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#$Date: 2024-03-21 02:58:21 +0200 (Thu, 21 Mar 2024) $
#$Revision: 290568 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/83/7248322.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_7248322
loop_
_publ_author_name
'Nowicki, Krzysztof'
'Krajewska, Joanna'
'Stępniewski, Tomasz'
'Wielechowska, Monika'
'Wińska, Patrycja'
'Kaczmarczyk, Anna'
'Korpowska, Julia'
'Selent, Jana'
'Marek-Urban, Paulina H.'
'Durka, Krzysztof'
'Wozniak, Krzysztof'
'Laudy, Agnieszka E.'
'Luliński, Sergiusz'
_publ_section_title
;
 Exploiting thiol-functionalized benzosiloxaboroles for achieving diverse
 substitution patterns -- synthesis, characterization and biological
 evaluation of promising antibacterial agents
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D4MD00061G
_journal_year                    2024
_chemical_formula_moiety         'C11 H12 B F2 N O2 S Si'
_chemical_formula_sum            'C11 H12 B F2 N O2 S Si'
_chemical_formula_weight         299.18
_chemical_name_systematic
;
3-((5,7-difluoro-3-hydroxy-1,1-dimethyl-1,3-dihydrobenzo[c][1,2,5]oxasilaborol-6-yl)thio)propanenitrile 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           6
_space_group_name_Hall           'P -2y'
_space_group_name_H-M_alt        'P 1 m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-07-15 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.038(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7169(3)
_cell_length_b                   7.4368(3)
_cell_length_c                   10.3692(3)
_cell_measurement_reflns_used    2047
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.3950
_cell_measurement_theta_min      4.3330
_cell_volume                     654.86(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1720
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.527
_diffrn_reflns_theta_min         4.377
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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            colourless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.083
_refine_diff_density_max         1.756
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Flack x determined using 324 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         1720
_refine_ls_number_restraints     148
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0.01
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0556P)²+1.4978P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1195
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                1623
_reflns_number_total             1720
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4md00061g2.cif
_cod_data_source_block           6
_cod_original_sg_symbol_H-M      'P m'
_cod_database_code               7248322
_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.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.780
_oxdiff_exptl_absorpt_empirical_full_max 1.457
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelxl_version_number           2013-4
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
C24 C 0.961(2) 0.0000 0.167(2) 0.036(4) Uani 1 2 d S TU P . .
C21 C 0.8064(11) 0.0921(13) 0.0817(11) 0.011(3) Uani 0.5 1 d . U P . .
H21A H 0.7606 0.1787 0.1351 0.014 Uiso 0.5 1 calc R U P . .
H21B H 0.8275 0.1541 0.0030 0.014 Uiso 0.5 1 calc R U P . .
C20 C 0.7058(12) 0.0621(12) 0.0449(10) 0.008(2) Uani 0.5 1 d D U P . .
H20A H 0.7577 0.1477 -0.0047 0.010 Uiso 0.5 1 calc R U P . .
H20B H 0.6915 0.1235 0.1262 0.010 Uiso 0.5 1 calc R U P . .
C15 C 0.5041(19) 0.0000 -0.5058(16) 0.012(2) Uani 1 2 d S TU P . .
B2 B 0.5158(19) 0.5000 0.0676(17) 0.011(3) Uani 1 2 d S TU P . .
C16 C 0.6688(19) 0.5000 -0.1317(15) 0.013(3) Uani 1 2 d S TU P . .
H16 H 0.7684 0.5000 -0.0712 0.016 Uiso 1 2 calc R U P . .
N1 N 1.0831(19) 0.0000 0.2204(15) 0.020(2) Uani 1 2 d S TU P . .
N2 N -0.039(2) 0.5000 -0.8118(16) 0.028(3) Uani 1 2 d S TU P . .
C26 C 0.082(3) 0.5000 -0.748(3) 0.068(7) Uani 1 2 d S TU P . .
C31 C 0.3515 0.4173 -0.6159 0.019(3) Uani 0.5 1 d D U P . .
H31A H 0.3679 0.3361 -0.6873 0.022 Uiso 0.5 1 calc R U P . .
H31B H 0.2979 0.3491 -0.5569 0.022 Uiso 0.5 1 calc R U P . .
