Aerobic radical-cascade cycloaddition of isocyanides, selenium and imidamides: facile access to 1,2,4-selenadiazoles under metal-free conditions
Fang, Yi; Zhu, Zheng-Lin; Xu, Pei; Wang, Shun-Yi; Ji, Shun-Jun; Green Chem. 19 (2017) 1613–; doi:10.1039/C6GC03521C

data_7227333
_publ_section_title
;
 Aerobic radical-cascade cycloaddition of isocyanides, selenium and
 imidamides: facile access to 1,2,4-selenadiazoles under metal-free
 conditions
;
_journal_issue                   7
_journal_name_full               'Green Chem.'
_journal_page_first              1613
_journal_paper_doi               10.1039/C6GC03521C
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C14 H16 Cl N3 Se, H2 O'
_chemical_formula_sum            'C14 H18 Cl N3 O Se'
_chemical_formula_weight         358.72
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-09-13 deposited with the CCDC.
2017-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   25.4682(9)
_cell_length_b                   25.4682(9)
_cell_length_c                   12.3160(5)
_cell_measurement_reflns_used    2093
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      27.1970
_cell_measurement_theta_min      3.2020
_cell_volume                     6918.3(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -55.00   46.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514    0.0000  -90.0000 101

  2 omega  -41.00  -14.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889   37.0000  120.0000 27
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0168718000
_diffrn_orient_matrix_UB_12      0.0154544000
_diffrn_orient_matrix_UB_13      0.0468003000
_diffrn_orient_matrix_UB_21      -0.0208493000
_diffrn_orient_matrix_UB_22      0.0101273000
_diffrn_orient_matrix_UB_23      0.0109738000
_diffrn_orient_matrix_UB_31      -0.0177393000
_diffrn_orient_matrix_UB_32      -0.0263166000
_diffrn_orient_matrix_UB_33      0.0317009000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7022
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.77
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             3276
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.752
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         3137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0706
_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^)+(0.0527P)^2^+13.3591P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1206
_reflns_number_gt                2344
_reflns_number_total             3137
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6gc03521c2.cif
_cod_data_source_block           g160613a
_cod_depositor_comments          'Adding full bibliography for 7227333.cif.'
_cod_original_cell_volume        6918.2(4)
_cod_database_code               7227333
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uiso(O1) = Uiso(O1A)
3. Others
 Sof(O1A)=1-FVAR(1)
 Sof(O1)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C1(H1A)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C10(H10), C11(H11), C13(H13), C14(H14)
;
_olex2_date_sample_data_collection 2016-06-13
_olex2_submission_special_instructions 'No special instructions were received'