#------------------------------------------------------------------------------
#$Date: 2020-05-05 15:48:48 +0300 (Tue, 05 May 2020) $
#$Revision: 251582 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/62/7126269.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_7126269
loop_
_publ_author_name
'Lamb, Katie J.'
'Dowsett, Mark R.'
'North, Michael'
'Parker, Rachel R.'
'Whitwood, Adrian C.'
_publ_section_title
;
 Unprecedented reductive cyclisation of salophen ligands to
 tetrahydroquinoxalines during metal complex formation.
;
_journal_issue                   35
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4844
_journal_page_last               4847
_journal_paper_doi               10.1039/d0cc01192d
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C22 H22 N2 O4'
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.41
_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             2019-09-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-10 deposited with the CCDC.	2020-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                97.383(5)
_cell_angle_beta                 104.649(6)
_cell_angle_gamma                99.610(6)
_cell_formula_units_Z            2
_cell_length_a                   7.3701(5)
_cell_length_b                   10.2836(7)
_cell_length_c                   12.5573(7)
_cell_measurement_reflns_used    2763
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      70.4420
_cell_measurement_theta_min      6.2520
_cell_volume                     893.22(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00 -32.00   1.00    1.00    --    0.00 -57.00  60.00   29
  2  ω    -20.00  21.00   1.00    1.00    --    0.00 -57.00  60.00   41
  3  ω    -16.00  18.00   1.00    1.00    --    0.00  57.00-150.00   34
  4  ω     30.00  56.00   1.00    1.00    --    0.00  57.00-150.00   26
  5  ω     32.00  95.00   1.00    1.00    --   54.00-125.00-120.00   63
  6  ω     26.00  80.00   1.00    1.00    --   54.00-125.00  90.00   54
  7  ω    -11.00 119.00   1.00    1.00    --   54.00   0.00 -90.00  130
  8  ω     95.00 120.00   1.00    1.00    --   54.00  57.00-120.00   25
  9  ω     -6.00  59.00   1.00    1.00    --   54.00 -37.00  60.00   65
 10  ω    -15.00  69.00   1.00    1.00    --   54.00 -77.00 -60.00   84
 11  ω     28.00  53.00   1.00    1.00    --   54.00-125.00 -60.00   25
 12  ω     94.00 168.00   1.00    1.00    --  108.00  63.00  30.00   74
 13  ω     42.00 123.00   1.00    1.00    --  108.00 -50.00-180.00   81
 14  ω     94.00 145.00   1.00    1.00    --  108.00 -91.00  30.00   51
 15  ω     36.00 146.00   1.00    1.00    --  108.00 -91.00 -30.00  110
 16  ω     89.00 178.00   1.00    1.00    --  108.00  37.00  90.00   89
 17  ω     39.00  72.00   1.00    1.00    --  108.00 -50.00  60.00   33
 18  ω     78.00 104.00   1.00    1.00    --  108.00-111.00-120.00   26
 19  ω     57.00 146.00   1.00    1.00    --  108.00 178.00 -60.00   89
 20  ω     38.00  93.00   1.00    1.00    --  108.00 -50.00 -30.00   55
 21  ω     97.00 175.00   1.00    1.00    --  108.00  63.00 120.00   78
 22  ω     89.00 119.00   1.00    1.00    --  108.00 -50.00  60.00   30
 23  ω     64.00 108.00   1.00    1.00    --  108.00-111.00 -60.00   44
 24  ω     98.00 145.00   1.00    1.00    --  108.00  77.00 150.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0433834000
_diffrn_orient_matrix_UB_12      -0.0419811000
_diffrn_orient_matrix_UB_13      -0.1276089000
_diffrn_orient_matrix_UB_21      0.1728379000
_diffrn_orient_matrix_UB_22      -0.0689298000
_diffrn_orient_matrix_UB_23      0.0175436000
_diffrn_orient_matrix_UB_31      -0.1305042000
_diffrn_orient_matrix_UB_32      -0.1316657000
_diffrn_orient_matrix_UB_33      0.0044490000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5380
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.036
_diffrn_reflns_theta_max         67.036
_diffrn_reflns_theta_min         3.698
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0047(5)
_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   1.032
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         3183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0436P)²+0.2669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0875
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2772
_reflns_number_total             3183
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc01192d2.cif
_cod_data_source_block           mn1908
_cod_depositor_comments
'Adding full bibliography for 7126266--7126270.cif.'
