#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/58/2205889.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_2205889
loop_
_publ_author_name
'Song, Yang'
'Baoan, Song'
'Guoping, Zhang'
'Linhong, Jin'
'Deyu, Hu'
'Wei, Xue'
_publ_section_title
;Diisopropyl
 {(4-methylbenzothiazol-2-ylamino)[4-(trifluoromethyl)phenyl]methyl}phosphonate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1662
_journal_page_last               o1664
_journal_paper_doi               10.1107/S1600536805014327
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C22 H26 F3 N2 O3 P S'
_chemical_formula_moiety         'C22 H26 F3 N2 O3 P S'
_chemical_formula_sum            'C22 H26 F3 N2 O3 P S'
_chemical_formula_weight         486.49
_chemical_name_systematic
;Diisopropyl
{(4-methylbenzothiazol-2-ylamino)[4-(trifluoromethyl)phenyl]methyl}phosphonate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 128.931(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.819(2)
_cell_length_b                   21.354(3)
_cell_length_c                   21.991(3)
_cell_measurement_reflns_used    3118
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.33
_cell_measurement_theta_min      2.25
_cell_volume                     5048.1(13)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART 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  0.0830
_diffrn_reflns_av_sigmaI/netI    0.1219
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29353
_diffrn_reflns_theta_full        26.53
_diffrn_reflns_theta_max         26.53
_diffrn_reflns_theta_min         1.53
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.257
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         10401
_refine_ls_number_restraints     186
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.2144
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1048P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.2280
_reflns_number_gt                3429
_reflns_number_total             10401
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6544.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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        5048.1(12)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2205889
_cod_database_fobs_code          2205889
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
P1 0.26354(13) 0.81905(7) 0.16031(8) 0.0689(4) Uani d . 1 C . P
P2 0.56179(12) 0.82014(7) 0.67057(8) 0.0686(4) Uani d . 1 . . P
S1 0.73905(13) 0.83127(8) 0.36680(9) 0.0931(5) Uani d . 1 . . S
S2 0.08986(13) 0.80018(7) 0.43290(8) 0.0835(5) Uani d . 1 . . S
F1 0.152(2) 0.5507(9) 0.2761(7) 0.209(9) Uani d PDU 0.416(16) A 1 F
F2 0.1695(16) 0.5989(6) 0.3696(11) 0.156(6) Uani d PDU 0.416(16) A 1 F
