Positional isomerism-directed formation of hydrogen-bonded organic frameworks with distinct single-crystal transformation pathways.
Yang, Wenyan; Li, Lele; Xue, Xinlei; Deng, Shengyong; Wei, Peifa; Chemical communications (Cambridge, England) 61 (2025) 13113–13116; doi:10.1039/d5cc03678j

data_7134857
_publ_section_title
;
 Positional isomerism-directed formation of hydrogen-bonded organic
 frameworks with distinct single-crystal transformation pathways.
;
_journal_issue                   70
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13113
_journal_page_last               13116
_journal_paper_doi               10.1039/d5cc03678j
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C54 H50 N2, 0.05(C H2 Cl2)'
_chemical_formula_sum            'C54.05 H50.1 Cl0.1 N2'
_chemical_formula_weight         731.20
_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
_audit_creation_date             2025-07-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-07-25 deposited with the CCDC.	2025-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                100.086(4)
_cell_angle_beta                 106.629(4)
_cell_angle_gamma                93.275(4)
_cell_formula_units_Z            2
_cell_length_a                   9.8175(3)
_cell_length_b                   15.0293(9)
_cell_length_c                   15.4757(7)
_cell_measurement_reflns_used    8577
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.7730
_cell_measurement_theta_min      3.0040
_cell_volume                     2140.17(18)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.934
_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    -54.00  24.00   0.50    0.68    --  -47.57  92.00  93.00  156
  2  \w    -21.00  73.00   0.50    0.68    --   47.57 -92.00 -18.00  188
  3  \w   -142.00-116.00   0.50    2.74    -- -103.74 -92.00 -18.00   52
  4  \w    -80.00 -48.00   0.50    2.74    -- -103.74  92.00  93.00   64
  5  \w     54.00  81.00   0.50    2.74    --  103.74 -92.00 -18.00   54
  6  \w     89.00 175.00   0.50    2.74    --  103.74  92.00  93.00  172
  7  \w    -26.00  17.00   0.50    0.68    --  -47.57  77.00-120.00   86
  8  \w    -65.00 -38.00   0.50    0.68    --  -47.57  77.00-120.00   54
  9  \w    -23.00  39.00   0.50    0.68    --   47.57 -38.00  30.00  124
 10  \w    -16.00  30.00   0.50    0.68    --   47.57 -19.00  60.00   92
 11  \w     -9.00  27.00   0.50    0.68    --   47.57 -19.00 -90.00   72
 12  \w     25.00  58.00   0.50    0.68    --   47.57-125.00-120.00   66
 13  \w    -14.00  29.00   0.50    0.68    --   47.57 -19.00 -30.00   86
 14  \w   -148.00-103.00   0.50    2.74    -- -103.74 -57.00-150.00   90
 15  \w    -62.00 -37.00   0.50    2.74    -- -103.74  57.00 -60.00   50
 16  \w   -107.00 -60.00   0.50    2.74    -- -103.74 125.00  90.00   94
 17  \w   -128.00 -91.00   0.50    2.74    -- -103.74 150.00 155.99   74
 18  \w    -64.00 -35.00   0.50    2.74    -- -103.74 150.00 155.99   58
 19  \w   -125.00 -91.00   0.50    2.74    -- -103.74 144.00 127.63   68
 20  \w   -173.00 -98.00   0.50    2.74    -- -103.74 -57.00 -60.00  150
 21  \w   -163.00 -99.00   0.50    2.74    -- -103.74 -38.00   0.00  128
 22  \w    -82.00 -36.00   0.50    2.74    -- -103.74 125.00 -30.00   92
 23  \w   -124.00 -80.00   0.50    2.74    -- -103.74 144.00 -72.12   88
 24  \w    -89.00 -59.00   0.50    2.74    -- -103.74 144.00 127.63   60
 25  \w    -62.00 -32.00   0.50    2.74    -- -103.74  57.00 -90.00   60
 26  \w   -125.00 -87.00   0.50    2.74    -- -103.74 -99.00-150.00   76
 27  \w    -60.00 -35.00   0.50    2.74    -- -103.74  57.00-180.00   50
 28  \w   -171.00-146.00   0.50    2.74    -- -103.74 -99.00-150.00   50
 29  \w    -68.00 -41.00   0.50    2.74    -- -103.74 137.00 -27.69   54
 30  \w   -121.00 -95.00   0.50    2.74    -- -103.74 137.00 -27.69   52
 31  \w   -105.00 -80.00   0.50    2.74    -- -103.74 -92.00 -18.00   50
 32  \w     41.00 105.00   0.50    2.74    --  103.74 -99.00 120.00  128
