# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_5_dm332ca
_database_code_depnum_ccdc_archive 'CCDC 1491835'
loop_
_audit_author_name
_audit_author_address
'Daniel Miguel'
;Universidad de Valladolid
Spain
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
_audit_creation_date             2016-07-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H10 Cl2 Cu N2 O2, H2 O'
_chemical_formula_sum            'C9 H12 Cl2 Cu N2 O3'
_chemical_formula_weight         330.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H9 N2 O2 Cl2 Cu1'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.8843(4)
_cell_length_b                   14.8928(5)
_cell_length_c                   10.1346(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.485(5)
_cell_angle_gamma                90
_cell_volume                     1247.76(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2404
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0200
_cell_measurement_theta_min      2.7300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.175
_exptl_absorpt_correction_T_max  0.856
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.1999
_exptl_crystal_size_mid          0.1625
_exptl_crystal_size_min          0.0821
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5007
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.607
_diffrn_reflns_theta_min         2.556
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -111.00  -78.00   1.0000   55.5100
omega____ theta____ kappa____ phi______ frames
    -      -19.7470  -37.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega  -24.00  116.00   1.0000   55.5100
omega____ theta____ kappa____ phi______ frames
    -       21.5439   77.0000 -180.0000 140

#__ type_ start__ end____ width___ exp.time_
  3 omega   73.00  118.00   1.0000   55.5100
omega____ theta____ kappa____ phi______ frames
    -       21.5439  144.0000  161.0000 45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0224024000
_diffrn_orient_matrix_UB_12      0.0335664000
_diffrn_orient_matrix_UB_13      0.0533466000
_diffrn_orient_matrix_UB_21      0.0296258000
_diffrn_orient_matrix_UB_22      -0.0336534000
_diffrn_orient_matrix_UB_23      0.0527588000
_diffrn_orient_matrix_UB_31      0.0773550000
_diffrn_orient_matrix_UB_32      0.0031433000
_diffrn_orient_matrix_UB_33      -0.0050778000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2204
_reflns_number_total             2804
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2804
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.047
_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)+(0.0321P)²+0.7815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0868
_refine_special_details          ?
_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 O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O90(H90A,H90B)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.83487(5) 0.43829(2) 0.84235(4) 0.03453(13) Uani 1 1 d . . . . .
Cl1 Cl 0.85579(11) 0.45919(6) 1.07005(8) 0.0429(2) Uani 1 1 d . . . . .
Cl2 Cl 0.64230(11) 0.54487(6) 0.75952(9) 0.0506(2) Uani 1 1 d . . . . .
N1 N 0.8492(3) 0.41896(15) 0.6491(2) 0.0289(5) Uani 1 1 d . . . . .
N2 N 0.9837(3) 0.32993(16) 0.8862(3) 0.0321(6) Uani 1 1 d . . . . .
O1 O 1.1219(3) 0.19486(17) 1.2783(3) 0.0520(6) Uani 1 1 d . . . . .
O2 O 0.8673(3) 0.15710(19) 1.2341(3) 0.0585(7) Uani 1 1 d . . . . .
H2 H 0.9049 0.1395 1.3164 0.088 Uiso 1 1 calc GR . . . .
C11 C 0.7762(4) 0.4641(2) 0.5293(3) 0.0407(8) Uani 1 1 d . . . . .
H11 H 0.7054 0.5102 0.5287 0.049 Uiso 1 1 calc R . . . .
C12 C 0.8018(4) 0.4449(2) 0.4058(3) 0.0452(8) Uani 1 1 d . . . . .
H12 H 0.7486 0.4775 0.3236 0.054 Uiso 1 1 calc R . . . .
C13 C 0.9055(4) 0.3779(2) 0.4057(3) 0.0456(8) Uani 1 1 d . . . . .
H13 H 0.9255 0.3648 0.3239 0.055 Uiso 1 1 calc R . . . .
C14 C 0.9810(4) 0.3295(2) 0.5287(4) 0.0433(8) Uani 1 1 d . . . . .
H14 H 1.0513 0.2828 0.5307 0.052 Uiso 1 1 calc R . . . .
C15 C 0.9502(4) 0.35154(19) 0.6478(3) 0.0320(7) Uani 1 1 d . . . . .
C16 C 1.0196(4) 0.3042(2) 0.7825(3) 0.0377(7) Uani 1 1 d . . . . .
H16 H 1.0891 0.2559 0.7920 0.045 Uiso 1 1 calc R . . . .
C17 C 1.0539(4) 0.2814(2) 1.0214(3) 0.0415(8) Uani 1 1 d . . . . .
H17A H 1.1035 0.3237 1.0977 0.050 Uiso 1 1 calc R . . . .
H17B H 1.1372 0.2406 1.0172 0.050 Uiso 1 1 calc R . . . .
C18 C 0.9233(4) 0.2287(2) 1.0508(3) 0.0423(8) Uani 1 1 d . . . . .
H18A H 0.8314 0.2676 1.0377 0.051 Uiso 1 1 calc R . . . .
H18B H 0.8873 0.1797 0.9835 0.051 Uiso 1 1 calc R . . . .
C19 C 0.9837(4) 0.1917(2) 1.1988(3) 0.0371(7) Uani 1 1 d . . . . .
O90 O 0.9895(4) 0.1107(2) 1.5016(4) 0.0757(9) Uani 1 1 d . . . . .
H90A H 0.9435 0.0894 1.5551 0.114 Uiso 1 1 d G . . . .
H90B H 1.0776 0.0829 1.5163 0.114 Uiso 1 1 d G . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 Cl1 2.2677(8) . ?
Cu1 Cl2 2.2582(9) . ?
Cu1 N1 2.029(2) . ?
Cu1 N2 2.030(2) . ?
N1 C11 1.330(4) . ?
N1 C15 1.350(4) . ?
N2 C16 1.264(4) . ?
N2 C17 1.471(4) . ?
O1 C19 1.197(4) . ?
O2 H2 0.8200 . ?
O2 C19 1.318(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.357(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.372(4) . ?
C15 C16 1.457(4) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.517(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.500(4) . ?
O90 H90A 0.8500 . ?
O90 H90B 0.8500 . ?

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
Cl2 Cu1 Cl1 92.89(3) . . ?
N1 Cu1 Cl1 172.28(7) . . ?
N1 Cu1 Cl2 92.73(7) . . ?
N1 Cu1 N2 80.36(9) . . ?
N2 Cu1 Cl1 94.72(7) . . ?
N2 Cu1 Cl2 169.87(8) . . ?
C11 N1 Cu1 128.8(2) . . ?
C11 N1 C15 118.1(3) . . ?
C15 N1 Cu1 113.06(19) . . ?
C16 N2 Cu1 113.6(2) . . ?
C16 N2 C17 118.4(3) . . ?
C17 N2 Cu1 127.9(2) . . ?
C19 O2 H2 109.5 . . ?
N1 C11 H11 118.8 . . ?
N1 C11 C12 122.4(3) . . ?
C12 C11 H11 118.8 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.2(3) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.7(3) . . ?
C15 C14 H14 120.6 . . ?
N1 C15 C14 122.3(3) . . ?
N1 C15 C16 113.9(3) . . ?
C14 C15 C16 123.8(3) . . ?
N2 C16 C15 118.9(3) . . ?
N2 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
N2 C17 H17A 109.6 . . ?
N2 C17 H17B 109.6 . . ?
N2 C17 C18 110.1(3) . . ?
H17A C17 H17B 108.2 . . ?
C18 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C17 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 C17 111.5(3) . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
O1 C19 O2 123.1(3) . . ?
O1 C19 C18 124.2(3) . . ?
O2 C19 C18 112.7(3) . . ?
H90A O90 H90B 109.5 . . ?

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
Cu1 N1 C11 C12 177.9(2) . . . . ?
Cu1 N1 C15 C14 -177.8(2) . . . . ?
Cu1 N1 C15 C16 3.3(3) . . . . ?
Cu1 N2 C16 C15 -1.5(4) . . . . ?
Cu1 N2 C17 C18 71.0(3) . . . . ?
N1 C11 C12 C13 -0.3(6) . . . . ?
N1 C15 C16 N2 -1.2(4) . . . . ?
N2 C17 C18 C19 -169.9(3) . . . . ?
C11 N1 C15 C14 0.9(5) . . . . ?
C11 N1 C15 C16 -177.9(3) . . . . ?
C11 C12 C13 C14 1.1(5) . . . . ?
C12 C13 C14 C15 -0.9(5) . . . . ?
C13 C14 C15 N1 -0.2(5) . . . . ?
C13 C14 C15 C16 178.6(3) . . . . ?
C14 C15 C16 N2 179.9(3) . . . . ?
C15 N1 C11 C12 -0.7(5) . . . . ?
C16 N2 C17 C18 -110.3(3) . . . . ?
C17 N2 C16 C15 179.7(3) . . . . ?
C17 C18 C19 O1 -7.6(5) . . . . ?
C17 C18 C19 O2 170.7(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
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
-10 -10 0 0.0441 -10.0125 -10.0196 -0.0013 -0.5607 0.0405 -0.8060
3 19 -5 0.0745 3.0132 19.0503 -5.0097 0.4397 -0.8161 0.3184
-4 -14 11 0.0619 -4.0160 -14.0369 11.0273 0.0271 0.9352 -0.4108
11 -1 -11 0.0710 11.0163 -1.0093 -11.0314 -0.3756 -0.2217 0.9050
2 16 -9 0.1143 2.0138 16.0436 -9.0212 0.1024 -0.9562 0.2520
-10 9 0 0.0741 -10.0051 9.0322 0.0030 0.0792 -0.6002 -0.7456
10 -10 1 0.0374 10.0041 -10.0351 0.9995 -0.0594 0.6868 0.7372
2 -15 -10 0.0949 2.0025 -15.0406 -10.0310 -0.9951 0.0363 0.1586
-8 11 11 0.0667 -8.0098 11.0342 11.0334 0.7795 -0.0265 -0.6409
10 10 0 0.0381 10.0125 10.0196 0.0013 0.5607 -0.0405 0.8060

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_8_dm323b
_database_code_depnum_ccdc_archive 'CCDC 1955678'
loop_
_audit_author_name
_audit_author_address
'Daniel Miguel'
;Universidad de Valladolid
Spain
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
_audit_creation_date             2019-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H32 Cl4 Cu4 N4 O6'
_chemical_formula_sum            'C30 H32 Cl4 Cu4 N4 O6'
_chemical_formula_weight         940.55
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H8Cl2Cu2N2O4
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'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   8.81004(20)
_cell_length_b                   8.81004(20)
_cell_length_c                   48.3804(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3755.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3778
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.5780
_cell_measurement_theta_min      2.4600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.564
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark green'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 68 0.0527
-5 2 -61 0.0291
-1 -10 -43 0.0601
6 7 46 0.0898
7 10 -13 0.1065
9 -6 -30 0.1004
0 -3 66 0.0529
-11 -1 35 0.0415
-1 12 14 0.0761
-1 -12 -8 0.0788
12 -1 3 0.1053
-1 3 -66 0.0302

_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.091
loop_
_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
-0.9986 -0.9614 68.2672 0.1891 0.8841 -0.4436
-5.0297 1.9074 -61.2329 -0.1177 -0.9888 -0.0424
-0.8966 -10.0662 -42.8878 -0.9518 -0.3661 0.1280
5.9416 7.1128 45.9451 0.7600 0.6179 0.2235
6.9190 10.0856 -13.3419 0.7617 -0.1935 0.6242
9.0903 -5.9443 -30.0041 -0.5335 0.0033 0.8212
0.0250 -2.9573 66.3054 0.0319 0.9320 -0.3632
-11.0247 -1.0890 35.2120 0.0003 0.1624 -1.0181
-1.1271 12.0285 13.7480 0.9793 -0.1168 -0.1169
-0.8792 -12.0445 -7.7154 -0.9666 0.1374 -0.0658
12.0448 -0.8768 2.9648 0.0026 0.4094 0.8834
-1.0279 2.9470 -66.2994 -0.0376 -0.9610 0.2880

