#------------------------------------------------------------------------------
#$Date: 2015-06-05 03:13:13 +0300 (Fri, 05 Jun 2015) $
#$Revision: 138049 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/29/4512931.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_4512931
loop_
_publ_author_name
'Titi, Hatem M.'
'Nandi, Goutam'
'Tripuramallu, Bharat Kumar'
'Goldberg, Israel'
_publ_section_title
;
 Exploring Supramolecular Self-Assembly of Tetraarylporphyrins by Halogen
 Interactions. 3. Tin(L)2(A2B2-Porphyrin) Arrays Supported by Concerted
 Halogen and Hydrogen Bonding
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3063
_journal_paper_doi               10.1021/acs.cgd.5b00543
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C54 H32 I4 N6 O2 Sn'
_chemical_formula_sum            'C54 H32 I4 N6 O2 Sn'
_chemical_formula_weight         1423.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90
_cell_angle_beta                 107.8540(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.1417(6)
_cell_length_b                   9.2708(2)
_cell_length_c                   25.2635(6)
_cell_measurement_reflns_used    6061
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.34
_cell_volume                     5827.9(2)
_computing_cell_refinement       'Saint, Bruker-AXS'
_computing_data_collection       'Apex2, Bruker-AXS'
_computing_data_reduction        'Saint, Bruker-AXS'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXTL-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 1.75
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'ApexdDuo, Bruker-AXS'
_diffrn_measurement_method       '1 deg.  φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_laue_measured_fraction_full 0.995
_diffrn_reflns_laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            21086
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.333
_diffrn_reflns_theta_min         1.637
_diffrn_source                   'ImuS micro-focus'
_exptl_absorpt_coefficient_mu    2.598
_exptl_absorpt_correction_T_max  0.599
_exptl_absorpt_correction_T_min  0.510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_description       prism
_exptl_crystal_F_000             2704
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_platon_squeeze_details
;
molecules of disordered DMF solvent
;
_refine_diff_density_max         2.423
_refine_diff_density_min         -2.106
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         7257
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0572P)²+1.1840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1064
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6030
_reflns_number_total             7257
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5b00543_si_001.cif
_cod_data_source_block           ti91sq-1
_cod_depositor_comments
'Adding full bibliography for 4512931--4512939.cif.'
_cod_database_code               4512931
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.510
_shelx_estimated_absorpt_t_max   0.599
_exptl_absorpt_special_details   'Sadabs, Bruker-AXS'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Sn Sn 0.2500 0.2500 0.5000 0.01555(9) Uani 1 2 d S . P
C1 C 0.22498(16) 0.2952(4) 0.35789(14) 0.0193(8) Uani 1 1 d . . .
C2 C 0.26920(16) 0.3702(4) 0.39290(14) 0.0185(7) Uani 1 1 d . . .
C3 C 0.30361(18) 0.4682(5) 0.37593(15) 0.0244(8) Uani 1 1 d . . .
H3 H 0.3003 0.4951 0.3387 0.029 Uiso 1 1 calc R U .
C4 C 0.34171(17) 0.5157(5) 0.42211(15) 0.0246(8) Uani 1 1 d . . .
H4 H 0.3703 0.5798 0.4230 0.030 Uiso 1 1 calc R U .
C5 C 0.33106(16) 0.4518(4) 0.46923(15) 0.0198(8) Uani 1 1 d . . .
C6 C 0.36186(16) 0.4739(4) 0.52598(15) 0.0183(7) Uani 1 1 d . . .
C7 C 0.34942(16) 0.4168(4) 0.57229(15) 0.0194(7) Uani 1 1 d . . .
C8 C 0.37946(19) 0.4444(5) 0.62967(15) 0.0281(9) Uani 1 1 d . . .
H8 H 0.4106 0.5031 0.6426 0.034 Uiso 1 1 calc R U .
C9 C 0.35510(19) 0.3713(5) 0.66152(15) 0.0288(9) Uani 1 1 d . . .
H9 H 0.3661 0.3698 0.7010 0.035 Uiso 1 1 calc R U .
C10 C 0.30996(16) 0.2965(4) 0.62550(14) 0.0189(7) Uani 1 1 d . . .
N11 N 0.28706(13) 0.3635(3) 0.45019(11) 0.0176(6) Uani 1 1 d . . .
N12 N 0.30749(13) 0.3272(3) 0.57162(12) 0.0176(6) Uani 1 1 d . . .
C13 C 0.21519(17) 0.3160(4) 0.29678(14) 0.0199(8) Uani 1 1 d . . .
C14 C 0.2506(2) 0.2587(5) 0.27176(17) 0.0326(11) Uani 1 1 d . . .
H14 H 0.2795 0.1999 0.2928 0.039 Uiso 1 1 calc R U .
C15 C 0.2444(2) 0.2861(5) 0.21562(16) 0.0312(10) Uani 1 1 d . . .
H15 H 0.2687 0.2452 0.1985 0.037 Uiso 1 1 calc R U .
C16 C 0.20352(17) 0.3714(4) 0.18584(14) 0.0220(8) Uani 1 1 d . . .
