#------------------------------------------------------------------------------
#$Date: 2020-03-07 02:22:51 +0200 (Sat, 07 Mar 2020) $
#$Revision: 249157 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/80/4038041.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_4038041
loop_
_publ_author_name
'Funt, Liya D.'
'Krivolapova, Yulia V.'
'Khoroshilova, Olesya V.'
'Novikov, Mikhail Sergeevich'
'Khlebnikov, Alexander F.'
_publ_section_title
;
 2H-Azirine-2-carbonyl Azides: Preparation and Use as N-Heterocyclic
 Building Blocks.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03367
_journal_year                    2020
_chemical_formula_moiety         'C15 H11 F3 N2 O4 S'
_chemical_formula_sum            'C15 H11 F3 N2 O4 S'
_chemical_formula_weight         372.32
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                108.010(4)
_cell_angle_beta                 94.612(3)
_cell_angle_gamma                103.904(3)
_cell_formula_units_Z            4
_cell_length_a                   7.4324(3)
_cell_length_b                   14.3291(5)
_cell_length_c                   15.9268(7)
_cell_measurement_reflns_used    5956
_cell_measurement_temperature    100(3)
_cell_measurement_theta_max      69.8800
_cell_measurement_theta_min      2.9460
_cell_volume                     1543.68(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.50a (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      100(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -80.00 -12.00   0.50    0.20    --  -38.70 141.00-170.00  136
  2  ω    -89.00 -43.00   0.50    0.20    --  -38.70 129.00  17.00   92
  3  ω     53.00  85.00   0.50    0.20    --   38.70-141.00 131.00   64
  4  ω     12.00  61.00   0.50    0.20    --   38.70-129.00 -56.00   98
  5  ω     81.00 106.00   0.50    0.67    --  100.00-141.00 131.00   50
  6  ω     66.00  92.00   0.50    0.67    --  100.00-129.00 -56.00   52
  7  ω     85.00 112.00   0.50    0.67    --  100.00 141.00-170.00   54
  8  ω    114.00 139.00   0.50    0.67    --  100.00 129.00  17.00   50
  9  ω    -41.00 -15.00   0.50    0.20    --  -38.70 -65.00-180.00   52
 10  ω    -52.00 -26.00   0.50    0.20    --  -38.70  43.00 -90.00   52
 11  ω    -56.00  15.00   0.50    0.20    --  -38.70  65.00 120.00  142
 12  ω     -1.00  24.00   0.50    0.20    --  -38.70  65.00-150.00   50
 13  ω    -84.00 -28.00   0.50    0.20    --  -38.70 -65.00 -60.00  112
 14  ω    -19.00   6.00   0.50    0.20    --  -38.70  43.00 -90.00   50
 15  ω    -63.00  15.00   0.50    0.20    --  -38.70 104.00 120.00  156
 16  ω    -39.00 -13.00   0.50    0.20    --  -38.70  21.00 150.00   52
 17  ω     -8.00  21.00   0.50    0.20    --  -38.70  21.00 150.00   58
 18  ω    -58.00  -7.00   0.50    0.20    --  -38.70  65.00-150.00  102
 19  ω   -104.00 -51.00   0.50    0.20    --  -38.70 -65.00-180.00  106
 20  ω     23.00  99.00   0.50    0.20    --   38.70  21.00-180.00  152
 21  ω     14.00  61.00   0.50    0.20    --   38.70 -65.00 -90.00   94
 22  ω     19.00  58.00   0.50    0.20    --   38.70  21.00  90.00   78
 23  ω    -24.00  58.00   0.50    0.20    --   38.70 -54.00 -60.00  164
 24  ω     62.00 107.00   0.50    0.20    --   38.70  21.00  90.00   90
 25  ω     22.00  83.00   0.50    0.20    --   38.70  43.00  60.00  122
 26  ω     82.00 110.00   0.50    0.67    --  100.00  93.00-120.00   56
