# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_mk680
_database_code_depnum_ccdc_archive 'CCDC 1430302'
_audit_update_record             
;
2015-10-08 deposited with the CCDC.
2016-03-03 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         'C20 H20 Br Cu N6 O +, 3(C H4 O), Br -'
_chemical_formula_sum            'C23 H32 Br2 Cu N6 O4'
_chemical_formula_weight         679.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   13.241(3)
_cell_length_b                   13.767(3)
_cell_length_c                   29.787(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.56(3)
_cell_angle_gamma                90
_cell_volume                     5412.4(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    59871
_cell_measurement_theta_min      1.372
_cell_measurement_theta_max      25.639

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_F_000             2744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    3.800
_shelx_estimated_absorpt_T_min   0.252
_shelx_estimated_absorpt_T_max   0.777
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2825
_exptl_absorpt_correction_T_max  0.5520
_exptl_absorpt_process_details   'X-RED (Stoe & Cie, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            59871
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_av_R_equivalents  0.1472
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.372
_diffrn_reflns_theta_max         25.639
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10199
_reflns_number_gt                8263
_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       'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2002)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2012)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0843P)²+6.7691P] 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         10199
_refine_ls_number_parameters     669
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1671
_refine_ls_wR_factor_gt          0.1585
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.66407(4) 0.76291(5) 0.66714(2) 0.02536(16) Uani 1 1 d . . . . .
Br1 Br 0.86577(3) 0.77896(4) 0.67880(2) 0.03221(16) Uani 1 1 d . . . . .
O1 O 0.6307(3) 0.7822(4) 0.50862(15) 0.0451(11) Uani 1 1 d . . . . .
H1 H 0.6723 0.8130 0.4942 0.068 Uiso 1 1 calc R U . . .
N1 N 0.6552(3) 0.6461(3) 0.70501(16) 0.0279(10) Uani 1 1 d . . . . .
N2 N 0.6291(3) 0.4885(3) 0.70900(16) 0.0270(10) Uani 1 1 d . . . . .
N3 N 0.6432(3) 0.6628(3) 0.61656(16) 0.0266(9) Uani 1 1 d . . . . .
N4 N 0.6378(3) 0.8643(3) 0.71211(16) 0.0271(9) Uani 1 1 d . . . . .
N5 N 0.5972(3) 1.0168(3) 0.72456(16) 0.0290(10) Uani 1 1 d . . . . .
N6 N 0.6309(3) 0.8731(3) 0.62354(16) 0.0267(9) Uani 1 1 d . . . . .
C1 C 0.6651(4) 0.7798(4) 0.5545(2) 0.0325(12) Uani 1 1 d . . . . .
C2 C 0.7809(4) 0.7881(5) 0.5597(2) 0.0411(14) Uani 1 1 d . . . . .
H2A H 0.8106 0.7386 0.5411 0.062 Uiso 1 1 calc R U . . .
H2B H 0.8050 0.7784 0.5913 0.062 Uiso 1 1 calc R U . . .
H2C H 0.8012 0.8528 0.5500 0.062 Uiso 1 1 calc R U . . .
C3 C 0.6353(4) 0.6809(4) 0.5730(2) 0.0316(12) Uani 1 1 d . . . . .
C4 C 0.6065(5) 0.6072(5) 0.5416(2) 0.0385(13) Uani 1 1 d . . . . .
H4 H 0.5995 0.6210 0.5102 0.046 Uiso 1 1 calc R U . . .
C5 C 0.5885(5) 0.5148(5) 0.5571(2) 0.0406(14) Uani 1 1 d . . . . .
H5 H 0.5701 0.4642 0.5364 0.049 Uiso 1 1 calc R U . . .
C6 C 0.5976(4) 0.4960(4) 0.6031(2) 0.0356(13) Uani 1 1 d . . . . .
H6 H 0.5851 0.4329 0.6142 0.043 Uiso 1 1 calc R U . . .
C7 C 0.6252(4) 0.5714(4) 0.63216(19) 0.0283(11) Uani 1 1 d . . . . .
C8 C 0.6355(3) 0.5654(4) 0.6814(2) 0.0271(11) Uani 1 1 d . . . . .
C9 C 0.6624(4) 0.6196(4) 0.7497(2) 0.0305(12) Uani 1 1 d . . . . .
H9 H 0.6767 0.6621 0.7745 0.037 Uiso 1 1 calc R U . . .
C10 C 0.6456(4) 0.5215(4) 0.7523(2) 0.0305(12) Uani 1 1 d . . . . .
H10 H 0.6454 0.4838 0.7790 0.037 Uiso 1 1 calc R U . . .
C11 C 0.6051(4) 0.3867(4) 0.6974(2) 0.0346(13) Uani 1 1 d . . . . .
H11A H 0.5387 0.3835 0.6804 0.052 Uiso 1 1 calc R U . . .
H11B H 0.6037 0.3484 0.7250 0.052 Uiso 1 1 calc R U . . .
H11C H 0.6569 0.3606 0.6790 0.052 Uiso 1 1 calc R U . . .
C12 C 0.6203(4) 0.8678(4) 0.5781(2) 0.0322(12) Uani 1 1 d . . . . .
C13 C 0.5746(5) 0.9423(5) 0.5522(2) 0.0403(14) Uani 1 1 d . . . . .
H13 H 0.5646 0.9359 0.5204 0.048 Uiso 1 1 calc R U . . .
C14 C 0.5442(5) 1.0249(5) 0.5729(2) 0.0422(14) Uani 1 1 d . . . . .
H14 H 0.5132 1.0762 0.5555 0.051 Uiso 1 1 calc R U . . .
C15 C 0.5587(4) 1.0335(4) 0.6194(2) 0.0361(13) Uani 1 1 d . . . . .
H15 H 0.5400 1.0913 0.6341 0.043 Uiso 1 1 calc R U . . .
C16 C 0.6010(4) 0.9560(4) 0.6439(2) 0.0288(11) Uani 1 1 d . . . . .
C17 C 0.6115(3) 0.9491(4) 0.6931(2) 0.0279(11) Uani 1 1 d . . . . .
C18 C 0.6402(4) 0.8782(4) 0.75712(19) 0.0307(12) Uani 1 1 d . . . . .
H18 H 0.6567 0.8304 0.7795 0.037 Uiso 1 1 calc R U . . .
C19 C 0.6147(4) 0.9734(4) 0.7652(2) 0.0311(12) Uani 1 1 d . . . . .
H19 H 0.6102 1.0029 0.7938 0.037 Uiso 1 1 calc R U . . .
C20 C 0.5723(5) 1.1196(4) 0.7184(2) 0.0405(14) Uani 1 1 d . . . . .
H20A H 0.6171 1.1486 0.6974 0.061 Uiso 1 1 calc R U . . .
H20B H 0.5815 1.1531 0.7474 0.061 Uiso 1 1 calc R U . . .
H20C H 0.5017 1.1261 0.7061 0.061 Uiso 1 1 calc R U . . .
Cu2 Cu 0.82549(4) 0.43740(5) 0.33766(2) 0.02517(16) Uani 1 1 d . . . . .
Br2 Br 0.62628(3) 0.45101(4) 0.31536(2) 0.03133(15) Uani 1 1 d . . . . .
O11 O 0.8260(3) 0.4495(3) 0.49576(13) 0.0344(9) Uani 1 1 d . . . . .
H11 H 0.7919 0.4075 0.5083 0.052 Uiso 1 1 calc R U . . .
N11 N 0.8577(3) 0.5432(3) 0.29596(15) 0.0270(9) Uani 1 1 d . . . . .
N12 N 0.9026(3) 0.6950(3) 0.28754(16) 0.0278(10) Uani 1 1 d . . . . .
N13 N 0.8510(3) 0.5442(3) 0.38430(15) 0.0257(9) Uani 1 1 d . . . . .
N14 N 0.8434(3) 0.3239(3) 0.29872(16) 0.0283(10) Uani 1 1 d . . . . .
N15 N 0.8798(3) 0.1685(3) 0.29324(16) 0.0274(10) Uani 1 1 d . . . . .
N16 N 0.8494(3) 0.3346(3) 0.38655(15) 0.0263(9) Uani 1 1 d . . . . .
C21 C 0.8057(4) 0.4429(4) 0.44854(18) 0.0291(11) Uani 1 1 d . . . . .
C22 C 0.6899(4) 0.4397(4) 0.4371(2) 0.0335(13) Uani 1 1 d . . . . .
H22A H 0.6620 0.3813 0.4503 0.050 Uiso 1 1 calc R U . . .
H22B H 0.6753 0.4383 0.4043 0.050 Uiso 1 1 calc R U . . .
H22C H 0.6587 0.4975 0.4494 0.050 Uiso 1 1 calc R U . . .
C23 C 0.8477(4) 0.5362(4) 0.42889(19) 0.0272(11) Uani 1 1 d . . . . .
C24 C 0.8776(4) 0.6130(5) 0.4575(2) 0.0364(13) Uani 1 1 d . . . . .
H24 H 0.8750 0.6067 0.4891 0.044 Uiso 1 1 calc R U . . .
C25 C 0.9107(4) 0.6979(5) 0.4395(2) 0.0385(14) Uani 1 1 d . . . . .
H25 H 0.9315 0.7504 0.4587 0.046 Uiso 1 1 calc R U . . .
C26 C 0.9140(4) 0.7072(4) 0.3940(2) 0.0362(13) Uani 1 1 d . . . . .
H26 H 0.9365 0.7659 0.3814 0.043 Uiso 1 1 calc R U . . .
C27 C 0.8836(4) 0.6288(4) 0.36627(19) 0.0284(11) Uani 1 1 d . . . . .
C28 C 0.8828(4) 0.6256(4) 0.31780(19) 0.0280(11) Uani 1 1 d . . . . .
C29 C 0.8620(4) 0.5599(4) 0.25092(19) 0.0296(12) Uani 1 1 d . . . . .
H29 H 0.8480 0.5139 0.2274 0.036 Uiso 1 1 calc R U . . .
C30 C 0.8898(4) 0.6540(4) 0.24576(18) 0.0285(11) Uani 1 1 d . . . . .
H30 H 0.8988 0.6857 0.2180 0.034 Uiso 1 1 calc R U . . .
C31 C 0.9321(4) 0.7973(4) 0.2956(2) 0.0339(12) Uani 1 1 d . . . . .
H31A H 0.8792 0.8307 0.3109 0.051 Uiso 1 1 calc R U . . .
H31B H 0.9407 0.8293 0.2668 0.051 Uiso 1 1 calc R U . . .
H31C H 0.9961 0.7998 0.3146 0.051 Uiso 1 1 calc R U . . .
C32 C 0.8537(4) 0.3499(4) 0.43116(19) 0.0289(11) Uani 1 1 d . . . . .
C33 C 0.8962(4) 0.2814(4) 0.46154(19) 0.0312(12) Uani 1 1 d . . . . .
H33 H 0.9005 0.2936 0.4930 0.037 Uiso 1 1 calc R U . . .
C34 C 0.9319(4) 0.1960(5) 0.4450(2) 0.0362(13) Uani 1 1 d . . . . .
H34 H 0.9608 0.1485 0.4653 0.043 Uiso 1 1 calc R U . . .
C35 C 0.9262(4) 0.1786(4) 0.3991(2) 0.0341(13) Uani 1 1 d . . . . .
H35 H 0.9511 0.1199 0.3875 0.041 Uiso 1 1 calc R U . . .
C36 C 0.8829(4) 0.2495(4) 0.37087(19) 0.0284(11) Uani 1 1 d . . . . .
C37 C 0.8714(4) 0.2439(4) 0.3213(2) 0.0284(11) Uani 1 1 d . . . . .
C38 C 0.8347(4) 0.2991(4) 0.2540(2) 0.0311(12) Uani 1 1 d . . . . .
H38 H 0.8162 0.3418 0.2297 0.037 Uiso 1 1 calc R U . . .
C39 C 0.8573(4) 0.2026(4) 0.25036(19) 0.0300(12) Uani 1 1 d . . . . .
H39 H 0.8573 0.1662 0.2233 0.036 Uiso 1 1 calc R U . . .
C40 C 0.9091(4) 0.0675(4) 0.3039(2) 0.0360(13) Uani 1 1 d . . . . .
H40A H 0.9798 0.0658 0.3165 0.054 Uiso 1 1 calc R U . . .
H40B H 0.9018 0.0282 0.2764 0.054 Uiso 1 1 calc R U . . .
H40C H 0.8654 0.0413 0.3260 0.054 Uiso 1 1 calc R U . . .
O21 O 0.4518(3) 0.7556(3) 0.64775(19) 0.0486(12) Uani 1 1 d . . . . .
H21 H 0.4268 0.7021 0.6546 0.073 Uiso 1 1 calc R U . . .
C41 C 0.3805(5) 0.8079(6) 0.6205(3) 0.0554(19) Uani 1 1 d . . . . .
H41A H 0.3286 0.8338 0.6389 0.083 Uiso 1 1 calc R U . . .
H41B H 0.3487 0.7649 0.5972 0.083 Uiso 1 1 calc R U . . .
H41C H 0.4142 0.8617 0.6061 0.083 Uiso 1 1 calc R U . . .
O31 O 1.0488(3) 0.4300(3) 0.35935(16) 0.0423(10) Uani 1 1 d . . . . .
H31 H 1.0649 0.3717 0.3555 0.063 Uiso 1 1 calc R U . . .
C42 C 1.1014(5) 0.4655(6) 0.3988(3) 0.0536(18) Uani 1 1 d . . . . .
H42A H 1.1084 0.5361 0.3966 0.080 Uiso 1 1 calc R U . . .
H42B H 1.1687 0.4356 0.4025 0.080 Uiso 1 1 calc R U . . .
H42C H 1.0637 0.4494 0.4248 0.080 Uiso 1 1 calc R U . . .
O41 O 0.9136(4) 0.1334(4) 0.55376(19) 0.0598(13) Uani 1 1 d . . . . .
H41 H 0.8797 0.1605 0.5728 0.090 Uiso 1 1 calc R U . . .
C43 C 0.9566(7) 0.0508(6) 0.5718(4) 0.087(4) Uani 1 1 d . . . . .
H43A H 0.9994 0.0671 0.5992 0.131 Uiso 1 1 calc R U . . .
H43B H 0.9981 0.0203 0.5499 0.131 Uiso 1 1 calc R U . . .
H43C H 0.9033 0.0057 0.5794 0.131 Uiso 1 1 calc R U . . .
O42 O 0.7113(4) 0.3218(4) 0.54021(17) 0.0508(12) Uani 1 1 d . . . . .
H42 H 0.7349 0.3124 0.5669 0.076 Uiso 1 1 calc R U . . .
C44 C 0.6512(8) 0.2428(7) 0.5257(4) 0.084(3) Uani 1 1 d . . . . .
H44A H 0.6938 0.1849 0.5240 0.127 Uiso 1 1 calc R U . . .
H44B H 0.6179 0.2567 0.4958 0.127 Uiso 1 1 calc R U . . .
H44C H 0.5998 0.2313 0.5470 0.127 Uiso 1 1 calc R U . . .
O43 O 0.7361(7) 0.9102(5) 0.4633(2) 0.100(3) Uani 1 1 d . . . . .
H43 H 0.7421 0.9009 0.4357 0.149 Uiso 1 1 calc R U . . .
C45 C 0.7567(10) 1.0040(8) 0.4735(3) 0.096(4) Uani 1 1 d . . . . .
H45A H 0.7661 1.0115 0.5062 0.144 Uiso 1 1 calc R U . . .
H45B H 0.7002 1.0449 0.4615 0.144 Uiso 1 1 calc R U . . .
H45C H 0.8187 1.0237 0.4600 0.144 Uiso 1 1 calc R U . . .
C46 C 0.6100(6) 0.6856(6) 0.3993(3) 0.060(2) Uani 1 1 d . . . . .
H46A H 0.6811 0.7052 0.4042 0.089 Uiso 1 1 calc R U . . .
H46B H 0.6061 0.6190 0.3877 0.089 Uiso 1 1 calc R U . . .
H46C H 0.5781 0.6886 0.4279 0.089 Uiso 1 1 calc R U . . .
O44 O 0.5606(5) 0.7467(5) 0.3689(4) 0.118(3) Uani 1 1 d . . . . .
H44 H 0.5989 0.7932 0.3636 0.177 Uiso 1 1 calc R U . . .
Br3 Br 0.79754(5) 0.23507(6) 0.63538(2) 0.0536(2) Uani 1 1 d . . . . .
Br4 Br 0.71791(5) 0.92130(5) 0.35747(2) 0.04464(18) 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 1.973(5) . ?
Cu1 N4 1.984(5) . ?
Cu1 N6 2.022(5) . ?
Cu1 N3 2.045(5) . ?
Cu1 Br1 2.6748(9) . ?
O1 C1 1.407(7) . ?
N1 C8 1.330(7) . ?
N1 C9 1.375(7) . ?
N2 C8 1.347(7) . ?
N2 C10 1.368(7) . ?
N2 C11 1.472(7) . ?
N3 C3 1.319(7) . ?
N3 C7 1.368(7) . ?
N4 C17 1.332(7) . ?
N4 C18 1.352(7) . ?
N5 C17 1.346(7) . ?
N5 C19 1.353(8) . ?
N5 C20 1.462(7) . ?
N6 C12 1.352(7) . ?
N6 C16 1.367(7) . ?
C1 C3 1.531(8) . ?
C1 C2 1.533(7) . ?
C1 C12 1.543(8) . ?
C3 C4 1.411(8) . ?
C4 C5 1.381(9) . ?
C5 C6 1.390(9) . ?
C6 C7 1.382(8) . ?
C7 C8 1.465(8) . ?
C9 C10 1.373(8) . ?
C12 C13 1.393(9) . ?
C13 C14 1.370(10) . ?
C14 C15 1.387(9) . ?
C15 C16 1.386(8) . ?
C16 C17 1.463(8) . ?
C18 C19 1.379(8) . ?
Cu2 N14 1.971(5) . ?
Cu2 N11 1.982(5) . ?
Cu2 N13 2.033(5) . ?
Cu2 N16 2.038(5) . ?
Cu2 Br2 2.6749(9) . ?
O11 C21 1.414(7) . ?
N11 C28 1.337(7) . ?
N11 C29 1.367(7) . ?
N12 C28 1.353(7) . ?
N12 C30 1.364(7) . ?
N12 C31 1.476(7) . ?
N13 C23 1.337(7) . ?
N13 C27 1.366(7) . ?
N14 C37 1.327(7) . ?
N14 C38 1.370(8) . ?
N15 C37 1.343(7) . ?
N15 C39 1.371(7) . ?
N15 C40 1.471(7) . ?
N16 C32 1.342(7) . ?
N16 C36 1.349(7) . ?
C21 C23 1.534(8) . ?
C21 C32 1.537(8) . ?
C21 C22 1.545(7) . ?
C23 C24 1.395(8) . ?
C24 C25 1.372(9) . ?
C25 C26 1.365(9) . ?
C26 C27 1.398(8) . ?
C27 C28 1.444(8) . ?
C29 C30 1.360(8) . ?
C32 C33 1.395(8) . ?
C33 C34 1.372(9) . ?
C34 C35 1.383(9) . ?
C35 C36 1.383(8) . ?
C36 C37 1.475(8) . ?
C38 C39 1.368(8) . ?
O21 C41 1.395(8) . ?
O31 C42 1.405(8) . ?
O41 C43 1.363(9) . ?
O42 C44 1.396(10) . ?
O43 C45 1.349(11) . ?
C46 O44 1.363(10) . ?

