#------------------------------------------------------------------------------
#$Date: 2024-10-06 11:30:36 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295287 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/68/7716861.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_7716861
loop_
_publ_author_name
'Mangue, Jordan'
'Wehrung, Iris'
'Pécaut, Jacques'
'Ménage, Stéphane'
'Orio, Maylis'
'Torelli, Stéphane'
_publ_section_title
;
 Bio-inspired copper complexes with Cu₂S cores: (solvent)
 effects on oxygen reduction reactions.
;
_journal_issue                   37
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              15576
_journal_page_last               15582
_journal_paper_doi               10.1039/d4dt01629g
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C18 H14 O4 S2'
_chemical_formula_sum            'C18 H14 O4 S2'
_chemical_formula_weight         358.41
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-04
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_audit_update_record
;
2024-06-04 deposited with the CCDC.	2024-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                96.363(3)
_cell_angle_beta                 104.018(3)
_cell_angle_gamma                108.327(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0729(3)
_cell_length_b                   9.8805(4)
_cell_length_c                   11.0153(4)
_cell_measurement_reflns_used    8087
_cell_measurement_temperature    92(1)
_cell_measurement_theta_max      32.1690
_cell_measurement_theta_min      2.6300
_cell_volume                     792.37(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      92(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9653
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  67.00   1.00   15.00    --   25.56 -99.00-180.00   92
  2  ω     -4.00  96.00   1.00   15.00    --   25.56  77.00 -60.00  100
  3  ω    -25.00  67.00   1.00   15.00    --   25.56 -99.00   0.00   92
  4  ω      4.00  94.00   1.00   15.00    --   25.56  57.00-120.00   90
  5  ω      4.00  94.00   1.00   15.00    --   25.56  57.00  60.00   90
  6  ω     -4.00  96.00   1.00   15.00    --   25.56  77.00 120.00  100
  7  ω    -48.00  42.00   1.00   15.00    --  -26.97  57.00 120.00   90
  8  ω    -53.00  45.00   1.00   15.00    --  -26.97  37.00  30.00   98
  9  ω    -71.00  46.00   1.00   15.00    --  -26.97  19.00 -60.00  117
 10  ω     35.00 101.00   1.00   15.00    --   25.56 178.00   0.00   66
 11  ω    -48.00   4.00   1.00   15.00    --  -26.97  56.00  89.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0820312000
_diffrn_orient_matrix_UB_12      0.0019166000
_diffrn_orient_matrix_UB_13      0.0432441000
_diffrn_orient_matrix_UB_21      -0.0478394000
_diffrn_orient_matrix_UB_22      -0.0671216000
_diffrn_orient_matrix_UB_23      0.0139848000
_diffrn_orient_matrix_UB_31      0.0189091000
_diffrn_orient_matrix_UB_32      -0.0381552000
_diffrn_orient_matrix_UB_33      -0.0502853000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19271
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         1.946
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent intense yellow'
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0312
_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)+(0.0321P)²+0.4575P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0805
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4333
_reflns_number_total             4827
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt01629g2.cif
_cod_data_source_block           mn5
_cod_depositor_comments
'Adding full bibliography for 7716861--7716862.cif.'
_cod_original_cell_volume        792.37(5)
_cod_database_code               7716861
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H20 S2 O4'
_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.
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.049
_oxdiff_exptl_absorpt_empirical_full_min 0.970
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
S1 S 0.65318(4) 0.49505(3) 0.28258(3) 0.01329(7) Uani 1 1 d . . . . .
S2 S 0.76815(4) 0.64897(3) 0.45297(3) 0.01276(7) Uani 1 1 d . . . . .
O1 O 0.90028(13) 0.74844(11) 0.03742(10) 0.0217(2) Uani 1 1 d . . . . .
O2 O 0.09556(13) 0.47883(11) 0.23491(10) 0.0217(2) Uani 1 1 d . . . . .
O3 O 1.33965(13) 0.71190(11) 0.49102(9) 0.01994(19) Uani 1 1 d . . . . .
O4 O 0.61180(13) 0.98154(11) 0.29183(9) 0.01962(19) Uani 1 1 d . . . . .
