#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:06:59 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178885 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/14/4111485.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_4111485
loop_
_publ_author_name
'Reyes García-Zarracino'
'Herbert Höpfl'
_publ_contact_author_address
;
     Centro de Inverstigaciones Químicas
     Universidad Autónoma del Estado de Morelos
     Av. Universidad 1001, C.P. 62210 Cuernavaca
     México
;
_publ_contact_author_email       hhopfl@buzon.uaem.mx
_publ_contact_author_fax         '+52 777-329-7997'
_publ_contact_author_name        'Herbert Höpfl'
_publ_contact_author_phone       '+52 777-329-7997'
_publ_section_title
;
 Self-Assembly of Diorganotin(IV) Oxides (R = Me,nBu, Ph) and
 2,5-Pyridinedicarboxylic Acid to Polymeric and Trinuclear Macrocyclic
 Hybrids with Porous Solid-State Structures: Influence of Substituents and
 Solvent on the Supramolecular Structure
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3120
_journal_page_last               3130
_journal_paper_doi               10.1021/ja0437095
_journal_volume                  127
_journal_year                    2005
_chemical_formula_moiety         'C9 H11 N O5 Sn , C2 H6 O'
_chemical_formula_sum            'C11 H17 N O6 Sn'
_chemical_formula_weight         377.95
_chemical_melting_point          543
_chemical_name_systematic
; 
 ? 
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 111.596(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5608(11)
_cell_length_b                   12.2314(12)
_cell_length_c                   11.4007(11)
_cell_measurement_reflns_used    5260
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.0
_cell_measurement_theta_min      5.0
_cell_volume                     1498.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11452
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    1.724
_exptl_absorpt_correction_T_max  0.733
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.104
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2937
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0352P)²+1.2340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0820
_reflns_number_gt                2644
_reflns_number_total             2937
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0437095si20041202_030437_1.cif
_cod_data_source_block           zareinx
_cod_database_code               4111485
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
Sn1 Sn 0.25170(2) 0.085020(19) 0.59545(2) 0.02957(11) Uani 1 1 d .
N1 N 0.2852(3) 0.2785(2) 0.6191(3) 0.0290(7) Uani 1 1 d .
O1 O 0.0748(2) 0.1747(2) 0.4851(3) 0.0402(7) Uani 1 1 d .
O2 O -0.0275(3) 0.3318(2) 0.4310(3) 0.0553(9) Uani 1 1 d .
O3 O 0.4636(3) 0.0949(2) 0.7327(3) 0.0436(7) Uani 1 1 d .
O4 O 0.3831(3) -0.0677(2) 0.6780(3) 0.0428(7) Uani 1 1 d .
O5 O 0.1235(3) -0.0553(2) 0.5004(3) 0.0483(8) Uani 1 1 d D
H51 H 0.062(3) -0.088(4) 0.512(5) 0.072 Uiso 1 1 d D
H52 H 0.136(5) -0.086(4) 0.438(3) 0.072 Uiso 1 1 d D
C1 C 0.1846(3) 0.3402(3) 0.5599(3) 0.0305(8) Uani 1 1 d .
C2 C 0.1879(4) 0.4526(3) 0.5642(4) 0.0386(9) Uani 1 1 d .
H2 H 0.1166 0.4934 0.5224 0.046 Uiso 1 1 calc R
C3 C 0.2991(4) 0.5040(3) 0.6317(4) 0.0373(9) Uani 1 1 d .
H3 H 0.3033 0.5798 0.6376 0.045 Uiso 1 1 calc R
C4 C 0.4033(3) 0.4413(3) 0.6899(4) 0.0306(8) Uani 1 1 d .
C5 C 0.3926(3) 0.3284(3) 0.6828(4) 0.0319(8) Uani 1 1 d .
H5 H 0.4627 0.2861 0.7239 0.038 Uiso 1 1 calc R
C6 C 0.0663(4) 0.2788(3) 0.4858(4) 0.0363(9) Uani 1 1 d .
