#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/16/2221631.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2221631
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Jebas, Samuel Robinson'
'Babu, M.'
'Kalluraya, B.'
_publ_section_title
;Ethyl
 4-(2,4-difluorophenyl)-6-methyl-1-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
;
_journal_coeditor_code           CV2538
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o981
_journal_page_last               o982
_journal_paper_doi               10.1107/S160053680901232X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H18 F2 N2 O2 S'
_chemical_formula_moiety         'C20 H18 F2 N2 O2 S'
_chemical_formula_sum            'C20 H18 F2 N2 O2 S'
_chemical_formula_weight         388.42
_chemical_name_systematic
'Ethyl 4-(2,4-difluorophenyl)-6-methyl-1-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.8070(10)
_cell_angle_beta                 93.7760(10)
_cell_angle_gamma                102.5060(10)
_cell_formula_units_Z            8
_cell_length_a                   11.3019(2)
_cell_length_b                   13.9550(2)
_cell_length_c                   24.3463(4)
_cell_measurement_reflns_used    9848
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.61
_cell_measurement_theta_min      2.12
_cell_volume                     3684.98(11)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            76910
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         0.85
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.9708
_exptl_absorpt_correction_T_min  0.8881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.331
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1034
_refine_ls_number_reflns         21361
_refine_ls_number_restraints     105
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max_lt       0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0548P)²+1.3360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1327
_reflns_number_gt                14585
_reflns_number_total             21361
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2538.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3684.98(10)
_cod_database_code               2221631
_cod_database_fobs_code          2221631
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1A 0.75838(4) 0.19688(3) 0.160405(18) 0.02552(10) Uani d . 1 . .
O O2A 0.88227(12) 0.68085(9) 0.25523(5) 0.0299(3) Uani d . 1 B .
F F2A 1.32384(11) 0.55763(8) 0.35317(5) 0.0408(3) Uani d . 1 A .
N N1A 0.82419(13) 0.37625(10) 0.12983(5) 0.0210(3) Uani d . 1 . .
N N2A 0.79954(14) 0.37477(10) 0.22300(6) 0.0228(3) Uani d . 1 . .
C C1A 0.73542(17) 0.28783(13) 0.03654(7) 0.0297(4) Uani d . 1 . .
H H1AA 0.6580 0.2880 0.0473 0.036 Uiso calc R 1 . .
C C2A 0.74994(19) 0.25026(15) -0.01824(8) 0.0372(5) Uani d . 1 . .
H H2AA 0.6820 0.2259 -0.0444 0.045 Uiso calc R 1 . .
C C3A 0.8645(2) 0.24892(14) -0.03401(7) 0.0355(5) Uani d . 1 . .
H H3AA 0.8738 0.2235 -0.0707 0.043 Uiso calc R 1 . .
C C4A 0.96586(19) 0.28542(15) 0.00479(7) 0.0333(4) Uani d . 1 . .
H H4AA 1.0432 0.2845 -0.0059 0.040 Uiso calc R 1 . .
C C5A 0.95199(16) 0.32340(13) 0.05967(7) 0.0256(4) Uani d . 1 . .
H H5AA 1.0197 0.3475 0.0859 0.031 Uiso calc R 1 . .
C C6A 0.83664(15) 0.32491(11) 0.07489(6) 0.0199(3) Uani d . 1 . .
C C7A 0.83666(15) 0.48118(11) 0.13756(7) 0.0205(3) Uani d . 1 . .
C C8A 0.84716(15) 0.53280(11) 0.18996(6) 0.0203(3) Uani d . 1 B .
C C9A 0.85118(16) 0.48197(12) 0.24026(6) 0.0217(3) Uani d . 1 . .
H H9AA 0.7990 0.5081 0.2665 0.026 Uiso calc R 1 . .
C C10A 0.79674(15) 0.32235(12) 0.17234(7) 0.0209(3) Uani d . 1 . .
C C11A 0.97837(16) 0.50213(11) 0.27052(6) 0.0224(3) Uani d . 1 A .
C C12A 1.07877(17) 0.48994(14) 0.24264(7) 0.0293(4) Uani d . 1 . .
H H12A 1.0670 0.4682 0.2042 0.035 Uiso calc PR 0.618(3) A 1
F F1A 1.0585(2) 0.4410(2) 0.19055(10) 0.0277(8) Uani d P 0.382(3) A 2
C C13A 1.19565(18) 0.50857(14) 0.26922(8) 0.0325(4) Uani d . 1 A .
H H13A 1.2614 0.5003 0.2494 0.039 Uiso calc R 1 . .
C C14A 1.21032(17) 0.53975(12) 0.32601(8) 0.0297(4) Uani d . 1 . .
C C15A 1.11583(19) 0.55307(13) 0.35638(7) 0.0312(4) Uani d . 1 A .
H H15A 1.1284 0.5741 0.3949 0.037 Uiso calc R 1 . .
C C16A 1.00078(18) 0.53433(12) 0.32796(7) 0.0275(4) Uani d . 1 . .
H H16C 0.9359 0.5436 0.3481 0.033 Uiso calc PR 0.382(3) A 2
F F3A 0.90942(17) 0.54105(14) 0.35765(7) 0.0382(6) Uani d P 0.618(3) A 1
C C17A 0.86280(16) 0.64179(12) 0.20659(7) 0.0245(3) Uani d . 1 . .
O O1A 0.86007(18) 0.69379(10) 0.16543(5) 0.0275(4) Uani d PDU 0.908(3) B 1
C C18A 0.8829(2) 0.80187(14) 0.18231(8) 0.0290(5) Uani d PDU 0.908(3) B 1
H H18A 0.9647 0.8281 0.2009 0.035 Uiso calc PR 0.908(3) B 1
H H18B 0.8252 0.8190 0.2077 0.035 Uiso calc PR 0.908(3) B 1
C C19A 0.8681(2) 0.84402(16) 0.12969(9) 0.0333(5) Uani d PDU 0.908(3) B 1
H H19A 0.8820 0.9152 0.1388 0.050 Uiso calc PR 0.908(3) B 1
H H19B 0.7870 0.8171 0.1117 0.050 Uiso calc PR 0.908(3) B 1
H H19C 0.9259 0.8266 0.1050 0.050 Uiso calc PR 0.908(3) B 1
O O1E 0.7873(18) 0.6727(9) 0.1611(6) 0.0275(4) Uani d PDU 0.092(3) B 2
C C18E 0.797(2) 0.7800(11) 0.1680(9) 0.030(4) Uani d PDU 0.092(3) B 2
H H18I 0.7242 0.7932 0.1502 0.036 Uiso calc PR 0.092(3) B 2
H H18J 0.8045 0.8081 0.2075 0.036 Uiso calc PR 0.092(3) B 2
C C19E 0.905(2) 0.8257(16) 0.1425(10) 0.0333(5) Uani d PDU 0.092(3) B 2
H H19M 0.9065 0.8948 0.1424 0.050 Uiso calc PR 0.092(3) B 2
H H19N 0.9015 0.7920 0.1047 0.050 Uiso calc PR 0.092(3) B 2
H H19O 0.9773 0.8202 0.1635 0.050 Uiso calc PR 0.092(3) B 2
C C20A 0.83525(18) 0.52424(13) 0.08446(7) 0.0277(4) Uani d . 1 . .
H H20A 0.8348 0.5936 0.0932 0.041 Uiso calc R 1 . .
H H20B 0.7636 0.4896 0.0601 0.041 Uiso calc R 1 . .
H H20C 0.9064 0.5170 0.0663 0.041 Uiso calc R 1 . .
S S1B 0.75338(4) 0.28831(3) 0.347157(17) 0.02507(10) Uani d . 1 . .
O O1B 0.65299(12) -0.20878(8) 0.34331(5) 0.0276(3) Uani d . 1 . .
O O2B 0.62896(12) -0.19589(9) 0.25299(5) 0.0313(3) Uani d . 1 . .
