# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_rg26m
_database_code_depnum_ccdc_archive 'CCDC 2040369'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Shiv Nadar University
India
;
_audit_update_record             
;
2020-12-22 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H26 N10 O6'
_chemical_formula_iupac          ?
_chemical_formula_weight         550.55

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.8247(2)
_cell_length_b                   27.5057(8)
_cell_length_c                   14.9858(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.1504(12)
_cell_angle_gamma                90
_cell_volume                     2400.90(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7979
_cell_measurement_theta_min      2.6043
_cell_measurement_theta_max      27.8700
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.072
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152

_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   'Numerical Mu Calculated'
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            27162
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         27.93
_diffrn_reflns_theta_full        27.93
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             5730
_reflns_number_gt                4571
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1186
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_number_reflns         5730
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0432P)²+1.8428P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.243
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 1.3429(3) 0.40604(6) 0.86265(11) 0.0176(3) Uani d . . . 1 . .
C C2 1.4221(3) 0.35995(6) 0.89108(12) 0.0183(3) Uani d . . . 1 . .
C C3 1.6187(3) 0.35690(7) 0.94379(12) 0.0231(4) Uani d . . . 1 . .
H H3 1.673497 0.326001 0.962512 0.028 Uiso calc U . R 1 . .
C C4 1.7347(3) 0.39857(7) 0.96908(12) 0.0243(4) Uani d . . . 1 . .
H H4A 1.869806 0.39608 1.00445 0.029 Uiso calc U . R 1 . .
C C5 1.6553(3) 0.44389(7) 0.94321(12) 0.0249(4) Uani d . . . 1 . .
H H5 1.733808 0.4724 0.962006 0.03 Uiso calc U . R 1 . .
C C6 1.4611(3) 0.44765(6) 0.88982(12) 0.0216(4) Uani d . . . 1 . .
H H6 1.408247 0.478786 0.871622 0.026 Uiso calc U . R 1 . .
C C7 0.8541(3) 0.37435(6) 0.73329(11) 0.0169(3) Uani d . . . 1 . .
C C8 0.7612(3) 0.32641(6) 0.71683(12) 0.0185(3) Uani d . . . 1 . .
C C9 0.4599(3) 0.27844(6) 0.64063(13) 0.0262(4) Uani d . . . 1 . .
H H9A 0.302206 0.276342 0.662974 0.039 Uiso calc U . R 1 . .
H H9B 0.551727 0.252047 0.666332 0.039 Uiso calc U . R 1 . .
H H9C 0.458992 0.275561 0.57545 0.039 Uiso calc U . R 1 . .
C C10 0.4509(3) 0.36562(6) 0.63158(11) 0.0177(3) Uani d . . . 1 . .
C C11 0.4239(3) 0.45394(6) 0.61963(13) 0.0215(4) Uani d . . . 1 . .
H H11A 0.390977 0.475233 0.670444 0.032 Uiso calc U . R 1 . .