_cod_original_cell_volume        893.21(10)
_cod_database_code               7126269
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H22 N2 O4'
_chemical_oxdiff_usercomment     'Katie Lamb KL 2,6 Cry'
_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     66.97
_olex2_refinement_description
;
;
_olex2_date_sample_data_collection 2019-09-11
_olex2_date_sample_submission    2019-08-21
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id 'KL 2,6 cry'
_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 1.291
_oxdiff_exptl_absorpt_empirical_full_min 0.776
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
C1 C 0.69526(18) 0.47666(14) 0.72646(11) 0.0163(3) Uani 1 1 d . . . . .
C2 C 0.6679(2) 0.38288(14) 0.79485(12) 0.0197(3) Uani 1 1 d . . . . .
H2 H 0.619(2) 0.2909(17) 0.7611(13) 0.024(4) Uiso 1 1 d . . . . .
C3 C 0.7095(2) 0.42573(15) 0.90845(12) 0.0217(3) Uani 1 1 d . . . . .
H3 H 0.690(3) 0.3599(18) 0.9581(15) 0.035(5) Uiso 1 1 d . . . . .
C4 C 0.7815(2) 0.56010(15) 0.95635(12) 0.0199(3) Uani 1 1 d . . . . .
H4 H 0.814(2) 0.5896(16) 1.0349(15) 0.028(4) Uiso 1 1 d . . . . .
C5 C 0.81113(18) 0.65313(13) 0.88809(11) 0.0152(3) Uani 1 1 d . . . . .
C6 C 0.76654(18) 0.61350(13) 0.77147(11) 0.0140(3) Uani 1 1 d . . . . .
C7 C 0.79189(18) 0.71462(13) 0.69562(11) 0.0134(3) Uani 1 1 d . . . . .
H7 H 0.873(2) 0.8019(15) 0.7410(12) 0.015(4) Uiso 1 1 d . . . . .
C8 C 0.89804(18) 0.73664(13) 0.52781(11) 0.0149(3) Uani 1 1 d . . . . .
C9 C 1.0424(2) 0.72992(13) 0.47512(11) 0.0174(3) Uani 1 1 d . . . . .
H9 H 1.133(2) 0.6733(16) 0.4989(13) 0.022(4) Uiso 1 1 d . . . . .
C10 C 1.0536(2) 0.80005(14) 0.38924(11) 0.0191(3) Uani 1 1 d . . . . .
H10 H 1.155(2) 0.7948(15) 0.3519(13) 0.019(4) Uiso 1 1 d . . . . .
C11 C 0.9201(2) 0.87852(14) 0.35547(12) 0.0197(3) Uani 1 1 d . . . . .
H11 H 0.924(2) 0.9288(16) 0.2950(13) 0.022(4) Uiso 1 1 d . . . . .
C12 C 0.7777(2) 0.88665(14) 0.40872(11) 0.0178(3) Uani 1 1 d . . . . .
H12 H 0.688(2) 0.9415(16) 0.3877(13) 0.023(4) Uiso 1 1 d . . . . .
C13 C 0.76541(18) 0.81664(13) 0.49524(11) 0.0146(3) Uani 1 1 d . . . . .
C14 C 0.59599(18) 0.74103(13) 0.63210(11) 0.0136(3) Uani 1 1 d . . . . .
H14 H 0.517(2) 0.6537(15) 0.5901(12) 0.011(3) Uiso 1 1 d . . . . .
C15 C 0.49997(18) 0.80260(13) 0.71363(11) 0.0141(3) Uani 1 1 d . . . . .
C16 C 0.36265(18) 0.72171(13) 0.74961(11) 0.0157(3) Uani 1 1 d . . . . .
C17 C 0.28268(19) 0.77412(15) 0.83047(11) 0.0196(3) Uani 1 1 d . . . . .
H17 H 0.186(2) 0.7169(16) 0.8544(13) 0.023(4) Uiso 1 1 d . . . . .
C18 C 0.3364(2) 0.90950(15) 0.87459(12) 0.0215(3) Uani 1 1 d . . . . .
H18 H 0.280(2) 0.9443(16) 0.9309(14) 0.024(4) Uiso 1 1 d . . . . .
