#------------------------------------------------------------------------------
#$Date: 2022-02-04 22:01:09 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272764 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/84/7158456.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_7158456
loop_
_publ_author_name
'Santiago, Carlos'
'Jiménez-Aberasturi, Xabier'
'Leicea, Eztizen'
'Lete, Marta G.'
'Sotomayor, Nuria'
'Lete, Esther'
_publ_section_title
;
 Microwave-assisted palladium catalysed C-H acylation with aldehydes:
 synthesis and diversification of 3-acylthiophenes.
;
_journal_issue                   4
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              852
_journal_page_last               861
_journal_paper_doi               10.1039/d1ob02176a
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C23 H20 N S, C F3 O3 S, C H3 O0.5'
_chemical_formula_sum            'C25 H23 F3 N O3.5 S2'
_chemical_formula_weight         514.56
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-02T11:13:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2021-09-03 deposited with the CCDC.	2021-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                109.356(9)
_cell_angle_beta                 100.318(9)
_cell_angle_gamma                106.611(9)
_cell_formula_units_Z            2
_cell_length_a                   9.1139(10)
_cell_length_b                   11.7059(12)
_cell_length_c                   12.6851(14)
_cell_measurement_reflns_used    1117
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      22.896
_cell_measurement_theta_min      1.778
_cell_volume                     1166.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2439
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00 -63.00   1.00    9.00    --  -23.50-155.00-133.00   26
  2  ω    -93.00 -67.00   1.00    9.00    --  -23.50 -57.00 -90.00   26
  3  ω    -54.00  38.00   1.00    9.00    --   24.74 -77.00  60.00   92
  4  ω     42.00 116.00   1.00    9.00    --   24.74-178.00-120.00   74
  5  ω    -55.00  66.00   1.00    9.00    --   24.74 -77.00 -60.00  121
  6  ω    -55.00  66.00   1.00    9.00    --   24.74 -77.00-180.00  121
;
_diffrn_measurement_device       'four-circleκ-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0774428
_diffrn_orient_matrix_UB_12      0.0025471
_diffrn_orient_matrix_UB_13      0.0254227
_diffrn_orient_matrix_UB_21      -0.0109703
_diffrn_orient_matrix_UB_22      0.0211172
_diffrn_orient_matrix_UB_23      0.0562561
_diffrn_orient_matrix_UB_31      -0.0338311
_diffrn_orient_matrix_UB_32      -0.065836
_diffrn_orient_matrix_UB_33      -0.0074961
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.2095
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7751
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_min         1.785
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (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            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       prism
_exptl_crystal_F_000             534
_exptl_crystal_size_max          0.407
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.08
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4588
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0679
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0346P)²+0.2450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1502
_reflns_Friedel_coverage         0
_reflns_number_gt                2749
_reflns_number_total             4588
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02176a2.cif
_cod_data_source_block           a20210181_csa637
_cod_depositor_comments          'Adding full bibliography for 7158456.cif.'
_cod_original_cell_volume        1166.1(2)
_cod_original_formula_sum        'C25 H23 F3 N O3.50 S2'
_cod_database_code               7158456
loop_
_symmetry_equiv_pos_as_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 0.81135(12) 0.59001(10) 0.56342(9) 0.0261(3) Uani 1 1 d . . . . .
S1A S 0.02180(13) 0.79836(10) 0.26868(9) 0.0275(3) Uani 1 1 d . . . . .
F1A F 0.3248(3) 0.8473(3) 0.3622(2) 0.0532(8) Uani 1 1 d . . . . .
F2A F 0.1635(3) 0.6588(2) 0.3366(2) 0.0408(7) Uani 1 1 d . . . . .
F3A F 0.2212(4) 0.6920(3) 0.1909(2) 0.0573(8) Uani 1 1 d . . . . .
O1A O 0.0167(4) 0.8553(3) 0.3866(2) 0.0390(8) Uani 1 1 d . . . . .
O2A O -0.1106(4) 0.6791(3) 0.1940(3) 0.0452(9) Uani 1 1 d . . . . .
O3A O 0.0693(4) 0.8889(3) 0.2159(2) 0.0364(8) Uani 1 1 d . . . . .
