# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_ABC
_database_code_depnum_ccdc_archive 'CCDC 1832845'
_audit_update_record             
;
2018-03-27 deposited with the CCDC.
2018-10-19 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         'C17 H21 Cu N3 O3, 0.5(H2 O)'
_chemical_formula_sum            'C17 H22 Cu N3 O3.50'
_chemical_formula_weight         387.91

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 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+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.7397(4)
_cell_length_b                   13.8992(5)
_cell_length_c                   21.0927(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.547(2)
_cell_angle_gamma                90
_cell_volume                     3441.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9184
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      34.79

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    1.293
_shelx_estimated_absorpt_T_min   0.606
_shelx_estimated_absorpt_T_max   0.773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.606
_exptl_absorpt_correction_T_max  0.773
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15674
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.931
_diffrn_reflns_theta_max         27.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4129
_reflns_number_gt                3758
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.0343P)²+4.0376P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4129
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0725
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 0.13295(15) -0.18253(11) 0.85096(8) 0.0221(3) Uani 1 1 d . . . . .
H1A H 0.1707 -0.2182 0.8859 0.026 Uiso 1 1 calc R U . . .
H1B H 0.0999 -0.2304 0.8213 0.026 Uiso 1 1 calc R U . . .
C2 C 0.03705(14) -0.12142(11) 0.87812(8) 0.0206(3) Uani 1 1 d . . . . .
C3 C 0.00293(13) 0.04203(11) 0.91471(7) 0.0179(3) Uani 1 1 d . . . . .
C4 C -0.10441(14) 0.03460(12) 0.94142(8) 0.0221(3) Uani 1 1 d . . . . .
H4 H -0.1434 -0.0253 0.9405 0.027 Uiso 1 1 calc R U . . .
C5 C -0.15615(14) 0.11517(13) 0.96994(8) 0.0239(3) Uani 1 1 d . . . . .
H5 H -0.2298 0.1084 0.9877 0.029 Uiso 1 1 calc R U . . .
C6 C -0.10305(14) 0.20265(12) 0.97267(8) 0.0224(3) Uani 1 1 d . . . . .
H6 H -0.1404 0.2562 0.9912 0.027 Uiso 1 1 calc R U . . .
C7 C 0.00831(14) 0.21296(11) 0.94766(8) 0.0185(3) Uani 1 1 d . . . . .
C8 C 0.07272(15) 0.29885(12) 0.95085(8) 0.0234(3) Uani 1 1 d . . . . .
H8 H 0.0410 0.3552 0.9691 0.028 Uiso 1 1 calc R U . . .
C9 C 0.18123(15) 0.30011(12) 0.92749(9) 0.0259(4) Uani 1 1 d . . . . .
H9 H 0.2253 0.3574 0.9299 0.031 Uiso 1 1 calc R U . . .
C10 C 0.22740(14) 0.21706(11) 0.90006(8) 0.0221(3) Uani 1 1 d . . . . .
H10 H 0.3029 0.2192 0.8842 0.027 Uiso 1 1 calc R U . . .
C11 C 0.06035(13) 0.13240(11) 0.91905(7) 0.0166(3) Uani 1 1 d . . . . .
C12 C 0.17950(15) -0.10825(12) 0.75081(8) 0.0236(3) Uani 1 1 d . . . . .
H12A H 0.1027 -0.0789 0.7520 0.028 Uiso 1 1 calc R U . . .
H12B H 0.1724 -0.1713 0.7292 0.028 Uiso 1 1 calc R U . . .
C13 C 0.25701(19) -0.04390(14) 0.71217(9) 0.0332(4) Uani 1 1 d . . . . .
H13A H 0.2721 0.0157 0.7356 0.050 Uiso 1 1 calc R U . . .
H13B H 0.2199 -0.0286 0.6716 0.050 Uiso 1 1 calc R U . . .
H13C H 0.3290 -0.0773 0.7044 0.050 Uiso 1 1 calc R U . . .
C14 C 0.33393(15) -0.17232(12) 0.81920(9) 0.0235(3) Uani 1 1 d . . . . .
H14A H 0.3589 -0.1767 0.8641 0.028 Uiso 1 1 calc R U . . .
H14B H 0.3892 -0.1308 0.7970 0.028 Uiso 1 1 calc R U . . .
C15 C 0.33921(19) -0.27244(14) 0.79031(11) 0.0378(5) Uani 1 1 d . . . . .
H15A H 0.2834 -0.3142 0.8110 0.057 Uiso 1 1 calc R U . . .
H15B H 0.4158 -0.2991 0.7965 0.057 Uiso 1 1 calc R U . . .
H15C H 0.3218 -0.2686 0.7448 0.057 Uiso 1 1 calc R U . . .
C16 C 0.42445(14) 0.03066(11) 0.89833(8) 0.0187(3) Uani 1 1 d . . . . .
C17 C 0.54397(14) 0.06776(13) 0.90655(9) 0.0264(4) Uani 1 1 d . . . . .
H17A H 0.5423 0.1379 0.9115 0.040 Uiso 1 1 calc R U . . .
H17B H 0.5888 0.0510 0.8692 0.040 Uiso 1 1 calc R U . . .
H17C H 0.5787 0.0386 0.9444 0.040 Uiso 1 1 calc R U . . .
Cu1 Cu 0.21910(2) 0.00720(2) 0.86215(2) 0.01603(7) Uani 1 1 d . . . . .
N1 N 0.22016(11) -0.12440(9) 0.81690(6) 0.0181(3) Uani 1 1 d . . . . .
N2 N 0.06801(12) -0.02884(10) 0.88526(7) 0.0193(3) Uani 1 1 d . . . . .
N3 N 0.16923(11) 0.13585(9) 0.89551(6) 0.0177(3) Uani 1 1 d . . . . .
O1 O 0.37588(9) 0.04749(8) 0.84474(5) 0.0193(2) Uani 1 1 d . . . . .
O2 O 0.37389(11) -0.01178(9) 0.94171(6) 0.0263(3) Uani 1 1 d . . . . .
O3 O -0.05381(10) -0.15942(9) 0.89284(6) 0.0282(3) Uani 1 1 d . . . . .
O4 O 0.5000 0.15614(13) 0.7500 0.0317(4) Uani 1 2 d GS T P . .
H4A H 0.4625 0.1258 0.7781 0.048 Uiso 0.5 1 d G U P . .
H4B H 0.5384 0.1165 0.7280 0.048 Uiso 0.5 1 d G U 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 1.494(2) . ?
C1 C2 1.526(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O3 1.233(2) . ?
C2 N2 1.345(2) . ?
C3 C4 1.389(2) . ?
C3 N2 1.396(2) . ?
C3 C11 1.428(2) . ?
C4 C5 1.411(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.367(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.422(2) . ?
C6 H6 0.9500 . ?
C7 C11 1.414(2) . ?
C7 C8 1.414(2) . ?
C8 C9 1.370(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.403(2) . ?
C9 H9 0.9500 . ?
C10 N3 1.322(2) . ?
C10 H10 0.9500 . ?
C11 N3 1.376(2) . ?
C12 N1 1.486(2) . ?
C12 C13 1.519(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N1 1.493(2) . ?
C14 C15 1.521(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 O2 1.244(2) . ?
C16 O1 1.283(2) . ?
C16 C17 1.503(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
Cu1 N2 1.9109(14) . ?
Cu1 O1 1.9618(11) . ?
Cu1 N3 2.0107(13) . ?
Cu1 N1 2.0633(13) . ?
O4 H4A 0.8529 . ?
O4 H4B 0.8524 . ?

