#------------------------------------------------------------------------------
#$Date: 2021-05-05 11:59:25 +0300 (Wed, 05 May 2021) $
#$Revision: 264937 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/04/7060475.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_7060475
loop_
_publ_author_name
'Kukkonen, Esa'
'Lahtinen, Elmeri'
'Myllyperkiö, Pasi'
'Haukka, Matti'
'Konu, Jari'
_publ_section_title
;
 Nonlinear optical properties of diaromatic stilbene, butadiene and
 thiophene derivatives
;
_journal_issue                   15
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6640
_journal_page_last               6650
_journal_paper_doi               10.1039/D1NJ00456E
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C16 H12 F N O2'
_chemical_formula_sum            'C16 H12 F N O2'
_chemical_formula_weight         269.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-12 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.703(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1272(2)
_cell_length_b                   12.8757(4)
_cell_length_c                   7.3763(3)
_cell_measurement_reflns_used    2735
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.1180
_cell_measurement_theta_min      3.4030
_cell_volume                     654.74(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -18.00   1.00    2.00    --  -41.65 -57.00 150.00   95
  2  ω    -74.00  34.00   1.00    2.00    --  -41.65  77.00-120.00  108
  3  ω   -105.00 -21.00   1.00    2.00    --  -41.65 -57.00   0.00   84
  4  ω     -7.00  70.00   1.00    2.00    --   41.65 -57.00   0.00   77
  5  ω     36.00 116.00   1.00    8.00    --  112.00-111.00   0.00   80
  6  ω     31.00 154.00   1.00    8.00    --  112.00 -15.00 120.00  123
  7  ω     37.00 137.00   1.00    8.00    --  112.00 -30.00  30.00  100
  8  ω     33.00  73.00   1.00    8.00    --  112.00 -94.00-120.00   40
  9  ω     65.00 122.00   1.00    8.00    --  112.00-126.00 123.00   57
 10  ω    106.00 131.00   1.00    8.00    --  112.00 111.00 -90.00   25
 11  ω    152.00 178.00   1.00    8.00    --  112.00 111.00 -90.00   26
 12  ω     72.00 123.00   1.00    8.00    --  112.00 178.00  30.00   51
 13  ω    108.00 178.00   1.00    8.00    --  112.00  30.00 120.00   70
 14  ω     36.00 102.00   1.00    8.00    --  112.00 -94.00 -90.00   66
 15  ω     30.00 108.00   1.00    8.00    --  112.00 -94.00 120.00   78
 16  ω     46.00 136.00   1.00    8.00    --  112.00 -45.00 -60.00   90
 17  ω     40.00 104.00   1.00    8.00    --  112.00-111.00-150.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0596964000
_diffrn_orient_matrix_UB_12      -0.1131870000
_diffrn_orient_matrix_UB_13      -0.0212480000
_diffrn_orient_matrix_UB_21      0.1921401000
_diffrn_orient_matrix_UB_22      0.0382345000
_diffrn_orient_matrix_UB_23      -0.0199978000
_diffrn_orient_matrix_UB_31      0.0784816000
_diffrn_orient_matrix_UB_32      -0.0074046000
_diffrn_orient_matrix_UB_33      0.2214361000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4854
_diffrn_reflns_point_group_measured_fraction_full 0.702
_diffrn_reflns_point_group_measured_fraction_max 0.632
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         85.299
_diffrn_reflns_theta_min         3.433
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_correction_T_min  0.746
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.532
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.133
_refine_diff_density_max         0.094
_refine_diff_density_min         -0.105
_refine_diff_density_rms         0.022
_refine_ls_abs_structure_details
;
 Flack x determined using 462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         1881
_refine_ls_number_restraints     484
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0334
_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)+(0.0648P)²+0.0266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0962
_reflns_Friedel_coverage         0.373
_reflns_Friedel_fraction_full    0.406
_reflns_Friedel_fraction_max     0.346
_reflns_number_gt                1777
_reflns_number_total             1881
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj00456e2.cif
_cod_data_source_block           compound_2a
_cod_depositor_comments
'Adding full bibliography for 7060468--7060480.cif.'
