# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_jmlac181204
_database_code_depnum_ccdc_archive 'CCDC 2014872'
loop_
_audit_author_name
_audit_author_address
'Lydia Karmazin'
;Institut de Chimie de Strasbourg
France
;
_audit_update_record             
;
2020-07-08 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 Cu N6 O2, 2(N O3)'
_chemical_formula_sum            'C16 H18 Cu N8 O8'
_chemical_formula_weight         513.92

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8003(3)
_cell_length_b                   10.8755(4)
_cell_length_c                   15.0688(5)
_cell_angle_alpha                70.9890(10)
_cell_angle_beta                 88.1620(10)
_cell_angle_gamma                70.8860(10)
_cell_volume                     1137.98(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9980
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      27.95

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             526
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.018
_shelx_estimated_absorpt_T_min   0.807
_shelx_estimated_absorpt_T_max   0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6969
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            59670
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.102
_diffrn_reflns_theta_max         28.036
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5494
_reflns_number_gt                4567
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0536P)²+1.6944P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5494
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1216
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.5980(4) 0.8108(3) 0.08649(18) 0.0275(5) Uani 1 1 d . . . . .
C2 C 0.7143(5) 0.8395(4) 0.0172(2) 0.0435(8) Uani 1 1 d . . . . .
H2 H 0.7149 0.8140 -0.0375 0.052 Uiso 1 1 calc R U . . .
C3 C 0.8289(6) 0.9065(5) 0.0303(3) 0.0623(12) Uani 1 1 d . . . . .
H3 H 0.9098 0.9287 -0.0158 0.075 Uiso 1 1 calc R U . . .
C4 C 0.8258(6) 0.9409(5) 0.1101(3) 0.0646(13) Uani 1 1 d . . . . .
H4 H 0.9044 0.9869 0.1198 0.078 Uiso 1 1 calc R U . . .
C5 C 0.7066(5) 0.9078(4) 0.1766(2) 0.0498(9) Uani 1 1 d . . . . .
H5 H 0.7057 0.9311 0.2322 0.060 Uiso 1 1 calc R U . . .
C6 C 0.4733(4) 0.7380(3) 0.07920(18) 0.0276(5) Uani 1 1 d . . . . .
H6 H 0.4663 0.7107 0.0260 0.033 Uiso 1 1 calc R U . . .
C7 C 0.1557(4) 0.6238(3) 0.2204(2) 0.0334(6) Uani 1 1 d . . . . .
C8 C 0.0338(6) 0.5432(5) 0.2183(3) 0.0611(11) Uani 1 1 d . . . . .
H8A H 0.0809 0.4514 0.2663 0.092 Uiso 1 1 calc R U . . .
H8B H 0.0297 0.5337 0.1560 0.092 Uiso 1 1 calc R U . . .
H8C H -0.0892 0.5917 0.2313 0.092 Uiso 1 1 calc R U . . .
C9 C 0.6171(3) 0.6239(3) 0.43154(17) 0.0239(5) Uani 1 1 d . . . . .
C10 C 0.7434(4) 0.5264(3) 0.50344(19) 0.0307(6) Uani 1 1 d . . . . .
H10 H 0.7700 0.5477 0.5567 0.037 Uiso 1 1 calc R U . . .
C11 C 0.8309(4) 0.3966(3) 0.4966(2) 0.0365(7) Uani 1 1 d . . . . .
H11 H 0.9193 0.3277 0.5447 0.044 Uiso 1 1 calc R U . . .
