# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_Cu-COOH
_database_code_depnum_ccdc_archive 'CCDC 1587111'
_audit_update_record             
;
2017-11-22 deposited with the CCDC.
2018-05-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H29 Cu N8 O7'
_chemical_formula_weight         677.15

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2 1/c'

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

_cell_length_a                   14.088(5)
_cell_length_b                   20.940(7)
_cell_length_c                   11.306(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.423(4)
_cell_angle_gamma                90.00
_cell_volume                     3060.5(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5397
_cell_measurement_theta_min      1.85
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1400
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_T_max  0.805
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21510
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5382
_reflns_number_gt                4066
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5382
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1520
_refine_ls_wR_factor_gt          0.1410
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.078
_refine_ls_shift/su_mean         0.007

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.30724(3) 0.416118(19) 0.58558(3) 0.05754(18) Uani 1 1 d . . .
O1 O 0.5355(2) 0.12112(13) 0.6431(3) 0.1037(10) Uani 1 1 d . . .
O2 O 0.58111(16) 0.18013(11) 0.5123(2) 0.0728(6) Uani 1 1 d . . .
H2B H 0.6349 0.1597 0.5456 0.109 Uiso 1 1 calc R . .
O3 O -0.1910(2) 0.34375(14) -0.0238(3) 0.0944(9) Uani 1 1 d . . .
O4 O -0.23983(17) 0.36288(12) 0.1338(2) 0.0759(7) Uani 1 1 d . . .
O5 O -0.2513(2) 0.39460(15) 0.3821(3) 0.1070(10) Uani 1 1 d . . .
H5A H -0.2740 0.4296 0.3986 0.160 Uiso 1 1 d R . .
H5C H -0.2655 0.3644 0.4225 0.160 Uiso 1 1 d R . .
O6 O -0.0798(2) 0.31432(13) -0.1763(3) 0.0962(8) Uani 1 1 d . . .
H6B H -0.1406 0.3280 -0.1934 0.144 Uiso 1 1 d R . .
H6D H -0.0812 0.2739 -0.1838 0.144 Uiso 1 1 d R . .
O7 O 0.8009(2) 0.28570(14) 0.5551(3) 0.1018(9) Uani 1 1 d . . .
H7B H 0.7964 0.2879 0.4779 0.153 Uiso 1 1 d R . .
H7C H 0.8523 0.3078 0.6037 0.153 Uiso 1 1 d R . .
C1 C 0.3471(3) 0.48539(15) 0.8407(3) 0.0614(8) Uani 1 1 d . . .
H1A H 0.4044 0.5047 0.8343 0.074 Uiso 1 1 calc R . .
C2 C 0.3258(3) 0.49745(16) 0.9469(3) 0.0709(9) Uani 1 1 d . . .
H2A H 0.3697 0.5243 1.0107 0.085 Uiso 1 1 calc R . .
C3 C 0.1858(2) 0.43434(15) 0.8683(3) 0.0583(8) Uani 1 1 d . . .
H3A H 0.1280 0.4160 0.8749 0.070 Uiso 1 1 calc R . .
C4 C 0.2061(2) 0.42079(12) 0.7601(3) 0.0436(6) Uani 1 1 d . . .
C5 C 0.1426(2) 0.37768(12) 0.6565(3) 0.0428(6) Uani 1 1 d . . .
C6 C 0.0503(2) 0.34602(14) 0.6324(3) 0.0572(8) Uani 1 1 d . . .
H6A H 0.0103 0.3476 0.6808 0.069 Uiso 1 1 calc R . .
C7 C 0.0310(2) 0.31221(14) 0.5228(3) 0.0576(8) Uani 1 1 d . . .
H7A H -0.0254 0.2856 0.4818 0.069 Uiso 1 1 calc R . .
C8 C 0.1248(2) 0.29808(14) 0.3746(3) 0.0514(7) Uani 1 1 d . . .
H8A H 0.1268 0.3327 0.3187 0.062 Uiso 1 1 calc R . .
H8B H 0.0675 0.2703 0.3255 0.062 Uiso 1 1 calc R . .
C9 C 0.2251(2) 0.26072(13) 0.4175(2) 0.0443(6) Uani 1 1 d . . .
C10 C 0.2472(2) 0.21377(14) 0.5114(3) 0.0572(7) Uani 1 1 d . . .
H10A H 0.1986 0.2038 0.5451 0.069 Uiso 1 1 calc R . .
C11 C 0.3400(2) 0.18180(14) 0.5551(3) 0.0592(8) Uani 1 1 d . . .
H11A H 0.3533 0.1506 0.6181 0.071 Uiso 1 1 calc R . .
C12 C 0.4146(2) 0.19539(12) 0.5065(3) 0.0482(7) Uani 1 1 d . . .
