#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:46:12 +0200 (lun 05 de jul de 2021) $
#$Revision: 267204 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/66/7706674.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_7706674
loop_
_publ_author_name
'Li, Jiahe'
'Yan, Hao'
'Wang, Zhiyuan'
'Liu, Rongping'
'Luo, Baomei'
'Yang, Dengfeng'
'Chen, Hailan'
'Pan, Lixia'
'Ma, Zhen'
_publ_section_title
;
 Copper chloride complexes with substituted 4'-phenyl-terpyridine ligands:
 synthesis, characterization, antiproliferative activities and DNA
 interactions.
;
_journal_issue                   23
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8243
_journal_page_last               8257
_journal_paper_doi               10.1039/d0dt03989f
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         'C21 H15 Cl2 Cu N3 O'
_chemical_formula_sum            'C21 H15 Cl2 Cu N3 O'
_chemical_formula_weight         459.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-11-15 deposited with the CCDC.	2021-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.105(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.922(3)
_cell_length_b                   12.541(2)
_cell_length_c                   10.8692(16)
_cell_measurement_reflns_used    4683
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0410
_cell_measurement_theta_min      3.8000
_cell_volume                     1823.2(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL2018 and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3818
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10154
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.550
_diffrn_reflns_theta_min         3.046
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.509
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_description       prism
_exptl_crystal_F_000             932
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0368
_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)+(0.0468P)²+0.7067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3450
_reflns_number_total             4303
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt03989f2.cif
_cod_data_source_block           D_CCDC4
_cod_depositor_comments
'Adding full bibliography for 7706668--7706674.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7706674
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.85286(2) 0.01572(2) 0.48255(2) 0.03578(12) Uani 1 1 d . . . . .
Cl1 Cl 0.69368(5) 0.03659(5) 0.55647(6) 0.04249(17) Uani 1 1 d . . . . .
Cl2 Cl 0.96948(5) -0.01498(6) 0.66513(6) 0.04799(19) Uani 1 1 d . . . . .
O1 O 0.42242(14) 0.16103(16) -0.43695(15) 0.0529(5) Uani 1 1 d . . . . .
H1A H 0.404910 0.105817 -0.477354 0.079 Uiso 1 1 calc R U . . .
N1 N 0.82023(15) -0.13611(16) 0.42065(17) 0.0351(4) Uani 1 1 d . . . . .
N2 N 0.78020(14) 0.03977(16) 0.30566(17) 0.0320(4) Uani 1 1 d . . . . .
N3 N 0.87172(14) 0.17553(17) 0.47066(16) 0.0343(4) Uani 1 1 d . . . . .
C1 C 0.8445(2) -0.2244(2) 0.4895(2) 0.0427(6) Uani 1 1 d . . . . .
H1B H 0.882089 -0.218485 0.574501 0.051 Uiso 1 1 calc R U . . .
C2 C 0.8166(2) -0.3237(2) 0.4406(3) 0.0482(7) Uani 1 1 d . . . . .
H2A H 0.834771 -0.383797 0.491827 0.058 Uiso 1 1 calc R U . . .
C3 C 0.7616(2) -0.3336(2) 0.3155(3) 0.0503(7) Uani 1 1 d . . . . .
H3A H 0.742973 -0.400556 0.279985 0.060 Uiso 1 1 calc R U . . .
C4 C 0.7345(2) -0.2427(2) 0.2432(2) 0.0432(6) Uani 1 1 d . . . . .
H4A H 0.696939 -0.247346 0.158011 0.052 Uiso 1 1 calc R U . . .
C5 C 0.76345(18) -0.14504(19) 0.2984(2) 0.0340(5) Uani 1 1 d . . . . .
C6 C 0.73892(17) -0.04160(19) 0.2330(2) 0.0316(5) Uani 1 1 d . . . . .
C7 C 0.67911(18) -0.0250(2) 0.1102(2) 0.0349(5) Uani 1 1 d . . . . .
H7A H 0.649634 -0.082711 0.060128 0.042 Uiso 1 1 calc R U . . .
C8 C 0.66276(17) 0.07776(19) 0.0612(2) 0.0329(5) Uani 1 1 d . . . . .
C9 C 0.70926(17) 0.1613(2) 0.1404(2) 0.0347(5) Uani 1 1 d . . . . .
H9A H 0.700865 0.231281 0.111036 0.042 Uiso 1 1 calc R U . . .
C10 C 0.76759(17) 0.13939(19) 0.2623(2) 0.0321(5) Uani 1 1 d . . . . .
C11 C 0.82308(17) 0.21790(19) 0.35667(19) 0.0324(5) Uani 1 1 d . . . . .
C12 C 0.8292(2) 0.3242(2) 0.3314(2) 0.0413(6) Uani 1 1 d . . . . .
H12A H 0.795768 0.352111 0.251734 0.050 Uiso 1 1 calc R U . . .
