# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_sad1
_database_code_depnum_ccdc_archive 'CCDC 1555395'
_audit_update_record             
;
2017-06-12 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;

_audit_creation_date             2017-06-11T19:03:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C20 H19 Cu N5 O6'
_chemical_formula_weight         488.8

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   9.3600(19)
_cell_length_b                   23.494(5)
_cell_length_c                   9.6076(19)
_cell_angle_alpha                90
_cell_angle_beta                 97.83(3)
_cell_angle_gamma                90
_cell_volume                     2093.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6003
_cell_measurement_theta_min      1.73
_cell_measurement_theta_max      23.28

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'Dark Blue'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.083
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_F_000             1004
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 7 0.02
1 -1 -7 0.143
2 3 -6 0.205
-1 -4 8 0.065
-2 1 -2 0.142
-1 3 -7 0.158
1 -1 2 0.091
1 0 0 0.16
0 3 5 0.097
-1 -5 -3 0.175
-8 1 -1 0.142
1 0 -6 0.15

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.092
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9213
_exptl_absorpt_correction_T_max  0.9666
_shelx_estimated_absorpt_T_min   0.757
_shelx_estimated_absorpt_T_max   0.915

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_av_R_equivalents  0.1225
_diffrn_reflns_number            15232
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.734
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             3682
_reflns_number_gt                1475
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3682
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1485
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1254
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   0.778
_refine_ls_restrained_S_all      0.778
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.06

