# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_rg166
_database_code_depnum_ccdc_archive 'CCDC 1863283'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2018-10-19 deposited with the CCDC.	2019-03-26 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 Cu N4 O7'
_chemical_formula_iupac          ?
_chemical_formula_weight         427.86
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   7.4893(3)
_cell_length_b                   9.7967(4)
_cell_length_c                   12.1077(5)
_cell_angle_alpha                97.4994(16)
_cell_angle_beta                 106.9521(16)
_cell_angle_gamma                107.5688(16)
_cell_volume                     786.51(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7544
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.18
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.340
_exptl_crystal_density_diffrn    1.807
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             438

_exptl_absorpt_coefficient_mu    1.441
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_T_max  0.64

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(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            11008
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         27.21
_diffrn_reflns_theta_full        27.21
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15

_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.
;

_reflns_number_total             5396
_reflns_number_gt                5089
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0645
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.029
_refine_ls_number_reflns         5396
_refine_ls_number_parameters     491
_refine_ls_number_restraints     471
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0315P)²+0.1106P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.363
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1727 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(9)

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'
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., 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2018)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'

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 0.23842(5) 0.36767(4) 0.73541(3) 0.01001(14) Uani d . . . 1 . .
Cu Cu2 0.42435(5) 0.60600(4) 0.32313(3) 0.01006(14) Uani d . . . 1 . .
C C1 0.0408(7) 0.4055(5) 0.5200(4) 0.0100(10) Uani d . . . 1 . .
C C2 -0.0634(5) 0.2407(4) 0.5110(3) 0.0115(7) Uani d . . . 1 . .
H H2 0.000789 0.184438 0.47068 0.014 Uiso calc U . R 1 . .
C C3 -0.2834(6) 0.1867(5) 0.4358(4) 0.0145(10) Uani d . . . 1 . .
H H3A -0.349333 0.247029 0.46847 0.017 Uiso calc U . R 1 . .
H H3B -0.298989 0.195746 0.353306 0.017 Uiso calc U . R 1 . .
C C4 0.1888(9) 0.1603(7) 0.8994(6) 0.0138(12) Uani d . . . 1 . .
H H4 0.079944 0.090052 0.834449 0.017 Uiso calc U . R 1 . .
C C5 0.2401(8) 0.1262(6) 1.0114(5) 0.0127(11) Uani d . . . 1 . .
H H5 0.162606 0.035184 1.021299 0.015 Uiso calc U . R 1 . .
C C6 0.3980(8) 0.2213(6) 1.1047(5) 0.0130(12) Uani d . . . 1 . .
H H6 0.432466 0.197439 1.179752 0.016 Uiso calc U . R 1 . .
C C7 0.5114(8) 0.3568(6) 1.0890(5) 0.0095(11) Uani d . . . 1 . .
C C8 0.6836(8) 0.4660(6) 1.1812(6) 0.0128(12) Uani d . . . 1 . .
H H8 0.728254 0.448131 1.257985 0.015 Uiso calc U . R 1 . .
C C9 0.7838(8) 0.5959(6) 1.1589(5) 0.0140(12) Uani d . . . 1 . .
H H9 0.898842 0.665871 1.220341 0.017 Uiso calc U . R 1 . .
C C10 0.7194(8) 0.6281(6) 1.0460(5) 0.0101(11) Uani d . . . 1 . .
C C11 0.8105(8) 0.7600(6) 1.0162(5) 0.0133(12) Uani d . . . 1 . .
H H11 0.923459 0.836232 1.074182 0.016 Uiso calc U . R 1 . .
C C12 0.7366(8) 0.7777(6) 0.9046(5) 0.0137(11) Uani d . . . 1 . .
H H12 0.799482 0.865553 0.884176 0.016 Uiso calc U . R 1 . .
C C13 0.5679(8) 0.6666(6) 0.8197(6) 0.0131(12) Uani d . . . 1 . .
H H13 0.516767 0.681359 0.742418 0.016 Uiso calc U . R 1 . .
C C14 0.5500(8) 0.5202(6) 0.9528(5) 0.0085(11) Uani d . . . 1 . .
C C15 0.4492(8) 0.3856(6) 0.9760(5) 0.0092(11) Uani d . . . 1 . .