C33 C 0.2423 0.4066 -0.6805 0.018(3) Uani 0.5 1 d . U P . .
H33A H 0.2479 0.3454 -0.5948 0.022 Uiso 0.5 1 calc R U P . .
H33B H 0.3010 0.3454 -0.7392 0.022 Uiso 0.5 1 calc R U P . .
S1 S 0.5075(10) 0.0000 -0.0594(10) 0.0182(7) Uani 1 2 d DS T P . .
Si4 Si 0.8110(10) 0.0000 -0.5094(10) 0.0174(8) Uani 1 2 d S T P . .
F1 F 0.2483(14) 0.0000 -0.2750(12) 0.024(2) Uani 1 2 d S T P . .
O3 O 0.4192(16) 0.0000 -0.7655(14) 0.019(2) Uani 1 2 d DS TU P . .
F3 F 0.8029(14) 0.0000 -0.1949(12) 0.025(2) Uani 1 2 d S TU P . .
C5 C 0.3651(19) 0.0000 -0.4592(15) 0.018(3) Uani 1 2 d S T P . .
H5 H 0.2640 0.0000 -0.5176 0.021 Uiso 1 2 calc R U P . .
O2 O 0.6837(16) 0.0000 -0.6574(13) 0.021(2) Uani 1 2 d S TU P . .
B1 B 0.532(2) 0.0000 -0.6489(19) 0.024(3) Uani 1 2 d S TU P . .
C4 C 0.654(2) 0.0000 -0.4072(16) 0.013(2) Uani 1 2 d S TU P . .
C14 C 0.9333(16) 0.2053(12) -0.4963(14) 0.021(2) Uani 1 1 d . . . . .
H14A H 0.8654 0.3117 -0.5045 0.031 Uiso 1 1 calc R U . . .
H14B H 0.9909 0.2059 -0.5673 0.031 Uiso 1 1 calc R U . . .
H14C H 1.0083 0.2071 -0.4103 0.031 Uiso 1 1 calc R U . . .
C3 C 0.658(2) 0.0000 -0.2783(15) 0.013(3) Uani 1 2 d S T P . .
C2 C 0.524(2) 0.0000 -0.2291(17) 0.022(3) Uani 1 2 d S TU P . .
C1 C 0.384(2) 0.0000 -0.3231(16) 0.017(3) Uani 1 2 d S TU P . .
H3A H 0.326(4) 0.0000 -0.751(12) 0.025 Uiso 1 2 d DS U P . .
Si2 Si 0.2298(10) 0.5000 -0.0740(9) 0.0160(8) Uani 1 2 d S T P . .
S2 S 0.5335(10) 0.5000 -0.5258(10) 0.0166(7) Uani 1 2 d DS T P . .
F2 F 0.7930(14) 0.5000 -0.3090(12) 0.0235(18) Uani 1 2 d S TU P . .
C8 C 0.381(2) 0.5000 -0.3055(17) 0.019(3) Uani 1 2 d S TU P . .
C10 C 0.661(2) 0.5000 -0.2649(16) 0.015(3) Uani 1 2 d S TU P . .
F4 F 0.2392(14) 0.5000 -0.3917(12) 0.0244(19) Uani 1 2 d S TU P . .
C6 C 0.531(2) 0.5000 -0.0847(17) 0.019(3) Uani 1 2 d S TU P . .
C9 C 0.516(2) 0.5000 -0.3611(14) 0.009(2) Uani 1 2 d S T P . .
O1 O 0.3567(15) 0.5000 0.0734(12) 0.017(2) Uani 1 2 d S T P . .
C13 C 0.1109(16) 0.2937(14) -0.0903(14) 0.025(2) Uani 1 1 d . . . . .
H13A H 0.0328 0.3038 -0.0359 0.037 Uiso 1 1 calc R U . . .
H13B H 0.1796 0.1904 -0.0604 0.037 Uiso 1 1 calc R U . . .
H13C H 0.0570 0.2767 -0.1832 0.037 Uiso 1 1 calc R U . . .
C7 C 0.387(2) 0.5000 -0.1669(16) 0.018(3) Uani 1 2 d S T P . .
