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_7249945
_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, 2(C H Cl3)'
_chemical_formula_sum            'C54 H48 Cl6 N12'
_chemical_formula_weight         1077.74
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-01
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-07-25 deposited with the CCDC.	2025-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.695(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6444(3)
_cell_length_b                   49.4450(13)
_cell_length_c                   11.0340(4)
_cell_measurement_reflns_used    2781
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      64.8110
_cell_measurement_theta_min      4.4350
_cell_volume                     5233.1(3)
_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 16.2595
_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   -107.00  -7.00   1.00    7.50    --  -36.03 -19.00-150.00  100
  2  \w     32.00  89.00   1.00    7.50    --   36.03-125.00  90.00   57
  3  \w    105.00 154.00   1.00   27.50    --   93.63  77.00  90.00   49
  4  \w     36.00 108.00   1.00   27.50    --   93.63-111.00-180.00   72
  5  \w    121.00 161.00   1.00   27.50    --   93.63  77.00  30.00   40
  6  \w     26.00 106.00   1.00   27.50    --   93.63 -95.00 -60.00   80
  7  \w     27.00  89.00   1.00   27.50    --   93.63 -61.00   0.00   62
  8  \w    103.00 159.00   1.00   27.50    --   93.63  77.00-120.00   56
  9  \w     81.00 141.00   1.00   27.50    --   93.63  30.00-150.00   60
;
_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      -0.0775017000
_diffrn_orient_matrix_UB_12      -0.0257067000
_diffrn_orient_matrix_UB_13      -0.0735089000
_diffrn_orient_matrix_UB_21      0.1155848000
_diffrn_orient_matrix_UB_22      -0.0175972000
_diffrn_orient_matrix_UB_23      0.1047968000
_diffrn_orient_matrix_UB_31      -0.0803257000
_diffrn_orient_matrix_UB_32      -0.0005051000
_diffrn_orient_matrix_UB_33      0.0872422000
_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  0.0525
_diffrn_reflns_av_unetI/netI     0.0917
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       55
_diffrn_reflns_limit_k_min       -56
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15475
_diffrn_reflns_point_group_measured_fraction_full 0.692
_diffrn_reflns_point_group_measured_fraction_max 0.692
_diffrn_reflns_theta_full        62.385
_diffrn_reflns_theta_max         62.385
_diffrn_reflns_theta_min         3.576
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.394
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91900
_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    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             2232
_exptl_crystal_preparation
'Crytals were grown by evaporation of a chloroform solution.'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.882
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 2005 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.30(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1305
_refine_ls_number_reflns         11518
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0715
_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^)+(0.0863P)^2^+4.2408P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1716
_refine_ls_wR_factor_ref         0.1850
_reflns_Friedel_coverage         0.381
_reflns_Friedel_fraction_full    0.387
_reflns_Friedel_fraction_max     0.387
_reflns_number_gt                9540
_reflns_number_total             11518
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00020c2.cif
_cod_data_source_block           1_chloroform
_cod_depositor_comments
'Adding full bibliography for 7249942--7249945.cif.'
_cod_database_code               7249945
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C60 H80 N12'
_chemical_oxdiff_usercomment     jns_219_261
_shelx_estimated_absorpt_t_max   0.876
_shelx_estimated_absorpt_t_min   0.648
_reflns_odcompleteness_completeness 98.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     62.30
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C101(H101), C104(H104), C102(H102), C103(H103)
1.b Secondary CH2 refined with riding coordinates:
 C46(H46A,H46B), C39(H39A,H39B), C13(H13A,H13B), C98(H98A,H98B), C20(H20A,
 H20B), C65(H65A,H65B), C72(H72A,H72B), C91(H91A,H91B)
1.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C30(H30), C90(H90), C82(H82), C56(H56), C88(H88), C36(H36), C62(H62),
 C12(H12), C10(H10), C38(H38), C64(H64), C67(H67), C52(H52), C94(H94), C93(H93),
  C95(H95), C24(H24), C19(H19), C16(H16), C48(H48), C15(H15), C50(H50),
 C49(H49), C51(H51), C69(H69), C68(H68), C71(H71), C18(H18), C108(H108),
 C70(H70), C25(H25), C78(H78), C17(H17), C45(H45), C100(H100), C23(H23),
 C96(H96), C41(H41), C106(H106), C97(H97), C22(H22), C107(H107), C105(H105),
 C26(H26), C77(H77), C44(H44), C74(H74), C43(H43), C42(H42), C75(H75), C76(H76)
1.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C86(H86A,H86B,H86C), C7(H7A,H7B,H7C), C59(H59A,H59B,
 H59C), C33(H33A,H33B,H33C), C85(H85A,H85B,H85C), C8(H8A,H8B,H8C), C60(H60A,
 H60B,H60C)
;
_shelx_res_checksum              13553
_ins_header
;
TITL jns2202 in P2(1) 
REM P2(1) (#4 in standard setting)
CELL 1.54184  10.644399  49.444959  11.034046  90.0000 115.6949  90.0000
ZERR    4.00   0.000333   0.001294   0.000395   0.0000   0.0042   0.0000
LATT -1
SYMM -x, y+1/2,-z 
SFAC C H N
UNIT 240.00 320.00 48.00
REM  CrysAlisPro recorded range (K): Min=150.0; max=150.0; aver:150.0
TEMP -123
SIZE 0.04 0.11 0.14
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 1.367
_oxdiff_exptl_absorpt_empirical_full_min 0.808