 27  ω     78.00 120.00   0.50    0.67    --  100.00  69.00 -60.00   84
 28  ω     92.00 127.00   0.50    0.67    --  100.00 111.00   0.00   70
 29  ω     58.00  84.00   0.50    0.67    --  100.00 -93.00 150.00   52
 30  ω     41.00  67.00   0.50    0.67    --  100.00-133.00-180.00   52
 31  ω     86.00 142.00   0.50    0.67    --  100.00  61.00  60.00  112
 32  ω    121.00 148.00   0.50    0.67    --  100.00  37.00-180.00   54
 33  ω     98.00 123.00   0.50    0.67    --  100.00-133.00-180.00   50
 34  ω    103.00 135.00   0.50    0.67    --  100.00  30.00 120.00   64
 35  ω     42.00  77.00   0.50    0.67    --  100.00 -45.00   0.00   70
 36  ω     37.00  79.00   0.50    0.67    --  100.00 -61.00-180.00   84
 37  ω     46.00  72.00   0.50    0.67    --  100.00-133.00  60.00   52
 38  ω     83.00 123.00   0.50    0.67    --  100.00-133.00  60.00   80
 39  ω    105.00 131.00   0.50    0.67    --  100.00 111.00  60.00   52
 40  ω     44.00 108.00   0.50    0.67    --  100.00 -53.00  60.00  128
 41  ω    121.00 150.00   0.50    0.67    --  100.00  77.00  30.00   58
 42  ω     77.00 103.00   0.50    0.67    --  100.00  77.00  30.00   52
 43  ω     87.00 119.00   0.50    0.67    --  100.00  37.00-180.00   64
 44  ω     51.00 119.00   0.50    0.67    --  100.00 -69.00 -60.00  136
 45  ω     75.00 107.00   0.50    0.67    --  100.00-111.00  60.00   64
 46  ω     81.00 113.00   0.50    0.67    --  100.00-133.00-120.00   64
 47  ω     70.00 122.00   0.50    0.67    --  100.00 133.00 -30.00  104
 48  ω     40.00  66.00   0.50    0.67    --  100.00-111.00  60.00   52
 49  ω     73.00 156.00   0.50    0.67    --  100.00  77.00 -30.00  166
 50  ω     35.00  60.00   0.50    0.67    --  100.00 -86.00-180.00   50
 51  ω     98.00 129.00   0.50    0.67    --  100.00 -86.00-180.00   62
 52  ω     96.00 157.00   0.50    0.67    --  100.00  45.00-120.00  122
 53  ω     37.00 117.00   0.50    0.67    --  100.00 -61.00  60.00  160
 54  ω    131.00 156.00   0.50    0.67    --  100.00 133.00-180.00   50
 55  ω     69.00 108.00   0.50    0.67    --  100.00 133.00-180.00   78
 56  ω     71.00 153.00   0.50    0.67    --  100.00 133.00 -90.00  164
 57  ω     35.00 106.00   0.50    0.67    --  100.00 -93.00  90.00  142
 58  ω     80.00 121.00   0.50    0.67    --  100.00  15.00 -30.00   82
 59  ω    124.00 156.00   0.50    0.67    --  100.00  93.00-120.00   64
 60  ω     75.00 101.00   0.50    0.67    --  100.00 -81.00 -42.26   52
 61  ω     85.00 154.00   0.50    0.67    --  100.00  37.00 120.00  138
 62  ω     92.00 117.00   0.50    0.67    --  100.00  93.00 150.00   50
 63  ω     30.00  98.00   0.50    0.67    --  100.00 -93.00 -60.00  136
 64  ω     40.00 113.00   0.50    0.67    --  100.00 -53.00 -90.00  146
 65  ω     36.00 101.00   0.50    0.67    --  100.00 -53.00-180.00  130
 66  ω     87.00 134.00   0.50    0.67    --  100.00  53.00   0.00   94
 67  ω     86.00 111.00   0.50    0.67    --  100.00-111.00-120.00   50
 68  ω     36.00  75.00   0.50    0.67    --  100.00-111.00 -30.00   78
 69  ω     67.00  92.00   0.50    0.67    --  100.00-111.00 120.00   50
 70  ω     34.00 108.00   0.50    0.67    --  100.00 -93.00-150.00  148
 71  ω    125.00 152.00   0.50    0.67    --  100.00  30.00 150.00   54
 72  ω     89.00 115.00   0.50    0.67    --  100.00  30.00 150.00   52