C C16 0.6460(7) 0.5464(5) 0.5228(4) 0.0101(9) Uani d . . . 1 . .
C C17 0.7943(5) 0.6912(4) 0.5181(3) 0.0111(7) Uani d . . . 1 . .
H H17 0.902579 0.668613 0.49581 0.013 Uiso calc U . R 1 . .
C C18 0.8897(8) 0.8006(5) 0.6376(4) 0.0209(11) Uani d . . . 1 . .
H H18A 0.783788 0.818877 0.66389 0.025 Uiso calc U . R 1 . .
H H18B 0.963838 0.758168 0.696857 0.025 Uiso calc U . R 1 . .
C C19 0.4723(8) 0.8197(6) 0.1626(6) 0.0122(12) Uani d . . . 1 . .
H H19 0.579779 0.889166 0.228701 0.015 Uiso calc U . R 1 . .
C C20 0.4258(8) 0.8574(6) 0.0536(5) 0.0128(11) Uani d . . . 1 . .
H H20 0.501629 0.950146 0.045409 0.015 Uiso calc U . R 1 . .
C C21 0.2672(8) 0.7578(6) -0.0429(5) 0.0134(12) Uani d . . . 1 . .
H H21 0.234272 0.781719 -0.118029 0.016 Uiso calc U . R 1 . .
C C22 0.1551(8) 0.6210(7) -0.0296(5) 0.0123(11) Uani d . . . 1 . .
C C23 -0.0169(8) 0.5123(6) -0.1222(6) 0.0126(12) Uani d . . . 1 . .
H H23 -0.059938 0.531094 -0.198761 0.015 Uiso calc U . R 1 . .
C C24 -0.1185(8) 0.3839(6) -0.1025(5) 0.0112(11) Uani d . . . 1 . .
H H24 -0.232708 0.314353 -0.164741 0.013 Uiso calc U . R 1 . .
C C25 -0.0549(8) 0.3515(6) 0.0126(5) 0.0119(11) Uani d . . . 1 . .
C C26 -0.1522(8) 0.2178(6) 0.0380(5) 0.0119(11) Uani d . . . 1 . .
H H26 -0.267852 0.144762 -0.020787 0.014 Uiso calc U . R 1 . .
C C27 -0.0760(8) 0.1954(6) 0.1501(5) 0.0132(12) Uani d . . . 1 . .
H H27 -0.137374 0.105431 0.168469 0.016 Uiso calc U . R 1 . .
C C28 0.0932(8) 0.3068(6) 0.2370(5) 0.0101(11) Uani d . . . 1 . .
H H28 0.144077 0.29102 0.313894 0.012 Uiso calc U . R 1 . .
C C29 0.1086(8) 0.4538(6) 0.1015(5) 0.0103(11) Uani d . . . 1 . .
C C30 0.2166(8) 0.5941(6) 0.0832(5) 0.0108(11) Uani d . . . 1 . .
N N1 -0.0265(7) 0.2160(5) 0.6326(4) 0.0126(10) Uani d . . . 1 . .
H H1A -0.02426 0.123664 0.632826 0.015 Uiso calc U . R 1 . .
H H1B -0.124421 0.2261 0.659491 0.015 Uiso calc U . R 1 . .
N N2 0.2878(7) 0.2867(5) 0.8827(4) 0.0101(10) Uani d . . . 1 . .
N N3 0.4778(7) 0.5423(5) 0.8436(4) 0.0102(10) Uani d . . . 1 . .
N N4 0.6919(7) 0.7554(6) 0.4248(4) 0.0162(11) Uani d . . . 1 . .
H H4A 0.76757 0.782594 0.379112 0.019 Uiso calc U . R 1 . .
H H4B 0.676713 0.837157 0.459805 0.019 Uiso calc U . R 1 . .
N N5 0.3718(7) 0.6898(5) 0.1783(4) 0.0107(10) Uani d . . . 1 . .
N N6 0.1842(7) 0.4346(5) 0.2135(4) 0.0102(10) Uani d . . . 1 . .
N N7 0.5088(7) 0.9768(5) 0.7356(5) 0.0166(11) Uani d . . . 1 . .
N N8 0.1341(7) 0.9928(5) 0.3264(4) 0.0131(10) Uani d . . . 1 . .