F F2B 0.21354(12) -0.05966(9) 0.14024(5) 0.0551(4) Uani d . 1 C .
N N1B 0.68304(13) 0.10938(10) 0.37749(5) 0.0201(3) Uani d . 1 . .
N N2B 0.72065(14) 0.11022(10) 0.28549(6) 0.0234(3) Uani d . 1 . .
C C1B 0.55091(15) 0.17504(12) 0.44143(7) 0.0231(3) Uani d . 1 . .
H H1BA 0.4869 0.1542 0.4131 0.028 Uiso calc R 1 . .
C C2B 0.53163(17) 0.21904(13) 0.49421(7) 0.0278(4) Uani d . 1 . .
H H2BA 0.4545 0.2279 0.5013 0.033 Uiso calc R 1 . .
C C3B 0.62774(19) 0.24983(13) 0.53636(7) 0.0308(4) Uani d . 1 . .
H H3BA 0.6150 0.2793 0.5717 0.037 Uiso calc R 1 . .
C C4B 0.74210(18) 0.23656(13) 0.52558(7) 0.0304(4) Uani d . 1 . .
H H4BA 0.8062 0.2569 0.5539 0.037 Uiso calc R 1 . .
C C5B 0.76198(16) 0.19320(12) 0.47299(7) 0.0252(4) Uani d . 1 . .
H H5BA 0.8392 0.1848 0.4658 0.030 Uiso calc R 1 . .
C C6B 0.66595(15) 0.16241(11) 0.43125(6) 0.0189(3) Uani d . 1 . .
C C7B 0.66750(14) 0.00404(11) 0.37000(7) 0.0200(3) Uani d . 1 . .
C C8B 0.66290(15) -0.04792(11) 0.31810(6) 0.0204(3) Uani d . 1 . .
C C9B 0.66849(16) 0.00325(12) 0.26761(7) 0.0224(3) Uani d . 1 . .
H H9BA 0.7238 -0.0236 0.2434 0.027 Uiso calc R 1 . .
C C10B 0.71625(15) 0.16289(12) 0.33534(7) 0.0205(3) Uani d . 1 . .
C C11B 0.54581(16) -0.01458(12) 0.23358(7) 0.0243(4) Uani d . 1 C .
C C12B 0.44191(18) -0.00158(14) 0.25786(8) 0.0331(4) Uani d . 1 . .
H H12B 0.4481 0.0186 0.2964 0.040 Uiso calc PR 0.618(3) C 1
F F1B 0.4577(2) 0.0489(2) 0.30888(10) 0.0306(8) Uani d P 0.382(3) C 2
C C13B 0.32909(19) -0.01707(15) 0.22775(9) 0.0391(5) Uani d . 1 C .
H H13B 0.2606 -0.0085 0.2453 0.047 Uiso calc R 1 . .
C C14B 0.3225(2) -0.04555(13) 0.17092(8) 0.0383(5) Uani d . 1 . .
C C15B 0.4209(2) -0.05954(14) 0.14403(8) 0.0410(5) Uani d . 1 C .
H H15B 0.4140 -0.0788 0.1054 0.049 Uiso calc R 1 . .
C C16B 0.53175(19) -0.04414(13) 0.17595(7) 0.0321(4) Uani d . 1 . .
H H16D 0.5994 -0.0540 0.1580 0.039 Uiso calc PR 0.382(3) C 2
F F3B 0.62696(19) -0.05051(14) 0.14996(7) 0.0416(6) Uani d P 0.618(3) C 1
C C17B 0.64673(15) -0.15711(12) 0.30179(7) 0.0229(3) Uani d . 1 . .
C C18B 0.63071(18) -0.31692(12) 0.32629(7) 0.0300(4) Uani d . 1 . .
H H18C 0.6890 -0.3335 0.3010 0.036 Uiso calc R 1 . .
H H18D 0.5493 -0.3431 0.3073 0.036 Uiso calc R 1 . .
C C19B 0.64424(19) -0.36055(14) 0.37831(8) 0.0358(4) Uani d . 1 . .
H H19D 0.6324 -0.4315 0.3685 0.054 Uiso calc R 1 . .
H H19E 0.5846 -0.3453 0.4025 0.054 Uiso calc R 1 . .
H H19F 0.7244 -0.3328 0.3972 0.054 Uiso calc R 1 . .
C C20B 0.65746(17) -0.03903(12) 0.42309(7) 0.0254(4) Uani d . 1 . .
H H20D 0.6340 -0.1104 0.4140 0.038 Uiso calc R 1 . .
H H20E 0.5972 -0.0148 0.4437 0.038 Uiso calc R 1 . .
H H20F 0.7348 -0.0193 0.4454 0.038 Uiso calc R 1 . .
S S1C 0.92583(4) 0.83676(3) 0.468491(17) 0.02691(10) Uani d . 1 . .
O O1C 0.92847(12) 0.84445(10) 0.74524(5) 0.0323(3) Uani d . 1 . .
O O2C 1.04966(12) 0.99326(9) 0.74164(5) 0.0315(3) Uani d . 1 . .
F F1C 0.74070(9) 0.91926(7) 0.58298(4) 0.0306(2) Uani d . 1 . .
F F2C 0.65175(11) 1.21670(9) 0.66815(5) 0.0391(3) Uani d . 1 . .
N N1C 0.91419(13) 0.77793(10) 0.56803(6) 0.0214(3) Uani d . 1 . .
N N2C 0.99707(13) 0.94456(10) 0.56861(6) 0.0211(3) Uani d . 1 . .
C C1C 0.9145(2) 0.62030(13) 0.50690(8) 0.0337(4) Uani d . 1 . .
H H1CA 0.9970 0.6430 0.5038 0.040 Uiso calc R 1 . .
C C2C 0.8524(3) 0.52555(15) 0.48020(9) 0.0495(6) Uani d . 1 . .
H H2CA 0.8934 0.4857 0.4581 0.059 Uiso calc R 1 . .
C C3C 0.7326(3) 0.49036(17) 0.48598(11) 0.0642(8) Uani d . 1 . .
H H3CA 0.6924 0.4266 0.4684 0.077 Uiso calc R 1 . .
C C4C 0.6715(3) 0.5496(2) 0.51788(13) 0.0709(9) Uani d . 1 . .
H H4CA 0.5900 0.5252 0.5224 0.085 Uiso calc R 1 . .
C C5C 0.73056(19) 0.64611(17) 0.54357(10) 0.0471(6) Uani d . 1 . .
H H5CA 0.6883 0.6869 0.5641 0.057 Uiso calc R 1 . .
C C6C 0.85196(16) 0.68006(12) 0.53807(7) 0.0257(4) Uani d . 1 . .
C C7C 0.93441(15) 0.79305(12) 0.62721(7) 0.0212(3) Uani d . 1 . .
C C8C 0.96774(15) 0.88628(12) 0.65661(7) 0.0214(3) Uani d . 1 . .
C C9C 0.99104(15) 0.97668(12) 0.62817(6) 0.0199(3) Uani d . 1 . .
H H9CA 1.0715 1.0177 0.6437 0.024 Uiso calc R 1 . .
C C10C 0.94492(15) 0.85531(12) 0.53858(7) 0.0207(3) Uani d . 1 . .
C C11C 0.89957(15) 1.04126(12) 0.63833(6) 0.0202(3) Uani d . 1 . .
C C12C 0.77895(15) 1.01087(12) 0.61542(7) 0.0226(3) Uani d . 1 . .
C C13C 0.69455(16) 1.06869(13) 0.62349(7) 0.0271(4) Uani d . 1 . .
H H13C 0.6150 1.0472 0.6065 0.033 Uiso calc R 1 . .
C C14C 0.73425(17) 1.16003(13) 0.65805(7) 0.0276(4) Uani d . 1 . .
C C15C 0.85183(17) 1.19531(13) 0.68213(7) 0.0274(4) Uani d . 1 . .
H H15C 0.8759 1.2575 0.7049 0.033 Uiso calc R 1 . .