 33  \w     37.00  68.00   0.50    2.74    --  103.74 -57.00  60.00   62
 34  \w     64.00 106.00   0.50    2.74    --  103.74 -99.00  30.00   84
 35  \w     43.00  72.00   0.50    2.74    --  103.74 -99.00 -30.00   58
 36  \w     36.00  93.00   0.50    2.74    --  103.74 -99.00-150.00  114
 37  \w    134.00 172.00   0.50    2.74    --  103.74  57.00  60.00   76
 38  \w     99.00 130.00   0.50    2.74    --  103.74  57.00  60.00   62
 39  \w     38.00  69.00   0.50    2.74    --  103.74 -57.00 120.00   62
 40  \w     43.00 106.00   0.50    2.74    --  103.74 -99.00 -90.00  126
 41  \w    129.00 173.00   0.50    2.74    --  103.74 125.00   0.00   88
 42  \w     86.00 122.00   0.50    2.74    --  103.74 125.00   0.00   72
 43  \w     38.00  84.00   0.50    2.74    --  103.74 -99.00  60.00   92
 44  \w     47.00  73.00   0.50    2.74    --  103.74-125.00-150.00   52
 45  \w     93.00 165.00   0.50    2.74    --  103.74  77.00   0.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25546
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.500
_diffrn_reflns_theta_min         3.006
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_description       block
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     627
_refine_ls_number_reflns         8508
_refine_ls_number_restraints     392
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0812
_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^)+(0.1037P)^2^+1.2653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2263
_refine_ls_wR_factor_ref         0.2423
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5888
_reflns_number_total             8508
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03678j2.cif
_cod_data_source_block           0523-b-dcm-fume_auto
_cod_depositor_comments
'Adding full bibliography for 7134851--7134861.cif.'
_cod_original_formula_sum        'C54.05 H50.10 Cl0.10 N2'
_cod_database_code               7134857
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.853
_olex2_refinement_description
;
1. Restrained distances
 Cl2-C55
 1.78 with sigma of 0.02
 Cl1-C55
 1.77 with sigma of 0.02
 Cl2-C55 = Cl1-C55
 1.771 with sigma of 0.01
 Cl2-Cl1
 2.916 with sigma of 0.03
 Cl2-Cl1
 2.92 with sigma of 0.04
2. Uiso/Uaniso restraints and constraints
Cl1 \\sim Cl2 \\sim C55: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41 \\sim C42 \\sim
C43 \\sim C44 \\sim C35A \\sim C36A \\sim C37A \\sim C38A \\sim C39A \\sim C40A
\\sim C41A \\sim C42A \\sim C43A \\sim C44A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
Uanis(Cl1) \\sim Ueq, Uanis(C55) \\sim Ueq, Uanis(Cl2) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 Cl1, Cl2, C55
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Same fragment restrains
{C35A, C36A, C37A, C38A, C39A, C40A, C41A, C42A, C43A, C44A} sigma for 1-2:
0.02, 1-3: 0.02
as in
{C35, C36, C37, C38, C39, C40, C41, C42, C43, C44}
5. Others
 Sof(C35A)=Sof(C36A)=Sof(H36A)=Sof(C37A)=Sof(C38A)=Sof(H38A)=Sof(C39A)=
 Sof(H39A)=Sof(C40A)=Sof(H40A)=Sof(C41A)=Sof(H41A)=Sof(C42A)=Sof(C43A)=
 Sof(H43A)=Sof(C44A)=Sof(H44A)=1-FVAR(1)
 Sof(C35)=Sof(C36)=Sof(H36)=Sof(C37)=Sof(C38)=Sof(H38)=Sof(C39)=Sof(H39)=
 Sof(C40)=Sof(H40)=Sof(C41)=Sof(H41)=Sof(C42)=Sof(C43)=Sof(H43)=Sof(C44)=
 Sof(H44)=FVAR(1)
 Fixed Sof: Cl1(0.05) Cl2(0.05) C55(0.05) H55A(0.05) H55B(0.05)
6.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C27(H27A,H27B), C52(H52A,H52B), C53(H53A,H53B), C55(H55A,H55B)
6.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C30(H30),
  C31(H31), C33(H33), C34(H34), C36(H36), C38(H38), C39(H39), C40(H40),
 C41(H41), C43(H43), C44(H44), C46(H46), C47(H47), C49(H49), C50(H50),
 C36A(H36A), C38A(H38A), C39A(H39A), C40A(H40A), C41A(H41A), C43A(H43A),
 C44A(H44A)
6.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C28(H28A,H28B,H28C), C51(H51A,H51B,H51C), C54(H54A,H54B,
 H54C)
;
_shelx_res_checksum              82726
_shelx_hkl_checksum              57898
_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
;