# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1536918'
_audit_update_record             
;
2017-03-09 deposited with the CCDC.
2017-03-24 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         'C43 H40 Cu2 N4 O6'
_chemical_formula_sum            'C43 H40 Cu2 N4 O6'
_chemical_formula_weight         835.87

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'

_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                   14.1141(3)
_cell_length_b                   16.4924(3)
_cell_length_c                   17.4915(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.647(2)
_cell_angle_gamma                90
_cell_volume                     3920.70(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3865
_cell_measurement_theta_min      3.240
_cell_measurement_theta_max      21.94

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.770
_shelx_estimated_absorpt_T_min   0.686
_shelx_estimated_absorpt_T_max   0.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.376785
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25906
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.586
_diffrn_reflns_theta_max         71.550
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7543
_reflns_number_gt                4935
_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       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97
_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)+(0.2000P)²] 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         7543
_refine_ls_number_parameters     430
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.1322
_refine_ls_R_factor_gt           0.1023
_refine_ls_wR_factor_ref         0.3495
_refine_ls_wR_factor_gt          0.3137
_refine_ls_goodness_of_fit_ref   1.244
_refine_ls_restrained_S_all      1.256
_refine_ls_shift/su_max          0.068
_refine_ls_shift/su_mean         0.002

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 0.89522(7) 0.43794(5) 0.44947(5) 0.0640(3) Uani 1 1 d . . . . .
Cu2 Cu 0.38429(7) 0.53584(5) 0.43560(5) 0.0657(3) Uani 1 1 d . . . . .
O1 O 0.8914(4) 0.5384(3) 0.5067(3) 0.0740(11) Uani 1 1 d . . . . .
O2 O 0.8967(4) 0.3754(3) 0.5436(3) 0.0784(12) Uani 1 1 d . . . . .
O3 O 0.3696(4) 0.6332(3) 0.4928(3) 0.0762(11) Uani 1 1 d . . . . .
O4 O 0.3973(4) 0.4714(3) 0.5296(2) 0.0736(11) Uani 1 1 d . . . . .
O5 O 0.7302(13) 0.3411(6) 0.1575(7) 0.344(11) Uani 1 1 d D U . . .
O6 O 0.4918(9) 0.4613(8) 0.1665(8) 0.242(7) Uani 1 1 d D . . . .
N1 N 0.9032(4) 0.3363(3) 0.3941(3) 0.0688(12) Uani 1 1 d . . . . .
N2 N 0.8821(4) 0.5008(3) 0.3523(3) 0.0655(12) Uani 1 1 d . . . . .
N3 N 0.3847(4) 0.4365(3) 0.3747(3) 0.0640(12) Uani 1 1 d . . . . .
N4 N 0.3741(4) 0.6016(3) 0.3406(3) 0.0717(13) Uani 1 1 d . . . . .
C1 C 0.8486(6) 0.6302(5) 0.5931(5) 0.096(2) Uani 1 1 d . . . . .
H1A H 0.8880 0.6661 0.5711 0.144 Uiso 1 1 calc R U . . .
H1B H 0.8679 0.6347 0.6499 0.144 Uiso 1 1 calc R U . . .
H1C H 0.7805 0.6447 0.5732 0.144 Uiso 1 1 calc R U . . .
C2 C 0.8632(5) 0.5451(4) 0.5698(4) 0.0697(15) Uani 1 1 d . . . . .
C3 C 0.8539(5) 0.4806(5) 0.6174(4) 0.0790(18) Uani 1 1 d . . . . .
H3 H 0.8319 0.4918 0.6618 0.095 Uiso 1 1 calc R U . . .
C4 C 0.8747(5) 0.4007(4) 0.6046(4) 0.0755(17) Uani 1 1 d . . . . .
C5 C 0.8708(7) 0.3370(5) 0.6649(5) 0.104(3) Uani 1 1 d . . . . .
H5A H 0.8335 0.2914 0.6388 0.157 Uiso 1 1 calc R U . . .
H5B H 0.8399 0.3589 0.7030 0.157 Uiso 1 1 calc R U . . .
H5C H 0.9364 0.3198 0.6915 0.157 Uiso 1 1 calc R U . . .
C6 C 0.3359(6) 0.7206(5) 0.5891(5) 0.105(3) Uani 1 1 d . . . . .
H6A H 0.3983 0.7449 0.6143 0.158 Uiso 1 1 calc R U . . .
H6B H 0.2974 0.7169 0.6266 0.158 Uiso 1 1 calc R U . . .
H6C H 0.3017 0.7534 0.5449 0.158 Uiso 1 1 calc R U . . .
C7 C 0.3521(5) 0.6358(4) 0.5599(4) 0.0739(16) Uani 1 1 d . . . . .
C8 C 0.3473(6) 0.5702(4) 0.6074(4) 0.0808(19) Uani 1 1 d . . . . .
H8 H 0.3251 0.5785 0.6523 0.097 Uiso 1 1 calc R U . . .
C9 C 0.3738(5) 0.4922(4) 0.5917(4) 0.0749(17) Uani 1 1 d . . . . .
C10 C 0.3743(7) 0.4259(5) 0.6503(5) 0.101(3) Uani 1 1 d . . . . .
H10A H 0.3601 0.3751 0.6228 0.152 Uiso 1 1 calc R U . . .
H10B H 0.3252 0.4369 0.6777 0.152 Uiso 1 1 calc R U . . .
H10C H 0.4378 0.4232 0.6879 0.152 Uiso 1 1 calc R U . . .
C11 C 0.9223(5) 0.2628(4) 0.4268(4) 0.0846(19) Uani 1 1 d . . . . .
H11 H 0.9335 0.2524 0.4808 0.102 Uiso 1 1 calc R U . . .
C12 C 0.9233(7) 0.2041(5) 0.3706(5) 0.112(3) Uani 1 1 d . . . . .
H12 H 0.9335 0.1488 0.3793 0.135 Uiso 1 1 calc R U . . .
C13 C 0.9065(9) 0.2433(5) 0.3013(6) 0.135(4) Uani 1 1 d . . . . .
H13 H 0.9034 0.2197 0.2524 0.162 Uiso 1 1 calc R U . . .
C14 C 0.8944(8) 0.3255(5) 0.3146(4) 0.105(3) Uani 1 1 d . . . . .
C15 C 0.8748(9) 0.3889(6) 0.2597(4) 0.132(4) Uani 1 1 d D . . . .
C16 C 0.8695(8) 0.4705(5) 0.2771(4) 0.101(3) Uani 1 1 d . . . . .
C17 C 0.8533(9) 0.5360(6) 0.2233(5) 0.138(4) Uani 1 1 d . . . . .
H17 H 0.8427 0.5321 0.1685 0.165 Uiso 1 1 calc R U . . .
C18 C 0.8560(8) 0.6043(5) 0.2641(5) 0.110(3) Uani 1 1 d . . . . .
H18 H 0.8475 0.6569 0.2441 0.132 Uiso 1 1 calc R U . . .
C19 C 0.8745(5) 0.5804(4) 0.3444(4) 0.0770(17) Uani 1 1 d . . . . .
H19 H 0.8806 0.6163 0.3865 0.092 Uiso 1 1 calc R U . . .
C20 C 0.8956(12) 0.3728(8) 0.1780(5) 0.385(9) Uani 1 1 d DG U . . .
C21 C 0.9808(11) 0.3807(8) 0.1531(6) 0.385(9) Uani 1 1 d G . . . .
C22 C 0.9808(12) 0.3577(8) 0.0767(7) 0.385(9) Uani 1 1 d G U . . .
C23 C 0.8956(13) 0.3269(7) 0.0251(4) 0.385(9) Uani 1 1 d G U . . .
C24 C 0.8105(12) 0.3190(7) 0.0500(6) 0.385(9) Uani 1 1 d G . . . .
C25 C 0.8105(11) 0.3419(9) 0.1264(7) 0.385(9) Uani 1 1 d DG U . . .
C26 C 0.6449(17) 0.3051(11) 0.0880(9) 0.385(9) Uani 1 1 d D U . . .
H26A H 0.6375 0.3314 0.0371 0.462 Uiso 1 1 calc R U . . .
H26B H 0.6468 0.2466 0.0831 0.462 Uiso 1 1 calc R U . . .
C27 C 0.5695(10) 0.3372(9) 0.1363(8) 0.203(8) Uani 1 1 d D . . . .
H27A H 0.5038 0.3172 0.1115 0.243 Uiso 1 1 calc R U . . .
H27B H 0.5895 0.3171 0.1904 0.243 Uiso 1 1 calc R U . . .
C28 C 0.5694(15) 0.4300(10) 0.1366(13) 0.275(12) Uani 1 1 d D . . . .
H28A H 0.6321 0.4494 0.1693 0.330 Uiso 1 1 calc R U . . .
H28B H 0.5615 0.4496 0.0830 0.330 Uiso 1 1 calc R U . . .
C29 C 0.4016(7) 0.4626(6) 0.1178(5) 0.152(5) Uani 1 1 d G . . . .
C30 C 0.3782(9) 0.4491(7) 0.0365(5) 0.330(12) Uani 1 1 d G . . . .
C31 C 0.2807(10) 0.4517(6) -0.0086(3) 0.330(12) Uani 1 1 d G . . . .
C32 C 0.2065(8) 0.4679(7) 0.0278(5) 0.330(12) Uani 1 1 d G . . . .
C33 C 0.2298(8) 0.4814(7) 0.1092(6) 0.295(12) Uani 1 1 d G . . . .
C34 C 0.3274(8) 0.4788(6) 0.1542(3) 0.198(8) Uani 1 1 d G . . . .
C35 C 0.3423(7) 0.4950(5) 0.2421(4) 0.102(3) Uani 1 1 d . . . . .
C36 C 0.3514(7) 0.5763(5) 0.2647(4) 0.089(2) Uani 1 1 d . . . . .
C37 C 0.3458(8) 0.6440(6) 0.2146(5) 0.119(3) Uani 1 1 d . . . . .
H37 H 0.3311 0.6437 0.1595 0.143 Uiso 1 1 calc R U . . .
C38 C 0.3655(8) 0.7079(6) 0.2613(6) 0.122(3) Uani 1 1 d . . . . .
H38 H 0.3687 0.7613 0.2452 0.147 Uiso 1 1 calc R U . . .
C39 C 0.3805(6) 0.6810(4) 0.3382(5) 0.088(2) Uani 1 1 d . . . . .
H39 H 0.3934 0.7146 0.3825 0.106 Uiso 1 1 calc R U . . .
C40 C 0.3993(5) 0.3598(4) 0.4018(4) 0.0755(16) Uani 1 1 d . . . . .
H40 H 0.4195 0.3463 0.4553 0.091 Uiso 1 1 calc R U . . .
C41 C 0.3808(6) 0.3040(4) 0.3413(5) 0.092(2) Uani 1 1 d . . . . .
H41 H 0.3853 0.2479 0.3463 0.110 Uiso 1 1 calc R U . . .
C42 C 0.3548(7) 0.3472(5) 0.2730(5) 0.107(3) Uani 1 1 d . . . . .
H42 H 0.3376 0.3260 0.2218 0.129 Uiso 1 1 calc R U . . .
C43 C 0.3585(6) 0.4291(4) 0.2930(4) 0.0825(19) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.939(4) . ?
Cu1 O1 1.943(4) . ?
Cu1 N1 1.953(5) . ?
Cu1 N2 1.957(5) . ?
Cu2 O4 1.925(4) . ?
Cu2 O3 1.932(4) . ?
Cu2 N4 1.958(5) . ?
Cu2 N3 1.954(5) . ?
O1 C2 1.277(7) . ?
O2 C4 1.260(7) . ?
O3 C7 1.264(8) . ?
O4 C9 1.265(8) . ?
O5 C25 1.384(16) . ?
O5 C26 1.58(2) . ?
O6 C29 1.327(14) . ?
O6 C28 1.432(12) . ?
N1 C11 1.336(8) . ?
N1 C14 1.375(8) . ?
N2 C19 1.322(8) . ?
N2 C16 1.374(8) . ?
N3 C40 1.347(8) . ?
N3 C43 1.381(8) . ?
N4 C39 1.314(9) . ?
N4 C36 1.345(9) . ?
C1 C2 1.492(9) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.377(9) . ?
C3 C4 1.381(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.500(9) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.528(9) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.379(10) . ?
C8 C9 1.387(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.497(9) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.382(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.338(12) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.395(12) . ?
C15 C16 1.385(11) . ?
C15 C20 1.558(11) . ?
C16 C17 1.411(10) . ?
C17 C18 1.330(12) . ?
C17 H17 0.9300 . ?
C18 C19 1.414(9) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.3900 . ?
C20 C25 1.3900 . ?
C21 C22 1.3900 . ?
C22 C23 1.3900 . ?
C23 C24 1.3900 . ?
C24 C25 1.3900 . ?
C26 C27 1.616(16) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.530(14) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.3900 . ?
C29 C34 1.3900 . ?
C30 C31 1.3900 . ?
C31 C32 1.3900 . ?
C32 C33 1.3900 . ?
C33 C34 1.3900 . ?
C34 C35 1.519(9) . ?
C35 C36 1.393(11) . ?
C35 C43 1.385(11) . ?
C36 C37 1.408(10) . ?
C37 C38 1.315(13) . ?
C37 H37 0.9300 . ?
C38 C39 1.377(11) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C40 C41 1.373(9) . ?
C40 H40 0.9300 . ?
C41 C42 1.355(11) . ?
C41 H41 0.9300 . ?
C42 C43 1.392(10) . ?
C42 H42 0.9300 . ?

