#------------------------------------------------------------------------------
#$Date: 2016-02-16 02:10:39 +0100 (mar 16 de feb de 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/87/7218770.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_7218770
loop_
_publ_author_name
'Rahiman, Kalilur'
'Arthi, P.'
'Reddy, Dastagiri'
'Sakthivel, Natarajan'
'arun, Y'
'Paramasivan Thirumalai, Perumal'
'haleel, azees'
'veena, V'
_publ_section_title
;
 DNA-binding, molecular docking and apoptotic inducing activity of
 nickel(II), copper(II) and zinc(II) complexes of pyridine-based
 tetrazolo[1,5-a]pyrimidine ligands
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA11197D
_journal_year                    2014
_chemical_formula_moiety
'(C28 H37 Cl2 N12 O4 Zn) * 2(C H4 O) * 0.5(H2 O)'
_chemical_formula_sum            'C28 H37 Cl2 N12 O6.5 Zn'
_chemical_formula_weight         781.97
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 93.851(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4600(4)
_cell_length_b                   13.5070(5)
_cell_length_c                   26.6520(9)
_cell_measurement_reflns_used    2119
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.0
_cell_measurement_theta_min      2.5
_cell_volume                     3757.0(2)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_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  0.1363
_diffrn_reflns_av_sigmaI/netI    0.2575
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11512
_diffrn_reflns_theta_full        23.58
_diffrn_reflns_theta_max         23.58
_diffrn_reflns_theta_min         2.47
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.853
_exptl_absorpt_correction_T_max  0.834
_exptl_absorpt_correction_T_min  0.721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1620
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         2751
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.1965
_refine_ls_R_factor_gt           0.0621
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0924P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1873
_reflns_number_gt                1308
_reflns_number_total             2751
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra11197d2.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C28 H37 Cl2 N12 O6.50 Zn'
_cod_database_code               7218770
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'
'-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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
H6A H 1.475(3) 0.605(5) 0.026(2) 0.08(2) Uiso 1 1 d D . .
C1 C 0.9579(7) 0.4668(5) 0.1554(3) 0.073(2) Uani 1 1 d . . .
H1 H 0.8752 0.4428 0.1578 0.088 Uiso 1 1 calc R . .
C2 C 0.9853(6) 0.5185(5) 0.1136(2) 0.073(2) Uani 1 1 d . . .
H2 H 0.9221 0.5292 0.0880 0.087 Uiso 1 1 calc R . .
C3 C 1.1063(5) 0.5546(5) 0.1096(2) 0.0525(16) Uani 1 1 d . . .
C4 C 1.1926(6) 0.5426(5) 0.1480(3) 0.072(2) Uani 1 1 d . . .
H4 H 1.2738 0.5702 0.1469 0.087 Uiso 1 1 calc R . .
C5 C 1.1611(6) 0.4887(6) 0.1901(2) 0.078(2) Uani 1 1 d . . .
H5 H 1.2224 0.4799 0.2167 0.093 Uiso 1 1 calc R . .
C6 C 1.1398(5) 0.6027(5) 0.0598(2) 0.0569(17) Uani 1 1 d . . .
H6 H 1.0610 0.6248 0.0412 0.068 Uiso 1 1 calc R . .
C7 C 1.3251(6) 0.5269(6) 0.0220(2) 0.0611(18) Uani 1 1 d . . .
C8 C 1.3546(6) 0.6839(6) 0.0560(2) 0.0663(19) Uani 1 1 d . . .
C9 C 1.2318(6) 0.6884(5) 0.0663(2) 0.0626(18) Uani 1 1 d . . .
C10 C 1.4549(6) 0.7630(5) 0.0642(3) 0.090(2) Uani 1 1 d . . .
H10A H 1.4186 0.8261 0.0546 0.134 Uiso 1 1 calc R . .
H10B H 1.5255 0.7488 0.0441 0.134 Uiso 1 1 calc R . .
H10C H 1.4845 0.7646 0.0991 0.134 Uiso 1 1 calc R . .