O O1 0.1788(6) 0.4813(5) 0.6198(4) 0.0141(9) Uani d . . . 1 . .
O O2 -0.0112(5) 0.4552(4) 0.4326(3) 0.0123(7) Uani d . . . 1 . .
O O3 -0.3736(5) 0.0357(4) 0.4364(4) 0.0178(9) Uani d . . . 1 . .
H H3 -0.491809 0.018972 0.433542 0.027 Uiso calc U . R 1 . .
O O4 0.4809(6) 0.4883(4) 0.4363(4) 0.0150(9) Uani d . . . 1 . .
O O5 0.6969(5) 0.4932(4) 0.6090(3) 0.0156(8) Uani d . . . 1 . .
O O6 1.0227(6) 0.9363(4) 0.6332(4) 0.0192(9) Uani d . . . 1 . .
H H6A 1.128903 0.926065 0.630676 0.029 Uiso calc U . R 1 . .
O O7 0.4255(5) 0.2705(4) 0.6550(3) 0.0168(9) Uani d . . . 1 . .
H H7A 0.348174 0.19657 0.596202 0.025 Uiso d U . R 1 . .
H H7B 0.496712 0.340993 0.633626 0.025 Uiso d U . R 1 . .
O O8 0.2416(5) 0.7028(4) 0.4065(3) 0.0154(9) Uani d . . . 1 . .
H H8A 0.31575 0.765516 0.479954 0.023 Uiso d U . R 1 . .
H H8B 0.14913 0.633035 0.424657 0.023 Uiso d U . R 1 . .
O O9 0.4519(6) 0.9922(5) 0.8215(4) 0.0239(10) Uani d . . . 1 . .
O O10 0.3799(6) 0.9076(5) 0.6354(4) 0.0345(11) Uani d . . . 1 . .
O O11 0.6905(6) 1.0273(5) 0.7479(4) 0.0225(10) Uani d . . . 1 . .
O O12 0.2546(6) 1.0424(5) 0.4326(4) 0.0233(9) Uani d . . . 1 . .
O O13 -0.0509(6) 0.9489(5) 0.3048(4) 0.0184(9) Uani d . . . 1 . .
O O14 0.2014(6) 0.9871(5) 0.2432(4) 0.0228(10) 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
Cu1 O1 . 1.934(4) ?
Cu1 N1 . 1.998(5) ?
Cu1 N3 . 2.013(5) ?
Cu1 N2 . 2.027(5) ?
Cu1 O7 . 2.275(3) ?
Cu2 O4 . 1.938(4) ?
Cu2 N4 . 1.999(5) ?
Cu2 N6 . 2.005(5) ?
Cu2 N5 . 2.018(5) ?
Cu2 O8 . 2.265(3) ?
C1 O2 . 1.232(6) ?
C1 O1 . 1.286(6) ?
C1 C2 . 1.540(6) ?
C2 N1 . 1.483(6) ?
C2 C3 . 1.516(5) ?
C3 O3 . 1.430(6) ?
C4 N2 . 1.312(8) ?
C4 C5 . 1.411(9) ?
C5 C6 . 1.350(8) ?
C6 C7 . 1.413(8) ?
C7 C15 . 1.407(8) ?
C7 C8 . 1.438(7) ?
C8 C9 . 1.374(8) ?
C9 C10 . 1.421(8) ?
C10 C11 . 1.414(8) ?
C10 C14 . 1.430(7) ?
C11 C12 . 1.358(8) ?
C12 C13 . 1.399(8) ?
C13 N3 . 1.315(7) ?
C14 N3 . 1.347(8) ?
C14 C15 . 1.417(8) ?
C15 N2 . 1.374(6) ?
C16 O5 . 1.240(6) ?
C16 O4 . 1.271(6) ?
C16 C17 . 1.535(6) ?
C17 N4 . 1.494(6) ?
C17 C18 . 1.511(6) ?
C18 O6 . 1.419(6) ?
C19 N5 . 1.338(8) ?
C19 C20 . 1.392(8) ?
C20 C21 . 1.386(8) ?
C21 C22 . 1.408(8) ?
C22 C30 . 1.395(8) ?
C22 C23 . 1.439(7) ?