 73  ω     18.00  44.00   0.50    0.20    --   38.70  77.00 -90.00   52
 74  ω    -51.00 -25.00   0.50    0.20    --    0.00 130.00-157.41   52
 75  ω    -33.00  -8.00   0.50    0.20    --   16.00 122.00  -3.35   50
 76  ω     -9.00  16.00   0.50    0.20    --   28.00 102.00 -56.17   50
 77  ω     -9.00  16.00   0.50    0.20    --   28.00 102.00 -87.97   50
 78  ω     -9.00  16.00   0.50    0.20    --   28.00 102.00  89.00   50
 79  ω     -1.00  24.00   0.50    0.20    --   32.00  94.00  17.20   50
 80  ω     -1.00  24.00   0.50    0.20    --   32.00  93.00 134.72   50
 81  ω      5.00  30.00   0.50    0.20    --   36.00  89.00  57.89   50
 82  ω      4.00  29.00   0.50    0.20    --   36.00  90.00-152.84   50
 83  ω      4.00  29.00   0.50    0.20    --   36.00  90.00-173.10   50
 84  ω      9.00  34.00   0.50    0.20    --   38.70  85.00 -73.27   50
 85  ω     11.00  36.00   0.50    0.20    --   40.00  84.00 -17.70   50
 86  ω     11.00  32.00   0.50    0.20    --   40.00  83.00-166.60   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0036784000
_diffrn_orient_matrix_UB_12      0.0021090000
_diffrn_orient_matrix_UB_13      0.0971352000
_diffrn_orient_matrix_UB_21      -0.1411336000
_diffrn_orient_matrix_UB_22      -0.1072163000
_diffrn_orient_matrix_UB_23      -0.0344578000
_diffrn_orient_matrix_UB_31      0.1642631000
_diffrn_orient_matrix_UB_32      -0.0486396000
_diffrn_orient_matrix_UB_33      -0.0046319000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16833
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.501
_diffrn_reflns_theta_min         2.959
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.431
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.50a (Rigaku Oxford Diffraction, 2019)
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    1.602
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         5838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0478
_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)+(0.0852P)²+0.6020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1385
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4969
_reflns_number_total             5838
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03367_si_005.cif
_cod_data_source_block           10681-13821_lia680
_cod_original_cell_volume        1543.68(11)
_cod_database_code               4038041
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C15 F3 N2 O4 S'
_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   0.683
_shelx_estimated_absorpt_t_min   0.617
_reflns_odcompleteness_completeness 95.24
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N1A(H1A), C9(H9), C12(H12), C12A(H12A), C10A(H10A), C9A(H9A),
 C10(H10), C11A(H11A), C11(H11)
2.b Idealised Me refined as rotating group:
 C5A(H5AA,H5AB,H5AC), C5(H5A,H5B,H5C), C1(H1B,H1C,H1D), C1A(H1AA,H1AB,H1AC)
;
_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 2.531
_oxdiff_exptl_absorpt_empirical_full_min 0.580
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
S1A S 0.50674(7) 0.63309(4) 0.81655(3) 0.02850(15) Uani 1 1 d . . . . .
S1 S 0.34529(8) 0.94146(4) 0.14105(4) 0.03120(16) Uani 1 1 d . . . . .
F3A F 0.6525(2) 0.77242(11) 0.96855(10) 0.0472(4) Uani 1 1 d . . . . .
F1A F 0.4491(2) 0.64392(13) 0.97882(10) 0.0494(4) Uani 1 1 d . . . . .