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -62
_diffrn_reflns_number            9186
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.652
_diffrn_reflns_theta_min         2.350
_diffrn_ambient_temperature      297.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00 -19.00   0.75   69.81    --   21.54 -37.00-120.00   36
  2  ω    -16.00  86.00   0.75   69.81    --   21.54  37.00-180.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0048813000
_diffrn_orient_matrix_UB_12      0.0773759000
_diffrn_orient_matrix_UB_13      0.0039306000
_diffrn_orient_matrix_UB_21      0.0291748000
_diffrn_orient_matrix_UB_22      -0.0219100000
_diffrn_orient_matrix_UB_23      0.0130687000
_diffrn_orient_matrix_UB_31      0.0749100000
_diffrn_orient_matrix_UB_32      0.0034220000
_diffrn_orient_matrix_UB_33      -0.0053536000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.644
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                3561
_reflns_number_total             4283
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.50(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0604
_refine_ls_restrained_S_all      1.196
_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)+(0.0422P)²+6.1166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1353
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.50(4)
 0.50(4)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C21(H21), C22(H22), C23(H23), C24(H24)
3.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.79559(12) 0.86559(12) 0.02808(2) 0.0371(3) Uani 1 1 d . . . . .
Cu2 Cu 0.77220(12) 0.68805(13) 0.08342(2) 0.0453(3) Uani 1 1 d . . . . .
Cl2 Cl 0.6391(3) 0.5867(3) 0.11764(5) 0.0585(7) Uani 1 1 d . . . . .
Cl3 Cl 0.5721(3) 0.7558(4) 0.05640(5) 0.0635(7) Uani 1 1 d . . . . .
O1 O 0.8989(6) 0.8214(7) 0.06213(10) 0.0404(14) Uani 1 1 d . . . . .
O2 O 0.7067(6) 0.9028(6) -0.00801(10) 0.0361(12) Uani 1 1 d . . . . .
O3 O 0.5229(7) 1.0558(7) -0.02750(13) 0.0487(15) Uani 1 1 d . . . . .
N1 N 0.7213(9) 1.0762(9) 0.03509(13) 0.0449(18) Uani 1 1 d . . . . .
N2 N 0.9660(8) 0.5880(10) 0.09148(14) 0.0483(19) Uani 1 1 d . . . . .
C11 C 0.7187(13) 1.1448(12) 0.05983(19) 0.060(3) Uani 1 1 d . . . . .
H11 H 0.7690 1.1012 0.0748 0.072 Uiso 1 1 calc R . . . .
C12 C 0.6410(15) 1.2813(14) 0.0632(2) 0.073(3) Uani 1 1 d . . . . .
H12 H 0.6328 1.3251 0.0807 0.087 Uiso 1 1 calc R . . . .
C13 C 0.5775(16) 1.3495(15) 0.0410(2) 0.083(4) Uani 1 1 d . . . . .
H13 H 0.5304 1.4435 0.0428 0.100 Uiso 1 1 calc R . . . .
C14 C 0.5828(14) 1.2788(13) 0.0153(2) 0.070(3) Uani 1 1 d . . . . .
H14 H 0.5391 1.3235 -0.0002 0.084 Uiso 1 1 calc R . . . .
C15 C 0.6557(10) 1.1389(11) 0.01352(17) 0.044(2) Uani 1 1 d . . . . .
C16 C 0.6659(9) 1.0511(10) -0.01413(16) 0.0374(19) Uani 1 1 d . . . . .
C17 C 0.7776(11) 1.1288(10) -0.03334(15) 0.0418(19) Uani 1 1 d . . . . .
H17A H 0.8767 1.1276 -0.0246 0.050 Uiso 1 1 calc R . . . .
H17B H 0.7474 1.2342 -0.0352 0.050 Uiso 1 1 calc R . . . .
C21 C 0.9851(11) 0.4620(13) 0.1067(2) 0.062(3) Uani 1 1 d . . . . .
H21 H 0.9007 0.4189 0.1152 0.074 Uiso 1 1 calc R . . . .
C22 C 1.1233(15) 0.3944(16) 0.1103(3) 0.083(4) Uani 1 1 d . . . . .
H22 H 1.1316 0.3029 0.1198 0.100 Uiso 1 1 calc R . . . .
C23 C 1.2493(13) 0.4639(15) 0.0996(2) 0.071(3) Uani 1 1 d . . . . .
H23 H 1.3450 0.4224 0.1026 0.085 Uiso 1 1 calc R . . . .
C24 C 1.2338(10) 0.5944(13) 0.08469(19) 0.056(3) Uani 1 1 d . . . . .
H24 H 1.3185 0.6434 0.0775 0.068 Uiso 1 1 calc R . . . .
C25 C 1.0876(9) 0.6531(12) 0.08041(17) 0.045(2) Uani 1 1 d . . . . .
C26 C 1.0596(10) 0.7937(11) 0.06289(15) 0.040(2) Uani 1 1 d . . . . .
C27 C 1.1355(12) 0.9337(12) 0.07623(18) 0.059(3) Uani 1 1 d . . . . .
H27A H 1.1131 1.0223 0.0654 0.089 Uiso 1 1 calc GR . . . .
H27B H 1.2433 0.9188 0.0769 0.089 Uiso 1 1 calc GR . . . .
H27C H 1.0971 0.9470 0.0946 0.089 Uiso 1 1 calc GR . . . .
C30 C 0.4040(12) 0.9824(15) -0.0139(2) 0.078(4) Uani 1 1 d . . . . .
H30A H 0.4343 0.8809 -0.0092 0.116 Uiso 1 1 calc GR . . . .
H30B H 0.3168 0.9789 -0.0258 0.116 Uiso 1 1 calc GR . . . .
H30C H 0.3791 1.0369 0.0027 0.116 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 Cu1 2.8537(18) 7 ?
Cu1 Cl3 2.587(3) . ?
Cu1 O1 1.922(5) . ?
Cu1 O2 1.942(5) . ?
Cu1 O2 1.948(5) 7 ?
Cu1 N1 1.997(8) . ?
Cu2 Cl2 2.217(2) . ?
Cu2 Cl3 2.274(3) . ?
Cu2 O1 1.920(5) . ?
Cu2 N2 1.960(8) . ?
O1 C26 1.438(10) . ?
O2 Cu1 1.948(5) 7 ?
O2 C16 1.387(10) . ?
O3 C16 1.416(10) . ?
O3 C30 1.396(12) . ?
N1 C11 1.341(11) . ?
N1 C15 1.314(11) . ?
N2 C21 1.344(12) . ?
N2 C25 1.328(11) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(15) . ?
C12 H12 0.9300 . ?
C12 C13 1.355(15) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(14) . ?
C14 H14 0.9300 . ?
C14 C15 1.392(14) . ?
C15 C16 1.548(11) . ?
C16 C17 1.517(11) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C26 1.561(10) 7 ?
C21 H21 0.9300 . ?
C21 C22 1.367(15) . ?
C22 H22 0.9300 . ?
C22 C23 1.369(16) . ?
C23 H23 0.9300 . ?
C23 C24 1.364(15) . ?
C24 H24 0.9300 . ?
C24 C25 1.404(12) . ?
C25 C26 1.521(13) . ?
C26 C17 1.561(10) 7 ?
C26 C27 1.544(13) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

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
Cl3 Cu1 Cu1 126.02(7) . 7 ?
O1 Cu1 Cu1 132.06(18) . 7 ?
O1 Cu1 Cl3 80.25(17) . . ?
O1 Cu1 O2 174.9(2) . . ?
O1 Cu1 O2 93.0(2) . 7 ?
O1 Cu1 N1 101.4(3) . . ?
O2 Cu1 Cu1 42.71(15) 7 7 ?
O2 Cu1 Cu1 42.88(16) . 7 ?
O2 Cu1 Cl3 103.45(18) . . ?
O2 Cu1 Cl3 111.37(18) 7 . ?
O2 Cu1 O2 82.4(2) . 7 ?
O2 Cu1 N1 155.7(3) 7 . ?
O2 Cu1 N1 82.2(3) . . ?
N1 Cu1 Cu1 115.7(2) . 7 ?
N1 Cu1 Cl3 90.5(2) . . ?
Cl2 Cu2 Cl3 97.17(10) . . ?
O1 Cu2 Cl2 162.69(19) . . ?
O1 Cu2 Cl3 88.95(18) . . ?
O1 Cu2 N2 82.8(3) . . ?
N2 Cu2 Cl2 97.5(2) . . ?
N2 Cu2 Cl3 155.1(2) . . ?
Cu2 Cl3 Cu1 79.19(8) . . ?
Cu2 O1 Cu1 108.0(3) . . ?
C26 O1 Cu1 121.5(4) . . ?
C26 O1 Cu2 117.1(5) . . ?
Cu1 O2 Cu1 94.4(2) . 7 ?
C16 O2 Cu1 117.1(4) . . ?
C16 O2 Cu1 122.4(5) . 7 ?
C30 O3 C16 116.0(7) . . ?
C11 N1 Cu1 125.1(7) . . ?
C15 N1 Cu1 113.6(6) . . ?
C15 N1 C11 120.8(9) . . ?
C21 N2 Cu2 126.1(7) . . ?
C25 N2 Cu2 115.4(6) . . ?
C25 N2 C21 118.5(8) . . ?
N1 C11 H11 119.9 . . ?
N1 C11 C12 120.2(10) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.4(9) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.9(11) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 121.1 . . ?
C13 C14 C15 117.8(10) . . ?
C15 C14 H14 121.1 . . ?
N1 C15 C14 121.7(9) . . ?
N1 C15 C16 116.8(8) . . ?
C14 C15 C16 121.4(8) . . ?
O2 C16 O3 110.8(7) . . ?
O2 C16 C15 107.5(6) . . ?
O2 C16 C17 112.8(7) . . ?
O3 C16 C15 109.2(7) . . ?
O3 C16 C17 106.5(7) . . ?
C17 C16 C15 110.0(7) . . ?
C16 C17 H17A 108.2 . . ?
C16 C17 H17B 108.2 . . ?
C16 C17 C26 116.4(7) . 7 ?
H17A C17 H17B 107.4 . . ?
C26 C17 H17A 108.2 7 . ?
C26 C17 H17B 108.2 7 . ?
N2 C21 H21 118.6 . . ?
N2 C21 C22 122.7(10) . . ?
C22 C21 H21 118.6 . . ?
C21 C22 H22 120.7 . . ?
C21 C22 C23 118.7(11) . . ?
C23 C22 H22 120.7 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.7(11) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 120.6 . . ?
C23 C24 C25 118.7(10) . . ?
C25 C24 H24 120.6 . . ?
N2 C25 C24 121.4(9) . . ?
N2 C25 C26 116.4(8) . . ?
C24 C25 C26 122.1(8) . . ?
O1 C26 C17 112.1(6) . 7 ?
O1 C26 C25 108.2(7) . . ?
O1 C26 C27 107.6(7) . . ?
C25 C26 C17 111.9(8) . 7 ?
C25 C26 C27 110.3(7) . . ?
C27 C26 C17 106.7(7) . 7 ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O3 C30 H30A 109.5 . . ?
O3 C30 H30B 109.5 . . ?
O3 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

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
Cu1 O1 C26 C17 -9.5(10) . . . 7 ?
Cu1 O1 C26 C25 -133.4(5) . . . . ?
Cu1 O1 C26 C27 107.4(6) . . . . ?
Cu1 O2 C16 O3 -137.4(5) . . . . ?
Cu1 O2 C16 O3 107.3(6) 7 . . . ?
Cu1 O2 C16 C15 -18.1(8) . . . . ?
Cu1 O2 C16 C15 -133.4(5) 7 . . . ?
Cu1 O2 C16 C17 -12.0(9) 7 . . . ?
Cu1 O2 C16 C17 103.3(6) . . . . ?
Cu1 N1 C11 C12 -168.9(8) . . . . ?
Cu1 N1 C15 C14 173.1(8) . . . . ?
Cu1 N1 C15 C16 -8.0(10) . . . . ?
Cu2 O1 C26 C17 126.6(6) . . . 7 ?
Cu2 O1 C26 C25 2.7(8) . . . . ?
Cu2 O1 C26 C27 -116.5(6) . . . . ?
Cu2 N2 C21 C22 176.6(10) . . . . ?
Cu2 N2 C25 C24 179.4(7) . . . . ?
Cu2 N2 C25 C26 -0.7(10) . . . . ?
O2 C16 C17 C26 63.5(10) . . . 7 ?
O3 C16 C17 C26 -58.3(9) . . . 7 ?
N1 C11 C12 C13 -4.8(18) . . . . ?
N1 C15 C16 O2 16.8(11) . . . . ?
N1 C15 C16 O3 137.1(8) . . . . ?
N1 C15 C16 C17 -106.4(9) . . . . ?
N2 C21 C22 C23 5(2) . . . . ?
N2 C25 C26 O1 -1.2(10) . . . . ?
N2 C25 C26 C17 -125.2(8) . . . 7 ?
N2 C25 C26 C27 116.2(9) . . . . ?
C11 N1 C15 C14 0.8(15) . . . . ?
C11 N1 C15 C16 179.6(8) . . . . ?
C11 C12 C13 C14 4(2) . . . . ?
C12 C13 C14 C15 -1(2) . . . . ?
C13 C14 C15 N1 -1.8(17) . . . . ?
C13 C14 C15 C16 179.4(11) . . . . ?
C14 C15 C16 O2 -164.3(9) . . . . ?
C14 C15 C16 O3 -44.0(12) . . . . ?
C14 C15 C16 C17 72.5(11) . . . . ?
C15 N1 C11 C12 2.5(15) . . . . ?
C15 C16 C17 C26 -176.4(7) . . . 7 ?
C21 N2 C25 C24 -1.0(14) . . . . ?
C21 N2 C25 C26 178.9(8) . . . . ?
C21 C22 C23 C24 -3(2) . . . . ?
C22 C23 C24 C25 -0.7(17) . . . . ?
C23 C24 C25 N2 2.7(15) . . . . ?
C23 C24 C25 C26 -177.1(9) . . . . ?
C24 C25 C26 O1 178.6(8) . . . . ?
C24 C25 C26 C17 54.6(11) . . . 7 ?
C24 C25 C26 C27 -64.0(11) . . . . ?
C25 N2 C21 C22 -3.0(17) . . . . ?
C30 O3 C16 O2 53.6(10) . . . . ?
C30 O3 C16 C15 -64.6(10) . . . . ?
C30 O3 C16 C17 176.7(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.149
_oxdiff_exptl_absorpt_empirical_full_min 0.921
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.50(4)
2 0.50(4)