C12 C 0.7869(4) 0.3699(3) 0.4184(2) 0.0396(7) Uani 1 1 d . . . . .
H12 H 0.8423 0.2811 0.4128 0.047 Uiso 1 1 calc R U . . .
C13 C 0.6607(4) 0.4738(3) 0.3480(2) 0.0345(6) Uani 1 1 d . . . . .
H13 H 0.6334 0.4551 0.2937 0.041 Uiso 1 1 calc R U . . .
C14 C 0.5127(4) 0.7620(3) 0.43372(18) 0.0267(5) Uani 1 1 d . . . . .
H14 H 0.5285 0.7926 0.4842 0.032 Uiso 1 1 calc R U . . .
C15 C 0.1790(4) 1.0306(3) 0.26914(19) 0.0270(5) Uani 1 1 d . . . . .
C16 C 0.0491(5) 1.1720(3) 0.2543(2) 0.0467(8) Uani 1 1 d . . . . .
H16A H 0.0598 1.2335 0.1919 0.070 Uiso 1 1 calc R U . . .
H16B H 0.0772 1.2061 0.3028 0.070 Uiso 1 1 calc R U . . .
H16C H -0.0754 1.1694 0.2584 0.070 Uiso 1 1 calc R U . . .
N1 N 0.5930(3) 0.8443(3) 0.16495(15) 0.0298(5) Uani 1 1 d . . . . .
N2 N 0.3744(3) 0.7132(2) 0.14754(15) 0.0233(4) Uani 1 1 d . . . . .
N3 N 0.2592(3) 0.6425(3) 0.14646(16) 0.0320(5) Uani 1 1 d . . . . .
H3N H 0.2523 0.6109 0.1003 0.038 Uiso 1 1 calc R U . . .
N4 N 0.5768(3) 0.5983(2) 0.35372(15) 0.0253(4) Uani 1 1 d . . . . .
N5 N 0.3989(3) 0.8377(2) 0.36254(15) 0.0246(4) Uani 1 1 d . . . . .
N6 N 0.2860(3) 0.9686(2) 0.35118(16) 0.0284(5) Uani 1 1 d . . . . .
H6N H 0.2829 1.0092 0.3934 0.034 Uiso 1 1 calc R U . . .
N7 N 0.2186(4) 1.0395(3) 0.55580(19) 0.0458(7) Uani 1 1 d . . . . .
N8 N 0.7334(4) 0.4244(4) 0.0597(3) 0.0633(11) Uani 1 1 d . . . . .
O1 O 0.1644(3) 0.6697(2) 0.28375(14) 0.0360(5) Uani 1 1 d . . . . .
O2 O 0.1910(3) 0.9706(2) 0.21090(13) 0.0309(4) Uani 1 1 d . . . . .
O3 O 0.2721(9) 0.9186(4) 0.5701(3) 0.138(2) Uani 1 1 d . . . . .
O4 O 0.2263(5) 1.1159(3) 0.4734(2) 0.0720(9) Uani 1 1 d . . . . .
O5 O 0.1717(5) 1.0869(3) 0.61902(19) 0.0771(10) Uani 1 1 d . . . . .
O6 O 0.7162(5) 0.5098(4) -0.0198(2) 0.0781(10) Uani 1 1 d . . . . .
O7 O 0.7187(4) 0.4599(3) 0.12972(18) 0.0604(8) Uani 1 1 d . . . . .
O8 O 0.7610(6) 0.3028(4) 0.0659(3) 0.123(2) Uani 1 1 d . . . . .
Cu1 Cu 0.38782(4) 0.77204(3) 0.25798(2) 0.02443(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
C1 N1 1.342(3) . ?
C1 C2 1.387(4) . ?
C1 C6 1.467(4) . ?
C2 C3 1.379(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.367(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.335(4) . ?
C5 H5 0.9500 . ?
C6 N2 1.278(3) . ?
C6 H6 0.9500 . ?
C7 O1 1.226(4) . ?
C7 N3 1.355(4) . ?
C7 C8 1.497(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N4 1.358(3) . ?
C9 C10 1.380(4) . ?
C9 C14 1.466(4) . ?
C10 C11 1.389(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(4) . ?
C12 H12 0.9500 . ?
C13 N4 1.327(4) . ?
C13 H13 0.9500 . ?
C14 N5 1.274(3) . ?
C14 H14 0.9500 . ?
C15 O2 1.238(3) . ?
C15 N6 1.354(3) . ?
C15 C16 1.486(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N1 Cu1 2.260(2) . ?
N2 N3 1.364(3) . ?
N2 Cu1 1.985(2) . ?
N3 H3N 0.8800 . ?
N4 Cu1 2.088(2) . ?
N5 N6 1.364(3) . ?
N5 Cu1 1.945(2) . ?
N6 H6N 0.8800 . ?
N7 O3 1.188(4) . ?
N7 O5 1.217(4) . ?
N7 O4 1.262(4) . ?
N8 O7 1.227(4) . ?
N8 O6 1.232(5) . ?
N8 O8 1.240(5) . ?
O1 Cu1 2.318(2) . ?
O2 Cu1 2.1032(19) . ?