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 99.53(19) . . ?
N1 Cu1 N6 163.47(16) . . ?
N4 Cu1 N6 82.26(19) . . ?
N1 Cu1 N3 82.01(19) . . ?
N4 Cu1 N3 161.97(16) . . ?
N6 Cu1 N3 91.30(18) . . ?
N1 Cu1 Br1 95.59(11) . . ?
N4 Cu1 Br1 94.66(12) . . ?
N6 Cu1 Br1 100.66(12) . . ?
N3 Cu1 Br1 103.09(11) . . ?
C8 N1 C9 106.6(5) . . ?
C8 N1 Cu1 113.4(4) . . ?
C9 N1 Cu1 140.0(4) . . ?
C8 N2 C10 107.6(5) . . ?
C8 N2 C11 128.8(5) . . ?
C10 N2 C11 123.5(5) . . ?
C3 N3 C7 120.4(5) . . ?
C3 N3 Cu1 126.4(4) . . ?
C7 N3 Cu1 112.7(4) . . ?
C17 N4 C18 106.4(5) . . ?
C17 N4 Cu1 112.5(4) . . ?
C18 N4 Cu1 141.0(4) . . ?
C17 N5 C19 107.1(5) . . ?
C17 N5 C20 128.7(5) . . ?
C19 N5 C20 124.1(5) . . ?
C12 N6 C16 118.6(5) . . ?
C12 N6 Cu1 127.1(4) . . ?
C16 N6 Cu1 113.4(4) . . ?
O1 C1 C3 107.2(5) . . ?
O1 C1 C2 109.9(5) . . ?
C3 C1 C2 108.3(5) . . ?
O1 C1 C12 108.5(5) . . ?
C3 C1 C12 114.6(5) . . ?
C2 C1 C12 108.3(5) . . ?
N3 C3 C4 120.8(5) . . ?
N3 C3 C1 121.3(5) . . ?
C4 C3 C1 117.7(5) . . ?
C5 C4 C3 119.0(6) . . ?
C4 C5 C6 119.8(6) . . ?
C7 C6 C5 118.4(6) . . ?
N3 C7 C6 121.4(5) . . ?
N3 C7 C8 112.8(5) . . ?
C6 C7 C8 125.7(5) . . ?
N1 C8 N2 110.7(5) . . ?
N1 C8 C7 118.7(5) . . ?
N2 C8 C7 130.6(5) . . ?
C10 C9 N1 108.5(5) . . ?
N2 C10 C9 106.7(5) . . ?
N6 C12 C13 121.5(6) . . ?
N6 C12 C1 119.0(5) . . ?
C13 C12 C1 119.5(5) . . ?
C14 C13 C12 119.4(6) . . ?
C13 C14 C15 119.9(6) . . ?
C16 C15 C14 118.6(6) . . ?
N6 C16 C15 121.9(5) . . ?
N6 C16 C17 112.5(5) . . ?
C15 C16 C17 125.5(5) . . ?
N4 C17 N5 110.9(5) . . ?
N4 C17 C16 118.9(5) . . ?
N5 C17 C16 130.2(5) . . ?
N4 C18 C19 108.7(5) . . ?
N5 C19 C18 106.9(5) . . ?
N14 Cu2 N11 99.88(19) . . ?
N14 Cu2 N13 162.61(17) . . ?
N11 Cu2 N13 82.21(19) . . ?
N14 Cu2 N16 81.41(19) . . ?
N11 Cu2 N16 158.32(17) . . ?
N13 Cu2 N16 90.36(18) . . ?
N14 Cu2 Br2 94.12(12) . . ?
N11 Cu2 Br2 92.86(12) . . ?
N13 Cu2 Br2 103.04(11) . . ?
N16 Cu2 Br2 108.69(12) . . ?
C28 N11 C29 107.9(5) . . ?
C28 N11 Cu2 112.1(4) . . ?
C29 N11 Cu2 140.0(4) . . ?
C28 N12 C30 107.4(5) . . ?
C28 N12 C31 128.8(5) . . ?
C30 N12 C31 123.8(5) . . ?
C23 N13 C27 119.9(5) . . ?
C23 N13 Cu2 127.0(4) . . ?
C27 N13 Cu2 112.8(4) . . ?
C37 N14 C38 106.5(5) . . ?
C37 N14 Cu2 113.7(4) . . ?
C38 N14 Cu2 139.8(4) . . ?
C37 N15 C39 106.9(5) . . ?
C37 N15 C40 129.0(5) . . ?
C39 N15 C40 124.0(5) . . ?
C32 N16 C36 119.4(5) . . ?
C32 N16 Cu2 126.1(4) . . ?
C36 N16 Cu2 113.1(4) . . ?
O11 C21 C23 106.3(4) . . ?
O11 C21 C32 109.7(4) . . ?
C23 C21 C32 113.3(4) . . ?
O11 C21 C22 109.2(4) . . ?
C23 C21 C22 108.9(4) . . ?
C32 C21 C22 109.4(5) . . ?
N13 C23 C24 120.9(5) . . ?
N13 C23 C21 119.3(5) . . ?
C24 C23 C21 119.7(5) . . ?
C25 C24 C23 119.4(6) . . ?
C26 C25 C24 120.3(6) . . ?
C25 C26 C27 118.9(6) . . ?
N13 C27 C26 120.7(5) . . ?
N13 C27 C28 113.0(5) . . ?
C26 C27 C28 126.3(5) . . ?
N11 C28 N12 109.2(5) . . ?
N11 C28 C27 119.6(5) . . ?
N12 C28 C27 131.2(5) . . ?
C30 C29 N11 107.7(5) . . ?
C29 C30 N12 107.8(5) . . ?
N16 C32 C33 121.2(5) . . ?
N16 C32 C21 118.6(5) . . ?
C33 C32 C21 120.1(5) . . ?
C34 C33 C32 118.6(5) . . ?
C33 C34 C35 120.7(5) . . ?
C34 C35 C36 117.8(6) . . ?
N16 C36 C35 122.2(5) . . ?
N16 C36 C37 112.4(5) . . ?
C35 C36 C37 125.3(5) . . ?
N14 C37 N15 111.2(5) . . ?
N14 C37 C36 117.8(5) . . ?
N15 C37 C36 131.0(5) . . ?
C39 C38 N14 108.5(5) . . ?
C38 C39 N15 106.9(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O43 0.84 1.87 2.680(8) 163.0 .
O21 H21 Br2 0.84 2.42 3.248(5) 171.0 3_666
O31 H31 Br1 0.84 2.52 3.324(5) 161.3 3_766
O41 H41 Br3 0.84 2.45 3.290(6) 173.0 .
O42 H42 Br3 0.84 2.39 3.202(5) 162.4 .
O43 H43 Br4 0.84 2.34 3.144(6) 159.5 .
O44 H44 Br4 0.84 2.38 3.216(7) 172.7 .

