# Electronic Supplementary Material (ESI) for Nanoscale.
# 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_publication_text
_database_code_depnum_ccdc_archive 'CCDC 1575192'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'aquabis-(3-ethylpyridine)diformatocopper (II)'
_chemical_name_common            
'bis-(3-ethylpyridine) copper(II) formate monohydrate'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 Cu N2 O5'
_exptl_crystal_recrystallization_method toluene
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_diffrn_ambient_temperature      200(2)
_diffrn_ambient_pressure         101.325
_chemical_formula_weight         385.89

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'
_chemical_absolute_configuration ?

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

_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. 
;

_cell_length_a                   10.8381(3)
_cell_length_b                   15.1085(4)
_cell_length_c                   11.1446(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.5042(16)
_cell_angle_gamma                90
_cell_volume                     1804.83(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4868
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      28.20
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             804
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.237
_shelx_estimated_absorpt_T_min   0.664
_shelx_estimated_absorpt_T_max   0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6356
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'X-ray Tube'
_diffrn_source_type              'Siemens KFF MO 2K-90'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7786
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.794
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2955
_reflns_number_gt                2755
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.990

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _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. 
;

_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0342P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.371(16)
_refine_ls_number_reflns         2955
_refine_ls_number_parameters     223
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0216
_refine_ls_wR_factor_ref         0.0538
_refine_ls_wR_factor_gt          0.0522
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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_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 0.69277(3) 0.01681(2) 0.65430(3) 0.02873(8) Uani 1 1 d . . . . .
O1 O 0.60104(16) 0.10253(11) 0.73978(17) 0.0351(4) Uani 1 1 d . . . . .
O2 O 0.5719(2) 0.20892(14) 0.6003(2) 0.0554(6) Uani 1 1 d . . . . .
O3 O 0.79146(16) -0.08086(12) 0.60501(17) 0.0361(4) Uani 1 1 d . . . . .
O4 O 0.8108(2) -0.13295(17) 0.7934(2) 0.0596(6) Uani 1 1 d . . . . .
O5 O 0.65857(19) 0.08132(13) 0.46281(18) 0.0435(5) Uani 1 1 d G . . . .
H5B H 0.7068 0.1009 0.4028 0.066(11) Uiso 1 1 d G . . . .
H5C H 0.6208 0.1333 0.5003 0.104(17) Uiso 1 1 d G . . . .
N1 N 0.84959(19) 0.08464(14) 0.7126(2) 0.0325(4) Uani 1 1 d . . . . .
N2 N 0.53431(18) -0.05382(14) 0.6159(2) 0.0319(4) Uani 1 1 d . . . . .
C1 C 0.5660(2) 0.17782(18) 0.6999(3) 0.0380(6) Uani 1 1 d . . . . .
H1A H 0.5306 0.2150 0.7546 0.046 Uiso 1 1 calc R U . . .
C2 C 0.8318(2) -0.13418(18) 0.6886(3) 0.0406(6) Uani 1 1 d . . . . .
H2A H 0.8843 -0.1804 0.6680 0.049 Uiso 1 1 calc R U . . .
C3 C 0.9282(2) 0.10919(17) 0.6366(2) 0.0350(5) Uani 1 1 d . . . . .
H3A H 0.9124 0.0891 0.5550 0.042 Uiso 1 1 calc R U . . .
C4 C 1.0315(2) 0.16238(19) 0.6709(3) 0.0398(6) Uani 1 1 d . . . . .
C5 C 1.0550(3) 0.1886(2) 0.7916(3) 0.0486(7) Uani 1 1 d . . . . .
H5A H 1.1249 0.2250 0.8192 0.058 Uiso 1 1 calc R U . . .
C6 C 0.9765(3) 0.1615(2) 0.8710(3) 0.0527(8) Uani 1 1 d . . . . .
H6A H 0.9922 0.1788 0.9538 0.063 Uiso 1 1 calc R U . . .
C7 C 0.8753(2) 0.1092(2) 0.8293(3) 0.0429(6) Uani 1 1 d . . . . .
H7A H 0.8222 0.0899 0.8847 0.051 Uiso 1 1 calc R U . . .
C8 C 1.1170(3) 0.1886(2) 0.5822(3) 0.0545(8) Uani 1 1 d . . . . .
H8A H 1.1346 0.2528 0.5903 0.065 Uiso 1 1 calc R U . . .
H8B H 1.0744 0.1777 0.4987 0.065 Uiso 1 1 calc R U . . .
C9 C 1.2391(3) 0.1383(3) 0.6017(3) 0.0659(10) Uani 1 1 d . . . . .
H9A H 1.2913 0.1577 0.5420 0.099 Uiso 1 1 calc R U . . .
H9B H 1.2826 0.1499 0.6837 0.099 Uiso 1 1 calc R U . . .
H9C H 1.2224 0.0748 0.5920 0.099 Uiso 1 1 calc R U . . .
C10 C 0.4616(2) -0.06672(17) 0.7011(2) 0.0346(5) Uani 1 1 d . . . . .
H10A H 0.4854 -0.0404 0.7785 0.041 Uiso 1 1 calc R U . . .
C11 C 0.3535(2) -0.11645(19) 0.6823(3) 0.0401(6) Uani 1 1 d . . . . .
C12 C 0.3202(3) -0.1535(2) 0.5689(3) 0.0530(8) Uani 1 1 d . . . . .
H12A H 0.2465 -0.1882 0.5518 0.064 Uiso 1 1 calc R U . . .
C13 C 0.3946(3) -0.1399(3) 0.4808(3) 0.0554(8) Uani 1 1 d . . . . .
H13A H 0.3724 -0.1648 0.4023 0.067 Uiso 1 1 calc R U . . .
C14 C 0.5015(3) -0.0898(2) 0.5070(3) 0.0424(6) Uani 1 1 d . . . . .
H14A H 0.5528 -0.0808 0.4460 0.051 Uiso 1 1 calc R U . . .
C15 C 0.2764(3) -0.1281(3) 0.7832(3) 0.0562(8) Uani 1 1 d . . . . .
H15A H 0.2544 -0.1914 0.7887 0.067 Uiso 1 1 calc R U . . .
H15B H 0.3272 -0.1110 0.8610 0.067 Uiso 1 1 calc R U . . .
C16 C 0.1592(4) -0.0743(3) 0.7657(5) 0.0829(14) Uani 1 1 d . . . . .
H16A H 0.1131 -0.0845 0.8338 0.124 Uiso 1 1 calc R U . . .
H16B H 0.1802 -0.0114 0.7621 0.124 Uiso 1 1 calc R U . . .
H16C H 0.1073 -0.0918 0.6898 0.124 Uiso 1 1 calc R U . . .


