#------------------------------------------------------------------------------
#$Date: 2025-03-04 21:53:39 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298222 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/96/7249667.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_7249667
loop_
_publ_author_name
'Zelenov, Victor P.'
'Fedyanin, Ivan V.'
'Samigullina, Aida I.'
'Larin, Alexandr A.'
'Sheremetev, Aleksei B.'
_publ_section_title
;
 R-Substituent vs. exocyclic oxygen: influence on synthesis and crystal
 packing of R-[1,2,5]oxadiazolo[3,4-c]cinnoline mono- and dioxides
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              372
_journal_page_last               385
_journal_paper_doi               10.1039/D4CE01068J
_journal_volume                  27
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C8 H3 F N4 O3'
_chemical_formula_sum            'C8 H3 F N4 O3'
_chemical_formula_weight         222.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           'Modified SHELXL output'
_audit_update_record
;
2024-06-24 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.4990(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.14289(10)
_cell_length_b                   5.60083(7)
_cell_length_c                   9.26194(11)
_cell_measurement_reflns_used    7007
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.0170
_cell_measurement_theta_min      4.9330
_cell_volume                     407.048(9)
_computing_cell_refinement       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.103a 64-bit (release 20-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     42.00  99.00   0.50    0.08    --  111.50-125.00 150.00  114
  2  ω     69.00 104.00   0.50    0.08    --  111.50 -95.00 120.00   70
  3  ω     42.00  70.00   0.50    0.08    --  111.50 -95.00   0.00   56
  4  ω     57.00 101.00   0.50    0.08    --  111.50 -95.00 -30.00   88
  5  ω     95.00 137.00   0.50    0.08    --  111.50 -86.00-142.81   84
  6  ω     50.00  99.00   0.50    0.08    --  111.50-125.00 -90.00   98
  7  ω     46.00  72.00   0.50    0.08    --  111.50 -77.00 -90.00   52
  8  ω     41.00  67.00   0.50    0.08    --  111.50 -61.00-120.00   52
  9  ω     42.00  86.00   0.50    0.08    --  111.50 -77.00-120.00   88
 10  ω     40.00  65.00   0.50    0.08    --  111.50 -61.00 -60.00   50
 11  ω     41.00  69.00   0.50    0.08    --  111.50 -61.00   0.00   56
 12  ω     40.00  65.00   0.50    0.08    --  111.50 -61.00  60.00   50
 13  ω     41.00  66.00   0.50    0.08    --  111.50 -61.00 120.00   50
 14  ω     44.00  70.00   0.50    0.08    --  111.50 -61.00 150.00   52
 15  ω     42.00  69.00   0.50    0.08    --  111.50 -61.00 -90.00   54
 16  ω    106.00 145.00   0.50    0.08    --  111.50  15.00 -60.00   78
 17  ω     90.00 117.00   0.50    0.08    --  111.50  77.00   0.00   54
 18  ω     92.00 161.00   0.50    0.08    --  111.50  77.00  30.00  138
 19  ω    144.00 170.00   0.50    0.08    --  111.50  77.00   0.00   52
 20  ω     95.00 143.00   0.50    0.08    --  111.50  77.00 -30.00   96
 21  ω     90.00 116.00   0.50    0.08    --  111.50  77.00 -60.00   52
 22  ω     90.00 129.00   0.50    0.08    --  111.50  77.00 -90.00   78
 23  ω    153.00 178.00   0.50    0.08    --  111.50  61.00  60.00   50
 24  ω    141.00 167.00   0.50    0.08    --  111.50  77.00 120.00   52
 25  ω    143.00 173.00   0.50    0.08    --  111.50  61.00 150.00   60
 26  ω    100.00 125.00   0.50    0.08    --  111.50  61.00 150.00   50
 27  ω     92.00 119.00   0.50    0.08    --  111.50  77.00 120.00   54
 28  ω     97.00 150.00   0.50    0.08    --  111.50  61.00   0.00  106
