Design and synthesis of macrocycles with tuneable diameters and helical foldamers with customizable peripheral side chains.
Farooq, Saquib; Crochet, Aurelien; Kilbinger, Andreas F. M.; Chemical science 16 (2025) 20570–20579; doi:10.1039/d5sc04138d

data_1575961
_publ_section_title
;
 Design and synthesis of macrocycles with tuneable diameters and helical
 foldamers with customizable peripheral side chains.
;
_journal_issue                   43
_journal_name_full               'Chemical science'
_journal_page_first              20570
_journal_page_last               20579
_journal_paper_doi               10.1039/d5sc04138d
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C23 H30 N2 O7'
_chemical_formula_sum            'C23 H30 N2 O7'
_chemical_formula_weight         446.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-21
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-02-17 deposited with the CCDC.	2025-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.483(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.3295(16)
_cell_length_b                   8.6597(4)
_cell_length_c                   16.7533(8)
_cell_measurement_reflns_used    13188
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      27.25
_cell_measurement_theta_min      1.25
_cell_volume                     4561.0(4)
_computing_cell_refinement       'X-Area Recipe 1.37.0.0 (STOE, 2021)'
_computing_data_collection       'X-Area WinXpose 2.0.25.0 (STOE, 2022)'
_computing_data_reduction
;
X-Area Integrate 2.5.3.0 (STOE, 2021)
X-Area LANA 2.7.5.0 (STOE, 2022)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      250(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
 173 frames, detector distance = 120 mm
;
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            32731
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.817
_diffrn_reflns_theta_min         1.295
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.9734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1904
_exptl_crystal_recrystallization_method
'crystallized by slow evaporation of DCM and methanol'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0509
_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^)+(0.0717P)^2^+2.6637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1515
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3230
_reflns_number_total             4858
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc04138d2.cif
_cod_data_source_block           sl-751
_cod_depositor_comments
'Adding full bibliography for 1575958--1575961.cif.'
_cod_database_code               1575961
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.974
_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, All O(H) groups
2.a Rotating group:
 N1(H1A,H1B)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C11(H11), C13(H13)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C23(H23A,H23B,
 H23C)
2.e Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_shelx_res_checksum              97012
_olex2_exptl_crystal_mounting_method 'mounted on loop with oil'
_olex2_submission_special_instructions 'No special instructions were received'
_stoe_detector_distance          '120.0 mm'
_stoe_detector_pixelsize_x       '0.150 mm'
_stoe_detector_pixelsize_y       '0.150 mm'
_stoe_detector_size_x            '34.0 cm'
_stoe_detector_size_y            '34.0 cm'
_stoe_evaluation_integration_a   9.0
_stoe_evaluation_integration_b   0.0
_stoe_evaluation_integration_ems 0.006
_stoe_evaluation_lana_bis_l_even_max -
_stoe_evaluation_lana_bis_l_odd_max -
_stoe_evaluation_lana_bos_l_even_max -
_stoe_evaluation_lana_bos_l_odd_max -
_stoe_evaluation_lana_completeness 99.2
_stoe_evaluation_lana_dxs_max_order -
_stoe_evaluation_lana_dys_max_order -
_stoe_evaluation_lana_fs_max_order 3
_stoe_evaluation_lana_max_2theta_available 53.7
_stoe_evaluation_lana_max_2theta_desired 53.7
_stoe_evaluation_lana_mean_redundancy 5.6
_stoe_evaluation_lana_number_refls_after_or 27046
_stoe_evaluation_lana_number_refls_outliers 5685
_stoe_evaluation_lana_number_refls_total 32731
_stoe_evaluation_lana_number_refls_unique 4858
_stoe_evaluation_lana_number_refls_written 32731
_stoe_evaluation_lana_or_c1      0.035
_stoe_evaluation_lana_or_c2      0
_stoe_evaluation_lana_or_c3      0
_stoe_evaluation_lana_or_c4      0.7
_stoe_evaluation_lana_point_group 2/m
_stoe_evaluation_lana_table
;
2Theta           4.9   10.7   16.5   22.3   28.1   33.9   39.7   45.5   51.3
<Resolution>    6.80   3.67   2.45   1.82   1.45   1.21   1.04   0.92   0.83
N(total)          91    459   1123   2136   3228   4573   6014   7331   7776
<Redundancy>     4.4    5.8    5.6    5.5    5.4    5.4    5.5    5.7    5.7
Complet. [%%]   100.0  100.0  100.0  100.0  100.0  100.0  100.0  100.0   97.0
<I/sigma>      355.0  297.9  112.9   66.4   23.5   15.9    8.2    2.8    0.9
R(int)         0.019  0.013  0.013  0.015  0.025  0.034  0.062  0.167  0.393
;
_stoe_measurement_identifier     SL-751
_stoe_measurement_max_exposure_per_frame '900.0 s'
_stoe_measurement_mean_exposure_per_frame '900.0 s'
_stoe_measurement_min_exposure_per_frame '900.0 s'
_stoe_measurement_total_exposure_time '43.3 h'
_stoe_measurement_total_frame_number 173
_stoe_measurement_total_run_number 2
_stoe_measurement_tube_power     '2.0 kW'