#------------------------------------------------------------------------------
#$Date: 2020-05-17 02:28:14 +0300 (Sun, 17 May 2020) $
#$Revision: 252114 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038370.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_4038370
loop_
_publ_author_name
'Schoemaker, Robin'
'Schwedtmann, Kai'
'Hennersdorf, Felix'
'Bauzá, Antonio'
'Frontera, Antonio'
'Weigand, Jan J.'
_publ_section_title
;
 Toward N,P-Doped π-Extended PAHs: A One-Pot Synthesis to Diannulated
 1,4,2-Diazaphospholium Triflate Salts.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00577
_journal_year                    2020
_chemical_formula_moiety         'C F3 O3 S, C18 H12 N2 P, C2 H3 N'
_chemical_formula_sum            'C21 H15 F3 N3 O3 P S'
_chemical_formula_weight         477.39
_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
_audit_creation_date             2016-07-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                116.376(3)
_cell_angle_beta                 101.678(3)
_cell_angle_gamma                96.308(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0876(3)
_cell_length_b                   12.8437(4)
_cell_length_c                   13.0350(4)
_cell_measurement_reflns_used    4806
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.0080
_cell_measurement_theta_min      3.9040
_cell_volume                     1013.70(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5700
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     18.00 112.00   0.50    1.00    --   42.50  57.00 -60.00  188
  2  ω     66.00 125.00   0.50    3.00    --  111.00  15.00  30.00  118
  3  ω    130.00 161.00   0.50    3.00    --  111.00  15.00  30.00   62
  4  ω    122.00 155.00   0.50    3.00    --  111.00  77.00 -60.00   66
  5  ω    153.00 178.00   0.50    3.00    --  111.00  45.00-150.00   50
  6  ω     99.00 152.00   0.50    3.00    --  111.00  45.00-180.00  106
  7  ω     95.00 161.00   0.50    3.00    --  111.00 125.00-120.00  132
  8  ω     94.00 123.00   0.50    3.00    --  111.00 125.00-180.00   58
  9  ω     87.00 119.00   0.50    3.00    --  111.00  77.00 -60.00   64
 10  ω     88.00 139.00   0.50    3.00    --  111.00  45.00-150.00  102
 11  ω     92.00 135.00   0.50    3.00    --  111.00 -45.00 -30.00   86
 12  ω     82.00 109.00   0.50    3.00    --  111.00 -94.00  60.00   54
 13  ω     86.00 121.00   0.50    3.00    --  111.00-125.00 120.00   70
 14  ω     99.00 138.00   0.50    3.00    --  111.00 -77.00 150.00   78
 15  ω     70.00 134.00   0.50    3.00    --  111.00 -30.00 150.00  128
 16  ω     65.00 108.00   0.50    3.00    --  111.00 -94.00   0.00   86
 17  ω     92.00 121.00   0.50    3.00    --  111.00-125.00 -30.00   58
 18  ω     91.00 120.00   0.50    3.00    --  111.00-125.00-120.00   58
 19  ω     96.00 126.00   0.50    3.00    --  111.00 -77.00-150.00   60
 20  ω     84.00 120.00   0.50    3.00    --  111.00-125.00-180.00   72
 21  ω     45.00  80.00   0.50    3.00    --  111.00-125.00 -30.00   70
 22  ω     32.00  61.00   0.50    3.00    --  111.00 -94.00   0.00   58
 23  ω     31.00  81.00   0.50    3.00    --  111.00 -94.00  60.00  100
 24  ω     40.00  72.00   0.50    3.00    --  111.00 -45.00 -30.00   64
 25  ω     38.00  80.00   0.50    3.00    --  111.00 -77.00-150.00   84
 26  ω     40.00  71.00   0.50    3.00    --  111.00-125.00-180.00   62
 27  ω    -61.00  28.00   0.50    1.00    --  -38.50  38.00-180.00  178
 28  ω    -37.00  -4.00   0.50    1.00    --  -38.50 125.00   0.00   66
 29  ω    138.00 177.00   0.50    3.00    --  111.00 125.00  90.00   78
 30  ω     38.00  91.00   0.50    3.00    --  111.00 -77.00 150.00  106
 31  ω     13.00  67.00   0.50    1.00    --   42.50 -57.00 150.00  108
 32  ω    -93.00 -58.00   0.50    1.00    --  -38.50 125.00   0.00   70
 33  ω   -110.00 -16.00   0.50    1.00    --  -38.50 -38.00   0.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0206057000
_diffrn_orient_matrix_UB_12      -0.1098575000
_diffrn_orient_matrix_UB_13      0.0170962000
_diffrn_orient_matrix_UB_21      0.2118158000
_diffrn_orient_matrix_UB_22      0.0128954000
_diffrn_orient_matrix_UB_23      -0.0123012000
_diffrn_orient_matrix_UB_31      0.0816562000
_diffrn_orient_matrix_UB_32      0.0816733000
_diffrn_orient_matrix_UB_33      0.1358829000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9124
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.658
_diffrn_reflns_theta_min         3.945
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.698
_exptl_absorpt_correction_T_max  0.811
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0413
_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)+(0.0726P)²+0.3423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1148
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3959
_reflns_number_total             4208
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00577_si_005.cif
_cod_data_source_block           jjw0478
_cod_database_code               4038370
_chemical_oxdiff_formula         'C42 H30 F6 N6 O6 P2 S2 '
_chemical_oxdiff_usercomment     MeCN/Et2O
_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
;
;
_shelx_shelxl_version_number     2014/7
_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 1.293
_oxdiff_exptl_absorpt_empirical_full_min 0.746
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 0.71551(6) 0.77436(4) 0.31105(3) 0.02855(13) Uani 1 1 d . . . . .
