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_7160438
_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             2021-02-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-02-24 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.318(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5123(5)
_cell_length_b                   10.4201(5)
_cell_length_c                   12.7453(5)
_cell_measurement_reflns_used    13854
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.6090
_cell_measurement_theta_min      5.0240
_cell_volume                     1527.67(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -110.00 -16.00   1.00    1.00    --  -42.02 -57.00-120.00   94
  2  \w    -80.00  14.00   1.00    1.00    --  -42.02  19.00  60.00   94
  3  \w      0.00  27.00   1.00    1.00    --   42.02 -77.00 -90.00   27
  4  \w     40.00  66.00   1.00    1.00    --   42.02 -77.00 -90.00   26
  5  \w     94.00 174.00   1.00    3.51    --  104.05  30.00 -90.00   80
  6  \w     46.00 112.00   1.00    1.00    --  104.05-125.00   0.00   66
  7  \w     34.00 132.00   1.00    1.00    --  104.05 -30.00  90.00   98
  8  \w    150.00 177.00   1.00    1.00    --  104.05  77.00   0.00   27
  9  \w    153.00 178.00   1.00    1.00    --  104.05  77.00-120.00   25
 10  \w     42.00 133.00   1.00    1.00    --  104.05 -77.00 -30.00   91
 11  \w    -94.00 -56.00   1.00    1.00    --  -42.28 -57.00  60.00   38
 12  \w    -90.00 -14.00   1.00    1.00    --  -42.28 -57.00 -30.00   76
 13  \w    -75.00 -49.00   1.00    1.00    --  -42.28 125.00  30.00   26
 14  \w    -49.00 -19.00   1.00    1.00    --  -42.28 -27.00 -39.64   30
 15  \w    -44.00 -12.00   1.00    1.00    --  -42.28 125.00  30.00   32
 16  \w    -20.00   5.00   1.00    1.00    --   42.43 -77.00-180.00   25
 17  \w     10.00  41.00   1.00    1.00    --   42.43  79.00  42.52   31
 18  \w      9.00  35.00   1.00    1.00    --   42.43  81.00 -45.26   26
 19  \w     20.00  54.00   1.00    1.00    --   42.43  57.00  60.00   34
 20  \w      8.00  33.00   1.00    1.00    --   42.43  83.00  -4.21   25
 21  \w   -115.00 -14.00   1.00    1.00    --  -42.28 -57.00 120.00  101
 22  \w   -116.00 -59.00   1.00    1.00    --  -42.28-152.00  80.00   57
 23  \w    -67.00  32.00   1.00    1.00    --  -42.28  38.00 -60.00   99
 24  \w     27.00  98.00   1.00    1.00    --   42.43-125.00-180.00   71
 25  \w      8.00  34.00   1.00    1.00    --   42.43  83.00 -60.06   26
 26  \w      8.00  34.00   1.00    1.00    --   42.43  83.00  -4.21   26
 27  \w      9.00  42.00   1.00    1.00    --   42.43  82.00-116.43   33
 28  \w     18.00 117.00   1.00    1.00    --   42.43  38.00 -30.00   99
 29  \w      9.00  42.00   1.00    1.00    --   42.43  82.00  87.75   33
 30  \w    -32.00  67.00   1.00    1.00    --   42.43 -38.00 -30.00   99
 31  \w      9.00  42.00   1.00    1.00    --   42.43  80.00-163.05   33
 32  \w      9.00  42.00   1.00    1.00    --   42.43  80.00 138.18   33
 33  \w      7.00  32.00   1.00    1.08    --   42.00  84.00  56.18   25
 34  \w     87.00 113.00   1.00    1.08    --   42.43  38.00 -90.00   26
 35  \w     80.00 106.00   1.00    1.08    --   42.43  57.00 150.00   26
 36  \w     37.00  70.00   1.00    1.08    --   42.43  38.00 -90.00   33
 37  \w      7.00  33.00   1.00    1.08    --   42.00  84.00  56.18   26
 38  \w    -67.00  32.00   1.00    1.08    --  -42.28  38.00-150.00   99
 39  \w   -115.00 -14.00   1.00    1.08    --  -42.28 -57.00   0.00  101
 40  \w   -117.00 -18.00   1.00    1.08    --  -42.28 -38.00  30.00   99
 41  \w    -83.00  38.00   1.00    1.08    --  -42.28  19.00 -60.00  121
 42  \w   -115.00 -14.00   1.00    1.08    --  -42.28 -57.00 150.00  101
 43  \w     14.00 116.00   1.00    1.08    --   42.43  57.00 -90.00  102
 44  \w     27.00  98.00   1.00    1.08    --   42.43-125.00-150.00   71
 45  \w     18.00 117.00   1.00    1.08    --   42.43  38.00 -90.00   99
