One-pot three-component strategy for functionalized 2-aminoimidazoles via ring opening of α-nitro epoxides.
Guo, Xiao; Chen, Wenteng; Chen, Binhui; Huang, Wei; Qi, Weixing; Zhang, Guolin; Yu, Yongping; Organic letters 17 (2015) 1157–1159; doi:10.1021/acs.orglett.5b00289

data_1554813
_publ_section_title
;
 One-pot three-component strategy for functionalized 2-aminoimidazoles via
 ring opening of \a-nitro epoxides.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1157
_journal_page_last               1159
_journal_paper_doi               10.1021/acs.orglett.5b00289
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C17 H16 Cl N3 O'
_chemical_formula_sum            'C17 H16 Cl N3 O'
_chemical_formula_weight         313.78
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                66.740(6)
_cell_angle_beta                 82.416(5)
_cell_angle_gamma                77.876(5)
_cell_formula_units_Z            4
_cell_length_a                   8.6811(5)
_cell_length_b                   13.1015(8)
_cell_length_c                   15.2298(9)
_cell_measurement_reflns_used    3106
_cell_measurement_temperature    171.6
_cell_measurement_theta_max      29.4524
_cell_measurement_theta_min      2.8726
_cell_volume                     1553.57(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      171.6
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0443609000
_diffrn_orient_matrix_UB_12      -0.0002009000
_diffrn_orient_matrix_UB_13      0.0426406000
_diffrn_orient_matrix_UB_21      -0.0393672000
_diffrn_orient_matrix_UB_22      0.0555682000
_diffrn_orient_matrix_UB_23      -0.0250989000
_diffrn_orient_matrix_UB_31      -0.0590525000
_diffrn_orient_matrix_UB_32      -0.0221890000
_diffrn_orient_matrix_UB_33      -0.0113718000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9914
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.88
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5675
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+0.4739P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1240
_reflns_number_gt                4284
_reflns_number_total             5675
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b00289_si_001.cif
_cod_data_source_block           150108_gx150108_1
_cod_original_cell_volume        1553.57(16)
_cod_database_code               1554813
_chemical_oxdiff_formula         'c10 h10 n2 o8 Cl1'
_reflns_odcompleteness_completeness 99.59
_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
 N4-H4B
 0.85 with sigma of 0.02
 N4-H4A
 0.85 with sigma of 0.02
 N1-H1A
 0.85 with sigma of 0.02
 N1-H1B
 0.85 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C12(H12), C13(H13), C15(H15), C16(H16),
 C18(H18), C19(H19), C21(H21), C22(H22), C29(H29), C30(H30), C32(H32), C33(H33)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C34(H34A,H34B,H34C)
;