# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 'picolinic acid magnesium nitrate tetrahydrate'
;
_chemical_name_common            ?
_chemical_melting_point          353-364
_chemical_formula_moiety         'C12 H14 Mg N2 O6, 2(N O3), 2(H2 O)'
_chemical_formula_sum            'C12 H18 Mg N4 O14'
_chemical_formula_weight         466.61

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'
Mg Mg 0.0486 0.0363 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   4.7079(4)
_cell_length_b                   7.0524(8)
_cell_length_c                   14.1691(17)
_cell_angle_alpha                94.124(4)
_cell_angle_beta                 91.235(3)
_cell_angle_gamma                102.963(3)
_cell_volume                     456.92(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10795
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.48

_exptl_crystal_description       cuboid
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_F_000             242
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.186
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  
; 
'Rigaku R-AXIS RAPID IP Image Plate diffractometer' 
;
_diffrn_measurement_method       'profile data from \\w-scans'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            10795
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.201
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2072
_reflns_number_gt                1805
_reflns_threshold_expression     'I > 2\\s(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       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
'ORTEP-3: Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.'
_computing_publication_material  
;    
enCIFer: Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, 
M. (2004). J. Appl. Cryst. 37, 335-338. 
;

_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/[\\s²(Fo²)+(0.0403P)²+0.1137P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2072
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0751
_refine_ls_wR_factor_gt          0.0732
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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
Mg1 Mg 0.5000 0.0000 0.0000 0.01281(14) Uani 1 2 d S . P . .
O1 O 0.23464(17) -0.01210(12) -0.11883(6) 0.01656(19) Uani 1 1 d . . . . .
N1 N 0.1144(2) -0.07654(14) -0.30413(7) 0.0141(2) Uani 1 1 d . . . . .
H1 H 0.271(3) 0.014(2) -0.2812(10) 0.019(4) Uiso 1 1 d . . . . .
C1 C -0.0891(2) -0.15548(16) -0.24393(8) 0.0137(2) Uani 1 1 d . . . . .
C2 C -0.3353(2) -0.28980(17) -0.27902(8) 0.0158(2) Uani 1 1 d . . . . .
H2 H -0.474(3) -0.344(2) -0.2367(10) 0.016(3) Uiso 1 1 d . . . . .
C3 C -0.3677(3) -0.34231(18) -0.37602(8) 0.0178(2) Uani 1 1 d . . . . .
H3 H -0.541(3) -0.440(2) -0.3997(11) 0.024(4) Uiso 1 1 d . . . . .
C4 C -0.1544(3) -0.25870(18) -0.43612(8) 0.0182(2) Uani 1 1 d . . . . .
H4 H -0.174(3) -0.291(2) -0.5034(11) 0.021(4) Uiso 1 1 d . . . . .
C5 C 0.0873(3) -0.12346(18) -0.39797(8) 0.0164(2) Uani 1 1 d . . . . .
H5 H 0.248(3) -0.057(2) -0.4360(10) 0.020(4) Uiso 1 1 d . . . . .
C6 C -0.0266(2) -0.09127(16) -0.13964(8) 0.0135(2) Uani 1 1 d . . . . .
O2 O 0.66802(19) 0.20825(14) -0.40563(6) 0.0234(2) Uani 1 1 d . . . . .
O3 O 0.64176(18) 0.20237(13) -0.25278(6) 0.0203(2) Uani 1 1 d . . . . .
O4 O 1.03755(18) 0.35877(13) -0.31375(6) 0.0207(2) Uani 1 1 d . . . . .
N2 N 0.7816(2) 0.25651(15) -0.32451(7) 0.0157(2) Uani 1 1 d . . . . .
O5 O 0.30890(18) -0.28478(13) 0.02605(6) 0.01632(19) Uani 1 1 d . . . . .
H5A H 0.283(4) -0.361(3) -0.0221(13) 0.030(4) Uiso 1 1 d . . . . .
H5B H 0.154(4) -0.312(3) 0.0553(14) 0.040(5) Uiso 1 1 d . . . . .
O6 O 0.23704(17) 0.12639(12) 0.08722(6) 0.01710(19) Uani 1 1 d . . . . .
O7 O -0.20293(19) -0.41637(13) 0.11886(6) 0.01820(19) Uani 1 1 d . . . . .
H7A H -0.154(4) -0.392(3) 0.1773(14) 0.033(4) Uiso 1 1 d . . . . .
H7B H -0.328(4) -0.351(3) 0.1101(13) 0.041(5) Uiso 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
Mg1 O1 2.0601(8) . ?
Mg1 O1 2.0601(8) 2_655 ?
Mg1 O6 2.0632(8) 2_655 ?
Mg1 O6 2.0632(8) . ?
Mg1 O5 2.0711(9) . ?
Mg1 O5 2.0711(9) 2_655 ?
O1 C6 1.2508(14) . ?
N1 C5 1.3431(15) . ?
N1 C1 1.3489(14) . ?
N1 H1 0.896(16) . ?
C1 C2 1.3796(16) . ?
C1 C6 1.5166(15) . ?
C2 C3 1.3934(16) . ?
C2 H2 0.930(15) . ?
C3 C4 1.3874(17) . ?
C3 H3 0.977(16) . ?
C4 C5 1.3817(17) . ?
C4 H4 0.961(15) . ?
C5 H5 0.987(15) . ?
C6 O6 1.2419(14) 2 ?
O2 N2 1.2484(13) . ?
O3 N2 1.2585(13) . ?
O4 N2 1.2578(13) . ?
O5 H5A 0.826(19) . ?
O5 H5B 0.84(2) . ?
O6 C6 1.2419(14) 2 ?
O7 H7A 0.851(19) . ?
O7 H7B 0.84(2) . ?

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 Mg1 O1 180.0 . 2_655 ?
O1 Mg1 O6 86.22(3) . 2_655 ?
O1 Mg1 O6 93.78(3) 2_655 2_655 ?
O1 Mg1 O6 93.78(3) . . ?
O1 Mg1 O6 86.22(3) 2_655 . ?
O6 Mg1 O6 180.0 2_655 . ?
O1 Mg1 O5 92.28(3) . . ?
O1 Mg1 O5 87.72(3) 2_655 . ?
O6 Mg1 O5 84.50(3) 2_655 . ?
O6 Mg1 O5 95.50(3) . . ?
O1 Mg1 O5 87.72(3) . 2_655 ?
O1 Mg1 O5 92.28(3) 2_655 2_655 ?
O6 Mg1 O5 95.50(3) 2_655 2_655 ?
O6 Mg1 O5 84.50(3) . 2_655 ?
O5 Mg1 O5 180.0 . 2_655 ?
C6 O1 Mg1 133.66(7) . . ?
C5 N1 C1 122.48(10) . . ?
C5 N1 H1 118.5(9) . . ?
C1 N1 H1 119.0(9) . . ?
N1 C1 C2 119.43(10) . . ?
N1 C1 C6 116.64(10) . . ?
C2 C1 C6 123.91(10) . . ?
C1 C2 C3 119.25(11) . . ?
C1 C2 H2 118.6(9) . . ?
C3 C2 H2 122.1(9) . . ?
C4 C3 C2 119.95(11) . . ?
C4 C3 H3 121.7(9) . . ?
C2 C3 H3 118.4(9) . . ?
C5 C4 C3 118.82(11) . . ?
C5 C4 H4 119.7(9) . . ?
C3 C4 H4 121.4(9) . . ?
N1 C5 C4 120.06(10) . . ?
N1 C5 H5 116.3(9) . . ?
C4 C5 H5 123.6(9) . . ?
O6 C6 O1 129.27(10) 2 . ?
O6 C6 C1 116.49(10) 2 . ?
O1 C6 C1 114.23(9) . . ?
O2 N2 O4 120.27(9) . . ?
O2 N2 O3 120.35(10) . . ?
O4 N2 O3 119.39(9) . . ?
Mg1 O5 H5A 113.3(12) . . ?
Mg1 O5 H5B 121.6(13) . . ?
H5A O5 H5B 105.6(17) . . ?
C6 O6 Mg1 144.01(8) 2 . ?
H7A O7 H7B 104.3(18) . . ?

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 0.05(17) . . . . ?
C5 N1 C1 C6 178.98(10) . . . . ?
N1 C1 C2 C3 0.49(17) . . . . ?
C6 C1 C2 C3 -178.36(10) . . . . ?
C1 C2 C3 C4 -0.41(18) . . . . ?
C2 C3 C4 C5 -0.19(18) . . . . ?
C1 N1 C5 C4 -0.67(18) . . . . ?
C3 C4 C5 N1 0.72(18) . . . . ?
Mg1 O1 C6 O6 30.07(19) . . . 2 ?
Mg1 O1 C6 C1 -148.73(8) . . . . ?
N1 C1 C6 O6 163.79(10) . . . 2 ?
C2 C1 C6 O6 -17.34(17) . . . 2 ?
N1 C1 C6 O1 -17.24(15) . . . . ?
C2 C1 C6 O1 161.63(11) . . . . ?