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 C1 C2 123.3(3) . . ?
N1 C1 C6 115.3(2) . . ?
C2 C1 C6 121.5(3) . . ?
C3 C2 C1 117.6(3) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 122.0(3) . . ?
N1 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
N2 C6 C1 117.0(2) . . ?
N2 C6 H6 121.5 . . ?
C1 C6 H6 121.5 . . ?
O1 C7 N3 121.5(3) . . ?
O1 C7 C8 123.5(3) . . ?
N3 C7 C8 115.0(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C9 C10 122.5(2) . . ?
N4 C9 C14 114.5(2) . . ?
C10 C9 C14 123.0(2) . . ?
C9 C10 C11 118.8(3) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C12 C11 C10 118.7(3) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C11 C12 C13 119.4(3) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
N4 C13 C12 122.4(3) . . ?
N4 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
N5 C14 C9 114.7(2) . . ?
N5 C14 H14 122.7 . . ?
C9 C14 H14 122.7 . . ?
O2 C15 N6 120.7(2) . . ?
O2 C15 C16 123.0(3) . . ?
N6 C15 C16 116.3(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 N1 C1 118.0(3) . . ?
C5 N1 Cu1 131.6(2) . . ?
C1 N1 Cu1 110.33(17) . . ?
C6 N2 N3 120.0(2) . . ?
C6 N2 Cu1 121.37(18) . . ?
N3 N2 Cu1 118.59(16) . . ?
C7 N3 N2 116.2(2) . . ?
C7 N3 H3N 121.9 . . ?
N2 N3 H3N 121.9 . . ?
C13 N4 C9 118.3(2) . . ?
C13 N4 Cu1 130.01(19) . . ?
C9 N4 Cu1 111.69(17) . . ?
C14 N5 N6 124.3(2) . . ?
C14 N5 Cu1 119.95(19) . . ?
N6 N5 Cu1 115.70(16) . . ?
C15 N6 N5 114.0(2) . . ?
C15 N6 H6N 123.0 . . ?
N5 N6 H6N 123.0 . . ?
O3 N7 O5 121.6(3) . . ?
O3 N7 O4 116.7(3) . . ?
O5 N7 O4 121.5(3) . . ?
O7 N8 O6 120.8(4) . . ?
O7 N8 O8 121.5(4) . . ?
O6 N8 O8 117.7(4) . . ?
C7 O1 Cu1 109.48(18) . . ?
C15 O2 Cu1 111.68(17) . . ?
N5 Cu1 N2 177.55(9) . . ?
N5 Cu1 N4 78.83(9) . . ?
N2 Cu1 N4 103.25(9) . . ?
N5 Cu1 O2 77.90(8) . . ?
N2 Cu1 O2 100.09(8) . . ?
N4 Cu1 O2 156.48(8) . . ?
N5 Cu1 N1 102.58(9) . . ?
N2 Cu1 N1 75.99(8) . . ?
N4 Cu1 N1 96.30(9) . . ?
O2 Cu1 N1 91.98(9) . . ?
N5 Cu1 O1 107.31(8) . . ?
N2 Cu1 O1 74.03(8) . . ?
N4 Cu1 O1 92.26(8) . . ?
O2 Cu1 O1 91.46(8) . . ?
N1 Cu1 O1 149.97(8) . . ?

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
N1 C1 C2 C3 -0.3(5) . . . . ?
C6 C1 C2 C3 -179.1(3) . . . . ?
C1 C2 C3 C4 0.5(7) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C3 C4 C5 N1 -0.6(7) . . . . ?
N1 C1 C6 N2 -0.5(4) . . . . ?
C2 C1 C6 N2 178.4(3) . . . . ?
N4 C9 C10 C11 -0.9(4) . . . . ?
C14 C9 C10 C11 177.7(3) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C10 C11 C12 C13 1.7(5) . . . . ?
C11 C12 C13 N4 -1.5(5) . . . . ?
N4 C9 C14 N5 0.2(3) . . . . ?
C10 C9 C14 N5 -178.4(3) . . . . ?
C4 C5 N1 C1 0.8(6) . . . . ?
C4 C5 N1 Cu1 178.6(3) . . . . ?
C2 C1 N1 C5 -0.3(5) . . . . ?
C6 C1 N1 C5 178.5(3) . . . . ?
C2 C1 N1 Cu1 -178.6(3) . . . . ?
C6 C1 N1 Cu1 0.2(3) . . . . ?
C1 C6 N2 N3 -178.2(2) . . . . ?
C1 C6 N2 Cu1 0.5(3) . . . . ?
O1 C7 N3 N2 1.0(4) . . . . ?
C8 C7 N3 N2 -178.7(3) . . . . ?
C6 N2 N3 C7 -178.3(3) . . . . ?
Cu1 N2 N3 C7 2.9(3) . . . . ?
C12 C13 N4 C9 0.1(4) . . . . ?
C12 C13 N4 Cu1 178.7(2) . . . . ?
C10 C9 N4 C13 1.1(4) . . . . ?
C14 C9 N4 C13 -177.5(2) . . . . ?
C10 C9 N4 Cu1 -177.7(2) . . . . ?
C14 C9 N4 Cu1 3.6(3) . . . . ?
C9 C14 N5 N6 178.8(2) . . . . ?
C9 C14 N5 Cu1 -4.5(3) . . . . ?
O2 C15 N6 N5 -1.6(4) . . . . ?
C16 C15 N6 N5 178.2(3) . . . . ?
C14 N5 N6 C15 178.8(3) . . . . ?
Cu1 N5 N6 C15 2.0(3) . . . . ?
N3 C7 O1 Cu1 -3.6(4) . . . . ?
C8 C7 O1 Cu1 176.0(3) . . . . ?
N6 C15 O2 Cu1 0.5(3) . . . . ?
C16 C15 O2 Cu1 -179.4(3) . . . . ?

