# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_s1
_database_code_depnum_ccdc_archive 'CCDC 1547468'
_audit_update_record             
;
2017-05-02 deposited with the CCDC.
2017-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        Co(CO3)(MeIm)2.2H2O
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H16 Co N4 O5'
_chemical_formula_weight         319.19

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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. 
;

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

_cell_length_a                   17.3114(19)
_cell_length_b                   14.2963(19)
_cell_length_c                   5.2538(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1300.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3949
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      25.65

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_F_000             660
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.343
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6915
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15494
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.751
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1388
_reflns_number_gt                1149
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0578P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1388
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0871
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
O5 O 0.45049(16) 0.7500 0.6503(6) 0.0488(8) Uani 1 2 d S T P . .
H7 H 0.010(3) 0.7500 0.188(11) 0.073 Uiso 1 2 d S U P . .
H8 H 0.071(3) 0.7500 0.333(10) 0.073 Uiso 1 2 d S U P . .
O4 O 0.01998(18) 0.7500 0.3401(7) 0.0752(13) Uani 1 2 d S T P . .
H10 H 0.464(4) 0.7500 0.783(14) 0.113 Uiso 1 2 d S U P . .
H9 H 0.406(4) 0.7500 0.642(13) 0.113 Uiso 1 2 d S U P . .
Co1 Co 0.26441(2) 0.7500 0.06052(7) 0.01958(16) Uani 1 2 d S T P . .
O1 O 0.19657(13) 0.7500 -0.2487(4) 0.0275(5) Uani 1 2 d S T P . .
O2 O 0.29871(13) 0.7500 0.4903(4) 0.0253(5) Uani 1 2 d S T P . .
O3 O 0.18209(11) 0.7500 0.3300(4) 0.0220(5) Uani 1 2 d S T P . .
N2 N 0.31950(11) 0.62479(14) 0.0323(3) 0.0246(4) Uani 1 1 d . . . . .
C1 C 0.22643(17) 0.7500 -0.4712(5) 0.0182(7) Uani 1 2 d S T P . .
C2 C 0.36735(13) 0.58459(17) 0.1950(4) 0.0271(5) Uani 1 1 d . . . . .
H2 H 0.3861 0.6133 0.3414 0.033 Uiso 1 1 calc R U . . .
C4 C 0.34718(15) 0.48005(18) -0.0998(4) 0.0310(6) Uani 1 1 d . . . . .
H4 H 0.3486 0.4252 -0.1951 0.037 Uiso 1 1 calc R U . . .
N1 N 0.38551(11) 0.49738(14) 0.1229(4) 0.0283(5) Uani 1 1 d . . . . .
C5 C 0.43538(16) 0.4314(2) 0.2568(6) 0.0444(7) Uani 1 1 d . . . . .
H5A H 0.4473 0.4555 0.4228 0.067 Uiso 1 1 calc R U . . .
H5B H 0.4823 0.4228 0.1623 0.067 Uiso 1 1 calc R U . . .
H5C H 0.4093 0.3724 0.2735 0.067 Uiso 1 1 calc R U . . .
C3 C 0.30702(14) 0.55836(17) -0.1535(4) 0.0291(5) Uani 1 1 d . . . . .
H3 H 0.2755 0.5664 -0.2952 0.035 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
Co1 O1 2.005(2) . ?
Co1 O3 2.009(2) . ?
Co1 N2 2.034(2) . ?
Co1 N2 2.034(2) 7_575 ?
Co1 O2 2.335(2) . ?
O1 C1 1.278(3) . ?
O2 C1 1.267(4) 1_556 ?
O3 C1 1.296(4) 1_556 ?
N2 C2 1.322(3) . ?
N2 C3 1.379(3) . ?
C1 O2 1.267(4) 1_554 ?
C1 O3 1.296(4) 1_554 ?
C2 N1 1.340(3) . ?
C4 C3 1.348(3) . ?
C4 N1 1.368(3) . ?
N1 C5 1.460(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 Co1 O3 98.96(9) . . ?
O1 Co1 N2 102.45(6) . . ?
O3 Co1 N2 112.58(6) . . ?
O1 Co1 N2 102.45(6) . 7_575 ?
O3 Co1 N2 112.58(6) . 7_575 ?
N2 Co1 N2 123.34(11) . 7_575 ?
O1 Co1 O2 158.88(9) . . ?
O3 Co1 O2 59.92(8) . . ?
N2 Co1 O2 87.20(6) . . ?
N2 Co1 O2 87.20(6) 7_575 . ?
C1 O1 Co1 120.3(2) . . ?
C1 O2 Co1 84.43(16) 1_556 . ?
C1 O3 Co1 98.50(17) 1_556 . ?
C2 N2 C3 104.9(2) . . ?
C2 N2 Co1 129.02(16) . . ?
C3 N2 Co1 125.75(15) . . ?
O2 C1 O1 123.0(3) 1_554 . ?
O2 C1 O3 117.2(2) 1_554 1_554 ?
O1 C1 O3 119.8(3) . 1_554 ?
N2 C2 N1 111.6(2) . . ?
C3 C4 N1 106.2(2) . . ?
C2 N1 C4 107.2(2) . . ?
C2 N1 C5 127.1(2) . . ?
C4 N1 C5 125.6(2) . . ?
C4 C3 N2 110.1(2) . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_s1
_database_code_depnum_ccdc_archive 'CCDC 1547467'
_audit_update_record             
;
2017-05-02 deposited with the CCDC.
2017-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        Zn(CO3)(MeIm)2.2H2O
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H16 N4 O5 Zn'
_chemical_formula_weight         325.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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. 
;