 29  ω    145.00 171.00   0.50    0.08    --  111.50  61.00 -60.00   52
 30  ω    110.00 177.00   0.50    0.08    --  111.50  61.00 -37.49  134
 31  ω     97.00 133.00   0.50    0.08    --  111.50  61.00 -60.00   72
 32  ω     97.00 135.00   0.50    0.08    --  111.50  61.00 -90.00   76
 33  ω    139.00 173.00   0.50    0.08    --  111.50  61.00 -90.00   68
 34  ω    102.00 178.00   0.50    0.08    --  111.50  34.00-134.00  152
 35  ω    102.00 178.00   0.50    0.08    --  111.50  34.00-134.00  152
 36  ω    152.00 178.00   0.50    0.08    --  111.50  15.00 -60.00   52
 37  ω    101.00 140.00   0.50    0.08    --  111.50  61.00  30.00   78
 38  ω    107.00 133.00   0.50    0.08    --  111.50  45.00  30.00   52
 39  ω    -24.00  39.00   0.50    0.05    --   48.14 -34.00  67.00  126
 40  ω     34.00 120.00   0.50    0.05    --   48.14  57.00   0.00  172
 41  ω    100.00 130.00   0.50    0.08    --  111.50 125.00-150.00   60
 42  ω    141.00 170.00   0.50    0.08    --  111.50 125.00-150.00   58
 43  ω     27.00 120.00   0.50    0.05    --   48.14  77.00 -60.00  186
 44  ω     38.00 122.00   0.50    0.05    --   48.14  34.00-134.00  168
 45  ω     38.00 122.00   0.50    0.05    --   48.14  34.00-134.00  168
 46  ω    -27.00  26.00   0.50    0.05    --  -48.14  19.00  30.00  106
 47  ω    -39.00  26.00   0.50    0.05    --  -48.14  34.00-134.00  130
 48  ω    -51.00 -18.00   0.50    0.08    --  -90.00  45.00  30.00   66
 49  ω    -71.00 -18.00   0.50    0.08    --  -90.00  61.00  60.00  106
 50  ω   -122.00 -37.00   0.50    0.05    --  -48.14 -34.00  67.00  170
 51  ω   -122.00 -37.00   0.50    0.05    --  -48.14 -34.00  67.00  170
 52  ω   -120.00 -37.00   0.50    0.05    --  -48.14 -38.00   0.00  166
 53  ω   -108.00 -74.00   0.50    0.08    --  -90.00 -68.00 -86.31   68
 54  ω   -161.00 -68.00   0.50    0.08    --  -90.00 -77.00 -60.00  186
 55  ω   -161.00 -68.00   0.50    0.08    --  -90.00 -77.00 -30.00  186
 56  ω   -161.00 -68.00   0.50    0.08    --  -90.00 -77.00   0.00  186
 57  ω   -161.00 -68.00   0.50    0.08    --  -90.00 -77.00  30.00  186
 58  ω   -163.00 -79.00   0.50    0.08    --  -90.00 -34.00  67.00  168
 59  ω   -161.00 -73.00   0.50    0.08    --  -90.00 -65.00 -26.23  176
 60  ω   -161.00 -73.00   0.50    0.08    --  -90.00 -65.00 -37.68  176
 61  ω   -161.00 -74.00   0.50    0.08    --  -90.00 -62.00 -66.56  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9091
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.527
_diffrn_reflns_theta_min         4.955
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.387
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.662
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023) 
Numerical absorption correction based on gaussian integration over 
a multifaceted crystal model 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
; 
 Flack x determined using 758 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1752
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0282
_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)+(0.0398P)²+0.0957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0714
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                1741
_reflns_number_total             1752
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01068j2.cif
_cod_data_source_block           1k_z475101
_cod_depositor_comments
'Adding full bibliography for 7249665--7249669.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7249667
_publ_contact_name               'Aida I. Samigullina'
_publ_contact_email              s_aida_88@mail.ru
_shelx_shelxl_version_number     2018/3
_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. 
