#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:43:23 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178478 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/99/4029979.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_4029979
loop_
_publ_author_name
'Ganapathi, Emandi'
'Lee, Way-Zen'
'Ravikanth, Mangalampalli'
_publ_section_title
;
 Stable nonaromatic [20]dithiaporphyrin (2.1.1.1) macrocycles: synthesis,
 structure, spectral, electrochemical, and metal ion sensing studies.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9603
_journal_page_last               9612
_journal_paper_doi               10.1021/jo501724d
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C43 H33 I N2 O2 S2'
_chemical_formula_sum            'C43 H33 I N2 O2 S2'
_chemical_formula_weight         800.73
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                115.884(10)
_cell_angle_beta                 104.725(9)
_cell_angle_gamma                90.077(10)
_cell_formula_units_Z            2
_cell_length_a                   9.779(5)
_cell_length_b                   15.510(9)
_cell_length_c                   15.774(8)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2064.4(19)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0892
_diffrn_reflns_av_sigmaI/netI    0.2255
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14193
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         1.47
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_correction_T_min  0.7843
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.564
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.314
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         7382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.314
_refine_ls_R_factor_all          0.2586
_refine_ls_R_factor_gt           0.0986
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0913P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2239
_refine_ls_wR_factor_ref         0.3150
_reflns_number_gt                2675
_reflns_number_total             7382
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            Iodo.cif
_cod_data_source_block           14863
_cod_depositor_comments
'Adding full bibliography for 4029978--4029979.cif.'
_cod_original_cell_volume        2064.3(18)
_cod_database_code               4029979
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.9001(4) 0.2053(2) 0.5171(3) 0.0399(10) Uani 1 1 d .
S2 S 0.8404(4) 0.3827(3) 0.7330(3) 0.0454(11) Uani 1 1 d .
C1 C 0.5533(18) -0.2426(10) 0.6813(10) 0.048(4) Uani 1 1 d .
C2 C 0.690(2) -0.2107(14) 0.7038(15) 0.096(7) Uani 1 1 d .
H2 H 0.7612 -0.2417 0.7289 0.115 Uiso 1 1 calc R
C3 C 0.7298(17) -0.1320(13) 0.6909(14) 0.081(6) Uani 1 1 d .
H3 H 0.8276 -0.1078 0.7095 0.097 Uiso 1 1 calc R
C4 C 0.6258(15) -0.0894(9) 0.6507(9) 0.035(3) Uani 1 1 d .
C5 C 0.4877(17) -0.1295(10) 0.6265(12) 0.061(5) Uani 1 1 d .
H5 H 0.4137 -0.1038 0.5961 0.073 Uiso 1 1 calc R
C6 C 0.4503(18) -0.2047(10) 0.6436(11) 0.060(5) Uani 1 1 d .
H6 H 0.3531 -0.2284 0.6285 0.072 Uiso 1 1 calc R
C7 C 0.6626(14) -0.0086(9) 0.6293(10) 0.037(4) Uani 1 1 d .
C8 C 0.7108(14) -0.0324(9) 0.5426(9) 0.036(4) Uani 1 1 d .
C9 C 0.7136(14) -0.1322(9) 0.4725(10) 0.039(4) Uani 1 1 d .
H9 H 0.6867 -0.1890 0.4761 0.047 Uiso 1 1 calc R
C10 C 0.7616(14) -0.1276(9) 0.4024(9) 0.036(4) Uani 1 1 d .
H10 H 0.7765 -0.1808 0.3470 0.043 Uiso 1 1 calc R
C11 C 0.7870(14) -0.0249(9) 0.4270(9) 0.036(4) Uani 1 1 d .
C12 C 0.8358(14) 0.0099(10) 0.3755(9) 0.040(4) Uani 1 1 d .
C13 C 0.8600(15) -0.0645(10) 0.2801(9) 0.037(4) Uani 1 1 d .
C14 C 0.9714(17) -0.1167(10) 0.2776(10) 0.049(4) Uani 1 1 d .
H14 H 1.0407 -0.1045 0.3373 0.058 Uiso 1 1 calc R
C15 C 0.9856(17) -0.1836(12) 0.1943(12) 0.059(5) Uani 1 1 d .
H15 H 1.0635 -0.2201 0.1954 0.071 Uiso 1 1 calc R
C16 C 0.892(2) -0.2021(11) 0.1065(13) 0.062(5) Uani 1 1 d .
C17 C 0.8204(19) -0.2910(13) -0.0691(12) 0.083(6) Uani 1 1 d .