C1 C 0.54070(15) 0.58589(12) 0.17863(11) 0.0110(2) Uani 1 1 d . . . . .
C2 C 0.63106(15) 0.66440(12) 0.10069(11) 0.0112(2) Uani 1 1 d . . . . .
C3 C 0.54525(16) 0.73804(13) 0.02044(11) 0.0121(2) Uani 1 1 d . . . . .
H3 H 0.610(3) 0.793(2) -0.0280(17) 0.023(4) Uiso 1 1 d . . . . .
C4 C 0.37009(16) 0.73513(13) 0.01394(11) 0.0129(2) Uani 1 1 d . . . . .
C5 C 0.27988(16) 0.65375(13) 0.08960(11) 0.0126(2) Uani 1 1 d . . . . .
H5 H 0.162(2) 0.6508(19) 0.0854(17) 0.022(4) Uiso 1 1 d . . . . .
C6 C 0.36209(16) 0.58040(12) 0.17180(11) 0.0118(2) Uani 1 1 d . . . . .
C7 C 0.81830(16) 0.67340(13) 0.09865(11) 0.0138(2) Uani 1 1 d . . . . .
H7 H 0.872(3) 0.618(2) 0.1490(18) 0.027(5) Uiso 1 1 d . . . . .
C8 C 0.27965(18) 0.81496(15) -0.07215(13) 0.0180(2) Uani 1 1 d . . . . .
H8A H 0.357(3) 0.884(3) -0.102(2) 0.053(7) Uiso 1 1 d . . . . .
H8B H 0.187(3) 0.751(3) -0.146(2) 0.051(7) Uiso 1 1 d . . . . .
H8C H 0.230(3) 0.872(3) -0.030(2) 0.054(7) Uiso 1 1 d . . . . .
C9 C 0.25497(17) 0.49664(14) 0.24871(12) 0.0153(2) Uani 1 1 d . . . . .
H9 H 0.321(2) 0.4612(19) 0.3158(16) 0.018(4) Uiso 1 1 d . . . . .
C10 C 0.92142(15) 0.79291(12) 0.40650(11) 0.0106(2) Uani 1 1 d . . . . .
C11 C 1.10162(15) 0.80206(12) 0.41592(11) 0.0112(2) Uani 1 1 d . . . . .
C12 C 1.20965(16) 0.90727(13) 0.36552(11) 0.0125(2) Uani 1 1 d . . . . .
H12 H 1.328(3) 0.909(2) 0.3718(17) 0.024(4) Uiso 1 1 d . . . . .
C13 C 1.14479(16) 1.00610(13) 0.30633(11) 0.0119(2) Uani 1 1 d . . . . .
C14 C 0.96960(16) 1.00072(13) 0.30361(11) 0.0117(2) Uani 1 1 d . . . . .
H14 H 0.921(2) 1.0671(19) 0.2664(17) 0.022(4) Uiso 1 1 d . . . . .
C15 C 0.85778(15) 0.89632(12) 0.35284(11) 0.0104(2) Uani 1 1 d . . . . .
C16 C 1.18627(17) 0.70689(14) 0.48352(12) 0.0157(2) Uani 1 1 d . . . . .
H16 H 1.113(3) 0.639(2) 0.5246(18) 0.027(5) Uiso 1 1 d . . . . .
C17 C 1.26219(18) 1.11509(15) 0.24896(14) 0.0180(2) Uani 1 1 d . . . . .
H17A H 1.191(3) 1.155(2) 0.189(2) 0.036(5) Uiso 1 1 d . . . . .
H17B H 1.324(3) 1.072(3) 0.205(2) 0.050(7) Uiso 1 1 d . . . . .
H17C H 1.355(3) 1.193(2) 0.316(2) 0.040(6) Uiso 1 1 d . . . . .
C18 C 0.67319(16) 0.90040(13) 0.34696(11) 0.0128(2) Uani 1 1 d . . . . .
H18 H 0.603(2) 0.8363(17) 0.3907(15) 0.011(4) Uiso 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 0.0033 0.0016 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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 1 0.0569
0 1 -1 0.0019
-1 0 1 0.0957
1 0 -1 0.1087
0 0 1 0.1500
1 -1 -2 0.0741
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
C1 S1 S2 102.10(4) . . ?