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
N1 H1 O3 0.896(16) 1.957(16) 2.8441(13) 169.7(14) .
C5 H5 O2 0.987(15) 2.407(15) 3.1843(15) 135.2(11) .
C5 H5 O2 0.987(15) 2.492(15) 3.1043(14) 119.9(11) 2_654
O5 H5A O7 0.826(19) 1.973(19) 2.7873(13) 168.5(17) 2_545
O5 H5B O7 0.84(2) 1.94(2) 2.7759(12) 171.4(19) .
O7 H7A O4 0.851(19) 1.98(2) 2.8285(13) 175.0(18) 2_655
O7 H7A N2 0.851(19) 2.671(19) 3.4600(13) 154.9(15) 2_655
O7 H7B O1 0.84(2) 2.49(2) 3.0587(13) 125.7(16) 2
O7 H7B O5 0.84(2) 2.21(2) 2.9790(13) 151.6(18) 1_455

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 964956'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 'picolinic acid magnesium nitrate tetrahydrate' 
;
_chemical_name_common            ?
_chemical_melting_point          358-361
_chemical_formula_moiety         'C12 H18 Mg N2 O8, 2(N O3)'
_chemical_formula_sum            'C12 H18 Mg N4 O14'
_chemical_formula_weight         466.61

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'
Mg Mg 0.0486 0.0363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      Triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.9760(12)
_cell_length_b                   10.184(2)
_cell_length_c                   13.819(3)
_cell_angle_alpha                80.832(7)
_cell_angle_beta                 83.325(6)
_cell_angle_gamma                77.664(5)
_cell_volume                     943.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11430
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.6

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   0.939
_exptl_transmission_factor_max   1.000
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scans
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
; 
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011) 
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  
; 
'Rigaku R-AXIS RAPID IP Image Plate diffractometer' 
;
_diffrn_measurement_method       'profile data from \\w-scans'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            22236
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.997
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4289
_reflns_number_gt                3075
_reflns_threshold_expression     'I > 2\\s(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       
; 
        CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011) 
;
_computing_cell_refinement       
; 
        CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011) 
;
_computing_data_reduction        
; 
        CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011) 
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;      
ORTEP-3: Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. 
;
_computing_publication_material  
; 
enCIFer: Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R.  
& Towler, M. (2004). J. Appl. Cryst. 37, 335-338. 
;

_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/[\\s²(Fo²)+(0.0464P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4289
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_restrained_S_all      1.226
_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
Mg1 Mg 0.23166(8) 0.75153(6) 0.01682(4) 0.01677(15) Uani 1 1 d . . . . .
O2 O 0.36106(17) 0.86282(12) -0.09983(9) 0.0205(3) Uani 1 1 d . . . . .
O3 O 0.11591(16) 0.62383(12) 0.13000(8) 0.0185(3) Uani 1 1 d . . . . .
O4 O -0.04606(17) 0.80585(13) -0.04008(9) 0.0187(3) Uani 1 1 d . . . . .
O5 O 0.49118(18) 0.69615(13) 0.08869(10) 0.0204(3) Uani 1 1 d . . . . .
O6 O 0.30085(18) 0.59342(13) -0.06392(10) 0.0204(3) Uani 1 1 d . . . . .
O7 O 0.13964(18) 0.90667(13) 0.10211(10) 0.0212(3) Uani 1 1 d . . . . .
O8 O 0.33444(17) 1.08417(12) -0.08784(9) 0.0216(3) Uani 1 1 d . . . . .
O9 O 0.15376(17) 0.41527(12) 0.08643(9) 0.0199(3) Uani 1 1 d . . . . .
N16 N -0.0478(2) 0.55287(15) 0.30493(10) 0.0169(3) Uani 1 1 d . . . . .
N17 N 0.5565(2) 0.89263(15) -0.27896(11) 0.0178(3) Uani 1 1 d . . . . .
C20 C 0.3826(2) 0.98156(17) -0.13069(12) 0.0165(4) Uani 1 1 d . . . . .
C21 C 0.4801(2) 1.00317(17) -0.23453(12) 0.0166(4) Uani 1 1 d . . . . .
C22 C 0.4923(3) 1.12870(18) -0.28554(13) 0.0200(4) Uani 1 1 d . . . . .
C23 C 0.5845(3) 1.13937(19) -0.37995(14) 0.0239(4) Uani 1 1 d . . . . .
C24 C 0.6659(3) 1.02357(19) -0.42221(14) 0.0237(4) Uani 1 1 d . . . . .
C25 C 0.6485(3) 0.89966(19) -0.37044(13) 0.0210(4) Uani 1 1 d . . . . .
C26 C 0.0969(2) 0.50252(17) 0.14297(12) 0.0166(4) Uani 1 1 d . . . . .
C27 C -0.0063(2) 0.45884(17) 0.24320(12) 0.0166(4) Uani 1 1 d . . . . .
C28 C -0.0551(2) 0.33487(18) 0.27427(13) 0.0189(4) Uani 1 1 d . . . . .
C29 C -0.1436(3) 0.30825(18) 0.36936(13) 0.0203(4) Uani 1 1 d . . . . .
C30 C -0.1838(3) 0.40813(18) 0.43016(14) 0.0209(4) Uani 1 1 d . . . . .
C31 C -0.1349(2) 0.53138(18) 0.39626(13) 0.0191(4) Uani 1 1 d . . . . .
H22 H 0.439(3) 1.206(2) -0.2565(14) 0.027(5) Uiso 1 1 d . . . . .
H23 H 0.590(3) 1.226(2) -0.4142(15) 0.027(5) Uiso 1 1 d . . . . .
H24 H 0.735(3) 1.025(2) -0.4846(15) 0.029(5) Uiso 1 1 d . . . . .
H25 H 0.690(3) 0.816(2) -0.3921(14) 0.023(5) Uiso 1 1 d . . . . .
H17 H 0.546(3) 0.806(2) -0.2510(15) 0.034(6) Uiso 1 1 d . . . . .
H28 H -0.030(3) 0.263(2) 0.2344(14) 0.026(5) Uiso 1 1 d . . . . .
H29 H -0.174(3) 0.217(2) 0.3889(14) 0.022(5) Uiso 1 1 d . . . . .
H30 H -0.242(3) 0.396(2) 0.4926(15) 0.026(5) Uiso 1 1 d . . . . .
H31 H -0.154(2) 0.6027(19) 0.4320(14) 0.019(5) Uiso 1 1 d . . . . .
H16 H -0.015(3) 0.639(2) 0.2880(16) 0.040(6) Uiso 1 1 d . . . . .
H6A H 0.278(3) 0.511(3) -0.0298(19) 0.060(8) Uiso 1 1 d . . . . .
H6B H 0.389(3) 0.585(2) -0.1136(18) 0.045(7) Uiso 1 1 d . . . . .
H7A H 0.083(3) 0.883(2) 0.1661(18) 0.049(7) Uiso 1 1 d . . . . .
H7B H 0.115(3) 0.993(3) 0.0869(17) 0.041(7) Uiso 1 1 d . . . . .
H4A H -0.080(3) 0.734(3) -0.0601(17) 0.045(7) Uiso 1 1 d . . . . .
H4B H -0.139(4) 0.834(3) 0.0036(19) 0.061(8) Uiso 1 1 d . . . . .
H5A H 0.545(3) 0.768(3) 0.0910(17) 0.043(7) Uiso 1 1 d . . . . .
H5B H 0.472(3) 0.655(2) 0.1482(18) 0.044(7) Uiso 1 1 d . . . . .
O13 O 0.54153(17) 0.61545(12) -0.23979(9) 0.0213(3) Uani 1 1 d . . . . .
O14 O 0.54497(19) 0.42539(13) -0.29332(10) 0.0274(3) Uani 1 1 d . . . . .
O15 O 0.63463(18) 0.59238(13) -0.39344(9) 0.0247(3) Uani 1 1 d . . . . .
N18 N 0.57411(19) 0.54377(15) -0.30975(11) 0.0189(3) Uani 1 1 d . . . . .
O10 O 0.0000(2) 0.81596(13) 0.28267(10) 0.0359(4) Uani 1 1 d . . . . .
O11 O -0.0924(2) 0.82424(13) 0.43654(9) 0.0318(3) Uani 1 1 d . . . . .
O12 O -0.09928(19) 1.01013(12) 0.33449(10) 0.0293(3) Uani 1 1 d . . . . .
N19 N -0.0647(2) 0.88502(15) 0.35232(11) 0.0200(3) 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
Mg1 O6 2.0459(14) . ?
Mg1 O2 2.0529(13) . ?
Mg1 O7 2.0693(14) . ?
Mg1 O3 2.0728(13) . ?
Mg1 O5 2.0941(14) . ?
Mg1 O4 2.1059(14) . ?
O2 C20 1.251(2) . ?
O3 C26 1.253(2) . ?
O4 H4A 0.91(3) . ?
O4 H4B 0.87(3) . ?
O5 H5A 0.89(3) . ?
O5 H5B 0.87(2) . ?
O6 H6A 0.93(3) . ?
O6 H6B 0.87(2) . ?
O7 H7A 0.94(2) . ?
O7 H7B 0.85(2) . ?
O8 C20 1.248(2) . ?
O9 C26 1.247(2) . ?
N16 C31 1.342(2) . ?
N16 C27 1.346(2) . ?
N16 H16 0.94(2) . ?
N17 C21 1.348(2) . ?
N17 C25 1.348(2) . ?
N17 H17 0.92(2) . ?
C20 C21 1.519(2) . ?
C21 C22 1.373(2) . ?
C22 C23 1.384(2) . ?
C22 H22 0.93(2) . ?
C23 C24 1.382(3) . ?
C23 H23 0.94(2) . ?
C24 C25 1.370(3) . ?
C24 H24 0.94(2) . ?
C25 H25 0.923(19) . ?
C26 C27 1.531(2) . ?
C27 C28 1.368(2) . ?
C28 C29 1.397(2) . ?
C28 H28 0.96(2) . ?
C29 C30 1.384(3) . ?
C29 H29 0.98(2) . ?
C30 C31 1.367(3) . ?
C30 H30 0.912(19) . ?
C31 H31 0.919(19) . ?
O13 N18 1.2735(18) . ?
O14 N18 1.2462(19) . ?
O15 N18 1.2467(18) . ?
O10 N19 1.2664(19) . ?
O11 N19 1.2427(19) . ?
O12 N19 1.2348(19) . ?