C23 C24 . 1.351(8) ?
C24 C25 . 1.446(8) ?
C25 C29 . 1.368(7) ?
C25 C26 . 1.414(8) ?
C26 C27 . 1.385(8) ?
C27 C28 . 1.412(7) ?
C28 N6 . 1.343(7) ?
C29 N6 . 1.370(8) ?
C29 C30 . 1.451(8) ?
C30 N5 . 1.355(7) ?
N7 O9 . 1.242(6) ?
N7 O10 . 1.253(6) ?
N7 O11 . 1.255(6) ?
N8 O14 . 1.253(6) ?
N8 O13 . 1.254(6) ?
N8 O12 . 1.265(6) ?

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
O1 Cu1 N1 . . 84.38(18) ?
O1 Cu1 N3 . . 91.13(19) ?
N1 Cu1 N3 . . 170.06(19) ?
O1 Cu1 N2 . . 165.59(17) ?
N1 Cu1 N2 . . 100.0(2) ?
N3 Cu1 N2 . . 82.3(2) ?
O1 Cu1 O7 . . 96.66(15) ?
N1 Cu1 O7 . . 96.24(16) ?
N3 Cu1 O7 . . 93.08(16) ?
N2 Cu1 O7 . . 96.51(17) ?
O4 Cu2 N4 . . 85.13(19) ?
O4 Cu2 N6 . . 91.07(19) ?
N4 Cu2 N6 . . 169.7(2) ?
O4 Cu2 N5 . . 166.03(17) ?
N4 Cu2 N5 . . 100.0(2) ?
N6 Cu2 N5 . . 81.6(2) ?
O4 Cu2 O8 . . 96.29(15) ?
N4 Cu2 O8 . . 96.65(17) ?
N6 Cu2 O8 . . 93.33(16) ?
N5 Cu2 O8 . . 96.01(17) ?
O2 C1 O1 . . 124.7(5) ?
O2 C1 C2 . . 118.7(4) ?
O1 C1 C2 . . 116.6(4) ?
N1 C2 C3 . . 113.4(3) ?
N1 C2 C1 . . 109.0(4) ?
C3 C2 C1 . . 111.4(3) ?
O3 C3 C2 . . 108.7(4) ?
N2 C4 C5 . . 121.6(6) ?
C6 C5 C4 . . 120.8(5) ?
C5 C6 C7 . . 119.1(5) ?
C15 C7 C6 . . 117.2(5) ?
C15 C7 C8 . . 118.6(5) ?
C6 C7 C8 . . 124.1(5) ?
C9 C8 C7 . . 120.4(6) ?
C8 C9 C10 . . 121.6(6) ?
C11 C10 C9 . . 125.3(5) ?
C11 C10 C14 . . 115.8(5) ?
C9 C10 C14 . . 118.9(5) ?
C12 C11 C10 . . 120.1(6) ?
C11 C12 C13 . . 120.0(5) ?
N3 C13 C12 . . 122.0(6) ?
N3 C14 C15 . . 118.0(5) ?
N3 C14 C10 . . 122.8(5) ?
C15 C14 C10 . . 119.2(5) ?
N2 C15 C7 . . 122.4(5) ?
N2 C15 C14 . . 116.3(5) ?
C7 C15 C14 . . 121.3(5) ?
O5 C16 O4 . . 124.8(5) ?
O5 C16 C17 . . 118.0(4) ?
O4 C16 C17 . . 117.2(4) ?
N4 C17 C18 . . 110.7(4) ?
N4 C17 C16 . . 110.1(4) ?
C18 C17 C16 . . 111.5(4) ?
O6 C18 C17 . . 111.8(4) ?
N5 C19 C20 . . 122.7(6) ?
C21 C20 C19 . . 119.1(5) ?
C20 C21 C22 . . 120.0(6) ?
C30 C22 C21 . . 116.1(5) ?
C30 C22 C23 . . 119.3(5) ?
C21 C22 C23 . . 124.6(6) ?
C24 C23 C22 . . 121.2(6) ?
C23 C24 C25 . . 120.6(5) ?
C29 C25 C26 . . 118.0(5) ?
C29 C25 C24 . . 118.8(5) ?
C26 C25 C24 . . 123.2(5) ?