C17 C 0.16630(19) 0.4262(5) 0.20929(17) 0.0318(10) Uani 1 1 d . . .
H17 H 0.1369 0.4823 0.1877 0.038 Uiso 1 1 calc R U .
C18 C 0.17260(19) 0.3978(5) 0.26537(16) 0.0300(10) Uani 1 1 d . . .
H18 H 0.1473 0.4352 0.2819 0.036 Uiso 1 1 calc R U .
I19 I 0.19961(2) 0.43356(3) 0.10442(2) 0.02185(8) Uani 1 1 d . . .
C20 C 0.41096(16) 0.5613(4) 0.53618(15) 0.0226(8) Uani 1 1 d . . .
C21 C 0.40921(18) 0.7056(5) 0.52231(17) 0.0263(9) Uani 1 1 d . . .
H21 H 0.3754 0.7516 0.5072 0.032 Uiso 1 1 calc R U .
C22 C 0.45635(18) 0.7852(5) 0.53017(18) 0.0278(9) Uani 1 1 d . . .
H22 H 0.4549 0.8846 0.5207 0.033 Uiso 1 1 calc R U .
C23 C 0.50489(18) 0.7167(5) 0.55188(18) 0.0305(9) Uani 1 1 d . . .
C24 C 0.5079(2) 0.5733(6) 0.5667(2) 0.0409(12) Uani 1 1 d . . .
H24 H 0.5418 0.5281 0.5824 0.049 Uiso 1 1 calc R U .
C25 C 0.46069(19) 0.4958(6) 0.5584(2) 0.0365(11) Uani 1 1 d . . .
H25 H 0.4624 0.3965 0.5681 0.044 Uiso 1 1 calc R U .
I26 I 0.57666(2) 0.83485(4) 0.56307(2) 0.04300(11) Uani 1 1 d . . .
O27 O 0.20206(12) 0.4258(3) 0.50060(10) 0.0218(6) Uani 1 1 d . . .
C28 C 0.17599(17) 0.5006(4) 0.45461(15) 0.0225(8) Uani 1 1 d . . .
C29 C 0.1988(2) 0.6207(5) 0.4376(2) 0.0364(10) Uani 1 1 d . U .
H29 H 0.2340 0.6517 0.4581 0.044 Uiso 1 1 calc R U .
C30 C 0.1694(2) 0.6945(7) 0.3902(2) 0.0496(13) Uani 1 1 d . U .
H30 H 0.1838 0.7768 0.3775 0.060 Uiso 1 1 calc R U .
C31 C 0.1194(3) 0.6454(7) 0.3625(3) 0.0554(15) Uani 1 1 d . U .
H31 H 0.0995 0.6971 0.3303 0.066 Uiso 1 1 calc R U .
N32 N 0.0962(2) 0.5326(6) 0.3766(2) 0.0525(12) Uani 1 1 d . U .
C33 C 0.1245(2) 0.4606(6) 0.4229(2) 0.0465(11) Uani 1 1 d . U .
H33 H 0.1084 0.3791 0.4342 0.054 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'
I I -0.4742 1.8119 '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'
Sn Sn -0.6537 1.4246 '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
O27 Sn O27 180.0 7_556 .
O27 Sn N11 90.09(12) 7_556 7_556
O27 Sn N11 89.91(12) . 7_556
O27 Sn N11 89.91(12) 7_556 .
O27 Sn N11 90.09(12) . .
N11 Sn N11 180.00(10) 7_556 .
O27 Sn N12 89.98(11) 7_556 .
O27 Sn N12 90.02(11) . .
N11 Sn N12 89.66(12) 7_556 .
N11 Sn N12 90.35(12) . .
O27 Sn N12 90.02(11) 7_556 7_556
O27 Sn N12 89.98(11) . 7_556
N11 Sn N12 90.35(12) 7_556 7_556
N11 Sn N12 89.65(12) . 7_556
N12 Sn N12 180.0 . 7_556
C2 C1 C10 126.6(3) . 7_556
C2 C1 C13 115.6(3) . .
C10 C1 C13 117.7(3) 7_556 .
N11 C2 C1 125.9(3) . .
N11 C2 C3 107.5(3) . .
C1 C2 C3 126.6(3) . .
C4 C3 C2 108.2(3) . .
C4 C3 H3 125.9 . .
C2 C3 H3 125.9 . .
C3 C4 C5 107.6(4) . .
C3 C4 H4 126.2 . .
C5 C4 H4 126.2 . .
N11 C5 C6 126.3(3) . .
N11 C5 C4 108.1(3) . .
C6 C5 C4 125.6(4) . .
C7 C6 C5 125.2(4) . .
C7 C6 C20 118.1(3) . .
C5 C6 C20 116.6(3) . .
N12 C7 C6 127.2(3) . .
N12 C7 C8 107.8(3) . .
C6 C7 C8 125.0(4) . .
C9 C8 C7 107.4(4) . .
C9 C8 H8 126.3 . .
C7 C8 H8 126.3 . .
C8 C9 C10 108.2(3) . .
