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_7160443
_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 ad
_chemical_formula_moiety         'C31 H25 N9 O2, C2 H6 O S'
_chemical_formula_sum            'C33 H31 N9 O3 S'
_chemical_formula_weight         633.73
_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             2025-02-06
_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                 90.842(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5089(5)
_cell_length_b                   10.4369(4)
_cell_length_c                   12.6459(5)
_cell_measurement_reflns_used    10525
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3140
_cell_measurement_theta_min      3.7870
_cell_volume                     1518.83(11)
_computing_cell_refinement       'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.128a 64-bit (release 20-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.128a (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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_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    -72.00 -10.00   1.00    4.72    --  -39.96 117.00 -49.00   62
  2  \w    -36.00 -10.00   1.00    4.72    --   39.96 -19.00  58.00   26
  3  \w    104.00 169.00   1.00   18.89    --  113.00 110.00  45.00   65
  4  \w     70.00 177.00   1.00   18.89    --  113.00  19.00-134.00  107
  5  \w     42.00 108.00   1.00   18.89    --  113.00-117.00-137.00   66
  6  \w   -104.00 -16.00   1.00    4.72    --  -39.96 -38.00-150.00   88
  7  \w     59.00  85.00   1.00    4.72    --   39.96 -19.00  58.00   26
  8  \w     66.00  95.00   1.00   18.89    --  113.00 178.00  60.00   29
  9  \w    117.00 146.00   1.00   18.89    --  113.00 178.00  60.00   29
 10  \w     39.00  93.00   1.00   18.89    --  113.00-111.00 150.00   54
 11  \w     27.00  52.00   1.00    4.72    --   40.58-110.00 -49.00   25
 12  \w    -17.00  15.00   1.00    4.72    --  -40.58  38.00  60.00   32
 13  \w    -62.00 -34.00   1.00    4.72    --  -40.58  38.00  60.00   28
 14  \w    -53.00 -11.00   1.00    4.72    --  -40.58 125.00-120.00   42
 15  \w   -103.00 -15.00   1.00    4.72    --  -40.58 -38.00  90.00   88
 16  \w     29.00  95.00   1.00    4.72    --   40.58-125.00-120.00   66
 17  \w    119.00 145.00   1.00   18.89    --  113.00  77.00 -60.00   26
 18  \w     37.00  65.00   1.00   18.89    --  113.00 -30.00 120.00   28
 19  \w     81.00 107.00   1.00   18.89    --  113.00-111.00 120.00   26
 20  \w     81.00 109.00   1.00   18.89    --  113.00-111.00  30.00   28
 21  \w     77.00 103.00   1.00   18.89    --  113.00-111.00  90.00   26
 22  \w     39.00  78.00   1.00   18.89    --  113.00-111.00 120.00   39
 23  \w     72.00  98.00   1.00   18.89    --  113.00 -30.00 120.00   26
 24  \w    108.00 141.00   1.00   18.89    --  113.00 -30.00 120.00   33
 25  \w     83.00 109.00   1.00   18.89    --  113.00-111.00-180.00   26
 26  \w     44.00  77.00   1.00   18.89    --  113.00-111.00-180.00   33
 27  \w    133.00 159.00   1.00   18.89    --  113.00  45.00-120.00   26
 28  \w    105.00 158.00   1.00   18.89    --  113.00  77.00  90.00   53
 29  \w     62.00 141.00   1.00   18.89    --  113.00 -30.00 -90.00   79
 30  \w     38.00  93.00   1.00   18.89    --  113.00-111.00 -90.00   55
 31  \w     51.00  77.00   1.00   18.89    --  113.00 -61.00-180.00   26
 32  \w     99.00 142.00   1.00   18.89    --  113.00 -61.00-180.00   43
 33  \w     78.00 109.00   1.00   18.89    --  113.00-111.00 -60.00   31
 34  \w     39.00 141.00   1.00   18.89    --  113.00 -61.00 -60.00  102
 35  \w     86.00 172.00   1.00   18.89    --  113.00  30.00  30.00   86
 36  \w     27.00  52.00   1.00    4.72    --   40.58-110.00 -49.00   25
 37  \w   -122.00   6.00   1.00    4.72    --  -40.58 -19.00 -60.00  128
 38  \w    -87.00  -6.00   1.00    4.72    --  -40.58 125.00  60.00   81
 39  \w   -115.00 -42.00   1.00    4.72    --  -40.58 -57.00-180.00   73
 40  \w   -115.00 -11.00   1.00    4.72    --  -40.58 -57.00  60.00  104
 41  \w      4.00  31.00   1.00    4.72    --   40.58  87.00 -58.22   27
 42  \w      3.00  30.00   1.00    4.72    --   40.58  89.00 114.87   27
 43  \w      3.00  30.00   1.00    4.72    --   40.58  88.00-130.77   27
 44  \w      2.00  29.00   1.00    4.72    --   40.58  90.00  75.23   27
 45  \w      3.00  30.00   1.00    4.72    --   40.58  88.00  11.02   27
 46  \w     27.00  52.00   1.00    4.72    --   40.58-110.00 -49.00   25
 47  \w    -87.00  -6.00   1.00    4.72    --  -40.58 125.00 150.00   81
 48  \w     11.00 115.00   1.00    4.72    --   40.58  57.00 -90.00  104
 49  \w     -6.00 118.00   1.00    4.72    --   40.58  19.00   0.00  124
 50  \w     11.00 115.00   1.00    4.72    --   40.58  57.00  90.00  104
 51  \w    -33.00  70.00   1.00    4.72    --   40.58 -57.00 150.00  103
 52  \w     11.00 115.00   1.00    4.72    --   40.58  57.00 120.00  104
 53  \w     11.00 115.00   1.00    4.72    --   40.58  57.00-150.00  104
 54  \w     11.00 115.00   1.00    4.72    --   40.58  57.00   0.00  104
;
_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      -0.1308762000
_diffrn_orient_matrix_UB_12      0.0102972000
_diffrn_orient_matrix_UB_13      -0.0258984000
_diffrn_orient_matrix_UB_21      0.0049161000
_diffrn_orient_matrix_UB_22      0.1455800000
_diffrn_orient_matrix_UB_23      0.0196972000
_diffrn_orient_matrix_UB_31      0.0277308000
_diffrn_orient_matrix_UB_32      0.0221624000
_diffrn_orient_matrix_UB_33      -0.1174029000
_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  0.0442
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23584
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.644
_diffrn_reflns_theta_min         3.495
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.373
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.128a (Rigaku Oxford Diffraction, 2024)
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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 1871 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     532
_refine_ls_number_reflns         6284
_refine_ls_number_restraints     363
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0788
_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^)+(0.1450P)^2^+0.5344P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2116
_refine_ls_wR_factor_ref         0.2337
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                5052
_reflns_number_total             6284
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00342c2.cif
_cod_data_source_block           1-DMSO
_cod_depositor_comments
'Adding full bibliography for 7160437--7160444.cif.'