N1 N 0.4576(4) 0.2444(3) 0.4247(3) 0.0196(7) Uani 1 1 d . . . . .
C1 C 0.8566(5) 0.5741(4) 0.4345(3) 0.0269(10) Uani 1 1 d . . . . .
H1 H 0.940131 0.639553 0.428118 0.032 Uiso 1 1 calc R . . . .
C2 C 0.7614(5) 0.4589(4) 0.3421(3) 0.0250(10) Uani 1 1 d . . . . .
H2 H 0.769938 0.434073 0.264889 0.03 Uiso 1 1 calc R . . . .
C3 C 0.6490(5) 0.3825(4) 0.3780(3) 0.0204(9) Uani 1 1 d . . . . .
C4 C 0.5163(5) 0.2486(4) 0.3196(3) 0.0216(9) Uani 1 1 d . . . . .
C5 C 0.3351(5) 0.1456(4) 0.4197(4) 0.0251(10) Uani 1 1 d . . . . .
H5 H 0.280039 0.070067 0.348625 0.03 Uiso 1 1 calc R . . . .
C6 C 0.2895(5) 0.1547(4) 0.5191(4) 0.0292(10) Uani 1 1 d . . . . .
H6 H 0.203132 0.084839 0.517425 0.035 Uiso 1 1 calc R . . . .
C7 C 0.3708(5) 0.2668(4) 0.6221(3) 0.0277(10) Uani 1 1 d . . . . .
H7 H 0.339552 0.273396 0.690747 0.033 Uiso 1 1 calc R . . . .
C8 C 0.4970(5) 0.3687(4) 0.6251(3) 0.0237(9) Uani 1 1 d . . . . .
H8 H 0.552407 0.445606 0.695049 0.028 Uiso 1 1 calc R . . . .
C9 C 0.5407(5) 0.3563(4) 0.5241(3) 0.0204(9) Uani 1 1 d . . . . .
C10 C 0.6595(5) 0.4395(4) 0.4934(3) 0.0209(9) Uani 1 1 d . . . . .
C11 C 0.5758(5) 0.1371(4) 0.2764(3) 0.0227(9) Uani 1 1 d . . . . .
C12 C 0.7161(5) 0.1420(4) 0.3460(3) 0.0281(10) Uani 1 1 d . . . . .
H12 H 0.771692 0.213448 0.419819 0.034 Uiso 1 1 calc R . . . .
C13 C 0.7757(5) 0.0446(4) 0.3093(4) 0.0292(10) Uani 1 1 d . . . . .
H13 H 0.872339 0.049792 0.357188 0.035 Uiso 1 1 calc R . . . .
C14 C 0.6940(5) -0.0608(4) 0.2022(4) 0.0334(11) Uani 1 1 d . . . . .
H14 H 0.734276 -0.128266 0.176217 0.04 Uiso 1 1 calc R . . . .
C15 C 0.5539(6) -0.0668(4) 0.1339(4) 0.0397(12) Uani 1 1 d . . . . .
H15 H 0.496842 -0.139463 0.061001 0.048 Uiso 1 1 calc R . . . .
C16 C 0.4950(5) 0.0321(4) 0.1703(4) 0.0340(11) Uani 1 1 d . . . . .
H16 H 0.398882 0.027275 0.121925 0.041 Uiso 1 1 calc R . . . .
C17 C 0.3818(5) 0.2420(4) 0.2306(3) 0.0219(9) Uani 1 1 d . . . . .
C18 C 0.2694(5) 0.2355(4) 0.1616(3) 0.0233(9) Uani 1 1 d . . . . .
C19 C 0.1278(5) 0.2273(4) 0.0781(3) 0.0253(10) Uani 1 1 d . . . . .
H19 H 0.13254 0.185701 -0.003283 0.03 Uiso 1 1 calc R . . . .
C20 C -0.0335(5) 0.1461(4) 0.0879(4) 0.0394(12) Uani 1 1 d D . . . .
