#------------------------------------------------------------------------------
#$Date: 2016-08-07 11:34:03 +0200 (dom 07 de ago de 2016) $
#$Revision: 185600 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/53/7055339.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_7055339
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            'C52 H74 N12 S2'
_chemical_formula_weight         931.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 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                 99.08(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.481(4)
_cell_length_b                   9.905(2)
_cell_length_c                   26.740(5)
_cell_measurement_temperature    213(2)
_cell_volume                     5095.1(18)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0669
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            24480
_diffrn_reflns_theta_full        28.06
_diffrn_reflns_theta_max         28.06
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.9775
_exptl_absorpt_correction_T_min  0.9775
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2008
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.889
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         6143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.889
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0677P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                4244
_reflns_number_total             6143
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5nj03197d2.cif
_cod_data_source_block           gr15
_cod_depositor_comments
'Adding full bibliography for 7055338--7055343.cif.'
_cod_original_sg_symbol_H-M      I2/a
_cod_database_code               7055339
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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 0.12893(7) 0.67520(13) 0.49847(5) 0.0232(3) Uani 1 1 d .
C2 C 0.09530(7) 0.69867(13) 0.54071(5) 0.0236(3) Uani 1 1 d .
C3 C 0.09491(7) 0.82879(14) 0.56052(5) 0.0255(3) Uani 1 1 d .
H3 H 0.0734 0.8432 0.5891 0.031 Uiso 1 1 calc R
C4 C 0.12508(7) 0.93822(13) 0.53968(5) 0.0247(3) Uani 1 1 d .
C5 C 0.15344(8) 0.91450(14) 0.49547(5) 0.0263(3) Uani 1 1 d .
H5 H 0.1723 0.9875 0.4797 0.032 Uiso 1 1 calc R
C6 C 0.15467(7) 0.78688(14) 0.47408(5) 0.0243(3) Uani 1 1 d .
C7 C 0.12299(8) 1.08181(14) 0.56138(5) 0.0293(3) Uani 1 1 d .
C8 C 0.11119(11) 1.08107(17) 0.61681(6) 0.0459(4) Uani 1 1 d .
H8A H 0.1477 1.0294 0.6371 0.069 Uiso 1 1 calc R
H8B H 0.0665 1.0404 0.6190 0.069 Uiso 1 1 calc R
H8C H 0.1119 1.1730 0.6294 0.069 Uiso 1 1 calc R
C9 C 0.06254(11) 1.15772(18) 0.52989(7) 0.0513(5) Uani 1 1 d .
H9A H 0.0599 1.2483 0.5432 0.077 Uiso 1 1 calc R
H9B H 0.0194 1.1103 0.5316 0.077 Uiso 1 1 calc R
H9C H 0.0701 1.1625 0.4949 0.077 Uiso 1 1 calc R
C10 C 0.19096(11) 1.15585(19) 0.55902(9) 0.0555(5) Uani 1 1 d .
H10A H 0.1972 1.1663 0.5239 0.083 Uiso 1 1 calc R
H10B H 0.2294 1.1043 0.5771 0.083 Uiso 1 1 calc R
H10C H 0.1896 1.2441 0.5745 0.083 Uiso 1 1 calc R
C11 C 0.18303(8) 0.76735(14) 0.42470(5) 0.0268(3) Uani 1 1 d .
H11A H 0.2336 0.7574 0.4324 0.032 Uiso 1 1 calc R
H11B H 0.1641 0.6833 0.4088 0.032 Uiso 1 1 calc R
C12 C 0.20765(8) 0.86357(16) 0.34668(5) 0.0327(3) Uani 1 1 d .
H12A H 0.2570 0.8683 0.3613 0.039 Uiso 1 1 calc R
H12B H 0.1976 0.9412 0.3240 0.039 Uiso 1 1 calc R
C13 C 0.19615(9) 0.73409(18) 0.31449(5) 0.0382(4) Uani 1 1 d .