_cod_database_code               7060475
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C16 H12 F1 N1 O2'
_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 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1C-N1C \\sim O2C-N1C
 with sigma of 0.001
 O1C-C1C \\sim C1C-O2C
 with sigma of 0.001
 C5C-C1C \\sim C5B-C1B
 with sigma of 0.04
 N1C-O1C \\sim N1B-O1B
 with sigma of 0.02
 N1C-O2C \\sim N1B-O2B
 with sigma of 0.02
 N1C-C1C \\sim N1B-C1B
 with sigma of 0.02
 F1C-C14C \\sim F1B-C14B
 with sigma of 0.02
 C15C-C13C \\sim C15B-C13B
 with sigma of 0.04
 O2C-C1C \\sim O2B-C1B
 with sigma of 0.04
 C11C-C16C \\sim C11B-C16B
 with sigma of 0.02
 C11C-C12C \\sim C11B-C12B
 with sigma of 0.02
 C11C-C10C \\sim C11B-C10B
 with sigma of 0.02
 C6C-C2C \\sim C6B-C2B
 with sigma of 0.04
 C16C-C15C \\sim C16B-C15B
 with sigma of 0.02
 C15C-C14C \\sim C15B-C14B
 with sigma of 0.02
 C14C-C13C \\sim C14B-C13B
 with sigma of 0.02
 C16C-C10C \\sim C16B-C10B
 with sigma of 0.04
 C14C-C12C \\sim C14B-C12B
 with sigma of 0.04
 C13C-C12C \\sim C13B-C12B
 with sigma of 0.02
 C8C-C4C \\sim C8B-C4B
 with sigma of 0.04
 C9C-C8C \\sim C9B-C8B
 with sigma of 0.02
 C9C-C10C \\sim C9B-C10B
 with sigma of 0.02
 C7C-C3C \\sim C7B-C3B
 with sigma of 0.04
 C4C-C2C \\sim C4B-C2B
 with sigma of 0.04
 C8C-C7C \\sim C8B-C7B
 with sigma of 0.02
 C7C-C4C \\sim C7B-C4B
 with sigma of 0.02
 C4C-C5C \\sim C4B-C5B
 with sigma of 0.02
 C4C-C3C \\sim C4B-C3B
 with sigma of 0.02
 C5C-C6C \\sim C5B-C6B
 with sigma of 0.02
 C6C-C1C \\sim C6B-C1B
 with sigma of 0.02
 C12C-C10C \\sim C12B-C10B
 with sigma of 0.04
 C1C-C2C \\sim C1B-C2B
 with sigma of 0.02
 C9C-C7C \\sim C9B-C7B
 with sigma of 0.04
 C2C-C3C \\sim C2B-C3B
 with sigma of 0.02
 C8C-C10C \\sim C8B-C10B
 with sigma of 0.04
 N1C-C6C \\sim N1B-C6B
 with sigma of 0.04
 N1C-C2C \\sim N1B-C2B
 with sigma of 0.04
 C7C-C5C \\sim C7B-C5B
 with sigma of 0.04
 F1C-C15C \\sim F1B-C15B
 with sigma of 0.04
 F1C-C13C \\sim F1B-C13B
 with sigma of 0.04
 O1C-O2C \\sim O1B-O2B
 with sigma of 0.04
 C4C-C6C \\sim C4B-C6B
 with sigma of 0.04
 O1C-C1C \\sim O1B-C1B
 with sigma of 0.04
 C11C-C15C \\sim C11B-C15B
 with sigma of 0.04
 C11C-C13C \\sim C11B-C13B
 with sigma of 0.04
 C11C-C9C \\sim C11B-C9B
 with sigma of 0.04
 C5C-C3C \\sim C5B-C3B
 with sigma of 0.04
 C1C-C3C \\sim C1B-C3B
 with sigma of 0.04
 C16C-C14C \\sim C16B-C14B
 with sigma of 0.04
 C16C-C12C \\sim C16B-C12B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: F1A(0.4) O1A(0.4) O2A(0.4) N1A(0.4) C1A(0.4) C2A(0.4) H2A(0.4)
 C3A(0.4) H3A(0.4) C4A(0.4) C5A(0.4) H5A(0.4) C6A(0.4) H6A(0.4) C7A(0.4)
 H7A(0.4) C8A(0.4) H8A(0.4) C9A(0.4) H9A(0.4) C10A(0.4) H10A(0.4) C11A(0.4)
 C12A(0.4) H12A(0.4) C13A(0.4) H13A(0.4) C14A(0.4) C15A(0.4) H15A(0.4)
 C16A(0.4) H16A(0.4) F1B(0.4) O1B(0.4) O2B(0.4) N1B(0.4) C1B(0.4) C2B(0.4)
 H2B(0.4) C3B(0.4) H3B(0.4) C4B(0.4) C5B(0.4) H5B(0.4) C6B(0.4) H6B(0.4)
 C7B(0.4) H7B(0.4) C8B(0.4) H8B(0.4) C9B(0.4) H9B(0.4) C10B(0.4) H10B(0.4)
 C11B(0.4) C12B(0.4) H12B(0.4) C13B(0.4) H13B(0.4) C14B(0.4) C15B(0.4)
 H15B(0.4) C16B(0.4) H16B(0.4) F1C(0.2) O1C(0.2) O2C(0.2) N1C(0.2) C4C(0.2)
