#------------------------------------------------------------------------------
#$Date: 2025-04-05 05:39:14 +0200 (Sat 05 de Apr de 2025) $
#$Revision: 298990 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/36/7063630.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_7063630
loop_
_publ_author_name
'Efanov, Daniil E.'
'Tolstikov, Svyatoslav E.'
'Romanenko, Galina V.'
'Letyagin, Gleb A.'
'Smirnova, Kristina A.'
'Chernavin, Platon A.'
'Veber, Sergey L.'
'Romashev, Nikolay F.'
'Osik, Natalya A.'
'Bogomyakov, Artem S.'
_publ_section_title
;
 Stable anion radicals based on a triazole-fused furazano[3,4-b]pyrazine
 scaffold
;
_journal_issue                   10
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3869
_journal_page_last               3876
_journal_paper_doi               10.1039/D4NJ05188B
_journal_volume                  49
_journal_year                    2025
_chemical_formula_sum            'C26 H41 N8 O'
_chemical_formula_weight         481.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-11-19 deposited with the CCDC.	2025-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.076(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5924(4)
_cell_length_b                   17.8690(7)
_cell_length_c                   18.4283(8)
_cell_measurement_reflns_used    3049
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.77
_cell_measurement_theta_min      2.49
_cell_volume                     2827.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22641
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.588
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_description       cube
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5550
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      0.947
_refine_ls_R_factor_all          0.1514
_refine_ls_R_factor_gt           0.0548
_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)+(0.1258P)²+0.0209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1654
_refine_ls_wR_factor_ref         0.2326
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2283
_reflns_number_total             5550
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj05188b2.cif
_cod_data_source_block           5211
_cod_depositor_comments
'Adding full bibliography for 7063629--7063631.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7063630
_shelx_shelxl_version_number     2019/3
_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'
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
O1 O 0.4391(3) 0.76481(15) 1.01764(14) 0.1188(8) Uani 1 1 d . U . . .
N2 N 0.3373(3) 0.82591(17) 1.02039(16) 0.1114(9) Uani 1 1 d . U . . .
C3 C 0.2793(4) 0.83163(19) 0.95366(19) 0.0887(8) Uani 1 1 d . U . . .
N4 N 0.1738(3) 0.88334(15) 0.93114(16) 0.0960(8) Uani 1 1 d . . . . .
C5 C 0.1423(3) 0.87344(16) 0.86052(18) 0.0791(8) Uani 1 1 d . . . . .
N6 N 0.0442(3) 0.91516(13) 0.82000(15) 0.0883(7) Uani 1 1 d . . . . .
N7 N 0.0528(3) 0.88450(12) 0.75361(14) 0.0840(7) Uani 1 1 d . . . . .
C8 C -0.0259(3) 0.91569(16) 0.69241(19) 0.0893(9) Uani 1 1 d . . . . .
C9 C -0.1156(4) 0.9790(2) 0.7013(2) 0.1235(13) Uani 1 1 d . . . . .
H9A H -0.130209 0.998918 0.747136 0.148 Uiso 1 1 calc R U . . .
C10 C -0.1831(5) 1.0121(2) 0.6397(3) 0.1553(17) Uani 1 1 d . . . . .
H10A H -0.240602 1.055761 0.644447 0.186 Uiso 1 1 calc R U . . .
C11 C -0.1672(5) 0.9820(2) 0.5725(3) 0.1486(16) Uani 1 1 d . . . . .
H11A H -0.213261 1.004999 0.531915 0.178 Uiso 1 1 calc R U . . .
C12 C -0.0832(5) 0.9180(2) 0.5652(2) 0.1329(13) Uani 1 1 d . . . . .
H12A H -0.073191 0.896774 0.519586 0.160 Uiso 1 1 calc R U . . .
C13 C -0.0131(4) 0.88467(18) 0.6254(2) 0.1076(10) Uani 1 1 d . . . . .
H13A H 0.043285 0.840695 0.620210 0.129 Uiso 1 1 calc R U . . .
N14 N 0.1492(3) 0.82496(12) 0.74765(14) 0.0891(7) Uani 1 1 d . . . . .
C15 C 0.2069(3) 0.81677(15) 0.81579(17) 0.0785(8) Uani 1 1 d . . . . .
N16 N 0.3097(3) 0.76423(13) 0.83748(15) 0.0955(7) Uani 1 1 d . . . . .
C17 C 0.3455(4) 0.77438(17) 0.9089(2) 0.0903(8) Uani 1 1 d . U . . .
N18 N 0.4441(3) 0.73317(16) 0.94778(19) 0.1150(9) Uani 1 1 d . U . . .
N1 N 0.1299(2) 0.16086(11) 0.88887(11) 0.0757(6) Uani 1 1 d . . . . .
C111 C 0.1584(3) 0.23777(14) 0.91985(16) 0.0828(8) Uani 1 1 d . . . . .
H11B H 0.158017 0.273185 0.879950 0.099 Uiso 1 1 calc R U . . .
