Structural diversity in 1D hydrogen-bonded chains assembled through bis(triazole) self-association
Smith, Jordan N.; White, Nicholas G.; CrystEngComm 27 (2025) 1568–1574; doi:10.1039/D5CE00020C

data_7249944
_publ_section_title
;
 Structural diversity in 1D hydrogen-bonded chains assembled through
 bis(triazole) self-association
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1568
_journal_page_last               1574
_journal_paper_doi               10.1039/D5CE00020C
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C52 H46 N12'
_chemical_formula_sum            'C52 H46 N12'
_chemical_formula_weight         839.01
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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             2024-07-23
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-25 deposited with the CCDC.	2025-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                68.942(8)
_cell_angle_beta                 77.748(6)
_cell_angle_gamma                63.780(8)
_cell_formula_units_Z            1
_cell_length_a                   10.8323(7)
_cell_length_b                   10.8523(10)
_cell_length_c                   13.3670(10)
_cell_measurement_reflns_used    3104
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.2550
_cell_measurement_theta_min      4.5670
_cell_volume                     1312.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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   -106.00 -15.00   1.00    5.00    --  -36.03 -19.00-180.00   91
  2  \w    -52.00  26.00   1.00    5.00    --  -36.03  57.00  90.00   78
  3  \w   -107.00  -7.00   1.00    5.00    --  -36.03 -19.00 -90.00  100
  4  \w     33.00  88.00   1.00    5.00    --   36.03-125.00   0.00   55
  5  \w      6.00  75.00   1.00    5.00    --   36.03 -99.00 150.00   69
  6  \w     74.00 101.00   1.00   20.00    --  105.15-111.00 -30.00   27
  7  \w     38.00 123.00   1.00   20.00    --  105.15 -61.00-150.00   85
  8  \w     36.00 109.00   1.00   20.00    --  105.15-111.00-120.00   73
  9  \w     45.00 130.00   1.00   20.00    --  105.15 -77.00  60.00   85
 10  \w     83.00 126.00   1.00   20.00    --  105.15 -30.00 120.00   43
 11  \w     84.00 175.00   1.00   20.00    --  105.15  30.00   0.00   91
 12  \w    116.00 160.00   1.00   20.00    --  105.15  77.00-150.00   44
 13  \w     53.00 106.00   1.00   20.00    --  105.15 -95.00   0.00   53
 14  \w     45.00 126.00   1.00   20.00    --  105.15 -30.00  30.00   81
 15  \w     37.00  68.00   1.00   20.00    --  105.15 -30.00 120.00   31
 16  \w     84.00 150.00   1.00   20.00    --  105.15  30.00 -60.00   66
 17  \w     39.00 115.00   1.00   20.00    --  105.15 -45.00 -60.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1440057000
_diffrn_orient_matrix_UB_12      -0.1044324000
_diffrn_orient_matrix_UB_13      -0.0296708000
_diffrn_orient_matrix_UB_21      0.0586183000
_diffrn_orient_matrix_UB_22      0.1119259000
_diffrn_orient_matrix_UB_23      -0.0147894000
_diffrn_orient_matrix_UB_31      0.0325775000
_diffrn_orient_matrix_UB_32      -0.0643081000
_diffrn_orient_matrix_UB_33      0.1192281000
_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  0.0291
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6788
_diffrn_reflns_point_group_measured_fraction_full 0.538
_diffrn_reflns_point_group_measured_fraction_max 0.538
_diffrn_reflns_theta_full        66.572
_diffrn_reflns_theta_max         66.572
_diffrn_reflns_theta_min         3.550
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.517
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022)
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    1.061
_exptl_crystal_description       block
_exptl_crystal_F_000             442
_exptl_crystal_preparation
'Crystals were grown by vapour diffusion of diethyl ether into a dichloromethane solution.'
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_coef       0.0073(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     618
_refine_ls_number_reflns         4990
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0777P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1208
_reflns_Friedel_coverage         0.089
_reflns_Friedel_fraction_full    0.088
_reflns_Friedel_fraction_max     0.088
_reflns_number_gt                4741
_reflns_number_total             4990
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00020c2.cif
_cod_data_source_block           1_DCM_ether
_cod_depositor_comments
'Adding full bibliography for 7249942--7249945.cif.'
_cod_database_code               7249944
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C40 H60 N1 O4'
_chemical_oxdiff_usercomment     jns_283+4-carboxylate
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.865
_reflns_odcompleteness_completeness 98.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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. Restrained distances
 C40-C41 = C41-C42 = C42-C43 = C43-C44 = C44-C45 = C45-C40
 1.395 with sigma of 0.01
 C40-C53 = C40-C56 = C43-C55 = C43-C54 = C53-C54 = C55-C56
 1.395 with sigma of 0.01
3. Others
 Fixed Sof: C41(0.6) H41(0.6) C42(0.6) H42(0.6) H43(0.6) H43A(0.4) C44(0.6)
 H44(0.6) C45(0.6) H45(0.6) C53(0.4) H53(0.4) C55(0.4) H55(0.4) C56(0.4)
 H56(0.4) C54(0.4) H54(0.4)
4.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C20(H20A,H20B), C39(H39A,H39B), C46(H46A,H46B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C30(H30), C36(H36), C38(H38),
  C41(H41), C42(H42), C43(H43), C43(H43A), C44(H44), C45(H45), C48(H48),
 C49(H49), C50(H50), C51(H51), C52(H52), C53(H53), C55(H55), C56(H56), C54(H54)
4.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              49556
_shelx_fab_checksum              50022
_ins_header
;
TITL jns2204 in P-1 
REM P-1 (#2 in standard setting)
CELL 1.54184  10.832295  10.852309  13.366994  68.9420  77.7476  63.7803
ZERR    2.00   0.000698   0.001046   0.000981   0.0080   0.0059   0.0078
LATT  1
SFAC C H N O
UNIT 80.00 120.00 2.00 8.00
REM  CrysAlisPro recorded range (K): Min=150.0; max=150.0; aver:150.0
TEMP -123
SIZE 0.06 0.24 0.29
TREF
HKLF 4
END
;
_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 1.475
_oxdiff_exptl_absorpt_empirical_full_min 0.736