_vrf_PLAT987_dm323b              
;
PROBLEM: The Flack x is >> 0 -  Do a BASF/TWIN Refinement     Please Check
RESPONSE: The molecule was refined as a 2-component inversion twin
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_7_lam387c
_database_code_depnum_ccdc_archive 'CCDC 1491836'
loop_
_audit_author_name
_audit_author_address
'Daniel Miguel'
;Universidad de Valladolid
Spain
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
_audit_creation_date             2016-07-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 Cl2 Cu2 N2 O4'
_chemical_formula_sum            'C14 H16 Cl2 Cu2 N2 O4'
_chemical_formula_weight         474.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C7 H8 Cl1 Cu1 N1 O2'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.6181(5)
_cell_length_b                   4.0692(2)
_cell_length_c                   19.2298(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.417(4)
_cell_angle_gamma                90
_cell_volume                     827.15(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1344
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.5720
_cell_measurement_theta_min      3.5570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.915
_exptl_absorpt_correction_T_max  0.860
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light blue'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.904
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.3014
_exptl_crystal_size_mid          0.0974
_exptl_crystal_size_min          0.058
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3121
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.398
_diffrn_reflns_theta_min         2.111
_diffrn_ambient_temperature      298.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -62.00  -26.00   1.0000   23.5900
omega____ theta____ kappa____ phi______ frames
    -      -19.7470   77.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega   -2.00  122.00   1.0000   23.5900
omega____ theta____ kappa____ phi______ frames
    -       21.5439   77.0000  -90.0000 124

#__ type_ start__ end____ width___ exp.time_
  3 omega  -21.00   40.00   1.0000   23.5900
omega____ theta____ kappa____ phi______ frames
    -       21.5439   77.0000 -180.0000 61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0159378000
_diffrn_orient_matrix_UB_12      -0.1560832000
_diffrn_orient_matrix_UB_13      0.0129803000
_diffrn_orient_matrix_UB_21      -0.0647195000
_diffrn_orient_matrix_UB_22      0.0298960000
_diffrn_orient_matrix_UB_23      -0.0107664000
_diffrn_orient_matrix_UB_31      0.0077291000
_diffrn_orient_matrix_UB_32      -0.0711847000
_diffrn_orient_matrix_UB_33      -0.0330327000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1417
_reflns_number_total             1840
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1840
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.086
_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)+(0.0361P)²+0.8501P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1089
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.63250(5) 0.13559(15) 0.50802(3) 0.0352(2) Uani 1 1 d . . . . .
Cl1 Cl 0.74562(11) 0.5133(3) 0.57032(6) 0.0420(3) Uani 1 1 d . . . . .
O1 O 0.5147(3) -0.0895(10) 0.44095(17) 0.0485(10) Uani 1 1 d . . . . .
O2 O 0.5068(3) -0.0110(8) 0.31990(17) 0.0422(8) Uani 1 1 d . . . . .
N1 N 0.7494(3) 0.0515(9) 0.43563(18) 0.0304(8) Uani 1 1 d . . . . .
C11 C 0.8739(4) 0.1189(13) 0.4387(2) 0.0382(11) Uani 1 1 d . . . . .
H11 H 0.9103 0.2405 0.4764 0.046 Uiso 1 1 calc R . . . .
C12 C 0.9491(4) 0.0173(14) 0.3893(3) 0.0433(12) Uani 1 1 d . . . . .
H12 H 1.0344 0.0735 0.3928 0.052 Uiso 1 1 calc R . . . .
C13 C 0.8970(5) -0.1708(13) 0.3339(3) 0.0451(13) Uani 1 1 d . . . . .
H13 H 0.9466 -0.2461 0.2999 0.054 Uiso 1 1 calc R . . . .
C14 C 0.7703(5) -0.2432(12) 0.3303(3) 0.0418(12) Uani 1 1 d . . . . .
H14 H 0.7329 -0.3693 0.2937 0.050 Uiso 1 1 calc R . . . .
C15 C 0.6984(4) -0.1275(11) 0.3816(2) 0.0298(10) Uani 1 1 d . . . . .
C16 C 0.5568(4) -0.1915(11) 0.3790(2) 0.0307(10) Uani 1 1 d . . . . .
H16 H 0.5396 -0.4263 0.3719 0.037 Uiso 1 1 calc R . . . .
C17 C 0.3833(5) -0.1060(14) 0.2923(3) 0.0501(14) Uani 1 1 d . . . . .
H17A H 0.3659 -0.0172 0.2461 0.075 Uiso 1 1 calc GR . . . .
H17B H 0.3224 -0.0236 0.3218 0.075 Uiso 1 1 calc GR . . . .
H17C H 0.3782 -0.3414 0.2903 0.075 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 Cu1 3.0110(10) 3_656 ?
Cu1 Cl1 2.2291(13) . ?
Cu1 O1 1.931(3) 3_656 ?
Cu1 O1 1.940(3) . ?
Cu1 N1 1.980(4) . ?
O1 Cu1 1.931(3) 3_656 ?
O1 C16 1.375(5) . ?
O2 C16 1.414(5) . ?
O2 C17 1.421(5) . ?
N1 C11 1.346(5) . ?
N1 C15 1.340(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.362(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.385(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(6) . ?
C15 C16 1.522(6) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
Cl1 Cu1 Cu1 139.35(5) . 3_656 ?
O1 Cu1 Cu1 38.84(9) . 3_656 ?
O1 Cu1 Cu1 39.04(9) 3_656 3_656 ?
O1 Cu1 Cl1 102.40(10) 3_656 . ?
O1 Cu1 Cl1 164.57(13) . . ?
O1 Cu1 O1 77.88(14) 3_656 . ?
O1 Cu1 N1 81.87(13) . . ?
O1 Cu1 N1 158.63(15) 3_656 . ?
N1 Cu1 Cu1 120.41(10) . 3_656 ?
N1 Cu1 Cl1 98.94(11) . . ?
Cu1 O1 Cu1 102.12(14) 3_656 . ?
C16 O1 Cu1 118.4(3) . . ?
C16 O1 Cu1 139.1(3) . 3_656 ?
C16 O2 C17 115.0(4) . . ?
C11 N1 Cu1 127.7(3) . . ?
C15 N1 Cu1 113.9(3) . . ?
C15 N1 C11 117.9(4) . . ?
N1 C11 H11 118.5 . . ?
N1 C11 C12 123.1(5) . . ?
C12 C11 H11 118.5 . . ?
C11 C12 H12 120.4 . . ?
C11 C12 C13 119.1(4) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 120.8 . . ?
C14 C13 C12 118.4(5) . . ?
C14 C13 H13 120.8 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.7(5) . . ?
C15 C14 H14 120.2 . . ?
N1 C15 C14 121.8(4) . . ?
N1 C15 C16 116.4(4) . . ?
C14 C15 C16 121.8(4) . . ?
O1 C16 O2 114.3(4) . . ?
O1 C16 C15 108.7(3) . . ?
O1 C16 H16 110.1 . . ?
O2 C16 C15 103.4(3) . . ?
O2 C16 H16 110.1 . . ?
C15 C16 H16 110.1 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
Cu1 O1 C16 O2 -109.2(4) . . . . ?
Cu1 O1 C16 O2 79.1(6) 3_656 . . . ?
Cu1 O1 C16 C15 5.8(5) . . . . ?
Cu1 O1 C16 C15 -165.9(4) 3_656 . . . ?
Cu1 N1 C11 C12 172.2(4) . . . . ?
Cu1 N1 C15 C14 -172.2(3) . . . . ?
Cu1 N1 C15 C16 8.9(5) . . . . ?
N1 C11 C12 C13 -1.6(8) . . . . ?
N1 C15 C16 O1 -9.5(5) . . . . ?
N1 C15 C16 O2 112.3(4) . . . . ?
C11 N1 C15 C14 0.4(6) . . . . ?
C11 N1 C15 C16 -178.6(4) . . . . ?
C11 C12 C13 C14 1.0(8) . . . . ?
C12 C13 C14 C15 0.1(7) . . . . ?
C13 C14 C15 N1 -0.8(7) . . . . ?
C13 C14 C15 C16 178.1(4) . . . . ?
C14 C15 C16 O1 171.6(4) . . . . ?
C14 C15 C16 O2 -66.6(5) . . . . ?
C15 N1 C11 C12 0.8(7) . . . . ?
C17 O2 C16 O1 -80.8(5) . . . . ?
C17 O2 C16 C15 161.2(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
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
0 0 27 0.0252 0.0279 0.0099 27.0123 0.3486 -0.2923 -0.8928
0 0 -27 0.0328 -0.0279 -0.0099 -27.0123 -0.3486 0.2923 0.8928
-2 2 -25 0.0459 -2.0260 1.9889 -25.0150 -0.6028 0.4599 0.6691
15 0 -2 0.0328 14.9984 0.0038 -1.9984 -0.2656 -0.9491 0.1817
-15 0 7 0.0578 -14.9933 -0.0019 7.0007 0.3301 0.8949 -0.3470
5 -5 -10 0.1002 4.9900 -4.9989 -9.9956 0.5710 -0.3648 0.7246
-6 5 13 0.1181 -5.9870 4.9998 12.9968 -0.5163 0.3970 -0.8315

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_11_dm351a
_database_code_depnum_ccdc_archive 'CCDC 1491841'
loop_
_audit_author_name
_audit_author_address
'Daniel Miguel'
;Universidad de Valladolid
Spain
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
_audit_creation_date             2016-04-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H9 Cu N3 O3'
_chemical_formula_sum            'C10 H9 Cu N3 O3'
_chemical_formula_weight         282.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H9 N3 O3 Cu1 '
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.6356(3)
_cell_length_b                   9.5813(3)
_cell_length_c                   13.5642(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.101(3)
_cell_angle_gamma                90
_cell_volume                     1078.29(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2039
_cell_measurement_temperature    297.15
_cell_measurement_theta_max      28.6863
_cell_measurement_theta_min      2.1213
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.024
_exptl_absorpt_correction_T_max  0.801
_exptl_absorpt_correction_T_min  0.630
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
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_absorpt_special_details   ?
_exptl_crystal_colour            'dark blue'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.2863
_exptl_crystal_size_min          0.128
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4505
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.750
_diffrn_reflns_theta_min         2.518
_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 -101.00  -56.00   1.0000    9.1700
omega____ theta____ kappa____ phi______ frames
    -      -19.7470  179.0000   90.0000 45

#__ type_ start__ end____ width___ exp.time_
  2 omega  -52.00   64.00   1.0000    9.1700
omega____ theta____ kappa____ phi______ frames
    -       21.5439  -37.0000    0.0000 116