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 113.01(13) . . ?
N1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
O3 C2 N2 127.97(16) . . ?
O3 C2 C1 119.95(14) . . ?
N2 C2 C1 112.02(14) . . ?
C4 C3 N2 129.09(14) . . ?
C4 C3 C11 117.96(15) . . ?
N2 C3 C11 112.90(14) . . ?
C3 C4 C5 120.65(15) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 121.71(15) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 119.63(15) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C11 C7 C8 117.12(14) . . ?
C11 C7 C6 118.77(14) . . ?
C8 C7 C6 124.09(15) . . ?
C9 C8 C7 119.48(15) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.14(15) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
N3 C10 C9 122.08(15) . . ?
N3 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
N3 C11 C7 122.21(14) . . ?
N3 C11 C3 116.55(14) . . ?
C7 C11 C3 121.22(14) . . ?
N1 C12 C13 113.80(14) . . ?
N1 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
N1 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 115.79(15) . . ?
N1 C14 H14A 108.3 . . ?
C15 C14 H14A 108.3 . . ?
N1 C14 H14B 108.3 . . ?
C15 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 O1 121.56(15) . . ?
O2 C16 C17 121.95(15) . . ?
O1 C16 C17 116.47(14) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 Cu1 O1 175.85(5) . . ?
N2 Cu1 N3 82.51(6) . . ?
O1 Cu1 N3 95.08(5) . . ?
N2 Cu1 N1 83.99(6) . . ?
O1 Cu1 N1 99.01(5) . . ?
N3 Cu1 N1 162.42(6) . . ?
C12 N1 C14 112.16(13) . . ?
C12 N1 C1 108.50(13) . . ?
C14 N1 C1 111.11(13) . . ?
C12 N1 Cu1 107.26(10) . . ?
C14 N1 Cu1 112.94(10) . . ?
C1 N1 Cu1 104.47(9) . . ?
C2 N2 C3 125.19(14) . . ?
C2 N2 Cu1 118.21(12) . . ?
C3 N2 Cu1 116.22(10) . . ?
C10 N3 C11 118.97(14) . . ?
C10 N3 Cu1 129.24(11) . . ?
C11 N3 Cu1 111.70(10) . . ?
C16 O1 Cu1 101.13(10) . . ?
H4A O4 H4B 109.7 . . ?

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 O3 161.54(15) . . . . ?
N1 C1 C2 N2 -21.1(2) . . . . ?
N2 C3 C4 C5 179.26(16) . . . . ?
C11 C3 C4 C5 2.1(2) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C7 -1.6(3) . . . . ?
C5 C6 C7 C11 1.5(2) . . . . ?
C5 C6 C7 C8 -176.82(17) . . . . ?
C11 C7 C8 C9 -1.0(2) . . . . ?
C6 C7 C8 C9 177.39(17) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C9 C10 N3 0.2(3) . . . . ?
C8 C7 C11 N3 0.5(2) . . . . ?
C6 C7 C11 N3 -177.95(15) . . . . ?
C8 C7 C11 C3 178.79(15) . . . . ?
C6 C7 C11 C3 0.3(2) . . . . ?
C4 C3 C11 N3 176.23(14) . . . . ?
N2 C3 C11 N3 -1.3(2) . . . . ?
C4 C3 C11 C7 -2.1(2) . . . . ?
N2 C3 C11 C7 -179.71(14) . . . . ?
C13 C12 N1 C14 -60.87(18) . . . . ?
C13 C12 N1 C1 176.01(14) . . . . ?
C13 C12 N1 Cu1 63.69(16) . . . . ?
C15 C14 N1 C12 -62.29(19) . . . . ?
C15 C14 N1 C1 59.3(2) . . . . ?
C15 C14 N1 Cu1 176.36(13) . . . . ?
C2 C1 N1 C12 -84.25(16) . . . . ?
C2 C1 N1 C14 152.00(14) . . . . ?
C2 C1 N1 Cu1 29.93(16) . . . . ?
O3 C2 N2 C3 3.8(3) . . . . ?
C1 C2 N2 C3 -173.28(15) . . . . ?
O3 C2 N2 Cu1 176.43(15) . . . . ?
C1 C2 N2 Cu1 -0.62(19) . . . . ?
C4 C3 N2 C2 -1.0(3) . . . . ?
C11 C3 N2 C2 176.21(15) . . . . ?
C4 C3 N2 Cu1 -173.81(14) . . . . ?
C11 C3 N2 Cu1 3.42(18) . . . . ?
C9 C10 N3 C11 -0.7(3) . . . . ?
C9 C10 N3 Cu1 -176.91(13) . . . . ?
C7 C11 N3 C10 0.3(2) . . . . ?
C3 C11 N3 C10 -178.03(15) . . . . ?
C7 C11 N3 Cu1 177.17(12) . . . . ?
C3 C11 N3 Cu1 -1.18(17) . . . . ?
O2 C16 O1 Cu1 7.46(17) . . . . ?
C17 C16 O1 Cu1 -170.59(12) . . . . ?