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
O6 Mg1 O2 87.00(6) . . ?
O6 Mg1 O7 175.27(6) . . ?
O2 Mg1 O7 96.60(6) . . ?
O6 Mg1 O3 88.31(6) . . ?
O2 Mg1 O3 174.91(5) . . ?
O7 Mg1 O3 88.19(6) . . ?
O6 Mg1 O5 94.57(5) . . ?
O2 Mg1 O5 92.50(6) . . ?
O7 Mg1 O5 88.36(6) . . ?
O3 Mg1 O5 85.92(6) . . ?
O6 Mg1 O4 88.86(6) . . ?
O2 Mg1 O4 92.92(5) . . ?
O7 Mg1 O4 87.89(6) . . ?
O3 Mg1 O4 88.95(5) . . ?
O5 Mg1 O4 173.73(6) . . ?
C20 O2 Mg1 141.24(11) . . ?
C26 O3 Mg1 135.68(11) . . ?
Mg1 O4 H4A 111.2(14) . . ?
Mg1 O4 H4B 111.9(17) . . ?
H4A O4 H4B 106(2) . . ?
Mg1 O5 H5A 111.8(14) . . ?
Mg1 O5 H5B 112.1(14) . . ?
H5A O5 H5B 109(2) . . ?
Mg1 O6 H6A 114.5(16) . . ?
Mg1 O6 H6B 126.3(16) . . ?
H6A O6 H6B 114(2) . . ?
Mg1 O7 H7A 116.6(14) . . ?
Mg1 O7 H7B 131.7(15) . . ?
H7A O7 H7B 110(2) . . ?
C31 N16 C27 123.32(16) . . ?
C31 N16 H16 114.2(13) . . ?
C27 N16 H16 122.5(13) . . ?
C21 N17 C25 122.91(16) . . ?
C21 N17 H17 123.2(13) . . ?
C25 N17 H17 113.8(13) . . ?
O8 C20 O2 128.78(16) . . ?
O8 C20 C21 115.89(15) . . ?
O2 C20 C21 115.33(15) . . ?
N17 C21 C22 118.55(16) . . ?
N17 C21 C20 117.84(15) . . ?
C22 C21 C20 123.61(16) . . ?
C21 C22 C23 119.91(17) . . ?
C21 C22 H22 119.8(12) . . ?
C23 C22 H22 120.3(12) . . ?
C24 C23 C22 119.94(17) . . ?
C24 C23 H23 121.1(12) . . ?
C22 C23 H23 119.0(12) . . ?
C25 C24 C23 118.99(17) . . ?
C25 C24 H24 117.8(12) . . ?
C23 C24 H24 123.2(12) . . ?
N17 C25 C24 119.66(17) . . ?
N17 C25 H25 113.4(12) . . ?
C24 C25 H25 126.9(12) . . ?
O9 C26 O3 128.56(15) . . ?
O9 C26 C27 117.62(15) . . ?
O3 C26 C27 113.81(15) . . ?
N16 C27 C28 118.88(15) . . ?
N16 C27 C26 115.19(15) . . ?
C28 C27 C26 125.91(15) . . ?
C27 C28 C29 119.38(17) . . ?
C27 C28 H28 123.4(12) . . ?
C29 C28 H28 117.2(12) . . ?
C30 C29 C28 119.68(17) . . ?
C30 C29 H29 123.8(11) . . ?
C28 C29 H29 116.5(11) . . ?
C31 C30 C29 119.34(17) . . ?
C31 C30 H30 117.9(13) . . ?
C29 C30 H30 122.7(13) . . ?
N16 C31 C30 119.38(17) . . ?
N16 C31 H31 115.6(12) . . ?
C30 C31 H31 125.1(12) . . ?
O14 N18 O15 120.86(15) . . ?
O14 N18 O13 119.26(14) . . ?
O15 N18 O13 119.89(14) . . ?
O12 N19 O11 122.13(15) . . ?
O12 N19 O10 119.18(15) . . ?
O11 N19 O10 118.69(15) . . ?

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
Mg1 O2 C20 O8 7.2(3) . . . . ?
Mg1 O2 C20 C21 -172.65(12) . . . . ?
C25 N17 C21 C22 1.6(3) . . . . ?
C25 N17 C21 C20 -179.14(16) . . . . ?
O8 C20 C21 N17 171.88(15) . . . . ?
O2 C20 C21 N17 -8.3(2) . . . . ?
O8 C20 C21 C22 -8.9(2) . . . . ?
O2 C20 C21 C22 170.98(16) . . . . ?
N17 C21 C22 C23 -1.0(3) . . . . ?
C20 C21 C22 C23 179.78(17) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
C22 C23 C24 C25 1.9(3) . . . . ?
C21 N17 C25 C24 -0.4(3) . . . . ?
C23 C24 C25 N17 -1.3(3) . . . . ?
Mg1 O3 C26 O9 2.7(3) . . . . ?
Mg1 O3 C26 C27 -178.87(10) . . . . ?
C31 N16 C27 C28 0.2(2) . . . . ?
C31 N16 C27 C26 -178.88(15) . . . . ?
O9 C26 C27 N16 173.93(14) . . . . ?
O3 C26 C27 N16 -4.7(2) . . . . ?
O9 C26 C27 C28 -5.1(3) . . . . ?
O3 C26 C27 C28 176.32(16) . . . . ?
N16 C27 C28 C29 -1.0(3) . . . . ?
C26 C27 C28 C29 177.93(15) . . . . ?
C27 C28 C29 C30 1.1(3) . . . . ?
C28 C29 C30 C31 -0.4(3) . . . . ?
C27 N16 C31 C30 0.5(3) . . . . ?
C29 C30 C31 N16 -0.4(3) . . . . ?

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
C22 H22 O14 0.93(2) 2.46(2) 3.104(2) 126.7(15) 1_565
C24 H24 O11 0.94(2) 2.49(2) 3.132(2) 126.2(15) 1_654
C24 H24 O12 0.94(2) 2.64(2) 3.575(2) 172.8(17) 1_654
C25 H25 O15 0.923(19) 2.39(2) 3.218(2) 148.5(15) .
C25 H25 O11 0.923(19) 2.659(18) 3.148(2) 113.8(14) 1_654
N17 H17 O13 0.92(2) 1.93(2) 2.810(2) 160.0(19) .
C31 H31 O11 0.919(19) 2.40(2) 3.200(2) 145.7(15) .
N16 H16 O10 0.94(2) 1.82(2) 2.735(2) 165(2) .
O6 H6A O5 0.93(3) 2.55(2) 3.0489(18) 114.1(18) 2_665
O6 H6A O9 0.93(3) 1.96(3) 2.7857(18) 148(2) .
O6 H6B O13 0.87(2) 1.95(2) 2.7954(18) 164(2) .
O7 H7A O10 0.94(2) 1.73(3) 2.6671(19) 172(2) .
O7 H7A N19 0.94(2) 2.66(2) 3.575(2) 164(2) .
O7 H7B O4 0.85(2) 2.02(3) 2.8715(19) 175(2) 2_575
O4 H4A O9 0.91(3) 1.80(3) 2.7093(18) 174(2) 2_565
O4 H4B O8 0.87(3) 1.84(3) 2.6959(17) 173(3) 2_575
O5 H5A O8 0.89(3) 1.87(3) 2.7633(19) 176(2) 2_675
O5 H5B O14 0.87(2) 2.04(3) 2.9058(19) 172(2) 2_665