F3 0.3217(11) 0.5483(8) 0.3932(11) 0.152(6) Uani d PDU 0.416(16) A 1 F
F1' 0.1057(6) 0.5729(5) 0.2867(7) 0.143(4) Uani d PDU 0.584(16) A 2 F
F2' 0.2547(18) 0.5879(7) 0.4092(7) 0.210(6) Uani d PDU 0.584(16) A 2 F
F3' 0.2806(11) 0.5314(4) 0.3408(10) 0.166(5) Uani d PDU 0.584(16) A 2 F
F4 0.5606(10) 0.5567(4) 0.4498(9) 0.170(5) Uani d PDU 0.689(19) B 1 F
F5 0.6571(11) 0.6225(5) 0.4317(6) 0.145(4) Uani d PDU 0.689(19) B 1 F
F6 0.7501(9) 0.5787(6) 0.5424(4) 0.146(4) Uani d PDU 0.689(19) B 1 F
F4' 0.598(2) 0.5970(11) 0.4121(6) 0.146(8) Uani d PDU 0.311(19) B 2 F
F5' 0.7695(10) 0.6069(11) 0.5286(12) 0.131(8) Uani d PDU 0.311(19) B 2 F
F6' 0.628(3) 0.5469(6) 0.5066(16) 0.150(8) Uani d PDU 0.311(19) B 2 F
O1 0.2726(3) 0.77682(16) 0.11200(18) 0.0803(10) Uani d . 1 . . O
O3 0.1367(3) 0.81859(17) 0.1434(2) 0.0826(10) Uani d . 1 . . O
O4 0.5828(3) 0.76527(17) 0.71781(18) 0.0911(11) Uani d . 1 . . O
O5 0.6809(3) 0.84813(16) 0.68845(18) 0.0759(10) Uani d . 1 . . O
O6 0.4958(3) 0.87014(19) 0.6825(2) 0.0934(11) Uani d . 1 . . O
N1 0.5914(4) 0.86479(17) 0.3963(2) 0.0611(10) Uani d . 1 . . N
N2 0.4986(4) 0.8015(2) 0.2849(2) 0.0718(13) Uani d . 1 . . N
H2A 0.516(4) 0.780(2) 0.259(3) 0.086 Uiso d . 1 . . H
N3 0.2502(3) 0.85380(17) 0.4246(2) 0.0579(10) Uani d . 1 . . N
N4 0.3383(4) 0.7931(2) 0.5366(2) 0.0699(12) Uani d . 1 . . N
H4A 0.328(4) 0.767(2) 0.564(3) 0.084 Uiso d . 1 . . H
C1 0.7981(5) 0.8789(3) 0.4468(3) 0.0818(16) Uani d . 1 . . C
C2 0.9177(6) 0.9034(4) 0.4990(4) 0.124(2) Uani d . 1 . . C
H2 0.9783 0.8953 0.4938 0.148 Uiso calc R 1 . . H
C3 0.9423(7) 0.9403(4) 0.5586(4) 0.135(3) Uani d . 1 . . C
H3 1.0220 0.9563 0.5954 0.162 Uiso calc R 1 . . H
C4 0.8524(7) 0.9539(3) 0.5649(4) 0.112(2) Uani d . 1 . . C
H4 0.8718 0.9801 0.6050 0.135 Uiso calc R 1 . . H
C5 0.7330(6) 0.9299(3) 0.5132(3) 0.0834(16) Uani d . 1 . . C
C6 0.7066(5) 0.8913(2) 0.4531(3) 0.0687(14) Uani d . 1 . . C
C7 0.6353(6) 0.9460(3) 0.5209(4) 0.113(2) Uani d . 1 . . C
H7A 0.6565 0.9272 0.5675 0.170 Uiso calc R 1 . . H
H7B 0.5562 0.9304 0.4763 0.170 Uiso calc R 1 . . H
H7C 0.6310 0.9906 0.5238 0.170 Uiso calc R 1 . . H
C8 0.5954(4) 0.8323(2) 0.3478(3) 0.0576(12) Uani d . 1 . . C
C9 0.3757(4) 0.8036(2) 0.2636(3) 0.0620(13) Uani d . 1 . . C
H9 0.3740 0.8391 0.2911 0.074 Uiso calc R 1 . . H
C10 0.3420(4) 0.7457(2) 0.2859(2) 0.0581(12) Uani d . 1 . . C
C11 0.3547(6) 0.6872(3) 0.2668(3) 0.0892(17) Uani d . 1 . . C
H11 0.3892 0.6827 0.2418 0.107 Uiso calc R 1 . . H
C12 0.3174(6) 0.6347(3) 0.2837(4) 0.110(2) Uani d . 1 . . C
H12 0.3257 0.5951 0.2698 0.132 Uiso calc R 1 . . H
C13 0.2676(6) 0.6414(3) 0.3216(4) 0.0932(18) Uani d . 1 A . C
C14 0.2562(5) 0.6993(3) 0.3417(3) 0.0855(17) Uani d . 1 . . C
H14 0.2234 0.7039 0.3676 0.103 Uiso calc R 1 . . H