_refine_diff_density_max         1.376
_refine_diff_density_min         -1.341
_refine_diff_density_rms         0.161

####################################################################### 
# 
# 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_mk299c
_database_code_depnum_ccdc_archive 'CCDC 1442849'
_audit_update_record             
;
2015-12-16 deposited with the CCDC.
2016-03-03 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         ?
_chemical_formula_sum            'C47 H38 Cu2 N6 O7'
_chemical_formula_weight         925.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
N N 0.0061 0.0033 '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                   11.231(2)
_cell_length_b                   12.002(2)
_cell_length_c                   15.218(3)
_cell_angle_alpha                98.67(3)
_cell_angle_beta                 97.62(3)
_cell_angle_gamma                95.17(3)
_cell_volume                     1997.3(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    25763
_cell_measurement_theta_min      1.37

_cell_measurement_theta_max      26.74

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.246
_exptl_crystal_size_mid          0.23

_exptl_crystal_size_min          0.086
_exptl_absorpt_coefficient_mu    1.128
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7367
_exptl_absorpt_correction_T_max  0.8794
_exptl_absorpt_process_details   'X-RED (Stoe & Cie, 2002)'


_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25763
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.369
_diffrn_reflns_theta_max         26.742
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8463
_reflns_number_gt                6357
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0610P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8463
_refine_ls_number_parameters     571
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.1009
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.04442(3) 0.74509(3) 0.31223(2) 0.02339(9) Uani 1 1 d . . . . .
Cu2 Cu -0.20474(3) 0.66357(3) 0.20077(2) 0.02375(9) Uani 1 1 d . . . . .
O1 O -0.09449(16) 0.62881(16) 0.30145(12) 0.0232(4) Uani 1 1 d . . . . .
O2 O 0.08121(16) 0.70012(18) 0.19124(14) 0.0299(4) Uani 1 1 d . . . . .
O3 O -0.09842(17) 0.61594(19) 0.11419(14) 0.0304(4) Uani 1 1 d . . . . .
O4 O 0.1840(2) 0.6492(2) 0.37210(18) 0.0467(6) Uani 1 1 d . . . . .
O5 O 0.24359(18) 0.4830(2) 0.39089(15) 0.0352(5) Uani 1 1 d . . . . .
O6 O -0.13635(19) 0.8466(2) 0.22569(16) 0.0418(6) Uani 1 1 d . . . . .
O7 O -0.3084(3) 0.9209(3) 0.2231(2) 0.0768(9) Uani 1 1 d . . . . .
N1 N 0.00019(19) 0.7825(2) 0.43251(16) 0.0238(5) Uani 1 1 d . . . . .
N2 N 0.15391(19) 0.8950(2) 0.35761(16) 0.0249(5) Uani 1 1 d . . . . .
N3 N 0.2430(2) 1.0135(2) 0.47907(16) 0.0257(5) Uani 1 1 d . . . . .
N4 N -0.32027(19) 0.6427(2) 0.28260(15) 0.0237(5) Uani 1 1 d . . . . .
N5 N -0.35917(19) 0.6658(2) 0.11549(15) 0.0244(5) Uani 1 1 d . . . . .
N6 N -0.55744(19) 0.6662(2) 0.10230(16) 0.0249(5) Uani 1 1 d . . . . .
C1 C -0.1435(2) 0.6167(2) 0.38101(18) 0.0231(5) Uani 1 1 d . . . . .
C2 C -0.1177(2) 0.5019(2) 0.4073(2) 0.0269(6) Uani 1 1 d . . . . .
H2A H -0.1557 0.4408 0.3589 0.040 Uiso 1 1 calc R U . . .
H2B H -0.1507 0.4930 0.4626 0.040 Uiso 1 1 calc R U . . .
H2C H -0.0302 0.4984 0.4172 0.040 Uiso 1 1 calc R U . . .
C3 C -0.0836(2) 0.7128(2) 0.45733(18) 0.0233(5) Uani 1 1 d . . . . .
C4 C -0.1057(3) 0.7270(3) 0.54589(19) 0.0284(6) Uani 1 1 d . . . . .
H4 H -0.1651 0.6776 0.5642 0.034 Uiso 1 1 calc R U . . .
C5 C -0.0388(3) 0.8154(3) 0.6066(2) 0.0322(6) Uani 1 1 d . . . . .
H5 H -0.0537 0.8276 0.6672 0.039 Uiso 1 1 calc R U . . .
C6 C 0.0501(3) 0.8865(3) 0.5803(2) 0.0304(6) Uani 1 1 d . . . . .
H6 H 0.0968 0.9462 0.6223 0.036 Uiso 1 1 calc R U . . .
C7 C 0.0683(2) 0.8681(2) 0.49163(19) 0.0254(6) Uani 1 1 d . . . . .
C8 C 0.1545(2) 0.9276(2) 0.44577(19) 0.0249(6) Uani 1 1 d . . . . .
C9 C 0.3008(2) 1.0381(2) 0.4081(2) 0.0260(6) Uani 1 1 d . . . . .
C10 C 0.2442(2) 0.9632(2) 0.3331(2) 0.0259(6) Uani 1 1 d . . . . .
C11 C 0.2669(3) 0.9562(2) 0.2396(2) 0.0305(6) Uani 1 1 d . . . . .
C12 C 0.1693(3) 0.9507(3) 0.1714(2) 0.0362(7) Uani 1 1 d . . . . .
H12 H 0.0891 0.9470 0.1852 0.043 Uiso 1 1 calc R U . . .
C13 C 0.1897(4) 0.9506(3) 0.0830(2) 0.0471(9) Uani 1 1 d . . . . .
H13 H 0.1234 0.9473 0.0365 0.056 Uiso 1 1 calc R U . . .
C14 C 0.3065(4) 0.9554(3) 0.0633(3) 0.0524(10) Uani 1 1 d . . . . .
H14 H 0.3204 0.9584 0.0034 0.063 Uiso 1 1 calc R U . . .
C15 C 0.4034(4) 0.9558(3) 0.1298(3) 0.0490(9) Uani 1 1 d . . . . .
H15 H 0.4830 0.9549 0.1150 0.059 Uiso 1 1 calc R U . . .
C16 C 0.3840(3) 0.9575(3) 0.2181(2) 0.0397(7) Uani 1 1 d . . . . .
H16 H 0.4506 0.9596 0.2640 0.048 Uiso 1 1 calc R U . . .
C17 C 0.4024(2) 1.1279(2) 0.4158(2) 0.0268(6) Uani 1 1 d . . . . .
C18 C 0.5033(3) 1.1395(3) 0.4823(2) 0.0333(7) Uani 1 1 d . . . . .
H18 H 0.5044 1.0929 0.5276 0.040 Uiso 1 1 calc R U . . .
C19 C 0.6019(3) 1.2183(3) 0.4830(2) 0.0379(7) Uani 1 1 d . . . . .
H19 H 0.6703 1.2252 0.5283 0.045 Uiso 1 1 calc R U . . .
C20 C 0.6004(3) 1.2862(3) 0.4179(3) 0.0413(8) Uani 1 1 d . . . . .
H20 H 0.6687 1.3388 0.4175 0.050 Uiso 1 1 calc R U . . .
C21 C 0.5005(3) 1.2784(3) 0.3532(2) 0.0399(7) Uani 1 1 d . . . . .
H21 H 0.4992 1.3268 0.3092 0.048 Uiso 1 1 calc R U . . .
C22 C 0.4013(3) 1.1995(3) 0.3522(2) 0.0327(6) Uani 1 1 d . . . . .
H22 H 0.3324 1.1947 0.3077 0.039 Uiso 1 1 calc R U . . .
C23 C 0.2705(3) 1.0732(3) 0.5724(2) 0.0319(6) Uani 1 1 d . . . . .
H23A H 0.1954 1.0932 0.5937 0.048 Uiso 1 1 calc R U . . .
H23B H 0.3252 1.1424 0.5750 0.048 Uiso 1 1 calc R U . . .
H23C H 0.3091 1.0238 0.6105 0.048 Uiso 1 1 calc R U . . .
C24 C -0.2810(2) 0.6201(2) 0.36362(18) 0.0226(5) Uani 1 1 d . . . . .
C25 C -0.3616(2) 0.5926(2) 0.42126(19) 0.0265(6) Uani 1 1 d . . . . .
H25 H -0.3340 0.5757 0.4790 0.032 Uiso 1 1 calc R U . . .
C26 C -0.4845(2) 0.5909(3) 0.3907(2) 0.0285(6) Uani 1 1 d . . . . .
H26 H -0.5419 0.5731 0.4285 0.034 Uiso 1 1 calc R U . . .
C27 C -0.5244(2) 0.6147(3) 0.3061(2) 0.0285(6) Uani 1 1 d . . . . .
H27 H -0.6083 0.6135 0.2859 0.034 Uiso 1 1 calc R U . . .
C28 C -0.4401(2) 0.6401(2) 0.25195(19) 0.0242(5) Uani 1 1 d . . . . .
C29 C -0.4556(2) 0.6585(2) 0.15848(19) 0.0249(6) Uani 1 1 d . . . . .
C30 C -0.5242(2) 0.6799(2) 0.02003(19) 0.0246(5) Uani 1 1 d . . . . .
C31 C -0.4006(2) 0.6797(2) 0.02948(18) 0.0247(5) Uani 1 1 d . . . . .
C32 C -0.3189(2) 0.6897(3) -0.03824(19) 0.0264(6) Uani 1 1 d . . . . .
C33 C -0.2074(3) 0.7543(3) -0.0152(2) 0.0347(7) Uani 1 1 d . . . . .
H33 H -0.1839 0.7943 0.0442 0.042 Uiso 1 1 calc R U . . .