C10 S2 S1 100.67(4) . . ?
C2 C1 S1 119.48(9) . . ?
C2 C1 C6 118.75(10) . . ?
C6 C1 S1 121.77(9) . . ?
C1 C2 C7 122.71(10) . . ?
C3 C2 C1 119.92(10) . . ?
C3 C2 C7 117.37(10) . . ?
C2 C3 H3 118.4(11) . . ?
C4 C3 C2 121.94(11) . . ?
C4 C3 H3 119.7(11) . . ?
C3 C4 C5 117.62(11) . . ?
C3 C4 C8 121.47(11) . . ?
C5 C4 C8 120.91(11) . . ?
C4 C5 H5 118.1(11) . . ?
C6 C5 C4 121.96(11) . . ?
C6 C5 H5 119.9(11) . . ?
C1 C6 C9 122.20(10) . . ?
C5 C6 C1 119.78(10) . . ?
C5 C6 C9 118.01(10) . . ?
O1 C7 C2 122.53(11) . . ?
O1 C7 H7 120.7(12) . . ?
C2 C7 H7 116.7(12) . . ?
C4 C8 H8A 114.9(15) . . ?
C4 C8 H8B 112.2(14) . . ?
C4 C8 H8C 112.1(15) . . ?
H8A C8 H8B 106(2) . . ?
H8A C8 H8C 101(2) . . ?
H8B C8 H8C 109(2) . . ?
O2 C9 C6 123.04(11) . . ?
O2 C9 H9 120.2(10) . . ?
C6 C9 H9 116.6(10) . . ?
C11 C10 S2 121.99(9) . . ?
C15 C10 S2 119.07(8) . . ?
C15 C10 C11 118.86(10) . . ?
C10 C11 C16 122.35(10) . . ?
C12 C11 C10 119.75(10) . . ?
C12 C11 C16 117.84(10) . . ?
C11 C12 H12 117.7(11) . . ?
C11 C12 C13 121.83(11) . . ?
C13 C12 H12 120.4(11) . . ?
C12 C13 C17 120.65(11) . . ?
C14 C13 C12 117.79(11) . . ?
C14 C13 C17 121.56(10) . . ?
C13 C14 H14 120.8(11) . . ?
C13 C14 C15 121.70(10) . . ?
C15 C14 H14 117.5(11) . . ?
C10 C15 C18 122.32(10) . . ?
C14 C15 C10 119.92(10) . . ?
C14 C15 C18 117.76(10) . . ?
O3 C16 C11 123.23(12) . . ?
O3 C16 H16 119.2(11) . . ?
C11 C16 H16 117.5(11) . . ?
C13 C17 H17A 112.1(12) . . ?
C13 C17 H17B 110.9(15) . . ?
C13 C17 H17C 110.1(13) . . ?
H17A C17 H17B 106.7(18) . . ?
H17A C17 H17C 110.0(17) . . ?
H17B C17 H17C 106.8(19) . . ?
O4 C18 C15 122.64(11) . . ?
O4 C18 H18 120.2(9) . . ?
C15 C18 H18 117.2(9) . . ?
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
S1 S2 2.0815(4) . ?
S1 C1 1.7827(11) . ?
S2 C10 1.7825(12) . ?
O1 C7 1.2088(16) . ?
O2 C9 1.2112(15) . ?
O3 C16 1.2056(15) . ?
O4 C18 1.2121(15) . ?
C1 C2 1.4022(16) . ?
C1 C6 1.4089(16) . ?
C2 C3 1.3977(16) . ?
C2 C7 1.4919(16) . ?
C3 H3 0.934(18) . ?
C3 C4 1.3894(16) . ?
C4 C5 1.3949(16) . ?
C4 C8 1.4991(16) . ?
C5 H5 0.935(18) . ?
C5 C6 1.3937(16) . ?
C6 C9 1.4869(16) . ?
C7 H7 0.946(19) . ?
C8 H8A 0.92(3) . ?