C15 0.2930(4) 0.7510(3) 0.3240(3) 0.0721(14) Uani d . 1 . . C
H15 0.2845 0.7904 0.3380 0.087 Uiso calc R 1 . . H
C16 0.2282(7) 0.5858(4) 0.3398(4) 0.138(3) Uani d D 1 . . C
O2 0.2879(4) 0.88942(17) 0.1558(2) 0.1036(13) Uani d D 1 . . O
C17 0.2958(14) 0.9127(7) 0.0967(7) 0.127(5) Uani d PDU 0.538(13) C 1 C
H17A 0.2772 0.8789 0.0606 0.152 Uiso calc PR 0.538(13) C 1 H
C18 0.4263(14) 0.9380(6) 0.1370(9) 0.138(6) Uani d PDU 0.538(13) C 1 C
H18A 0.4866 0.9075 0.1734 0.206 Uiso calc PR 0.538(13) C 1 H
H18B 0.4379 0.9759 0.1644 0.206 Uiso calc PR 0.538(13) C 1 H
H18C 0.4367 0.9467 0.0985 0.206 Uiso calc PR 0.538(13) C 1 H
C19 0.196(2) 0.9629(10) 0.0539(14) 0.212(10) Uani d PDU 0.538(13) C 1 C
H19A 0.1193 0.9468 0.0402 0.318 Uiso calc PR 0.538(13) C 1 H
H19B 0.1828 0.9750 0.0073 0.318 Uiso calc PR 0.538(13) C 1 H
H19C 0.2212 0.9988 0.0872 0.318 Uiso calc PR 0.538(13) C 1 H
C17' 0.2025(15) 0.9199(9) 0.0781(8) 0.137(7) Uani d PDU 0.462(13) C 2 C
H17B 0.1393 0.8903 0.0389 0.164 Uiso calc PR 0.462(13) C 2 H
C18' 0.284(3) 0.9417(14) 0.0577(18) 0.212(12) Uani d PDU 0.462(13) C 2 C
H18D 0.3541 0.9140 0.0813 0.317 Uiso calc PR 0.462(13) C 2 H
H18E 0.3133 0.9834 0.0770 0.317 Uiso calc PR 0.462(13) C 2 H
H18F 0.2367 0.9413 0.0020 0.317 Uiso calc PR 0.462(13) C 2 H
C19' 0.144(3) 0.9769(13) 0.0795(14) 0.234(13) Uani d PU 0.462(13) C 2 C
H19D 0.0915 0.9660 0.0926 0.350 Uiso calc PR 0.462(13) C 2 H
H19E 0.0946 0.9964 0.0289 0.350 Uiso calc PR 0.462(13) C 2 H
H19F 0.2072 1.0055 0.1178 0.350 Uiso calc PR 0.462(13) C 2 H
C20 0.0349(6) 0.7764(4) 0.0878(4) 0.113(2) Uani d . 1 . . C
H20 0.0700 0.7395 0.0814 0.135 Uiso calc R 1 . . H
C21 -0.0224(6) 0.7559(4) 0.1235(4) 0.159(3) Uani d . 1 . . C
H21A 0.0353 0.7299 0.1681 0.239 Uiso calc R 1 . . H
H21B -0.0968 0.7325 0.0859 0.239 Uiso calc R 1 . . H
H21C -0.0426 0.7919 0.1397 0.239 Uiso calc R 1 . . H
C22 -0.0508(8) 0.8076(5) 0.0111(5) 0.201(5) Uani d . 1 . . C
H22A -0.0766 0.8471 0.0175 0.302 Uiso calc R 1 . . H
H22B -0.1224 0.7815 -0.0236 0.302 Uiso calc R 1 . . H
H22C -0.0092 0.8144 -0.0105 0.302 Uiso calc R 1 . . H
C23 0.1322(5) 0.8713(2) 0.3573(3) 0.0598(12) Uani d . 1 . . C
C24 0.1103(5) 0.9091(2) 0.2982(3) 0.0700(14) Uani d . 1 . . C
C25 -0.0138(6) 0.9211(3) 0.2356(3) 0.0950(19) Uani d . 1 . . C
H25 -0.0316 0.9473 0.1959 0.114 Uiso calc R 1 . . H
C26 -0.1111(6) 0.8964(4) 0.2294(4) 0.122(2) Uani d . 1 . . C
H26 -0.1924 0.9047 0.1853 0.146 Uiso calc R 1 . . H
C27 -0.0894(6) 0.8596(4) 0.2873(4) 0.112(2) Uani d . 1 . . C
H27 -0.1551 0.8438 0.2843 0.135 Uiso calc R 1 . . H
C28 0.0330(5) 0.8463(3) 0.3512(3) 0.0784(15) Uani d . 1 . . C
C29 0.2409(4) 0.8177(2) 0.4680(3) 0.0574(12) Uani d . 1 . . C
C30 0.2146(5) 0.9355(2) 0.3023(3) 0.0827(16) Uani d . 1 . . C