C13 C 0.8858(2) 0.3890(2) 0.4263(2) 0.0470(6) Uani 1 1 d . . . . .
H13A H 0.891925 0.461318 0.410931 0.056 Uiso 1 1 calc R U . . .
C14 C 0.9327(2) 0.3466(2) 0.5429(2) 0.0447(6) Uani 1 1 d . . . . .
H14A H 0.970082 0.389650 0.608516 0.054 Uiso 1 1 calc R U . . .
C15 C 0.92411(18) 0.2396(2) 0.5619(2) 0.0397(6) Uani 1 1 d . . . . .
H15A H 0.956068 0.210794 0.641602 0.048 Uiso 1 1 calc R U . . .
C16 C 0.59904(17) 0.0989(2) -0.0696(2) 0.0343(5) Uani 1 1 d . . . . .
C17 C 0.5752(2) 0.2013(2) -0.1140(2) 0.0515(7) Uani 1 1 d . . . . .
H17A H 0.598863 0.258671 -0.059990 0.062 Uiso 1 1 calc R U . . .
C18 C 0.5173(2) 0.2199(2) -0.2365(3) 0.0557(8) Uani 1 1 d . . . . .
H18A H 0.502642 0.289680 -0.264324 0.067 Uiso 1 1 calc R U . . .
C19 C 0.48063(18) 0.1371(2) -0.3184(2) 0.0396(6) Uani 1 1 d . . . . .
C20 C 0.5036(2) 0.0346(2) -0.2769(2) 0.0432(6) Uani 1 1 d . . . . .
H20A H 0.479923 -0.022416 -0.331556 0.052 Uiso 1 1 calc R U . . .
C21 C 0.5620(2) 0.0165(2) -0.1539(2) 0.0405(6) Uani 1 1 d . . . . .
H21A H 0.576870 -0.053382 -0.126599 0.049 Uiso 1 1 calc R U . . .
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'
Cu Cu 0.3201 1.2651 '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'
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
N2 Cu1 N1 79.00(8) . . ?
N2 Cu1 N3 79.85(8) . . ?
N1 Cu1 N3 157.90(7) . . ?
N2 Cu1 Cl2 165.32(6) . . ?
N1 Cu1 Cl2 100.05(6) . . ?
N3 Cu1 Cl2 98.78(5) . . ?
N2 Cu1 Cl1 92.08(6) . . ?
N1 Cu1 Cl1 93.79(6) . . ?
N3 Cu1 Cl1 93.28(6) . . ?
Cl2 Cu1 Cl1 102.60(3) . . ?
C1 N1 C5 118.3(2) . . ?
C1 N1 Cu1 126.71(16) . . ?
C5 N1 Cu1 114.87(16) . . ?
C6 N2 C10 121.40(19) . . ?
C6 N2 Cu1 119.72(16) . . ?
C10 N2 Cu1 118.74(15) . . ?
C15 N3 C11 118.8(2) . . ?
C15 N3 Cu1 127.19(16) . . ?
C11 N3 Cu1 114.05(15) . . ?
N1 C1 C2 122.7(2) . . ?
C1 C2 C3 119.3(3) . . ?
C2 C3 C4 118.7(3) . . ?
C5 C4 C3 119.2(2) . . ?
N1 C5 C4 121.6(2) . . ?
N1 C5 C6 113.3(2) . . ?
C4 C5 C6 125.0(2) . . ?
N2 C6 C7 120.5(2) . . ?
N2 C6 C5 112.81(19) . . ?
C7 C6 C5 126.7(2) . . ?
C6 C7 C8 120.1(2) . . ?
C7 C8 C9 117.5(2) . . ?
C7 C8 C16 121.8(2) . . ?
C9 C8 C16 120.8(2) . . ?
C10 C9 C8 119.5(2) . . ?
N2 C10 C9 120.9(2) . . ?
N2 C10 C11 112.83(19) . . ?
C9 C10 C11 126.2(2) . . ?
N3 C11 C12 121.7(2) . . ?
N3 C11 C10 114.2(2) . . ?
C12 C11 C10 124.0(2) . . ?
C11 C12 C13 118.6(2) . . ?
C14 C13 C12 119.6(2) . . ?
C13 C14 C15 119.0(2) . . ?
N3 C15 C14 122.3(2) . . ?
C17 C16 C21 117.0(2) . . ?
C17 C16 C8 121.7(2) . . ?
C21 C16 C8 121.2(2) . . ?
C18 C17 C16 121.2(2) . . ?
C19 C18 C17 120.9(3) . . ?
O1 C19 C20 123.1(2) . . ?
O1 C19 C18 117.8(2) . . ?
C20 C19 C18 119.1(2) . . ?
C19 C20 C21 119.7(2) . . ?
C20 C21 C16 122.1(2) . . ?
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
Cu1 N2 1.9318(18) . ?
