# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_mh238ab
_database_code_depnum_ccdc_archive 'CCDC 1836719'
_audit_update_record             
;
2018-04-12 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_formula_moiety         'C14 H9 Cu N3 O5, H2O'
_chemical_formula_sum            'C14 H11 Cu N3 O6'
_chemical_formula_weight         380.80

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.344(3)
_cell_length_b                   8.507(3)
_cell_length_c                   12.926(4)
_cell_angle_alpha                73.95(3)
_cell_angle_beta                 83.60(3)
_cell_angle_gamma                80.66(3)
_cell_volume                     763.9(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6057
_cell_measurement_theta_min      1.64
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             386
_exptl_absorpt_coefficient_mu    1.467
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.787
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_process_details   'Stoe, X-area ver. 1.54'

_diffrn_ambient_temperature      100(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  IPDS2
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5636
_diffrn_reflns_av_R_equivalents  0.1141
_diffrn_reflns_av_sigmaI/netI    0.1004
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2686
_reflns_number_gt                1922
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0730P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2686
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1483
_refine_ls_wR_factor_gt          0.1425
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_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 0.22710(9) 0.86335(7) 0.22623(6) 0.0324(2) Uani 1 1 d . . .
N1 N 0.0829(6) 0.6757(5) 0.2623(4) 0.0346(11) Uani 1 1 d . . .
N2 N 0.0145(5) 0.9737(4) 0.1452(4) 0.0305(10) Uani 1 1 d . . .
N3 N 0.2955(6) 1.0919(5) 0.1862(4) 0.0328(11) Uani 1 1 d . . .
O1 O -0.2607(5) 0.9247(4) 0.0933(3) 0.0357(9) Uani 1 1 d . . .
O2 O -0.1147(5) 1.2339(4) 0.0467(3) 0.0375(10) Uani 1 1 d . . .
O3 O 0.4192(5) 0.7596(4) 0.3251(3) 0.0346(9) Uani 1 1 d . . .
O4 O 0.2325(6) 0.8769(5) 0.4381(4) 0.0513(11) Uani 1 1 d . . .
O1W O 0.4112(5) 0.8007(4) 0.0816(3) 0.0323(9) Uani 1 1 d . . .
O2W O 0.1518(6) 0.9843(5) 0.6233(4) 0.0545(12) Uani 1 1 d . . .
C1 C 0.1272(8) 0.5261(6) 0.3295(5) 0.0383(14) Uani 1 1 d . . .
H1A H 0.2402 0.5033 0.3636 0.046 Uiso 1 1 calc R . .
C2 C 0.0157(8) 0.4048(6) 0.3511(5) 0.0431(15) Uani 1 1 d . . .
H2A H 0.0499 0.3003 0.3997 0.052 Uiso 1 1 calc R . .
C3 C -0.1469(8) 0.4379(6) 0.3006(5) 0.0444(16) Uani 1 1 d . . .
H3A H -0.2267 0.3559 0.3142 0.053 Uiso 1 1 calc R . .
C4 C -0.1941(7) 0.5920(6) 0.2295(5) 0.0361(13) Uani 1 1 d . . .
H4A H -0.3042 0.6158 0.1925 0.043 Uiso 1 1 calc R . .
C5 C -0.0779(7) 0.7084(6) 0.2143(5) 0.0319(13) Uani 1 1 d . . .
C6 C -0.1197(7) 0.8827(5) 0.1433(5) 0.0313(12) Uani 1 1 d . . .
C7 C 0.0067(7) 1.1405(6) 0.0997(5) 0.0335(13) Uani 1 1 d . . .
C8 C 0.1713(7) 1.2034(6) 0.1250(5) 0.0331(13) Uani 1 1 d . . .
C9 C 0.1999(7) 1.3672(6) 0.0857(5) 0.0389(14) Uani 1 1 d . . .
H9A H 0.1129 1.4449 0.0419 0.047 Uiso 1 1 calc R . .
C10 C 0.3561(8) 1.4164(6) 0.1108(5) 0.0421(15) Uani 1 1 d . . .
H10A H 0.3764 1.5286 0.0857 0.050 Uiso 1 1 calc R . .
C11 C 0.4813(8) 1.3014(6) 0.1722(5) 0.0375(14) Uani 1 1 d . . .
H11A H 0.5910 1.3323 0.1888 0.045 Uiso 1 1 calc R . .
C12 C 0.4464(7) 1.1397(6) 0.2098(5) 0.0384(14) Uani 1 1 d . . .
H12A H 0.5322 1.0605 0.2536 0.046 Uiso 1 1 calc R . .
C13 C 0.3834(8) 0.7974(6) 0.4154(6) 0.0408(15) Uani 1 1 d . . .
C14 C 0.5298(9) 0.7394(7) 0.4954(5) 0.0493(16) Uani 1 1 d . . .
H14A H 0.6379 0.6795 0.4645 0.074 Uiso 1 1 calc R . .
H14B H 0.4808 0.6659 0.5616 0.074 Uiso 1 1 calc R . .
H14C H 0.5661 0.8349 0.5123 0.074 Uiso 1 1 calc R . .