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
N3 H3N O6 0.88 2.02 2.873(4) 164.2 2_665
N6 H6N O4 0.88 1.88 2.748(4) 168.2 .

_refine_diff_density_max         1.071
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.079

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.459 0.247 0.247 48 15 ' '
2 0.540 0.753 0.753 49 15 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
 The residual electron density was assigned to one molecule of
 the acetonitrile solvent [30/2 = 15 e per asymmetric unit;
 one molecule of CH3CN would give 22e].
;



####################################################################### 
# 
# 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_jmlac190410
_database_code_depnum_ccdc_archive 'CCDC 2014873'
loop_
_audit_author_name
_audit_author_address
'Lydia Karmazin'
;Institut de Chimie de Strasbourg
France
;
_audit_update_record             
;
2020-07-08 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 Cu N6 O2, N O3'
_chemical_formula_sum            'C16 H17 Cu N7 O5'
_chemical_formula_weight         450.90

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.4150(3)
_cell_length_b                   13.2916(5)
_cell_length_c                   16.6694(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.3220(10)
_cell_angle_gamma                90
_cell_volume                     1834.28(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9906
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      29.01

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.237
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6637
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28986
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.972
_diffrn_reflns_theta_max         29.025
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4897
_reflns_number_gt                4099
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0284P)²+1.4662P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4897
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0725
_refine_ls_wR_factor_gt          0.0665
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
C1 C 0.4764(2) 0.85332(13) 0.44070(10) 0.0141(3) Uani 1 1 d . . . . .
C2 C 0.6245(2) 0.89949(13) 0.44398(10) 0.0173(3) Uani 1 1 d . . . . .
H2 H 0.6567 0.9234 0.3956 0.021 Uiso 1 1 calc R U . . .
C3 C 0.7256(2) 0.91045(13) 0.51908(11) 0.0184(3) Uani 1 1 d . . . . .
H3 H 0.8278 0.9422 0.5230 0.022 Uiso 1 1 calc R U . . .
C4 C 0.6749(2) 0.87429(14) 0.58801(10) 0.0185(3) Uani 1 1 d . . . . .
H4 H 0.7427 0.8799 0.6399 0.022 Uiso 1 1 calc R U . . .
C5 C 0.5231(2) 0.82945(13) 0.58057(10) 0.0173(3) Uani 1 1 d . . . . .
H5 H 0.4884 0.8055 0.6283 0.021 Uiso 1 1 calc R U . . .
C6 C 0.3597(2) 0.84157(13) 0.36512(10) 0.0161(3) Uani 1 1 d . . . . .
H6 H 0.3848 0.8560 0.3130 0.019 Uiso 1 1 calc R U . . .
C7 C -0.0379(2) 0.77641(12) 0.34409(10) 0.0141(3) Uani 1 1 d . . . . .
C8 C -0.1940(2) 0.76852(14) 0.28558(11) 0.0189(3) Uani 1 1 d . . . . .
H8A H -0.2472 0.7049 0.2945 0.028 Uiso 1 1 calc R U . . .
