#------------------------------------------------------------------------------
#$Date: 2025-03-04 21:53:39 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298222 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/96/7249669.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_7249669
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 O3'
_chemical_formula_sum            'C9 H6 N4 O3'
_chemical_formula_weight         218.18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                77.3481(15)
_cell_angle_beta                 87.0582(15)
_cell_angle_gamma                80.0249(18)
_cell_formula_units_Z            2
_cell_length_a                   5.89689(13)
_cell_length_b                   8.54466(18)
_cell_length_c                   9.10721(12)
_cell_measurement_reflns_used    7668
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      80.4840
_cell_measurement_theta_min      4.9550
_cell_volume                     440.931(15)
_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 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     17.00  80.00   0.50    0.05    --   44.13  77.00 150.00  126
  2  ω     17.00 117.00   0.50    0.05    --   44.13  77.00  60.00  200
  3  ω     17.00 117.00   0.50    0.05    --   44.13  77.00 -30.00  200
  4  ω     25.00 121.00   0.50    0.05    --   44.13  33.00 -47.00  192
  5  ω     25.00 121.00   0.50    0.05    --   44.13  33.00 -47.00  192
  6  ω     91.00 178.00   0.50    0.10    --  117.50  77.00-120.00  174
  7  ω     97.00 178.00   0.50    0.10    --  117.50  61.00-180.00  162
  8  ω     97.00 178.00   0.50    0.10    --  117.50  61.00-180.00  162
  9  ω     98.00 178.00   0.50    0.10    --  117.50  45.00 -90.00  160
 10  ω     91.00 178.00   0.50    0.10    --  117.50  77.00 120.00  174
 11  ω     91.00 178.00   0.50    0.10    --  117.50  77.00 150.00  174
 12  ω     91.00 178.00   0.50    0.10    --  117.50  77.00 150.00  174
 13  ω     98.00 178.00   0.50    0.10    --  117.50  45.00 120.00  160
 14  ω     98.00 178.00   0.50    0.10    --  117.50  45.00  90.00  160
 15  ω     98.00 178.00   0.50    0.10    --  117.50  30.00   0.00  160
 16  ω     98.00 178.00   0.50    0.10    --  117.50  45.00 -30.00  160
 17  ω     98.00 178.00   0.50    0.10    --  117.50  33.00 -47.00  160
 18  ω     98.00 178.00   0.50    0.10    --  117.50  45.00 -90.00  160
 19  ω     98.00 178.00   0.50    0.10    --  117.50  45.00-150.00  160
 20  ω     86.00 178.00   0.50    0.10    --  117.50  15.00-120.00  184
 21  ω     86.00 178.00   0.50    0.10    --  117.50  15.00  60.00  184
 22  ω     86.00 178.00   0.50    0.10    --  117.50  15.00  60.00  184
 23  ω     98.00 178.00   0.50    0.10    --  117.50  30.00  90.00  160
 24  ω     86.00 178.00   0.50    0.10    --  117.50  15.00 150.00  184
 25  ω     45.00 147.00   0.50    0.10    --  117.50 -83.00 -24.56  204
 26  ω     47.00 111.00   0.50    0.10    --  117.50-125.00 120.00  128
 27  ω     34.00  94.00   0.50    0.05    --   44.13-125.00  60.00  120
 28  ω     47.00 111.00   0.50    0.10    --  117.50-125.00  30.00  128
 29  ω     47.00 111.00   0.50    0.10    --  117.50-125.00   0.00  128
 30  ω     45.00 105.00   0.50    0.10    --  117.50 -95.00  30.00  120
 31  ω     47.00 111.00   0.50    0.10    --  117.50-125.00-150.00  128
 32  ω     47.00 111.00   0.50    0.10    --  117.50-125.00-180.00  128
 33  ω     47.00 111.00   0.50    0.10    --  117.50-125.00-180.00  128
 34  ω     45.00 105.00   0.50    0.10    --  117.50 -95.00-180.00  120
