# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_mo_dg011412_0m_shelxl_a
_database_code_depnum_ccdc_archive 'CCDC 1846767'
_audit_update_record             
;
2018-06-01 deposited with the CCDC.
2018-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'Cu(II) isonicotinate-N-oxide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 Cu3 N6 O18'
_chemical_formula_weight         867.05

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'
Cu Cu 0.3201 1.2651 '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/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                   8.892(2)
_cell_length_b                   15.096(4)
_cell_length_c                   11.178(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.646(9)
_cell_angle_gamma                90
_cell_volume                     1458.0(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9020
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      35.72

_exptl_crystal_description       PLATE
_exptl_crystal_colour            GREEN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.975
_exptl_crystal_F_000             866
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.267
_shelx_estimated_absorpt_T_min   0.569
_shelx_estimated_absorpt_T_max   0.839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6640
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0944 before and 0.0693 after correction. The Ratio of minimum to maximum transmission is 0.8889. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50042
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.968
_diffrn_reflns_theta_max         27.334
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3288
_reflns_number_gt                3052
_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       'SAINT V8.35A (?, 2016)'
_computing_cell_refinement       'SAINT V8.35A (?, 2016)'
_computing_data_reduction        'SAINT V8.35A (?, 2016)'
_computing_structure_solution    'SAINT V8.35A (?, 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY CSD 3.8'
_computing_publication_material  'MERCURY CSD 3.8'
_refine_special_details          'disordered oxygen atom refined by FVAR'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0319P)²+1.4595P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3288
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0218
_refine_ls_wR_factor_ref         0.0597
_refine_ls_wR_factor_gt          0.0581
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.0000 0.5000 0.01057(7) Uani 1 2 d S . P . .
Cu2 Cu 1.06973(2) 0.45757(2) 0.33541(2) 0.01311(7) Uani 1 1 d . . . . .
O2 O 0.41649(14) 0.11864(8) 0.45665(12) 0.0173(2) Uani 1 1 d . . . . .
N3 N 0.52026(16) 0.18263(10) 0.46147(14) 0.0159(3) Uani 1 1 d . . . . .
C4 C 0.5769(2) 0.22493(12) 0.56876(17) 0.0187(3) Uani 1 1 d . . . . .
H4 H 0.5398 0.2105 0.6394 0.022 Uiso 1 1 calc R U . . .
C5 C 0.6889(2) 0.28931(12) 0.57580(17) 0.0186(3) Uani 1 1 d . . . . .
H5 H 0.7286 0.3197 0.6511 0.022 Uiso 1 1 calc R U . . .
C7 C 0.6799(2) 0.26535(12) 0.36267(17) 0.0202(4) Uani 1 1 d . . . . .
H7 H 0.7144 0.2790 0.2906 0.024 Uiso 1 1 calc R U . . .
C6 C 0.7433(2) 0.30945(11) 0.47220(16) 0.0164(3) Uani 1 1 d . . . . .
C8 C 0.5674(2) 0.20202(12) 0.35844(17) 0.0191(3) Uani 1 1 d . . . . .
H8 H 0.5233 0.1722 0.2835 0.023 Uiso 1 1 calc R U . . .
C9 C 0.87069(19) 0.37706(11) 0.47990(16) 0.0159(3) Uani 1 1 d . . . . .
O10 O 0.93333(15) 0.40885(9) 0.58099(12) 0.0214(3) Uani 1 1 d . . . . .
O11 O 0.90054(15) 0.39398(9) 0.37694(12) 0.0220(3) Uani 1 1 d . . . . .
O12 O 0.92002(13) 0.49610(9) 0.18518(11) 0.0161(2) Uani 1 1 d . . . . .
N13 N 0.76805(16) 0.49033(10) 0.18496(13) 0.0138(3) Uani 1 1 d . . . . .
C14 C 0.68013(19) 0.42961(11) 0.11260(16) 0.0154(3) Uani 1 1 d . . . . .
H14 H 0.7248 0.3903 0.0642 0.019 Uiso 1 1 calc R U . . .
C15 C 0.52423(19) 0.42502(11) 0.10945(15) 0.0149(3) Uani 1 1 d . . . . .
H15 H 0.4601 0.3839 0.0565 0.018 Uiso 1 1 calc R U . . .
C16 C 0.46111(19) 0.48080(12) 0.18403(15) 0.0141(3) Uani 1 1 d . . . . .
C17 C 0.5569(2) 0.54014(13) 0.26049(17) 0.0199(4) Uani 1 1 d . . . . .
H17 H 0.5167 0.5773 0.3140 0.024 Uiso 1 1 calc R U . . .
C18 C 0.7117(2) 0.54506(13) 0.25855(17) 0.0197(4) Uani 1 1 d . . . . .
H18 H 0.7776 0.5868 0.3089 0.024 Uiso 1 1 calc R U . . .