H H11B 0.279393 0.443984 0.591378 0.032 Uiso calc U . R 1 . .
H H11C 0.518309 0.471458 0.576198 0.032 Uiso calc U . R 1 . .
C C12 0.7480(3) 0.41587(6) 0.69809(11) 0.0159(3) Uani d . . . 1 . .
C C13 0.8556(3) 0.36660(6) 0.21721(11) 0.0155(3) Uani d . . . 1 . .
C C14 0.9047(3) 0.41652(6) 0.20556(11) 0.0164(3) Uani d . . . 1 . .
C C15 1.0982(3) 0.43007(6) 0.15688(12) 0.0193(3) Uani d . . . 1 . .
H H15 1.134304 0.463543 0.150075 0.023 Uiso calc U . R 1 . .
C C16 1.2379(3) 0.39538(7) 0.11849(12) 0.0210(4) Uani d . . . 1 . .
H H16 1.369055 0.405174 0.085509 0.025 Uiso calc U . R 1 . .
C C17 1.1879(3) 0.34616(6) 0.12778(12) 0.0200(4) Uani d . . . 1 . .
H H17 1.282821 0.322424 0.100312 0.024 Uiso calc U . R 1 . .
C C18 0.9994(3) 0.33203(6) 0.17716(11) 0.0181(3) Uani d . . . 1 . .
H H18 0.966709 0.298409 0.184119 0.022 Uiso calc U . R 1 . .
C C19 0.3569(3) 0.36838(6) 0.35221(11) 0.0149(3) Uani d . . . 1 . .
C C20 0.2296(3) 0.40943(6) 0.38407(11) 0.0155(3) Uani d . . . 1 . .
C C21 -0.1169(3) 0.43963(6) 0.45947(12) 0.0207(4) Uani d . . . 1 . .
H H21A -0.279516 0.432379 0.449132 0.031 Uiso calc U . R 1 . .
H H21B -0.07535 0.469475 0.427645 0.031 Uiso calc U . R 1 . .
H H21C -0.089757 0.444052 0.523522 0.031 Uiso calc U . R 1 . .
C C22 -0.0500(3) 0.35322(6) 0.44938(11) 0.0171(3) Uani d . . . 1 . .
C C23 0.0040(3) 0.26541(6) 0.44170(13) 0.0241(4) Uani d . . . 1 . .
H H23A -0.029491 0.247474 0.386678 0.036 Uiso calc U . R 1 . .
H H23B -0.135403 0.267592 0.477925 0.036 Uiso calc U . R 1 . .
H H23C 0.123807 0.24836 0.475441 0.036 Uiso calc U . R 1 . .
C C24 0.2835(3) 0.32081(6) 0.37262(11) 0.0157(3) Uani d . . . 1 . .
N N1 1.1508(2) 0.41356(5) 0.80688(10) 0.0176(3) Uani d . . . 1 . .
N N2 1.0468(2) 0.37375(5) 0.78528(10) 0.0171(3) Uani d . . . 1 . .
N N3 0.5597(2) 0.32538(5) 0.66629(10) 0.0185(3) Uani d . . . 1 . .
N N4 0.5480(2) 0.41072(5) 0.65088(10) 0.0168(3) Uani d . . . 1 . .
N N5 0.8365(3) 0.45987(5) 0.70886(10) 0.0184(3) Uani d . . . 1 . .
H H1N 0.971(4) 0.4611(8) 0.7431(15) 0.028 Uiso d U . . 1 . .
H H2N 0.773(4) 0.4863(8) 0.6859(15) 0.028 Uiso d U . . 1 . .
N N6 0.6728(2) 0.34770(5) 0.26831(10) 0.0162(3) Uani d . . . 1 . .
N N7 0.5445(2) 0.38076(5) 0.30261(9) 0.0154(3) Uani d . . . 1 . .
N N8 0.0236(2) 0.39925(5) 0.42673(9) 0.0159(3) Uani d . . . 1 . .
N N9 0.0837(2) 0.31452(5) 0.41929(10) 0.0168(3) Uani d . . . 1 . .
N N10 0.4039(2) 0.28235(5) 0.34777(11) 0.0191(3) Uani d . . . 1 . .
H H3N 0.541(4) 0.2883(8) 0.3126(15) 0.029 Uiso d U . . 1 . .
H H4N 0.363(4) 0.2537(8) 0.3591(15) 0.029 Uiso d U . . 1 . .
O O1 1.3125(2) 0.31865(4) 0.86762(9) 0.0254(3) Uani d . . . 1 . .
H H1 1.199303 0.325463 0.835113 0.038 Uiso calc U . R 1 . .
O O2 0.8475(2) 0.28853(4) 0.74433(9) 0.0260(3) Uani d . . . 1 . .
O O3 0.2766(2) 0.36211(5) 0.58766(9) 0.0238(3) Uani d . . . 1 . .