 35  ω     45.00 105.00   0.50    0.10    --  117.50 -95.00-120.00  120
 36  ω     45.00 105.00   0.50    0.10    --  117.50 -95.00 -90.00  120
 37  ω     45.00 105.00   0.50    0.10    --  117.50 -95.00 -60.00  120
 38  ω     34.00  94.00   0.50    0.05    --   44.13-125.00-180.00  120
 39  ω     45.00 105.00   0.50    0.10    --  117.50 -95.00   0.00  120
 40  ω     45.00 150.00   0.50    0.10    --  117.50 -88.00  60.98  210
 41  ω     45.00 150.00   0.50    0.10    --  117.50 -88.00  60.98  210
 42  ω     45.00 147.00   0.50    0.10    --  117.50 -83.00 -24.56  204
 43  ω     45.00 145.00   0.50    0.10    --  117.50 -79.00-163.36  200
 44  ω     45.00 145.00   0.50    0.10    --  117.50 -79.00-163.36  200
 45  ω     45.00 105.00   0.50    0.10    --  117.50 -77.00-180.00  120
 46  ω     45.00  71.00   0.50    0.10    --  117.50 -61.00-150.00   52
 47  ω     45.00 105.00   0.50    0.10    --  117.50 -77.00-150.00  120
 48  ω     45.00  71.00   0.50    0.10    --  117.50 -61.00-120.00   52
 49  ω     45.00 105.00   0.50    0.10    --  117.50 -77.00  60.00  120
 50  ω     45.00  71.00   0.50    0.10    --  117.50 -61.00  30.00   52
 51  ω     45.00  71.00   0.50    0.10    --  117.50 -61.00  60.00   52
 52  ω     45.00  71.00   0.50    0.10    --  117.50 -61.00  90.00   52
 53  ω     45.00  71.00   0.50    0.10    --  117.50 -61.00 120.00   52
 54  ω    -34.00  27.00   0.50    0.05    --   44.13 -19.00  90.00  122
 55  ω    -34.00  27.00   0.50    0.05    --   44.13 -19.00   0.00  122
 56  ω    -32.00  38.00   0.50    0.05    --   44.13 -33.00 153.00  140
 57  ω     95.00 178.00   0.50    0.10    --  117.50 125.00 120.00  166
 58  ω    -38.00  33.00   0.50    0.05    --  -44.13  33.00 -47.00  142
 59  ω    -51.00 -21.00   0.50    0.10    --  -96.00  45.00  90.00   60
 60  ω    -51.00 -21.00   0.50    0.10    --  -96.00  45.00 120.00   60
 61  ω    -51.00 -21.00   0.50    0.10    --  -96.00  45.00 150.00   60
 62  ω    -86.00 -25.00   0.50    0.10    --  -96.00 125.00 150.00  122
 63  ω    -86.00 -25.00   0.50    0.10    --  -96.00 125.00   0.00  122
 64  ω   -121.00 -24.00   0.50    0.05    --  -44.13 -33.00 153.00  194
 65  ω   -173.00 -75.00   0.50    0.10    --  -96.00 -33.00 153.00  196
;
_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  0.0261
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.742
_diffrn_reflns_theta_min         4.977
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.096
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.813
_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    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0073(13)
_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   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0359
_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)+(0.0529P)²+0.1804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1004
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1832
_reflns_number_total             1923
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01068j2.cif
_cod_data_source_block           1n_z481102
_cod_depositor_comments
'Adding full bibliography for 7249665--7249669.cif.'
_cod_database_code               7249669
_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   0.779
_shelx_estimated_absorpt_t_max   0.880
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.97625(15) 0.46730(11) 0.34003(10) 0.0251(2) Uani 1 1 d . . . . .
O2 O 0.86076(16) 0.42461(11) 0.11548(10) 0.0259(2) Uani 1 1 d . . . . .
O5 O 0.13734(15) 0.09759(11) 0.32874(10) 0.0231(2) Uani 1 1 d . . . . .