_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 O3 1.9487(17) . ?
Cu1 O1 1.9629(17) . ?
Cu1 N1 2.009(2) . ?
Cu1 N2 2.013(2) . ?
Cu1 O5 2.325(2) . ?
O1 C1 1.259(3) . ?
O2 C1 1.216(4) . ?
O3 C2 1.260(3) . ?
O4 C2 1.222(4) . ?
N1 C3 1.340(3) . ?
N1 C7 1.342(3) . ?
N2 C14 1.329(4) . ?
N2 C10 1.335(3) . ?
C3 C4 1.385(4) . ?
C4 C5 1.388(4) . ?
C4 C8 1.505(4) . ?
C5 C6 1.377(5) . ?
C6 C7 1.376(4) . ?
C8 C9 1.514(5) . ?
C10 C11 1.382(4) . ?
C11 C12 1.382(4) . ?
C11 C15 1.506(4) . ?
C12 C13 1.375(5) . ?
C13 C14 1.379(4) . ?
C15 C16 1.496(5) . ?

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
O3 Cu1 O1 167.14(8) . . ?
O3 Cu1 N1 90.23(8) . . ?
O1 Cu1 N1 88.36(8) . . ?
O3 Cu1 N2 91.45(8) . . ?
O1 Cu1 N2 88.60(8) . . ?
N1 Cu1 N2 173.47(10) . . ?
O3 Cu1 O5 94.49(8) . . ?
O1 Cu1 O5 98.36(8) . . ?
N1 Cu1 O5 95.48(8) . . ?
N2 Cu1 O5 90.68(8) . . ?
C1 O1 Cu1 124.94(17) . . ?
C2 O3 Cu1 114.87(17) . . ?
C3 N1 C7 118.4(2) . . ?
C3 N1 Cu1 121.58(17) . . ?
C7 N1 Cu1 119.96(18) . . ?
C14 N2 C10 118.9(2) . . ?
C14 N2 Cu1 121.03(18) . . ?
C10 N2 Cu1 120.04(17) . . ?
O2 C1 O1 128.1(3) . . ?
O4 C2 O3 127.1(3) . . ?
N1 C3 C4 123.3(2) . . ?
C3 C4 C5 117.3(3) . . ?
C3 C4 C8 121.5(3) . . ?
C5 C4 C8 121.2(3) . . ?
C6 C5 C4 119.7(3) . . ?
C7 C6 C5 119.4(3) . . ?
N1 C7 C6 121.8(3) . . ?
C4 C8 C9 112.6(3) . . ?
N2 C10 C11 123.2(3) . . ?
C12 C11 C10 117.4(3) . . ?
C12 C11 C15 122.5(3) . . ?
C10 C11 C15 120.1(3) . . ?
C13 C12 C11 119.5(3) . . ?
C12 C13 C14 119.6(3) . . ?
N2 C14 C13 121.4(3) . . ?
C16 C15 C11 113.2(3) . . ?