H20A H -0.09769 0.072899 0.011178 0.047 Uiso 0.612(18) 1 calc R . P A 1
H20B H -0.011525 0.109212 0.146108 0.047 Uiso 0.612(18) 1 calc R . P A 1
H20C H -0.081153 0.056425 0.025764 0.047 Uiso 0.388(18) 1 calc R . P A 2
H20D H -0.020828 0.142525 0.165756 0.047 Uiso 0.388(18) 1 calc R . P A 2
C21 C -0.1237(9) 0.2291(6) 0.1237(9) 0.034(2) Uani 0.612(18) 1 d D U P A 1
H21A H -0.09752 0.270092 0.210098 0.041 Uiso 0.612(18) 1 calc R . P A 1
H21B H -0.240993 0.180061 0.088538 0.041 Uiso 0.612(18) 1 calc R . P A 1
C22 C -0.0649(9) 0.3274(11) 0.0755(10) 0.040(3) Uani 0.612(18) 1 d D U P A 1
H22A H -0.086342 0.406663 0.114972 0.048 Uiso 0.612(18) 1 calc R . P A 1
H22B H -0.120855 0.291381 -0.0095 0.048 Uiso 0.612(18) 1 calc R . P A 1
C23 C 0.1156(5) 0.3612(4) 0.0969(4) 0.0340(11) Uani 1 1 d D . . . .
H23A H 0.177701 0.426978 0.177465 0.041 Uiso 0.612(18) 1 calc R . P A 1
H23B H 0.152901 0.393629 0.039795 0.041 Uiso 0.612(18) 1 calc R . P A 1
H23C H 0.203033 0.429093 0.167547 0.041 Uiso 0.388(18) 1 calc R . P A 2
H23D H 0.132071 0.381337 0.028978 0.041 Uiso 0.388(18) 1 calc R . P A 2
C1A C 0.1907(5) 0.7460(4) 0.2888(4) 0.0300(10) Uani 1 1 d . . . . .
C21B C -0.1306(14) 0.2279(10) 0.0702(17) 0.047(4) Uani 0.388(18) 1 d D U P A 2
H21C H -0.18878 0.192917 -0.01433 0.056 Uiso 0.388(18) 1 calc R . P A 2
H21D H -0.212117 0.217928 0.112109 0.056 Uiso 0.388(18) 1 calc R . P A 2
C22B C -0.0365(13) 0.3677(12) 0.1106(16) 0.045(4) Uani 0.388(18) 1 d D U P A 2
H22C H -0.082268 0.406113 0.060646 0.053 Uiso 0.388(18) 1 calc R . P A 2
H22D H -0.027107 0.417211 0.193324 0.053 Uiso 0.388(18) 1 calc R . P A 2
O1D O 0.5834(9) 0.4839(7) 0.1166(7) 0.0622(13) Uani 0.5 1 d D . P B 1
C1D C 0.5159(8) 0.4439(5) 0.0098(6) 0.0622(13) Uani 1 1 d D . . . .
H1DA H 0.421(3) 0.382(4) -0.002(4) 0.071(18) Uiso 1 1 d D . . . .
H1DB H 0.561(8) 0.411(6) -0.045(6) 0.23(5) Uiso 1 1 d D . . . .
H1D H 0.65(2) 0.565(7) 0.161(4) 0.279 Uiso 0.5 1 d DR . P C 1
H1DC H 0.582(7) 0.465(11) 0.081(4) 0.279 Uiso 0.5 1 d DR . P D 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
-6 -11 4 0.1756
-11 11 -4 0.0378
3 14 -5 0.1991
11 -11 4 0.0259
-1 1 16 0.0297
1 -1 -16 0.0281
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
C10 S1 C1 90.09(19) . . ?
O1A S1A O3A 115.28(18) . . ?
O1A S1A C1A 102.43(19) . . ?
O2A S1A O1A 114.79(19) . . ?
O2A S1A O3A 115.17(18) . . ?
O2A S1A C1A 103.3(2) . . ?
O3A S1A C1A 103.4(2) . . ?
C5 N1 C4 124.1(3) . . ?
C5 N1 C9 123.3(3) . . ?
C9 N1 C4 112.5(3) . . ?
S1 C1 H1 123.1 . . ?
