Solvatomorphism of a 2,6-pyridyldicarboxamide-based foldamer.
Ozturk, Sena; Davis, Alexander R.; Seaton, Colin C.; Male, Louise; Pike, Sarah J.; Organic & biomolecular chemistry 23 (2025) 5590–5599; doi:10.1039/d5ob00342c

data_7160442
_publ_section_title
;
 Solvatomorphism of a 2,6-pyridyldicarboxamide-based foldamer.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5590
_journal_page_last               5599
_journal_paper_doi               10.1039/d5ob00342c
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C31 H25 N9 O2, C4 H8 O'
_chemical_formula_sum            'C35 H33 N9 O3'
_chemical_formula_weight         627.70
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-25
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-25 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.4610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.7137(2)
_cell_length_b                   10.3944(2)
_cell_length_c                   12.6481(2)
_cell_measurement_reflns_used    15697
_cell_measurement_temperature    99.99(16)
_cell_measurement_theta_max      78.1730
_cell_measurement_theta_min      3.4900
_cell_volume                     1537.18(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 42.54a 64-bit (release 26-04-2022))'
_computing_data_reduction        'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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    -34.00  25.00   0.50    3.44    --  -49.13  18.00 -60.00  118
  2  \w   -122.00 -38.00   0.50    3.44    --  -49.13 -18.00 130.00  168
  3  \w     39.00 124.00   0.50    3.44    --   49.13  18.00 -60.00  170
  4  \w   -163.00 -79.00   0.50   13.76    --  -90.00 -18.00 130.00  168
  5  \w    102.00 178.00   0.50   13.76    --  111.50  18.00 -60.00  152
  6  \w   -121.00 -38.00   0.50    3.44    --  -49.13 -38.00  60.00  166
  7  \w    -47.00  21.00   0.50    3.44    --  -49.13  38.00  30.00  136
  8  \w    -77.00 -51.00   0.50    3.44    --  -49.13 -49.00   3.30   52
  9  \w   -108.00 -81.00   0.50    3.44    --  -49.13 -49.00   3.30   54
 10  \w    -90.00 -39.00   0.50    3.44    --  -49.13 -19.00  30.00  102
 11  \w   -120.00 -95.00   0.50    3.44    --  -49.13 -57.00-150.00   50
 12  \w    -77.00 -47.00   0.50    3.44    --  -49.13 -51.00  45.12   60
 13  \w    -68.00 -37.00   0.50    3.44    --  -49.13 -50.00 -65.50   62
 14  \w    -63.00 -37.00   0.50    3.44    --  -49.13 -47.00 -47.99   52
 15  \w     41.00  68.00   0.50    3.44    --   49.13  50.00  54.79   54
 16  \w     38.00  68.00   0.50    3.44    --   49.13  52.00  72.98   60
 17  \w     37.00  80.00   0.50    3.44    --   49.13  51.00 131.93   86
 18  \w     -7.00  21.00   0.50    3.44    --   49.13 -18.00 130.00   56
 19  \w     38.00  63.00   0.50    3.44    --   49.13  50.00  46.56   50
 20  \w     37.00  63.00   0.50    3.44    --   49.13  51.00 109.90   52
 21  \w     37.00  66.00   0.50    3.44    --   49.13  51.00  96.08   58
 22  \w   -103.00 -78.00   0.50   13.76    --  -90.00 -49.00  -5.13   50
 23  \w   -105.00 -80.00   0.50   13.76    --  -90.00 -52.00 -10.04   50
 24  \w   -115.00 -79.00   0.50   13.76    --  -90.00 -47.00  16.31   72
 25  \w   -103.00 -78.00   0.50   13.76    --  -90.00 -48.00  99.54   50
 26  \w   -106.00 -80.00   0.50   13.76    --  -90.00 -52.00  -8.51   52
 27  \w   -118.00 -80.00   0.50   13.76    --  -90.00 -52.00  32.49   76
 28  \w   -108.00 -81.00   0.50   13.76    --  -90.00 -51.00  78.55   54
 29  \w   -104.00 -78.00   0.50   13.76    --  -90.00 -49.00  55.30   52
 30  \w   -109.00 -81.00   0.50   13.76    --  -90.00 -51.00 -57.69   56
 31  \w   -104.00 -78.00   0.50   13.76    --  -90.00 -51.00 -43.04   52
 32  \w   -113.00 -81.00   0.50   13.76    --  -90.00 -48.00   5.35   64
 33  \w   -107.00 -81.00   0.50   13.76    --  -90.00 -52.00  43.89   52
 34  \w   -104.00 -78.00   0.50   13.76    --  -90.00 -49.00 -23.47   52
 35  \w   -107.00 -81.00   0.50   13.76    --  -90.00 -49.00  64.55   52
 36  \w   -105.00 -80.00   0.50   13.76    --  -90.00 -52.00  85.83   50
 37  \w   -104.00 -78.00   0.50   13.76    --  -90.00 -47.00  -5.00   52
 38  \w   -155.00-129.00   0.50   13.76    --  -90.00 -52.00  85.83   52
 39  \w   -106.00 -80.00   0.50   13.76    --  -90.00 -52.00 -51.02   52
 40  \w   -106.00 -80.00   0.50   13.76    --  -90.00 -52.00  50.66   52