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.32 1.265 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.011 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.32083(7) 0.00185(3) 0.67450(7) 0.0622(2) Uani 1 d . .
O4 O 0.5219(5) -0.0476(2) 0.7882(7) 0.118(2) Uani 1 d . .
O1 O 0.1384(6) 0.0391(3) 0.4593(6) 0.123(2) Uani 1 d . .
O5 O 0.6542(7) -0.1196(3) 0.8018(6) 0.138(2) Uani 1 d . .
O2 O 0.2938(5) -0.02946(18) 0.4816(5) 0.0750(12) Uani 1 d . .
O6 O 0.4878(8) -0.1137(3) 0.6414(7) 0.168(3) Uani 1 d . .
O3 O 0.1546(6) -0.0162(3) 0.2833(6) 0.124(2) Uani 1 d . .
N5 N 0.4437(7) 0.0697(3) 0.6484(7) 0.0655(17) Uani 1 d . .
N1 N 0.1911(6) -0.0015(3) 0.4033(7) 0.0861(15) Uani 1 d . .
N3 N 0.2958(5) 0.04169(18) 0.8488(5) 0.0559(12) Uani 1 d . .
N2 N 0.5558(6) -0.0930(3) 0.7412(6) 0.0654(14) Uani 1 d . .
N4 N 0.1894(5) -0.05355(19) 0.7546(5) 0.0585(12) Uani 1 d . .
C3 C 0.2334(6) 0.0148(2) 0.9372(6) 0.0552(15) Uani 1 d . .
H5 H 0.23 0.0283 1.0277 0.066 Uiso 1 calc . .
C2 C 0.3632(6) 0.0980(2) 0.8689(6) 0.0572(15) Uani 1 d . .
H11 H 0.3962 0.1039 0.9692 0.069 Uiso 1 calc . .
C1 C 0.4974(6) 0.0935(2) 0.7884(6) 0.0551(15) Uani 1 d . .
H17 H 0.5624 0.0651 0.8377 0.066 Uiso 1 calc . .
C10 C 0.1344(7) 0.1336(3) 0.7274(7) 0.0773(19) Uani 1 d . .
H10 H 0.114 0.0968 0.695 0.093 Uiso 1 calc . .
C15 C 0.5803(6) 0.1493(2) 0.7922(7) 0.0575(16) Uani 1 d . .
C16 C 0.6511(6) 0.1679(3) 0.9212(7) 0.0673(17) Uani 1 d . .
H16 H 0.6494 0.1453 1.0005 0.081 Uiso 1 calc . .
C9 C 0.2572(6) 0.1440(2) 0.8175(6) 0.0535(14) Uani 1 d . .
C14 C 0.2824(6) 0.1994(3) 0.8656(7) 0.0699(17) Uani 1 d . .
H6 H 0.3641 0.207 0.9294 0.084 Uiso 1 calc . .
C4 C 0.1669(6) -0.0391(2) 0.8865(7) 0.0561(15) Uani 1 d . .
C20 C 0.5857(7) 0.1836(3) 0.6766(7) 0.0747(18) Uani 1 d . .
H12 H 0.5411 0.1717 0.5889 0.09 Uiso 1 calc . .
C8 C 0.0850(6) -0.0723(3) 0.9659(7) 0.0649(17) Uani 1 d . .
H1 H 0.0733 -0.0622 1.0573 0.078 Uiso 1 calc . .
C17 C 0.7237(7) 0.2193(3) 0.9334(9) 0.080(2) Uani 1 d . .
H15 H 0.7718 0.2307 1.02 0.096 Uiso 1 calc . .
C7 C 0.0217(7) -0.1207(3) 0.9039(8) 0.0774(19) Uani 1 d . .
H2 H -0.0357 -0.1434 0.9529 0.093 Uiso 1 calc . .
C19 C 0.6572(8) 0.2357(3) 0.6893(9) 0.084(2) Uani 1 d . .
H13 H 0.6594 0.2586 0.6106 0.101 Uiso 1 calc . .
C12 C 0.0656(8) 0.2328(3) 0.7295(8) 0.086(2) Uani 1 d . .
H8 H 0.0018 0.2621 0.6998 0.103 Uiso 1 calc . .
C6 C 0.0431(7) -0.1355(3) 0.7701(8) 0.0767(19) Uani 1 d . .
H3 H 0.0007 -0.1681 0.7278 0.092 Uiso 1 calc . .
C18 C 0.7247(7) 0.2532(3) 0.8184(10) 0.090(2) Uani 1 d . .
H14 H 0.7711 0.2883 0.8273 0.108 Uiso 1 calc . .
C13 C 0.1895(8) 0.2435(3) 0.8211(8) 0.0820(19) Uani 1 d . .
H7 H 0.2104 0.2804 0.8529 0.098 Uiso 1 calc . .
C5 C 0.1291(7) -0.1011(3) 0.6993(7) 0.0713(18) Uani 1 d . .
H4 H 0.1453 -0.1116 0.6094 0.086 Uiso 1 calc . .
C11 C 0.0383(8) 0.1781(4) 0.6829(8) 0.097(2) Uani 1 d . .
H9 H -0.0448 0.1704 0.6212 0.116 Uiso 1 calc . .
H18 H 0.498(4) 0.0591(16) 0.621(4) 0.001(12) Uiso 1 d . .
H19 H 0.393(6) 0.099(2) 0.589(6) 0.070(19) Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N3 1.960(5) . ?
Cu1 O2 1.978(4) . ?
Cu1 N5 2.002(6) . ?
Cu1 N4 2.014(5) . ?
Cu1 O4 2.351(5) . ?
Cu1 O1 2.645(5) . ?
Cu1 H18 2.25(4) . ?
O4 N2 1.217(6) . ?
O1 N1 1.231(7) . ?
O5 N2 1.196(6) . ?
O2 N1 1.313(7) . ?
O6 N2 1.180(7) . ?
O3 N1 1.207(6) . ?
N5 C1 1.480(8) . ?
N5 H18 0.65(3) . ?
N5 H19 0.97(5) . ?
N3 C3 1.263(6) . ?
N3 C2 1.468(6) . ?
N4 C5 1.329(7) . ?
N4 C4 1.357(6) . ?
C3 C4 1.466(7) . ?
C3 H5 0.93 . ?
C2 C9 1.504(7) . ?
C2 C1 1.566(7) . ?
C2 H11 0.98 . ?
C1 C15 1.522(7) . ?
C1 H17 0.98 . ?
C10 C9 1.363(8) . ?
C10 C11 1.407(9) . ?
C10 H10 0.93 . ?
C15 C20 1.378(8) . ?
C15 C16 1.393(8) . ?
C16 C17 1.383(8) . ?
C16 H16 0.93 . ?
C9 C14 1.392(7) . ?
C14 C13 1.383(8) . ?
C14 H6 0.93 . ?
C4 C8 1.391(7) . ?
C20 C19 1.393(8) . ?
C20 H12 0.93 . ?
C8 C7 1.380(8) . ?
C8 H1 0.93 . ?
C17 C18 1.364(9) . ?
C17 H15 0.93 . ?
C7 C6 1.372(8) . ?
C7 H2 0.93 . ?
C19 C18 1.377(9) . ?
C19 H13 0.93 . ?
C12 C11 1.372(9) . ?
C12 C13 1.380(9) . ?
C12 H8 0.93 . ?
C6 C5 1.383(8) . ?
C6 H3 0.93 . ?
C18 H14 0.93 . ?
C13 H7 0.93 . ?
C5 H4 0.93 . ?
C11 H9 0.93 . ?

