#------------------------------------------------------------------------------
#$Date: 2022-08-03 00:57:45 +0300 (Wed, 03 Aug 2022) $
#$Revision: 277043 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/04/7130463.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_7130463
loop_
_publ_author_name
'Yu, Ke-Yin'
'Ge, Xiao-Min'
'Fan, Yi-Jun'
'Liu, Xiao-Tao'
'Yang, Xue'
'Yang, Yu-Han'
'Zhao, Xian-He'
'An, Xian-Tao'
'Fan, Chun-An'
_publ_section_title
;
 Iron(III)-catalyzed tandem annulation of indolyl-substituted
 p-quinone methides with ynamides for the synthesis of
 cyclopenta[b]indoles.
;
_journal_issue                   62
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8710
_journal_page_last               8713
_journal_paper_doi               10.1039/d2cc03252j
_journal_volume                  58
_journal_year                    2022
_chemical_formula_moiety         'C46 H47 F N2 O4 S'
_chemical_formula_sum            'C46 H47 F N2 O4 S'
_chemical_formula_weight         742.91
_chemical_melting_point          472.6(5)
_chemical_name_systematic        'Compound 3fa'
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-11-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-02-15 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                95.174(7)
_cell_angle_beta                 99.059(7)
_cell_angle_gamma                113.378(8)
_cell_formula_units_Z            2
_cell_length_a                   12.2295(10)
_cell_length_b                   12.9142(10)
_cell_length_c                   14.2096(12)
_cell_measurement_reflns_used    4921
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9740
_cell_measurement_theta_min      4.5140
_cell_volume                     2005.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    121.00 178.00   1.50    1.50    --  108.00  12.00 120.00   38
  2  ω     86.00 176.00   1.50    1.50    --  108.00  63.00 150.00   60
  3  ω    112.00 148.00   1.50    1.50    --  108.00 178.00 -60.00   24
  4  ω     59.00  86.00   1.50    1.50    --   54.00  77.00   0.00   18
  5  ω     34.00  59.50   1.50    1.50    --   54.00  77.00  30.00   17
  6  ω     31.00 121.00   1.50    1.50    --   54.00  77.00  60.00   60
  7  ω     58.00  89.50   1.50    1.50    --  108.00 178.00 -60.00   21
  8  ω     31.00 124.00   1.50    1.50    --   54.00  77.00 -60.00   62
  9  ω     74.00 104.00   1.50    1.50    --  108.00  25.00-120.00   20
 10  ω    118.00 178.00   1.50    1.50    --  108.00  25.00-120.00   40
 11  ω     56.00 114.50   1.50    1.50    --  108.00 -63.00-120.00   39
 12  ω     54.00 126.00   1.50    1.50    --  108.00 -38.00   0.00   48
 13  ω     52.00 115.00   1.50    1.50    --  108.00-111.00 -90.00   42
 14  ω     57.00 132.00   1.50    1.50    --  108.00 -77.00  30.00   50
 15  ω     85.00 112.00   1.50    1.50    --  108.00-111.00 150.00   18
 16  ω     50.00 129.50   1.50    1.50    --  108.00 -50.00 120.00   53
 17  ω     44.00  75.50   1.50    1.50    --  108.00  12.00 120.00   21
 18  ω     30.00  55.50   1.50    1.50    --   54.00  77.00   0.00   17
 19  ω     27.00  60.00   1.50    1.50    --    0.00  38.00 120.00   22
 20  ω     42.00 111.00   1.50    1.50    --  108.00-111.00  30.00   46
 21  ω     38.00  68.00   1.50    1.50    --  108.00 -50.00   0.00   20
 22  ω     24.00 111.00   1.50    1.50    --   54.00-125.00 -90.00   58
 23  ω     39.00 133.50   1.50    1.50    --  108.00 -38.00-150.00   63
 24  ω     39.00 112.50   1.50    1.50    --   54.00  57.00-150.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0886826000
_diffrn_orient_matrix_UB_12      0.0072887000
_diffrn_orient_matrix_UB_13      0.0929075000
_diffrn_orient_matrix_UB_21      0.1065364000
_diffrn_orient_matrix_UB_22      0.0873089000
_diffrn_orient_matrix_UB_23      -0.0357774000
_diffrn_orient_matrix_UB_31      -0.0224151000
_diffrn_orient_matrix_UB_32      0.0985340000
_diffrn_orient_matrix_UB_33      0.0499437000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12108
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        66.591
_diffrn_reflns_theta_max         66.591
_diffrn_reflns_theta_min         4.524
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             788
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane and methanol'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     500
_refine_ls_number_reflns         6924
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0478
_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)+(0.0685P)²+0.4647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1348
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5780
_reflns_number_total             6924
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc03252j2.cif
_cod_data_source_block           Compound_3fa
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '472.15-473.15' was changed
to '472.6(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7130463
_shelx_shelxl_version_number     2018/3
_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   0.906
_shelx_estimated_absorpt_t_min   0.850
_reflns_odcompleteness_completeness 97.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Restrained distances
 H43A-H12
 2 with sigma of 0.01
 H12-H53C
 2 with sigma of 0.01
2.a Ternary CH refined with riding coordinates:
 C28(H28)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C15(H15), C20(H20), C21(H21), C24(H24), C25(H25),
 C26(H26), C27(H27), C29(H29), C31(H31), C34(H34), C35(H35), C37(H37), C41(H41),
  C50(H50), C1AA(H1AA), C0AA(H0AA)
2.c Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C38(H38A,H38B,H38C), C42(H42A,H42B,H42C), C43(H43A,H43B,
 H43C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C), C52(H52A,H52B,H52C), C53(H53A,
 H53B,H53C), C60(H60A,H60B,H60C)
;
_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 4.765
_oxdiff_exptl_absorpt_empirical_full_min 0.711
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 0.24065(4) 0.48854(4) 0.16902(3) 0.04650(14) Uani 1 1 d . . . . .
