#------------------------------------------------------------------------------
#$Date: 2019-11-12 04:56:28 +0200 (Tue, 12 Nov 2019) $
#$Revision: 227637 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/18/7701880.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_7701880
loop_
_publ_author_name
'Alvarez-Miguel, Lucia'
'Álvarez-Miguel, Ines'
'Martín Álvarez, Jose Miguel'
'Alvarez, Celedonio M.'
'Rogez, Guillaume'
'García-Rodríguez, Raúl'
'Miguel, Daniel'
_publ_section_title
;
 Copper complexes for the promotion of iminopyridine ligands derived from
 β-alanine and self-aldol additions: Relaxivity and cytotoxic properties
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/C9DT03822A
_journal_year                    2019
_chemical_formula_moiety         'C14 H14 Cl4 Cu2 N2 O2'
_chemical_formula_sum            'C14 H14 Cl4 Cu2 N2 O2'
_chemical_formula_weight         511.15
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2019-09-24 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                103.091(17)
_cell_angle_beta                 111.393(18)
_cell_angle_gamma                107.507(17)
_cell_formula_units_Z            1
_cell_length_a                   7.9027(15)
_cell_length_b                   8.1307(16)
_cell_length_c                   8.3402(18)
_cell_measurement_reflns_used    1212
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.4696
_cell_measurement_theta_min      2.8283
_cell_volume                     440.4(2)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      297.15
_diffrn_detector_area_resol_mean 10.4757
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -10.00   97.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       21.5439   77.0000  -90.0000 107

#__ type_ start__ end____ width___ exp.time_
  2 omega  -12.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       21.5439   77.0000  150.0000 113

#__ type_ start__ end____ width___ exp.time_
  3 omega  -12.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       21.5439   77.0000   30.0000 110
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0727299000
_diffrn_orient_matrix_UB_12      0.0367288000
_diffrn_orient_matrix_UB_13      -0.0196503000
_diffrn_orient_matrix_UB_21      0.0773352000
_diffrn_orient_matrix_UB_22      0.0916626000
_diffrn_orient_matrix_UB_23      0.0518128000
_diffrn_orient_matrix_UB_31      0.0066618000
_diffrn_orient_matrix_UB_32      0.0040969000
_diffrn_orient_matrix_UB_33      -0.0816600000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            2813
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.532
_diffrn_reflns_theta_min         2.834
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.030
_exptl_absorpt_correction_T_max  0.540
_exptl_absorpt_correction_T_min  0.270
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.927
_exptl_crystal_description       block
_exptl_crystal_F_000             254
_exptl_crystal_size_max          0.3988
_exptl_crystal_size_mid          0.3608
_exptl_crystal_size_min          0.1896
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0385P)²+0.0114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0997
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1573
_reflns_number_total             1972
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt03822a2.cif
_cod_data_source_block           Compound_1b_dm356c
_cod_original_cell_volume        440.43(17)
_cod_database_code               7701880
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C14 H14 N2 O2 Cl4 Cu4'
_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.
;
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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 0.23137(6) 0.53349(6) 0.01363(6) 0.03082(17) Uani 1 1 d .
Cl1 Cl 0.01009(14) 0.28771(12) 0.02048(14) 0.0362(3) Uani 1 1 d .
Cl2 Cl 0.14956(15) 0.39449(14) -0.28203(14) 0.0427(3) Uani 1 1 d .
N1 N 0.3901(4) 0.6657(4) 0.2919(4) 0.0275(7) Uani 1 1 d .
O1 O 0.4608(4) 0.7546(4) 0.0376(4) 0.0384(7) Uani 1 1 d .
C11 C 0.3456(6) 0.6172(5) 0.4178(5) 0.0324(9) Uani 1 1 d .
H11 H 0.2257 0.5159 0.3785 0.039 Uiso 1 1 calc R
C12 C 0.4736(6) 0.7140(5) 0.6067(6) 0.0385(10) Uani 1 1 d .
H12 H 0.4408 0.6758 0.6926 0.046 Uiso 1 1 calc R
C13 C 0.6462(6) 0.8640(5) 0.6656(6) 0.0375(10) Uani 1 1 d .
H13 H 0.7330 0.9294 0.7922 0.045 Uiso 1 1 calc R
C14 C 0.6924(6) 0.9191(5) 0.5365(5) 0.0335(9) Uani 1 1 d .
H14 H 0.8093 1.0231 0.5742 0.040 Uiso 1 1 calc R
C15 C 0.5625(5) 0.8173(5) 0.3516(5) 0.0269(8) Uani 1 1 d .
C16 C 0.5917(5) 0.8577(5) 0.1969(5) 0.0299(8) Uani 1 1 d .