H30A 0.2022 0.9251 0.2554 0.124 Uiso calc R 1 . . H
H30B 0.2920 0.9181 0.3466 0.124 Uiso calc R 1 . . H
H30C 0.2164 0.9802 0.3076 0.124 Uiso calc R 1 . . H
C31 0.4652(4) 0.8043(2) 0.5669(2) 0.0610(13) Uani d . 1 . . C
H31 0.4644 0.8423 0.5416 0.073 Uiso calc R 1 . . H
C32 0.5171(4) 0.7520(2) 0.5481(3) 0.0613(12) Uani d . 1 . . C
C33 0.5114(6) 0.6915(3) 0.5651(3) 0.0901(17) Uani d . 1 . . C
H33 0.4797 0.6826 0.5910 0.108 Uiso calc R 1 . . H
C34 0.5518(6) 0.6430(3) 0.5446(4) 0.106(2) Uani d . 1 . . C
H34 0.5463 0.6019 0.5562 0.127 Uiso calc R 1 . . H
C35 0.5995(6) 0.6550(3) 0.5077(4) 0.0910(18) Uani d . 1 B . C
C36 0.6091(5) 0.7156(4) 0.4912(3) 0.0876(17) Uani d . 1 . . C
H36 0.6437 0.7240 0.4670 0.105 Uiso calc R 1 . . H
C37 0.5667(4) 0.7645(3) 0.5110(3) 0.0719(14) Uani d . 1 . . C
H37 0.5717 0.8055 0.4991 0.086 Uiso calc R 1 . . H
C38 0.6428(7) 0.6040(4) 0.4854(4) 0.129(3) Uani d D 1 . . C
C39 0.8070(6) 0.8271(3) 0.7531(4) 0.1015(19) Uani d U 1 . . C
H39 0.8005 0.7877 0.7732 0.122 Uiso calc R 1 . . H
C40 0.8664(8) 0.8729(5) 0.8154(5) 0.180(4) Uani d U 1 . . C
H40A 0.8777 0.9113 0.7977 0.270 Uiso calc R 1 . . H
H40B 0.9459 0.8573 0.8597 0.270 Uiso calc R 1 . . H
H40C 0.8151 0.8806 0.8301 0.270 Uiso calc R 1 . . H
C41 0.8729(8) 0.8145(4) 0.7222(5) 0.180(4) Uani d U 1 . . C
H41A 0.8299 0.7825 0.6829 0.270 Uiso calc R 1 . . H
H41B 0.9560 0.8008 0.7638 0.270 Uiso calc R 1 . . H
H41C 0.8761 0.8521 0.6995 0.270 Uiso calc R 1 . . H
C42 0.4516(7) 0.9288(3) 0.6437(4) 0.112(2) Uani d . 1 . . C
H42 0.4408 0.9279 0.5953 0.134 Uiso calc R 1 . . H
C43 0.5400(8) 0.9792(4) 0.6964(6) 0.198(4) Uani d U 1 . . C
H43A 0.6185 0.9723 0.7078 0.297 Uiso calc PR 0.50 . . H
H43B 0.5514 0.9786 0.7442 0.297 Uiso calc PR 0.50 . . H
H43C 0.5071 1.0191 0.6713 0.297 Uiso calc PR 0.50 . . H
H43D 0.4995 1.0077 0.7078 0.297 Uiso calc PR 0.50 . . H
H43E 0.5667 1.0014 0.6713 0.297 Uiso calc PR 0.50 . . H
H43F 0.6109 0.9610 0.7442 0.297 Uiso calc PR 0.50 . . H
C44 0.3268(7) 0.9402(4) 0.6260(5) 0.149(3) Uani d U 1 . . C
H44A 0.2806 0.9018 0.6094 0.223 Uiso calc R 1 . . H
H44B 0.2803 0.9709 0.5852 0.223 Uiso calc R 1 . . H
H44C 0.3412 0.9552 0.6722 0.223 Uiso calc R 1 . . H
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'
P P 0.1023 0.0942 '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
_geom_angle_publ_flag
O1 P1 O3 115.1(2) y
O1 P1 O2 115.5(2) y
O3 P1 O2 104.4(2) y
O1 P1 C9 113.9(2) y
O3 P1 C9 104.4(2) y
O2 P1 C9 102.0(2) y
O4 P2 O6 108.0(2) y
O4 P2 O5 114.9(2) y
O6 P2 O5 109.8(2) y
O4 P2 C31 113.8(2) y
O6 P2 C31 107.4(2) y
O5 P2 C31 102.5(2) y
C1 S1 C8 88.6(3) ?
C28 S2 C29 88.5(3) ?
C20 O3 P1 123.8(3) ?
C39 O5 P2 123.6(3) ?
C42 O6 P2 126.3(4) ?
C8 N1 C6 109.9(4) ?