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.075

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 964957'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
isonicotinic acid magnesium nitrate tetrahydrate 
;
_chemical_name_common            ?
_chemical_melting_point          390-400
_chemical_formula_moiety         '(C12 H18 Mg N2 O8), 2(N O3)'
_chemical_formula_sum            'C12 H18 Mg N4 O14'
_chemical_formula_weight         466.61

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'
Mg Mg 0.0486 0.0363 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.1279(6)
_cell_length_b                   8.1151(10)
_cell_length_c                   9.4126(12)
_cell_angle_alpha                89.443(5)
_cell_angle_beta                 86.609(4)
_cell_angle_gamma                88.628(4)
_cell_volume                     467.11(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    11191
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_F_000             242
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.181
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  
; 
'Rigaku R-AXIS RAPID IP Image Plate diffractometer' 
;
_diffrn_measurement_method       'profile data from \\w-scans'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            11191
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.304
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2125
_reflns_number_gt                1808
_reflns_threshold_expression     'I > 2\\s(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       
; 
        CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011) 
;
_computing_cell_refinement       
; 
        CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011) 
;
_computing_data_reduction        
; 
        CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011) 
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;      
ORTEP-3: Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. 
;
_computing_publication_material  
; 
enCIFer: Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R.  
& Towler, M. (2004). J. Appl. Cryst. 37, 335-338. 
;

_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/[\\s²(Fo²)+(0.0469P)²+0.1181P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2125
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
Mg1 Mg 0.0000 0.0000 0.0000 0.01705(16) Uani 1 2 d S . P . .
O4 O 0.43290(16) -0.05655(13) 0.30781(10) 0.0267(2) Uani 1 1 d . . . . .
O5 O 0.12144(16) -0.02791(12) 0.19620(10) 0.0225(2) Uani 1 1 d . . . . .
O6 O 0.30704(16) -0.05884(13) -0.09178(11) 0.0223(2) Uani 1 1 d . . . . .
O7 O 0.05019(17) 0.25366(12) 0.00132(10) 0.0210(2) Uani 1 1 d . . . . .
N2 N -0.09658(19) -0.34024(14) 0.63314(12) 0.0216(3) Uani 1 1 d . . . . .
C1 C 0.2344(2) -0.07621(16) 0.29574(13) 0.0180(3) Uani 1 1 d . . . . .
C2 C 0.1137(2) -0.16968(15) 0.41719(13) 0.0173(3) Uani 1 1 d . . . . .
C3 C 0.2078(2) -0.19019(16) 0.54722(14) 0.0191(3) Uani 1 1 d . . . . .
C4 C 0.0975(2) -0.27586(17) 0.65586(14) 0.0214(3) Uani 1 1 d . . . . .
C5 C -0.1932(2) -0.32142(17) 0.50905(15) 0.0225(3) Uani 1 1 d . . . . .
C6 C -0.0913(2) -0.23431(17) 0.39875(14) 0.0200(3) Uani 1 1 d . . . . .
H3 H 0.347(3) -0.141(2) 0.5634(18) 0.028(4) Uiso 1 1 d . . . . .
H4 H 0.146(3) -0.294(2) 0.7462(18) 0.020(4) Uiso 1 1 d . . . . .
H5 H -0.333(3) -0.371(2) 0.5022(17) 0.022(4) Uiso 1 1 d . . . . .
H6 H -0.159(3) -0.219(2) 0.3149(19) 0.024(4) Uiso 1 1 d . . . . .
H7 H -0.157(3) -0.404(2) 0.703(2) 0.039(5) Uiso 1 1 d . . . . .
H8 H 0.378(3) -0.123(3) -0.050(2) 0.039(6) Uiso 1 1 d . . . . .
H9 H 0.398(3) -0.019(3) -0.158(2) 0.046(6) Uiso 1 1 d . . . . .
H10 H 0.173(3) 0.287(2) -0.023(2) 0.039(5) Uiso 1 1 d . . . . .
H11 H -0.038(3) 0.314(2) -0.046(2) 0.043(5) Uiso 1 1 d . . . . .
O1 O 0.23386(15) -0.43584(12) 0.16418(10) 0.0235(2) Uani 1 1 d . . . . .
O2 O 0.51793(16) -0.32411(12) 0.05829(11) 0.0246(2) Uani 1 1 d . . . . .
O3 O 0.55324(17) -0.47778(13) 0.24681(12) 0.0301(3) Uani 1 1 d . . . . .
N1 N 0.43839(18) -0.41267(14) 0.15707(12) 0.0199(2) 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
Mg1 O5 2.0401(10) . ?
Mg1 O5 2.0402(10) 2 ?
Mg1 O6 2.0705(10) . ?
Mg1 O6 2.0705(10) 2 ?
Mg1 O7 2.0889(10) . ?
Mg1 O7 2.0889(10) 2 ?
O4 C1 1.2423(16) . ?
O5 C1 1.2520(16) . ?
O6 H8 0.78(2) . ?
O6 H9 0.88(2) . ?
O7 H10 0.82(2) . ?
O7 H11 0.86(2) . ?
N2 C4 1.3397(18) . ?
N2 C5 1.3464(19) . ?
N2 H7 0.90(2) . ?
C1 C2 1.5295(17) . ?
C2 C3 1.3906(19) . ?
C2 C6 1.3937(18) . ?
C3 C4 1.3832(18) . ?
C3 H3 0.968(17) . ?
C4 H4 0.927(17) . ?
C5 C6 1.3776(18) . ?
C5 H5 0.961(17) . ?
C6 H6 0.918(17) . ?
O1 N1 1.2696(14) . ?
O2 N1 1.2526(14) . ?
O3 N1 1.2377(15) . ?

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
O5 Mg1 O5 180.0 . 2 ?
O5 Mg1 O6 89.25(4) . . ?
O5 Mg1 O6 90.75(4) 2 . ?
O5 Mg1 O6 90.75(4) . 2 ?
O5 Mg1 O6 89.25(4) 2 2 ?
O6 Mg1 O6 180.0 . 2 ?
O5 Mg1 O7 91.46(4) . . ?
O5 Mg1 O7 88.54(4) 2 . ?
O6 Mg1 O7 94.74(4) . . ?
O6 Mg1 O7 85.26(4) 2 . ?
O5 Mg1 O7 88.54(4) . 2 ?
O5 Mg1 O7 91.46(4) 2 2 ?
O6 Mg1 O7 85.26(4) . 2 ?
O6 Mg1 O7 94.74(4) 2 2 ?
O7 Mg1 O7 180.0 . 2 ?
C1 O5 Mg1 162.16(9) . . ?
Mg1 O6 H8 116.4(15) . . ?
Mg1 O6 H9 137.8(13) . . ?
H8 O6 H9 104.5(19) . . ?
Mg1 O7 H10 118.3(14) . . ?
Mg1 O7 H11 116.4(13) . . ?
H10 O7 H11 104.6(19) . . ?
C4 N2 C5 122.63(12) . . ?
C4 N2 H7 116.9(12) . . ?
C5 N2 H7 120.3(12) . . ?
O4 C1 O5 127.66(12) . . ?
O4 C1 C2 116.16(11) . . ?
O5 C1 C2 116.18(11) . . ?
C3 C2 C6 119.52(12) . . ?
C3 C2 C1 120.06(12) . . ?
C6 C2 C1 120.42(12) . . ?
C4 C3 C2 119.47(12) . . ?
C4 C3 H3 119.9(10) . . ?
C2 C3 H3 120.6(10) . . ?
N2 C4 C3 119.41(13) . . ?
N2 C4 H4 115.1(10) . . ?
C3 C4 H4 125.5(10) . . ?
N2 C5 C6 119.97(13) . . ?
N2 C5 H5 117.1(10) . . ?
C6 C5 H5 122.9(10) . . ?
C5 C6 C2 118.96(13) . . ?
C5 C6 H6 120.1(10) . . ?
C2 C6 H6 121.0(10) . . ?
O3 N1 O2 121.93(11) . . ?
O3 N1 O1 119.56(11) . . ?
O2 N1 O1 118.51(11) . . ?

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
Mg1 O5 C1 O4 65.1(4) . . . . ?
Mg1 O5 C1 C2 -115.2(3) . . . . ?
O4 C1 C2 C3 16.50(18) . . . . ?
O5 C1 C2 C3 -163.20(12) . . . . ?
O4 C1 C2 C6 -163.73(12) . . . . ?
O5 C1 C2 C6 16.57(18) . . . . ?
C6 C2 C3 C4 0.6(2) . . . . ?
C1 C2 C3 C4 -179.60(12) . . . . ?
C5 N2 C4 C3 -1.9(2) . . . . ?
C2 C3 C4 N2 1.2(2) . . . . ?
C4 N2 C5 C6 0.6(2) . . . . ?
N2 C5 C6 C2 1.3(2) . . . . ?
C3 C2 C6 C5 -1.9(2) . . . . ?
C1 C2 C6 C5 178.38(12) . . . . ?

