#------------------------------------------------------------------------------
#$Date: 2023-05-05 14:24:37 +0300 (Fri, 05 May 2023) $
#$Revision: 283524 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/90/1569039.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_1569039
loop_
_publ_author_name
'Caltagirone, Claudia'
'Aragoni, Maria Carla'
'Arca, Massimiliano'
'Blake, Alexander John'
'Demartin, Francesco'
'Garau, Alessandra'
'Podda, Enrico'
'Pop, Alexandra'
'Lippolis, Vito'
'Silvestru, Cristian'
_publ_section_title
;
 Functionalization and Coordination Effects on the Structural Chemistry of
 Pendant Arm Derivatives of 1,4,7-trithia-10-aza-cyclododecane
 ([12]aneNS3)
;
_journal_issue                   4
_journal_name_full               Crystals
_journal_page_first              616
_journal_paper_doi               10.3390/cryst13040616
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C18 H23 Cl N2 O S3'
_chemical_formula_sum            'C18 H23 Cl N2 O S3'
_chemical_formula_weight         415.01
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-02-17
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-03-13 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                99.469(2)
_cell_angle_beta                 99.016(2)
_cell_angle_gamma                93.623(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4811(6)
_cell_length_b                   9.8093(7)
_cell_length_c                   11.8739(9)
_cell_measurement_reflns_used    5249
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.45
_cell_volume                     958.31(12)
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2002)'
_computing_data_collection       'Bruker SMART version 5.624 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker SMART1000 CCD area detector'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_av_unetI/netI     0.021
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8758
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        27.474
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_min         2.114
_diffrn_source                   'normal-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.536
_exptl_absorpt_correction_T_max  0.411
_exptl_absorpt_correction_T_min  0.301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SHELXTL version 6.12; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.98
_exptl_crystal_size_mid          0.9
_exptl_crystal_size_min          0.59
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0078(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0404P)²+0.3236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0793
_reflns_number_gt                3769
_reflns_number_total             4271
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            2248158.cif
_cod_data_source_block           quinss
_cod_database_code               1569039
_shelx_shelxl_version_number     2018/3
_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.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B),
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
1.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C20(H20), C21(H21), C22(H22)
1.c Idealised tetrahedral OH refined as rotating group:
 O24(H24)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
N1 N 0.19454(14) 0.36813(12) 0.67411(10) 0.0189(2) Uani 1 1 d . . . . .
N23 N -0.14699(14) 0.12757(12) 1.00946(11) 0.0211(3) Uani 1 1 d . . . . .
O24 O 0.12977(12) 0.13555(10) 0.91919(9) 0.0223(2) Uani 1 1 d . . . . .
H24 H 0.088102 0.076110 0.951781 0.033 Uiso 1 1 calc R U . . .
S4 S -0.07477(5) 0.15325(5) 0.37128(4) 0.03250(12) Uani 1 1 d . . . . .
S7 S 0.37391(5) 0.05860(4) 0.23759(3) 0.02798(11) Uani 1 1 d . . . . .
S10 S 0.63365(4) 0.31299(5) 0.56835(3) 0.02995(11) Uani 1 1 d . . . . .
Cl25 Cl -0.30036(4) 0.57600(4) 0.86025(3) 0.02373(10) Uani 1 1 d . . . . .
C2 C 0.09170(17) 0.25572(15) 0.59327(12) 0.0217(3) Uani 1 1 d . . . . .
H2A H -0.000575 0.228351 0.629047 0.026 Uiso 1 1 calc R U . . .
H2B H 0.153407 0.173979 0.579558 0.026 Uiso 1 1 calc R U . . .
C3 C 0.02967(18) 0.29766(16) 0.47770(13) 0.0256(3) Uani 1 1 d . . . . .
H3A H 0.121083 0.337158 0.447086 0.031 Uiso 1 1 calc R U . . .
H3B H -0.044051 0.370930 0.490149 0.031 Uiso 1 1 calc R U . . .
C5 C 0.09149(19) 0.06002(16) 0.33191(14) 0.0269(3) Uani 1 1 d . . . . .
H5A H 0.163262 0.048740 0.403357 0.032 Uiso 1 1 calc R U . . .
H5B H 0.049887 -0.033743 0.288776 0.032 Uiso 1 1 calc R U . . .
C6 C 0.18772(18) 0.13333(17) 0.25790(13) 0.0265(3) Uani 1 1 d . . . . .
H6A H 0.212493 0.232099 0.294719 0.032 Uiso 1 1 calc R U . . .
H6B H 0.120976 0.130006 0.181050 0.032 Uiso 1 1 calc R U . . .
C8 C 0.48939(18) 0.10896(16) 0.38222(13) 0.0259(3) Uani 1 1 d . . . . .
H8A H 0.425826 0.078414 0.438227 0.031 Uiso 1 1 calc R U . . .
