#------------------------------------------------------------------------------
#$Date: 2024-03-04 22:43:21 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290274 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/97/7159797.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_7159797
loop_
_publ_author_name
'Fujita, Ryohei'
'Ooka, Kaito'
'Wasada, Hiroaki'
'Ichikawa, Yoshiyasu'
'Hosokawa, Seijiro'
_publ_section_title
;
 First synthesis of (±)-halichonadins A-D.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1901
_journal_page_last               1906
_journal_paper_doi               10.1039/d4ob00088a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C16 H25 N'
_chemical_formula_sum            'C16 H25 N'
_chemical_formula_weight         231.37
_chemical_melting_point          406.5(5)
_chemical_name_systematic        'halichonadin C'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-20
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-11-25 deposited with the CCDC.	2024-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.166(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5724(2)
_cell_length_b                   19.8160(4)
_cell_length_c                   7.59510(10)
_cell_measurement_reflns_used    5010
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.0330
_cell_measurement_theta_min      4.4710
_cell_volume                     1418.07(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_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 0.946
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00 -22.00   0.50    0.21    --  -96.00  45.00 120.00   58
  2  ω    -50.00 -23.00   0.50    0.21    --  -96.00  45.00   0.00   54
  3  ω    -63.00 -30.00   0.50    0.21    --  -96.00  61.00 -30.00   66
  4  ω    -50.00 -21.00   0.50    0.21    --  -96.00  45.00 -60.00   58
  5  ω    -49.00 -22.00   0.50    0.21    --  -96.00  45.00 -90.00   54
  6  ω    -49.00 -24.00   0.50    0.21    --  -96.00  45.00-180.00   50
  7  ω    -47.00 -21.00   0.50    0.21    --  -96.00  45.00  30.00   52
  8  ω    -49.00 -23.00   0.50    0.21    --  -96.00  45.00  90.00   52
  9  ω    -70.00 -45.00   0.50    0.05    --  -42.99 117.00 160.00   50
 10  ω    -69.00 -32.00   0.50    0.21    --  -96.00 164.00 -50.00   74
 11  ω    -97.00 -72.00   0.50    0.05    --  -42.99 164.00 -50.00   50
 12  ω   -148.00-122.00   0.50    0.21    --  -96.00-117.00  73.00   52
 13  ω   -114.00 -83.00   0.50    0.05    --  -42.99-164.00 -75.00   62
 14  ω    -77.00 -48.00   0.50    0.05    --  -42.99-164.00 -75.00   58
 15  ω   -116.00 -22.00   0.50    0.05    --  -42.99 -57.00 -30.00  188
 16  ω    127.00 178.00   0.50    0.21    --  108.01  30.00 -30.00  102
 17  ω     88.00 113.00   0.50    0.21    --  108.01 164.00 -50.00   50
 18  ω     84.00 114.00   0.50    0.21    --  108.01  30.00 -30.00   60
 19  ω     38.00  68.00   0.50    0.21    --  108.01 -61.00-150.00   60
 20  ω     45.00  70.00   0.50    0.21    --  108.01 -61.00-120.00   50
 21  ω    -33.00  32.00   0.50    0.05    --   42.99 -19.00 120.00  130
 22  ω     71.00  99.00   0.50    0.21    --  108.01 -77.00  90.00   56
 23  ω     42.00  68.00   0.50    0.21    --  108.01 -77.00  90.00   52
 24  ω     34.00  60.00   0.50    0.21    --  108.01 -61.00  90.00   52
 25  ω     50.00  76.00   0.50    0.21    --  108.01 -95.00  90.00   52
 26  ω     37.00 106.00   0.50    0.21    --  108.01-117.00  73.00  138
 27  ω     59.00  84.00   0.50    0.05    --   42.99-117.00  73.00   50
 28  ω     81.00 106.00   0.50    0.21    --  108.01 -95.00  90.00   50
 29  ω     63.00 109.00   0.50    0.05    --   42.99-164.00 -75.00   92
 30  ω     96.00 133.00   0.50    0.21    --  108.01-164.00 -75.00   74
 31  ω     54.00  87.00   0.50    0.21    --  108.01-164.00 -75.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1346032000
_diffrn_orient_matrix_UB_12      0.0347068000
_diffrn_orient_matrix_UB_13      -0.1013232000
_diffrn_orient_matrix_UB_21      -0.0770484000
_diffrn_orient_matrix_UB_22      -0.0685802000
_diffrn_orient_matrix_UB_23      -0.0210609000
_diffrn_orient_matrix_UB_31      -0.0520283000
_diffrn_orient_matrix_UB_32      0.0115686000
_diffrn_orient_matrix_UB_33      0.1781803000
_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  0.0363
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            9021
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.070
_diffrn_reflns_theta_min         4.463
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.459
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.312
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
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_colour_primary    colourless
_exptl_crystal_density_diffrn    1.084
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane-dichloromethane'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0429
_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)+(0.0514P)²+0.3504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2441
_reflns_number_total             2768
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00088a2.cif
_cod_data_source_block           exp_329_auto
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '406-407' was changed to
'406.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159796--7159798.cif.
