#------------------------------------------------------------------------------
#$Date: 2022-07-04 12:31:56 +0300 (Mon, 04 Jul 2022) $
#$Revision: 276536 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/56/8105636.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_8105636
loop_
_publ_author_name
'Mi, Xia'
'Wang, Xinling'
_publ_section_title
;
 Crystal structure of 3-nitroquinoline 1-oxide, C9H6N2O3
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              335
_journal_page_last               336
_journal_paper_doi               10.1515/ncrs-2018-0397
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C9 H6 N2 O3'
_chemical_formula_sum            'C9 H6 N2 O3'
_chemical_formula_weight         190.16
_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     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 97.426(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.7156(3)
_cell_length_b                   9.4003(3)
_cell_length_c                   19.8188(7)
_cell_measurement_reflns_used    2337
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.2540
_cell_measurement_theta_min      4.4900
_cell_volume                     1610.12(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -21.00    6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega -103.00  -67.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000 -135.0000  -98.0000 36

#__ type_ start__ end____ width___ exp.time_
  3 omega  -90.00  -31.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  133.0000  147.0000 59

#__ type_ start__ end____ width___ exp.time_
  4 omega -110.00  -21.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -61.0000 -120.0000 89

#__ type_ start__ end____ width___ exp.time_
  5 omega   -8.00   24.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
  6 omega  -12.00   58.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000   60.0000 70

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00   81.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -60.0000 41

#__ type_ start__ end____ width___ exp.time_
  8 omega   58.00   90.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
  9 omega   43.00   80.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 37

#__ type_ start__ end____ width___ exp.time_
 10 omega   49.00   98.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 49

#__ type_ start__ end____ width___ exp.time_
 11 omega   42.00   89.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 47

#__ type_ start__ end____ width___ exp.time_
 12 omega   40.00   70.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
 13 omega   50.00  100.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 50

#__ type_ start__ end____ width___ exp.time_
 14 omega   42.00   88.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 46

#__ type_ start__ end____ width___ exp.time_
 15 omega   93.00  177.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00  108.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  150.0000 64