 C5C(0.2) H5C(0.2) C6C(0.2) H6C(0.2) C1C(0.2) C2C(0.2) H2C(0.2) C3C(0.2)
 H3C(0.2) C7C(0.2) H7C(0.2) C8C(0.2) H8C(0.2) C9C(0.2) H9C(0.2) C10C(0.2)
 H10C(0.2) C11C(0.2) C16C(0.2) H16C(0.2) C15C(0.2) H15C(0.2) C14C(0.2)
 C13C(0.2) H13C(0.2) C12C(0.2) H12C(0.2)
5.a Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A),
 C10A(H10A), C12A(H12A), C13A(H13A), C15A(H15A), C16A(H16A), C2B(H2B), C3B(H3B),
  C5B(H5B), C6B(H6B), C7B(H7B), C8B(H8B), C9B(H9B), C10B(H10B), C12B(H12B),
 C13B(H13B), C15B(H15B), C16B(H16B), C5C(H5C), C6C(H6C), C2C(H2C), C3C(H3C),
 C7C(H7C), C8C(H8C), C9C(H9C), C10C(H10C), C16C(H16C), C15C(H15C), C13C(H13C),
 C12C(H12C)
5.b Fitted hexagon refined as free rotating group:
 C4C(C5C,C6C,C1C,C2C,C3C), C11C(C16C,C15C,C14C,C13C,C12C)
;
_ins_header
;
TITL ek1926_a_Pc_small in Pc 
REM Pc (#7 in standard setting)
CELL 1.54184   7.376128  12.878279   7.126359  90.0000 104.7024  90.0000
ZERR    2.00   0.000357   0.000410   0.000224   0.0000   0.0040   0.0000
LATT -1
SYMM  x,-y, z+1/2 
SFAC C H N O F
UNIT 32.00 24.00 2.00 4.00 2.00
TREF
HKLF 4
END
;
_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 1.521
_oxdiff_exptl_absorpt_empirical_full_min 0.660
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, 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
F1A F 1.4901(11) 0.9102(5) 1.1098(10) 0.0478(15) Uani 0.4 1 d . U P A 1
O1A O -0.3490(10) 0.5195(6) -0.2031(14) 0.0590(16) Uani 0.4 1 d . U P A 1
O2A O -0.4550(11) 0.6339(5) -0.0318(14) 0.0556(15) Uani 0.4 1 d . U P A 1
N1A N -0.3212(15) 0.5886(8) -0.071(2) 0.0403(17) Uani 0.4 1 d . U P A 1
C1A C -0.1281(12) 0.6102(7) 0.0438(16) 0.0344(17) Uani 0.4 1 d . U P A 1
C2A C -0.0975(12) 0.6973(6) 0.1654(13) 0.0353(16) Uani 0.4 1 d . U P A 1
H2A H -0.199986 0.739819 0.175050 0.042 Uiso 0.4 1 calc R . P A 1
C3A C 0.0821(12) 0.7160(7) 0.2649(16) 0.0356(17) Uani 0.4 1 d . U P A 1
H3A H 0.108112 0.774008 0.342385 0.043 Uiso 0.4 1 calc R . P A 1
C4A C 0.2303(12) 0.6493(7) 0.2535(14) 0.0362(16) Uani 0.4 1 d . U P A 1
C5A C 0.1928(11) 0.5609(7) 0.1349(15) 0.0392(18) Uani 0.4 1 d . U P A 1
H5A H 0.293564 0.515752 0.130948 0.047 Uiso 0.4 1 calc R . P A 1
C6A C 0.0146(13) 0.5417(8) 0.0290(16) 0.0340(17) Uani 0.4 1 d . U P A 1
H6A H -0.011540 0.484680 -0.050956 0.041 Uiso 0.4 1 calc R . P A 1
C7A C 0.4304(12) 0.6705(8) 0.3688(16) 0.049(2) Uani 0.4 1 d . U P A 1
H7A H 0.522226 0.620592 0.360556 0.059 Uiso 0.4 1 calc R . P A 1
C8A C 0.495(2) 0.7472(12) 0.478(2) 0.045(3) Uani 0.4 1 d . U P A 1
H8A H 0.406300 0.797460 0.491478 0.054 Uiso 0.4 1 calc R . P A 1
C9A C 0.6931(15) 0.7621(9) 0.5803(17) 0.046(2) Uani 0.4 1 d . U P A 1
H9A H 0.779501 0.710019 0.568093 0.055 Uiso 0.4 1 calc R . P A 1
C10A C 0.7671(12) 0.8403(6) 0.6894(15) 0.0438(18) Uani 0.4 1 d . U P A 1
H10A H 0.680638 0.893567 0.695018 0.053 Uiso 0.4 1 calc R . P A 1
C11A C 0.9566(13) 0.8555(9) 0.7986(15) 0.0401(19) Uani 0.4 1 d . U P A 1
C12A C 0.9995(16) 0.9408(7) 0.9170(16) 0.0446(18) Uani 0.4 1 d . U P A 1
H12A H 0.900155 0.986023 0.925051 0.054 Uiso 0.4 1 calc R . P A 1
C13A C 1.1817(15) 0.9600(6) 1.0209(13) 0.0397(15) Uani 0.4 1 d . U P A 1
H13A H 1.210359 1.017537 1.099246 0.048 Uiso 0.4 1 calc R . P A 1