H17A H 0.8489 -0.3422 -0.1229 0.125 Uiso 1 1 calc R
H17B H 0.8203 -0.2317 -0.0769 0.125 Uiso 1 1 calc R
H17C H 0.7246 -0.3112 -0.0704 0.125 Uiso 1 1 calc R
C18 C 0.7723(17) -0.1510(12) 0.1010(11) 0.056(4) Uani 1 1 d .
H18 H 0.7061 -0.1629 0.0402 0.067 Uiso 1 1 calc R
C19 C 0.7584(16) -0.0813(11) 0.1918(12) 0.057(4) Uani 1 1 d .
H19 H 0.6797 -0.0455 0.1933 0.068 Uiso 1 1 calc R
C20 C 0.8800(14) 0.1086(9) 0.4018(8) 0.035(3) Uani 1 1 d .
C21 C 0.9200(16) 0.1424(10) 0.3435(11) 0.057(4) Uani 1 1 d .
H21 H 0.9179 0.1021 0.2772 0.068 Uiso 1 1 calc R
C22 C 0.9653(17) 0.2440(11) 0.3921(12) 0.063(5) Uani 1 1 d .
H22 H 0.9913 0.2780 0.3598 0.075 Uiso 1 1 calc R
C23 C 0.9682(15) 0.2882(10) 0.4889(11) 0.044(4) Uani 1 1 d .
C24 C 1.0339(16) 0.3873(11) 0.5576(12) 0.049(4) Uani 1 1 d .
C25 C 1.1629(17) 0.4216(11) 0.5415(12) 0.068(5) Uani 1 1 d .
H25A H 1.1830 0.3704 0.4837 0.102 Uiso 1 1 calc R
H25B H 1.2445 0.4382 0.5994 0.102 Uiso 1 1 calc R
H25C H 1.1460 0.4789 0.5309 0.102 Uiso 1 1 calc R
C26 C 0.9827(15) 0.4417(10) 0.6310(10) 0.038(4) Uani 1 1 d .
C27 C 1.0612(17) 0.5409(10) 0.7105(10) 0.066(5) Uani 1 1 d .
H27A H 1.0066 0.5700 0.7581 0.098 Uiso 1 1 calc R
H27B H 1.0712 0.5828 0.6801 0.098 Uiso 1 1 calc R
H27C H 1.1558 0.5331 0.7442 0.098 Uiso 1 1 calc R
C28 C 0.8482(16) 0.4141(9) 0.6414(10) 0.038(4) Uani 1 1 d .
C29 C 0.7124(18) 0.4059(10) 0.5834(11) 0.053(4) Uani 1 1 d .
H29 H 0.6927 0.4194 0.5286 0.063 Uiso 1 1 calc R
C30 C 0.6017(16) 0.3745(10) 0.6148(11) 0.049(4) Uani 1 1 d .
H30 H 0.5027 0.3664 0.5830 0.059 Uiso 1 1 calc R
C31 C 0.6548(16) 0.3580(10) 0.6943(10) 0.046(4) Uani 1 1 d .
C32 C 0.5812(15) 0.3274(10) 0.7502(9) 0.040(4) Uani 1 1 d .
C33 C 0.4907(16) 0.3952(9) 0.8059(9) 0.037(4) Uani 1 1 d .
C34 C 0.5251(15) 0.4927(10) 0.8417(10) 0.041(4) Uani 1 1 d .
H34 H 0.6044 0.5162 0.8299 0.049 Uiso 1 1 calc R
C35 C 0.4452(17) 0.5578(10) 0.8954(10) 0.049(4) Uani 1 1 d .
H35 H 0.4688 0.6252 0.9184 0.059 Uiso 1 1 calc R
C36 C 0.3316(16) 0.5247(13) 0.9153(11) 0.049(4) Uani 1 1 d .
C37 C 0.1484(18) 0.5654(12) 0.9932(11) 0.065(5) Uani 1 1 d .
H37A H 0.1077 0.6217 1.0327 0.097 Uiso 1 1 calc R
H37B H 0.1828 0.5295 1.0307 0.097 Uiso 1 1 calc R
H37C H 0.0751 0.5235 0.9325 0.097 Uiso 1 1 calc R
C38 C 0.2937(17) 0.4268(11) 0.8754(11) 0.048(4) Uani 1 1 d .
H38 H 0.2129 0.4030 0.8855 0.057 Uiso 1 1 calc R
C39 C 0.3703(17) 0.3638(11) 0.8215(10) 0.048(4) Uani 1 1 d .
H39 H 0.3410 0.2964 0.7938 0.057 Uiso 1 1 calc R
C40 C 0.5993(14) 0.2396(10) 0.7479(9) 0.036(4) Uani 1 1 d .
C41 C 0.5634(15) 0.2005(10) 0.8070(10) 0.048(4) Uani 1 1 d .
