#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:22:24 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268910 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158162.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7158162
loop_
_publ_author_name
'Shi, Di'
'Cao, Jinlian'
'Weng, Peimin'
'Yan, Xiaosheng'
'Li, Zhao'
'Jiang, Yun-Bao'
_publ_section_title
;
 Chalcogen bonding mediates the formation of supramolecular helices of
 azapeptides in crystals.
;
_journal_issue                   29
_journal_name_full               'Organic & 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/[σ²(Fo²)+(0.0571P)²+0.1849P] where P=(Fo²+2Fc²)/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 > 2σ(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
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.33730(9) 0.47846(9) 0.76206(6) 0.02255(19) Uani 1 1 d . . . . .
S002 S -0.12657(9) 0.23213(11) 0.65739(7) 0.0294(2) Uani 1 1 d . U . . .
O003 O 0.3139(2) 0.1936(2) 0.33312(18) 0.0192(5) Uani 1 1 d . . . . .
O004 O 0.4384(2) 0.5664(3) 0.40856(19) 0.0217(5) Uani 1 1 d . . . . .
N005 N 0.2800(3) 0.3113(3) 0.5759(2) 0.0176(5) Uani 1 1 d . . . . .
H005 H 0.3150 0.2789 0.5161 0.021 Uiso 1 1 calc R . . . .
N006 N 0.5093(3) 0.4232(3) 0.6042(2) 0.0188(5) Uani 1 1 d . . . . .
H006 H 0.5738 0.4742 0.6448 0.023 Uiso 1 1 calc R . . . .
N007 N 0.5477(3) 0.3687(3) 0.5037(2) 0.0180(5) Uani 1 1 d . . . . .
H007 H 0.5977 0.2850 0.5005 0.022 Uiso 1 1 calc R . . . .
N008 N 0.4333(3) 0.3536(3) 0.2249(2) 0.0190(5) Uani 1 1 d . . . . .
H008 H 0.4318 0.4051 0.1645 0.023 Uiso 1 1 calc R . . . .
N009 N 0.4174(3) 0.6049(4) 0.0547(3) 0.0288(6) Uani 1 1 d . . . . .
C00A C -0.0859(3) 0.1153(4) 0.5470(2) 0.0190(6) Uani 1 1 d . U . . .
H00A H -0.1482 0.0433 0.5112 0.023 Uiso 1 1 calc R . . . .
C00B C 0.1327(3) 0.2656(4) 0.5927(3) 0.0185(6) Uani 1 1 d . U . . .
C00C C 0.3751(3) 0.7270(4) 0.0664(3) 0.0224(6) Uani 1 1 d . . . . .
C00D C 0.3207(3) 0.2602(3) 0.2433(2) 0.0164(6) Uani 1 1 d . . . . .
C00E C 0.5069(3) 0.4466(3) 0.4098(3) 0.0169(6) Uani 1 1 d . . . . .
C00F C 0.3723(3) 0.3988(4) 0.6411(3) 0.0178(6) Uani 1 1 d . . . . .
C00G C 0.2063(3) 0.2352(4) 0.1499(2) 0.0178(6) Uani 1 1 d . . . . .
C00H C 0.5580(3) 0.3693(4) 0.3058(3) 0.0192(6) Uani 1 1 d . . . . .
H00H H 0.5966 0.2670 0.3253 0.023 Uiso 1 1 calc R . . . .
C00I C 0.0010(4) 0.1513(4) -0.0210(3) 0.0233(7) Uani 1 1 d . . . . .
H00I H -0.0666 0.1208 -0.0781 0.028 Uiso 1 1 calc R . . . .
C00J C 0.1359(3) 0.2137(4) -0.0446(3) 0.0210(6) Uani 1 1 d . . . . .
H00J H 0.1583 0.2276 -0.1175 0.025 Uiso 1 1 calc R . . . .
C00K C 0.0410(4) 0.3194(4) 0.6686(3) 0.0221(6) Uani 1 1 d . U . . .
H00K H 0.0676 0.3950 0.7202 0.027 Uiso 1 1 calc R . . . .
C00L C 0.2376(3) 0.2555(4) 0.0409(2) 0.0185(6) Uani 1 1 d . . . . .
H00L H 0.3282 0.2977 0.0248 0.022 Uiso 1 1 calc R . . . .
C00M C 0.0695(3) 0.1759(4) 0.1732(3) 0.0220(7) Uani 1 1 d . . . . .
