#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/53/7055343.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_7055343
loop_
_publ_author_name
'Gressenbuch, Mathias'
'Lehmann, Ulrike'
'Kersting, Berthold'
_publ_section_title
;
 Synthesis and structural chemistry of bicyclic hexaaza-dithia macrocycles
 containing pendant donor groups
;
_journal_issue                   7
_journal_name_full               'New J. Chem.'
_journal_page_first              5731
_journal_paper_doi               10.1039/C5NJ03197D
_journal_volume                  40
_journal_year                    2016
_chemical_formula_sum            'C48 H80 N6 O4 S2'
_chemical_formula_weight         869.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-11-11 deposited with the CCDC.
2016-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.50(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.007(3)
_cell_length_b                   10.269(2)
_cell_length_c                   19.285(4)
_cell_measurement_temperature    213(2)
_cell_volume                     2553.8(10)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-AREA, STOE X-RED'
_computing_molecular_graphics    'ORTEP 3 (Farrugia, 1999)'
_computing_publication_material  'ORTEP 3 (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'STOE IPDS-1'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_av_sigmaI/netI    0.1805
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16066
_diffrn_reflns_theta_full        24.00
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.9706
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.00066(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.554
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.554
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0001P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0446
_refine_ls_wR_factor_ref         0.0519
_reflns_number_gt                1609
_reflns_number_total             3945
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5nj03197d2.cif
_cod_data_source_block           ul_22
_cod_depositor_comments
'Adding full bibliography for 7055338--7055343.cif.'
_cod_original_cell_volume        2553.7(9)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7055343
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.0453(2) 0.8155(2) -0.05132(12) 0.0312(7) Uani 1 1 d .
C2 C -0.0347(2) 0.9024(2) -0.07543(13) 0.0322(7) Uani 1 1 d .
C3 C -0.0176(2) 0.9934(2) -0.12622(13) 0.0364(8) Uani 1 1 d .
H3 H -0.0714 1.0512 -0.1425 0.044 Uiso 1 1 calc R
C4 C 0.0754(2) 1.0024(2) -0.15394(13) 0.0354(7) Uani 1 1 d .
C5 C 0.1546(2) 0.9171(2) -0.12742(12) 0.0369(7) Uani 1 1 d .
H5 H 0.2189 0.9224 -0.1445 0.044 Uiso 1 1 calc R
C6 C 0.1416(2) 0.8249(2) -0.07658(13) 0.0336(7) Uani 1 1 d .
C7 C 0.0946(3) 1.1044(3) -0.20889(14) 0.0430(8) Uani 1 1 d .
C8 C 0.1286(3) 1.0410(3) -0.27181(15) 0.0998(16) Uani 1 1 d .
H8A H 0.0748 0.9822 -0.2926 0.150 Uiso 1 1 calc R
H8B H 0.1919 0.9924 -0.2581 0.150 Uiso 1 1 calc R
H8C H 0.1411 1.1072 -0.3056 0.150 Uiso 1 1 calc R
C9 C 0.1766(3) 1.1982(4) -0.17704(16) 0.1019(15) Uani 1 1 d .
H9A H 0.1537 1.2398 -0.1366 0.153 Uiso 1 1 calc R
H9B H 0.1884 1.2639 -0.2113 0.153 Uiso 1 1 calc R
H9C H 0.2406 1.1512 -0.1627 0.153 Uiso 1 1 calc R
C10 C -0.0003(3) 1.1840(4) -0.2319(2) 0.1318(19) Uani 1 1 d .
H10A H -0.0555 1.1274 -0.2529 0.198 Uiso 1 1 calc R
H10B H 0.0153 1.2482 -0.2659 0.198 Uiso 1 1 calc R
H10C H -0.0221 1.2279 -0.1917 0.198 Uiso 1 1 calc R
C11 C -0.1349(2) 0.9088(2) -0.04526(12) 0.0376(7) Uani 1 1 d .
H11A H -0.1204 0.8946 0.0053 0.045 Uiso 1 1 calc R
H11B H -0.1635 0.9967 -0.0526 0.045 Uiso 1 1 calc R
C12 C -0.2526(2) 0.8471(2) -0.14625(13) 0.0452(9) Uani 1 1 d .