C14A C 1.3156(14) 0.8933(7) 1.0054(15) 0.0394(17) Uani 0.4 1 d . U P A 1
C15A C 1.2798(12) 0.8040(7) 0.8845(15) 0.0325(17) Uani 0.4 1 d . U P A 1
H15A H 1.380103 0.759383 0.876662 0.039 Uiso 0.4 1 calc R . P A 1
C16A C 1.0975(14) 0.7867(8) 0.7831(16) 0.0361(18) Uani 0.4 1 d . U P A 1
H16A H 1.068024 0.729309 0.704409 0.043 Uiso 0.4 1 calc R . P A 1
F1B F -0.3839(13) 0.5866(9) -0.0825(16) 0.072(3) Uani 0.4 1 d D U P B 2
O1B O 1.5652(7) 0.8735(5) 1.0789(10) 0.0532(13) Uani 0.4 1 d D U P B 2
O2B O 1.4508(10) 0.9838(5) 1.2396(11) 0.0630(17) Uani 0.4 1 d D U P B 2
N1B N 1.4314(12) 0.9248(9) 1.1161(17) 0.0364(17) Uani 0.4 1 d D U P B 2
C1B C 1.2447(10) 0.8980(7) 1.0004(14) 0.0316(16) Uani 0.4 1 d D U P B 2
C2B C 1.1046(11) 0.9633(6) 1.0150(14) 0.0329(18) Uani 0.4 1 d D U P B 2
H2B H 1.129275 1.020293 1.095050 0.039 Uiso 0.4 1 calc R . P B 2
C3B C 0.9227(10) 0.9425(5) 0.9063(11) 0.0291(13) Uani 0.4 1 d D U P B 2
H3B H 0.821337 0.986506 0.913598 0.035 Uiso 0.4 1 calc R . P B 2
C4B C 0.8829(10) 0.8560(5) 0.7825(11) 0.0267(13) Uani 0.4 1 d D U P B 2
C5B C 1.0295(12) 0.7909(6) 0.7770(14) 0.0298(15) Uani 0.4 1 d D U P B 2
H5B H 1.006001 0.732835 0.699618 0.036 Uiso 0.4 1 calc R . P B 2
C6B C 1.2113(11) 0.8098(6) 0.8841(14) 0.0339(15) Uani 0.4 1 d D U P B 2
H6B H 1.312615 0.764978 0.880539 0.041 Uiso 0.4 1 calc R . P B 2
C7B C 0.6925(10) 0.8401(4) 0.6744(9) 0.0265(12) Uani 0.4 1 d D U P B 2
H7B H 0.603738 0.892892 0.675485 0.032 Uiso 0.4 1 calc R . P B 2
C8B C 0.6238(14) 0.7534(6) 0.5661(12) 0.0257(16) Uani 0.4 1 d D U P B 2
H8B H 0.709233 0.699298 0.562719 0.031 Uiso 0.4 1 calc R . P B 2
C9B C 0.4293(12) 0.7442(7) 0.4609(12) 0.0303(19) Uani 0.4 1 d D U P B 2
H9B H 0.343133 0.797604 0.466674 0.036 Uiso 0.4 1 calc R . P B 2
C10B C 0.3629(11) 0.6602(6) 0.3512(11) 0.0341(15) Uani 0.4 1 d D U P B 2
H10B H 0.451460 0.608325 0.343557 0.041 Uiso 0.4 1 calc R . P B 2
C11B C 0.1604(12) 0.6461(7) 0.2440(13) 0.0333(17) Uani 0.4 1 d D U P B 2
C12B C 0.0113(14) 0.7115(6) 0.2496(14) 0.0339(17) Uani 0.4 1 d D U P B 2
H12B H 0.029891 0.768916 0.328509 0.041 Uiso 0.4 1 calc R . P B 2
C13B C -0.1639(14) 0.6892(9) 0.1357(17) 0.046(2) Uani 0.4 1 d D U P B 2
H13B H -0.266900 0.733609 0.135665 0.055 Uiso 0.4 1 calc R . P B 2
C14B C -0.1972(14) 0.6054(8) 0.0216(15) 0.043(2) Uani 0.4 1 d D U P B 2
C15B C -0.0555(14) 0.5384(8) 0.0096(14) 0.045(2) Uani 0.4 1 d D U P B 2
H15B H -0.078427 0.482159 -0.072034 0.054 Uiso 0.4 1 calc R . P B 2
C16B C 0.1222(13) 0.5580(7) 0.1237(14) 0.0377(17) Uani 0.4 1 d D U P B 2
H16B H 0.223052 0.512222 0.123252 0.045 Uiso 0.4 1 calc R . P B 2
F1C F 1.426(2) 0.9652(13) 1.137(3) 0.092(5) Uani 0.2 1 d D U P C 3
O1C O -0.2925(17) 0.4901(11) -0.149(2) 0.080(5) Uani 0.2 1 d D U P C 3
O2C O -0.4845(14) 0.5992(13) -0.071(3) 0.076(4) Uani 0.2 1 d D U P C 3
N1C N -0.332(2) 0.5613(14) -0.064(3) 0.052(4) Uani 0.2 1 d D U P C 3
C4C C 0.1516(11) 0.7014(8) 0.2929(13) 0.034(2) Uani 0.2 1 d D U P C 3
C5C C 0.1703(12) 0.6101(8) 0.1983(16) 0.032(2) Uani 0.2 1 d DG U P C 3
H5C H 0.291430 0.579308 0.214522 0.039 Uiso 0.2 1 calc R . P C 3
C6C C 0.0079(16) 0.5650(8) 0.0792(19) 0.038(3) Uani 0.2 1 d DG U P C 3