N1 N 0.25767(14) 0.36831(12) 0.14616(10) 0.0424(3) Uani 1 1 d . . . . .
O2 O 0.12956(14) 0.32165(16) -0.04130(11) 0.0715(4) Uani 1 1 d . . . . .
O3 O 0.31896(13) 0.55411(12) 0.25924(11) 0.0602(4) Uani 1 1 d . . . . .
F4 F 0.76503(13) 0.70456(13) 0.35395(11) 0.0856(4) Uani 1 1 d . . . . .
C5 C 0.23853(17) 0.06890(15) 0.32939(13) 0.0455(4) Uani 1 1 d . . . . .
C6 C 0.50099(17) 0.44185(16) 0.34439(12) 0.0448(4) Uani 1 1 d . . . . .
C8 C 0.24513(19) 0.32863(18) -0.02930(14) 0.0546(5) Uani 1 1 d . . . . .
N9 N 0.45200(15) 0.30930(14) 0.44536(11) 0.0504(4) Uani 1 1 d . . . . .
C10 C 0.42841(19) 0.35892(19) 0.08178(15) 0.0558(5) Uani 1 1 d . . . . .
H10 H 0.472422 0.374239 0.144904 0.067 Uiso 1 1 calc R U . . .
C11 C 0.09014(17) 0.44223(16) 0.18529(13) 0.0444(4) Uani 1 1 d . . . . .
O12 O 0.27533(19) -0.23675(15) 0.32062(18) 0.0854(6) Uani 1 1 d . . . . .
C13 C 0.2997(3) 0.3138(2) -0.10516(15) 0.0689(6) Uani 1 1 d . . . . .
H13 H 0.257039 0.299025 -0.168666 0.083 Uiso 1 1 calc R U . . .
C14 C 0.05938(18) 0.14375(17) 0.19019(15) 0.0521(5) Uani 1 1 d . . . . .
C15 C 0.7317(2) 0.5717(2) 0.46159(16) 0.0653(6) Uani 1 1 d . . . . .
H15 H 0.809193 0.616579 0.498859 0.078 Uiso 1 1 calc R U . . .
C16 C 0.38008(16) 0.35577(15) 0.30667(12) 0.0428(4) Uani 1 1 d . . . . .
C17 C 0.31148(17) 0.35242(16) 0.06556(13) 0.0457(4) Uani 1 1 d . . . . .
C18 C 0.18408(17) 0.21539(15) 0.24469(13) 0.0439(4) Uani 1 1 d . . . . .
C19 C 0.26583(19) -0.13417(17) 0.32040(16) 0.0542(5) Uani 1 1 d . . . . .
C20 C 0.6579(2) 0.4735(2) 0.48950(15) 0.0589(5) Uani 1 1 d . . . . .
H20 H 0.683838 0.450741 0.545846 0.071 Uiso 1 1 calc R U . . .
C21 C 0.30472(18) 0.04483(16) 0.26686(14) 0.0485(4) Uani 1 1 d . . . . .
H21 H 0.339059 0.097563 0.227697 0.058 Uiso 1 1 calc R U . . .
C22 C 0.35576(17) 0.28043(16) 0.36986(12) 0.0452(4) Uani 1 1 d . . . . .
