#------------------------------------------------------------------------------
#$Date: 2023-12-08 16:16:31 +0200 (Fri, 08 Dec 2023) $
#$Revision: 288183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/04/4310493.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4310493
loop_
_publ_author_name
'Dilovan S. Cati'
'Joan Ribas'
'Jordi Ribas-Ariño'
'Helen Stoeckli-Evans'
_publ_section_title
;
 Self-Assembly of CuII and NiII [2 x 2] Grid Complexes and a Binuclear
 CuII Complex with a New Semiflexible Substituted Pyrazine Ligand:
 Multiple Anion Encapsulation and Magnetic Properties
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1021
_journal_page_last               1030
_journal_paper_doi               10.1021/ic030174s
_journal_volume                  43
_journal_year                    2004
_chemical_formula_sum            'C18 H16 N6 O2'
_chemical_formula_weight         348.37
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.082(18)
_cell_angle_beta                 98.610(18)
_cell_angle_gamma                97.538(18)
_cell_formula_units_Z            2
_cell_length_a                   4.9882(7)
_cell_length_b                   12.079(2)
_cell_length_c                   14.454(2)
_cell_measurement_reflns_used    2791
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.85
_cell_measurement_theta_min      2.69
_cell_volume                     808.8(2)
_computing_cell_refinement       'CELL (Stoe IPDS Software, 2000)'
_computing_data_collection       'EXPOSE (Stoe IPDS Software, 2000)'
_computing_data_reduction        'INTEGRATE (Stoe IPDS Software, 2000)'
_computing_molecular_graphics    'PLATON99 (Spek, 1990)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 0.81\%A
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'phi oscillation'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1401
_diffrn_reflns_av_sigmaI/netI    0.1874
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5978
_diffrn_reflns_theta_full        25.84
_diffrn_reflns_theta_max         25.84
_diffrn_reflns_theta_min         2.69
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.845
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         2910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.845
_refine_ls_R_factor_all          0.1408
_refine_ls_R_factor_gt           0.0766
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1007P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1899
_refine_ls_wR_factor_ref         0.2149
_reflns_number_gt                1309
_reflns_number_total             2910
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ic030174s_si2_1.cif
_cod_data_source_block           H2L
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_database_code               4310493
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6868(7) 0.1364(3) 0.5302(2) 0.0547(10) Uani 1 1 d . . .
O2 O 0.7331(6) 0.3653(3) 0.6705(2) 0.0423(8) Uani 1 1 d . . .
N1 N 0.9895(8) 0.0654(3) 0.2208(3) 0.0427(10) Uani 1 1 d . . .
N2 N 0.7948(8) 0.1246(3) 0.3818(3) 0.0386(10) Uani 1 1 d . . .
H2N H 0.774(10) 0.155(4) 0.344(3) 0.036(15) Uiso 1 1 d . . .
N3 N 0.4716(7) 0.2767(3) 0.3562(3) 0.0382(10) Uani 1 1 d . . .
N4 N 0.2246(7) 0.4003(3) 0.5045(3) 0.0372(9) Uani 1 1 d . . .
N5 N 0.2803(7) 0.3365(3) 0.6778(2) 0.0354(9) Uani 1 1 d . . .
H5N H 0.089(8) 0.348(3) 0.653(3) 0.023(10) Uiso 1 1 d . . .
N6 N 0.6843(8) 0.5023(4) 0.9122(3) 0.0507(12) Uani 1 1 d . . .
C1 C 1.1015(10) 0.0463(4) 0.1390(3) 0.0460(13) Uani 1 1 d . . .
H1A H 1.0650 0.0927 0.0973 0.055 Uiso 1 1 calc R . .
C2 C 1.2612(11) -0.0343(4) 0.1136(4) 0.0504(13) Uani 1 1 d . . .
H2A H 1.3366 -0.0429 0.0558 0.060 Uiso 1 1 calc R . .
C3 C 1.3165(11) -0.1051(4) 0.1712(3) 0.0502(13) Uani 1 1 d . . .
H3A H 1.4259 -0.1639 0.1539 0.060 Uiso 1 1 calc R . .
C4 C 1.2029(10) -0.0858(4) 0.2567(3) 0.0432(12) Uani 1 1 d . . .
H4A H 1.2338 -0.1321 0.2988 0.052 Uiso 1 1 calc R . .
C5 C 1.0466(9) 0.0006(3) 0.2788(3) 0.0320(10) Uani 1 1 d . . .
C6 C 0.9331(9) 0.0265(4) 0.3730(3) 0.0408(12) Uani 1 1 d . . .
H6B H 0.8024 -0.0435 0.3714 0.049 Uiso 1 1 calc R . .
H6A H 1.0856 0.0450 0.4307 0.049 Uiso 1 1 calc R . .
C7 C 0.6740(9) 0.1706(4) 0.4579(3) 0.0369(11) Uani 1 1 d . . .
