#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/98/1559880.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_1559880
loop_
_publ_author_name
'Rajak, Sanil'
'Schott, Olivier'
'Kaur, Prabhjyot'
'Maris, Thierry'
'Hanan, Gary S.'
'Duong, Adam'
_publ_section_title
;
 Synthesis, crystal structure, characterization of pyrazine
 diaminotriazine based complexes and their systematic comparative study
 with pyridyl diaminotriazine based complexes for light-driven hydrogen
 production
;
_journal_name_full               Polyhedron
_journal_page_first              114412
_journal_paper_doi               10.1016/j.poly.2020.114412
_journal_volume                  180
_journal_year                    2020
_chemical_formula_moiety         'C14 H14 Cu N15 O3, N O3'
_chemical_formula_sum            'C14 H14 Cu N16 O6'
_chemical_formula_weight         565.95
_chemical_name_systematic
;
(nitrato)-bis[6-(pyrazin-2-yl)-1,3,5-triazine-2,4-diamine]-copper(ii) nitrate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                93.120(2)
_cell_angle_beta                 96.497(2)
_cell_angle_gamma                97.972(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3550(4)
_cell_length_b                   10.4080(5)
_cell_length_c                   12.2948(5)
_cell_measurement_reflns_used    5190
_cell_measurement_temperature    100
_cell_measurement_theta_max      52.199
_cell_measurement_theta_min      3.156
_cell_volume                     1049.33(8)
_computing_cell_refinement
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data. 
Bruker AXS Inc., Madison, WI 53719-1173.'
;
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data. 
Bruker AXS Inc., Madison, WI 53719-1173.'
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3582
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        52.238
_diffrn_reflns_theta_max         52.238
_diffrn_reflns_theta_min         3.155
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    6.058
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_correction_T_min  0.497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 34764 reflections, Rint = 0.0681
 (29284 with I > 3sig(I), Rint = 0.0667)
;
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_description       Frgament
_exptl_crystal_F_000             574
_exptl_crystal_recrystallization_method 'crystallized from MeOH/H2O'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.206
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       0.0094(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1219P)²+0.4271P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1645
_refine_ls_wR_factor_ref         0.1677
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3410
_reflns_number_total             3582
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            rm196.cif
_cod_data_source_block           rm196
_cod_database_code               1559880
_cod_database_fobs_code          1559880
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_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 0.49860(6) 0.23536(6) 0.25348(4) 0.0337(2) Uani 1 1 d . . . . .
O1 O 0.3520(4) 0.2972(3) 0.1149(3) 0.0468(8) Uani 1 1 d . . . . .
N1 N 0.5019(4) 0.2606(3) 0.4217(3) 0.0350(7) Uani 1 1 d . . . . .
C1 C 0.4257(5) 0.1884(5) 0.4924(4) 0.0411(10) Uani 1 1 d . . . . .
H1 H 0.350618 0.113211 0.465881 0.049 Uiso 1 1 calc R . . . .
N2 N 0.5627(5) 0.3239(4) 0.6487(3) 0.0434(9) Uani 1 1 d . . . . .
O2 O 0.2125(5) 0.3676(4) 0.2397(3) 0.0551(9) Uani 1 1 d . . . . .
C2 C 0.4559(6) 0.2228(5) 0.6048(4) 0.0440(10) Uani 1 1 d . . . . .
H2 H 0.396816 0.171243 0.652478 0.053 Uiso 1 1 calc R . . . .
N3 N 0.6380(5) 0.4080(4) 0.2789(3) 0.0345(7) Uani 1 1 d . . . . .
C3 C 0.6404(5) 0.3944(4) 0.5772(4) 0.0378(10) Uani 1 1 d . . . . .
H3 H 0.719243 0.467174 0.604377 0.045 Uiso 1 1 calc R . . . .
O3 O 0.1688(5) 0.4201(4) 0.0727(3) 0.0529(9) Uani 1 1 d . . . . .
C4 C 0.6090(5) 0.3643(4) 0.4649(3) 0.0362(9) Uani 1 1 d . . . . .
