# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_HK29
_audit_block_doi                 10.5517/cc130pyr
_database_code_depnum_ccdc_archive 'CCDC 1013574'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.ica.2015.01.046 2015
_audit_update_record             
;
2014-07-12 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'pyridine-2,6-dicarboxylato-2,6-bis(hydroxymethyl)pyridine-nickel(II) monohydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N2 Ni O7'
_chemical_formula_weight         380.98

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'
Ni Ni 0.3393 1.1124 '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'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.5850(10)
_cell_length_b                   25.608(4)
_cell_length_c                   8.6560(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.730(10)
_cell_angle_gamma                90
_cell_volume                     1449.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      4.20
_cell_measurement_theta_max      8.65

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    1.381
_shelx_estimated_absorpt_T_min   0.491
_shelx_estimated_absorpt_T_max   0.742
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.51
_exptl_absorpt_correction_T_max  0.76
_exptl_absorpt_process_details   '(XEMP; Siemens, 1994)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Siemens P4 diffractometer'
_diffrn_measurement_method       '2θ/ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        1.0
_diffrn_reflns_number            3876
_diffrn_reflns_av_unetI/netI     0.1651
_diffrn_reflns_av_R_equivalents  0.1275
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.207
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2942
_reflns_number_gt                1599
_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       'XSCANS (Siemens, 1994)'
_computing_cell_refinement       XSCANS
_computing_data_reduction        XSCANS
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2008)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  ?

_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)+(0.0364P)²+0.6202P] 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         2942
_refine_ls_number_parameters     217
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1499
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.1431
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.015
_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
Ni1 Ni 0.40173(12) 0.61400(3) 0.79449(10) 0.0213(2) Uani 1 1 d . . . . .
O1 O 0.1435(6) 0.66360(18) 0.7895(5) 0.0293(11) Uani 1 1 d . . . . .
O2 O 0.0272(7) 0.7328(2) 0.9112(6) 0.0396(13) Uani 1 1 d . . . . .
O3 O 0.7100(6) 0.58889(18) 0.8668(5) 0.0288(11) Uani 1 1 d . . . . .
O4 O 0.9701(6) 0.60369(17) 1.0560(5) 0.0292(11) Uani 1 1 d . . . . .
O5 O 0.2811(6) 0.55988(17) 0.9433(5) 0.0246(10) Uani 1 1 d . . . . .
H5O H 0.1714 0.5728 0.9588 0.037 Uiso 1 1 d R U . . .
O6 O 0.4772(7) 0.64599(18) 0.5803(5) 0.0331(12) Uani 1 1 d . . . . .
H6O H 0.5935 0.6536 0.5633 0.050 Uiso 1 1 d R U . . .
N1 N 0.4903(7) 0.66348(19) 0.9619(6) 0.0193(11) Uani 1 1 d . . . . .
N2 N 0.3036(7) 0.5583(2) 0.6432(6) 0.0234(12) Uani 1 1 d . . . . .
C1 C 0.3574(9) 0.6998(2) 0.9994(7) 0.0215(14) Uani 1 1 d . . . . .
C2 C 0.4121(10) 0.7335(3) 1.1221(8) 0.0271(15) Uani 1 1 d . . . . .
H2 H 0.3207 0.7588 1.1485 0.033 Uiso 1 1 calc R U . . .
C3 C 0.6057(11) 0.7293(3) 1.2057(8) 0.0313(15) Uani 1 1 d . . . . .
H3 H 0.6453 0.7522 1.2870 0.038 Uiso 1 1 calc R U . . .
C4 C 0.7393(10) 0.6907(3) 1.1670(8) 0.0293(16) Uani 1 1 d . . . . .
H4 H 0.8679 0.6871 1.2231 0.035 Uiso 1 1 calc R U . . .
C5 C 0.6780(9) 0.6580(2) 1.0447(7) 0.0193(14) Uani 1 1 d . . . . .
C6 C 0.1562(9) 0.6996(3) 0.8941(7) 0.0230(15) Uani 1 1 d . . . . .
C7 C 0.7970(8) 0.6134(3) 0.9832(7) 0.0209(13) Uani 1 1 d . . . . .
C8 C 0.3179(9) 0.5648(3) 0.4887(7) 0.0242(15) Uani 1 1 d . . . . .
C9 C 0.2759(9) 0.5242(3) 0.3877(8) 0.0320(18) Uani 1 1 d . . . . .
H9 H 0.2811 0.5292 0.2818 0.038 Uiso 1 1 calc R U . . .
C10 C 0.2255(9) 0.4755(3) 0.4420(9) 0.0360(19) Uani 1 1 d . . . . .
H10 H 0.2011 0.4476 0.3738 0.043 Uiso 1 1 calc R U . . .
C11 C 0.2119(9) 0.4690(3) 0.6005(9) 0.0335(18) Uani 1 1 d . . . . .
H11 H 0.1792 0.4367 0.6400 0.040 Uiso 1 1 calc R U . . .
C12 C 0.2486(9) 0.5121(2) 0.6985(8) 0.0253(15) Uani 1 1 d . . . . .
C13 C 0.2359(11) 0.5105(3) 0.8725(8) 0.0342(18) Uani 1 1 d . . . . .
H13A H 0.0994 0.4999 0.8909 0.041 Uiso 1 1 calc R U . . .
H13B H 0.3315 0.4847 0.9200 0.041 Uiso 1 1 calc R U . . .
C14 C 0.3772(10) 0.6195(3) 0.4477(7) 0.0342(18) Uani 1 1 d . . . . .
H14A H 0.4677 0.6181 0.3671 0.041 Uiso 1 1 calc R U . . .
H14B H 0.2557 0.6388 0.4073 0.041 Uiso 1 1 calc R U . . .
O1W O 0.8593(7) 0.6701(2) 0.5388(5) 0.0453(14) Uani 1 1 d D . . . .
H1WA H 0.8633 0.7016 0.5222 0.068 Uiso 1 1 d DR U . . .
H1WB H 0.9328 0.6615 0.6178 0.068 Uiso 1 1 d DR 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
Ni1 N1 1.962(5) . y
Ni1 N2 1.992(5) . y
Ni1 O5 2.110(4) . y
Ni1 O1 2.119(4) . y
Ni1 O6 2.138(4) . y
Ni1 O3 2.151(4) . y
O1 C6 1.288(7) . ?
O2 C6 1.224(7) . ?
O3 C7 1.266(7) . ?
O4 C7 1.261(6) . ?
O5 C13 1.421(8) . ?
O5 H5O 0.8199 . ?
O6 C14 1.426(7) . ?
O6 H6O 0.8201 . ?
N1 C1 1.343(7) . ?
N1 C5 1.361(7) . ?
N2 C12 1.342(8) . ?
N2 C8 1.362(8) . ?
C1 C2 1.383(8) . ?
C1 C6 1.518(8) . ?
C2 C3 1.395(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(8) . ?
C4 H4 0.9300 . ?
C5 C7 1.515(8) . ?
C8 C9 1.367(9) . ?
C8 C14 1.507(9) . ?
C9 C10 1.386(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.395(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.518(9) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
O1W H1WA 0.8200 . ?
O1W H1WB 0.8201 . ?

