#------------------------------------------------------------------------------
#$Date: 2025-03-04 21:53:39 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298222 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/96/7249666.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_7249666
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_formula_moiety         'C8 H3 Br N4 O3'
_chemical_formula_sum            'C8 H3 Br N4 O3'
_chemical_formula_weight         283.05
_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
_atom_sites_solution_primary     dual
_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                 91.796(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6295(2)
_cell_length_b                   6.38437(16)
_cell_length_c                   16.6319(4)
_cell_measurement_reflns_used    2187
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.7830
_cell_measurement_theta_min      5.2990
_cell_volume                     915.87(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      8.00 117.00   0.50    0.10    --   41.39  75.00 163.00  218
  2  ω    -34.00  76.00   0.50    0.05    --    0.00  75.00 163.00  220
  3  ω    -34.00  76.00   0.50    0.05    --    0.00  75.00 163.00  220
  4  ω    -33.00  75.00   0.50    0.10    --   41.39 -75.00  36.00  216
  5  ω    -33.00  75.00   0.50    0.10    --   41.39 -75.00  36.00  216
  6  ω    -75.00  34.00   0.50    0.05    --    0.00 -75.00  36.00  218
  7  ω     34.00  99.00   0.50    0.10    --   41.39-125.00  60.00  130
  8  ω     34.00  99.00   0.50    0.10    --   41.39-125.00 -60.00  130
  9  ω     41.00 106.00   0.50    0.15    --  121.50 -95.00 -60.00  130
 10  ω     41.00 106.00   0.50    0.15    --  121.50 -95.00 -60.00  130
 11  ω     41.00 106.00   0.50    0.15    --  121.50 -95.00   0.00  130
 12  ω     56.00  82.00   0.50    0.15    --  121.50 -95.00  30.00   52
 13  ω     45.00 158.00   0.50    0.15    --  121.50 -82.00 -14.91  226
 14  ω     45.00 158.00   0.50    0.15    --  121.50 -82.00 -14.91  226
 15  ω     47.00  98.00   0.50    0.15    --  121.50 -75.00  36.00  102
 16  ω     47.00 105.00   0.50    0.15    --  121.50 -77.00 120.00  116
 17  ω     69.00 110.00   0.50    0.15    --  121.50 -78.00 163.36   82
 18  ω     47.00 105.00   0.50    0.15    --  121.50 -77.00  90.00  116
 19  ω     47.00 105.00   0.50    0.15    --  121.50 -77.00  60.00  116
 20  ω     62.00  87.00   0.50    0.15    --  121.50 -77.00 -90.00   50
 21  ω     53.00  79.00   0.50    0.15    --  121.50  11.00-173.02   52
 22  ω     87.00 178.00   0.50    0.15    --  121.50  77.00-180.00  182
 23  ω     87.00 178.00   0.50    0.15    --  121.50  77.00-180.00  182
 24  ω     92.00 178.00   0.50    0.15    --  121.50  61.00-120.00  172
 25  ω    147.00 177.00   0.50    0.15    --  121.50  61.00-120.00   60
 26  ω     91.00 170.00   0.50    0.15    --  121.50  77.00 -60.00  158
 27  ω     93.00 119.00   0.50    0.15    --  121.50  61.00  30.00   52
 28  ω     92.00 178.00   0.50    0.15    --  121.50  45.00  60.00  172
 29  ω     92.00 178.00   0.50    0.15    --  121.50  45.00  90.00  172
 30  ω     92.00 178.00   0.50    0.15    --  121.50  45.00 120.00  172
 31  ω     88.00 178.00   0.50    0.15    --  121.50  75.00 163.00  180
 32  ω     96.00 134.00   0.50    0.15    --  121.50  61.00 120.00   76
 33  ω     92.00 120.00   0.50    0.15    --  121.50  45.00 120.00   56
 34  ω     63.00 146.00   0.50    0.15    --  121.50 178.00 -60.00  166
 35  ω     63.00 146.00   0.50    0.15    --  121.50 178.00  30.00  166
 36  ω     63.00 146.00   0.50    0.15    --  121.50 178.00  30.00  166
 37  ω     -1.00  29.00   0.50    0.10    --   41.39  96.00 -82.03   60
 38  ω    -86.00 -13.00   0.50    0.10    --  -41.39 125.00 -90.00  146
 39  ω    -51.00 -21.00   0.50    0.15    -- -100.00  45.00-120.00   60
 40  ω    -51.00 -21.00   0.50    0.15    -- -100.00  45.00 -60.00   60
 41  ω    -51.00 -21.00   0.50    0.15    -- -100.00  45.00  30.00   60
 42  ω    -98.00 -24.00   0.50    0.15    -- -100.00  75.00 163.00  148
 43  ω   -175.00 -66.00   0.50    0.15    -- -100.00 -75.00  36.00  218
 44  ω   -175.00 -66.00   0.50    0.15    -- -100.00 -75.00  36.00  218
;
_diffrn_measurement_device       'four-circle diffractometer'
_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  0.0238
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12248
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.299
_diffrn_reflns_theta_min         5.322
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.169
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.472
_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    2.053
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.762
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.00130(18)
_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   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0254
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0353P)²+1.0468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0701
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1947
_reflns_number_total             1994
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01068j2.cif
_cod_data_source_block           1m_z476101
_cod_depositor_comments
'Adding full bibliography for 7249665--7249669.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7249666
_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   0.357
_shelx_estimated_absorpt_t_max   0.672
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
Br7 Br 0.10970(2) 0.76225(3) 0.43677(2) 0.02141(11) Uani 1 1 d . . . . .