C8 C 0.5190(8) 0.2649(4) 0.4471(3) 0.0331(10) Uani 1 1 d . . .
C9 C 0.4048(8) 0.3305(4) 0.5217(3) 0.0307(10) Uani 1 1 d . . .
C10 C 0.4891(8) 0.3437(4) 0.6301(3) 0.0340(10) Uani 1 1 d . . .
C11 C 0.3381(9) 0.3573(4) 0.7843(3) 0.0435(12) Uani 1 1 d . . .
H11B H 0.4737 0.3089 0.7992 0.052 Uiso 1 1 calc R . .
H11A H 0.1660 0.3302 0.8040 0.052 Uiso 1 1 calc R . .
C12 C 0.4482(9) 0.4836(4) 0.8454(3) 0.0381(11) Uani 1 1 d . . .
C13 C 0.3188(10) 0.5711(4) 0.8332(3) 0.0500(13) Uani 1 1 d . . .
H13A H 0.1563 0.5539 0.7840 0.060 Uiso 1 1 calc R . .
C14 C 0.4246(12) 0.6870(5) 0.8930(4) 0.0623(16) Uani 1 1 d . . .
H14A H 0.3353 0.7498 0.8863 0.075 Uiso 1 1 calc R . .
C15 C 0.6611(12) 0.7071(5) 0.9617(4) 0.0595(16) Uani 1 1 d . . .
H15A H 0.7405 0.7851 1.0033 0.071 Uiso 1 1 calc R . .
C16 C 0.7810(11) 0.6162(5) 0.9702(3) 0.0617(17) Uani 1 1 d . . .
H16A H 0.9426 0.6323 1.0196 0.074 Uiso 1 1 calc R . .
C17 C 0.1705(9) 0.4069(4) 0.4127(3) 0.0369(11) Uani 1 1 d . . .
H17A H 0.0381 0.4517 0.3968 0.044 Uiso 1 1 calc R . .
C18 C 0.3046(9) 0.3496(4) 0.3410(3) 0.0377(11) Uani 1 1 d . . .
H18A H 0.2766 0.3626 0.2789 0.045 Uiso 1 1 calc R . .
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'
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
C5 N1 C1 117.1(4) . . ?
C7 N2 C6 124.1(4) . . ?
C7 N2 H2N 111(4) . . ?
C6 N2 H2N 125(4) . . ?
C18 N3 C8 117.6(4) . . ?
C17 N4 C9 117.0(4) . . ?
C10 N5 C11 119.9(4) . . ?
C10 N5 H5N 123(2) . . ?
C11 N5 H5N 113(2) . . ?
C12 N6 C16 115.7(5) . . ?
C2 C1 N1 123.7(5) . . ?
C2 C1 H1A 118.2 . . ?
N1 C1 H1A 118.2 . . ?
C1 C2 C3 120.2(5) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 C4 116.7(5) . . ?
C2 C3 H3A 121.6 . . ?
C4 C3 H3A 121.6 . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
N1 C5 C4 122.7(4) . . ?
N1 C5 C6 117.0(4) . . ?
C4 C5 C6 120.4(4) . . ?
N2 C6 C5 109.3(4) . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
N2 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
H6B C6 H6A 108.3 . . ?
O1 C7 N2 122.7(5) . . ?
O1 C7 C8 122.5(4) . . ?
N2 C7 C8 114.9(4) . . ?
N3 C8 C9 120.4(4) . . ?
N3 C8 C7 116.2(4) . . ?
C9 C8 C7 123.1(4) . . ?
N4 C9 C8 121.6(4) . . ?
N4 C9 C10 113.3(4) . . ?
C8 C9 C10 124.7(4) . . ?
O2 C10 N5 123.6(4) . . ?
O2 C10 C9 121.1(4) . . ?
N5 C10 C9 115.2(4) . . ?
N5 C11 C12 114.4(4) . . ?
N5 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
N5 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
H11B C11 H11A 107.6 . . ?
C13 C12 N6 123.2(4) . . ?
C13 C12 C11 121.6(4) . . ?
N6 C12 C11 115.2(4) . . ?
C12 C13 C14 119.8(5) . . ?
C12 C13 H13A 120.1 . . ?
C14 C13 H13A 120.1 . . ?
C15 C14 C13 117.8(6) . . ?
C15 C14 H14A 121.1 . . ?
C13 C14 H14A 121.1 . . ?
C16 C15 C14 119.7(5) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C15 C16 N6 123.9(5) . . ?
C15 C16 H16A 118.1 . . ?
N6 C16 H16A 118.1 . . ?
N4 C17 C18 120.9(4) . . ?
N4 C17 H17A 119.5 . . ?
C18 C17 H17A 119.5 . . ?
N3 C18 C17 122.1(4) . . ?
N3 C18 H18A 119.0 . . ?