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
O2 Cu1 O1 90.69(19) . . ?
O2 Cu1 N1 88.6(2) . . ?
O1 Cu1 N1 178.2(2) . . ?
O2 Cu1 N2 175.4(2) . . ?
O1 Cu1 N2 89.21(19) . . ?
N1 Cu1 N2 91.6(2) . . ?
O4 Cu2 O3 90.88(18) . . ?
O4 Cu2 N4 178.8(2) . . ?
O3 Cu2 N4 89.2(2) . . ?
O4 Cu2 N3 89.39(19) . . ?
O3 Cu2 N3 174.2(2) . . ?
N4 Cu2 N3 90.7(2) . . ?
C2 O1 Cu1 125.3(4) . . ?
C4 O2 Cu1 126.4(4) . . ?
C7 O3 Cu2 125.8(4) . . ?
C9 O4 Cu2 126.6(4) . . ?
C25 O5 C26 103.7(11) . . ?
C29 O6 C28 117.9(13) . . ?
C11 N1 C14 105.5(6) . . ?
C11 N1 Cu1 126.8(5) . . ?
C14 N1 Cu1 127.7(5) . . ?
C19 N2 C16 106.1(5) . . ?
C19 N2 Cu1 127.1(4) . . ?
C16 N2 Cu1 126.6(4) . . ?
C40 N3 C43 104.7(5) . . ?
C40 N3 Cu2 128.2(4) . . ?
C43 N3 Cu2 126.8(4) . . ?
C39 N4 C36 106.2(6) . . ?
C39 N4 Cu2 126.1(5) . . ?
C36 N4 Cu2 127.5(5) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 123.9(6) . . ?
O1 C2 C1 114.5(6) . . ?
C3 C2 C1 121.3(6) . . ?
C2 C3 C4 125.5(6) . . ?
C2 C3 H3 117.3 . . ?
C4 C3 H3 117.3 . . ?
O2 C4 C3 124.4(6) . . ?
O2 C4 C5 115.3(6) . . ?
C3 C4 C5 120.3(6) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 C8 126.0(6) . . ?
O3 C7 C6 115.3(7) . . ?
C8 C7 C6 118.7(6) . . ?
C7 C8 C9 123.2(6) . . ?
C7 C8 H8 118.4 . . ?
C9 C8 H8 118.4 . . ?
O4 C9 C8 124.7(6) . . ?
O4 C9 C10 115.8(7) . . ?
C8 C9 C10 119.5(7) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 111.8(7) . . ?
N1 C11 H11 124.1 . . ?
C12 C11 H11 124.1 . . ?
C13 C12 C11 105.8(7) . . ?
C13 C12 H12 127.1 . . ?
C11 C12 H12 127.1 . . ?
C12 C13 C14 108.6(7) . . ?
C12 C13 H13 125.7 . . ?
C14 C13 H13 125.7 . . ?
N1 C14 C15 123.1(6) . . ?
N1 C14 C13 108.2(7) . . ?
C15 C14 C13 128.7(7) . . ?
C14 C15 C16 126.1(7) . . ?
C14 C15 C20 116.8(8) . . ?
C16 C15 C20 113.6(9) . . ?
N2 C16 C15 124.2(6) . . ?
N2 C16 C17 108.4(6) . . ?
C15 C16 C17 127.3(7) . . ?
C18 C17 C16 108.3(7) . . ?
C18 C17 H17 125.8 . . ?
C16 C17 H17 125.8 . . ?
C17 C18 C19 105.6(7) . . ?
C17 C18 H18 127.2 . . ?
C19 C18 H18 127.2 . . ?
N2 C19 C18 111.6(6) . . ?
N2 C19 H19 124.2 . . ?
C18 C19 H19 124.2 . . ?
C21 C20 C25 120.0 . . ?
C21 C20 C15 131.6(10) . . ?
C25 C20 C15 108.3(10) . . ?
C20 C21 C22 120.0 . . ?
C21 C22 C23 120.0 . . ?
C24 C23 C22 120.0 . . ?
C25 C24 C23 120.0 . . ?
O5 C25 C24 126.0(10) . . ?
O5 C25 C20 113.9(10) . . ?
C24 C25 C20 120.0 . . ?
C27 C26 O5 86.9(9) . . ?
C27 C26 H26A 114.2 . . ?
O5 C26 H26A 114.2 . . ?
C27 C26 H26B 114.2 . . ?
O5 C26 H26B 114.2 . . ?
H26A C26 H26B 111.3 . . ?
C28 C27 C26 109.3(12) . . ?
C28 C27 H27A 109.8 . . ?
C26 C27 H27A 109.8 . . ?
C28 C27 H27B 109.8 . . ?
C26 C27 H27B 109.8 . . ?
H27A C27 H27B 108.3 . . ?
O6 C28 C27 111.3(14) . . ?
O6 C28 H28A 109.4 . . ?
C27 C28 H28A 109.4 . . ?
O6 C28 H28B 109.4 . . ?
C27 C28 H28B 109.4 . . ?
H28A C28 H28B 108.0 . . ?
O6 C29 C30 125.1(8) . . ?
O6 C29 C34 114.9(8) . . ?
C30 C29 C34 120.0 . . ?
C31 C30 C29 120.0 . . ?
C30 C31 C32 120.0 . . ?
C33 C32 C31 120.0 . . ?
C32 C33 C34 120.0 . . ?
C33 C34 C29 120.0 . . ?
C33 C34 C35 114.5(8) . . ?
C29 C34 C35 125.5(8) . . ?
C36 C35 C43 125.9(7) . . ?
C36 C35 C34 115.7(7) . . ?
C43 C35 C34 117.8(8) . . ?
N4 C36 C35 123.9(6) . . ?
N4 C36 C37 109.0(7) . . ?
C35 C36 C37 127.0(7) . . ?
C38 C37 C36 106.4(8) . . ?
C38 C37 H37 126.8 . . ?
C36 C37 H37 126.8 . . ?
C37 C38 C39 107.4(8) . . ?
C37 C38 H38 126.3 . . ?
C39 C38 H38 126.3 . . ?
N4 C39 C38 110.9(8) . . ?
N4 C39 H39 124.5 . . ?
C38 C39 H39 124.5 . . ?
N3 C40 C41 112.3(6) . . ?
N3 C40 H40 123.8 . . ?
C41 C40 H40 123.8 . . ?
C42 C41 C40 106.1(7) . . ?
C42 C41 H41 127.0 . . ?
C40 C41 H41 127.0 . . ?
C41 C42 C43 107.8(7) . . ?
C41 C42 H42 126.1 . . ?
C43 C42 H42 126.1 . . ?
N3 C43 C42 109.2(6) . . ?
N3 C43 C35 123.2(6) . . ?
C42 C43 C35 127.6(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
Cu1 O1 C2 C3 16.4(10) . . . . ?
Cu1 O1 C2 C1 -168.6(5) . . . . ?
O1 C2 C3 C4 0.9(12) . . . . ?
C1 C2 C3 C4 -173.8(7) . . . . ?
Cu1 O2 C4 C3 -6.1(11) . . . . ?
Cu1 O2 C4 C5 173.1(5) . . . . ?
C2 C3 C4 O2 -6.5(13) . . . . ?
C2 C3 C4 C5 174.2(7) . . . . ?
Cu2 O3 C7 C8 5.1(11) . . . . ?
Cu2 O3 C7 C6 -175.4(5) . . . . ?
O3 C7 C8 C9 8.6(13) . . . . ?
C6 C7 C8 C9 -170.9(7) . . . . ?
Cu2 O4 C9 C8 -9.8(10) . . . . ?
Cu2 O4 C9 C10 169.3(5) . . . . ?
C7 C8 C9 O4 -6.1(12) . . . . ?
C7 C8 C9 C10 174.9(7) . . . . ?
C14 N1 C11 C12 -1.8(10) . . . . ?
Cu1 N1 C11 C12 -179.5(6) . . . . ?
N1 C11 C12 C13 1.4(12) . . . . ?
C11 C12 C13 C14 -0.5(13) . . . . ?
C11 N1 C14 C15 -179.6(10) . . . . ?
Cu1 N1 C14 C15 -1.9(15) . . . . ?
C11 N1 C14 C13 1.4(11) . . . . ?
Cu1 N1 C14 C13 179.1(7) . . . . ?
C12 C13 C14 N1 -0.5(14) . . . . ?
C12 C13 C14 C15 -179.4(12) . . . . ?
N1 C14 C15 C16 6(2) . . . . ?
C13 C14 C15 C16 -175.7(12) . . . . ?
N1 C14 C15 C20 163.3(11) . . . . ?
C13 C14 C15 C20 -18(2) . . . . ?
C19 N2 C16 C15 178.2(10) . . . . ?
Cu1 N2 C16 C15 -7.4(14) . . . . ?
C19 N2 C16 C17 -0.3(11) . . . . ?
Cu1 N2 C16 C17 174.1(7) . . . . ?
C14 C15 C16 N2 -1(2) . . . . ?
C20 C15 C16 N2 -159.1(10) . . . . ?
C14 C15 C16 C17 177.5(12) . . . . ?
C20 C15 C16 C17 19.2(18) . . . . ?
N2 C16 C17 C18 0.0(14) . . . . ?
C15 C16 C17 C18 -178.4(11) . . . . ?
C16 C17 C18 C19 0.2(13) . . . . ?
C16 N2 C19 C18 0.4(10) . . . . ?
Cu1 N2 C19 C18 -173.9(5) . . . . ?
C17 C18 C19 N2 -0.4(12) . . . . ?
C14 C15 C20 C21 -86.4(15) . . . . ?
C16 C15 C20 C21 74.1(14) . . . . ?
C14 C15 C20 C25 90.4(11) . . . . ?
C16 C15 C20 C25 -109.0(10) . . . . ?
C25 C20 C21 C22 0.0 . . . . ?
C15 C20 C21 C22 176.5(12) . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C26 O5 C25 C24 2.5(16) . . . . ?
C26 O5 C25 C20 179.3(9) . . . . ?
C23 C24 C25 O5 176.6(16) . . . . ?
C23 C24 C25 C20 0.0 . . . . ?
C21 C20 C25 O5 -177.0(14) . . . . ?
C15 C20 C25 O5 5.7(11) . . . . ?
C21 C20 C25 C24 0.0 . . . . ?
C15 C20 C25 C24 -177.2(10) . . . . ?
C25 O5 C26 C27 -165.6(12) . . . . ?
O5 C26 C27 C28 67.6(15) . . . . ?
C29 O6 C28 C27 -79(2) . . . . ?
C26 C27 C28 O6 169.9(14) . . . . ?
C28 O6 C29 C30 -11.6(18) . . . . ?
C28 O6 C29 C34 168.2(11) . . . . ?
O6 C29 C30 C31 179.8(13) . . . . ?
C34 C29 C30 C31 0.0 . . . . ?
C29 C30 C31 C32 0.0 . . . . ?
C30 C31 C32 C33 0.0 . . . . ?
C31 C32 C33 C34 0.0 . . . . ?
C32 C33 C34 C29 0.0 . . . . ?
C32 C33 C34 C35 179.7(9) . . . . ?
O6 C29 C34 C33 -179.8(12) . . . . ?
C30 C29 C34 C33 0.0 . . . . ?
O6 C29 C34 C35 0.5(13) . . . . ?
C30 C29 C34 C35 -179.7(10) . . . . ?
C33 C34 C35 C36 -86.7(10) . . . . ?
C29 C34 C35 C36 93.0(10) . . . . ?
C33 C34 C35 C43 101.6(9) . . . . ?
C29 C34 C35 C43 -78.7(12) . . . . ?
C39 N4 C36 C35 177.1(9) . . . . ?
Cu2 N4 C36 C35 -7.8(12) . . . . ?
C39 N4 C36 C37 1.1(10) . . . . ?
Cu2 N4 C36 C37 176.2(6) . . . . ?
C43 C35 C36 N4 -2.7(16) . . . . ?
C34 C35 C36 N4 -173.6(8) . . . . ?
C43 C35 C36 C37 172.6(10) . . . . ?
C34 C35 C36 C37 1.7(15) . . . . ?
N4 C36 C37 C38 0.3(12) . . . . ?
C35 C36 C37 C38 -175.6(10) . . . . ?
C36 C37 C38 C39 -1.5(12) . . . . ?
C36 N4 C39 C38 -2.1(10) . . . . ?
Cu2 N4 C39 C38 -177.2(6) . . . . ?
C37 C38 C39 N4 2.3(12) . . . . ?
C43 N3 C40 C41 -1.8(8) . . . . ?
Cu2 N3 C40 C41 171.4(5) . . . . ?
N3 C40 C41 C42 0.9(10) . . . . ?
C40 C41 C42 C43 0.4(10) . . . . ?
C40 N3 C43 C42 2.0(9) . . . . ?
Cu2 N3 C43 C42 -171.3(6) . . . . ?
C40 N3 C43 C35 -176.3(8) . . . . ?
Cu2 N3 C43 C35 10.4(12) . . . . ?
C41 C42 C43 N3 -1.5(11) . . . . ?
C41 C42 C43 C35 176.6(9) . . . . ?
C36 C35 C43 N3 1.3(15) . . . . ?
C34 C35 C43 N3 172.0(8) . . . . ?
C36 C35 C43 C42 -176.6(9) . . . . ?
C34 C35 C43 C42 -5.9(16) . . . . ?

_refine_diff_density_max         1.215
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.109

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1505322'
_audit_update_record             
;
2017-03-09 deposited with the CCDC.
2017-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C44 H48  N6 Ni2 O2 S4'
_chemical_formula_sum            'C44 H48  N6 Ni2 O2 S4'
_exptl_crystal_recrystallization_method 'DCM, Hexane'
_chemical_melting_point          340

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_diffrn_ambient_temperature      301(2)
_chemical_formula_weight         938.54