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
N1 Ni1 N2 173.5(2) . . y
N1 Ni1 O5 94.2(2) . . y
N2 Ni1 O5 79.3(2) . . y
N1 Ni1 O1 78.3(2) . . y
N2 Ni1 O1 102.6(2) . . y
O5 Ni1 O1 92.7(2) . . y
N1 Ni1 O6 108.3(2) . . y
N2 Ni1 O6 78.2(2) . . y
O5 Ni1 O6 157.4(2) . . y
O1 Ni1 O6 91.2(2) . . y
N1 Ni1 O3 77.8(2) . . y
N2 Ni1 O3 101.5(2) . . y
O5 Ni1 O3 92.1(2) . . y
O1 Ni1 O3 155.9(2) . . y
O6 Ni1 O3 93.4(2) . . y
C6 O1 Ni1 115.4(4) . . ?
C7 O3 Ni1 114.0(4) . . ?
C13 O5 Ni1 113.3(4) . . ?
C13 O5 H5O 106.6 . . ?
Ni1 O5 H5O 103.7 . . ?
C14 O6 Ni1 112.5(4) . . ?
C14 O6 H6O 108.8 . . ?
Ni1 O6 H6O 124.3 . . ?
C1 N1 C5 121.4(5) . . ?
C1 N1 Ni1 118.7(4) . . ?
C5 N1 Ni1 119.7(4) . . ?
C12 N2 C8 120.8(6) . . ?
C12 N2 Ni1 118.5(4) . . ?
C8 N2 Ni1 120.2(4) . . ?
N1 C1 C2 120.0(5) . . ?
N1 C1 C6 113.6(5) . . ?
C2 C1 C6 126.4(6) . . ?
C1 C2 C3 119.3(6) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 119.7(6) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 118.8(6) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 120.6(6) . . ?
N1 C5 C7 111.6(5) . . ?
C4 C5 C7 127.8(5) . . ?
O2 C6 O1 126.4(6) . . ?
O2 C6 C1 119.6(6) . . ?
O1 C6 C1 113.9(5) . . ?
O4 C7 O3 126.7(6) . . ?
O4 C7 C5 116.6(5) . . ?
O3 C7 C5 116.7(5) . . ?
N2 C8 C9 120.2(6) . . ?
N2 C8 C14 113.3(6) . . ?
C9 C8 C14 126.5(6) . . ?
C8 C9 C10 120.4(7) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 119.1(7) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 118.5(7) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
N2 C12 C11 121.0(6) . . ?
N2 C12 C13 115.2(6) . . ?
C11 C12 C13 123.8(6) . . ?
O5 C13 C12 111.8(5) . . ?
O5 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
O5 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
O6 C14 C8 111.1(5) . . ?
O6 C14 H14A 109.4 . . ?
C8 C14 H14A 109.4 . . ?
O6 C14 H14B 109.4 . . ?
C8 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
H1WA O1W H1WB 112.4 . . ?

