Photochemical synthesis of 1,2,4-triazoles <i>via</i> addition reaction of triplet intermediates to diazoalkanes and azomethine ylide intermediates.
Cai, Bao-Gui; Bao, Ye-Peng; Pei, Chao; Li, Qian; Li, Lei; Koenigs, Rene M.; Xuan, Jun; Chemical science 13 (2022) 13141–13146; doi:10.1039/d2sc04720a

data_1567835
_publ_section_title
;
 Photochemical synthesis of 1,2,4-triazoles <i>via</i> addition reaction
 of triplet intermediates to diazoalkanes and azomethine ylide
 intermediates.
;
_journal_issue                   44
_journal_name_full               'Chemical science'
_journal_page_first              13141
_journal_page_last               13146
_journal_paper_doi               10.1039/d2sc04720a
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C21 H27 N3 O6'
_chemical_formula_sum            'C21 H27 N3 O6'
_chemical_formula_weight         417.45
_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     dual
_audit_creation_date             2021-12-30
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-04-14 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                77.872(6)
_cell_angle_beta                 89.269(6)
_cell_angle_gamma                87.510(6)
_cell_formula_units_Z            4
_cell_length_a                   9.4970(7)
_cell_length_b                   14.1349(10)
_cell_length_c                   16.2663(11)
_cell_measurement_reflns_used    5240
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      28.1840
_cell_measurement_theta_min      2.5570
_cell_volume                     2132.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -12.00  84.00   1.00    5.00    --   11.90  57.00  30.00   96
  2  \w     37.00  64.00   1.00    5.00    --   11.90 178.00-150.00   27
  3  \w    -17.00  79.00   1.00    5.00    --   11.90  77.00 150.00   96
  4  \w    -58.00  40.00   1.00    5.00    --   11.90 -57.00-120.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0119534000
_diffrn_orient_matrix_UB_12      -0.0397909000
_diffrn_orient_matrix_UB_13      0.0336263000
_diffrn_orient_matrix_UB_21      0.0578750000
_diffrn_orient_matrix_UB_22      0.0126807000
_diffrn_orient_matrix_UB_23      0.0220217000
_diffrn_orient_matrix_UB_31      -0.0457861000
_diffrn_orient_matrix_UB_32      0.0299141000
_diffrn_orient_matrix_UB_33      0.0193282000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0522
_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       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15262
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.146
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     557
_refine_ls_number_reflns         7515
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0709
_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^)+(0.0873P)^2^+1.9194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1756
_refine_ls_wR_factor_ref         0.1955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5438
_reflns_number_total             7515
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04720a3.cif
_cod_data_source_block           1131
_cod_depositor_comments          'Adding full bibliography for 1567835.cif.'
_cod_database_code               1567835
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 O10, C41
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
O10 \\sim C41: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
4. Rigid body (RIGU) restrains
 O2, C11, C12, C13, C14, C15
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(H13C)=Sof(H13D)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(H15C)=Sof(H15D)=1-FVAR(1)
 Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H15A)=Sof(H15B)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C11(H11), C22(H22)
6.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C13(H13C,H13D), C14(H14A,H14B), C14A(H14C,
 H14D), C15(H15A,H15B), C15(H15C,H15D), C17(H17A,H17B), C20(H20A,H20B),
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C38(H38A,H38B),
  C41(H41A,H41B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C30(H30), C31(H31), C32(H32),
 C33(H33), C34(H34)
6.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C36(H36A,H36B,
 H36C), C39(H39A,H39B,H39C), C42(H42A,H42B,H42C)
;
_shelx_res_checksum              81560
_shelx_hkl_checksum              64169
_olex2_date_sample_data_collection 2021-12-30
_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 3.257
_oxdiff_exptl_absorpt_empirical_full_min 0.608