H11C H 0.261801 0.238563 0.942759 0.099 Uiso 1 1 calc R U . . .
C112 C 0.0449(4) 0.26462(15) 0.97413(17) 0.0980(9) Uani 1 1 d . . . . .
H11D H 0.047498 0.231343 1.015738 0.118 Uiso 1 1 calc R U . . .
H11E H -0.059621 0.263722 0.952418 0.118 Uiso 1 1 calc R U . . .
C113 C 0.0846(4) 0.3436(2) 0.9989(2) 0.1209(12) Uani 1 1 d . . . . .
H11F H 0.187957 0.343410 1.021881 0.145 Uiso 1 1 calc R U . A 1
H11G H 0.087770 0.375692 0.956497 0.145 Uiso 1 1 calc R U . A 1
C114 C -0.0218(6) 0.3750(3) 1.0484(3) 0.1365(18) Uani 0.816(5) 1 d . . P B 1
H11H H 0.011023 0.424669 1.061396 0.205 Uiso 0.816(5) 1 calc R U P B 1
H11I H -0.124130 0.376784 1.025723 0.205 Uiso 0.816(5) 1 calc R U P B 1
H11J H -0.023798 0.344455 1.091202 0.205 Uiso 0.816(5) 1 calc R U P B 1
C11X C 0.027(2) 0.3981(13) 0.9594(13) 0.1365(18) Uani 0.184(5) 1 d . . P B 2
H11X H 0.059804 0.445118 0.980076 0.205 Uiso 0.184(5) 1 calc R U P B 2
H11Y H 0.064046 0.394105 0.910966 0.205 Uiso 0.184(5) 1 calc R U P B 2
H11Z H -0.084387 0.395273 0.957976 0.205 Uiso 0.184(5) 1 calc R U P B 2
C121 C -0.0307(3) 0.15584(15) 0.85226(15) 0.0849(8) Uani 1 1 d . . . . .
H12B H -0.043836 0.105877 0.832400 0.102 Uiso 1 1 calc R U . . .
H12C H -0.107547 0.162193 0.889065 0.102 Uiso 1 1 calc R U . . .
C122 C -0.0655(3) 0.2117(2) 0.79213(17) 0.1069(10) Uani 1 1 d . . . . .
H12D H -0.051563 0.262044 0.810920 0.128 Uiso 1 1 calc R U . . .
H12E H 0.007237 0.204490 0.753704 0.128 Uiso 1 1 calc R U . . .
C123 C -0.2296(3) 0.2029(2) 0.76150(19) 0.1158(11) Uani 1 1 d . . . . .
H12F H -0.245380 0.151509 0.746065 0.139 Uiso 1 1 calc R U . . .
H12G H -0.302091 0.213324 0.799385 0.139 Uiso 1 1 calc R U . . .
C124 C -0.2644(5) 0.2538(2) 0.6986(2) 0.1509(15) Uani 1 1 d . . . . .
H12H H -0.369804 0.246129 0.681088 0.226 Uiso 1 1 calc R U . . .
H12I H -0.251225 0.304854 0.713774 0.226 Uiso 1 1 calc R U . . .
H12J H -0.194515 0.243040 0.660455 0.226 Uiso 1 1 calc R U . . .
C131 C 0.2568(3) 0.14798(15) 0.83486(15) 0.0860(8) Uani 1 1 d . . . . .
H13B H 0.252159 0.188421 0.799734 0.103 Uiso 1 1 calc R U . . .
H13C H 0.356773 0.151294 0.860820 0.103 Uiso 1 1 calc R U . . .
C132 C 0.2511(4) 0.07517(17) 0.79408(17) 0.1063(10) Uani 1 1 d . . . . .
H13D H 0.150365 0.070118 0.769098 0.128 Uiso 1 1 calc R U . . .
H13E H 0.262933 0.034087 0.828236 0.128 Uiso 1 1 calc R U . . .
C133 C 0.3776(4) 0.0705(2) 0.73943(19) 0.1178(11) Uani 1 1 d . . . . .
H13F H 0.363317 0.110645 0.704397 0.141 Uiso 1 1 calc R U . . .
H13G H 0.477925 0.077700 0.764316 0.141 Uiso 1 1 calc R U . . .
C134 C 0.3785(5) -0.0028(3) 0.6999(3) 0.180(2) Uani 1 1 d . . . . .
H13H H 0.460756 -0.002776 0.666020 0.271 Uiso 1 1 calc R U . . .
H13I H 0.395010 -0.042706 0.734185 0.271 Uiso 1 1 calc R U . . .
H13J H 0.280384 -0.009756 0.674256 0.271 Uiso 1 1 calc R U . . .
C141 C 0.1339(3) 0.10142(14) 0.94849(14) 0.0849(8) Uani 1 1 d . . . . .
H14A H 0.043687 0.108586 0.977893 0.102 Uiso 1 1 calc R U . . .
H14B H 0.123531 0.052687 0.925643 0.102 Uiso 1 1 calc R U . . .
C142 C 0.2764(4) 0.10038(16) 0.99801(16) 0.0948(9) Uiso 1 1 d . . . . .