C34 C -0.1292(3) 0.7608(3) -0.0790(2) 0.0418(8) Uani 1 1 d . . . . .
H34 H -0.0524 0.8044 -0.0625 0.050 Uiso 1 1 calc R U . . .
C35 C -0.1631(3) 0.7044(3) -0.1651(2) 0.0421(8) Uani 1 1 d . . . . .
H35 H -0.1096 0.7085 -0.2082 0.051 Uiso 1 1 calc R U . . .
C36 C -0.2759(3) 0.6412(3) -0.1894(2) 0.0379(7) Uani 1 1 d . . . . .
H36 H -0.3000 0.6030 -0.2494 0.046 Uiso 1 1 calc R U . . .
C37 C -0.3530(3) 0.6340(3) -0.1261(2) 0.0316(6) Uani 1 1 d . . . . .
H37 H -0.4298 0.5905 -0.1429 0.038 Uiso 1 1 calc R U . . .
C38 C -0.6112(2) 0.6953(2) -0.05751(19) 0.0263(6) Uani 1 1 d . . . . .
C39 C -0.7191(3) 0.6240(3) -0.0855(2) 0.0320(6) Uani 1 1 d . . . . .
H39 H -0.7373 0.5622 -0.0553 0.038 Uiso 1 1 calc R U . . .
C40 C -0.8001(3) 0.6435(3) -0.1577(2) 0.0401(8) Uani 1 1 d . . . . .
H40 H -0.8732 0.5947 -0.1772 0.048 Uiso 1 1 calc R U . . .
C41 C -0.7738(3) 0.7343(3) -0.2010(2) 0.0408(8) Uani 1 1 d . . . . .
H41 H -0.8305 0.7485 -0.2490 0.049 Uiso 1 1 calc R U . . .
C42 C -0.6663(3) 0.8047(3) -0.1755(2) 0.0371(7) Uani 1 1 d . . . . .
H42 H -0.6482 0.8657 -0.2065 0.045 Uiso 1 1 calc R U . . .
C43 C -0.5848(3) 0.7847(3) -0.1035(2) 0.0310(6) Uani 1 1 d . . . . .
H43 H -0.5107 0.8323 -0.0856 0.037 Uiso 1 1 calc R U . . .
C44 C -0.6794(2) 0.6717(3) 0.1274(2) 0.0291(6) Uani 1 1 d . . . . .
H44A H -0.7180 0.5947 0.1257 0.044 Uiso 1 1 calc R U . . .
H44B H -0.7280 0.7095 0.0851 0.044 Uiso 1 1 calc R U . . .
H44C H -0.6732 0.7145 0.1883 0.044 Uiso 1 1 calc R U . . .
C45 C 0.0140(3) 0.6443(3) 0.1246(2) 0.0310(6) Uani 1 1 d D . . . .
C46 C 0.1820(2) 0.5463(3) 0.3519(2) 0.0275(6) Uani 1 1 d D . . . .
C47 C -0.1906(3) 0.9182(3) 0.2141(2) 0.0352(7) Uani 1 1 d D . . . .
H45H H 0.054(4) 0.614(4) 0.073(2) 0.080 Uiso 1 1 d D U . . .
H46H H 0.122(3) 0.508(4) 0.297(2) 0.080 Uiso 1 1 d D U . . .
H47H H -0.145(4) 0.999(2) 0.216(3) 0.080 Uiso 1 1 d D 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 O2 1.948(2) . ?
Cu1 N1 1.958(2) . ?
Cu1 O1 1.970(2) . ?
Cu1 N2 2.056(2) . ?
Cu1 O4 2.208(2) . ?
Cu2 N4 1.939(2) . ?
Cu2 O3 1.950(2) . ?
Cu2 O1 1.9589(19) . ?
Cu2 N5 2.029(2) . ?
Cu2 O6 2.220(3) . ?
O1 C1 1.416(3) . ?
O2 C45 1.244(4) . ?
O3 C45 1.260(3) . ?
O4 C46 1.224(4) . ?
O5 C46 1.237(4) . ?
O6 C47 1.119(4) . ?
O7 C47 1.351(5) . ?
N1 C3 1.333(4) . ?
N1 C7 1.359(4) . ?
N2 C8 1.339(4) . ?
N2 C10 1.371(4) . ?
N3 C8 1.354(4) . ?
N3 C9 1.387(4) . ?
N3 C23 1.470(4) . ?
N4 C24 1.329(4) . ?
N4 C28 1.360(3) . ?
N5 C29 1.341(3) . ?
N5 C31 1.369(4) . ?
N6 C29 1.353(3) . ?
N6 C30 1.382(4) . ?
N6 C44 1.474(3) . ?
C1 C2 1.533(4) . ?
C1 C24 1.537(3) . ?
C1 C3 1.543(4) . ?
C3 C4 1.391(4) . ?
C4 C5 1.386(4) . ?
C5 C6 1.393(4) . ?
C6 C7 1.380(4) . ?
C7 C8 1.462(4) . ?
C9 C10 1.382(4) . ?
C9 C17 1.477(4) . ?
C10 C11 1.471(4) . ?
C11 C12 1.395(5) . ?
C11 C16 1.397(4) . ?
C12 C13 1.394(5) . ?
C13 C14 1.383(6) . ?
C14 C15 1.384(6) . ?
C15 C16 1.386(5) . ?
C17 C22 1.387(4) . ?
C17 C18 1.398(4) . ?
C18 C19 1.388(5) . ?
C19 C20 1.374(5) . ?
C20 C21 1.378(5) . ?
C21 C22 1.392(4) . ?
C24 C25 1.394(4) . ?
C25 C26 1.394(4) . ?
C26 C27 1.385(4) . ?
C27 C28 1.379(4) . ?
C28 C29 1.462(4) . ?
C30 C31 1.377(4) . ?
C30 C38 1.474(4) . ?
C31 C32 1.478(4) . ?
C32 C33 1.386(4) . ?
C32 C37 1.389(4) . ?
C33 C34 1.398(4) . ?
C34 C35 1.369(5) . ?
C35 C36 1.391(5) . ?
C36 C37 1.386(4) . ?
C38 C39 1.396(4) . ?
C38 C43 1.397(4) . ?
C39 C40 1.393(4) . ?
C40 C41 1.385(5) . ?
C41 C42 1.384(5) . ?
C42 C43 1.395(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 N1 176.62(9) . . ?
O2 Cu1 O1 95.77(9) . . ?
N1 Cu1 O1 80.86(9) . . ?
O2 Cu1 N2 103.33(9) . . ?
N1 Cu1 N2 80.04(10) . . ?
O1 Cu1 N2 158.81(9) . . ?
O2 Cu1 O4 92.69(10) . . ?
N1 Cu1 O4 87.46(10) . . ?
O1 Cu1 O4 97.50(9) . . ?
N2 Cu1 O4 90.76(9) . . ?
N4 Cu2 O3 155.93(10) . . ?
N4 Cu2 O1 81.21(8) . . ?
O3 Cu2 O1 92.55(8) . . ?
N4 Cu2 N5 81.22(9) . . ?
O3 Cu2 N5 99.80(9) . . ?
O1 Cu2 N5 160.15(9) . . ?
N4 Cu2 O6 107.04(10) . . ?
O3 Cu2 O6 96.53(10) . . ?
O1 Cu2 O6 93.98(9) . . ?
N5 Cu2 O6 99.93(10) . . ?
C1 O1 Cu2 116.84(15) . . ?
C1 O1 Cu1 116.91(16) . . ?
Cu2 O1 Cu1 102.70(9) . . ?
C45 O2 Cu1 128.47(19) . . ?
C45 O3 Cu2 125.0(2) . . ?
C46 O4 Cu1 122.7(2) . . ?
C47 O6 Cu2 126.3(2) . . ?
C3 N1 C7 122.2(2) . . ?
C3 N1 Cu1 118.43(19) . . ?
C7 N1 Cu1 118.56(19) . . ?
C8 N2 C10 106.9(2) . . ?
C8 N2 Cu1 110.63(18) . . ?
C10 N2 Cu1 141.0(2) . . ?
C8 N3 C9 107.3(2) . . ?
C8 N3 C23 126.7(3) . . ?
C9 N3 C23 125.9(2) . . ?
C24 N4 C28 122.0(2) . . ?
C24 N4 Cu2 118.91(17) . . ?
C28 N4 Cu2 118.75(18) . . ?
C29 N5 C31 107.0(2) . . ?
C29 N5 Cu2 110.69(18) . . ?
C31 N5 Cu2 142.14(19) . . ?
C29 N6 C30 107.5(2) . . ?
C29 N6 C44 125.9(2) . . ?
C30 N6 C44 126.3(2) . . ?
O1 C1 C2 108.9(2) . . ?
O1 C1 C24 109.3(2) . . ?
C2 C1 C24 109.0(2) . . ?
O1 C1 C3 109.4(2) . . ?
C2 C1 C3 109.4(2) . . ?
C24 C1 C3 110.8(2) . . ?
N1 C3 C4 120.4(3) . . ?
N1 C3 C1 113.5(2) . . ?
C4 C3 C1 126.1(2) . . ?
C5 C4 C3 118.1(3) . . ?
C4 C5 C6 121.0(3) . . ?
C7 C6 C5 118.3(3) . . ?
N1 C7 C6 120.0(3) . . ?
N1 C7 C8 109.8(2) . . ?
C6 C7 C8 130.2(3) . . ?
N2 C8 N3 110.6(2) . . ?
N2 C8 C7 119.4(2) . . ?
N3 C8 C7 130.0(3) . . ?
C10 C9 N3 106.2(2) . . ?
C10 C9 C17 129.2(3) . . ?
N3 C9 C17 124.6(3) . . ?
N2 C10 C9 108.9(3) . . ?
N2 C10 C11 122.6(3) . . ?
C9 C10 C11 128.5(3) . . ?
C12 C11 C16 119.6(3) . . ?
C12 C11 C10 119.0(3) . . ?
C16 C11 C10 121.4(3) . . ?
C13 C12 C11 119.8(3) . . ?
C14 C13 C12 119.8(4) . . ?
C13 C14 C15 120.7(3) . . ?
C14 C15 C16 119.8(3) . . ?
C15 C16 C11 120.2(3) . . ?
C22 C17 C18 118.5(3) . . ?
C22 C17 C9 119.3(3) . . ?
C18 C17 C9 122.1(3) . . ?
C19 C18 C17 120.7(3) . . ?
C20 C19 C18 119.8(3) . . ?
C19 C20 C21 120.4(3) . . ?
C20 C21 C22 120.0(3) . . ?
C17 C22 C21 120.5(3) . . ?
N4 C24 C25 121.1(2) . . ?
N4 C24 C1 113.3(2) . . ?
C25 C24 C1 125.4(2) . . ?
C24 C25 C26 117.2(3) . . ?
C27 C26 C25 121.2(3) . . ?
C28 C27 C26 118.8(2) . . ?
N4 C28 C27 119.7(3) . . ?
N4 C28 C29 109.4(2) . . ?
C27 C28 C29 130.6(2) . . ?
N5 C29 N6 110.2(2) . . ?
N5 C29 C28 119.7(2) . . ?
N6 C29 C28 130.0(2) . . ?
C31 C30 N6 106.4(2) . . ?
C31 C30 C38 130.5(3) . . ?
N6 C30 C38 123.1(2) . . ?
N5 C31 C30 108.9(2) . . ?
N5 C31 C32 122.2(2) . . ?
C30 C31 C32 128.9(2) . . ?
C33 C32 C37 119.0(3) . . ?
C33 C32 C31 120.7(3) . . ?
C37 C32 C31 120.3(3) . . ?
C32 C33 C34 120.4(3) . . ?
C35 C34 C33 120.1(3) . . ?
C34 C35 C36 120.0(3) . . ?
C37 C36 C35 119.9(3) . . ?
C36 C37 C32 120.6(3) . . ?
C39 C38 C43 119.3(3) . . ?
C39 C38 C30 121.9(3) . . ?
C43 C38 C30 118.7(3) . . ?
C40 C39 C38 119.9(3) . . ?
C41 C40 C39 119.9(3) . . ?
C42 C41 C40 121.1(3) . . ?
C41 C42 C43 119.0(3) . . ?
C42 C43 C38 120.8(3) . . ?
O2 C45 O3 129.1(3) . . ?
O4 C46 O5 127.5(3) . . ?
O6 C47 O7 125.5(3) . . ?

