Unexpected synthesis of 4,4'-bis(1,2,3-triazole)s from calcium carbide as an acetylene source <i>via</i> a click reaction.
Fu, Rugang; Cao, Cheng; Wang, Junke; Wen, Fei; Qiu, Dong; Zong, Yingxiao; Organic & biomolecular chemistry 23 (2025) 10508–10513; doi:10.1039/d5ob01202c

data_7160838
_publ_section_title
;
 Unexpected synthesis of 4,4'-bis(1,2,3-triazole)s from calcium carbide as
 an acetylene source <i>via</i> a click reaction.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10508
_journal_page_last               10513
_journal_paper_doi               10.1039/d5ob01202c
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C20 H20 N6'
_chemical_formula_sum            'C20 H20 N6'
_chemical_formula_weight         344.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-09-14
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-01-03 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.3739(2)
_cell_length_b                   13.2079(3)
_cell_length_c                   32.2928(8)
_cell_measurement_reflns_used    4150
_cell_measurement_temperature    213.00(10)
_cell_measurement_theta_max      76.2480
_cell_measurement_theta_min      2.7140
_cell_volume                     3571.64(15)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      213.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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   -162.00-136.00   1.00    1.70    --  -91.75 -16.00  33.00   26
  2  \w   -158.00 -82.00   1.00    1.70    --  -91.75-114.00-142.00   76
  3  \w    -12.00  19.00   1.00    0.40    --  -48.42  19.00-120.00   31
  4  \w    -37.00  25.00   1.00    0.40    --  -48.42  38.00 -90.00   62
  5  \w    -25.00  16.00   1.00    0.40    --  -48.42  19.00 -30.00   41
  6  \w     94.00 162.00   1.00    1.70    --  106.65  19.00-120.00   68
  7  \w     76.00 102.00   1.00    0.40    --   48.42 155.00-167.00   26
  8  \w     36.00  65.00   1.00    1.70    --  106.65 -57.00 -90.00   29
  9  \w     43.00 111.00   1.00    1.70    --  106.65-125.00   0.00   68
 10  \w     76.00 132.00   1.00    1.70    --  106.65-155.00 155.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0227773000
_diffrn_orient_matrix_UB_12      0.0117947000
_diffrn_orient_matrix_UB_13      -0.0470913000
_diffrn_orient_matrix_UB_21      -0.1797493000
_diffrn_orient_matrix_UB_22      -0.0216782000
_diffrn_orient_matrix_UB_23      0.0049051000
_diffrn_orient_matrix_UB_31      -0.0318042000
_diffrn_orient_matrix_UB_32      0.1140086000
_diffrn_orient_matrix_UB_33      0.0058374000
_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  0.0368
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            10695
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         2.737
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.281
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0593P)^2^+1.0004P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2561
_reflns_number_total             3158
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01202c2.cif
_cod_data_source_block           ws_1
_cod_depositor_comments          'Adding full bibliography for 7160838.cif.'
_cod_database_code               7160838
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHCaCl
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.951
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 C19(H19A,H19B,H19C)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C16(H16), C18(H18), C20(H20), C3(H3), C13(H13), C7(H7), C15(H15),
 C2(H2), C17(H17)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              69638
_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 1.282
_oxdiff_exptl_absorpt_empirical_full_min 0.796