N1 N 0.83960(17) 0.40992(12) 0.27853(12) 0.0205(2) Uani 1 1 d . . . . .
N3 N 0.69549(19) 0.35095(14) 0.06982(13) 0.0258(3) Uani 1 1 d . . . . .
N4 N 0.40017(18) 0.21646(13) 0.19104(11) 0.0214(2) Uani 1 1 d . . . . .
N5 N 0.30489(17) 0.17114(12) 0.32209(11) 0.0187(2) Uani 1 1 d . . . . .
C3A C 0.5816(2) 0.29705(14) 0.19347(14) 0.0203(3) Uani 1 1 d . . . . .
C5A C 0.37736(19) 0.19918(13) 0.46432(13) 0.0172(2) Uani 1 1 d . . . . .
C6 C 0.25561(19) 0.14422(14) 0.59423(13) 0.0189(3) Uani 1 1 d . . . . .
H6 H 0.129540 0.089741 0.589714 0.023 Uiso 1 1 calc R U . . .
C7 C 0.3190(2) 0.16926(14) 0.73123(14) 0.0201(3) Uani 1 1 d . . . . .
C8 C 0.5098(2) 0.24771(14) 0.73457(14) 0.0206(3) Uani 1 1 d . . . . .
H8 H 0.556319 0.262666 0.828187 0.025 Uiso 1 1 calc R U . . .
C9 C 0.63072(19) 0.30337(14) 0.60516(13) 0.0198(3) Uani 1 1 d . . . . .
H9 H 0.757690 0.356932 0.609850 0.024 Uiso 1 1 calc R U . . .
C9A C 0.56441(19) 0.28012(13) 0.46691(13) 0.0175(2) Uani 1 1 d . . . . .
C9B C 0.66601(19) 0.33123(14) 0.32247(13) 0.0192(3) Uani 1 1 d . . . . .
C10 C 0.1842(2) 0.11524(17) 0.87253(14) 0.0261(3) Uani 1 1 d . . . . .
H10A H 0.096918 0.210812 0.904597 0.039 Uiso 1 1 calc R U . . .
H10B H 0.290269 0.053385 0.952128 0.039 Uiso 1 1 calc R U . . .
H10C H 0.077477 0.046333 0.852911 0.039 Uiso 1 1 calc 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 0.0634
0 -1 0 0.0653
-1 0 0 0.0497
1 0 0 0.0745
1 1 1 0.0812
0 0 1 0.1183
0 0 -1 0.0877
1 -1 1 0.0783
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 108.77(8) . . ?
O1 N1 C9B 135.96(11) . . ?
O1 N1 O2 118.00(9) . . ?
C9B N1 O2 106.03(9) . . ?
C3A N3 O2 105.12(10) . . ?
N5 N4 C3A 114.37(10) . . ?
O5 N5 N4 118.06(9) . . ?
O5 N5 C5A 116.61(10) . . ?
N4 N5 C5A 125.33(10) . . ?
N3 C3A N4 121.62(11) . . ?
N3 C3A C9B 112.98(11) . . ?
N4 C3A C9B 125.40(11) . . ?
C6 C5A C9A 121.68(11) . . ?
C6 C5A N5 118.07(10) . . ?
C9A C5A N5 120.26(10) . . ?
C5A C6 C7 119.65(10) . . ?
C5A C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C8 118.78(11) . . ?
C6 C7 C10 120.36(11) . . ?
C8 C7 C10 120.85(11) . . ?
C9 C8 C7 121.69(11) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C9A 119.42(10) . . ?
C8 C9 H9 120.3 . . ?
C9A C9 H9 120.3 . . ?
C9 C9A C5A 118.77(11) . . ?
C9 C9A C9B 127.19(11) . . ?
C5A C9A C9B 114.04(10) . . ?
N1 C9B C3A 107.09(11) . . ?
N1 C9B C9A 132.31(11) . . ?
