# 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_ah81w
_database_code_depnum_ccdc_archive 'CCDC 1551503'
_audit_update_record             
;
2018-09-07 deposited with the CCDC.
2018-09-11 downloaded from the CCDC.
;
_audit_creation_date             2018-09-07
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5356)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.25(C12 H24 Cu4 N12 O12), 1[H2O]'
_chemical_formula_sum            'C3 H8 Cu N3 O4'
_chemical_formula_weight         213.66
_chemical_melting_point          ?
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'
Cu Cu -1.9646 0.5888 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   14.5619(4)
_cell_length_b                   6.4760(2)
_cell_length_c                   7.4973(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.469(3)
_cell_angle_gamma                90
_cell_volume                     703.80(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2919
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      76.0950
_cell_measurement_theta_min      6.0980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.251
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.016
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.1282
_exptl_crystal_size_mid          0.1004
_exptl_crystal_size_min          0.0706
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3958
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.260
_diffrn_reflns_theta_min         6.106
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    9.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6798 -104.0000   29.0000 53

#__ type_ start__ end____ width___ exp.time_
  2 omega  -81.00    0.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  104.0000  130.0000 81

#__ type_ start__ end____ width___ exp.time_
  3 omega   51.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -104.0000   29.0000 53

#__ type_ start__ end____ width___ exp.time_
  4 omega  108.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  104.0000  130.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega -120.00  -92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
  6 omega -122.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000  -60.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega -122.00  -87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
  8 omega -125.00  -85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000   60.0000 40

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
 10 omega   75.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   82.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000 -180.0000 57

#__ type_ start__ end____ width___ exp.time_
 12 omega   58.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  150.0000 40

#__ type_ start__ end____ width___ exp.time_
 13 omega   41.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  150.0000 69

#__ type_ start__ end____ width___ exp.time_
 14 omega  145.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 15 omega   39.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
 16 omega   40.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 17 omega   97.00  144.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000   60.0000 47

#__ type_ start__ end____ width___ exp.time_
 18 omega   53.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega  108.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000 -150.0000 66

#__ type_ start__ end____ width___ exp.time_
 20 omega -118.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  -77.0000  150.0000 109

#__ type_ start__ end____ width___ exp.time_
 21 omega -116.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -61.0000   60.0000 102

#__ type_ start__ end____ width___ exp.time_
 22 omega -120.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -77.0000  -30.0000 109

#__ type_ start__ end____ width___ exp.time_
 23 omega -116.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -61.0000 -150.0000 102

#__ type_ start__ end____ width___ exp.time_
 24 omega   82.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000 -120.0000 96

#__ type_ start__ end____ width___ exp.time_
 25 omega   28.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000 -120.0000 81

#__ type_ start__ end____ width___ exp.time_
 26 omega   83.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000   90.0000 95

#__ type_ start__ end____ width___ exp.time_
 27 omega   38.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000   90.0000 60

#__ type_ start__ end____ width___ exp.time_
 28 omega   78.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
 29 omega   82.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000   30.0000 68

