#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/36/2233620.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2233620
loop_
_publ_author_name
'Li, Yuanyuan'
'Liu, Jianmin'
'Li, Dacheng'
_publ_section_title
;
 catena-Poly[[trimethyltin(IV)]-μ-1,2,3-benzotriazol-1-ido-κ²N¹:N³]
;
_journal_coeditor_code           RZ2693
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m169
_journal_paper_doi               10.1107/S1600536811055176
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Sn (C H3)3 (C6 H4 N3)]'
_chemical_formula_moiety         'C9 H13 N3 Sn'
_chemical_formula_sum            'C9 H13 N3 Sn'
_chemical_formula_weight         281.93
_chemical_name_systematic
;
catena-Poly[[trimethyltin(IV)]-μ-1,2,3-benzotriazol-1-ido-
κ²N¹:N³]
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.8168(14)
_cell_length_b                   10.6687(9)
_cell_length_c                   7.3518(7)
_cell_measurement_reflns_used    2591
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.119
_cell_measurement_theta_min      2.25
_cell_volume                     1162.14(18)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 1000 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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5549
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    2.162
_exptl_absorpt_correction_T_max  0.5183
_exptl_absorpt_correction_T_min  0.4235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.492
_refine_ls_abs_structure_details 'Flack (1983), 801 Fiedel pairs'
_refine_ls_abs_structure_Flack   -0.11(13)
_refine_ls_extinction_coef       0.025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1920
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0835P)²+1.6416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.1368
_reflns_number_gt                1253
_reflns_number_total             1920
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            rz2693.cif
_cod_data_source_block           I
_cod_database_code               2233620
_cod_database_fobs_code          2233620
loop_
_symmetry_equiv_pos_as_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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N1 0.1848(6) 0.4850(7) 0.0322(11) 0.065(2) Uani d . 1 1
Sn Sn1 0.25035(3) 0.15544(4) 0.3757(6) 0.0479(3) Uani d . 1 1
C C4 -0.0362(7) 0.3651(9) -0.123(2) 0.081(3) Uani d . 1 1
H H4 -0.0862 0.3824 -0.1949 0.097 Uiso calc R 1 1
C C5 0.0335(6) 0.4485(8) -0.120(2) 0.075(3) Uani d . 1 1
H H5 0.0331 0.5201 -0.1917 0.090 Uiso calc R 1 1
N N3 0.1867(5) 0.3116(7) 0.1954(13) 0.067(2) Uani d . 1 1
C C6 0.1055(7) 0.4217(8) -0.0033(13) 0.061(2) Uani d . 1 1
C C7 0.3625(7) 0.2679(9) 0.4423(16) 0.079(3) Uani d . 1 1
H H7A 0.4164 0.2180 0.4382 0.118 Uiso calc R 1 1
H H7B 0.3549 0.3014 0.5625 0.118 Uiso calc R 1 1
H H7C 0.3673 0.3354 0.3565 0.118 Uiso calc R 1 1
C C1 0.1073(7) 0.3123(8) 0.0980(14) 0.060(2) Uani d . 1 1
C C9 0.1374(7) 0.1572(11) 0.555(2) 0.102(5) Uani d . 1 1
H H9A 0.1208 0.2423 0.5812 0.152 Uiso calc R 1 1
H H9B 0.1530 0.1152 0.6662 0.152 Uiso calc R 1 1
H H9C 0.0875 0.1149 0.4987 0.152 Uiso calc R 1 1
N N2 0.2332(6) 0.4168(8) 0.1502(15) 0.067(2) Uani d . 1 1
C C8 0.2505(6) 0.0421(12) 0.139(2) 0.076(4) Uani d . 1 1
H H8A 0.3055 0.0554 0.0726 0.115 Uiso calc R 1 1
H H8B 0.2000 0.0640 0.0637 0.115 Uiso calc R 1 1
H H8C 0.2462 -0.0445 0.1732 0.115 Uiso calc R 1 1
C C2 0.0372(9) 0.2279(11) 0.0931(19) 0.085(4) Uani d . 1 1