C C17C 0.98855(16) 0.91343(13) 0.71814(7) 0.0244(3) Uani d . 1 . .
C C18C 0.9448(2) 0.86862(15) 0.80605(7) 0.0372(5) Uani d . 1 . .
H H18E 0.9032 0.9204 0.8191 0.045 Uiso calc R 1 . .
H H18F 1.0306 0.8917 0.8194 0.045 Uiso calc R 1 . .
C C19C 0.8910(2) 0.77396(18) 0.82669(9) 0.0488(6) Uani d . 1 . .
H H19G 0.8957 0.7868 0.8667 0.073 Uiso calc R 1 . .
H H19H 0.9358 0.7246 0.8150 0.073 Uiso calc R 1 . .
H H19I 0.8074 0.7501 0.8115 0.073 Uiso calc R 1 . .
C C20C 0.92231(17) 0.69861(12) 0.65126(7) 0.0276(4) Uani d . 1 . .
H H20G 0.9666 0.7132 0.6877 0.041 Uiso calc R 1 . .
H H20H 0.9547 0.6515 0.6273 0.041 Uiso calc R 1 . .
H H20I 0.8379 0.6710 0.6541 0.041 Uiso calc R 1 . .
S S1D 0.56431(4) 0.66307(3) 1.034717(17) 0.02846(10) Uani d . 1 . .
O O1D 0.56232(13) 0.66675(10) 0.75837(5) 0.0343(3) Uani d . 1 . .
O O2D 0.43475(12) 0.52084(10) 0.76128(5) 0.0335(3) Uani d . 1 . .
F F2D 0.83022(11) 0.28243(9) 0.83084(5) 0.0396(3) Uani d . 1 . .
F F1D 0.75066(9) 0.58129(8) 0.91963(4) 0.0316(2) Uani d . 1 . .
N N1D 0.58169(13) 0.72586(10) 0.93662(5) 0.0212(3) Uani d . 1 . .
N N2D 0.49398(13) 0.55931(10) 0.93340(6) 0.0215(3) Uani d . 1 . .
C C1D 0.59595(18) 0.88982(13) 0.99457(7) 0.0305(4) Uani d . 1 . .
H H1DA 0.5114 0.8781 0.9920 0.037 Uiso calc R 1 . .
C C2D 0.6675(2) 0.97884(14) 1.02477(8) 0.0374(5) Uani d . 1 . .
H H2DA 0.6305 1.0269 1.0423 0.045 Uiso calc R 1 . .
C C3D 0.7924(2) 0.99603(15) 1.02882(9) 0.0437(5) Uani d . 1 . .
H H3DA 0.8396 1.0562 1.0482 0.052 Uiso calc R 1 . .
C C4D 0.8475(2) 0.92390(16) 1.00414(9) 0.0436(5) Uani d . 1 . .
H H4DA 0.9319 0.9344 1.0081 0.052 Uiso calc R 1 . .
C C5D 0.77699(17) 0.83532(14) 0.97322(8) 0.0327(4) Uani d . 1 . .
H H5DA 0.8141 0.7872 0.9558 0.039 Uiso calc R 1 . .
C C6D 0.65208(15) 0.81957(12) 0.96858(7) 0.0223(3) Uani d . 1 . .
C C7D 0.56196(15) 0.71469(12) 0.87761(7) 0.0215(3) Uani d . 1 . .
C C8D 0.52512(15) 0.62249(12) 0.84687(7) 0.0219(3) Uani d . 1 . .
C C9D 0.50040(15) 0.53038(11) 0.87357(6) 0.0204(3) Uani d . 1 . .
H H9DA 0.4196 0.4907 0.8575 0.024 Uiso calc R 1 . .
C C10D 0.54763(15) 0.64690(12) 0.96469(7) 0.0211(3) Uani d . 1 . .
C C11D 0.59026(15) 0.46450(11) 0.86199(6) 0.0203(3) Uani d . 1 . .
C C12D 0.71052(15) 0.49119(12) 0.88551(7) 0.0235(3) Uani d . 1 . .
C C13D 0.79177(17) 0.43117(13) 0.87703(7) 0.0282(4) Uani d . 1 . .
H H13D 0.8709 0.4502 0.8946 0.034 Uiso calc R 1 . .
C C14D 0.75037(17) 0.34137(13) 0.84127(7) 0.0287(4) Uani d . 1 . .
C C15D 0.63312(17) 0.30988(13) 0.81591(7) 0.0274(4) Uani d . 1 . .
H H15D 0.6078 0.2489 0.7921 0.033 Uiso calc R 1 . .
C C16C 0.93428(16) 1.13519(12) 0.67144(7) 0.0232(3) Uani d . 1 . .
H H16A 1.0148 1.1586 0.6869 0.028 Uiso calc R 1 . .
C C17D 0.50025(16) 0.59825(13) 0.78517(7) 0.0257(4) Uani d . 1 . .
C C18D 0.5410(2) 0.64679(16) 0.69772(7) 0.0406(5) Uani d . 1 . .
H H18G 0.4544 0.6272 0.6857 0.049 Uiso calc R 1 . .
H H18H 0.5787 0.5938 0.6824 0.049 Uiso calc R 1 . .
C C19D 0.5972(3) 0.7420(2) 0.67881(9) 0.0572(7) Uani d . 1 . .
H H19J 0.5875 0.7325 0.6387 0.086 Uiso calc R 1 . .
H H19K 0.6824 0.7613 0.6919 0.086 Uiso calc R 1 . .
H H19L 0.5578 0.7933 0.6937 0.086 Uiso calc R 1 . .
C C20D 0.57818(18) 0.81196(12) 0.85654(7) 0.0281(4) Uani d . 1 . .
H H20J 0.5495 0.7996 0.8175 0.042 Uiso calc R 1 . .
H H20K 0.6629 0.8451 0.8617 0.042 Uiso calc R 1 . .
H H20L 0.5325 0.8533 0.8770 0.042 Uiso calc R 1 . .
C C16D 0.55333(16) 0.37216(12) 0.82703(7) 0.0235(3) Uani d . 1 . .
H H16B 0.4733 0.3516 0.8107 0.028 Uiso calc R 1 . .
H H1NA 0.777(2) 0.3407(16) 0.2484(9) 0.042(6) Uiso d . 1 . .
H H1NB 0.7418(18) 0.1428(15) 0.2587(8) 0.031(5) Uiso d . 1 . .
H H1NC 1.0197(19) 0.9954(16) 0.5500(8) 0.037(6) Uiso d . 1 . .
H H1ND 0.4711(18) 0.5074(15) 0.9495(8) 0.031(5) Uiso d . 1 . .
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 0.0000 0.0000 '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 0.0060 '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'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10A N1A C7A . . 122.11(13) ?
C10A N1A C6A . . 119.68(13) ?
C7A N1A C6A . . 118.18(12) ?
C10A N2A C9A . . 126.17(14) ?
C10A N2A H1NA . . 115.5(15) ?
C9A N2A H1NA . . 117.8(15) ?
C6A C1A C2A . . 119.57(18) ?
C6A C1A H1AA . . 120.2 ?
C2A C1A H1AA . . 120.2 ?
C3A C2A C1A . . 120.26(17) ?
C3A C2A H2AA . . 119.9 ?
C1A C2A H2AA . . 119.9 ?
C2A C3A C4A . . 119.99(17) ?
C2A C3A H3AA . . 120.0 ?
C4A C3A H3AA . . 120.0 ?
C3A C4A C5A . . 120.04(18) ?
C3A C4A H4AA . . 120.0 ?
C5A C4A H4AA . . 120.0 ?
C6A C5A C4A . . 119.42(16) ?
C6A C5A H5AA . . 120.3 ?
C4A C5A H5AA . . 120.3 ?
C1A C6A C5A . . 120.71(15) ?
C1A C6A N1A . . 119.92(15) ?
C5A C6A N1A . . 119.00(14) ?
