#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/96/7029642.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_7029642
loop_
_publ_author_name
'Adhami, Forogh'
'Safavi, Maliheh'
'Ehsani, Maryam'
'Ardestani, Sussan K.'
'Emmerling, Franziska'
'Simyari, Farzaneh'
_publ_section_title
;
 Synthesis, crystal structure, and cytotoxic activity of novel cyclic
 systems in [1,2,4]thiadiazolo[2,3-a]pyridine benzamide derivatives and
 their copper(ii) complexes.
;
_journal_issue                   21
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7945
_journal_page_last               7957
_journal_paper_doi               10.1039/c3dt52905c
_journal_volume                  43
_journal_year                    2014
_chemical_formula_moiety         'C28 H22 Cl2 Cu N6 O2 S2'
_chemical_formula_sum            'C28 H22 Cl2 Cu N6 O2 S2'
_chemical_formula_weight         673.08
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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                78.716(8)
_cell_angle_beta                 76.857(8)
_cell_angle_gamma                71.514(8)
_cell_formula_units_Z            1
_cell_length_a                   8.158(5)
_cell_length_b                   8.426(5)
_cell_length_c                   11.183(6)
_cell_measurement_reflns_used    35
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      4
_cell_volume                     703.6(7)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'SHELXTL (Bruker, 2001), ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω/2θ
_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  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5539
_diffrn_reflns_theta_full        29.49
_diffrn_reflns_theta_max         29.49
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    1.154
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'SHELXTL (Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             343
_exptl_crystal_size_max          .14
_exptl_crystal_size_mid          .11
_exptl_crystal_size_min          .05
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0406
_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)+(0.0499P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1028
_reflns_number_gt                2770
_reflns_number_total             3840
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt52905c5.cif
_cod_data_source_block           C2
_cod_depositor_comments
'Adding full bibliography for 7029640--7029646.cif.'
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_database_code               7029642
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
Cu1 Cu 0.5000 0.5000 0.0000 0.03483(12) Uani 1 2 d S
Cl1 Cl 0.76632(8) 0.54168(7) -0.08041(6) 0.05141(17) Uani 1 1 d .
S1 S 0.30605(7) 1.01025(6) 0.13118(6) 0.04097(15) Uani 1 1 d .
O1 O 0.4145(2) 0.9315(2) 0.29603(16) 0.0540(4) Uani 1 1 d .
N1 N 0.2380(2) 1.0203(2) -0.01259(17) 0.0370(4) Uani 1 1 d .
N2 N 0.3939(2) 0.7439(2) 0.01640(17) 0.0372(4) Uani 1 1 d .
N3 N 0.5007(3) 0.6952(2) 0.20132(18) 0.0417(4) Uani 1 1 d .
C1 C 0.1348(3) 1.1597(3) -0.0725(2) 0.0442(6) Uani 1 1 d .
H1 H 0.0946 1.2614 -0.0399 0.053 Uiso 1 1 calc R
C2 C 0.0915(3) 1.1488(3) -0.1795(2) 0.0474(6) Uani 1 1 d .
H2 H 0.0213 1.2440 -0.2204 0.057 Uiso 1 1 calc R
C3 C 0.1508(3) 0.9954(3) -0.2305(2) 0.0451(5) Uani 1 1 d .
C4 C 0.2525(3) 0.8557(3) -0.1673(2) 0.0433(5) Uani 1 1 d .
H4 H 0.2922 0.7527 -0.1981 0.052 Uiso 1 1 calc R
C5 C 0.2956(3) 0.8691(2) -0.0570(2) 0.0367(5) Uani 1 1 d .
C6 C 0.4104(3) 0.7963(2) 0.1169(2) 0.0372(5) Uani 1 1 d .
C7 C 0.4975(3) 0.7773(3) 0.2939(2) 0.0430(5) Uani 1 1 d .
C8 C 0.5953(3) 0.6841(3) 0.3949(2) 0.0439(5) Uani 1 1 d .
C9 C 0.7132(4) 0.5261(3) 0.3842(3) 0.0595(7) Uani 1 1 d .
H9 H 0.7323 0.4763 0.3132 0.071 Uiso 1 1 calc R
C10 C 0.8027(4) 0.4429(4) 0.4801(3) 0.0751(9) Uani 1 1 d .
H10 H 0.8828 0.3369 0.4733 0.090 Uiso 1 1 calc R
C11 C 0.7736(5) 0.5164(4) 0.5855(3) 0.0730(9) Uani 1 1 d .
H11 H 0.8327 0.4585 0.6502 0.088 Uiso 1 1 calc R
C12 C 0.6602(4) 0.6718(4) 0.5962(3) 0.0684(8) Uani 1 1 d .