Cu1 N1 2.029(2) . ?
Cu1 N3 2.030(2) . ?
Cu1 Cl2 2.2214(8) . ?
Cu1 Cl1 2.5716(8) . ?
O1 C19 1.352(3) . ?
N1 C1 1.326(3) . ?
N1 C5 1.350(3) . ?
N2 C6 1.321(3) . ?
N2 C10 1.330(3) . ?
N3 C15 1.327(3) . ?
N3 C11 1.346(3) . ?
C1 C2 1.367(4) . ?
C2 C3 1.369(4) . ?
C3 C4 1.377(4) . ?
C4 C5 1.374(3) . ?
C5 C6 1.473(3) . ?
C6 C7 1.379(3) . ?
C7 C8 1.389(3) . ?
C8 C9 1.396(3) . ?
C8 C16 1.476(3) . ?
C9 C10 1.376(3) . ?
C10 C11 1.476(3) . ?
C11 C12 1.369(3) . ?
C12 C13 1.376(3) . ?
C13 C14 1.363(4) . ?
C14 C15 1.367(4) . ?
C16 C17 1.379(4) . ?
C16 C21 1.382(3) . ?
C17 C18 1.371(3) . ?
C18 C19 1.371(4) . ?
C19 C20 1.370(4) . ?
C20 C21 1.377(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
C5 N1 C1 C2 1.7(4) . . . . ?
Cu1 N1 C1 C2 177.9(2) . . . . ?
N1 C1 C2 C3 0.3(4) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C1 N1 C5 C4 -2.8(4) . . . . ?
Cu1 N1 C5 C4 -179.42(19) . . . . ?
C1 N1 C5 C6 178.3(2) . . . . ?
Cu1 N1 C5 C6 1.7(3) . . . . ?
C3 C4 C5 N1 1.9(4) . . . . ?
C3 C4 C5 C6 -179.4(2) . . . . ?
C10 N2 C6 C7 -1.6(4) . . . . ?
Cu1 N2 C6 C7 173.98(17) . . . . ?
C10 N2 C6 C5 179.0(2) . . . . ?
Cu1 N2 C6 C5 -5.3(3) . . . . ?
N1 C5 C6 N2 2.1(3) . . . . ?
C4 C5 C6 N2 -176.7(2) . . . . ?
N1 C5 C6 C7 -177.1(2) . . . . ?
C4 C5 C6 C7 4.0(4) . . . . ?
N2 C6 C7 C8 0.8(4) . . . . ?
C5 C6 C7 C8 -179.9(2) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C6 C7 C8 C16 -179.8(2) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C16 C8 C9 C10 179.5(2) . . . . ?
C6 N2 C10 C9 1.3(4) . . . . ?
Cu1 N2 C10 C9 -174.41(17) . . . . ?
C6 N2 C10 C11 -177.7(2) . . . . ?
Cu1 N2 C10 C11 6.6(3) . . . . ?
C8 C9 C10 N2 -0.1(4) . . . . ?
C8 C9 C10 C11 178.8(2) . . . . ?
C15 N3 C11 C12 2.3(4) . . . . ?
Cu1 N3 C11 C12 -178.75(19) . . . . ?
C15 N3 C11 C10 179.8(2) . . . . ?
Cu1 N3 C11 C10 -1.3(3) . . . . ?
N2 C10 C11 N3 -3.2(3) . . . . ?
C9 C10 C11 N3 177.8(2) . . . . ?
N2 C10 C11 C12 174.2(2) . . . . ?
C9 C10 C11 C12 -4.7(4) . . . . ?
N3 C11 C12 C13 -0.8(4) . . . . ?
C10 C11 C12 C13 -178.1(2) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
C12 C13 C14 C15 1.4(4) . . . . ?
C11 N3 C15 C14 -2.0(4) . . . . ?
Cu1 N3 C15 C14 179.24(19) . . . . ?
C13 C14 C15 N3 0.1(4) . . . . ?
C7 C8 C16 C17 173.8(2) . . . . ?
C9 C8 C16 C17 -6.3(4) . . . . ?
C7 C8 C16 C21 -7.3(4) . . . . ?
C9 C8 C16 C21 172.5(2) . . . . ?
C21 C16 C17 C18 0.0(4) . . . . ?
C8 C16 C17 C18 178.9(3) . . . . ?
C16 C17 C18 C19 0.4(5) . . . . ?
C17 C18 C19 O1 178.8(3) . . . . ?
C17 C18 C19 C20 -0.8(5) . . . . ?
O1 C19 C20 C21 -178.8(2) . . . . ?
C18 C19 C20 C21 0.7(4) . . . . ?
C19 C20 C21 C16 -0.3(4) . . . . ?
C17 C16 C21 C20 -0.1(4) . . . . ?
C8 C16 C21 C20 -179.0(2) . . . . ?