P1 P 0.70266(6) 0.52138(4) 0.39196(3) 0.02485(13) Uani 1 1 d . . . . .
F2 F 0.5082(2) 0.56545(11) 0.13761(11) 0.0510(3) Uani 1 1 d . . . . .
F3 F 0.34490(18) 0.70339(13) 0.18384(13) 0.0537(3) Uani 1 1 d . . . . .
F1 F 0.5526(2) 0.70017(14) 0.08399(11) 0.0585(4) Uani 1 1 d . . . . .
O1 O 0.7158(2) 0.89401(12) 0.33129(12) 0.0363(3) Uani 1 1 d . . . . .
O3 O 0.6469(2) 0.74663(13) 0.39500(12) 0.0423(3) Uani 1 1 d . . . . .
O2 O 0.8883(2) 0.73241(13) 0.28349(14) 0.0436(3) Uani 1 1 d . . . . .
N1 N 0.78526(19) 0.51254(12) 0.59306(12) 0.0243(3) Uani 1 1 d . . . . .
N2 N 0.73604(19) 0.39061(12) 0.39776(12) 0.0244(3) Uani 1 1 d . . . . .
C1 C 0.7436(2) 0.58806(15) 0.54454(14) 0.0248(3) Uani 1 1 d . . . . .
C14 C 0.7228(2) 0.28290(15) 0.29616(14) 0.0255(3) Uani 1 1 d . . . . .
C2 C 0.7301(2) 0.70626(15) 0.62066(15) 0.0264(3) Uani 1 1 d . . . . .
C5 C 0.8447(2) 0.55836(15) 0.71969(14) 0.0249(3) Uani 1 1 d . . . . .
C13 C 0.7459(2) 0.18208(15) 0.30938(15) 0.0281(3) Uani 1 1 d . . . . .
C4 C 0.8119(2) 0.67097(15) 0.79020(14) 0.0269(3) Uani 1 1 d . . . . .
C10 C 0.7685(2) 0.39791(15) 0.50714(14) 0.0249(3) Uani 1 1 d . . . . .
C3 C 0.7516(2) 0.74409(15) 0.73803(15) 0.0277(3) Uani 1 1 d . . . . .
C11 C 0.7707(2) 0.29399(15) 0.52040(15) 0.0280(3) Uani 1 1 d . . . . .
C6 C 0.9475(2) 0.50000(15) 0.77310(15) 0.0274(3) Uani 1 1 d . . . . .
N3 N 0.7943(4) 1.03296(18) 0.82862(17) 0.0555(5) Uani 1 1 d . . . . .
C12 C 0.7630(3) 0.18957(16) 0.42364(16) 0.0300(3) Uani 1 1 d . . . . .
C15 C 0.6881(2) 0.27713(16) 0.18381(15) 0.0283(3) Uani 1 1 d . . . . .
C9 C 0.8619(3) 0.71661(16) 0.91498(15) 0.0303(3) Uani 1 1 d . . . . .
C17 C 0.7226(3) 0.07270(16) 0.09996(16) 0.0338(4) Uani 1 1 d . . . . .
C18 C 0.7462(3) 0.07596(16) 0.20861(16) 0.0322(4) Uani 1 1 d . . . . .
C7 C 1.0011(3) 0.55002(17) 0.89654(15) 0.0309(4) Uani 1 1 d . . . . .
C8 C 0.9531(3) 0.65600(17) 0.96764(15) 0.0328(4) Uani 1 1 d . . . . .
