# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2002

data_global #  *** Added by check_cif

_journal_coden_Cambridge      207

loop_
_publ_author_name
'Wang, Quanrui'
'Ding, Zongbiao'
'Liu, Yi'
'Tao, Fenggang'
'Yang, Haiyan'

_publ_contact_author_name	  'Dr Quanrui Wang'
_publ_contact_author_addess       
;
Department of Chemistry, 
Fudan University
200433 Shanghai, 
PR China
;

_publ_contact_author_email       'QRWANGB@ONLINE.SH.CN'

_publ_requested_journal           'Perkin Transactions 1'
_publ_section_title               
;
A facile route to poly (1,2,4-triazol-5-yl) alkane derivatives
;

data_b110059a 

_database_code_CSD	149370


_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum             'C59 H68 Cl40 N12 O4 Sb4' 
_chemical_formula_weight          2914.25 

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' 
'O'  'O'   0.0106   0.0060 
'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' 
'Cl'  'Cl'   0.1484   0.1585 
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
'Sb'  'Sb'  -0.5866   1.5461 
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

_symmetry_cell_setting            tetragonal 
_symmetry_space_group_name_H-M    'P 42/n' 

loop_ 
_symmetry_equiv_pos_as_xyz 
'x, y, z' 
'-x+1/2, -y+1/2, z' 
'-y, x+1/2, z+1/2' 
'y+1/2, -x, z+1/2' 
'-x, -y, -z' 
'x-1/2, y-1/2, -z' 
'y, -x-1/2, -z-1/2' 
'-y-1/2, x, -z-1/2' 

_cell_length_a                    20.310(4) 
_cell_length_b                    20.310(4) 
_cell_length_c                    13.971(3) 
_cell_angle_alpha                 90.00(2) 
_cell_angle_beta                  90.00(2) 
_cell_angle_gamma                 90.00(2) 
_cell_volume                      5763(2) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     25 
_cell_measurement_theta_min       14.52 
_cell_measurement_theta_max       21.65 

_exptl_crystal_description        'prismatic' 
_exptl_crystal_colour             'colorless' 
_exptl_crystal_size_max           0.30 
_exptl_crystal_size_mid           0.25 
_exptl_crystal_size_min           0.20 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.680 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              2844 
_exptl_absorpt_coefficient_mu     1.898 
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_details ? 
_exptl_absorpt_correction_T_min   0.5998 
_exptl_absorpt_correction_T_max   0.7027 

_exptl_special_details 
; 
? 
; 

_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71069 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'AFC7R' 
_diffrn_measurement_method        'omega/2-theta scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  200 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         -9.49 
_diffrn_reflns_number             6977 
_diffrn_reflns_av_R_equivalents   0.0289 
_diffrn_reflns_av_sigmaI/netI     0.0780 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        26 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        26 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        18 
_diffrn_reflns_theta_min          2.48 
_diffrn_reflns_theta_max          27.52 
_reflns_number_total              6614 
_reflns_number_gt                 2486 
_reflns_threshold_expression      >2sigma(I) 

_computing_data_collection        'MSC/AFC Diffractometer Contol' 
_computing_cell_refinement        'MSC/AFC Diffractometer Contol' 
_computing_data_reduction         'teXsan: PROCESS (MSC)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'ORTEP-3 for Windows V1.05(Farrugia, 1999)' 
_computing_publication_material   'SHELXL-97 (Sheldrick, 1997)' 

_refine_special_details 
; 
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
goodness of fit S are based on F^2^, conventional R-factors R are based 
on F, with F set to zero for negative F^2^. The threshold expression of 
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
not relevant to the choice of reflections for refinement.  R-factors based 
on F^2^ are statistically about twice as large as those based on F, and R- 
factors based on ALL data will be even larger. 
; 

_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1445P)^2^+5.4200P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          6614 
_refine_ls_number_parameters      202 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.2063 
_refine_ls_R_factor_gt            0.0796 
_refine_ls_wR_factor_ref          0.3040 
_refine_ls_wR_factor_gt           0.2280 
_refine_ls_goodness_of_fit_ref    1.016 
_refine_ls_restrained_S_all       1.016 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 