C23 C 0.19988(19) -0.11198(17) 0.38538(15) 0.0532(5) Uani 1 1 d . . . . .
C24 C -0.1195(2) 0.3894(3) 0.12145(19) 0.0880(9) Uani 1 1 d . . . . .
H24 H -0.182037 0.375375 0.068648 0.106 Uiso 1 1 calc R U . . .
C25 C -0.0519(2) 0.3997(2) 0.28791(17) 0.0677(6) Uani 1 1 d . . . . .
H25 H -0.067962 0.392204 0.349372 0.081 Uiso 1 1 calc R U . . .
C26 C 0.06612(19) 0.4313(2) 0.27569(15) 0.0604(5) Uani 1 1 d . . . . .
H26 H 0.128713 0.444991 0.328325 0.072 Uiso 1 1 calc R U . . .
C27 C 0.0236(2) 0.1336(2) 0.0913(2) 0.0848(8) Uani 1 1 d . . . . .
H27 H 0.079870 0.174776 0.056504 0.102 Uiso 1 1 calc R U . . .
C28 C 0.23263(17) 0.18428(15) 0.33950(13) 0.0457(4) Uani 1 1 d . . . . .
H28 H 0.183277 0.187828 0.386721 0.055 Uiso 1 1 calc R U . . .
C29 C 0.57786(18) 0.54270(18) 0.31793(14) 0.0527(5) Uani 1 1 d . . . . .
H29 H 0.553743 0.567403 0.262092 0.063 Uiso 1 1 calc R U . . .
C30 C -0.1463(2) 0.3792(2) 0.21175(17) 0.0636(5) Uani 1 1 d . . . . .
C31 C -0.0026(2) 0.4199(3) 0.10745(16) 0.0774(8) Uani 1 1 d . . . . .
H31 H 0.013286 0.425249 0.045768 0.093 Uiso 1 1 calc R U . . .
C32 C 0.32142(18) -0.05595(17) 0.26085(14) 0.0504(4) Uani 1 1 d . . . . .
C33 C 0.27099(16) 0.31323(15) 0.22797(12) 0.0405(4) Uani 1 1 d . . . . .
C34 C 0.18774(18) -0.00936(17) 0.38761(14) 0.0515(4) Uani 1 1 d . . . . .
H34 H 0.143798 0.007235 0.429856 0.062 Uiso 1 1 calc R U . . .
C35 C 0.4813(2) 0.3430(2) 0.00575(17) 0.0708(6) Uani 1 1 d . . . . .
H35 H 0.560173 0.347467 0.017494 0.085 Uiso 1 1 calc R U . . .
C36 C 0.0560(3) 0.2871(4) -0.1360(2) 0.1208(14) Uani 1 1 d . . . . .
H36A H 0.095071 0.339298 -0.176836 0.181 Uiso 1 1 calc R U . . .
H36B H -0.021994 0.287245 -0.133955 0.181 Uiso 1 1 calc R U . . .
H36C H 0.045283 0.211418 -0.161248 0.181 Uiso 1 1 calc R U . . .
C37 C 0.4163(3) 0.3208(2) -0.08675(17) 0.0749(7) Uani 1 1 d . . . . .
H37 H 0.451532 0.310168 -0.138115 0.090 Uiso 1 1 calc R U . . .
C38 C 0.4588(2) 0.2467(2) 0.52422(15) 0.0646(6) Uani 1 1 d . . . . .
H38A H 0.380996 0.215299 0.542014 0.097 Uiso 1 1 calc R U . . .
H38B H 0.519294 0.297541 0.578769 0.097 Uiso 1 1 calc R U . . .
H38C H 0.480576 0.185764 0.504066 0.097 Uiso 1 1 calc R U . . .
C39 C 0.54325(18) 0.40893(17) 0.43141(13) 0.0489(4) Uani 1 1 d . . . . .
C40 C 0.4007(2) -0.0772(2) 0.19414(17) 0.0622(5) Uani 1 1 d . . . . .
C41 C -0.0273(2) 0.0766(3) 0.2374(2) 0.0887(9) Uani 1 1 d . . . . .
H41 H -0.006186 0.078790 0.303563 0.106 Uiso 1 1 calc R U . . .
C42 C 0.0809(3) -0.1499(3) 0.5187(2) 0.0944(9) Uani 1 1 d . . . . .
H42A H 0.136896 -0.078113 0.557913 0.142 Uiso 1 1 calc R U . . .
H42B H 0.047369 -0.204388 0.559655 0.142 Uiso 1 1 calc R U . . .
H42C H 0.016381 -0.139529 0.478679 0.142 Uiso 1 1 calc R U . . .
