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_7134859
_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, C4 H8 O2'
_chemical_formula_sum            'C58 H58 N2 O2'
_chemical_formula_weight         815.06
_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   mixed
_audit_creation_date             2025-07-22
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-07-22 deposited with the CCDC.	2025-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                75.227(5)
_cell_angle_beta                 89.808(6)
_cell_angle_gamma                72.190(6)
_cell_formula_units_Z            2
_cell_length_a                   9.7222(8)
_cell_length_b                   15.4668(9)
_cell_length_c                   16.2481(10)
_cell_measurement_reflns_used    5017
_cell_measurement_temperature    195(100)
_cell_measurement_theta_max      74.3550
_cell_measurement_theta_min      2.7890
_cell_volume                     2241.9(3)
_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_environment      N~2~
_diffrn_ambient_temperature      195(100)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.874
_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   -109.00 -42.00   0.50    0.80    --  -47.32 -70.00   5.00  134
  2  \w     -8.00  25.00   0.50    0.80    --  -47.32  70.00 137.00   66
  3  \w     50.00  75.00   0.50    0.80    --   47.32  70.00 137.00   50
  4  \w    -22.00  61.00   0.50    0.80    --   47.32 -70.00   5.00  166
  5  \w   -170.00 -87.00   0.50    4.00    -- -103.74 -70.00   5.00  166
  6  \w    -64.00 -37.00   0.50    4.00    -- -103.74  70.00 137.00   54
  7  \w     35.00  89.00   0.50    4.00    --  103.74 -70.00   5.00  108
  8  \w    145.00 170.00   0.50    4.00    --  103.74  70.00 137.00   50
  9  \w    -21.00  22.00   0.50    0.80    --  -47.32  19.00 -60.00   86
 10  \w    -22.00  22.00   0.50    0.80    --  -47.32  19.00 150.00   88
 11  \w   -168.00 -78.00   0.50    4.00    -- -103.74-125.00 -30.00  180
 12  \w    -60.00 -34.00   0.50    4.00    -- -103.74  57.00 -90.00   52
 13  \w    -60.00 -33.00   0.50    4.00    -- -103.74  57.00   0.00   54
 14  \w     41.00  66.00   0.50    4.00    --  103.74 -57.00  60.00   50
 15  \w     34.00  66.00   0.50    4.00    --  103.74 -57.00  30.00   64
 16  \w    113.00 174.00   0.50    4.00    --  103.74  38.00  30.00  122
 17  \w     32.00  59.00   0.50    4.00    --  103.74 -57.00-150.00   54
 18  \w     37.00  64.00   0.50    4.00    --  103.74 -57.00 150.00   54
 19  \w     85.00 169.00   0.50    4.00    --  103.74 125.00  60.00  168
 20  \w     36.00  68.00   0.50    4.00    --  103.74 -57.00-120.00   64
 21  \w     40.00  65.00   0.50    4.00    --  103.74 -57.00 -60.00   50
 22  \w    129.00 155.00   0.50    4.00    --  103.74  38.00  60.00   52
 23  \w     -2.00  52.00   0.50    0.80    --   48.32 -51.00-168.00  108
 24  \w    -23.00   6.00   0.50    0.80    --  -48.32  19.00  60.00   58
 25  \w    -88.00 -19.00   0.50    0.80    --  -48.32 125.00 120.00  138
 26  \w     93.00 119.00   0.50    0.80    --   48.32  38.00 -30.00   52
 27  \w     48.00  75.00   0.50    0.80    --   48.32  38.00 -30.00   54
 28  \w    -85.00 -58.00   0.50    4.00    -- -103.74 125.00 -90.00   54
 29  \w   -111.00 -86.00   0.50    4.00    -- -103.74 125.00   0.00   50
 30  \w    -65.00 -37.00   0.50    4.00    -- -103.74 132.00 -88.61   56
 31  \w   -108.00 -80.00   0.50    4.00    -- -103.74 113.00 140.52   56
 32  \w   -174.00-105.00   0.50    4.00    -- -103.74 -38.00-150.00  138
 33  \w   -165.00-139.00   0.50    4.00    -- -103.74 -19.00-120.00   52
 34  \w   -124.00 -98.00   0.50    4.00    -- -103.74 144.00 168.94   52
 35  \w   -122.00 -94.00   0.50    4.00    -- -103.74 139.00 -78.95   56
 36  \w   -157.00-131.00   0.50    4.00    -- -103.74-125.00   0.00   52
 37  \w   -125.00 -82.00   0.50    4.00    -- -103.74-125.00   0.00   86
 38  \w   -172.00-146.00   0.50    4.00    -- -103.74 -19.00  30.00   52
 39  \w   -123.00 -98.00   0.50    4.00    -- -103.74 -19.00  30.00   50
 40  \w     72.00 103.00   0.50    4.00    --  103.74 -99.00  60.00   62
 41  \w     41.00 105.00   0.50    4.00    --  103.74-125.00-120.00  128
 42  \w     50.00 105.00   0.50    4.00    --  103.74 -99.00   0.00  110
 43  \w     55.00  89.00   0.50    4.00    --  103.74 -99.00  30.00   68
 44  \w     54.00 105.00   0.50    4.00    --  103.74 -99.00-120.00  102
