#------------------------------------------------------------------------------
#$Date: 2019-11-17 13:21:43 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230132 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/10/7121054.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_7121054
loop_
_publ_author_name
'Hu, Jiyong'
'Liao, Chunli'
'Mao, Ruina'
'Zhang, Junshuai'
'Zhao, Jin'an'
'Gu, Zhenzhen'
_publ_section_title
;
 DNA interactions and in vitro anticancer evaluations of
 pyridine-benzimidazole-based Cu complexes.
;
_journal_issue                   2
_journal_name_full               MedChemComm
_journal_page_first              337
_journal_page_last               343
_journal_paper_doi               10.1039/c7md00462a
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C20 H14 Cl Cu N4 S, C H4 O'
_chemical_formula_sum            'C21 H18 Cl Cu N4 O S'
_chemical_formula_weight         473.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-08-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_audit_update_record
;
2017-02-10 deposited with the CCDC.
2017-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                87.064(7)
_cell_angle_beta                 67.901(8)
_cell_angle_gamma                71.422(7)
_cell_formula_units_Z            2
_cell_length_a                   9.4142(8)
_cell_length_b                   10.2389(8)
_cell_length_c                   11.9095(10)
_cell_measurement_reflns_used    2939
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.4080
_cell_measurement_theta_min      4.0070
_cell_volume                     1005.13(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 10.5281
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -43.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2335   37.0000 -180.0000 79

#__ type_ start__ end____ width___ exp.time_
  2 omega -119.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2335  -77.0000   60.0000 109

#__ type_ start__ end____ width___ exp.time_
  3 omega  -95.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2335  125.0000 -180.0000 79

#__ type_ start__ end____ width___ exp.time_
  4 omega   59.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2335 -125.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega -115.00  -39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -60.0000 76

#__ type_ start__ end____ width___ exp.time_
  6 omega  -51.00   -3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000   45.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 47

#__ type_ start__ end____ width___ exp.time_
  8 omega   53.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   60.0000 123

#__ type_ start__ end____ width___ exp.time_
  9 omega   46.00  143.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -60.0000 97

#__ type_ start__ end____ width___ exp.time_
 10 omega  135.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
 11 omega   79.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   30.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -30.0000 40

#__ type_ start__ end____ width___ exp.time_
 13 omega   82.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega  106.00  171.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000 -120.0000 65

#__ type_ start__ end____ width___ exp.time_
 15 omega   79.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 16 omega   48.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega   59.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -150.0000 57

#__ type_ start__ end____ width___ exp.time_
 18 omega  114.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 19 omega   43.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega   36.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -60.0000 80

#__ type_ start__ end____ width___ exp.time_
 21 omega   71.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -30.0000 61