#__ type_ start__ end____ width___ exp.time_
  3 omega  -31.00   38.00   1.0000    9.1700
omega____ theta____ kappa____ phi______ frames
    -       21.5439  -77.0000  -60.0000 69
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0818166000
_diffrn_orient_matrix_UB_12      0.0152315000
_diffrn_orient_matrix_UB_13      -0.0252330000
_diffrn_orient_matrix_UB_21      -0.0055556000
_diffrn_orient_matrix_UB_22      -0.0621912000
_diffrn_orient_matrix_UB_23      -0.0291549000
_diffrn_orient_matrix_UB_31      -0.0242241000
_diffrn_orient_matrix_UB_32      -0.0370967000
_diffrn_orient_matrix_UB_33      0.0384475000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1934
_reflns_number_total             2411
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2411
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.060
_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)+(0.0343P)²+0.3673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0861
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.85792(4) 0.38334(4) 0.17190(2) 0.03529(13) Uani 1 1 d . . . . .
N1 N 0.8477(3) 0.5348(2) 0.06533(16) 0.0357(5) Uani 1 1 d . . . . .
N2 N 0.6949(3) 0.3004(2) 0.05428(15) 0.0328(5) Uani 1 1 d . . . . .
N3 N 1.0462(3) 0.4651(3) 0.27355(18) 0.0479(6) Uani 1 1 d . . . . .
C1 C 1.1686(5) 0.4428(4) 0.3146(2) 0.0480(8) Uani 1 1 d . . . . .
O1 O 0.8769(3) 0.2129(2) 0.25136(14) 0.0542(6) Uani 1 1 d . . . . .
O2 O 0.8473(2) -0.0061(2) 0.28689(15) 0.0491(5) Uani 1 1 d . . . . .
O3 O 1.3094(4) 0.4256(4) 0.3628(2) 0.0942(10) Uani 1 1 d . . . . .
C11 C 0.9270(4) 0.6550(3) 0.0750(2) 0.0451(7) Uani 1 1 d . . . . .
H11 H 1.0014 0.6759 0.1373 0.054 Uiso 1 1 calc R . . . .
C12 C 0.9027(4) 0.7503(3) -0.0047(3) 0.0491(8) Uani 1 1 d . . . . .
H12 H 0.9600 0.8337 0.0040 0.059 Uiso 1 1 calc R . . . .
C13 C 0.7935(4) 0.7201(3) -0.0962(2) 0.0495(8) Uani 1 1 d . . . . .
H13 H 0.7774 0.7820 -0.1509 0.059 Uiso 1 1 calc R . . . .
C14 C 0.7074(4) 0.5974(3) -0.1069(2) 0.0428(7) Uani 1 1 d . . . . .
H14 H 0.6306 0.5759 -0.1680 0.051 Uiso 1 1 calc R . . . .
C15 C 0.7380(3) 0.5074(3) -0.02453(19) 0.0343(6) Uani 1 1 d . . . . .
C16 C 0.6558(3) 0.3738(3) -0.02666(19) 0.0356(6) Uani 1 1 d . . . . .
H16 H 0.5780 0.3438 -0.0850 0.043 Uiso 1 1 calc R . . . .
C17 C 0.6199(4) 0.1664(3) 0.0613(2) 0.0415(7) Uani 1 1 d . . . . .
H17A H 0.5632 0.1342 -0.0070 0.050 Uiso 1 1 calc R . . . .
H17B H 0.5419 0.1768 0.1003 0.050 Uiso 1 1 calc R . . . .
C18 C 0.7451(4) 0.0605(3) 0.1126(2) 0.0419(7) Uani 1 1 d . . . . .
H18A H 0.8266 0.0562 0.0758 0.050 Uiso 1 1 calc R . . . .
H18B H 0.6944 -0.0305 0.1076 0.050 Uiso 1 1 calc R . . . .
C19 C 0.8272(3) 0.0914(3) 0.2251(2) 0.0394(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 N1 2.033(2) . ?
Cu1 N2 1.978(2) . ?
Cu1 N3 1.979(3) . ?
Cu1 O1 1.938(2) . ?
Cu1 O2 2.264(2) 2_655 ?
N1 C11 1.328(4) . ?
N1 C15 1.346(3) . ?
N2 C16 1.268(3) . ?
N2 C17 1.453(3) . ?
N3 C1 1.071(4) . ?
C1 O3 1.222(4) . ?
O1 C19 1.258(4) . ?
O2 Cu1 2.264(2) 2_645 ?
O2 C19 1.235(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.365(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(4) . ?
C15 C16 1.460(4) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.505(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.522(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
N1 Cu1 O2 87.64(9) . 2_655 ?
N2 Cu1 N1 80.35(9) . . ?
N2 Cu1 N3 169.92(10) . . ?
N2 Cu1 O2 87.48(8) . 2_655 ?
N3 Cu1 N1 94.47(10) . . ?
N3 Cu1 O2 101.01(9) . 2_655 ?
O1 Cu1 N1 167.72(9) . . ?
O1 Cu1 N2 92.40(9) . . ?
O1 Cu1 N3 91.13(10) . . ?
O1 Cu1 O2 102.03(9) . 2_655 ?
C11 N1 Cu1 129.02(19) . . ?
C11 N1 C15 118.2(2) . . ?
C15 N1 Cu1 112.67(18) . . ?
C16 N2 Cu1 115.77(19) . . ?
C16 N2 C17 122.0(2) . . ?
C17 N2 Cu1 122.18(16) . . ?
C1 N3 Cu1 141.7(3) . . ?
N3 C1 O3 176.2(4) . . ?
C19 O1 Cu1 130.74(18) . . ?
C19 O2 Cu1 123.32(19) . 2_645 ?
N1 C11 H11 118.9 . . ?
N1 C11 C12 122.1(3) . . ?
C12 C11 H11 118.9 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.5(3) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 120.9 . . ?
C13 C14 C15 118.2(3) . . ?
C15 C14 H14 120.9 . . ?
N1 C15 C14 122.7(3) . . ?
N1 C15 C16 113.9(2) . . ?
C14 C15 C16 123.4(3) . . ?
N2 C16 C15 117.2(2) . . ?
N2 C16 H16 121.4 . . ?
C15 C16 H16 121.4 . . ?
N2 C17 H17A 109.6 . . ?
N2 C17 H17B 109.6 . . ?
N2 C17 C18 110.5(2) . . ?
H17A C17 H17B 108.1 . . ?
C18 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C17 C18 C19 114.1(2) . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
O1 C19 C18 119.4(2) . . ?
O2 C19 O1 122.3(3) . . ?
O2 C19 C18 118.2(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
Cu1 N1 C11 C12 -177.8(2) . . . . ?
Cu1 N1 C15 C14 178.2(2) . . . . ?
Cu1 N1 C15 C16 -2.1(3) . . . . ?
Cu1 N2 C16 C15 1.6(3) . . . . ?
Cu1 N2 C17 C18 -46.3(3) . . . . ?
Cu1 O1 C19 O2 -178.5(2) . . . . ?
Cu1 O1 C19 C18 4.0(4) . . . . ?
Cu1 O2 C19 O1 115.0(3) 2_645 . . . ?
Cu1 O2 C19 C18 -67.5(3) 2_645 . . . ?
N1 C11 C12 C13 0.1(5) . . . . ?
N1 C15 C16 N2 0.4(4) . . . . ?
N2 C17 C18 C19 66.5(3) . . . . ?
C11 N1 C15 C14 1.3(4) . . . . ?
C11 N1 C15 C16 -179.1(2) . . . . ?
C11 C12 C13 C14 1.4(5) . . . . ?
C12 C13 C14 C15 -1.5(5) . . . . ?
C13 C14 C15 N1 0.2(4) . . . . ?
C13 C14 C15 C16 -179.4(3) . . . . ?
C14 C15 C16 N2 -180.0(3) . . . . ?
C15 N1 C11 C12 -1.4(4) . . . . ?
C16 N2 C17 C18 136.2(3) . . . . ?
C17 N2 C16 C15 179.3(2) . . . . ?
C17 C18 C19 O1 -46.4(4) . . . . ?
C17 C18 C19 O2 136.0(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
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 9 0 0.0796 9.0000 9.0000 0.0000 -0.5989 -0.6091 -0.5524
8 2 10 0.1150 8.0000 2.0000 10.0000 -0.8769 -0.4601 0.1163
10 -7 2 0.1288 10.0000 -7.0000 2.0000 -0.9757 0.3212 0.0946
0 -11 -11 0.0717 0.0000 -11.0000 -11.0000 0.1102 1.0041 -0.0142
0 11 11 0.0563 0.0000 11.0000 11.0000 -0.1102 -1.0041 0.0142
-12 -1 10 0.1136 -12.0000 -1.0000 10.0000 0.7135 -0.1628 0.7123
-11 -3 11 0.1141 -11.0000 -3.0000 11.0000 0.5759 -0.0733 0.8008
-4 -13 3 0.1039 -4.0000 -13.0000 3.0000 0.0528 0.7424 0.6951
-1 8 -14 0.1393 -1.0000 8.0000 -14.0000 0.5582 -0.0834 -0.8111
-9 9 0 0.1531 -9.0000 9.0000 0.0000 0.8738 -0.5093 -0.1163
-8 -3 -9 0.1606 -8.0000 -3.0000 -9.0000 0.8364 0.4931 -0.0407
-5 8 15 0.0796 -5.0000 8.0000 15.0000 0.1518 -0.9066 0.4006

_olex2_submission_special_instructions 'No special instructions were received'

#===END

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_2B_dm3562a
_database_code_depnum_ccdc_archive 'CCDC 1955681'
loop_
_audit_author_name
_audit_author_address
'Daniel Miguel'
;Universidad de Valladolid
Spain
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
_audit_creation_date             2019-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 Cl2 Cu N2 O2'
_chemical_formula_sum            'C14 H14 Cl2 Cu N2 O2'
_chemical_formula_weight         376.71
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H14 Cl2 Cu1 N2 O2'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5026(8)
_cell_length_b                   7.5541(9)
_cell_length_c                   8.0228(10)
_cell_angle_alpha                98.797(10)
_cell_angle_beta                 110.504(11)
_cell_angle_gamma                109.976(10)
_cell_volume                     380.59(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1239
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.6755
_cell_measurement_theta_min      2.8450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1388
_reflns_number_total             1696
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.074
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.0000 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 . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 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_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
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_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
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) . . . . ?

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

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_4(b-alaH)_lam375a
_database_code_depnum_ccdc_archive 'CCDC 1955682'
loop_
_audit_author_name
_audit_author_address
'Daniel Miguel'
;Universidad de Valladolid
Spain
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
_audit_creation_date             2019-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H11 Cl2 Cu N2 O2, C3 H8 N O2'
_chemical_formula_sum            'C13 H19 Cl2 Cu N3 O4'
_chemical_formula_weight         415.75
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0134(6)
_cell_length_b                   8.7640(7)
_cell_length_c                   13.5581(10)
_cell_angle_alpha                71.195(7)
_cell_angle_beta                 80.719(6)
_cell_angle_gamma                66.268(8)
_cell_volume                     824.59(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2456
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.5508
_cell_measurement_theta_min      2.6432
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.670
_exptl_absorpt_correction_T_max  0.844
_exptl_absorpt_correction_T_min  0.726
_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            'light blue'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.3468
_exptl_crystal_size_mid          0.1971
_exptl_crystal_size_min          0.1384
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5267
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.614
_diffrn_reflns_theta_min         2.649
_diffrn_ambient_temperature      297.15
_diffrn_detector_area_resol_mean 10.4757
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -17.00  100.00   1.0000   12.7600
omega____ theta____ kappa____ phi______ frames
    -       21.5439   77.0000 -180.0000 117

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   98.00   1.0000   12.7600
omega____ theta____ kappa____ phi______ frames
    -       21.5439   77.0000   60.0000 107