C43 C 0.3236(3) -0.1780(2) 0.1121(2) 0.0862(8) Uani 1 1 d . . . . .
H43A H 0.286511 -0.246044 0.138971 0.129 Uiso 1 1 calc DR U . . .
H43B H 0.374689 -0.189142 0.071155 0.129 Uiso 1 1 calc R U . . .
H43C H 0.261215 -0.162001 0.074934 0.129 Uiso 1 1 calc R U . . .
C44 C 0.69037(19) 0.60399(19) 0.37744(16) 0.0603(5) Uani 1 1 d . . . . .
C45 C -0.2742(2) 0.3487(3) 0.2274(3) 0.1052(11) Uani 1 1 d . . . . .
H45A H -0.297382 0.409839 0.215038 0.158 Uiso 1 1 calc R U . . .
H45B H -0.276808 0.337101 0.292914 0.158 Uiso 1 1 calc R U . . .
H45C H -0.329633 0.279756 0.184054 0.158 Uiso 1 1 calc R U . . .
C46 C 0.4585(3) 0.0265(3) 0.1452(2) 0.0980(10) Uani 1 1 d . . . . .
H46A H 0.395450 0.041844 0.108163 0.147 Uiso 1 1 calc R U . . .
H46B H 0.506131 0.010647 0.103136 0.147 Uiso 1 1 calc R U . . .
H46C H 0.509975 0.092056 0.193592 0.147 Uiso 1 1 calc R U . . .
C47 C 0.1474(2) -0.1936(2) 0.45558(18) 0.0669(6) Uani 1 1 d . . . . .
C52 C 0.2526(3) -0.2053(3) 0.5224(3) 0.1120(12) Uani 1 1 d . . . . .
H52A H 0.285970 -0.247039 0.485591 0.168 Uiso 1 1 calc R U . . .
H52B H 0.222484 -0.245476 0.573004 0.168 Uiso 1 1 calc R U . . .
H52C H 0.315018 -0.130531 0.550237 0.168 Uiso 1 1 calc R U . . .
C53 C 0.5052(3) -0.0988(3) 0.2524(2) 0.0938(9) Uani 1 1 d . . . . .
H53A H 0.547089 -0.039259 0.307667 0.141 Uiso 1 1 calc R U . . .
H53B H 0.561255 -0.099162 0.212258 0.141 Uiso 1 1 calc R U . . .
H53C H 0.472098 -0.171424 0.273587 0.141 Uiso 1 1 calc DR U . . .
O56 O 0.25250(15) 0.54064(13) 0.08445(11) 0.0663(4) Uani 1 1 d . . . . .
C60 C 0.0555(3) -0.3111(2) 0.4009(3) 0.0954(9) Uani 1 1 d . . . . .
H60A H -0.010278 -0.303294 0.360080 0.143 Uiso 1 1 calc R U . . .
H60B H 0.024037 -0.360090 0.446245 0.143 Uiso 1 1 calc R U . . .
H60C H 0.094875 -0.343947 0.361937 0.143 Uiso 1 1 calc R U . . .
C50 C -0.1784(3) 0.0008(3) 0.0918(3) 0.1072(11) Uani 1 1 d . . . . .
H50 H -0.258111 -0.045339 0.059357 0.129 Uiso 1 1 calc R U . . .
C1AA C -0.0948(3) 0.0631(3) 0.0431(3) 0.1079(12) Uani 1 1 d . . . . .
H1AA H -0.117182 0.058510 -0.023310 0.129 Uiso 1 1 calc R U . . .
C0AA C -0.1444(3) 0.0067(3) 0.1877(3) 0.1163(13) Uani 1 1 d . . . . .
H0AA H -0.200892 -0.037191 0.221159 0.140 Uiso 1 1 calc R U . . .
H12 H 0.2955(12) -0.246(3) 0.2794(8) 0.095(12) Uiso 1 1 d 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
N1 S1 C11 103.94(8) . . ?
O3 S1 N1 109.71(8) . . ?
O3 S1 C11 107.08(9) . . ?
O56 S1 N1 107.00(8) . . ?
O56 S1 O3 118.31(10) . . ?
O56 S1 C11 109.89(9) . . ?
C17 N1 S1 118.83(12) . . ?
C33 N1 S1 115.68(11) . . ?
C33 N1 C17 119.48(14) . . ?
C8 O2 C36 118.3(2) . . ?
C21 C5 C28 119.77(16) . . ?
C34 C5 C21 118.96(17) . . ?
C34 C5 C28 121.03(16) . . ?
C29 C6 C16 136.13(17) . . ?
C29 C6 C39 118.52(17) . . ?