C8 N2 C9 121.6(4) ?
C8 N2 H2A 115(3) ?
C9 N2 H2A 123(3) ?
C29 N3 C23 110.4(4) ?
C29 N4 C31 121.3(4) ?
C29 N4 H4A 122(3) ?
C31 N4 H4A 117(3) ?
C6 C1 C2 122.3(5) ?
C6 C1 S1 109.7(4) ?
C2 C1 S1 128.0(5) ?
C3 C2 C1 117.0(6) ?
C3 C2 H2 121.5 ?
C1 C2 H2 121.5 ?
C4 C3 C2 121.5(7) ?
C4 C3 H3 119.2 ?
C2 C3 H3 119.2 ?
C3 C4 C5 121.9(6) ?
C3 C4 H4 119.0 ?
C5 C4 H4 119.0 ?
C4 C5 C6 117.5(6) ?
C4 C5 C7 121.0(6) ?
C6 C5 C7 121.5(5) ?
C1 C6 N1 116.0(5) ?
C1 C6 C5 119.7(5) ?
N1 C6 C5 124.3(5) ?
C5 C7 H7A 109.5 ?
C5 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C5 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
N1 C8 N2 125.2(4) ?
N1 C8 S1 115.8(4) ?
N2 C8 S1 119.0(3) ?
N2 C9 C10 114.1(4) y
N2 C9 P1 108.6(3) y
C10 C9 P1 111.4(3) y
N2 C9 H9 107.5 ?
C10 C9 H9 107.5 ?
P1 C9 H9 107.5 ?
C11 C10 C15 118.2(5) ?
C11 C10 C9 121.6(4) ?
C15 C10 C9 120.2(4) ?
C10 C11 C12 121.2(5) ?
C10 C11 H11 119.4 ?
C12 C11 H11 119.4 ?
C11 C12 C13 119.4(6) ?
C11 C12 H12 120.3 ?
C13 C12 H12 120.3 ?
C14 C13 C12 119.7(6) ?
C14 C13 C16 120.8(7) ?
C12 C13 C16 119.5(7) ?
C13 C14 C15 120.1(5) ?
C13 C14 H14 119.9 ?
C15 C14 H14 119.9 ?
C14 C15 C10 121.4(5) ?
C14 C15 H15 119.3 ?
C10 C15 H15 119.3 ?
F1 C16 F3 106.2(10) ?
F2' C16 F1' 106.9(9) ?
F1 C16 F2 107.6(10) ?
F3 C16 F2 103.9(9) ?
F2' C16 F3' 104.5(9) ?
F1' C16 F3' 101.9(8) ?
F1 C16 C13 110.8(10) ?
F3 C16 C13 113.9(9) ?
F2 C16 C13 113.8(9) ?
C17 O2 P1 121.7(7) ?
C17' O2 P1 116.7(8) ?
O2 C17 C19 104.0(13) ?
O2 C17 C18 109.1(10) ?
C19 C17 C18 113.2(14) ?
O2 C17 H17A 110.1 ?
C19 C17 H17A 110.1 ?
C18 C17 H17A 110.1 ?
C17 C18 H18A 109.5 ?
C17 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C17 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C17 C19 H19A 109.5 ?
C17 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C17 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C19' C17' O2 112.9(16) ?
C19' C17' C18' 105.8(19) ?
O2 C17' C18' 105.8(15) ?
C19' C17' H17B 110.7 ?
O2 C17' H17B 110.7 ?
C18' C17' H17B 110.7 ?
C17' C18' H18D 109.5 ?
C17' C18' H18E 109.5 ?
H18D C18' H18E 109.5 ?
C17' C18' H18F 109.5 ?
H18D C18' H18F 109.5 ?
H18E C18' H18F 109.5 ?
C17' C19' H19D 109.5 ?
C17' C19' H19E 109.5 ?
H19D C19' H19E 109.5 ?
C17' C19' H19F 109.5 ?
H19D C19' H19F 109.5 ?
H19E C19' H19F 109.5 ?
O3 C20 C22 109.8(7) ?
O3 C20 C21 106.9(5) ?
C22 C20 C21 115.1(6) ?
O3 C20 H20 108.3 ?
C22 C20 H20 108.3 ?
C21 C20 H20 108.3 ?
C20 C21 H21A 109.5 ?
