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

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

data_compound1
_database_code_depnum_ccdc_archive 'CCDC 1517751'
_audit_update_record             
;
2018-03-09 deposited with the CCDC.
2018-03-16 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         'C28 H34 Cu3 N6 O10'
_chemical_formula_sum            'C28 H34 Cu3 N6 O10'
_chemical_formula_weight         805.23

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                   15.225(3)
_cell_length_b                   19.518(4)
_cell_length_c                   10.927(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.42(3)
_cell_angle_gamma                90
_cell_volume                     3241.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2952
_cell_measurement_theta_min      0.27480
_cell_measurement_theta_max      0.3845

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             1644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    2.015
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2748
_exptl_absorpt_correction_T_max  0.3845
_exptl_absorpt_process_details   SADABS
_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  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10463
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.698
_diffrn_reflns_theta_max         25.364
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2952
_reflns_number_gt                2672
_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)+(0.0299P)²+0.8504P] 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         2952
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0192
_refine_ls_wR_factor_ref         0.0530
_refine_ls_wR_factor_gt          0.0522
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.52192(2) 0.2500 0.02096(8) Uani 1 2 d S T P . .
Cu2 Cu 0.53223(2) 0.42772(2) 0.47660(2) 0.02171(7) Uani 1 1 d . . . . .
O1 O 0.58891(8) 0.43811(7) 0.20267(11) 0.0359(3) Uani 1 1 d . . . . .
O2 O 0.62701(7) 0.39132(6) 0.38511(10) 0.0293(3) Uani 1 1 d . . . . .
O3 O 0.54857(7) 0.52250(6) 0.41892(10) 0.0200(2) Uani 1 1 d . . . . .
H3A H 0.5885(13) 0.5329(11) 0.4098(18) 0.030 Uiso 1 1 d . U . . .
O4 O 0.39744(8) 0.58240(7) 0.32022(11) 0.0352(3) Uani 1 1 d . . . . .
O5 O 0.29778(8) 0.56292(8) 0.16763(11) 0.0406(3) Uani 1 1 d . . . . .
C12 C 0.24674(15) 0.59133(18) 0.3616(2) 0.0773(9) Uani 1 1 d . . . . .
H12A H 0.1925 0.5998 0.3146 0.116 Uiso 1 1 calc R U . . .
H12B H 0.2619 0.6307 0.4111 0.116 Uiso 1 1 calc R U . . .
H12C H 0.2399 0.5523 0.4135 0.116 Uiso 1 1 calc R U . . .
N1 N 0.90937(10) 0.25387(8) 0.05362(14) 0.0341(3) Uani 1 1 d . . . . .
N2 N 0.98938(9) 0.16682(7) 0.00019(13) 0.0282(3) Uani 1 1 d . . . . .
C11 C 0.31880(12) 0.57755(10) 0.27605(17) 0.0336(4) Uani 1 1 d . . . . .
C1 C 0.93061(11) 0.18772(9) 0.07259(16) 0.0326(4) Uani 1 1 d . . . . .
H1 H 0.9060 0.1602 0.1309 0.039 Uiso 1 1 calc R U . . .
C2 C 0.95896(15) 0.27614(11) -0.0394(2) 0.0562(6) Uani 1 1 d . . . . .
H2 H 0.9588 0.3198 -0.0736 0.067 Uiso 1 1 calc R U . . .
C3 C 1.00748(15) 0.22260(10) -0.0710(2) 0.0514(6) Uani 1 1 d . . . . .
H3 H 1.0475 0.2230 -0.1320 0.062 Uiso 1 1 calc R U . . .
C4 C 0.84270(12) 0.29120(9) 0.11102(16) 0.0335(4) Uani 1 1 d . . . . .
C5 C 0.79898(12) 0.34313(10) 0.04692(16) 0.0369(4) Uani 1 1 d . . . . .
H5 H 0.8134 0.3539 -0.0323 0.044 Uiso 1 1 calc R U . . .
C6 C 0.73347(12) 0.37890(10) 0.10167(16) 0.0353(4) Uani 1 1 d . . . . .
H6 H 0.7044 0.4142 0.0589 0.042 Uiso 1 1 calc R U . . .
C7 C 0.71046(11) 0.36312(9) 0.21825(15) 0.0292(4) Uani 1 1 d . . . . .
C8 C 0.75575(13) 0.31148(10) 0.28248(17) 0.0425(5) Uani 1 1 d . . . . .
H8 H 0.7414 0.3009 0.3619 0.051 Uiso 1 1 calc R U . . .
C9 C 0.82224(14) 0.27540(11) 0.22959(18) 0.0447(5) Uani 1 1 d . . . . .