C39 C6 C16 105.33(17) . . ?
O2 C8 C13 124.0(2) . . ?
O2 C8 C17 117.05(17) . . ?
C13 C8 C17 118.9(2) . . ?
C22 N9 C38 126.75(18) . . ?
C22 N9 C39 106.79(15) . . ?
C39 N9 C38 126.45(17) . . ?
C17 C10 H10 119.4 . . ?
C17 C10 C35 121.1(2) . . ?
C35 C10 H10 119.4 . . ?
C26 C11 S1 120.06(15) . . ?
C26 C11 C31 120.26(19) . . ?
C31 C11 S1 119.67(16) . . ?
C19 O12 H12 106(3) . . ?
C8 C13 H13 119.8 . . ?
C37 C13 C8 120.3(2) . . ?
C37 C13 H13 119.8 . . ?
C27 C14 C18 123.4(2) . . ?
C27 C14 C41 116.7(2) . . ?
C41 C14 C18 119.8(2) . . ?
C20 C15 H15 120.2 . . ?
C20 C15 C44 119.7(2) . . ?
C44 C15 H15 120.2 . . ?
C6 C16 C33 146.62(17) . . ?
C22 C16 C6 106.86(16) . . ?
C22 C16 C33 106.52(16) . . ?
C8 C17 N1 120.45(17) . . ?
C10 C17 N1 120.16(16) . . ?
C10 C17 C8 119.39(17) . . ?
C14 C18 C28 119.77(16) . . ?
C33 C18 C14 130.93(17) . . ?
C33 C18 C28 109.27(16) . . ?
O12 C19 C23 115.04(19) . . ?
O12 C19 C32 122.33(19) . . ?
C23 C19 C32 122.61(17) . . ?
C15 C20 H20 120.9 . . ?
C15 C20 C39 118.2(2) . . ?
C39 C20 H20 120.9 . . ?
C5 C21 H21 119.0 . . ?
C5 C21 C32 122.00(17) . . ?
C32 C21 H21 119.0 . . ?
N9 C22 C28 134.75(17) . . ?
C16 C22 N9 112.06(17) . . ?
C16 C22 C28 113.16(16) . . ?
C19 C23 C47 122.40(18) . . ?
C34 C23 C19 117.08(18) . . ?
C34 C23 C47 120.45(18) . . ?
C30 C24 H24 119.2 . . ?
C31 C24 H24 119.2 . . ?
C31 C24 C30 121.6(2) . . ?
C26 C25 H25 119.1 . . ?
C30 C25 H25 119.1 . . ?
C30 C25 C26 121.8(2) . . ?
C11 C26 C25 119.32(19) . . ?
C11 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C14 C27 H27 119.4 . . ?
C14 C27 C1AA 121.1(3) . . ?
C1AA C27 H27 119.4 . . ?
C5 C28 C18 114.99(15) . . ?
C5 C28 H28 109.6 . . ?
C18 C28 H28 109.6 . . ?
C22 C28 C5 112.04(15) . . ?
C22 C28 C18 100.81(15) . . ?
C22 C28 H28 109.6 . . ?
C6 C29 H29 121.3 . . ?
C44 C29 C6 117.47(19) . . ?
C44 C29 H29 121.3 . . ?
C24 C30 C45 121.5(2) . . ?
C25 C30 C24 117.6(2) . . ?
C25 C30 C45 120.9(2) . . ?
C11 C31 C24 119.4(2) . . ?
C11 C31 H31 120.3 . . ?
C24 C31 H31 120.3 . . ?
C19 C32 C40 122.51(18) . . ?
C21 C32 C19 116.92(17) . . ?
C21 C32 C40 120.54(18) . . ?
N1 C33 C16 124.82(16) . . ?
C18 C33 N1 124.94(16) . . ?
C18 C33 C16 110.23(16) . . ?
C5 C34 C23 122.40(18) . . ?
C5 C34 H34 118.8 . . ?
C23 C34 H34 118.8 . . ?
C10 C35 H35 120.4 . . ?
C37 C35 C10 119.2(2) . . ?
C37 C35 H35 120.4 . . ?
O2 C36 H36A 109.5 . . ?
O2 C36 H36B 109.5 . . ?
O2 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C13 C37 H37 119.5 . . ?
C35 C37 C13 121.1(2) . . ?
C35 C37 H37 119.5 . . ?
N9 C38 H38A 109.5 . . ?
N9 C38 H38B 109.5 . . ?
N9 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N9 C39 C6 108.96(16) . . ?
N9 C39 C20 128.92(18) . . ?
C20 C39 C6 122.1(2) . . ?