C19 C 0.4686(2) 0.99276(15) 0.83975(12) 0.0212(3) Uani 1 1 d . . . . .
H19 H 0.506(2) 1.0890(17) 0.8692(14) 0.027(4) Uiso 1 1 d . . . . .
C20 C 0.55098(19) 0.93951(13) 0.76058(11) 0.0163(3) Uani 1 1 d . . . . .
C21 C 0.9406(3) 0.82874(17) 1.04748(12) 0.0271(4) Uani 1 1 d . . . . .
H21A H 1.031(3) 0.7773(18) 1.0836(15) 0.034(5) Uiso 1 1 d . . . . .
H21B H 0.828(3) 0.8161(18) 1.0770(15) 0.037(5) Uiso 1 1 d . . . . .
H21C H 0.995(3) 0.926(2) 1.0609(15) 0.039(5) Uiso 1 1 d . . . . .
C22 C 0.2543(2) 0.49442(15) 0.76368(13) 0.0221(3) Uani 1 1 d . . . . .
H22A H 0.255(2) 0.4068(17) 0.7246(14) 0.023(4) Uiso 1 1 d . . . . .
H22B H 0.350(2) 0.5159(17) 0.8372(15) 0.028(4) Uiso 1 1 d . . . . .
H22C H 0.127(3) 0.4955(17) 0.7727(14) 0.028(4) Uiso 1 1 d . . . . .
N1 N 0.88042(16) 0.65894(11) 0.61133(9) 0.0150(3) Uani 1 1 d . . . . .
H1 H 0.993(3) 0.6388(17) 0.6441(14) 0.025(4) Uiso 1 1 d . . . . .
N2 N 0.62706(17) 0.83408(11) 0.55430(9) 0.0159(3) Uani 1 1 d . . . . .
H2A H 0.518(3) 0.8341(17) 0.5060(15) 0.027(4) Uiso 1 1 d . . . . .
O1 O 0.64866(14) 0.43056(10) 0.61408(8) 0.0200(2) Uani 1 1 d . . . . .
H1A H 0.715(3) 0.496(2) 0.5854(17) 0.046(6) Uiso 1 1 d . . . . .
O2 O 0.88551(14) 0.78681(9) 0.92862(7) 0.0189(2) Uani 1 1 d . . . . .
O3 O 0.30735(13) 0.58983(9) 0.69727(8) 0.0197(2) Uani 1 1 d . . . . .
O4 O 0.68401(14) 1.02536(9) 0.73027(9) 0.0212(2) Uani 1 1 d . . . . .
H4A H 0.694(3) 0.980(2) 0.6632(19) 0.053(6) 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 0.0181 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 0.0669
2 1 -2 0.0600
1 0 -1 0.0551
0 1 0 0.0464
-1 2 0 0.0756
2 0 -1 0.0725
-2 1 0 0.0959
0 -2 1 0.0728
1 0 2 0.0948
0 0 1 0.0870
0 0 -1 0.0952
0 -2 -1 0.0684
-1 0 1 0.1190
-1 0 -2 0.1021
0 1 -2 0.1021
-2 1 2 0.1079
1 -2 -1 0.0612
-1 -1 0 0.1121
0 -1 -2 0.0852
1 0 -2 0.0704
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
C2 C1 C6 121.25(13) . . ?
O1 C1 C2 117.43(12) . . ?
O1 C1 C6 121.32(12) . . ?
C3 C2 C1 119.22(13) . . ?
C2 C3 C4 121.30(13) . . ?
C3 C4 C5 119.34(13) . . ?
C4 C5 C6 120.96(12) . . ?
O2 C5 C4 123.11(12) . . ?
O2 C5 C6 115.93(11) . . ?
C1 C6 C5 117.92(12) . . ?
C1 C6 C7 120.57(11) . . ?
C5 C6 C7 121.51(11) . . ?
C6 C7 C14 111.05(10) . . ?
N1 C7 C6 108.63(10) . . ?
N1 C7 C14 107.71(10) . . ?
C9 C8 C13 119.89(12) . . ?
C9 C8 N1 120.41(12) . . ?
C13 C8 N1 119.66(12) . . ?
C10 C9 C8 120.55(13) . . ?
C9 C10 C11 119.74(13) . . ?
C12 C11 C10 119.80(13) . . ?