C11 C 1.1736(8) 0.7775(7) 0.0834(3) 0.080(2) Uani 1 1 d . A .
C12 C 0.991(2) 0.8453(13) 0.1146(9) 0.120(6) Uani 0.727(17) 1 d PDU A 3
H12A H 0.9936 0.9013 0.0919 0.144 Uiso 0.727(17) 1 calc PR A 3
H12B H 1.0276 0.8646 0.1476 0.144 Uiso 0.727(17) 1 calc PR A 3
C13 C 0.8562(13) 0.8039(12) 0.1168(7) 0.160(7) Uani 0.727(17) 1 d PDU A 3
H13A H 0.8314 0.7711 0.0857 0.240 Uiso 0.727(17) 1 calc PR A 3
H13B H 0.7977 0.8571 0.1221 0.240 Uiso 0.727(17) 1 calc PR A 3
H13C H 0.8545 0.7575 0.1441 0.240 Uiso 0.727(17) 1 calc PR A 3
O4 O 1.0000 0.695(3) 0.2500 0.160(14) Uani 0.297(17) 2 d SPU B 3
C12' C 0.969(6) 0.826(4) 0.1191(19) 0.123(11) Uani 0.273(17) 1 d PDU A 4
H12C H 0.8854 0.8215 0.1014 0.147 Uiso 0.273(17) 1 calc PR A 4
H12D H 0.9992 0.8936 0.1162 0.147 Uiso 0.273(17) 1 calc PR A 4
C13' C 0.957(4) 0.802(3) 0.1744(17) 0.176(16) Uani 0.273(17) 1 d PDU A 4
H13D H 1.0344 0.8211 0.1935 0.265 Uiso 0.273(17) 1 calc PR A 4
H13E H 0.9442 0.7318 0.1781 0.265 Uiso 0.273(17) 1 calc PR A 4
H13F H 0.8858 0.8370 0.1864 0.265 Uiso 0.273(17) 1 calc PR A 4
N1 N 1.0448(5) 0.4493(4) 0.19296(19) 0.0605(14) Uani 1 1 d . . .
N2 N 1.2021(4) 0.5274(4) 0.03073(17) 0.0562(14) Uani 1 1 d . . .
N3 N 1.1459(5) 0.4452(4) 0.0118(2) 0.0671(15) Uani 1 1 d . . .
N4 N 1.2334(5) 0.3953(4) -0.0087(2) 0.0759(17) Uani 1 1 d . . .
N5 N 1.3476(5) 0.4462(5) -0.0032(2) 0.0753(17) Uani 1 1 d . . .
N6 N 1.4024(5) 0.6001(5) 0.0363(2) 0.0757(18) Uani 1 1 d D . .
O1 O 1.2231(5) 0.8581(4) 0.0865(2) 0.1084(18) Uani 1 1 d . . .
O2 O 1.0554(5) 0.7612(4) 0.0958(2) 0.0924(16) Uani 1 1 d D . .
Cl1 Cl 0.8286(2) 0.27640(19) 0.22238(9) 0.1257(10) Uani 1 1 d . . .
Zn1 Zn 1.0000 0.35884(9) 0.2500 0.0767(5) Uani 1 2 d S . .
C14 C 0.860(3) 0.090(4) 0.3485(15) 0.217(12) Uani 0.57(2) 1 d PDU C -5
O3 O 0.9862(17) 0.0999(17) 0.3330(9) 0.241(11) Uani 0.57(2) 1 d PDU C -5
O4' O 1.031(8) 0.783(4) 0.250(6) 0.152(16) Uani 0.102(8) 1 d PU D -5
C14' C 0.936(4) 0.041(3) 0.2823(19) 0.271(14) Uani 0.43(2) 1 d PDU C -6
O3' O 0.845(3) 0.086(3) 0.3145(16) 0.243(12) Uani 0.43(2) 1 d PDU C -6
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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
N1 C1 C2 122.5(6) . .
N1 C1 H1 118.8 . .
C2 C1 H1 118.8 . .
C1 C2 C3 119.6(7) . .
C1 C2 H2 120.2 . .