C32 C40 C53 110.6(2) . . ?
C43 C40 C32 110.9(2) . . ?
C43 C40 C53 110.4(2) . . ?
C46 C40 C32 111.09(18) . . ?
C46 C40 C43 106.0(2) . . ?
C46 C40 C53 107.6(2) . . ?
C14 C41 H41 119.5 . . ?
C0AA C41 C14 121.1(3) . . ?
C0AA C41 H41 119.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C47 C42 H42A 109.5 . . ?
C47 C42 H42B 109.5 . . ?
C47 C42 H42C 109.5 . . ?
C40 C43 H43A 109.5 . . ?
C40 C43 H43B 109.5 . . ?
C40 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
F4 C44 C15 117.88(19) . . ?
F4 C44 C29 118.1(2) . . ?
C29 C44 C15 124.0(2) . . ?
C30 C45 H45A 109.5 . . ?
C30 C45 H45B 109.5 . . ?
C30 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C40 C46 H46A 109.5 . . ?
C40 C46 H46B 109.5 . . ?
C40 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C23 C47 C52 109.1(2) . . ?
C42 C47 C23 112.17(19) . . ?
C42 C47 C52 107.8(3) . . ?
C42 C47 C60 106.5(2) . . ?
C60 C47 C23 111.2(2) . . ?
C60 C47 C52 110.0(3) . . ?
C47 C52 H52A 109.5 . . ?
C47 C52 H52B 109.5 . . ?
C47 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C40 C53 H53A 109.5 . . ?
C40 C53 H53B 109.5 . . ?
C40 C53 H53C 109.5 . . ?
H53A C53 H53B 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C47 C60 H60A 109.5 . . ?
C47 C60 H60B 109.5 . . ?
C47 C60 H60C 109.5 . . ?
H60A C60 H60B 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C1AA C50 H50 120.5 . . ?
C0AA C50 H50 120.5 . . ?
C0AA C50 C1AA 119.1(3) . . ?
C27 C1AA H1AA 119.6 . . ?
C50 C1AA C27 120.8(3) . . ?
C50 C1AA H1AA 119.6 . . ?
C41 C0AA H0AA 119.4 . . ?
C50 C0AA C41 121.2(3) . . ?
C50 C0AA H0AA 119.4 . . ?
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 N1 1.6571(15) . ?
S1 O3 1.4324(15) . ?
S1 C11 1.7563(19) . ?
S1 O56 1.4287(15) . ?
N1 C17 1.445(2) . ?
N1 C33 1.437(2) . ?
O2 C8 1.362(3) . ?
O2 C36 1.418(3) . ?
F4 C44 1.366(3) . ?
C5 C21 1.385(3) . ?
C5 C28 1.515(2) . ?
C5 C34 1.381(3) . ?
C6 C16 1.431(3) . ?
C6 C29 1.396(3) . ?
C6 C39 1.430(3) . ?
C8 C13 1.391(3) . ?
C8 C17 1.398(3) . ?
N9 C22 1.363(2) . ?
N9 C38 1.451(3) . ?
N9 C39 1.384(3) . ?
C10 H10 0.9300 . ?
C10 C17 1.379(3) . ?
C10 C35 1.383(3) . ?
C11 C26 1.369(3) . ?
C11 C31 1.372(3) . ?
O12 C19 1.375(2) . ?
O12 H12 0.688(15) . ?
C13 H13 0.9300 . ?
C13 C37 1.373(4) . ?
C14 C18 1.470(3) . ?
C14 C27 1.382(3) . ?
C14 C41 1.387(3) . ?
C15 H15 0.9300 . ?
C15 C20 1.370(3) . ?
C15 C44 1.388(3) . ?
C16 C22 1.361(3) . ?
C16 C33 1.473(2) . ?
C18 C28 1.538(3) . ?
C18 C33 1.360(3) . ?
C19 C23 1.398(3) . ?
C19 C32 1.410(3) . ?
C20 H20 0.9300 . ?
C20 C39 1.388(3) . ?
C21 H21 0.9300 . ?
C21 C32 1.393(3) . ?
C22 C28 1.487(3) . ?
C23 C34 1.389(3) . ?
C23 C47 1.540(3) . ?
C24 H24 0.9300 . ?
C24 C30 1.378(4) . ?
C24 C31 1.377(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.380(3) . ?
C25 C30 1.373(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C27 C1AA 1.387(4) . ?
C28 H28 0.9800 . ?
C29 H29 0.9300 . ?
C29 C44 1.372(3) . ?
C30 C45 1.513(3) . ?
C31 H31 0.9300 . ?