H13A H 0.1466 0.7112 0.3094 0.046 Uiso 1 1 calc R
H13B H 0.2090 0.7520 0.2811 0.046 Uiso 1 1 calc R
C14 C 0.19076(8) 0.62520(17) 0.66821(6) 0.0352(3) Uani 1 1 d .
H14A H 0.1744 0.7180 0.6616 0.042 Uiso 1 1 calc R
H14B H 0.1859 0.6029 0.7032 0.042 Uiso 1 1 calc R
C15 C 0.14480(9) 0.53002(15) 0.63236(5) 0.0330(3) Uani 1 1 d .
H15A H 0.1653 0.5179 0.6015 0.040 Uiso 1 1 calc R
H15B H 0.1434 0.4416 0.6486 0.040 Uiso 1 1 calc R
C16 C 0.05378(8) 0.59142(14) 0.56359(5) 0.0279(3) Uani 1 1 d .
H16A H 0.0042 0.6131 0.5556 0.034 Uiso 1 1 calc R
H16B H 0.0611 0.5038 0.5482 0.034 Uiso 1 1 calc R
C17 C 0.22762(7) 0.48360(14) 0.47388(5) 0.0277(3) Uani 1 1 d .
H17A H 0.2343 0.3978 0.4571 0.033 Uiso 1 1 calc R
H17B H 0.2436 0.5560 0.4536 0.033 Uiso 1 1 calc R
C18 C 0.09208(8) 0.89149(16) 0.37114(5) 0.0324(3) Uani 1 1 d .
H18A H 0.0676 0.8866 0.4004 0.039 Uiso 1 1 calc R
H18B H 0.0762 0.8160 0.3486 0.039 Uiso 1 1 calc R
C19 C 0.07385(9) 1.02467(18) 0.34308(6) 0.0411(4) Uani 1 1 d .
H19A H 0.0941 1.0251 0.3118 0.049 Uiso 1 1 calc R
H19B H 0.0232 1.0314 0.3338 0.049 Uiso 1 1 calc R
C20 C 0.09941(11) 1.14167(19) 0.37370(7) 0.0514(5) Uani 1 1 d .
C21 C 0.20323(10) 0.48714(19) 0.32361(6) 0.0450(4) Uani 1 1 d .
H21A H 0.1584 0.4842 0.3359 0.054 Uiso 1 1 calc R
H21B H 0.2326 0.4158 0.3411 0.054 Uiso 1 1 calc R
C22 C 0.19095(13) 0.4569(2) 0.26600(8) 0.0588(5) Uani 1 1 d .
H22A H 0.1547 0.5168 0.2488 0.071 Uiso 1 1 calc R
H22B H 0.2338 0.4740 0.2521 0.071 Uiso 1 1 calc R
C23 C 0.16962(13) 0.3146(2) 0.25691(8) 0.0645(6) Uani 1 1 d .
C24 C 0.02055(9) 0.50815(17) 0.64091(6) 0.0384(4) Uani 1 1 d .
H24A H 0.0224 0.4122 0.6323 0.046 Uiso 1 1 calc R
H24B H -0.0255 0.5424 0.6264 0.046 Uiso 1 1 calc R
C25 C 0.03094(11) 0.5236(2) 0.69864(7) 0.0497(5) Uani 1 1 d .
H25A H -0.0074 0.4786 0.7117 0.060 Uiso 1 1 calc R
H25B H 0.0742 0.4785 0.7133 0.060 Uiso 1 1 calc R
C26 C 0.03388(11) 0.6643(2) 0.71477(7) 0.0507(5) Uani 1 1 d .
N1 N 0.16663(6) 0.87856(12) 0.38829(4) 0.0266(2) Uani 1 1 d .
N2 N 0.23602(7) 0.61790(14) 0.33706(5) 0.0342(3) Uani 1 1 d .