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
C3 H3 O4 0.968(17) 2.492(18) 3.3671(17) 150.3(14) 2_656
C4 H4 O7 0.927(17) 2.619(16) 3.3048(17) 131.3(12) 2_556
C4 H4 O3 0.927(17) 2.584(16) 3.0674(17) 113.0(12) 2_646
N2 H7 O1 0.90(2) 1.85(2) 2.7322(15) 168.3(18) 2_546
N2 H7 O3 0.90(2) 2.65(2) 3.3286(16) 133.2(15) 2_546
N2 H7 N1 0.90(2) 2.60(2) 3.4556(16) 160.0(16) 2_546
O6 H8 O2 0.78(2) 2.11(2) 2.8849(15) 169(2) .
O6 H9 O4 0.88(2) 1.81(2) 2.6837(14) 175(2) 2_655
O7 H10 O2 0.82(2) 1.94(2) 2.7453(14) 167.7(19) 2_655
O7 H11 O1 0.86(2) 1.93(2) 2.7920(14) 175.2(19) 2

_refine_diff_density_max         0.412
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 964958'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_4

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
'picolinic acid magnesium nitrate trihydrate' 
;
_chemical_name_common            ?
_chemical_melting_point          393-406
_chemical_formula_moiety         '(C6 H11 Mg N2 O8), (N O3)'
_chemical_formula_sum            'C6 H11 Mg N3 O11'
_chemical_formula_weight         325.49

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'
Mg Mg 0.0486 0.0363 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.9683(6)
_cell_length_b                   6.8418(3)
_cell_length_c                   18.8376(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.938(2)
_cell_angle_gamma                90
_cell_volume                     1246.92(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    15569
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.211
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  
; 
        'Rigaku R-AXIS RAPID IP Image Plate diffractometer' 
;
_diffrn_measurement_method       'profile data from \\w-scans'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            15569
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.179
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2829
_reflns_number_gt                2318
_reflns_threshold_expression     'I > 2\\s(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       
; 
        CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011) 
;
_computing_cell_refinement       
; 
        CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011) 
;
_computing_data_reduction        
; 
        CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011) 
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;      
ORTEP-3: Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. 
;
_computing_publication_material  
; 
enCIFer: Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R.  
& Towler, M. (2004). J. Appl. Cryst. 37, 335-338. 
;

_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/[\\s²(Fo²)+(0.0441P)²+0.6606P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2829
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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
Mg1 Mg 0.42357(6) 0.38918(8) 0.25102(3) 0.01501(15) Uani 1 1 d . . . . .
O2 O 0.29465(12) 0.38835(17) 0.32270(6) 0.0166(3) Uani 1 1 d . . . . .
O3 O 0.56117(12) 0.39652(17) 0.18011(6) 0.0182(3) Uani 1 1 d . . . . .
O4 O 0.71861(13) 0.59320(18) 0.24342(7) 0.0211(3) Uani 1 1 d . . . . .
O5 O 0.75848(13) 0.43455(18) 0.15134(6) 0.0217(3) Uani 1 1 d . . . . .
O7 O 0.57104(13) 0.27403(19) 0.33609(7) 0.0199(3) Uani 1 1 d . . . . .
O8 O 0.27339(13) 0.4849(2) 0.16425(7) 0.0196(3) Uani 1 1 d . . . . .
O9 O 0.37056(13) 0.11265(17) 0.21620(6) 0.0191(3) Uani 1 1 d . . . . .
O10 O 0.47864(14) 0.67350(18) 0.28247(7) 0.0190(3) Uani 1 1 d . . . . .
N6 N 0.67981(14) 0.4747(2) 0.19208(7) 0.0166(3) Uani 1 1 d . . . . .
N21 N 0.19095(16) 0.3179(2) 0.44081(8) 0.0174(3) Uani 1 1 d . . . . .
C15 C 0.18471(17) 0.4767(2) 0.32400(8) 0.0152(3) Uani 1 1 d . . . . .
C16 C 0.11162(18) 0.4044(2) 0.38061(9) 0.0163(3) Uani 1 1 d . . . . .
C17 C -0.02892(18) 0.4163(3) 0.37318(9) 0.0182(4) Uani 1 1 d . . . . .
C18 C -0.0868(2) 0.3335(3) 0.42691(10) 0.0229(4) Uani 1 1 d . . . . .
C19 C -0.0015(2) 0.2463(3) 0.48780(10) 0.0238(4) Uani 1 1 d . . . . .
C20 C 0.1387(2) 0.2415(3) 0.49395(9) 0.0221(4) Uani 1 1 d . . . . .
H1 H 0.564(3) 0.683(4) 0.2815(16) 0.053(8) Uiso 1 1 d . . . . .
H3 H 0.475(3) 0.723(4) 0.3232(17) 0.049(8) Uiso 1 1 d . . . . .
H4 H 0.617(3) 0.172(4) 0.3344(14) 0.041(7) Uiso 1 1 d . . . . .
H5 H 0.554(3) 0.271(4) 0.3789(16) 0.047(7) Uiso 1 1 d . . . . .
H6 H 0.230(3) 0.581(4) 0.1671(14) 0.043(8) Uiso 1 1 d . . . . .
H7 H 0.234(3) 0.421(4) 0.1274(15) 0.045(7) Uiso 1 1 d . . . . .
H8 H -0.082(2) 0.477(3) 0.3345(11) 0.013(4) Uiso 1 1 d . . . . .
H9 H -0.187(2) 0.343(3) 0.4215(12) 0.029(6) Uiso 1 1 d . . . . .
H10 H -0.035(2) 0.189(3) 0.5287(13) 0.033(6) Uiso 1 1 d . . . . .
H11 H 0.203(2) 0.187(3) 0.5348(13) 0.030(6) Uiso 1 1 d . . . . .
H12 H 0.290(3) 0.315(4) 0.4448(13) 0.039(6) Uiso 1 1 d . . . . .
O12 O 0.52177(14) 0.8046(2) 0.42944(7) 0.0279(3) Uani 1 1 d . . . . .
O13 O 0.32770(13) 0.7596(2) 0.46057(7) 0.0267(3) Uani 1 1 d . . . . .
O14 O 0.52303(13) 0.7085(2) 0.53925(6) 0.0265(3) Uani 1 1 d . . . . .
N11 N 0.45637(16) 0.7582(2) 0.47568(8) 0.0212(3) 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
Mg1 O9 2.0303(13) . ?
Mg1 O8 2.0404(13) . ?
Mg1 O7 2.0529(13) . ?
Mg1 O10 2.0687(13) . ?
Mg1 O2 2.0761(13) . ?
Mg1 O3 2.1333(13) . ?
O2 C15 1.257(2) . ?
O3 N6 1.2678(18) . ?
O4 N6 1.2498(18) . ?
O5 N6 1.2527(18) . ?
O7 H4 0.84(3) . ?
O7 H5 0.87(3) . ?
O8 H6 0.79(3) . ?
O8 H7 0.84(3) . ?
O9 C15 1.241(2) 2_545 ?
O10 H1 0.86(3) . ?
O10 H3 0.85(3) . ?
N21 C20 1.341(2) . ?
N21 C16 1.353(2) . ?
N21 H12 0.97(3) . ?
C15 O9 1.241(2) 2 ?
C15 C16 1.512(2) . ?
C16 C17 1.376(2) . ?
C17 C18 1.400(3) . ?
C17 H8 0.89(2) . ?
C18 C19 1.387(3) . ?
C18 H9 0.99(2) . ?
C19 C20 1.374(3) . ?
C19 H10 0.99(2) . ?
C20 H11 0.95(2) . ?
O12 N11 1.248(2) . ?
O13 N11 1.245(2) . ?
O14 N11 1.2679(18) . ?

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
O9 Mg1 O8 87.52(6) . . ?
O9 Mg1 O7 88.64(5) . . ?
O8 Mg1 O7 176.16(6) . . ?
O9 Mg1 O10 177.75(6) . . ?
O8 Mg1 O10 91.16(6) . . ?
O7 Mg1 O10 92.67(5) . . ?
O9 Mg1 O2 93.09(5) . . ?
O8 Mg1 O2 94.14(5) . . ?
O7 Mg1 O2 86.01(5) . . ?
O10 Mg1 O2 88.82(5) . . ?
O9 Mg1 O3 88.64(5) . . ?
O8 Mg1 O3 87.09(5) . . ?
O7 Mg1 O3 92.88(5) . . ?
O10 Mg1 O3 89.48(5) . . ?
O2 Mg1 O3 177.93(5) . . ?
C15 O2 Mg1 133.67(11) . . ?
N6 O3 Mg1 127.70(10) . . ?
Mg1 O7 H4 125.8(18) . . ?
Mg1 O7 H5 118.0(18) . . ?
H4 O7 H5 105(2) . . ?
Mg1 O8 H6 121.1(19) . . ?
Mg1 O8 H7 127.3(18) . . ?
H6 O8 H7 110(3) . . ?
C15 O9 Mg1 159.71(11) 2_545 . ?
Mg1 O10 H1 105.3(19) . . ?
Mg1 O10 H3 124.8(18) . . ?
H1 O10 H3 104(3) . . ?
O4 N6 O5 119.58(14) . . ?
O4 N6 O3 120.85(14) . . ?
O5 N6 O3 119.56(13) . . ?
C20 N21 C16 122.86(16) . . ?
C20 N21 H12 120.3(14) . . ?
C16 N21 H12 116.9(14) . . ?
O9 C15 O2 127.54(16) 2 . ?
O9 C15 C16 117.19(15) 2 . ?
O2 C15 C16 115.27(14) . . ?
N21 C16 C17 119.11(16) . . ?
N21 C16 C15 116.78(15) . . ?
C17 C16 C15 124.08(15) . . ?
C16 C17 C18 119.27(17) . . ?
C16 C17 H8 120.0(12) . . ?
C18 C17 H8 120.7(12) . . ?
C19 C18 C17 119.66(18) . . ?
C19 C18 H9 121.3(13) . . ?
C17 C18 H9 118.9(13) . . ?
C20 C19 C18 119.22(17) . . ?
C20 C19 H10 116.9(14) . . ?
C18 C19 H10 123.9(14) . . ?
N21 C20 C19 119.84(17) . . ?
N21 C20 H11 116.8(14) . . ?
C19 C20 H11 123.3(14) . . ?
O13 N11 O12 121.39(14) . . ?
O13 N11 O14 119.64(15) . . ?
O12 N11 O14 118.96(15) . . ?