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 O2 6.7(4) . . . . ?
Cu1 O3 C2 O4 3.6(4) . . . . ?
C7 N1 C3 C4 -3.3(4) . . . . ?
Cu1 N1 C3 C4 174.3(2) . . . . ?
N1 C3 C4 C5 2.0(4) . . . . ?
N1 C3 C4 C8 -179.7(3) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C8 C4 C5 C6 -178.4(3) . . . . ?
C4 C5 C6 C7 -0.4(5) . . . . ?
C3 N1 C7 C6 2.7(4) . . . . ?
Cu1 N1 C7 C6 -174.9(2) . . . . ?
C5 C6 C7 N1 -0.9(5) . . . . ?
C3 C4 C8 C9 -104.8(3) . . . . ?
C5 C4 C8 C9 73.4(4) . . . . ?
C14 N2 C10 C11 0.5(4) . . . . ?
Cu1 N2 C10 C11 -178.2(2) . . . . ?
N2 C10 C11 C12 -0.5(4) . . . . ?
N2 C10 C11 C15 179.9(3) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C15 C11 C12 C13 179.7(3) . . . . ?
C11 C12 C13 C14 0.3(6) . . . . ?
C10 N2 C14 C13 -0.1(4) . . . . ?
Cu1 N2 C14 C13 178.5(3) . . . . ?
C12 C13 C14 N2 -0.3(5) . . . . ?
C12 C11 C15 C16 -74.1(4) . . . . ?
C10 C11 C15 C16 105.5(4) . . . . ?

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_publication_text_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1575195'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'bis(2-amino-6methylheptane)diformatocopper (II)'
_chemical_name_common            
'bis(2-amino-6methylheptane) copper (II) formate'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H40 Cu N2 O4'
_exptl_crystal_recrystallization_method acetonitrile
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            purple

_diffrn_ambient_temperature      200(2)
_diffrn_ambient_pressure         101.325
_chemical_formula_weight         412.06

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration ?

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'

_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. 
;

_cell_length_a                   15.9235(15)
_cell_length_b                   6.9220(6)
_cell_length_c                   10.4447(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.090(5)
_cell_angle_gamma                90
_cell_volume                     1142.44(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3341
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      24.67
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_F_000             446
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.977
_shelx_estimated_absorpt_T_min   0.814
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3340
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with three batch runs at phi = 0.00 deg 
 (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg 
 (650 frames). 
 Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'X-ray Tube'
_diffrn_source_type              'Siemens KFF MO 2K-90'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8559
_diffrn_reflns_av_unetI/netI     0.0845
_diffrn_reflns_av_R_equivalents  0.0921
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.578
_diffrn_reflns_theta_max         24.894
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.939
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.939
_reflns_number_total             1939
_reflns_number_gt                1247
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _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. 
;