#__ type_ start__ end____ width___ exp.time_
 22 omega   87.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 89
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0665400000
_diffrn_orient_matrix_UB_12      -0.1552147000
_diffrn_orient_matrix_UB_13      0.0153222000
_diffrn_orient_matrix_UB_21      0.0675478000
_diffrn_orient_matrix_UB_22      0.0340835000
_diffrn_orient_matrix_UB_23      0.0901809000
_diffrn_orient_matrix_UB_31      -0.1607760000
_diffrn_orient_matrix_UB_32      0.0098755000
_diffrn_orient_matrix_UB_33      0.1060384000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7630
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.432
_diffrn_reflns_theta_min         4.019
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.895
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0428P)²+0.5202P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3310
_reflns_number_total             4103
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7md00462a2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7121054--7121055.cif.'
_cod_database_code               7121054
_shelxl_version_number           2013-2
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.721
_shelx_estimated_absorpt_t_min   0.593
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C16(H16), C1(H1), C8(H8), C10(H10), C17(H17), C3(H3), C4(H4),
 C2(H2), C20(H20), C19(H19), C9(H9)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Cu1 Cu 0.26163(4) 1.02713(4) 0.23065(3) 0.01805(11) Uani 1 1 d .
Cl1 Cl 0.42085(7) 1.04053(7) 0.32920(6) 0.02333(15) Uani 1 1 d .
S1 S 0.58145(7) 1.22549(7) -0.08643(6) 0.02267(15) Uani 1 1 d .
N2 N 0.1426(2) 0.9190(2) 0.34997(19) 0.0171(4) Uani 1 1 d .
N3 N -0.0548(2) 0.8248(2) 0.40857(19) 0.0177(4) Uani 1 1 d .
N4 N 0.3598(3) 1.1347(3) 0.1030(2) 0.0241(5) Uani 1 1 d .
N1 N 0.0643(2) 1.0663(2) 0.18456(19) 0.0190(4) Uani 1 1 d .
O1 O 0.3630(4) 0.3678(3) 0.3397(2) 0.0541(8) Uani 1 1 d .
H1A H 0.3983 0.2862 0.3145 0.081 Uiso 1 1 calc GR
C13 C 0.4513(3) 1.1719(3) 0.0250(2) 0.0202(5) Uani 1 1 d .
C6 C 0.0114(3) 0.9131(3) 0.3350(2) 0.0159(5) Uani 1 1 d .
C12 C 0.1662(3) 0.8282(3) 0.4360(2) 0.0187(5) Uani 1 1 d .
C15 C -0.1254(3) 0.6906(3) 0.2825(2) 0.0184(5) Uani 1 1 d .
C14 C -0.1800(3) 0.7716(3) 0.4031(2) 0.0204(5) Uani 1 1 d .
H14A H -0.2779 0.8484 0.4143 0.024 Uiso 1 1 calc R
H14B H -0.2055 0.7123 0.4687 0.024 Uiso 1 1 calc R
C5 C -0.0412(3) 0.9988(3) 0.2469(2) 0.0171(5) Uani 1 1 d .
C18 C -0.0259(3) 0.5377(2) 0.0602(2) 0.0160(5) Uani 1 1 d .
C11 C 0.2875(3) 0.7902(3) 0.4846(2) 0.0233(6) Uani 1 1 d .
H11 H 0.3703 0.8290 0.4605 0.028 Uiso 1 1 calc R
C7 C 0.0416(3) 0.7685(3) 0.4747(2) 0.0195(5) Uani 1 1 d .
C16 C -0.2367(3) 0.6914(3) 0.2323(2) 0.0215(5) Uani 1 1 d .
H16 H -0.3451 0.7433 0.2721 0.026 Uiso 1 1 calc R
C1 C 0.0326(3) 1.1503(3) 0.1024(2) 0.0234(5) Uani 1 1 d .
H1 H 0.1053 1.1965 0.0607 0.028 Uiso 1 1 calc R