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.531(5)
_cell_length_b                   16.488(9)
_cell_length_c                   16.546(9)
_cell_angle_alpha                61.418(14)
_cell_angle_beta                 88.048(14)
_cell_angle_gamma                79.414(14)
_cell_volume                     2240(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    380
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      20.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             980
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    1.070
_shelx_estimated_absorpt_T_min   0.864
_shelx_estimated_absorpt_T_max   0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.36543
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker, 1997'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24043
_diffrn_reflns_av_unetI/netI     0.1209
_diffrn_reflns_av_R_equivalents  0.1081
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.178
_diffrn_reflns_theta_max         24.381
_diffrn_reflns_theta_full        24.381
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_Laue_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_point_group_measured_fraction_full 0.914
_reflns_number_total             6593
_reflns_number_gt                2648
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97
_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)+(0.0649P)²+1.0413P] 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         6680
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1436
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1493
_refine_ls_wR_factor_gt          0.1189
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
Ni1 Ni 0.06521(11) 0.75083(10) 0.78461(10) 0.0482(5) Uani 1 1 d . . . . .
Ni2 Ni 0.59128(12) 0.23091(10) 0.75381(10) 0.0511(5) Uani 1 1 d . . . . .
S1 S 0.0296(3) 0.7506(2) 0.9173(2) 0.0643(10) Uani 1 1 d . . . . .
S3 S 0.6642(3) 0.0932(2) 0.7611(2) 0.0689(10) Uani 1 1 d . . . . .
S4 S 0.7997(3) 0.2466(2) 0.6926(2) 0.0677(10) Uani 1 1 d . . . . .
S2 S 0.2700(3) 0.7721(2) 0.8184(2) 0.0720(11) Uani 1 1 d . . . . .
O1 O -0.3237(7) 0.8570(7) 0.4998(5) 0.069(2) Uani 1 1 d . . . . .
O2 O 0.3153(7) 0.4403(5) 0.9003(5) 0.071(2) Uani 1 1 d . . . . .
N5 N 0.5327(9) 0.3584(6) 0.7213(6) 0.047(2) Uani 1 1 d . . . . .
N1 N -0.1242(7) 0.7391(5) 0.7655(6) 0.042(2) Uani 1 1 d . . . . .
N4 N 0.4355(8) 0.1961(7) 0.8288(6) 0.045(2) Uani 1 1 d . . . . .
N2 N 0.1257(8) 0.7484(6) 0.6762(6) 0.046(2) Uani 1 1 d . . . . .
N3 N 0.2647(9) 0.7770(7) 0.9797(8) 0.079(3) Uani 1 1 d . . . . .
C5 C -0.0978(10) 0.7281(7) 0.6234(7) 0.041(3) Uani 1 1 d . . . . .
N6 N 0.9280(10) 0.0815(9) 0.6960(6) 0.073(3) Uani 1 1 d . . . . .
C26 C 0.3239(11) 0.2538(10) 0.8425(8) 0.046(3) Uani 1 1 d . . . . .
C4 C -0.1778(9) 0.7278(7) 0.6957(8) 0.044(3) Uani 1 1 d . . . . .
C27 C 0.3067(10) 0.3508(9) 0.7975(7) 0.040(3) Uani 1 1 d . . . . .
C11 C -0.2831(11) 0.7755(10) 0.4959(8) 0.053(3) Uani 1 1 d . . . . .
C10 C -0.1703(11) 0.7116(9) 0.5555(8) 0.052(3) Uani 1 1 d . . . . .
C6 C 0.0454(9) 0.7361(7) 0.6148(7) 0.043(3) Uani 1 1 d . . . . .
C32 C 0.1775(11) 0.4022(8) 0.8147(7) 0.047(3) Uani 1 1 d . . . . .
C8 C 0.2627(11) 0.7478(8) 0.5614(8) 0.063(4) Uani 1 1 d . . . . .
H8 H 0.3418 0.7510 0.5263 0.076 Uiso 1 1 calc R U . . .
C28 C 0.4035(12) 0.4001(10) 0.7402(8) 0.049(3) Uani 1 1 d . . . . .
C33 C 0.1808(12) 0.4492(8) 0.8651(8) 0.059(3) Uani 1 1 d . . . . .
C23 C 0.4201(11) 0.1083(9) 0.8886(9) 0.065(4) Uani 1 1 d . . . . .
H23 H 0.4806 0.0542 0.8950 0.078 Uiso 1 1 calc R U . . .
C37 C 0.0446(12) 0.4061(8) 0.7793(8) 0.067(4) Uani 1 1 d . . . . .
H37 H 0.0398 0.3763 0.7441 0.080 Uiso 1 1 calc R U . . .
C40 C 0.8186(11) 0.1317(9) 0.7124(7) 0.057(3) Uani 1 1 d . . . . .
C7 C 0.1324(11) 0.7351(7) 0.5446(8) 0.059(3) Uani 1 1 d . . . . .
H7 H 0.1054 0.7272 0.4957 0.071 Uiso 1 1 calc R U . . .
C18 C 0.2014(10) 0.7677(8) 0.9165(8) 0.062(4) Uani 1 1 d . . . . .
C15 C -0.1221(11) 0.6289(10) 0.5507(8) 0.065(4) Uani 1 1 d . . . . .
H15 H -0.0455 0.5856 0.5903 0.078 Uiso 1 1 calc R U . . .
C13 C -0.2970(13) 0.6713(12) 0.4335(9) 0.076(4) Uani 1 1 d . . . . .
H13 H -0.3420 0.6584 0.3931 0.092 Uiso 1 1 calc R U . . .
C14 C -0.1835(14) 0.6087(10) 0.4898(10) 0.080(4) Uani 1 1 d . . . . .
H14 H -0.1479 0.5535 0.4873 0.096 Uiso 1 1 calc R U . . .
C12 C -0.3449(11) 0.7526(10) 0.4363(8) 0.068(4) Uani 1 1 d . . . . .
H12 H -0.4222 0.7948 0.3967 0.082 Uiso 1 1 calc R U . . .
C25 C 0.2403(11) 0.1997(10) 0.9113(9) 0.067(4) Uani 1 1 d . . . . .
H25 H 0.1590 0.2223 0.9326 0.080 Uiso 1 1 calc R U . . .
C9 C 0.2538(10) 0.7550(8) 0.6416(9) 0.067(4) Uani 1 1 d . . . . .
H9 H 0.3298 0.7637 0.6686 0.080 Uiso 1 1 calc R U . . .
C1 C -0.2318(10) 0.7349(8) 0.8233(7) 0.066(4) Uani 1 1 d . . . . .
H1 H -0.2264 0.7413 0.8759 0.079 Uiso 1 1 calc R U . . .
C3 C -0.3192(10) 0.7148(8) 0.7128(9) 0.070(4) Uani 1 1 d . . . . .
H3 H -0.3799 0.7048 0.6770 0.084 Uiso 1 1 calc R U . . .
C38 C 0.3292(11) 0.4897(8) 0.9496(9) 0.077(4) Uani 1 1 d . . . . .
H38A H 0.2810 0.4639 1.0067 0.092 Uiso 1 1 calc R U . . .
H38B H 0.2865 0.5557 0.9130 0.092 Uiso 1 1 calc R U . . .
C31 C 0.5906(13) 0.4293(11) 0.6627(9) 0.075(4) Uani 1 1 d . . . . .
H31 H 0.6778 0.4217 0.6378 0.090 Uiso 1 1 calc R U . . .
C2 C -0.3507(10) 0.7193(9) 0.7901(10) 0.079(4) Uani 1 1 d . . . . .
H2 H -0.4379 0.7131 0.8173 0.094 Uiso 1 1 calc R U . . .
C16 C -0.4410(11) 0.9257(9) 0.4402(9) 0.074(4) Uani 1 1 d . . . . .
H16A H -0.5259 0.8981 0.4511 0.089 Uiso 1 1 calc R U . . .
H16B H -0.4191 0.9465 0.3763 0.089 Uiso 1 1 calc R U . . .
C34 C 0.0581(14) 0.4954(9) 0.8829(8) 0.076(4) Uani 1 1 d . . . . .
H34 H 0.0614 0.5238 0.9194 0.091 Uiso 1 1 calc R U . . .
C29 C 0.3914(12) 0.4970(11) 0.6922(10) 0.075(4) Uani 1 1 d . . . . .
H29 H 0.3171 0.5415 0.6937 0.090 Uiso 1 1 calc R U . . .
C17 C -0.4687(12) 1.0088(10) 0.4581(8) 0.080(4) Uani 1 1 d . . . . .
H17A H -0.3788 1.0285 0.4578 0.096 Uiso 1 1 calc R U . . .
H17B H -0.5311 1.0606 0.4079 0.096 Uiso 1 1 calc R U . . .
C21 C 0.1915(14) 0.7770(11) 1.0576(9) 0.096(5) Uani 1 1 d . . . . .
H21A H 0.2596 0.7493 1.1104 0.115 Uiso 1 1 calc R U . . .
H21B H 0.1195 0.7381 1.0730 0.115 Uiso 1 1 calc R U . . .
C24 C 0.2996(12) 0.1088(11) 0.9407(9) 0.078(4) Uani 1 1 d . . . . .
H24 H 0.2675 0.0566 0.9864 0.093 Uiso 1 1 calc R U . . .
C19 C 0.4231(14) 0.7789(10) 0.9758(10) 0.101(5) Uani 1 1 d . . . . .
H19A H 0.4651 0.7575 1.0369 0.121 Uiso 1 1 calc R U . . .
H19B H 0.4714 0.7380 0.9524 0.121 Uiso 1 1 calc R U . . .
C30 C 0.5108(16) 0.5146(11) 0.6421(10) 0.100(5) Uani 1 1 d . . . . .
H30 H 0.5323 0.5732 0.6022 0.120 Uiso 1 1 calc R U . . .
C35 C -0.0722(13) 0.4980(9) 0.8436(11) 0.087(5) Uani 1 1 d . . . . .
H35 H -0.1557 0.5321 0.8515 0.104 Uiso 1 1 calc R U . . .
C43 C 1.0601(11) 0.1186(9) 0.6696(8) 0.090(4) Uani 1 1 d . . . . .
H43A H 1.0382 0.1867 0.6410 0.108 Uiso 1 1 calc R U . . .
H43B H 1.1052 0.1015 0.6251 0.108 Uiso 1 1 calc R U . . .
C41 C 0.9200(15) -0.0120(10) 0.7067(11) 0.109(5) Uani 1 1 d . . . . .
H41A H 0.8425 -0.0358 0.7452 0.131 Uiso 1 1 calc R U . . .
H41B H 1.0085 -0.0557 0.7369 0.131 Uiso 1 1 calc R U . . .
C39 C 0.4871(12) 0.4787(8) 0.9699(8) 0.077(4) Uani 1 1 d . . . . .
H39A H 0.5325 0.5091 0.9123 0.093 Uiso 1 1 calc R U . . .
H39B H 0.5303 0.4124 1.0007 0.093 Uiso 1 1 calc R U . . .
C22 C 0.1217(13) 0.8734(10) 1.0392(10) 0.109(5) Uani 1 1 d . . . . .
H22A H 0.0746 0.8698 1.0927 0.164 Uiso 1 1 calc R U . . .
H22B H 0.1927 0.9119 1.0252 0.164 Uiso 1 1 calc R U . . .
H22C H 0.0526 0.9006 0.9878 0.164 Uiso 1 1 calc R U . . .
C20 C 0.4375(13) 0.8727(11) 0.9164(13) 0.144(7) Uani 1 1 d . . . . .
H20A H 0.5371 0.8764 0.9124 0.215 Uiso 1 1 calc R U . . .
H20B H 0.3958 0.8930 0.8562 0.215 Uiso 1 1 calc R U . . .
H20C H 0.3895 0.9125 0.9403 0.215 Uiso 1 1 calc R U . . .
C42 C 0.8950(16) -0.0052(11) 0.6123(13) 0.145(7) Uani 1 1 d . . . . .
H42A H 0.8902 -0.0663 0.6205 0.218 Uiso 1 1 calc R U . . .
H42B H 0.8068 0.0374 0.5828 0.218 Uiso 1 1 calc R U . . .
H42C H 0.9725 0.0175 0.5746 0.218 Uiso 1 1 calc R U . . .
C44 C 1.1601(12) 0.0799(11) 0.7527(10) 0.158(8) Uani 1 1 d . . . . .
H44A H 1.2464 0.1046 0.7347 0.237 Uiso 1 1 calc R U . . .
H44B H 1.1157 0.0977 0.7963 0.237 Uiso 1 1 calc R U . . .
H44C H 1.1825 0.0125 0.7804 0.237 Uiso 1 1 calc R U . . .
C36 C -0.0801(13) 0.4526(10) 0.7948(10) 0.083(4) Uani 1 1 d . . . . .
H36 H -0.1680 0.4527 0.7720 0.099 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
Ni1 N2 1.882(8) . ?
Ni1 N1 1.903(6) . ?
Ni1 S2 2.182(3) . ?
Ni1 S1 2.208(3) . ?
Ni2 N5 1.878(9) . ?
Ni2 N4 1.891(8) . ?
Ni2 S3 2.195(4) . ?
Ni2 S4 2.200(3) . ?
S1 C18 1.710(9) . ?
S3 C40 1.729(10) . ?
S4 C40 1.736(13) . ?
S2 C18 1.701(12) . ?
O1 C11 1.360(12) . ?
O1 C16 1.431(12) . ?
O2 C33 1.379(11) . ?
O2 C38 1.425(11) . ?
N5 C31 1.314(12) . ?
N5 C28 1.399(12) . ?
N1 C1 1.366(11) . ?
N1 C4 1.383(11) . ?
N4 C23 1.340(12) . ?
N4 C26 1.382(12) . ?
N2 C9 1.332(11) . ?
N2 C6 1.402(11) . ?
N3 C18 1.309(12) . ?
N3 C21 1.444(14) . ?
N3 C19 1.515(13) . ?
C5 C6 1.391(11) . ?
C5 C4 1.394(12) . ?
C5 C10 1.492(13) . ?
N6 C40 1.313(13) . ?
N6 C43 1.464(12) . ?
N6 C41 1.481(15) . ?
C26 C27 1.382(13) . ?
C26 C25 1.397(14) . ?
C4 C3 1.402(11) . ?
C27 C28 1.374(13) . ?
C27 C32 1.463(13) . ?
C11 C10 1.378(14) . ?
C11 C12 1.394(14) . ?
C10 C15 1.396(14) . ?
C6 C7 1.408(13) . ?
C32 C33 1.389(13) . ?
C32 C37 1.391(12) . ?
C8 C7 1.355(12) . ?
C8 C9 1.386(14) . ?
C8 H8 0.9300 . ?
C28 C29 1.385(14) . ?
C33 C34 1.377(14) . ?
C23 C24 1.414(13) . ?
C23 H23 0.9300 . ?
C37 C36 1.378(15) . ?
C37 H37 0.9300 . ?
C7 H7 0.9300 . ?
C15 C14 1.380(14) . ?
C15 H15 0.9300 . ?
C13 C14 1.357(15) . ?
C13 C12 1.356(15) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C12 H12 0.9300 . ?
C25 C24 1.346(14) . ?
C25 H25 0.9300 . ?
C9 H9 0.9300 . ?
C1 C2 1.392(13) . ?
C1 H1 0.9300 . ?
C3 C2 1.338(14) . ?
C3 H3 0.9300 . ?
C38 C39 1.512(13) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C31 C30 1.357(15) . ?
C31 H31 0.9300 . ?
C2 H2 0.9300 . ?
C16 C17 1.512(15) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C34 C35 1.406(15) . ?
C34 H34 0.9300 . ?
C29 C30 1.376(14) . ?
C29 H29 0.9300 . ?
C17 C17 1.41(2) 2_476 ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C21 C22 1.492(16) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C24 H24 0.9300 . ?
C19 C20 1.411(16) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C30 H30 0.9300 . ?
C35 C36 1.349(16) . ?
C35 H35 0.9300 . ?
C43 C44 1.494(15) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C41 C42 1.536(18) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C39 C39 1.517(18) 2_667 ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C36 H36 0.9300 . ?

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 Ni1 N1 93.1(3) . . ?
N2 Ni1 S2 94.1(2) . . ?
N1 Ni1 S2 172.3(3) . . ?
N2 Ni1 S1 171.2(2) . . ?
N1 Ni1 S1 95.5(3) . . ?
S2 Ni1 S1 77.41(11) . . ?
N5 Ni2 N4 92.6(4) . . ?
N5 Ni2 S3 168.1(3) . . ?
N4 Ni2 S3 95.4(3) . . ?
N5 Ni2 S4 95.3(3) . . ?
N4 Ni2 S4 167.8(3) . . ?
S3 Ni2 S4 78.32(12) . . ?
C18 S1 Ni1 87.2(4) . . ?
C40 S3 Ni2 87.8(5) . . ?
C40 S4 Ni2 87.4(4) . . ?
C18 S2 Ni1 88.3(3) . . ?
C11 O1 C16 119.1(9) . . ?
C33 O2 C38 117.9(9) . . ?
C31 N5 C28 104.8(10) . . ?
C31 N5 Ni2 127.3(10) . . ?
C28 N5 Ni2 126.8(9) . . ?
C1 N1 C4 106.9(7) . . ?
C1 N1 Ni1 125.1(7) . . ?
C4 N1 Ni1 127.8(7) . . ?
C23 N4 C26 105.1(9) . . ?
C23 N4 Ni2 126.3(9) . . ?
C26 N4 Ni2 128.2(9) . . ?
C9 N2 C6 104.3(8) . . ?
C9 N2 Ni1 128.5(8) . . ?
C6 N2 Ni1 127.2(6) . . ?
C18 N3 C21 122.1(10) . . ?
C18 N3 C19 118.8(11) . . ?
C21 N3 C19 118.8(9) . . ?
C6 C5 C4 124.4(8) . . ?
C6 C5 C10 118.9(9) . . ?
C4 C5 C10 116.5(8) . . ?
C40 N6 C43 118.5(12) . . ?
C40 N6 C41 121.0(10) . . ?
C43 N6 C41 120.5(11) . . ?
N4 C26 C27 123.1(11) . . ?
N4 C26 C25 110.2(11) . . ?
C27 C26 C25 126.5(12) . . ?
N1 C4 C5 123.3(8) . . ?
N1 C4 C3 108.3(9) . . ?
C5 C4 C3 128.4(10) . . ?
C28 C27 C26 124.3(11) . . ?
C28 C27 C32 119.2(11) . . ?
C26 C27 C32 116.5(10) . . ?
O1 C11 C10 116.5(10) . . ?
O1 C11 C12 125.4(12) . . ?
C10 C11 C12 118.1(13) . . ?
C11 C10 C15 118.0(11) . . ?
C11 C10 C5 122.7(11) . . ?
C15 C10 C5 119.3(11) . . ?
C5 C6 N2 123.9(9) . . ?
C5 C6 C7 127.1(10) . . ?
N2 C6 C7 109.0(8) . . ?
C33 C32 C37 117.4(11) . . ?
C33 C32 C27 122.6(10) . . ?
C37 C32 C27 120.1(10) . . ?
C7 C8 C9 106.0(9) . . ?
C7 C8 H8 127.0 . . ?
C9 C8 H8 127.0 . . ?
C27 C28 C29 127.0(12) . . ?
C27 C28 N5 124.2(12) . . ?
C29 C28 N5 108.9(10) . . ?
C34 C33 O2 123.5(12) . . ?
C34 C33 C32 122.1(11) . . ?
O2 C33 C32 114.3(10) . . ?
N4 C23 C24 111.0(10) . . ?
N4 C23 H23 124.5 . . ?
C24 C23 H23 124.5 . . ?
C36 C37 C32 122.0(12) . . ?
C36 C37 H37 119.0 . . ?
C32 C37 H37 119.0 . . ?
N6 C40 S3 125.6(10) . . ?
N6 C40 S4 128.0(9) . . ?
S3 C40 S4 106.5(7) . . ?
C8 C7 C6 107.4(10) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
N3 C18 S2 127.6(8) . . ?
N3 C18 S1 125.2(9) . . ?
S2 C18 S1 107.2(6) . . ?
C14 C15 C10 122.7(11) . . ?
C14 C15 H15 118.7 . . ?
C10 C15 H15 118.7 . . ?
C14 C13 C12 119.9(12) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 118.4(13) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C13 C12 C11 122.8(12) . . ?
C13 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
C24 C25 C26 107.1(11) . . ?
C24 C25 H25 126.5 . . ?
C26 C25 H25 126.5 . . ?
N2 C9 C8 113.3(9) . . ?
N2 C9 H9 123.4 . . ?
C8 C9 H9 123.4 . . ?
N1 C1 C2 108.5(10) . . ?
N1 C1 H1 125.8 . . ?
C2 C1 H1 125.8 . . ?
C2 C3 C4 107.4(9) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
O2 C38 C39 107.5(9) . . ?
O2 C38 H38A 110.2 . . ?
C39 C38 H38A 110.2 . . ?
O2 C38 H38B 110.2 . . ?
C39 C38 H38B 110.2 . . ?
H38A C38 H38B 108.5 . . ?
N5 C31 C30 113.5(12) . . ?
N5 C31 H31 123.3 . . ?
C30 C31 H31 123.3 . . ?
C3 C2 C1 108.9(9) . . ?
C3 C2 H2 125.6 . . ?
C1 C2 H2 125.6 . . ?
O1 C16 C17 109.7(10) . . ?
O1 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
O1 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C33 C34 C35 117.5(12) . . ?
C33 C34 H34 121.2 . . ?
C35 C34 H34 121.2 . . ?
C30 C29 C28 106.7(12) . . ?
C30 C29 H29 126.7 . . ?
C28 C29 H29 126.7 . . ?
C17 C17 C16 114.5(15) 2_476 . ?
C17 C17 H17A 108.6 2_476 . ?
C16 C17 H17A 108.6 . . ?
C17 C17 H17B 108.6 2_476 . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
N3 C21 C22 112.5(12) . . ?
N3 C21 H21A 109.1 . . ?
C22 C21 H21A 109.1 . . ?
N3 C21 H21B 109.1 . . ?
C22 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C25 C24 C23 106.6(11) . . ?
C25 C24 H24 126.7 . . ?
C23 C24 H24 126.7 . . ?
C20 C19 N3 107.3(12) . . ?
C20 C19 H19A 110.2 . . ?
N3 C19 H19A 110.2 . . ?
C20 C19 H19B 110.2 . . ?
N3 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
C31 C30 C29 106.1(12) . . ?
C31 C30 H30 126.9 . . ?
C29 C30 H30 126.9 . . ?
C36 C35 C34 122.1(13) . . ?
C36 C35 H35 118.9 . . ?
C34 C35 H35 118.9 . . ?
N6 C43 C44 110.1(10) . . ?
N6 C43 H43A 109.6 . . ?
C44 C43 H43A 109.6 . . ?
N6 C43 H43B 109.6 . . ?
C44 C43 H43B 109.6 . . ?
H43A C43 H43B 108.2 . . ?
N6 C41 C42 110.6(12) . . ?
N6 C41 H41A 109.5 . . ?
C42 C41 H41A 109.5 . . ?
N6 C41 H41B 109.5 . . ?
C42 C41 H41B 109.5 . . ?
H41A C41 H41B 108.1 . . ?
C38 C39 C39 111.5(12) . 2_667 ?
C38 C39 H39A 109.3 . . ?
C39 C39 H39A 109.3 2_667 . ?
C38 C39 H39B 109.3 . . ?
C39 C39 H39B 109.3 2_667 . ?
H39A C39 H39B 108.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C35 C36 C37 118.8(12) . . ?
C35 C36 H36 120.6 . . ?
C37 C36 H36 120.6 . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.072

