#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:05:36 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179612 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/76/4507646.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_4507646
loop_
_publ_author_name
'Patra, Ranjan'
'Titi, Hatem M.'
'Goldberg, Israel'
_publ_section_title
;
 Crystal Engineering of Molecular Networks: Tailoring Hydrogen-Bonding
 Self-Assembly of Tin-Tetrapyridylporphyrins with Multidentate Carboxylic
 Acids As Axial Ligands
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1342
_journal_paper_doi               10.1021/cg400007y
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C58 H34 N8 O12 Sn, 4(C2 H6 O S)'
_chemical_formula_sum            'C66 H58 N8 O16 S4 Sn'
_chemical_formula_weight         1466.13
_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                102.8828(11)
_cell_angle_beta                 94.2657(12)
_cell_angle_gamma                91.9333(16)
_cell_formula_units_Z            1
_cell_length_a                   9.7550(2)
_cell_length_b                   11.6924(3)
_cell_length_c                   14.9150(4)
_cell_measurement_reflns_used    5715
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      2.10
_cell_volume                     1651.56(7)
_computing_cell_refinement       Denzo
_computing_data_collection       'Collect, Nonius B.V.'
_computing_data_reduction        'Denzo & Scalepack'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 12.8
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '1 deg. φ & ω scans'
_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  0.0800
_diffrn_reflns_av_sigmaI/netI    0.0882
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14935
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         1.79
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  0.9435
_exptl_absorpt_correction_T_min  0.8669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.892
_refine_diff_density_min         -0.966
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         6375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0561
_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)+(0.0646P)²+0.3098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1299
_reflns_number_gt                4985
_reflns_number_total             6375
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400007y_si_001.cif
_cod_data_source_block           2
_cod_database_code               4507646
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
Sn1 Sn 0.0000 0.5000 0.5000 0.01630(13) Uani 1 2 d S
C2 C 0.2050(4) 0.3823(3) 0.6153(3) 0.0169(8) Uani 1 1 d .
C3 C 0.2325(4) 0.3646(3) 0.7069(3) 0.0177(8) Uani 1 1 d .
H3 H 0.3091 0.3267 0.7280 0.021 Uiso 1 1 calc R
C4 C 0.1308(4) 0.4112(3) 0.7580(3) 0.0176(8) Uani 1 1 d .
H4 H 0.1224 0.4111 0.8210 0.021 Uiso 1 1 calc R
C5 C -0.0374(4) 0.5389(3) 0.3004(2) 0.0154(8) Uani 1 1 d .
C6 C 0.0828(4) 0.4814(3) 0.2751(3) 0.0165(8) Uani 1 1 d .
C7 C 0.1732(4) 0.4304(3) 0.3306(3) 0.0161(8) Uani 1 1 d .
C8 C 0.2937(4) 0.3696(4) 0.3036(3) 0.0226(9) Uani 1 1 d .
H8 H 0.3274 0.3571 0.2442 0.027 Uiso 1 1 calc R
C9 C 0.3519(4) 0.3326(4) 0.3771(3) 0.0237(9) Uani 1 1 d .
H9 H 0.4330 0.2900 0.3786 0.028 Uiso 1 1 calc R
C10 C 0.2673(4) 0.3704(3) 0.4529(3) 0.0168(8) Uani 1 1 d .
C11 C 0.2869(4) 0.3478(3) 0.5415(3) 0.0171(8) Uani 1 1 d .
N12 N -0.0856(3) 0.5585(3) 0.3875(2) 0.0147(7) Uani 1 1 d .
N13 N 0.1611(3) 0.4306(3) 0.4226(2) 0.0167(7) Uani 1 1 d .
C14 C 0.1173(4) 0.4769(3) 0.1777(3) 0.0174(8) Uani 1 1 d .
C15 C 0.1592(4) 0.5793(4) 0.1532(3) 0.0228(9) Uani 1 1 d .
