Reverse Turn and Loop Secondary Structures in Stereodefined Cyclic Peptoid Scaffolds.
D'Amato, Assunta; Pierri, Giovanni; Tedesco, Consiglia; Della Sala, Giorgio; Izzo, Irene; Costabile, Chiara; De Riccardis, Francesco; The Journal of organic chemistry 84 (2019) 10911–10928; doi:10.1021/acs.joc.9b01509

data_4033869
_publ_section_title
;
 Reverse Turn and Loop Secondary Structures in Stereodefined Cyclic
 Peptoid Scaffolds.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10911
_journal_page_last               10928
_journal_paper_doi               10.1021/acs.joc.9b01509
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C30 H31 N3 O3'
_chemical_formula_sum            'C30 H31 N3 O3'
_chemical_formula_weight         481.58
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-02-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8492(7)
_cell_length_b                   23.7824(12)
_cell_length_c                   8.4063(4)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      70.64
_cell_measurement_theta_min      3.91
_cell_volume                     2568.8(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      299.15
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            34823
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.529
_diffrn_reflns_theta_min         3.910
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1126 before and 0.0719 after correction.
The Ratio of minimum to maximum transmission is 0.8808.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1710 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.25(8)
_refine_ls_extinction_coef       0.0029(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0766P)^2^+0.4488P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1439
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                4422
_reflns_number_total             4896
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01509_si_002.cif
_cod_data_source_block           tbe226_1
_cod_database_code               4033869
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C11(H11), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C12(H12A,H12B,H12C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              9708
_shelx_hkl_checksum              72560
_olex2_submission_special_instructions 'No special instructions were received'