C27 C26 C25 . . 118.8(5) ?
C26 C27 C28 . . 119.6(5) ?
N6 C28 C27 . . 121.6(5) ?
C25 C29 N6 . . 124.0(5) ?
C25 C29 C30 . . 121.5(5) ?
N6 C29 C30 . . 114.5(5) ?
N5 C30 C22 . . 124.8(5) ?
N5 C30 C29 . . 116.8(5) ?
C22 C30 C29 . . 118.5(5) ?
C2 N1 Cu1 . . 106.5(3) ?
C4 N2 C15 . . 118.8(5) ?
C4 N2 Cu1 . . 129.8(4) ?
C15 N2 Cu1 . . 111.4(3) ?
C13 N3 C14 . . 119.4(5) ?
C13 N3 Cu1 . . 128.7(4) ?
C14 N3 Cu1 . . 111.9(4) ?
C17 N4 Cu2 . . 109.5(3) ?
C19 N5 C30 . . 117.4(5) ?
C19 N5 Cu2 . . 129.6(4) ?
C30 N5 Cu2 . . 113.0(4) ?
C28 N6 C29 . . 117.9(5) ?
C28 N6 Cu2 . . 128.0(4) ?
C29 N6 Cu2 . . 114.1(4) ?
O9 N7 O10 . . 118.3(5) ?
O9 N7 O11 . . 121.5(5) ?
O10 N7 O11 . . 120.2(5) ?
O14 N8 O13 . . 120.4(5) ?
O14 N8 O12 . . 119.4(5) ?
O13 N8 O12 . . 120.2(5) ?
C1 O1 Cu1 . . 114.6(4) ?
C16 O4 Cu2 . . 116.4(3) ?


# start Validation Reply Form
_vrf_PLAT111_rg166               
;
PROBLEM: ADDSYM Detects New (Pseudo) Centre of Symmetry .        100 %Fit  
RESPONSE: The molecule is enantiomerically pure and confirmed by CD and
E-stat also suggests a chiral space group.
;
_vrf_PLAT113_rg166               
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        P-1 Check 
RESPONSE: he molecule is enantiomerically pure and confirmed by CD and
E-stat also suggests a chiral space group.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_rg121s
_database_code_depnum_ccdc_archive 'CCDC 1863287'
loop_
_audit_author_name
_audit_author_address
'Rakesh Ganguly'
;Division of Chemistry and Biological Chemistry, Nanyang Technological University, 637371 Singapore
Singapore
;
_audit_update_record             
;
2018-08-22 deposited with the CCDC.	2019-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'aqua(1.10-phenanthroline)(oxazolidine-4-carboxylato)copper(II) nitrate monohydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 Cu N3 O4, N O3, H2 O '
_chemical_formula_sum            'C16 H18 Cu N4 O8'
_chemical_formula_weight         457.88

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   6.6836(3)
_cell_length_b                   12.2756(4)
_cell_length_c                   21.8809(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1795.22(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    6587
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      28.91
_chemical_absolute_configuration abs
_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             940
_exptl_absorpt_coefficient_mu    1.273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6299
_exptl_absorpt_correction_T_max  0.9050
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      103(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24705
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         31.02
_reflns_number_total             5708
_reflns_number_gt                5088
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0368P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(8)
_refine_ls_number_reflns         5708
_refine_ls_number_parameters     277
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0726
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.62448(4) 0.581281(17) 0.943404(9) 0.01331(6) Uani 1 1 d . . .
C1 C 0.6718(3) 0.79443(14) 0.89822(8) 0.0139(4) Uani 1 1 d . . .
H1 H 0.8087 0.8015 0.8802 0.017 Uiso 1 1 calc R . .
C2 C 0.6856(3) 0.79770(15) 0.96806(8) 0.0145(4) Uani 1 1 d . . .
C3 C 0.5346(3) 0.88460(15) 0.87231(9) 0.0187(4) Uani 1 1 d . . .
H3A H 0.4735 0.9273 0.9058 0.022 Uiso 1 1 calc R . .
H3B H 0.6115 0.9346 0.8457 0.022 Uiso 1 1 calc R . .
C4 C 0.3699(4) 0.72341(14) 0.86431(7) 0.0166(3) Uani 1 1 d . . .