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

_cell_length_a                   17.309(2)
_cell_length_b                   14.2310(16)
_cell_length_c                   5.2931(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1303.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9765
_cell_measurement_theta_min      5.98
_cell_measurement_theta_max      74.30

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.860
_shelx_estimated_absorpt_T_min   0.674
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6312
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23584
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         5.984
_diffrn_reflns_theta_max         74.292
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1388
_reflns_number_gt                1230
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0734P)²+0.4381P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1388
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0.001
_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
O4 O 0.9523(2) 0.7500 0.6477(7) 0.0628(10) Uani 1 2 d S T P . .
H7 H 0.905(4) 0.7500 0.638(15) 0.094 Uiso 1 2 d S U P . .
H8 H 0.958(5) 0.7500 0.774(16) 0.094 Uiso 1 2 d S U P . .
O5 O 1.0224(2) 0.7500 1.1588(8) 0.0858(15) Uani 1 2 d S T P . .
H9 H 1.079(6) 0.7500 1.152(18) 0.129 Uiso 1 2 d S U P . .
H10 H 1.015(6) 0.7500 1.29(2) 0.129 Uiso 1 2 d S U P . .
Zn1 Zn 0.76250(3) 0.7500 0.03921(9) 0.0313(2) Uani 1 2 d S T P . .
O1 O 0.69360(14) 0.7500 -0.2619(5) 0.0364(6) Uani 1 2 d S T P . .
O2 O 0.79947(16) 0.7500 -0.5013(5) 0.0356(6) Uani 1 2 d S T P . .
O3 O 0.68470(14) 0.7500 0.3194(4) 0.0318(5) Uani 1 2 d S T P . .
N2 N 0.81777(13) 0.62533(14) 0.0205(4) 0.0338(5) Uani 1 1 d . . . . .
C1 C 0.7276(2) 0.7500 -0.4779(6) 0.0294(7) Uani 1 2 d S T P . .
N1 N 0.88507(13) 0.49921(14) 0.1172(5) 0.0380(5) Uani 1 1 d . . . . .
C3 C 0.80670(16) 0.55816(17) -0.1633(5) 0.0387(6) Uani 1 1 d . . . . .
H3 H 0.7760 0.5654 -0.3061 0.046 Uiso 1 1 calc R U . . .
C4 C 0.84738(17) 0.48017(18) -0.1041(5) 0.0415(6) Uani 1 1 d . . . . .
H4 H 0.8494 0.4245 -0.1959 0.050 Uiso 1 1 calc R U . . .
C2 C 0.86573(15) 0.58724(17) 0.1852(5) 0.0363(6) Uani 1 1 d . . . . .
H2 H 0.8838 0.6173 0.3295 0.044 Uiso 1 1 calc R U . . .
C5 C 0.93447(18) 0.4340(2) 0.2563(7) 0.0533(8) Uani 1 1 d . . . . .
H5A H 0.9467 0.4602 0.4186 0.080 Uiso 1 1 calc R U . . .
H5B H 0.9813 0.4236 0.1631 0.080 Uiso 1 1 calc R U . . .
H5C H 0.9079 0.3754 0.2786 0.080 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
Zn1 O1 1.991(3) . ?
Zn1 O3 2.003(2) . ?
Zn1 N2 2.018(2) 7_575 ?
Zn1 N2 2.018(2) . ?
O1 C1 1.286(4) . ?
O2 C1 1.250(5) . ?
O3 C1 1.305(4) 1_556 ?
N2 C2 1.320(3) . ?
N2 C3 1.377(3) . ?
C1 O3 1.305(4) 1_554 ?
N1 C2 1.346(3) . ?
N1 C4 1.368(4) . ?
N1 C5 1.461(4) . ?
C3 C4 1.351(4) . ?