N4 N 0.8156(4) 0.5932(4) 0.2376(3) 0.0392(9) Uani 1 1 d . . . . .
C5 C 0.6885(5) 0.4452(4) 0.3854(3) 0.0353(9) Uani 1 1 d . . . . .
N5 N 0.7953(4) 0.5451(4) 0.4244(3) 0.0385(8) Uani 1 1 d . . . . .
C6 C 0.7035(5) 0.4910(4) 0.2058(4) 0.0389(9) Uani 1 1 d . . . . .
N6 N 0.6531(5) 0.4647(4) 0.0999(3) 0.0448(9) Uani 1 1 d . . . . .
H6A H 0.693942 0.514863 0.051477 0.054 Uiso 1 1 calc R . . . .
H6B H 0.578671 0.397109 0.078009 0.054 Uiso 1 1 calc R . . . .
N7 N 0.9714(5) 0.7169(4) 0.3806(3) 0.0473(9) Uani 1 1 d . . . . .
H7A H 1.016440 0.766190 0.333175 0.057 Uiso 1 1 calc R . . . .
H7B H 1.001516 0.734143 0.451437 0.057 Uiso 1 1 calc R . . . .
C7 C 0.8596(5) 0.6177(5) 0.3459(4) 0.0398(10) Uani 1 1 d . . . . .
C8 C 0.7999(5) 0.1856(5) 0.1368(4) 0.0404(10) Uani 1 1 d . . . . .
H8 H 0.845528 0.273759 0.156244 0.048 Uiso 1 1 calc R . . . .
N8 N 0.6522(4) 0.1403(4) 0.1641(3) 0.0364(8) Uani 1 1 d . . . . .
N9 N 0.8305(4) -0.0206(4) 0.0529(3) 0.0441(9) Uani 1 1 d . . . . .
C9 C 0.8861(5) 0.1052(5) 0.0808(4) 0.0421(10) Uani 1 1 d . . . . .
H9 H 0.989003 0.140663 0.061166 0.051 Uiso 1 1 calc R . . . .
C10 C 0.6850(6) -0.0665(5) 0.0844(4) 0.0416(10) Uani 1 1 d . . . . .
H10 H 0.642885 -0.156216 0.070226 0.050 Uiso 1 1 calc R . . . .
N10 N 0.3664(5) 0.0590(4) 0.2249(3) 0.0365(8) Uani 1 1 d . . . . .
N11 N 0.1368(4) -0.1064(4) 0.2244(3) 0.0380(8) Uani 1 1 d . . . . .
C11 C 0.5964(5) 0.0148(4) 0.1370(3) 0.0378(9) Uani 1 1 d . . . . .
C12 C 0.4328(5) -0.0315(4) 0.1687(3) 0.0367(9) Uani 1 1 d . . . . .
N12 N 0.3667(4) -0.1517(4) 0.1364(3) 0.0383(8) Uani 1 1 d . . . . .
C13 C 0.2122(5) 0.0151(4) 0.2482(3) 0.0366(9) Uani 1 1 d . . . . .
N13 N 0.1317(4) 0.0993(4) 0.2963(3) 0.0411(8) Uani 1 1 d . . . . .
H13A H 0.032203 0.074145 0.311323 0.049 Uiso 1 1 calc R . . . .
H13B H 0.178010 0.180281 0.313033 0.049 Uiso 1 1 calc R . . . .
C14 C 0.2154(5) -0.1867(5) 0.1679(3) 0.0405(10) Uani 1 1 d . . . . .
N14 N 0.1410(5) -0.3058(4) 0.1382(3) 0.0459(9) Uani 1 1 d . . . . .
H14A H 0.042595 -0.330646 0.155428 0.055 Uiso 1 1 calc R . . . .
H14B H 0.189792 -0.360312 0.101078 0.055 Uiso 1 1 calc R . . . .
N15 N 0.2430(5) 0.3629(4) 0.1421(3) 0.0424(9) Uani 1 1 d . . . . .