H6C H 0.020396 0.503975 0.015892 0.046 Uiso 0.2 1 calc R . P C 3
C1C C -0.1732(13) 0.6111(11) 0.055(2) 0.038(4) Uani 0.2 1 d DG U P C 3
C2C C -0.1919(11) 0.7023(10) 0.150(2) 0.038(3) Uani 0.2 1 d DG U P C 3
H2C H -0.313006 0.733121 0.133352 0.046 Uiso 0.2 1 calc R . P C 3
C3C C -0.0295(14) 0.7474(6) 0.2686(14) 0.034(2) Uani 0.2 1 d DG U P C 3
H3C H -0.041974 0.808456 0.331983 0.041 Uiso 0.2 1 calc R . P C 3
C7C C 0.3032(18) 0.7525(9) 0.4126(18) 0.039(2) Uani 0.2 1 d D U P C 3
H7C H 0.269451 0.810668 0.472119 0.047 Uiso 0.2 1 calc R . P C 3
C8C C 0.495(3) 0.730(3) 0.455(5) 0.043(5) Uani 0.2 1 d D U P C 3
H8C H 0.537190 0.673226 0.397356 0.052 Uiso 0.2 1 calc R . P C 3
C9C C 0.631(2) 0.7895(13) 0.585(3) 0.035(3) Uani 0.2 1 d D U P C 3
H9C H 0.595078 0.850517 0.635265 0.042 Uiso 0.2 1 calc R . P C 3
C10C C 0.8168(17) 0.7539(9) 0.6344(17) 0.041(2) Uani 0.2 1 d D U P C 3
H10C H 0.843933 0.690890 0.585033 0.049 Uiso 0.2 1 calc R . P C 3
C11C C 0.9762(14) 0.8099(11) 0.7609(18) 0.043(3) Uani 0.2 1 d D U P C 3
C16C C 1.1648(18) 0.7726(10) 0.793(2) 0.055(4) Uani 0.2 1 d DG U P C 3
H16C H 1.190024 0.713374 0.730564 0.066 Uiso 0.2 1 calc R . P C 3
C15C C 1.3157(13) 0.8240(14) 0.917(3) 0.062(4) Uani 0.2 1 d DG U P C 3
H15C H 1.441855 0.799040 0.937814 0.074 Uiso 0.2 1 calc R . P C 3
C14C C 1.278(2) 0.9125(14) 1.009(3) 0.066(6) Uani 0.2 1 d DG U P C 3
C13C C 1.089(3) 0.9498(11) 0.978(3) 0.064(6) Uani 0.2 1 d DG U P C 3
H13C H 1.064103 1.009009 1.039597 0.077 Uiso 0.2 1 calc R . P C 3
C12C C 0.9385(17) 0.8984(11) 0.853(2) 0.048(3) Uani 0.2 1 d DG U P C 3
H12C H 0.812268 0.923344 0.832348 0.058 Uiso 0.2 1 calc R . P C 3
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'
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'
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
-3 -1 4 0.1020
3 1 -4 0.1020
-1 -1 5 0.1490
1 1 -5 0.1860
0 1 0 0.0647
0 -1 0 0.0687
5 1 -1 0.2132
-5 -1 1 0.1472
1 -7 2 0.1090
4 -1 -3 0.1286
-3 5 2 0.0970
3 -6 -2 0.0979
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
O1A N1A C1A 120.9(7) . . ?
O2A N1A O1A 121.9(9) . . ?
O2A N1A C1A 117.1(9) . . ?
C2A C1A N1A 119.5(7) . . ?
C6A C1A N1A 116.3(8) . . ?
C6A C1A C2A 124.1(8) . . ?
C1A C2A H2A 121.1 . . ?
C3A C2A C1A 117.8(7) . . ?
C3A C2A H2A 121.1 . . ?
C2A C3A H3A 120.0 . . ?
C2A C3A C4A 120.0(7) . . ?
C4A C3A H3A 120.0 . . ?
C3A C4A C5A 120.6(7) . . ?
C3A C4A C7A 119.2(8) . . ?
C5A C4A C7A 120.2(7) . . ?
C4A C5A H5A 119.6 . . ?
C6A C5A C4A 120.8(7) . . ?
C6A C5A H5A 119.6 . . ?
C1A C6A H6A 121.7 . . ?
C5A C6A C1A 116.7(8) . . ?
C5A C6A H6A 121.7 . . ?
C4A C7A H7A 115.1 . . ?
C8A C7A C4A 129.8(10) . . ?
C8A C7A H7A 115.1 . . ?
C7A C8A H8A 117.1 . . ?
C7A C8A C9A 125.7(13) . . ?
C9A C8A H8A 117.1 . . ?
C8A C9A H9A 116.0 . . ?
C10A C9A C8A 127.9(11) . . ?
C10A C9A H9A 116.0 . . ?
C9A C10A H10A 115.1 . . ?
C9A C10A C11A 129.7(9) . . ?
C11A C10A H10A 115.1 . . ?
C12A C11A C10A 119.9(10) . . ?
C16A C11A C10A 118.9(10) . . ?
C16A C11A C12A 121.1(9) . . ?
C11A C12A H12A 119.1 . . ?
C13A C12A C11A 121.8(9) . . ?
C13A C12A H12A 119.1 . . ?
C12A C13A H13A 121.7 . . ?
C14A C13A C12A 116.6(7) . . ?
C14A C13A H13A 121.7 . . ?