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 Zn1 O3 100.95(10) . . ?
O1 Zn1 N2 104.17(7) . 7_575 ?
O3 Zn1 N2 110.79(6) . 7_575 ?
O1 Zn1 N2 104.17(7) . . ?
O3 Zn1 N2 110.79(6) . . ?
N2 Zn1 N2 123.08(13) 7_575 . ?
C1 O1 Zn1 116.0(2) . . ?
C1 O3 Zn1 103.1(2) 1_556 . ?
C2 N2 C3 105.6(2) . . ?
C2 N2 Zn1 128.79(18) . . ?
C3 N2 Zn1 125.37(18) . . ?
O2 C1 O1 122.9(3) . . ?
O2 C1 O3 119.0(3) . 1_554 ?
O1 C1 O3 118.1(3) . 1_554 ?
C2 N1 C4 107.2(2) . . ?
C2 N1 C5 127.0(3) . . ?
C4 N1 C5 125.8(2) . . ?
C4 C3 N2 109.5(2) . . ?
C3 C4 N1 106.5(2) . . ?
N2 C2 N1 111.2(2) . . ?

_refine_diff_density_max         0.790
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_s1
_database_code_depnum_ccdc_archive 'CCDC 1510901'
_audit_update_record             
;
2016-10-20 deposited with the CCDC.
2017-05-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_SYMMS02_s1                  
;
PROBLEM: The unit-cell lengths a and c should not be equal for a
RESPONSE: It appears that the identical a and c unit-cell lengths are entirely coincidental.
;
# Added during the CSD deposition process: Thursday 20 October 2016 04:48 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        Cu(CO3)(1-methylimidazole)3
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H18 Cu N6 O3'
_chemical_formula_weight         369.87

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'

_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. 
;

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'

_cell_length_a                   13.232(4)
_cell_length_b                   8.981(3)
_cell_length_c                   13.232(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.292(4)
_cell_angle_gamma                90
_cell_volume                     1569.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7828
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      25.58

_exptl_crystal_description       Fragment
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             764
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.416
_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6205
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'Bruker AXScale'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20773
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.742
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3594
_reflns_number_gt                3373
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.987
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.998