O4 O 0.6256(17) 0.5000 0.1798(14) 0.023(2) Uani 1 2 d DS TU P . .
H4A H 0.725(7) 0.5000 0.179(13) 0.035 Uiso 1 2 d DS U P . .
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'
B B 0.0090 0.0039 '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'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -2 0.0692
4 3 -1 0.0431
4 0 -5 0.0534
-5 -2 2 0.0626
0 1 0 0.0279
0 -1 0 0.0550
-1 -1 5 0.1044
-3 1 -4 0.0706
2 -1 1 0.0904
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
N1 C24 C21 153.6(7) . 2 ?
N1 C24 C21 153.6(7) . . ?
C21 C24 C21 51.0(9) 2 . ?
C20 C21 C24 101.1(7) 2 . ?
C20 C21 H21A 111.6 2 . ?
C24 C21 H21A 110.0 . . ?
C20 C21 H21B 111.6 2 . ?
C24 C21 H21B 112.9 . . ?
H21A C21 H21B 109.4 . . ?
C21 C20 S1 112.5(6) 2 . ?
C21 C20 H20A 109.1 2 . ?
S1 C20 H20A 109.1 . . ?
C21 C20 H20B 109.2 2 . ?
S1 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
C5 C15 C4 117.5(12) . . ?
C5 C15 B1 131.5(13) . . ?
C4 C15 B1 110.9(13) . . ?
O4 B2 O1 119.2(13) . . ?
O4 B2 C6 130.9(14) . . ?
O1 B2 C6 110.0(11) . . ?
C10 C16 C6 120.0(14) . . ?
C10 C16 H16 119.8 . . ?
C6 C16 H16 120.2 . . ?
N2 C26 C33 153.0(7) . 2_565 ?
N2 C26 C33 153.0(7) . . ?
C33 C26 C33 52.4(9) 2_565 . ?
C33 C31 S2 107.65(9) 2_565 . ?
C33 C31 H31A 110.2 2_565 . ?
S2 C31 H31A 110.1 . . ?
C33 C31 H31B 110.2 2_565 . ?
S2 C31 H31B 110.2 . . ?
H31A C31 H31B 108.5 . . ?
C33 C33 C26 63.8(5) 2_565 . ?
C33 C33 H33A 117.3 2_565 . ?
C26 C33 H33A 115.0 . . ?
C33 C33 H33B 117.3 2_565 . ?
C26 C33 H33B 119.9 . . ?
H33A C33 H33B 114.4 . . ?
C2 S1 C20 107.2(6) . . ?
C2 S1 C20 107.2(6) . 2 ?
C20 S1 C20 28.5(6) . 2 ?
O2 Si4 C14 108.6(4) . . ?
O2 Si4 C14 108.6(4) . 2 ?
C14 Si4 C14 111.3(6) . 2 ?
O2 Si4 C4 95.7(6) . . ?
C14 Si4 C4 115.6(4) . . ?
C14 Si4 C4 115.6(4) 2 . ?
B1 O3 H3A 111(8) . . ?
C1 C5 C15 115.9(13) . . ?
C1 C5 H5 122.2 . . ?
C15 C5 H5 121.9 . . ?
B1 O2 Si4 113.4(10) . . ?
O2 B1 O3 117.6(15) . . ?
O2 B1 C15 115.6(14) . . ?
O3 B1 C15 126.8(16) . . ?
C3 C4 C15 121.2(14) . . ?
C3 C4 Si4 134.4(12) . . ?
C15 C4 Si4 104.5(9) . . ?
Si4 C14 H14A 109.5 . . ?
Si4 C14 H14B 109.4 . . ?
H14A C14 H14B 109.5 . . ?
Si4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C3 F3 116.5(14) . . ?
C4 C3 C2 122.9(13) . . ?
F3 C3 C2 120.6(12) . . ?
C3 C2 C1 115.3(13) . . ?
C3 C2 S1 128.8(11) . . ?
C1 C2 S1 115.9(13) . . ?
C2 C1 C5 127.2(15) . . ?
C2 C1 F1 116.0(11) . . ?
C5 C1 F1 116.9(13) . . ?
O1 Si2 C13 109.1(4) . . ?
O1 Si2 C13 109.1(4) . 2_565 ?