H15 H 0.1664 0.6523 0.1971 0.027 Uiso 1 1 calc R
C16 C 0.1906(5) 0.5731(4) 0.0632(3) 0.0298(10) Uani 1 1 d .
H16 H 0.2195 0.6438 0.0472 0.036 Uiso 1 1 calc R
N17 N 0.1828(4) 0.4742(3) -0.0026(2) 0.0280(8) Uani 1 1 d .
C18 C 0.1416(4) 0.3762(4) 0.0227(3) 0.0265(10) Uani 1 1 d .
H18 H 0.1345 0.3048 -0.0230 0.032 Uiso 1 1 calc R
C19 C 0.1087(4) 0.3719(3) 0.1107(3) 0.0210(9) Uani 1 1 d .
H19 H 0.0813 0.2997 0.1249 0.025 Uiso 1 1 calc R
C20 C 0.4075(4) 0.2776(3) 0.5599(3) 0.0189(8) Uani 1 1 d .
C21 C 0.5423(4) 0.3214(4) 0.5648(3) 0.0228(9) Uani 1 1 d .
H21 H 0.5619 0.3982 0.5562 0.027 Uiso 1 1 calc R
C22 C 0.6487(4) 0.2509(4) 0.5824(3) 0.0259(10) Uani 1 1 d .
H22 H 0.7410 0.2812 0.5856 0.031 Uiso 1 1 calc R
N23 N 0.6265(3) 0.1426(3) 0.5951(2) 0.0254(8) Uani 1 1 d .
C24 C 0.4954(4) 0.1007(4) 0.5918(3) 0.0258(9) Uani 1 1 d .
H24 H 0.4789 0.0242 0.6019 0.031 Uiso 1 1 calc R
C25 C 0.3840(4) 0.1645(3) 0.5742(3) 0.0225(9) Uani 1 1 d .
H25 H 0.2928 0.1321 0.5718 0.027 Uiso 1 1 calc R
O26 O 0.0971(3) 0.6663(2) 0.54078(18) 0.0198(6) Uani 1 1 d .
O27 O 0.2966(3) 0.6507(2) 0.6220(2) 0.0250(6) Uani 1 1 d .
C28 C 0.1999(4) 0.7070(3) 0.6010(3) 0.0187(8) Uani 1 1 d .
C29 C 0.1917(4) 0.8355(3) 0.6457(3) 0.0199(8) Uani 1 1 d .
C30 C 0.0753(4) 0.8949(3) 0.6271(3) 0.0206(9) Uani 1 1 d .
H30 H 0.0030 0.8556 0.5839 0.025 Uiso 1 1 calc R
C31 C 0.0648(4) 1.0119(4) 0.6720(3) 0.0238(9) Uani 1 1 d .
C32 C 0.1693(4) 1.0690(3) 0.7358(3) 0.0232(9) Uani 1 1 d .
H32 H 0.1613 1.1485 0.7667 0.028 Uiso 1 1 calc R
C33 C 0.2855(4) 1.0107(4) 0.7549(3) 0.0232(9) Uani 1 1 d .
C34 C 0.2968(4) 0.8933(4) 0.7090(3) 0.0224(9) Uani 1 1 d .
H34 H 0.3766 0.8532 0.7214 0.027 Uiso 1 1 calc R
C35 C -0.0600(4) 1.0778(4) 0.6554(3) 0.0274(10) Uani 1 1 d .
O36 O -0.1596(3) 1.0126(3) 0.6002(2) 0.0340(8) Uani 1 1 d .
H36 H -0.2415 1.0582 0.6015 0.041 Uiso 1 1 d R
O37 O -0.0693(3) 1.1808(3) 0.6908(3) 0.0422(9) Uani 1 1 d .
C38 C 0.3992(5) 1.0683(4) 0.8242(3) 0.0312(10) Uani 1 1 d .
O39 O 0.3796(3) 1.1793(3) 0.8615(2) 0.0377(8) Uani 1 1 d .