F2A F 0.7235(2) 0.63208(13) 0.95461(10) 0.0490(4) Uani 1 1 d . . . . .
O1 O 0.2949(2) 0.58780(11) 0.45498(11) 0.0331(4) Uani 1 1 d . . . . .
O2 O 0.2533(2) 0.83009(12) 0.14104(11) 0.0351(4) Uani 1 1 d . . . . .
F3 F 0.2696(3) 1.00105(13) 0.00957(11) 0.0540(4) Uani 1 1 d . . . . .
O2A O 0.4415(2) 0.51552(12) 0.80367(10) 0.0322(4) Uani 1 1 d . . . . .
F1 F 0.0392(2) 0.88789(15) 0.02474(12) 0.0555(4) Uani 1 1 d . . . . .
O3A O 0.3527(2) 0.67266(12) 0.80698(11) 0.0359(4) Uani 1 1 d . . . . .
O1A O -0.1853(2) 0.09481(11) 0.47580(11) 0.0326(4) Uani 1 1 d . . . . .
O4A O 0.6655(2) 0.65625(13) 0.77636(12) 0.0371(4) Uani 1 1 d . . . . .
F2 F 0.2712(3) 0.84417(14) -0.03150(10) 0.0587(5) Uani 1 1 d . . . . .
N1 N 0.5635(2) 0.89969(13) 0.43125(12) 0.0252(4) Uani 1 1 d . . . . .
H1 H 0.6250 0.9641 0.4426 0.030 Uiso 1 1 calc R . . . .
O4 O 0.5388(3) 0.95802(17) 0.13726(13) 0.0498(5) Uani 1 1 d . . . . .
N2 N 0.4130(3) 0.87069(13) 0.28398(12) 0.0272(4) Uani 1 1 d . . . . .
N2A N 0.3019(3) 0.47545(13) 0.65756(12) 0.0272(4) Uani 1 1 d . . . . .
O3 O 0.2758(3) 1.01398(14) 0.20082(12) 0.0493(5) Uani 1 1 d . . . . .
N1A N 0.1447(2) 0.42150(13) 0.50694(12) 0.0260(4) Uani 1 1 d . . . . .
H1A H 0.1863 0.4806 0.4991 0.031 Uiso 1 1 calc R . . . .
C3 C 0.4538(3) 0.74723(15) 0.44740(14) 0.0245(4) Uani 1 1 d . . . . .
C8A C 0.1326(3) 0.26886(16) 0.64832(14) 0.0257(4) Uani 1 1 d . . . . .
C7 C 0.4465(3) 0.83744(16) 0.35286(14) 0.0254(4) Uani 1 1 d . . . . .
C8 C 0.2530(3) 0.66540(16) 0.27927(15) 0.0258(4) Uani 1 1 d . . . . .
C7A C 0.1857(3) 0.40261(15) 0.58391(14) 0.0250(4) Uani 1 1 d . . . . .
C4A C 0.0301(3) 0.33555(15) 0.44412(14) 0.0252(4) Uani 1 1 d . . . . .
C3A C -0.0076(3) 0.25741(15) 0.48157(14) 0.0249(4) Uani 1 1 d . . . . .
C9 C 0.1732(3) 0.56089(16) 0.26737(15) 0.0285(5) Uani 1 1 d . . . . .
H9 H 0.2011 0.5355 0.3139 0.034 Uiso 1 1 calc R . . . .
C6 C 0.3738(3) 0.74052(15) 0.35842(14) 0.0248(4) Uani 1 1 d . . . . .
C2 C 0.4151(3) 0.67061(15) 0.49114(14) 0.0251(4) Uani 1 1 d . . . . .
C13A C 0.2543(3) 0.34343(16) 0.72666(15) 0.0267(4) Uani 1 1 d . . . . .
C4 C 0.5707(3) 0.84770(15) 0.48858(14) 0.0246(4) Uani 1 1 d . . . . .
