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_7156920
_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         'C10 H17 N3 O2'
_chemical_formula_sum            'C10 H17 N3 O2'
_chemical_formula_weight         211.26
_chemical_name_systematic
; 
Ethyl 2-amino-5-isobutyl-1H-imidazole-4-carboxylate 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 96.0696(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.7186(3)
_cell_length_b                   11.7583(4)
_cell_length_c                   20.8375(6)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.58
_cell_measurement_theta_min      5.25
_cell_volume                     2367.84(13)
_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)'
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_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    65.000    0.000    0.000    0.000  54.781   1.000   1.000
Omega   65.000   82.960 -111.941   90.000  54.740  12.800   0.800 210.400 pos
Omega   65.000   70.337 -124.564 -104.000  54.740  10.100   0.800 210.400 pos
Omega   65.000  112.960  -81.941  -36.000  54.740  24.000   0.800 210.400 pos
Omega   65.000  112.960  -81.941 -144.000  54.740  24.000   0.800 210.400 pos
Omega   65.000  -32.188 -227.089 -160.000  54.740   6.000   0.800 210.400 pos
Omega   65.000  112.960  -81.941    0.000  54.740  24.000   0.800 210.400 pos
Omega   65.000  112.960  -81.941  135.000  54.740  24.000   0.800 210.400 pos
Phi     65.000  112.960  -82.540  -70.601  54.781  24.000   0.800 260.800 pos
Omega   65.000  112.960  -81.941   54.000  54.740  24.000   0.800 210.400 pos
Omega   65.000  -55.337 -250.238  180.000  54.740   7.800   0.800 210.400 pos
Omega   65.000  -55.337 -250.238    0.000  54.740   7.800   0.800 210.400 pos
Omega   65.000  112.960  -81.941  108.000  54.740  24.000   0.800 210.400 pos
Omega   65.000   70.337 -124.564   96.000  54.740  10.100   0.800 210.400 pos
Omega   65.000  112.960  -81.941   27.000  54.740  24.000   0.800 210.400 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      -1.6971240e-002
_diffrn_orient_matrix_UB_12      5.5345014e-002
_diffrn_orient_matrix_UB_13      3.4740932e-002
_diffrn_orient_matrix_UB_21      2.9391903e-002
_diffrn_orient_matrix_UB_22      -5.8558222e-002
_diffrn_orient_matrix_UB_23      3.3471033e-002
_diffrn_orient_matrix_UB_31      9.7751379e-002
_diffrn_orient_matrix_UB_32      2.7216097e-002
_diffrn_orient_matrix_UB_33      1.3692902e-003
_diffrn_radiation_collimation    'focussed source'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            37770
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         4.267
_diffrn_source_type              'Incoatec microfocus 3.0 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  0.9617
_exptl_absorpt_correction_T_min  0.8086
_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    1.185
_exptl_crystal_description       Lath
_exptl_crystal_F_000             912
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol and water'
_exptl_crystal_size_max          0.593
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.066
_exptl_transmission_factor_max   1.0000
_exptl_transmission_factor_min   0.6439
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0694P)^2^+0.4644P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1153
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3803
_reflns_number_total             4186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01100e2.cif
_cod_data_source_block           4g
_cod_depositor_comments
'Adding full bibliography for 7156920--7156921.cif.'
_cod_database_code               7156920
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.686
_shelx_estimated_absorpt_t_max   0.956
_computing_data_merging          SHELXL
_shelx_res_checksum              72636