H39 H 0.4470 1.2010 0.9160 0.045 Uiso 1 1 d R
O40 O 0.4996(4) 1.0177(3) 0.8440(3) 0.0623(12) Uani 1 1 d .
S41 S -0.15915(16) 0.95139(13) 0.86901(11) 0.0529(4) Uani 1 1 d .
O42 O -0.0199(4) 0.9015(3) 0.8810(3) 0.0527(10) Uani 1 1 d .
C43 C -0.1361(7) 1.1059(5) 0.9018(5) 0.0622(17) Uani 1 1 d .
H43A H -0.0881 1.1288 0.9637 0.093 Uiso 1 1 calc R
H43B H -0.2261 1.1407 0.9021 0.093 Uiso 1 1 calc R
H43C H -0.0813 1.1339 0.8578 0.093 Uiso 1 1 calc R
C44 C -0.2476(6) 0.9385(5) 0.9674(4) 0.0546(15) Uani 1 1 d .
H44A H -0.2684 0.8553 0.9653 0.082 Uiso 1 1 calc R
H44B H -0.3335 0.9795 0.9669 0.082 Uiso 1 1 calc R
H44C H -0.1893 0.9736 1.0238 0.082 Uiso 1 1 calc R
S45 S -0.44121(16) 1.29672(15) 1.09718(10) 0.0617(5) Uani 1 1 d .
O46 O -0.4331(4) 1.2683(4) 0.9941(2) 0.0663(13) Uani 1 1 d .
C47 C -0.4657(5) 1.4503(6) 1.1283(4) 0.0580(17) Uani 1 1 d .
H47A H -0.3947 1.4927 1.1033 0.087 Uiso 1 1 calc R
H47B H -0.4589 1.4766 1.1957 0.087 Uiso 1 1 calc R
H47C H -0.5568 1.4662 1.1029 0.087 Uiso 1 1 calc R
C48 C -0.2700(6) 1.2998(5) 1.1439(4) 0.0539(15) Uani 1 1 d .
H48A H -0.2364 1.2203 1.1298 0.081 Uiso 1 1 calc R
H48B H -0.2656 1.3292 1.2110 0.081 Uiso 1 1 calc R
H48C H -0.2125 1.3516 1.1171 0.081 Uiso 1 1 calc R
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'
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
O26 Sn1 O26 180.0 . 2_566
O26 Sn1 N12 94.54(11) . 2_566
O26 Sn1 N12 85.45(11) 2_566 2_566
O26 Sn1 N12 85.45(11) . .
O26 Sn1 N12 94.55(11) 2_566 .
N12 Sn1 N12 180.0 2_566 .
O26 Sn1 N13 86.73(11) . 2_566
O26 Sn1 N13 93.27(11) 2_566 2_566
N12 Sn1 N13 89.88(11) 2_566 2_566
N12 Sn1 N13 90.12(11) . 2_566
O26 Sn1 N13 93.27(11) . .
O26 Sn1 N13 86.73(11) 2_566 .
N12 Sn1 N13 90.13(11) 2_566 .
N12 Sn1 N13 89.88(11) . .
N13 Sn1 N13 180.00(14) 2_566 .
N12 C2 C11 125.7(4) 2_566 .
N12 C2 C3 108.3(3) 2_566 .
C11 C2 C3 126.0(3) . .
C4 C3 C2 108.2(3) . .
C4 C3 H3 125.9 . .
C2 C3 H3 125.9 . .
C3 C4 C5 107.6(3) . 2_566
C3 C4 H4 126.2 . .
C5 C4 H4 126.2 2_566 .
N12 C5 C6 125.4(3) . .
N12 C5 C4 108.1(3) . 2_566
C6 C5 C4 126.6(3) . 2_566
C7 C6 C5 127.2(3) . .
C7 C6 C14 117.6(3) . .
C5 C6 C14 115.3(3) . .
N13 C7 C6 125.5(3) . .
N13 C7 C8 107.7(3) . .
C6 C7 C8 126.8(3) . .
C9 C8 C7 108.6(3) . .