C8A C7A N1A . . 119.05(14) ?
C8A C7A C20A . . 125.95(14) ?
N1A C7A C20A . . 115.00(13) ?
C7A C8A C17A . . 127.13(14) ?
C7A C8A C9A . . 121.28(14) ?
C17A C8A C9A . . 111.50(13) ?
N2A C9A C8A . . 109.21(13) ?
N2A C9A C11A . . 111.38(13) ?
C8A C9A C11A . . 112.98(14) ?
N2A C9A H9AA . . 107.7 ?
C8A C9A H9AA . . 107.7 ?
C11A C9A H9AA . . 107.7 ?
N2A C10A N1A . . 116.49(14) ?
N2A C10A S1A . . 121.62(12) ?
N1A C10A S1A . . 121.87(12) ?
C12A C11A C16A . . 116.12(16) ?
C12A C11A C9A . . 122.20(14) ?
C16A C11A C9A . . 121.68(16) ?
F1A C12A C13A . . 117.73(19) ?
F1A C12A C11A . . 117.79(19) ?
C13A C12A C11A . . 123.27(16) ?
C13A C12A H12A . . 118.4 ?
C11A C12A H12A . . 118.4 ?
C14A C13A C12A . . 117.16(18) ?
C14A C13A H13A . . 121.4 ?
C12A C13A H13A . . 121.4 ?
F2A C14A C15A . . 118.70(16) ?
F2A C14A C13A . . 118.34(18) ?
C15A C14A C13A . . 122.95(17) ?
C14A C15A C16A . . 117.85(16) ?
C14A C15A H15A . . 121.1 ?
C16A C15A H15A . . 121.1 ?
F3A C16A C15A . . 117.58(17) ?
F3A C16A C11A . . 119.60(18) ?
C15A C16A C11A . . 122.65(18) ?
C15A C16A H16C . . 118.7 ?
C11A C16A H16C . . 118.7 ?
O2A C17A O1A . . 122.39(15) ?
O2A C17A C8A . . 121.07(15) ?
O1A C17A C8A . . 116.46(14) ?
O2A C17A O1E . . 126.1(5) ?
C8A C17A O1E . . 105.1(5) ?
C17A O1A C18A . . 115.92(14) ?
O1A C18A C19A . . 106.50(15) ?
O1A C18A H18A . . 110.4 ?
C19A C18A H18A . . 110.4 ?
O1A C18A H18B . . 110.4 ?
C19A C18A H18B . . 110.4 ?
H18A C18A H18B . . 108.6 ?
C18E O1E C17A . . 113.7(13) ?
C19E C18E O1E . . 108.7(14) ?
C19E C18E H18I . . 110.0 ?
O1E C18E H18I . . 110.0 ?
C19E C18E H18J . . 110.0 ?
O1E C18E H18J . . 110.0 ?
H18I C18E H18J . . 108.3 ?
C18E C19E H19M . . 109.5 ?
C18E C19E H19N . . 109.5 ?
H19M C19E H19N . . 109.5 ?
C18E C19E H19O . . 109.5 ?
H19M C19E H19O . . 109.5 ?
H19N C19E H19O . . 109.5 ?
C7A C20A H20A . . 109.5 ?
C7A C20A H20B . . 109.5 ?
H20A C20A H20B . . 109.5 ?
C7A C20A H20C . . 109.5 ?
H20A C20A H20C . . 109.5 ?
H20B C20A H20C . . 109.5 ?
C17B O1B C18B . . 115.51(13) ?
C10B N1B C7B . . 122.06(13) ?
C10B N1B C6B . . 118.97(13) ?
C7B N1B C6B . . 118.95(13) ?
C10B N2B C9B . . 126.02(14) ?
C10B N2B H1NB . . 117.6(13) ?
C9B N2B H1NB . . 115.0(13) ?
C6B C1B C2B . . 119.55(15) ?
C6B C1B H1BA . . 120.2 ?
C2B C1B H1BA . . 120.2 ?
C1B C2B C3B . . 119.92(17) ?
C1B C2B H2BA . . 120.0 ?
C3B C2B H2BA . . 120.0 ?
C4B C3B C2B . . 119.86(16) ?
C4B C3B H3BA . . 120.1 ?
C2B C3B H3BA . . 120.1 ?
C3B C4B C5B . . 120.47(16) ?
C3B C4B H4BA . . 119.8 ?
C5B C4B H4BA . . 119.8 ?
C6B C5B C4B . . 119.44(16) ?
C6B C5B H5BA . . 120.3 ?
C4B C5B H5BA . . 120.3 ?
C1B C6B C5B . . 120.76(15) ?
C1B C6B N1B . . 119.10(14) ?
C5B C6B N1B . . 119.97(15) ?
C8B C7B N1B . . 119.36(14) ?
C8B C7B C20B . . 125.95(14) ?
N1B C7B C20B . . 114.69(13) ?
C7B C8B C17B . . 127.42(15) ?
C7B C8B C9B . . 121.09(14) ?
C17B C8B C9B . . 111.44(13) ?
N2B C9B C8B . . 109.39(13) ?
N2B C9B C11B . . 110.81(13) ?
C8B C9B C11B . . 113.25(14) ?
N2B C9B H9BA . . 107.7 ?
C8B C9B H9BA . . 107.7 ?
C11B C9B H9BA . . 107.7 ?
N2B C10B N1B . . 116.59(14) ?
N2B C10B S1B . . 121.74(12) ?
N1B C10B S1B . . 121.64(12) ?
C12B C11B C16B . . 116.02(17) ?
C12B C11B C9B . . 122.21(15) ?
C16B C11B C9B . . 121.76(16) ?
F1B C12B C11B . . 116.75(19) ?
F1B C12B C13B . . 118.0(2) ?
C11B C12B C13B . . 123.32(18) ?
C11B C12B H12B . . 118.3 ?
C13B C12B H12B . . 118.3 ?
C14B C13B C12B . . 117.3(2) ?
C14B C13B H13B . . 121.3 ?
C12B C13B H13B . . 121.3 ?
F2B C14B C15B . . 118.68(18) ?
F2B C14B C13B . . 118.6(2) ?
C15B C14B C13B . . 122.72(18) ?
C14B C15B C16B . . 117.95(18) ?
C14B C15B H15B . . 121.0 ?
C16B C15B H15B . . 121.0 ?
F3B C16B C15B . . 117.85(18) ?
F3B C16B C11B . . 119.27(19) ?
C15B C16B C11B . . 122.7(2) ?
C15B C16B H16D . . 118.7 ?
C11B C16B H16D . . 118.7 ?
O2B C17B O1B . . 122.80(15) ?
O2B C17B C8B . . 120.63(15) ?
O1B C17B C8B . . 116.57(14) ?
O1B C18B C19B . . 107.26(14) ?
O1B C18B H18C . . 110.3 ?
C19B C18B H18C . . 110.3 ?
O1B C18B H18D . . 110.3 ?
C19B C18B H18D . . 110.3 ?
H18C C18B H18D . . 108.5 ?
C18B C19B H19D . . 109.5 ?
C18B C19B H19E . . 109.5 ?
H19D C19B H19E . . 109.5 ?
C18B C19B H19F . . 109.5 ?
H19D C19B H19F . . 109.5 ?
H19E C19B H19F . . 109.5 ?
C7B C20B H20D . . 109.5 ?
C7B C20B H20E . . 109.5 ?
H20D C20B H20E . . 109.5 ?
C7B C20B H20F . . 109.5 ?
H20D C20B H20F . . 109.5 ?
H20E C20B H20F . . 109.5 ?
C17C O1C C18C . . 116.06(15) ?
C10C N1C C7C . . 121.77(13) ?
C10C N1C C6C . . 119.11(13) ?
C7C N1C C6C . . 118.98(13) ?
C10C N2C C9C . . 126.50(14) ?
C10C N2C H1NC . . 117.6(13) ?
C9C N2C H1NC . . 113.5(13) ?