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_mo_HP_CuSb_230117_0m
_database_code_depnum_ccdc_archive 'CCDC 1832852'
_audit_update_record             
;
2018-03-27 deposited with the CCDC.
2018-10-19 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         'C15 H18 Cl Cu N3 O'
_chemical_formula_sum            'C15 H18 Cl Cu N3 O'
_chemical_formula_weight         355.31

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 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+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.5925(6)
_cell_length_b                   13.2202(6)
_cell_length_c                   16.1405(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.955(2)
_cell_angle_gamma                90
_cell_volume                     3046.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9931
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      30.51

_exptl_crystal_description       PLATE
_exptl_crystal_colour            BLUE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_F_000             1464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.081
_exptl_absorpt_coefficient_mu    1.611
_shelx_estimated_absorpt_T_min   0.632
_shelx_estimated_absorpt_T_max   0.881
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_T_max  0.881
_exptl_absorpt_process_details   'SADABS (BRUKER, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            22589
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.304
_diffrn_reflns_theta_max         30.515
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4633
_reflns_number_gt                4253
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0258P)²+3.8293P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4633
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0598
_refine_ls_wR_factor_gt          0.0582
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.003
_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
Cu1 Cu 0.22492(2) 0.70777(2) 0.26247(2) 0.01237(5) Uani 1 1 d . . . . .
Cl1 Cl 0.11127(2) 0.64205(2) 0.16533(2) 0.01975(7) Uani 1 1 d . . . . .
O1 O 0.46539(6) 0.85082(7) 0.36344(6) 0.01898(18) Uani 1 1 d . . . . .
N1 N 0.27683(7) 0.80122(8) 0.18019(7) 0.01474(19) Uani 1 1 d . . . . .
N2 N 0.33330(7) 0.74912(8) 0.34315(6) 0.01428(18) Uani 1 1 d . . . . .
N3 N 0.19664(7) 0.63314(7) 0.36270(6) 0.01308(18) Uani 1 1 d . . . . .
C1 C 0.35532(8) 0.86072(9) 0.23224(8) 0.0158(2) Uani 1 1 d . . . . .
H1A H 0.3337 0.9310 0.2375 0.019 Uiso 1 1 calc R U . . .
H1B H 0.4078 0.8633 0.2020 0.019 Uiso 1 1 calc R U . . .
C2 C 0.39146(8) 0.81818(9) 0.32057(8) 0.0142(2) Uani 1 1 d . . . . .
C3 C 0.34507(8) 0.70559(8) 0.42331(8) 0.0136(2) Uani 1 1 d . . . . .
C4 C 0.41836(9) 0.71751(9) 0.49241(8) 0.0173(2) Uani 1 1 d . . . . .
H4 H 0.4707 0.7582 0.4878 0.021 Uiso 1 1 calc R U . . .
C5 C 0.41516(9) 0.66921(10) 0.56957(8) 0.0200(2) Uani 1 1 d . . . . .
H5 H 0.4659 0.6782 0.6165 0.024 Uiso 1 1 calc R U . . .
C6 C 0.34095(10) 0.60949(9) 0.57915(8) 0.0195(2) Uani 1 1 d . . . . .
H6 H 0.3410 0.5776 0.6319 0.023 Uiso 1 1 calc R U . . .
C7 C 0.26449(9) 0.59574(9) 0.51017(8) 0.0160(2) Uani 1 1 d . . . . .
C8 C 0.18337(9) 0.53836(9) 0.51425(8) 0.0189(2) Uani 1 1 d . . . . .
H8 H 0.1783 0.5053 0.5654 0.023 Uiso 1 1 calc R U . . .
C9 C 0.11237(9) 0.53086(9) 0.44428(8) 0.0188(2) Uani 1 1 d . . . . .
H9 H 0.0575 0.4933 0.4466 0.023 Uiso 1 1 calc R U . . .
C10 C 0.12157(8) 0.57942(9) 0.36880(8) 0.0155(2) Uani 1 1 d . . . . .
H10 H 0.0721 0.5735 0.3204 0.019 Uiso 1 1 calc R U . . .
C11 C 0.26772(8) 0.64314(8) 0.43261(7) 0.0130(2) Uani 1 1 d . . . . .
C12 C 0.31265(9) 0.73773(10) 0.11702(8) 0.0189(2) Uani 1 1 d . . . . .
H12A H 0.3410 0.7827 0.0802 0.023 Uiso 1 1 calc R U . . .
H12B H 0.2591 0.7026 0.0807 0.023 Uiso 1 1 calc R U . . .
C13 C 0.38458(10) 0.65950(10) 0.15629(9) 0.0234(3) Uani 1 1 d . . . . .
H13A H 0.4395 0.6937 0.1898 0.035 Uiso 1 1 calc R U . . .
H13B H 0.4034 0.6197 0.1114 0.035 Uiso 1 1 calc R U . . .
H13C H 0.3573 0.6146 0.1930 0.035 Uiso 1 1 calc R U . . .
C14 C 0.20323(9) 0.86926(10) 0.13131(8) 0.0188(2) Uani 1 1 d . . . . .
H14B H 0.1581 0.8278 0.0910 0.023 Uiso 1 1 calc R U . . .
H14A H 0.2332 0.9170 0.0978 0.023 Uiso 1 1 calc R U . . .
C15 C 0.15011(10) 0.92930(10) 0.18610(9) 0.0233(3) Uani 1 1 d . . . . .
H15B H 0.1186 0.8827 0.2183 0.035 Uiso 1 1 calc R U . . .
H15A H 0.1034 0.9722 0.1500 0.035 Uiso 1 1 calc R U . . .
H15C H 0.1940 0.9719 0.2254 0.035 Uiso 1 1 calc R U . . .


