#------------------------------------------------------------------------------
#$Date: 2025-03-04 21:53:39 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298222 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/96/7249668.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_7249668
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         'C9 H6 N4 O2'
_chemical_formula_sum            'C9 H6 N4 O2'
_chemical_formula_weight         202.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_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                 108.588(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.2076(3)
_cell_length_b                   6.3054(2)
_cell_length_c                   8.5808(3)
_cell_measurement_reflns_used    2923
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.3350
_cell_measurement_theta_min      5.6650
_cell_volume                     420.91(3)
_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 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -123.00 -32.00   0.50    0.20    --  -46.47 -24.00 140.00  182
  2  ω    -30.00  30.00   0.50    0.20    --  -46.47  24.00 -54.00  120
  3  ω     32.00 123.00   0.50    0.20    --   46.47  24.00 -54.00  182
  4  ω    -29.00  30.00   0.50    0.20    --   46.47 -24.00 140.00  118
  5  ω   -167.00 -77.00   0.50    0.80    --  -91.75 -24.00 140.00  180
  6  ω     99.00 178.00   0.50    0.80    --  113.25  24.00 -54.00  158
  7  ω     30.00 119.00   0.50    0.20    --   46.47  57.00  90.00  178
  8  ω     23.00 119.00   0.50    0.20    --   46.47  76.00  -3.62  192
  9  ω     30.00 119.00   0.50    0.20    --   46.47  57.00  90.00  178
 10  ω     32.00 120.00   0.50    0.20    --   46.47  38.00  30.00  176
 11  ω    -29.00  27.00   0.50    0.20    --   46.47 -19.00  30.00  112
 12  ω     32.00 120.00   0.50    0.20    --   46.47  38.00  90.00  176
 13  ω    -51.00 -19.00   0.50    0.80    --  -91.75  45.00  60.00   64
 14  ω   -164.00 -74.00   0.50    0.80    --  -91.75 -61.00  60.00  180
 15  ω    -51.00 -19.00   0.50    0.80    --  -91.75  45.00 120.00   64
 16  ω   -164.00 -69.00   0.50    0.80    --  -91.75 -73.00  52.40  190
 17  ω   -164.00 -68.00   0.50    0.80    --  -91.75 -77.00 120.00  192
 18  ω   -164.00 -68.00   0.50    0.80    --  -91.75 -77.00  90.00  192
 19  ω   -164.00 -69.00   0.50    0.80    --  -91.75 -74.00  10.53  190
 20  ω   -146.00 -74.00   0.50    0.80    --  -91.75 -65.00  29.82  144
 21  ω    -94.00 -68.00   0.50    0.80    --  -91.75 -77.00  60.00   52
 22  ω   -151.00-124.00   0.50    0.80    --  -91.75 -76.00  75.40   54
 23  ω    -96.00 -71.00   0.50    0.80    --  -91.75 -77.00   0.00   50
 24  ω    -94.00 -68.00   0.50    0.80    --  -91.75 -77.00  30.00   52
 25  ω    -99.00 -68.00   0.50    0.80    --  -91.75 -76.00  75.40   62
 26  ω   -157.00-131.00   0.50    0.80    --  -91.75 -74.00  10.53   52
 27  ω   -124.00 -72.00   0.50    0.80    --  -91.75 -66.00  53.50  104
 28  ω    -51.00 -26.00   0.50    0.80    --  -91.75  45.00  90.00   50
 29  ω    -95.00 -69.00   0.50    0.80    --  -91.75 -74.00  99.43   52
 30  ω    117.00 143.00   0.50    0.80    --  113.25  61.00  60.00   52
 31  ω    142.00 168.00   0.50    0.80    --  113.25  15.00   0.00   52
 32  ω    153.00 178.00   0.50    0.80    --  113.25 125.00 150.00   50
 33  ω     42.00  71.00   0.50    0.80    --  113.25 -61.00 150.00   58
 34  ω    102.00 135.00   0.50    0.80    --  113.25 125.00  30.00   66
 35  ω     92.00 137.00   0.50    0.80    --  113.25  77.00 -30.00   90
 36  ω    107.00 177.00   0.50    0.80    --  113.25  61.00   0.00  140
 37  ω    105.00 131.00   0.50    0.80    --  113.25 125.00 150.00   52