F1A C14A C13A 116.5(8) . . ?
F1A C14A C15A 119.5(7) . . ?
C13A C14A C15A 124.0(8) . . ?
C14A C15A H15A 120.9 . . ?
C16A C15A C14A 118.2(7) . . ?
C16A C15A H15A 120.9 . . ?
C11A C16A H16A 120.9 . . ?
C15A C16A C11A 118.3(8) . . ?
C15A C16A H16A 120.9 . . ?
O1B N1B C1B 112.9(8) . . ?
O2B N1B O1B 124.8(9) . . ?
O2B N1B C1B 122.1(8) . . ?
C2B C1B N1B 113.8(7) . . ?
C2B C1B C6B 123.0(7) . . ?
C6B C1B N1B 123.2(7) . . ?
C1B C2B H2B 121.7 . . ?
C1B C2B C3B 116.7(7) . . ?
C3B C2B H2B 121.7 . . ?
C2B C3B H3B 118.8 . . ?
C2B C3B C4B 122.3(6) . . ?
C4B C3B H3B 118.8 . . ?
C5B C4B C3B 118.4(6) . . ?
C5B C4B C7B 122.6(6) . . ?
C7B C4B C3B 119.0(6) . . ?
C4B C5B H5B 119.9 . . ?
C4B C5B C6B 120.3(7) . . ?
C6B C5B H5B 119.9 . . ?
C1B C6B H6B 120.4 . . ?
C5B C6B C1B 119.2(7) . . ?
C5B C6B H6B 120.4 . . ?
C4B C7B H7B 116.8 . . ?
C8B C7B C4B 126.4(6) . . ?
C8B C7B H7B 116.8 . . ?
C7B C8B H8B 118.7 . . ?
C7B C8B C9B 122.6(9) . . ?
C9B C8B H8B 118.7 . . ?
C8B C9B H9B 118.7 . . ?
C10B C9B C8B 122.6(8) . . ?
C10B C9B H9B 118.7 . . ?
C9B C10B H10B 117.9 . . ?
C9B C10B C11B 124.3(8) . . ?
C11B C10B H10B 117.9 . . ?
C12B C11B C10B 125.0(7) . . ?
C12B C11B C16B 118.9(7) . . ?
C16B C11B C10B 116.1(8) . . ?
C11B C12B H12B 121.4 . . ?
C13B C12B C11B 117.1(8) . . ?
C13B C12B H12B 121.4 . . ?
C12B C13B H13B 118.5 . . ?
C12B C13B C14B 123.1(9) . . ?
C14B C13B H13B 118.5 . . ?
C13B C14B F1B 118.6(10) . . ?
C15B C14B F1B 119.0(9) . . ?
C15B C14B C13B 122.4(8) . . ?
C14B C15B H15B 122.0 . . ?
C14B C15B C16B 116.0(7) . . ?
C16B C15B H15B 122.0 . . ?
C11B C16B H16B 118.8 . . ?
C15B C16B C11B 122.4(8) . . ?
C15B C16B H16B 118.8 . . ?
O1C N1C C1C 115.2(9) . . ?
O2C N1C O1C 129.4(19) . . ?
O2C N1C C1C 115.2(9) . . ?
C5C C4C C3C 120.0 . . ?
C7C C4C C5C 124.5(8) . . ?
C7C C4C C3C 115.5(8) . . ?
C4C C5C H5C 120.0 . . ?
C4C C5C C6C 120.0 . . ?
C6C C5C H5C 120.0 . . ?
C5C C6C H6C 120.0 . . ?
C1C C6C C5C 120.0 . . ?
C1C C6C H6C 120.0 . . ?
C6C C1C N1C 117.4(6) . . ?
C6C C1C C2C 120.0 . . ?
C2C C1C N1C 122.6(6) . . ?
C1C C2C H2C 120.0 . . ?
C3C C2C C1C 120.0 . . ?
C3C C2C H2C 120.0 . . ?
C4C C3C H3C 120.0 . . ?
C2C C3C C4C 120.0 . . ?
C2C C3C H3C 120.0 . . ?
C4C C7C H7C 115.7 . . ?
C8C C7C C4C 128.7(14) . . ?
C8C C7C H7C 115.7 . . ?
C7C C8C H8C 119.4 . . ?
C7C C8C C9C 121.1(19) . . ?
C9C C8C H8C 119.4 . . ?
C8C C9C H9C 121.6 . . ?
C10C C9C C8C 116.9(15) . . ?
C10C C9C H9C 121.6 . . ?
C9C C10C H10C 118.3 . . ?
C9C C10C C11C 123.4(13) . . ?
C11C C10C H10C 118.3 . . ?
C16C C11C C10C 119.9(11) . . ?
C16C C11C C12C 120.0 . . ?
C12C C11C C10C 120.1(11) . . ?
C11C C16C H16C 120.0 . . ?
C15C C16C C11C 120.0 . . ?
C15C C16C H16C 120.0 . . ?
C16C C15C H15C 120.0 . . ?
C14C C15C C16C 120.0 . . ?
C14C C15C H15C 120.0 . . ?
C15C C14C F1C 121.4(14) . . ?
C15C C14C C13C 120.0 . . ?