O4 O 1.1233(4) 0.7857(3) 0.6033(3) 0.0478(8) Uani 1 1 d . . . . .
O5 O 1.2477(4) 0.9039(3) 0.4899(3) 0.0513(8) Uani 1 1 d . . . . .
O6 O 1.1825(4) 0.9939(4) 0.6393(3) 0.0532(8) Uani 1 1 d . . . . .
N16 N 1.1859(5) 0.8974(5) 0.5771(4) 0.0434(9) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 -2.7968 3.6874 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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
N1 Cu1 O1 133.91(13) . .
N1 Cu1 N8 128.75(13) . .
N3 Cu1 O1 92.37(15) . .
N3 Cu1 N1 81.31(14) . .
N3 Cu1 N8 97.75(14) . .
N3 Cu1 N10 177.49(12) . .
N8 Cu1 O1 97.32(13) . .
N10 Cu1 O1 88.19(15) . .
N10 Cu1 N1 100.06(14) . .
N10 Cu1 N8 79.75(14) . .
N15 O1 Cu1 113.6(3) . .
C1 N1 Cu1 131.3(3) . .
C1 N1 C4 116.8(4) . .
C4 N1 Cu1 111.7(3) . .
N1 C1 H1 119.8 . .
N1 C1 C2 120.4(4) . .
C2 C1 H1 119.8 . .
C2 N2 C3 115.6(4) . .
C1 C2 H2 118.2 . .
N2 C2 C1 123.5(4) . .
N2 C2 H2 118.2 . .
C5 N3 Cu1 114.4(3) . .
C5 N3 C6 114.4(4) . .
C6 N3 Cu1 130.9(3) . .
N2 C3 H3 119.1 . .
N2 C3 C4 121.9(4) . .
C4 C3 H3 119.1 . .
N1 C4 C3 121.8(4) . .
N1 C4 C5 116.0(4) . .
C3 C4 C5 122.2(4) . .
C6 N4 C7 117.1(4) . .
N3 C5 C4 115.2(4) . .
N5 C5 N3 127.0(4) . .
N5 C5 C4 117.7(4) . .
C5 N5 C7 114.3(4) . .
N4 C6 N3 122.7(4) . .
N6 C6 N3 118.0(4) . .
N6 C6 N4 119.3(4) . .
C6 N6 H6A 120.0 . .
C6 N6 H6B 120.0 . .
H6A N6 H6B 120.0 . .
H7A N7 H7B 120.0 . .
C7 N7 H7A 120.0 . .
C7 N7 H7B 120.0 . .
N4 C7 N5 124.3(4) . .
N7 C7 N4 119.0(4) . .
N7 C7 N5 116.8(4) . .
N8 C8 H8 119.7 . .
N8 C8 C9 120.6(4) . .
C9 C8 H8 119.7 . .
C8 N8 Cu1 129.3(3) . .
C11 N8 Cu1 113.7(3) . .
C11 N8 C8 116.9(4) . .
C9 N9 C10 116.2(4) . .
C8 C9 H9 118.6 . .
N9 C9 C8 122.8(4) . .
N9 C9 H9 118.6 . .
N9 C10 H10 119.5 . .
N9 C10 C11 121.0(5) . .
C11 C10 H10 119.5 . .
C12 N10 Cu1 116.4(3) . .
C12 N10 C13 113.4(4) . .
C13 N10 Cu1 130.1(3) . .
C13 N11 C14 116.5(4) . .
N8 C11 C10 122.4(4) . .
N8 C11 C12 115.2(4) . .
C10 C11 C12 122.3(4) . .
N10 C12 C11 114.8(4) . .
N12 C12 N10 127.5(4) . .
N12 C12 C11 117.7(4) . .
C12 N12 C14 114.2(4) . .
N11 C13 N10 124.2(4) . .
N13 C13 N10 118.1(4) . .
N13 C13 N11 117.7(4) . .
C13 N13 H13A 120.0 . .
C13 N13 H13B 120.0 . .
H13A N13 H13B 120.0 . .