_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 N2 1.940(4) . ?
Cu1 O3 1.943(4) . ?
Cu1 N1 1.978(4) . ?
Cu1 N3 2.000(4) . ?
Cu1 O1W 2.315(4) . ?
N1 C1 1.341(7) . ?
N1 C5 1.348(7) . ?
N2 C6 1.354(6) . ?
N2 C7 1.372(6) . ?
N3 C12 1.333(7) . ?
N3 C8 1.350(7) . ?
O1 C6 1.232(6) . ?
O2 C7 1.226(6) . ?
O3 C13 1.283(7) . ?
O4 C13 1.251(7) . ?
C1 C2 1.370(7) . ?
C1 H1A 0.9500 . ?
C2 C3 1.377(8) . ?
C2 H2A 0.9500 . ?
C3 C4 1.393(7) . ?
C3 H3A 0.9500 . ?
C4 C5 1.370(7) . ?
C4 H4A 0.9500 . ?
C5 C6 1.516(7) . ?
C7 C8 1.499(7) . ?
C8 C9 1.387(7) . ?
C9 C10 1.382(8) . ?
C9 H9A 0.9500 . ?
C10 C11 1.369(8) . ?
C10 H10A 0.9500 . ?
C11 C12 1.382(7) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C14 1.504(8) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
N2 Cu1 O3 171.87(18) . . ?
N2 Cu1 N1 81.97(17) . . ?
O3 Cu1 N1 96.85(17) . . ?
N2 Cu1 N3 82.59(17) . . ?
O3 Cu1 N3 97.26(16) . . ?
N1 Cu1 N3 162.49(17) . . ?
N2 Cu1 O1W 96.07(16) . . ?
O3 Cu1 O1W 92.06(15) . . ?
N1 Cu1 O1W 98.32(16) . . ?
N3 Cu1 O1W 91.47(16) . . ?
C1 N1 C5 118.7(4) . . ?
C1 N1 Cu1 126.9(4) . . ?
C5 N1 Cu1 114.3(3) . . ?
C6 N2 C7 125.1(4) . . ?
C6 N2 Cu1 117.7(3) . . ?
C7 N2 Cu1 117.1(3) . . ?
C12 N3 C8 119.7(4) . . ?
C12 N3 Cu1 127.7(4) . . ?
C8 N3 Cu1 112.5(3) . . ?
C13 O3 Cu1 111.7(3) . . ?
N1 C1 C2 122.6(5) . . ?
N1 C1 H1A 118.7 . . ?
C2 C1 H1A 118.7 . . ?
C1 C2 C3 118.5(5) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 H2A 120.8 . . ?
C2 C3 C4 119.7(5) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C5 C4 C3 118.3(5) . . ?
C5 C4 H4A 120.8 . . ?
C3 C4 H4A 120.8 . . ?
N1 C5 C4 122.1(5) . . ?
N1 C5 C6 115.0(4) . . ?
C4 C5 C6 123.0(5) . . ?
O1 C6 N2 128.6(5) . . ?
O1 C6 C5 120.4(4) . . ?
N2 C6 C5 110.9(4) . . ?
O2 C7 N2 127.9(5) . . ?
O2 C7 C8 121.2(4) . . ?
N2 C7 C8 110.8(4) . . ?
N3 C8 C9 120.6(5) . . ?
N3 C8 C7 117.0(4) . . ?
C9 C8 C7 122.4(5) . . ?
C10 C9 C8 119.4(5) . . ?
C10 C9 H9A 120.3 . . ?
C8 C9 H9A 120.3 . . ?
C11 C10 C9 119.2(5) . . ?
C11 C10 H10A 120.4 . . ?
C9 C10 H10A 120.4 . . ?
C10 C11 C12 119.2(5) . . ?
C10 C11 H11A 120.4 . . ?
C12 C11 H11A 120.4 . . ?
N3 C12 C11 121.8(5) . . ?
N3 C12 H12A 119.1 . . ?
C11 C12 H12A 119.1 . . ?
O4 C13 O3 122.2(6) . . ?
O4 C13 C14 120.5(6) . . ?
O3 C13 C14 117.3(5) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.65
_refine_diff_density_min         -0.86
_refine_diff_density_rms         0.12