H41 H 0.5258 0.2342 0.8609 0.057 Uiso 1 1 calc R
C42 C 0.5911(15) 0.1081(10) 0.7748(11) 0.049(4) Uani 1 1 d .
H42 H 0.5794 0.0667 0.8032 0.059 Uiso 1 1 calc R
C43 C 0.6405(15) 0.0838(10) 0.6914(10) 0.041(4) Uani 1 1 d .
N1 N 0.7528(11) 0.0320(7) 0.5162(8) 0.035(3) Uani 1 1 d .
N2 N 0.6530(12) 0.1654(7) 0.6806(8) 0.039(3) Uani 1 1 d .
H2A H 0.6896 0.1707 0.6373 0.047 Uiso 1 1 calc R
I1 I 0.50814(15) -0.36437(9) 0.70158(10) 0.0910(7) Uani 1 1 d .
O1 O 0.9153(12) -0.2741(8) 0.0192(8) 0.072(3) Uani 1 1 d .
O2 O 0.2631(13) 0.5966(8) 0.9699(8) 0.066(3) 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
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
H H 0.0000 0.0000 '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
C23 S1 C20 94.5(7)
C28 S2 C31 94.0(7)
C2 C1 C6 122.6(14)
C2 C1 I1 116.5(12)
C6 C1 I1 120.8(11)
C1 C2 C3 120.5(15)
C1 C2 H2 119.8
C3 C2 H2 119.7
C4 C3 C2 119.5(15)
C4 C3 H3 120.2
C2 C3 H3 120.3
C5 C4 C3 115.8(12)
C5 C4 C7 122.3(12)
C3 C4 C7 121.8(12)
C4 C5 C6 123.8(14)
C4 C5 H5 118.1
C6 C5 H5 118.1
C1 C6 C5 117.7(15)
C1 C6 H6 121.1
C5 C6 H6 121.2
C43 C7 C8 124.5(11)
C43 C7 C4 117.2(12)
C8 C7 C4 118.2(12)
N1 C8 C7 125.0(12)
N1 C8 C9 112.7(12)
C7 C8 C9 122.3(12)
C10 C9 C8 106.5(11)
C10 C9 H9 126.8
C8 C9 H9 126.8
C9 C10 C11 107.2(12)
C9 C10 H10 126.4
C11 C10 H10 126.4
C12 C11 N1 125.1(12)
C12 C11 C10 125.8(14)
N1 C11 C10 109.1(11)
C11 C12 C20 128.4(14)
C11 C12 C13 116.2(12)
C20 C12 C13 115.2(11)
C14 C13 C19 119.5(13)
C14 C13 C12 122.8(12)
C19 C13 C12 117.6(14)
C15 C14 C13 121.4(13)
C15 C14 H14 119.3
C13 C14 H14 119.3
C16 C15 C14 121.7(16)
C16 C15 H15 119.1
C14 C15 H15 119.2
C15 C16 C18 121.3(16)
C15 C16 O1 118.6(17)
C18 C16 O1 120.0(16)
O1 C17 H17A 109.5
O1 C17 H17B 109.5
H17A C17 H17B 109.5
O1 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C16 C18 C19 115.5(15)
C16 C18 H18 122.3
C19 C18 H18 122.2
C13 C19 C18 120.6(15)
C13 C19 H19 119.7
C18 C19 H19 119.7
C21 C20 C12 126.6(12)
C21 C20 S1 108.5(10)
C12 C20 S1 124.8(10)
C20 C21 C22 113.5(13)
C20 C21 H21 123.2
C22 C21 H21 123.3
C23 C22 C21 114.4(13)
C23 C22 H22 122.8
C21 C22 H22 122.8
C22 C23 C24 124.1(13)
C22 C23 S1 108.9(11)
C24 C23 S1 126.7(11)
C26 C24 C23 121.3(14)
C26 C24 C25 122.5(14)
C23 C24 C25 116.2(14)
C24 C25 H25A 109.5
C24 C25 H25B 109.5
H25A C25 H25B 109.5
C24 C25 H25C 109.4
H25A C25 H25C 109.5
H25B C25 H25C 109.5
C24 C26 C28 123.3(13)
C24 C26 C27 121.6(13)
C28 C26 C27 115.2(14)
C26 C27 H27A 109.5
C26 C27 H27B 109.4
H27A C27 H27B 109.5
C26 C27 H27C 109.5
H27A C27 H27C 109.5
H27B C27 H27C 109.5
C29 C28 C26 128.1(12)
C29 C28 S2 109.7(10)
C26 C28 S2 122.1(11)
C28 C29 C30 113.2(12)