C3 C2 H2 120.2 . .
C4 C3 C2 118.7(6) . .
C4 C3 C6 122.3(5) . .
C2 C3 C6 119.0(6) . .
C3 C4 C5 119.9(6) . .
C3 C4 H4 120.0 . .
C5 C4 H4 120.0 . .
N1 C5 C4 121.3(6) . .
N1 C5 H5 119.4 . .
C4 C5 H5 119.4 . .
N2 C6 C9 106.9(5) . .
N2 C6 C3 107.4(5) . .
C9 C6 C3 114.0(5) . .
N2 C6 H6 109.5 . .
C9 C6 H6 109.5 . .
C3 C6 H6 109.5 . .
N5 C7 N6 130.1(6) . .
N5 C7 N2 107.8(6) . .
N6 C7 N2 122.0(7) . .
C9 C8 N6 120.2(6) . .
C9 C8 C10 127.7(7) . .
N6 C8 C10 112.1(6) . .
C8 C9 C11 122.6(6) . .
C8 C9 C6 123.9(7) . .
C11 C9 C6 113.5(6) . .
C8 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C8 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
O1 C11 O2 122.5(8) . .
O1 C11 C9 126.1(7) . .
O2 C11 C9 111.4(7) . .
O2 C12 C13 100.3(13) . .
O2 C12 H12A 111.7 . .
C13 C12 H12A 111.7 . .
O2 C12 H12B 111.7 . .
C13 C12 H12B 111.7 . .
H12A C12 H12B 109.5 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
O2 C12' C13' 113(3) . .
O2 C12' H12C 109.1 . .
C13' C12' H12C 109.1 . .
O2 C12' H12D 109.1 . .
C13' C12' H12D 109.1 . .
H12C C12' H12D 107.8 . .
C12' C13' H13D 109.5 . .
C12' C13' H13E 109.5 . .
H13D C13' H13E 109.5 . .
C12' C13' H13F 109.5 . .
H13D C13' H13F 109.5 . .
H13E C13' H13F 109.5 . .
C1 N1 C5 117.9(5) . .
C1 N1 Zn1 119.4(4) . .
C5 N1 Zn1 122.7(5) . .
C7 N2 N3 109.7(5) . .
C7 N2 C6 124.9(6) . .
N3 N2 C6 125.3(4) . .
N4 N3 N2 106.7(5) . .
N3 N4 N5 109.2(5) . .
C7 N5 N4 106.6(5) . .
C7 N6 C8 120.2(5) . .
C7 N6 H6A 122(5) . .
C8 N6 H6A 115(5) . .
C11 O2 C12 115.1(11) . .
C11 O2 C12' 129(3) . .
C12 O2 C12' 15(4) . .
N1 Zn1 N1 106.0(3) . 2_755
N1 Zn1 Cl1 106.18(18) . .
N1 Zn1 Cl1 109.40(17) 2_755 .
N1 Zn1 Cl1 109.41(17) . 2_755
N1 Zn1 Cl1 106.18(18) 2_755 2_755
Cl1 Zn1 Cl1 119.03(15) . 2_755
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.326(8) .
C1 C2 1.363(9) .
C1 H1 0.9300 .
C2 C3 1.367(7) .
C2 H2 0.9300 .
C3 C4 1.329(8) .
C3 C6 1.538(8) .
C4 C5 1.395(9) .
C4 H4 0.9300 .
C5 N1 1.335(7) .
C5 H5 0.9300 .
C6 N2 1.460(7) .
C6 C9 1.508(8) .
C6 H6 0.9800 .
C7 N5 1.309(8) .
C7 N6 1.318(8) .
C7 N2 1.322(7) .
C8 C9 1.332(8) .
C8 N6 1.358(8) .
C8 C10 1.503(8) .
C9 C11 1.437(10) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 O1 1.206(8) .
C11 O2 1.320(8) .
C12 O2 1.427(12) .
C12 C13 1.526(19) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C12' O2 1.427(19) .
C12' C13' 1.52(2) .
C12' H12C 0.9700 .