O O4 0.7736(2) 0.45226(4) 0.24131(9) 0.0217(3) Uani d . . . 1 . .
H H4 0.663858 0.439824 0.269495 0.033 Uiso calc U . R 1 . .
O O5 0.2931(2) 0.45193(4) 0.37499(8) 0.0193(3) Uani d . . . 1 . .
O O6 -0.2238(2) 0.34669(5) 0.49201(9) 0.0222(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.396(2) ?
C1 N1 . 1.410(2) ?
C1 C2 . 1.415(2) ?
C2 O1 . 1.349(2) ?
C2 C3 . 1.392(2) ?
C3 C4 . 1.383(3) ?
C4 C5 . 1.385(3) ?
C5 C6 . 1.388(3) ?
C7 N2 . 1.365(2) ?
C7 C12 . 1.401(2) ?
C7 C8 . 1.446(2) ?
C8 O2 . 1.228(2) ?
C8 N3 . 1.396(2) ?
C9 N3 . 1.467(2) ?
C10 O3 . 1.212(2) ?
C10 N3 . 1.377(2) ?
C10 N4 . 1.393(2) ?
C11 N4 . 1.467(2) ?
C12 N5 . 1.325(2) ?
C12 N4 . 1.369(2) ?
C13 C18 . 1.403(2) ?
C13 N6 . 1.412(2) ?
C13 C14 . 1.413(2) ?
C14 O4 . 1.356(2) ?
C14 C15 . 1.395(2) ?
C15 C16 . 1.380(2) ?
C16 C17 . 1.392(3) ?
C17 C18 . 1.381(2) ?
C19 N7 . 1.366(2) ?
C19 C24 . 1.410(2) ?
C19 C20 . 1.433(2) ?
C20 O5 . 1.234(2) ?
C20 N8 . 1.390(2) ?
C21 N8 . 1.465(2) ?
C22 O6 . 1.212(2) ?
C22 N8 . 1.379(2) ?
C22 N9 . 1.395(2) ?
C23 N9 . 1.468(2) ?
C24 N10 . 1.323(2) ?
C24 N9 . 1.370(2) ?
N1 N2 . 1.2920(19) ?
N6 N7 . 1.2852(19) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 N1 . . 116.30(15) ?
C6 C1 C2 . . 119.12(16) ?
N1 C1 C2 . . 124.58(15) ?
O1 C2 C3 . . 119.02(16) ?
O1 C2 C1 . . 121.50(15) ?
C3 C2 C1 . . 119.48(16) ?
C4 C3 C2 . . 120.42(17) ?
C3 C4 C5 . . 120.45(17) ?
C4 C5 C6 . . 119.97(17) ?
C5 C6 C1 . . 120.53(17) ?
N2 C7 C12 . . 125.87(15) ?
N2 C7 C8 . . 113.15(14) ?
C12 C7 C8 . . 120.98(15) ?
O2 C8 N3 . . 120.53(15) ?
O2 C8 C7 . . 124.33(16) ?
N3 C8 C7 . . 115.14(14) ?
O3 C10 N3 . . 121.68(16) ?
O3 C10 N4 . . 121.49(16) ?
N3 C10 N4 . . 116.81(14) ?
N5 C12 N4 . . 119.20(15) ?
N5 C12 C7 . . 121.85(15) ?
N4 C12 C7 . . 118.95(15) ?
C18 C13 N6 . . 115.74(14) ?
C18 C13 C14 . . 118.96(15) ?
N6 C13 C14 . . 125.28(15) ?
O4 C14 C15 . . 117.99(15) ?
O4 C14 C13 . . 122.78(15) ?
C15 C14 C13 . . 119.22(15) ?
C16 C15 C14 . . 120.74(16) ?
C15 C16 C17 . . 120.46(16) ?
C18 C17 C16 . . 119.60(16) ?
C17 C18 C13 . . 120.98(16) ?
N7 C19 C24 . . 126.34(15) ?
N7 C19 C20 . . 113.57(14) ?
C24 C19 C20 . . 120.09(15) ?
O5 C20 N8 . . 120.09(15) ?
O5 C20 C19 . . 123.66(15) ?
N8 C20 C19 . . 116.25(14) ?
O6 C22 N8 . . 121.76(16) ?
O6 C22 N9 . . 121.69(16) ?
N8 C22 N9 . . 116.54(14) ?
N10 C24 N9 . . 119.63(15) ?
N10 C24 C19 . . 121.29(15) ?
N9 C24 C19 . . 119.08(15) ?
N2 N1 C1 . . 113.27(14) ?
N1 N2 C7 . . 121.14(14) ?
C10 N3 C8 . . 125.06(14) ?
C10 N3 C9 . . 115.26(14) ?
C8 N3 C9 . . 119.49(14) ?
C12 N4 C10 . . 122.95(14) ?
C12 N4 C11 . . 119.93(14) ?
C10 N4 C11 . . 117.10(14) ?
N7 N6 C13 . . 113.36(13) ?
N6 N7 C19 . . 120.53(14) ?
C22 N8 C20 . . 124.59(14) ?
C22 N8 C21 . . 116.05(14) ?
C20 N8 C21 . . 119.01(14) ?
C24 N9 C22 . . 122.99(14) ?
C24 N9 C23 . . 120.16(14) ?
C22 N9 C23 . . 116.84(14) ?



