#------------------------------------------------------------------------------
#$Date: 2025-04-05 05:39:14 +0200 (Sat 05 de Apr de 2025) $
#$Revision: 298990 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/36/7063629.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_7063629
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            'C10 H2 F5 N7 O'
_chemical_formula_weight         331.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 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                 114.975(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2914(17)
_cell_length_b                   28.492(7)
_cell_length_c                   7.258(2)
_cell_measurement_reflns_used    747
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.06
_cell_measurement_theta_min      3.41
_cell_volume                     1179.4(6)
_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 0.986
_diffrn_measured_fraction_theta_max 0.964
_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  0.0525
_diffrn_reflns_av_unetI/netI     0.1325
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5120
_diffrn_reflns_point_group_measured_fraction_full 0.861
_diffrn_reflns_point_group_measured_fraction_max 0.783
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.428
_diffrn_reflns_theta_min         2.860
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.4479
_exptl_absorpt_correction_T_min  0.4138
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.2(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.738
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2333
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.738
_refine_ls_R_factor_all          0.1310
_refine_ls_R_factor_gt           0.0370
_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)+(0.0065P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0383
_refine_ls_wR_factor_ref         0.0514
_reflns_Friedel_coverage         0.613
_reflns_Friedel_fraction_full    0.734
_reflns_Friedel_fraction_max     0.599
_reflns_number_gt                995
_reflns_number_total             2333
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj05188b2.cif
_cod_data_source_block           158s
_cod_depositor_comments
'Adding full bibliography for 7063629--7063631.cif.'
_cod_original_cell_volume        1179.3(6)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7063629
_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, -y, z+1/2'
'x+1/2, y+1/2, 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 1.0377(7) 0.14808(15) 0.4347(7) 0.0568(13) Uani 1 1 d . . . . .
N2 N 1.1308(8) 0.19264(17) 0.4343(8) 0.0447(13) Uani 1 1 d . . . . .
C3 C 0.9717(10) 0.2214(2) 0.4320(9) 0.0411(17) Uani 1 1 d . . . . .
N4 N 0.9813(7) 0.26900(16) 0.4316(7) 0.0500(15) Uani 1 1 d . . . . .
H4A H 1.097518 0.284151 0.427601 0.060 Uiso 1 1 calc R U . . .
C5 C 0.7870(10) 0.2914(2) 0.4383(10) 0.0387(16) Uani 1 1 d . . . . .
N6 N 0.7555(7) 0.33690(17) 0.4469(8) 0.0487(15) Uani 1 1 d . . . . .
N7 N 0.5409(8) 0.33887(18) 0.4495(8) 0.0467(15) Uani 1 1 d . . . . .
N8 N 0.4385(7) 0.29664(16) 0.4450(7) 0.0388(13) Uani 1 1 d . . . . .
C9 C 0.5972(9) 0.26700(19) 0.4377(9) 0.0354(15) Uani 1 1 d . . . . .
N10 N 0.5824(7) 0.21897(15) 0.4312(7) 0.0438(14) Uani 1 1 d . . . . .
H10A H 0.461652 0.204089 0.427184 0.053 Uiso 1 1 calc R U . . .
C11 C 0.7757(10) 0.1965(2) 0.4315(10) 0.0418(17) Uani 1 1 d . . . . .
N12 N 0.8131(8) 0.15133(18) 0.4335(8) 0.0564(15) Uani 1 1 d . . . . .
C13 C 0.4372(11) 0.3808(2) 0.4720(10) 0.0418(16) Uani 1 1 d . . . . .
C14 C 0.5680(10) 0.4144(2) 0.6143(10) 0.056(2) Uani 1 1 d . . . . .
F15 F 0.7942(5) 0.40711(12) 0.7348(6) 0.0770(12) Uani 1 1 d . . . . .
C16 C 0.4602(13) 0.4541(3) 0.6441(12) 0.073(2) Uani 1 1 d . . . . .
F17 F 0.5851(7) 0.48535(15) 0.7848(7) 0.1176(19) Uani 1 1 d . . . . .