 41  \w    -65.00 -19.00   0.50   13.76    --  -90.00  61.00  90.00   92
 42  \w   -111.00 -85.00   0.50   13.76    --  -90.00 -53.00 -27.25   52
 43  \w     47.00 104.00   0.50   13.76    --  111.50 -95.00  30.00  114
 44  \w     40.00  83.00   0.50   13.76    --  111.50 -77.00  60.00   86
 45  \w    143.00 169.00   0.50   13.76    --  111.50  61.00  90.00   52
 46  \w    103.00 129.00   0.50   13.76    --  111.50  61.00  90.00   52
 47  \w    150.00 177.00   0.50   13.76    --  111.50  45.00  30.00   54
 48  \w    147.00 177.00   0.50   13.76    --  111.50  61.00   0.00   60
 49  \w     98.00 128.00   0.50   13.76    --  111.50  61.00   0.00   60
 50  \w    105.00 142.00   0.50   13.76    --  111.50  45.00  30.00   74
 51  \w     99.00 155.00   0.50   13.76    --  111.50  61.00  60.00  112
 52  \w     78.00 105.00   0.50   13.76    --  111.50 -95.00   0.00   54
 53  \w     47.00  73.00   0.50   13.76    --  111.50 -95.00   0.00   52
 54  \w     40.00  67.00   0.50   13.76    --  111.50 -61.00-120.00   54
 55  \w     40.00  66.00   0.50   13.76    --  111.50 -61.00-150.00   52
 56  \w    103.00 130.00   0.50   13.76    --  111.50  45.00  90.00   54
 57  \w    101.00 144.00   0.50   13.76    --  111.50  61.00  30.00   86
 58  \w    101.00 129.00   0.50   13.76    --  111.50  45.00   0.00   56
 59  \w    115.00 175.00   0.50   13.76    --  111.50  45.00 -30.00  120
 60  \w     40.00  67.00   0.50   13.76    --  111.50 -77.00 -30.00   54
 61  \w     40.00  96.00   0.50   13.76    --  111.50 -77.00-120.00  112
 62  \w     50.00  85.00   0.50   13.76    --  111.50 -77.00 150.00   70
 63  \w     40.00  67.00   0.50   13.76    --  111.50 -61.00 150.00   54
 64  \w     40.00  67.00   0.50   13.76    --  111.50 -77.00  30.00   54
 65  \w    102.00 151.00   0.50   13.76    --  111.50  45.00  60.00   98
 66  \w     40.00  66.00   0.50   13.76    --  111.50-125.00-180.00   52
 67  \w     83.00 109.00   0.50   13.76    --  111.50-125.00-180.00   52
 68  \w     99.00 154.00   0.50   13.76    --  111.50  55.00-173.80  110
 69  \w     40.00  87.00   0.50   13.76    --  111.50 -95.00 -60.00   94
 70  \w     40.00  65.00   0.50   13.76    --  111.50 -61.00  30.00   50
 71  \w     49.00 109.00   0.50   13.76    --  111.50-125.00   0.00  120
 72  \w    107.00 165.00   0.50   13.76    --  111.50  78.00  83.36  116
 73  \w    106.00 177.00   0.50   13.76    --  111.50  77.00  60.00  142
 74  \w     98.00 169.00   0.50   13.76    --  111.50  61.00 120.00  142
 75  \w    103.00 147.00   0.50   13.76    --  111.50  61.00 -30.00   88
 76  \w     40.00  66.00   0.50   13.76    --  111.50 -61.00-180.00   52
;
_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      -0.1142789000
_diffrn_orient_matrix_UB_12      0.0234020000
_diffrn_orient_matrix_UB_13      0.0511126000
_diffrn_orient_matrix_UB_21      0.0650633000
_diffrn_orient_matrix_UB_22      0.0220613000
_diffrn_orient_matrix_UB_23      0.1080167000
_diffrn_orient_matrix_UB_31      0.0086413000
_diffrn_orient_matrix_UB_32      0.1446800000
_diffrn_orient_matrix_UB_33      -0.0245741000
_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  0.0390
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            28058
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.071
_diffrn_reflns_theta_min         3.501
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.733
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.93a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       needle
_exptl_crystal_F_000             660
_exptl_crystal_preparation       'see experimental'
_exptl_crystal_recrystallization_method 'slow evaporation from butanone'
_exptl_crystal_size_max          0.434
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 2092 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         5534
_refine_ls_number_restraints     127
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0754P)^2^+0.2836P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1215
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.901
_reflns_Friedel_fraction_max     0.892
_reflns_number_gt                5140
_reflns_number_total             5534
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00342c2.cif
_cod_data_source_block           1-Butanone
_cod_depositor_comments
'Adding full bibliography for 7160437--7160444.cif.'