H00M H 0.0464 0.1640 0.2461 0.026 Uiso 1 1 calc R . . . .
C00N C 0.0652(4) 0.1532(4) 0.5223(3) 0.0248(7) Uani 1 1 d . U . . .
H00N H 0.1129 0.1075 0.4654 0.030 Uiso 1 1 calc R . . . .
C00O C 0.3218(4) 0.8832(4) 0.0811(3) 0.0308(8) Uani 1 1 d . . . . .
H00E H 0.3850 0.9540 0.0460 0.046 Uiso 1 1 calc GR . . . .
H00F H 0.3232 0.9063 0.1585 0.046 Uiso 1 1 calc GR . . . .
H00G H 0.2223 0.8922 0.0486 0.046 Uiso 1 1 calc GR . . . .
C00P C -0.0336(4) 0.1341(4) 0.0876(3) 0.0269(7) Uani 1 1 d . . . . .
H00P H -0.1254 0.0947 0.1034 0.032 Uiso 1 1 calc R . . . .
C00Q C 0.6802(4) 0.4630(5) 0.2586(3) 0.0265(7) Uani 1 1 d . . . . .
H00B H 0.7112 0.4137 0.1934 0.040 Uiso 1 1 calc GR . . . .
H00C H 0.7630 0.4707 0.3123 0.040 Uiso 1 1 calc GR . . . .
H00D H 0.6437 0.5639 0.2402 0.040 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00K S002 C00A 95.08(16) . . ?
C00B N005 H005 115.7 . . ?
C00F N005 H005 115.7 . . ?
C00F N005 C00B 128.5(3) . . ?
N007 N006 H006 119.0 . . ?
C00F N006 H006 119.0 . . ?
C00F N006 N007 122.0(3) . . ?
N006 N007 H007 119.9 . . ?
C00E N007 N006 120.2(2) . . ?
C00E N007 H007 119.9 . . ?
C00D N008 H008 119.7 . . ?
C00D N008 C00H 120.6(3) . . ?
C00H N008 H008 119.7 . . ?
S002 C00A H00A 127.0 . . ?
C00N C00A S002 106.1(2) . . ?
C00N C00A H00A 127.0 . . ?
C00K C00B N005 128.4(3) . . ?
C00K C00B C00N 113.0(3) . . ?
C00N C00B N005 118.5(3) . . ?
N009 C00C C00O 179.7(4) . . ?
O003 C00D N008 121.2(3) . . ?
O003 C00D C00G 121.7(3) . . ?
N008 C00D C00G 117.1(3) . . ?
O004 C00E N007 123.3(3) . . ?
O004 C00E C00H 123.5(3) . . ?
N007 C00E C00H 113.2(3) . . ?
N005 C00F S001 127.1(2) . . ?
N005 C00F N006 115.7(3) . . ?
N006 C00F S001 117.1(2) . . ?
C00L C00G C00D 122.0(3) . . ?
C00L C00G C00M 119.2(3) . . ?
C00M C00G C00D 118.5(3) . . ?
N008 C00H C00E 109.6(2) . . ?
N008 C00H H00H 108.9 . . ?
N008 C00H C00Q 110.2(3) . . ?
C00E C00H H00H 108.9 . . ?
C00Q C00H C00E 110.2(3) . . ?
C00Q C00H H00H 108.9 . . ?
C00J C00I H00I 120.0 . . ?
C00J C00I C00P 120.1(3) . . ?
C00P C00I H00I 120.0 . . ?
C00I C00J H00J 120.2 . . ?
C00I C00J C00L 119.7(3) . . ?
C00L C00J H00J 120.2 . . ?
S002 C00K H00K 124.0 . . ?
C00B C00K S002 111.9(3) . . ?
C00B C00K H00K 124.0 . . ?
C00G C00L C00J 120.9(3) . . ?
C00G C00L H00L 119.5 . . ?
C00J C00L H00L 119.5 . . ?
C00G C00M H00M 119.9 . . ?
C00G C00M C00P 120.2(3) . . ?
C00P C00M H00M 119.9 . . ?
C00A C00N H00N 123.1 . . ?
C00B C00N C00A 113.8(3) . . ?
C00B C00N H00N 123.1 . . ?
C00C C00O H00E 109.5 . . ?
C00C C00O H00F 109.5 . . ?
C00C C00O H00G 109.5 . . ?
H00E C00O H00F 109.5 . . ?