;
_shelx_estimated_absorpt_t_min   0.689
_shelx_estimated_absorpt_t_max   0.909
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
F8 F 0.97335(16) 0.0424(3) 0.89127(14) 0.0280(3) Uani 1 1 d . . . . .
O1 O 0.40078(18) 0.4388(3) 0.93215(16) 0.0240(3) Uani 1 1 d . . . . .
O2 O 0.28746(18) 0.7796(3) 0.80254(16) 0.0219(3) Uani 1 1 d . . . . .
O5 O 0.77431(18) 0.9396(3) 0.49413(16) 0.0233(3) Uani 1 1 d . . . . .
N1 N 0.4177(2) 0.5932(3) 0.84253(18) 0.0190(4) Uani 1 1 d . . . . .
N3 N 0.3301(2) 0.9348(4) 0.70262(18) 0.0222(4) Uani 1 1 d . . . . .
N4 N 0.5549(2) 0.9580(3) 0.58793(18) 0.0192(4) Uani 1 1 d . . . . .
N5 N 0.6946(2) 0.8520(3) 0.57997(18) 0.0174(3) Uani 1 1 d . . . . .
C3A C 0.4731(2) 0.8494(4) 0.6827(2) 0.0176(4) Uani 1 1 d . . . . .
C5A C 0.7673(2) 0.6398(4) 0.6636(2) 0.0167(4) Uani 1 1 d . . . . .
C6 C 0.9195(2) 0.5507(4) 0.6444(2) 0.0190(4) Uani 1 1 d . . . . .
H6 H 0.974433 0.627528 0.578596 0.023 Uiso 1 1 calc R U . . .
C7 C 0.9894(2) 0.3485(4) 0.7227(2) 0.0207(4) Uani 1 1 d . . . . .
H7 H 1.093335 0.284035 0.711754 0.025 Uiso 1 1 calc R U . . .
C8 C 0.9050(3) 0.2413(4) 0.8176(2) 0.0192(4) Uani 1 1 d . . . . .
C9 C 0.7541(2) 0.3241(4) 0.8389(2) 0.0186(4) Uani 1 1 d . . . . .
H9 H 0.699854 0.245141 0.904376 0.022 Uiso 1 1 calc R U . . .
C9A C 0.6841(2) 0.5281(4) 0.7606(2) 0.0159(4) Uani 1 1 d . . . . .
C9B C 0.5296(2) 0.6430(4) 0.7670(2) 0.0173(4) 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 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0380
0 0 -1 0.0456
1 0 0 0.0238
-1 0 0 0.0434
0 1 0 0.1150
0 -1 0 0.1756
-1 0 1 0.0457
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
N3 O2 N1 108.90(13) . . ?
O1 N1 C9B 136.36(19) . . ?
O1 N1 O2 117.87(15) . . ?
C9B N1 O2 105.77(16) . . ?
C3A N3 O2 104.80(17) . . ?
N5 N4 C3A 114.41(17) . . ?
O5 N5 N4 117.76(17) . . ?
O5 N5 C5A 116.84(16) . . ?
N4 N5 C5A 125.39(16) . . ?
N3 C3A N4 121.70(19) . . ?
N3 C3A C9B 113.13(18) . . ?
N4 C3A C9B 125.18(18) . . ?
C6 C5A C9A 121.29(18) . . ?
C6 C5A N5 118.32(17) . . ?
C9A C5A N5 120.39(17) . . ?
C7 C6 C5A 118.87(19) . . ?
C7 C6 H6 120.6 . . ?
C5A C6 H6 120.6 . . ?
C6 C7 C8 118.81(18) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
F8 C8 C9 118.06(19) . . ?
F8 C8 C7 118.10(17) . . ?
C9 C8 C7 123.8(2) . . ?
C8 C9 C9A 117.36(19) . . ?
C8 C9 H9 121.3 . . ?