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7159797
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C16H25N
_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_max   0.964
_shelx_estimated_absorpt_t_min   0.856
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C002(H002), C003(H003), C004(H004), C007(H007)
2.b Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C00B(H00I,H00J), C00D(H00M,H00N), C00E(H00O,H00P), C00F(H00Q,
 H00R)
2.c X=CH2 refined with riding coordinates:
 C00C(H00K,H00L)
2.d Idealised Me refined as rotating group:
 C009(H00C,H00D,H00E), C00A(H00F,H00G,H00H), C00G(H00S,H00T,H00U)
;
_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 1.298
_oxdiff_exptl_absorpt_empirical_full_min 0.738
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N001 N 0.48142(11) 0.61354(6) 0.51018(13) 0.0319(3) Uani 1 1 d . . . . .
C002 C 0.39912(11) 0.61256(6) 0.65245(14) 0.0207(2) Uani 1 1 d . . . . .
H002 H 0.398909 0.565654 0.700965 0.025 Uiso 1 1 calc R U . . .
C003 C 0.46920(12) 0.66020(6) 0.80299(14) 0.0233(3) Uani 1 1 d . . . . .
H003 H 0.464346 0.706680 0.750973 0.028 Uiso 1 1 calc R U . . .
C004 C 0.24589(12) 0.63340(5) 0.57647(14) 0.0216(3) Uani 1 1 d . . . . .
H004 H 0.251029 0.680870 0.533356 0.026 Uiso 1 1 calc R U . . .
C005 C 0.15237(12) 0.63566(6) 0.72457(15) 0.0252(3) Uani 1 1 d . . . . .
C006 C 0.17098(12) 0.59320(6) 0.41759(14) 0.0246(3) Uani 1 1 d . . . . .
C007 C 0.62737(12) 0.64478(6) 0.86972(15) 0.0262(3) Uani 1 1 d . . . . .
H007 H 0.674939 0.644748 0.762603 0.031 Uiso 1 1 calc R U . . .
C008 C 0.37884(13) 0.66094(7) 0.95016(16) 0.0294(3) Uani 1 1 d . . . . .
H00A H 0.379449 0.615470 1.004321 0.035 Uiso 1 1 calc R U . . .
H00B H 0.420322 0.693002 1.045078 0.035 Uiso 1 1 calc R U . . .
C009 C 0.13039(14) 0.56514(7) 0.79684(17) 0.0312(3) Uani 1 1 d . . . . .
H00C H 0.090349 0.535402 0.697602 0.047 Uiso 1 1 calc R U . . .
H00D H 0.064982 0.567800 0.882384 0.047 Uiso 1 1 calc R U . . .
H00E H 0.221738 0.547043 0.856858 0.047 Uiso 1 1 calc R U . . .