_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1908P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1939
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1363
_refine_ls_R_factor_gt           0.0978
_refine_ls_wR_factor_ref         0.2758
_refine_ls_wR_factor_gt          0.2381
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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_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 0.0000 0.0000 0.5000 0.0390(5) Uani 1 2 d S . P . .
O1 O 0.0859(3) 0.1341(7) 0.4139(4) 0.0474(12) Uani 1 1 d . . . . .
O2 O 0.0136(3) 0.0229(7) 0.2311(5) 0.0511(13) Uani 1 1 d . . . . .
N1 N -0.0639(3) 0.2501(8) 0.4948(5) 0.0410(13) Uani 1 1 d . . . . .
H1B H -0.0420 0.3232 0.5734 0.049 Uiso 1 1 calc R U . . .
H1C H -0.0483 0.3244 0.4203 0.049 Uiso 1 1 calc R U . . .
C1 C 0.0705(5) 0.1203(9) 0.2925(6) 0.0497(19) Uani 1 1 d . . . . .
H1A H 0.1061 0.1916 0.2432 0.060 Uiso 1 1 calc R U . . .
C2 C -0.1582(5) 0.2527(10) 0.4860(6) 0.0452(17) Uani 1 1 d . . . . .
H2A H -0.1748 0.1739 0.5591 0.054 Uiso 1 1 calc R U . . .
C3 C -0.1963(5) 0.1591(12) 0.3625(7) 0.064(2) Uani 1 1 d . . . . .
H3A H -0.1742 0.0275 0.3579 0.095 Uiso 1 1 calc R U . . .
H3B H -0.1815 0.2343 0.2890 0.095 Uiso 1 1 calc R U . . .
H3C H -0.2580 0.1545 0.3600 0.095 Uiso 1 1 calc R U . . .
C4 C -0.1881(5) 0.4593(11) 0.5036(8) 0.056(2) Uani 1 1 d . . . . .
H4A H -0.1765 0.5357 0.4275 0.067 Uiso 1 1 calc R U . . .
H4B H -0.1535 0.5151 0.5799 0.067 Uiso 1 1 calc R U . . .
C5 C -0.2817(5) 0.4844(10) 0.5207(8) 0.054(2) Uani 1 1 d . . . . .
H5A H -0.3169 0.4551 0.4381 0.064 Uiso 1 1 calc R U . . .
H5B H -0.2968 0.3910 0.5860 0.064 Uiso 1 1 calc R U . . .
C6 C -0.3013(5) 0.6858(13) 0.5627(8) 0.070(2) Uani 1 1 d . . . . .
H6A H -0.2675 0.7095 0.6473 0.084 Uiso 1 1 calc R U . . .
H6B H -0.2809 0.7772 0.5005 0.084 Uiso 1 1 calc R U . . .
C7 C -0.3911(6) 0.7358(15) 0.5751(8) 0.079(3) Uani 1 1 d . . . . .
H7A H -0.4242 0.7155 0.4883 0.095 Uiso 1 1 calc R U . . .
C8 C -0.3984(8) 0.9511(17) 0.6077(13) 0.105(4) Uani 1 1 d . . . . .
H8A H -0.3743 1.0290 0.5429 0.158 Uiso 1 1 calc R U . . .
H8B H -0.3674 0.9766 0.6931 0.158 Uiso 1 1 calc R U . . .
H8C H -0.4581 0.9851 0.6081 0.158 Uiso 1 1 calc R U . . .
C9 C -0.4293(8) 0.604(2) 0.6690(12) 0.118(4) Uani 1 1 d . . . . .
H9A H -0.4250 0.4690 0.6414 0.177 Uiso 1 1 calc R U . . .
H9B H -0.4890 0.6371 0.6705 0.177 Uiso 1 1 calc R U . . .
H9C H -0.3986 0.6196 0.7556 0.177 Uiso 1 1 calc R U . . .


_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 1.961(4) 3_556 ?
Cu1 O1 1.961(4) . ?
Cu1 N1 2.005(5) 3_556 ?
Cu1 N1 2.005(5) . ?
O1 C1 1.265(8) . ?
O2 C1 1.242(9) . ?
N1 C2 1.494(8) . ?
C2 C3 1.503(9) . ?
C2 C4 1.525(10) . ?
C4 C5 1.534(11) . ?
C5 C6 1.506(11) . ?
C6 C7 1.493(11) . ?
C7 C9 1.522(14) . ?
C7 C8 1.537(14) . ?

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 3_556 . ?
O1 Cu1 N1 87.6(2) 3_556 3_556 ?
O1 Cu1 N1 92.4(2) . 3_556 ?
O1 Cu1 N1 92.4(2) 3_556 . ?
O1 Cu1 N1 87.7(2) . . ?
N1 Cu1 N1 180.0 3_556 . ?
C1 O1 Cu1 111.3(4) . . ?
C2 N1 Cu1 121.0(4) . . ?
O2 C1 O1 126.7(6) . . ?
N1 C2 C3 110.1(5) . . ?
N1 C2 C4 109.2(6) . . ?
C3 C2 C4 114.1(6) . . ?
C2 C4 C5 116.2(6) . . ?
C6 C5 C4 112.2(7) . . ?
C7 C6 C5 118.4(8) . . ?
C6 C7 C9 112.3(9) . . ?
C6 C7 C8 110.1(9) . . ?
C9 C7 C8 113.1(9) . . ?

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 O2 -5.8(8) . . . . ?
Cu1 N1 C2 C3 -62.1(6) . . . . ?
Cu1 N1 C2 C4 171.8(4) . . . . ?
N1 C2 C4 C5 -169.8(6) . . . . ?
C3 C2 C4 C5 66.5(9) . . . . ?
C2 C4 C5 C6 168.9(6) . . . . ?
C4 C5 C6 C7 176.1(7) . . . . ?
C5 C6 C7 C9 57.6(12) . . . . ?
C5 C6 C7 C8 -175.3(8) . . . . ?

_refine_diff_density_max         2.184
_refine_diff_density_min         -0.929
_refine_diff_density_rms         0.171

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_publication_text_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1575194'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'aquabis-(2-ethylhexylamine)difromatocopper (II)'
_chemical_name_common            
'bis(2-ethylhexylamine) copper (II) formate monohydrate'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H42 Cu N2 O5'
_exptl_crystal_recrystallization_method '1:1 acetonitrile:methanol'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_diffrn_ambient_temperature      200(2)
_diffrn_ambient_pressure         101.325
_chemical_formula_weight         430.07

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yn'
_chemical_absolute_configuration ?

