#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:49:30 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179598 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/62/4506292.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_4506292
loop_
_publ_author_name
'Chandrasekhar, Vadapalli'
'Mohapatra, Chandrajeet'
'Butcher, Ray J.'
_publ_section_title
;
 Synthesis of One- and Two-Dimensional Coordination Polymers Containing
 Organotin Macrocycles. Reactions of (n-Bu3Sn)2O with Pyridine
 Dicarboxylic Acids. Structure-Directing Role of the Ancillary
 4,4′-Bipyridine Ligand
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3285
_journal_paper_doi               10.1021/cg3004189
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C27 H49 N O5 Sn2'
_chemical_formula_weight         705.05
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_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                65.629(5)
_cell_angle_beta                 66.635(5)
_cell_angle_gamma                65.246(5)
_cell_formula_units_Z            2
_cell_length_a                   12.007(5)
_cell_length_b                   12.451(5)
_cell_length_c                   12.779(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1521.4(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8344
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    1.675
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.655417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             716
_exptl_crystal_size_max          .23
_exptl_crystal_size_mid          .17
_exptl_crystal_size_min          .12
_refine_diff_density_max         1.545
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0415
_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)+(0.0555P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                4594
_reflns_number_total             5784
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3004189_si_001.cif
_cod_data_source_block           compound-1
_cod_database_code               4506292
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 0.29008(3) -0.02999(3) 0.14673(3) 0.01876(11) Uani 1 1 d .
Sn2 Sn 0.17866(3) 0.34272(3) -0.02411(3) 0.01776(11) Uani 1 1 d .
O1 O 0.4244(3) -0.2460(3) 0.2182(3) 0.0217(7) Uani 1 1 d .
O2 O 0.6201(3) -0.2451(3) 0.0967(3) 0.0201(7) Uani 1 1 d .
O3 O -0.0421(3) 0.4030(3) 0.0902(3) 0.0196(7) Uani 1 1 d .
O4 O -0.0484(3) 0.2228(3) 0.2344(3) 0.0258(8) Uani 1 1 d .
O5 O 0.1786(3) 0.1609(3) 0.0862(3) 0.0241(8) Uani 1 1 d .
N1 N 0.7129(3) -0.4882(4) 0.1938(3) 0.0181(8) Uani 1 1 d .
C1 C 0.5397(4) -0.2983(4) 0.1818(4) 0.0181(10) Uani 1 1 d .
C2 C 0.5908(4) -0.4332(4) 0.2435(4) 0.0175(10) Uani 1 1 d .
C3 C 0.5176(4) -0.4962(4) 0.3452(4) 0.0209(10) Uani 1 1 d .
H3 H 0.4325 -0.4565 0.3767 0.025 Uiso 1 1 calc R
C4 C 0.5735(4) -0.6203(5) 0.3996(4) 0.0259(11) Uani 1 1 d .
H4 H 0.5276 -0.6644 0.4698 0.031 Uiso 1 1 calc R
C5 C 0.6984(4) -0.6764(5) 0.3470(4) 0.0239(11) Uani 1 1 d .
H5 H 0.7375 -0.7597 0.3805 0.029 Uiso 1 1 calc R
C6 C 0.7649(4) -0.6082(4) 0.2445(4) 0.0167(9) Uani 1 1 d .
C7 C -0.0947(4) 0.3302(5) 0.1856(4) 0.0167(10) Uani 1 1 d .
C8 C 0.4310(4) 0.0241(4) 0.1554(4) 0.0221(10) Uani 1 1 d .
H8A H 0.5107 -0.0427 0.1500 0.026 Uiso 1 1 calc R
H8B H 0.4442 0.0955 0.0874 0.026 Uiso 1 1 calc R
C9 C 0.3959(5) 0.0562(5) 0.2687(4) 0.0270(11) Uani 1 1 d .
H9A H 0.3081 0.1086 0.2835 0.032 Uiso 1 1 calc R
H9B H 0.4490 0.1033 0.2572 0.032 Uiso 1 1 calc R
C10 C 0.4111(5) -0.0574(5) 0.3789(4) 0.0283(12) Uani 1 1 d .
H10A H 0.3668 -0.1101 0.3847 0.034 Uiso 1 1 calc R
H10B H 0.5007 -0.1043 0.3686 0.034 Uiso 1 1 calc R
C11 C 0.3598(6) -0.0237(6) 0.4944(5) 0.0391(14) Uani 1 1 d .
H11A H 0.3894 0.0418 0.4836 0.059 Uiso 1 1 calc R
H11B H 0.3893 -0.0949 0.5566 0.059 Uiso 1 1 calc R
H11C H 0.2684 0.0032 0.5159 0.059 Uiso 1 1 calc R
C12 C 0.1408(4) -0.0671(4) 0.3075(4) 0.0217(10) Uani 1 1 d .
