#------------------------------------------------------------------------------
#$Date: 2019-11-12 04:56:28 +0200 (Tue, 12 Nov 2019) $
#$Revision: 227637 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/18/7701877.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_7701877
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 Cl2 Cu N2 O2'
_chemical_formula_sum            'C14 H14 Cl2 Cu N2 O2'
_chemical_formula_weight         376.71
_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     dual
_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                98.797(10)
_cell_angle_beta                 110.504(11)
_cell_angle_gamma                109.976(10)
_cell_formula_units_Z            1
_cell_length_a                   7.5026(8)
_cell_length_b                   7.5541(9)
_cell_length_c                   8.0228(10)
_cell_measurement_reflns_used    1239
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.6755
_cell_measurement_theta_min      2.8450
_cell_volume                     380.59(10)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297.15
_diffrn_detector_area_resol_mean 10.4757
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -13.00   99.00   1.0000   10.2500
omega____ theta____ kappa____ phi______ frames
    -       21.5439   77.0000  -60.0000 112

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   97.00   1.0000   10.2500
omega____ theta____ kappa____ phi______ frames
    -       21.5439   77.0000   60.0000 106

#__ type_ start__ end____ width___ exp.time_
  3 omega  -10.00   99.00   1.0000   10.2500
omega____ theta____ kappa____ phi______ frames
    -       21.5439   77.0000 -180.0000 109
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0071303000
_diffrn_orient_matrix_UB_12      0.0876840000
_diffrn_orient_matrix_UB_13      0.0364713000
_diffrn_orient_matrix_UB_21      0.1110033000
_diffrn_orient_matrix_UB_22      0.0527407000
_diffrn_orient_matrix_UB_23      0.0385789000
_diffrn_orient_matrix_UB_31      -0.0092951000
_diffrn_orient_matrix_UB_32      0.0238754000
_diffrn_orient_matrix_UB_33      -0.0838806000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2393
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.739
_diffrn_reflns_theta_min         2.851
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.789
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_correction_T_min  0.575
_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    1.644
_exptl_crystal_description       prism
_exptl_crystal_F_000             191
_exptl_crystal_size_max          0.2398
_exptl_crystal_size_mid          0.1713
_exptl_crystal_size_min          0.0986
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         1696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0352
_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)+(0.0307P)²+0.0510P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0792
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1388
_reflns_number_total             1696
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt03822a2.cif
_cod_data_source_block           Compound_2B_dm3562a
_cod_original_cell_volume        380.59(9)
_cod_database_code               7701877
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C14 H14 Cl2 Cu1 N2 O2'
_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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.0000 0.5000 0.5000 0.03342(16) Uani 1 2 d S T P
Cl1 Cl 0.04630(11) 0.79684(10) 0.68007(9) 0.0460(2) Uani 1 1 d . . .
N1 N 0.1893(3) 0.6464(3) 0.3969(3) 0.0320(5) Uani 1 1 d . . .
O1 O -0.2256(3) 0.5457(3) 0.2328(2) 0.0441(5) Uani 1 1 d . . .
C11 C 0.3932(4) 0.6898(4) 0.4734(4) 0.0417(7) Uani 1 1 d . . .
H11 H 0.4478 0.6543 0.5795 0.050 Uiso 1 1 calc R . .
C12 C 0.5275(4) 0.7860(4) 0.4013(4) 0.0468(7) Uani 1 1 d . . .
H12 H 0.6697 0.8141 0.4577 0.056 Uiso 1 1 calc R . .
C13 C 0.4478(4) 0.8388(4) 0.2462(4) 0.0487(8) Uani 1 1 d . . .
H13 H 0.5350 0.9038 0.1952 0.058 Uiso 1 1 calc R . .
C14 C 0.2353(4) 0.7946(4) 0.1653(4) 0.0418(7) Uani 1 1 d . . .
H14 H 0.1780 0.8290 0.0592 0.050 Uiso 1 1 calc R . .
C15 C 0.1101(4) 0.6991(4) 0.2440(3) 0.0317(6) Uani 1 1 d . . .
C16 C -0.1223(4) 0.6427(4) 0.1655(3) 0.0338(6) Uani 1 1 d . . .
C17 C -0.2198(4) 0.7085(4) 0.0046(4) 0.0447(7) Uani 1 1 d . . .
H17A H -0.3696 0.6519 -0.0377 0.067 Uiso 1 1 calc GR . .
H17B H -0.1876 0.6654 -0.0957 0.067 Uiso 1 1 calc GR . .