_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 1.9086(10) . ?
Cu1 N3 2.0093(10) . ?
Cu1 N1 2.0690(10) . ?
Cu1 Cl1 2.2105(3) . ?
O1 C2 1.2327(15) . ?
N1 C14 1.4946(16) . ?
N1 C1 1.4959(15) . ?
N1 C12 1.4960(16) . ?
N2 C2 1.3472(15) . ?
N2 C3 1.3937(15) . ?
N3 C10 1.3262(15) . ?
N3 C11 1.3719(15) . ?
C1 C2 1.5216(17) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 C4 1.3850(17) . ?
C3 C11 1.4312(16) . ?
C4 C5 1.4090(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3745(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.4152(18) . ?
C6 H6 0.9500 . ?
C7 C11 1.4094(16) . ?
C7 C8 1.4190(17) . ?
C8 C9 1.3689(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.4078(17) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C12 C13 1.5157(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.5157(18) . ?
C14 H14B 0.9900 . ?
C14 H14A 0.9900 . ?
C15 H15B 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15C 0.9800 . ?

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 82.57(4) . . ?
N2 Cu1 N1 84.55(4) . . ?
N3 Cu1 N1 166.80(4) . . ?
N2 Cu1 Cl1 172.07(3) . . ?
N3 Cu1 Cl1 97.42(3) . . ?
N1 Cu1 Cl1 95.74(3) . . ?
C14 N1 C1 111.28(9) . . ?
C14 N1 C12 106.99(10) . . ?
C1 N1 C12 110.05(9) . . ?
C14 N1 Cu1 112.31(7) . . ?
C1 N1 Cu1 107.04(7) . . ?
C12 N1 Cu1 109.18(7) . . ?
C2 N2 C3 124.58(10) . . ?
C2 N2 Cu1 119.27(8) . . ?
C3 N2 Cu1 116.13(8) . . ?
C10 N3 C11 119.08(10) . . ?
C10 N3 Cu1 129.30(9) . . ?
C11 N3 Cu1 111.62(7) . . ?
N1 C1 C2 114.10(9) . . ?
N1 C1 H1A 108.7 . . ?
C2 C1 H1A 108.7 . . ?
N1 C1 H1B 108.7 . . ?
C2 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
O1 C2 N2 127.77(12) . . ?
O1 C2 C1 119.32(11) . . ?
N2 C2 C1 112.86(10) . . ?
C4 C3 N2 128.80(11) . . ?
C4 C3 C11 118.38(11) . . ?
N2 C3 C11 112.79(10) . . ?
C3 C4 C5 119.92(12) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 122.06(12) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 119.76(12) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C11 C7 C6 118.40(11) . . ?
C11 C7 C8 117.43(11) . . ?
C6 C7 C8 124.16(12) . . ?
C9 C8 C7 119.77(11) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 119.30(11) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
N3 C10 C9 122.46(12) . . ?
N3 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
N3 C11 C7 121.94(10) . . ?
N3 C11 C3 116.59(10) . . ?
C7 C11 C3 121.46(11) . . ?
N1 C12 C13 114.03(11) . . ?
N1 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
N1 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 113.93(11) . . ?
N1 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
N1 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
H14B C14 H14A 107.7 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15A 109.5 . . ?
H15B C15 H15A 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H15A C15 H15C 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
C14 N1 C1 C2 138.85(10) . . . . ?
C12 N1 C1 C2 -102.73(11) . . . . ?
Cu1 N1 C1 C2 15.80(11) . . . . ?
C3 N2 C2 O1 3.8(2) . . . . ?
Cu1 N2 C2 O1 -177.59(10) . . . . ?
C3 N2 C2 C1 -173.65(10) . . . . ?
Cu1 N2 C2 C1 5.01(13) . . . . ?
N1 C1 C2 O1 168.03(10) . . . . ?
N1 C1 C2 N2 -14.33(14) . . . . ?
C2 N2 C3 C4 -4.6(2) . . . . ?
Cu1 N2 C3 C4 176.71(10) . . . . ?
C2 N2 C3 C11 173.53(11) . . . . ?
Cu1 N2 C3 C11 -5.17(13) . . . . ?
N2 C3 C4 C5 177.60(12) . . . . ?
C11 C3 C4 C5 -0.43(17) . . . . ?
C3 C4 C5 C6 0.14(19) . . . . ?
C4 C5 C6 C7 -0.4(2) . . . . ?
C5 C6 C7 C11 0.95(18) . . . . ?
C5 C6 C7 C8 -177.91(12) . . . . ?
C11 C7 C8 C9 0.08(17) . . . . ?
C6 C7 C8 C9 178.96(12) . . . . ?
C7 C8 C9 C10 0.76(18) . . . . ?
C11 N3 C10 C9 -0.85(17) . . . . ?
Cu1 N3 C10 C9 179.75(9) . . . . ?
C8 C9 C10 N3 -0.39(18) . . . . ?
C10 N3 C11 C7 1.75(16) . . . . ?
Cu1 N3 C11 C7 -178.76(9) . . . . ?
C10 N3 C11 C3 -177.33(10) . . . . ?
Cu1 N3 C11 C3 2.17(12) . . . . ?
C6 C7 C11 N3 179.70(11) . . . . ?
C8 C7 C11 N3 -1.36(17) . . . . ?
C6 C7 C11 C3 -1.27(17) . . . . ?
C8 C7 C11 C3 177.67(11) . . . . ?
C4 C3 C11 N3 -179.91(10) . . . . ?
N2 C3 C11 N3 1.76(15) . . . . ?
C4 C3 C11 C7 1.01(17) . . . . ?
N2 C3 C11 C7 -177.32(10) . . . . ?
C14 N1 C12 C13 -176.69(11) . . . . ?
C1 N1 C12 C13 62.28(13) . . . . ?
Cu1 N1 C12 C13 -54.92(12) . . . . ?
C1 N1 C14 C15 -67.52(13) . . . . ?
C12 N1 C14 C15 172.23(10) . . . . ?
Cu1 N1 C14 C15 52.46(12) . . . . ?