C7 C 0.4733(3) -0.0075(3) 0.7357(4) 0.0340(8) Uani 1 1 d .
C8 C 0.1970(5) 0.0795(4) 0.7513(4) 0.0489(11) Uani 1 1 d .
H81 H 0.1630 0.1489 0.7610 0.059 Uiso 1 1 calc R
H82 H 0.2679 0.0632 0.8259 0.059 Uiso 1 1 calc R
H83 H 0.1352 0.0236 0.7384 0.059 Uiso 1 1 calc R
C9 C 0.3091(5) 0.0870(4) 0.4410(4) 0.0475(11) Uani 1 1 d .
H91 H 0.3684 0.1447 0.4518 0.084(18) Uiso 1 1 calc R
H92 H 0.2383 0.0991 0.3649 0.09(2) Uiso 1 1 calc R
H93 H 0.3467 0.0182 0.4357 0.11(2) Uiso 1 1 calc R
O11 O 0.1675(4) 0.8307(3) 0.3225(4) 0.0830(12) Uani 1 1 d .
H11 H 0.1165 0.8294 0.2500 0.124 Uiso 1 1 calc R
C11 C 0.2328(7) 0.7301(6) 0.3499(8) 0.123(3) Uani 1 1 d .
H11A H 0.1855 0.6786 0.3791 0.147 Uiso 1 1 calc R
H11B H 0.2373 0.7012 0.2725 0.147 Uiso 1 1 calc R
C12 C 0.3528(7) 0.7364(6) 0.4398(8) 0.107(2) Uani 1 1 d .
H12A H 0.4033 0.7808 0.4081 0.161 Uiso 1 1 calc R
H12B H 0.3877 0.6643 0.4577 0.161 Uiso 1 1 calc R
H12C H 0.3502 0.7684 0.5157 0.161 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'
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_3
C8 Sn1 C9 178.57(18) .
C8 Sn1 O1 89.66(15) .
C9 Sn1 O1 91.61(16) .
C8 Sn1 O5 91.86(16) .
C9 Sn1 O5 87.76(16) .
O1 Sn1 O5 78.58(10) .
C8 Sn1 O4 89.25(14) .
C9 Sn1 O4 89.33(15) .
O1 Sn1 O4 157.20(9) .
O5 Sn1 O4 78.69(11) .
C8 Sn1 O3 90.17(16) .
C9 Sn1 O3 89.10(16) .
O1 Sn1 O3 147.92(8) .
O5 Sn1 O3 133.48(10) .
O4 Sn1 O3 54.86(9) .
C8 Sn1 N1 91.33(14) .
C9 Sn1 N1 89.72(15) .
O1 Sn1 N1 70.00(9) .
O5 Sn1 N1 148.39(11) .
O4 Sn1 N1 132.80(9) .
O3 Sn1 N1 77.93(9) .
C5 N1 C1 118.5(3) .
C5 N1 Sn1 126.4(2) .
C1 N1 Sn1 115.2(2) .
C6 O1 Sn1 122.5(2) .
C7 O3 Sn1 91.6(2) .
C7 O4 Sn1 91.9(2) .
N1 C1 C2 122.5(3) .
N1 C1 C6 116.0(3) .
C2 C1 C6 121.5(3) .
C1 C2 C3 118.8(3) .
C4 C3 C2 119.1(3) .
C3 C4 C5 118.9(3) .
C3 C4 C7 121.4(3) 2_656
C5 C4 C7 119.6(3) 2_656
N1 C5 C4 122.2(3) .
O2 C6 O1 125.6(4) .
O2 C6 C1 118.2(3) .
O1 C6 C1 116.2(3) .
O4 C7 O3 121.6(3) .
O4 C7 C4 119.1(3) 2_646
O3 C7 C4 119.2(3) 2_646
C12 C11 O11 114.9(6) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sn1 C8 2.095(4) .