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1505320'
_audit_update_record             
;
2017-03-09 deposited with the CCDC.
2017-03-24 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         'C39 H38 Cu N4 O2'
_chemical_formula_sum            'C39 H38 Cu N4 O2'
_chemical_formula_weight         658.27

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                   25.9984(10)
_cell_length_b                   9.3703(2)
_cell_length_c                   28.3965(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.343(3)
_cell_angle_gamma                90
_cell_volume                     6671.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3743
_cell_measurement_theta_min      3.3600
_cell_measurement_theta_max      21.7280

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             2760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.695
_shelx_estimated_absorpt_T_min   0.803
_shelx_estimated_absorpt_T_max   0.868
_exptl_absorpt_correction_T_min  0.37759
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            26373
_diffrn_reflns_av_unetI/netI     0.0999
_diffrn_reflns_av_R_equivalents  0.1095
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.067
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5865
_reflns_number_gt                3345
_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       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+3.2172P] 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         5865
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1611
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
Cu1 Cu 0.67148(2) 0.20320(6) 0.14329(2) 0.0508(2) Uani 1 1 d . . . . .
O1 O 0.56937(16) 0.0313(4) -0.03049(12) 0.0707(11) Uani 1 1 d . . . . .
O2 O 0.60400(17) 0.6226(4) 0.22689(13) 0.0838(13) Uani 1 1 d . . . . .
N1 N 0.66601(16) 0.0031(4) 0.12319(13) 0.0510(10) Uani 1 1 d . . . . .
N2 N 0.67411(16) 0.2674(4) 0.07891(13) 0.0546(11) Uani 1 1 d . . . . .
N3 N 0.62798(16) 0.1932(4) 0.18988(13) 0.0502(10) Uani 1 1 d . . . . .
N4 N 0.71522(17) 0.3565(4) 0.18012(13) 0.0496(10) Uani 1 1 d . . . . .
C1 C 0.6656(2) -0.1108(5) 0.15095(18) 0.0592(14) Uani 1 1 d . . . . .
H1 H 0.6676 -0.1057 0.1841 0.071 Uiso 1 1 calc R U . . .
C2 C 0.6619(2) -0.2384(5) 0.1254(2) 0.0644(15) Uani 1 1 d . . . . .
H2 H 0.6606 -0.3300 0.1376 0.077 Uiso 1 1 calc R U . . .
C3 C 0.6607(2) -0.2010(5) 0.07855(18) 0.0593(14) Uani 1 1 d . . . . .
H3 H 0.6582 -0.2632 0.0525 0.071 Uiso 1 1 calc R U . . .
C4 C 0.66383(19) -0.0496(5) 0.07694(16) 0.0467(12) Uani 1 1 d . . . . .
C5 C 0.66513(19) 0.0341(5) 0.03743(17) 0.0505(12) Uani 1 1 d . . . . .
C6 C 0.6706(2) 0.1834(5) 0.03758(16) 0.0521(13) Uani 1 1 d . . . . .
C7 C 0.6698(2) 0.2747(6) -0.00195(19) 0.0746(17) Uani 1 1 d . . . . .
H7 H 0.6682 0.2464 -0.0337 0.089 Uiso 1 1 calc R U . . .
C8 C 0.6718(3) 0.4122(6) 0.0143(2) 0.085(2) Uani 1 1 d . . . . .
H8 H 0.6714 0.4949 -0.0038 0.102 Uiso 1 1 calc R U . . .
C9 C 0.6743(2) 0.4025(5) 0.0639(2) 0.0712(17) Uani 1 1 d . . . . .
H9 H 0.6759 0.4812 0.0842 0.085 Uiso 1 1 calc R U . . .
C10 C 0.5862(2) 0.1080(5) 0.1865(2) 0.0652(15) Uani 1 1 d . . . . .
H10 H 0.5757 0.0366 0.1631 0.078 Uiso 1 1 calc R U . . .
C11 C 0.5599(2) 0.1390(6) 0.2222(2) 0.0797(18) Uani 1 1 d . . . . .
H11 H 0.5296 0.0943 0.2267 0.096 Uiso 1 1 calc R U . . .
C12 C 0.5878(2) 0.2482(6) 0.2492(2) 0.0658(15) Uani 1 1 d . . . . .
H12 H 0.5802 0.2910 0.2761 0.079 Uiso 1 1 calc R U . . .
C13 C 0.6299(2) 0.2844(5) 0.22912(16) 0.0479(12) Uani 1 1 d . . . . .
C14 C 0.6673(2) 0.3943(5) 0.24291(17) 0.0489(12) Uani 1 1 d . . . . .
C15 C 0.7075(2) 0.4275(5) 0.22116(16) 0.0492(12) Uani 1 1 d . . . . .
C16 C 0.7477(2) 0.5322(5) 0.23541(18) 0.0609(15) Uani 1 1 d . . . . .
H16 H 0.7515 0.5960 0.2612 0.073 Uiso 1 1 calc R U . . .
C17 C 0.7798(2) 0.5235(6) 0.20481(19) 0.0673(15) Uani 1 1 d . . . . .
H17 H 0.8100 0.5781 0.2059 0.081 Uiso 1 1 calc R U . . .
C18 C 0.7582(2) 0.4150(5) 0.17100(18) 0.0606(14) Uani 1 1 d . . . . .
H18 H 0.7723 0.3876 0.1455 0.073 Uiso 1 1 calc R U . . .
C19 C 0.6590(2) -0.0341(5) -0.01152(18) 0.0571(14) Uani 1 1 d . . . . .
C20 C 0.7008(3) -0.0986(6) -0.0242(2) 0.0842(19) Uani 1 1 d . . . . .
H20 H 0.7335 -0.1074 -0.0009 0.101 Uiso 1 1 calc R U . . .
C21 C 0.6955(3) -0.1508(7) -0.0709(3) 0.097(2) Uani 1 1 d . . . . .
H21 H 0.7243 -0.1935 -0.0790 0.117 Uiso 1 1 calc R U . . .
C22 C 0.6479(3) -0.1393(7) -0.1048(2) 0.092(2) Uani 1 1 d . . . . .
H22 H 0.6442 -0.1753 -0.1361 0.111 Uiso 1 1 calc R U . . .
C23 C 0.6052(3) -0.0753(6) -0.0937(2) 0.0810(18) Uani 1 1 d . . . . .
H23 H 0.5728 -0.0664 -0.1173 0.097 Uiso 1 1 calc R U . . .
C24 C 0.6108(2) -0.0238(5) -0.04668(19) 0.0608(14) Uani 1 1 d . . . . .
C25 C 0.6628(2) 0.4870(5) 0.28499(17) 0.0516(12) Uani 1 1 d . . . . .
C26 C 0.6917(2) 0.4636(6) 0.33252(19) 0.0751(17) Uani 1 1 d . . . . .
H26 H 0.7152 0.3870 0.3397 0.090 Uiso 1 1 calc R U . . .
C27 C 0.6861(3) 0.5536(8) 0.3699(2) 0.087(2) Uani 1 1 d . . . . .
H27 H 0.7053 0.5361 0.4020 0.105 Uiso 1 1 calc R U . . .
C28 C 0.6526(3) 0.6667(8) 0.3592(2) 0.087(2) Uani 1 1 d . . . . .
H28 H 0.6487 0.7260 0.3843 0.104 Uiso 1 1 calc R U . . .
C29 C 0.6244(3) 0.6954(6) 0.3124(2) 0.0769(17) Uani 1 1 d . . . . .
H29 H 0.6019 0.7743 0.3056 0.092 Uiso 1 1 calc R U . . .
C30 C 0.6296(2) 0.6053(5) 0.27478(18) 0.0593(14) Uani 1 1 d . . . . .
C31 C 0.5322(3) 0.1192(7) -0.0628(2) 0.093(2) Uani 1 1 d . . . . .
H31A H 0.5119 0.0635 -0.0903 0.112 Uiso 1 1 calc R U . . .
H31B H 0.5505 0.1946 -0.0752 0.112 Uiso 1 1 calc R U . . .
C32 C 0.4950(3) 0.1831(7) -0.0350(2) 0.0829(19) Uani 1 1 d . . . . .
H32A H 0.4736 0.1069 -0.0268 0.099 Uiso 1 1 calc R U . . .
H32B H 0.4708 0.2486 -0.0565 0.099 Uiso 1 1 calc R U . . .
C33 C 0.5229(3) 0.2623(6) 0.0117(2) 0.088(2) Uani 1 1 d . . . . .
H33A H 0.5460 0.1960 0.0338 0.106 Uiso 1 1 calc R U . . .
H33B H 0.5452 0.3364 0.0037 0.106 Uiso 1 1 calc R U . . .
C34 C 0.4854(3) 0.3296(6) 0.0377(3) 0.092(2) Uani 1 1 d . . . . .
H34A H 0.4612 0.2567 0.0434 0.110 Uiso 1 1 calc R U . . .
H34B H 0.4641 0.4009 0.0164 0.110 Uiso 1 1 calc R U . . .
C35 C 0.5121(3) 0.3995(6) 0.0861(3) 0.096(2) Uani 1 1 d . . . . .
H35A H 0.5338 0.4782 0.0802 0.115 Uiso 1 1 calc R U . . .
H35B H 0.5357 0.3307 0.1065 0.115 Uiso 1 1 calc R U . . .
C36 C 0.4735(3) 0.4553(7) 0.1136(3) 0.102(2) Uani 1 1 d . . . . .
H36A H 0.4501 0.3783 0.1175 0.123 Uiso 1 1 calc R U . . .
H36B H 0.4516 0.5294 0.0943 0.123 Uiso 1 1 calc R U . . .
C37 C 0.5015(3) 0.5163(7) 0.1643(3) 0.103(2) Uani 1 1 d . . . . .
H37A H 0.4758 0.5180 0.1836 0.124 Uiso 1 1 calc R U . . .
H37B H 0.5297 0.4509 0.1801 0.124 Uiso 1 1 calc R U . . .
C38 C 0.5248(3) 0.6600(7) 0.1656(2) 0.094(2) Uani 1 1 d . . . . .
H38A H 0.4961 0.7279 0.1540 0.113 Uiso 1 1 calc R U . . .
H38B H 0.5470 0.6624 0.1431 0.113 Uiso 1 1 calc R U . . .
C39 C 0.5573(3) 0.7075(6) 0.2144(2) 0.0813(18) Uani 1 1 d . . . . .
H39A H 0.5666 0.8075 0.2134 0.098 Uiso 1 1 calc R U . . .
H39B H 0.5372 0.6958 0.2386 0.098 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 1.943(4) . ?
Cu1 N1 1.954(4) . ?
Cu1 N4 1.955(4) . ?
Cu1 N3 1.957(4) . ?
O1 C24 1.379(6) . ?
O1 C31 1.410(6) . ?
O2 C30 1.356(6) . ?
O2 C39 1.417(6) . ?
N1 C1 1.329(5) . ?
N1 C4 1.390(5) . ?
N2 C9 1.337(6) . ?
N2 C6 1.396(5) . ?
N3 C10 1.331(6) . ?
N3 C13 1.395(5) . ?
N4 C18 1.331(6) . ?
N4 C15 1.402(5) . ?
C1 C2 1.389(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.367(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.423(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(6) . ?
C5 C6 1.406(6) . ?
C5 C19 1.500(6) . ?
C6 C7 1.407(6) . ?
C7 C8 1.365(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(7) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.394(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.402(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.399(6) . ?
C14 C15 1.383(7) . ?
C14 C25 1.507(6) . ?
C15 C16 1.413(6) . ?
C16 C17 1.358(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.409(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.373(7) . ?
C19 C24 1.383(7) . ?
C20 C21 1.387(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.356(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.371(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.391(7) . ?
C23 H23 0.9300 . ?
C25 C26 1.378(7) . ?
C25 C30 1.387(7) . ?
C26 C27 1.393(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.355(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.363(8) . ?
C28 H28 0.9300 . ?
C29 C30 1.397(7) . ?
C29 H29 0.9300 . ?
C31 C32 1.524(8) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.527(8) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.509(8) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.514(8) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.517(9) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.541(8) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C38 1.472(8) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.487(8) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N1 92.29(16) . . ?
N2 Cu1 N4 96.65(15) . . ?
N1 Cu1 N4 148.05(16) . . ?
N2 Cu1 N3 145.22(17) . . ?
N1 Cu1 N3 98.11(16) . . ?
N4 Cu1 N3 91.84(16) . . ?
C24 O1 C31 117.6(5) . . ?
C30 O2 C39 118.6(4) . . ?
C1 N1 C4 105.7(4) . . ?
C1 N1 Cu1 127.5(3) . . ?
C4 N1 Cu1 126.8(3) . . ?
C9 N2 C6 105.7(4) . . ?
C9 N2 Cu1 126.7(3) . . ?
C6 N2 Cu1 127.3(3) . . ?
C10 N3 C13 106.3(4) . . ?
C10 N3 Cu1 125.9(3) . . ?
C13 N3 Cu1 127.3(3) . . ?
C18 N4 C15 106.3(4) . . ?
C18 N4 Cu1 126.7(3) . . ?
C15 N4 Cu1 127.0(3) . . ?
N1 C1 C2 113.0(5) . . ?
N1 C1 H1 123.5 . . ?
C2 C1 H1 123.5 . . ?
C3 C2 C1 105.6(4) . . ?
C3 C2 H2 127.2 . . ?
C1 C2 H2 127.2 . . ?
C2 C3 C4 107.4(4) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
C5 C4 N1 124.3(4) . . ?
C5 C4 C3 127.5(4) . . ?
N1 C4 C3 108.2(4) . . ?
C4 C5 C6 126.1(4) . . ?
C4 C5 C19 119.5(4) . . ?
C6 C5 C19 114.4(4) . . ?
N2 C6 C5 123.2(4) . . ?
N2 C6 C7 108.2(4) . . ?
C5 C6 C7 128.5(4) . . ?
C8 C7 C6 108.2(5) . . ?
C8 C7 H7 125.9 . . ?
C6 C7 H7 125.9 . . ?
C7 C8 C9 105.5(5) . . ?
C7 C8 H8 127.2 . . ?
C9 C8 H8 127.2 . . ?
N2 C9 C8 112.4(5) . . ?
N2 C9 H9 123.8 . . ?
C8 C9 H9 123.8 . . ?
N3 C10 C11 111.7(5) . . ?
N3 C10 H10 124.2 . . ?
C11 C10 H10 124.2 . . ?
C12 C11 C10 106.0(5) . . ?
C12 C11 H11 127.0 . . ?
C10 C11 H11 127.0 . . ?
C11 C12 C13 107.9(5) . . ?
C11 C12 H12 126.1 . . ?
C13 C12 H12 126.1 . . ?
N3 C13 C14 123.3(4) . . ?
N3 C13 C12 108.1(4) . . ?
C14 C13 C12 128.5(5) . . ?
C15 C14 C13 126.3(4) . . ?
C15 C14 C25 116.8(4) . . ?
C13 C14 C25 116.9(4) . . ?
C14 C15 N4 123.8(4) . . ?
C14 C15 C16 128.2(4) . . ?
N4 C15 C16 108.0(4) . . ?
C17 C16 C15 108.0(5) . . ?
C17 C16 H16 126.0 . . ?
C15 C16 H16 126.0 . . ?
C16 C17 C18 106.2(5) . . ?
C16 C17 H17 126.9 . . ?
C18 C17 H17 126.9 . . ?
N4 C18 C17 111.6(5) . . ?
N4 C18 H18 124.2 . . ?
C17 C18 H18 124.2 . . ?
C20 C19 C24 118.1(5) . . ?
C20 C19 C5 122.2(5) . . ?
C24 C19 C5 119.6(5) . . ?
C19 C20 C21 121.3(6) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C22 C21 C20 119.6(7) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 120.9(6) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C24 119.1(6) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
O1 C24 C19 115.1(5) . . ?
O1 C24 C23 123.8(6) . . ?
C19 C24 C23 121.0(6) . . ?
C26 C25 C30 118.7(5) . . ?
C26 C25 C14 123.3(5) . . ?
C30 C25 C14 118.0(4) . . ?
C25 C26 C27 120.7(6) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C28 C27 C26 119.5(6) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C29 121.5(6) . . ?
C27 C28 H28 119.3 . . ?
C29 C28 H28 119.3 . . ?
C28 C29 C30 119.3(6) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
O2 C30 C25 114.7(4) . . ?
O2 C30 C29 125.0(5) . . ?
C25 C30 C29 120.3(5) . . ?
O1 C31 C32 108.2(5) . . ?
O1 C31 H31A 110.1 . . ?
C32 C31 H31A 110.1 . . ?
O1 C31 H31B 110.1 . . ?
C32 C31 H31B 110.1 . . ?
H31A C31 H31B 108.4 . . ?
C31 C32 C33 114.9(6) . . ?
C31 C32 H32A 108.5 . . ?
C33 C32 H32A 108.5 . . ?
C31 C32 H32B 108.5 . . ?
C33 C32 H32B 108.5 . . ?
H32A C32 H32B 107.5 . . ?
C34 C33 C32 114.1(6) . . ?
C34 C33 H33A 108.7 . . ?
C32 C33 H33A 108.7 . . ?
C34 C33 H33B 108.7 . . ?
C32 C33 H33B 108.7 . . ?
H33A C33 H33B 107.6 . . ?
C33 C34 C35 115.1(6) . . ?
C33 C34 H34A 108.5 . . ?
C35 C34 H34A 108.5 . . ?
C33 C34 H34B 108.5 . . ?
C35 C34 H34B 108.5 . . ?
H34A C34 H34B 107.5 . . ?
C34 C35 C36 114.1(6) . . ?
C34 C35 H35A 108.7 . . ?
C36 C35 H35A 108.7 . . ?
C34 C35 H35B 108.7 . . ?
C36 C35 H35B 108.7 . . ?
H35A C35 H35B 107.6 . . ?
C35 C36 C37 113.3(6) . . ?
C35 C36 H36A 108.9 . . ?
C37 C36 H36A 108.9 . . ?
C35 C36 H36B 108.9 . . ?
C37 C36 H36B 108.9 . . ?
H36A C36 H36B 107.7 . . ?
C38 C37 C36 116.9(6) . . ?
C38 C37 H37A 108.1 . . ?
C36 C37 H37A 108.1 . . ?
C38 C37 H37B 108.1 . . ?
C36 C37 H37B 108.1 . . ?
H37A C37 H37B 107.3 . . ?
C37 C38 C39 115.3(6) . . ?
C37 C38 H38A 108.5 . . ?
C39 C38 H38A 108.5 . . ?
C37 C38 H38B 108.5 . . ?
C39 C38 H38B 108.5 . . ?
H38A C38 H38B 107.5 . . ?
O2 C39 C38 107.6(5) . . ?
O2 C39 H39A 110.2 . . ?
C38 C39 H39A 110.2 . . ?
O2 C39 H39B 110.2 . . ?
C38 C39 H39B 110.2 . . ?
H39A C39 H39B 108.5 . . ?