H8B H -0.1732 0.7706 0.2296 0.028 Uiso 1 1 calc R U . . .
H8C H -0.2642 0.8249 0.2942 0.028 Uiso 1 1 calc R U . . .
C9 C 0.2065(2) 0.55457(13) 0.54387(10) 0.0151(3) Uani 1 1 d . . . . .
C10 C 0.2077(2) 0.45098(14) 0.55297(10) 0.0191(3) Uani 1 1 d . . . . .
H10 H 0.1772 0.4209 0.5996 0.023 Uiso 1 1 calc R U . . .
C11 C 0.2545(2) 0.39207(14) 0.49236(11) 0.0220(4) Uani 1 1 d . . . . .
H11 H 0.2551 0.3208 0.4964 0.026 Uiso 1 1 calc R U . . .
C12 C 0.3002(2) 0.43893(14) 0.42603(11) 0.0222(4) Uani 1 1 d . . . . .
H12 H 0.3355 0.4005 0.3845 0.027 Uiso 1 1 calc R U . . .
C13 C 0.2935(2) 0.54361(14) 0.42107(10) 0.0196(3) Uani 1 1 d . . . . .
H13 H 0.3239 0.5754 0.3750 0.023 Uiso 1 1 calc R U . . .
C14 C 0.1620(2) 0.62107(13) 0.60636(10) 0.0161(3) Uani 1 1 d . . . . .
H14 H 0.1397 0.5945 0.6561 0.019 Uiso 1 1 calc R U . . .
C15 C 0.1117(2) 0.87910(13) 0.63603(10) 0.0147(3) Uani 1 1 d . . . . .
C16 C 0.0792(2) 0.94457(14) 0.70441(11) 0.0196(3) Uani 1 1 d . . . . .
H16A H 0.1784 0.9800 0.7286 0.029 Uiso 1 1 calc R U . . .
H16B H 0.0426 0.9028 0.7460 0.029 Uiso 1 1 calc R U . . .
H16C H -0.0048 0.9937 0.6834 0.029 Uiso 1 1 calc R U . . .
N1 N 0.42551(17) 0.81909(11) 0.50894(8) 0.0137(3) Uani 1 1 d . . . . .
N2 N 0.22081(17) 0.81022(11) 0.37503(8) 0.0133(3) Uani 1 1 d . . . . .
N3 N 0.09184(17) 0.79963(11) 0.31188(8) 0.0147(3) Uani 1 1 d . . . . .
N4 N 0.24650(18) 0.60113(11) 0.47804(8) 0.0161(3) Uani 1 1 d . . . . .
N5 N 0.15389(17) 0.71579(11) 0.59237(8) 0.0133(3) Uani 1 1 d . . . . .
N6 N 0.11733(18) 0.77831(11) 0.65192(8) 0.0152(3) Uani 1 1 d . . . . .
N7 N 0.45737(19) 0.46848(12) 0.73620(9) 0.0205(3) Uani 1 1 d . . . . .
O1 O -0.03593(15) 0.76236(9) 0.42035(7) 0.0162(2) Uani 1 1 d . . . . .
O2 O 0.13177(15) 0.91204(9) 0.57007(7) 0.0188(3) Uani 1 1 d . . . . .
O3 O 0.53451(19) 0.54853(11) 0.73123(9) 0.0319(3) Uani 1 1 d . . . . .
O4 O 0.52617(18) 0.38533(11) 0.73523(9) 0.0287(3) Uani 1 1 d . . . . .
O5 O 0.31131(16) 0.47309(11) 0.74285(8) 0.0241(3) Uani 1 1 d . . . . .
Cu1 Cu 0.19073(2) 0.77101(2) 0.48310(2) 0.01314(6) Uani 1 1 d . . . . .
H6N H 0.108(3) 0.7535(18) 0.6984(16) 0.031(6) 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
C1 N1 1.364(2) . ?
C1 C2 1.381(2) . ?
C1 C6 1.461(2) . ?
C2 C3 1.389(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.330(2) . ?
C5 H5 0.9500 . ?
C6 N2 1.279(2) . ?
C6 H6 0.9500 . ?
C7 O1 1.2821(19) . ?
C7 N3 1.336(2) . ?
C7 C8 1.493(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N4 1.354(2) . ?
C9 C10 1.385(2) . ?
C9 C14 1.465(2) . ?
C10 C11 1.390(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(3) . ?
C12 H12 0.9500 . ?
C13 N4 1.333(2) . ?
C13 H13 0.9500 . ?
C14 N5 1.280(2) . ?
C14 H14 0.9500 . ?
C15 O2 1.223(2) . ?
C15 N6 1.365(2) . ?
C15 C16 1.498(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N1 Cu1 2.0475(14) . ?
N2 N3 1.3771(19) . ?
N2 Cu1 1.9351(13) . ?
N4 Cu1 2.3109(15) . ?
N5 N6 1.3711(19) . ?
N5 Cu1 2.0383(13) . ?
N6 H6N 0.86(3) . ?
N7 O4 1.249(2) . ?
N7 O5 1.255(2) . ?
N7 O3 1.257(2) . ?
O1 Cu1 2.0076(12) . ?