_refine_diff_density_max         0.418
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_NNNCuTHFrepeat290715_0m
_database_code_depnum_ccdc_archive 'CCDC 1832853'
_audit_update_record             
;
2018-03-27 deposited with the CCDC.
2018-10-19 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         'C34 H42 Cu2 N6 O6'
_chemical_formula_sum            'C34 H42 Cu2 N6 O6'
_chemical_formula_weight         757.81

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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.750(3)
_cell_length_b                   7.8669(17)
_cell_length_c                   16.223(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.271(10)
_cell_angle_gamma                90
_cell_volume                     1736.6(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4913
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      28.13

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             788
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    1.277
_shelx_estimated_absorpt_T_min   0.616
_shelx_estimated_absorpt_T_max   0.766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_T_max  0.766
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14107
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.817
_diffrn_reflns_theta_max         28.660
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4256
_reflns_number_gt                3365
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.0546P)²+0.9310P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4256
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1253
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
O1 O 0.46290(14) 0.5700(3) 0.70090(13) 0.0437(5) Uani 1 1 d . . . . .
O2 O 0.37769(17) 0.3740(4) 0.75543(16) 0.0599(6) Uani 1 1 d . . . . .
O3 O 0.81192(13) 0.1467(3) 0.80537(12) 0.0452(5) Uani 1 1 d . . . . .
Cu1 Cu 0.57638(2) 0.45180(4) 0.75726(2) 0.03223(12) Uani 1 1 d . . . . .
N1 N 0.59350(14) 0.2716(3) 0.66636(13) 0.0302(5) Uani 1 1 d . . . . .
N2 N 0.68355(16) 0.3288(3) 0.81994(13) 0.0343(5) Uani 1 1 d . . . . .
N3 N 0.57595(16) 0.5672(3) 0.86945(14) 0.0351(5) Uani 1 1 d . . . . .
C1 C 0.69896(19) 0.2259(4) 0.68545(17) 0.0368(6) Uani 1 1 d . . . . .
H1A H 0.7371 0.3051 0.6573 0.044 Uiso 1 1 calc R U . . .
H1B H 0.7085 0.1132 0.6637 0.044 Uiso 1 1 calc R U . . .
C2 C 0.73724(18) 0.2281(4) 0.77787(17) 0.0343(6) Uani 1 1 d . . . . .
C3 C 0.70068(18) 0.3590(4) 0.90505(16) 0.0350(6) Uani 1 1 d . . . . .
C4 C 0.7635(2) 0.2764(5) 0.96558(19) 0.0477(8) Uani 1 1 d . . . . .
H4 H 0.8029 0.1883 0.9510 0.057 Uiso 1 1 calc R U . . .
C5 C 0.7684(2) 0.3250(5) 1.04944(19) 0.0531(9) Uani 1 1 d . . . . .
H5 H 0.8098 0.2650 1.0897 0.064 Uiso 1 1 calc R U . . .
C6 C 0.7155(2) 0.4551(5) 1.07381(18) 0.0520(9) Uani 1 1 d . . . . .
H6 H 0.7225 0.4862 1.1297 0.062 Uiso 1 1 calc R U . . .
C7 C 0.6493(2) 0.5444(4) 1.01425(18) 0.0422(7) Uani 1 1 d . . . . .
C8 C 0.5887(2) 0.6778(5) 1.0330(2) 0.0496(8) Uani 1 1 d . . . . .
H8 H 0.5928 0.7171 1.0875 0.060 Uiso 1 1 calc R U . . .
C9 C 0.5241(3) 0.7497(4) 0.9720(2) 0.0516(8) Uani 1 1 d . . . . .
H9 H 0.4834 0.8377 0.9844 0.062 Uiso 1 1 calc R U . . .
C10 C 0.5192(2) 0.6902(4) 0.8900(2) 0.0434(7) Uani 1 1 d . . . . .
H10 H 0.4743 0.7396 0.8487 0.052 Uiso 1 1 calc R U . . .
C11 C 0.64162(19) 0.4928(4) 0.93025(16) 0.0332(6) Uani 1 1 d . . . . .
C12 C 0.5299(2) 0.1192(4) 0.6702(2) 0.0497(8) Uani 1 1 d . . . . .
H12A H 0.5476 0.0359 0.6308 0.060 Uiso 1 1 calc R U . . .
H12B H 0.4623 0.1525 0.6517 0.060 Uiso 1 1 calc R U . . .
C13 C 0.5342(3) 0.0346(5) 0.7531(3) 0.0692(11) Uani 1 1 d . . . . .
H13A H 0.6003 -0.0014 0.7721 0.104 Uiso 1 1 calc R U . . .
H13B H 0.4914 -0.0625 0.7481 0.104 Uiso 1 1 calc R U . . .
H13C H 0.5136 0.1133 0.7924 0.104 Uiso 1 1 calc R U . . .
C14 C 0.5706(2) 0.3499(4) 0.58247(16) 0.0384(6) Uani 1 1 d . . . . .
H14A H 0.6076 0.4549 0.5824 0.046 Uiso 1 1 calc R U . . .
H14B H 0.5015 0.3795 0.5734 0.046 Uiso 1 1 calc R U . . .
C15 C 0.5921(3) 0.2428(6) 0.5095(2) 0.0714(12) Uani 1 1 d . . . . .
H15A H 0.6614 0.2217 0.5145 0.107 Uiso 1 1 calc R U . . .
H15B H 0.5708 0.3024 0.4584 0.107 Uiso 1 1 calc R U . . .
H15C H 0.5576 0.1367 0.5094 0.107 Uiso 1 1 calc R U . . .
C16 C 0.3819(2) 0.5032(5) 0.71545(17) 0.0419(7) Uani 1 1 d . . . . .
C17 C 0.2893(3) 0.5969(7) 0.6795(3) 0.0789(14) Uani 1 1 d . . . . .
H17A H 0.2328 0.5323 0.6893 0.118 Uiso 1 1 calc R U . . .
H17B H 0.2883 0.6116 0.6206 0.118 Uiso 1 1 calc R U . . .
H17C H 0.2880 0.7062 0.7056 0.118 Uiso 1 1 calc R U . . .