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
C4 N1 C1 C2 -1.5(6) . . . . ?
Cu1 N1 C1 C2 -179.2(4) . . . . ?
N1 C1 C2 C3 0.8(6) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
C1 N1 C4 C5 -177.9(5) . . . . ?
Cu1 N1 C4 C5 -0.1(7) . . . . ?
C1 N1 C4 C3 1.5(5) . . . . ?
Cu1 N1 C4 C3 179.3(3) . . . . ?
C2 C3 C4 C5 178.3(5) . . . . ?
C2 C3 C4 N1 -1.1(6) . . . . ?
N1 C4 C5 C6 2.3(8) . . . . ?
C3 C4 C5 C6 -177.0(5) . . . . ?
N1 C4 C5 C19 -176.1(5) . . . . ?
C3 C4 C5 C19 4.5(8) . . . . ?
C9 N2 C6 C5 -174.8(5) . . . . ?
Cu1 N2 C6 C5 -0.8(7) . . . . ?
C9 N2 C6 C7 1.1(6) . . . . ?
Cu1 N2 C6 C7 175.1(4) . . . . ?
C4 C5 C6 N2 -1.8(8) . . . . ?
C19 C5 C6 N2 176.7(5) . . . . ?
C4 C5 C6 C7 -176.8(5) . . . . ?
C19 C5 C6 C7 1.7(8) . . . . ?
N2 C6 C7 C8 -1.0(7) . . . . ?
C5 C6 C7 C8 174.6(5) . . . . ?
C6 C7 C8 C9 0.6(7) . . . . ?
C6 N2 C9 C8 -0.7(7) . . . . ?
Cu1 N2 C9 C8 -174.8(4) . . . . ?
C7 C8 C9 N2 0.1(8) . . . . ?
C13 N3 C10 C11 -0.1(6) . . . . ?
Cu1 N3 C10 C11 -172.7(4) . . . . ?
N3 C10 C11 C12 -0.7(7) . . . . ?
C10 C11 C12 C13 1.2(7) . . . . ?
C10 N3 C13 C14 -177.1(4) . . . . ?
Cu1 N3 C13 C14 -4.6(6) . . . . ?
C10 N3 C13 C12 0.8(5) . . . . ?
Cu1 N3 C13 C12 173.2(3) . . . . ?
C11 C12 C13 N3 -1.2(6) . . . . ?
C11 C12 C13 C14 176.5(5) . . . . ?
N3 C13 C14 C15 -1.1(8) . . . . ?
C12 C13 C14 C15 -178.5(5) . . . . ?
N3 C13 C14 C25 177.8(4) . . . . ?
C12 C13 C14 C25 0.4(7) . . . . ?
C13 C14 C15 N4 2.3(8) . . . . ?
C25 C14 C15 N4 -176.5(4) . . . . ?
C13 C14 C15 C16 -176.4(5) . . . . ?
C25 C14 C15 C16 4.7(7) . . . . ?
C18 N4 C15 C14 -178.1(5) . . . . ?
Cu1 N4 C15 C14 2.2(7) . . . . ?
C18 N4 C15 C16 0.8(5) . . . . ?
Cu1 N4 C15 C16 -178.8(3) . . . . ?
C14 C15 C16 C17 177.5(5) . . . . ?
N4 C15 C16 C17 -1.4(6) . . . . ?
C15 C16 C17 C18 1.4(6) . . . . ?
C15 N4 C18 C17 0.1(6) . . . . ?
Cu1 N4 C18 C17 179.7(3) . . . . ?
C16 C17 C18 N4 -0.9(6) . . . . ?
C4 C5 C19 C20 -81.5(7) . . . . ?
C6 C5 C19 C20 99.9(6) . . . . ?
C4 C5 C19 C24 103.1(6) . . . . ?
C6 C5 C19 C24 -75.5(6) . . . . ?
C24 C19 C20 C21 0.7(9) . . . . ?
C5 C19 C20 C21 -174.7(5) . . . . ?
C19 C20 C21 C22 -0.5(10) . . . . ?
C20 C21 C22 C23 0.7(11) . . . . ?
C21 C22 C23 C24 -1.0(10) . . . . ?
C31 O1 C24 C19 143.9(5) . . . . ?
C31 O1 C24 C23 -40.3(7) . . . . ?
C20 C19 C24 O1 174.8(5) . . . . ?
C5 C19 C24 O1 -9.6(7) . . . . ?
C20 C19 C24 C23 -1.1(8) . . . . ?
C5 C19 C24 C23 174.5(5) . . . . ?
C22 C23 C24 O1 -174.3(5) . . . . ?
C22 C23 C24 C19 1.2(9) . . . . ?
C15 C14 C25 C26 -85.8(6) . . . . ?
C13 C14 C25 C26 95.2(6) . . . . ?
C15 C14 C25 C30 91.2(6) . . . . ?
C13 C14 C25 C30 -87.8(6) . . . . ?
C30 C25 C26 C27 2.6(8) . . . . ?
C14 C25 C26 C27 179.6(5) . . . . ?
C25 C26 C27 C28 -1.2(10) . . . . ?
C26 C27 C28 C29 -0.6(11) . . . . ?
C27 C28 C29 C30 0.9(10) . . . . ?
C39 O2 C30 C25 159.2(5) . . . . ?
C39 O2 C30 C29 -20.6(8) . . . . ?
C26 C25 C30 O2 177.9(5) . . . . ?
C14 C25 C30 O2 0.8(7) . . . . ?
C26 C25 C30 C29 -2.3(8) . . . . ?
C14 C25 C30 C29 -179.4(5) . . . . ?
C28 C29 C30 O2 -179.7(6) . . . . ?
C28 C29 C30 C25 0.5(9) . . . . ?
C24 O1 C31 C32 -172.4(5) . . . . ?
O1 C31 C32 C33 54.5(7) . . . . ?
C31 C32 C33 C34 177.8(5) . . . . ?
C32 C33 C34 C35 175.7(5) . . . . ?
C33 C34 C35 C36 -175.1(6) . . . . ?
C34 C35 C36 C37 175.9(5) . . . . ?
C35 C36 C37 C38 77.7(8) . . . . ?
C36 C37 C38 C39 -172.5(6) . . . . ?
C30 O2 C39 C38 -155.3(5) . . . . ?
C37 C38 C39 O2 68.5(7) . . . . ?

_refine_diff_density_max         0.479
_refine_diff_density_min         -0.413
_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_41
_database_code_depnum_ccdc_archive 'CCDC 1505321'
_audit_update_record             
;
2017-03-09 deposited with the CCDC.
2017-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H21 Cu N2 O3'
_chemical_formula_sum            'C22 H21 Cu N2 O3'
_exptl_crystal_recrystallization_method DCM/Hexane
_chemical_melting_point          ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Red