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_calc_flag 
_atom_site_refinement_flags 
_atom_site_disorder_assembly 
_atom_site_disorder_group 
Sb1 Sb 0.48499(4) 0.68867(3) 0.04386(5) 0.0741(3) Uani 1 d . . . 
Cl1 Cl 0.14639(16) 0.06058(17) 0.1334(2) 0.1048(10) Uani 1 d . . . 
Cl2 Cl 0.2236(3) -0.1656(3) 0.2913(4) 0.196(3) Uani 1 d . . . 
Cl3 Cl 0.3359(2) -0.0825(2) -0.0319(3) 0.1455(16) Uani 1 d . . . 
Cl4 Cl 0.60090(15) 0.68484(15) 0.0546(2) 0.0973(9) Uani 1 d . . . 
Cl5 Cl 0.36943(17) 0.6923(2) 0.0337(3) 0.1249(13) Uani 1 d . . . 
Cl6 Cl 0.4791(2) 0.68169(18) 0.2132(2) 0.1210(13) Uani 1 d . . . 
Cl7 Cl 0.49553(18) 0.6930(2) -0.1237(2) 0.1240(13) Uani 1 d . . . 
Cl8 Cl 0.48851(18) 0.80439(14) 0.0519(3) 0.1124(11) Uani 1 d . . . 
Cl9 Cl 0.4820(2) 0.57293(15) 0.0395(3) 0.1167(12) Uani 1 d . . . 
O1 O 0.2997(3) 0.1765(3) 0.1349(5) 0.079(2) Uani 1 d . . . 
N1 N 0.2045(5) 0.0357(5) -0.0901(7) 0.084(3) Uani 1 d . . . 
N2 N 0.2458(4) 0.0317(4) -0.0143(6) 0.076(2) Uani 1 d . . . 
N3 N 0.2774(5) 0.1136(4) -0.1025(7) 0.091(3) Uani 1 d . . . 
C1 C 0.2247(6) 0.0879(6) -0.1433(9) 0.086(3) Uiso 1 d . . . 
C2 C 0.2901(5) 0.0817(5) -0.0250(8) 0.074(3) Uiso 1 d . . . 
C3 C 0.1926(6) 0.1099(6) -0.2337(8) 0.105(4) Uiso 1 d . . . 
H3A H 0.2086 0.0838 -0.2861 0.157 Uiso 1 calc R . . 
H3B H 0.2027 0.1554 -0.2449 0.157 Uiso 1 calc R . . 
H3C H 0.1458 0.1045 -0.2283 0.157 Uiso 1 calc R . . 
C4 C 0.1495(6) -0.0106(6) -0.1062(9) 0.095(3) Uiso 1 d . . . 
H4A H 0.1313 -0.0237 -0.0449 0.114 Uiso 1 calc R . . 
H4B H 0.1150 0.0117 -0.1418 0.114 Uiso 1 calc R . . 
C5 C 0.1700(7) -0.0700(7) -0.1594(10) 0.120(5) Uiso 1 d . . . 
H5A H 0.1855 -0.0575 -0.2216 0.181 Uiso 1 calc R . . 
H5B H 0.1331 -0.0992 -0.1660 0.181 Uiso 1 calc R . . 
H5C H 0.2046 -0.0918 -0.1250 0.181 Uiso 1 calc R . . 
C6 C 0.2398(5) -0.0168(5) 0.0589(8) 0.076(3) Uiso 1 d . . . 
C7 C 0.1955(6) -0.0078(6) 0.1320(8) 0.084(3) Uiso 1 d . . . 
C8 C 0.1918(6) -0.0558(6) 0.2048(9) 0.101(4) Uiso 1 d . . . 
H8 H 0.1622 -0.0510 0.2552 0.121 Uiso 1 calc R . . 
C9 C 0.2308(7) -0.1074(7) 0.2002(9) 0.106(4) Uiso 1 d . . . 
C10 C 0.2753(7) -0.1176(7) 0.1324(9) 0.108(4) Uiso 1 d . . . 
H10 H 0.3027 -0.1544 0.1340 0.130 Uiso 1 calc R . . 
C11 C 0.2799(6) -0.0724(6) 0.0597(9) 0.095(3) Uiso 1 d . . . 
C12 C 0.3472(6) 0.0913(6) 0.0420(7) 0.087(3) Uiso 1 d . . . 
H12A H 0.3414 0.0628 0.0971 0.104 Uiso 1 calc R . . 
H12B H 0.3874 0.0781 0.0098 0.104 Uiso 1 calc R . . 
C13 C 0.3543(6) 0.1605(6) 0.0755(8) 0.089(3) Uiso 1 d . . . 
H13A H 0.3950 0.1654 0.1113 0.107 Uiso 1 calc R . . 
H13B H 0.3558 0.1901 0.0210 0.107 Uiso 1 calc R . . 
C14 C 0.3089(5) 0.2362(5) 0.1873(7) 0.072(3) Uiso 1 d . . . 
H14A H 0.3152 0.2725 0.1431 0.086 Uiso 1 calc R . . 
H14B H 0.3480 0.2326 0.2267 0.086 Uiso 1 calc R . . 
C15 C 0.2500 0.2500 0.2500 0.059(4) Uiso 1 d S . . 
C16 C 1.014(2) 0.018(2) 0.682(3) 0.179(15) Uiso 0.50 d P . . 
Cl10 Cl 0.9338(5) 0.0123(5) 0.6175(7) 0.150(3) Uiso 0.50 d P . . 
Cl11 Cl 1.0165(9) -0.0647(9) 0.7252(12) 0.131(5) Uiso 0.25 d P . . 
Cl12 Cl 1.0518(13) -0.0314(13) 0.6642(18) 0.192(9) Uiso 0.25 d P . . 