H12A H 0.1355 -0.0246 0.3590 0.026 Uiso 1 1 calc R
H12B H 0.0609 -0.0301 0.2861 0.026 Uiso 1 1 calc R
C13 C 0.1515(4) -0.2012(4) 0.3799(4) 0.0225(11) Uani 1 1 d .
H13A H 0.2291 -0.2385 0.4053 0.027 Uiso 1 1 calc R
H13B H 0.1584 -0.2453 0.3292 0.027 Uiso 1 1 calc R
C14 C 0.0392(5) -0.2171(5) 0.4893(4) 0.0266(11) Uani 1 1 d .
H14A H 0.0355 -0.1780 0.5429 0.032 Uiso 1 1 calc R
H14B H -0.0391 -0.1758 0.4649 0.032 Uiso 1 1 calc R
C15 C 0.0489(5) -0.3517(5) 0.5548(5) 0.0328(13) Uani 1 1 d .
H15A H 0.0515 -0.3905 0.5024 0.049 Uiso 1 1 calc R
H15B H -0.0238 -0.3577 0.6228 0.049 Uiso 1 1 calc R
H15C H 0.1252 -0.3925 0.5809 0.049 Uiso 1 1 calc R
C16 C 0.2925(4) -0.0847(5) 0.0088(4) 0.0249(11) Uani 1 1 d .
H16A H 0.3080 -0.0209 -0.0664 0.030 Uiso 1 1 calc R
H16B H 0.3625 -0.1600 0.0026 0.030 Uiso 1 1 calc R
C17 C 0.1686(5) -0.1071(5) 0.0288(4) 0.0270(11) Uani 1 1 d .
H17A H 0.1535 -0.1710 0.1040 0.032 Uiso 1 1 calc R
H17B H 0.0987 -0.0318 0.0356 0.032 Uiso 1 1 calc R
C18 C 0.1678(5) -0.1460(5) -0.0699(5) 0.0323(12) Uani 1 1 d .
H18A H 0.2361 -0.2225 -0.0754 0.039 Uiso 1 1 calc R
H18B H 0.0880 -0.1622 -0.0482 0.039 Uiso 1 1 calc R
C19 C 0.1838(6) -0.0496(6) -0.1915(5) 0.0384(14) Uani 1 1 d .
H19A H 0.1192 0.0278 -0.1860 0.058 Uiso 1 1 calc R
H19B H 0.1761 -0.0766 -0.2479 0.058 Uiso 1 1 calc R
H19C H 0.2663 -0.0390 -0.2173 0.058 Uiso 1 1 calc R
C20 C 0.1052(4) 0.3431(5) -0.1506(4) 0.0216(10) Uani 1 1 d .
H20A H 0.0539 0.2871 -0.1102 0.026 Uiso 1 1 calc R
H20B H 0.0487 0.4255 -0.1772 0.026 Uiso 1 1 calc R
C21 C 0.2017(5) 0.3067(5) -0.2603(4) 0.0265(11) Uani 1 1 d .
H21A H 0.2579 0.2238 -0.2349 0.032 Uiso 1 1 calc R
H21B H 0.2532 0.3625 -0.3018 0.032 Uiso 1 1 calc R
C22 C 0.1416(5) 0.3099(5) -0.3472(4) 0.0259(11) Uani 1 1 d .
H22A H 0.0717 0.3860 -0.3588 0.031 Uiso 1 1 calc R
H22B H 0.1069 0.2412 -0.3126 0.031 Uiso 1 1 calc R
C23 C 0.2372(5) 0.3020(6) -0.4688(5) 0.0434(16) Uani 1 1 d .
H23A H 0.2674 0.3729 -0.5060 0.065 Uiso 1 1 calc R
H23B H 0.1962 0.3002 -0.5187 0.065 Uiso 1 1 calc R
H23C H 0.3078 0.2280 -0.4576 0.065 Uiso 1 1 calc R
C24 C 0.2140(4) 0.3969(4) 0.0942(4) 0.0208(10) Uani 1 1 d .
H24A H 0.1628 0.4824 0.0890 0.025 Uiso 1 1 calc R
H24B H 0.1839 0.3473 0.1749 0.025 Uiso 1 1 calc R
C25 C 0.3516(5) 0.3864(5) 0.0752(4) 0.0256(11) Uani 1 1 d .
H25A H 0.3801 0.4422 -0.0022 0.031 Uiso 1 1 calc R
H25B H 0.4050 0.3028 0.0742 0.031 Uiso 1 1 calc R
C26 C 0.3700(5) 0.4166(5) 0.1710(5) 0.0319(12) Uani 1 1 d .
H26A H 0.3403 0.3618 0.2486 0.038 Uiso 1 1 calc R
H26B H 0.4602 0.4006 0.1572 0.038 Uiso 1 1 calc R
C27 C 0.3004(6) 0.5489(6) 0.1728(6) 0.0496(17) Uani 1 1 d .