C17 C18 H18A 119.0 . . ?
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
O1 C7 1.227(5) . ?
O2 C10 1.227(5) . ?
N1 C5 1.330(5) . ?
N1 C1 1.355(6) . ?
N2 C7 1.345(6) . ?
N2 C6 1.431(6) . ?
N2 H2N 0.75(4) . ?
N3 C18 1.329(6) . ?
N3 C8 1.351(5) . ?
N4 C17 1.342(5) . ?
N4 C9 1.355(6) . ?
N5 C10 1.339(5) . ?
N5 C11 1.462(5) . ?
N5 H5N 1.01(4) . ?
N6 C12 1.354(5) . ?
N6 C16 1.362(6) . ?
C1 C2 1.342(7) . ?
C1 H1A 0.9500 . ?
C2 C3 1.382(7) . ?
C2 H2A 0.9500 . ?
C3 C4 1.406(7) . ?
C3 H3A 0.9500 . ?
C4 C5 1.375(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.515(6) . ?
C6 H6B 0.9900 . ?
C6 H6A 0.9900 . ?
C7 C8 1.491(7) . ?
C8 C9 1.384(6) . ?
C9 C10 1.515(6) . ?
C11 C12 1.501(6) . ?
C11 H11B 0.9900 . ?
C11 H11A 0.9900 . ?
C12 C13 1.349(7) . ?
C13 C14 1.394(7) . ?
C13 H13A 0.9500 . ?
C14 C15 1.367(8) . ?
C14 H14A 0.9500 . ?
C15 C16 1.345(8) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C18 1.382(6) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
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
_geom_hbond_publ_flag
N2 H2N N1 0.74(5) 2.29(5) 2.598(6) 106(4) . yes
N2 H2N N3 0.74(5) 2.23(5) 2.666(5) 118(4) . yes
N5 H5N O2 1.01(4) 1.86(4) 2.787(5) 151(3) 1_455 yes
C4 H4A O1 0.9500 2.4600 3.294(5) 146.00 2_756 yes
C17 H17A N4 0.9500 2.5700 3.319(6) 135.00 2_566 yes
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 0.9(6) . . . . ?
N1 C1 C2 C3 1.0(7) . . . . ?
C1 C2 C3 C4 -1.3(7) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
C1 N1 C5 C4 -2.6(6) . . . . ?
C1 N1 C5 C6 176.9(4) . . . . ?
C3 C4 C5 N1 2.2(6) . . . . ?
C3 C4 C5 C6 -177.2(4) . . . . ?
C7 N2 C6 C5 -179.2(4) . . . . ?
N1 C5 C6 N2 -3.3(5) . . . . ?
C4 C5 C6 N2 176.2(4) . . . . ?
C6 N2 C7 O1 4.5(6) . . . . ?
C6 N2 C7 C8 -174.4(4) . . . . ?
C18 N3 C8 C9 -2.5(5) . . . . ?
C18 N3 C8 C7 171.7(3) . . . . ?
O1 C7 C8 N3 -166.3(4) . . . . ?
N2 C7 C8 N3 12.6(5) . . . . ?
O1 C7 C8 C9 7.7(6) . . . . ?
N2 C7 C8 C9 -173.4(3) . . . . ?
C17 N4 C9 C8 -2.7(5) . . . . ?
C17 N4 C9 C10 170.6(3) . . . . ?
N3 C8 C9 N4 5.8(5) . . . . ?
C7 C8 C9 N4 -168.0(3) . . . . ?
N3 C8 C9 C10 -166.8(3) . . . . ?
C7 C8 C9 C10 19.5(6) . . . . ?
C11 N5 C10 O2 1.2(7) . . . . ?
C11 N5 C10 C9 -175.2(4) . . . . ?
N4 C9 C10 O2 -126.9(4) . . . . ?
C8 C9 C10 O2 46.2(6) . . . . ?
N4 C9 C10 N5 49.5(5) . . . . ?
C8 C9 C10 N5 -137.4(4) . . . . ?
C10 N5 C11 C12 71.7(5) . . . . ?
C16 N6 C12 C13 2.3(6) . . . . ?
C16 N6 C12 C11 -178.0(4) . . . . ?
N5 C11 C12 C13 51.8(6) . . . . ?
N5 C11 C12 N6 -127.9(4) . . . . ?
N6 C12 C13 C14 -1.8(7) . . . . ?
C11 C12 C13 C14 178.6(4) . . . . ?
C12 C13 C14 C15 0.9(7) . . . . ?
C13 C14 C15 C16 -0.8(8) . . . . ?
C14 C15 C16 N6 1.5(8) . . . . ?
C12 N6 C16 C15 -2.2(7) . . . . ?
C9 N4 C17 C18 -3.2(5) . . . . ?
C8 N3 C18 C17 -3.5(6) . . . . ?
N4 C17 C18 N3 6.6(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21131132