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
N3 Cu1 O2 164.42(18) . . ?
N3 Cu1 N5 82.2(2) . . ?
O2 Cu1 N5 100.4(2) . . ?
N3 Cu1 N4 80.3(2) . . ?
O2 Cu1 N4 96.36(19) . . ?
N5 Cu1 N4 162.5(2) . . ?
N3 Cu1 O4 91.17(19) . . ?
O2 Cu1 O4 104.1(2) . . ?
N5 Cu1 O4 90.8(2) . . ?
N4 Cu1 O4 89.73(19) . . ?
N3 Cu1 O1 111.76(18) . . ?
O2 Cu1 O1 53.40(17) . . ?
N5 Cu1 O1 87.7(2) . . ?
N4 Cu1 O1 98.58(19) . . ?
O4 Cu1 O1 156.56(19) . . ?
N3 Cu1 H18 95.1(10) . . ?
O2 Cu1 H18 90.6(10) . . ?
N5 Cu1 H18 16.4(9) . . ?
N4 Cu1 H18 169.1(10) . . ?
O4 Cu1 H18 80.4(10) . . ?
O1 Cu1 H18 92.3(10) . . ?
N2 O4 Cu1 119.6(4) . . ?
N1 O1 Cu1 80.3(4) . . ?
N1 O2 Cu1 109.9(4) . . ?
C1 N5 Cu1 108.4(4) . . ?
C1 N5 H18 109(4) . . ?
Cu1 N5 H18 104(4) . . ?
C1 N5 H19 110(3) . . ?
Cu1 N5 H19 113(3) . . ?
H18 N5 H19 112(5) . . ?
O3 N1 O1 124.0(7) . . ?
O3 N1 O2 119.7(7) . . ?
O1 N1 O2 116.3(6) . . ?
C3 N3 C2 126.3(5) . . ?
C3 N3 Cu1 117.1(4) . . ?
C2 N3 Cu1 116.4(4) . . ?
O6 N2 O5 118.4(7) . . ?
O6 N2 O4 121.5(7) . . ?
O5 N2 O4 119.9(6) . . ?
C5 N4 C4 118.2(5) . . ?
C5 N4 Cu1 129.7(5) . . ?
C4 N4 Cu1 112.1(4) . . ?
N3 C3 C4 115.0(5) . . ?
N3 C3 H5 122.5 . . ?
C4 C3 H5 122.5 . . ?
N3 C2 C9 110.6(5) . . ?
N3 C2 C1 103.5(4) . . ?
C9 C2 C1 115.1(5) . . ?
N3 C2 H11 109.2 . . ?
C9 C2 H11 109.2 . . ?
C1 C2 H11 109.2 . . ?
N5 C1 C15 117.1(5) . . ?
N5 C1 C2 106.2(5) . . ?
C15 C1 C2 111.7(4) . . ?
N5 C1 H17 107.1 . . ?
C15 C1 H17 107.1 . . ?
C2 C1 H17 107.1 . . ?
C9 C10 C11 120.6(6) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C20 C15 C16 118.0(6) . . ?
C20 C15 C1 123.9(6) . . ?
C16 C15 C1 118.0(5) . . ?
C17 C16 C15 121.1(6) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C10 C9 C14 117.9(6) . . ?
C10 C9 C2 122.9(5) . . ?
C14 C9 C2 119.2(5) . . ?
C13 C14 C9 121.8(6) . . ?
C13 C14 H6 119.1 . . ?
C9 C14 H6 119.1 . . ?
N4 C4 C8 122.6(5) . . ?
N4 C4 C3 114.4(5) . . ?
C8 C4 C3 122.9(6) . . ?
C15 C20 C19 120.8(7) . . ?
C15 C20 H12 119.6 . . ?
C19 C20 H12 119.6 . . ?
C7 C8 C4 117.5(6) . . ?
C7 C8 H1 121.3 . . ?
C4 C8 H1 121.3 . . ?
C18 C17 C16 120.0(7) . . ?
C18 C17 H15 120 . . ?
C16 C17 H15 120 . . ?
C6 C7 C8 120.3(6) . . ?
C6 C7 H2 119.9 . . ?
C8 C7 H2 119.9 . . ?
C18 C19 C20 119.9(7) . . ?
C18 C19 H13 120.1 . . ?
C20 C19 H13 120.1 . . ?
C11 C12 C13 118.8(7) . . ?
C11 C12 H8 120.6 . . ?
C13 C12 H8 120.6 . . ?
C7 C6 C5 118.8(6) . . ?
C7 C6 H3 120.6 . . ?
C5 C6 H3 120.6 . . ?
C17 C18 C19 120.1(7) . . ?
C17 C18 H14 119.9 . . ?
C19 C18 H14 119.9 . . ?
C12 C13 C14 119.9(6) . . ?
C12 C13 H7 120 . . ?
C14 C13 H7 120 . . ?
N4 C5 C6 122.6(6) . . ?
N4 C5 H4 118.7 . . ?
C6 C5 H4 118.7 . . ?
C12 C11 C10 120.9(7) . . ?
C12 C11 H9 119.6 . . ?
C10 C11 H9 119.6 . . ?