H27A H 0.3304 0.6038 0.0968 0.074 Uiso 1 1 calc R
H27B H 0.3159 0.5623 0.2340 0.074 Uiso 1 1 calc R
H27C H 0.2107 0.5648 0.1889 0.074 Uiso 1 1 calc R
H1B H 0.128(5) 0.153(5) 0.140(5) 0.022(16) Uiso 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'
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
C8 Sn1 C16 128.19(18) . .
C8 Sn1 C12 117.37(19) . .
C16 Sn1 C12 113.46(19) . .
C8 Sn1 O5 91.61(16) . .
C16 Sn1 O5 95.82(17) . .
C12 Sn1 O5 92.34(16) . .
C8 Sn1 O1 85.85(15) . .
C16 Sn1 O1 86.11(16) . .
C12 Sn1 O1 88.45(14) . .
O5 Sn1 O1 177.43(12) . .
O5 Sn2 C24 97.47(17) . .
O5 Sn2 C20 95.49(17) . .
C24 Sn2 C20 162.85(18) . .
O5 Sn2 O2 81.86(12) . 2_655
C24 Sn2 O2 95.57(15) . 2_655
C20 Sn2 O2 97.35(15) . 2_655
O5 Sn2 O3 84.81(12) . .
C24 Sn2 O3 84.34(15) . .
C20 Sn2 O3 85.70(15) . .
O2 Sn2 O3 166.54(11) 2_655 .
O5 Sn2 N1 150.71(12) . 2_655
C24 Sn2 N1 88.61(16) . 2_655
C20 Sn2 N1 85.55(16) . 2_655
O2 Sn2 N1 69.01(12) 2_655 2_655
O3 Sn2 N1 124.40(11) . 2_655
C1 O1 Sn1 131.3(3) . .
C1 O2 Sn2 124.5(3) . 2_655
C7 O3 Sn2 124.4(3) . .
Sn2 O5 Sn1 147.11(18) . .
C6 N1 C2 118.6(4) . .
C6 N1 Sn2 127.5(3) . 2_655
C2 N1 Sn2 113.6(3) . 2_655
O1 C1 O2 125.2(4) . .
O1 C1 C2 117.7(4) . .
O2 C1 C2 117.1(4) . .
N1 C2 C3 122.3(4) . .
N1 C2 C1 115.4(4) . .
C3 C2 C1 122.3(4) . .
C2 C3 C4 118.7(4) . .
C5 C4 C3 118.5(4) . .
C6 C5 C4 119.5(4) . .
N1 C6 C5 122.3(4) . .
N1 C6 C7 117.8(4) . 1_645
C5 C6 C7 119.9(4) . 1_645
O4 C7 O3 128.7(4) . .
O4 C7 C6 116.9(4) . 1_465
O3 C7 C6 114.5(4) . 1_465
C9 C8 Sn1 113.0(3) . .
C8 C9 C10 113.7(4) . .
C11 C10 C9 113.1(4) . .
C13 C12 Sn1 117.8(3) . .
C12 C13 C14 113.5(4) . .
C15 C14 C13 112.1(4) . .
C17 C16 Sn1 113.4(3) . .
C18 C17 C16 114.4(4) . .
C19 C18 C17 113.5(5) . .
C21 C20 Sn2 116.8(3) . .
C20 C21 C22 113.7(4) . .
C21 C22 C23 112.6(4) . .
C25 C24 Sn2 117.3(3) . .
C24 C25 C26 113.7(4) . .
C27 C26 C25 113.3(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sn1 C8 2.120(5) .
Sn1 C16 2.122(5) .
Sn1 C12 2.153(4) .
Sn1 O5 2.163(4) .
Sn1 O1 2.485(3) .
Sn2 O5 2.117(4) .
Sn2 C24 2.124(5) .
Sn2 C20 2.125(5) .
Sn2 O2 2.207(3) 2_655
Sn2 O3 2.427(3) .
Sn2 N1 2.484(4) 2_655
O1 C1 1.242(5) .
O2 C1 1.288(5) .
O2 Sn2 2.207(3) 2_655
O3 C7 1.290(5) .
O4 C7 1.204(6) .
N1 C6 1.335(6) .
N1 C2 1.343(5) .
N1 Sn2 2.484(4) 2_655
C1 C2 1.499(6) .
C2 C3 1.381(6) .
C3 C4 1.391(7) .
C4 C5 1.379(6) .
C5 C6 1.376(6) .
C6 C7 1.544(6) 1_645
C7 C6 1.544(6) 1_465
C8 C9 1.511(7) .
C9 C10 1.536(7) .
C10 C11 1.519(7) .
C12 C13 1.517(7) .
C13 C14 1.520(6) .
C14 C15 1.510(7) .
C16 C17 1.531(7) .
C17 C18 1.530(7) .
C18 C19 1.519(7) .
C20 C21 1.519(6) .
C21 C22 1.526(7) .
C22 C23 1.536(7) .
C24 C25 1.528(6) .
C25 C26 1.533(7) .
C26 C27 1.509(8) .