#__ type_ start__ end____ width___ exp.time_
 17 omega   41.00   67.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega  -69.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 19 omega   35.00  125.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000   30.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0281345000
_diffrn_orient_matrix_UB_12      0.1485870000
_diffrn_orient_matrix_UB_13      -0.0319804000
_diffrn_orient_matrix_UB_21      0.0142274000
_diffrn_orient_matrix_UB_22      0.0665981000
_diffrn_orient_matrix_UB_23      0.0715544000
_diffrn_orient_matrix_UB_31      0.1754788000
_diffrn_orient_matrix_UB_32      0.0185053000
_diffrn_orient_matrix_UB_33      -0.0006341000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6132
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.50
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.029
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0536P)²+0.6154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1347
_reflns_number_gt                2376
_reflns_number_total             2882
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2018-0397_suppl.cif
_cod_data_source_block           2
_cod_database_code               8105636
_chemical_oxdiff_formula         C20H20N4O4
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C9(H9), C1'(H1'), C2'(H2'), C3'(H3'),
 C4'(H4'), C7'(H7'), C9'(H9')
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.4429(2) 0.1239(2) 0.58047(9) 0.0565(5) Uani 1 d . . .
O2 O 0.3112(2) 0.3027(2) 0.61027(9) 0.0646(5) Uani 1 d . . .
O3 O -0.0138(2) 0.4577(2) 0.40873(9) 0.0611(5) Uani 1 d . . .
N1 N 0.3450(2) 0.2179(2) 0.56810(10) 0.0453(5) Uani 1 d . . .
N2 N 0.0891(2) 0.3590(2) 0.42195(10) 0.0422(4) Uani 1 d . . .
C1 C 0.2806(3) 0.0869(3) 0.32617(12) 0.0473(6) Uani 1 d . . .
H1 H 0.3524 0.0136 0.3338 0.057 Uiso 1 calc . . R
C2 C 0.2131(3) 0.1152(3) 0.26172(12) 0.0518(6) Uani 1 d . . .
H2 H 0.2406 0.0622 0.2255 0.062 Uiso 1 calc . . R
C3 C 0.1030(3) 0.2230(3) 0.24952(12) 0.0548(6) Uani 1 d . . .
H3 H 0.0574 0.2403 0.2052 0.066 Uiso 1 calc . . R
C4 C 0.0609(3) 0.3038(3) 0.30174(12) 0.0491(6) Uani 1 d . . .
H4 H -0.0126 0.3754 0.2932 0.059 Uiso 1 calc . . R
C5 C 0.1305(3) 0.2765(2) 0.36809(11) 0.0394(5) Uani 1 d . . .
C6 C 0.2423(3) 0.1679(2) 0.38138(11) 0.0385(5) Uani 1 d . . .
C7 C 0.3135(3) 0.1466(2) 0.44879(11) 0.0400(5) Uani 1 d . . .
H7 H 0.3885 0.0767 0.4590 0.048 Uiso 1 calc . . R
C8 C 0.2689(3) 0.2314(2) 0.49809(11) 0.0390(5) Uani 1 d . . .
C9 C 0.1560(3) 0.3364(2) 0.48570(12) 0.0424(5) Uani 1 d . . .
H9 H 0.1275 0.3904 0.5214 0.051 Uiso 1 calc . . R
O1' O 0.6543(2) 0.4153(2) 0.57929(9) 0.0617(5) Uani 1 d . . .
O2' O 0.8159(3) 0.2475(2) 0.61189(9) 0.0747(6) Uani 1 d . . .
O3' O 0.8993(2) -0.0126(2) 0.41109(10) 0.0613(5) Uani 1 d . . .
N1' N 0.7366(2) 0.3145(2) 0.56788(10) 0.0498(5) Uani 1 d . . .
N2' N 0.8196(2) 0.0991(2) 0.42249(10) 0.0447(5) Uani 1 d . . .
C1' C 0.5633(3) 0.3579(3) 0.32214(13) 0.0526(6) Uani 1 d . . .
H1' H 0.5103 0.4419 0.3282 0.063 Uiso 1 calc . . R
C2' C 0.5592(3) 0.3020(3) 0.25883(13) 0.0573(7) Uani 1 d . . .
H2' H 0.5039 0.3481 0.2219 0.069 Uiso 1 calc . . R
C3' C 0.6379(3) 0.1751(3) 0.24884(13) 0.0585(7) Uani 1 d . . .
H3' H 0.6321 0.1364 0.2054 0.070 Uiso 1 calc . . R
C4' C 0.7231(3) 0.1075(3) 0.30230(13) 0.0531(6) Uani 1 d . . .
H4' H 0.7763 0.0241 0.2953 0.064 Uiso 1 calc . . R
C5' C 0.7292(3) 0.1654(2) 0.36770(12) 0.0424(5) Uani 1 d . . .
C6' C 0.6472(3) 0.2901(2) 0.37913(12) 0.0416(5) Uani 1 d . . .
C7' C 0.6491(3) 0.3421(2) 0.44592(12) 0.0439(5) Uani 1 d . . .
H7' H 0.5939 0.4231 0.4549 0.053 Uiso 1 calc . . R
C8' C 0.7350(3) 0.2689(2) 0.49686(11) 0.0405(5) Uani 1 d . . .
C9' C 0.8225(3) 0.1493(2) 0.48569(11) 0.0424(5) Uani 1 d . . .
H9' H 0.8824 0.1048 0.5219 0.051 Uiso 1 calc . . R
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'
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_
_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