H12A H -0.1955 0.8471 -0.1740 0.068 Uiso 1 1 calc R
H12B H -0.2841 0.9328 -0.1478 0.068 Uiso 1 1 calc R
H12C H -0.3039 0.7833 -0.1650 0.068 Uiso 1 1 calc R
C13 C -0.2972(2) 0.8134(2) -0.03048(12) 0.0376(7) Uani 1 1 d .
H13A H -0.3244 0.9021 -0.0282 0.045 Uiso 1 1 calc R
H13B H -0.2679 0.7882 0.0170 0.045 Uiso 1 1 calc R
C14 C -0.3866(2) 0.7221(2) -0.05541(13) 0.0395(8) Uani 1 1 d .
H14A H -0.4319 0.7155 -0.0187 0.047 Uiso 1 1 calc R
H14B H -0.4273 0.7602 -0.0968 0.047 Uiso 1 1 calc R
C15 C -0.4105(3) 0.5305(3) -0.12703(15) 0.0399(8) Uani 1 1 d .
C16 C -0.4287(3) 0.3205(3) -0.18731(15) 0.0483(9) Uani 1 1 d .
C17 C -0.4248(3) 0.3767(3) -0.25967(15) 0.0689(11) Uani 1 1 d .
H17A H -0.3532 0.3909 -0.2667 0.103 Uiso 1 1 calc R
H17B H -0.4619 0.4589 -0.2639 0.103 Uiso 1 1 calc R
H17C H -0.4569 0.3163 -0.2946 0.103 Uiso 1 1 calc R
C18 C -0.5376(3) 0.2950(3) -0.17497(16) 0.0747(11) Uani 1 1 d .
H18A H -0.5379 0.2591 -0.1285 0.112 Uiso 1 1 calc R
H18B H -0.5694 0.2335 -0.2095 0.112 Uiso 1 1 calc R
H18C H -0.5764 0.3759 -0.1789 0.112 Uiso 1 1 calc R
C19 C -0.3615(3) 0.2001(3) -0.17709(17) 0.0805(12) Uani 1 1 d .
H19A H -0.3646 0.1646 -0.1308 0.121 Uiso 1 1 calc R
H19B H -0.2904 0.2227 -0.1819 0.121 Uiso 1 1 calc R
H19C H -0.3863 0.1355 -0.2120 0.121 Uiso 1 1 calc R
C20 C 0.2740(2) 0.4752(2) 0.02599(13) 0.0387(8) Uani 1 1 d .
H20A H 0.2439 0.5446 0.0518 0.046 Uiso 1 1 calc R
H20B H 0.2187 0.4134 0.0097 0.046 Uiso 1 1 calc R
C21 C 0.3170(2) 0.5336(2) -0.03675(13) 0.0447(8) Uani 1 1 d .
H21A H 0.3775 0.5877 -0.0207 0.054 Uiso 1 1 calc R
H21B H 0.3394 0.4636 -0.0659 0.054 Uiso 1 1 calc R
C22 C 0.2583(3) 0.6211(3) -0.15054(14) 0.0596(10) Uani 1 1 d .
H22A H 0.2594 0.5340 -0.1699 0.089 Uiso 1 1 calc R
H22B H 0.3250 0.6624 -0.1520 0.089 Uiso 1 1 calc R
H22C H 0.2045 0.6719 -0.1778 0.089 Uiso 1 1 calc R
C23 C 0.2352(2) 0.7444(2) -0.04792(13) 0.0423(8) Uani 1 1 d .
H23A H 0.2981 0.7910 -0.0564 0.051 Uiso 1 1 calc R
H23B H 0.2366 0.7360 0.0028 0.051 Uiso 1 1 calc R
C24 C 0.0045(2) 0.5524(2) -0.02731(11) 0.0347(8) Uani 1 1 d .
H24A H -0.0598 0.5577 -0.0598 0.042 Uiso 1 1 calc R
H24B H 0.0616 0.5321 -0.0540 0.042 Uiso 1 1 calc R
N1 N -0.21421(17) 0.81423(19) -0.07455(10) 0.0312(6) Uani 1 1 d .