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 N1 O3 177.9(7) . . . . ?
Cu1 O1 N1 O2 -2.7(5) . . . . ?
Cu1 O2 N1 O3 -176.8(5) . . . . ?
Cu1 O2 N1 O1 3.7(7) . . . . ?
Cu1 O4 N2 O6 -1.9(9) . . . . ?
Cu1 O4 N2 O5 -176.8(5) . . . . ?
C2 N3 C3 C4 176.1(5) . . . . ?
Cu1 N3 C3 C4 -9.8(6) . . . . ?
C3 N3 C2 C9 -92.0(6) . . . . ?
Cu1 N3 C2 C9 93.8(4) . . . . ?
C3 N3 C2 C1 144.2(5) . . . . ?
Cu1 N3 C2 C1 -29.9(5) . . . . ?
Cu1 N5 C1 C15 -173.6(4) . . . . ?
Cu1 N5 C1 C2 -48.1(5) . . . . ?
N3 C2 C1 N5 49.1(6) . . . . ?
C9 C2 C1 N5 -71.6(6) . . . . ?
N3 C2 C1 C15 177.9(5) . . . . ?
C9 C2 C1 C15 57.2(7) . . . . ?
N5 C1 C15 C20 12.1(8) . . . . ?
C2 C1 C15 C20 -110.6(6) . . . . ?
N5 C1 C15 C16 -170.1(5) . . . . ?
C2 C1 C15 C16 67.1(6) . . . . ?
C20 C15 C16 C17 0.5(8) . . . . ?
C1 C15 C16 C17 -177.4(5) . . . . ?
C11 C10 C9 C14 1.2(9) . . . . ?
C11 C10 C9 C2 179.7(6) . . . . ?
N3 C2 C9 C10 -18.7(8) . . . . ?
C1 C2 C9 C10 98.1(6) . . . . ?
N3 C2 C9 C14 159.8(5) . . . . ?
C1 C2 C9 C14 -83.4(6) . . . . ?
C10 C9 C14 C13 -2.0(9) . . . . ?
C2 C9 C14 C13 179.4(5) . . . . ?
C5 N4 C4 C8 0.7(8) . . . . ?
Cu1 N4 C4 C8 -177.1(4) . . . . ?
C5 N4 C4 C3 -178.1(5) . . . . ?
Cu1 N4 C4 C3 4.1(5) . . . . ?
N3 C3 C4 N4 3.5(7) . . . . ?
N3 C3 C4 C8 -175.3(5) . . . . ?
C16 C15 C20 C19 -1.4(8) . . . . ?
C1 C15 C20 C19 176.4(5) . . . . ?
N4 C4 C8 C7 -2.0(8) . . . . ?
C3 C4 C8 C7 176.7(5) . . . . ?
C15 C16 C17 C18 1.2(9) . . . . ?
C4 C8 C7 C6 1.6(9) . . . . ?
C15 C20 C19 C18 0.6(9) . . . . ?
C8 C7 C6 C5 0.1(9) . . . . ?
C16 C17 C18 C19 -1.9(10) . . . . ?
C20 C19 C18 C17 1.1(10) . . . . ?
C11 C12 C13 C14 -0.8(11) . . . . ?
C9 C14 C13 C12 1.8(10) . . . . ?
C4 N4 C5 C6 1.0(8) . . . . ?
Cu1 N4 C5 C6 178.4(4) . . . . ?
C7 C6 C5 N4 -1.4(10) . . . . ?
C13 C12 C11 C10 0.0(11) . . . . ?
C9 C10 C11 C12 -0.2(11) . . . . ?