C8 C9 H9 125.9 . .
C10 C9 H9 125.9 . .
N12 C10 C1 125.8(3) . 7_556
N12 C10 C9 108.0(3) . .
C1 C10 C9 126.1(3) 7_556 .
C2 N11 C5 108.6(3) . .
C2 N11 Sn 125.7(3) . .
C5 N11 Sn 125.6(2) . .
C10 N12 C7 108.6(3) . .
C10 N12 Sn 126.2(3) . .
C7 N12 Sn 125.3(2) . .
C18 C13 C14 119.1(3) . .
C18 C13 C1 121.1(3) . .
C14 C13 C1 119.8(4) . .
C13 C14 C15 120.7(4) . .
C13 C14 H14 119.7 . .
C15 C14 H14 119.7 . .
C16 C15 C14 119.6(4) . .
C16 C15 H15 120.2 . .
C14 C15 H15 120.2 . .
C15 C16 C17 121.0(3) . .
C15 C16 I19 119.6(3) . .
C17 C16 I19 119.2(3) . .
C16 C17 C18 119.0(4) . .
C16 C17 H17 120.5 . .
C18 C17 H17 120.5 . .
C13 C18 C17 120.6(4) . .
C13 C18 H18 119.7 . .
C17 C18 H18 119.7 . .
C21 C20 C25 118.8(4) . .
C21 C20 C6 122.0(4) . .
C25 C20 C6 119.2(4) . .
C20 C21 C22 121.1(4) . .
C20 C21 H21 119.4 . .
C22 C21 H21 119.4 . .
C23 C22 C21 118.6(4) . .
C23 C22 H22 120.7 . .
C21 C22 H22 120.7 . .
C22 C23 C24 121.6(4) . .
C22 C23 I26 119.1(3) . .
C24 C23 I26 119.3(3) . .
C23 C24 C25 119.0(5) . .
C23 C24 H24 120.5 . .
C25 C24 H24 120.5 . .
C24 C25 C20 120.9(4) . .
C24 C25 H25 119.5 . .
C20 C25 H25 119.5 . .
C28 O27 Sn 123.4(2) . .
O27 C28 C29 121.8(4) . .
O27 C28 C33 120.3(4) . .
C29 C28 C33 117.8(4) . .
C30 C29 C28 118.9(5) . .
C30 C29 H29 120.5 . .
C28 C29 H29 120.5 . .
C31 C30 C29 118.0(6) . .
C31 C30 H30 121.0 . .
C29 C30 H30 121.0 . .
N32 C31 C30 125.4(6) . .
N32 C31 H31 117.3 . .
C30 C31 H31 117.3 . .
C31 N32 C33 116.9(5) . .
N32 C33 C28 122.9(5) . .
N32 C33 H33 118.6 . .
C28 C33 H33 118.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sn O27 2.059(3) 7_556
Sn O27 2.059(3) .
Sn N11 2.092(3) 7_556
Sn N11 2.092(3) .
Sn N12 2.092(3) .
Sn N12 2.092(3) 7_556
C1 C2 1.405(6) .
C1 C10 1.403(5) 7_556
C1 C13 1.498(4) .
C2 N11 1.379(4) .
C2 C3 1.433(5) .
C3 C4 1.354(6) .
C3 H3 0.9500 .
C4 C5 1.431(5) .
C4 H4 0.9500 .
C5 N11 1.373(5) .
C5 C6 1.427(5) .
C6 C7 1.410(5) .
C6 C20 1.472(5) .
C7 N12 1.372(5) .
C7 C8 1.444(5) .
C8 C9 1.352(6) .
C8 H8 0.9500 .
C9 C10 1.429(6) .
C9 H9 0.9500 .
C10 N12 1.372(4) .
C10 C1 1.403(5) 7_556
C13 C18 1.379(6) .
C13 C14 1.377(6) .
C14 C15 1.401(5) .
C14 H14 0.9500 .
C15 C16 1.357(6) .
C15 H15 0.9500 .
C16 C17 1.382(6) .
C16 I19 2.108(3) .
C17 C18 1.400(5) .
C17 H17 0.9500 .
C18 H18 0.9500 .
C20 C21 1.380(6) .
C20 C25 1.388(6) .
C21 C22 1.397(6) .
C21 H21 0.9500 .
C22 C23 1.374(6) .
C22 H22 0.9500 .
C23 C24 1.377(7) .
C23 I26 2.115(4) .
C24 C25 1.388(7) .
C24 H24 0.9500 .
C25 H25 0.9500 .
O27 C28 1.345(5) .
C28 C29 1.393(7) .
C28 C33 1.390(7) .
C29 C30 1.388(7) .
C29 H29 0.9500 .
C30 C31 1.359(9) .
C30 H30 0.9500 .
C31 N32 1.311(8) .
C31 H31 0.9500 .
N32 C33 1.353(7) .
C33 H33 0.9500 .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.025 0.250 403 104 ' '
2 0.000 -0.053 0.750 403 104 ' '
3 0.500 -0.023 0.250 403 104 ' '
4 0.500 -0.016 0.750 403 104 ' '
