Thermal and photochemical annulation of vinyl azides to 2-aminoimidazoles.
Man, Lucas; Copley, Royston C. B.; Handlon, Anthony L.; Organic & biomolecular chemistry 17 (2019) 6566–6569; doi:10.1039/c9ob01100e

data_7156921
_publ_section_title
;
 Thermal and photochemical annulation of vinyl azides to
 2-aminoimidazoles.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6566
_journal_page_last               6569
_journal_paper_doi               10.1039/c9ob01100e
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C11 H19 N3 O2'
_chemical_formula_sum            'C11 H19 N3 O2'
_chemical_formula_weight         225.29
_chemical_name_systematic
; 
Ethyl 2-amino-5-neopentyl-1H-imidazole-4-carboxylate 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-04-23 deposited with the CCDC.    2019-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.6022(7)
_cell_length_b                   22.9041(13)
_cell_length_c                   9.5733(5)
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.65
_cell_measurement_theta_min      4.27
_cell_volume                     2544.0(2)
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service v6.2.6'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Bruker XP, PLATON, and CSD Mercury'
_computing_publication_material  'SHELXL, XCIF, and local software'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
Collection strategy, angles in degrees, time in seconds
Scan_type dx 2theta omega phi chi exposure_time width scan_range direction
Fast    80.000    0.000    0.000    0.000  54.781   1.000   1.000
Omega   80.000   68.684 -136.442  162.000  54.740   9.800   0.500 230.500 pos
Omega   80.000  112.960  -92.166    0.000  54.740  24.000   0.500 230.500 pos
Omega   80.000  112.960  -92.166  -72.000  54.740  24.000   0.500 230.500 pos
Omega   80.000   68.684 -136.442  108.000  54.740   9.800   0.500 230.500 pos
Omega   80.000  112.960  -92.166   72.000  54.740  24.000   0.500 230.500 pos
Omega   80.000  -27.880 -233.007  -80.000  54.740   6.000   0.500 230.500 pos
Omega   80.000  112.960  -92.166 -168.000  54.740  24.000   0.500 230.500 pos
Omega   80.000   82.960 -122.166    0.000  54.740  12.900   0.500 230.500 pos
Omega   80.000  112.960  -92.166  144.000  54.740  24.000   0.500 230.500 pos
Phi     80.000   97.960 -107.415    0.000  54.781  17.600   0.500 360.000 pos
Omega   80.000   97.960 -107.166  180.000  54.740  17.600   0.500 230.500 pos
Omega   80.000   82.960 -122.166   90.000  54.740  12.900   0.500 230.500 pos
Omega   80.000  112.960  -92.166  168.000  54.740  24.000   0.500 230.500 pos
Omega   80.000  112.960  -92.166  120.000  54.740  24.000   0.500 230.500 pos
Omega   80.000  -38.684 -243.810  270.000  54.740   6.500   0.500 230.500 pos
Omega   80.000  112.960  -92.166   48.000  54.740  24.000   0.500 230.500 pos
Omega   80.000   68.684 -136.442  135.000  54.740   9.800   0.500 230.500 pos
Omega   80.000   68.684 -136.442   54.000  54.740   9.800   0.500 230.500 pos
Omega   80.000   97.960 -107.166   90.000  54.740  17.600   0.500 230.500 pos
Omega   80.000  112.960  -92.166 -144.000  54.740  24.000   0.500 230.500 pos
;
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_orient_matrix_type       'Bruker AXS Inc. convention APEX3'
_diffrn_orient_matrix_UB_11      -8.0403566e-002
_diffrn_orient_matrix_UB_12      -1.5682977e-002
_diffrn_orient_matrix_UB_13      2.8434682e-003
_diffrn_orient_matrix_UB_21      -2.9430024e-002
_diffrn_orient_matrix_UB_22      3.9546628e-002
_diffrn_orient_matrix_UB_23      2.6212515e-002
_diffrn_orient_matrix_UB_31      -9.8942267e-003
_diffrn_orient_matrix_UB_32      9.8147076e-003
_diffrn_orient_matrix_UB_33      -1.0107511e-001
_diffrn_radiation_collimation    'focussed source'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0217
_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       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            50345
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.660
_diffrn_reflns_theta_max         66.660
_diffrn_reflns_theta_min         3.860
_diffrn_source_type              'Incoatec microfocus 3.0 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  0.9779
_exptl_absorpt_correction_T_min  0.7992
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       Needle
_exptl_crystal_F_000             976
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol and water'
_exptl_crystal_size_max          0.886
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   1.0000
_exptl_transmission_factor_min   0.6412
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2252
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0690
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0728P)^2^+4.3310P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1892
_refine_ls_wR_factor_ref         0.1896
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2195
_reflns_number_total             2252
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01100e2.cif
_cod_data_source_block           4h
_cod_depositor_comments
'Adding full bibliography for 7156920--7156921.cif.'
_cod_database_code               7156921
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.589
_shelx_estimated_absorpt_t_max   0.967
_computing_data_merging          SHELXL
_shelx_res_checksum              55874