Visible-light-promoted decarboxylative addition cyclization of N-aryl glycines and azobenzenes to access 1,2,4-triazolidines
Yang, Jingya; Song, Menghui; Zhou, Hongyan; Qi, Yanfang; Ma, Ben; Wang, Xi-Cun; Green Chemistry 23 (2021) 5806–5811; doi:10.1039/D1GC02272E

data_7243271
_publ_section_title
;
 Visible-light-promoted decarboxylative addition cyclization of N-aryl
 glycines and azobenzenes to access 1,2,4-triazolidines
;
_journal_issue                   16
_journal_name_full               'Green Chemistry'
_journal_page_first              5806
_journal_page_last               5811
_journal_paper_doi               10.1039/D1GC02272E
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C20 H17 Br2 N3'
_chemical_formula_sum            'C20 H17 Br2 N3'
_chemical_formula_weight         459.18
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-12-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2021-05-17 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.1994(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.62006(16)
_cell_length_b                   5.80584(6)
_cell_length_c                   22.6165(2)
_cell_measurement_reflns_used    9655
_cell_measurement_temperature    294.65(10)
_cell_measurement_theta_max      75.2480
_cell_measurement_theta_min      3.1110
_cell_volume                     1861.08(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.65(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.918
_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      9.00  36.00   0.50    0.05    --   43.05 -37.00  60.00   54
  2  \w    -11.00  15.00   0.50    0.05    --   43.05 -19.00  90.00   52
  3  \w     36.00  68.00   0.50    0.05    --  109.26 -69.00  72.00   64
  4  \w     44.00  99.00   0.50    0.05    --  109.26 -77.00   0.00  110
  5  \w     56.00 105.00   0.50    0.05    --  109.26 -94.00-120.00   98
  6  \w     38.00  64.00   0.50    0.05    --  109.26 -61.00-150.00   52
  7  \w    105.00 130.00   0.50    0.05    --  109.26  69.00-155.00   50
  8  \w    124.00 150.00   0.50    0.05    --  109.26  45.00 120.00   52
  9  \w     92.00 117.00   0.50    0.05    --  109.26  45.00 120.00   50
 10  \w    -27.00  23.00   0.50    0.05    --   43.05 -19.00 -90.00  100
 11  \w    -67.00  23.00   0.50    0.05    --  -43.05  69.00-155.00  180
 12  \w   -111.00 -18.00   0.50    0.05    --  -43.05 -69.00  72.00  186
 13  \w    -49.00 -24.00   0.50    0.05    -- -100.00  45.00  60.00   50
 14  \w    -54.00 -25.00   0.50    0.05    -- -100.00  45.00   0.00   58
 15  \w    -61.00 -36.00   0.50    0.05    -- -100.00  61.00  60.00   50
 16  \w    -56.00 -31.00   0.50    0.05    -- -100.00  61.00  30.00   50
 17  \w    -67.00 -26.00   0.50    0.05    -- -100.00  77.00 -60.00   82
 18  \w    -85.00 -26.00   0.50    0.05    -- -100.00  69.00-155.00  118
 19  \w    -74.00 -29.00   0.50    0.05    -- -100.00  61.00-180.00   90
 20  \w   -105.00 -76.00   0.50    0.05    -- -100.00  77.00 -60.00   58
 21  \w   -159.00 -76.00   0.50    0.05    -- -100.00 -69.00  72.00  166
 22  \w    -50.00 -24.00   0.50    0.05    -- -100.00  45.00 150.00   52
 23  \w    -74.00 -48.00   0.50    0.05    -- -100.00  61.00 150.00   52
 24  \w   -176.00 -82.00   0.50    0.05    -- -100.00 -45.00 150.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0520381000
_diffrn_orient_matrix_UB_12      -0.1597202000
_diffrn_orient_matrix_UB_13      0.0352729000
_diffrn_orient_matrix_UB_21      -0.0916722000
_diffrn_orient_matrix_UB_22      0.1372509000
_diffrn_orient_matrix_UB_23      -0.0243578000
_diffrn_orient_matrix_UB_31      -0.0264973000
_diffrn_orient_matrix_UB_32      -0.1614224000
_diffrn_orient_matrix_UB_33      -0.0556748000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11202
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.059
_diffrn_reflns_theta_min         3.271
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0673P)^2^+1.7856P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3298
_reflns_number_total             3576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc02272e2.cif
_cod_data_source_block           songmh_1210_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7243270--7243271.cif.'
_cod_original_cell_volume        1861.08(4)
_cod_database_code               7243271
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.851
_shelx_estimated_absorpt_t_min   0.579
_reflns_odcompleteness_completeness 98.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C10(H10), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              46188
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.678
_oxdiff_exptl_absorpt_empirical_full_min 0.680