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 C1 C2 122.10(15) . . ?
N1 C1 C6 114.87(15) . . ?
C2 C1 C6 122.97(15) . . ?
C1 C2 C3 118.99(16) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 118.83(16) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 119.28(16) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 122.19(16) . . ?
N1 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
N2 C6 C1 114.35(14) . . ?
N2 C6 H6 122.8 . . ?
C1 C6 H6 122.8 . . ?
O1 C7 N3 124.44(15) . . ?
O1 C7 C8 119.41(15) . . ?
N3 C7 C8 116.14(14) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C9 C10 123.04(16) . . ?
N4 C9 C14 115.65(15) . . ?
C10 C9 C14 121.31(15) . . ?
C9 C10 C11 118.55(16) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 118.89(17) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 118.90(17) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
N4 C13 C12 122.95(16) . . ?
N4 C13 H13 118.5 . . ?
C12 C13 H13 118.5 . . ?
N5 C14 C9 118.42(15) . . ?
N5 C14 H14 120.8 . . ?
C9 C14 H14 120.8 . . ?
O2 C15 N6 121.36(16) . . ?
O2 C15 C16 123.35(16) . . ?
N6 C15 C16 115.29(14) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 N1 C1 118.60(15) . . ?
C5 N1 Cu1 129.71(12) . . ?
C1 N1 Cu1 111.36(11) . . ?
C6 N2 N3 123.21(14) . . ?
C6 N2 Cu1 118.88(11) . . ?
N3 N2 Cu1 117.87(11) . . ?
C7 N3 N2 107.77(13) . . ?
C13 N4 C9 117.63(15) . . ?
C13 N4 Cu1 132.42(12) . . ?
C9 N4 Cu1 109.60(11) . . ?
C14 N5 N6 118.40(14) . . ?
C14 N5 Cu1 120.35(11) . . ?
N6 N5 Cu1 121.24(11) . . ?
C15 N6 N5 117.30(14) . . ?
C15 N6 H6N 123.2(16) . . ?
N5 N6 H6N 119.3(16) . . ?
O4 N7 O5 120.52(16) . . ?
O4 N7 O3 120.14(16) . . ?
O5 N7 O3 119.34(17) . . ?
C7 O1 Cu1 110.52(11) . . ?
N2 Cu1 O1 78.52(5) . . ?
N2 Cu1 N5 174.33(6) . . ?
O1 Cu1 N5 99.35(5) . . ?
N2 Cu1 N1 80.18(6) . . ?
O1 Cu1 N1 156.69(5) . . ?
N5 Cu1 N1 102.70(6) . . ?
N2 Cu1 N4 99.66(5) . . ?
O1 Cu1 N4 96.04(5) . . ?
N5 Cu1 N4 75.24(5) . . ?
N1 Cu1 N4 96.78(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
N1 C1 C2 C3 0.7(3) . . . . ?
C6 C1 C2 C3 177.77(16) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 N1 0.8(3) . . . . ?
N1 C1 C6 N2 6.7(2) . . . . ?
C2 C1 C6 N2 -170.55(16) . . . . ?
N4 C9 C10 C11 1.0(3) . . . . ?
C14 C9 C10 C11 -178.60(17) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C10 C11 C12 C13 -1.7(3) . . . . ?
C11 C12 C13 N4 0.7(3) . . . . ?
N4 C9 C14 N5 4.4(2) . . . . ?
C10 C9 C14 N5 -175.95(17) . . . . ?
C4 C5 N1 C1 0.2(3) . . . . ?
C4 C5 N1 Cu1 -172.50(13) . . . . ?
C2 C1 N1 C5 -1.0(3) . . . . ?
C6 C1 N1 C5 -178.26(15) . . . . ?
C2 C1 N1 Cu1 173.01(13) . . . . ?
C6 C1 N1 Cu1 -4.27(18) . . . . ?
C1 C6 N2 N3 176.29(14) . . . . ?
C1 C6 N2 Cu1 -6.0(2) . . . . ?
O1 C7 N3 N2 -3.0(2) . . . . ?
C8 C7 N3 N2 175.97(14) . . . . ?
C6 N2 N3 C7 -173.26(16) . . . . ?
Cu1 N2 N3 C7 8.97(17) . . . . ?
C12 C13 N4 C9 1.2(3) . . . . ?
C12 C13 N4 Cu1 -171.21(14) . . . . ?
C10 C9 N4 C13 -2.0(3) . . . . ?
C14 C9 N4 C13 177.59(16) . . . . ?
C10 C9 N4 Cu1 171.99(14) . . . . ?
C14 C9 N4 Cu1 -8.38(18) . . . . ?
C9 C14 N5 N6 -177.93(15) . . . . ?
C9 C14 N5 Cu1 3.2(2) . . . . ?
O2 C15 N6 N5 3.0(2) . . . . ?
C16 C15 N6 N5 -177.19(14) . . . . ?
C14 N5 N6 C15 179.07(16) . . . . ?
Cu1 N5 N6 C15 -2.0(2) . . . . ?
N3 C7 O1 Cu1 -3.8(2) . . . . ?
C8 C7 O1 Cu1 177.25(12) . . . . ?