#__ type_ start__ end____ width___ exp.time_
  3 omega   -9.00   96.00   1.0000   12.7600
omega____ theta____ kappa____ phi______ frames
    -       21.5439   77.0000  -60.0000 105
;
_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_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2970
_reflns_number_total             3682
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3682
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.069
_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)+(0.0304P)²+0.2763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0883
_refine_special_details          
;
 ?
;
_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
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C92(H92A,H92B), C93(H93A,H93B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.68104(5) 0.26240(4) 0.19427(2) 0.02492(11) Uani 1 1 d . . . . .
Cl1 Cl 0.62136(13) 0.02625(10) 0.20844(6) 0.0405(2) Uani 1 1 d . . . . .
Cl2 Cl 1.01836(11) 0.14061(10) 0.24313(6) 0.0378(2) Uani 1 1 d . . . . .
N1 N 0.7483(3) 0.3093(3) 0.04208(17) 0.0254(5) Uani 1 1 d . . . . .
N2 N 0.6460(3) 0.5112(3) 0.16055(17) 0.0261(5) Uani 1 1 d . . . . .
O1 O 0.5806(3) 0.2560(3) 0.33679(14) 0.0288(5) Uani 1 1 d . . . . .
O2 O 0.6291(3) 0.2622(3) 0.49061(14) 0.0289(5) Uani 1 1 d . . . . .
C11 C 0.8028(4) 0.1970(4) -0.0150(2) 0.0328(7) Uani 1 1 d . . . . .
H11 H 0.7978 0.0874 0.0152 0.039 Uiso 1 1 calc R . . . .
C12 C 0.8660(5) 0.2382(4) -0.1168(2) 0.0407(8) Uani 1 1 d . . . . .
H12 H 0.9038 0.1574 -0.1544 0.049 Uiso 1 1 calc R . . . .
C13 C 0.8725(5) 0.3999(5) -0.1618(2) 0.0464(9) Uani 1 1 d . . . . .
H13 H 0.9154 0.4301 -0.2304 0.056 Uiso 1 1 calc R . . . .
C14 C 0.8145(5) 0.5180(4) -0.1041(2) 0.0402(8) Uani 1 1 d . . . . .
H14 H 0.8169 0.6288 -0.1336 0.048 Uiso 1 1 calc R . . . .
C15 C 0.7533(4) 0.4688(4) -0.0025(2) 0.0267(6) Uani 1 1 d . . . . .
C16 C 0.6899(4) 0.5829(4) 0.0680(2) 0.0263(6) Uani 1 1 d . . . . .
C17 C 0.6822(5) 0.7651(4) 0.0242(2) 0.0412(8) Uani 1 1 d . . . . .
H17A H 0.6498 0.8205 0.0789 0.062 Uiso 1 1 calc GR . . . .
H17B H 0.5925 0.8282 -0.0283 0.062 Uiso 1 1 calc GR . . . .
H17C H 0.7994 0.7639 -0.0061 0.062 Uiso 1 1 calc GR . . . .
C18 C 0.5781(5) 0.6006(4) 0.2415(2) 0.0330(7) Uani 1 1 d . . . . .
H18A H 0.4468 0.6338 0.2502 0.040 Uiso 1 1 calc R . . . .
H18B H 0.6042 0.7058 0.2201 0.040 Uiso 1 1 calc R . . . .
C19 C 0.6655(4) 0.4859(4) 0.3442(2) 0.0288(7) Uani 1 1 d . . . . .
H19A H 0.7968 0.4499 0.3335 0.035 Uiso 1 1 calc R . . . .
H19B H 0.6284 0.5547 0.3931 0.035 Uiso 1 1 calc R . . . .
N90 N 1.3137(4) 0.0820(4) 0.3981(2) 0.0296(6) Uani 1 1 d . . . . .
H90A H 1.226(5) 0.105(4) 0.348(3) 0.053(11) Uiso 1 1 d . . . . .
H90B H 1.405(5) 0.095(4) 0.366(3) 0.041(10) Uiso 1 1 d . . . . .
H90C H 1.342(5) -0.035(5) 0.434(3) 0.044(10) Uiso 1 1 d . . . . .
C20 C 0.6209(4) 0.3255(4) 0.3933(2) 0.0243(6) Uani 1 1 d . . . . .
C91 C 0.9722(4) 0.3136(4) 0.5812(2) 0.0285(6) Uani 1 1 d . . . . .
C92 C 1.0619(4) 0.1840(4) 0.5195(2) 0.0291(6) Uani 1 1 d . . . . .
H92A H 1.0899 0.0672 0.5661 0.035 Uiso 1 1 calc R . . . .
H92B H 0.9781 0.2021 0.4688 0.035 Uiso 1 1 calc R . . . .
C93 C 1.2334(4) 0.2013(4) 0.4643(3) 0.0349(7) Uani 1 1 d . . . . .
H93A H 1.2070 0.3202 0.4213 0.042 Uiso 1 1 calc R . . . .
H93B H 1.3206 0.1750 0.5152 0.042 Uiso 1 1 calc R . . . .
O91 O 1.0550(3) 0.3722(3) 0.61409(17) 0.0405(6) Uani 1 1 d . . . . .
O92 O 0.7935(3) 0.3613(3) 0.59900(18) 0.0363(5) Uani 1 1 d . . . . .
H92 H 0.749(4) 0.326(4) 0.571(2) 0.030(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 Cl1 2.2493(8) . ?
Cu1 Cl2 2.5854(9) . ?
Cu1 N1 1.997(2) . ?
Cu1 N2 1.987(2) . ?
Cu1 O1 1.9621(18) . ?
N1 C11 1.340(3) . ?
N1 C15 1.347(3) . ?
N2 C16 1.273(3) . ?
N2 C18 1.461(3) . ?
O1 C20 1.265(3) . ?
O2 C20 1.257(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.370(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(4) . ?
C15 C16 1.491(4) . ?
C16 C17 1.492(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.512(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.507(4) . ?
N90 H90A 0.97(4) . ?
N90 H90B 0.81(3) . ?
N90 H90C 0.93(4) . ?
N90 C93 1.480(4) . ?
C91 C92 1.505(4) . ?
C91 O91 1.192(3) . ?
C91 O92 1.325(4) . ?
C92 H92A 0.9700 . ?
C92 H92B 0.9700 . ?
C92 C93 1.495(4) . ?
C93 H93A 0.9700 . ?
C93 H93B 0.9700 . ?
O92 H92 0.75(3) . ?

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
Cl1 Cu1 Cl2 104.72(3) . . ?
N1 Cu1 Cl1 95.82(7) . . ?
N1 Cu1 Cl2 91.98(7) . . ?
N2 Cu1 Cl1 159.47(8) . . ?
N2 Cu1 Cl2 95.62(7) . . ?
N2 Cu1 N1 80.46(9) . . ?
O1 Cu1 Cl1 88.87(6) . . ?
O1 Cu1 Cl2 95.34(7) . . ?
O1 Cu1 N1 170.03(9) . . ?
O1 Cu1 N2 92.07(8) . . ?
C11 N1 Cu1 127.4(2) . . ?
C11 N1 C15 118.7(2) . . ?
C15 N1 Cu1 113.61(17) . . ?
C16 N2 Cu1 116.80(18) . . ?
C16 N2 C18 123.4(2) . . ?
C18 N2 Cu1 119.76(18) . . ?
C20 O1 Cu1 122.90(17) . . ?
N1 C11 H11 118.8 . . ?
N1 C11 C12 122.3(3) . . ?
C12 C11 H11 118.8 . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.0(3) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.3(3) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 118.9(3) . . ?
C15 C14 H14 120.5 . . ?
N1 C15 C14 121.8(3) . . ?
N1 C15 C16 114.2(2) . . ?
C14 C15 C16 124.0(3) . . ?
N2 C16 C15 114.6(2) . . ?
N2 C16 C17 127.3(3) . . ?
C15 C16 C17 118.1(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 . . ?
N2 C18 H18A 109.4 . . ?
N2 C18 H18B 109.4 . . ?
N2 C18 C19 111.2(2) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C18 C19 H19A 108.4 . . ?
C18 C19 H19B 108.4 . . ?
H19A C19 H19B 107.4 . . ?
C20 C19 C18 115.7(2) . . ?
C20 C19 H19A 108.4 . . ?
C20 C19 H19B 108.4 . . ?
H90A N90 H90B 109(3) . . ?
H90A N90 H90C 104(3) . . ?
H90B N90 H90C 109(3) . . ?
C93 N90 H90A 110(2) . . ?
C93 N90 H90B 111(2) . . ?
C93 N90 H90C 114(2) . . ?
O1 C20 C19 120.1(2) . . ?
O2 C20 O1 121.8(2) . . ?
O2 C20 C19 118.1(2) . . ?
O91 C91 C92 122.9(3) . . ?
O91 C91 O92 119.9(3) . . ?
O92 C91 C92 117.2(3) . . ?
C91 C92 H92A 109.4 . . ?
C91 C92 H92B 109.4 . . ?
H92A C92 H92B 108.0 . . ?
C93 C92 C91 111.3(2) . . ?
C93 C92 H92A 109.4 . . ?
C93 C92 H92B 109.4 . . ?
N90 C93 C92 110.9(2) . . ?
N90 C93 H93A 109.5 . . ?
N90 C93 H93B 109.5 . . ?
C92 C93 H93A 109.5 . . ?
C92 C93 H93B 109.5 . . ?
H93A C93 H93B 108.0 . . ?
C91 O92 H92 114(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
Cu1 N1 C11 C12 -172.2(2) . . . . ?
Cu1 N1 C15 C14 173.4(2) . . . . ?
Cu1 N1 C15 C16 -5.9(3) . . . . ?
Cu1 N2 C16 C15 2.8(3) . . . . ?
Cu1 N2 C16 C17 -178.0(3) . . . . ?
Cu1 N2 C18 C19 41.4(3) . . . . ?
Cu1 O1 C20 O2 -147.3(2) . . . . ?
Cu1 O1 C20 C19 31.2(4) . . . . ?
N1 C11 C12 C13 -0.4(5) . . . . ?
N1 C15 C16 N2 2.1(4) . . . . ?
N1 C15 C16 C17 -177.1(3) . . . . ?
N2 C18 C19 C20 -65.1(3) . . . . ?
C11 N1 C15 C14 -0.7(4) . . . . ?
C11 N1 C15 C16 -179.9(3) . . . . ?
C11 C12 C13 C14 -0.3(5) . . . . ?
C12 C13 C14 C15 0.6(5) . . . . ?
C13 C14 C15 N1 -0.1(5) . . . . ?
C13 C14 C15 C16 179.1(3) . . . . ?
C14 C15 C16 N2 -177.1(3) . . . . ?
C14 C15 C16 C17 3.6(5) . . . . ?
C15 N1 C11 C12 0.9(5) . . . . ?
C16 N2 C18 C19 -136.6(3) . . . . ?
C18 N2 C16 C15 -179.1(3) . . . . ?
C18 N2 C16 C17 0.1(5) . . . . ?
C18 C19 C20 O1 27.5(4) . . . . ?
C18 C19 C20 O2 -154.0(3) . . . . ?
C91 C92 C93 N90 -176.0(3) . . . . ?
O91 C91 C92 C93 -26.4(4) . . . . ?
O92 C91 C92 C93 154.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_10b_dm268py
_database_code_depnum_ccdc_archive 'CCDC 1491840'
loop_
_audit_author_name
_audit_author_address
'Daniel Miguel'
;Universidad de Valladolid
Spain
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
_audit_creation_date             2016-04-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 Cu N5 O2'
_chemical_formula_sum            'C9 H9 Cu N5 O2'
_chemical_formula_weight         282.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H9 N5 O2 Cu1'
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   7.4821(4)
_cell_length_b                   18.0234(7)
_cell_length_c                   7.8559(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.848(5)
_cell_angle_gamma                90
_cell_volume                     1046.79(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1226
_cell_measurement_temperature    297.15
_cell_measurement_theta_max      25.6840
_cell_measurement_theta_min      2.8490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.083
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark green'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.2255
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.028
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4420
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.550
_diffrn_reflns_theta_min         2.260
_diffrn_ambient_temperature      297.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -62.00   48.00   1.0000   82.9300
omega____ theta____ kappa____ phi______ frames
    -       21.5439  -77.0000 -150.0000 110

#__ type_ start__ end____ width___ exp.time_
  2 omega  -79.00   38.00   1.0000   82.9300
omega____ theta____ kappa____ phi______ frames
    -       21.5439  -77.0000  -60.0000 117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0940013000
_diffrn_orient_matrix_UB_12      0.0066671000
_diffrn_orient_matrix_UB_13      -0.0236207000
_diffrn_orient_matrix_UB_21      0.0116620000
_diffrn_orient_matrix_UB_22      0.0029839000
_diffrn_orient_matrix_UB_23      -0.0875766000
_diffrn_orient_matrix_UB_31      -0.0154623000
_diffrn_orient_matrix_UB_32      -0.0386712000
_diffrn_orient_matrix_UB_33      -0.0110539000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1499
_reflns_number_total             2351
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2351
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.018
_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)+(0.0289P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.1035
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.03492(7) 0.03951(3) 0.20500(7) 0.03530(19) Uani 1 1 d . . . . .
N1 N 0.1491(5) 0.12885(18) 0.1082(4) 0.0338(9) Uani 1 1 d . . . . .
N2 N -0.1306(5) 0.1189(2) 0.2646(4) 0.0348(9) Uani 1 1 d . . . . .
N3 N 0.1904(5) -0.0302(2) 0.1000(5) 0.0382(9) Uani 1 1 d . . . . .
N4 N 0.2251(5) -0.0911(2) 0.1544(4) 0.0365(9) Uani 1 1 d . . . . .
N5 N 0.2600(6) -0.1511(2) 0.1995(6) 0.0593(13) Uani 1 1 d . . . . .
O1 O -0.0731(4) -0.03877(15) 0.3244(4) 0.0382(8) Uani 1 1 d . . . . .
O2 O -0.2443(4) -0.06551(17) 0.5223(4) 0.0448(8) Uani 1 1 d . . . . .
C11 C 0.3008(6) 0.1314(3) 0.0381(6) 0.0427(12) Uani 1 1 d . . . . .
H11 H 0.3575 0.0872 0.0166 0.051 Uiso 1 1 calc R . . . .
C12 C 0.3758(7) 0.1978(3) -0.0035(6) 0.0504(13) Uani 1 1 d . . . . .
H12 H 0.4817 0.1982 -0.0518 0.060 Uiso 1 1 calc R . . . .
C13 C 0.2923(7) 0.2631(3) 0.0272(6) 0.0506(14) Uani 1 1 d . . . . .
H13 H 0.3417 0.3083 0.0015 0.061 Uiso 1 1 calc R . . . .
C14 C 0.1353(7) 0.2608(3) 0.0964(6) 0.0456(13) Uani 1 1 d . . . . .
H14 H 0.0763 0.3045 0.1175 0.055 Uiso 1 1 calc R . . . .
C15 C 0.0657(6) 0.1934(2) 0.1344(5) 0.0369(11) Uani 1 1 d . . . . .
C16 C -0.0955(6) 0.1829(3) 0.2164(6) 0.0422(12) Uani 1 1 d . . . . .
H16 H -0.1701 0.2228 0.2324 0.051 Uiso 1 1 calc R . . . .
C17 C -0.2854(6) 0.1040(3) 0.3532(6) 0.0438(12) Uani 1 1 d . . . . .
H17A H -0.3814 0.1393 0.3152 0.053 Uiso 1 1 calc R . . . .
H17B H -0.2495 0.1101 0.4764 0.053 Uiso 1 1 calc R . . . .
C18 C -0.3537(6) 0.0263(3) 0.3153(6) 0.0432(12) Uani 1 1 d . . . . .
H18A H -0.3787 0.0190 0.1916 0.052 Uiso 1 1 calc R . . . .
H18B H -0.4658 0.0194 0.3611 0.052 Uiso 1 1 calc R . . . .
C19 C -0.2171(6) -0.0305(2) 0.3939(5) 0.0351(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 N1 2.025(3) . ?
Cu1 N2 1.995(3) . ?
Cu1 N3 1.977(3) . ?
Cu1 O1 1.938(3) . ?
N1 C11 1.336(5) . ?
N1 C15 1.351(5) . ?
N2 C16 1.254(5) . ?
N2 C17 1.466(5) . ?
N3 N4 1.192(5) . ?
N4 N5 1.154(5) . ?
O1 C19 1.289(5) . ?
O2 C19 1.233(5) . ?
C11 C12 1.383(6) . ?
C12 C13 1.371(6) . ?
C13 C14 1.369(6) . ?
C14 C15 1.372(6) . ?
C15 C16 1.464(6) . ?
C17 C18 1.506(6) . ?
C18 C19 1.510(6) . ?