_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
O1 C16 1.284(4) . ?
O1 Cu1 1.9302(19) . ?
O2 C16 1.211(4) . ?
O3 C2 1.237(3) . ?
Cu1 N2 1.926(2) . ?
Cu1 N3 2.035(2) . ?
Cu1 N1 2.083(2) . ?
N1 C1 1.483(3) . ?
N1 C14 1.486(3) . ?
N1 C12 1.491(4) . ?
N2 C2 1.336(4) . ?
N2 C3 1.387(3) . ?
N3 C10 1.316(4) . ?
N3 C11 1.369(4) . ?
C1 C2 1.516(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 C4 1.375(4) . ?
C3 C11 1.425(4) . ?
C4 C5 1.406(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.348(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.415(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.401(5) . ?
C7 C11 1.411(4) . ?
C8 C9 1.355(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.403(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C12 C13 1.494(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.516(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.514(4) . ?
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
C16 O1 Cu1 112.3(2) . . ?
N2 Cu1 O1 175.59(9) . . ?
N2 Cu1 N3 81.50(9) . . ?
O1 Cu1 N3 95.89(9) . . ?
N2 Cu1 N1 82.89(9) . . ?
O1 Cu1 N1 99.12(9) . . ?
N3 Cu1 N1 162.18(9) . . ?
C1 N1 C14 111.3(2) . . ?
C1 N1 C12 111.0(2) . . ?
C14 N1 C12 108.9(2) . . ?
C1 N1 Cu1 102.94(15) . . ?
C14 N1 Cu1 109.63(17) . . ?
C12 N1 Cu1 113.03(18) . . ?
C2 N2 C3 125.7(2) . . ?
C2 N2 Cu1 117.73(17) . . ?
C3 N2 Cu1 116.55(18) . . ?
C10 N3 C11 119.0(3) . . ?
C10 N3 Cu1 129.3(2) . . ?
C11 N3 Cu1 111.55(18) . . ?
N1 C1 C2 113.2(2) . . ?
N1 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
N1 C1 H1B 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.8 . . ?
O3 C2 N2 127.9(3) . . ?
O3 C2 C1 120.2(2) . . ?
N2 C2 C1 111.9(2) . . ?
C4 C3 N2 129.0(3) . . ?
C4 C3 C11 118.0(3) . . ?
N2 C3 C11 112.9(2) . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 122.6(3) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C11 117.5(3) . . ?
C8 C7 C6 124.6(3) . . ?
C11 C7 C6 117.9(3) . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 119.3(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
N3 C10 C9 122.5(3) . . ?
N3 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
N3 C11 C7 121.5(3) . . ?
N3 C11 C3 116.9(2) . . ?
C7 C11 C3 121.5(3) . . ?
N1 C12 C13 116.6(3) . . ?
N1 C12 H12A 108.1 . . ?
C13 C12 H12A 108.1 . . ?
N1 C12 H12B 108.1 . . ?
C13 C12 H12B 108.1 . . ?
H12A C12 H12B 107.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 116.5(3) . . ?
N1 C14 H14A 108.2 . . ?
C15 C14 H14A 108.2 . . ?
N1 C14 H14B 108.2 . . ?
C15 C14 H14B 108.2 . . ?
H14A C14 H14B 107.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 O1 123.5(3) . . ?
O2 C16 C17 120.8(3) . . ?
O1 C16 C17 115.7(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 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
C14 N1 C1 C2 152.0(2) . . . . ?
C12 N1 C1 C2 -86.6(3) . . . . ?
Cu1 N1 C1 C2 34.6(3) . . . . ?
C3 N2 C2 O3 -1.5(5) . . . . ?
Cu1 N2 C2 O3 175.4(2) . . . . ?
C3 N2 C2 C1 -179.2(3) . . . . ?
Cu1 N2 C2 C1 -2.2(3) . . . . ?
N1 C1 C2 O3 158.3(3) . . . . ?
N1 C1 C2 N2 -23.8(4) . . . . ?
C2 N2 C3 C4 -11.2(5) . . . . ?
Cu1 N2 C3 C4 171.8(3) . . . . ?
C2 N2 C3 C11 170.3(3) . . . . ?
Cu1 N2 C3 C11 -6.7(3) . . . . ?
N2 C3 C4 C5 -178.6(3) . . . . ?
C11 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 -2.2(5) . . . . ?
C4 C5 C6 C7 2.3(5) . . . . ?
C5 C6 C7 C8 177.9(3) . . . . ?
C5 C6 C7 C11 -0.2(4) . . . . ?
C11 C7 C8 C9 1.5(4) . . . . ?
C6 C7 C8 C9 -176.7(3) . . . . ?
C7 C8 C9 C10 -0.5(5) . . . . ?
C11 N3 C10 C9 0.7(4) . . . . ?
Cu1 N3 C10 C9 176.0(2) . . . . ?
C8 C9 C10 N3 -0.6(5) . . . . ?
C10 N3 C11 C7 0.4(4) . . . . ?
Cu1 N3 C11 C7 -175.7(2) . . . . ?
C10 N3 C11 C3 179.4(2) . . . . ?
Cu1 N3 C11 C3 3.3(3) . . . . ?
C8 C7 C11 N3 -1.4(4) . . . . ?
C6 C7 C11 N3 176.9(3) . . . . ?
C8 C7 C11 C3 179.6(3) . . . . ?
C6 C7 C11 C3 -2.1(4) . . . . ?
C4 C3 C11 N3 -176.7(3) . . . . ?
N2 C3 C11 N3 2.0(3) . . . . ?
C4 C3 C11 C7 2.3(4) . . . . ?
N2 C3 C11 C7 -179.0(2) . . . . ?
C1 N1 C12 C13 63.9(4) . . . . ?
C14 N1 C12 C13 -173.3(3) . . . . ?
Cu1 N1 C12 C13 -51.2(3) . . . . ?
C1 N1 C14 C15 59.1(3) . . . . ?
C12 N1 C14 C15 -63.5(3) . . . . ?
Cu1 N1 C14 C15 172.3(2) . . . . ?
Cu1 O1 C16 O2 -4.6(4) . . . . ?
Cu1 O1 C16 C17 175.1(2) . . . . ?