C19 C 0.28977(19) 0.47725(11) 0.17847(15) 0.0130(3) Uani 1 1 d . . . . .
O20 O 0.20640(13) 0.45340(8) 0.07700(11) 0.0155(2) Uani 1 1 d . . . . .
O21 O 0.24852(14) 0.49842(9) 0.27394(12) 0.0200(3) Uani 1 1 d . . . . .
O22 O 1.21973(16) 0.40090(10) 0.47050(13) 0.0285(3) Uani 1 1 d . . . . .
N23 N 1.2111(2) 0.31568(14) 0.46840(17) 0.0345(4) Uani 1 1 d . . . . .
O24 O 1.181(4) 0.2823(15) 0.3654(12) 0.056(4) Uani 0.61(10) 1 d . . P A 1
O24A O 1.137(5) 0.271(2) 0.379(4) 0.068(7) Uani 0.39(10) 1 d . . P A 2
O25 O 1.2514(2) 0.27694(11) 0.56758(16) 0.0458(4) 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
Cu1 O2 1.9555(13) . ?
Cu1 O2 1.9555(13) 3_656 ?
Cu1 O20 1.9643(12) 4_666 ?
Cu1 O20 1.9643(12) 2_545 ?
Cu1 O12 2.3427(13) 2_645 ?
Cu1 O12 2.3427(13) 4_566 ?
Cu2 O11 1.9312(13) . ?
Cu2 O22 1.9598(14) . ?
Cu2 O12 1.9686(13) . ?
Cu2 O21 1.9736(13) 1_655 ?
Cu2 O10 2.2254(14) 3_766 ?
O2 N3 1.3282(19) . ?
N3 C4 1.347(2) . ?
N3 C8 1.347(2) . ?
C4 C5 1.381(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.377(3) . ?
C7 C6 1.391(3) . ?
C7 H7 0.9500 . ?
C6 C9 1.512(2) . ?
C8 H8 0.9500 . ?
C9 O10 1.233(2) . ?
C9 O11 1.267(2) . ?
O10 Cu2 2.2255(14) 3_766 ?
O12 N13 1.3535(18) . ?
O12 Cu1 2.3427(13) 2_655 ?
N13 C18 1.344(2) . ?
N13 C14 1.344(2) . ?
C14 C15 1.380(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.393(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(3) . ?
C16 C19 1.511(2) . ?
C17 C18 1.383(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 O21 1.249(2) . ?
C19 O20 1.253(2) . ?
O20 Cu1 1.9643(12) 2 ?
O21 Cu2 1.9737(13) 1_455 ?
O22 N23 1.289(3) . ?
N23 O24 1.227(16) . ?
N23 O25 1.230(3) . ?
N23 O24A 1.26(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
O2 Cu1 O2 180.0 . 3_656 ?
O2 Cu1 O20 92.37(5) . 4_666 ?
O2 Cu1 O20 87.63(5) 3_656 4_666 ?
O2 Cu1 O20 87.63(5) . 2_545 ?
O2 Cu1 O20 92.37(5) 3_656 2_545 ?
O20 Cu1 O20 180.0 4_666 2_545 ?
O2 Cu1 O12 88.90(5) . 2_645 ?
O2 Cu1 O12 91.10(5) 3_656 2_645 ?
O20 Cu1 O12 87.08(5) 4_666 2_645 ?
O20 Cu1 O12 92.92(5) 2_545 2_645 ?
O2 Cu1 O12 91.10(5) . 4_566 ?
O2 Cu1 O12 88.90(5) 3_656 4_566 ?
O20 Cu1 O12 92.92(5) 4_666 4_566 ?
O20 Cu1 O12 87.08(5) 2_545 4_566 ?
O12 Cu1 O12 180.0 2_645 4_566 ?
O11 Cu2 O22 91.43(6) . . ?
O11 Cu2 O12 86.77(6) . . ?
O22 Cu2 O12 170.59(6) . . ?
O11 Cu2 O21 167.45(6) . 1_655 ?
O22 Cu2 O21 86.96(6) . 1_655 ?
O12 Cu2 O21 92.80(5) . 1_655 ?
O11 Cu2 O10 105.19(6) . 3_766 ?
O22 Cu2 O10 98.37(6) . 3_766 ?
O12 Cu2 O10 91.01(5) . 3_766 ?
O21 Cu2 O10 87.35(5) 1_655 3_766 ?
N3 O2 Cu1 115.88(10) . . ?
O2 N3 C4 119.41(14) . . ?
O2 N3 C8 118.45(15) . . ?
C4 N3 C8 122.13(15) . . ?
N3 C4 C5 119.83(16) . . ?
N3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 119.66(17) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C8 C7 C6 120.20(17) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C5 C6 C7 118.70(16) . . ?
C5 C6 C9 120.23(16) . . ?
C7 C6 C9 121.06(16) . . ?
N3 C8 C7 119.44(17) . . ?
N3 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
O10 C9 O11 127.44(16) . . ?
O10 C9 C6 119.03(16) . . ?
O11 C9 C6 113.52(15) . . ?
C9 O10 Cu2 133.62(12) . 3_766 ?
C9 O11 Cu2 131.36(12) . . ?
N13 O12 Cu2 117.15(10) . . ?
N13 O12 Cu1 120.73(9) . 2_655 ?
Cu2 O12 Cu1 118.42(6) . 2_655 ?
C18 N13 C14 122.65(15) . . ?
C18 N13 O12 118.42(14) . . ?
C14 N13 O12 118.92(14) . . ?
N13 C14 C15 119.19(16) . . ?
N13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C16 119.90(16) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 118.99(16) . . ?
C17 C16 C19 121.09(16) . . ?
C15 C16 C19 119.91(15) . . ?
C18 C17 C16 119.66(16) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
N13 C18 C17 119.53(16) . . ?
N13 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
O21 C19 O20 128.09(16) . . ?
O21 C19 C16 116.89(15) . . ?
O20 C19 C16 115.03(15) . . ?
C19 O20 Cu1 125.87(11) . 2 ?
C19 O21 Cu2 129.83(12) . 1_455 ?
N23 O22 Cu2 113.26(13) . . ?
O24 N23 O25 127.1(9) . . ?
O25 N23 O24A 117(2) . . ?
O24 N23 O22 115.2(10) . . ?
O25 N23 O22 117.06(19) . . ?
O24A N23 O22 124.8(19) . . ?

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.063


_exptl_crystal_recrystallization_method 
'Mixing metal salt and ligand in ethanol and heating'
_chemical_properties_physical    Moisture-sensitive