C13C C14C F1C 118.6(14) . . ?
C14C C13C H13C 120.0 . . ?
C12C C13C C14C 120.0 . . ?
C12C C13C H13C 120.0 . . ?
C11C C12C H12C 120.0 . . ?
C13C C12C C11C 120.0 . . ?
C13C C12C H12C 120.0 . . ?
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
F1A C14A 1.304(11) . ?
O1A N1A 1.296(13) . ?
O2A N1A 1.215(12) . ?
N1A C1A 1.448(11) . ?
C1A C2A 1.418(10) . ?
C1A C6A 1.371(9) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.326(10) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.381(10) . ?
C4A C5A 1.420(11) . ?
C4A C7A 1.488(10) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.334(11) . ?
C6A H6A 0.9300 . ?
C7A H7A 0.9300 . ?
C7A C8A 1.283(15) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.433(12) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.313(13) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.399(11) . ?
C11A C12A 1.388(15) . ?
C11A C16A 1.366(11) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.353(12) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.310(11) . ?
C14A C15A 1.439(10) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.343(10) . ?
C16A H16A 0.9300 . ?
F1B C14B 1.378(8) . ?
O1B N1B 1.246(8) . ?
O2B N1B 1.167(13) . ?
N1B C1B 1.428(9) . ?
C1B C2B 1.331(9) . ?
C1B C6B 1.407(10) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.367(8) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.424(8) . ?
C4B C5B 1.348(9) . ?
C4B C7B 1.403(8) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.357(9) . ?
C6B H6B 0.9300 . ?
C7B H7B 0.9300 . ?
C7B C8B 1.388(8) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.411(8) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.362(9) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.470(9) . ?
C11B C12B 1.364(11) . ?
C11B C16B 1.423(10) . ?
C12B H12B 0.9300 . ?
C12B C13B 1.347(9) . ?
C13B H13B 0.9300 . ?
C13B C14B 1.353(12) . ?
C14B C15B 1.347(13) . ?
C15B H15B 0.9300 . ?
C15B C16B 1.355(9) . ?
C16B H16B 0.9300 . ?
F1C C14C 1.402(16) . ?
O1C N1C 1.182(11) . ?
O2C N1C 1.182(11) . ?
N1C C1C 1.399(18) . ?
C4C C5C 1.3900 . ?
C4C C3C 1.3900 . ?
C4C C7C 1.377(14) . ?
C5C H5C 0.9300 . ?
C5C C6C 1.3900 . ?
C6C H6C 0.9300 . ?
C6C C1C 1.3900 . ?
C1C C2C 1.3900 . ?
C2C H2C 0.9300 . ?
C2C C3C 1.3900 . ?
C3C H3C 0.9300 . ?
C7C H7C 0.9300 . ?
C7C C8C 1.35(2) . ?
C8C H8C 0.9300 . ?
C8C C9C 1.41(2) . ?
C9C H9C 0.9300 . ?
C9C C10C 1.363(15) . ?
C10C H10C 0.9300 . ?
C10C C11C 1.463(15) . ?
C11C C16C 1.3900 . ?
C11C C12C 1.3900 . ?
C16C H16C 0.9300 . ?
C16C C15C 1.3900 . ?
C15C H15C 0.9300 . ?
C15C C14C 1.3900 . ?
C14C C13C 1.3900 . ?
C13C H13C 0.9300 . ?
C13C C12C 1.3900 . ?
C12C H12C 0.9300 . ?
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
F1A C14A C15A C16A 177.9(10) . . . . ?
O1A N1A C1A C2A 169.6(11) . . . . ?
O1A N1A C1A C6A -11.6(15) . . . . ?
O2A N1A C1A C2A -14.1(15) . . . . ?
O2A N1A C1A C6A 164.6(10) . . . . ?
N1A C1A C2A C3A -178.3(9) . . . . ?
N1A C1A C6A C5A -179.8(9) . . . . ?
C1A C2A C3A C4A -2.5(13) . . . . ?
C2A C1A C6A C5A -1.1(13) . . . . ?
C2A C3A C4A C5A 0.4(13) . . . . ?
C2A C3A C4A C7A -178.9(8) . . . . ?
C3A C4A C5A C6A 1.5(13) . . . . ?
C3A C4A C7A C8A -3.7(18) . . . . ?
C4A C5A C6A C1A -1.1(13) . . . . ?
C4A C7A C8A C9A -178.4(12) . . . . ?
C5A C4A C7A C8A 177.0(15) . . . . ?
C6A C1A C2A C3A 3.0(14) . . . . ?
C7A C4A C5A C6A -179.1(8) . . . . ?
C7A C8A C9A C10A 178.1(14) . . . . ?
C8A C9A C10A C11A 176.6(13) . . . . ?
C9A C10A C11A C12A -174.4(10) . . . . ?
C9A C10A C11A C16A 7.0(15) . . . . ?
C10A C11A C12A C13A -178.1(8) . . . . ?
C10A C11A C16A C15A 178.0(9) . . . . ?
C11A C12A C13A C14A -0.6(13) . . . . ?
C12A C11A C16A C15A -0.5(14) . . . . ?
C12A C13A C14A F1A -178.1(8) . . . . ?