C9A C9 H9 121.3 . . ?
C9 C9A C5A 119.84(17) . . ?
C9 C9A C9B 126.24(18) . . ?
C5A C9A C9B 113.92(18) . . ?
N1 C9B C3A 107.40(18) . . ?
N1 C9B C9A 131.92(19) . . ?
C3A C9B C9A 120.68(18) . . ?
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
F8 C8 1.346(3) . ?
O1 N1 1.232(2) . ?
O2 N3 1.380(2) . ?
O2 N1 1.463(2) . ?
O5 N5 1.253(2) . ?
N1 C9B 1.319(3) . ?
N3 C3A 1.316(3) . ?
N4 N5 1.303(2) . ?
N4 C3A 1.377(3) . ?
N5 C5A 1.455(2) . ?
C3A C9B 1.402(3) . ?
C5A C6 1.391(3) . ?
C5A C9A 1.408(3) . ?
C6 C7 1.383(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.376(3) . ?
C9 C9A 1.391(3) . ?
C9 H9 0.9500 . ?
C9A C9B 1.428(3) . ?
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
N3 O2 N1 O1 179.53(16) . . . . ?
N3 O2 N1 C9B -0.04(19) . . . . ?
N1 O2 N3 C3A 0.4(2) . . . . ?
C3A N4 N5 O5 179.05(16) . . . . ?
C3A N4 N5 C5A -1.4(3) . . . . ?
O2 N3 C3A N4 179.56(16) . . . . ?
O2 N3 C3A C9B -0.6(2) . . . . ?
N5 N4 C3A N3 -179.87(18) . . . . ?
N5 N4 C3A C9B 0.3(3) . . . . ?
O5 N5 C5A C6 0.7(3) . . . . ?
N4 N5 C5A C6 -178.85(17) . . . . ?
O5 N5 C5A C9A -178.98(17) . . . . ?
N4 N5 C5A C9A 1.4(3) . . . . ?
C9A C5A C6 C7 0.0(3) . . . . ?
N5 C5A C6 C7 -179.71(16) . . . . ?
C5A C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 F8 178.97(18) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
F8 C8 C9 C9A -179.24(17) . . . . ?
C7 C8 C9 C9A -0.4(3) . . . . ?
C8 C9 C9A C5A 0.5(3) . . . . ?
C8 C9 C9A C9B -179.81(19) . . . . ?
C6 C5A C9A C9 -0.3(3) . . . . ?
N5 C5A C9A C9 179.43(17) . . . . ?
C6 C5A C9A C9B 179.97(17) . . . . ?
N5 C5A C9A C9B -0.3(2) . . . . ?
O1 N1 C9B C3A -179.8(2) . . . . ?
O2 N1 C9B C3A -0.3(2) . . . . ?
O1 N1 C9B C9A 0.0(4) . . . . ?
O2 N1 C9B C9A 179.43(19) . . . . ?
N3 C3A C9B N1 0.6(2) . . . . ?
N4 C3A C9B N1 -179.57(18) . . . . ?
N3 C3A C9B C9A -179.16(17) . . . . ?
N4 C3A C9B C9A 0.7(3) . . . . ?
C9 C9A C9B N1 0.0(3) . . . . ?
C5A C9A C9B N1 179.7(2) . . . . ?
C9 C9A C9B C3A 179.67(18) . . . . ?
C5A C9A C9B C3A -0.6(3) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0001 0.0001 0.9994 -0.1046 -0.1371 0.0059
0.0001 -0.0001 -0.9994 0.1046 0.1371 -0.0059
0.9994 0.0000 -0.0002 0.1017 -0.1471 -0.0807
-0.9994 -0.0000 0.0002 -0.1017 0.1471 0.0807
-0.0000 0.9996 0.0000 0.1005 -0.0661 0.2472
0.0000 -0.9996 -0.0000 -0.1005 0.0661 -0.2472
-0.9995 0.0000 0.9996 -0.2063 0.0100 0.0866