O1 N1 C8 117.96(19) . .
O2 N1 O1 123.8(2) . .
O2 N1 C8 118.2(2) . .
O3 N2 C5 118.80(19) . .
O3 N2 C9 120.7(2) . .
C9 N2 C5 120.46(19) . .
C2 C1 H1 119.8 . .
C2 C1 C6 120.4(2) . .
C6 C1 H1 119.8 . .
C1 C2 H2 119.7 . .
C1 C2 C3 120.6(2) . .
C3 C2 H2 119.7 . .
C2 C3 H3 119.4 . .
C4 C3 C2 121.1(2) . .
C4 C3 H3 119.4 . .
C3 C4 H4 120.6 . .
C3 C4 C5 118.8(2) . .
C5 C4 H4 120.6 . .
N2 C5 C6 119.76(19) . .
C4 C5 N2 119.4(2) . .
C4 C5 C6 120.8(2) . .
C1 C6 C5 118.3(2) . .
C1 C6 C7 122.6(2) . .
C5 C6 C7 119.2(2) . .
C6 C7 H7 121.1 . .
C8 C7 C6 117.7(2) . .
C8 C7 H7 121.1 . .
C7 C8 N1 119.6(2) . .
C7 C8 C9 123.5(2) . .
C9 C8 N1 116.9(2) . .
N2 C9 C8 119.4(2) . .
N2 C9 H9 120.3 . .
C8 C9 H9 120.3 . .
O1' N1' C8' 117.9(2) . .
O2' N1' O1' 124.0(2) . .
O2' N1' C8' 118.0(2) . .
O3' N2' C5' 119.1(2) . .
O3' N2' C9' 120.3(2) . .
C9' N2' C5' 120.6(2) . .
C2' C1' H1' 119.6 . .
C2' C1' C6' 120.9(3) . .
C6' C1' H1' 119.6 . .
C1' C2' H2' 119.8 . .
C1' C2' C3' 120.3(2) . .
C3' C2' H2' 119.8 . .
C2' C3' H3' 119.6 . .
C4' C3' C2' 120.8(2) . .
C4' C3' H3' 119.6 . .
C3' C4' H4' 120.4 . .
C3' C4' C5' 119.2(3) . .
C5' C4' H4' 120.4 . .
N2' C5' C6' 119.5(2) . .
C4' C5' N2' 119.6(2) . .
C4' C5' C6' 120.9(2) . .
C5' C6' C1' 117.9(2) . .
C5' C6' C7' 119.7(2) . .
C7' C6' C1' 122.4(2) . .
C6' C7' H7' 121.3 . .
C8' C7' C6' 117.3(2) . .
C8' C7' H7' 121.3 . .
C7' C8' N1' 119.9(2) . .
C7' C8' C9' 123.3(2) . .
C9' C8' N1' 116.8(2) . .
N2' C9' C8' 119.4(2) . .
N2' C9' H9' 120.3 . .
C8' C9' H9' 120.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N1 1.230(3) .
O2 N1 1.219(3) .
O3 N2 1.293(2) .
N1 C8 1.464(3) .
N2 C5 1.404(3) .
N2 C9 1.338(3) .
C1 H1 0.9300 .
C1 C2 1.362(3) .
C1 C6 1.408(3) .
C2 H2 0.9300 .
C2 C3 1.394(4) .
C3 H3 0.9300 .
C3 C4 1.372(4) .
C4 H4 0.9300 .
C4 C5 1.399(3) .
C5 C6 1.412(3) .
C6 C7 1.413(3) .
C7 H7 0.9300 .
C7 C8 1.356(3) .
C8 C9 1.393(3) .
C9 H9 0.9300 .
O1' N1' 1.227(3) .
O2' N1' 1.216(3) .
O3' N2' 1.295(3) .
N1' C8' 1.470(3) .
N2' C5' 1.402(3) .
N2' C9' 1.336(3) .
C1' H1' 0.9300 .
C1' C2' 1.356(4) .
C1' C6' 1.415(3) .
C2' H2' 0.9300 .
C2' C3' 1.403(4) .
C3' H3' 0.9300 .
C3' C4' 1.370(4) .
C4' H4' 0.9300 .
C4' C5' 1.400(3) .
C5' C6' 1.407(3) .
C6' C7' 1.409(3) .
C7' H7' 0.9300 .
C7' C8' 1.363(3) .
C8' C9' 1.393(3) .
C9' H9' 0.9300 .
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
O1 N1 C8 C7 -3.6(3) . . . .
O1 N1 C8 C9 178.6(2) . . . .
O2 N1 C8 C7 174.3(2) . . . .
O2 N1 C8 C9 -3.5(3) . . . .
O3 N2 C5 C4 0.6(3) . . . .
O3 N2 C5 C6 -179.8(2) . . . .
O3 N2 C9 C8 -178.6(2) . . . .
N1 C8 C9 N2 176.1(2) . . . .
N2 C5 C6 C1 179.7(2) . . . .
N2 C5 C6 C7 -1.6(3) . . . .
C1 C2 C3 C4 0.6(4) . . . .
C1 C6 C7 C8 179.5(2) . . . .
C2 C1 C6 C5 1.2(4) . . . .
C2 C1 C6 C7 -177.4(2) . . . .
C2 C3 C4 C5 0.0(4) . . . .
C3 C4 C5 N2 179.7(2) . . . .
C3 C4 C5 C6 0.0(4) . . . .
C4 C5 C6 C1 -0.6(3) . . . .
C4 C5 C6 C7 178.0(2) . . . .
C5 N2 C9 C8 0.8(3) . . . .
C5 C6 C7 C8 0.9(3) . . . .
C6 C1 C2 C3 -1.2(4) . . . .
C6 C7 C8 N1 -176.97(19) . . . .
C6 C7 C8 C9 0.7(3) . . . .
C7 C8 C9 N2 -1.6(3) . . . .
C9 N2 C5 C4 -178.9(2) . . . .
C9 N2 C5 C6 0.8(3) . . . .
O1' N1' C8' C7' 2.8(3) . . . .
O1' N1' C8' C9' -176.5(2) . . . .
O2' N1' C8' C7' -179.2(2) . . . .
O2' N1' C8' C9' 1.5(3) . . . .
O3' N2' C5' C4' 1.9(3) . . . .
O3' N2' C5' C6' -177.4(2) . . . .
O3' N2' C9' C8' -179.5(2) . . . .
N1' C8' C9' N2' 176.9(2) . . . .
N2' C5' C6' C1' 177.0(2) . . . .
N2' C5' C6' C7' -3.9(3) . . . .
C1' C2' C3' C4' -1.6(4) . . . .
C1' C6' C7' C8' -179.4(2) . . . .
C2' C1' C6' C5' 1.7(4) . . . .
C2' C1' C6' C7' -177.4(2) . . . .
C2' C3' C4' C5' 1.0(4) . . . .
C3' C4' C5' N2' -178.3(2) . . . .
C3' C4' C5' C6' 1.0(4) . . . .
C4' C5' C6' C1' -2.3(3) . . . .
C4' C5' C6' C7' 176.8(2) . . . .
C5' N2' C9' C8' -0.1(3) . . . .
C5' C6' C7' C8' 1.5(3) . . . .
C6' C1' C2' C3' 0.3(4) . . . .
C6' C7' C8' N1' -177.6(2) . . . .
C6' C7' C8' C9' 1.7(4) . . . .
C7' C8' C9' N2' -2.4(4) . . . .
C9' N2' C5' C4' -177.5(2) . . . .
C9' N2' C5' C6' 3.2(3) . . . .