C16 C 0.6889(3) 0.17241(17) 0.08713(15) 0.0314(4) Uani 1 1 d . . . . .
C20 C 0.7666(3) 1.03643(17) 0.74102(17) 0.0383(4) Uani 1 1 d . . . . .
C19 C 0.5209(3) 0.68100(18) 0.17153(16) 0.0363(4) Uani 1 1 d . . . . .
C21 C 0.7323(3) 1.0407(2) 0.62924(18) 0.0411(4) Uani 1 1 d . . . . .
H9 H 0.837(3) 0.794(2) 0.9642(19) 0.028(5) Uiso 1 1 d . . . . .
H15 H 0.662(3) 0.344(2) 0.1777(18) 0.026(5) Uiso 1 1 d . . . . .
H11 H 0.775(3) 0.302(2) 0.599(2) 0.034(5) Uiso 1 1 d . . . . .
H2 H 0.700(3) 0.756(2) 0.5853(19) 0.031(5) Uiso 1 1 d . . . . .
H17 H 0.732(3) 0.004(2) 0.033(2) 0.033(5) Uiso 1 1 d . . . . .
H6 H 0.986(3) 0.430(2) 0.7284(19) 0.027(5) Uiso 1 1 d . . . . .
H3 H 0.741(3) 0.824(2) 0.7889(19) 0.028(5) Uiso 1 1 d . . . . .
H12 H 0.765(4) 0.121(2) 0.431(2) 0.039(6) Uiso 1 1 d . . . . .
H8 H 0.987(4) 0.687(2) 1.053(2) 0.043(6) Uiso 1 1 d . . . . .
H18 H 0.758(3) 0.009(2) 0.2171(19) 0.031(5) Uiso 1 1 d . . . . .
H7 H 1.078(4) 0.510(2) 0.934(2) 0.038(6) Uiso 1 1 d . . . . .
H16 H 0.671(4) 0.169(2) 0.012(2) 0.039(6) Uiso 1 1 d . . . . .
H21A H 0.713(5) 0.961(3) 0.563(3) 0.067(9) Uiso 1 1 d . . . . .
H21B H 0.625(5) 1.075(3) 0.619(3) 0.067(9) Uiso 1 1 d . . . . .
H21C H 0.847(5) 1.097(3) 0.638(3) 0.073(9) 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'
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'
P P 0.2955 0.4335 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -8 2 0.0399
1 6 -8 0.0624
-1 -6 8 0.0445
1 7 -1 0.0686
-4 2 -1 0.1033
4 -2 1 0.1109
0 1 7 0.0867
-2 3 6 0.1152
5 -2 -2 0.1062
-1 8 -6 0.0795
-4 -3 6 0.0868
-2 -6 1 0.0732
4 3 -5 0.1020
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
O1 S1 O3 114.36(8) . . ?
O1 S1 C19 104.00(8) . . ?
O3 S1 C19 102.91(9) . . ?
O2 S1 O1 115.28(9) . . ?
O2 S1 O3 115.05(9) . . ?
O2 S1 C19 102.89(9) . . ?
C1 P1 N2 86.83(7) . . ?
C1 N1 C5 120.48(14) . . ?
C10 N1 C1 112.45(13) . . ?
C10 N1 C5 127.03(14) . . ?
C14 N2 P1 123.07(11) . . ?
C10 N2 P1 115.76(11) . . ?
C10 N2 C14 121.13(14) . . ?
N1 C1 P1 113.86(12) . . ?
N1 C1 C2 119.38(14) . . ?
C2 C1 P1 126.70(12) . . ?
C13 C14 N2 118.88(14) . . ?
C15 C14 N2 120.20(15) . . ?
C15 C14 C13 120.92(15) . . ?
C1 C2 H2 118.0(13) . . ?
C3 C2 C1 120.35(15) . . ?
C3 C2 H2 121.5(13) . . ?
C4 C5 N1 117.14(14) . . ?
C6 C5 N1 122.23(15) . . ?
C6 C5 C4 120.38(15) . . ?
C14 C13 C12 118.75(15) . . ?
C14 C13 C18 118.86(16) . . ?
C18 C13 C12 122.37(16) . . ?
C5 C4 C3 120.56(15) . . ?
C5 C4 C9 118.52(15) . . ?
C9 C4 C3 120.49(16) . . ?
N1 C10 C11 128.45(15) . . ?
N2 C10 N1 110.75(14) . . ?
N2 C10 C11 120.70(15) . . ?
C2 C3 C4 120.30(16) . . ?
C2 C3 H3 120.1(13) . . ?
C4 C3 H3 119.2(13) . . ?