H9 H 0.8527 0.2410 0.2732 0.054 Uiso 1 1 calc R U . . .
C10 C 0.63589(10) 0.40117(9) 0.27215(15) 0.0258(4) 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 O3 1.9471(12) 2_655 ?
Cu1 O3 1.9471(12) . ?
Cu1 O4 2.1362(13) . ?
Cu1 O4 2.1362(13) 2_655 ?
Cu1 O1 2.2043(13) 2_655 ?
Cu1 O1 2.2043(13) . ?
Cu2 O2 1.9386(11) . ?
Cu2 O3 1.9749(12) . ?
Cu2 N2 1.9792(14) 8_456 ?
Cu2 O3 1.9819(12) 5_666 ?
Cu2 O4 2.4148(14) 5_666 ?
Cu2 Cu2 3.0407(6) 5_666 ?
O1 C10 1.242(2) . ?
O2 C10 1.264(2) . ?
O3 Cu2 1.9818(12) 5_666 ?
O3 H3A 0.65(2) . ?
O4 C11 1.268(2) . ?
O4 Cu2 2.4148(14) 5_666 ?
O5 C11 1.242(2) . ?
C12 C11 1.507(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 C1 1.344(2) . ?
N1 C2 1.372(2) . ?
N1 C4 1.425(2) . ?
N2 C1 1.295(2) . ?
N2 C3 1.375(2) . ?
N2 Cu2 1.9792(14) 8 ?
C1 H1 0.9300 . ?
C2 C3 1.337(3) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.380(3) . ?
C4 C9 1.385(3) . ?
C5 C6 1.383(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.388(3) . ?
C7 C10 1.506(2) . ?
C8 C9 1.387(3) . ?
C8 H8 0.9300 . ?
C9 H9 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
O3 Cu1 O3 179.33(7) 2_655 . ?
O3 Cu1 O4 95.33(5) 2_655 . ?
O3 Cu1 O4 84.30(5) . . ?
O3 Cu1 O4 84.30(5) 2_655 2_655 ?
O3 Cu1 O4 95.33(5) . 2_655 ?
O4 Cu1 O4 112.91(7) . 2_655 ?
O3 Cu1 O1 91.31(5) 2_655 2_655 ?
O3 Cu1 O1 89.18(5) . 2_655 ?
O4 Cu1 O1 81.58(5) . 2_655 ?
O4 Cu1 O1 165.15(5) 2_655 2_655 ?
O3 Cu1 O1 89.18(5) 2_655 . ?
O3 Cu1 O1 91.31(5) . . ?
O4 Cu1 O1 165.15(5) . . ?
O4 Cu1 O1 81.58(5) 2_655 . ?
O1 Cu1 O1 84.18(7) 2_655 . ?
O2 Cu2 O3 93.84(5) . . ?
O2 Cu2 N2 89.24(5) . 8_456 ?
O3 Cu2 N2 164.52(5) . 8_456 ?
O2 Cu2 O3 169.52(5) . 5_666 ?
O3 Cu2 O3 79.56(5) . 5_666 ?
N2 Cu2 O3 99.29(5) 8_456 5_666 ?
O2 Cu2 O4 98.12(5) . 5_666 ?
O3 Cu2 O4 108.21(5) . 5_666 ?
N2 Cu2 O4 86.31(5) 8_456 5_666 ?
O3 Cu2 O4 76.53(5) 5_666 5_666 ?
O2 Cu2 Cu2 133.19(4) . 5_666 ?
O3 Cu2 Cu2 39.87(3) . 5_666 ?
N2 Cu2 Cu2 136.98(4) 8_456 5_666 ?
O3 Cu2 Cu2 39.70(3) 5_666 5_666 ?
O4 Cu2 Cu2 92.93(3) 5_666 5_666 ?
C10 O1 Cu1 128.80(11) . . ?
C10 O2 Cu2 125.02(11) . . ?
Cu1 O3 Cu2 104.42(5) . . ?
Cu1 O3 Cu2 109.58(6) . 5_666 ?
Cu2 O3 Cu2 100.44(5) . 5_666 ?
Cu1 O3 H3A 99.3(18) . . ?
Cu2 O3 H3A 118.3(19) . . ?
Cu2 O3 H3A 123.4(19) 5_666 . ?
C11 O4 Cu1 121.07(12) . . ?
C11 O4 Cu2 134.51(12) . 5_666 ?
Cu1 O4 Cu2 89.51(5) . 5_666 ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 N1 C2 106.29(14) . . ?
C1 N1 C4 126.47(15) . . ?
C2 N1 C4 127.00(16) . . ?
C1 N2 C3 105.37(15) . . ?
C1 N2 Cu2 128.19(12) . 8 ?
C3 N2 Cu2 125.86(12) . 8 ?
O5 C11 O4 124.35(16) . . ?
O5 C11 C12 118.48(17) . . ?
O4 C11 C12 117.17(18) . . ?
N2 C1 N1 112.15(15) . . ?
N2 C1 H1 123.9 . . ?
N1 C1 H1 123.9 . . ?
C3 C2 N1 106.29(17) . . ?
C3 C2 H2 126.9 . . ?
N1 C2 H2 126.9 . . ?
C2 C3 N2 109.90(17) . . ?
C2 C3 H3 125.0 . . ?
N2 C3 H3 125.0 . . ?
C5 C4 C9 120.63(16) . . ?
C5 C4 N1 119.13(16) . . ?
C9 C4 N1 120.24(16) . . ?
C4 C5 C6 119.32(16) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C7 C6 C5 121.17(17) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 118.98(16) . . ?
C6 C7 C10 119.42(16) . . ?
C8 C7 C10 121.59(15) . . ?
C9 C8 C7 120.72(17) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C4 C9 C8 119.14(18) . . ?
C4 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
O1 C10 O2 126.42(15) . . ?
O1 C10 C7 117.86(15) . . ?
O2 C10 C7 115.71(15) . . ?

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
O3 H3A O5 0.65(2) 2.06(2) 2.6931(18) 164(2) 2_655
C1 H1 O4 0.93 2.58 3.459(2) 158.9 3_545
C1 H1 O5 0.93 2.56 3.369(2) 145.7 3_545

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.045

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
1 0.000 0.500 -0.011 353.2 101.6
2 0.500 1.000 -0.008 353.2 101.6
_platon_squeeze_details          
;
;