H00E C00O H00G 109.5 . . ?
H00F C00O H00G 109.5 . . ?
C00I C00P C00M 119.9(3) . . ?
C00I C00P H00P 120.0 . . ?
C00M C00P H00P 120.0 . . ?
C00H C00Q H00B 109.5 . . ?
C00H C00Q H00C 109.5 . . ?
C00H C00Q H00D 109.5 . . ?
H00B C00Q H00C 109.5 . . ?
H00B C00Q H00D 109.5 . . ?
H00C C00Q H00D 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 C00F 1.675(3) . ?
S002 C00A 1.743(3) . ?
S002 C00K 1.691(3) . ?
O003 C00D 1.241(4) . ?
O004 C00E 1.212(4) . ?
N005 H005 0.8600 . ?
N005 C00B 1.418(4) . ?
N005 C00F 1.346(4) . ?
N006 H006 0.8600 . ?
N006 N007 1.377(4) . ?
N006 C00F 1.363(4) . ?
N007 H007 0.8600 . ?
N007 C00E 1.357(4) . ?
N008 H008 0.8600 . ?
N008 C00D 1.334(4) . ?
N008 C00H 1.448(4) . ?
N009 C00C 1.142(5) . ?
C00A H00A 0.9300 . ?
C00A C00N 1.457(4) . ?
C00B C00K 1.364(4) . ?
C00B C00N 1.410(5) . ?
C00C C00O 1.459(5) . ?
C00D C00G 1.497(4) . ?
C00E C00H 1.531(4) . ?
C00G C00L 1.385(4) . ?
C00G C00M 1.387(4) . ?
C00H H00H 0.9800 . ?
C00H C00Q 1.518(4) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.383(4) . ?
C00I C00P 1.386(5) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.386(4) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00P 1.394(5) . ?
C00N H00N 0.9300 . ?
C00O H00E 0.9600 . ?
C00O H00F 0.9600 . ?
C00O H00G 0.9600 . ?
C00P H00P 0.9300 . ?
C00Q H00B 0.9600 . ?
C00Q H00C 0.9600 . ?
C00Q H00D 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S002 C00A C00N C00B 1.2(3) . . . . ?
O003 C00D C00G C00L -153.9(3) . . . . ?
O003 C00D C00G C00M 19.8(5) . . . . ?
O004 C00E C00H N008 -52.0(4) . . . . ?
O004 C00E C00H C00Q 69.5(4) . . . . ?
N005 C00B C00K S002 179.4(3) . . . . ?
N005 C00B C00N C00A -179.9(3) . . . . ?
N006 N007 C00E O004 1.2(4) . . . . ?
N006 N007 C00E C00H -179.7(2) . . . . ?
N007 N006 C00F S001 -177.2(2) . . . . ?
N007 N006 C00F N005 3.4(4) . . . . ?
N007 C00E C00H N008 128.9(3) . . . . ?
N007 C00E C00H C00Q -109.6(3) . . . . ?
N008 C00D C00G C00L 24.1(5) . . . . ?
N008 C00D C00G C00M -162.2(3) . . . . ?
C00A S002 C00K C00B -0.4(3) . . . . ?
C00B N005 C00F S001 0.1(5) . . . . ?
C00B N005 C00F N006 179.5(3) . . . . ?
C00D N008 C00H C00E -66.9(4) . . . . ?
C00D N008 C00H C00Q 171.7(3) . . . . ?
C00D C00G C00L C00J 172.0(3) . . . . ?
C00D C00G C00M C00P -172.4(3) . . . . ?
C00F N005 C00B C00K 12.1(5) . . . . ?
C00F N005 C00B C00N -169.8(3) . . . . ?
C00F N006 N007 C00E 81.3(4) . . . . ?
C00G C00M C00P C00I 0.3(5) . . . . ?
C00H N008 C00D O003 5.7(5) . . . . ?
C00H N008 C00D C00G -172.3(3) . . . . ?
C00I C00J C00L C00G 0.2(5) . . . . ?
C00J C00I C00P C00M -1.8(5) . . . . ?
C00K S002 C00A C00N -0.4(2) . . . . ?
C00K C00B C00N C00A -1.6(4) . . . . ?
C00L C00G C00M C00P 1.5(5) . . . . ?
C00M C00G C00L C00J -1.7(5) . . . . ?
C00N C00B C00K S002 1.2(4) . . . . ?
C00P C00I C00J C00L 1.6(5) . . . . ?