C8 C 0.0307(4) 0.6725(3) 0.5618(3) 0.0272(6) Uani 1 1 d .
H8 H -0.0527 0.6344 0.5873 0.033 Uiso 1 1 calc R
C10 C 0.2785(4) 0.6932(3) 0.5693(3) 0.0298(6) Uani 1 1 d .
H10 H 0.3585 0.6642 0.6015 0.036 Uiso 1 1 calc R
C17 C -0.1884(3) 0.6158(3) 0.1235(2) 0.0213(5) Uani 1 1 d .
H17 H -0.2653 0.6169 0.0919 0.026 Uiso 1 1 calc R
C3 C -0.2125(3) 1.1033(3) 0.1389(3) 0.0248(6) Uani 1 1 d .
H3 H -0.3054 1.1155 0.1232 0.030 Uiso 1 1 calc R
C4 C -0.1806(3) 1.0162(3) 0.2251(2) 0.0222(5) Uani 1 1 d .
H4 H -0.2521 0.9696 0.2683 0.027 Uiso 1 1 calc R
C2 C -0.1044(3) 1.1724(3) 0.0758(3) 0.0262(6) Uani 1 1 d .
H2 H -0.1233 1.2318 0.0175 0.031 Uiso 1 1 calc R
C20 C 0.0358(3) 0.6104(3) 0.2225(3) 0.0264(6) Uani 1 1 d .
H20 H 0.1116 0.6067 0.2560 0.032 Uiso 1 1 calc R
C19 C 0.0840(3) 0.5358(3) 0.1130(3) 0.0260(6) Uani 1 1 d .
H19 H 0.1923 0.4832 0.0740 0.031 Uiso 1 1 calc R
C9 C 0.1512(4) 0.6371(3) 0.6083(3) 0.0325(7) Uani 1 1 d .
H9 H 0.1479 0.5739 0.6674 0.039 Uiso 1 1 calc R
C21 C 0.4385(4) 0.4441(4) 0.2497(3) 0.0359(7) Uani 1 1 d .
H21A H 0.4135 0.4380 0.1795 0.054 Uiso 1 1 calc GR
H21B H 0.5537 0.4076 0.2277 0.054 Uiso 1 1 calc GR
H21C H 0.4002 0.5391 0.2803 0.054 Uiso 1 1 calc GR
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_3
N2 Cu1 Cl1 96.29(7) .
N2 Cu1 N1 80.52(9) .
N4 Cu1 Cl1 90.99(7) .
N4 Cu1 N2 172.69(10) .
N4 Cu1 N1 92.36(9) .
N1 Cu1 Cl1 160.98(6) .
C6 N2 Cu1 114.03(17) .
C6 N2 C12 106.5(2) .
C12 N2 Cu1 138.55(18) .
C6 N3 C14 127.8(2) .
C6 N3 C7 106.9(2) .
C7 N3 C14 123.9(2) .
C13 N4 Cu1 163.2(2) .
C5 N1 Cu1 114.74(17) .
C1 N1 Cu1 125.93(18) .
C1 N1 C5 119.3(2) .
N4 C13 S1 179.8(3) .
N2 C6 N3 112.0(2) .
N2 C6 C5 118.4(2) .
N3 C6 C5 129.6(2) .
N2 C12 C11 131.3(3) .
N2 C12 C7 108.5(2) .
C7 C12 C11 120.2(2) .
C16 C15 C14 120.4(2) .
C16 C15 C20 118.7(2) .
C20 C15 C14 120.9(2) .
N3 C14 C15 111.8(2) .
N1 C5 C6 111.8(2) .
N1 C5 C4 120.9(2) .
C4 C5 C6 127.3(2) .
C17 C18 C18 120.6(3) 2_565
C19 C18 C18 122.1(3) 2_565
C19 C18 C17 117.3(2) .
C10 C11 C12 117.2(3) .
N3 C7 C12 106.0(2) .
C8 C7 N3 131.4(3) .
C8 C7 C12 122.6(3) .
C15 C16 C17 120.8(2) .
N1 C1 C2 122.9(3) .
C9 C8 C7 116.1(3) .
C11 C10 C9 121.5(3) .
C16 C17 C18 121.2(2) .
C4 C3 C2 119.2(3) .
C3 C4 C5 119.6(2) .
C3 C2 C1 118.1(3) .
C19 C20 C15 120.3(3) .
C20 C19 C18 121.6(2) .
C8 C9 C10 122.3(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Cl1 2.2615(7) .
Cu1 N2 1.983(2) .
Cu1 N4 1.949(2) .
Cu1 N1 2.045(2) .
S1 C13 1.641(3) .
N2 C6 1.332(3) .
N2 C12 1.380(3) .
N3 C6 1.357(3) .
N3 C14 1.470(3) .
N3 C7 1.391(3) .
N4 C13 1.149(4) .
N1 C5 1.359(3) .
N1 C1 1.325(4) .
O1 C21 1.400(4) .
C6 C5 1.461(3) .
C12 C11 1.408(4) .
C12 C7 1.408(4) .
C15 C14 1.519(3) .
C15 C16 1.386(4) .
C15 C20 1.392(4) .
C5 C4 1.387(4) .
C18 C18 1.496(5) 2_565
C18 C17 1.401(3) .
C18 C19 1.393(4) .
C11 C10 1.378(4) .
C7 C8 1.390(4) .
C16 C17 1.386(4) .
C1 C2 1.389(4) .
C8 C9 1.384(4) .
C10 C9 1.405(4) .
C3 C4 1.381(4) .
C3 C2 1.389(4) .
C20 C19 1.388(4) .