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 80.25(14) . . ?
N3 Cu1 N1 92.26(15) . . ?
N3 Cu1 N2 168.63(15) . . ?
O1 Cu1 N1 172.72(13) . . ?
O1 Cu1 N2 95.08(13) . . ?
O1 Cu1 N3 93.16(13) . . ?
C11 N1 Cu1 128.0(3) . . ?
C11 N1 C15 118.4(4) . . ?
C15 N1 Cu1 113.3(3) . . ?
C16 N2 Cu1 115.0(3) . . ?
C16 N2 C17 121.9(4) . . ?
C17 N2 Cu1 123.0(3) . . ?
N4 N3 Cu1 123.1(3) . . ?
N5 N4 N3 176.9(4) . . ?
C19 O1 Cu1 124.0(3) . . ?
N1 C11 C12 121.9(4) . . ?
C13 C12 C11 119.3(5) . . ?
C14 C13 C12 119.0(5) . . ?
C13 C14 C15 119.4(5) . . ?
N1 C15 C14 121.9(4) . . ?
N1 C15 C16 112.8(4) . . ?
C14 C15 C16 125.2(4) . . ?
N2 C16 C15 118.4(4) . . ?
N2 C17 C18 110.2(3) . . ?
C17 C18 C19 111.3(4) . . ?
O1 C19 C18 117.5(4) . . ?
O2 C19 O1 122.8(4) . . ?
O2 C19 C18 119.6(4) . . ?

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
Cu1 N1 C11 C12 -171.7(3) . . . . ?
Cu1 N1 C15 C14 172.2(3) . . . . ?
Cu1 N1 C15 C16 -4.0(5) . . . . ?
Cu1 N2 C16 C15 -4.0(5) . . . . ?
Cu1 N2 C17 C18 -27.4(5) . . . . ?
Cu1 O1 C19 O2 -149.3(3) . . . . ?
Cu1 O1 C19 C18 29.0(5) . . . . ?
N1 C11 C12 C13 -0.2(7) . . . . ?
N1 C15 C16 N2 5.4(6) . . . . ?
N2 C17 C18 C19 67.0(5) . . . . ?
C11 N1 C15 C14 -2.1(6) . . . . ?
C11 N1 C15 C16 -178.3(4) . . . . ?
C11 C12 C13 C14 -0.8(8) . . . . ?
C12 C13 C14 C15 0.4(7) . . . . ?
C13 C14 C15 N1 1.1(7) . . . . ?
C13 C14 C15 C16 176.8(4) . . . . ?
C14 C15 C16 N2 -170.7(4) . . . . ?
C15 N1 C11 C12 1.7(7) . . . . ?
C16 N2 C17 C18 150.7(4) . . . . ?
C17 N2 C16 C15 177.8(4) . . . . ?
C17 C18 C19 O1 -71.9(5) . . . . ?
C17 C18 C19 O2 106.4(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
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
-2 -25 0 0.0195 -2.0000 -25.0000 -0.0000 0.0213 -0.0979 0.9977
2 25 0 0.0085 2.0000 25.0000 0.0000 -0.0213 0.0979 -0.9977
2 -2 -11 0.1056 2.0000 -2.0000 -11.0000 0.0585 0.9807 0.1680
-2 2 11 0.1126 -2.0000 2.0000 11.0000 -0.0585 -0.9807 -0.1680
10 4 0 0.0288 10.0000 4.0000 0.0000 -0.9133 0.1286 -0.3093
-10 -4 0 0.0448 -10.0000 -4.0000 -0.0000 0.9133 -0.1286 0.3093
4 -23 -1 0.0299 4.0000 -23.0000 -1.0000 -0.5057 0.0656 0.8386

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_1b_dm356c
_database_code_depnum_ccdc_archive 'CCDC 1955683'
loop_
_audit_author_name
_audit_author_address
'Daniel Miguel'
;Universidad de Valladolid
Spain
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
_audit_creation_date             2019-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 Cl4 Cu2 N2 O2'
_chemical_formula_sum            'C14 H14 Cl4 Cu2 N2 O2'
_chemical_formula_weight         511.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H14 N2 O2 Cl4 Cu4'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9027(15)
_cell_length_b                   8.1307(16)
_cell_length_c                   8.3402(18)
_cell_angle_alpha                103.091(17)
_cell_angle_beta                 111.393(18)
_cell_angle_gamma                107.507(17)
_cell_volume                     440.43(17)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1212
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.4696
_cell_measurement_theta_min      2.8283
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.927
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1573
_reflns_number_total             1972
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.036
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.23137(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 . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 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_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
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_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
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) . . . . ?

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

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_6_cuclbala
_database_code_depnum_ccdc_archive 'CCDC 1491837'
loop_
_audit_author_name
_audit_author_address
'Daniel Miguel'
;Universidad de Valladolid
Spain
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
_audit_creation_date             2016-04-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 Cl Cu N2 O2'
_chemical_formula_sum            'C9 H9 Cl Cu N2 O2'
_chemical_formula_weight         276.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         C9H9Cl1Cu1N2O2
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   7.9634(8)
_cell_length_b                   9.7573(7)
_cell_length_c                   13.5662(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.354(9)
_cell_angle_gamma                90
_cell_volume                     1025.61(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2497
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      29.4282
_cell_measurement_theta_min      2.0872
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.368
_exptl_absorpt_correction_T_max  0.826
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark green'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             556
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 10 0 0.0621
8 10 0 0.0534
-3 13 5 0.0540
10 -3 4 0.0394
-10 -4 -4 0.0708
-8 -9 8 0.0702
-9 3 13 0.0592
-2 -10 -11 0.0558
11 1 -1 0.0512
-1 -5 -17 0.0886
7 -11 -1 0.0502
1 9 14 0.0486
4 9 -14 0.1123

_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.11
loop_
_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
-7.0040 10.0328 -0.0094 0.5902 -0.5681 -0.5188
8.0211 9.9970 0.0239 0.4942 0.8015 -0.4268
-2.9901 13.0253 5.0150 0.5513 -0.1171 -0.8305
10.0184 -3.0309 4.0314 -0.3691 0.9434 0.0494
-10.0238 -3.9804 -4.0357 -0.0127 -0.9931 0.2838
-8.0125 -8.9999 7.9986 -0.7227 -0.6913 0.0698
-8.9999 3.0190 13.0175 -0.2387 -0.6329 -0.7008
-2.0219 -10.0052 -11.0408 -0.1435 -0.3955 0.8891
11.0182 0.9759 -0.9776 0.0195 0.9987 0.0585
-1.0223 -4.9961 -17.0519 0.3351 -0.3460 0.8894
7.0023 -11.0339 -0.9939 -0.6093 0.5482 0.6051
1.0224 9.0042 14.0462 -0.0108 0.3357 -0.9637
3.9998 9.0129 -14.0240 0.9605 0.2487 0.1377