#__ type_ start__ end____ width___ exp.time_
 30 omega   58.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000    0.0000 120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                773
_reflns_number_total             794
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         794
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0242
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0406P)²+1.1121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0657
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 O2-H2C
 0.84 with sigma of 0.01
 O2-H2D
 0.84 with sigma of 0.01
3. Others
 Fixed Sof: H2A(0.5) H2B(0.5) H3A(0.5) H3B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.250000 0.750000 1.000000 0.00873(15) Uani 1 2 d S T P . .
O1 O 0.35804(8) 0.82627(18) 0.87762(15) 0.0124(3) Uani 1 1 d . . . . .
N1 N 0.23156(14) 0.500000 0.8405(2) 0.0109(4) Uani 1 2 d S T P . .
N2 N 0.25733(13) 0.500000 0.6916(3) 0.0115(4) Uani 1 2 d S T P . .
N3 N 0.27983(18) 0.500000 0.5502(3) 0.0243(5) Uani 1 2 d S T P . .
C1 C 0.39220(16) 1.000000 0.8450(3) 0.0105(4) Uani 1 2 d S T P . .
C2 C 0.48023(16) 1.000000 0.7526(3) 0.0143(5) Uani 1 2 d S T P . .
H2A H 0.517297 0.876152 0.788715 0.017 Uiso 0.5 1 calc R . . . .
H2B H 0.517297 1.123848 0.788716 0.017 Uiso 0.5 1 calc R . . . .
C3 C 0.45648(16) 1.000000 0.5488(3) 0.0129(5) Uani 1 2 d S T P . .
H3A H 0.419132 0.876305 0.513504 0.015 Uiso 0.5 1 calc R . . . .
H3B H 0.419132 1.123695 0.513504 0.015 Uiso 0.5 1 calc R . . . .
O2 O 0.16001(12) 1.000000 0.8119(2) 0.0152(4) Uani 1 2 d DS T P . .
H2C H 0.172(3) 1.000000 0.704(2) 0.042(11) Uiso 1 2 d DS T P . .
H2D H 0.1018(7) 1.000000 0.794(7) 0.076(17) Uiso 1 2 d DS T P . .


_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 1.9587(11) . ?
Cu1 O1 1.9587(11) 7_567 ?
Cu1 N1 2.0154(11) . ?
Cu1 N1 2.0154(11) 7_567 ?
Cu1 O2 2.4443(13) . ?
O1 C1 1.2634(15) . ?
N1 N2 1.211(3) . ?
N2 N3 1.139(3) . ?
C1 C2 1.514(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.534(3) . ?
C3 C3 1.523(4) 5_676 ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
O2 H2C 0.840(10) . ?
O2 H2D 0.845(10) . ?

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 O1 180.0 . 7_567 ?
O1 Cu1 N1 90.45(6) 7_567 . ?
O1 Cu1 N1 90.45(6) . 7_567 ?
O1 Cu1 N1 89.55(6) . . ?
O1 Cu1 N1 89.55(6) 7_567 7_567 ?
O1 Cu1 O2 91.54(5) 7_567 . ?
O1 Cu1 O2 88.46(5) . . ?
N1 Cu1 N1 180.0 . 7_567 ?
N1 Cu1 O2 81.02(5) 7_567 . ?
N1 Cu1 O2 98.98(5) . . ?
C1 O1 Cu1 131.60(12) . . ?
Cu1 N1 Cu1 106.90(8) . 4_547 ?
N2 N1 Cu1 120.76(7) . 4_547 ?
N2 N1 Cu1 120.76(7) . . ?
N3 N2 N1 178.7(2) . . ?
O1 C1 O1 125.9(2) 6_575 . ?
O1 C1 C2 117.05(10) . . ?
O1 C1 C2 117.04(10) 6_575 . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
C1 C2 C3 109.59(19) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C3 C3 C2 111.1(2) 5_676 . ?
C3 C3 H3A 109.4 5_676 . ?
C3 C3 H3B 109.4 5_676 . ?
H3A C3 H3B 108.0 . . ?
Cu1 O2 H2C 114(2) . . ?
Cu1 O2 H2D 124(2) . . ?
H2C O2 H2D 98(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 O1 -4.9(3) . . . 6_575 ?
Cu1 O1 C1 C2 177.44(13) . . . . ?
O1 C1 C2 C3 88.96(17) . . . . ?
O1 C1 C2 C3 -88.96(17) 6_575 . . . ?
C1 C2 C3 C3 180.000(0) . . . 5_676 ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 36 electrons were 
found in a volume of 124Å^3 in 1 void. 
This is consistent with the presence of 
1[H2O] per formula unit 
which account for 40.0 electrons.
;

loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.029 61.9 17.9 '1/2 water'
2 0.500 0.500 -0.814 61.9 17.9 '1/2 water'

_smtbx_masks_void_probe_radius   1.0
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