_diffrn_ambient_temperature      273(2)
_chemical_formula_weight         424.95

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.2758(2)
_cell_length_b                   14.6438(6)
_cell_length_c                   18.4718(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.516(3)
_cell_angle_gamma                90.00
_cell_volume                     1967.40(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    5700
_cell_measurement_theta_min      3.5680
_cell_measurement_theta_max      30.4130
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    1.135
_exptl_absorpt_correction_T_min  0.7883
_exptl_absorpt_correction_T_max  0.8758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25113
_diffrn_reflns_av_R_equivalents  0.1085
_diffrn_reflns_av_sigmaI/netI    0.1202
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         32.55
_reflns_number_total             6593
_reflns_number_gt                2648
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0838P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6593
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1732
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.2148
_refine_ls_wR_factor_gt          0.1494
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.981
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H17B H 0.964(6) 0.906(3) 0.500(3) 0.084(16) Uiso 1 1 d . . .
H17A H 0.853(8) 0.966(3) 0.538(3) 0.10(2) Uiso 1 1 d . . .
Cu1 Cu -0.33150(6) 0.95174(3) 0.12977(3) 0.0559(2) Uani 1 1 d . . .
O2 O -0.5246(4) 1.04172(17) 0.11602(17) 0.0630(8) Uani 1 1 d . . .
N1 N -0.1934(4) 1.0402(2) 0.18982(19) 0.0569(8) Uani 1 1 d . . .
O1 O -0.4667(4) 0.86527(19) 0.06971(17) 0.0699(8) Uani 1 1 d . . .
N2 N -0.1432(4) 0.8582(2) 0.14712(18) 0.0577(8) Uani 1 1 d . . .
C5 C 0.0504(5) 0.9382(3) 0.2389(2) 0.0565(10) Uani 1 1 d . . .
C6 C 0.0074(5) 0.8625(3) 0.1957(2) 0.0558(10) Uani 1 1 d . . .
C4 C -0.0421(5) 1.0223(3) 0.2351(2) 0.0556(10) Uani 1 1 d . . .
O3 O 0.6471(4) 0.9157(2) 0.44028(18) 0.0803(10) Uani 1 1 d . . .
C21 C -0.6238(5) 0.8775(3) 0.0386(2) 0.0633(11) Uani 1 1 d . . .
C20 C -0.7281(6) 0.9546(3) 0.0436(3) 0.0660(12) Uani 1 1 d . . .
H20 H -0.8421 0.9549 0.0196 0.079 Uiso 1 1 calc R . .
C7 C 0.1078(5) 0.7811(3) 0.1887(3) 0.0683(12) Uani 1 1 d . . .
H7 H 0.2137 0.7653 0.2151 0.082 Uiso 1 1 calc R . .
C9 C -0.1306(6) 0.7785(3) 0.1127(2) 0.0653(11) Uani 1 1 d . . .
H9 H -0.2140 0.7583 0.0771 0.078 Uiso 1 1 calc R . .
C19 C -0.6776(5) 1.0321(3) 0.0815(2) 0.0598(10) Uani 1 1 d . . .
C11 C 0.3616(5) 0.9877(3) 0.2837(2) 0.0643(11) Uani 1 1 d . . .
H11 H 0.3618 1.0303 0.2463 0.077 Uiso 1 1 calc R . .
C3 C -0.0028(6) 1.1029(3) 0.2761(2) 0.0625(11) Uani 1 1 d . . .
H3 H 0.0899 1.1098 0.3113 0.075 Uiso 1 1 calc R . .
C17 C 0.9230(8) 0.9653(4) 0.4993(4) 0.0785(16) Uani 1 1 d . . .
C10 C 0.2118(5) 0.9300(3) 0.2898(2) 0.0604(11) Uani 1 1 d . . .
C12 C 0.5113(5) 0.9837(3) 0.3318(2) 0.0650(11) Uani 1 1 d . . .
H12 H 0.6113 1.0223 0.3260 0.078 Uiso 1 1 calc R . .
C8 C 0.0225(6) 0.7295(3) 0.1365(3) 0.0755(13) Uani 1 1 d . . .
H8 H 0.0597 0.6726 0.1200 0.091 Uiso 1 1 calc R . .
C22 C -0.6893(6) 0.7968(3) -0.0061(3) 0.0829(14) Uani 1 1 d . . .
H22A H -0.5995 0.7825 -0.0415 0.124 Uiso 1 1 calc R . .
H22B H -0.8040 0.8117 -0.0302 0.124 Uiso 1 1 calc R . .
H22C H -0.7059 0.7451 0.0249 0.124 Uiso 1 1 calc R . .
C1 C -0.2404(5) 1.1268(3) 0.2019(2) 0.0638(11) Uani 1 1 d . . .
H1 H -0.3381 1.1564 0.1784 0.077 Uiso 1 1 calc R . .
C13 C 0.5105(5) 0.9219(3) 0.3885(3) 0.0653(11) Uani 1 1 d . . .
C2 C -0.1253(6) 1.1676(3) 0.2542(2) 0.0693(12) Uani 1 1 d . . .
H2 H -0.1315 1.2275 0.2707 0.083 Uiso 1 1 calc R . .
C15 C 0.2143(6) 0.8672(3) 0.3464(3) 0.0698(12) Uani 1 1 d . . .
H15 H 0.1161 0.8272 0.3514 0.084 Uiso 1 1 calc R . .
C18 C -0.8019(6) 1.1136(3) 0.0834(3) 0.0742(13) Uani 1 1 d . . .
H18A H -0.7440 1.1610 0.1117 0.111 Uiso 1 1 calc R . .
H18B H -0.9158 1.0967 0.1048 0.111 Uiso 1 1 calc R . .
H18C H -0.8255 1.1352 0.0350 0.111 Uiso 1 1 calc R . .
C14 C 0.3613(6) 0.8638(3) 0.3951(3) 0.0756(14) Uani 1 1 d . . .
H14 H 0.3603 0.8219 0.4329 0.091 Uiso 1 1 calc R . .
C16 C 0.7890(6) 0.9813(3) 0.4376(3) 0.0761(14) Uani 1 1 d . . .
H16A H 0.7376 1.0422 0.4409 0.091 Uiso 1 1 calc R . .
H16B H 0.8513 0.9764 0.3920 0.091 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.935(3) . ?
Cu1 O2 1.938(3) . ?
Cu1 N2 1.958(3) . ?
Cu1 N1 1.965(3) . ?
O2 C19 1.276(5) . ?
N1 C1 1.334(5) . ?
N1 C4 1.390(5) . ?
O1 C21 1.279(4) . ?
N2 C9 1.333(5) . ?
N2 C6 1.400(5) . ?
C5 C6 1.396(5) . ?
C5 C4 1.404(5) . ?
C5 C10 1.489(5) . ?
C6 C7 1.405(5) . ?
C4 C3 1.428(5) . ?
O3 C13 1.364(4) . ?
O3 C16 1.412(5) . ?
C21 C20 1.365(6) . ?
C21 C22 1.511(6) . ?
C20 C19 1.378(6) . ?
C20 H20 0.9300 . ?
C7 C8 1.362(6) . ?
C7 H7 0.9300 . ?
C9 C8 1.387(5) . ?
C9 H9 0.9300 . ?
C19 C18 1.498(6) . ?
C11 C10 1.386(6) . ?
C11 C12 1.389(5) . ?
C11 H11 0.9300 . ?
C3 C2 1.355(5) . ?
C3 H3 0.9300 . ?
C17 C16 1.499(6) . ?
C17 C17 1.513(10) 3_776 ?
C17 H17B 0.92(4) . ?
C17 H17A 0.89(6) . ?
C10 C15 1.393(5) . ?
C12 C13 1.385(6) . ?
C12 H12 0.9300 . ?
C8 H8 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C1 C2 1.395(6) . ?
C1 H1 0.9300 . ?
C13 C14 1.387(6) . ?
C2 H2 0.9300 . ?
C15 C14 1.380(6) . ?
C15 H15 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 H14 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 90.81(12) . . ?
O1 Cu1 N2 88.78(13) . . ?
O2 Cu1 N2 177.35(14) . . ?
O1 Cu1 N1 179.39(14) . . ?
O2 Cu1 N1 89.07(12) . . ?
N2 Cu1 N1 91.37(13) . . ?
C19 O2 Cu1 127.6(3) . . ?
C1 N1 C4 106.3(3) . . ?
C1 N1 Cu1 126.3(3) . . ?
C4 N1 Cu1 126.9(3) . . ?
C21 O1 Cu1 127.0(3) . . ?
C9 N2 C6 106.5(3) . . ?
C9 N2 Cu1 126.2(3) . . ?
C6 N2 Cu1 127.3(3) . . ?
C6 C5 C4 124.6(4) . . ?
C6 C5 C10 117.2(4) . . ?
C4 C5 C10 118.1(4) . . ?
C5 C6 N2 124.2(3) . . ?
C5 C6 C7 128.1(4) . . ?
N2 C6 C7 107.6(4) . . ?
N1 C4 C5 124.5(4) . . ?
N1 C4 C3 107.9(3) . . ?
C5 C4 C3 127.6(4) . . ?
C13 O3 C16 116.8(3) . . ?
O1 C21 C20 125.2(4) . . ?
O1 C21 C22 113.7(4) . . ?
C20 C21 C22 121.1(4) . . ?
C21 C20 C19 125.1(4) . . ?
C21 C20 H20 117.5 . . ?
C19 C20 H20 117.5 . . ?
C8 C7 C6 107.9(4) . . ?
C8 C7 H7 126.0 . . ?
C6 C7 H7 126.0 . . ?
N2 C9 C8 111.5(4) . . ?
N2 C9 H9 124.3 . . ?
C8 C9 H9 124.3 . . ?
O2 C19 C20 124.2(4) . . ?
O2 C19 C18 114.8(4) . . ?
C20 C19 C18 121.0(4) . . ?
C10 C11 C12 121.8(4) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C2 C3 C4 107.4(3) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
C16 C17 C17 111.9(5) . 3_776 ?
C16 C17 H17B 111(3) . . ?
C17 C17 H17B 113(3) 3_776 . ?
C16 C17 H17A 103(4) . . ?
C17 C17 H17A 115(4) 3_776 . ?
H17B C17 H17A 101(4) . . ?
C11 C10 C15 118.0(4) . . ?
C11 C10 C5 120.5(4) . . ?
C15 C10 C5 121.4(4) . . ?
C13 C12 C11 119.5(4) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C7 C8 C9 106.5(4) . . ?
C7 C8 H8 126.7 . . ?
C9 C8 H8 126.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C1 C2 111.8(4) . . ?
N1 C1 H1 124.1 . . ?
C2 C1 H1 124.1 . . ?
O3 C13 C12 123.8(4) . . ?
O3 C13 C14 117.1(4) . . ?
C12 C13 C14 119.1(4) . . ?
C3 C2 C1 106.6(4) . . ?
C3 C2 H2 126.7 . . ?
C1 C2 H2 126.7 . . ?
C14 C15 C10 120.5(4) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C14 C13 121.0(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
O3 C16 C17 109.2(4) . . ?
O3 C16 H16A 109.9 . . ?
C17 C16 H16A 109.8 . . ?
O3 C16 H16B 109.8 . . ?
C17 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Cu1 O2 C19 3.1(4) . . . . ?
N2 Cu1 O2 C19 -78(3) . . . . ?
N1 Cu1 O2 C19 -177.5(4) . . . . ?
O1 Cu1 N1 C1 74(12) . . . . ?
O2 Cu1 N1 C1 -4.7(4) . . . . ?
N2 Cu1 N1 C1 177.9(4) . . . . ?
O1 Cu1 N1 C4 -115(11) . . . . ?
O2 Cu1 N1 C4 166.3(4) . . . . ?
N2 Cu1 N1 C4 -11.1(4) . . . . ?
O2 Cu1 O1 C21 -0.5(4) . . . . ?
N2 Cu1 O1 C21 176.8(4) . . . . ?
N1 Cu1 O1 C21 -79(12) . . . . ?
O1 Cu1 N2 C9 10.3(4) . . . . ?
O2 Cu1 N2 C9 92(3) . . . . ?
N1 Cu1 N2 C9 -169.1(4) . . . . ?
O1 Cu1 N2 C6 -172.1(3) . . . . ?
O2 Cu1 N2 C6 -91(3) . . . . ?
N1 Cu1 N2 C6 8.5(3) . . . . ?
C4 C5 C6 N2 -5.5(7) . . . . ?
C10 C5 C6 N2 177.8(4) . . . . ?
C4 C5 C6 C7 170.1(4) . . . . ?
C10 C5 C6 C7 -6.7(7) . . . . ?
C9 N2 C6 C5 175.7(4) . . . . ?
Cu1 N2 C6 C5 -2.3(6) . . . . ?
C9 N2 C6 C7 -0.6(5) . . . . ?
Cu1 N2 C6 C7 -178.6(3) . . . . ?
C1 N1 C4 C5 -179.8(4) . . . . ?
Cu1 N1 C4 C5 7.7(6) . . . . ?
C1 N1 C4 C3 0.9(5) . . . . ?
Cu1 N1 C4 C3 -171.6(3) . . . . ?
C6 C5 C4 N1 2.6(7) . . . . ?
C10 C5 C4 N1 179.4(4) . . . . ?
C6 C5 C4 C3 -178.3(4) . . . . ?
C10 C5 C4 C3 -1.5(7) . . . . ?
Cu1 O1 C21 C20 -1.6(7) . . . . ?
Cu1 O1 C21 C22 178.6(3) . . . . ?
O1 C21 C20 C19 1.8(8) . . . . ?
C22 C21 C20 C19 -178.3(5) . . . . ?
C5 C6 C7 C8 -175.1(4) . . . . ?
N2 C6 C7 C8 1.0(5) . . . . ?
C6 N2 C9 C8 0.0(5) . . . . ?
Cu1 N2 C9 C8 178.0(3) . . . . ?
Cu1 O2 C19 C20 -3.8(7) . . . . ?
Cu1 O2 C19 C18 177.4(3) . . . . ?
C21 C20 C19 O2 1.0(8) . . . . ?
C21 C20 C19 C18 179.8(4) . . . . ?
N1 C4 C3 C2 -1.4(5) . . . . ?
C5 C4 C3 C2 179.4(4) . . . . ?
C12 C11 C10 C15 0.4(7) . . . . ?
C12 C11 C10 C5 177.8(4) . . . . ?
C6 C5 C10 C11 118.9(5) . . . . ?
C4 C5 C10 C11 -58.1(6) . . . . ?
C6 C5 C10 C15 -63.8(6) . . . . ?
C4 C5 C10 C15 119.2(5) . . . . ?
C10 C11 C12 C13 -1.4(7) . . . . ?
C6 C7 C8 C9 -1.0(6) . . . . ?
N2 C9 C8 C7 0.6(6) . . . . ?
C4 N1 C1 C2 -0.1(5) . . . . ?
Cu1 N1 C1 C2 172.4(3) . . . . ?
C16 O3 C13 C12 4.7(7) . . . . ?
C16 O3 C13 C14 -173.6(4) . . . . ?
C11 C12 C13 O3 -177.0(4) . . . . ?
C11 C12 C13 C14 1.3(8) . . . . ?
C4 C3 C2 C1 1.3(5) . . . . ?
N1 C1 C2 C3 -0.8(5) . . . . ?
C11 C10 C15 C14 0.6(7) . . . . ?
C5 C10 C15 C14 -176.7(4) . . . . ?
C10 C15 C14 C13 -0.7(8) . . . . ?
O3 C13 C14 C15 178.1(5) . . . . ?
C12 C13 C14 C15 -0.4(8) . . . . ?
C13 O3 C16 C17 178.6(5) . . . . ?
C17 C17 C16 O3 -178.7(7) 3_776 . . . ?

_diffrn_measured_fraction_theta_max 0.923
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1505319'
_audit_update_record             
;
2017-03-09 deposited with the CCDC.
2017-03-24 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         'C37 H34 Cu N4 O2'
_chemical_formula_sum            'C37 H34 Cu N4 O2'
_chemical_formula_weight         630.22

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   14.9525(3)
_cell_length_b                   15.1818(3)
_cell_length_c                   27.7558(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6300.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11640
_cell_measurement_theta_min      3.3620
_cell_measurement_theta_max      24.1340