C13 Si2 C13 113.2(7) . 2_565 ?
O1 Si2 C7 93.5(6) . . ?
C13 Si2 C7 114.9(4) . . ?
C13 Si2 C7 114.9(4) 2_565 . ?
C9 S2 C31 104.5(6) . . ?
C9 S2 C31 104.5(6) . 2_565 ?
C31 S2 C31 40.87(18) . 2_565 ?
F4 C8 C9 116.7(12) . . ?
F4 C8 C7 118.9(15) . . ?
C9 C8 C7 124.4(14) . . ?
F2 C10 C16 119.6(13) . . ?
F2 C10 C9 117.3(11) . . ?
C16 C10 C9 123.1(14) . . ?
C7 C6 C16 122.2(13) . . ?
C7 C6 B2 110.3(13) . . ?
C16 C6 B2 127.5(13) . . ?
C8 C9 C10 113.5(11) . . ?
C8 C9 S2 131.3(10) . . ?
C10 C9 S2 115.2(10) . . ?
B2 O1 Si2 114.7(9) . . ?
Si2 C13 H13A 109.5 . . ?
Si2 C13 H13B 109.4 . . ?
H13A C13 H13B 109.5 . . ?
Si2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C7 C8 116.8(15) . . ?
C6 C7 Si2 111.4(10) . . ?
C8 C7 Si2 131.8(13) . . ?
B2 O4 H4A 121(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
C24 N1 1.08(2) . ?
C24 C21 1.591(19) 2 ?
C24 C21 1.591(19) . ?
C21 C20 1.442(14) 2 ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C20 C21 1.442(14) 2 ?
C20 S1 1.879(10) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C15 C5 1.40(2) . ?
C15 C4 1.466(19) . ?
C15 B1 1.56(2) . ?
B2 O4 1.329(18) . ?
B2 O1 1.402(18) . ?
B2 C6 1.61(2) . ?
C16 C10 1.366(18) . ?
C16 C6 1.40(2) . ?
C16 H16 0.9500 . ?
N2 C26 1.12(3) . ?
C26 C33 1.57(3) 2_565 ?
C26 C33 1.57(3) . ?
C31 C33 1.66800(10) 2_565 ?
C31 S2 1.761(7) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C33 C33 1.38920(10) 2_565 ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
S1 C2 1.798(16) . ?
S1 C20 1.879(10) 2 ?
Si4 O2 1.679(10) . ?
Si4 C14 1.849(10) . ?
Si4 C14 1.849(10) 2 ?
Si4 C4 1.912(16) . ?
F1 C1 1.385(16) . ?
O3 B1 1.38(2) . ?
O3 H3A 0.86(3) . ?
F3 C3 1.363(16) . ?
C5 C1 1.384(17) . ?
C5 H5 0.9500 . ?
O2 B1 1.34(2) . ?
C4 C3 1.330(19) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C3 C2 1.37(2) . ?
C2 C1 1.38(2) . ?
Si2 O1 1.672(9) . ?
Si2 C13 1.838(11) . ?
Si2 C13 1.838(11) 2_565 ?
Si2 C7 1.842(17) . ?
S2 C9 1.749(12) . ?
S2 C31 1.761(7) 2_565 ?
F2 C10 1.335(17) . ?
C8 F4 1.352(18) . ?
C8 C9 1.42(2) . ?
C8 C7 1.43(2) . ?
C10 C9 1.42(2) . ?
C6 C7 1.35(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O4 H4A 0.87(3) . ?
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
0.0008 -1.0004 -1.9982 0.0233 0.0870 0.3574
3.9995 2.9923 -1.0016 -0.2826 -0.8869 -0.1349
3.9999 -0.0084 -4.9963 -0.0662 -0.6356 0.6701
-4.9980 -1.9903 1.9990 0.1111 0.9698 -0.0895
0.0012 0.9999 -0.0017 -0.1697 -0.0772 -0.0902
-0.0012 -0.9999 0.0017 0.1697 0.0772 0.0902
-1.0049 -0.9970 5.0006 0.4608 0.2178 -0.5783
-2.9910 1.0045 -4.0042 -0.6875 0.4374 0.4425
1.9953 -1.0034 1.0034 0.3929 -0.2577 -0.0423