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
Mg1 O3 N6 O4 -14.7(2) . . . . ?
Mg1 O3 N6 O5 166.26(10) . . . . ?
Mg1 O2 C15 O9 -9.1(3) . . . 2 ?
Mg1 O2 C15 C16 169.69(10) . . . . ?
C20 N21 C16 C17 0.4(2) . . . . ?
C20 N21 C16 C15 -177.67(15) . . . . ?
O9 C15 C16 N21 -154.60(14) 2 . . . ?
O2 C15 C16 N21 26.5(2) . . . . ?
O9 C15 C16 C17 27.5(2) 2 . . . ?
O2 C15 C16 C17 -151.49(16) . . . . ?
N21 C16 C17 C18 -1.9(2) . . . . ?
C15 C16 C17 C18 175.95(15) . . . . ?
C16 C17 C18 C19 2.0(3) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C16 N21 C20 C19 1.1(3) . . . . ?
C18 C19 C20 N21 -1.0(3) . . . . ?

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
O10 H1 O4 0.86(3) 1.95(3) 2.7226(19) 149(3) .
O10 H1 O5 0.86(3) 2.57(3) 3.1683(18) 128(2) 2_655
O10 H1 N6 0.86(3) 2.67(3) 3.227(2) 124(2) .
O10 H3 O12 0.85(3) 2.02(3) 2.8427(18) 164(3) .
O7 H4 O4 0.84(3) 2.51(3) 3.1119(19) 130(2) 2_645
O7 H4 O5 0.84(3) 2.02(3) 2.8539(18) 170(2) 2_645
O7 H4 N6 0.84(3) 2.58(3) 3.358(2) 155(2) 2_645
O7 H5 O14 0.87(3) 1.88(3) 2.7330(19) 167(3) 3_666
O8 H6 O2 0.79(3) 2.14(3) 2.8668(18) 154(3) 2
O8 H6 O9 0.79(3) 2.64(3) 3.0741(18) 117(2) 2
O8 H7 O12 0.84(3) 2.64(3) 3.2852(19) 136(2) 2_545
O8 H7 O13 0.84(3) 1.96(3) 2.7894(18) 170(3) 2_545
O8 H7 N11 0.84(3) 2.61(3) 3.4195(19) 163(2) 2_545
C17 H8 O4 0.89(2) 2.42(2) 3.288(2) 162.5(16) 1_455
C20 H11 O5 0.95(2) 2.29(2) 3.156(2) 151.8(19) 4_566
N21 H12 O14 0.97(3) 1.82(3) 2.790(2) 174(2) 3_666
N21 H12 N11 0.97(3) 2.66(3) 3.527(2) 149.1(19) 3_666

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 964959'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_5

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 2,4-pyridine dicarboxylate pentahydrate' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(Mg1 C7 N1 O8 H11),0.5(H2 O)'
_chemical_formula_sum            'C7 H12 Mg N O8.50'
_chemical_formula_weight         270.49

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'
Mg Mg 0.0486 0.0363 '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'

_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                   9.5610(8)
_cell_length_b                   8.3362(6)
_cell_length_c                   13.9891(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.135(7)
_cell_angle_gamma                90
_cell_volume                     1090.05(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7082
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.201
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
; 
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  
; 
'Rigaku R-AXIS RAPID IP Image Plate diffractometer' 
;
_diffrn_measurement_method       'profile data from \\w-scans'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            13467
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.275
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_full        24.200
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2498
_reflns_number_gt                1414
_reflns_threshold_expression     'I > 2\\s(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       
; 
        CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011) 
;
_computing_cell_refinement       
; 
        CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011) 
;
_computing_data_reduction        
; 
        CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011) 
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;      
ORTEP-3: Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. 
;
_computing_publication_material  
; 
enCIFer: Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R.  
& Towler, M. (2004). J. Appl. Cryst. 37, 335-338. 
;