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
C5 N1 C1 C2 1.6(9) . . . . ?
Ni1 N1 C1 C2 176.8(5) . . . . ?
C5 N1 C1 C6 -179.6(5) . . . . ?
Ni1 N1 C1 C6 -4.5(7) . . . . ?
N1 C1 C2 C3 0.0(10) . . . . ?
C6 C1 C2 C3 -178.6(6) . . . . ?
C1 C2 C3 C4 -1.3(10) . . . . ?
C2 C3 C4 C5 1.1(10) . . . . ?
C1 N1 C5 C4 -1.9(9) . . . . ?
Ni1 N1 C5 C4 -177.0(5) . . . . ?
C1 N1 C5 C7 178.3(5) . . . . ?
Ni1 N1 C5 C7 3.2(7) . . . . ?
C3 C4 C5 N1 0.5(10) . . . . ?
C3 C4 C5 C7 -179.7(6) . . . . ?
Ni1 O1 C6 O2 178.9(5) . . . . ?
Ni1 O1 C6 C1 1.0(7) . . . . ?
N1 C1 C6 O2 -176.0(6) . . . . ?
C2 C1 C6 O2 2.7(10) . . . . ?
N1 C1 C6 O1 2.1(8) . . . . ?
C2 C1 C6 O1 -179.3(6) . . . . ?
Ni1 O3 C7 O4 173.9(5) . . . . ?
Ni1 O3 C7 C5 -3.9(7) . . . . ?
N1 C5 C7 O4 -177.2(5) . . . . ?
C4 C5 C7 O4 3.0(9) . . . . ?
N1 C5 C7 O3 0.8(8) . . . . ?
C4 C5 C7 O3 -179.0(6) . . . . ?
C12 N2 C8 C9 0.1(8) . . . . ?
Ni1 N2 C8 C9 171.4(4) . . . . ?
C12 N2 C8 C14 178.8(5) . . . . ?
Ni1 N2 C8 C14 -9.9(7) . . . . ?
N2 C8 C9 C10 -2.3(9) . . . . ?
C14 C8 C9 C10 179.2(6) . . . . ?
C8 C9 C10 C11 2.0(9) . . . . ?
C9 C10 C11 C12 0.4(9) . . . . ?
C8 N2 C12 C11 2.4(9) . . . . ?
Ni1 N2 C12 C11 -169.1(4) . . . . ?
C8 N2 C12 C13 -179.2(5) . . . . ?
Ni1 N2 C12 C13 9.4(7) . . . . ?
C10 C11 C12 N2 -2.6(9) . . . . ?
C10 C11 C12 C13 179.1(6) . . . . ?
Ni1 O5 C13 C12 -10.6(7) . . . . ?
N2 C12 C13 O5 1.5(8) . . . . ?
C11 C12 C13 O5 179.8(6) . . . . ?
Ni1 O6 C14 C8 -23.3(6) . . . . ?
N2 C8 C14 O6 21.8(7) . . . . ?
C9 C8 C14 O6 -159.6(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5O O4 0.82 1.83 2.622(6) 162 1_455
O6 H6O O1W 0.82 1.84 2.656(6) 176 .
O1W H1WB O1 0.82 1.91 2.700(6) 161 1_655

_refine_diff_density_max         0.669
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.117

_shelxl_version_number           2014-3