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

_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. 
;

_cell_length_a                   34.494(4)
_cell_length_b                   6.7114(7)
_cell_length_c                   9.7554(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.350(5)
_cell_angle_gamma                90
_cell_volume                     2258.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9134
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      28.20
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             932
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.995
_shelx_estimated_absorpt_T_min   0.873
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.381889
_exptl_absorpt_correction_T_max  0.745683
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'X-ray Tube'
_diffrn_source_type              'Siemens KFF MO 2K-90'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6407
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.362
_diffrn_reflns_theta_max         28.470
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             2748
_reflns_number_gt                2234
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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. 
;

_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1045P)²+2.6404P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2748
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1639
_refine_ls_wR_factor_gt          0.1541
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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_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 0.0000 0.34530(8) 0.2500 0.0227(2) Uani 1 2 d S T P . .
O1 O -0.03039(11) 0.3298(5) 0.0789(4) 0.0311(8) Uani 1 1 d . . . . .
O2 O -0.03816(11) 0.0017(5) 0.0981(5) 0.0484(11) Uani 1 1 d . . . . .
O3 O 0.0000 -0.3031(6) 0.2500 0.0387(10) Uani 1 2 d S T P . .
H3B H -0.0156 -0.2375 0.1926 0.046 Uiso 1 1 d R U . . .
N1 N 0.04711(12) 0.3440(5) 0.1281(6) 0.0302(10) Uani 1 1 d . . . . .
H1B H 0.0482 0.2230 0.0863 0.036 Uiso 1 1 calc R U . . .
H1C H 0.0432 0.4365 0.0613 0.036 Uiso 1 1 calc R U . . .
C1 C -0.04153(14) 0.1602(7) 0.0376(6) 0.0321(11) Uani 1 1 d . . . . .
H1A H -0.0538 0.1557 -0.0497 0.039 Uiso 1 1 calc R U . . .
C2 C 0.08563(13) 0.3829(8) 0.1911(6) 0.0366(12) Uani 1 1 d . . . . .
H2A H 0.0908 0.2773 0.2597 0.044 Uiso 1 1 calc R U . . .
H2B H 0.0842 0.5110 0.2412 0.044 Uiso 1 1 calc R U . . .
C3 C 0.11990(14) 0.3924(8) 0.0954(6) 0.0326(11) Uani 1 1 d . . . . .
H3A H 0.1145 0.5018 0.0283 0.039 Uiso 1 1 calc R U . . .
C4 C 0.15609(14) 0.4532(8) 0.1771(6) 0.0377(12) Uani 1 1 d . . . . .
H4A H 0.1514 0.5865 0.2170 0.045 Uiso 1 1 calc R U . . .
H4B H 0.1592 0.3587 0.2543 0.045 Uiso 1 1 calc R U . . .
C5 C 0.19406(14) 0.4609(8) 0.0999(7) 0.0437(15) Uani 1 1 d . . . . .
H5A H 0.2013 0.3237 0.0729 0.052 Uiso 1 1 calc R U . . .
H5B H 0.1901 0.5390 0.0149 0.052 Uiso 1 1 calc R U . . .
C6 C 0.22728(15) 0.5513(9) 0.1801(7) 0.0469(15) Uani 1 1 d . . . . .
H6A H 0.2291 0.4845 0.2703 0.056 Uiso 1 1 calc R U . . .
H6B H 0.2216 0.6939 0.1966 0.056 Uiso 1 1 calc R U . . .
C7 C 0.26618(15) 0.5345(9) 0.1085(9) 0.0525(16) Uani 1 1 d . . . . .
H7A H 0.2861 0.6033 0.1629 0.079 Uiso 1 1 calc R U . . .
H7B H 0.2644 0.5958 0.0175 0.079 Uiso 1 1 calc R U . . .
H7C H 0.2732 0.3937 0.0990 0.079 Uiso 1 1 calc R U . . .
C8 C 0.12562(16) 0.1993(9) 0.0115(7) 0.0433(14) Uani 1 1 d . . . . .
H8A H 0.1014 0.1713 -0.0403 0.052 Uiso 1 1 calc R U . . .
H8B H 0.1465 0.2219 -0.0561 0.052 Uiso 1 1 calc R U . . .
C9 C 0.13597(19) 0.0162(9) 0.0971(10) 0.062(2) Uani 1 1 d . . . . .
H9A H 0.1388 -0.0996 0.0368 0.093 Uiso 1 1 calc R U . . .
H9B H 0.1153 -0.0095 0.1634 0.093 Uiso 1 1 calc R U . . .
H9C H 0.1604 0.0400 0.1462 0.093 Uiso 1 1 calc R U . . .