 38  ω    131.00 176.00   0.50    0.80    --  113.25  30.00-180.00   90
 39  ω     43.00  68.00   0.50    0.80    --  113.25 -61.00 120.00   50
 40  ω     78.00 106.00   0.50    0.80    --  113.25-106.00  27.50   56
 41  ω     41.00  70.00   0.50    0.80    --  113.25 -77.00   0.00   58
 42  ω    107.00 178.00   0.50    0.80    --  113.25  45.00 150.00  142
 43  ω     41.00  68.00   0.50    0.80    --  113.25 -61.00 -60.00   54
 44  ω    136.00 162.00   0.50    0.80    --  113.25  77.00  90.00   52
 45  ω     90.00 128.00   0.50    0.80    --  113.25  77.00  90.00   76
 46  ω     41.00  69.00   0.50    0.80    --  113.25 -95.00  60.00   56
 47  ω    136.00 162.00   0.50    0.80    --  113.25  77.00-120.00   52
 48  ω    105.00 131.00   0.50    0.80    --  113.25  77.00-120.00   52
 49  ω     44.00  70.00   0.50    0.80    --  113.25 -61.00-120.00   52
 50  ω    111.00 137.00   0.50    0.80    --  113.25  61.00  90.00   52
 51  ω     90.00 134.00   0.50    0.80    --  113.25  77.00  30.00   88
 52  ω     90.00 119.00   0.50    0.80    --  113.25  77.00  60.00   58
 53  ω     98.00 145.00   0.50    0.80    --  113.25  61.00-150.00   94
 54  ω    100.00 145.00   0.50    0.80    --  113.25  45.00  30.00   90
 55  ω    141.00 167.00   0.50    0.80    --  113.25  61.00  30.00   52
 56  ω     83.00 109.00   0.50    0.80    --  113.25-125.00 -60.00   52
 57  ω     43.00  69.00   0.50    0.80    --  113.25 -61.00   0.00   52
 58  ω    104.00 144.00   0.50    0.80    --  113.25  61.00 120.00   80
 59  ω    149.00 175.00   0.50    0.80    --  113.25  61.00 120.00   52
 60  ω    100.00 125.00   0.50    0.80    --  113.25  15.00   0.00   50
 61  ω     55.00  81.00   0.50    0.80    --  113.25 -77.00-150.00   52
 62  ω    100.00 126.00   0.50    0.80    --  113.25  15.00 120.00   52
 63  ω     51.00  77.00   0.50    0.80    --  113.25-125.00   0.00   52
 64  ω    153.00 178.00   0.50    0.80    --  113.25 125.00  30.00   50
 65  ω     99.00 151.00   0.50    0.80    --  113.25  61.00-120.00  104
 66  ω     99.00 130.00   0.50    0.80    --  113.25  61.00  30.00   62
 67  ω     43.00  91.00   0.50    0.80    --  113.25 -95.00 120.00   96
 68  ω     62.00  93.00   0.50    0.80    --  113.25 -77.00  60.00   62
 69  ω    112.00 138.00   0.50    0.80    --  113.25 -88.00 -35.15   52
 70  ω    153.00 178.00   0.50    0.80    --  113.25  61.00  60.00   50
 71  ω    113.00 143.00   0.50    0.80    --  113.25  45.00   0.00   60
 72  ω     81.00 106.00   0.50    0.80    --  113.25 -95.00 -90.00   50
 73  ω     44.00  70.00   0.50    0.80    --  113.25 -95.00 -90.00   52
;
_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  0.0254
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8017
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.668
_diffrn_reflns_theta_min         5.439
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.004
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.544
_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            colorless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.057
_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     91
_refine_ls_number_reflns         979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0382
_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)+(0.0549P)²+0.1653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1041
_reflns_Friedel_coverage         0.000
_reflns_number_gt                918
_reflns_number_total             979
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01068j2.cif
_cod_data_source_block           1q_z480101
_cod_depositor_comments
'Adding full bibliography for 7249665--7249669.cif.'
