5)
_cell_measurement_reflns_used    12012
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      32.7670
_cell_measurement_theta_min      2.9970
_cell_volume                     2126.48(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7d (Rigaku OD, 2015)'
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.934
_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    -69.00 118.20   0.30   20.00    --   29.89  54.00-180.00  624
  2  \w    -69.00 118.20   0.30   20.00    --   29.89  54.00  30.00  624
  3  \w    -69.00 118.20   0.30   20.00    --   29.89  54.00  30.00  624
  4  \w    -69.00 118.20   0.30   20.00    --   29.89  54.00 -60.00  624
  5  \w    -69.00  64.20   0.30   20.00    --   29.89  54.00 120.00  444
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0153583000
_diffrn_orient_matrix_UB_12      -0.0123237000
_diffrn_orient_matrix_UB_13      0.0391464000
_diffrn_orient_matrix_UB_21      -0.0649575000
_diffrn_orient_matrix_UB_22      -0.0030500000
_diffrn_orient_matrix_UB_23      0.0094066000
_diffrn_orient_matrix_UB_31      0.0173211000
_diffrn_orient_matrix_UB_32      -0.0629289000
_diffrn_orient_matrix_UB_33      0.0015997000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            47662
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.763
_diffrn_reflns_theta_min         2.595
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7d (Rigaku Oxford Diffraction, 2015)
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    1.198
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_refine_diff_density_max         1.608
_refine_diff_density_min         -0.721
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     514
_refine_ls_number_reflns         14677
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0553
_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^)+(0.0958P)^2^+0.4853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1545
_refine_ls_wR_factor_ref         0.1705
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11138
_reflns_number_total             14677
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b03021_si_002.cif
_cod_data_source_block           skg36_100k
_cod_depositor_comments          'Adding full bibliography for 4032182.cif.'
_cod_database_code               4032182
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C20 H21 N3 O5'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N1(H1), C7(H7), C35(H35), C34(H34), C3(H3), C14(H14), C15(H15),
 C38(H38), C23(H23), C37(H37), C18(H18), C27(H27), C17(H17)
2.c X=CH2 refined with riding coordinates:
 N6(H6A,H6B)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C19(H19A,H19B,H19C), C8(H8A,H8B,H8C), C29(H29A,H29B,
 H29C), C9(H9A,H9B,H9C), C28(H28A,H28B,H28C), C39(H39A,H39B,H39C), C30(H30A,
 H30B,H30C)
;
_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 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.776