H8B H 0.587849 0.059610 0.386788 0.031 Uiso 1 1 calc R U . . .
C9 C 0.53694(18) 0.26369(16) 0.41801(13) 0.0249(3) Uani 1 1 d . . . . .
H9A H 0.439904 0.314032 0.405603 0.030 Uiso 1 1 calc R U . . .
H9B H 0.610752 0.292646 0.367696 0.030 Uiso 1 1 calc R U . . .
C11 C 0.46627(17) 0.28579(17) 0.64269(13) 0.0252(3) Uani 1 1 d . . . . .
H11A H 0.406440 0.195126 0.606877 0.030 Uiso 1 1 calc R U . . .
H11B H 0.508355 0.281519 0.724528 0.030 Uiso 1 1 calc R U . . .
C12 C 0.35006(17) 0.39951(15) 0.63933(13) 0.0218(3) Uani 1 1 d . . . . .
H12A H 0.403599 0.485200 0.690604 0.026 Uiso 1 1 calc R U . . .
H12B H 0.329717 0.419341 0.559482 0.026 Uiso 1 1 calc R U . . .
C13 C 0.21896(17) 0.33870(15) 0.79273(12) 0.0214(3) Uani 1 1 d . . . . .
H13A H 0.299044 0.410019 0.842726 0.026 Uiso 1 1 calc R U . . .
H13B H 0.262770 0.247489 0.792488 0.026 Uiso 1 1 calc R U . . .
C14 C 0.06645(16) 0.33700(14) 0.84319(12) 0.0186(3) Uani 1 1 d . . . . .
C15 C -0.03807(16) 0.44275(14) 0.83079(12) 0.0196(3) Uani 1 1 d . . . . .
H15 H -0.011545 0.514553 0.790338 0.024 Uiso 1 1 calc R U . . .
C16 C -0.17592(16) 0.44283(14) 0.87604(12) 0.0185(3) Uani 1 1 d . . . . .
C17 C -0.22173(16) 0.33782(14) 0.93661(12) 0.0178(3) Uani 1 1 d . . . . .
C18 C -0.11570(16) 0.23317(14) 0.95167(11) 0.0174(3) Uani 1 1 d . . . . .
C19 C 0.02832(16) 0.23552(14) 0.90467(12) 0.0180(3) Uani 1 1 d . . . . .
C20 C -0.36495(17) 0.32770(15) 0.98199(13) 0.0222(3) Uani 1 1 d . . . . .
H20 H -0.440034 0.394596 0.972854 0.027 Uiso 1 1 calc R U . . .
C21 C -0.39581(18) 0.22162(16) 1.03914(14) 0.0262(3) Uani 1 1 d . . . . .
H21 H -0.492130 0.213632 1.069963 0.031 Uiso 1 1 calc R U . . .
C22 C -0.28199(18) 0.12435(15) 1.05143(13) 0.0250(3) Uani 1 1 d . . . . .
H22 H -0.303750 0.051912 1.092505 0.030 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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
C12 N1 C2 113.65(11) . . ?
C13 N1 C2 111.20(11) . . ?
C13 N1 C12 110.18(11) . . ?
C22 N23 C18 117.59(12) . . ?
C19 O24 H24 109.5 . . ?
C5 S4 C3 101.03(7) . . ?
C8 S7 C6 100.60(7) . . ?
C11 S10 C9 101.05(7) . . ?
N1 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
N1 C2 C3 112.52(12) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
S4 C3 H3A 109.1 . . ?
S4 C3 H3B 109.1 . . ?
C2 C3 S4 112.68(11) . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
S4 C5 H5A 109.0 . . ?
S4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 S4 112.75(11) . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
S7 C6 H6A 108.8 . . ?
S7 C6 H6B 108.8 . . ?
C5 C6 S7 113.71(11) . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
S7 C8 H8A 108.7 . . ?
S7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 S7 114.27(11) . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
S10 C9 H9A 108.9 . . ?
S10 C9 H9B 108.9 . . ?
C8 C9 S10 113.18(11) . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.8 . . ?
S10 C11 H11A 108.9 . . ?
S10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 S10 113.57(10) . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
N1 C12 C11 116.02(12) . . ?
N1 C12 H12A 108.3 . . ?
N1 C12 H12B 108.3 . . ?
C11 C12 H12A 108.3 . . ?
C11 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
N1 C13 H13A 109.0 . . ?
N1 C13 H13B 109.0 . . ?
N1 C13 C14 112.71(11) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C15 C14 C13 120.20(12) . . ?
C19 C14 C13 120.93(12) . . ?
C19 C14 C15 118.84(12) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.90(13) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 Cl25 119.49(11) . . ?
C15 C16 C17 121.89(12) . . ?
C17 C16 Cl25 118.62(10) . . ?