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
C2 H11 O5 0.98 2.34 3.230(8) 150.3 3_657
C8 H1 O3 0.93 2.45 3.305(8) 152.4 1_556
N5 H18 O2 0.65(3) 2.40(4) 3.054(7) 174(4) 3_656
####################################################################### 
# 
# 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_sad1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1555394'
_audit_update_record             
;
2017-06-12 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;

_audit_creation_date             2017-06-11T18:17:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 Cl2 Cu N3'
_chemical_formula_sum            'C20 H18 Cl2 Cu N3'
_chemical_formula_weight         434.68
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_chemical_absolute_configuration ?
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1742(14)
_cell_length_b                   11.350(2)
_cell_length_c                   12.470(3)
_cell_angle_alpha                76.80(3)
_cell_angle_beta                 75.49(3)
_cell_angle_gamma                83.62(3)
_cell_volume                     955.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1026
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      21.18
_exptl_crystal_recrystallization_method acetonitrile

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prisma
_exptl_crystal_colour            green
_diffrn_ambient_temperature      293(2)
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_F_000             444
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 4 1 0.011
-2 -2 -1 0.229
4 5 2 0.154
0 -4 -1 0.134
0 0 -1 0.044
5 3 0 0.221
-5 -3 -5 0.231
0 0 1 0.068
3 2 5 0.202

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.431
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.8046
_exptl_absorpt_correction_T_max  0.9293
_shelx_estimated_absorpt_T_min   0.62
_shelx_estimated_absorpt_T_max   0.858
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_av_R_equivalents  0.4104
_diffrn_reflns_number            5909
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.041
_diffrn_reflns_theta_max         23.254
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.79
_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.99
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.99
_diffrn_reflns_point_group_measured_fraction_max 0.972
_reflns_number_total             2668
_reflns_number_gt                393
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0001P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2668
_refine_ls_number_parameters     235
_refine_ls_number_restraints     227
_refine_ls_R_factor_all          0.3636
_refine_ls_R_factor_gt           0.0879
_refine_ls_wR_factor_ref         0.2442
_refine_ls_wR_factor_gt          0.1337
_refine_ls_goodness_of_fit_ref   0.587
_refine_ls_restrained_S_all      0.569
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.075