H H2 0.0384 0.1557 0.1639 0.102 Uiso calc R 1 1
C C3 -0.0351(10) 0.2533(11) -0.020(2) 0.088(4) Uani d . 1 1
H H3 -0.0828 0.1969 -0.0286 0.106 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.074(5) 0.059(5) 0.062(6) 0.000(4) 0.001(4) 0.014(4)
Sn1 0.0570(4) 0.0380(4) 0.0489(4) 0.0003(2) 0.0018(3) 0.0109(3)
C4 0.083(7) 0.084(7) 0.075(7) 0.001(6) -0.009(9) 0.004(8)
C5 0.082(6) 0.068(6) 0.075(7) 0.001(5) 0.004(9) 0.020(7)
N3 0.073(5) 0.058(5) 0.069(6) 0.001(4) 0.001(5) 0.013(4)
C6 0.073(6) 0.057(5) 0.054(6) 0.005(5) 0.003(5) 0.001(5)
C7 0.097(7) 0.054(6) 0.086(8) 0.002(5) -0.018(6) 0.012(5)
C1 0.067(6) 0.053(5) 0.060(7) -0.005(5) -0.002(5) 0.004(5)
C9 0.083(8) 0.103(10) 0.119(12) 0.018(6) 0.022(9) 0.042(8)
N2 0.087(6) 0.040(4) 0.073(7) -0.001(4) -0.009(5) 0.015(4)
C8 0.096(9) 0.053(6) 0.080(9) -0.003(4) -0.020(6) -0.018(5)
C2 0.087(7) 0.073(7) 0.094(10) -0.005(6) -0.002(8) 0.018(7)
C3 0.078(7) 0.075(8) 0.112(11) -0.010(6) -0.009(8) 0.008(7)
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_site_symmetry_3
_geom_angle
N2 N1 C6 . 108.2(7)
N2 N1 Sn1 4_554 121.1(6)
C6 N1 Sn1 4_554 129.2(6)
C7 Sn1 C8 . 121.0(5)
C7 Sn1 C9 . 118.1(6)
C8 Sn1 C9 . 120.9(5)
C7 Sn1 N3 . 92.5(3)
C8 Sn1 N3 . 86.6(5)
C9 Sn1 N3 . 91.6(4)
C7 Sn1 N1 4_545 90.3(4)
C8 Sn1 N1 4_545 87.7(5)
C9 Sn1 N1 4_545 91.4(4)
N3 Sn1 N1 4_545 174.3(4)
C5 C4 C3 . 122.3(11)
C5 C4 H4 . 118.9
C3 C4 H4 . 118.9
C4 C5 C6 . 117.1(10)
C4 C5 H5 . 121.5
C6 C5 H5 . 121.5
N2 N3 C1 . 107.6(8)
N2 N3 Sn1 . 121.6(6)
C1 N3 Sn1 . 130.2(6)
N1 C6 C1 . 107.1(9)
N1 C6 C5 . 131.8(9)
C1 C6 C5 . 121.1(9)
Sn1 C7 H7A . 109.5
Sn1 C7 H7B . 109.5
H7A C7 H7B . 109.5
Sn1 C7 H7C . 109.5
H7A C7 H7C . 109.5
H7B C7 H7C . 109.5
N3 C1 C2 . 131.0(9)
N3 C1 C6 . 107.5(8)
C2 C1 C6 . 121.5(10)
Sn1 C9 H9A . 109.5
Sn1 C9 H9B . 109.5
H9A C9 H9B . 109.5
Sn1 C9 H9C . 109.5
H9A C9 H9C . 109.5
H9B C9 H9C . 109.5
N1 N2 N3 . 109.6(8)
Sn1 C8 H8A . 109.5
Sn1 C8 H8B . 109.5
H8A C8 H8B . 109.5
Sn1 C8 H8C . 109.5
H8A C8 H8C . 109.5
H8B C8 H8C . 109.5
C3 C2 C1 . 118.2(11)
C3 C2 H2 . 120.9
C1 C2 H2 . 120.9
C2 C3 C4 . 119.7(12)
C2 C3 H3 . 120.1
C4 C3 H3 . 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 N2 . 1.340(11)
N1 C6 . 1.380(12)
N1 Sn1 4_554 2.356(8)
Sn1 C7 . 2.107(10)
Sn1 C8 . 2.120(13)
Sn1 C9 . 2.131(13)
Sn1 N3 . 2.329(8)
Sn1 N1 4_545 2.356(8)
C4 C5 . 1.364(12)
C4 C3 . 1.411(16)
C4 H4 . 0.9300
C5 C6 . 1.397(15)
C5 H5 . 0.9300
N3 N2 . 1.359(11)
N3 C1 . 1.376(12)
C6 C1 . 1.385(12)
C7 H7A . 0.9600
C7 H7B . 0.9600
C7 H7C . 0.9600
C1 C2 . 1.375(13)
C9 H9A . 0.9600
C9 H9B . 0.9600
C9 H9C . 0.9600
C8 H8A . 0.9600
C8 H8B . 0.9600
C8 H8C . 0.9600
C2 C3 . 1.384(19)
C2 H2 . 0.9300
C3 H3 . 0.9300
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_site_symmetry_1
_geom_torsion
C3 C4 C5 C6 . -2.8(17)
C7 Sn1 N3 N2 . 10.1(9)
C8 Sn1 N3 N2 . -110.8(9)
C9 Sn1 N3 N2 . 128.3(9)
C7 Sn1 N3 C1 . -179.4(10)
C8 Sn1 N3 C1 . 59.7(9)
C9 Sn1 N3 C1 . -61.2(10)
N2 N1 C6 C1 . 0.1(11)
Sn1 N1 C6 C1 4_554 166.2(7)
N2 N1 C6 C5 . -177.5(11)
Sn1 N1 C6 C5 4_554 -11.5(16)
C4 C5 C6 N1 . -179.9(10)
C4 C5 C6 C1 . 2.7(15)
N2 N3 C1 C2 . 179.6(12)
Sn1 N3 C1 C2 . 8.2(19)
N2 N3 C1 C6 . -1.6(12)
Sn1 N3 C1 C6 . -173.1(7)
N1 C6 C1 N3 . 0.9(11)
C5 C6 C1 N3 . 178.9(10)
N1 C6 C1 C2 . 179.8(11)
C5 C6 C1 C2 . -2.2(16)
C6 N1 N2 N3 . -1.2(12)
Sn1 N1 N2 N3 4_554 -168.6(7)
C1 N3 N2 N1 . 1.7(12)
Sn1 N3 N2 N1 . 174.1(6)
N3 C1 C2 C3 . -179.8(13)
C6 C1 C2 C3 . 1.6(19)
C1 C2 C3 C4 . -2(2)
C5 C4 C3 C2 . 2(2)
