Chalcogen bonding mediates the formation of supramolecular helices of azapeptides in crystals.
Shi, Di; Cao, Jinlian; Weng, Peimin; Yan, Xiaosheng; Li, Zhao; Jiang, Yun-Bao; Organic & biomolecular chemistry 19 (2021) 6397–6401; doi:10.1039/d1ob01053k

data_7158162
_publ_section_title
;
 Chalcogen bonding mediates the formation of supramolecular helices of
 azapeptides in crystals.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6397
_journal_page_last               6401
_journal_paper_doi               10.1039/d1ob01053k
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H16 N4 O2 S2, C2 H3 N'
_chemical_formula_sum            'C17 H19 N5 O2 S2'
_chemical_formula_weight         389.49
_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   geom
_audit_creation_date             2021-05-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2021-05-17 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.034(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0334(2)
_cell_length_b                   8.7125(2)
_cell_length_c                   12.1508(3)
_cell_measurement_reflns_used    3433
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      30.1320
_cell_measurement_theta_min      4.1760
_cell_volume                     953.94(4)
_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_temperature      100.01(10)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5890
_diffrn_reflns_point_group_measured_fraction_full 0.887
_diffrn_reflns_point_group_measured_fraction_max 0.707
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.716
_diffrn_reflns_theta_min         3.588
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1298 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4193
_refine_ls_number_restraints     63
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0571P)^2^+0.1849P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.550
_reflns_Friedel_fraction_full    0.762
_reflns_Friedel_fraction_max     0.533
_reflns_number_gt                3862
_reflns_number_total             4193
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01053k2.cif
_cod_data_source_block           exp_12393
_cod_depositor_comments
'Adding full bibliography for 7158162--7158163.cif.'
_cod_database_code               7158162
_shelx_shelxl_version_number     2014/8
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained planarity
 C00K, C00B, C00N, C00A, S002
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
Uanis(S002) \\sim Ueq, Uanis(C00A) \\sim Ueq, Uanis(C00N) \\sim Ueq,
Uanis(C00K) \\sim Ueq, Uanis(C00B) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
4. Rigid body (RIGU) restrains
 C00A, C00N, S002, C00K, C00B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5.a Ternary CH refined with riding coordinates:
 C00H(H00H)
5.b Aromatic/amide H refined with riding coordinates:
 N005(H005), N006(H006), N007(H007), N008(H008), C00A(H00A), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00P(H00P)
5.c Idealised Me refined as rotating group:
 C00O(H00E,H00F,H00G), C00Q(H00B,H00C,H00D)
;
_shelx_res_checksum              96391
_olex2_submission_special_instructions 'No special instructions were received'