C6C C1C C2C . . 119.1(2) ?
C6C C1C H1CA . . 120.4 ?
C2C C1C H1CA . . 120.4 ?
C3C C2C C1C . . 120.9(2) ?
C3C C2C H2CA . . 119.5 ?
C1C C2C H2CA . . 119.5 ?
C2C C3C C4C . . 119.6(2) ?
C2C C3C H3CA . . 120.2 ?
C4C C3C H3CA . . 120.2 ?
C3C C4C C5C . . 120.6(3) ?
C3C C4C H4CA . . 119.7 ?
C5C C4C H4CA . . 119.7 ?
C6C C5C C4C . . 119.1(2) ?
C6C C5C H5CA . . 120.4 ?
C4C C5C H5CA . . 120.4 ?
C5C C6C C1C . . 120.58(18) ?
C5C C6C N1C . . 118.54(18) ?
C1C C6C N1C . . 120.80(16) ?
C8C C7C N1C . . 119.93(14) ?
C8C C7C C20C . . 125.62(15) ?
N1C C7C C20C . . 114.36(14) ?
C7C C8C C17C . . 125.96(14) ?
C7C C8C C9C . . 121.75(14) ?
C17C C8C C9C . . 112.28(14) ?
N2C C9C C8C . . 109.13(13) ?
N2C C9C C11C . . 111.92(12) ?
C8C C9C C11C . . 113.61(13) ?
N2C C9C H9CA . . 107.3 ?
C8C C9C H9CA . . 107.3 ?
C11C C9C H9CA . . 107.3 ?
N2C C10C N1C . . 116.46(14) ?
N2C C10C S1C . . 121.64(12) ?
N1C C10C S1C . . 121.79(12) ?
C12C C11C C16C . . 116.66(15) ?
C12C C11C C9C . . 122.63(14) ?
C16C C11C C9C . . 120.71(15) ?
F1C C12C C13C . . 117.59(15) ?
F1C C12C C11C . . 118.72(14) ?
C13C C12C C11C . . 123.68(16) ?
C14C C13C C12C . . 116.63(16) ?
C14C C13C H13C . . 121.7 ?
C12C C13C H13C . . 121.7 ?
F2C C14C C15C . . 119.22(16) ?
F2C C14C C13C . . 117.68(16) ?
C15C C14C C13C . . 123.10(16) ?
C14C C15C C16C . . 117.98(16) ?
C14C C15C H15C . . 121.0 ?
C16C C15C H15C . . 121.0 ?
O2C C17C O1C . . 123.25(16) ?
O2C C17C C8C . . 122.56(16) ?
O1C C17C C8C . . 114.09(15) ?
O1C C18C C19C . . 106.16(17) ?
O1C C18C H18E . . 110.5 ?
C19C C18C H18E . . 110.5 ?
O1C C18C H18F . . 110.5 ?
C19C C18C H18F . . 110.5 ?
H18E C18C H18F . . 108.7 ?
C18C C19C H19G . . 109.5 ?
C18C C19C H19H . . 109.5 ?
H19G C19C H19H . . 109.5 ?
C18C C19C H19I . . 109.5 ?
H19G C19C H19I . . 109.5 ?
H19H C19C H19I . . 109.5 ?
C7C C20C H20G . . 109.5 ?
C7C C20C H20H . . 109.5 ?
H20G C20C H20H . . 109.5 ?
C7C C20C H20I . . 109.5 ?
H20G C20C H20I . . 109.5 ?
H20H C20C H20I . . 109.5 ?
C17D O1D C18D . . 116.44(15) ?
C10D N1D C7D . . 122.12(13) ?
C10D N1D C6D . . 117.90(13) ?
C7D N1D C6D . . 119.59(13) ?
C10D N2D C9D . . 126.23(14) ?
C10D N2D H1ND . . 119.4(13) ?
C9D N2D H1ND . . 111.7(13) ?
C6D C1D C2D . . 119.13(19) ?
C6D C1D H1DA . . 120.4 ?
C2D C1D H1DA . . 120.4 ?
C3D C2D C1D . . 120.47(19) ?
C3D C2D H2DA . . 119.8 ?
C1D C2D H2DA . . 119.8 ?
C2D C3D C4D . . 119.87(19) ?
C2D C3D H3DA . . 120.1 ?
C4D C3D H3DA . . 120.1 ?
C3D C4D C5D . . 120.2(2) ?
C3D C4D H4DA . . 119.9 ?
C5D C4D H4DA . . 119.9 ?
C6D C5D C4D . . 119.50(19) ?
C6D C5D H5DA . . 120.3 ?
C4D C5D H5DA . . 120.3 ?
C5D C6D C1D . . 120.83(17) ?
C5D C6D N1D . . 117.91(15) ?
C1D C6D N1D . . 121.24(16) ?
C8D C7D N1D . . 119.46(14) ?
C8D C7D C20D . . 126.84(15) ?
N1D C7D C20D . . 113.58(14) ?
C7D C8D C17D . . 126.09(15) ?
C7D C8D C9D . . 121.85(14) ?
C17D C8D C9D . . 112.04(14) ?
N2D C9D C8D . . 109.30(13) ?
N2D C9D C11D . . 112.04(12) ?
C8D C9D C11D . . 113.85(13) ?
N2D C9D H9DA . . 107.1 ?
C8D C9D H9DA . . 107.1 ?
C11D C9D H9DA . . 107.1 ?
N2D C10D N1D . . 116.46(14) ?
N2D C10D S1D . . 122.06(12) ?
N1D C10D S1D . . 121.34(12) ?
C12D C11D C16D . . 116.66(15) ?
C12D C11D C9D . . 122.91(14) ?
C16D C11D C9D . . 120.42(14) ?
F1D C12D C13D . . 117.75(15) ?
F1D C12D C11D . . 118.55(14) ?
C13D C12D C11D . . 123.69(16) ?
C12D C13D C14D . . 116.90(17) ?
C12D C13D H13D . . 121.6 ?
C14D C13D H13D . . 121.6 ?
F2D C14D C15D . . 119.14(16) ?
F2D C14D C13D . . 117.89(17) ?
C15D C14D C13D . . 122.97(16) ?
C14D C15D C16D . . 117.94(16) ?
C14D C15D H15D . . 121.0 ?
C16D C15D H15D . . 121.0 ?
C11C C16C C15C . . 121.89(16) ?
C11C C16C H16A . . 119.1 ?
C15C C16C H16A . . 119.1 ?
O2D C17D O1D . . 123.09(16) ?
O2D C17D C8D . . 122.62(16) ?
O1D C17D C8D . . 114.16(15) ?
O1D C18D C19D . . 105.99(18) ?
O1D C18D H18G . . 110.5 ?
C19D C18D H18G . . 110.5 ?
O1D C18D H18H . . 110.5 ?
C19D C18D H18H . . 110.5 ?
H18G C18D H18H . . 108.7 ?
C18D C19D H19J . . 109.5 ?
C18D C19D H19K . . 109.5 ?
H19J C19D H19K . . 109.5 ?
C18D C19D H19L . . 109.5 ?
H19J C19D H19L . . 109.5 ?
H19K C19D H19L . . 109.5 ?
C7D C20D H20J . . 109.5 ?
C7D C20D H20K . . 109.5 ?
H20J C20D H20K . . 109.5 ?
C7D C20D H20L . . 109.5 ?
H20J C20D H20L . . 109.5 ?
H20K C20D H20L . . 109.5 ?
C15D C16D C11D . . 121.80(16) ?
C15D C16D H16B . . 119.1 ?
C11D C16D H16B . . 119.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1A C10A . 1.6844(16) ?
O2A C17A . 1.210(2) ?
F2A C14A . 1.358(2) ?
N1A C10A . 1.383(2) ?
N1A C7A . 1.4219(19) ?
N1A C6A . 1.4483(19) ?
N2A C10A . 1.329(2) ?
N2A C9A . 1.467(2) ?