####################################################################### 
# 
# 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_rgtm8s
_database_code_depnum_ccdc_archive 'CCDC 2040370'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Nanyang Technology University 
India
;
_audit_update_record             
;
2020-10-23 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H48 Cu4 N20 O14'
_chemical_formula_iupac          ?
_chemical_formula_weight         1383.22

_chemical_melting_point          ?

_space_group_crystal_system      tetragonal
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   13.2660(4)
_cell_length_b                   13.2660(4)
_cell_length_c                   28.9624(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5097.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1016
_cell_measurement_theta_min      3.6391
_cell_measurement_theta_max      66.1884
_cell_measurement_temperature    143.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2816

_exptl_absorpt_coefficient_mu    2.664
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.35
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      143.(2)

_diffrn_source                   'Incoatec Microfocus Source'
_diffrn_source_type              'Bruker Kappa Duo APEX2'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            20922
_diffrn_reflns_av_R_equivalents  0.1424
_diffrn_reflns_av_unetI/netI     0.0826
_diffrn_reflns_theta_min         3.67
_diffrn_reflns_theta_max         66.63
_diffrn_reflns_theta_full        66.63
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34

_refine_special_details          
;
;

_reflns_number_total             2262
_reflns_number_gt                1688
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1526
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.064
_refine_ls_number_reflns         2262
_refine_ls_number_parameters     208
_refine_ls_number_restraints     3
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²+24.7958P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.724
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.07224(5) 0.36029(5) 1.08421(2) 0.0211(3) Uani d . . . 1 . .
C C1 -0.1310(4) 0.3694(3) 1.06677(16) 0.0218(10) Uani d . . . 1 . .
C C2 -0.2355(4) 0.3710(4) 1.07159(17) 0.0271(11) Uani d . . . 1 . .
H H2 -0.2655 0.3685 1.1014 0.033 Uiso calc U . R 1 . .
C C3 -0.2957(4) 0.3765(4) 1.03202(18) 0.0299(11) Uani d . . . 1 . .
H H3 -0.3669 0.3784 1.0351 0.036 Uiso calc U . R 1 . .
C C4 -0.2532(4) 0.3790(4) 0.98833(17) 0.0280(11) Uani d . . . 1 . .
H H4 -0.2952 0.3813 0.9618 0.034 Uiso calc U . R 1 . .
C C5 -0.1492(4) 0.3784(3) 0.98346(16) 0.0236(10) Uani d . . . 1 . .
H H5 -0.1198 0.3808 0.9536 0.028 Uiso calc U . R 1 . .
C C6 -0.0878(4) 0.3742(3) 1.02258(15) 0.0209(10) Uani d . . . 1 . .
C C7 0.1637(3) 0.3782(3) 0.98111(15) 0.0188(9) Uani d . . . 1 . .
C C8 0.2004(4) 0.3850(4) 0.93349(16) 0.0266(11) Uani d . . . 1 . .
C C9 0.3448(5) 0.4018(5) 0.88102(17) 0.0411(14) Uani d . . . 1 . .
H H9A 0.4028 0.4474 0.8824 0.062 Uiso calc U . R 1 . .
H H9B 0.2924 0.4315 0.8614 0.062 Uiso calc U . R 1 . .
H H9C 0.3659 0.337 0.868 0.062 Uiso calc U . R 1 . .
C C10 0.3751(4) 0.3830(4) 0.96314(17) 0.0281(11) Uani d . . . 1 . .
C C11 0.4113(4) 0.3664(5) 1.04416(18) 0.0383(13) Uani d . . . 1 . .
H H11A 0.421 0.4327 1.0584 0.057 Uiso calc U . R 1 . .
H H11B 0.4753 0.3431 1.0311 0.057 Uiso calc U . R 1 . .
H H11C 0.3882 0.3184 1.0676 0.057 Uiso calc U . R 1 . .
C C12 0.2344(4) 0.3758(3) 1.01861(15) 0.0213(10) Uani d . . . 1 . .
N N1 0.0183(3) 0.3732(3) 1.02299(12) 0.0201(8) Uani d . . . 1 . .
N N2 0.0631(3) 0.3783(3) 0.98383(12) 0.0209(8) Uani d . . . 1 . .
N N3 0.3046(3) 0.3862(3) 0.92782(13) 0.0283(9) Uani d . . . 1 . .
N N4 0.3362(3) 0.3740(3) 1.00762(13) 0.0247(9) Uani d . . . 1 . .
N N5 0.2061(3) 0.3742(3) 1.06179(12) 0.0226(9) Uani d . . . 1 . .
H H5N 0.254 0.3801 1.0827 0.027 Uiso calc U . R 1 . .
O O1 -0.0681(2) 0.3608(2) 1.10308(11) 0.0249(7) Uani d . . . 1 . .
O O2 0.1457(3) 0.3898(3) 0.89963(11) 0.0329(8) Uani d . . . 1 . .
O O3 0.4639(3) 0.3882(3) 0.95567(13) 0.0402(10) Uani d . . . 1 . .
O O4 0.4472(7) 0.2008(8) 0.1306(3) 0.053(2) Uani d . P D 0.5 A -1
H H2O 0.413(8) 0.247(8) 0.143(5) 0.08 Uiso d U P D 0.5 B -1
H H1O 0.508(3) 0.219(10) 0.134(5) 0.08 Uiso d U P D 0.5 C -1