C10 C11 H11 117.1(14) . . ?
C12 C11 C10 118.68(15) . . ?
C12 C11 H11 124.2(14) . . ?
C5 C6 H6 122.2(13) . . ?
C7 C6 C5 119.02(16) . . ?
C7 C6 H6 118.7(13) . . ?
C13 C12 H12 119.3(15) . . ?
C11 C12 C13 121.27(16) . . ?
C11 C12 H12 119.4(15) . . ?
C14 C15 H15 118.3(13) . . ?
C16 C15 C14 118.80(16) . . ?
C16 C15 H15 122.9(13) . . ?
C4 C9 H9 118.8(12) . . ?
C8 C9 C4 120.95(16) . . ?
C8 C9 H9 120.2(12) . . ?
C18 C17 C16 120.39(16) . . ?
C18 C17 H17 120.9(14) . . ?
C16 C17 H17 118.7(14) . . ?
C13 C18 H18 118.8(13) . . ?
C17 C18 C13 119.89(17) . . ?
C17 C18 H18 121.3(14) . . ?
C6 C7 C8 121.38(16) . . ?
C6 C7 H7 118.6(14) . . ?
C8 C7 H7 120.0(14) . . ?
C9 C8 C7 119.26(16) . . ?
C9 C8 H8 120.9(15) . . ?
C7 C8 H8 119.8(15) . . ?
C15 C16 C17 120.95(16) . . ?
C15 C16 H16 119.0(15) . . ?
C17 C16 H16 120.1(15) . . ?
N3 C20 C21 179.7(3) . . ?
F2 C19 S1 111.19(13) . . ?
F2 C19 F3 107.40(17) . . ?
F3 C19 S1 110.82(13) . . ?
F1 C19 S1 111.67(15) . . ?
F1 C19 F2 108.04(16) . . ?
F1 C19 F3 107.53(16) . . ?
C20 C21 H21A 109.8(19) . . ?
C20 C21 H21B 110.4(19) . . ?
C20 C21 H21C 106(2) . . ?
H21A C21 H21B 112(3) . . ?
H21A C21 H21C 113(3) . . ?
H21B C21 H21C 105(3) . . ?
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 O1 1.4388(13) . ?
S1 O3 1.4438(14) . ?
S1 O2 1.4388(14) . ?
S1 C19 1.8252(19) . ?
P1 N2 1.7538(14) . ?
P1 C1 1.7238(16) . ?
F2 C19 1.333(2) . ?
F3 C19 1.336(2) . ?
F1 C19 1.324(2) . ?
N1 C1 1.400(2) . ?
N1 C5 1.4315(19) . ?
N1 C10 1.371(2) . ?
N2 C14 1.403(2) . ?
N2 C10 1.356(2) . ?
C1 C2 1.425(2) . ?
C14 C13 1.402(2) . ?
C14 C15 1.402(2) . ?
C2 C3 1.352(2) . ?
C2 H2 0.96(2) . ?
C5 C4 1.404(2) . ?
C5 C6 1.398(2) . ?
C13 C12 1.428(2) . ?
C13 C18 1.412(2) . ?
C4 C3 1.437(2) . ?
C4 C9 1.410(2) . ?
C10 C11 1.421(2) . ?
C3 H3 0.96(2) . ?
C11 C12 1.358(2) . ?
C11 H11 0.98(2) . ?
C6 C7 1.388(2) . ?
C6 H6 0.94(2) . ?
N3 C20 1.141(3) . ?
C12 H12 0.93(3) . ?
C15 C16 1.377(2) . ?
C15 H15 0.94(2) . ?
C9 C8 1.379(3) . ?
C9 H9 0.98(2) . ?
C17 C18 1.373(3) . ?
C17 C16 1.402(3) . ?
C17 H17 0.95(2) . ?
C18 H18 0.93(2) . ?
C7 C8 1.391(3) . ?
C7 H7 0.99(2) . ?
C8 H8 0.96(2) . ?
C16 H16 0.94(2) . ?
C20 C21 1.455(3) . ?
C21 H21A 0.97(3) . ?
C21 H21B 0.93(3) . ?
C21 H21C 0.97(4) . ?
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
P1 N2 C14 C13 -178.10(11) . . . . ?
P1 N2 C14 C15 2.2(2) . . . . ?
P1 N2 C10 N1 -5.36(17) . . . . ?
P1 N2 C10 C11 171.39(12) . . . . ?
P1 C1 C2 C3 174.96(13) . . . . ?
O1 S1 C19 F2 177.25(14) . . . . ?
O1 S1 C19 F3 -63.37(16) . . . . ?