_refine_diff_density_max         0.903
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_mk312b
_database_code_depnum_ccdc_archive 'CCDC 1442850'
_audit_update_record             
;
2015-12-16 deposited with the CCDC.
2016-03-03 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         ?
_chemical_formula_sum            'C23.50 H22.50 Cu2 N6 O9'
_chemical_formula_weight         660.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.8934(18)
_cell_length_b                   10.975(2)
_cell_length_c                   13.212(3)
_cell_angle_alpha                79.75(3)
_cell_angle_beta                 80.08(3)
_cell_angle_gamma                84.89(3)
_cell_volume                     1247.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    13815
_cell_measurement_theta_min      1.59
_cell_measurement_theta_max      26.73

_exptl_crystal_description       block

_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_F_000             671
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.772
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical

_exptl_absorpt_correction_T_min  0.6297
_exptl_absorpt_correction_T_max  0.8408
_exptl_absorpt_process_details   'X-RED (Stoe & Cie, 2002)'


_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13815
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.587
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5294
_reflns_number_gt                4522
_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       'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2002)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0680P)²+1.0725P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5294
_refine_ls_number_parameters     390
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1130
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.29464(4) 0.45675(3) 0.76293(3) 0.02299(11) Uani 1 1 d . . . . .
Cu2 Cu 0.45956(4) 0.23605(3) 0.65558(3) 0.02277(11) Uani 1 1 d . . . . .
N1 N 0.1641(3) 0.3490(2) 0.8696(2) 0.0243(5) Uani 1 1 d . . . . .
N2 N 0.3154(3) 0.5300(2) 0.8893(2) 0.0276(6) Uani 1 1 d . . . . .
N3 N 0.2638(3) 0.5136(3) 1.0610(2) 0.0318(6) Uani 1 1 d . . . . .
N4 N 0.3258(3) 0.1002(2) 0.6762(2) 0.0230(5) Uani 1 1 d . . . . .
N5 N 0.6121(3) 0.1058(2) 0.6045(2) 0.0230(5) Uani 1 1 d . . . . .
N6 N 0.6602(3) -0.0930(2) 0.5957(2) 0.0242(5) Uani 1 1 d . . . . .
O1 O 0.2618(2) 0.33041(18) 0.67980(16) 0.0236(4) Uani 1 1 d . . . . .
O2 O 0.4750(3) 0.5291(2) 0.67254(19) 0.0318(5) Uani 1 1 d . . . . .
O3 O 0.5860(3) 0.3721(2) 0.5909(2) 0.0373(6) Uani 1 1 d . . . . .
C32 C 0.5732(4) 0.4812(3) 0.6091(3) 0.0325(7) Uani 1 1 d D . . . .
O4 O 0.1294(3) 0.6020(2) 0.71585(18) 0.0290(5) Uani 1 1 d D . . . .
O5 O 0.0000(3) 0.7095(2) 0.5953(2) 0.0349(5) Uani 1 1 d D . . . .
C33 C 0.1024(4) 0.6341(3) 0.6241(3) 0.0292(7) Uani 1 1 d D . . . .
C1 C 0.1347(3) 0.2571(3) 0.7234(2) 0.0234(6) Uani 1 1 d . . . . .
C2 C -0.0016(3) 0.3077(3) 0.6685(3) 0.0282(6) Uani 1 1 d . . . . .
H2A H -0.0233 0.3957 0.6735 0.042 Uiso 1 1 calc R U . . .
H2B H -0.0915 0.2615 0.7018 0.042 Uiso 1 1 calc R U . . .
H2C H 0.0226 0.2982 0.5950 0.042 Uiso 1 1 calc R U . . .
C3 C 0.0926(3) 0.2631(3) 0.8399(2) 0.0243(6) Uani 1 1 d . . . . .
C4 C -0.0127(3) 0.1934(3) 0.9128(3) 0.0282(6) Uani 1 1 d . . . . .
H4 H -0.0655 0.1322 0.8929 0.034 Uiso 1 1 calc R U . . .
C5 C -0.0391(4) 0.2149(3) 1.0151(3) 0.0297(7) Uani 1 1 d . . . . .
H5 H -0.1110 0.1682 1.0654 0.036 Uiso 1 1 calc R U . . .
C6 C 0.0386(3) 0.3042(3) 1.0447(2) 0.0288(6) Uani 1 1 d . . . . .
H6 H 0.0209 0.3193 1.1145 0.035 Uiso 1 1 calc R U . . .
C7 C 0.1421(3) 0.3698(3) 0.9696(2) 0.0260(6) Uani 1 1 d . . . . .
C8 C 0.2381(3) 0.4684(3) 0.9768(3) 0.0273(6) Uani 1 1 d . . . . .
C9 C 0.3887(4) 0.6194(3) 0.9186(3) 0.0336(7) Uani 1 1 d . . . . .
H9 H 0.4505 0.6788 0.8726 0.040 Uiso 1 1 calc R U . . .
C10 C 0.3585(4) 0.6094(3) 1.0245(3) 0.0370(8) Uani 1 1 d . . . . .
H10 H 0.3961 0.6594 1.0653 0.044 Uiso 1 1 calc R U . . .
C11 C 0.2143(4) 0.4642(4) 1.1703(3) 0.0446(9) Uani 1 1 d . . . . .
H11A H 0.1026 0.4743 1.1866 0.067 Uiso 1 1 calc R U . . .
H11B H 0.2603 0.5090 1.2139 0.067 Uiso 1 1 calc R U . . .
H11C H 0.2466 0.3759 1.1840 0.067 Uiso 1 1 calc R U . . .
C12 C 0.1783(3) 0.1222(3) 0.7085(2) 0.0234(6) Uani 1 1 d . . . . .
C13 C 0.0793(3) 0.0265(3) 0.7249(2) 0.0267(6) Uani 1 1 d . . . . .
H13 H -0.0274 0.0413 0.7463 0.032 Uiso 1 1 calc R U . . .
C14 C 0.1401(4) -0.0907(3) 0.7093(2) 0.0273(6) Uani 1 1 d . . . . .
H14 H 0.0745 -0.1573 0.7210 0.033 Uiso 1 1 calc R U . . .
C15 C 0.2958(3) -0.1120(3) 0.6766(2) 0.0259(6) Uani 1 1 d . . . . .
H15 H 0.3381 -0.1924 0.6668 0.031 Uiso 1 1 calc R U . . .
C16 C 0.3871(3) -0.0125(3) 0.6587(2) 0.0232(6) Uani 1 1 d . . . . .
C17 C 0.5517(3) -0.0050(3) 0.6195(2) 0.0223(6) Uani 1 1 d . . . . .
C18 C 0.7648(3) 0.0861(3) 0.5704(2) 0.0247(6) Uani 1 1 d . . . . .
H18 H 0.8374 0.1480 0.5532 0.030 Uiso 1 1 calc R U . . .
C19 C 0.7962(3) -0.0373(3) 0.5648(2) 0.0253(6) Uani 1 1 d . . . . .
H19 H 0.8933 -0.0765 0.5437 0.030 Uiso 1 1 calc R U . . .
C31 C 0.6419(4) -0.2259(3) 0.6042(3) 0.0299(7) Uani 1 1 d . . . . .
H31A H 0.5967 -0.2594 0.6757 0.045 Uiso 1 1 calc R U . . .
H31B H 0.7420 -0.2686 0.5866 0.045 Uiso 1 1 calc R U . . .
H31C H 0.5746 -0.2386 0.5561 0.045 Uiso 1 1 calc R U . . .
C35A C 0.706(2) 0.9116(15) 0.8319(12) 0.0349(16) Uani 0.618(6) 1 d D . P A 1
H35A H 0.7896 0.8594 0.8063 0.042 Uiso 0.618(6) 1 calc R U P A 1
O8A O 0.5747(16) 0.8718(9) 0.8435(11) 0.056(2) Uani 0.618(6) 1 d D . P A 1
O9A O 0.7370(6) 1.0169(5) 0.8515(5) 0.0559(12) Uani 0.618(6) 1 d D . P A 1
C35B C 0.705(4) 0.914(2) 0.849(2) 0.0349(16) Uani 0.382(6) 1 d D . P A 2
H35B H 0.7616 0.9289 0.7807 0.042 Uiso 0.382(6) 1 calc R U P A 2
O8B O 0.601(3) 0.8406(17) 0.863(2) 0.056(2) Uani 0.382(6) 1 d D . P A 2
O9B O 0.7463(10) 0.9733(9) 0.9144(8) 0.0559(12) Uani 0.382(6) 1 d D . P A 2
O6A O 0.5318(17) 0.1968(15) 0.8196(12) 0.030(4) Uiso 0.25 1 d . . P B 3
O7A O 0.3289(6) 0.0067(5) 0.9255(4) 0.0211(11) Uiso 0.35 1 d . . P C 3
O6C O 0.5012(14) 0.2046(13) 0.8298(10) 0.012(3) Uiso 0.25 1 d . . P B 4
O7C O 0.4367(18) -0.0384(14) 0.9637(12) 0.032(3) Uiso 0.15 1 d . . P D 4
C34B C 0.4696(7) 0.1672(6) 0.8837(6) 0.0313(14) Uiso 0.5 1 d D . P B 5
H34B H 0.5104 0.1695 0.9452 0.038 Uiso 0.5 1 calc R U P B 5
O7B O 0.3728(7) 0.0889(5) 0.8923(5) 0.0492(13) Uiso 0.5 1 d D . P B 5
O6B O 0.5215(7) 0.2443(5) 0.8043(4) 0.0266(12) Uiso 0.5 1 d D . P B 5
H32H H 0.650(5) 0.537(4) 0.560(4) 0.080 Uiso 1 1 d D U . . .
H33H H 0.173(5) 0.602(5) 0.564(3) 0.080 Uiso 1 1 d D 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 N1 1.954(3) . ?
Cu1 O2 1.964(2) . ?
Cu1 O1 1.985(2) . ?
Cu1 N2 2.020(3) . ?
Cu1 O4 2.152(2) . ?
Cu2 O3 1.933(2) . ?
Cu2 N4 1.942(2) . ?
Cu2 O1 1.967(2) . ?
Cu2 N5 2.005(3) . ?
Cu2 O6B 2.148(5) . ?
Cu2 O6A 2.323(15) . ?
Cu2 O6C 2.354(12) . ?
N1 C3 1.331(4) . ?
N1 C7 1.359(4) . ?
N2 C8 1.340(4) . ?
N2 C9 1.369(4) . ?
N3 C8 1.356(4) . ?
N3 C10 1.374(5) . ?
N3 C11 1.456(5) . ?
N4 C12 1.322(4) . ?
N4 C16 1.349(4) . ?
N5 C17 1.342(4) . ?
N5 C18 1.366(4) . ?
N6 C17 1.342(4) . ?
N6 C19 1.370(4) . ?
N6 C31 1.464(4) . ?
O1 C1 1.424(3) . ?
O2 C32 1.251(4) . ?
O3 C32 1.254(4) . ?
O4 C33 1.259(4) . ?
O5 C33 1.238(4) . ?
C1 C2 1.531(4) . ?
C1 C3 1.533(4) . ?
C1 C12 1.535(4) . ?
C3 C4 1.394(4) . ?
C4 C5 1.390(5) . ?
C5 C6 1.393(4) . ?
C6 C7 1.378(5) . ?
C7 C8 1.462(4) . ?
C9 C10 1.365(5) . ?
C12 C13 1.394(4) . ?
C13 C14 1.387(4) . ?
C14 C15 1.390(4) . ?
C15 C16 1.381(4) . ?
C16 C17 1.471(4) . ?
C18 C19 1.371(4) . ?
C35A O8A 1.256(10) . ?
C35A O9A 1.292(11) . ?
C35B O8B 1.251(13) . ?
C35B O9B 1.280(14) . ?
C34B O7B 1.248(8) . ?
C34B O6B 1.272(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 O2 162.24(10) . . ?
N1 Cu1 O1 80.55(10) . . ?
O2 Cu1 O1 98.54(9) . . ?
N1 Cu1 N2 80.57(11) . . ?
O2 Cu1 N2 96.43(11) . . ?
O1 Cu1 N2 158.69(10) . . ?
N1 Cu1 O4 100.50(10) . . ?
O2 Cu1 O4 97.09(10) . . ?
O1 Cu1 O4 100.89(9) . . ?
N2 Cu1 O4 92.18(10) . . ?
O3 Cu2 N4 162.32(11) . . ?
O3 Cu2 O1 98.86(9) . . ?
N4 Cu2 O1 81.32(9) . . ?
O3 Cu2 N5 94.26(10) . . ?
N4 Cu2 N5 80.90(10) . . ?
O1 Cu2 N5 158.12(9) . . ?
O3 Cu2 O6B 90.45(18) . . ?
N4 Cu2 O6B 107.16(18) . . ?
O1 Cu2 O6B 95.52(17) . . ?
N5 Cu2 O6B 101.83(17) . . ?
O3 Cu2 O6A 99.8(4) . . ?
N4 Cu2 O6A 97.4(4) . . ?
O1 Cu2 O6A 102.7(4) . . ?
N5 Cu2 O6A 92.2(4) . . ?
O3 Cu2 O6C 102.6(3) . . ?
N4 Cu2 O6C 94.9(3) . . ?
O1 Cu2 O6C 95.7(3) . . ?
N5 Cu2 O6C 98.5(3) . . ?
C3 N1 C7 122.6(3) . . ?
C3 N1 Cu1 118.4(2) . . ?
C7 N1 Cu1 118.9(2) . . ?
C8 N2 C9 106.6(3) . . ?
C8 N2 Cu1 111.7(2) . . ?
C9 N2 Cu1 141.5(3) . . ?
C8 N3 C10 107.0(3) . . ?
C8 N3 C11 127.4(3) . . ?
C10 N3 C11 125.3(3) . . ?
C12 N4 C16 122.8(3) . . ?
C12 N4 Cu2 118.3(2) . . ?
C16 N4 Cu2 118.9(2) . . ?
C17 N5 C18 106.3(2) . . ?
C17 N5 Cu2 111.9(2) . . ?
C18 N5 Cu2 141.2(2) . . ?
C17 N6 C19 107.6(2) . . ?
C17 N6 C31 127.4(3) . . ?
C19 N6 C31 124.9(3) . . ?
C1 O1 Cu2 115.01(17) . . ?
C1 O1 Cu1 114.53(17) . . ?
Cu2 O1 Cu1 105.59(9) . . ?
C32 O2 Cu1 129.3(2) . . ?
C32 O3 Cu2 128.4(2) . . ?
O2 C32 O3 128.6(3) . . ?
C33 O4 Cu1 124.6(2) . . ?
O5 C33 O4 126.6(3) . . ?
O1 C1 C2 109.3(2) . . ?
O1 C1 C3 109.4(2) . . ?
C2 C1 C3 109.5(2) . . ?
O1 C1 C12 109.1(2) . . ?
C2 C1 C12 110.1(2) . . ?
C3 C1 C12 109.5(2) . . ?
N1 C3 C4 119.4(3) . . ?
N1 C3 C1 113.3(3) . . ?
C4 C3 C1 127.3(3) . . ?
C5 C4 C3 119.0(3) . . ?
C4 C5 C6 120.6(3) . . ?
C7 C6 C5 118.0(3) . . ?
N1 C7 C6 120.4(3) . . ?
N1 C7 C8 109.2(3) . . ?
C6 C7 C8 130.4(3) . . ?
N2 C8 N3 110.3(3) . . ?
N2 C8 C7 119.2(3) . . ?
N3 C8 C7 130.5(3) . . ?
C10 C9 N2 108.9(3) . . ?
C9 C10 N3 107.1(3) . . ?
N4 C12 C13 119.7(3) . . ?
N4 C12 C1 113.7(2) . . ?
C13 C12 C1 126.6(3) . . ?
C14 C13 C12 118.5(3) . . ?
C13 C14 C15 120.8(3) . . ?
C16 C15 C14 117.9(3) . . ?
N4 C16 C15 120.2(3) . . ?
N4 C16 C17 109.5(2) . . ?
C15 C16 C17 130.3(3) . . ?
N5 C17 N6 110.5(3) . . ?
N5 C17 C16 118.4(3) . . ?
N6 C17 C16 131.1(3) . . ?
N5 C18 C19 109.0(3) . . ?
N6 C19 C18 106.6(3) . . ?
O8A C35A O9A 125.9(17) . . ?
O8B C35B O9B 129(3) . . ?
O7B C34B O6B 129.1(7) . . ?
C34B O6B Cu2 119.6(5) . . ?

_refine_diff_density_max         0.517
_refine_diff_density_min         -1.095
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_mk340_sq
_database_code_depnum_ccdc_archive 'CCDC 1442851'
_audit_update_record             
;
2015-12-16 deposited with the CCDC.
2016-03-03 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         'C45 H38 Cu2 N6 O5'
_chemical_formula_sum            'C45 H38 Cu2 N6 O5'
_chemical_formula_weight         869.89

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

_cell_length_a                   15.2115(3)
_cell_length_b                   16.7551(4)
_cell_length_c                   19.9050(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5073.19(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    59629
_cell_measurement_theta_min      1.589
_cell_measurement_theta_max      25.679