_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 1.969(4) . ?
Cu1 O1 1.969(4) 2 ?
Cu1 N1 2.019(4) . ?
Cu1 N1 2.019(4) 2 ?
Cu1 O3 2.360(4) 1_565 ?
O1 C1 1.266(6) . ?
O2 C1 1.222(6) . ?
O3 Cu1 2.360(4) 1_545 ?
N1 C2 1.484(7) . ?
C2 C3 1.512(7) . ?
C3 C4 1.532(7) . ?
C3 C8 1.546(8) . ?
C4 C5 1.515(7) . ?
C5 C6 1.511(8) . ?
C6 C7 1.521(7) . ?
C8 C9 1.527(9) . ?

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 173.94(18) . 2 ?
O1 Cu1 N1 85.8(2) . . ?
O1 Cu1 N1 94.2(2) 2 . ?
O1 Cu1 N1 94.2(2) . 2 ?
O1 Cu1 N1 85.8(2) 2 2 ?
N1 Cu1 N1 179.5(2) . 2 ?
O1 Cu1 O3 93.03(9) . 1_565 ?
O1 Cu1 O3 93.03(9) 2 1_565 ?
N1 Cu1 O3 90.25(11) . 1_565 ?
N1 Cu1 O3 90.25(11) 2 1_565 ?
C1 O1 Cu1 118.4(3) . . ?
C2 N1 Cu1 118.5(4) . . ?
O2 C1 O1 127.0(6) . . ?
N1 C2 C3 117.0(5) . . ?
C2 C3 C4 109.1(5) . . ?
C2 C3 C8 113.2(4) . . ?
C4 C3 C8 113.1(4) . . ?
C5 C4 C3 117.0(5) . . ?
C6 C5 C4 114.3(5) . . ?
C5 C6 C7 113.7(6) . . ?
C9 C8 C3 114.5(6) . . ?

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 O2 6.2(7) . . . . ?
Cu1 N1 C2 C3 -176.6(3) . . . . ?
N1 C2 C3 C4 174.7(4) . . . . ?
N1 C2 C3 C8 -58.4(6) . . . . ?
C2 C3 C4 C5 177.0(5) . . . . ?
C8 C3 C4 C5 50.0(7) . . . . ?
C3 C4 C5 C6 171.1(5) . . . . ?
C4 C5 C6 C7 172.7(5) . . . . ?
C2 C3 C8 C9 -64.9(7) . . . . ?
C4 C3 C8 C9 59.9(7) . . . . ?