C20 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
C20 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
C20 C22 H22A 109.5 ?
C20 C22 H22B 109.5 ?
H22A C22 H22B 109.5 ?
C20 C22 H22C 109.5 ?
H22A C22 H22C 109.5 ?
H22B C22 H22C 109.5 ?
C24 C23 C28 120.4(5) ?
C24 C23 N3 124.6(5) ?
C28 C23 N3 115.0(4) ?
C25 C24 C23 116.2(5) ?
C25 C24 C30 122.1(5) ?
C23 C24 C30 121.7(5) ?
C26 C25 C24 123.3(6) ?
C26 C25 H25 118.3 ?
C24 C25 H25 118.3 ?
C27 C26 C25 120.3(6) ?
C27 C26 H26 119.8 ?
C25 C26 H26 119.8 ?
C26 C27 C28 118.4(6) ?
C26 C27 H27 120.8 ?
C28 C27 H27 120.8 ?
C27 C28 C23 121.3(5) ?
C27 C28 S2 129.1(5) ?
C23 C28 S2 109.7(4) ?
N3 C29 N4 124.4(4) ?
N3 C29 S2 116.5(4) ?
N4 C29 S2 119.1(4) ?
C24 C30 H30A 109.5 ?
C24 C30 H30B 109.5 ?
H30A C30 H30B 109.5 ?
C24 C30 H30C 109.5 ?
H30A C30 H30C 109.5 ?
H30B C30 H30C 109.5 ?
N4 C31 C32 113.3(4) y
N4 C31 P2 109.3(3) y
C32 C31 P2 112.3(3) y
N4 C31 H31 107.2 ?
C32 C31 H31 107.2 ?
P2 C31 H31 107.2 ?
C33 C32 C37 118.6(5) ?
C33 C32 C31 120.4(4) ?
C37 C32 C31 120.9(5) ?
C32 C33 C34 121.2(6) ?
C32 C33 H33 119.4 ?
C34 C33 H33 119.4 ?
C35 C34 C33 120.2(6) ?
C35 C34 H34 119.9 ?
C33 C34 H34 119.9 ?
C34 C35 C36 120.1(6) ?
C34 C35 C38 120.9(7) ?
C36 C35 C38 119.0(7) ?
C35 C36 C37 119.7(5) ?
C35 C36 H36 120.2 ?
C37 C36 H36 120.2 ?
C32 C37 C36 120.2(5) ?
C32 C37 H37 119.9 ?
C36 C37 H37 119.9 ?
F6 C38 F4 106.3(8) ?
F4' C38 F6' 105.0(10) ?
F4' C38 F5' 105.2(11) ?
F6' C38 F5' 101.8(9) ?
F6 C38 F5 104.6(8) ?
F4 C38 F5 103.9(7) ?
F6 C38 C35 116.1(7) ?
F4 C38 C35 112.4(7) ?
F5 C38 C35 112.6(7) ?
C40 C39 O5 109.5(6) ?
C40 C39 C41 114.5(7) ?
O5 C39 C41 108.2(6) ?
C40 C39 H39 108.2 ?
O5 C39 H39 108.2 ?
C41 C39 H39 108.2 ?
C39 C40 H40A 109.5 ?
C39 C40 H40B 109.5 ?
H40A C40 H40B 109.5 ?
C39 C40 H40C 109.5 ?
H40A C40 H40C 109.5 ?
H40B C40 H40C 109.5 ?
C39 C41 H41A 109.5 ?
C39 C41 H41B 109.5 ?
H41A C41 H41B 109.5 ?
C39 C41 H41C 109.5 ?
H41A C41 H41C 109.5 ?
H41B C41 H41C 109.5 ?
O6 C42 C43 109.7(6) ?
O6 C42 C44 106.6(5) ?
C43 C42 C44 109.0(7) ?
O6 C42 H42 110.5 ?
C43 C42 H42 110.5 ?
C44 C42 H42 110.5 ?
C42 C43 H43A 109.5 ?
C42 C43 H43B 109.5 ?
H43A C43 H43B 109.5 ?
C42 C43 H43C 109.5 ?
H43A C43 H43C 109.5 ?
H43B C43 H43C 109.5 ?
C42 C43 H43D 109.5 ?
H43A C43 H43D 141.1 ?
H43B C43 H43D 56.3 ?
H43C C43 H43D 56.3 ?