H14C H 0.287902 0.148371 1.022222 0.114 Uiso 1 1 calc R U . . .
H14D H 0.367960 0.092005 0.969825 0.114 Uiso 1 1 calc R U . . .
C144 C 0.3973(4) 0.0368(2) 1.1077(2) 0.1453(14) Uani 1 1 d . . . . .
H14E H 0.382790 -0.002967 1.141784 0.218 Uiso 1 1 calc R U . . .
H14F H 0.491747 0.028625 1.082626 0.218 Uiso 1 1 calc R U . . .
H14G H 0.403751 0.083689 1.133146 0.218 Uiso 1 1 calc R U . . .
C143 C 0.2630(4) 0.03870(17) 1.05429(17) 0.1071(10) Uiso 1 1 d . . . . .
H14H H 0.167797 0.045852 1.080128 0.129 Uiso 1 1 calc R U . . .
H14I H 0.255769 -0.009198 1.029622 0.129 Uiso 1 1 calc R U . . .
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
N2 O1 N18 112.7(2) . . ?
C3 N2 O1 104.0(3) . . ?
N2 C3 N4 124.7(3) . . ?
N2 C3 C17 109.6(3) . . ?
N4 C3 C17 125.7(3) . . ?
C5 N4 C3 108.7(3) . . ?
N4 C5 N6 125.1(3) . . ?
N4 C5 C15 126.0(3) . . ?
N6 C5 C15 108.9(3) . . ?
C5 N6 N7 103.1(2) . . ?
N6 N7 N14 116.6(2) . . ?
N6 N7 C8 121.8(2) . . ?
N14 N7 C8 121.5(2) . . ?
C13 C8 C9 120.3(3) . . ?
C13 C8 N7 120.8(3) . . ?
C9 C8 N7 118.9(3) . . ?
C10 C9 C8 118.1(3) . . ?
C11 C10 C9 121.5(4) . . ?
C10 C11 C12 119.5(4) . . ?
C11 C12 C13 120.1(4) . . ?
C8 C13 C12 120.4(3) . . ?
C15 N14 N7 102.5(2) . . ?
N14 C15 N16 125.0(3) . . ?
N14 C15 C5 108.9(3) . . ?
N16 C15 C5 126.1(3) . . ?
C15 N16 C17 108.7(3) . . ?
N18 C17 N16 125.1(3) . . ?
N18 C17 C3 110.1(3) . . ?
N16 C17 C3 124.8(3) . . ?
C17 N18 O1 103.5(3) . . ?
C111 N1 C121 110.82(19) . . ?
C111 N1 C141 111.28(19) . . ?
C121 N1 C141 105.95(19) . . ?
C111 N1 C131 106.03(18) . . ?
C121 N1 C131 111.3(2) . . ?
C141 N1 C131 111.6(2) . . ?
N1 C111 C112 116.4(2) . . ?
C111 C112 C113 110.7(3) . . ?
C11X C113 C112 116.8(10) . . ?
C114 C113 C112 114.5(3) . . ?
C122 C121 N1 116.1(2) . . ?
C123 C122 C121 111.3(3) . . ?
C124 C123 C122 112.7(3) . . ?
C132 C131 N1 116.6(2) . . ?
C131 C132 C133 111.8(2) . . ?
C134 C133 C132 112.9(3) . . ?
C142 C141 N1 116.3(2) . . ?
C141 C142 C143 110.1(2) . . ?
C144 C143 C142 113.0(3) . . ?
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 N2 1.401(3) . ?
O1 N18 1.408(3) . ?
N2 C3 1.314(4) . ?
C3 N4 1.349(4) . ?
C3 C17 1.444(4) . ?
N4 C5 1.331(3) . ?
C5 N6 1.333(3) . ?
C5 C15 1.431(4) . ?
N6 N7 1.345(3) . ?
N7 N14 1.355(3) . ?
N7 C8 1.409(3) . ?
C8 C13 1.362(4) . ?
C8 C9 1.382(4) . ?
C9 C10 1.387(5) . ?
C10 C11 1.361(5) . ?
C11 C12 1.361(5) . ?
C12 C13 1.378(4) . ?
N14 C15 1.342(3) . ?
C15 N16 1.340(3) . ?
N16 C17 1.353(4) . ?
C17 N18 1.316(4) . ?
N1 C111 1.505(3) . ?
N1 C121 1.517(3) . ?
N1 C141 1.528(3) . ?
N1 C131 1.520(3) . ?
C111 C112 1.501(4) . ?
C112 C113 1.519(4) . ?
C113 C11X 1.30(2) . ?
C113 C114 1.429(5) . ?
C121 C122 1.513(4) . ?
C122 C123 1.508(4) . ?
C123 C124 1.495(4) . ?
C131 C132 1.503(4) . ?
C132 C133 1.511(4) . ?
C133 C134 1.498(5) . ?
C141 C142 1.501(4) . ?
C142 C143 1.521(4) . ?
C144 C143 1.489(4) . ?