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             2632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.733
_shelx_estimated_absorpt_T_min   0.789
_shelx_estimated_absorpt_T_max   0.838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            55068
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.916
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5539
_reflns_number_gt                4174
_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       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97
_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)+(0.0656P)²+7.8435P] 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         5539
_refine_ls_number_parameters     397
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1524
_refine_ls_wR_factor_gt          0.1378
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.042
_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
Cu1 Cu 0.09079(3) 0.14655(3) 0.87849(2) 0.04445(17) Uani 1 1 d . . . . .
O1 O 0.1318(3) 0.4751(2) 0.90399(13) 0.1097(14) Uani 1 1 d . . . . .
O2 O -0.2217(2) 0.1083(3) 0.83209(13) 0.1047(13) Uani 1 1 d . . . . .
N1 N 0.20261(19) 0.2111(2) 0.87726(10) 0.0462(7) Uani 1 1 d . . . . .
N2 N 0.0565(2) 0.1968(2) 0.94124(10) 0.0479(7) Uani 1 1 d . . . . .
N3 N 0.0588(2) 0.16433(19) 0.81055(10) 0.0475(7) Uani 1 1 d . . . . .
N4 N 0.02349(19) 0.03763(19) 0.88255(10) 0.0458(7) Uani 1 1 d . . . . .
C1 C 0.2706(3) 0.2007(3) 0.84695(14) 0.0597(10) Uani 1 1 d . . . . .
H1 H 0.2733 0.1572 0.8234 0.072 Uiso 1 1 calc R U . . .
C2 C 0.3374(3) 0.2633(3) 0.85488(16) 0.0649(11) Uani 1 1 d . . . . .
H2 H 0.3913 0.2683 0.8384 0.078 Uiso 1 1 calc R U . . .
C3 C 0.3082(2) 0.3155(3) 0.89145(14) 0.0557(10) Uani 1 1 d . . . . .
H3 H 0.3381 0.3636 0.9044 0.067 Uiso 1 1 calc R U . . .
C4 C 0.2240(2) 0.2830(2) 0.90605(12) 0.0430(8) Uani 1 1 d . . . . .
C5 C 0.1704(2) 0.3143(2) 0.94358(12) 0.0459(8) Uani 1 1 d . . . . .
C6 C 0.0923(2) 0.2739(2) 0.96083(12) 0.0485(9) Uani 1 1 d . . . . .
C7 C 0.0350(3) 0.3033(3) 0.99799(13) 0.0614(11) Uani 1 1 d . . . . .
H7 H 0.0430 0.3532 1.0169 0.074 Uiso 1 1 calc R U . . .
C8 C -0.0339(3) 0.2453(3) 1.00092(15) 0.0686(12) Uani 1 1 d . . . . .
H8 H -0.0818 0.2475 1.0223 0.082 Uiso 1 1 calc R U . . .
C9 C -0.0188(3) 0.1817(3) 0.96549(14) 0.0572(10) Uani 1 1 d . . . . .
H9 H -0.0568 0.1344 0.9595 0.069 Uiso 1 1 calc R U . . .
C10 C 0.0814(3) 0.2329(3) 0.78288(14) 0.0594(10) Uani 1 1 d . . . . .
H10 H 0.1277 0.2717 0.7900 0.071 Uiso 1 1 calc R U . . .
C11 C 0.0273(3) 0.2393(3) 0.74225(15) 0.0682(12) Uani 1 1 d . . . . .
H11 H 0.0310 0.2815 0.7180 0.082 Uiso 1 1 calc R U . . .
C12 C -0.0322(3) 0.1714(3) 0.74489(14) 0.0608(11) Uani 1 1 d . . . . .
H12 H -0.0770 0.1585 0.7227 0.073 Uiso 1 1 calc R U . . .
C13 C -0.0133(2) 0.1240(2) 0.78769(12) 0.0453(8) Uani 1 1 d . . . . .
C14 C -0.0593(2) 0.0518(2) 0.80625(12) 0.0430(8) Uani 1 1 d . . . . .
C15 C -0.0393(2) 0.0082(2) 0.84907(12) 0.0434(8) Uani 1 1 d . . . . .
C16 C -0.0777(3) -0.0706(2) 0.86673(15) 0.0553(10) Uani 1 1 d . . . . .
H16 H -0.1218 -0.1038 0.8516 0.066 Uiso 1 1 calc R U . . .
C17 C -0.0386(3) -0.0889(3) 0.90975(15) 0.0608(10) Uani 1 1 d . . . . .
H17 H -0.0501 -0.1370 0.9295 0.073 Uiso 1 1 calc R U . . .
C18 C 0.0223(3) -0.0210(2) 0.91830(14) 0.0546(9) Uani 1 1 d . . . . .
H18 H 0.0578 -0.0172 0.9457 0.065 Uiso 1 1 calc R U . . .
C19 C 0.1985(3) 0.3981(3) 0.96719(13) 0.0540(9) Uani 1 1 d . . . . .
C20 C 0.2474(3) 0.3977(3) 1.00977(17) 0.0822(15) Uani 1 1 d . . . . .
H20 H 0.2618 0.3444 1.0243 0.099 Uiso 1 1 calc R U . . .
C21 C 0.2746(4) 0.4753(5) 1.0307(2) 0.106(2) Uani 1 1 d . . . . .
H21 H 0.3060 0.4743 1.0596 0.127 Uiso 1 1 calc R U . . .
C22 C 0.2557(4) 0.5536(5) 1.0092(2) 0.104(2) Uani 1 1 d . . . . .
H22 H 0.2755 0.6057 1.0232 0.125 Uiso 1 1 calc R U . . .
C23 C 0.2081(4) 0.5566(3) 0.9674(2) 0.0962(18) Uani 1 1 d . . . . .
H23 H 0.1954 0.6104 0.9529 0.115 Uiso 1 1 calc R U . . .
C24 C 0.1784(3) 0.4775(3) 0.94629(16) 0.0701(12) Uani 1 1 d . . . . .
C25 C 0.0614(6) 0.5346(4) 0.8967(3) 0.137(3) Uani 1 1 d D U . . .
H25A H 0.0643 0.5805 0.9210 0.165 Uiso 1 1 calc R U . . .
H25B H 0.0679 0.5620 0.8654 0.165 Uiso 1 1 calc R U . . .
C26 C -0.0195(6) 0.4939(5) 0.8993(4) 0.182(4) Uani 1 1 d D U . . .
H26A H -0.0632 0.5381 0.8901 0.219 Uiso 1 1 calc R U . . .
H26B H -0.0295 0.4820 0.9332 0.219 Uiso 1 1 calc R U . . .
C27 C -0.0456(5) 0.4137(6) 0.8739(2) 0.128(3) Uani 1 1 d D U . . .
H27A H -0.0406 0.4264 0.8397 0.153 Uiso 1 1 calc R U . . .
H27B H -0.0003 0.3699 0.8811 0.153 Uiso 1 1 calc R U . . .
C28 C -0.1274(7) 0.3730(5) 0.8804(4) 0.161(4) Uani 1 1 d D . . . .
H28A H -0.1724 0.4184 0.8763 0.194 Uiso 1 1 calc R U . . .
H28B H -0.1298 0.3555 0.9140 0.194 Uiso 1 1 calc R U . . .
C29 C -0.1581(5) 0.2966(6) 0.8524(2) 0.130(3) Uani 1 1 d D . . . .
H29A H -0.1678 0.3158 0.8195 0.156 Uiso 1 1 calc R U . . .
H29B H -0.1101 0.2536 0.8518 0.156 Uiso 1 1 calc R U . . .
C30 C -0.2386(6) 0.2524(6) 0.8687(3) 0.162(3) Uani 1 1 d D U . . .
H30A H -0.2835 0.2969 0.8754 0.195 Uiso 1 1 calc R U . . .
H30B H -0.2253 0.2230 0.8989 0.195 Uiso 1 1 calc R U . . .
C31 C -0.2788(4) 0.1855(6) 0.8348(2) 0.150(4) Uani 1 1 d D U . . .
H31A H -0.3377 0.1685 0.8462 0.180 Uiso 1 1 calc R U . . .
H31B H -0.2853 0.2112 0.8030 0.180 Uiso 1 1 calc R U . . .
C32 C -0.2226(3) 0.0555(3) 0.79197(15) 0.0642(11) Uani 1 1 d . . . . .
C33 C -0.2987(3) 0.0351(4) 0.76533(19) 0.0817(14) Uani 1 1 d . . . . .
H33 H -0.3540 0.0577 0.7743 0.098 Uiso 1 1 calc R U . . .
C34 C -0.2914(4) -0.0187(3) 0.72564(19) 0.0801(15) Uani 1 1 d . . . . .
H34 H -0.3422 -0.0324 0.7078 0.096 Uiso 1 1 calc R U . . .
C35 C -0.2108(4) -0.0520(3) 0.71218(18) 0.0815(14) Uani 1 1 d . . . . .
H35 H -0.2063 -0.0886 0.6854 0.098 Uiso 1 1 calc R U . . .
C36 C -0.1355(3) -0.0312(3) 0.73871(15) 0.0682(12) Uani 1 1 d . . . . .
H36 H -0.0804 -0.0540 0.7294 0.082 Uiso 1 1 calc R U . . .
C37 C -0.1401(2) 0.0224(2) 0.77845(13) 0.0485(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.938(3) . ?
Cu1 N4 1.939(3) . ?
Cu1 N3 1.964(3) . ?
Cu1 N2 1.969(3) . ?
O1 C24 1.366(6) . ?
O1 C25 1.402(7) . ?
O2 C32 1.372(5) . ?
O2 C31 1.452(6) . ?
N1 C1 1.329(5) . ?
N1 C4 1.390(4) . ?
N2 C9 1.332(5) . ?
N2 C6 1.397(5) . ?
N3 C10 1.337(5) . ?
N3 C13 1.394(4) . ?
N4 C18 1.334(4) . ?
N4 C15 1.394(4) . ?
C1 C2 1.396(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.360(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.412(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(5) . ?
C5 C6 1.403(5) . ?
C5 C19 1.493(5) . ?
C6 C7 1.413(5) . ?
C7 C8 1.357(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.397(6) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.392(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.364(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.417(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(5) . ?
C14 C15 1.392(5) . ?
C14 C37 1.501(5) . ?
C15 C16 1.415(5) . ?
C16 C17 1.358(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.395(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C24 1.370(6) . ?
C19 C20 1.389(6) . ?
C20 C21 1.375(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.359(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.361(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.409(6) . ?
C23 H23 0.9300 . ?
C25 C26 1.360(9) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.461(10) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.383(10) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.470(9) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.452(10) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.510(9) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C37 1.384(5) . ?
C32 C33 1.392(6) . ?
C33 C34 1.376(7) . ?
C33 H33 0.9300 . ?
C34 C35 1.360(7) . ?
C34 H34 0.9300 . ?
C35 C36 1.381(6) . ?
C35 H35 0.9300 . ?
C36 C37 1.372(5) . ?
C36 H36 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N4 151.62(12) . . ?
N1 Cu1 N3 97.10(12) . . ?
N4 Cu1 N3 92.67(12) . . ?
N1 Cu1 N2 92.55(12) . . ?
N4 Cu1 N2 98.27(12) . . ?
N3 Cu1 N2 137.09(13) . . ?
C24 O1 C25 119.3(4) . . ?
C32 O2 C31 120.6(4) . . ?
C1 N1 C4 106.3(3) . . ?
C1 N1 Cu1 127.7(2) . . ?
C4 N1 Cu1 125.8(2) . . ?
C9 N2 C6 105.8(3) . . ?
C9 N2 Cu1 126.9(3) . . ?
C6 N2 Cu1 124.7(2) . . ?
C10 N3 C13 106.1(3) . . ?
C10 N3 Cu1 126.6(3) . . ?
C13 N3 Cu1 124.4(2) . . ?
C18 N4 C15 105.8(3) . . ?
C18 N4 Cu1 128.3(3) . . ?
C15 N4 Cu1 125.7(2) . . ?
N1 C1 C2 111.5(3) . . ?
N1 C1 H1 124.2 . . ?
C2 C1 H1 124.2 . . ?
C3 C2 C1 106.5(3) . . ?
C3 C2 H2 126.7 . . ?
C1 C2 H2 126.7 . . ?
C2 C3 C4 107.3(3) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
N1 C4 C5 124.3(3) . . ?
N1 C4 C3 108.3(3) . . ?
C5 C4 C3 127.3(3) . . ?
C4 C5 C6 125.7(3) . . ?
C4 C5 C19 117.1(3) . . ?
C6 C5 C19 117.2(3) . . ?
N2 C6 C5 123.5(3) . . ?
N2 C6 C7 108.4(3) . . ?
C5 C6 C7 128.1(4) . . ?
C8 C7 C6 107.4(4) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C7 C8 C9 106.4(4) . . ?
C7 C8 H8 126.8 . . ?
C9 C8 H8 126.8 . . ?
N2 C9 C8 111.9(4) . . ?
N2 C9 H9 124.0 . . ?
C8 C9 H9 124.0 . . ?
N3 C10 C11 111.9(4) . . ?
N3 C10 H10 124.1 . . ?
C11 C10 H10 124.1 . . ?
C12 C11 C10 106.5(4) . . ?
C12 C11 H11 126.8 . . ?
C10 C11 H11 126.8 . . ?
C11 C12 C13 107.4(3) . . ?
C11 C12 H12 126.3 . . ?
C13 C12 H12 126.3 . . ?
C14 C13 N3 124.0(3) . . ?
C14 C13 C12 127.7(3) . . ?
N3 C13 C12 108.2(3) . . ?
C15 C14 C13 125.7(3) . . ?
C15 C14 C37 118.1(3) . . ?
C13 C14 C37 116.2(3) . . ?
C14 C15 N4 124.2(3) . . ?
C14 C15 C16 127.6(3) . . ?
N4 C15 C16 108.3(3) . . ?
C17 C16 C15 107.6(3) . . ?
C17 C16 H16 126.2 . . ?
C15 C16 H16 126.2 . . ?
C16 C17 C18 106.2(3) . . ?
C16 C17 H17 126.9 . . ?
C18 C17 H17 126.9 . . ?
N4 C18 C17 112.1(3) . . ?
N4 C18 H18 124.0 . . ?
C17 C18 H18 124.0 . . ?
C24 C19 C20 118.7(4) . . ?
C24 C19 C5 120.1(4) . . ?
C20 C19 C5 121.1(4) . . ?
C21 C20 C19 120.7(5) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 120.2(5) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 120.7(5) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C24 119.4(6) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
O1 C24 C19 116.9(4) . . ?
O1 C24 C23 122.8(5) . . ?
C19 C24 C23 120.3(5) . . ?
C26 C25 O1 111.6(7) . . ?
C26 C25 H25A 109.3 . . ?
O1 C25 H25A 109.3 . . ?
C26 C25 H25B 109.3 . . ?
O1 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
C25 C26 C27 126.2(8) . . ?
C25 C26 H26A 105.8 . . ?
C27 C26 H26A 105.8 . . ?
C25 C26 H26B 105.8 . . ?
C27 C26 H26B 105.8 . . ?
H26A C26 H26B 106.2 . . ?
C28 C27 C26 123.0(7) . . ?
C28 C27 H27A 106.6 . . ?
C26 C27 H27A 106.6 . . ?
C28 C27 H27B 106.6 . . ?
C26 C27 H27B 106.6 . . ?
H27A C27 H27B 106.5 . . ?
C27 C28 C29 123.9(8) . . ?
C27 C28 H28A 106.3 . . ?
C29 C28 H28A 106.3 . . ?
C27 C28 H28B 106.3 . . ?
C29 C28 H28B 106.3 . . ?
H28A C28 H28B 106.4 . . ?
C30 C29 C28 117.3(7) . . ?
C30 C29 H29A 108.0 . . ?
C28 C29 H29A 108.0 . . ?
C30 C29 H29B 108.0 . . ?
C28 C29 H29B 108.0 . . ?
H29A C29 H29B 107.2 . . ?
C29 C30 C31 116.5(7) . . ?
C29 C30 H30A 108.2 . . ?
C31 C30 H30A 108.2 . . ?
C29 C30 H30B 108.2 . . ?
C31 C30 H30B 108.2 . . ?
H30A C30 H30B 107.3 . . ?
O2 C31 C30 110.0(5) . . ?
O2 C31 H31A 109.7 . . ?
C30 C31 H31A 109.7 . . ?
O2 C31 H31B 109.7 . . ?
C30 C31 H31B 109.7 . . ?
H31A C31 H31B 108.2 . . ?
O2 C32 C37 115.1(4) . . ?
O2 C32 C33 124.6(4) . . ?
C37 C32 C33 120.3(4) . . ?
C34 C33 C32 119.5(5) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C35 C34 C33 120.7(4) . . ?
C35 C34 H34 119.6 . . ?
C33 C34 H34 119.6 . . ?
C34 C35 C36 119.4(5) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?
C37 C36 C35 121.6(4) . . ?
C37 C36 H36 119.2 . . ?
C35 C36 H36 119.2 . . ?
C36 C37 C32 118.5(4) . . ?
C36 C37 C14 123.3(4) . . ?
C32 C37 C14 118.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 0.5(5) . . . . ?
Cu1 N1 C1 C2 175.7(3) . . . . ?
N1 C1 C2 C3 -1.0(5) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C1 N1 C4 C5 -178.3(4) . . . . ?
Cu1 N1 C4 C5 6.4(5) . . . . ?
C1 N1 C4 C3 0.1(4) . . . . ?
Cu1 N1 C4 C3 -175.2(3) . . . . ?
C2 C3 C4 N1 -0.7(4) . . . . ?
C2 C3 C4 C5 177.6(4) . . . . ?
N1 C4 C5 C6 6.3(6) . . . . ?
C3 C4 C5 C6 -171.8(4) . . . . ?
N1 C4 C5 C19 -173.3(3) . . . . ?
C3 C4 C5 C19 8.6(6) . . . . ?
C9 N2 C6 C5 -177.2(3) . . . . ?
Cu1 N2 C6 C5 -14.7(5) . . . . ?
C9 N2 C6 C7 0.4(4) . . . . ?
Cu1 N2 C6 C7 162.9(3) . . . . ?
C4 C5 C6 N2 -1.7(6) . . . . ?
C19 C5 C6 N2 177.9(3) . . . . ?
C4 C5 C6 C7 -178.8(4) . . . . ?
C19 C5 C6 C7 0.8(6) . . . . ?
N2 C6 C7 C8 0.1(4) . . . . ?
C5 C6 C7 C8 177.6(4) . . . . ?
C6 C7 C8 C9 -0.5(5) . . . . ?
C6 N2 C9 C8 -0.7(4) . . . . ?
Cu1 N2 C9 C8 -162.7(3) . . . . ?
C7 C8 C9 N2 0.8(5) . . . . ?
C13 N3 C10 C11 -0.5(5) . . . . ?
Cu1 N3 C10 C11 -161.7(3) . . . . ?
N3 C10 C11 C12 0.3(5) . . . . ?
C10 C11 C12 C13 0.0(5) . . . . ?
C10 N3 C13 C14 -177.1(4) . . . . ?
Cu1 N3 C13 C14 -15.3(5) . . . . ?
C10 N3 C13 C12 0.5(4) . . . . ?
Cu1 N3 C13 C12 162.3(3) . . . . ?
C11 C12 C13 C14 177.1(4) . . . . ?
C11 C12 C13 N3 -0.3(5) . . . . ?
N3 C13 C14 C15 -1.6(6) . . . . ?
C12 C13 C14 C15 -178.7(4) . . . . ?
N3 C13 C14 C37 175.0(3) . . . . ?
C12 C13 C14 C37 -2.1(6) . . . . ?
C13 C14 C15 N4 8.1(6) . . . . ?
C37 C14 C15 N4 -168.4(3) . . . . ?
C13 C14 C15 C16 -172.7(4) . . . . ?
C37 C14 C15 C16 10.8(5) . . . . ?
C18 N4 C15 C14 179.4(3) . . . . ?
Cu1 N4 C15 C14 3.4(5) . . . . ?
C18 N4 C15 C16 0.0(4) . . . . ?
Cu1 N4 C15 C16 -176.0(2) . . . . ?
C14 C15 C16 C17 -179.8(4) . . . . ?
N4 C15 C16 C17 -0.5(4) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
C15 N4 C18 C17 0.4(4) . . . . ?
Cu1 N4 C18 C17 176.3(3) . . . . ?
C16 C17 C18 N4 -0.7(5) . . . . ?
C4 C5 C19 C24 81.0(5) . . . . ?
C6 C5 C19 C24 -98.6(5) . . . . ?
C4 C5 C19 C20 -97.2(5) . . . . ?
C6 C5 C19 C20 83.1(5) . . . . ?
C24 C19 C20 C21 0.3(7) . . . . ?
C5 C19 C20 C21 178.6(5) . . . . ?
C19 C20 C21 C22 -1.5(9) . . . . ?
C20 C21 C22 C23 1.4(10) . . . . ?
C21 C22 C23 C24 -0.1(9) . . . . ?
C25 O1 C24 C19 137.2(6) . . . . ?
C25 O1 C24 C23 -45.1(8) . . . . ?
C20 C19 C24 O1 178.8(4) . . . . ?
C5 C19 C24 O1 0.5(6) . . . . ?
C20 C19 C24 C23 1.0(7) . . . . ?
C5 C19 C24 C23 -177.3(4) . . . . ?
C22 C23 C24 O1 -178.8(5) . . . . ?
C22 C23 C24 C19 -1.2(8) . . . . ?
C24 O1 C25 C26 -107.3(8) . . . . ?
O1 C25 C26 C27 -49.6(14) . . . . ?
C25 C26 C27 C28 175.9(10) . . . . ?
C26 C27 C28 C29 174.7(8) . . . . ?
C27 C28 C29 C30 170.0(8) . . . . ?
C28 C29 C30 C31 168.9(7) . . . . ?
C32 O2 C31 C30 -154.3(6) . . . . ?
C29 C30 C31 O2 70.3(10) . . . . ?
C31 O2 C32 C37 142.1(6) . . . . ?
C31 O2 C32 C33 -37.4(8) . . . . ?
O2 C32 C33 C34 180.0(5) . . . . ?
C37 C32 C33 C34 0.5(7) . . . . ?
C32 C33 C34 C35 -0.1(8) . . . . ?
C33 C34 C35 C36 -0.2(8) . . . . ?
C34 C35 C36 C37 0.1(8) . . . . ?
C35 C36 C37 C32 0.3(7) . . . . ?
C35 C36 C37 C14 -175.7(4) . . . . ?
O2 C32 C37 C36 179.8(4) . . . . ?
C33 C32 C37 C36 -0.6(6) . . . . ?
O2 C32 C37 C14 -4.0(6) . . . . ?
C33 C32 C37 C14 175.6(4) . . . . ?
C15 C14 C37 C36 -100.6(4) . . . . ?
C13 C14 C37 C36 82.5(5) . . . . ?
C15 C14 C37 C32 83.4(4) . . . . ?
C13 C14 C37 C32 -93.4(4) . . . . ?