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
N6 H6N N3 0.86(3) 2.05(3) 2.9041(19) 177(2) 4_576

_refine_diff_density_max         0.449
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_jmlac190709
_database_code_depnum_ccdc_archive 'CCDC 2014874'
loop_
_audit_author_name
_audit_author_address
'Lydia Karmazin'
;Institut de Chimie de Strasbourg
France
;
_audit_update_record             
;
2020-07-08 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 Cl Cu2 N6 O2'
_chemical_formula_sum            'C16 H16 Cl Cu2 N6 O2'
_chemical_formula_weight         486.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   9.3690(4)
_cell_length_b                   8.7013(5)
_cell_length_c                   12.1951(6)
_cell_angle_alpha                90
_cell_angle_beta                 112.512(3)
_cell_angle_gamma                90
_cell_volume                     918.42(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2645
_cell_measurement_theta_min      5.08
_cell_measurement_theta_max      66.31

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_F_000             490
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.415
_shelx_estimated_absorpt_T_min   0.307
_shelx_estimated_absorpt_T_max   0.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5666
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Cu-ImuS microfocus tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9027
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.083
_diffrn_reflns_theta_max         66.646
_diffrn_reflns_theta_full        66.646
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1622
_reflns_number_gt                1165
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0759P)²+1.7138P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1622
_refine_ls_number_parameters     125
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1498
_refine_ls_wR_factor_gt          0.1344
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.2800(6) 0.8253(8) 0.5710(5) 0.0411(15) Uani 1 1 d . . . . .
H1 H 0.2200 0.8274 0.6186 0.049 Uiso 1 1 calc R U . . .
C2 C 0.2313(6) 0.9104(7) 0.4679(6) 0.0412(15) Uani 1 1 d . . . . .
H2 H 0.1408 0.9719 0.4456 0.049 Uiso 1 1 calc R U . . .
C3 C 0.3163(7) 0.9044(7) 0.3983(5) 0.0394(15) Uani 1 1 d . . . . .
H3 H 0.2834 0.9603 0.3259 0.047 Uiso 1 1 calc R U . . .
C4 C 0.4501(6) 0.8170(6) 0.4331(5) 0.0313(12) Uani 1 1 d . . . . .
H4 H 0.5095 0.8107 0.3851 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4943(6) 0.7394(6) 0.5399(4) 0.0277(11) Uani 1 1 d . . . . .
C6 C 0.6392(6) 0.6543(6) 0.5903(4) 0.0271(11) Uani 1 1 d . . . . .
H6 H 0.7135 0.6559 0.5548 0.032 Uiso 1 1 calc R U . . .
C7 C 0.7833(6) 0.4071(7) 0.8263(5) 0.0310(12) Uani 1 1 d . . . . .
C8 C 0.9216(6) 0.3097(8) 0.8957(6) 0.0433(16) Uani 1 1 d . . . . .
H8A H 0.9476 0.3245 0.9808 0.065 Uiso 1 1 calc R U . . .
H8B H 1.0096 0.3401 0.8760 0.065 Uiso 1 1 calc R U . . .
H8C H 0.8973 0.2013 0.8754 0.065 Uiso 1 1 calc R U . . .
N1 N 0.4069(5) 0.7408(6) 0.6064(4) 0.0343(11) Uani 1 1 d . . . . .
N2 N 0.6609(5) 0.5772(5) 0.6850(4) 0.0264(10) Uani 1 1 d . . . . .
N3 N 0.7982(5) 0.4994(5) 0.7431(4) 0.0278(10) Uani 1 1 d . . . . .
O1 O 0.6634(4) 0.3981(5) 0.8481(3) 0.0402(10) Uani 1 1 d . . . . .
Cu1 Cu 0.5000 0.57407(13) 0.7500 0.0280(3) Uani 1 2 d S T P . .
Cu2 Cu 1.0000 0.57292(14) 0.7500 0.0314(3) Uani 1 2 d S T P . .
Cl1 Cl 1.0000 0.8369(2) 0.7500 0.0448(6) Uani 1 2 d S T P . .