N11 C14 N12 124.1(4) . .
N14 C14 N11 118.2(4) . .
N14 C14 N12 117.7(4) . .
C14 N14 H14A 120.0 . .
C14 N14 H14B 120.0 . .
H14A N14 H14B 120.0 . .
O2 N15 O1 119.4(4) . .
O3 N15 O1 119.8(4) . .
O3 N15 O2 120.9(4) . .
O5 N16 O4 118.4(4) . .
O6 N16 O4 118.9(4) . .
O6 N16 O5 122.7(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 2.164(3) .
Cu1 N1 2.067(3) .
Cu1 N3 1.990(4) .
Cu1 N8 2.094(3) .
Cu1 N10 1.998(4) .
O1 N15 1.275(5) .
N1 C1 1.338(5) .
N1 C4 1.345(5) .
C1 H1 0.9500 .
C1 C2 1.393(6) .
N2 C2 1.328(6) .
N2 C3 1.342(6) .
O2 N15 1.254(5) .
C2 H2 0.9500 .
N3 C5 1.348(6) .
N3 C6 1.385(6) .
C3 H3 0.9500 .
C3 C4 1.387(6) .
O3 N15 1.227(5) .
C4 C5 1.478(6) .
N4 C6 1.326(6) .
N4 C7 1.341(6) .
C5 N5 1.304(6) .
N5 C7 1.369(6) .
C6 N6 1.324(6) .
N6 H6A 0.8800 .
N6 H6B 0.8800 .
N7 H7A 0.8800 .
N7 H7B 0.8800 .
N7 C7 1.309(6) .
C8 H8 0.9500 .
C8 N8 1.344(6) .
C8 C9 1.382(6) .
N8 C11 1.335(6) .
N9 C9 1.340(6) .
N9 C10 1.350(6) .
C9 H9 0.9500 .
C10 H10 0.9500 .
C10 C11 1.380(6) .
N10 C12 1.354(6) .
N10 C13 1.373(6) .
N11 C13 1.334(6) .
N11 C14 1.344(6) .
C11 C12 1.487(6) .
C12 N12 1.316(6) .
N12 C14 1.370(6) .
C13 N13 1.329(5) .
N13 H13A 0.8800 .
N13 H13B 0.8800 .
C14 N14 1.320(6) .
N14 H14A 0.8800 .
N14 H14B 0.8800 .
O4 N16 1.280(6) .
O5 N16 1.243(6) .
O6 N16 1.234(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
_geom_hbond_publ_flag
C1 H1 N13 0.95 2.60 3.239(6) 125.2 . yes
C1 H1 O5 0.95 2.28 3.120(6) 147.7 1_445 yes
C2 H2 O6 0.95 2.37 3.145(6) 138.4 1_445 yes
C3 H3 O2 0.95 2.47 3.261(6) 141.2 2_666 yes
N6 H6A O3 0.88 2.10 2.942(6) 160.6 2_665 yes
N6 H6B O1 0.88 2.14 2.885(5) 142.3 . yes
N7 H7A N11 0.88 2.16 3.043(5) 176.6 1_665 yes
N7 H7B O4 0.88 2.03 2.892(5) 166.5 . yes
N7 H7B O5 0.88 2.50 2.948(5) 112.1 . yes
N7 H7B N16 0.88 2.47 3.190(6) 139.4 . yes
C9 H9 N9 0.95 2.57 3.223(6) 126.0 2_755 yes
C10 H10 O1 0.95 2.65 3.294(6) 125.7 2_655 yes
N13 H13A O4 0.88 2.36 2.940(5) 123.2 2_666 yes
N13 H13A O6 0.88 2.01 2.883(5) 173.1 2_666 yes
N13 H13A N16 0.88 2.44 3.228(6) 149.1 2_666 yes
N13 H13B O2 0.88 2.19 2.921(5) 140.3 . yes
N14 H14A N4 0.88 2.31 3.176(5) 167.0 1_445 yes
N14 H14B O3 0.88 2.27 2.969(6) 136.1 1_545 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168307035