C13 C 0.3913(2) 0.24166(14) 0.4119(3) 0.0537(7) Uani 1 1 d . . .
H13A H 0.4392 0.2512 0.3768 0.064 Uiso 1 1 calc R . .
C14 C 0.2979(2) 0.27412(14) 0.3682(3) 0.0513(7) Uani 1 1 d . . .
H14A H 0.2842 0.3053 0.3049 0.062 Uiso 1 1 calc R . .
C15 C 0.5159(2) 0.16170(15) 0.5600(3) 0.0572(7) Uani 1 1 d . . .
C16 C 0.5136(2) 0.33976(16) 0.6960(3) 0.0665(9) Uani 1 1 d . . .
H16A H 0.4969 0.3268 0.7641 0.080 Uiso 1 1 calc R . .
C17 C 0.6052(3) 0.31833(17) 0.6901(4) 0.0782(11) Uani 1 1 d . . .
H17A H 0.6484 0.2917 0.7551 0.094 Uiso 1 1 calc R . .
C18 C 0.5697(2) 0.37309(15) 0.5072(3) 0.0639(8) Uani 1 1 d . . .
H18A H 0.5869 0.3852 0.4391 0.077 Uiso 1 1 calc R . .
C19 C 0.4787(2) 0.39657(14) 0.5115(3) 0.0473(7) Uani 1 1 d . . .
C20 C 0.40916(19) 0.44114(13) 0.4173(2) 0.0446(6) Uani 1 1 d . . .
C21 C 0.4106(2) 0.47010(15) 0.3077(3) 0.0575(8) Uani 1 1 d . . .
H21A H 0.4589 0.4641 0.2718 0.069 Uiso 1 1 calc R . .
C22 C 0.3266(2) 0.50915(15) 0.2638(3) 0.0572(8) Uani 1 1 d . . .
H22A H 0.3063 0.5350 0.1911 0.069 Uiso 1 1 calc R . .
C23 C 0.1803(2) 0.53181(14) 0.3333(3) 0.0574(8) Uani 1 1 d . . .
H23A H 0.1678 0.5705 0.2822 0.069 Uiso 1 1 calc R . .
H23B H 0.1845 0.5433 0.4184 0.069 Uiso 1 1 calc R . .
C24 C 0.0907(2) 0.48590(13) 0.2707(3) 0.0484(7) Uani 1 1 d . . .
C25 C 0.0717(2) 0.45918(15) 0.1518(3) 0.0573(8) Uani 1 1 d . . .
H25A H 0.1163 0.4678 0.1114 0.069 Uiso 1 1 calc R . .
C26 C -0.0128(2) 0.41982(15) 0.0921(3) 0.0584(8) Uani 1 1 d . . .
H26A H -0.0239 0.4017 0.0125 0.070 Uiso 1 1 calc R . .
C27 C -0.0812(2) 0.40709(13) 0.1503(3) 0.0509(7) Uani 1 1 d . . .
C28 C -0.0609(2) 0.43260(14) 0.2712(3) 0.0543(7) Uani 1 1 d . . .
H28A H -0.1047 0.4235 0.3125 0.065 Uiso 1 1 calc R . .
C29 C 0.0244(2) 0.47164(14) 0.3310(3) 0.0547(7) Uani 1 1 d . . .
H29A H 0.0374 0.4884 0.4121 0.066 Uiso 1 1 calc R . .
C30 C -0.1772(2) 0.36847(16) 0.0793(3) 0.0619(8) Uani 1 1 d . . .
N1 N 0.2451(2) 0.47222(15) 0.9619(2) 0.0691(8) Uani 1 1 d . . .
N2 N 0.28795(18) 0.44672(11) 0.7463(2) 0.0488(6) Uani 1 1 d . . .
N3 N 0.17859(16) 0.36440(9) 0.5659(2) 0.0398(5) Uani 1 1 d . . .
N4 N 0.10805(15) 0.32403(10) 0.4841(2) 0.0450(5) Uani 1 1 d . . .
N5 N 0.6325(2) 0.33438(15) 0.5960(3) 0.0739(8) Uani 1 1 d . . .
N6 N 0.44936(17) 0.37848(11) 0.6062(2) 0.0504(6) Uani 1 1 d . . .
N7 N 0.32681(16) 0.46116(10) 0.4389(2) 0.0432(5) Uani 1 1 d . . .
N8 N 0.27815(17) 0.50355(11) 0.3443(2) 0.0474(5) 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 N7 2.020(2) . ?
Cu1 N2 2.044(2) . ?
Cu1 N3 2.046(2) . ?
Cu1 N6 2.077(2) . ?
O1 C15 1.215(4) . ?
O2 C15 1.294(3) . ?
O3 C30 1.218(4) . ?
O4 C30 1.267(4) . ?
C1 N2 1.335(4) . ?
C1 C2 1.372(4) . ?
C2 N1 1.325(5) . ?
C3 N1 1.321(4) . ?
C3 C4 1.391(4) . ?
C4 N2 1.339(3) . ?
C4 C5 1.468(4) . ?
C5 N3 1.341(3) . ?
C5 C6 1.386(4) . ?
C6 C7 1.358(4) . ?
C7 N4 1.344(4) . ?
C8 N4 1.455(3) . ?
C8 C9 1.516(4) . ?
C9 C14 1.377(4) . ?
C9 C10 1.388(4) . ?
C10 C11 1.374(4) . ?
C11 C12 1.395(4) . ?
C12 C13 1.383(4) . ?
C12 C15 1.488(4) . ?
C13 C14 1.386(4) . ?
C16 N6 1.333(4) . ?
C16 C17 1.393(5) . ?
C17 N5 1.311(5) . ?
C18 N5 1.320(4) . ?
C18 C19 1.392(4) . ?
C19 N6 1.346(4) . ?
C19 C20 1.461(4) . ?
C20 N7 1.344(3) . ?
C20 C21 1.386(4) . ?
C21 C22 1.359(4) . ?
C22 N8 1.343(3) . ?
C23 N8 1.460(4) . ?
C23 C24 1.519(4) . ?
C24 C25 1.381(4) . ?
C24 C29 1.389(4) . ?
C25 C26 1.383(4) . ?
C26 C27 1.393(4) . ?
C27 C28 1.387(4) . ?
C27 C30 1.505(4) . ?
C28 C29 1.387(4) . ?
N3 N4 1.352(3) . ?
N7 N8 1.348(3) . ?