_refine_diff_density_max         1.183
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_mo_Et2NNNCuBr2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1832854'
_audit_update_record             
;
2018-03-27 deposited with the CCDC.
2018-10-19 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         'C15 H18 Br Cu N3 O'
_chemical_formula_sum            'C15 H18 Br Cu N3 O'
_chemical_formula_weight         399.77

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 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+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.8335(5)
_cell_length_b                   13.3212(4)
_cell_length_c                   16.1662(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.8220(10)
_cell_angle_gamma                90
_cell_volume                     3126.68(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      30.49

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_F_000             1608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    3.954
_shelx_estimated_absorpt_T_min   0.477
_shelx_estimated_absorpt_T_max   0.858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.477
_exptl_absorpt_correction_T_max  0.858
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20717
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.574
_diffrn_reflns_theta_max         30.503
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4765
_reflns_number_gt                4288
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.0230P)²+3.7213P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4765
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0209
_refine_ls_wR_factor_ref         0.0527
_refine_ls_wR_factor_gt          0.0510
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
Br1 Br 0.11013(2) 0.35604(2) 0.16035(2) 0.01681(4) Uani 1 1 d . . . . .
Cu1 Cu 0.22873(2) 0.28669(2) 0.26365(2) 0.01159(4) Uani 1 1 d . . . . .
O1 O 0.46649(7) 0.14722(8) 0.36498(7) 0.0181(2) Uani 1 1 d . . . . .
N1 N 0.28022(8) 0.19350(9) 0.18196(7) 0.0140(2) Uani 1 1 d . . . . .
N2 N 0.33570(8) 0.24700(9) 0.34422(7) 0.0136(2) Uani 1 1 d . . . . .
N3 N 0.20043(8) 0.36158(8) 0.36343(7) 0.0126(2) Uani 1 1 d . . . . .
C1 C 0.35785(10) 0.13519(11) 0.23433(9) 0.0154(3) Uani 1 1 d . . . . .
H1A H 0.4094 0.1325 0.2040 0.018 Uiso 1 1 calc R U . . .
H1B H 0.3369 0.0655 0.2403 0.018 Uiso 1 1 calc R U . . .
C2 C 0.39342(9) 0.17851(10) 0.32211(9) 0.0135(2) Uani 1 1 d . . . . .
C3 C 0.34740(9) 0.29223(10) 0.42359(9) 0.0130(2) Uani 1 1 d . . . . .
C4 C 0.42030(10) 0.28277(11) 0.49202(9) 0.0168(3) Uani 1 1 d . . . . .
H4 H 0.4719 0.2424 0.4876 0.020 Uiso 1 1 calc R U . . .
C5 C 0.41793(11) 0.33318(12) 0.56842(10) 0.0199(3) Uani 1 1 d . . . . .
H5 H 0.4686 0.3264 0.6147 0.024 Uiso 1 1 calc R U . . .
C6 C 0.34438(11) 0.39168(11) 0.57765(9) 0.0200(3) Uani 1 1 d . . . . .
H6 H 0.3448 0.4250 0.6297 0.024 Uiso 1 1 calc R U . . .
C7 C 0.26810(10) 0.40227(10) 0.50965(9) 0.0159(3) Uani 1 1 d . . . . .
C8 C 0.18784(11) 0.45817(11) 0.51386(10) 0.0183(3) Uani 1 1 d . . . . .
H8 H 0.1830 0.4917 0.5646 0.022 Uiso 1 1 calc R U . . .
C9 C 0.11738(11) 0.46370(11) 0.44465(10) 0.0181(3) Uani 1 1 d . . . . .
H9 H 0.0630 0.5003 0.4472 0.022 Uiso 1 1 calc R U . . .
C10 C 0.12628(10) 0.41460(10) 0.36963(9) 0.0153(3) Uani 1 1 d . . . . .
H10 H 0.0774 0.4196 0.3216 0.018 Uiso 1 1 calc R U . . .
C11 C 0.27091(10) 0.35337(10) 0.43259(9) 0.0126(2) Uani 1 1 d . . . . .
C12 C 0.20868(10) 0.12454(11) 0.13392(9) 0.0175(3) Uani 1 1 d . . . . .
H12B H 0.2390 0.0760 0.1020 0.021 Uiso 1 1 calc R U . . .
H12A H 0.1647 0.1644 0.0924 0.021 Uiso 1 1 calc R U . . .
C13 C 0.15542(11) 0.06667(12) 0.18943(10) 0.0223(3) Uani 1 1 d . . . . .
H13B H 0.1982 0.0254 0.2298 0.033 Uiso 1 1 calc R U . . .
H13C H 0.1098 0.0233 0.1540 0.033 Uiso 1 1 calc R U . . .
H13A H 0.1240 0.1140 0.2203 0.033 Uiso 1 1 calc R U . . .
C14 C 0.31571(11) 0.25533(11) 0.11807(9) 0.0184(3) Uani 1 1 d . . . . .
H14A H 0.2630 0.2884 0.0805 0.022 Uiso 1 1 calc R U . . .
H14B H 0.3452 0.2102 0.0828 0.022 Uiso 1 1 calc R U . . .
C15 C 0.38467(12) 0.33510(12) 0.15664(11) 0.0230(3) Uani 1 1 d . . . . .
H15A H 0.3561 0.3804 0.1916 0.034 Uiso 1 1 calc R U . . .
H15B H 0.4038 0.3735 0.1115 0.034 Uiso 1 1 calc R U . . .
H15C H 0.4386 0.3029 0.1917 0.034 Uiso 1 1 calc R U . . .