C28 C29 H29 123.4
C30 C29 H29 123.4
C31 C30 C29 113.2(14)
C31 C30 H30 123.4
C29 C30 H30 123.4
C30 C31 C32 130.8(14)
C30 C31 S2 109.9(11)
C32 C31 S2 119.2(10)
C40 C32 C31 118.3(14)
C40 C32 C33 123.6(12)
C31 C32 C33 118.1(12)
C39 C33 C34 117.7(14)
C39 C33 C32 123.1(12)
C34 C33 C32 119.2(13)
C35 C34 C33 120.8(13)
C35 C34 H34 119.6
C33 C34 H34 119.6
C36 C35 C34 120.2(14)
C36 C35 H35 119.9
C34 C35 H35 119.9
C35 C36 O2 114.2(15)
C35 C36 C38 118.6(16)
O2 C36 C38 127.1(15)
O2 C37 H37A 109.5
O2 C37 H37B 109.5
H37A C37 H37B 109.5
O2 C37 H37C 109.5
H37A C37 H37C 109.5
H37B C37 H37C 109.5
C39 C38 C36 120.8(16)
C39 C38 H38 119.6
C36 C38 H38 119.6
C38 C39 C33 121.7(14)
C38 C39 H39 119.1
C33 C39 H39 119.1
C32 C40 N2 125.5(12)
C32 C40 C41 129.5(14)
N2 C40 C41 104.9(11)
C42 C41 C40 109.5(13)
C42 C41 H41 125.3
C40 C41 H41 125.3
C41 C42 C43 107.9(12)
C41 C42 H42 126.0
C43 C42 H42 126.0
N2 C43 C7 127.3(12)
N2 C43 C42 107.2(12)
C7 C43 C42 125.4(12)
C8 N1 C11 104.6(10)
C43 N2 C40 110.2(11)
C43 N2 H2A 124.9
C40 N2 H2A 124.9
C17 O1 C16 117.9(14)
C36 O2 C37 115.7(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C23 1.716(13)
S1 C20 1.742(13)
S2 C28 1.732(13)
S2 C31 1.745(15)
C1 C2 1.33(2)
C1 C6 1.310(19)
C1 I1 2.113(13)
C2 C3 1.39(2)
C2 H2 0.9500
C3 C4 1.383(18)
C3 H3 0.9500
C4 C5 1.373(18)
C4 C7 1.497(15)
C5 C6 1.375(18)
C5 H5 0.9500
C6 H6 0.9500
C7 C43 1.394(18)
C7 C8 1.455(17)
C8 N1 1.336(14)
C8 C9 1.463(17)
C9 C10 1.333(16)
C9 H9 0.9500
C10 C11 1.469(17)
C10 H10 0.9500
C11 C12 1.325(16)
C11 N1 1.424(16)
C12 C20 1.433(17)
C12 C13 1.524(18)
C13 C14 1.356(18)
C13 C19 1.405(18)
C14 C15 1.314(18)
C14 H14 0.9500
C15 C16 1.36(2)
C15 H15 0.9500
C16 C18 1.42(2)
C16 O1 1.420(18)
C17 O1 1.376(18)
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 C19 1.409(19)
C18 H18 0.9500
C19 H19 0.9500
C20 C21 1.370(17)
C21 C22 1.428(19)
C21 H21 0.9500
C22 C23 1.367(18)
C22 H22 0.9500
C23 C24 1.463(19)
C24 C26 1.321(19)
C24 C25 1.489(19)
C25 H25A 0.9800
C25 H25B 0.9800
C25 H25C 0.9800
C26 C28 1.453(18)
C26 C27 1.533(18)
C27 H27A 0.9800
C27 H27B 0.9800
C27 H27C 0.9800
C28 C29 1.378(18)
C29 C30 1.462(18)
C29 H29 0.9500
C30 C31 1.363(17)
C30 H30 0.9500
C31 C32 1.485(17)
C32 C40 1.360(17)
C32 C33 1.501(19)
C33 C39 1.391(18)
C33 C34 1.370(17)
C34 C35 1.392(18)
C34 H34 0.9500
C35 C36 1.382(19)
C35 H35 0.9500
C36 O2 1.375(18)
C36 C38 1.37(2)
C37 O2 1.411(17)
C37 H37A 0.9800
C37 H37B 0.9800
C37 H37C 0.9800
C38 C39 1.356(19)
C38 H38 0.9500
C39 H39 0.9500
C40 N2 1.394(16)
C40 C41 1.422(16)
C41 C42 1.349(18)
C41 H41 0.9500
C42 C43 1.414(17)
C42 H42 0.9500
C43 N2 1.358(14)
N2 H2A 0.8800