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.148 0.159 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.32 1.265 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.2228(4) 0.2887(2) 0.0398(3) 0.0867(12) Uani 1 d . .
Cl1 Cl 1.3697(8) 0.1249(5) 0.1637(6) 0.096(2) Uani 1 d . .
Cl2 Cl 1.4832(8) 0.3791(5) -0.0848(5) 0.100(2) Uani 1 d . .
N1 N 1.162(3) 0.1911(13) -0.0647(18) 0.085(4) Uani 1 d . .
N2 N 0.935(2) 0.2832(15) 0.0999(17) 0.085(4) Uani 1 d . .
N3 N 1.186(2) 0.4101(13) 0.1406(16) 0.084(4) Uani 1 d . .
H1 H 1.2029 0.4064 0.2252 0.1 Uiso 1 d . .
C1 C 0.965(3) 0.1694(16) -0.046(2) 0.081(5) Uani 1 d . .
C2 C 0.856(3) 0.2288(18) 0.043(2) 0.091(6) Uani 1 d . .
H14 H 0.7227 0.2282 0.0602 0.109 Uiso 1 calc . .
C3 C 0.847(3) 0.3492(18) 0.188(2) 0.084(4) Uani 1 d . .
H13 H 0.7229 0.3848 0.1721 0.101 Uiso 1 calc . .
C4 C 0.979(3) 0.4589(18) 0.170(2) 0.091(5) Uani 1 d . .
H7 H 0.9551 0.5196 0.1043 0.109 Uiso 1 calc . .
C5 C 0.930(3) 0.5193(16) 0.271(2) 0.078(5) Uani 1 d . .
C6 C 0.733(3) 0.545(2) 0.316(2) 0.099(6) Uani 1 d . .
H6 H 0.6386 0.5185 0.2897 0.119 Uiso 1 calc . .
C7 C 0.684(4) 0.6091(18) 0.401(2) 0.099(6) Uani 1 d . .
H5 H 0.5543 0.6261 0.4322 0.118 Uiso 1 calc . .
C8 C 0.819(4) 0.648(2) 0.441(2) 0.114(7) Uani 1 d . .
H4 H 0.7803 0.6862 0.5024 0.137 Uiso 1 calc . .
C9 C 1.026(4) 0.631(2) 0.390(2) 0.103(6) Uani 1 d . .
H3 H 1.1182 0.6633 0.4139 0.123 Uiso 1 calc . .
C10 C 1.082(4) 0.565(2) 0.302(2) 0.109(7) Uani 1 d . .
H2 H 1.2103 0.5521 0.2662 0.131 Uiso 1 calc . .
C11 C 0.802(3) 0.2712(18) 0.307(2) 0.083(5) Uani 1 d . .
C12 C 0.947(4) 0.2161(19) 0.365(2) 0.099(7) Uani 1 d . .
H12 H 1.0764 0.2295 0.3317 0.118 Uiso 1 calc . .
C13 C 0.894(3) 0.1427(17) 0.471(2) 0.082(6) Uani 1 d . .
H11 H 0.9886 0.1138 0.511 0.098 Uiso 1 calc . .
C14 C 0.708(4) 0.110(2) 0.520(3) 0.111(7) Uani 1 d . .
H10 H 0.6744 0.0587 0.5902 0.134 Uiso 1 calc . .
C15 C 0.574(3) 0.160(2) 0.456(2) 0.110(8) Uani 1 d . .
H9 H 0.4439 0.1476 0.4881 0.131 Uiso 1 calc . .
C16 C 0.624(3) 0.223(2) 0.351(3) 0.117(7) Uani 1 d . .
H8 H 0.536 0.2365 0.3059 0.141 Uiso 1 calc . .
C17 C 0.892(3) 0.1108(17) -0.1044(19) 0.073(5) Uani 1 d . .
H18 H 0.7596 0.1052 -0.0919 0.088 Uiso 1 calc . .
C18 C 1.012(3) 0.0614(17) -0.180(2) 0.078(5) Uani 1 d . .
H17 H 0.9612 0.0141 -0.2165 0.093 Uiso 1 calc . .
C19 C 1.215(3) 0.0731(17) -0.212(2) 0.080(5) Uani 1 d . .
H16 H 1.3028 0.0422 -0.2693 0.096 Uiso 1 calc . .
C20 C 1.257(3) 0.1418(18) -0.139(2) 0.081(5) Uani 1 d . .
H15 H 1.3881 0.1511 -0.1521 0.097 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N2 2.016(16) . ?
Cu1 N3 2.023(18) . ?
Cu1 N1 2.043(18) . ?
Cu1 Cl2 2.281(6) . ?
Cu1 Cl1 2.454(6) . ?
N1 C20 1.22(3) . ?
N1 C1 1.41(2) . ?
N2 C2 1.30(2) . ?
N2 C3 1.44(3) . ?
N3 C4 1.51(3) . ?
N3 H1 1.0843 . ?
C1 C17 1.32(3) . ?
C1 C2 1.44(3) . ?
C2 H14 0.93 . ?
C3 C11 1.52(3) . ?
C3 C4 1.59(3) . ?
C3 H13 0.98 . ?
C4 C5 1.51(3) . ?
C4 H7 0.98 . ?
C5 C6 1.41(3) . ?
C5 C10 1.42(3) . ?
C6 C7 1.37(3) . ?
C6 H6 0.93 . ?
C7 C8 1.35(3) . ?
C7 H5 0.93 . ?
C8 C9 1.48(3) . ?
C8 H4 0.93 . ?
C9 C10 1.42(3) . ?
C9 H3 0.93 . ?
C10 H2 0.93 . ?
C11 C16 1.38(3) . ?
C11 C12 1.42(3) . ?
C12 C13 1.38(3) . ?
C12 H12 0.93 . ?
C13 C14 1.37(3) . ?
C13 H11 0.93 . ?
C14 C15 1.39(3) . ?
C14 H10 0.93 . ?
C15 C16 1.32(3) . ?
C15 H9 0.93 . ?
C16 H8 0.93 . ?
C17 C18 1.29(3) . ?
C17 H18 0.93 . ?
C18 C19 1.42(3) . ?
C18 H17 0.93 . ?
C19 C20 1.43(3) . ?
C19 H16 0.93 . ?
C20 H15 0.93 . ?