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0277P)²+1.0692P] 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_abs_structure_details 
; 
 Flack x determined using 1573 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.002(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3594
_refine_ls_number_parameters     211
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0628
_refine_ls_wR_factor_gt          0.0615
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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_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
Cu Cu 0.12670(3) -0.10515(4) 0.37175(3) 0.01776(11) Uani 1 1 d . . . . .
O1 O 0.2101(2) -0.1922(4) 0.2685(2) 0.0321(7) Uani 1 1 d . . . . .
O2 O 0.04616(19) -0.1875(3) 0.2525(2) 0.0268(6) Uani 1 1 d . . . . .
O3 O 0.1328(2) -0.2873(3) 0.12716(18) 0.0269(6) Uani 1 1 d . . . . .
N1 N 0.0093(2) -0.1079(3) 0.4625(2) 0.0194(6) Uani 1 1 d . . . . .
N3 N -0.0883(2) -0.0913(3) 0.5917(2) 0.0221(7) Uani 1 1 d . . . . .
N7 N 0.2391(2) -0.1093(3) 0.4803(2) 0.0202(6) Uani 1 1 d . . . . .
N9 N 0.3509(2) -0.0591(4) 0.6053(2) 0.0202(6) Uani 1 1 d . . . . .
N13 N 0.1268(3) 0.1387(3) 0.3416(2) 0.0218(7) Uani 1 1 d . . . . .
N15 N 0.0986(2) 0.3768(3) 0.3748(3) 0.0228(7) Uani 1 1 d . . . . .
C2 C 0.0058(3) -0.0736(4) 0.5598(3) 0.0208(8) Uani 1 1 d . . . . .
H2 H 0.0623 -0.0409 0.6015 0.025 Uiso 1 1 calc R U . . .
C4 C -0.1491(3) -0.1360(4) 0.5108(3) 0.0243(8) Uani 1 1 d . . . . .
H4 H -0.2197 -0.1558 0.5100 0.029 Uiso 1 1 calc R U . . .
C5 C -0.0884(3) -0.1467(4) 0.4309(3) 0.0219(8) Uani 1 1 d . . . . .
H5 H -0.1100 -0.1762 0.3641 0.026 Uiso 1 1 calc R U . . .
C6 C -0.1202(3) -0.0622(5) 0.6946(3) 0.0294(9) Uani 1 1 d . . . . .
H6A H -0.1486 0.0383 0.6977 0.044 Uiso 1 1 calc R U . . .
H6B H -0.0616 -0.0705 0.7430 0.044 Uiso 1 1 calc R U . . .
H6C H -0.1717 -0.1352 0.7116 0.044 Uiso 1 1 calc R U . . .
C8 C 0.2682(3) -0.0105(4) 0.5501(3) 0.0192(7) Uani 1 1 d . . . . .
H8 H 0.2355 0.0821 0.5602 0.023 Uiso 1 1 calc R U . . .
C10 C 0.3758(3) -0.1964(5) 0.5686(3) 0.0251(8) Uani 1 1 d . . . . .
H10 H 0.4305 -0.2579 0.5924 0.030 Uiso 1 1 calc R U . . .
C11 C 0.3068(3) -0.2267(4) 0.4920(3) 0.0265(8) Uani 1 1 d . . . . .
H11 H 0.3050 -0.3150 0.4523 0.032 Uiso 1 1 calc R U . . .
C12 C 0.4071(3) 0.0203(5) 0.6871(3) 0.0331(10) Uani 1 1 d . . . . .
H12A H 0.3596 0.0739 0.7281 0.050 Uiso 1 1 calc R U . . .
H12B H 0.4537 0.0914 0.6583 0.050 Uiso 1 1 calc R U . . .
H12C H 0.4457 -0.0513 0.7299 0.050 Uiso 1 1 calc R U . . .
C14 C 0.0858(3) 0.2330(4) 0.4028(3) 0.0223(8) Uani 1 1 d . . . . .
H14 H 0.0510 0.2039 0.4604 0.027 Uiso 1 1 calc R U . . .
C16 C 0.1510(3) 0.3719(4) 0.2885(3) 0.0274(9) Uani 1 1 d . . . . .
H16 H 0.1711 0.4546 0.2497 0.033 Uiso 1 1 calc R U . . .
C17 C 0.1687(3) 0.2264(5) 0.2694(3) 0.0268(8) Uani 1 1 d . . . . .
H17 H 0.2047 0.1902 0.2144 0.032 Uiso 1 1 calc R U . . .
C18 C 0.0646(4) 0.5067(4) 0.4297(3) 0.0347(10) Uani 1 1 d . . . . .
H18A H 0.0997 0.5100 0.4969 0.052 Uiso 1 1 calc R U . . .
H18B H -0.0086 0.5000 0.4368 0.052 Uiso 1 1 calc R U . . .
H18C H 0.0799 0.5973 0.3922 0.052 Uiso 1 1 calc R U . . .
C19 C 0.1298(3) -0.2265(4) 0.2109(3) 0.0177(7) Uani 1 1 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
Cu O1 1.966(3) . ?
Cu O2 1.995(3) . ?
Cu N7 2.007(3) . ?
Cu N1 2.018(3) . ?
Cu N13 2.226(3) . ?
Cu C19 2.394(4) . ?
O1 C19 1.309(5) . ?
O2 C19 1.312(4) . ?
O3 C19 1.237(4) . ?
N1 C2 1.327(5) . ?
N1 C5 1.380(5) . ?
N3 C2 1.347(5) . ?
N3 C4 1.363(5) . ?
N3 C6 1.472(5) . ?
N7 C8 1.323(5) . ?
N7 C11 1.387(5) . ?
N9 C8 1.352(5) . ?
N9 C10 1.372(5) . ?
N9 C12 1.463(5) . ?
N13 C14 1.311(5) . ?
N13 C17 1.379(5) . ?
N15 C14 1.356(5) . ?
N15 C16 1.370(5) . ?
N15 C18 1.459(5) . ?
C4 C5 1.368(5) . ?
C10 C11 1.352(6) . ?
C16 C17 1.354(6) . ?