C11 C12 C13 120.86(13) . . ?
C8 C13 N2 120.78(12) . . ?
C12 C13 C8 119.15(12) . . ?
C12 C13 N2 119.94(12) . . ?
C15 C14 C7 110.48(10) . . ?
N2 C14 C7 109.06(10) . . ?
N2 C14 C15 109.42(10) . . ?
C16 C15 C14 120.40(12) . . ?
C16 C15 C20 117.41(12) . . ?
C20 C15 C14 122.09(12) . . ?
C17 C16 C15 121.52(13) . . ?
O3 C16 C15 116.00(12) . . ?
O3 C16 C17 122.43(12) . . ?
C18 C17 C16 119.33(13) . . ?
C19 C18 C17 120.81(13) . . ?
C18 C19 C20 119.67(13) . . ?
C19 C20 C15 121.23(12) . . ?
O4 C20 C15 121.17(12) . . ?
O4 C20 C19 117.60(12) . . ?
C8 N1 C7 115.48(10) . . ?
C13 N2 C14 118.03(10) . . ?
C5 O2 C21 117.04(11) . . ?
C16 O3 C22 116.19(11) . . ?
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
C1 C2 1.3941(19) . ?
C1 C6 1.4051(19) . ?
C1 O1 1.3648(16) . ?
C2 C3 1.377(2) . ?
C3 C4 1.390(2) . ?
C4 C5 1.3904(19) . ?
C5 C6 1.4061(18) . ?
C5 O2 1.3700(16) . ?
C6 C7 1.5176(17) . ?
C7 C14 1.5488(18) . ?
C7 N1 1.4806(16) . ?
C8 C9 1.3938(19) . ?
C8 C13 1.3973(19) . ?
C8 N1 1.4159(16) . ?
C9 C10 1.3838(19) . ?
C10 C11 1.394(2) . ?
C11 C12 1.388(2) . ?
C12 C13 1.3913(18) . ?
C13 N2 1.4252(17) . ?
C14 C15 1.5164(18) . ?
C14 N2 1.4841(16) . ?
C15 C16 1.4025(18) . ?
C15 C20 1.4032(19) . ?
C16 C17 1.3917(19) . ?
C16 O3 1.3741(16) . ?
C17 C18 1.382(2) . ?
C18 C19 1.381(2) . ?
C19 C20 1.391(2) . ?
C20 O4 1.3680(16) . ?
C21 O2 1.4311(17) . ?
C22 O3 1.4346(16) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A N1 0.93(2) 1.84(2) 2.6731(15) 148.3(18) . yes
O4 H4A N2 0.94(2) 1.80(2) 2.6583(15) 150.9(19) . yes
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
0.0014 -1.0013 -0.0005 0.0420 0.0692 0.1317
1.9979 1.0009 -1.9966 0.1261 0.2413 -0.4014
0.9996 -0.0002 -0.9986 0.0841 0.1553 -0.1349
-0.0014 1.0013 0.0005 -0.0420 -0.0692 -0.1317
-1.0017 2.0022 -0.0001 -0.0406 -0.3111 -0.1329
1.9986 0.0003 -0.9975 0.0406 0.3279 -0.2653
-1.9993 1.0003 -0.0017 0.0450 -0.4145 0.1292
0.0021 -2.0020 0.9987 -0.0435 0.1559 0.2678
0.9977 0.0019 2.0003 -0.2986 0.2074 -0.1216
-0.0006 0.0007 0.9996 -0.1276 0.0174 0.0044
0.0006 -0.0007 -0.9996 0.1276 -0.0174 -0.0044
0.0033 -2.0034 -1.0006 0.2116 0.1211 0.2589
-0.9996 0.0002 0.9986 -0.0841 -0.1553 0.1349
-0.9977 -0.0019 -2.0003 0.2986 -0.2074 0.1216
-0.0001 0.9999 -1.9988 0.2131 -0.1040 -0.1405
-2.0006 1.0018 1.9976 -0.2102 -0.3798 0.1381
1.0023 -2.0029 -0.9995 0.1681 0.2938 0.1285
-0.9976 -1.0018 -0.0015 0.0855 -0.1034 0.2621
0.0026 -1.0028 -1.9997 0.2972 0.0345 0.1228
1.0003 -0.0009 -1.9982 0.2116 0.1379 -0.1393