_refine_diff_density_max         0.590
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_Tom14_0m
_database_code_depnum_ccdc_archive 'CCDC 1575193'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2017-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_systematic        
'aquabis-(cis-3,5-dimethylpiperidine)diformatocopper (II)'
_chemical_name_common            
'bis-(cis-3,5-dimethylpiperidine) copper (II) formate monohydrate'
_chemical_formula_moiety         'C16 H34 Cu N2 O5'
_chemical_formula_sum            'C16 H34 Cu N2 O5'
_chemical_formula_weight         398.00
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu 0.34125 1.28947 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration ?
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2
_cell_length_a                   12.5495(11)
_cell_length_b                   11.6952(8)
_cell_length_c                   13.8103(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.169(3)
_cell_angle_gamma                90
_cell_volume                     2015.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.869
_cell_measurement_theta_min      2.387
_exptl_absorpt_coefficient_mu    1.109
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0857 before and 0.0528 after correction.
The Ratio of minimum to maximum transmission is 0.8269.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_recrystallization_method 'slow evaporation from toluene'
_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_pressure         101.325
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.3117
_exptl_crystal_F_000             853.7187
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33541
_diffrn_reflns_theta_full        26.1889
_diffrn_reflns_theta_max         26.19
_diffrn_reflns_theta_min         2.29
_diffrn_measured_fraction_theta_full 0.9938
_diffrn_measured_fraction_theta_max 0.9938
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'X-ray tube'
_diffrn_source_type              'Siemens KFF MO 2K-90'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3360
_reflns_number_total             4024
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.4777
_refine_diff_density_min         -0.3911
_refine_diff_density_rms         0.0868
_refine_ls_d_res_high            0.8052
_refine_ls_d_res_low             8.9032
_refine_ls_goodness_of_fit_ref   0.8777
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4024
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0304
_refine_ls_restrained_S_all      0.8777
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1118
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H10b(0.02)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Cu1 Cu 0.514270(19) 0.27316(2) 0.060563(18) 0.01324(12) Uani 1.000000 .
O3 O 0.43464(12) 0.12666(12) 0.06742(11) 0.0190(3) Uani 1.000000 .
O1 O 0.59292(12) 0.39101(12) -0.00980(10) 0.0149(3) Uani 1.000000 .
O2 O 0.60109(13) 0.25762(13) -0.12425(12) 0.0206(4) Uani 1.000000 .
N1 N 0.37687(15) 0.34926(17) 0.00224(14) 0.0159(4) Uani 1.000000 .
N2 N 0.65194(16) 0.20440(16) 0.12498(15) 0.0167(4) Uani 1.000000 .
C2 C 0.8240(2) 0.2311(2) 0.2307(2) 0.0254(5) Uani 1.000000 .
C15 C 0.61684(17) 0.35489(18) -0.09179(16) 0.0159(5) Uani 1.000000 .
C10 C 0.34435(18) 0.3141(2) -0.09859(17) 0.0208(5) Uani 1.000000 .
C6 C 0.28649(18) 0.3417(2) 0.06139(17) 0.0186(5) Uani 1.000000 .
C1 C 0.7318(2) 0.28743(19) 0.16856(19) 0.0198(5) Uani 1.000000 .
C4 C 0.7980(2) 0.0577(2) 0.12160(19) 0.0267(6) Uani 1.000000 .
C8 C 0.15400(19) 0.3702(2) -0.08359(18) 0.0231(5) Uani 1.000000 .
C7 C 0.18692(18) 0.4076(2) 0.01986(17) 0.0214(5) Uani 1.000000 .
C9 C 0.24686(19) 0.3803(2) -0.14598(17) 0.0230(5) Uani 1.000000 .
C5 C 0.70218(19) 0.11830(19) 0.06625(17) 0.0201(5) Uani 1.000000 .
C3 C 0.8781(2) 0.1445(2) 0.1691(2) 0.0289(6) Uani 1.000000 .
O5 O 0.49016(15) 0.34361(16) 0.20923(13) 0.0220(4) Uani 1.000000 .
O4 O 0.50693(14) 0.05590(14) 0.21004(12) 0.0259(4) Uani 1.000000 .
C16 C 0.4459(2) 0.05220(19) 0.13379(17) 0.0226(5) Uani 1.000000 .
C13 C 0.0983(2) 0.3921(3) 0.0849(2) 0.0339(6) Uani 1.000000 .
C12 C 0.8490(3) -0.0221(2) 0.0535(3) 0.0400(7) Uani 1.000000 .
C11 C 0.9021(2) 0.3222(3) 0.2745(2) 0.0395(7) Uani 1.000000 .
C14 C 0.2154(2) 0.3361(3) -0.2481(2) 0.0337(6) Uani 1.000000 .
H5a H 0.725(2) 0.151(2) 0.0070(19) 0.018(6) Uiso 1.000000 .
H8a H 0.1328(18) 0.294(2) -0.0871(17) 0.006(5) Uiso 1.000000 .
H3a H 0.910(2) 0.177(2) 0.1152(19) 0.020(6) Uiso 1.000000 .
H10a H 0.409(2) 0.317(2) -0.1398(19) 0.024(6) Uiso 1.000000 .
H1a H 0.7594(18) 0.320(2) 0.1204(18) 0.008(6) Uiso 1.000000 .
H1b H 0.701(2) 0.337(2) 0.2059(19) 0.019(7) Uiso 1.000000 .
H6a H 0.268(2) 0.264(2) 0.067(2) 0.026(7) Uiso 1.000000 .
H6b H 0.3065(19) 0.373(2) 0.1290(19) 0.017(6) Uiso 1.000000 .
H14a H 0.199(3) 0.248(3) -0.241(2) 0.048(10) Uiso 1.000000 .
H2 H 0.6321(19) 0.171(2) 0.1665(18) 0.010(6) Uiso 1.000000 .
H16 H 0.399(2) -0.018(2) 0.1239(19) 0.032(7) Uiso 1.000000 .
H1 H 0.391(2) 0.405(2) 0.0003(18) 0.009(7) Uiso 1.000000 .
H9 H 0.266(2) 0.462(2) -0.1581(17) 0.021(6) Uiso 1.000000 .
H14b H 0.282(3) 0.341(3) -0.287(3) 0.062(10) Uiso 1.000000 .
H7 H 0.203(2) 0.480(3) 0.0195(19) 0.029(7) Uiso 1.000000 .
H13a H 0.079(2) 0.313(3) 0.083(2) 0.033(8) Uiso 1.000000 .
H5c H 0.519(2) 0.311(3) 0.249(2) 0.027(8) Uiso 1.000000 .
H4 H 0.7721(17) 0.0031(18) 0.1753(16) 0.008(5) Uiso 1.000000 .
H12a H 0.869(2) 0.024(3) -0.005(2) 0.036(8) Uiso 1.000000 .
H15 H 0.649(2) 0.408(2) -0.1315(18) 0.019(6) Uiso 1.000000 .
H8b H 0.091(2) 0.415(2) -0.1095(18) 0.022(7) Uiso 1.000000 .
H3b H 0.936(3) 0.096(3) 0.214(2) 0.054(10) Uiso 1.000000 .
H14c H 0.150(3) 0.385(3) -0.290(3) 0.065(10) Uiso 1.000000 .
H12b H 0.794(3) -0.080(3) 0.018(3) 0.080(13) Uiso 1.000000 .
H12c H 0.909(3) -0.067(3) 0.091(2) 0.049(9) Uiso 1.000000 .
H13b H 0.125(3) 0.417(3) 0.153(2) 0.046(9) Uiso 1.000000 .
H13c H 0.036(3) 0.435(3) 0.061(2) 0.044(9) Uiso 1.000000 .
H11a H 0.861(3) 0.375(3) 0.313(2) 0.050(9) Uiso 1.000000 .
H11b H 0.925(3) 0.369(3) 0.216(3) 0.063(11) Uiso 1.000000 .
H11c H 0.966(3) 0.284(3) 0.310(3) 0.063(11) Uiso 1.000000 .
H5d H 0.491(2) 0.410(3) 0.227(2) 0.028(8) Uiso 1.000000 .
H2a H 0.798(2) 0.189(2) 0.291(2) 0.022(6) Uiso 1.000000 .
H5b H 0.6474(17) 0.0638(18) 0.0419(15) 0.003(5) Uiso 1.000000 .
H10b H 0.329(2) 0.234(2) -0.095(2) 0.020000 Uiso 1.000000 .