H4A H 0.3067 0.6718 0.8354 0.020 Uiso 1 1 calc R . .
H4B H 0.2899 0.7255 0.9024 0.020 Uiso 1 1 calc R . .
C5 C 0.5927(3) 0.42332(16) 0.83592(8) 0.0180(4) Uani 1 1 d . . .
H5 H 0.5847 0.4841 0.8092 0.022 Uiso 1 1 calc R . .
C6 C 0.6015(4) 0.31799(15) 0.81090(8) 0.0205(4) Uani 1 1 d . . .
H6 H 0.6005 0.3084 0.7678 0.025 Uiso 1 1 calc R . .
C7 C 0.6116(3) 0.22919(15) 0.84861(8) 0.0193(4) Uani 1 1 d . . .
H7 H 0.6167 0.1579 0.8318 0.023 Uiso 1 1 calc R . .
C8 C 0.6143(3) 0.24420(14) 0.91254(8) 0.0151(3) Uani 1 1 d . . .
C9 C 0.6214(3) 0.15814(14) 0.95675(8) 0.0178(4) Uani 1 1 d . . .
H9 H 0.6281 0.0848 0.9430 0.021 Uiso 1 1 calc R . .
C10 C 0.6189(3) 0.17857(14) 1.01763(8) 0.0172(4) Uani 1 1 d . . .
H10 H 0.6199 0.1195 1.0457 0.021 Uiso 1 1 calc R . .
C11 C 0.6148(3) 0.28870(14) 1.04027(8) 0.0140(3) Uani 1 1 d . . .
C12 C 0.6114(4) 0.31657(16) 1.10253(8) 0.0188(4) Uani 1 1 d . . .
H12 H 0.6140 0.2615 1.1330 0.023 Uiso 1 1 calc R . .
C13 C 0.6043(3) 0.42473(17) 1.11865(8) 0.0198(4) Uani 1 1 d . . .
H13 H 0.5980 0.4450 1.1605 0.024 Uiso 1 1 calc R . .
C14 C 0.6064(3) 0.50471(15) 1.07324(8) 0.0169(4) Uani 1 1 d . . .
H14 H 0.6037 0.5791 1.0851 0.020 Uiso 1 1 calc R . .
C15 C 0.6122(3) 0.37404(14) 0.99784(8) 0.0123(3) Uani 1 1 d . . .
C16 C 0.6073(3) 0.35244(13) 0.93341(7) 0.0122(3) Uani 1 1 d . . .
N1 N 0.5788(3) 0.69111(12) 0.87734(7) 0.0141(3) Uani 1 1 d . . .
H1N H 0.645(4) 0.6694(17) 0.8406(10) 0.021 Uiso 1 1 d . . .
N2 N 0.5951(3) 0.44043(11) 0.89605(6) 0.0135(3) Uani 1 1 d . . .
N3 N 0.6120(3) 0.48064(11) 1.01417(6) 0.0129(3) Uani 1 1 d . . .
N4 N 0.1332(3) 0.45034(13) 0.77549(7) 0.0192(3) Uani 1 1 d . . .
O1 O 0.6628(2) 0.70751(10) 0.99595(6) 0.0163(3) Uani 1 1 d . . .
O2 O 0.7149(2) 0.88714(10) 0.99283(6) 0.0173(3) Uani 1 1 d . . .
O3 O 0.3844(2) 0.82893(10) 0.83801(5) 0.0184(3) Uani 1 1 d . . .
O4 O 0.9518(2) 0.58126(13) 0.91397(6) 0.0202(3) Uani 1 1 d D . .
H1O H 0.999(4) 0.5402(19) 0.8902(10) 0.030 Uiso 1 1 d D . .
H2O H 1.037(3) 0.585(2) 0.9387(10) 0.030 Uiso 1 1 d D . .
O5 O 0.0901(3) 0.42568(12) 0.82913(6) 0.0290(4) Uani 1 1 d . . .
O6 O 0.1529(4) 0.37854(13) 0.73642(8) 0.0451(5) Uani 1 1 d . . .
O7 O 0.1596(3) 0.54783(11) 0.76046(7) 0.0289(4) Uani 1 1 d . . .
O8 O 0.7155(3) 0.34429(13) 0.26328(7) 0.0294(4) Uani 1 1 d D . .