_cod_database_code               7160443
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C35 H44 N9 O3 S1'
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.734
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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
 N5-H5A = N5-H5B
 0.88 with sigma of 0.02
 O101-S101
 1.69 with sigma of 0.005
 O11A-S11A
 1.69 with sigma of 0.008
 S101-C101 = S101-C102 = S11A-C11A = S11A-C12A
 1.89 with sigma of 0.02
 N6-H6
 0.87 with sigma of 0.02
 O101-C101 = O101-C102 = O11A-C11A = O11A-C12A
 2.79 with sigma of 0.04
 N4-C13 \\sim N8-C26
 with sigma of 0.01
 N4-C13 \\sim N8-C26A
 with sigma of 0.01
 C28-C27 \\sim C28A-C27A
 with sigma of 0.02
 C28-C29 \\sim C28A-C29A
 with sigma of 0.02
 N9-C27 \\sim N9A-C27A
 with sigma of 0.02
 C26-C31 \\sim C26A-C31A
 with sigma of 0.02
 C26-C27 \\sim C26A-C27A
 with sigma of 0.02
 C31-C30 \\sim C31A-C30A
 with sigma of 0.02
 C30-C29 \\sim C30A-C29A
 with sigma of 0.02
 N8-C31 \\sim N8-C31A
 with sigma of 0.04
 N8-C27 \\sim N8-C27A
 with sigma of 0.04
 C28-N9 \\sim C28A-N9A
 with sigma of 0.04
 C28-C26 \\sim C28A-C26A
 with sigma of 0.04
 C28-C30 \\sim C28A-C30A
 with sigma of 0.04
 N9-C26 \\sim N9A-C26A
 with sigma of 0.04
 C26-C30 \\sim C26A-C30A
 with sigma of 0.04
 C31-C27 \\sim C31A-C27A
 with sigma of 0.04
 C31-C29 \\sim C31A-C29A
 with sigma of 0.04
 C27-C29 \\sim C27A-C29A
 with sigma of 0.04
 S101-C102 \\sim S101-C101
 with sigma of 0.02
 C102-O101 \\sim C101-O101
 with sigma of 0.04
 S11A-C11A \\sim S11A-C12A
 with sigma of 0.02
 C11A-O11A \\sim C12A-O11A
 with sigma of 0.04
 C5-C19 \\sim C6-C1
 with sigma of 0.02
3. Rigid bond restraints
 C26, C26, C26, C27, C31, N8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C26A, C26A, C26A, C27A, C31A, N8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C26A \\sim C27A
\\sim C28A \\sim C29A \\sim C30A \\sim C31A \\sim N9 \\sim N9A: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C101 \\sim C102 \\sim C11A \\sim C12A \\sim O101 \\sim O11A \\sim S101 \\sim
S11A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
2A
5. Rigid body (RIGU) restrains
 C101, C102, O101, S101
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C11A, C12A, O11A, S11A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C26A)=Sof(C27A)=Sof(C28A)=Sof(H28A)=Sof(C29A)=Sof(H29A)=Sof(C30A)=
 Sof(H30A)=Sof(C31A)=Sof(H31A)=Sof(N9A)=Sof(H9AA)=Sof(H9AB)=1-FVAR(1)
 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(1)
 Sof(C11A)=Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(C12A)=Sof(H12A)=Sof(H12B)=
 Sof(H12C)=Sof(O11A)=Sof(S11A)=1-FVAR(2)
 Sof(C101)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(C102)=Sof(H10D)=Sof(H10E)=
 Sof(H10F)=Sof(O101)=Sof(S101)=FVAR(2)
7.a 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), C28A(H28A), C29A(H29A), C30A(H30A), C31A(H31A)
7.b X=CH2 refined with riding coordinates:
 N9(H9A,H9B), N9A(H9AA,H9AB)
7.c Idealised Me refined as rotating group:
 C101(H10A,H10B,H10C), C102(H10D,H10E,H10F), C11A(H11A,H11B,H11C), C12A(H12A,
 H12B,H12C)
;
_shelx_res_checksum              90799
_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 1.424
_oxdiff_exptl_absorpt_empirical_full_min 0.683