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 N3 81.4(7) . . ?
N2 Cu1 N1 80.5(8) . . ?
N3 Cu1 N1 159.1(6) . . ?
N2 Cu1 Cl2 150.0(5) . . ?
N3 Cu1 Cl2 93.5(5) . . ?
N1 Cu1 Cl2 96.9(6) . . ?
N2 Cu1 Cl1 106.8(5) . . ?
N3 Cu1 Cl1 95.8(5) . . ?
N1 Cu1 Cl1 99.3(5) . . ?
Cl2 Cu1 Cl1 103.1(2) . . ?
C20 N1 C1 110(2) . . ?
C20 N1 Cu1 135.0(17) . . ?
C1 N1 Cu1 115.0(15) . . ?
C2 N2 C3 130.1(18) . . ?
C2 N2 Cu1 112.0(16) . . ?
C3 N2 Cu1 117.4(14) . . ?
C4 N3 Cu1 112.3(12) . . ?
C4 N3 H1 92 . . ?
Cu1 N3 H1 134.7 . . ?
C17 C1 N1 125(2) . . ?
C17 C1 C2 126(2) . . ?
N1 C1 C2 108.5(19) . . ?
N2 C2 C1 124(2) . . ?
N2 C2 H14 118.1 . . ?
C1 C2 H14 118.1 . . ?
N2 C3 C11 114.5(18) . . ?
N2 C3 C4 106.6(19) . . ?
C11 C3 C4 115.2(19) . . ?
N2 C3 H13 106.7 . . ?
C11 C3 H13 106.7 . . ?
C4 C3 H13 106.7 . . ?
N3 C4 C5 114.3(18) . . ?
N3 C4 C3 106.9(15) . . ?
C5 C4 C3 112(2) . . ?
N3 C4 H7 107.7 . . ?
C5 C4 H7 107.7 . . ?
C3 C4 H7 107.7 . . ?
C6 C5 C10 123(2) . . ?
C6 C5 C4 117(2) . . ?
C10 C5 C4 119(2) . . ?
C7 C6 C5 119(2) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C8 C7 C6 122(3) . . ?
C8 C7 H5 119.2 . . ?
C6 C7 H5 119.2 . . ?
C7 C8 C9 121(3) . . ?
C7 C8 H4 119.4 . . ?
C9 C8 H4 119.4 . . ?
C10 C9 C8 118(2) . . ?
C10 C9 H3 120.8 . . ?
C8 C9 H3 120.8 . . ?
C9 C10 C5 117(3) . . ?
C9 C10 H2 121.7 . . ?
C5 C10 H2 121.7 . . ?
C16 C11 C12 115(2) . . ?
C16 C11 C3 120(2) . . ?
C12 C11 C3 123(2) . . ?
C13 C12 C11 119(2) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 123(2) . . ?
C14 C13 H11 118.5 . . ?
C12 C13 H11 118.5 . . ?
C13 C14 C15 115(3) . . ?
C13 C14 H10 122.4 . . ?
C15 C14 H10 122.4 . . ?
C16 C15 C14 122(3) . . ?
C16 C15 H9 118.8 . . ?
C14 C15 H9 118.8 . . ?
C15 C16 C11 123(3) . . ?
C15 C16 H8 118.7 . . ?
C11 C16 H8 118.7 . . ?
C18 C17 C1 117(2) . . ?
C18 C17 H18 121.3 . . ?
C1 C17 H18 121.3 . . ?
C17 C18 C19 126(2) . . ?
C17 C18 H17 117.2 . . ?
C19 C18 H17 117.2 . . ?
C18 C19 C20 106(2) . . ?
C18 C19 H16 127 . . ?
C20 C19 H16 127 . . ?
N1 C20 C19 135(2) . . ?
N1 C20 H15 112.3 . . ?
C19 C20 H15 112.3 . . ?