Sn1 C9 2.097(4) .
Sn1 O1 2.253(2) .
Sn1 O5 2.266(3) .
Sn1 O4 2.372(3) .
Sn1 O3 2.375(3) .
Sn1 N1 2.397(3) .
N1 C5 1.334(4) .
N1 C1 1.342(4) .
O1 C6 1.278(4) .
O2 C6 1.220(4) .
O3 C7 1.257(4) .
O4 C7 1.248(4) .
C1 C2 1.376(5) .
C1 C6 1.516(5) .
C2 C3 1.382(5) .
C3 C4 1.375(5) .
C4 C5 1.386(5) .
C4 C7 1.502(5) 2_656
C7 C4 1.502(5) 2_646
O11 C11 1.417(7) .
C11 C12 1.391(9) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C8 Sn1 N1 C5 93.6(3) . .
C9 Sn1 N1 C5 -85.4(3) . .
O1 Sn1 N1 C5 -177.2(3) . .
O5 Sn1 N1 C5 -170.7(3) . .
O4 Sn1 N1 C5 3.4(4) . .
O3 Sn1 N1 C5 3.7(3) . .
C8 Sn1 N1 C1 -87.4(3) . .
C9 Sn1 N1 C1 93.5(3) . .
O1 Sn1 N1 C1 1.7(3) . .
O5 Sn1 N1 C1 8.3(4) . .
O4 Sn1 N1 C1 -177.6(2) . .
O3 Sn1 N1 C1 -177.3(3) . .
C8 Sn1 O1 C6 88.9(3) . .
C9 Sn1 O1 C6 -91.8(3) . .
O5 Sn1 O1 C6 -179.2(3) . .
O4 Sn1 O1 C6 176.1(3) . .
O3 Sn1 O1 C6 -0.9(4) . .
N1 Sn1 O1 C6 -2.7(3) . .
C8 Sn1 O3 C7 89.8(3) . .
C9 Sn1 O3 C7 -89.0(3) . .
O1 Sn1 O3 C7 179.4(2) . .
O5 Sn1 O3 C7 -2.9(3) . .
O4 Sn1 O3 C7 0.8(2) . .
N1 Sn1 O3 C7 -178.9(3) . .
C8 Sn1 O4 C7 -91.6(3) . .
C9 Sn1 O4 C7 88.5(3) . .
O1 Sn1 O4 C7 -178.9(3) . .
O5 Sn1 O4 C7 176.4(3) . .
O3 Sn1 O4 C7 -0.8(2) . .
N1 Sn1 O4 C7 -0.5(3) . .
C5 N1 C1 C2 -1.1(6) . .
Sn1 N1 C1 C2 179.9(3) . .
C5 N1 C1 C6 178.1(3) . .
Sn1 N1 C1 C6 -0.9(4) . .
N1 C1 C2 C3 0.3(6) . .
C6 C1 C2 C3 -178.9(4) . .
C1 C2 C3 C4 1.5(6) . .
C2 C3 C4 C5 -2.3(6) . .
C2 C3 C4 C7 179.9(4) . 2_656
C1 N1 C5 C4 0.2(6) . .
Sn1 N1 C5 C4 179.1(3) . .
C3 C4 C5 N1 1.5(6) . .
C7 C4 C5 N1 179.3(3) 2_656 .
Sn1 O1 C6 O2 -177.9(3) . .
Sn1 O1 C6 C1 3.2(5) . .
N1 C1 C6 O2 179.6(4) . .
C2 C1 C6 O2 -1.1(6) . .
N1 C1 C6 O1 -1.3(5) . .
C2 C1 C6 O1 177.9(4) . .
Sn1 O4 C7 O3 1.5(4) . .
Sn1 O4 C7 C4 -178.3(3) . 2_646
Sn1 O3 C7 O4 -1.5(4) . .
Sn1 O3 C7 C4 178.3(3) . 2_646