loop_ 
_atom_site_aniso_label 
_atom_site_aniso_U_11 
_atom_site_aniso_U_22 
_atom_site_aniso_U_33 
_atom_site_aniso_U_23 
_atom_site_aniso_U_13 
_atom_site_aniso_U_12 
Sb1 0.0776(5) 0.0665(5) 0.0780(5) 0.0061(4) -0.0044(4) -0.0068(3) 
Cl1 0.101(2) 0.109(2) 0.105(2) -0.0076(19) 0.0197(18) 0.0042(18) 
Cl2 0.254(6) 0.165(4) 0.168(4) 0.086(4) -0.074(4) -0.066(4) 
Cl3 0.138(3) 0.133(3) 0.166(4) -0.029(3) 0.006(3) 0.051(3) 
Cl4 0.0818(19) 0.089(2) 0.121(2) 0.0090(18) -0.0198(17) 0.0046(15) 
Cl5 0.078(2) 0.145(3) 0.152(3) 0.022(3) 0.005(2) -0.018(2) 
Cl6 0.173(4) 0.115(3) 0.0744(19) 0.0014(18) 0.008(2) -0.030(2) 
Cl7 0.116(3) 0.179(4) 0.077(2) 0.021(2) -0.0098(19) 0.000(2) 
Cl8 0.111(2) 0.0661(18) 0.160(3) 0.0191(19) 0.014(2) 0.0015(16) 
Cl9 0.137(3) 0.0659(18) 0.147(3) -0.0118(19) -0.026(2) -0.0167(17) 
O1 0.078(5) 0.080(5) 0.079(5) -0.022(4) 0.013(4) -0.014(4) 
N1 0.087(6) 0.090(6) 0.076(6) -0.010(5) 0.009(5) 0.007(5) 
N2 0.068(5) 0.092(6) 0.067(5) 0.005(5) 0.000(4) -0.002(5) 
N3 0.096(7) 0.073(6) 0.104(7) -0.006(5) 0.026(6) -0.001(5) 

_geom_special_details 
; 
All esds (except the esd in the dihedral angle between two l.s. planes) 
are estimated using the full covariance matrix.  The cell esds are taken 
into account individually in the estimation of esds in distances, angles 
and torsion angles; correlations between esds in cell parameters are only 
used when they are defined by crystal symmetry.  An approximate (isotropic) 
treatment of cell esds is used for estimating esds involving l.s. planes. 
; 