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 N5 . 1.900(4) ?
Cu1 N1 . 1.920(4) ?
Cu1 O1 . 1.940(3) ?
Cu1 O1 15_557 1.969(3) ?
C1 O1 . 1.347(6) ?
C1 C2 . 1.394(7) ?
C1 C6 . 1.403(6) ?
C2 C3 . 1.398(7) ?
C3 C4 . 1.386(7) ?
C4 C5 . 1.386(7) ?
C5 C6 . 1.396(6) ?
C6 N1 . 1.408(6) ?
C7 N2 . 1.337(6) ?
C7 C12 . 1.435(6) ?
C7 C8 . 1.465(6) ?
C8 O2 . 1.221(6) ?
C8 N3 . 1.393(7) ?
C9 N3 . 1.471(6) ?
C10 O3 . 1.199(6) ?
C10 N3 . 1.387(6) ?
C10 N4 . 1.393(6) ?
C11 N4 . 1.457(6) ?
C12 N5 . 1.306(6) ?
C12 N4 . 1.388(6) ?
N1 N2 . 1.282(5) ?
O1 Cu1 12_668 1.968(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N5 Cu1 N1 . . 91.39(16) ?
N5 Cu1 O1 . . 173.15(15) ?
N1 Cu1 O1 . . 84.39(15) ?
N5 Cu1 O1 . 15_557 95.74(15) ?
N1 Cu1 O1 . 15_557 167.05(15) ?
O1 Cu1 O1 . 15_557 89.45(14) ?
O1 C1 C2 . . 122.6(4) ?
O1 C1 C6 . . 117.6(4) ?
C2 C1 C6 . . 119.8(4) ?
C1 C2 C3 . . 119.1(4) ?
C4 C3 C2 . . 121.2(5) ?
C3 C4 C5 . . 119.8(4) ?
C4 C5 C6 . . 119.9(4) ?
C5 C6 C1 . . 120.3(4) ?
C5 C6 N1 . . 126.2(4) ?
C1 C6 N1 . . 113.6(4) ?
N2 C7 C12 . . 127.4(4) ?
N2 C7 C8 . . 112.8(4) ?
C12 C7 C8 . . 119.7(4) ?
O2 C8 N3 . . 119.6(4) ?
O2 C8 C7 . . 124.2(5) ?
N3 C8 C7 . . 116.2(4) ?
O3 C10 N3 . . 121.8(4) ?
O3 C10 N4 . . 122.4(5) ?
N3 C10 N4 . . 115.8(4) ?
N5 C12 N4 . . 119.9(4) ?
N5 C12 C7 . . 122.5(4) ?
N4 C12 C7 . . 117.6(4) ?
N2 N1 C6 . . 117.1(4) ?
N2 N1 Cu1 . . 130.5(3) ?
C6 N1 Cu1 . . 112.4(3) ?
N1 N2 C7 . . 121.0(4) ?
C10 N3 C8 . . 125.6(4) ?
C10 N3 C9 . . 116.1(4) ?
C8 N3 C9 . . 118.0(4) ?
C12 N4 C10 . . 124.8(4) ?
C12 N4 C11 . . 120.0(4) ?
C10 N4 C11 . . 115.1(4) ?
C12 N5 Cu1 . . 126.7(3) ?
C1 O1 Cu1 . . 112.0(3) ?
C1 O1 Cu1 . 12_668 124.5(3) ?
Cu1 O1 Cu1 . 12_668 122.14(16) ?