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_F_000             1792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.882
_shelx_estimated_absorpt_T_min   0.667
_shelx_estimated_absorpt_T_max   0.872
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6961
_exptl_absorpt_correction_T_max  0.9033
_exptl_absorpt_process_details   'X-RED (Stoe & Cie, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            59629
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.589
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9580
_reflns_number_gt                8583
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2002)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2012)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0534P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3380 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         9580
_refine_ls_number_parameters     528
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0853
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.31430(3) 0.53965(3) 0.48460(2) 0.03417(12) Uani 1 1 d . . . . .
Cu2 Cu 0.32539(3) 0.53227(3) 0.65169(2) 0.03651(12) Uani 1 1 d . . . . .
N1 N 0.22641(18) 0.4591(2) 0.46486(15) 0.0320(6) Uani 1 1 d . . . . .
N2 N 0.3673(2) 0.4955(2) 0.39954(16) 0.0363(7) Uani 1 1 d . . . . .
N3 N 0.3426(2) 0.4097(2) 0.31321(16) 0.0401(8) Uani 1 1 d . . . . .
N4 N 0.23660(19) 0.4550(2) 0.67605(15) 0.0341(7) Uani 1 1 d . . . . .
N5 N 0.3796(2) 0.4921(2) 0.73618(16) 0.0408(8) Uani 1 1 d . . . . .
N6 N 0.3631(2) 0.4069(2) 0.82368(16) 0.0388(8) Uani 1 1 d . . . . .
O1 O 0.25191(14) 0.53927(14) 0.57053(13) 0.0326(5) Uani 1 1 d . . . . .
O2 O 0.4035(2) 0.6154(2) 0.51153(15) 0.0618(9) Uani 1 1 d . . . . .
O3 O 0.4262(2) 0.5882(3) 0.61781(17) 0.0768(13) Uani 1 1 d . . . . .
O4 O 0.2428(2) 0.64002(16) 0.42843(17) 0.0472(7) Uani 1 1 d D . . . .
O5 O 0.2714(2) 0.63774(18) 0.71017(16) 0.0514(8) Uani 1 1 d D . . . .
C1 C 0.1701(2) 0.4975(2) 0.57226(19) 0.0327(7) Uani 1 1 d . . . . .
C2 C 0.0945(2) 0.5580(2) 0.5724(2) 0.0422(9) Uani 1 1 d . . . . .
H2A H 0.0983 0.5912 0.6128 0.063 Uiso 1 1 calc R U . . .
H2B H 0.0383 0.5295 0.5720 0.063 Uiso 1 1 calc R U . . .
H2C H 0.0987 0.5919 0.5324 0.063 Uiso 1 1 calc R U . . .
C3 C 0.1626(2) 0.4463(2) 0.50901(18) 0.0335(8) Uani 1 1 d . . . . .
C4 C 0.0960(3) 0.3924(3) 0.4919(2) 0.0428(9) Uani 1 1 d . . . . .
H4A H 0.0488 0.3825 0.5219 0.051 Uiso 1 1 calc R U . . .
C5 C 0.0998(3) 0.3538(3) 0.4309(3) 0.0493(10) Uani 1 1 d . . . . .
H5A H 0.0552 0.3165 0.4194 0.059 Uiso 1 1 calc R U . . .
C6 C 0.1667(3) 0.3681(2) 0.3863(2) 0.0415(9) Uani 1 1 d . . . . .
H6 H 0.1685 0.3421 0.3440 0.050 Uiso 1 1 calc R U . . .
C7 C 0.2319(2) 0.4219(2) 0.40496(19) 0.0334(8) Uani 1 1 d . . . . .
C8 C 0.3119(3) 0.4425(2) 0.36949(18) 0.0361(8) Uani 1 1 d . . . . .
C9 C 0.4404(3) 0.4946(3) 0.3590(2) 0.0419(9) Uani 1 1 d . . . . .
C10 C 0.4251(3) 0.4416(3) 0.3068(2) 0.0425(10) Uani 1 1 d . . . . .
C11 C 0.5205(2) 0.5401(3) 0.3756(2) 0.0461(9) Uani 1 1 d . . . . .
C12 C 0.6041(3) 0.5024(3) 0.3738(2) 0.0533(11) Uani 1 1 d . . . . .
H12 H 0.6087 0.4474 0.3625 0.064 Uiso 1 1 calc R U . . .
C13 C 0.6783(3) 0.5461(4) 0.3884(3) 0.0664(13) Uani 1 1 d . . . . .
H13 H 0.7343 0.5211 0.3862 0.080 Uiso 1 1 calc R U . . .
C14 C 0.6731(4) 0.6239(4) 0.4057(3) 0.0727(15) Uani 1 1 d . . . . .
H14 H 0.7250 0.6528 0.4163 0.087 Uiso 1 1 calc R U . . .
C15 C 0.5917(4) 0.6615(4) 0.4081(3) 0.0689(15) Uani 1 1 d . . . . .
H15 H 0.5877 0.7162 0.4203 0.083 Uiso 1 1 calc R U . . .
C16 C 0.5166(3) 0.6186(3) 0.3925(3) 0.0539(12) Uani 1 1 d . . . . .
H16 H 0.4611 0.6447 0.3936 0.065 Uiso 1 1 calc R U . . .
C17 C 0.4847(3) 0.4154(3) 0.2524(2) 0.0531(12) Uani 1 1 d . . . . .
C18 C 0.5460(3) 0.4657(5) 0.2238(2) 0.0681(15) Uani 1 1 d . . . . .
H18 H 0.5481 0.5205 0.2359 0.082 Uiso 1 1 calc R U . . .
C19 C 0.6070(4) 0.4336(5) 0.1748(3) 0.0779(19) Uani 1 1 d . . . . .
H19 H 0.6499 0.4673 0.1549 0.094 Uiso 1 1 calc R U . . .
C20 C 0.6031(5) 0.3567(6) 0.1577(3) 0.097(3) Uani 1 1 d . . . . .
H20 H 0.6448 0.3364 0.1266 0.116 Uiso 1 1 calc R U . . .
C21 C 0.5407(5) 0.3058(5) 0.1837(3) 0.087(2) Uani 1 1 d . . . . .
H21 H 0.5376 0.2518 0.1695 0.105 Uiso 1 1 calc R U . . .
C22 C 0.4822(4) 0.3358(4) 0.2314(2) 0.0664(15) Uani 1 1 d . . . . .
H22 H 0.4393 0.3011 0.2502 0.080 Uiso 1 1 calc R U . . .
C23 C 0.1664(2) 0.4463(2) 0.63637(18) 0.0365(8) Uani 1 1 d . . . . .
C24 C 0.0975(3) 0.3977(3) 0.6568(3) 0.0618(13) Uani 1 1 d . . . . .
H24 H 0.0460 0.3921 0.6302 0.074 Uiso 1 1 calc R U . . .
C25 C 0.1066(4) 0.3574(3) 0.7179(3) 0.0650(14) Uani 1 1 d . . . . .
H25 H 0.0605 0.3235 0.7329 0.078 Uiso 1 1 calc R U . . .
C26 C 0.1812(3) 0.3658(3) 0.7568(2) 0.0530(11) Uani 1 1 d . . . . .
H26 H 0.1876 0.3373 0.7978 0.064 Uiso 1 1 calc R U . . .
C27 C 0.2462(3) 0.4167(2) 0.73456(19) 0.0374(9) Uani 1 1 d . . . . .
C28 C 0.3297(2) 0.4373(2) 0.76717(18) 0.0353(8) Uani 1 1 d . . . . .
C29 C 0.4534(3) 0.4984(3) 0.7770(2) 0.0439(10) Uani 1 1 d D . . . .
C30 C 0.4422(2) 0.4455(3) 0.83026(19) 0.0408(9) Uani 1 1 d . . . . .
C31A C 0.5318(4) 0.5458(4) 0.7600(6) 0.0421(18) Uani 0.652(12) 1 d DG . P A 1
C32A C 0.5192(4) 0.6258(4) 0.7442(5) 0.047(2) Uani 0.652(12) 1 d G . P A 1
H32A H 0.4613 0.6471 0.7420 0.056 Uiso 0.652(12) 1 calc R U P A 1
C33A C 0.5911(5) 0.6747(4) 0.7315(4) 0.056(2) Uani 0.652(12) 1 d G . P A 1
H33A H 0.5825 0.7293 0.7207 0.067 Uiso 0.652(12) 1 calc R U P A 1
C34A C 0.6757(4) 0.6435(5) 0.7347(4) 0.069(3) Uani 0.652(12) 1 d G . P A 1
H34A H 0.7249 0.6769 0.7261 0.083 Uiso 0.652(12) 1 calc R U P A 1
C35A C 0.6884(4) 0.5636(5) 0.7506(5) 0.071(3) Uani 0.652(12) 1 d G . P A 1
H35A H 0.7462 0.5423 0.7528 0.085 Uiso 0.652(12) 1 calc R U P A 1
C36A C 0.6164(4) 0.5147(4) 0.7632(5) 0.053(2) Uani 0.652(12) 1 d G . P A 1
H36A H 0.6250 0.4601 0.7741 0.063 Uiso 0.652(12) 1 calc R U P A 1
C31B C 0.5188(8) 0.5679(8) 0.7643(12) 0.0421(18) Uani 0.348(12) 1 d DG . P A 2
C32B C 0.4960(7) 0.6465(8) 0.7502(11) 0.047(2) Uani 0.348(12) 1 d G . P A 2
H32B H 0.4358 0.6617 0.7490 0.056 Uiso 0.348(12) 1 calc R U P A 2
C33B C 0.5611(9) 0.7028(8) 0.7378(8) 0.056(2) Uani 0.348(12) 1 d G . P A 2
H33B H 0.5455 0.7565 0.7281 0.067 Uiso 0.348(12) 1 calc R U P A 2
C34B C 0.6491(8) 0.6805(9) 0.7395(9) 0.069(3) Uani 0.348(12) 1 d G . P A 2
H34B H 0.6936 0.7190 0.7310 0.083 Uiso 0.348(12) 1 calc R U P A 2
C35B C 0.6719(7) 0.6020(10) 0.7536(10) 0.071(3) Uani 0.348(12) 1 d G . P A 2
H35B H 0.7321 0.5867 0.7548 0.085 Uiso 0.348(12) 1 calc R U P A 2
C36B C 0.6068(9) 0.5457(8) 0.7660(11) 0.053(2) Uani 0.348(12) 1 d G . P A 2
H36B H 0.6224 0.4920 0.7757 0.063 Uiso 0.348(12) 1 calc R U P A 2