C00A C 0.65433(13) 0.57602(6) 0.95875(16) 0.0304(3) Uani 1 1 d . . . . .
H00F H 0.614519 0.575206 1.069080 0.046 Uiso 1 1 calc R U . . .
H00G H 0.756747 0.567680 0.987228 0.046 Uiso 1 1 calc R U . . .
H00H H 0.609062 0.540907 0.877227 0.046 Uiso 1 1 calc R U . . .
C00B C 0.03032(13) 0.62367(6) 0.33514(17) 0.0310(3) Uani 1 1 d . . . . .
H00I H -0.015874 0.594928 0.234972 0.037 Uiso 1 1 calc R U . . .
H00J H 0.046043 0.668849 0.286506 0.037 Uiso 1 1 calc R U . . .
C00C C 0.21648(13) 0.53551(7) 0.36081(16) 0.0322(3) Uani 1 1 d . . . . .
H00K H 0.159936 0.511863 0.265049 0.039 Uiso 1 1 calc R U . . .
H00L H 0.305717 0.517704 0.415787 0.039 Uiso 1 1 calc R U . . .
C00D C -0.06662(13) 0.63001(7) 0.47374(18) 0.0330(3) Uani 1 1 d . . . . .
H00M H -0.095271 0.584471 0.507475 0.040 Uiso 1 1 calc R U . . .
H00N H -0.153509 0.655066 0.421250 0.040 Uiso 1 1 calc R U . . .
C00E C 0.22603(14) 0.68157(7) 0.87575(18) 0.0349(3) Uani 1 1 d . . . . .
H00O H 0.225814 0.728415 0.830377 0.042 Uiso 1 1 calc R U . . .
H00P H 0.170696 0.681071 0.974238 0.042 Uiso 1 1 calc R U . . .
C00F C 0.00863(14) 0.66692(7) 0.64049(19) 0.0347(3) Uani 1 1 d . . . . .
H00Q H -0.054231 0.667096 0.730945 0.042 Uiso 1 1 calc R U . . .
H00R H 0.024237 0.714425 0.608550 0.042 Uiso 1 1 calc R U . . .
C00G C 0.69773(14) 0.70011(7) 0.99545(18) 0.0361(3) Uani 1 1 d . . . . .
H00S H 0.675566 0.744330 0.939724 0.054 Uiso 1 1 calc R U . . .
H00T H 0.800782 0.693397 1.018651 0.054 Uiso 1 1 calc R U . . .
H00U H 0.661927 0.698033 1.108503 0.054 Uiso 1 1 calc R U . . .
C00H C 0.54728(16) 0.61547(11) 0.39700(19) 0.0574(5) Uani 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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 5 0.1257
-5 6 1 0.1231
-5 6 -1 0.1207
2 0 -5 0.1473
5 -6 1 0.1180
-2 -12 0 0.0112
2 12 0 0.0655
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
C00H N001 C002 178.87(16) . . ?
N001 C002 C003 108.84(9) . . ?
N001 C002 C004 109.03(9) . . ?
C004 C002 C003 112.08(9) . . ?
C007 C003 C002 113.35(9) . . ?
C008 C003 C002 108.64(9) . . ?
C008 C003 C007 114.29(9) . . ?
C002 C004 C005 111.67(9) . . ?
C006 C004 C002 116.36(9) . . ?
C006 C004 C005 109.79(9) . . ?
C009 C005 C004 111.48(9) . . ?
C009 C005 C00E 110.31(10) . . ?
C009 C005 C00F 110.28(10) . . ?
C00E C005 C004 108.09(10) . . ?
C00E C005 C00F 109.29(10) . . ?
C00F C005 C004 107.30(10) . . ?
C00B C006 C004 112.48(10) . . ?
C00C C006 C004 125.24(11) . . ?
C00C C006 C00B 122.16(11) . . ?
C00A C007 C003 113.79(10) . . ?
C00A C007 C00G 110.04(10) . . ?
C00G C007 C003 111.24(10) . . ?