C42 C43 H43E 109.5 ?
H43A C43 H43E 56.3 ?
H43B C43 H43E 141.1 ?
H43C C43 H43E 56.3 ?
H43D C43 H43E 109.5 ?
C42 C43 H43F 109.5 ?
H43A C43 H43F 56.3 ?
H43B C43 H43F 56.3 ?
H43C C43 H43F 141.1 ?
H43D C43 H43F 109.5 ?
H43E C43 H43F 109.5 ?
C42 C44 H44A 109.5 ?
C42 C44 H44B 109.5 ?
H44A C44 H44B 109.5 ?
C42 C44 H44C 109.5 ?
H44A C44 H44C 109.5 ?
H44B C44 H44C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 1.458(3) y
P1 O3 1.547(4) y
P1 O2 1.556(4) y
P1 C9 1.802(5) y
P2 O4 1.469(3) y
P2 O6 1.530(4) y
P2 O5 1.552(3) y
P2 C31 1.808(4) y
S1 C1 1.730(5) y
S1 C8 1.753(5) y
S2 C28 1.745(5) y
S2 C29 1.751(5) y
F1 C16 1.333(9) ?
F2 C16 1.356(9) ?
F3 C16 1.336(9) ?
F1' C16 1.349(8) ?
F2' C16 1.329(8) ?
F3' C16 1.362(8) ?
F4 C38 1.345(8) ?
F5 C38 1.374(8) ?
F6 C38 1.314(7) ?
F4' C38 1.324(9) ?
F5' C38 1.372(9) ?
F6' C38 1.366(9) ?
O3 C20 1.458(7) ?
O5 C39 1.464(6) ?
O6 C42 1.419(6) ?
N1 C8 1.303(5) y
N1 C6 1.384(6) y
N2 C8 1.344(6) y
N2 C9 1.451(6) y
N2 H2A 0.87(5) ?
N3 C29 1.295(5) y
N3 C23 1.398(5) y
N4 C29 1.346(6) y
N4 C31 1.453(6) y
N4 H4A 0.90(5) ?
C1 C6 1.381(7) ?
C1 C2 1.392(7) ?
C2 C3 1.376(8) ?
C2 H2 0.93 ?
C3 C4 1.365(8) ?
C3 H3 0.93 ?
C4 C5 1.386(8) ?
C4 H4 0.93 ?
C5 C6 1.398(7) ?
C5 C7 1.501(7) ?
C7 H7A 0.96 ?
C7 H7B 0.96 ?
C7 H7C 0.96 ?
C9 C10 1.508(6) ?
C9 H9 0.98 ?
C10 C11 1.364(6) ?
C10 C15 1.372(6) ?
C11 C12 1.381(8) ?
C11 H11 0.93 ?
C12 C13 1.381(8) ?
C12 H12 0.93 ?
C13 C14 1.354(8) ?
C13 C16 1.464(9) ?
C14 C15 1.371(7) ?
C14 H14 0.93 ?
C15 H15 0.93 ?
O2 C17 1.459(9) ?
O2 C17' 1.485(10) ?
C17 C19 1.523(10) ?
C17 C18 1.524(9) ?
C17 H17A 0.98 ?
C18 H18A 0.96 ?
C18 H18B 0.96 ?
C18 H18C 0.96 ?
C19 H19A 0.96 ?
C19 H19B 0.96 ?
C19 H19C 0.96 ?
C17' C19' 1.47(3) ?
C17' C18' 1.526(7) ?
C17' H17B 0.98 ?
C18' H18D 0.96 ?
C18' H18E 0.96 ?
C18' H18F 0.96 ?
C19' H19D 0.96 ?
C19' H19E 0.96 ?
C19' H19F 0.96 ?
C20 C22 1.476(9) ?
C20 C21 1.491(8) ?
C20 H20 0.98 ?
C21 H21A 0.96 ?
C21 H21B 0.96 ?
C21 H21C 0.96 ?
C22 H22A 0.96 ?
C22 H22B 0.96 ?
C22 H22C 0.96 ?
C23 C24 1.393(6) ?
C23 C28 1.395(7) ?
C24 C25 1.391(7) ?
C24 C30 1.497(7) ?
C25 C26 1.370(8) ?
C25 H25 0.93 ?
C26 C27 1.360(8) ?
C26 H26 0.93 ?