N2A H1NA . 0.86(2) ?
C1A C6A . 1.380(2) ?
C1A C2A . 1.390(3) ?
C1A H1AA . 0.9300 ?
C2A C3A . 1.377(3) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.386(3) ?
C3A H3AA . 0.9300 ?
C4A C5A . 1.392(2) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.382(2) ?
C5A H5AA . 0.9300 ?
C7A C8A . 1.350(2) ?
C7A C20A . 1.507(2) ?
C8A C17A . 1.481(2) ?
C8A C9A . 1.509(2) ?
C9A C11A . 1.520(2) ?
C9A H9AA . 0.9800 ?
C11A C12A . 1.388(2) ?
C11A C16A . 1.390(2) ?
C12A F1A . 1.325(3) ?
C12A C13A . 1.385(3) ?
C12A H12A . 0.9300 ?
C13A C14A . 1.372(3) ?
C13A H13A . 0.9300 ?
C14A C15A . 1.367(3) ?
C15A C16A . 1.385(3) ?
C15A H15A . 0.9300 ?
C16A F3A . 1.310(2) ?
C16A H16C . 0.9300 ?
C17A O1A . 1.327(2) ?
C17A O1E . 1.523(15) ?
O1A C18A . 1.462(2) ?
C18A C19A . 1.503(3) ?
C18A H18A . 0.9700 ?
C18A H18B . 0.9700 ?
C19A H19A . 0.9600 ?
C19A H19B . 0.9600 ?
C19A H19C . 0.9600 ?
O1E C18E . 1.460(15) ?
C18E C19E . 1.474(17) ?
C18E H18I . 0.9700 ?
C18E H18J . 0.9700 ?
C19E H19M . 0.9600 ?
C19E H19N . 0.9600 ?
C19E H19O . 0.9600 ?
C20A H20A . 0.9600 ?
C20A H20B . 0.9600 ?
C20A H20C . 0.9600 ?
S1B C10B . 1.6834(16) ?
O1B C17B . 1.3350(19) ?
O1B C18B . 1.4639(19) ?
O2B C17B . 1.2123(19) ?
F2B C14B . 1.357(2) ?
N1B C10B . 1.384(2) ?
N1B C7B . 1.4237(19) ?
N1B C6B . 1.4481(19) ?
N2B C10B . 1.329(2) ?
N2B C9B . 1.467(2) ?
N2B H1NB . 0.87(2) ?
C1B C6B . 1.382(2) ?
C1B C2B . 1.389(2) ?
C1B H1BA . 0.9300 ?
C2B C3B . 1.391(3) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.381(3) ?
C3B H3BA . 0.9300 ?
C4B C5B . 1.384(2) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.384(2) ?
C5B H5BA . 0.9300 ?
C7B C8B . 1.349(2) ?
C7B C20B . 1.508(2) ?
C8B C17B . 1.482(2) ?
C8B C9B . 1.511(2) ?
C9B C11B . 1.519(2) ?
C9B H9BA . 0.9800 ?
C11B C12B . 1.383(3) ?
C11B C16B . 1.389(2) ?
C12B F1B . 1.311(3) ?
C12B C13B . 1.385(3) ?
C12B H12B . 0.9300 ?
C13B C14B . 1.372(3) ?
C13B H13B . 0.9300 ?
C14B C15B . 1.362(3) ?
C15B C16B . 1.387(3) ?
C15B H15B . 0.9300 ?
C16B F3B . 1.296(3) ?
C16B H16D . 0.9300 ?
C18B C19B . 1.500(2) ?
C18B H18C . 0.9700 ?
C18B H18D . 0.9700 ?
C19B H19D . 0.9600 ?
C19B H19E . 0.9600 ?
C19B H19F . 0.9600 ?
C20B H20D . 0.9600 ?
C20B H20E . 0.9600 ?
C20B H20F . 0.9600 ?
S1C C10C . 1.6786(16) ?
O1C C17C . 1.339(2) ?
O1C C18C . 1.458(2) ?
O2C C17C . 1.210(2) ?
F1C C12C . 1.3607(19) ?
F2C C14C . 1.3585(19) ?
N1C C10C . 1.381(2) ?
N1C C7C . 1.419(2) ?
N1C C6C . 1.450(2) ?
N2C C10C . 1.334(2) ?
N2C C9C . 1.462(2) ?
N2C H1NC . 0.90(2) ?
C1C C6C . 1.380(3) ?
C1C C2C . 1.392(3) ?
C1C H1CA . 0.9300 ?
C2C C3C . 1.361(4) ?
C2C H2CA . 0.9300 ?
C3C C4C . 1.373(4) ?
C3C H3CA . 0.9300 ?
C4C C5C . 1.396(3) ?
C4C H4CA . 0.9300 ?
C5C C6C . 1.374(3) ?
C5C H5CA . 0.9300 ?
C7C C8C . 1.347(2) ?
C7C C20C . 1.506(2) ?
C8C C17C . 1.478(2) ?
C8C C9C . 1.513(2) ?
C9C C11C . 1.520(2) ?
C9C H9CA . 0.9800 ?
C11C C12C . 1.388(2) ?
C11C C16C . 1.391(2) ?
C12C C13C . 1.382(2) ?
C13C C14C . 1.381(3) ?
C13C H13C . 0.9300 ?
C14C C15C . 1.370(3) ?
C15C C16C . 1.394(2) ?
C15C H15C . 0.9300 ?
C18C C19C . 1.504(3) ?
C18C H18E . 0.9700 ?
C18C H18F . 0.9700 ?
C19C H19G . 0.9600 ?
C19C H19H . 0.9600 ?
C19C H19I . 0.9600 ?
C20C H20G . 0.9600 ?
C20C H20H . 0.9600 ?
C20C H20I . 0.9600 ?
S1D C10D . 1.6777(16) ?
O1D C17D . 1.339(2) ?
O1D C18D . 1.454(2) ?
O2D C17D . 1.207(2) ?
F2D C14D . 1.3575(19) ?
F1D C12D . 1.3639(19) ?
N1D C10D . 1.3824(19) ?
N1D C7D . 1.419(2) ?
N1D C6D . 1.451(2) ?
N2D C10D . 1.332(2) ?
N2D C9D . 1.462(2) ?
N2D H1ND . 0.87(2) ?
C1D C6D . 1.377(2) ?
C1D C2D . 1.395(3) ?
C1D H1DA . 0.9300 ?
C2D C3D . 1.373(3) ?
C2D H2DA . 0.9300 ?
C3D C4D . 1.377(3) ?
C3D H3DA . 0.9300 ?
C4D C5D . 1.392(3) ?
C4D H4DA . 0.9300 ?
C5D C6D . 1.375(3) ?
C5D H5DA . 0.9300 ?
C7D C8D . 1.349(2) ?
C7D C20D . 1.502(2) ?
C8D C17D . 1.482(2) ?
C8D C9D . 1.509(2) ?
C9D C11D . 1.523(2) ?
C9D H9DA . 0.9800 ?
C11D C12D . 1.388(2) ?
C11D C16D . 1.394(2) ?
C12D C13D . 1.376(2) ?
C13D C14D . 1.380(3) ?
C13D H13D . 0.9300 ?
C14D C15D . 1.374(3) ?
C15D C16D . 1.393(2) ?
C15D H15D . 0.9300 ?
C16C H16A . 0.9300 ?
C18D C19D . 1.497(3) ?
C18D H18G . 0.9700 ?
C18D H18H . 0.9700 ?
C19D H19J . 0.9600 ?
C19D H19K . 0.9600 ?
C19D H19L . 0.9600 ?
C20D H20J . 0.9600 ?
C20D H20K . 0.9600 ?
C20D H20L . 0.9600 ?