C8 H8B 0.95(2) . ?
C8 H8C 0.93(3) . ?
C9 H9 0.967(17) . ?
C10 C11 1.4061(15) . ?
C10 C15 1.4051(15) . ?
C11 C12 1.3935(16) . ?
C11 C16 1.4894(16) . ?
C12 H12 0.938(19) . ?
C12 C13 1.3965(16) . ?
C13 C14 1.3913(16) . ?
C13 C17 1.5021(17) . ?
C14 H14 0.947(18) . ?
C14 C15 1.3959(16) . ?
C15 C18 1.4893(16) . ?
C16 H16 0.973(19) . ?
C17 H17A 0.97(2) . ?
C17 H17B 0.93(2) . ?
C17 H17C 0.97(2) . ?
C18 H18 0.964(16) . ?
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
S1 S2 C10 C11 -88.88(9) . . . . ?
S1 S2 C10 C15 87.85(9) . . . . ?
S1 C1 C2 C3 -178.92(9) . . . . ?
S1 C1 C2 C7 1.23(16) . . . . ?
S1 C1 C6 C5 179.66(9) . . . . ?
S1 C1 C6 C9 -1.14(16) . . . . ?
S2 S1 C1 C2 94.25(9) . . . . ?
S2 S1 C1 C6 -86.16(10) . . . . ?
S2 C10 C11 C12 172.99(9) . . . . ?
S2 C10 C11 C16 -9.78(16) . . . . ?
S2 C10 C15 C14 -173.29(9) . . . . ?
S2 C10 C15 C18 7.23(15) . . . . ?
C1 C2 C3 C4 -0.66(18) . . . . ?
C1 C2 C7 O1 -175.27(12) . . . . ?
C1 C6 C9 O2 -172.47(12) . . . . ?
C2 C1 C6 C5 -0.74(17) . . . . ?
C2 C1 C6 C9 178.46(11) . . . . ?
C2 C3 C4 C5 -0.89(18) . . . . ?
C2 C3 C4 C8 179.78(12) . . . . ?
C3 C2 C7 O1 4.87(18) . . . . ?
C3 C4 C5 C6 1.65(18) . . . . ?
C4 C5 C6 C1 -0.85(18) . . . . ?
C4 C5 C6 C9 179.93(11) . . . . ?
C5 C6 C9 O2 6.73(19) . . . . ?
C6 C1 C2 C3 1.47(17) . . . . ?
C6 C1 C2 C7 -178.38(10) . . . . ?
C7 C2 C3 C4 179.20(11) . . . . ?
C8 C4 C5 C6 -179.02(12) . . . . ?
C10 C11 C12 C13 0.64(18) . . . . ?
C10 C11 C16 O3 178.96(12) . . . . ?
C10 C15 C18 O4 -173.93(12) . . . . ?
C11 C10 C15 C14 3.54(17) . . . . ?
C11 C10 C15 C18 -175.94(10) . . . . ?
C11 C12 C13 C14 2.65(18) . . . . ?
C11 C12 C13 C17 -177.93(12) . . . . ?
C12 C11 C16 O3 -3.76(19) . . . . ?
C12 C13 C14 C15 -2.87(17) . . . . ?
C13 C14 C15 C10 -0.21(17) . . . . ?
C13 C14 C15 C18 179.30(11) . . . . ?
C14 C15 C18 O4 6.58(18) . . . . ?
C15 C10 C11 C12 -3.74(17) . . . . ?
C15 C10 C11 C16 173.48(11) . . . . ?
C16 C11 C12 C13 -176.71(11) . . . . ?
C17 C13 C14 C15 177.72(12) . . . . ?
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
-0.0183 -0.9745 1.0058 0.0401 0.0804 -0.0137
0.0183 0.9745 -1.0058 -0.0401 -0.0804 0.0137
-1.0022 0.0082 0.9943 -0.0392 0.0613 -0.0693
1.0022 -0.0082 -0.9943 0.0392 -0.0613 0.0693
-0.0024 -0.0012 0.9982 0.0430 0.0142 -0.0502
0.9887 -0.9804 -1.9849 -0.0066 -0.0093 0.1559