C13 C 0.2127(3) 0.69841(16) 0.20574(15) 0.0265(4) Uani 1 1 d . . . . .
C2A C -0.1327(3) 0.15463(15) 0.43521(15) 0.0260(4) Uani 1 1 d . . . . .
C14 C 0.2994(3) 0.80209(16) 0.21571(15) 0.0277(4) Uani 1 1 d . . . . .
C14A C 0.3273(3) 0.44380(16) 0.72375(14) 0.0265(4) Uani 1 1 d . . . . .
C12 C 0.0909(3) 0.62997(17) 0.12664(15) 0.0296(5) Uani 1 1 d . . . . .
H12 H 0.0635 0.6531 0.0785 0.036 Uiso 1 1 calc R . . . .
C6A C 0.0949(3) 0.30154(15) 0.57348(14) 0.0247(4) Uani 1 1 d . . . . .
C12A C 0.3021(3) 0.31760(17) 0.80270(15) 0.0300(5) Uani 1 1 d . . . . .
H12A H 0.3839 0.3678 0.8541 0.036 Uiso 1 1 calc R . . . .
C10A C 0.1085(3) 0.14586(17) 0.72648(16) 0.0315(5) Uani 1 1 d . . . . .
H10A H 0.0576 0.0786 0.7270 0.038 Uiso 1 1 calc R . . . .
C9A C 0.0618(3) 0.16928(16) 0.65154(15) 0.0280(4) Uani 1 1 d . . . . .
H9A H -0.0197 0.1175 0.6009 0.034 Uiso 1 1 calc R . . . .
C10 C 0.0560(3) 0.49588(17) 0.18951(16) 0.0315(5) Uani 1 1 d . . . . .
H10 H 0.0037 0.4263 0.1833 0.038 Uiso 1 1 calc R . . . .
C11A C 0.2301(3) 0.21982(18) 0.80192(16) 0.0319(5) Uani 1 1 d . . . . .
H11A H 0.2627 0.2021 0.8527 0.038 Uiso 1 1 calc R . . . .
C11 C 0.0122(3) 0.53013(17) 0.11909(15) 0.0306(5) Uani 1 1 d . . . . .
H11 H -0.0717 0.4844 0.0664 0.037 Uiso 1 1 calc R . . . .
C5A C -0.0289(3) 0.34177(16) 0.35434(15) 0.0295(5) Uani 1 1 d . . . . .
H5AA H 0.0160 0.4126 0.3562 0.044 Uiso 1 1 calc GR . . . .
H5AB H -0.1664 0.3187 0.3390 0.044 Uiso 1 1 calc GR . . . .
H5AC H 0.0250 0.2981 0.3090 0.044 Uiso 1 1 calc GR . . . .
C5 C 0.6887(3) 0.90492(16) 0.57922(15) 0.0283(4) Uani 1 1 d . . . . .
H5A H 0.7563 0.9738 0.5818 0.043 Uiso 1 1 calc GR . . . .
H5B H 0.7794 0.8686 0.5901 0.043 Uiso 1 1 calc GR . . . .
H5C H 0.6077 0.9098 0.6251 0.043 Uiso 1 1 calc GR . . . .
C1 C 0.5206(3) 0.69100(17) 0.58280(15) 0.0314(5) Uani 1 1 d . . . . .
H1B H 0.4903 0.7477 0.6265 0.047 Uiso 1 1 calc GR . . . .
H1C H 0.6561 0.7089 0.5819 0.047 Uiso 1 1 calc GR . . . .
H1D H 0.4842 0.6296 0.5996 0.047 Uiso 1 1 calc GR . . . .
C1A C -0.1984(3) 0.11806(16) 0.33578(16) 0.0315(5) Uani 1 1 d . . . . .
H1AA H -0.2707 0.0459 0.3153 0.047 Uiso 1 1 calc GR . . . .
H1AB H -0.0893 0.1258 0.3052 0.047 Uiso 1 1 calc GR . . . .