C2 C1 S1 113.9(3) . . ?
C2 C1 H1 123.1 . . ?
C1 C2 H2 125 . . ?
C1 C2 C3 110.1(4) . . ?
C3 C2 H2 125 . . ?
C2 C3 C4 135.4(3) . . ?
C10 C3 C2 114.2(4) . . ?
C10 C3 C4 110.3(3) . . ?
C3 C4 N1 99.3(3) . . ?
C3 C4 C11 113.9(3) . . ?
C11 C4 N1 109.0(3) . . ?
C17 C4 N1 107.3(3) . . ?
C17 C4 C3 112.4(3) . . ?
C17 C4 C11 113.7(3) . . ?
N1 C5 H5 120.5 . . ?
N1 C5 C6 119.0(4) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.6(4) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.4(4) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.7 . . ?
C9 C8 C7 118.6(4) . . ?
C9 C8 H8 120.7 . . ?
N1 C9 C8 119.1(4) . . ?
N1 C9 C10 106.5(3) . . ?
C8 C9 C10 134.4(4) . . ?
C3 C10 S1 111.8(3) . . ?
C3 C10 C9 111.3(3) . . ?
C9 C10 S1 136.9(3) . . ?
C12 C11 C4 119.1(3) . . ?
C16 C11 C4 121.9(4) . . ?
C16 C11 C12 119.0(4) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(4) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(4) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.3(4) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.9(4) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 C15 120.0(4) . . ?
C11 C16 H16 120 . . ?
C15 C16 H16 120 . . ?
C18 C17 C4 177.3(4) . . ?
C17 C18 C19 178.6(4) . . ?
C18 C19 H19 108.7 . . ?
C18 C19 C20 112.8(3) . . ?
C18 C19 C23 113.6(3) . . ?
C20 C19 H19 108.7 . . ?
C23 C19 H19 108.7 . . ?
C23 C19 C20 104.2(3) . . ?
C19 C20 H20A 109.7 . . ?
C19 C20 H20B 109.7 . . ?
C19 C20 H20C 111.9 . . ?
C19 C20 H20D 111.9 . . ?
H20A C20 H20B 108.2 . . ?
H20C C20 H20D 109.6 . . ?
C21 C20 C19 109.8(4) . . ?
C21 C20 H20A 109.7 . . ?
C21 C20 H20B 109.7 . . ?
C21B C20 C19 99.2(7) . . ?
C21B C20 H20C 111.9 . . ?
C21B C20 H20D 111.9 . . ?
C20 C21 H21A 111.6 . . ?
C20 C21 H21B 111.6 . . ?
C20 C21 C22 100.9(7) . . ?
H21A C21 H21B 109.4 . . ?
C22 C21 H21A 111.6 . . ?
C22 C21 H21B 111.6 . . ?
C21 C22 H22A 110.1 . . ?
C21 C22 H22B 110.1 . . ?
C21 C22 C23 108.0(6) . . ?
H22A C22 H22B 108.4 . . ?
C23 C22 H22A 110.1 . . ?
C23 C22 H22B 110.1 . . ?
C19 C23 H23A 111.5 . . ?
C19 C23 H23B 111.5 . . ?
C19 C23 H23C 108.8 . . ?
C19 C23 H23D 108.8 . . ?
C22 C23 C19 101.2(5) . . ?
C22 C23 H23A 111.5 . . ?
C22 C23 H23B 111.5 . . ?
H23A C23 H23B 109.3 . . ?
H23C C23 H23D 107.7 . . ?
C22B C23 C19 113.8(6) . . ?
C22B C23 H23C 108.8 . . ?
C22B C23 H23D 108.8 . . ?
F1A C1A S1A 110.7(3) . . ?
F2A C1A S1A 110.6(3) . . ?
F2A C1A F1A 106.9(3) . . ?
F3A C1A S1A 113.6(3) . . ?
F3A C1A F1A 107.5(4) . . ?
F3A C1A F2A 107.2(3) . . ?
C20 C21B H21C 108.5 . . ?
C20 C21B H21D 108.5 . . ?
H21C C21B H21D 107.5 . . ?