C9 C8 H8 125.7 . .
C7 C8 H8 125.7 . .
C8 C9 C10 107.2(3) . .
C8 C9 H9 126.4 . .
C10 C9 H9 126.4 . .
N13 C10 C11 125.4(3) . .
N13 C10 C9 108.1(3) . .
C11 C10 C9 126.5(4) . .
C2 C11 C10 127.3(4) . .
C2 C11 C20 115.6(3) . .
C10 C11 C20 117.0(3) . .
C2 N12 C5 107.9(3) 2_566 .
C2 N12 Sn1 125.9(2) 2_566 .
C5 N12 Sn1 126.2(2) . .
C10 N13 C7 108.5(3) . .
C10 N13 Sn1 125.6(2) . .
C7 N13 Sn1 125.7(2) . .
C15 C14 C19 118.5(4) . .
C15 C14 C6 119.7(3) . .
C19 C14 C6 121.9(3) . .
C16 C15 C14 118.7(4) . .
C16 C15 H15 120.7 . .
C14 C15 H15 120.7 . .
N17 C16 C15 124.3(4) . .
N17 C16 H16 117.8 . .
C15 C16 H16 117.8 . .
C16 N17 C18 116.0(4) . .
N17 C18 C19 124.6(4) . .
N17 C18 H18 117.7 . .
C19 C18 H18 117.7 . .
C18 C19 C14 117.9(4) . .
C18 C19 H19 121.0 . .
C14 C19 H19 121.0 . .
C21 C20 C25 118.4(4) . .
C21 C20 C11 122.3(4) . .
C25 C20 C11 119.3(4) . .
C20 C21 C22 118.9(4) . .
C20 C21 H21 120.6 . .
C22 C21 H21 120.6 . .
N23 C22 C21 122.8(4) . .
N23 C22 H22 118.6 . .
C21 C22 H22 118.6 . .
C22 N23 C24 118.4(4) . .
N23 C24 C25 122.6(4) . .
N23 C24 H24 118.7 . .
C25 C24 H24 118.7 . .
C24 C25 C20 119.0(4) . .
C24 C25 H25 120.5 . .
C20 C25 H25 120.5 . .
C28 O26 Sn1 131.3(2) . .
O27 C28 O26 125.8(4) . .
O27 C28 C29 121.1(4) . .
O26 C28 C29 113.1(3) . .
C34 C29 C30 119.7(3) . .
C34 C29 C28 120.1(4) . .
C30 C29 C28 120.1(4) . .
C29 C30 C31 120.1(4) . .
C29 C30 H30 120.0 . .
C31 C30 H30 120.0 . .
C32 C31 C30 120.1(4) . .
C32 C31 C35 118.3(3) . .
C30 C31 C35 121.5(4) . .
C31 C32 C33 120.4(4) . .
C31 C32 H32 119.8 . .
C33 C32 H32 119.8 . .
C32 C33 C34 119.6(4) . .
C32 C33 C38 122.0(4) . .
C34 C33 C38 118.4(4) . .
C29 C34 C33 120.2(4) . .
C29 C34 H34 119.9 . .
C33 C34 H34 119.9 . .
O37 C35 O36 123.4(4) . .
O37 C35 C31 122.7(4) . .
O36 C35 C31 113.8(3) . .
C35 O36 H36 108.3 . .
O40 C38 O39 123.6(4) . .
O40 C38 C33 123.0(4) . .
O39 C38 C33 113.4(4) . .
C38 O39 H39 105.5 . .
O42 S41 C43 107.4(3) . .
O42 S41 C44 106.6(3) . .
C43 S41 C44 94.8(3) . .
S41 C43 H43A 109.5 . .
S41 C43 H43B 109.5 . .
H43A C43 H43B 109.5 . .
S41 C43 H43C 109.5 . .
H43A C43 H43C 109.5 . .
H43B C43 H43C 109.5 . .
S41 C44 H44A 109.5 . .
S41 C44 H44B 109.5 . .