loop_ 
_geom_bond_atom_site_label_1 
_geom_bond_atom_site_label_2 
_geom_bond_distance 
_geom_bond_site_symmetry_2 
_geom_bond_publ_flag 
Sb1 Cl9 2.352(3) . ? 
Sb1 Cl5 2.352(4) . ? 
Sb1 Cl7 2.353(4) . ? 
Sb1 Cl8 2.354(3) . ? 
Sb1 Cl4 2.360(3) . ? 
Sb1 Cl6 2.373(3) . ? 
Cl1 C7 1.709(12) . ? 
Cl2 C9 1.743(14) . ? 
Cl3 C11 1.726(13) . ? 
O1 C13 1.423(12) . ? 
O1 C14 1.429(11) . ? 
N1 N2 1.354(11) . ? 
N1 C1 1.357(13) . ? 
N1 C4 1.478(14) . ? 
N2 C2 1.365(13) . ? 
N2 C6 1.426(13) . ? 
N3 C2 1.288(12) . ? 
N3 C1 1.322(14) . ? 
C1 C3 1.489(15) . ? 
C2 C12 1.502(14) . ? 
C4 C5 1.476(16) . ? 
C6 C7 1.374(14) . ? 
C6 C11 1.392(15) . ? 
C7 C8 1.410(15) . ? 
C8 C9 1.316(16) . ? 
C9 C10 1.327(16) . ? 
C10 C11 1.373(16) . ? 
C12 C13 1.489(15) . ? 
C14 C15 1.508(9) . ? 
C15 C14 1.508(9) 7_566 ? 
C15 C14 1.508(9) 8_656 ? 
C15 C14 1.508(9) 2 ? 
C16 Cl12 1.28(4) . ? 
C16 Cl11 1.78(4) . ? 
C16 Cl10 1.87(4) . ? 
Cl11 Cl12 1.30(3) . ? 

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 
_geom_angle_publ_flag 
Cl9 Sb1 Cl5 90.22(14) . . ? 
Cl9 Sb1 Cl7 90.80(14) . . ? 
Cl5 Sb1 Cl7 91.71(13) . . ? 
Cl9 Sb1 Cl8 178.74(13) . . ? 
Cl5 Sb1 Cl8 90.11(13) . . ? 
Cl7 Sb1 Cl8 90.40(14) . . ? 
Cl9 Sb1 Cl4 89.69(12) . . ? 
Cl5 Sb1 Cl4 179.79(12) . . ? 
Cl7 Sb1 Cl4 88.49(12) . . ? 
Cl8 Sb1 Cl4 89.97(11) . . ? 
Cl9 Sb1 Cl6 87.99(13) . . ? 
Cl5 Sb1 Cl6 90.64(14) . . ? 
Cl7 Sb1 Cl6 177.36(15) . . ? 
Cl8 Sb1 Cl6 90.79(13) . . ? 
Cl4 Sb1 Cl6 89.16(13) . . ? 
C13 O1 C14 113.0(7) . . ? 
N2 N1 C1 106.7(9) . . ? 
N2 N1 C4 123.4(9) . . ? 
C1 N1 C4 129.9(10) . . ? 
N1 N2 C2 106.2(8) . . ? 
N1 N2 C6 123.3(9) . . ? 
C2 N2 C6 130.5(9) . . ? 
C2 N3 C1 109.0(10) . . ? 
N3 C1 N1 108.5(10) . . ? 
N3 C1 C3 127.0(12) . . ? 
N1 C1 C3 124.5(11) . . ? 
N3 C2 N2 109.5(9) . . ? 
N3 C2 C12 127.8(11) . . ? 
N2 C2 C12 122.4(10) . . ? 
C5 C4 N1 112.5(11) . . ? 
C7 C6 C11 119.0(10) . . ? 
C7 C6 N2 119.9(10) . . ? 
C11 C6 N2 121.0(10) . . ? 
C6 C7 C8 118.6(11) . . ? 
C6 C7 Cl1 119.9(9) . . ? 
C8 C7 Cl1 121.4(9) . . ? 
C9 C8 C7 118.9(13) . . ? 
C8 C9 C10 124.8(14) . . ? 
C8 C9 Cl2 117.1(11) . . ? 
C10 C9 Cl2 118.2(11) . . ? 
C9 C10 C11 118.0(14) . . ? 
C10 C11 C6 120.7(12) . . ? 
C10 C11 Cl3 120.9(10) . . ? 
C6 C11 Cl3 118.5(9) . . ? 
C13 C12 C2 113.1(10) . . ? 
O1 C13 C12 108.9(9) . . ? 
O1 C14 C15 110.6(7) . . ? 
C14 C15 C14 109.0(8) 7_566 8_656 ? 
C14 C15 C14 109.7(4) 7_566 . ? 
C14 C15 C14 109.7(4) 8_656 . ? 
C14 C15 C14 109.7(4) 7_566 2 ? 
C14 C15 C14 109.7(4) 8_656 2 ? 
C14 C15 C14 109.0(8) . 2 ? 
Cl12 C16 Cl11 47.0(19) . . ? 
Cl12 C16 Cl10 113(3) . . ? 
Cl11 C16 Cl10 98(2) . . ? 
Cl12 Cl11 C16 46.0(16) . . ? 
C16 Cl12 Cl11 87(3) . . ? 