N2 N -0.35437(18) 0.5918(2) -0.07277(10) 0.0346(6) Uani 1 1 d .
N3 N 0.23717(18) 0.61353(19) -0.07852(10) 0.0376(6) Uani 1 1 d .
O1 O -0.48140(17) 0.58020(18) -0.16547(9) 0.0515(6) Uani 1 1 d .
O2 O -0.37693(16) 0.40785(17) -0.13342(9) 0.0519(6) Uani 1 1 d .
S1 S 0.02912(7) 0.70638(6) 0.01878(3) 0.0415(2) Uani 1 1 d .
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
C2 C1 C6 119.8(2) . .
C2 C1 S1 119.6(2) . .
C6 C1 S1 120.2(2) . .
C3 C2 C1 118.7(3) . .
C3 C2 C11 118.1(3) . .
C1 C2 C11 123.0(2) . .
C4 C3 C2 122.9(3) . .
C3 C4 C5 117.1(3) . .
C3 C4 C7 122.7(3) . .
C5 C4 C7 120.1(3) . .
C6 C5 C4 122.3(3) . .
C5 C6 C1 119.2(3) . .
C5 C6 C23 117.6(3) . .
C1 C6 C23 123.1(2) . .
C8 C7 C10 108.5(3) . .
C8 C7 C9 109.9(3) . .
C10 C7 C9 106.5(3) . .
C8 C7 C4 110.8(2) . .
C10 C7 C4 112.0(3) . .
C9 C7 C4 109.0(2) . .
N1 C11 C2 115.1(2) . .
N1 C13 C14 114.4(2) . .
N2 C14 C13 114.1(2) . .
O1 C15 O2 124.5(3) . .
O1 C15 N2 124.5(3) . .
O2 C15 N2 111.0(3) . .
O2 C16 C18 110.6(2) . .
O2 C16 C19 101.8(2) . .
C18 C16 C19 112.4(3) . .
O2 C16 C17 110.6(2) . .
C18 C16 C17 111.1(3) . .
C19 C16 C17 110.1(2) . .
N2 C20 C21 111.7(2) 3_565 .
N3 C21 C20 110.4(2) . .
N3 C23 C6 114.1(2) . .
C24 C24 S1 107.5(2) 3_565 .
C12 N1 C13 111.7(2) . .
C12 N1 C11 110.44(19) . .
C13 N1 C11 108.34(19) . .
C15 N2 C14 117.7(2) . .
C15 N2 C20 122.0(2) . 3_565
C14 N2 C20 119.7(2) . 3_565
C22 N3 C23 110.5(2) . .
C22 N3 C21 110.1(2) . .
C23 N3 C21 109.7(2) . .
C15 O2 C16 120.9(2) . .
C1 S1 C24 101.84(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.403(3) .
C1 C6 1.405(4) .
C1 S1 1.789(2) .
C2 C3 1.392(3) .
C2 C11 1.496(3) .
C3 C4 1.388(3) .
C4 C5 1.397(4) .
C4 C7 1.534(3) .
C5 C6 1.389(3) .
C6 C23 1.515(4) .
C7 C8 1.494(4) .
C7 C10 1.498(4) .
C7 C9 1.507(4) .
C11 N1 1.475(3) .
C12 N1 1.447(3) .
C13 N1 1.458(3) .
C13 C14 1.522(3) .
C14 N2 1.454(3) .
C15 O1 1.217(3) .
C15 O2 1.344(3) .
C15 N2 1.351(3) .
C16 O2 1.468(3) .
C16 C18 1.490(4) .
C16 C19 1.512(4) .
C16 C17 1.517(3) .
C20 N2 1.460(3) 3_565
C20 C21 1.520(3) .
C21 N3 1.477(3) .
C22 N3 1.453(3) .
C23 N3 1.469(3) .
C24 C24 1.522(4) 3_565
C24 S1 1.821(2) .
N2 C20 1.460(3) 3_565
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132595582