H1AC H -0.2780 0.1586 0.3220 0.047 Uiso 1 1 calc GR . . . .
C15 C 0.2222(4) 0.91557(19) 0.02802(16) 0.0362(5) Uani 1 1 d . . . . .
C15A C 0.5891(3) 0.67111(18) 0.93759(16) 0.0336(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'
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O2A S1A C15A 93.45(10) . . ?
O3A S1A O2A 111.98(10) . . ?
O3A S1A C15A 106.70(11) . . ?
O4A S1A O2A 111.16(10) . . ?
O4A S1A O3A 122.00(11) . . ?
O4A S1A C15A 107.42(11) . . ?
O2 S1 C15 93.58(10) . . ?
O4 S1 O2 111.21(12) . . ?
O4 S1 C15 107.66(12) . . ?
O3 S1 O2 111.43(11) . . ?
O3 S1 O4 121.85(13) . . ?
O3 S1 C15 107.14(12) . . ?
C14 O2 S1 120.32(14) . . ?
C14A O2A S1A 121.01(14) . . ?
C7 N1 H1 125.0 . . ?
C4 N1 H1 125.0 . . ?
C4 N1 C7 110.01(17) . . ?
C14 N2 C7 113.84(18) . . ?
C14A N2A C7A 113.74(18) . . ?
C7A N1A H1A 125.1 . . ?
C4A N1A H1A 125.1 . . ?
C4A N1A C7A 109.82(17) . . ?
C6 C3 C2 128.86(19) . . ?
C4 C3 C6 106.37(18) . . ?
C4 C3 C2 124.6(2) . . ?
C13A C8A C6A 117.21(19) . . ?
C9A C8A C13A 116.7(2) . . ?
C9A C8A C6A 126.1(2) . . ?
N1 C7 C6 109.30(19) . . ?
N2 C7 N1 122.21(19) . . ?
N2 C7 C6 128.49(19) . . ?
C9 C8 C6 125.6(2) . . ?
C9 C8 C13 117.2(2) . . ?
C13 C8 C6 117.25(19) . . ?
N2A C7A C6A 127.8(2) . . ?
N1A C7A N2A 122.13(18) . . ?
N1A C7A C6A 110.05(18) . . ?
N1A C4A C3A 108.59(19) . . ?
N1A C4A C5A 117.33(18) . . ?
C3A C4A C5A 134.08(19) . . ?
C4A C3A C2A 124.5(2) . . ?
C4A C3A C6A 106.55(18) . . ?
C2A C3A C6A 128.9(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 H9 119.6 . . ?
C7 C6 C3 105.52(18) . . ?
C7 C6 C8 115.61(19) . . ?
C8 C6 C3 138.83(19) . . ?
O1 C2 C3 121.4(2) . . ?
O1 C2 C1 117.98(19) . . ?
C3 C2 C1 120.61(19) . . ?
C14A C13A C8A 117.03(19) . . ?
C12A C13A C8A 121.1(2) . . ?
C12A C13A C14A 121.9(2) . . ?
N1 C4 C3 108.79(19) . . ?
N1 C4 C5 117.40(18) . . ?
C3 C4 C5 133.8(2) . . ?
C14 C13 C8 117.45(19) . . ?
C12 C13 C8 120.7(2) . . ?
C12 C13 C14 121.9(2) . . ?
O1A C2A C3A 121.4(2) . . ?
O1A C2A C1A 118.01(19) . . ?
C3A C2A C1A 120.54(19) . . ?
O2 C14 C13 114.72(18) . . ?
N2 C14 O2 118.00(19) . . ?
N2 C14 C13 127.3(2) . . ?
O2A C14A C13A 114.91(19) . . ?
N2A C14A O2A 117.31(19) . . ?
N2A C14A C13A 127.8(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C8A C6A C3A 138.53(19) . . ?
C7A C6A C8A 116.35(19) . . ?
C7A C6A C3A 104.99(18) . . ?
C13A C12A H12A 120.1 . . ?