_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/[\\s²(Fo²)+(0.1648P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2498
_refine_ls_number_parameters     200
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1317
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_ref         0.2809
_refine_ls_wR_factor_gt          0.2056
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.132
_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
Mg1 Mg 0.60736(16) 0.06277(17) 0.18983(10) 0.0268(5) Uani 1 1 d . . . . .
O1 O 0.6694(3) 0.2933(4) 0.2335(2) 0.0303(8) Uani 1 1 d . . . . .
O2 O 0.5261(3) 0.0303(4) 0.3161(2) 0.0275(7) Uani 1 1 d D . . . .
O3 O 0.5996(4) -0.1730(4) 0.1547(2) 0.0308(8) Uani 1 1 d D . . . .
O4 O 0.6701(4) 0.1098(4) 0.0600(2) 0.0315(8) Uani 1 1 d D . . . .
O5 O 0.3990(4) 0.1178(5) 0.1279(3) 0.0448(10) Uani 1 1 d D . . . .
O6 O 0.8279(3) 0.4482(4) 0.3326(2) 0.0330(8) Uani 1 1 d . . . . .
O7 O 1.2917(3) -0.0868(4) 0.5122(2) 0.0309(8) Uani 1 1 d . . . . .
O8 O 1.2979(3) 0.1786(4) 0.4867(2) 0.0310(8) Uani 1 1 d . . . . .
N1 N 0.8225(4) 0.0319(4) 0.2823(3) 0.0277(9) Uani 1 1 d . . . . .
C1 C 0.8949(5) -0.1039(6) 0.3099(3) 0.0275(10) Uani 1 1 d . . . . .
C2 C 1.0271(5) -0.1075(5) 0.3718(3) 0.0283(10) Uani 1 1 d . . . . .
C3 C 1.0940(5) 0.0365(5) 0.4059(3) 0.0285(10) Uani 1 1 d . . . . .
C4 C 1.0185(5) 0.1784(6) 0.3781(3) 0.0291(10) Uani 1 1 d . . . . .
C5 C 0.8833(5) 0.1713(5) 0.3188(3) 0.0269(10) Uani 1 1 d . . . . .
C6 C 0.7887(5) 0.3179(5) 0.2938(3) 0.0285(10) Uani 1 1 d . . . . .
C7 C 1.2390(5) 0.0413(5) 0.4724(3) 0.0294(10) Uani 1 1 d . . . . .
O9 O 0.9290(9) 0.0310(10) 0.0257(6) 0.0477(19) Uiso 0.5 1 d D . P . .
H1 H 0.848(6) -0.200(7) 0.281(4) 0.042(15) Uiso 1 1 d . . . . .
H2 H 1.081(5) -0.212(5) 0.398(3) 0.023(11) Uiso 1 1 d . . . . .
H4 H 1.064(6) 0.285(7) 0.404(4) 0.059(18) Uiso 1 1 d . . . . .
H2A H 0.572(8) 0.035(9) 0.377(2) 0.089 Uiso 1 1 d D U . . .
H2B H 0.462(6) -0.041(7) 0.321(6) 0.089 Uiso 1 1 d D U . . .
H3A H 0.548(7) -0.249(6) 0.173(5) 0.089 Uiso 1 1 d D U . . .
H3B H 0.636(7) -0.209(9) 0.107(4) 0.089 Uiso 1 1 d D U . . .
H4A H 0.619(7) 0.084(9) 0.003(3) 0.089 Uiso 1 1 d D U . . .
H4B H 0.679(8) 0.206(4) 0.038(5) 0.089 Uiso 1 1 d D U . . .
H5B H 0.369(8) 0.184(7) 0.080(4) 0.089 Uiso 1 1 d D U . . .
H5A H 0.327(6) 0.062(8) 0.139(6) 0.089 Uiso 1 1 d D U . . .
H9A H 0.860(11) 0.054(16) 0.055(10) 0.089 Uiso 0.5 1 d D U P . .
H9B H 1.015(6) -0.001(18) 0.053(10) 0.089 Uiso 0.5 1 d D U P . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mg1 O3 2.024(4) . ?
Mg1 O5 2.050(4) . ?
Mg1 O1 2.066(3) . ?
Mg1 O4 2.067(3) . ?
Mg1 O2 2.092(3) . ?
Mg1 N1 2.203(4) . ?
O1 C6 1.284(5) . ?
O2 H2A 0.871(10) . ?
O2 H2B 0.869(10) . ?
O3 H3A 0.871(10) . ?
O3 H3B 0.872(10) . ?
O4 H4A 0.870(10) . ?
O4 H4B 0.873(10) . ?
O5 H5B 0.872(10) . ?
O5 H5A 0.871(10) . ?
O6 C6 1.236(5) . ?
O7 C7 1.259(5) . ?
O8 C7 1.272(5) . ?
N1 C1 1.341(6) . ?
N1 C5 1.350(6) . ?
C1 C2 1.374(6) . ?
C1 H1 0.96(6) . ?
C2 C3 1.397(6) . ?
C2 H2 1.04(4) . ?
C3 C4 1.398(6) . ?
C3 C7 1.499(7) . ?
C4 C5 1.383(6) . ?
C4 H4 1.03(6) . ?
C5 C6 1.517(6) . ?
O9 O9 1.741(17) 3_755 ?
O9 H9A 0.873(10) . ?
O9 H9B 0.873(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Mg1 O5 97.58(17) . . ?
O3 Mg1 O1 165.73(15) . . ?
O5 Mg1 O1 96.32(16) . . ?
O3 Mg1 O4 88.46(14) . . ?
O5 Mg1 O4 91.24(15) . . ?
O1 Mg1 O4 88.00(14) . . ?
O3 Mg1 O2 94.50(14) . . ?
O5 Mg1 O2 83.42(14) . . ?
O1 Mg1 O2 90.30(13) . . ?
O4 Mg1 O2 174.18(15) . . ?
O3 Mg1 N1 90.65(15) . . ?
O5 Mg1 N1 168.16(17) . . ?
O1 Mg1 N1 76.12(14) . . ?
O4 Mg1 N1 97.50(14) . . ?
O2 Mg1 N1 87.48(14) . . ?
C6 O1 Mg1 120.2(3) . . ?
Mg1 O2 H2A 128(5) . . ?
Mg1 O2 H2B 123(5) . . ?
H2A O2 H2B 101(7) . . ?
Mg1 O3 H3A 129(5) . . ?
Mg1 O3 H3B 122(5) . . ?
H3A O3 H3B 108(7) . . ?
Mg1 O4 H4A 123(5) . . ?
Mg1 O4 H4B 124(5) . . ?
H4A O4 H4B 89(6) . . ?
Mg1 O5 H5B 127(5) . . ?
Mg1 O5 H5A 123(6) . . ?
H5B O5 H5A 109(7) . . ?
C1 N1 C5 117.6(4) . . ?
C1 N1 Mg1 129.0(3) . . ?
C5 N1 Mg1 113.3(3) . . ?
N1 C1 C2 123.4(4) . . ?
N1 C1 H1 115(3) . . ?
C2 C1 H1 122(3) . . ?
C1 C2 C3 119.4(4) . . ?
C1 C2 H2 124(2) . . ?
C3 C2 H2 116(2) . . ?
C2 C3 C4 117.4(4) . . ?
C2 C3 C7 122.2(4) . . ?
C4 C3 C7 120.5(4) . . ?
C5 C4 C3 119.6(4) . . ?
C5 C4 H4 122(3) . . ?
C3 C4 H4 119(3) . . ?
N1 C5 C4 122.5(4) . . ?
N1 C5 C6 114.7(4) . . ?
C4 C5 C6 122.7(4) . . ?
O6 C6 O1 125.0(4) . . ?
O6 C6 C5 119.7(4) . . ?
O1 C6 C5 115.3(4) . . ?
O7 C7 O8 124.8(4) . . ?
O7 C7 C3 118.9(4) . . ?
O8 C7 C3 116.2(4) . . ?
O9 O9 H9A 174(10) 3_755 . ?
O9 O9 H9B 49(10) 3_755 . ?
H9A O9 H9B 127(10) . . ?

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 -0.8(6) . . . . ?
Mg1 N1 C1 C2 -177.0(3) . . . . ?
N1 C1 C2 C3 -2.5(7) . . . . ?
C1 C2 C3 C4 2.9(6) . . . . ?
C1 C2 C3 C7 -179.1(4) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C7 C3 C4 C5 -178.3(4) . . . . ?
C1 N1 C5 C4 3.6(6) . . . . ?
Mg1 N1 C5 C4 -179.6(3) . . . . ?
C1 N1 C5 C6 -173.4(4) . . . . ?
Mg1 N1 C5 C6 3.4(5) . . . . ?
C3 C4 C5 N1 -3.1(6) . . . . ?
C3 C4 C5 C6 173.7(4) . . . . ?
Mg1 O1 C6 O6 -171.6(3) . . . . ?
Mg1 O1 C6 C5 7.0(5) . . . . ?
N1 C5 C6 O6 171.9(4) . . . . ?
C4 C5 C6 O6 -5.1(7) . . . . ?
N1 C5 C6 O1 -6.7(6) . . . . ?
C4 C5 C6 O1 176.3(4) . . . . ?
C2 C3 C7 O7 -12.4(6) . . . . ?
C4 C3 C7 O7 165.5(4) . . . . ?
C2 C3 C7 O8 169.9(4) . . . . ?
C4 C3 C7 O8 -12.2(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
C1 H1 O3 0.96(6) 2.66(5) 3.231(6) 119(4) .
C2 H2 O9 1.04(4) 2.40(5) 3.326(9) 147(3) 2_745
C4 H4 O9 1.03(6) 2.27(6) 3.228(9) 155(5) 2_755
O2 H2A O7 0.871(10) 1.85(3) 2.696(4) 162(8) 3_756
O2 H2B O1 0.869(10) 1.91(4) 2.708(4) 152(7) 2_645
O3 H3A O2 0.871(10) 1.99(3) 2.817(4) 158(7) 2_645
O3 H3B O8 0.872(10) 1.824(19) 2.687(4) 169(8) 2_745
O4 H4A O5 0.870(10) 2.46(5) 3.196(5) 142(7) 3_655
O4 H4B O7 0.873(10) 1.904(12) 2.776(4) 177(7) 2_755
O5 H5B O8 0.872(10) 1.758(13) 2.629(5) 176(7) 4_465
O5 H5A O6 0.871(10) 1.872(12) 2.742(5) 178(8) 2_645
O9 H9A O4 0.873(10) 1.89(7) 2.701(9) 154(14) .
O9 H9B O6 0.873(10) 2.00(7) 2.806(9) 153(13) 2_745

_refine_diff_density_max         0.576
_refine_diff_density_min         -0.851
_refine_diff_density_rms         0.138

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 964960'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_p14ccw7_twin1_hklf4

_audit_creation_date             2014-02-04T15:14:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
'diaqua-bis(pyridine-2,4-dicarboxylato)-magnesium(ii),
magnesium hexahydrate, water solvate'
;
_chemical_melting_point          ?
_chemical_formula_sum            'C14 H28 Mg2 N2 O19'
_chemical_formula_moiety         ?
_chemical_formula_analytical     ?
_chemical_formula_weight         577.06

