Ruthenium-catalyzed synthesis of tricyclic 1,5-fused 1,2,3-triazole piperazines.
Said Stålsmeden, Anna; Ferrara, Flavia; Ekebergh, Andreas; Gumbo, Maureen; Runemark, August; Johansson, Johan R.; Norrby, Per-Ola; Kann, Nina; Organic & biomolecular chemistry 23 (2025) 8001–8011; doi:10.1039/d5ob01137j

data_7160694
_publ_section_title
;
 Ruthenium-catalyzed synthesis of tricyclic 1,5-fused 1,2,3-triazole
 piperazines.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8001
_journal_page_last               8011
_journal_paper_doi               10.1039/d5ob01137j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C12 H16 N6 O'
_chemical_formula_sum            'C12 H16 N6 O'
_chemical_formula_weight         260.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-08
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-08 deposited with the CCDC.	2025-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.228(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5086(3)
_cell_length_b                   6.6541(2)
_cell_length_c                   10.6871(4)
_cell_measurement_reflns_used    4122
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.4650
_cell_measurement_theta_min      4.4440
_cell_volume                     625.94(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.130a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.130a 64-bit (release 05-07-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.130a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.956
_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     95.00 178.00   0.50    0.46    --  108.56  45.00  90.00  166
  2  \w     30.00 121.00   0.50    0.11    --   43.25  38.00  60.00  182
  3  \w     34.00  79.00   0.50    0.46    --  108.56 -77.00  55.00   90
  4  \w     34.00  79.00   0.50    0.46    --  108.56 -77.00 -30.00   90
  5  \w    109.00 178.00   0.50    0.46    --  108.56  77.00-178.00  138
  6  \w     34.00  79.00   0.50    0.46    --  108.56 -77.00-120.00   90
  7  \w    -30.00  49.00   0.50    0.11    --   43.25 -57.00 -90.00  158
  8  \w    -30.00  49.00   0.50    0.11    --   43.25 -57.00 -90.00  158
  9  \w    -66.00  21.00   0.50    0.11    --  -43.25  77.00-178.00  174
 10  \w    -15.00  34.00   0.50    0.11    --  -43.25  38.00 -90.00   98
 11  \w    -14.00  66.00   0.50    0.11    --   43.25 -77.00  55.00  160
 12  \w     35.00  93.00   0.50    0.46    --  108.56 -94.00  90.00  116
 13  \w    -15.00  34.00   0.50    0.11    --  -43.25  38.00-120.00   98
 14  \w    -72.00 -30.00   0.50    0.46    -- -104.50  77.00-178.00   84
 15  \w    -72.00 -30.00   0.50    0.46    -- -104.50  77.00 -90.00   84
 16  \w    -72.00 -30.00   0.50    0.46    -- -104.50  77.00 120.00   84
 17  \w    -72.00 -30.00   0.50    0.46    -- -104.50  77.00 150.00   84
 18  \w   -120.00 -29.00   0.50    0.11    --  -43.25 -38.00   0.00  182
 19  \w   -120.00 -29.00   0.50    0.11    --  -43.25 -38.00-180.00  182
 20  \w   -120.00 -29.00   0.50    0.11    --  -43.25 -38.00 -90.00  182
 21  \w   -120.00 -29.00   0.50    0.11    --  -43.25 -38.00 120.00  182
 22  \w   -132.00 -89.00   0.50    0.46    -- -104.50 -15.00 120.00   86
 23  \w   -132.00 -89.00   0.50    0.46    -- -104.50 -15.00  90.00   86
 24  \w   -174.00-103.00   0.50    0.46    -- -104.50 -77.00  55.00  142
 25  \w   -132.00 -89.00   0.50    0.46    -- -104.50 -15.00 -30.00   86
 26  \w   -163.00 -90.00   0.50    0.46    -- -104.50 -30.00 -30.00  146
 27  \w   -163.00 -90.00   0.50    0.46    -- -104.50 -30.00 -30.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0239823000
_diffrn_orient_matrix_UB_12      -0.0919369000
_diffrn_orient_matrix_UB_13      -0.1227602000
_diffrn_orient_matrix_UB_21      0.1112158000
_diffrn_orient_matrix_UB_22      0.1708705000
_diffrn_orient_matrix_UB_23      0.0046642000
_diffrn_orient_matrix_UB_31      0.1330151000
_diffrn_orient_matrix_UB_32      -0.1265250000
_diffrn_orient_matrix_UB_33      0.0954139000
_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  0.0315
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6417
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.595
_diffrn_reflns_theta_min         4.469
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.700
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.130a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.252
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1.1(4)
_refine_ls_extinction_coef       0.0072(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2208
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0555P)^2^+0.0200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0936
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                2006
_reflns_number_total             2208
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01137j2.cif
_cod_data_source_block           amine_3jb_auto
_cod_depositor_comments
'Adding full bibliography for 7160694--7160695.cif.'
_cod_database_code               7160694
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.828
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: -0.1(4)
 1.1(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
3.a Ternary CH refined with riding coordinates:
 C00E(H00F)
3.b Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00C(H00C,H00D), C00H(H00I,H00J), C00I(H00K,H00L), C00J(H00M,
 H00N)
3.c Aromatic/amide H refined with riding coordinates:
 C00F(H00G)
3.d Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_shelx_res_checksum              50213
_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 2.106
_oxdiff_exptl_absorpt_empirical_full_min 0.568