C00E C008 C003 111.11(10) . . ?
C006 C00B C00D 110.71(10) . . ?
C00B C00D C00F 110.85(10) . . ?
C008 C00E C005 113.66(10) . . ?
C00D C00F C005 114.01(10) . . ?
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
N001 C002 1.4454(14) . ?
N001 C00H 1.1529(18) . ?
C002 C003 1.5420(15) . ?
C002 C004 1.5349(15) . ?
C003 C007 1.5401(16) . ?
C003 C008 1.5294(16) . ?
C004 C005 1.5570(15) . ?
C004 C006 1.5164(15) . ?
C005 C009 1.5294(17) . ?
C005 C00E 1.5354(17) . ?
C005 C00F 1.5409(17) . ?
C006 C00B 1.5073(17) . ?
C006 C00C 1.3225(18) . ?
C007 C00A 1.5229(17) . ?
C007 C00G 1.5298(17) . ?
C008 C00E 1.5279(18) . ?
C00B C00D 1.5264(18) . ?
C00D C00F 1.5283(18) . ?
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
N001 C002 C003 C007 -53.80(12) . . . . ?
N001 C002 C003 C008 178.00(9) . . . . ?
N001 C002 C004 C005 -178.14(9) . . . . ?
N001 C002 C004 C006 54.74(12) . . . . ?
C002 C003 C007 C00A -64.55(12) . . . . ?
C002 C003 C007 C00G 170.49(9) . . . . ?
C002 C003 C008 C00E -56.47(13) . . . . ?
C002 C004 C005 C009 -67.35(12) . . . . ?
C002 C004 C005 C00E 54.05(12) . . . . ?
C002 C004 C005 C00F 171.81(9) . . . . ?
C002 C004 C006 C00B -171.31(9) . . . . ?
C002 C004 C006 C00C 12.65(16) . . . . ?
C003 C002 C004 C005 -57.59(11) . . . . ?
C003 C002 C004 C006 175.30(9) . . . . ?
C003 C008 C00E C005 58.03(15) . . . . ?
C004 C002 C003 C007 -174.47(9) . . . . ?
C004 C002 C003 C008 57.33(12) . . . . ?
C004 C005 C00E C008 -54.94(14) . . . . ?
C004 C005 C00F C00D 56.10(14) . . . . ?
C004 C006 C00B C00D -57.25(13) . . . . ?
C005 C004 C006 C00B 60.65(12) . . . . ?
C005 C004 C006 C00C -115.39(13) . . . . ?
C006 C004 C005 C009 63.25(12) . . . . ?
C006 C004 C005 C00E -175.35(10) . . . . ?
C006 C004 C005 C00F -57.59(12) . . . . ?
C006 C00B C00D C00F 52.33(14) . . . . ?
C007 C003 C008 C00E 175.87(10) . . . . ?
C008 C003 C007 C00A 60.67(13) . . . . ?
C008 C003 C007 C00G -64.29(13) . . . . ?
C009 C005 C00E C008 67.17(14) . . . . ?
C009 C005 C00F C00D -65.49(14) . . . . ?
C00B C00D C00F C005 -54.22(15) . . . . ?
C00C C006 C00B C00D 118.93(13) . . . . ?
C00E C005 C00F C00D 173.08(11) . . . . ?
C00F C005 C00E C008 -171.42(11) . . . . ?
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
-0.3186 -1.3730 4.8635 -0.4976 0.0163 0.8673
-5.4599 5.9830 1.3020 0.8107 -0.0171 0.5853
-5.0960 6.2836 -0.7287 0.9779 -0.0229 0.2080
1.5044 -0.0074 -4.9209 0.2959 -0.0118 -0.9552
4.7292 -6.1181 1.4738 -0.9982 0.0242 -0.0542
-1.9229 -12.2274 0.1809 -0.1839 0.9829 -0.0092
2.0070 12.1710 -0.3130 0.1840 -0.9827 -0.0194