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.854
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5162
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.428
_diffrn_reflns_theta_min         2.596
_diffrn_ambient_temperature      297.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00 100.00   1.00   27.30    --   12.43 179.00  30.00   65
  2  ω    -47.00  37.00   1.00   27.30    --   12.43 -37.00  30.00   84
  3  ω    -32.00  15.00   1.00   27.30    --   12.43 -37.00 150.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0061797000
_diffrn_orient_matrix_UB_12      0.0544783000
_diffrn_orient_matrix_UB_13      -0.0352422000
_diffrn_orient_matrix_UB_21      0.0911483000
_diffrn_orient_matrix_UB_22      0.0070149000
_diffrn_orient_matrix_UB_23      0.0127686000
_diffrn_orient_matrix_UB_31      0.0060943000
_diffrn_orient_matrix_UB_32      -0.0474945000
_diffrn_orient_matrix_UB_33      -0.0386068000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1998
_reflns_number_total             2423
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2423
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.014
_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)+(0.0297P)²+0.9295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0823
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.69528(5) 0.37820(3) 0.31055(2) 0.03283(12) Uani 1 1 d . . . . .
Cl1 Cl 0.82506(12) 0.44670(9) 0.18785(5) 0.0539(2) Uani 1 1 d . . . . .
O1 O 0.6254(3) 0.2066(2) 0.24143(14) 0.0506(6) Uani 1 1 d . . . . .
O2 O 0.5684(3) -0.0131(2) 0.22151(15) 0.0449(5) Uani 1 1 d . . . . .
N1 N 0.7853(3) 0.5392(2) 0.40380(16) 0.0348(5) Uani 1 1 d . . . . .
N2 N 0.6456(3) 0.3093(2) 0.43834(15) 0.0297(5) Uani 1 1 d . . . . .
C11 C 0.8543(4) 0.6568(3) 0.3827(2) 0.0445(7) Uani 1 1 d . . . . .
H11 H 0.8682 0.6714 0.3173 0.053 Uiso 1 1 calc R . . . .
C12 C 0.9059(4) 0.7578(3) 0.4546(3) 0.0479(8) Uani 1 1 d . . . . .
H12 H 0.9531 0.8390 0.4373 0.057 Uiso 1 1 calc R . . . .
C13 C 0.8873(4) 0.7379(3) 0.5510(3) 0.0483(8) Uani 1 1 d . . . . .
H13 H 0.9227 0.8047 0.6003 0.058 Uiso 1 1 calc R . . . .
C14 C 0.8149(4) 0.6170(3) 0.5744(2) 0.0436(7) Uani 1 1 d . . . . .
H14 H 0.8006 0.6009 0.6395 0.052 Uiso 1 1 calc R . . . .
C15 C 0.7645(3) 0.5207(3) 0.49896(19) 0.0325(6) Uani 1 1 d . . . . .
C16 C 0.6859(4) 0.3883(3) 0.51433(19) 0.0346(6) Uani 1 1 d . . . . .
H16 H 0.6666 0.3637 0.5770 0.042 Uiso 1 1 calc R . . . .
C17 C 0.5662(4) 0.1761(3) 0.4452(2) 0.0402(7) Uani 1 1 d . . . . .
H17A H 0.4435 0.1813 0.4151 0.048 Uiso 1 1 calc R . . . .
H17B H 0.5811 0.1506 0.5158 0.048 Uiso 1 1 calc R . . . .
C18 C 0.6477(4) 0.0689(3) 0.3910(2) 0.0423(7) Uani 1 1 d . . . . .
H18A H 0.6070 -0.0208 0.4057 0.051 Uiso 1 1 calc R . . . .
H18B H 0.7718 0.0710 0.4172 0.051 Uiso 1 1 calc R . . . .
C20 C 0.6082(4) 0.0886(3) 0.2769(2) 0.0360(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 Cl1 2.2541(8) . ?
Cu1 O1 1.937(2) . ?
Cu1 O2 2.303(2) 2_655 ?
Cu1 N1 2.040(2) . ?
Cu1 N2 1.983(2) . ?
O1 C20 1.268(3) . ?
O2 Cu1 2.303(2) 2_645 ?
O2 C20 1.240(3) . ?
N1 C11 1.332(4) . ?
N1 C15 1.351(3) . ?
N2 C16 1.268(3) . ?
N2 C17 1.457(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.364(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(4) . ?
C15 C16 1.471(4) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.509(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C20 1.519(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
Cl1 Cu1 O2 106.11(6) . 2_655 ?
O1 Cu1 Cl1 91.62(6) . . ?
O1 Cu1 O2 99.16(9) . 2_655 ?
O1 Cu1 N1 170.49(9) . . ?
O1 Cu1 N2 92.13(8) . . ?
N1 Cu1 Cl1 94.26(7) . . ?
N1 Cu1 O2 86.39(9) . 2_655 ?
N2 Cu1 Cl1 164.68(7) . . ?
N2 Cu1 O2 87.94(8) . 2_655 ?
N2 Cu1 N1 80.30(9) . . ?
C20 O1 Cu1 130.24(18) . . ?
C20 O2 Cu1 125.23(18) . 2_645 ?
C11 N1 Cu1 129.32(19) . . ?
C11 N1 C15 117.9(2) . . ?
C15 N1 Cu1 112.77(18) . . ?
C16 N2 Cu1 116.14(18) . . ?
C16 N2 C17 121.5(2) . . ?
C17 N2 Cu1 122.38(16) . . ?
N1 C11 H11 118.9 . . ?
N1 C11 C12 122.3(3) . . ?
C12 C11 H11 118.9 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C14 119.0(3) . . ?
C14 C13 H13 120.5 . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.5(3) . . ?
C15 C14 H14 120.7 . . ?
N1 C15 C14 122.6(3) . . ?
N1 C15 C16 113.7(2) . . ?
C14 C15 C16 123.6(2) . . ?
N2 C16 C15 117.1(2) . . ?
N2 C16 H16 121.5 . . ?
C15 C16 H16 121.5 . . ?
N2 C17 H17A 109.6 . . ?
N2 C17 H17B 109.6 . . ?
N2 C17 C18 110.2(2) . . ?
H17A C17 H17B 108.1 . . ?
C18 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C17 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
C17 C18 C20 113.4(2) . . ?
H18A C18 H18B 107.7 . . ?
C20 C18 H18A 108.9 . . ?
C20 C18 H18B 108.9 . . ?
O1 C20 C18 119.1(2) . . ?
O2 C20 O1 122.1(3) . . ?
O2 C20 C18 118.7(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
Cu1 O1 C20 O2 -177.0(2) . . . . ?
Cu1 O1 C20 C18 -0.7(4) . . . . ?
Cu1 O2 C20 O1 -108.0(3) 2_645 . . . ?
Cu1 O2 C20 C18 75.7(3) 2_645 . . . ?
Cu1 N1 C11 C12 178.5(2) . . . . ?
Cu1 N1 C15 C14 -179.5(2) . . . . ?
Cu1 N1 C15 C16 1.4(3) . . . . ?
Cu1 N2 C16 C15 -0.1(3) . . . . ?
Cu1 N2 C17 C18 43.9(3) . . . . ?
N1 C11 C12 C13 0.3(5) . . . . ?
N1 C15 C16 N2 -0.9(4) . . . . ?
N2 C17 C18 C20 -67.8(3) . . . . ?
C11 N1 C15 C14 -1.4(4) . . . . ?
C11 N1 C15 C16 179.5(3) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C13 C14 C15 N1 1.0(5) . . . . ?
C13 C14 C15 C16 -180.0(3) . . . . ?
C14 C15 C16 N2 -180.0(3) . . . . ?
C15 N1 C11 C12 0.7(5) . . . . ?
C16 N2 C17 C18 -136.6(3) . . . . ?
C17 N2 C16 C15 -179.7(2) . . . . ?
C17 C18 C20 O1 47.4(4) . . . . ?
C17 C18 C20 O2 -136.1(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.083
_oxdiff_exptl_absorpt_empirical_full_min 0.913
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_9_dm266a
_database_code_depnum_ccdc_archive 'CCDC 1491838'
loop_
_audit_author_name
_audit_author_address
'Daniel Miguel'
;Universidad de Valladolid
Spain
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
_audit_creation_date             2016-04-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H13 Cu N3 O3 S'
_chemical_formula_sum            'C11 H13 Cu N3 O3 S'
_chemical_formula_weight         330.84
_chemical_melting_point          ?
_chemical_oxdiff_formula         C10H9Cl1Cu1N3O2S1
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   7.8730(3)
_cell_length_b                   14.0579(6)
_cell_length_c                   12.7811(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.857(4)
_cell_angle_gamma                90
_cell_volume                     1411.38(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2172
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.5994
_cell_measurement_theta_min      2.1519
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.701
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_correction_T_min  0.726
_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_absorpt_special_details   ?
_exptl_crystal_colour            'dark blue'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.2069
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.0687
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5953
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.662
_diffrn_reflns_theta_min         2.156
_diffrn_ambient_temperature      297.15
_diffrn_detector_area_resol_mean 10.4757
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   68.00  114.00   1.0000   39.7700
omega____ theta____ kappa____ phi______ frames
    -       21.5439  151.0000  -23.0000 46

#__ type_ start__ end____ width___ exp.time_
  2 omega  -23.00  118.00   1.0000   39.7700
omega____ theta____ kappa____ phi______ frames
    -       21.5439   77.0000    0.0000 141

#__ type_ start__ end____ width___ exp.time_
  3 omega   70.00  108.00   1.0000   39.7700
omega____ theta____ kappa____ phi______ frames
    -       21.5439   77.0000   90.0000 38
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0393148000
_diffrn_orient_matrix_UB_12      -0.0350870000
_diffrn_orient_matrix_UB_13      -0.0332835000
_diffrn_orient_matrix_UB_21      -0.0479785000
_diffrn_orient_matrix_UB_22      0.0358869000
_diffrn_orient_matrix_UB_23      -0.0274830000
_diffrn_orient_matrix_UB_31      0.0654432000
_diffrn_orient_matrix_UB_32      0.0052177000
_diffrn_orient_matrix_UB_33      -0.0351841000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2356
_reflns_number_total             3187
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.828
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.048
_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)+(0.0406P)²+0.3543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1089
_refine_special_details          ?
_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:
 C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16)
2.c Tetrahedral OH refined with riding coordinates:
 O30(H30)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.76802(5) 0.21913(3) 0.25265(3) 0.03734(15) Uani 1 1 d . . . . .
S1 S 0.44127(15) 0.18471(10) -0.06685(9) 0.0848(4) Uani 1 1 d . . . . .
O1 O 0.8332(3) 0.34360(15) 0.20689(17) 0.0485(6) Uani 1 1 d . . . . .
O2 O 0.9295(4) 0.48873(18) 0.2159(2) 0.0696(8) Uani 1 1 d . . . . .
O30 O 1.0124(3) 0.15456(16) 0.19623(17) 0.0467(6) Uani 1 1 d . . . . .
H30 H 1.0242 0.0985 0.2129 0.070 Uiso 1 1 calc R . . . .
N1 N 0.7047(3) 0.09482(18) 0.3178(2) 0.0397(6) Uani 1 1 d . . . . .
N2 N 0.8697(3) 0.2405(2) 0.3957(2) 0.0375(6) Uani 1 1 d . . . . .
N3 N 0.6235(4) 0.2012(2) 0.1237(2) 0.0483(7) Uani 1 1 d . . . . .
C3 C 0.5474(4) 0.1925(2) 0.0455(3) 0.0460(8) Uani 1 1 d . . . . .
C11 C 0.6203(5) 0.0211(2) 0.2739(3) 0.0515(9) Uani 1 1 d . . . . .
H11 H 0.5780 0.0256 0.2044 0.062 Uiso 1 1 calc R . . . .
C12 C 0.5939(5) -0.0615(3) 0.3287(4) 0.0623(11) Uani 1 1 d . . . . .
H12 H 0.5335 -0.1116 0.2966 0.075 Uiso 1 1 calc R . . . .
C13 C 0.6575(6) -0.0691(3) 0.4307(3) 0.0632(11) Uani 1 1 d . . . . .
H13 H 0.6413 -0.1244 0.4687 0.076 Uiso 1 1 calc R . . . .
C14 C 0.7466(5) 0.0071(2) 0.4763(3) 0.0550(9) Uani 1 1 d . . . . .
H14 H 0.7919 0.0036 0.5453 0.066 Uiso 1 1 calc R . . . .
C15 C 0.7669(4) 0.0873(2) 0.4183(2) 0.0391(7) Uani 1 1 d . . . . .
C16 C 0.8566(4) 0.1719(2) 0.4582(3) 0.0451(8) Uani 1 1 d . . . . .
H16 H 0.9024 0.1752 0.5271 0.054 Uiso 1 1 calc R . . . .
C17 C 0.9574(5) 0.3279(2) 0.4292(3) 0.0522(10) Uani 1 1 d . . . . .
H17A H 1.0752 0.3245 0.4117 0.063 Uiso 1 1 calc R . . . .
H17B H 0.9561 0.3341 0.5048 0.063 Uiso 1 1 calc R . . . .
C18 C 0.8742(5) 0.4145(2) 0.3774(3) 0.0522(9) Uani 1 1 d . . . . .
H18A H 0.9296 0.4712 0.4065 0.063 Uiso 1 1 calc R . . . .
H18B H 0.7559 0.4167 0.3941 0.063 Uiso 1 1 calc R . . . .
C19 C 0.8820(4) 0.4162(2) 0.2585(3) 0.0435(8) Uani 1 1 d . . . . .
C30 C 1.1719(5) 0.1995(3) 0.2022(4) 0.0754(13) Uani 1 1 d . . . . .
H30A H 1.2437 0.1698 0.1539 0.113 Uiso 1 1 calc GR . . . .
H30B H 1.2234 0.1939 0.2721 0.113 Uiso 1 1 calc GR . . . .
H30C H 1.1578 0.2655 0.1845 0.113 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O1 1.925(2) . ?
Cu1 O30 2.288(2) . ?
Cu1 N1 2.013(3) . ?
Cu1 N2 1.969(3) . ?
Cu1 N3 1.955(3) . ?
S1 C3 1.616(4) . ?
O1 C19 1.261(4) . ?
O2 C19 1.227(4) . ?
O30 H30 0.8200 . ?
O30 C30 1.403(4) . ?
N1 C11 1.334(4) . ?
N1 C15 1.348(4) . ?
N2 C16 1.261(4) . ?
N2 C17 1.460(4) . ?
N3 C3 1.137(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.364(4) . ?
C15 C16 1.459(4) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.514(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.525(4) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

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
O1 Cu1 O30 91.03(10) . . ?
O1 Cu1 N1 173.26(10) . . ?
O1 Cu1 N2 92.50(10) . . ?
O1 Cu1 N3 90.74(11) . . ?
N1 Cu1 O30 91.32(9) . . ?
N2 Cu1 O30 93.16(10) . . ?
N2 Cu1 N1 81.07(11) . . ?
N3 Cu1 O30 97.89(11) . . ?
N3 Cu1 N1 95.19(11) . . ?
N3 Cu1 N2 168.43(11) . . ?
C19 O1 Cu1 130.9(2) . . ?
Cu1 O30 H30 112.5 . . ?
C30 O30 Cu1 125.0(2) . . ?
C30 O30 H30 109.5 . . ?
C11 N1 Cu1 129.1(2) . . ?
C11 N1 C15 118.6(3) . . ?
C15 N1 Cu1 112.2(2) . . ?
C16 N2 Cu1 115.3(2) . . ?
C16 N2 C17 121.0(3) . . ?
C17 N2 Cu1 123.8(2) . . ?
C3 N3 Cu1 175.9(3) . . ?
N3 C3 S1 177.6(4) . . ?
N1 C11 H11 119.1 . . ?
N1 C11 C12 121.9(3) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.5(4) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.8(4) . . ?
C14 C13 H13 120.6 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.0(4) . . ?
C15 C14 H14 120.5 . . ?
N1 C15 C14 122.3(3) . . ?
N1 C15 C16 113.9(3) . . ?
C14 C15 C16 123.8(3) . . ?
N2 C16 C15 117.4(3) . . ?
N2 C16 H16 121.3 . . ?
C15 C16 H16 121.3 . . ?
N2 C17 H17A 109.3 . . ?
N2 C17 H17B 109.3 . . ?
N2 C17 C18 111.5(3) . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
C17 C18 C19 113.8(3) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
O1 C19 C18 118.6(3) . . ?
O2 C19 O1 122.2(3) . . ?
O2 C19 C18 119.2(3) . . ?
O30 C30 H30A 109.5 . . ?
O30 C30 H30B 109.5 . . ?
O30 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O30 H30 O2 0.82 1.82 2.615(3) 164.2 2_745