_refine_diff_density_max         0.626
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1505370'
_audit_update_record             
;
2017-03-09 deposited with the CCDC.
2017-03-24 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         'C40 H40 Cu N4 O2'
_chemical_formula_sum            'C40 H40 Cu N4 O2'
_chemical_formula_weight         672.30

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.9995(17)
_cell_length_b                   14.841(3)
_cell_length_c                   26.069(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3481.9(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5023
_cell_measurement_theta_min      1.50
_cell_measurement_theta_max      26.78

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             1412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.265
_exptl_crystal_size_min          0.215
_exptl_absorpt_coefficient_mu    0.667
_shelx_estimated_absorpt_T_min   0.875
_shelx_estimated_absorpt_T_max   0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.37656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'SADABS, Bruker, 1997'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5658
_diffrn_reflns_av_unetI/netI     0.3485
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.394
_diffrn_reflns_theta_max         30.055
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.554
_diffrn_reflns_point_group_measured_fraction_full 0.565
_reflns_number_total             5658
_reflns_number_gt                1880
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97
_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)+(0.0537P)²] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.33(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5658
_refine_ls_number_parameters     401
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.3477
_refine_ls_R_factor_gt           0.1298
_refine_ls_wR_factor_ref         0.1987
_refine_ls_wR_factor_gt          0.1460
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.003

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
C16 C 0.5575(16) 0.5713(11) -0.0436(6) 0.106(5) Uani 1 1 d . . . . .
H16A H 0.5147 0.6064 -0.0713 0.127 Uiso 1 1 calc R U . . .
H16B H 0.6599 0.5571 -0.0521 0.127 Uiso 1 1 calc R U . . .
C21 C 0.182(2) 0.6776(17) 0.1467(8) 0.231(6) Uani 1 1 d D . . . .
H21A H 0.2570 0.6989 0.1705 0.277 Uiso 1 1 calc R U . . .
H21B H 0.1710 0.6138 0.1539 0.277 Uiso 1 1 calc R U . . .
C18 C 0.4002(18) 0.6515(12) 0.0243(8) 0.176(11) Uani 1 1 d D . . . .
H18A H 0.3293 0.6050 0.0151 0.211 Uiso 1 1 calc R U . . .
H18B H 0.3738 0.7055 0.0054 0.211 Uiso 1 1 calc R U . . .
C20 C 0.249(3) 0.6792(17) 0.1029(8) 0.231(6) Uani 1 1 d D . . . .
H20A H 0.2160 0.7365 0.0891 0.277 Uiso 1 1 calc R U . . .
H20B H 0.1931 0.6345 0.0837 0.277 Uiso 1 1 calc R U . . .
C22 C 0.040(2) 0.7181(17) 0.1670(8) 0.231(6) Uani 1 1 d D . . . .
H22A H 0.0159 0.6906 0.1997 0.277 Uiso 1 1 calc R U . . .
H22B H 0.0545 0.7821 0.1727 0.277 Uiso 1 1 calc R U . . .
C23 C -0.076(2) 0.7055(19) 0.1335(9) 0.231(6) Uani 1 1 d D . . . .
H23A H -0.0958 0.6419 0.1284 0.277 Uiso 1 1 calc R U . . .
H23B H -0.0552 0.7331 0.1005 0.277 Uiso 1 1 calc R U . . .
Cu1 Cu 0.02496(11) 0.39982(9) 0.08700(4) 0.0443(4) Uani 1 1 d . . . . .
N1 N 0.0318(9) 0.4677(5) 0.0226(3) 0.040(2) Uani 1 1 d . . . . .
N3 N 0.0769(8) 0.4035(6) 0.1587(3) 0.045(2) Uani 1 1 d . . . . .
C5 C 0.2328(10) 0.3879(8) -0.0208(4) 0.040(3) Uani 1 1 d . . . . .
O1 O 0.4745(9) 0.4921(6) -0.0348(3) 0.078(3) Uani 1 1 d . . . . .
C4 C 0.1275(11) 0.4569(7) -0.0185(4) 0.040(3) Uani 1 1 d . . . . .
C9 C 0.2387(11) 0.2487(7) 0.0884(4) 0.050(3) Uani 1 1 d . . . . .
H9 H 0.2075 0.2303 0.1207 0.060 Uiso 1 1 calc R U . . .
C6 C 0.2590(10) 0.3235(7) 0.0170(4) 0.036(3) Uani 1 1 d . . . . .
C1 C -0.0481(12) 0.5404(8) 0.0128(4) 0.062(3) Uani 1 1 d . . . . .
H1 H -0.1215 0.5633 0.0342 0.074 Uiso 1 1 calc R U . . .
C8 C 0.3457(12) 0.2045(8) 0.0604(5) 0.059(3) Uani 1 1 d . . . . .
H8 H 0.3965 0.1525 0.0697 0.071 Uiso 1 1 calc R U . . .
N2 N 0.1840(8) 0.3211(6) 0.0641(3) 0.037(2) Uani 1 1 d . . . . .
C36 C 0.2143(10) 0.4035(8) 0.1795(4) 0.052(3) Uani 1 1 d . . . . .
H36 H 0.2996 0.3874 0.1615 0.063 Uiso 1 1 calc R U . . .
C15 C 0.4418(13) 0.4397(8) -0.0763(5) 0.063(4) Uani 1 1 d . . . . .
C3 C 0.1014(12) 0.5274(8) -0.0536(4) 0.053(3) Uani 1 1 d . . . . .
H3 H 0.1504 0.5370 -0.0845 0.064 Uiso 1 1 calc R U . . .
C33 C -0.0155(12) 0.4306(6) 0.1987(4) 0.050(3) Uani 1 1 d . . . . .
C31 C -0.2572(12) 0.4730(10) 0.2401(5) 0.052(3) Uani 1 1 d . . . . .
C32 C -0.1677(13) 0.4431(7) 0.1942(4) 0.053(3) Uani 1 1 d . . . . .
C30 C -0.2932(13) 0.4161(9) 0.2779(5) 0.070(4) Uani 1 1 d . . . . .
H30 H -0.2577 0.3573 0.2764 0.084 Uiso 1 1 calc R U . . .
N4 N -0.1844(8) 0.4170(6) 0.1016(3) 0.045(2) Uani 1 1 d . . . . .
C26 C -0.3012(15) 0.5609(11) 0.2448(5) 0.074(4) Uani 1 1 d . . . . .
C10 C 0.3199(12) 0.3824(8) -0.0689(4) 0.048(3) Uani 1 1 d . . . . .
C40 C -0.2978(11) 0.4080(8) 0.0687(4) 0.053(3) Uani 1 1 d . . . . .
H40 H -0.2862 0.3951 0.0340 0.064 Uiso 1 1 calc R U . . .
C38 C -0.4032(11) 0.4376(7) 0.1425(5) 0.065(4) Uani 1 1 d . . . . .
H38 H -0.4725 0.4498 0.1680 0.078 Uiso 1 1 calc R U . . .
C13 C 0.4766(18) 0.3806(10) -0.1596(5) 0.087(5) Uani 1 1 d . . . . .
H13 H 0.5295 0.3801 -0.1903 0.105 Uiso 1 1 calc R U . . .
C29 C -0.3821(16) 0.4413(12) 0.3197(5) 0.094(5) Uani 1 1 d . . . . .
H29 H -0.4122 0.3995 0.3442 0.113 Uiso 1 1 calc R U . . .
C35 C 0.2146(13) 0.4299(8) 0.2303(4) 0.060(4) Uani 1 1 d . . . . .
H35 H 0.2971 0.4354 0.2515 0.072 Uiso 1 1 calc R U . . .
C39 C -0.4343(10) 0.4200(7) 0.0922(4) 0.054(3) Uani 1 1 d . . . . .
H39 H -0.5276 0.4169 0.0770 0.064 Uiso 1 1 calc R U . . .
C12 C 0.3605(16) 0.3231(10) -0.1547(5) 0.082(4) Uani 1 1 d . . . . .
H12 H 0.3333 0.2846 -0.1812 0.099 Uiso 1 1 calc R U . . .
C2 C -0.0074(12) 0.5777(7) -0.0337(4) 0.061(3) Uani 1 1 d . . . . .
H2 H -0.0486 0.6289 -0.0485 0.073 Uiso 1 1 calc R U . . .
O2 O -0.2630(11) 0.6172(7) 0.2056(4) 0.107(3) Uani 1 1 d . . . . .
C7 C 0.3621(11) 0.2529(7) 0.0158(4) 0.044(3) Uani 1 1 d . . . . .
H7 H 0.4294 0.2409 -0.0104 0.053 Uiso 1 1 calc R U . . .
C37 C -0.2495(10) 0.4339(6) 0.1489(4) 0.036(3) Uani 1 1 d . . . . .
C14 C 0.5204(15) 0.4397(9) -0.1219(5) 0.082(4) Uani 1 1 d . . . . .
H14 H 0.6004 0.4785 -0.1269 0.099 Uiso 1 1 calc R U . . .
C11 C 0.2833(14) 0.3238(9) -0.1082(5) 0.071(4) Uani 1 1 d . . . . .
H11 H 0.2050 0.2837 -0.1036 0.085 Uiso 1 1 calc R U . . .
C27 C -0.3870(13) 0.5917(11) 0.2855(5) 0.082(4) Uani 1 1 d . . . . .
H27 H -0.4189 0.6512 0.2873 0.099 Uiso 1 1 calc R U . . .
C34 C 0.0709(13) 0.4463(7) 0.2431(4) 0.060(3) Uani 1 1 d . . . . .
H34 H 0.0360 0.4645 0.2750 0.072 Uiso 1 1 calc R U . . .
C24 C -0.208(3) 0.7522(10) 0.1601(7) 0.164(9) Uani 1 1 d . . . . .
H24A H -0.2863 0.7586 0.1347 0.197 Uiso 1 1 calc R U . . .
H24B H -0.1762 0.8126 0.1691 0.197 Uiso 1 1 calc R U . . .
C19 C 0.384(3) 0.6714(18) 0.0818(8) 0.231(6) Uani 1 1 d . . . . .
H19A H 0.4357 0.6241 0.1002 0.277 Uiso 1 1 calc R U . . .
H19B H 0.4367 0.7271 0.0887 0.277 Uiso 1 1 calc R U . . .
C17 C 0.5477(18) 0.6225(10) 0.0077(7) 0.125(6) Uani 1 1 d . . . . .
H17A H 0.5890 0.5843 0.0343 0.150 Uiso 1 1 calc R U . . .
H17B H 0.6105 0.6755 0.0053 0.150 Uiso 1 1 calc R U . . .
C25 C -0.2807(19) 0.7105(10) 0.2090(6) 0.115(6) Uani 1 1 d . . . . .
H25A H -0.2324 0.7333 0.2396 0.138 Uiso 1 1 calc R U . . .
H25B H -0.3853 0.7259 0.2106 0.138 Uiso 1 1 calc R U . . .
C28 C -0.4227(15) 0.5299(14) 0.3231(6) 0.097(6) Uani 1 1 d . . . . .
H28 H -0.4761 0.5491 0.3516 0.117 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
C16 O1 1.412(14) . ?
C16 C17 1.543(17) . ?
C21 C20 1.293(15) . ?
C21 C22 1.506(16) . ?
C18 C17 1.460(19) . ?
C18 C19 1.53(2) . ?
C20 C19 1.34(2) . ?
C22 C23 1.375(16) . ?
C23 C24 1.54(2) . ?
Cu1 N3 1.926(7) . ?
Cu1 N4 1.939(7) . ?
Cu1 N2 1.941(8) . ?
Cu1 N1 1.959(7) . ?
N1 C1 1.322(12) . ?
N1 C4 1.383(11) . ?
N3 C36 1.351(10) . ?
N3 C33 1.394(11) . ?
C5 C4 1.396(13) . ?
C5 C6 1.392(13) . ?
C5 C10 1.482(12) . ?
O1 C15 1.363(12) . ?
C4 C3 1.411(13) . ?
C9 N2 1.341(12) . ?
C9 C8 1.374(13) . ?
C6 C7 1.400(13) . ?
C6 N2 1.402(11) . ?
C1 C2 1.381(13) . ?
C8 C7 1.374(13) . ?
C36 C35 1.381(12) . ?
C15 C14 1.383(15) . ?
C15 C10 1.401(14) . ?
C3 C2 1.336(13) . ?
C33 C32 1.387(14) . ?
C33 C34 1.414(13) . ?
C31 C30 1.337(15) . ?
C31 C26 1.368(16) . ?
C31 C32 1.508(14) . ?
C32 C37 1.400(14) . ?
C30 C29 1.404(15) . ?
N4 C40 1.339(10) . ?
N4 C37 1.388(11) . ?
C26 O2 1.364(14) . ?
C26 C27 1.390(15) . ?
C10 C11 1.384(14) . ?
C40 C39 1.385(12) . ?
C38 C39 1.365(12) . ?
C38 C37 1.394(13) . ?
C13 C14 1.377(16) . ?
C13 C12 1.354(17) . ?
C29 C28 1.367(18) . ?
C35 C34 1.357(13) . ?
C12 C11 1.396(14) . ?
O2 C25 1.396(15) . ?
C27 C28 1.380(18) . ?
C24 C25 1.56(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
O1 C16 C17 103.8(11) . . ?
C20 C21 C22 134(2) . . ?
C17 C18 C19 115.7(18) . . ?
C21 C20 C19 142(3) . . ?
C23 C22 C21 112(2) . . ?
C22 C23 C24 104(2) . . ?
N3 Cu1 N4 92.4(3) . . ?
N3 Cu1 N2 97.8(3) . . ?
N4 Cu1 N2 148.9(3) . . ?
N3 Cu1 N1 144.0(4) . . ?
N4 Cu1 N1 97.5(3) . . ?
N2 Cu1 N1 91.3(3) . . ?
C1 N1 C4 106.5(8) . . ?
C1 N1 Cu1 124.7(7) . . ?
C4 N1 Cu1 128.5(7) . . ?
C36 N3 C33 104.2(8) . . ?
C36 N3 Cu1 127.7(7) . . ?
C33 N3 Cu1 126.1(7) . . ?
C4 C5 C6 126.0(9) . . ?
C4 C5 C10 115.8(10) . . ?
C6 C5 C10 118.2(10) . . ?
C15 O1 C16 117.4(11) . . ?
N1 C4 C5 122.8(10) . . ?
N1 C4 C3 108.2(9) . . ?
C5 C4 C3 129.0(10) . . ?
N2 C9 C8 112.9(11) . . ?
C7 C6 C5 127.6(10) . . ?
C7 C6 N2 108.6(9) . . ?
C5 C6 N2 123.8(10) . . ?
N1 C1 C2 110.7(10) . . ?
C7 C8 C9 106.0(11) . . ?
C9 N2 C6 104.9(9) . . ?
C9 N2 Cu1 127.4(7) . . ?
C6 N2 Cu1 127.5(8) . . ?
N3 C36 C35 112.8(9) . . ?
C14 C15 O1 124.8(13) . . ?
C14 C15 C10 121.2(12) . . ?
O1 C15 C10 114.0(11) . . ?
C2 C3 C4 106.5(10) . . ?
C32 C33 N3 124.4(9) . . ?
C32 C33 C34 126.2(10) . . ?
N3 C33 C34 109.4(9) . . ?
C30 C31 C26 117.8(12) . . ?
C30 C31 C32 121.9(13) . . ?
C26 C31 C32 120.3(12) . . ?
C33 C32 C37 125.3(9) . . ?
C33 C32 C31 120.0(10) . . ?
C37 C32 C31 114.6(10) . . ?
C31 C30 C29 122.9(13) . . ?
C40 N4 C37 105.4(8) . . ?
C40 N4 Cu1 127.0(7) . . ?
C37 N4 Cu1 127.5(6) . . ?
O2 C26 C31 116.4(12) . . ?
O2 C26 C27 120.7(15) . . ?
C31 C26 C27 122.8(15) . . ?
C11 C10 C15 117.8(11) . . ?
C11 C10 C5 122.4(11) . . ?
C15 C10 C5 119.8(11) . . ?
N4 C40 C39 112.3(9) . . ?
C39 C38 C37 108.1(10) . . ?
C14 C13 C12 123.7(13) . . ?
C28 C29 C30 117.2(15) . . ?
C34 C35 C36 106.6(10) . . ?
C38 C39 C40 105.5(9) . . ?
C13 C12 C11 117.5(13) . . ?
C3 C2 C1 108.1(10) . . ?
C26 O2 C25 122.1(12) . . ?
C8 C7 C6 107.5(10) . . ?
N4 C37 C32 123.1(9) . . ?
N4 C37 C38 108.6(9) . . ?
C32 C37 C38 128.3(10) . . ?
C13 C14 C15 117.9(13) . . ?
C10 C11 C12 121.8(12) . . ?
C26 C27 C28 116.9(15) . . ?
C35 C34 C33 107.1(10) . . ?
C23 C24 C25 120.8(17) . . ?
C20 C19 C18 120(2) . . ?
C18 C17 C16 117.0(13) . . ?
O2 C25 C24 107.1(13) . . ?
C29 C28 C27 122.1(14) . . ?

_refine_diff_density_max         0.478
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.073