_cod_database_code               7160442
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C36 H34 N8 O3'
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.743
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O101-C102 \\sim O102-C106
 with sigma of 0.02
 C101-C102 \\sim C105-C106
 with sigma of 0.02
 C102-C103 \\sim C106-C107
 with sigma of 0.02
 C103-C104 \\sim C107-C108
 with sigma of 0.02
 O101-C101 \\sim O102-C105
 with sigma of 0.04
 O101-C103 \\sim O102-C107
 with sigma of 0.04
 C101-C103 \\sim C105-C107
 with sigma of 0.04
 C102-C104 \\sim C106-C108
 with sigma of 0.04
 N8-C26 \\sim N8-C26A
 with sigma of 0.005
 C26-C27 \\sim C26A-C27A
 with sigma of 0.02
 C26-C31 \\sim C26A-C31A
 with sigma of 0.02
 C27-C28 \\sim C27A-C28A
 with sigma of 0.02
 C28-C29 \\sim C28A-C29A
 with sigma of 0.02
 C29-C30 \\sim C29A-C30A
 with sigma of 0.02
 C30-C31 \\sim C30A-C31A
 with sigma of 0.02
 N8-C27 \\sim N8-C27A
 with sigma of 0.04
 N8-C31 \\sim N8-C31A
 with sigma of 0.04
 N9-C28 \\sim N9A-C28A
 with sigma of 0.04
 C26-C28 \\sim C26A-C28A
 with sigma of 0.04
 C26-C30 \\sim C26A-C30A
 with sigma of 0.04
 C27-C29 \\sim C27A-C29A
 with sigma of 0.04
 C27-C31 \\sim C27A-C31A
 with sigma of 0.04
 C28-C30 \\sim C28A-C30A
 with sigma of 0.04
 C29-C31 \\sim C29A-C31A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C26A \\sim C27A \\sim C28A \\sim C29A \\sim C30A \\sim C31A \\sim N9A: within
1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31: within 1.7A with sigma
of 0.005 and sigma for terminal atoms of 0.02 within 1.7A
C105 \\sim C106 \\sim C107 \\sim C108 \\sim O102: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 1.7A
4. Others
 Sof(C105)=Sof(H10I)=Sof(H10J)=Sof(H10K)=Sof(C106)=Sof(C107)=Sof(H10L)=
 Sof(H10M)=Sof(C108)=Sof(H10N)=Sof(H10O)=Sof(H10P)=Sof(O102)=1-FVAR(1)
 Sof(C101)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(C102)=Sof(C103)=Sof(H10D)=
 Sof(H10E)=Sof(C104)=Sof(H10F)=Sof(H10G)=Sof(H10H)=Sof(O101)=FVAR(1)
 Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(H30A)=Sof(C31A)=Sof(H31A)=Sof(C26A)=
 Sof(C27A)=Sof(C28A)=Sof(H28A)=Sof(N9A)=Sof(H9AA)=Sof(H9AB)=1-FVAR(2)
 Sof(C26)=Sof(C27)=Sof(C28)=Sof(H28)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30)=
 Sof(C31)=Sof(H31)=Sof(N9)=Sof(H9A)=Sof(H9B)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C103(H10D,H10E), C107(H10L,H10M)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28),
  C29(H29), C30(H30), C31(H31), C29A(H29A), C30A(H30A), C31A(H31A), C28A(H28A)
5.c Fitted hexagon refined as free rotating group:
 C29A(C30A,C31A,C26A,C27A,C28A)
5.d X=CH2 refined with riding coordinates:
 N9A(H9AA,H9AB)
5.e Idealised Me refined as rotating group:
 C101(H10A,H10B,H10C), C104(H10F,H10G,H10H), C105(H10I,H10J,H10K), C108(H10N,
 H10O,H10P)
;
_shelx_res_checksum              62512
_olex2_exptl_crystal_mounting_method 'using Fomblin'
_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 2.866
_oxdiff_exptl_absorpt_empirical_full_min 0.560