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7249668
_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   0.753
_shelx_estimated_absorpt_t_max   0.952
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-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
O2 O -0.11377(14) 0.750000 0.38791(14) 0.0226(3) Uani 1 2 d S T P . .
O5 O 0.57554(16) 0.750000 0.45053(17) 0.0329(4) Uani 1 2 d S T P . .
N1 N -0.02331(18) 0.750000 0.55654(17) 0.0215(3) Uani 1 2 d S T P . .
N3 N -0.00557(18) 0.750000 0.29378(17) 0.0222(3) Uani 1 2 d S T P . .
N4 N 0.29470(18) 0.750000 0.35703(17) 0.0230(3) Uani 1 2 d S T P . .
N5 N 0.43610(18) 0.750000 0.48079(18) 0.0226(3) Uani 1 2 d S T P . .
C3A C 0.1484(2) 0.750000 0.4014(2) 0.0190(4) Uani 1 2 d S T P . .
C5A C 0.4464(2) 0.750000 0.6540(2) 0.0212(4) Uani 1 2 d S T P . .
C6 C 0.6095(2) 0.750000 0.7697(2) 0.0260(4) Uani 1 2 d S T P . .
H6 H 0.709709 0.750000 0.737028 0.031 Uiso 1 2 calc R U P . .
C7 C 0.6211(2) 0.750000 0.9340(2) 0.0278(4) Uani 1 2 d S T P . .
H7 H 0.731112 0.750000 1.015548 0.033 Uiso 1 2 calc R U P . .
C8 C 0.4742(3) 0.750000 0.9819(2) 0.0268(4) Uani 1 2 d S T P . .
H8 H 0.486401 0.750000 1.095775 0.032 Uiso 1 2 calc R U P . .
C9 C 0.3098(2) 0.750000 0.8675(2) 0.0217(4) Uani 1 2 d S T P . .
C9A C 0.2972(2) 0.750000 0.69967(19) 0.0186(4) Uani 1 2 d S T P . .
C9B C 0.1383(2) 0.750000 0.56410(19) 0.0180(4) Uani 1 2 d S T P . .
C10 C 0.1517(3) 0.750000 0.9201(2) 0.0280(4) Uani 1 2 d S T P . .
H10D H 0.185025 0.750000 1.037941 0.042 Uiso 1 2 d R U P . .
H10A H 0.084635 0.874310 0.877911 0.042 Uiso 1 1 d 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 0.0181 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.1340
1 0 0 0.0932
-1 0 0 0.1070
0 0 1 0.0194
0 0 -1 0.0269
2 1 0 0.1037
-2 2 1 0.1110
-2 1 0 0.1000
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 112.17(11) . . ?
C9B N1 O2 104.28(13) . . ?
C3A N3 O2 104.17(13) . . ?
N5 N4 C3A 113.98(13) . . ?
O5 N5 N4 117.90(14) . . ?
O5 N5 C5A 116.79(14) . . ?
N4 N5 C5A 125.31(14) . . ?
N3 C3A N4 122.68(15) . . ?
N3 C3A C9B 110.32(15) . . ?
N4 C3A C9B 127.01(15) . . ?
C6 C5A C9A 121.99(16) . . ?
C6 C5A N5 117.17(16) . . ?
C9A C5A N5 120.84(14) . . ?
C7 C6 C5A 117.78(17) . . ?
C7 C6 H6 121.1 . . ?
C5A C6 H6 121.1 . . ?
C6 C7 C8 121.10(16) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C9 121.81(16) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C9A 117.33(17) . . ?
C8 C9 C10 121.53(16) . . ?
C9A C9 C10 121.14(15) . . ?
C5A C9A C9 119.99(15) . . ?
C5A C9A C9B 114.87(14) . . ?
C9 C9A C9B 125.14(16) . . ?
N1 C9B C3A 109.06(14) . . ?
N1 C9B C9A 132.95(15) . . ?