C16 C17 C18 117.52(12) . . ?
C20 C17 C16 125.28(12) . . ?
C20 C17 C18 117.20(12) . . ?
N23 C18 C17 122.55(12) . . ?
N23 C18 C19 117.69(12) . . ?
C19 C18 C17 119.75(12) . . ?
O24 C19 C14 119.20(12) . . ?
O24 C19 C18 119.74(12) . . ?
C14 C19 C18 121.05(12) . . ?
C17 C20 H20 120.0 . . ?
C21 C20 C17 119.94(13) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.7 . . ?
C20 C21 C22 118.65(14) . . ?
C22 C21 H21 120.7 . . ?
N23 C22 C21 124.05(14) . . ?
N23 C22 H22 118.0 . . ?
C21 C22 H22 118.0 . . ?
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
N1 C2 1.4717(18) . ?
N1 C12 1.4719(17) . ?
N1 C13 1.4697(18) . ?
N23 C18 1.3676(18) . ?
N23 C22 1.3190(19) . ?
O24 H24 0.8400 . ?
O24 C19 1.3592(16) . ?
S4 C3 1.8137(16) . ?
S4 C5 1.8089(16) . ?
S7 C6 1.8156(16) . ?
S7 C8 1.8125(16) . ?
S10 C9 1.8166(16) . ?
S10 C11 1.8132(15) . ?
Cl25 C16 1.7460(14) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.522(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.521(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.518(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.536(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5085(19) . ?
C14 C15 1.4175(19) . ?
C14 C19 1.3787(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.361(2) . ?
C16 C17 1.4177(19) . ?
C17 C18 1.4217(18) . ?
C17 C20 1.4082(19) . ?
C18 C19 1.4206(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.366(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.408(2) . ?
C22 H22 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O24 H24 N23 0.84 2.19 2.8511(16) 135.2 2_557 yes
O24 H24 N23 0.84 2.27 2.7308(15) 115.0 . yes
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
N1 C2 C3 S4 172.33(9) . . . . ?
N1 C13 C14 C15 -45.14(18) . . . . ?
N1 C13 C14 C19 136.69(14) . . . . ?
N23 C18 C19 O24 -0.67(19) . . . . ?
N23 C18 C19 C14 178.62(13) . . . . ?
S4 C5 C6 S7 170.11(8) . . . . ?
S7 C8 C9 S10 173.80(8) . . . . ?
S10 C11 C12 N1 166.59(10) . . . . ?
Cl25 C16 C17 C18 -177.93(10) . . . . ?
Cl25 C16 C17 C20 2.9(2) . . . . ?
C2 N1 C12 C11 -67.17(16) . . . . ?
C2 N1 C13 C14 -65.77(15) . . . . ?
C3 S4 C5 C6 -72.82(12) . . . . ?
C5 S4 C3 C2 -74.73(12) . . . . ?
C6 S7 C8 C9 -68.68(12) . . . . ?
C8 S7 C6 C5 -70.09(12) . . . . ?
C9 S10 C11 C12 -75.58(12) . . . . ?
C11 S10 C9 C8 -70.47(12) . . . . ?
C12 N1 C2 C3 -69.41(15) . . . . ?
C12 N1 C13 C14 167.30(11) . . . . ?
C13 N1 C2 C3 165.58(11) . . . . ?
C13 N1 C12 C11 58.39(16) . . . . ?
C13 C14 C15 C16 -179.85(13) . . . . ?
C13 C14 C19 O24 -0.3(2) . . . . ?
C13 C14 C19 C18 -179.61(12) . . . . ?
C14 C15 C16 Cl25 179.31(10) . . . . ?
C14 C15 C16 C17 -0.4(2) . . . . ?
C15 C14 C19 O24 -178.52(12) . . . . ?
C15 C14 C19 C18 2.2(2) . . . . ?
C15 C16 C17 C18 1.7(2) . . . . ?
C15 C16 C17 C20 -177.44(13) . . . . ?
C16 C17 C18 N23 179.45(13) . . . . ?
C16 C17 C18 C19 -1.17(19) . . . . ?
C16 C17 C20 C21 -179.85(14) . . . . ?
C17 C18 C19 O24 179.92(12) . . . . ?
C17 C18 C19 C14 -0.8(2) . . . . ?
C17 C20 C21 C22 0.1(2) . . . . ?
C18 N23 C22 C21 0.8(2) . . . . ?
C18 C17 C20 C21 1.0(2) . . . . ?
C19 C14 C15 C16 -1.6(2) . . . . ?
C20 C17 C18 N23 -1.3(2) . . . . ?
C20 C17 C18 C19 178.08(12) . . . . ?
C20 C21 C22 N23 -1.1(3) . . . . ?
C22 N23 C18 C17 0.4(2) . . . . ?
C22 N23 C18 C19 -178.95(13) . . . . ?