C37 C 0.5021(3) 0.4297(3) 0.88662(19) 0.0430(10) Uani 1 1 d . . . . .
C38 C 0.5522(3) 0.4901(3) 0.9153(2) 0.0503(11) Uani 1 1 d . . . . .
H38 H 0.5462 0.5431 0.8991 0.060 Uiso 1 1 calc R U . . .
C39 C 0.6105(3) 0.4747(4) 0.9667(2) 0.0594(13) Uani 1 1 d . . . . .
H39 H 0.6441 0.5168 0.9858 0.071 Uiso 1 1 calc R U . . .
C40 C 0.6197(3) 0.3982(4) 0.9901(2) 0.0622(14) Uani 1 1 d . . . . .
H40 H 0.6604 0.3874 1.0251 0.075 Uiso 1 1 calc R U . . .
C41 C 0.5721(3) 0.3385(3) 0.9640(2) 0.0596(13) Uani 1 1 d . . . . .
H41 H 0.5791 0.2859 0.9810 0.072 Uiso 1 1 calc R U . . .
C42 C 0.5116(3) 0.3531(3) 0.9117(2) 0.0533(12) Uani 1 1 d . . . . .
H42 H 0.4776 0.3105 0.8938 0.064 Uiso 1 1 calc R U . . .
C43 C 0.4428(3) 0.6205(3) 0.5648(2) 0.0473(10) Uani 1 1 d . . . . .
H43 H 0.4931 0.6542 0.5647 0.057 Uiso 1 1 calc R U . . .
C44 C 0.2201(3) 0.7147(3) 0.4553(3) 0.0567(12) Uani 1 1 d . . . . .
H44A H 0.1592 0.7131 0.4713 0.085 Uiso 1 1 calc R U . . .
H44B H 0.2258 0.7557 0.4204 0.085 Uiso 1 1 calc R U . . .
H44C H 0.2594 0.7274 0.4928 0.085 Uiso 1 1 calc R U . . .
C45 C 0.2545(4) 0.7130(3) 0.6790(3) 0.0685(15) Uani 1 1 d . . . . .
H45A H 0.2315 0.7504 0.7126 0.103 Uiso 1 1 calc R U . . .
H45B H 0.3092 0.7342 0.6601 0.103 Uiso 1 1 calc R U . . .
H45C H 0.2111 0.7061 0.6431 0.103 Uiso 1 1 calc R U . . .
H4 H 0.209(3) 0.628(3) 0.398(2) 0.062(16) Uiso 1 1 d D . . . .
H5 H 0.2200(18) 0.634(3) 0.720(3) 0.049(15) Uiso 1 1 d 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 1.934(3) . ?
Cu1 N1 1.940(3) . ?
Cu1 O1 1.956(2) . ?
Cu1 N2 2.016(3) . ?
Cu1 O4 2.293(3) . ?
Cu2 O3 1.920(3) . ?
Cu2 N4 1.932(3) . ?
Cu2 O1 1.968(2) . ?
Cu2 N5 1.991(3) . ?
Cu2 O5 2.270(3) . ?
N1 C3 1.327(5) . ?
N1 C7 1.348(5) . ?
N2 C8 1.363(5) . ?
N2 C9 1.374(5) . ?
N3 C8 1.332(5) . ?
N3 C10 1.370(5) . ?
N4 C23 1.336(5) . ?
N4 C27 1.338(5) . ?
N5 C28 1.342(5) . ?
N5 C29 1.389(5) . ?
N6 C28 1.335(5) . ?
N6 C30 1.373(5) . ?
O1 C1 1.427(4) . ?
O2 C43 1.219(5) . ?
O3 C43 1.213(5) . ?
O4 C44 1.404(5) . ?
O5 C45 1.429(6) . ?
C1 C3 1.528(5) . ?
C1 C2 1.532(5) . ?
C1 C23 1.539(5) . ?
C3 C4 1.400(5) . ?
C4 C5 1.377(6) . ?
C5 C6 1.371(6) . ?
C6 C7 1.391(6) . ?
C7 C8 1.448(5) . ?
C9 C10 1.388(6) . ?
C9 C11 1.475(6) . ?
C10 C17 1.478(6) . ?
C11 C16 1.359(7) . ?
C11 C12 1.420(6) . ?
C12 C13 1.377(7) . ?
C13 C14 1.350(9) . ?
C14 C15 1.390(8) . ?
C15 C16 1.385(7) . ?
C17 C18 1.380(8) . ?
C17 C22 1.399(8) . ?
C18 C19 1.449(8) . ?
C19 C20 1.333(10) . ?
C20 C21 1.376(11) . ?
C21 C22 1.396(8) . ?
C23 C24 1.388(6) . ?
C24 C25 1.398(7) . ?
C25 C26 1.382(7) . ?
C26 C27 1.378(6) . ?
C27 C28 1.467(6) . ?
C29 C30 1.393(6) . ?
C29 C31A 1.472(6) . ?
C29 C31B 1.553(11) . ?
C30 C37 1.469(5) . ?
C31A C32A 1.3900 . ?
C31A C36A 1.3900 . ?
C32A C33A 1.3900 . ?
C33A C34A 1.3900 . ?
C34A C35A 1.3900 . ?
C35A C36A 1.3900 . ?
C31B C32B 1.3900 . ?
C31B C36B 1.3900 . ?
C32B C33B 1.3900 . ?
C33B C34B 1.3900 . ?
C34B C35B 1.3900 . ?
C35B C36B 1.3900 . ?
C37 C42 1.386(7) . ?
C37 C38 1.389(7) . ?
C38 C39 1.379(6) . ?
C39 C40 1.370(8) . ?
C40 C41 1.340(8) . ?
C41 C42 1.410(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 N1 175.11(13) . . ?
O2 Cu1 O1 95.76(12) . . ?
N1 Cu1 O1 80.82(11) . . ?
O2 Cu1 N2 101.15(14) . . ?
N1 Cu1 N2 81.36(13) . . ?
O1 Cu1 N2 157.98(12) . . ?
O2 Cu1 O4 89.23(14) . . ?
N1 Cu1 O4 94.86(12) . . ?
O1 Cu1 O4 101.45(11) . . ?
N2 Cu1 O4 92.83(12) . . ?
O3 Cu2 N4 166.80(18) . . ?
O3 Cu2 O1 97.83(12) . . ?
N4 Cu2 O1 81.31(11) . . ?
O3 Cu2 N5 97.53(14) . . ?
N4 Cu2 N5 81.44(13) . . ?
O1 Cu2 N5 161.64(13) . . ?
O3 Cu2 O5 95.09(17) . . ?
N4 Cu2 O5 98.04(13) . . ?
O1 Cu2 O5 99.73(11) . . ?
N5 Cu2 O5 88.86(13) . . ?
C3 N1 C7 123.8(3) . . ?
C3 N1 Cu1 118.9(3) . . ?
C7 N1 Cu1 117.2(3) . . ?
C8 N2 C9 103.7(3) . . ?
C8 N2 Cu1 111.2(2) . . ?
C9 N2 Cu1 145.1(3) . . ?
C8 N3 C10 103.8(3) . . ?
C23 N4 C27 123.3(3) . . ?
C23 N4 Cu2 118.9(2) . . ?
C27 N4 Cu2 117.6(3) . . ?
C28 N5 C29 103.9(3) . . ?
C28 N5 Cu2 112.6(2) . . ?
C29 N5 Cu2 143.4(3) . . ?
C28 N6 C30 103.6(3) . . ?
C1 O1 Cu1 116.5(2) . . ?
C1 O1 Cu2 116.5(2) . . ?
Cu1 O1 Cu2 116.26(11) . . ?
C43 O2 Cu1 129.1(3) . . ?
C43 O3 Cu2 133.6(3) . . ?
C44 O4 Cu1 125.8(3) . . ?
C45 O5 Cu2 122.0(3) . . ?
O1 C1 C3 108.7(3) . . ?
O1 C1 C2 109.3(3) . . ?
C3 C1 C2 108.5(3) . . ?
O1 C1 C23 109.0(3) . . ?
C3 C1 C23 111.5(3) . . ?
C2 C1 C23 109.9(3) . . ?
N1 C3 C4 118.2(3) . . ?
N1 C3 C1 113.6(3) . . ?
C4 C3 C1 128.1(3) . . ?
C5 C4 C3 119.2(4) . . ?
C6 C5 C4 121.2(4) . . ?
C5 C6 C7 118.1(4) . . ?
N1 C7 C6 119.4(4) . . ?
N1 C7 C8 112.0(3) . . ?
C6 C7 C8 128.6(4) . . ?
N3 C8 N2 114.9(4) . . ?
N3 C8 C7 127.4(4) . . ?
N2 C8 C7 117.4(3) . . ?
N2 C9 C10 108.1(4) . . ?
N2 C9 C11 122.2(4) . . ?
C10 C9 C11 129.7(4) . . ?
N3 C10 C9 109.5(3) . . ?
N3 C10 C17 121.0(4) . . ?
C9 C10 C17 129.4(4) . . ?
C16 C11 C12 118.5(4) . . ?
C16 C11 C9 121.3(4) . . ?
C12 C11 C9 120.2(4) . . ?
C13 C12 C11 119.4(5) . . ?
C14 C13 C12 121.3(5) . . ?
C13 C14 C15 119.9(5) . . ?
C16 C15 C14 119.5(6) . . ?
C11 C16 C15 121.4(5) . . ?
C18 C17 C22 118.5(5) . . ?
C18 C17 C10 122.4(5) . . ?
C22 C17 C10 119.0(5) . . ?
C17 C18 C19 118.9(7) . . ?
C20 C19 C18 120.2(7) . . ?
C19 C20 C21 122.2(6) . . ?
C20 C21 C22 118.2(7) . . ?
C21 C22 C17 122.0(6) . . ?
N4 C23 C24 119.6(4) . . ?
N4 C23 C1 113.6(3) . . ?
C24 C23 C1 126.7(4) . . ?
C23 C24 C25 117.6(4) . . ?
C26 C25 C24 121.3(4) . . ?
C27 C26 C25 118.2(4) . . ?
N4 C27 C26 119.9(4) . . ?
N4 C27 C28 111.5(3) . . ?
C26 C27 C28 128.6(4) . . ?
N6 C28 N5 115.6(3) . . ?
N6 C28 C27 127.8(4) . . ?
N5 C28 C27 116.6(3) . . ?
N5 C29 C30 107.3(4) . . ?
N5 C29 C31A 124.1(5) . . ?
C30 C29 C31A 128.1(5) . . ?
N5 C29 C31B 118.7(9) . . ?
C30 C29 C31B 132.8(9) . . ?
N6 C30 C29 109.5(3) . . ?
N6 C30 C37 122.2(4) . . ?
C29 C30 C37 128.3(4) . . ?
C32A C31A C36A 120.0 . . ?
C32A C31A C29 117.5(4) . . ?
C36A C31A C29 122.4(4) . . ?
C31A C32A C33A 120.0 . . ?
C34A C33A C32A 120.0 . . ?
C35A C34A C33A 120.0 . . ?
C34A C35A C36A 120.0 . . ?
C35A C36A C31A 120.0 . . ?
C32B C31B C36B 120.0 . . ?
C32B C31B C29 125.7(8) . . ?
C36B C31B C29 114.3(8) . . ?
C33B C32B C31B 120.0 . . ?
C34B C33B C32B 120.0 . . ?
C33B C34B C35B 120.0 . . ?
C34B C35B C36B 120.0 . . ?
C35B C36B C31B 120.0 . . ?
C42 C37 C38 118.0(4) . . ?
C42 C37 C30 120.4(4) . . ?
C38 C37 C30 121.6(4) . . ?
C39 C38 C37 121.5(5) . . ?
C40 C39 C38 119.5(5) . . ?
C41 C40 C39 120.8(4) . . ?
C40 C41 C42 120.6(5) . . ?
C37 C42 C41 119.6(5) . . ?
O3 C43 O2 128.5(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 N6 0.81(3) 1.94(3) 2.750(5) 175(5) 2_564
O5 H5 N3 0.81(2) 2.22(4) 2.801(5) 130(5) 2_565
O5 H5 N3 0.81(2) 2.22(4) 2.801(5) 130(5) 2_565