_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
Br1 Cu1 2.3523(2) . ?
Cu1 N2 1.9097(12) . ?
Cu1 N3 2.0128(12) . ?
Cu1 N1 2.0691(12) . ?
O1 C2 1.2334(17) . ?
N1 C12 1.4951(19) . ?
N1 C14 1.4983(18) . ?
N1 C1 1.4988(18) . ?
N2 C2 1.3485(17) . ?
N2 C3 1.3959(17) . ?
N3 C10 1.3281(17) . ?
N3 C11 1.3697(18) . ?
C1 C2 1.5226(19) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 C4 1.385(2) . ?
C3 C11 1.4280(19) . ?
C4 C5 1.413(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.373(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.414(2) . ?
C6 H6 0.9500 . ?
C7 C11 1.4139(19) . ?
C7 C8 1.418(2) . ?
C8 C9 1.368(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.408(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C12 C13 1.521(2) . ?
C12 H12B 0.9900 . ?
C12 H12A 0.9900 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 H13A 0.9800 . ?
C14 C15 1.518(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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 82.60(5) . . ?
N2 Cu1 N1 84.57(5) . . ?
N3 Cu1 N1 166.84(5) . . ?
N2 Cu1 Br1 171.48(4) . . ?
N3 Cu1 Br1 97.23(3) . . ?
N1 Cu1 Br1 95.90(3) . . ?
C12 N1 C14 106.97(11) . . ?
C12 N1 C1 110.88(11) . . ?
C14 N1 C1 109.66(11) . . ?
C12 N1 Cu1 112.62(9) . . ?
C14 N1 Cu1 109.75(9) . . ?
C1 N1 Cu1 106.96(8) . . ?
C2 N2 C3 124.72(12) . . ?
C2 N2 Cu1 119.37(9) . . ?
C3 N2 Cu1 115.91(9) . . ?
C10 N3 C11 119.10(12) . . ?
C10 N3 Cu1 129.50(10) . . ?
C11 N3 Cu1 111.40(9) . . ?
N1 C1 C2 114.17(11) . . ?
N1 C1 H1A 108.7 . . ?
C2 C1 H1A 108.7 . . ?
N1 C1 H1B 108.7 . . ?
C2 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
O1 C2 N2 127.76(13) . . ?
O1 C2 C1 119.50(12) . . ?
N2 C2 C1 112.69(12) . . ?
C4 C3 N2 128.65(13) . . ?
C4 C3 C11 118.50(12) . . ?
N2 C3 C11 112.83(12) . . ?
C3 C4 C5 119.98(14) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 121.83(14) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 119.94(13) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C11 118.41(13) . . ?
C6 C7 C8 124.14(13) . . ?
C11 C7 C8 117.45(13) . . ?
C9 C8 C7 119.84(13) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 119.27(13) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
N3 C10 C9 122.51(14) . . ?
N3 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
N3 C11 C7 121.80(12) . . ?
N3 C11 C3 116.87(12) . . ?
C7 C11 C3 121.32(13) . . ?
N1 C12 C13 113.83(12) . . ?
N1 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
N1 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
H12B C12 H12A 107.7 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
H13B C13 H13A 109.5 . . ?
H13C C13 H13A 109.5 . . ?
N1 C14 C15 113.83(12) . . ?
N1 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
N1 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C12 N1 C1 C2 -139.13(12) . . . . ?
C14 N1 C1 C2 102.97(13) . . . . ?
Cu1 N1 C1 C2 -15.99(13) . . . . ?
C3 N2 C2 O1 -3.1(2) . . . . ?
Cu1 N2 C2 O1 177.38(12) . . . . ?
C3 N2 C2 C1 174.39(12) . . . . ?
Cu1 N2 C2 C1 -5.08(16) . . . . ?
N1 C1 C2 O1 -167.74(12) . . . . ?
N1 C1 C2 N2 14.50(17) . . . . ?
C2 N2 C3 C4 4.7(2) . . . . ?
Cu1 N2 C3 C4 -175.78(12) . . . . ?
C2 N2 C3 C11 -173.47(12) . . . . ?
Cu1 N2 C3 C11 6.02(15) . . . . ?
N2 C3 C4 C5 -178.25(14) . . . . ?
C11 C3 C4 C5 -0.1(2) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
C5 C6 C7 C11 -1.4(2) . . . . ?
C5 C6 C7 C8 177.85(14) . . . . ?
C6 C7 C8 C9 -179.75(14) . . . . ?
C11 C7 C8 C9 -0.5(2) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
C11 N3 C10 C9 0.5(2) . . . . ?
Cu1 N3 C10 C9 -179.44(10) . . . . ?
C8 C9 C10 N3 0.9(2) . . . . ?
C10 N3 C11 C7 -1.94(19) . . . . ?
Cu1 N3 C11 C7 178.03(10) . . . . ?
C10 N3 C11 C3 177.54(12) . . . . ?
Cu1 N3 C11 C3 -2.49(14) . . . . ?
C6 C7 C11 N3 -178.79(13) . . . . ?
C8 C7 C11 N3 1.92(19) . . . . ?
C6 C7 C11 C3 1.8(2) . . . . ?
C8 C7 C11 C3 -177.54(13) . . . . ?
C4 C3 C11 N3 179.52(12) . . . . ?
N2 C3 C11 N3 -2.08(17) . . . . ?
C4 C3 C11 C7 -1.0(2) . . . . ?
N2 C3 C11 C7 177.41(12) . . . . ?
C14 N1 C12 C13 -171.60(12) . . . . ?
C1 N1 C12 C13 68.87(15) . . . . ?
Cu1 N1 C12 C13 -50.94(14) . . . . ?
C12 N1 C14 C15 175.89(12) . . . . ?
C1 N1 C14 C15 -63.80(15) . . . . ?
Cu1 N1 C14 C15 53.43(14) . . . . ?

_refine_diff_density_max         1.118
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.071