C3A C9B C9A 117.99(15) . . ?
C9 C10 H10D 109.5 . . ?
C9 C10 H10A 109.5 . . ?
H10D C10 H10A 109.5 . . ?
C9 C10 H10A 109.47(5) . 4_575 ?
H10D C10 H10A 109.5 . 4_575 ?
H10A C10 H10A 109.5 . 4_575 ?
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
O2 N3 1.3779(18) . ?
O2 N1 1.4000(17) . ?
O5 N5 1.2517(18) . ?
N1 C9B 1.307(2) . ?
N3 C3A 1.306(2) . ?
N4 N5 1.300(2) . ?
N4 C3A 1.370(2) . ?
N5 C5A 1.462(2) . ?
C3A C9B 1.425(2) . ?
C5A C6 1.390(2) . ?
C5A C9A 1.399(2) . ?
C6 C7 1.382(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(2) . ?
C8 H8 0.9500 . ?
C9 C9A 1.410(2) . ?
C9 C10 1.503(3) . ?
C9A C9B 1.445(2) . ?
C10 H10D 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10A 0.9600 4_575 ?
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 C9B 0.000(0) . . . . ?
N1 O2 N3 C3A 0.000(0) . . . . ?
C3A N4 N5 O5 180.000(0) . . . . ?
C3A N4 N5 C5A 0.000(0) . . . . ?
O2 N3 C3A N4 180.000(0) . . . . ?
O2 N3 C3A C9B 0.000(0) . . . . ?
N5 N4 C3A N3 180.000(0) . . . . ?
N5 N4 C3A C9B 0.000(1) . . . . ?
O5 N5 C5A C6 0.000(1) . . . . ?
N4 N5 C5A C6 180.000(1) . . . . ?
O5 N5 C5A C9A 180.000(0) . . . . ?
N4 N5 C5A C9A 0.000(1) . . . . ?
C9A C5A C6 C7 0.000(1) . . . . ?
N5 C5A C6 C7 180.000(1) . . . . ?
C5A C6 C7 C8 0.000(1) . . . . ?
C6 C7 C8 C9 0.000(1) . . . . ?
C7 C8 C9 C9A 0.000(1) . . . . ?
C7 C8 C9 C10 180.000(1) . . . . ?
C6 C5A C9A C9 0.000(1) . . . . ?
N5 C5A C9A C9 180.000(1) . . . . ?
C6 C5A C9A C9B 180.000(1) . . . . ?
N5 C5A C9A C9B 0.000(1) . . . . ?
C8 C9 C9A C5A 0.000(1) . . . . ?
C10 C9 C9A C5A 180.000(1) . . . . ?
C8 C9 C9A C9B 180.000(1) . . . . ?
C10 C9 C9A C9B 0.000(1) . . . . ?
O2 N1 C9B C3A 0.000(0) . . . . ?
O2 N1 C9B C9A 180.000(1) . . . . ?
N3 C3A C9B N1 0.000(0) . . . . ?
N4 C3A C9B N1 180.000(0) . . . . ?
N3 C3A C9B C9A 180.000(0) . . . . ?
N4 C3A C9B C9A 0.000(1) . . . . ?
C5A C9A C9B N1 180.000(1) . . . . ?
C9 C9A C9B N1 0.000(1) . . . . ?
C5A C9A C9B C3A 0.000(1) . . . . ?
C9 C9A C9B C3A 180.000(1) . . . . ?
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
-0.0013 -0.9998 0.0008 -0.0564 -0.0515 -0.2319
0.9988 0.0001 0.0010 -0.1058 -0.1558 0.0606
-0.9988 -0.0001 -0.0010 0.1058 0.1558 -0.0606
-0.0014 -0.0003 0.9997 -0.1781 0.0564 0.0307
0.0014 0.0003 -0.9997 0.1781 -0.0564 -0.0307
1.9989 1.0000 0.0012 -0.1552 -0.2600 0.3532
-1.9963 1.9992 0.9960 0.1463 0.4711 0.3733
-1.9963 0.9997 -0.0029 0.2680 0.3631 0.1107