H44A C44 H44B 109.5 . .
S41 C44 H44C 109.5 . .
H44A C44 H44C 109.5 . .
H44B C44 H44C 109.5 . .
O46 S45 C48 104.9(2) . .
O46 S45 C47 105.5(3) . .
C48 S45 C47 98.1(3) . .
S45 C47 H47A 109.5 . .
S45 C47 H47B 109.5 . .
H47A C47 H47B 109.5 . .
S45 C47 H47C 109.5 . .
H47A C47 H47C 109.5 . .
H47B C47 H47C 109.5 . .
S45 C48 H48A 109.5 . .
S45 C48 H48B 109.5 . .
H48A C48 H48B 109.5 . .
S45 C48 H48C 109.5 . .
H48A C48 H48C 109.5 . .
H48B C48 H48C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sn1 O26 2.076(3) .
Sn1 O26 2.076(3) 2_566
Sn1 N12 2.079(3) 2_566
Sn1 N12 2.079(3) .
Sn1 N13 2.098(3) 2_566
Sn1 N13 2.098(3) .
C2 N12 1.377(5) 2_566
C2 C11 1.403(5) .
C2 C3 1.434(5) .
C3 C4 1.351(5) .
C3 H3 0.9500 .
C4 C5 1.440(5) 2_566
C4 H4 0.9500 .
C5 N12 1.387(4) .
C5 C6 1.405(5) .
C5 C4 1.440(5) 2_566
C6 C7 1.402(5) .
C6 C14 1.504(5) .
C7 N13 1.385(5) .
C7 C8 1.432(5) .
C8 C9 1.360(6) .
C8 H8 0.9500 .
C9 C10 1.446(5) .
C9 H9 0.9500 .
C10 N13 1.377(5) .
C10 C11 1.406(5) .
C11 C20 1.500(5) .
N12 C2 1.377(5) 2_566
C14 C15 1.385(6) .
C14 C19 1.396(5) .
C15 C16 1.385(6) .
C15 H15 0.9500 .
C16 N17 1.335(5) .
C16 H16 0.9500 .
N17 C18 1.342(6) .
C18 C19 1.386(5) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 C21 1.386(6) .
C20 C25 1.400(6) .
C21 C22 1.393(6) .
C21 H21 0.9500 .
C22 N23 1.335(5) .
C22 H22 0.9500 .
N23 C24 1.347(5) .
C24 C25 1.380(6) .
C24 H24 0.9500 .
C25 H25 0.9500 .
O26 C28 1.297(5) .
O27 C28 1.229(5) .
C28 C29 1.509(5) .
C29 C34 1.388(6) .
C29 C30 1.393(5) .
C30 C31 1.393(5) .
C30 H30 0.9500 .
C31 C32 1.385(6) .
C31 C35 1.497(6) .
C32 C33 1.386(6) .
C32 H32 0.9500 .
C33 C34 1.403(6) .
C33 C38 1.490(6) .
C34 H34 0.9500 .
C35 O37 1.212(5) .
C35 O36 1.324(5) .
O36 H36 0.9741 .
C38 O40 1.213(6) .
C38 O39 1.319(5) .
O39 H39 0.9867 .
S41 O42 1.510(4) .
S41 C43 1.765(6) .
S41 C44 1.788(6) .
C43 H43A 0.9800 .
C43 H43B 0.9800 .
C43 H43C 0.9800 .
C44 H44A 0.9800 .
C44 H44B 0.9800 .
C44 H44C 0.9800 .
S45 O46 1.507(4) .
S45 C48 1.757(6) .
S45 C47 1.781(7) .
C47 H47A 0.9800 .
C47 H47B 0.9800 .
C47 H47C 0.9800 .
C48 H48A 0.9800 .
C48 H48B 0.9800 .
C48 H48C 0.9800 .
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
O36 H36 N23 0.97 1.66 2.629(4) 174 1_465
O39 H39 O46 0.99 1.63 2.598(5) 164 1_655