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 O3 1.9908(15) . ?
Cu1 O1 2.0060(14) . ?
Cu1 N1 2.0287(19) . ?
Cu1 N2 2.0230(19) . ?
Cu1 O5 2.2626(17) . ?
O3 C16 1.261(3) . ?
O1 C15 1.274(3) . ?
O2 C15 1.231(3) . ?
N1 C10 1.467(3) . ?
N1 C6 1.470(3) . ?
N2 C1 1.477(3) . ?
N2 C5 1.476(3) . ?
C2 C1 1.515(3) . ?
C2 C3 1.529(4) . ?
C2 C11 1.528(4) . ?
C10 C9 1.534(3) . ?
C6 C7 1.526(3) . ?
C4 C5 1.528(3) . ?
C4 C3 1.527(4) . ?
C4 C12 1.515(4) . ?
C8 C7 1.509(3) . ?
C8 C9 1.527(3) . ?
C7 C13 1.513(3) . ?
C9 C14 1.514(3) . ?
O4 C16 1.234(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
O1 Cu1 O3 152.86(6) . . ?
N1 Cu1 O3 89.25(7) . . ?
N1 Cu1 O1 87.00(7) . . ?
N2 Cu1 O3 92.65(7) . . ?
N2 Cu1 O1 92.56(7) . . ?
N2 Cu1 N1 176.61(8) . . ?
O5 Cu1 O3 98.83(7) . . ?
O5 Cu1 O1 108.06(6) . . ?
O5 Cu1 N1 90.56(7) . . ?
O5 Cu1 N2 86.38(8) . . ?
C16 O3 Cu1 127.67(14) . . ?
C15 O1 Cu1 112.20(13) . . ?
C10 N1 Cu1 113.06(14) . . ?
C6 N1 Cu1 115.25(14) . . ?
C6 N1 C10 110.98(18) . . ?
C1 N2 Cu1 115.34(14) . . ?
C5 N2 Cu1 115.12(14) . . ?
C5 N2 C1 111.18(18) . . ?
C3 C2 C1 109.3(2) . . ?
C11 C2 C1 109.9(2) . . ?
C11 C2 C3 112.2(2) . . ?
O2 C15 O1 125.9(2) . . ?
C9 C10 N1 113.02(18) . . ?
C7 C6 N1 114.22(19) . . ?
C2 C1 N2 112.87(19) . . ?
C3 C4 C5 110.72(19) . . ?
C12 C4 C5 109.7(2) . . ?
C12 C4 C3 111.9(2) . . ?
C9 C8 C7 111.3(2) . . ?
C8 C7 C6 109.83(19) . . ?
C13 C7 C6 109.9(2) . . ?
C13 C7 C8 112.5(2) . . ?
C8 C9 C10 110.0(2) . . ?
C14 C9 C10 109.9(2) . . ?
C14 C9 C8 111.1(2) . . ?
C4 C5 N2 113.63(19) . . ?
C4 C3 C2 111.6(2) . . ?
O4 C16 O3 127.3(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'