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 Cu O2 66.35(11) . . ?
O1 Cu N7 93.86(12) . . ?
O2 Cu N7 154.03(12) . . ?
O1 Cu N1 152.94(13) . . ?
O2 Cu N1 94.09(11) . . ?
N7 Cu N1 97.95(13) . . ?
O1 Cu N13 105.08(13) . . ?
O2 Cu N13 103.23(12) . . ?
N7 Cu N13 97.97(12) . . ?
N1 Cu N13 97.30(12) . . ?
O1 Cu C19 33.12(12) . . ?
O2 Cu C19 33.23(11) . . ?
N7 Cu C19 125.29(12) . . ?
N1 Cu C19 125.21(12) . . ?
N13 Cu C19 106.76(11) . . ?
C19 O1 Cu 91.7(2) . . ?
C19 O2 Cu 90.4(2) . . ?
C2 N1 C5 105.6(3) . . ?
C2 N1 Cu 130.2(3) . . ?
C5 N1 Cu 124.2(2) . . ?
C2 N3 C4 107.7(3) . . ?
C2 N3 C6 126.0(3) . . ?
C4 N3 C6 126.2(3) . . ?
C8 N7 C11 105.7(3) . . ?
C8 N7 Cu 131.4(3) . . ?
C11 N7 Cu 122.8(2) . . ?
C8 N9 C10 107.6(3) . . ?
C8 N9 C12 127.1(3) . . ?
C10 N9 C12 125.3(3) . . ?
C14 N13 C17 104.8(3) . . ?
C14 N13 Cu 121.4(2) . . ?
C17 N13 Cu 133.7(2) . . ?
C14 N15 C16 105.9(3) . . ?
C14 N15 C18 125.3(3) . . ?
C16 N15 C18 128.7(3) . . ?
N1 C2 N3 111.1(3) . . ?
N3 C4 C5 106.3(3) . . ?
C4 C5 N1 109.2(3) . . ?
N7 C8 N9 110.8(3) . . ?
C11 C10 N9 106.3(3) . . ?
C10 C11 N7 109.6(3) . . ?
N13 C14 N15 112.6(3) . . ?
C17 C16 N15 106.7(3) . . ?
C16 C17 N13 109.9(3) . . ?
O3 C19 O1 124.0(3) . . ?
O3 C19 O2 124.4(3) . . ?
O1 C19 O2 111.6(3) . . ?
O3 C19 Cu 178.7(3) . . ?
O1 C19 Cu 55.18(17) . . ?
O2 C19 Cu 56.42(17) . . ?

_refine_diff_density_max         0.488
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.053

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'crystallization during formation'