C22B C21B C20 115.1(9) . . ?
C22B C21B H21C 108.5 . . ?
C22B C21B H21D 108.5 . . ?
C23 C22B C21B 99.6(9) . . ?
C23 C22B H22C 111.9 . . ?
C23 C22B H22D 111.9 . . ?
C21B C22B H22C 111.9 . . ?
C21B C22B H22D 111.9 . . ?
H22C C22B H22D 109.6 . . ?
C1D O1D H1D 124.3(19) . . ?
O1D C1D C1D 106.8(7) . 2_665 ?
O1D C1D H1DA 103(3) . . ?
O1D C1D H1DB 123(7) . . ?
C1D C1D H1DA 109(4) 2_665 . ?
C1D C1D H1DB 106(7) 2_665 . ?
C1D C1D H1DC 115(8) 2_665 . ?
H1DA C1D H1DB 109(2) . . ?
H1DA C1D H1DC 109(3) . . ?
H1DB C1D H1DC 109(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 C1 1.722(4) . ?
S1 C10 1.714(4) . ?
S1A O1A 1.437(3) . ?
S1A O2A 1.433(3) . ?
S1A O3A 1.438(3) . ?
S1A C1A 1.820(4) . ?
F1A C1A 1.342(5) . ?
F2A C1A 1.339(5) . ?
F3A C1A 1.313(4) . ?
N1 C4 1.533(5) . ?
N1 C5 1.333(5) . ?
N1 C9 1.369(5) . ?
C1 H1 0.95 . ?
C1 C2 1.365(5) . ?
C2 H2 0.95 . ?
C2 C3 1.403(5) . ?
C3 C4 1.515(5) . ?
C3 C10 1.364(5) . ?
C4 C11 1.527(5) . ?
C4 C17 1.475(5) . ?
C5 H5 0.95 . ?
C5 C6 1.378(5) . ?
C6 H6 0.95 . ?
C6 C7 1.392(5) . ?
C7 H7 0.95 . ?
C7 C8 1.385(5) . ?
C8 H8 0.95 . ?
C8 C9 1.383(5) . ?
C9 C10 1.439(5) . ?
C11 C12 1.392(5) . ?
C11 C16 1.377(5) . ?
C12 H12 0.95 . ?
C12 C13 1.380(5) . ?
C13 H13 0.95 . ?
C13 C14 1.387(5) . ?
C14 H14 0.95 . ?
C14 C15 1.378(6) . ?
C15 H15 0.95 . ?
C15 C16 1.390(6) . ?
C16 H16 0.95 . ?
C17 C18 1.188(5) . ?
C18 C19 1.472(5) . ?
C19 H19 1 . ?
C19 C20 1.557(6) . ?
C19 C23 1.546(5) . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C20 H20C 0.99 . ?
C20 H20D 0.99 . ?
C20 C21 1.457(7) . ?
C20 C21B 1.519(9) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C21 C22 1.488(8) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C22 C23 1.527(7) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C23 H23C 0.99 . ?
C23 H23D 0.99 . ?
C23 C22B 1.448(9) . ?
C21B H21C 0.99 . ?
C21B H21D 0.99 . ?
C21B C22B 1.469(9) . ?
C22B H22C 0.99 . ?
C22B H22D 0.99 . ?
O1D C1D 1.245(9) . ?
O1D H1D 0.891(10) . ?
C1D C1D 1.510(12) 2_665 ?
C1D H1DA 0.906(10) . ?
C1D H1DB 0.903(10) . ?
C1D H1DC 0.903(10) . ?
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
S1 C1 C2 C3 0.2(5) . . . . ?
O1A S1A C1A F1A -57.7(3) . . . . ?
O1A S1A C1A F2A 60.6(3) . . . . ?
O1A S1A C1A F3A -178.8(3) . . . . ?
O2A S1A C1A F1A -177.2(3) . . . . ?
O2A S1A C1A F2A -58.9(3) . . . . ?
O2A S1A C1A F3A 61.7(4) . . . . ?
O3A S1A C1A F1A 62.5(3) . . . . ?
O3A S1A C1A F2A -179.2(3) . . . . ?