C16D H16B . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2A H1NA S1B . 0.86(2) 2.63(2) 3.4521(15) 161.1(19)
N2B H1NB S1A . 0.87(2) 2.624(19) 3.4632(15) 163.1(18)
N2C H1NC S1C 2_776 0.90(2) 2.41(2) 3.2686(15) 160.0(17)
N2D H1ND S1D 2_667 0.87(2) 2.42(2) 3.2537(15) 159.7(17)
C9B H9BA O2C 2_766 0.98 2.50 3.199(2) 128
C16C H16A O2A 2_776 0.93 2.46 3.143(2) 130
C16D H16B O2B 2_656 0.93 2.47 3.146(2) 130
C18A H18B O2B 1_565 0.97 2.52 3.446(3) 159
C18B H18C O2A 1_545 0.97 2.50 3.427(2) 160
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6A C1A C2A C3A . . . . 0.8(3) ?
C1A C2A C3A C4A . . . . -0.2(3) ?
C2A C3A C4A C5A . . . . 0.0(3) ?
C3A C4A C5A C6A . . . . -0.4(3) ?
C2A C1A C6A C5A . . . . -1.2(3) ?
C2A C1A C6A N1A . . . . 171.70(16) ?
C4A C5A C6A C1A . . . . 1.0(2) ?
C4A C5A C6A N1A . . . . -171.93(15) ?
C10A N1A C6A C1A . . . . 87.56(19) ?
C7A N1A C6A C1A . . . . -90.26(19) ?
C10A N1A C6A C5A . . . . -99.42(18) ?
C7A N1A C6A C5A . . . . 82.75(19) ?
C10A N1A C7A C8A . . . . 14.0(2) ?
C6A N1A C7A C8A . . . . -168.28(15) ?
C10A N1A C7A C20A . . . . -165.36(15) ?
C6A N1A C7A C20A . . . . 12.4(2) ?
N1A C7A C8A C17A . . . . 178.96(15) ?
C20A C7A C8A C17A . . . . -1.8(3) ?
N1A C7A C8A C9A . . . . 2.6(2) ?
C20A C7A C8A C9A . . . . -178.18(16) ?
C10A N2A C9A C8A . . . . 26.3(2) ?
C10A N2A C9A C11A . . . . -99.17(18) ?
C7A C8A C9A N2A . . . . -20.1(2) ?
C17A C8A C9A N2A . . . . 163.02(14) ?
C7A C8A C9A C11A . . . . 104.46(18) ?
C17A C8A C9A C11A . . . . -72.43(17) ?
C9A N2A C10A N1A . . . . -12.7(2) ?
C9A N2A C10A S1A . . . . 168.72(13) ?
C7A N1A C10A N2A . . . . -9.3(2) ?
C6A N1A C10A N2A . . . . 172.99(14) ?
C7A N1A C10A S1A . . . . 169.28(12) ?
C6A N1A C10A S1A . . . . -8.5(2) ?
N2A C9A C11A C12A . . . . 73.41(19) ?
C8A C9A C11A C12A . . . . -49.9(2) ?
N2A C9A C11A C16A . . . . -106.84(17) ?
C8A C9A C11A C16A . . . . 129.81(16) ?
C16A C11A C12A F1A . . . . 166.80(19) ?
C9A C11A C12A F1A . . . . -13.4(3) ?
C16A C11A C12A C13A . . . . -0.3(3) ?
C9A C11A C12A C13A . . . . 179.47(16) ?
F1A C12A C13A C14A . . . . -166.5(2) ?
C11A C12A C13A C14A . . . . 0.6(3) ?
C12A C13A C14A F2A . . . . 179.39(16) ?
C12A C13A C14A C15A . . . . -0.3(3) ?
F2A C14A C15A C16A . . . . -179.91(15) ?
C13A C14A C15A C16A . . . . -0.2(3) ?
C14A C15A C16A F3A . . . . 175.75(17) ?
C14A C15A C16A C11A . . . . 0.5(3) ?
C12A C11A C16A F3A . . . . -175.39(17) ?
C9A C11A C16A F3A . . . . 4.8(2) ?
C12A C11A C16A C15A . . . . -0.3(2) ?
C9A C11A C16A C15A . . . . 179.97(15) ?
C7A C8A C17A O2A . . . . -173.23(17) ?
C9A C8A C17A O2A . . . . 3.4(2) ?
C7A C8A C17A O1A . . . . 3.7(3) ?
C9A C8A C17A O1A . . . . -179.66(16) ?
C7A C8A C17A O1E . . . . 35.7(7) ?
C9A C8A C17A O1E . . . . -147.7(7) ?
O2A C17A O1A C18A . . . . 0.4(3) ?
C8A C17A O1A C18A . . . . -176.45(16) ?
O1E C17A O1A C18A . . . . 108.0(9) ?
C17A O1A C18A C19A . . . . -176.8(2) ?
O2A C17A O1E C18E . . . . 34.5(16) ?
O1A C17A O1E C18E . . . . -60.2(12) ?
C8A C17A O1E C18E . . . . -176.3(11) ?
C17A O1E C18E C19E . . . . 85(2) ?
C6B C1B C2B C3B . . . . -0.1(2) ?
C1B C2B C3B C4B . . . . 0.0(3) ?
C2B C3B C4B C5B . . . . 0.3(3) ?
C3B C4B C5B C6B . . . . -0.5(3) ?
C2B C1B C6B C5B . . . . -0.1(2) ?
C2B C1B C6B N1B . . . . 175.12(14) ?
C4B C5B C6B C1B . . . . 0.4(2) ?
C4B C5B C6B N1B . . . . -174.76(15) ?
C10B N1B C6B C1B . . . . 92.31(18) ?
C7B N1B C6B C1B . . . . -88.92(18) ?
C10B N1B C6B C5B . . . . -92.45(18) ?
C7B N1B C6B C5B . . . . 86.31(19) ?
C10B N1B C7B C8B . . . . -12.3(2) ?
C6B N1B C7B C8B . . . . 168.95(15) ?
C10B N1B C7B C20B . . . . 167.73(15) ?
C6B N1B C7B C20B . . . . -11.0(2) ?
N1B C7B C8B C17B . . . . -179.67(15) ?
C20B C7B C8B C17B . . . . 0.3(3) ?
N1B C7B C8B C9B . . . . -2.7(2) ?
C20B C7B C8B C9B . . . . 177.27(15) ?
C10B N2B C9B C8B . . . . -26.8(2) ?
C10B N2B C9B C11B . . . . 98.75(19) ?
C7B C8B C9B N2B . . . . 19.7(2) ?
C17B C8B C9B N2B . . . . -162.91(13) ?
C7B C8B C9B C11B . . . . -104.48(18) ?
C17B C8B C9B C11B . . . . 72.96(17) ?
C9B N2B C10B N1B . . . . 14.6(2) ?
C9B N2B C10B S1B . . . . -167.28(13) ?
C7B N1B C10B N2B . . . . 6.8(2) ?
C6B N1B C10B N2B . . . . -174.44(14) ?
C7B N1B C10B S1B . . . . -171.33(12) ?
C6B N1B C10B S1B . . . . 7.4(2) ?
N2B C9B C11B C12B . . . . -74.1(2) ?
C8B C9B C11B C12B . . . . 49.3(2) ?
N2B C9B C11B C16B . . . . 105.33(17) ?
C8B C9B C11B C16B . . . . -131.32(16) ?
C16B C11B C12B F1B . . . . -163.7(2) ?
C9B C11B C12B F1B . . . . 15.8(3) ?
C16B C11B C12B C13B . . . . 0.4(3) ?
C9B C11B C12B C13B . . . . 179.81(17) ?
F1B C12B C13B C14B . . . . 163.0(2) ?
C11B C12B C13B C14B . . . . -0.8(3) ?
C12B C13B C14B F2B . . . . -178.93(17) ?
C12B C13B C14B C15B . . . . 0.6(3) ?
F2B C14B C15B C16B . . . . 179.56(16) ?
C13B C14B C15B C16B . . . . 0.0(3) ?
C14B C15B C16B F3B . . . . -175.16(18) ?
C14B C15B C16B C11B . . . . -0.5(3) ?