O1 O 0.58170(17) -0.0754(2) 0.62944(8) 0.0206(3) Uani 1 1 d . . . . .
O2 O 0.63682(17) 0.0455(3) 0.75871(8) 0.0216(3) Uani 1 1 d . . . . .
O5 O 0.32665(18) 0.8057(3) 0.73822(9) 0.0210(3) Uani 1 1 d . . . . .
N1 N 0.56664(19) 0.0683(3) 0.67766(9) 0.0172(3) Uani 1 1 d . . . . .
N3 N 0.6023(2) 0.2213(3) 0.80299(11) 0.0217(4) Uani 1 1 d . . . . .
N4 N 0.4655(2) 0.5341(3) 0.77637(10) 0.0189(3) Uani 1 1 d . . . . .
N5 N 0.38312(19) 0.6317(3) 0.72140(10) 0.0169(3) Uani 1 1 d . . . . .
C3A C 0.5208(2) 0.3419(3) 0.75353(11) 0.0173(4) Uani 1 1 d . . . . .
C5A C 0.3501(2) 0.5533(3) 0.63974(11) 0.0162(4) Uani 1 1 d . . . . .
C6 C 0.2599(2) 0.6768(3) 0.58797(12) 0.0181(4) Uani 1 1 d . . . . .
H6 H 0.221577 0.809025 0.604425 0.022 Uiso 1 1 calc R U . . .
C7 C 0.2278(2) 0.5997(3) 0.51128(11) 0.0177(4) Uani 1 1 d . . . . .
C8 C 0.2802(2) 0.4036(3) 0.48663(12) 0.0190(4) Uani 1 1 d . . . . .
H8 H 0.253774 0.353481 0.434197 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3703(2) 0.2830(3) 0.53858(13) 0.0176(4) Uani 1 1 d . . . . .
H9 H 0.407494 0.150355 0.521989 0.021 Uiso 1 1 calc R U . . .
C9A C 0.4064(2) 0.3582(3) 0.61609(11) 0.0155(4) Uani 1 1 d . . . . .
C9B C 0.4970(2) 0.2521(3) 0.67685(13) 0.0165(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'
Br Br -0.6763 1.2805 '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 0.0327
0 0 -1 0.0327
-1 0 0 0.0544
1 0 0 0.0563
0 1 0 0.1175
0 -1 0 0.0928
1 1 1 0.0848
-1 0 1 0.0495
1 0 1 0.0481
0 1 1 0.0981
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 108.65(15) . . ?
O1 N1 C9B 135.70(18) . . ?
O1 N1 O2 118.48(16) . . ?
C9B N1 O2 105.81(16) . . ?
C3A N3 O2 105.22(17) . . ?
N5 N4 C3A 114.88(16) . . ?
O5 N5 N4 118.56(16) . . ?
O5 N5 C5A 116.43(17) . . ?
N4 N5 C5A 125.02(17) . . ?
N3 C3A N4 122.23(18) . . ?
N3 C3A C9B 112.86(19) . . ?
N4 C3A C9B 124.91(19) . . ?
C6 C5A C9A 121.64(18) . . ?
C6 C5A N5 118.01(18) . . ?
C9A C5A N5 120.34(18) . . ?
C7 C6 C5A 117.44(19) . . ?
C7 C6 H6 121.3 . . ?
C5A C6 H6 121.3 . . ?
C6 C7 C8 122.08(19) . . ?
C6 C7 Br7 119.73(16) . . ?