 45  \w     80.00 105.00   0.50    4.00    --  103.74 -99.00  90.00   50
 46  \w     32.00  63.00   0.50    4.00    --  103.74 -57.00 120.00   62
 47  \w     37.00  93.00   0.50    4.00    --  103.74 -99.00 -90.00  112
 48  \w     58.00 102.00   0.50    4.00    --  103.74 -99.00 150.00   88
 49  \w     55.00  82.00   0.50    4.00    --  103.74-125.00  30.00   54
 50  \w     34.00  81.00   0.50    4.00    --  103.74 -99.00-180.00   94
;
_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      -0.0375016000
_diffrn_orient_matrix_UB_12      -0.0069174000
_diffrn_orient_matrix_UB_13      0.0931733000
_diffrn_orient_matrix_UB_21      -0.0853402000
_diffrn_orient_matrix_UB_22      -0.0674890000
_diffrn_orient_matrix_UB_23      -0.0062528000
_diffrn_orient_matrix_UB_31      0.1385307000
_diffrn_orient_matrix_UB_32      -0.0847982000
_diffrn_orient_matrix_UB_33      0.0309882000
_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  0.1710
_diffrn_reflns_av_unetI/netI     0.1060
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25088
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         84.388
_diffrn_reflns_theta_min         2.822
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.554
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82315
_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 yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.758
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     620
_refine_ls_number_reflns         8818
_refine_ls_number_restraints     212
_refine_ls_restrained_S_all      1.754
_refine_ls_R_factor_all          0.2453
_refine_ls_R_factor_gt           0.1897
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4790
_refine_ls_wR_factor_ref         0.5264
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4770
_reflns_number_total             8818
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03678j2.cif
_cod_data_source_block           2_auto
_cod_depositor_comments
'Adding full bibliography for 7134851--7134861.cif.'
_cod_database_code               7134859
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N'
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.851
_reflns_odcompleteness_completeness 98.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Restrained distances
 O2-C5
 1.32 with sigma of 0.02
 O2-C6
 1.46 with sigma of 0.02
 O3-C5
 1.22 with sigma of 0.02
 C4-C5
 1.49 with sigma of 0.02
 C6-C7
 1.5 with sigma of 0.02
 O2-C4
 2.35 with sigma of 0.04
 O3-C4
 2.4 with sigma of 0.04
 O2-O3
 2.24 with sigma of 0.04
 O2-C7
 2.38 with sigma of 0.04
 C4-C5 \\sim C6-C7
 with sigma of 0.02
2. Restrained planarity
 O2, O3, C4, C5, C6, C7
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
O2 \\sim O3 \\sim C4 \\sim C5 \\sim C6 \\sim C7: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08 within 2A
O2A \\sim O3A \\sim C4A \\sim C5A \\sim C6A \\sim C7A \\sim O2 \\sim O3 \\sim
C4 \\sim C5 \\sim C6 \\sim C7: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 O2, O3, C4, C5, C6, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{O2A, O3A, C4A, C5A, C6A, C7A} sigma for 1-2: 0.02, 1-3: 0.02
as in
{O2, O3, C4, C5, C6, C7}
6. Others
 Sof(O2A)=Sof(O3A)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(H4AC)=Sof(C5A)=Sof(C6A)=
 Sof(H6AA)=Sof(H6AB)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=1-FVAR(1)
 Sof(O2)=Sof(O3)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(H4C)=Sof(C5)=Sof(C6)=Sof(H6A)=
 Sof(H6B)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=FVAR(1)
 Fixed Y: C7A(0.79276)
7.a Riding coordinates:
 C7A(H7AA,H7AB,H7AC)
7.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C43(H43A,H43B), C44(H44A,H44B), C6A(H6AA,H6AB),
 C6(H6A,H6B)
7.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C16(H16), C17(H17), C21(H21), C22(H22), C24(H24),
 C25(H25), C27(H27), C28(H28), C30(H30), C31(H31), C32(H32), C33(H33), C35(H35),
  C37(H37), C38(H38), C40(H40), C41(H41), C47(H47), C48(H48), C50(H50),
 C51(H51), C53(H53), C54(H54), C56(H56), C57(H57), C58(H58), C59(H59), C61(H61)
7.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C42(H42A,H42B,H42C), C45(H45A,H45B,
 H45C), C4A(H4AA,H4AB,H4AC), C4(H4A,H4B,H4C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              83994
_shelx_hkl_checksum              39860
_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 2.190
_oxdiff_exptl_absorpt_empirical_full_min 0.380