#==============================================================================

# CRYSTAL DATA

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

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

_cell_length_a                   7.0638(6)
_cell_length_b                   8.9852(8)
_cell_length_c                   9.6628(12)
_cell_angle_alpha                83.104(9)
_cell_angle_beta                 75.593(9)
_cell_angle_gamma                83.597(7)
_cell_volume                     587.58(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3839
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      28.958
_cell_measurement_temperature    150(2)
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_F_000             302
_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.90415
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3795
_diffrn_reflns_number            7669
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_theta_min         2.988
_diffrn_reflns_theta_max         29.745
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 Refined as a 3-component twin.
;
_reflns_number_total             7669
_reflns_number_gt                4917
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1925
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.079
_refine_ls_number_reflns         7669
_refine_ls_number_parameters     210
_refine_ls_number_restraints     19
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0992P)²+0.1736P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.856
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mg Mg 0.0486 0.0363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.3445(5) 0.3582(4) 0.3274(4) 0.0173(8) Uani d 1 . . C
H1 0.3595 0.2618 0.2932 0.021 Uiso calc 1 . . H
C2 0.2566(5) 0.3719(4) 0.4705(4) 0.0165(8) Uani d 1 . . C
H2 0.2108 0.2863 0.5324 0.02 Uiso calc 1 . . H
C3 0.2358(5) 0.5102(4) 0.5230(4) 0.0139(7) Uani d 1 . . C
C4 0.3092(5) 0.6310(4) 0.4286(4) 0.0144(7) Uani d 1 . . C
H4 0.3009 0.7277 0.4611 0.017 Uiso calc 1 . . H
C5 0.3940(5) 0.6088(4) 0.2876(4) 0.0136(7) Uani d 1 . . C
C6 0.4785(5) 0.7372(4) 0.1822(4) 0.0152(7) Uani d 1 . . C
C7 0.1353(5) 0.5323(4) 0.6782(4) 0.0152(7) Uani d 1 . . C
N1 0.4095(4) 0.4756(3) 0.2349(3) 0.0142(6) Uani d 1 . . N
O1 0.4990(4) 0.8535(3) 0.2297(3) 0.0237(6) Uani d 1 . . O
O2 0.5248(4) 0.7127(3) 0.0501(3) 0.0169(6) Uani d 1 . . O
O3 0.2131(4) 0.5568(3) -0.0013(3) 0.0214(6) Uani d 1 . . O
O4 0.1181(4) 0.6618(3) 0.7164(3) 0.0249(7) Uani d 1 . . O
O5 0.0787(4) 0.4198(3) 0.7588(3) 0.0270(7) Uani d 1 . . O
O6 0.1103(4) 0.1717(3) 0.0725(3) 0.0218(6) Uani d 1 . . O
O7 0.0157(4) -0.1307(3) 0.1858(3) 0.0216(6) Uani d 1 . . O
O8 0.2824(4) -0.0789(3) -0.0959(3) 0.0190(6) Uani d 1 . . O
O9 -0.1163(5) 0.0399(3) 0.4066(3) 0.0313(7) Uani d 1 . . O
O10 -0.5 0 0.5 0.120(4) Uani d 1 . . O
Mg2 0 0 0 0.0154(4) Uani d 1 . . Mg
Mg1 0.5 0.5 0 0.0142(4) Uani d 1 . . Mg
H6A 0.046(5) 0.228(4) 0.134(4) 0.021 Uiso d 1 . . H
H6B 0.220(3) 0.203(4) 0.034(4) 0.021 Uiso d 1 . . H
H7A -0.014(6) -0.084(4) 0.261(3) 0.021 Uiso d 1 . . H
H7B -0.021(6) -0.218(2) 0.208(4) 0.021 Uiso d 1 . . H
H8A 0.340(5) -0.141(3) -0.043(4) 0.021 Uiso d 1 . . H
H8B 0.359(5) -0.013(3) -0.137(4) 0.021 Uiso d 1 . . H
H3A 0.119(4) 0.570(5) 0.070(2) 0.021 Uiso d 1 . . H
H3B 0.173(5) 0.576(5) -0.077(2) 0.021 Uiso d 1 . . H
H10A -0.556(11) 0.054(10) 0.568(8) 0.021 Uiso d 0.5 . . H
H10B -0.378(4) 0.018(9) 0.479(10) 0.021 Uiso d 0.5 . . H
H9A -0.115(6) 0.133(2) 0.379(4) 0.021 Uiso d 1 . . H
H9B -0.142(4) 0.024(4) 0.4947(17) 0.021 Uiso d 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.341(5) ?
C1 C2 . 1.382(5) ?
C1 H1 . 0.95 ?
C2 C3 . 1.378(5) ?
C2 H2 . 0.95 ?
C3 C4 . 1.390(5) ?
C3 C7 . 1.517(5) ?
C4 C5 . 1.373(5) ?
C4 H4 . 0.95 ?
C5 N1 . 1.340(5) ?
C5 C6 . 1.514(5) ?
C6 O1 . 1.228(4) ?
C6 O2 . 1.275(5) ?
C7 O5 . 1.239(4) ?
C7 O4 . 1.247(4) ?
N1 Mg1 . 2.190(3) ?
O2 Mg1 . 2.064(2) ?
O3 Mg1 . 2.036(2) ?
O3 H3A . 0.840(15) ?
O3 H3B . 0.838(15) ?
O6 Mg2 . 2.068(3) ?
O6 H6A . 0.842(15) ?
O6 H6B . 0.835(15) ?
O7 Mg2 . 2.044(3) ?
O7 H7A . 0.847(15) ?
O7 H7B . 0.841(15) ?
O8 Mg2 . 2.065(2) ?
O8 H8A . 0.846(15) ?
O8 H8B . 0.843(15) ?
O9 H9A . 0.845(15) ?
O9 H9B . 0.824(15) ?
O10 H10A . 0.853(16) ?
O10 H10B . 0.864(16) ?
Mg2 O7 2 2.044(3) ?
Mg2 O8 2 2.065(2) ?
Mg2 O6 2 2.068(3) ?
Mg1 O3 2_665 2.036(2) ?
Mg1 O2 2_665 2.064(2) ?
Mg1 N1 2_665 2.190(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
N1 C1 C2 122.7(3) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 117.8(3) . . ?
C2 C3 C7 121.8(3) . . ?
C4 C3 C7 120.4(3) . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 123.3(3) . . ?
N1 C5 C6 116.0(3) . . ?
C4 C5 C6 120.7(3) . . ?
O1 C6 O2 125.7(3) . . ?
O1 C6 C5 118.2(3) . . ?
O2 C6 C5 116.0(3) . . ?
O5 C7 O4 124.4(4) . . ?
O5 C7 C3 117.7(3) . . ?
O4 C7 C3 117.9(3) . . ?
C1 N1 C5 117.3(3) . . ?
C1 N1 Mg1 131.0(2) . . ?
C5 N1 Mg1 111.0(2) . . ?
C6 O2 Mg1 118.0(2) . . ?
Mg1 O3 H3A 127(3) . . ?
Mg1 O3 H3B 123(3) . . ?
H3A O3 H3B 110(2) . . ?
Mg2 O6 H6A 126(2) . . ?
Mg2 O6 H6B 124(2) . . ?
H6A O6 H6B 110(2) . . ?
Mg2 O7 H7A 115(3) . . ?
Mg2 O7 H7B 126(3) . . ?
H7A O7 H7B 108(2) . . ?
Mg2 O8 H8A 116(3) . . ?
Mg2 O8 H8B 116(3) . . ?
H8A O8 H8B 108(2) . . ?
H9A O9 H9B 112(2) . . ?
H10A O10 H10B 105(3) . . ?
O7 Mg2 O7 180 . 2 ?
O7 Mg2 O8 90.51(11) . . ?
O7 Mg2 O8 89.49(11) 2 . ?
O7 Mg2 O8 89.49(11) . 2 ?
O7 Mg2 O8 90.51(11) 2 2 ?
O8 Mg2 O8 180 . 2 ?
O7 Mg2 O6 90.69(11) . 2 ?
O7 Mg2 O6 89.31(11) 2 2 ?
O8 Mg2 O6 90.39(10) . 2 ?
O8 Mg2 O6 89.61(10) 2 2 ?
O7 Mg2 O6 89.31(11) . . ?
O7 Mg2 O6 90.69(11) 2 . ?
O8 Mg2 O6 89.61(10) . . ?
O8 Mg2 O6 90.39(10) 2 . ?
O6 Mg2 O6 180.00(8) 2 . ?
O3 Mg1 O3 180 2_665 . ?
O3 Mg1 O2 90.36(10) 2_665 2_665 ?
O3 Mg1 O2 89.64(10) . 2_665 ?
O3 Mg1 O2 89.64(10) 2_665 . ?
O3 Mg1 O2 90.36(10) . . ?
O2 Mg1 O2 180 2_665 . ?
O3 Mg1 N1 87.88(11) 2_665 2_665 ?
O3 Mg1 N1 92.12(11) . 2_665 ?
O2 Mg1 N1 77.79(10) 2_665 2_665 ?
O2 Mg1 N1 102.21(10) . 2_665 ?
O3 Mg1 N1 92.12(11) 2_665 . ?
O3 Mg1 N1 87.88(11) . . ?
O2 Mg1 N1 102.21(10) 2_665 . ?
O2 Mg1 N1 77.79(10) . . ?
N1 Mg1 N1 180 2_665 . ?

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
C4 H4 O9 0.95 2.63 3.506(4) 154.1 2_566
O6 H6A O4 0.842(15) 1.911(15) 2.749(4) 173(4) 2_566
O6 H6B O2 0.835(15) 1.978(16) 2.812(4) 177(3) 2_665
O7 H7A O9 0.847(15) 1.856(17) 2.691(4) 169(4) .
O7 H7B O5 0.841(15) 1.874(15) 2.712(4) 174(4) 2_556
O8 H8A O2 0.846(15) 2.044(18) 2.878(4) 169(4) 1_545
O8 H8B O1 0.843(15) 1.852(15) 2.690(4) 173(4) 2_665
O3 H3A O5 0.840(15) 1.884(15) 2.721(4) 174(4) 2_566
O3 H3B O4 0.838(15) 2.165(17) 2.988(4) 167(4) 1_554
O3 H3B O5 0.838(15) 2.49(3) 3.136(4) 134(4) 1_554
O10 H10A O1 0.853(16) 2.35(6) 3.064(3) 141(8) 2_566
O10 H10B O9 0.864(16) 1.83(2) 2.685(3) 170(8) .
O9 H9A O4 0.845(15) 1.962(15) 2.799(4) 170(4) 2_566

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 992450'