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.049


# SQUEEZE RESULTS (Version =  11015)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.250 0.500 773 168 ' '
2 -0.021 0.750 0.000 773 168 ' '
# Missing Reflections Below sin(th)/lambda = 0.25
loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
1 1 0 1.808
0 2 0 2.431
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
TITL mk340     P 21 21 21   R = 0.07
CELL   15.2115   16.7551   19.9050     90.00     90.00     90.00
SPGR P212121
# Solvent Accessible Volume =    1542.0
# Electrons Found in S.A.V. =     335.4
# Note: Atoms in Void as Cxxx and Qxxx all others
C101 0.110 0.735 0.033 !       2.55 eA-3
C102 0.505 0.823 0.934 !       2.44 eA-3
C103 0.815 0.232 0.427 !       2.43 eA-3
C104 0.014 0.708 0.933 !       2.41 eA-3
C105 0.782 0.298 0.426 !       2.41 eA-3
C106 0.342 0.169 0.360 !       2.30 eA-3
C107 0.602 0.658 0.079 !       2.19 eA-3
C108 0.150 0.997 0.420 !       2.19 eA-3
C109 0.559 0.837 0.985 !       2.07 eA-3
C110 0.736 0.422 0.611 !       2.06 eA-3
C111 0.677 0.458 0.565 !       1.93 eA-3
C112 0.972 0.664 0.184 !       1.83 eA-3
C113 0.530 0.863 0.879 !       1.78 eA-3
C114 0.269 0.157 0.388 !       1.70 eA-3
C115 0.097 0.718 0.096 !       1.37 eA-3
C116 0.405 0.883 0.910 !       1.37 eA-3
C117 0.076 0.695 0.988 !       1.23 eA-3
C118 0.968 0.599 0.146 !       1.21 eA-3
C119 0.306 0.175 0.449 !       0.91 eA-3
C120 0.391 0.941 0.963 !       0.87 eA-3
C121 0.748 0.371 0.514 !       0.68 eA-3
Q122 0.232 0.205 0.254 !       0.66 eA-3
C123 0.626 0.731 0.150 !       0.62 eA-3
Q124 0.675 1.000 0.026 !       0.56 eA-3
C125 0.720 0.300 0.350 !       0.54 eA-3
C126 0.988 0.763 0.930 !       0.52 eA-3
;