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
C20 N1 C1 C17 -4(3) . . . . ?
Cu1 N1 C1 C17 178.5(17) . . . . ?
C20 N1 C1 C2 -180(2) . . . . ?
Cu1 N1 C1 C2 2(2) . . . . ?
C3 N2 C2 C1 178(2) . . . . ?
Cu1 N2 C2 C1 6(3) . . . . ?
C17 C1 C2 N2 178(2) . . . . ?
N1 C1 C2 N2 -5(3) . . . . ?
C2 N2 C3 C11 88(3) . . . . ?
Cu1 N2 C3 C11 -100.3(18) . . . . ?
C2 N2 C3 C4 -144(2) . . . . ?
Cu1 N2 C3 C4 28(2) . . . . ?
Cu1 N3 C4 C5 162.6(14) . . . . ?
Cu1 N3 C4 C3 38(2) . . . . ?
N2 C3 C4 N3 -41(2) . . . . ?
C11 C3 C4 N3 87(2) . . . . ?
N2 C3 C4 C5 -167.0(17) . . . . ?
C11 C3 C4 C5 -39(2) . . . . ?
N3 C4 C5 C6 -167.6(17) . . . . ?
C3 C4 C5 C6 -46(3) . . . . ?
N3 C4 C5 C10 23(3) . . . . ?
C3 C4 C5 C10 144.6(19) . . . . ?
C10 C5 C6 C7 -5(3) . . . . ?
C4 C5 C6 C7 -174(2) . . . . ?
C5 C6 C7 C8 0(4) . . . . ?
C6 C7 C8 C9 5(4) . . . . ?
C7 C8 C9 C10 -5(4) . . . . ?
C8 C9 C10 C5 0(3) . . . . ?
C6 C5 C10 C9 5(3) . . . . ?
C4 C5 C10 C9 174(2) . . . . ?
N2 C3 C11 C16 -92(3) . . . . ?
C4 C3 C11 C16 144(2) . . . . ?
N2 C3 C11 C12 70(3) . . . . ?
C4 C3 C11 C12 -54(3) . . . . ?
C16 C11 C12 C13 -14(3) . . . . ?
C3 C11 C12 C13 -177(2) . . . . ?
C11 C12 C13 C14 6(4) . . . . ?
C12 C13 C14 C15 -2(3) . . . . ?
C13 C14 C15 C16 7(4) . . . . ?
C14 C15 C16 C11 -16(4) . . . . ?
C12 C11 C16 C15 20(4) . . . . ?
C3 C11 C16 C15 -177(2) . . . . ?
N1 C1 C17 C18 5(3) . . . . ?
C2 C1 C17 C18 -179(2) . . . . ?
C1 C17 C18 C19 -6(3) . . . . ?
C17 C18 C19 C20 4(3) . . . . ?
C1 N1 C20 C19 3(4) . . . . ?
Cu1 N1 C20 C19 179.6(16) . . . . ?
C18 C19 C20 N1 -3(4) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
# start Validation Reply Form

_vrf_RINTA01_I                   
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: limited resolution and Poor quality data due to the thin
plate crystals with low diffracting power.
;
_vrf_PLAT020_I                   
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.410 Report
RESPONSE: low crystal quality,
;
_vrf_PLAT026_I                   
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..         15 %     
RESPONSE: limited resolution and Poor quality data due to the thin
plate crystals with low diffracting power.
;