H17C H -0.1649 0.8503 0.0437 0.067 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'
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'
Cu Cu 0.3201 1.2651 '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
-8 9 0 0.0589 -8.0000 9.0000 0.0000 0.8456 -0.4154 0.2893
0 -10 0 0.0472 -0.0000 -10.0000 0.0000 -0.8769 -0.5262 -0.2401
0 0 -10 0.0872 0.0000 0.0000 -10.0000 -0.3656 -0.3875 0.8379
2 -2 9 0.0630 2.0000 -2.0000 9.0000 0.1395 0.4658 -0.8204
8 -1 -10 0.1098 8.0000 -1.0000 -10.0000 -0.5096 0.4488 0.7406
-3 -1 11 0.0865 -3.0000 -1.0000 11.0000 0.3356 0.0403 -0.9182
0 10 0 0.0514 0.0000 10.0000 -0.0000 0.8769 0.5262 0.2401
-8 -2 9 0.0994 -8.0000 -2.0000 9.0000 0.2100 -0.6455 -0.7288
7 -10 0 0.0518 7.0000 -10.0000 0.0000 -0.9262 0.2516 -0.3042
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
Cl1 Cu1 Cl1 180.00(4) 2_566 .
Cl1 Cu1 O1 91.26(5) . 2_566
Cl1 Cu1 O1 88.74(5) 2_566 2_566
Cl1 Cu1 O1 91.26(5) 2_566 .
Cl1 Cu1 O1 88.74(5) . .
N1 Cu1 Cl1 90.24(6) . .
N1 Cu1 Cl1 90.24(6) 2_566 2_566
N1 Cu1 Cl1 89.76(6) . 2_566
N1 Cu1 Cl1 89.76(6) 2_566 .
N1 Cu1 N1 180.0 2_566 .
N1 Cu1 O1 75.25(7) . .
N1 Cu1 O1 104.75(7) . 2_566
N1 Cu1 O1 75.25(7) 2_566 2_566
N1 Cu1 O1 104.75(7) 2_566 .
O1 Cu1 O1 180.00(8) . 2_566
C11 N1 Cu1 121.14(19) . .
C11 N1 C15 118.9(2) . .
C15 N1 Cu1 119.94(16) . .
C16 O1 Cu1 109.55(15) . .
N1 C11 H11 118.8 . .
N1 C11 C12 122.5(3) . .
C12 C11 H11 118.8 . .
C11 C12 H12 120.6 . .
C13 C12 C11 118.8(3) . .
C13 C12 H12 120.6 . .
C12 C13 H13 120.4 . .
C12 C13 C14 119.2(3) . .
C14 C13 H13 120.4 . .
C13 C14 H14 120.4 . .
C15 C14 C13 119.2(3) . .
C15 C14 H14 120.4 . .
N1 C15 C14 121.4(2) . .
N1 C15 C16 115.4(2) . .
C14 C15 C16 123.2(2) . .
O1 C16 C15 119.7(2) . .
O1 C16 C17 121.5(2) . .
C17 C16 C15 118.8(2) . .
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 2.3154(8) .
Cu1 Cl1 2.3154(8) 2_566
Cu1 N1 1.989(2) .
Cu1 N1 1.989(2) 2_566
Cu1 O1 2.3798(18) 2_566
Cu1 O1 2.3798(18) .
N1 C11 1.327(3) .
N1 C15 1.348(3) .
O1 C16 1.207(3) .
C11 H11 0.9300 .
C11 C12 1.384(4) .
C12 H12 0.9300 .
C12 C13 1.364(4) .
C13 H13 0.9300 .
C13 C14 1.385(4) .
C14 H14 0.9300 .
C14 C15 1.376(3) .
C15 C16 1.503(3) .
C16 C17 1.494(3) .
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 177.9(2)
Cu1 N1 C15 C14 -177.78(19)
Cu1 N1 C15 C16 1.0(3)
Cu1 O1 C16 C15 4.9(3)
Cu1 O1 C16 C17 -175.16(19)
N1 C11 C12 C13 0.2(4)
N1 C15 C16 O1 -4.5(3)
N1 C15 C16 C17 175.6(2)
C11 N1 C15 C14 0.7(4)
C11 N1 C15 C16 179.5(2)
C11 C12 C13 C14 -0.1(4)
C12 C13 C14 C15 0.3(4)
C13 C14 C15 N1 -0.6(4)
C13 C14 C15 C16 -179.3(2)
C14 C15 C16 O1 174.3(2)
C14 C15 C16 C17 -5.6(4)
C15 N1 C11 C12 -0.5(4)