C32 C40 1.538(3) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C35 C37 1.365(4) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C40 C43 1.533(3) . ?
C40 C46 1.532(3) . ?
C40 C53 1.546(4) . ?
C41 H41 0.9300 . ?
C41 C0AA 1.380(4) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C42 C47 1.512(4) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C47 C52 1.541(4) . ?
C47 C60 1.526(4) . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C53 H53A 0.9600 . ?
C53 H53B 0.9600 . ?
C53 H53C 0.9600 . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 0.9600 . ?
C50 H50 0.9300 . ?
C50 C1AA 1.357(5) . ?
C50 C0AA 1.348(5) . ?
C1AA H1AA 0.9300 . ?
C0AA H0AA 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
S1 N1 C17 C8 -73.8(2) . . . . ?
S1 N1 C17 C10 107.24(19) . . . . ?
S1 N1 C33 C16 -71.88(19) . . . . ?
S1 N1 C33 C18 107.03(17) . . . . ?
S1 C11 C26 C25 177.12(19) . . . . ?
S1 C11 C31 C24 -176.6(2) . . . . ?
N1 S1 C11 C26 91.09(18) . . . . ?
N1 S1 C11 C31 -90.5(2) . . . . ?
O2 C8 C13 C37 -179.2(2) . . . . ?
O2 C8 C17 N1 0.1(3) . . . . ?
O2 C8 C17 C10 179.15(19) . . . . ?
O3 S1 N1 C17 -113.00(14) . . . . ?
O3 S1 N1 C33 39.60(15) . . . . ?
O3 S1 C11 C26 -25.00(19) . . . . ?
O3 S1 C11 C31 153.37(19) . . . . ?
C5 C21 C32 C19 1.1(3) . . . . ?
C5 C21 C32 C40 -177.02(19) . . . . ?
C6 C16 C22 N9 -1.0(2) . . . . ?
C6 C16 C22 C28 -179.27(14) . . . . ?
C6 C16 C33 N1 -1.6(4) . . . . ?
C6 C16 C33 C18 179.4(2) . . . . ?
C6 C29 C44 F4 -178.06(18) . . . . ?
C6 C29 C44 C15 0.0(3) . . . . ?
C8 C13 C37 C35 -0.4(4) . . . . ?
N9 C22 C28 C5 -55.5(3) . . . . ?
N9 C22 C28 C18 -178.30(19) . . . . ?
C10 C35 C37 C13 -0.1(4) . . . . ?
C11 S1 N1 C17 132.77(14) . . . . ?
C11 S1 N1 C33 -74.62(14) . . . . ?
O12 C19 C23 C34 -179.9(2) . . . . ?
O12 C19 C23 C47 3.0(3) . . . . ?
O12 C19 C32 C21 179.7(2) . . . . ?
O12 C19 C32 C40 -2.2(3) . . . . ?
C13 C8 C17 N1 -179.97(18) . . . . ?
C13 C8 C17 C10 -1.0(3) . . . . ?
C14 C18 C28 C5 61.7(2) . . . . ?
C14 C18 C28 C22 -177.57(15) . . . . ?
C14 C18 C33 N1 -1.7(3) . . . . ?
C14 C18 C33 C16 177.36(17) . . . . ?
C14 C27 C1AA C50 -0.9(6) . . . . ?
C14 C41 C0AA C50 0.3(6) . . . . ?
C15 C20 C39 C6 0.0(3) . . . . ?
C15 C20 C39 N9 -178.12(19) . . . . ?
C16 C6 C29 C44 178.5(2) . . . . ?
C16 C6 C39 N9 -0.61(19) . . . . ?
C16 C6 C39 C20 -179.09(17) . . . . ?
C16 C22 C28 C5 122.25(17) . . . . ?
C16 C22 C28 C18 -0.53(19) . . . . ?
C17 N1 C33 C16 80.5(2) . . . . ?
C17 N1 C33 C18 -100.6(2) . . . . ?
C17 C8 C13 C37 1.0(3) . . . . ?
C17 C10 C35 C37 0.1(4) . . . . ?
C18 C14 C27 C1AA 178.8(3) . . . . ?
C18 C14 C41 C0AA -178.6(3) . . . . ?
C19 C23 C34 C5 -0.5(3) . . . . ?
C19 C23 C47 C42 179.5(2) . . . . ?
C19 C23 C47 C52 60.1(3) . . . . ?
C19 C23 C47 C60 -61.3(3) . . . . ?
C19 C32 C40 C43 67.5(3) . . . . ?
C19 C32 C40 C46 -174.8(2) . . . . ?