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
N7 Cu1 N2 133.89(9) . . ?
N7 Cu1 N3 124.19(8) . . ?
N2 Cu1 N3 80.67(8) . . ?
N7 Cu1 N6 80.17(9) . . ?
N2 Cu1 N6 118.81(9) . . ?
N3 Cu1 N6 125.74(9) . . ?
N2 C1 C2 121.8(3) . . ?
N1 C2 C1 122.5(3) . . ?
N1 C3 C4 122.7(3) . . ?
N2 C4 C3 120.5(3) . . ?
N2 C4 C5 115.8(2) . . ?
C3 C4 C5 123.6(3) . . ?
N3 C5 C6 111.1(2) . . ?
N3 C5 C4 116.2(2) . . ?
C6 C5 C4 132.7(2) . . ?
C7 C6 C5 105.1(3) . . ?
N4 C7 C6 107.8(2) . . ?
N4 C8 C9 111.5(2) . . ?
C14 C9 C10 118.4(3) . . ?
C14 C9 C8 120.9(3) . . ?
C10 C9 C8 120.6(3) . . ?
C11 C10 C9 120.9(3) . . ?
C10 C11 C12 121.1(3) . . ?
C13 C12 C11 117.6(3) . . ?
C13 C12 C15 122.8(3) . . ?
C11 C12 C15 119.6(3) . . ?
C14 C13 C12 121.3(3) . . ?
C9 C14 C13 120.7(3) . . ?
O1 C15 O2 123.3(3) . . ?
O1 C15 C12 122.2(3) . . ?
O2 C15 C12 114.5(3) . . ?
N6 C16 C17 121.4(3) . . ?
N5 C17 C16 122.2(3) . . ?
N5 C18 C19 122.6(3) . . ?
N6 C19 C18 120.4(3) . . ?
N6 C19 C20 115.5(2) . . ?
C18 C19 C20 124.0(3) . . ?
N7 C20 C21 110.2(3) . . ?
N7 C20 C19 116.3(2) . . ?
C21 C20 C19 133.4(3) . . ?
C22 C21 C20 105.7(3) . . ?
N8 C22 C21 107.6(3) . . ?
N8 C23 C24 111.4(2) . . ?
C25 C24 C29 118.9(3) . . ?
C25 C24 C23 120.9(3) . . ?
C29 C24 C23 120.2(3) . . ?
C24 C25 C26 120.9(3) . . ?
C25 C26 C27 120.4(3) . . ?
C28 C27 C26 118.8(3) . . ?
C28 C27 C30 121.5(3) . . ?
C26 C27 C30 119.6(3) . . ?
C27 C28 C29 120.4(3) . . ?
C24 C29 C28 120.6(3) . . ?
O3 C30 O4 123.3(3) . . ?
O3 C30 C27 120.5(3) . . ?
O4 C30 C27 116.2(3) . . ?
C3 N1 C2 116.0(3) . . ?
C1 N2 C4 116.5(2) . . ?
C1 N2 Cu1 129.7(2) . . ?
C4 N2 Cu1 113.70(17) . . ?
C5 N3 N4 104.7(2) . . ?
C5 N3 Cu1 113.25(17) . . ?
N4 N3 Cu1 141.64(17) . . ?
C7 N4 N3 111.2(2) . . ?
C7 N4 C8 129.3(2) . . ?
N3 N4 C8 119.5(2) . . ?
C17 N5 C18 116.8(3) . . ?
C16 N6 C19 116.5(3) . . ?
C16 N6 Cu1 130.5(2) . . ?
C19 N6 Cu1 112.99(19) . . ?
C20 N7 N8 105.4(2) . . ?
C20 N7 Cu1 114.40(18) . . ?
N8 N7 Cu1 140.00(17) . . ?
C22 N8 N7 111.1(2) . . ?
C22 N8 C23 128.6(3) . . ?
N7 N8 C23 120.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.049