_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
C1 N1 1.322(7) . ?
C1 C2 1.378(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.369(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(7) . ?
C4 H4 0.9500 . ?
C5 N1 1.355(7) . ?
C5 C6 1.460(7) . ?
C6 N2 1.283(7) . ?
C6 H6 0.9500 . ?
C7 O1 1.253(6) . ?
C7 N3 1.342(7) . ?
C7 C8 1.508(8) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N1 Cu1 2.183(5) . ?
N2 N3 1.385(6) . ?
N2 Cu1 1.953(4) . ?
N3 Cu2 1.967(4) . ?
O1 Cu1 2.172(4) . ?
Cu1 N2 1.953(4) 2_656 ?
Cu1 O1 2.172(4) 2_656 ?
Cu1 N1 2.183(5) 2_656 ?
Cu2 N3 1.967(4) 2_756 ?
Cu2 Cl1 2.297(2) . ?

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 C1 C2 122.6(6) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 118.5(6) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.2(6) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 117.7(6) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
N1 C5 C4 121.9(5) . . ?
N1 C5 C6 115.5(4) . . ?
C4 C5 C6 122.6(5) . . ?
N2 C6 C5 116.5(5) . . ?
N2 C6 H6 121.8 . . ?
C5 C6 H6 121.8 . . ?
O1 C7 N3 124.0(5) . . ?
O1 C7 C8 119.5(5) . . ?
N3 C7 C8 116.5(5) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 N1 C5 118.9(5) . . ?
C1 N1 Cu1 131.6(4) . . ?
C5 N1 Cu1 109.1(3) . . ?
C6 N2 N3 120.8(4) . . ?
C6 N2 Cu1 119.5(4) . . ?
N3 N2 Cu1 119.7(3) . . ?
C7 N3 N2 109.5(4) . . ?
C7 N3 Cu2 122.6(3) . . ?
N2 N3 Cu2 123.5(3) . . ?
C7 O1 Cu1 109.8(4) . . ?
N2 Cu1 N2 178.4(3) . 2_656 ?
N2 Cu1 O1 106.07(16) . 2_656 ?
N2 Cu1 O1 75.09(16) 2_656 2_656 ?
N2 Cu1 O1 75.09(16) . . ?
N2 Cu1 O1 106.07(16) 2_656 . ?
O1 Cu1 O1 90.3(2) 2_656 . ?
N2 Cu1 N1 78.37(18) . . ?
N2 Cu1 N1 100.55(17) 2_656 . ?
O1 Cu1 N1 92.62(17) 2_656 . ?
O1 Cu1 N1 153.07(16) . . ?
N2 Cu1 N1 100.55(17) . 2_656 ?
N2 Cu1 N1 78.37(18) 2_656 2_656 ?
O1 Cu1 N1 153.07(16) 2_656 2_656 ?
O1 Cu1 N1 92.62(17) . 2_656 ?
N1 Cu1 N1 96.7(3) . 2_656 ?
N3 Cu2 N3 142.0(3) . 2_756 ?
N3 Cu2 Cl1 108.99(14) . . ?
N3 Cu2 Cl1 108.99(14) 2_756 . ?

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
N1 C1 C2 C3 1.4(9) . . . . ?
C1 C2 C3 C4 -1.5(9) . . . . ?
C2 C3 C4 C5 -0.9(8) . . . . ?
C3 C4 C5 N1 3.5(8) . . . . ?
C3 C4 C5 C6 -174.9(5) . . . . ?
N1 C5 C6 N2 7.0(7) . . . . ?
C4 C5 C6 N2 -174.6(5) . . . . ?
C2 C1 N1 C5 1.1(9) . . . . ?
C2 C1 N1 Cu1 -171.5(4) . . . . ?
C4 C5 N1 C1 -3.6(8) . . . . ?
C6 C5 N1 C1 174.8(5) . . . . ?
C4 C5 N1 Cu1 170.5(4) . . . . ?
C6 C5 N1 Cu1 -11.0(6) . . . . ?
C5 C6 N2 N3 -176.5(4) . . . . ?
C5 C6 N2 Cu1 2.0(6) . . . . ?
O1 C7 N3 N2 -1.7(8) . . . . ?
C8 C7 N3 N2 178.2(5) . . . . ?
O1 C7 N3 Cu2 155.5(5) . . . . ?
C8 C7 N3 Cu2 -24.6(7) . . . . ?
C6 N2 N3 C7 -169.4(5) . . . . ?
Cu1 N2 N3 C7 12.1(5) . . . . ?
C6 N2 N3 Cu2 33.7(6) . . . . ?
Cu1 N2 N3 Cu2 -144.8(3) . . . . ?
N3 C7 O1 Cu1 -7.7(7) . . . . ?
C8 C7 O1 Cu1 172.4(4) . . . . ?

_refine_diff_density_max         0.541
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.113