N3 N 0.07375(7) 0.58146(12) 0.61883(4) 0.0284(3) Uani 1 1 d .
N4 N 0.12015(14) 1.2330(2) 0.39729(9) 0.0817(7) Uani 1 1 d .
N5 N 0.15537(13) 0.2043(2) 0.25085(8) 0.0807(7) Uani 1 1 d .
N6 N 0.03899(11) 0.7717(2) 0.72904(7) 0.0752(6) Uani 1 1 d .
S1 S 0.134727(19) 0.50676(3) 0.475347(13) 0.02742(10) 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 118.87(12) .
C2 C1 S1 119.52(10) .
C6 C1 S1 121.56(10) .
C3 C2 C1 119.17(12) .
C3 C2 C16 117.24(12) .
C1 C2 C16 123.39(12) .
C4 C3 C2 122.71(12) .
C3 C4 C5 117.07(12) .
C3 C4 C7 122.09(12) .
C5 C4 C7 120.69(12) .
C6 C5 C4 122.31(12) .
C5 C6 C1 119.42(12) .
C5 C6 C11 120.33(12) .
C1 C6 C11 120.25(12) .
C10 C7 C9 109.79(15) .
C10 C7 C8 107.80(15) .
C9 C7 C8 108.29(14) .
C10 C7 C4 110.75(12) .
C9 C7 C4 108.06(12) .
C8 C7 C4 112.11(12) .
N1 C11 C6 114.09(11) .
N1 C12 C13 117.16(13) .
N2 C13 C12 113.77(12) .
N2 C14 C15 113.20(13) 2_556
N3 C15 C14 112.16(12) .
N3 C16 C2 112.20(11) .
C17 C17 S1 113.86(13) 2_556
N1 C18 C19 111.86(13) .
C20 C19 C18 112.12(14) .
N4 C20 C19 179.1(3) .
N2 C21 C22 114.07(15) .
C23 C22 C21 110.04(18) .
N5 C23 C22 177.7(3) .
N3 C24 C25 111.54(14) .
C26 C25 C24 112.75(15) .
N6 C26 C25 176.5(2) .
C18 N1 C11 112.06(11) .
C18 N1 C12 113.73(11) .
C11 N1 C12 109.66(11) .
C14 N2 C21 114.58(13) 2_556
C14 N2 C13 112.63(13) 2_556
C21 N2 C13 114.31(14) .
C24 N3 C15 115.41(12) .
C24 N3 C16 110.28(12) .
C15 N3 C16 111.17(12) .
C1 S1 C17 103.93(6) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.4116(19) .
C1 C6 1.4154(18) .
C1 S1 1.7890(14) .
C2 C3 1.3939(19) .
C2 C16 1.5210(19) .
C3 C4 1.3908(19) .
C4 C5 1.4016(19) .
C4 C7 1.5390(19) .
C5 C6 1.3892(19) .
C6 C11 1.5220(18) .
C7 C10 1.524(2) .
C7 C9 1.532(2) .
C7 C8 1.535(2) .
C11 N1 1.4715(17) .
C12 N1 1.4763(18) .
C12 C13 1.541(2) .
C13 N2 1.464(2) .
C14 N2 1.457(2) 2_556
C14 C15 1.529(2) .
C15 N3 1.466(2) .
C16 N3 1.4704(18) .
C17 C17 1.526(3) 2_556
C17 S1 1.8306(15) .
C18 N1 1.458(2) .
C18 C19 1.531(2) .
C19 C20 1.460(3) .
C20 N4 1.140(3) .
C21 N2 1.464(2) .
C21 C22 1.551(3) .
C22 C23 1.478(3) .
C23 N5 1.133(3) .
C24 N3 1.4638(19) .
C24 C25 1.533(2) .
C25 C26 1.457(3) .
C26 N6 1.130(3) .
N2 C14 1.457(2) 2_556