 46  \w    -21.00  75.00   1.00    1.08    --   42.43 -77.00  60.00   96
 47  \w     27.00  98.00   1.00    1.08    --   42.43-125.00  90.00   71
 48  \w      1.00 122.00   1.00    1.08    --   42.43  19.00-180.00  121
 49  \w     27.00  98.00   1.00    1.08    --   42.43-125.00 -60.00   71
 50  \w     14.00  56.00   1.00    1.08    --   42.43  57.00 -30.00   42
 51  \w    -38.00  83.00   1.00    1.08    --   42.43 -19.00 -60.00  121
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1290407000
_diffrn_orient_matrix_UB_12      -0.0125197000
_diffrn_orient_matrix_UB_13      0.0258208000
_diffrn_orient_matrix_UB_21      -0.0348289000
_diffrn_orient_matrix_UB_22      0.0130393000
_diffrn_orient_matrix_UB_23      -0.1175598000
_diffrn_orient_matrix_UB_31      0.0078633000
_diffrn_orient_matrix_UB_32      -0.1467140000
_diffrn_orient_matrix_UB_33      -0.0126661000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24759
_diffrn_reflns_point_group_measured_fraction_full 0.774
_diffrn_reflns_point_group_measured_fraction_max 0.772
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.228
_diffrn_reflns_theta_min         3.843
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.805
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.74a (Rigaku Oxford Diffraction, 2020)
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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.083
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1251 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         4334
_refine_ls_number_restraints     137
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0667P)^2^+0.5793P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1161
_reflns_Friedel_coverage         0.459
_reflns_Friedel_fraction_full    0.521
_reflns_Friedel_fraction_max     0.517
_reflns_number_gt                3961
_reflns_number_total             4334
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00342c2.cif
_cod_data_source_block           SP031
_cod_depositor_comments
'Adding full bibliography for 7160437--7160444.cif.'
_cod_database_code               7160438
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C31 H25 N9 O2'
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     42.65
_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
2. Restrained distances
 C101-C102 \\sim C14A-C13A
 with sigma of 0.02
 C101-O101 \\sim C14A-O11A
 with sigma of 0.02
 C102-C103 \\sim C13A-C12A
 with sigma of 0.02
 C103-C104 \\sim C12A-C11A
 with sigma of 0.02
 C104-O101 \\sim C11A-O11A
 with sigma of 0.02
 C101-C103 \\sim C14A-C12A
 with sigma of 0.04
 C101-C104 \\sim C14A-C11A
 with sigma of 0.04
 C102-C104 \\sim C13A-C11A
 with sigma of 0.04
 C102-O101 \\sim C13A-O11A
 with sigma of 0.04
 C103-O101 \\sim C12A-O11A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O101 \\sim C101 \\sim C102 \\sim C103 \\sim C104 \\sim O11A \\sim C11A \\sim
C12A \\sim C13A \\sim C14A: within 1.7A with sigma of 0.03 and sigma for
terminal atoms of 0.06
4. Others
 Sof(C11A)=Sof(H11A)=Sof(H11B)=Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(C13A)=
 Sof(H13A)=Sof(H13B)=Sof(C14A)=Sof(H14A)=Sof(H14B)=Sof(O11A)=1-FVAR(1)
 Sof(C101)=Sof(H10A)=Sof(H10B)=Sof(C102)=Sof(H10C)=Sof(H10D)=Sof(C103)=
 Sof(H10E)=Sof(H10F)=Sof(C104)=Sof(H10G)=Sof(H10H)=Sof(O101)=FVAR(1)
5.a Rotating group:
 N1(H1A,H1B)
5.b Secondary CH2 refined with riding coordinates:
 C101(H10A,H10B), C102(H10C,H10D), C103(H10E,H10F), C104(H10G,H10H), C11A(H11A,
 H11B), C12A(H12A,H12B), C13A(H13A,H13B), C14A(H14A,H14B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C17(H17), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28),
  C29(H29), C30(H30), C31(H31)
5.d X=CH2 refined with riding coordinates:
 N9(H9A,H9B)
;
_shelx_res_checksum              55993
_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 1.230
_oxdiff_exptl_absorpt_empirical_full_min 0.820