C12' H12D 0.9700 .
C13' H13D 0.9600 .
C13' H13E 0.9600 .
C13' H13F 0.9600 .
N1 Zn1 2.030(5) .
N2 N3 1.339(6) .
N3 N4 1.288(7) .
N4 N5 1.377(7) .
N6 H6A 0.83(2) .
Cl1 Zn1 2.195(2) .
Zn1 N1 2.030(5) 2_755
Zn1 Cl1 2.195(2) 2_755
C14 O3 1.414(19) .
C14' O3' 1.45(2) .
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
C1 H1 O1 0.93 2.65 3.310(10) 128.2 3_445
C1 H1 Cl1 0.93 2.89 3.456(7) 120.3 .
C4 H4 O3 0.93 2.56 3.452(19) 160.1 4_755
C6 H6 N3 0.98 2.68 3.497(8) 141.6 5_765
C10 H10A O1 0.96 2.31 2.842(9) 114.3 .
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_4
N1 C1 C2 C3 -0.2(11) .
C1 C2 C3 C4 -3.6(10) .
C1 C2 C3 C6 173.3(6) .
C2 C3 C4 C5 4.0(10) .
C6 C3 C4 C5 -172.8(6) .
C3 C4 C5 N1 -0.8(11) .
C4 C3 C6 N2 80.1(7) .
C2 C3 C6 N2 -96.7(7) .
C4 C3 C6 C9 -38.2(9) .
C2 C3 C6 C9 145.0(6) .
N6 C8 C9 C11 -175.0(6) .
C10 C8 C9 C11 5.7(10) .
N6 C8 C9 C6 3.3(9) .
C10 C8 C9 C6 -175.9(6) .
N2 C6 C9 C8 -12.6(8) .
C3 C6 C9 C8 105.9(7) .
N2 C6 C9 C11 165.9(5) .
C3 C6 C9 C11 -75.6(7) .
C8 C9 C11 O1 6.6(12) .
C6 C9 C11 O1 -171.9(7) .
C8 C9 C11 O2 -173.7(6) .
C6 C9 C11 O2 7.8(8) .
C2 C1 N1 C5 3.4(10) .
C2 C1 N1 Zn1 -173.3(5) .
C4 C5 N1 C1 -2.9(10) .
C4 C5 N1 Zn1 173.6(5) .
N5 C7 N2 N3 1.2(7) .
N6 C7 N2 N3 179.3(6) .
N5 C7 N2 C6 177.1(5) .
N6 C7 N2 C6 -4.9(9) .
C9 C6 N2 C7 13.4(8) .
C3 C6 N2 C7 -109.3(6) .
C9 C6 N2 N3 -171.3(5) .
C3 C6 N2 N3 65.9(7) .
C7 N2 N3 N4 -0.5(6) .
C6 N2 N3 N4 -176.4(5) .
N2 N3 N4 N5 -0.3(7) .
N6 C7 N5 N4 -179.2(7) .
N2 C7 N5 N4 -1.3(7) .
N3 N4 N5 C7 1.0(7) .
N5 C7 N6 C8 170.6(7) .
N2 C7 N6 C8 -7.0(9) .
C9 C8 N6 C7 7.6(9) .
C10 C8 N6 C7 -173.1(6) .
O1 C11 O2 C12 -1.9(15) .
C9 C11 O2 C12 178.3(12) .
O1 C11 O2 C12' -7(3) .
C9 C11 O2 C12' 173(3) .
C13 C12 O2 C11 171.7(10) .
C13 C12 O2 C12' -24(12) .
C13' C12' O2 C11 -104(5) .
C13' C12' O2 C12 -123(17) .
C1 N1 Zn1 N1 -99.8(5) 2_755
C5 N1 Zn1 N1 83.8(5) 2_755
C1 N1 Zn1 Cl1 16.5(5) .
C5 N1 Zn1 Cl1 -160.0(5) .
C1 N1 Zn1 Cl1 146.2(5) 2_755
C5 N1 Zn1 Cl1 -30.3(5) 2_755