H3O H 0.687(5) 0.2849(14) 0.2574(13) 0.044 Uiso 1 1 d D . .
H4O H 0.615(3) 0.378(2) 0.2696(13) 0.044 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 O1 1.9465(12) . ?
Cu1 N3 1.9827(14) . ?
Cu1 N1 2.0002(15) . ?
Cu1 N2 2.0253(14) . ?
Cu1 O4 2.2808(15) . ?
C1 N1 1.484(2) . ?
C1 C2 1.531(3) . ?
C1 C3 1.545(3) . ?
C2 O2 1.240(2) . ?
C2 O1 1.273(2) . ?
C3 O3 1.428(3) . ?
C4 O3 1.421(2) . ?
C4 N1 1.479(3) . ?
C5 N2 1.332(2) . ?
C5 C6 1.405(3) . ?
C6 C7 1.369(3) . ?
C7 C8 1.411(2) . ?
C8 C16 1.406(2) . ?
C8 C9 1.433(2) . ?
C9 C10 1.356(2) . ?
C10 C11 1.440(2) . ?
C11 C15 1.400(2) . ?
C11 C12 1.405(2) . ?
C12 C13 1.375(3) . ?
C13 C14 1.397(2) . ?
C14 N3 1.326(2) . ?
C15 N3 1.356(2) . ?
C15 C16 1.435(2) . ?
C16 N2 1.357(2) . ?
N4 O6 1.235(2) . ?
N4 O5 1.246(2) . ?
N4 O7 1.254(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N3 92.31(6) . . ?
O1 Cu1 N1 84.86(6) . . ?
N3 Cu1 N1 167.98(8) . . ?
O1 Cu1 N2 174.05(6) . . ?
N3 Cu1 N2 82.16(6) . . ?
N1 Cu1 N2 101.00(6) . . ?
O1 Cu1 O4 92.32(6) . . ?
N3 Cu1 O4 105.12(7) . . ?
N1 Cu1 O4 86.70(6) . . ?
N2 Cu1 O4 87.04(6) . . ?
N1 C1 C2 110.78(14) . . ?
N1 C1 C3 104.52(15) . . ?
C2 C1 C3 112.52(15) . . ?
O2 C2 O1 125.39(17) . . ?
O2 C2 C1 117.96(16) . . ?
O1 C2 C1 116.64(15) . . ?
O3 C3 C1 105.51(15) . . ?
O3 C4 N1 104.97(17) . . ?
N2 C5 C6 121.95(17) . . ?
C7 C6 C5 119.99(17) . . ?
C6 C7 C8 119.62(17) . . ?
C16 C8 C7 116.43(16) . . ?
C16 C8 C9 118.59(15) . . ?
C7 C8 C9 124.98(16) . . ?
C10 C9 C8 121.77(16) . . ?
C9 C10 C11 120.80(16) . . ?
C15 C11 C12 117.44(16) . . ?
C15 C11 C10 118.33(16) . . ?
C12 C11 C10 124.23(16) . . ?
C13 C12 C11 118.98(16) . . ?
C12 C13 C14 119.74(16) . . ?
N3 C14 C13 122.47(17) . . ?
N3 C15 C11 123.17(15) . . ?
N3 C15 C16 115.92(15) . . ?
C11 C15 C16 120.90(16) . . ?
N2 C16 C8 123.95(15) . . ?
N2 C16 C15 116.50(15) . . ?
C8 C16 C15 119.54(15) . . ?
C4 N1 C1 103.03(14) . . ?
C4 N1 Cu1 117.64(12) . . ?
C1 N1 Cu1 106.83(11) . . ?
C5 N2 C16 118.04(15) . . ?
C5 N2 Cu1 129.87(13) . . ?
C16 N2 Cu1 111.43(11) . . ?
C14 N3 C15 118.14(15) . . ?
C14 N3 Cu1 128.57(12) . . ?
C15 N3 Cu1 113.28(11) . . ?
O6 N4 O5 120.23(17) . . ?
O6 N4 O7 119.00(17) . . ?
O5 N4 O7 120.77(16) . . ?
C2 O1 Cu1 115.13(11) . . ?
C4 O3 C3 105.73(14) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        31.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.071