C19 C32 C40 C53 -55.3(3) . . . . ?
C20 C15 C44 F4 177.7(2) . . . . ?
C20 C15 C44 C29 -0.4(4) . . . . ?
C21 C5 C28 C18 56.7(2) . . . . ?
C21 C5 C28 C22 -57.6(2) . . . . ?
C21 C5 C34 C23 -0.4(3) . . . . ?
C21 C32 C40 C43 -114.5(2) . . . . ?
C21 C32 C40 C46 3.2(3) . . . . ?
C21 C32 C40 C53 122.7(2) . . . . ?
C22 N9 C39 C6 0.0(2) . . . . ?
C22 N9 C39 C20 178.39(19) . . . . ?
C22 C16 C33 N1 179.39(15) . . . . ?
C22 C16 C33 C18 0.3(2) . . . . ?
C23 C19 C32 C21 -2.0(3) . . . . ?
C23 C19 C32 C40 176.0(2) . . . . ?
C26 C11 C31 C24 1.8(4) . . . . ?
C26 C25 C30 C24 1.0(4) . . . . ?
C26 C25 C30 C45 -177.9(3) . . . . ?
C27 C14 C18 C28 -152.7(2) . . . . ?
C27 C14 C18 C33 29.4(3) . . . . ?
C27 C14 C41 C0AA -2.3(5) . . . . ?
C28 C5 C21 C32 174.57(18) . . . . ?
C28 C5 C34 C23 -174.83(18) . . . . ?
C28 C18 C33 N1 -179.73(14) . . . . ?
C28 C18 C33 C16 -0.69(19) . . . . ?
C29 C6 C16 C22 -177.4(2) . . . . ?
C29 C6 C16 C33 3.6(4) . . . . ?
C29 C6 C39 N9 178.09(16) . . . . ?
C29 C6 C39 C20 -0.4(3) . . . . ?
C30 C24 C31 C11 -0.9(5) . . . . ?
C30 C25 C26 C11 -0.2(4) . . . . ?
C31 C11 C26 C25 -1.2(4) . . . . ?
C31 C24 C30 C25 -0.5(5) . . . . ?
C31 C24 C30 C45 178.4(3) . . . . ?
C32 C19 C23 C34 1.7(3) . . . . ?
C32 C19 C23 C47 -175.4(2) . . . . ?
C33 N1 C17 C8 134.70(19) . . . . ?
C33 N1 C17 C10 -44.3(2) . . . . ?
C33 C16 C22 N9 178.45(14) . . . . ?
C33 C16 C22 C28 0.2(2) . . . . ?
C33 C18 C28 C5 -119.97(17) . . . . ?
C33 C18 C28 C22 0.73(18) . . . . ?
C34 C5 C21 C32 0.1(3) . . . . ?
C34 C5 C28 C18 -128.9(2) . . . . ?
C34 C5 C28 C22 116.7(2) . . . . ?
C34 C23 C47 C42 2.5(3) . . . . ?
C34 C23 C47 C52 -116.9(3) . . . . ?
C34 C23 C47 C60 121.7(2) . . . . ?
C35 C10 C17 N1 179.5(2) . . . . ?
C35 C10 C17 C8 0.4(3) . . . . ?
C36 O2 C8 C13 5.9(4) . . . . ?
C36 O2 C8 C17 -174.2(3) . . . . ?
C38 N9 C22 C16 -178.26(18) . . . . ?
C38 N9 C22 C28 -0.5(3) . . . . ?
C38 N9 C39 C6 178.90(18) . . . . ?
C38 N9 C39 C20 -2.7(3) . . . . ?
C39 C6 C16 C22 0.94(19) . . . . ?
C39 C6 C16 C33 -178.1(2) . . . . ?
C39 C6 C29 C44 0.3(3) . . . . ?
C39 N9 C22 C16 0.6(2) . . . . ?
C39 N9 C22 C28 178.39(19) . . . . ?
C41 C14 C18 C28 23.4(3) . . . . ?
C41 C14 C18 C33 -154.5(2) . . . . ?
C41 C14 C27 C1AA 2.6(4) . . . . ?
C44 C15 C20 C39 0.3(3) . . . . ?
C47 C23 C34 C5 176.7(2) . . . . ?
O56 S1 N1 C17 16.52(16) . . . . ?
O56 S1 N1 C33 169.12(13) . . . . ?
O56 S1 C11 C26 -154.70(17) . . . . ?
O56 S1 C11 C31 23.7(2) . . . . ?
C1AA C50 C0AA C41 1.5(7) . . . . ?
C0AA C50 C1AA C27 -1.1(6) . . . . ?