C12A C13A C14A C15A 0.9(13) . . . . ?
C13A C14A C15A C16A -1.1(14) . . . . ?
C14A C15A C16A C11A 0.8(14) . . . . ?
C16A C11A C12A C13A 0.4(14) . . . . ?
F1B C14B C15B C16B -176.3(9) . . . . ?
O1B N1B C1B C2B -169.0(10) . . . . ?
O1B N1B C1B C6B 12.0(16) . . . . ?
O2B N1B C1B C2B 15.8(16) . . . . ?
O2B N1B C1B C6B -163.3(12) . . . . ?
N1B C1B C2B C3B 179.4(9) . . . . ?
N1B C1B C6B C5B -179.2(9) . . . . ?
C1B C2B C3B C4B -0.3(13) . . . . ?
C2B C1B C6B C5B 1.8(15) . . . . ?
C2B C3B C4B C5B 2.0(12) . . . . ?
C2B C3B C4B C7B -179.6(7) . . . . ?
C3B C4B C5B C6B -1.7(11) . . . . ?
C3B C4B C7B C8B -171.1(7) . . . . ?
C4B C5B C6B C1B 0.0(13) . . . . ?
C4B C7B C8B C9B -179.8(7) . . . . ?
C5B C4B C7B C8B 7.3(11) . . . . ?
C6B C1B C2B C3B -1.6(14) . . . . ?
C7B C4B C5B C6B 179.9(8) . . . . ?
C7B C8B C9B C10B 178.5(8) . . . . ?
C8B C9B C10B C11B 178.0(7) . . . . ?
C9B C10B C11B C12B -4.3(13) . . . . ?
C9B C10B C11B C16B 174.3(9) . . . . ?
C10B C11B C12B C13B 177.1(9) . . . . ?
C10B C11B C16B C15B -176.5(8) . . . . ?
C11B C12B C13B C14B 1.2(16) . . . . ?
C12B C11B C16B C15B 2.2(14) . . . . ?
C12B C13B C14B F1B 176.8(11) . . . . ?
C12B C13B C14B C15B -1.6(17) . . . . ?
C13B C14B C15B C16B 2.1(14) . . . . ?
C14B C15B C16B C11B -2.4(14) . . . . ?
C16B C11B C12B C13B -1.5(13) . . . . ?
F1C C14C C13C C12C -179.1(19) . . . . ?
O1C N1C C1C C6C -8(3) . . . . ?
O1C N1C C1C C2C 173.1(16) . . . . ?
O2C N1C C1C C6C 175.2(18) . . . . ?
O2C N1C C1C C2C -4(3) . . . . ?
N1C C1C C2C C3C 179(2) . . . . ?
C4C C5C C6C C1C 0.0 . . . . ?
C4C C7C C8C C9C -178(2) . . . . ?
C5C C4C C3C C2C 0.0 . . . . ?
C5C C4C C7C C8C 3(3) . . . . ?
C5C C6C C1C N1C -179.1(19) . . . . ?
C5C C6C C1C C2C 0.0 . . . . ?
C6C C1C C2C C3C 0.0 . . . . ?
C1C C2C C3C C4C 0.0 . . . . ?
C3C C4C C5C C6C 0.0 . . . . ?
C3C C4C C7C C8C -176(3) . . . . ?
C7C C4C C5C C6C -179.5(12) . . . . ?
C7C C4C C3C C2C 179.5(11) . . . . ?
C7C C8C C9C C10C 173(3) . . . . ?
C8C C9C C10C C11C 177(2) . . . . ?
C9C C10C C11C C16C -174.9(14) . . . . ?
C9C C10C C11C C12C 7(2) . . . . ?
C10C C11C C16C C15C -178.2(14) . . . . ?
C10C C11C C12C C13C 178.2(14) . . . . ?
C11C C16C C15C C14C 0.0 . . . . ?
C16C C11C C12C C13C 0.0 . . . . ?
C16C C15C C14C F1C 179.0(19) . . . . ?
C16C C15C C14C C13C 0.0 . . . . ?
C15C C14C C13C C12C 0.0 . . . . ?
C14C C13C C12C C11C 0.0 . . . . ?
C12C C11C C16C C15C 0.0 . . . . ?
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
-3.0000 -1.0000 4.0000 -0.1509 -0.6946 0.6577
3.0000 1.0000 -4.0000 0.1509 0.6946 -0.6577
-1.0000 -1.0000 5.0000 -0.0527 -0.3304 1.0361
1.0000 1.0000 -5.0000 0.0527 0.3304 -1.0361
-0.0000 1.0000 0.0000 -0.1132 0.0382 -0.0074
0.0000 -1.0000 -0.0000 0.1132 -0.0382 0.0074
5.0000 1.0000 -1.0000 0.2065 1.0189 0.1636
-5.0000 -1.0000 1.0000 -0.2065 -1.0189 -0.1636
1.0000 -7.0000 2.0000 0.8095 -0.1155 0.5732
4.0000 -1.0000 -3.0000 0.4157 0.7903 -0.3430
-3.0000 5.0000 2.0000 -0.7875 -0.4252 0.1704
3.0000 -6.0000 -2.0000 0.9007 0.3870 -0.1630