C3A C9B C9A 120.60(11) . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
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 N1 1.2275(14) . ?
O2 N3 1.3739(14) . ?
O2 N1 1.4633(14) . ?
O5 N5 1.2518(13) . ?
N1 C9B 1.3185(15) . ?
N3 C3A 1.3167(16) . ?
N4 N5 1.3016(14) . ?
N4 C3A 1.3724(15) . ?
N5 C5A 1.4650(15) . ?
C3A C9B 1.4050(17) . ?
C5A C6 1.3864(16) . ?
C5A C9A 1.4034(15) . ?
C6 C7 1.3910(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.4103(16) . ?
C7 C10 1.5045(16) . ?
C8 C9 1.3818(16) . ?
C8 H8 0.9500 . ?
C9 C9A 1.4016(16) . ?
C9 H9 0.9500 . ?
C9A C9B 1.4276(16) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
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 179.05(10) . . . . ?
N3 O2 N1 C9B -0.45(12) . . . . ?
N1 O2 N3 C3A 0.50(12) . . . . ?
C3A N4 N5 O5 179.64(10) . . . . ?
C3A N4 N5 C5A -0.30(16) . . . . ?
O2 N3 C3A N4 179.61(10) . . . . ?
O2 N3 C3A C9B -0.38(14) . . . . ?
N5 N4 C3A N3 -179.84(10) . . . . ?
N5 N4 C3A C9B 0.14(17) . . . . ?
O5 N5 C5A C6 -0.53(15) . . . . ?
N4 N5 C5A C6 179.41(10) . . . . ?
O5 N5 C5A C9A 179.72(10) . . . . ?
N4 N5 C5A C9A -0.35(17) . . . . ?
C9A C5A C6 C7 -0.01(17) . . . . ?
N5 C5A C6 C7 -179.76(10) . . . . ?
C5A C6 C7 C8 -1.22(17) . . . . ?
C5A C6 C7 C10 178.02(11) . . . . ?
C6 C7 C8 C9 1.59(17) . . . . ?
C10 C7 C8 C9 -177.65(11) . . . . ?
C7 C8 C9 C9A -0.67(18) . . . . ?
C8 C9 C9A C5A -0.58(17) . . . . ?
C8 C9 C9A C9B 178.96(11) . . . . ?
C6 C5A C9A C9 0.93(17) . . . . ?
N5 C5A C9A C9 -179.32(9) . . . . ?
C6 C5A C9A C9B -178.67(10) . . . . ?
N5 C5A C9A C9B 1.07(15) . . . . ?
O1 N1 C9B C3A -179.15(13) . . . . ?
O2 N1 C9B C3A 0.22(12) . . . . ?
O1 N1 C9B C9A 0.2(2) . . . . ?
O2 N1 C9B C9A 179.57(12) . . . . ?
N3 C3A C9B N1 0.09(15) . . . . ?
N4 C3A C9B N1 -179.89(11) . . . . ?
N3 C3A C9B C9A -179.35(10) . . . . ?
N4 C3A C9B C9A 0.67(19) . . . . ?
C9 C9A C9B N1 -0.1(2) . . . . ?
C5A C9A C9B N1 179.50(12) . . . . ?
C9 C9A C9B C3A 179.22(11) . . . . ?
C5A C9A C9B C3A -1.22(16) . . . . ?
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 0.9997 0.0002 -0.1398 -0.1179 0.0406
-0.0001 -0.9997 -0.0002 0.1398 0.1179 -0.0406
-0.9990 0.0004 -0.0003 0.1402 -0.2197 0.0480
0.9990 -0.0004 0.0003 -0.1402 0.2197 -0.0480
0.9990 0.9988 0.9995 -0.2353 0.1616 0.1489
-0.0001 -0.0005 0.9989 0.0446 0.0598 0.1563
0.0001 0.0005 -0.9989 -0.0446 -0.0598 -0.1563
0.9988 -1.0006 0.9990 0.0442 0.3974 0.0677