C18 C 0.2289(12) 0.4609(3) 0.5312(12) 0.079(3) Uani 1 1 d . . . . .
F19 F 0.1242(7) 0.50040(14) 0.5566(7) 0.131(2) Uani 1 1 d . . . . .
C20 C 0.0986(10) 0.4289(2) 0.3864(11) 0.060(2) Uani 1 1 d . . . . .
F21 F -0.1335(5) 0.43598(12) 0.2753(6) 0.0876(14) Uani 1 1 d . . . . .
C22 C 0.2018(9) 0.3899(2) 0.3591(9) 0.0471(17) Uani 1 1 d . . . . .
F23 F 0.0720(6) 0.35839(11) 0.2185(5) 0.0566(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 0.0033 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'
F F 0.0171 0.0103 '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 N12 111.1(4) . . ?
C3 N2 O1 104.6(5) . . ?
N2 C3 N4 126.9(6) . . ?
N2 C3 C11 110.6(6) . . ?
N4 C3 C11 122.5(5) . . ?
C3 N4 C5 114.6(5) . . ?
N6 C5 C9 110.4(5) . . ?
N6 C5 N4 127.0(5) . . ?
C9 C5 N4 122.5(5) . . ?
C5 N6 N7 102.2(5) . . ?
N8 N7 N6 115.2(4) . . ?
N8 N7 C13 121.2(5) . . ?
N6 N7 C13 123.4(5) . . ?
C9 N8 N7 102.0(4) . . ?
N8 C9 N10 126.6(5) . . ?
N8 C9 C5 110.1(5) . . ?
N10 C9 C5 123.3(5) . . ?
C9 N10 C11 114.8(5) . . ?
N12 C11 N10 127.9(6) . . ?
N12 C11 C3 109.8(5) . . ?
N10 C11 C3 122.3(6) . . ?
C11 N12 O1 103.9(5) . . ?
C22 C13 C14 117.4(6) . . ?
C22 C13 N7 121.7(6) . . ?
C14 C13 N7 120.9(6) . . ?
F15 C14 C16 118.9(6) . . ?
F15 C14 C13 120.7(6) . . ?
C16 C14 C13 120.2(6) . . ?
F17 C16 C18 120.4(7) . . ?
F17 C16 C14 119.8(6) . . ?
C18 C16 C14 119.8(7) . . ?
C16 C18 F19 119.8(7) . . ?
C16 C18 C20 120.9(7) . . ?
F19 C18 C20 119.3(7) . . ?
C22 C20 F21 120.2(6) . . ?
C22 C20 C18 119.6(6) . . ?
F21 C20 C18 120.2(6) . . ?
C20 C22 F23 119.2(5) . . ?
C20 C22 C13 122.1(6) . . ?
F23 C22 C13 118.7(6) . . ?
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 1.399(5) . ?
O1 N12 1.412(6) . ?
N2 C3 1.288(7) . ?
C3 N4 1.359(6) . ?
C3 C11 1.421(8) . ?
N4 C5 1.398(7) . ?
C5 N6 1.316(6) . ?
C5 C9 1.380(7) . ?
N6 N7 1.359(6) . ?
N7 N8 1.358(6) . ?
N7 C13 1.403(7) . ?
N8 C9 1.325(6) . ?
C9 N10 1.371(6) . ?
N10 C11 1.373(7) . ?
C11 N12 1.307(6) . ?
C13 C22 1.381(6) . ?
C13 C14 1.395(7) . ?
C14 F15 1.335(6) . ?
C14 C16 1.382(9) . ?
C16 F17 1.333(6) . ?
C16 C18 1.349(8) . ?
C18 F19 1.356(7) . ?
C18 C20 1.371(8) . ?
C20 C22 1.343(8) . ?
C20 F21 1.353(6) . ?
C22 F23 1.345(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
N4 H4A N8 0.86 2.13 2.944(6) 159.0 1_655 yes
N4 H4A F23 0.86 2.57 3.154(6) 126.3 1_655 yes
N10 H10A N2 0.86 2.13 2.948(7) 159.1 1_455 yes
N10 H10A F23 0.86 2.62 3.054(6) 112.2 4 yes