O3A S1A C1A F3A -58.7(3) . . . . ?
N1 C4 C11 C12 -69.3(4) . . . . ?
N1 C4 C11 C16 111.0(4) . . . . ?
N1 C5 C6 C7 0.6(6) . . . . ?
N1 C9 C10 S1 -178.1(3) . . . . ?
N1 C9 C10 C3 1.1(5) . . . . ?
C1 S1 C10 C3 0.7(3) . . . . ?
C1 S1 C10 C9 179.9(5) . . . . ?
C1 C2 C3 C4 -178.9(4) . . . . ?
C1 C2 C3 C10 0.4(5) . . . . ?
C2 C3 C4 N1 179.4(4) . . . . ?
C2 C3 C4 C11 63.6(6) . . . . ?
C2 C3 C4 C17 -67.4(6) . . . . ?
C2 C3 C10 S1 -0.8(5) . . . . ?
C2 C3 C10 C9 179.8(3) . . . . ?
C3 C4 C11 C12 40.6(5) . . . . ?
C3 C4 C11 C16 -139.1(4) . . . . ?
C4 N1 C5 C6 -177.8(3) . . . . ?
C4 N1 C9 C8 177.6(3) . . . . ?
C4 N1 C9 C10 -1.1(4) . . . . ?
C4 C3 C10 S1 178.7(3) . . . . ?
C4 C3 C10 C9 -0.8(5) . . . . ?
C4 C11 C12 C13 -178.8(4) . . . . ?
C4 C11 C16 C15 179.5(4) . . . . ?
C5 N1 C4 C3 178.0(4) . . . . ?
C5 N1 C4 C11 -62.6(5) . . . . ?
C5 N1 C4 C17 60.9(5) . . . . ?
C5 N1 C9 C8 0.2(6) . . . . ?
C5 N1 C9 C10 -178.5(4) . . . . ?
C5 C6 C7 C8 -0.1(6) . . . . ?
C6 C7 C8 C9 -0.4(6) . . . . ?
C7 C8 C9 N1 0.3(6) . . . . ?
C7 C8 C9 C10 178.6(4) . . . . ?
C8 C9 C10 S1 3.5(8) . . . . ?
C8 C9 C10 C3 -177.2(4) . . . . ?
C9 N1 C4 C3 0.6(4) . . . . ?
C9 N1 C4 C11 120.0(3) . . . . ?
C9 N1 C4 C17 -116.5(3) . . . . ?
C9 N1 C5 C6 -0.7(6) . . . . ?
C10 S1 C1 C2 -0.5(3) . . . . ?
C10 C3 C4 N1 0.1(4) . . . . ?
C10 C3 C4 C11 -115.6(4) . . . . ?
C10 C3 C4 C17 113.3(4) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
C12 C11 C16 C15 -0.2(6) . . . . ?
C12 C13 C14 C15 -0.1(7) . . . . ?
C13 C14 C15 C16 0.9(7) . . . . ?
C14 C15 C16 C11 -0.7(7) . . . . ?
C16 C11 C12 C13 1.0(6) . . . . ?
C17 C4 C11 C12 171.0(4) . . . . ?
C17 C4 C11 C16 -8.7(5) . . . . ?
C18 C19 C20 C21 117.0(6) . . . . ?
C18 C19 C20 C21B 141.3(8) . . . . ?
C18 C19 C23 C22 -140.4(5) . . . . ?
C18 C19 C23 C22B -126.1(9) . . . . ?
C19 C20 C21 C22 28.1(9) . . . . ?
C19 C20 C21B C22B -29.8(18) . . . . ?
C19 C23 C22B C21B -13.8(16) . . . . ?
C20 C19 C23 C22 -17.3(6) . . . . ?
C20 C19 C23 C22B -3.0(9) . . . . ?
C20 C21 C22 C23 -40.6(11) . . . . ?
C20 C21B C22B C23 28(2) . . . . ?
C21 C22 C23 C19 36.5(10) . . . . ?
C23 C19 C20 C21 -6.6(6) . . . . ?
C23 C19 C20 C21B 17.7(8) . . . . ?