C17 C 0.7700(6) 1.0154(5) 0.2288(6) 0.0413(10) Uani 1 1 d .
H17A H 0.8426 0.9688 0.1744 0.062 Uiso 1 1 calc GR
H17B H 0.8550 1.0832 0.3602 0.062 Uiso 1 1 calc GR
H17C H 0.7283 1.0966 0.1728 0.062 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 0.0033 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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-9 0 -1 0.0495 -9.0000 0.0000 -1.0000 0.6777 -0.7487 0.0166
5 8 -4 0.1121 5.0000 8.0000 -4.0000 0.0052 0.9124 0.3979
10 0 -9 0.1048 10.0000 -0.0000 -9.0000 -0.5515 0.3013 0.8025
-10 0 9 0.0848 -10.0000 0.0000 9.0000 0.5515 -0.3013 -0.8025
2 -11 7 0.1510 2.0000 -11.0000 7.0000 -0.6856 -0.4892 -0.6052
10 -1 -9 0.1004 10.0000 -1.0000 -9.0000 -0.5878 0.2094 0.7978
0 -7 -6 0.1779 -0.0000 -7.0000 -6.0000 -0.1349 -0.9584 0.4546
9 2 0 0.1387 9.0000 2.0000 0.0000 -0.5850 0.8801 0.0739
8 4 -1 0.1089 8.0000 4.0000 -1.0000 -0.4193 0.9341 0.1572
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
Cl1 Cu1 Cl1 92.41(4) 2_565
Cl2 Cu1 Cl1 94.55(5) .
Cl2 Cu1 Cl1 100.76(4) 2_565
N1 Cu1 Cl1 95.04(9) .
N1 Cu1 Cl1 93.92(9) 2_565
N1 Cu1 Cl2 162.08(9) .
N1 Cu1 O1 78.97(11) .
O1 Cu1 Cl1 172.20(8) .
O1 Cu1 Cl1 92.98(8) 2_565
O1 Cu1 Cl2 89.98(9) .
Cu1 Cl1 Cu1 87.59(4) 2_565
C11 N1 Cu1 127.0(3) .
C11 N1 C15 118.5(3) .
C15 N1 Cu1 114.5(2) .
C16 O1 Cu1 116.0(2) .
N1 C11 H11 119.2 .
N1 C11 C12 121.5(3) .
C12 C11 H11 119.2 .
C11 C12 H12 120.1 .
C13 C12 C11 119.8(4) .
C13 C12 H12 120.1 .
C12 C13 H13 120.3 .
C12 C13 C14 119.4(4) .
C14 C13 H13 120.3 .
C13 C14 H14 120.7 .
C15 C14 C13 118.5(4) .
C15 C14 H14 120.7 .
N1 C15 C14 122.2(4) .
N1 C15 C16 112.8(3) .
C14 C15 C16 124.9(3) .
O1 C16 C15 117.5(3) .
O1 C16 C17 120.2(4) .
C17 C16 C15 122.3(3) .
C16 C17 H17A 109.5 .
C16 C17 H17B 109.5 .
C16 C17 H17C 109.5 .
H17A C17 H17B 109.5 .
H17A C17 H17C 109.5 .
H17B C17 H17C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Cl1 2.2532(11) .
Cu1 Cl1 2.7011(12) 2_565
Cu1 Cl2 2.2160(13) .
Cu1 N1 2.012(3) .
Cu1 O1 2.042(3) .
Cl1 Cu1 2.7011(12) 2_565
N1 C11 1.325(5) .
N1 C15 1.357(4) .
O1 C16 1.228(4) .
C11 H11 0.9300 .
C11 C12 1.386(5) .
C12 H12 0.9300 .
C12 C13 1.352(5) .
C13 H13 0.9300 .
C13 C14 1.379(5) .
C14 H14 0.9300 .
C14 C15 1.368(5) .
C15 C16 1.480(5) .
C16 C17 1.478(5) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
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
Cu1 N1 C11 C12 176.1(3)
Cu1 N1 C15 C14 -177.3(3)
Cu1 N1 C15 C16 2.7(4)
Cu1 O1 C16 C15 -3.7(4)
Cu1 O1 C16 C17 176.5(3)
N1 C11 C12 C13 1.4(6)
N1 C15 C16 O1 0.7(5)
N1 C15 C16 C17 -179.5(3)
C11 N1 C15 C14 1.0(5)
C11 N1 C15 C16 -178.9(3)
C11 C12 C13 C14 0.2(6)
C12 C13 C14 C15 -1.1(6)
C13 C14 C15 N1 0.5(6)
C13 C14 C15 C16 -179.5(4)
C14 C15 C16 O1 -179.3(4)
C14 C15 C16 C17 0.5(6)
C15 N1 C11 C12 -2.0(5)