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_2 
_geom_torsion_site_symmetry_3 
_geom_torsion_site_symmetry_4 
_geom_torsion_publ_flag 
C1 N1 N2 C2 -0.3(11) . . . . ? 
C4 N1 N2 C2 179.1(10) . . . . ? 
C1 N1 N2 C6 179.1(10) . . . . ? 
C4 N1 N2 C6 -1.4(15) . . . . ? 
C2 N3 C1 N1 -2.0(13) . . . . ? 
C2 N3 C1 C3 179.5(11) . . . . ? 
N2 N1 C1 N3 1.4(12) . . . . ? 
C4 N1 C1 N3 -178.0(10) . . . . ? 
N2 N1 C1 C3 179.9(10) . . . . ? 
C4 N1 C1 C3 0.5(18) . . . . ? 
C1 N3 C2 N2 1.8(13) . . . . ? 
C1 N3 C2 C12 176.6(11) . . . . ? 
N1 N2 C2 N3 -0.9(11) . . . . ? 
C6 N2 C2 N3 179.7(10) . . . . ? 
N1 N2 C2 C12 -176.0(9) . . . . ? 
C6 N2 C2 C12 4.6(17) . . . . ? 
N2 N1 C4 C5 -86.9(13) . . . . ? 
C1 N1 C4 C5 92.5(14) . . . . ? 
N1 N2 C6 C7 -81.6(13) . . . . ? 
C2 N2 C6 C7 97.8(14) . . . . ? 
N1 N2 C6 C11 100.9(12) . . . . ? 
C2 N2 C6 C11 -79.8(15) . . . . ? 
C11 C6 C7 C8 -0.8(16) . . . . ? 
N2 C6 C7 C8 -178.4(10) . . . . ? 
C11 C6 C7 Cl1 179.2(9) . . . . ? 
N2 C6 C7 Cl1 1.6(15) . . . . ? 
C6 C7 C8 C9 0.0(18) . . . . ? 
Cl1 C7 C8 C9 -179.9(10) . . . . ? 
C7 C8 C9 C10 2(2) . . . . ? 
C7 C8 C9 Cl2 -179.4(9) . . . . ? 
C8 C9 C10 C11 -2(2) . . . . ? 
Cl2 C9 C10 C11 178.7(10) . . . . ? 
C9 C10 C11 C6 1(2) . . . . ? 
C9 C10 C11 Cl3 -179.3(11) . . . . ? 
C7 C6 C11 C10 0.1(18) . . . . ? 
N2 C6 C11 C10 177.6(11) . . . . ? 
C7 C6 C11 Cl3 -179.2(9) . . . . ? 
N2 C6 C11 Cl3 -1.7(15) . . . . ? 
N3 C2 C12 C13 53.5(15) . . . . ? 
N2 C2 C12 C13 -132.3(11) . . . . ? 
C14 O1 C13 C12 167.0(9) . . . . ? 
C2 C12 C13 O1 67.3(12) . . . . ? 
C13 O1 C14 C15 -179.1(7) . . . . ? 
O1 C14 C15 C14 54.0(4) . . . 7_566 ? 
O1 C14 C15 C14 173.7(8) . . . 8_656 ? 
O1 C14 C15 C14 -66.1(6) . . . 2 ? 
Cl10 C16 Cl11 Cl12 114(3) . . . . ? 
Cl10 C16 Cl12 Cl11 -79(3) . . . . ? 

_diffrn_measured_fraction_theta_max    0.957 
_diffrn_reflns_theta_full              27.52 
_diffrn_measured_fraction_theta_full   0.957 
_refine_diff_density_max    1.277 
_refine_diff_density_min   -0.567 
_refine_diff_density_rms    0.132 
############################################################################