O1 S1 C19 F1 56.49(16) . . . . ?
O3 S1 C19 F2 -63.19(16) . . . . ?
O3 S1 C19 F3 56.19(16) . . . . ?
O3 S1 C19 F1 176.05(14) . . . . ?
O2 S1 C19 F2 56.68(16) . . . . ?
O2 S1 C19 F3 176.06(14) . . . . ?
O2 S1 C19 F1 -64.08(16) . . . . ?
N1 C1 C2 C3 -1.9(2) . . . . ?
N1 C5 C4 C3 -9.9(2) . . . . ?
N1 C5 C4 C9 177.62(14) . . . . ?
N1 C5 C6 C7 179.72(15) . . . . ?
N1 C10 C11 C12 -176.27(16) . . . . ?
N2 P1 C1 N1 1.69(12) . . . . ?
N2 P1 C1 C2 -175.30(15) . . . . ?
N2 C14 C13 C12 6.0(2) . . . . ?
N2 C14 C13 C18 -175.71(14) . . . . ?
N2 C14 C15 C16 175.76(15) . . . . ?
N2 C10 C11 C12 7.6(2) . . . . ?
C1 P1 N2 C14 179.65(13) . . . . ?
C1 P1 N2 C10 2.12(12) . . . . ?
C1 N1 C5 C4 15.5(2) . . . . ?
C1 N1 C5 C6 -158.77(15) . . . . ?
C1 N1 C10 N2 6.47(18) . . . . ?
C1 N1 C10 C11 -169.96(15) . . . . ?
C1 C2 C3 C4 7.6(2) . . . . ?
C14 N2 C10 N1 177.06(13) . . . . ?
C14 N2 C10 C11 -6.2(2) . . . . ?
C14 C13 C12 C11 -4.5(3) . . . . ?
C14 C13 C18 C17 -0.5(3) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C5 N1 C1 P1 172.85(11) . . . . ?
C5 N1 C1 C2 -9.9(2) . . . . ?
C5 N1 C10 N2 -171.29(14) . . . . ?
C5 N1 C10 C11 12.3(3) . . . . ?
C5 C4 C3 C2 -1.5(2) . . . . ?
C5 C4 C9 C8 4.3(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C13 C14 C15 C16 -3.9(2) . . . . ?
C4 C5 C6 C7 5.6(2) . . . . ?
C4 C9 C8 C7 1.8(3) . . . . ?
C10 N1 C1 P1 -5.08(17) . . . . ?
C10 N1 C1 C2 172.15(14) . . . . ?
C10 N1 C5 C4 -166.88(15) . . . . ?
C10 N1 C5 C6 18.8(2) . . . . ?
C10 N2 C14 C13 -0.7(2) . . . . ?
C10 N2 C14 C15 179.62(14) . . . . ?
C10 C11 C12 C13 -2.2(3) . . . . ?
C3 C4 C9 C8 -168.28(17) . . . . ?
C6 C5 C4 C3 164.55(16) . . . . ?
C6 C5 C4 C9 -8.0(2) . . . . ?
C6 C7 C8 C9 -4.3(3) . . . . ?
C12 C13 C18 C17 177.80(16) . . . . ?
C15 C14 C13 C12 -174.36(15) . . . . ?
C15 C14 C13 C18 4.0(2) . . . . ?
C9 C4 C3 C2 170.88(16) . . . . ?
C18 C13 C12 C11 177.22(17) . . . . ?
C18 C17 C16 C15 3.1(3) . . . . ?
C16 C17 C18 C13 -3.0(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
0.0006 -8.0020 2.0133 0.9135 -0.1278 -0.3799
0.9997 5.9994 -8.0050 -0.7753 0.3876 -0.5161
-0.9997 -5.9994 8.0050 0.7753 -0.3876 0.5161
1.0004 7.0033 -1.0139 -0.7661 0.3147 0.5159
-4.0037 1.9955 -0.9970 -0.3188 -0.8100 -0.2994
4.0037 -1.9955 0.9970 0.3188 0.8100 0.2994
0.0007 1.0039 6.9911 0.0093 -0.0729 1.0320
-2.0012 3.0018 5.9912 -0.2686 -0.4589 0.8959
5.0042 -1.9959 -2.0015 0.2882 1.0589 -0.0264
-1.0019 7.9988 -6.0079 -1.0021 -0.0352 -0.2449
-4.0027 -3.0028 6.0056 0.3501 -0.9604 0.2440
-2.0014 -6.0041 1.0134 0.6357 -0.5138 -0.5161
4.0028 3.0034 -5.0066 -0.3331 0.9482 -0.1082