H12 H 0.6427 0.7211 0.6672 0.082 Uiso 1 1 calc R
C13 C 0.5704(4) 0.7569(4) 0.5012(2) 0.0577(7) Uani 1 1 d .
H13 H 0.4926 0.8639 0.5084 0.069 Uiso 1 1 calc R
C14 C 0.1025(4) 0.9882(4) -0.3508(2) 0.0616(7) Uani 1 1 d .
H14A H 0.1562 0.8769 -0.3739 0.092 Uiso 1 1 calc R
H14B H 0.1433 1.0688 -0.4142 0.092 Uiso 1 1 calc R
H14C H -0.0228 1.0143 -0.3412 0.092 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
S S 0.1246 0.1234 '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
N2 Cu1 N2 180.0 . 2_665
N2 Cu1 Cl1 91.10(6) . .
N2 Cu1 Cl1 88.90(6) 2_665 .
N2 Cu1 Cl1 88.90(6) . 2_665
N2 Cu1 Cl1 91.10(6) 2_665 2_665
Cl1 Cu1 Cl1 180.0 . 2_665
C6 S1 N1 85.53(10) . .
C6 S1 O1 79.71(9) . .
N1 S1 O1 165.22(7) . .
C7 O1 S1 105.68(15) . .
C5 N1 C1 121.4(2) . .
C5 N1 S1 112.92(14) . .
C1 N1 S1 125.63(15) . .
C6 N2 C5 112.73(18) . .
C6 N2 Cu1 117.29(14) . .
C5 N2 Cu1 129.87(15) . .
C6 N3 C7 111.69(19) . .
C2 C1 N1 119.4(2) . .
C2 C1 H1 120.3 . .
N1 C1 H1 120.3 . .
C1 C2 C3 121.2(2) . .
C1 C2 H2 119.4 . .
C3 C2 H2 119.4 . .
C4 C3 C2 118.3(2) . .
C4 C3 C14 121.8(2) . .
C2 C3 C14 119.9(2) . .
C3 C4 C5 119.7(2) . .
C3 C4 H4 120.1 . .
C5 C4 H4 120.1 . .
N1 C5 N2 113.1(2) . .
N1 C5 C4 119.90(19) . .
N2 C5 C4 127.03(19) . .
N3 C6 N2 122.93(19) . .
N3 C6 S1 121.32(17) . .
N2 C6 S1 115.75(16) . .
O1 C7 N3 121.6(2) . .
O1 C7 C8 119.6(2) . .
N3 C7 C8 118.8(2) . .
C9 C8 C13 119.3(2) . .
C9 C8 C7 120.9(2) . .
C13 C8 C7 119.7(2) . .
C8 C9 C10 119.4(3) . .
C8 C9 H9 120.3 . .
C10 C9 H9 120.3 . .
C11 C10 C9 120.3(3) . .
C11 C10 H10 119.9 . .
C9 C10 H10 119.9 . .
C12 C11 C10 120.8(3) . .
C12 C11 H11 119.6 . .
C10 C11 H11 119.6 . .
C11 C12 C13 119.7(3) . .
C11 C12 H12 120.1 . .
C13 C12 H12 120.1 . .
C12 C13 C8 120.5(3) . .
C12 C13 H13 119.7 . .
C8 C13 H13 119.7 . .
C3 C14 H14A 109.5 . .
C3 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C3 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N2 1.988(2) .
Cu1 N2 1.988(2) 2_665
Cu1 Cl1 2.2637(14) .
Cu1 Cl1 2.2637(14) 2_665
S1 C6 1.754(2) .
S1 N1 1.795(2) .
S1 O1 2.124(2) .
O1 C7 1.262(3) .
N1 C5 1.361(3) .
N1 C1 1.364(3) .
N2 C6 1.333(3) .
N2 C5 1.362(3) .
N3 C6 1.328(3) .
N3 C7 1.345(3) .
C1 C2 1.349(3) .
C1 H1 0.9300 .
C2 C3 1.413(3) .
C2 H2 0.9300 .
C3 C4 1.377(3) .
C3 C14 1.502(4) .
C4 C5 1.390(3) .
C4 H4 0.9300 .
C7 C8 1.481(3) .
C8 C9 1.382(3) .
C8 C13 1.389(4) .
C9 C10 1.382(4) .
C9 H9 0.9300 .
C10 C11 1.377(5) .
C10 H10 0.9300 .
C11 C12 1.352(4) .
C11 H11 0.9300 .
C12 C13 1.378(4) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