C11A C12A C13A 119.7(2) . . ?
C11A C12A H12A 120.1 . . ?
C9A C10A H10A 119.5 . . ?
C9A C10A C11A 120.9(2) . . ?
C11A C10A H10A 119.5 . . ?
C8A C9A H9A 119.3 . . ?
C10A C9A C8A 121.4(2) . . ?
C10A C9A H9A 119.3 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.4(2) . . ?
C11 C10 H10 119.3 . . ?
C12A C11A C10A 120.2(2) . . ?
C12A C11A H11A 119.9 . . ?
C10A C11A H11A 119.9 . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C4A C5A H5AA 109.5 . . ?
C4A C5A H5AB 109.5 . . ?
C4A C5A H5AC 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
H1B C1 H1C 109.5 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
C2A C1A H1AA 109.5 . . ?
C2A C1A H1AB 109.5 . . ?
C2A C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
F3 C15 S1 107.53(17) . . ?
F1 C15 S1 110.61(17) . . ?
F1 C15 F3 108.9(2) . . ?
F2 C15 S1 111.08(17) . . ?
F2 C15 F3 109.1(2) . . ?
F2 C15 F1 109.5(2) . . ?
F3A C15A S1A 106.86(17) . . ?
F1A C15A S1A 110.75(16) . . ?
F1A C15A F3A 108.1(2) . . ?
F2A C15A S1A 112.03(16) . . ?
F2A C15A F3A 109.5(2) . . ?
F2A C15A F1A 109.5(2) . . ?
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
S1A O2A 1.5789(16) . ?
S1A O3A 1.4118(18) . ?
S1A O4A 1.4062(18) . ?
S1A C15A 1.841(2) . ?
S1 O2 1.5778(16) . ?
S1 O4 1.410(2) . ?
S1 O3 1.4064(19) . ?
S1 C15 1.837(2) . ?
F3A C15A 1.328(3) . ?
F1A C15A 1.319(3) . ?
F2A C15A 1.305(3) . ?
O1 C2 1.234(3) . ?
O2 C14 1.410(3) . ?
F3 C15 1.320(3) . ?
O2A C14A 1.412(3) . ?
F1 C15 1.314(3) . ?
O1A C2A 1.236(3) . ?
F2 C15 1.309(3) . ?
N1 H1 0.8800 . ?
N1 C7 1.369(3) . ?
N1 C4 1.350(3) . ?
N2 C7 1.352(3) . ?
N2 C14 1.286(3) . ?
N2A C7A 1.363(3) . ?
N2A C14A 1.287(3) . ?
N1A H1A 0.8800 . ?
N1A C7A 1.362(3) . ?
N1A C4A 1.357(3) . ?
C3 C6 1.457(3) . ?
C3 C2 1.459(3) . ?
C3 C4 1.407(3) . ?
C8A C13A 1.430(3) . ?
C8A C6A 1.440(3) . ?
C8A C9A 1.416(3) . ?
C7 C6 1.397(3) . ?
C8 C9 1.418(3) . ?
C8 C6 1.438(3) . ?
C8 C13 1.428(3) . ?
C7A C6A 1.394(3) . ?
C4A C3A 1.406(3) . ?
C4A C5A 1.497(3) . ?
C3A C2A 1.462(3) . ?
C3A C6A 1.463(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.373(3) . ?
C2 C1 1.508(3) . ?
C13A C14A 1.427(3) . ?
C13A C12A 1.415(3) . ?
C4 C5 1.498(3) . ?
C13 C14 1.423(3) . ?
C13 C12 1.412(3) . ?
C2A C1A 1.503(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.372(3) . ?
C12A H12A 0.9500 . ?
C12A C11A 1.370(3) . ?
C10A H10A 0.9500 . ?
C10A C9A 1.376(3) . ?
C10A C11A 1.400(3) . ?
C9A H9A 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.401(3) . ?
C11A H11A 0.9500 . ?
C11 H11 0.9500 . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A H5AC 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