C12B C11B C16B F3B . . . . 174.88(18) ?
C9B C11B C16B F3B . . . . -4.6(3) ?
C12B C11B C16B C15B . . . . 0.3(3) ?
C9B C11B C16B C15B . . . . -179.13(16) ?
C18B O1B C17B O2B . . . . -3.0(2) ?
C18B O1B C17B C8B . . . . 177.07(14) ?
C7B C8B C17B O2B . . . . 170.72(17) ?
C9B C8B C17B O2B . . . . -6.5(2) ?
C7B C8B C17B O1B . . . . -9.4(3) ?
C9B C8B C17B O1B . . . . 173.40(14) ?
C17B O1B C18B C19B . . . . 178.89(15) ?
C6C C1C C2C C3C . . . . -2.2(3) ?
C1C C2C C3C C4C . . . . 1.0(3) ?
C2C C3C C4C C5C . . . . 1.2(4) ?
C3C C4C C5C C6C . . . . -2.2(4) ?
C4C C5C C6C C1C . . . . 1.0(3) ?
C4C C5C C6C N1C . . . . -175.91(19) ?
C2C C1C C6C C5C . . . . 1.1(3) ?
C2C C1C C6C N1C . . . . 177.95(15) ?
C10C N1C C6C C5C . . . . -107.12(19) ?
C7C N1C C6C C5C . . . . 68.7(2) ?
C10C N1C C6C C1C . . . . 76.0(2) ?
C7C N1C C6C C1C . . . . -108.22(18) ?
C10C N1C C7C C8C . . . . 9.8(2) ?
C6C N1C C7C C8C . . . . -165.86(15) ?
C10C N1C C7C C20C . . . . -166.89(15) ?
C6C N1C C7C C20C . . . . 17.4(2) ?
N1C C7C C8C C17C . . . . 178.20(15) ?
C20C C7C C8C C17C . . . . -5.5(3) ?
N1C C7C C8C C9C . . . . -3.3(2) ?
C20C C7C C8C C9C . . . . 173.04(15) ?
C10C N2C C9C C8C . . . . 25.2(2) ?
C10C N2C C9C C11C . . . . -101.43(17) ?
C7C C8C C9C N2C . . . . -12.0(2) ?
C17C C8C C9C N2C . . . . 166.75(13) ?
C7C C8C C9C C11C . . . . 113.68(17) ?
C17C C8C C9C C11C . . . . -67.59(18) ?
C9C N2C C10C N1C . . . . -20.7(2) ?
C9C N2C C10C S1C . . . . 163.05(12) ?
C7C N1C C10C N2C . . . . 1.4(2) ?
C6C N1C C10C N2C . . . . 177.09(14) ?
C7C N1C C10C S1C . . . . 177.69(12) ?
C6C N1C C10C S1C . . . . -6.6(2) ?
N2C C9C C11C C12C . . . . 54.2(2) ?
C8C C9C C11C C12C . . . . -70.00(19) ?
N2C C9C C11C C16C . . . . -125.58(16) ?
C8C C9C C11C C16C . . . . 110.26(17) ?
C16C C11C C12C F1C . . . . -179.65(14) ?
C9C C11C C12C F1C . . . . 0.6(2) ?
C16C C11C C12C C13C . . . . 0.6(2) ?
C9C C11C C12C C13C . . . . -179.18(15) ?
F1C C12C C13C C14C . . . . 177.93(14) ?
C11C C12C C13C C14C . . . . -2.3(3) ?
C12C C13C C14C F2C . . . . -177.77(14) ?
C12C C13C C14C C15C . . . . 2.3(3) ?
F2C C14C C15C C16C . . . . 179.43(14) ?
C13C C14C C15C C16C . . . . -0.7(3) ?
C18C O1C C17C O2C . . . . -2.7(2) ?
C18C O1C C17C C8C . . . . -179.13(14) ?
C7C C8C C17C O2C . . . . 158.63(17) ?
C9C C8C C17C O2C . . . . -20.0(2) ?
C7C C8C C17C O1C . . . . -24.9(2) ?
C9C C8C C17C O1C . . . . 156.40(14) ?
C17C O1C C18C C19C . . . . -168.78(15) ?
C6D C1D C2D C3D . . . . -0.4(3) ?
C1D C2D C3D C4D . . . . -1.7(3) ?
C2D C3D C4D C5D . . . . 2.6(3) ?
C3D C4D C5D C6D . . . . -1.4(3) ?
C4D C5D C6D C1D . . . . -0.7(3) ?
C4D C5D C6D N1D . . . . -179.23(16) ?
C2D C1D C6D C5D . . . . 1.5(3) ?
C2D C1D C6D N1D . . . . -179.93(15) ?
C10D N1D C6D C5D . . . . 90.06(19) ?
C7D N1D C6D C5D . . . . -82.95(19) ?
C10D N1D C6D C1D . . . . -88.51(19) ?
C7D N1D C6D C1D . . . . 98.48(19) ?
C10D N1D C7D C8D . . . . -9.7(2) ?
C6D N1D C7D C8D . . . . 162.99(15) ?
C10D N1D C7D C20D . . . . 166.60(15) ?
C6D N1D C7D C20D . . . . -20.7(2) ?
N1D C7D C8D C17D . . . . 179.80(15) ?
C20D C7D C8D C17D . . . . 4.0(3) ?
N1D C7D C8D C9D . . . . 1.9(2) ?
C20D C7D C8D C9D . . . . -173.87(16) ?
C10D N2D C9D C8D . . . . -25.7(2) ?
C10D N2D C9D C11D . . . . 101.43(18) ?
C7D C8D C9D N2D . . . . 13.5(2) ?
C17D C8D C9D N2D . . . . -164.67(13) ?
C7D C8D C9D C11D . . . . -112.62(18) ?
C17D C8D C9D C11D . . . . 69.20(18) ?
C9D N2D C10D N1D . . . . 20.1(2) ?
C9D N2D C10D S1D . . . . -164.18(12) ?
C7D N1D C10D N2D . . . . -0.6(2) ?
C6D N1D C10D N2D . . . . -173.40(14) ?
C7D N1D C10D S1D . . . . -176.36(12) ?
C6D N1D C10D S1D . . . . 10.8(2) ?
N2D C9D C11D C12D . . . . -53.4(2) ?
C8D C9D C11D C12D . . . . 71.2(2) ?
N2D C9D C11D C16D . . . . 125.69(15) ?
C8D C9D C11D C16D . . . . -109.64(17) ?
C16D C11D C12D F1D . . . . 179.49(14) ?
C9D C11D C12D F1D . . . . -1.4(2) ?
C16D C11D C12D C13D . . . . -1.5(2) ?
C9D C11D C12D C13D . . . . 177.69(15) ?
F1D C12D C13D C14D . . . . -178.42(15) ?
C11D C12D C13D C14D . . . . 2.5(3) ?
C12D C13D C14D F2D . . . . 177.85(15) ?
C12D C13D C14D C15D . . . . -1.8(3) ?
F2D C14D C15D C16D . . . . -179.53(15) ?
C13D C14D C15D C16D . . . . 0.1(3) ?
C12C C11C C16C C15C . . . . 1.2(2) ?
C9C C11C C16C C15C . . . . -179.01(14) ?
C14C C15C C16C C11C . . . . -1.2(2) ?
C18D O1D C17D O2D . . . . 4.0(2) ?
C18D O1D C17D C8D . . . . -179.82(14) ?
C7D C8D C17D O2D . . . . -157.11(18) ?
C9D C8D C17D O2D . . . . 21.0(2) ?
C7D C8D C17D O1D . . . . 26.7(2) ?
C9D C8D C17D O1D . . . . -155.20(14) ?
C17D O1D C18D C19D . . . . 167.69(16) ?
C14D C15D C16D C11D . . . . 1.0(2) ?
C12D C11D C16D C15D . . . . -0.4(2) ?
C9D C11D C16D C15D . . . . -179.55(15) ?