C8 C7 Br7 118.19(15) . . ?
C9 C8 C7 119.85(18) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C9A 119.35(19) . . ?
C8 C9 H9 120.3 . . ?
C9A C9 H9 120.3 . . ?
C5A C9A C9 119.63(18) . . ?
C5A C9A C9B 114.25(17) . . ?
C9 C9A C9B 126.12(19) . . ?
N1 C9B C3A 107.45(19) . . ?
N1 C9B C9A 131.94(19) . . ?
C3A C9B C9A 120.58(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
Br7 C7 1.890(2) . ?
O1 N1 1.228(2) . ?
O2 N3 1.380(2) . ?
O2 N1 1.468(2) . ?
O5 N5 1.248(2) . ?
N1 C9B 1.318(3) . ?
N3 C3A 1.314(3) . ?
N4 N5 1.300(2) . ?
N4 C3A 1.374(3) . ?
N5 C5A 1.467(2) . ?
C3A C9B 1.407(3) . ?
C5A C6 1.388(3) . ?
C5A C9A 1.399(3) . ?
C6 C7 1.387(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(3) . ?
C8 C9 1.379(3) . ?
C8 H8 0.9500 . ?
C9 C9A 1.401(3) . ?
C9 H9 0.9500 . ?
C9A C9B 1.429(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 -178.45(16) . . . . ?
N3 O2 N1 C9B 0.7(2) . . . . ?
N1 O2 N3 C3A -0.8(2) . . . . ?
C3A N4 N5 O5 178.75(17) . . . . ?
C3A N4 N5 C5A -1.2(3) . . . . ?
O2 N3 C3A N4 -179.64(17) . . . . ?
O2 N3 C3A C9B 0.7(2) . . . . ?
N5 N4 C3A N3 -178.08(18) . . . . ?
N5 N4 C3A C9B 1.5(3) . . . . ?
O5 N5 C5A C6 0.1(3) . . . . ?
N4 N5 C5A C6 180.00(18) . . . . ?
O5 N5 C5A C9A -178.91(17) . . . . ?
N4 N5 C5A C9A 1.0(3) . . . . ?
C9A C5A C6 C7 -0.2(3) . . . . ?
N5 C5A C6 C7 -179.18(17) . . . . ?
C5A C6 C7 C8 1.5(3) . . . . ?
C5A C6 C7 Br7 -178.54(14) . . . . ?
C6 C7 C8 C9 -1.8(3) . . . . ?
Br7 C7 C8 C9 178.20(15) . . . . ?
C7 C8 C9 C9A 0.8(3) . . . . ?
C6 C5A C9A C9 -0.7(3) . . . . ?
N5 C5A C9A C9 178.27(17) . . . . ?
C6 C5A C9A C9B -179.92(18) . . . . ?
N5 C5A C9A C9B -1.0(3) . . . . ?
C8 C9 C9A C5A 0.3(3) . . . . ?
C8 C9 C9A C9B 179.50(19) . . . . ?
O1 N1 C9B C3A 178.7(2) . . . . ?
O2 N1 C9B C3A -0.3(2) . . . . ?
O1 N1 C9B C9A 0.7(4) . . . . ?
O2 N1 C9B C9A -178.2(2) . . . . ?
N3 C3A C9B N1 -0.3(2) . . . . ?
N4 C3A C9B N1 -179.93(18) . . . . ?
N3 C3A C9B C9A 177.96(18) . . . . ?
N4 C3A C9B C9A -1.7(3) . . . . ?
C5A C9A C9B N1 179.1(2) . . . . ?
C9 C9A C9B N1 -0.1(4) . . . . ?
C5A C9A C9B C3A 1.3(3) . . . . ?
C9 C9A C9B C3A -177.89(19) . . . . ?
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
0.0003 -0.0001 0.9995 -0.0344 0.0446 0.0735
-0.0003 0.0001 -0.9995 0.0344 -0.0446 -0.0735
-0.9990 -0.0005 0.0007 0.1656 0.0548 0.0372
0.9990 0.0005 -0.0007 -0.1656 -0.0548 -0.0372
-0.0010 0.9989 0.0013 0.0346 -0.1965 0.1354
0.0010 -0.9989 -0.0013 -0.0346 0.1965 -0.1354
0.9983 0.9993 1.0001 -0.1655 -0.2068 0.1717
-0.9987 -0.0006 1.0002 0.1312 0.0994 0.1107
0.9993 0.0004 0.9988 -0.2001 -0.0103 0.0364
-0.0006 0.9988 1.0008 0.0002 -0.1519 0.2089