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
Cu1 O1 C19 O2 175.1(3) . . . . ?
Cu1 O1 C19 C18 -7.5(5) . . . . ?
Cu1 N1 C11 C12 176.8(3) . . . . ?
Cu1 N1 C15 C14 -176.7(3) . . . . ?
Cu1 N1 C15 C16 3.2(3) . . . . ?
Cu1 N2 C16 C15 -1.0(4) . . . . ?
Cu1 N2 C17 C18 36.2(4) . . . . ?
N1 C11 C12 C13 -0.8(6) . . . . ?
N1 C15 C16 N2 -1.6(4) . . . . ?
N2 C17 C18 C19 -63.7(4) . . . . ?
C11 N1 C15 C14 0.1(5) . . . . ?
C11 N1 C15 C16 -180.0(3) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C12 C13 C14 C15 0.5(6) . . . . ?
C13 C14 C15 N1 -0.6(5) . . . . ?
C13 C14 C15 C16 179.4(3) . . . . ?
C14 C15 C16 N2 178.4(3) . . . . ?
C15 N1 C11 C12 0.7(5) . . . . ?
C16 N2 C17 C18 -144.9(3) . . . . ?
C17 N2 C16 C15 179.9(3) . . . . ?
C17 C18 C19 O1 51.0(5) . . . . ?
C17 C18 C19 O2 -131.6(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
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
10 7 1 0.0399 10.0000 7.0000 1.0000 -0.6760 -0.2583 0.6534
-10 -7 -1 0.0288 -10.0000 -7.0000 -1.0000 0.6760 0.2583 -0.6534
2 -4 -18 0.1135 2.0000 -4.0000 -18.0000 0.6577 0.2530 0.7440
10 -9 0 0.0256 10.0000 -9.0000 0.0000 -0.0823 -0.8048 0.6059
-10 9 0 0.0451 -10.0000 9.0000 -0.0000 0.0823 0.8048 -0.6059
8 -8 8 0.0559 8.0000 -8.0000 8.0000 -0.3032 -0.8916 0.1987
-9 -2 12 0.0667 -9.0000 -2.0000 12.0000 0.0298 0.0335 -1.0204
-4 3 17 0.0767 -4.0000 3.0000 17.0000 -0.5100 -0.1651 -0.8445
0 0 -18 0.1082 -0.0000 0.0000 -18.0000 0.5971 0.4929 0.6343

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_10a_dm537a
_database_code_depnum_ccdc_archive 'CCDC 1491839'
loop_
_audit_author_name
_audit_author_address
'Daniel Miguel'
;Universidad de Valladolid
Spain
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
_audit_creation_date             2016-04-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 Cu N5 O2'
_chemical_formula_sum            'C9 H9 Cu N5 O2'
_chemical_formula_weight         282.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H9 N5 O2'
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.6172(3)
_cell_length_b                   9.2484(3)
_cell_length_c                   14.1381(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.055(4)
_cell_angle_gamma                90
_cell_volume                     1077.19(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2760
_cell_measurement_temperature    297.15
_cell_measurement_theta_max      28.4450
_cell_measurement_theta_min      3.0110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.025
_exptl_absorpt_correction_T_max  0.824
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark green'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.3675
_exptl_crystal_size_mid          0.2176
_exptl_crystal_size_min          0.1224
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5732
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.717
_diffrn_reflns_theta_min         2.490
_diffrn_ambient_temperature      297.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4757
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   85.00   1.0000   10.4900
omega____ theta____ kappa____ phi______ frames
    -       11.7464   57.0000   90.0000 97

#__ type_ start__ end____ width___ exp.time_
  2 omega  -24.00   74.00   1.0000   10.4900
omega____ theta____ kappa____ phi______ frames
    -       11.7464   19.0000 -150.0000 98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0804982000
_diffrn_orient_matrix_UB_12      -0.0063398000
_diffrn_orient_matrix_UB_13      -0.0317337000
_diffrn_orient_matrix_UB_21      0.0069294000
_diffrn_orient_matrix_UB_22      0.0688797000
_diffrn_orient_matrix_UB_23      -0.0204464000
_diffrn_orient_matrix_UB_31      0.0298190000
_diffrn_orient_matrix_UB_32      -0.0331295000
_diffrn_orient_matrix_UB_33      -0.0364358000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2081
_reflns_number_total             2565
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2565
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.086
_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)+(0.0290P)²+0.2589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0756
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.85785(3) 0.40558(3) 0.16410(2) 0.02776(11) Uani 1 1 d . . . . .
O1 O 0.8893(2) 0.23672(19) 0.24846(12) 0.0434(4) Uani 1 1 d . . . . .
O2 O 0.8467(2) 0.0200(2) 0.29746(13) 0.0416(4) Uani 1 1 d . . . . .
N1 N 0.8453(2) 0.5495(2) 0.05421(14) 0.0286(4) Uani 1 1 d . . . . .
N2 N 0.6937(2) 0.3084(2) 0.05503(13) 0.0287(4) Uani 1 1 d . . . . .
N3 N 1.0384(2) 0.5096(2) 0.25650(16) 0.0389(5) Uani 1 1 d . . . . .
N4 N 1.1522(3) 0.4518(2) 0.31075(16) 0.0355(5) Uani 1 1 d . . . . .
N5 N 1.2680(3) 0.4037(3) 0.3646(2) 0.0634(8) Uani 1 1 d . . . . .
C11 C 0.9253(3) 0.6738(3) 0.05844(19) 0.0363(6) Uani 1 1 d . . . . .
H11 H 0.9975 0.7025 0.1183 0.044 Uiso 1 1 calc R . . . .
C12 C 0.9039(3) 0.7612(3) -0.0239(2) 0.0401(6) Uani 1 1 d . . . . .
H12 H 0.9609 0.8476 -0.0191 0.048 Uiso 1 1 calc R . . . .
C13 C 0.7985(3) 0.7198(3) -0.11211(19) 0.0380(6) Uani 1 1 d . . . . .
H13 H 0.7845 0.7767 -0.1682 0.046 Uiso 1 1 calc R . . . .
C14 C 0.7129(3) 0.5924(3) -0.11704(19) 0.0358(6) Uani 1 1 d . . . . .
H14 H 0.6395 0.5627 -0.1762 0.043 Uiso 1 1 calc R . . . .
C15 C 0.7383(3) 0.5101(2) -0.03256(16) 0.0284(5) Uani 1 1 d . . . . .
C16 C 0.6556(3) 0.3731(3) -0.02802(17) 0.0308(5) Uani 1 1 d . . . . .
H16 H 0.5789 0.3353 -0.0832 0.037 Uiso 1 1 calc R . . . .
C17 C 0.6174(3) 0.1725(3) 0.06804(18) 0.0385(6) Uani 1 1 d . . . . .
H17A H 0.5607 0.1323 0.0038 0.046 Uiso 1 1 calc R . . . .
H17B H 0.5385 0.1897 0.1036 0.046 Uiso 1 1 calc R . . . .
C18 C 0.7436(3) 0.0658(3) 0.12502(18) 0.0360(6) Uani 1 1 d . . . . .
H18A H 0.8241 0.0528 0.0901 0.043 Uiso 1 1 calc R . . . .
H18B H 0.6914 -0.0268 0.1260 0.043 Uiso 1 1 calc R . . . .
C19 C 0.8298(3) 0.1101(3) 0.23091(18) 0.0307(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O1 1.9352(17) . ?
Cu1 O2 2.2549(17) 2_655 ?
Cu1 N1 2.0248(19) . ?
Cu1 N2 1.9769(18) . ?
Cu1 N3 1.965(2) . ?
O1 C19 1.273(3) . ?
O2 Cu1 2.2549(17) 2_645 ?
O2 C19 1.233(3) . ?
N1 C11 1.332(3) . ?
N1 C15 1.351(3) . ?
N2 C16 1.273(3) . ?
N2 C17 1.455(3) . ?
N3 N4 1.181(3) . ?
N4 N5 1.152(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.365(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(3) . ?
C15 C16 1.464(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.513(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.519(3) . ?

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
O1 Cu1 O2 102.03(8) . 2_655 ?
O1 Cu1 N1 165.88(8) . . ?
O1 Cu1 N2 93.02(7) . . ?
O1 Cu1 N3 92.57(8) . . ?
N1 Cu1 O2 90.39(7) . 2_655 ?
N2 Cu1 O2 88.29(7) . 2_655 ?
N2 Cu1 N1 80.54(8) . . ?
N3 Cu1 O2 97.61(8) . 2_655 ?
N3 Cu1 N1 92.40(8) . . ?
N3 Cu1 N2 170.86(8) . . ?
C19 O1 Cu1 130.27(16) . . ?
C19 O2 Cu1 125.13(15) . 2_645 ?
C11 N1 Cu1 128.48(17) . . ?
C11 N1 C15 118.7(2) . . ?
C15 N1 Cu1 112.84(15) . . ?
C16 N2 Cu1 115.94(16) . . ?
C16 N2 C17 121.3(2) . . ?
C17 N2 Cu1 122.73(15) . . ?
N4 N3 Cu1 123.71(18) . . ?
N5 N4 N3 175.7(3) . . ?
N1 C11 H11 119.1 . . ?
N1 C11 C12 121.8(2) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.2(2) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.7(2) . . ?
C15 C14 H14 120.6 . . ?
N1 C15 C14 122.1(2) . . ?
N1 C15 C16 113.89(19) . . ?
C14 C15 C16 124.0(2) . . ?
N2 C16 C15 116.8(2) . . ?
N2 C16 H16 121.6 . . ?
C15 C16 H16 121.6 . . ?
N2 C17 H17A 109.6 . . ?
N2 C17 H17B 109.6 . . ?
N2 C17 C18 110.47(19) . . ?
H17A C17 H17B 108.1 . . ?
C18 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C17 C18 H18A 108.6 . . ?
C17 C18 H18B 108.6 . . ?
C17 C18 C19 114.6(2) . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
O1 C19 C18 119.5(2) . . ?
O2 C19 O1 121.5(2) . . ?
O2 C19 C18 118.9(2) . . ?

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
Cu1 O1 C19 O2 -170.56(17) . . . . ?
Cu1 O1 C19 C18 12.7(3) . . . . ?
Cu1 O2 C19 O1 123.3(2) 2_645 . . . ?
Cu1 O2 C19 C18 -59.9(3) 2_645 . . . ?
Cu1 N1 C11 C12 179.84(17) . . . . ?
Cu1 N1 C15 C14 -179.22(17) . . . . ?
Cu1 N1 C15 C16 0.0(2) . . . . ?
Cu1 N2 C16 C15 0.4(3) . . . . ?
Cu1 N2 C17 C18 -46.1(3) . . . . ?
N1 C11 C12 C13 -0.1(4) . . . . ?
N1 C15 C16 N2 -0.3(3) . . . . ?
N2 C17 C18 C19 64.8(3) . . . . ?
C11 N1 C15 C14 1.8(3) . . . . ?
C11 N1 C15 C16 -178.97(19) . . . . ?
C11 C12 C13 C14 1.2(4) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C13 C14 C15 N1 -0.7(3) . . . . ?
C13 C14 C15 C16 -179.9(2) . . . . ?
C14 C15 C16 N2 179.0(2) . . . . ?
C15 N1 C11 C12 -1.3(3) . . . . ?
C16 N2 C17 C18 135.1(2) . . . . ?
C17 N2 C16 C15 179.2(2) . . . . ?
C17 C18 C19 O1 -49.4(3) . . . . ?
C17 C18 C19 O2 133.8(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
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
-1 10 -11 0.0495 -1.0000 10.0000 -11.0000 0.3662 0.9068 0.0397
1 -11 11 0.0666 1.0000 -11.0000 11.0000 -0.3598 -0.9757 -0.0066
8 -9 1 0.0658 8.0000 -9.0000 1.0000 -0.6187 -0.5849 0.5003
9 0 8 0.1058 9.0000 0.0000 8.0000 -0.9784 -0.1012 -0.0231
-9 -8 -1 0.0701 -9.0000 -8.0000 -1.0000 0.8069 -0.5930 0.0331
-8 9 -2 0.0871 -8.0000 9.0000 -2.0000 0.6504 0.6054 -0.4638
-1 -11 -9 0.0845 -1.0000 -11.0000 -9.0000 0.4358 -0.5806 0.6625
2 10 12 0.1412 2.0000 10.0000 12.0000 -0.6052 0.4573 -0.7089
-4 -11 10 0.0737 -4.0000 -11.0000 10.0000 0.0744 -0.9899 -0.1192
-12 -2 4 0.1069 -12.0000 -2.0000 4.0000 0.8517 -0.3027 -0.4373
-11 4 12 0.1466 -11.0000 4.0000 12.0000 0.4793 -0.0461 -0.8978
4 12 -8 0.0837 4.0000 12.0000 -8.0000 -0.1442 1.0178 0.0132

_olex2_submission_special_instructions 'No special instructions were received'