C27 C28 1.389(7) ?
C27 H27 0.93 ?
C30 H30A 0.96 ?
C30 H30B 0.96 ?
C30 H30C 0.96 ?
C31 C32 1.517(6) ?
C31 H31 0.98 ?
C32 C33 1.362(7) ?
C32 C37 1.383(6) ?
C33 C34 1.379(8) ?
C33 H33 0.93 ?
C34 C35 1.354(8) ?
C34 H34 0.93 ?
C35 C36 1.372(8) ?
C35 C38 1.467(9) ?
C36 C37 1.392(7) ?
C36 H36 0.93 ?
C37 H37 0.93 ?
C39 C40 1.447(9) ?
C39 C41 1.466(9) ?
C39 H39 0.98 ?
C40 H40A 0.96 ?
C40 H40B 0.96 ?
C40 H40C 0.96 ?
C41 H41A 0.96 ?
C41 H41B 0.96 ?
C41 H41C 0.96 ?
C42 C43 1.488(10) ?
C42 C44 1.529(8) ?
C42 H42 0.98 ?
C43 H43A 0.96 ?
C43 H43B 0.96 ?
C43 H43C 0.96 ?
C43 H43D 0.96 ?
C43 H43E 0.96 ?
C43 H43F 0.96 ?
C44 H44A 0.96 ?
C44 H44B 0.96 ?
C44 H44C 0.96 ?
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
N2 H2A O4 4_575 0.87(5) 1.91(6) 2.779(7) 170(5)
N4 H4A O1 4_576 0.90(5) 1.90(6) 2.774(7) 167(6)
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
O1 P1 O3 C20 4.4(5)
O2 P1 O3 C20 132.0(5)
C9 P1 O3 C20 -121.3(5)
O4 P2 O5 C39 -7.0(5)
O6 P2 O5 C39 115.1(4)
C31 P2 O5 C39 -130.9(4)
O4 P2 O6 C42 -175.8(5)
O5 P2 O6 C42 58.2(5)
C31 P2 O6 C42 -52.6(5)
C8 S1 C1 C6 0.4(4)
C8 S1 C1 C2 -178.9(6)
C6 C1 C2 C3 0.9(10)
S1 C1 C2 C3 -179.9(6)
C1 C2 C3 C4 -2.1(12)
C2 C3 C4 C5 2.0(12)
C3 C4 C5 C6 -0.7(10)
C3 C4 C5 C7 -179.5(7)
C2 C1 C6 N1 178.8(5)
S1 C1 C6 N1 -0.6(6)
C2 C1 C6 C5 0.4(9)
S1 C1 C6 C5 -179.0(4)
C8 N1 C6 C1 0.5(6)
C8 N1 C6 C5 178.8(5)
C4 C5 C6 C1 -0.5(8)
C7 C5 C6 C1 178.3(5)
C4 C5 C6 N1 -178.7(5)
C7 C5 C6 N1 0.1(8)
C6 N1 C8 N2 -178.6(4)
C6 N1 C8 S1 -0.2(5)
C9 N2 C8 N1 2.0(7)
C9 N2 C8 S1 -176.4(4)
C1 S1 C8 N1 -0.1(4)
C1 S1 C8 N2 178.4(4)
C8 N2 C9 C10 -102.1(5)
C8 N2 C9 P1 133.1(4)
O1 P1 C9 N2 52.2(4)
O3 P1 C9 N2 178.6(3)
O2 P1 C9 N2 -72.9(3)
O1 P1 C9 C10 -74.2(4)
O3 P1 C9 C10 52.2(4)
O2 P1 C9 C10 160.7(3)
N2 C9 C10 C11 -50.7(6)
P1 C9 C10 C11 72.6(5)
N2 C9 C10 C15 131.8(4)
P1 C9 C10 C15 -104.9(4)
C15 C10 C11 C12 1.1(8)
C9 C10 C11 C12 -176.4(5)
C10 C11 C12 C13 -0.8(10)
C11 C12 C13 C14 -0.1(10)
C11 C12 C13 C16 -179.9(6)
C12 C13 C14 C15 0.5(9)
C16 C13 C14 C15 -179.7(6)
C13 C14 C15 C10 -0.1(8)
C11 C10 C15 C14 -0.7(7)
C9 C10 C15 C14 176.9(4)
C14 C13 C16 F2' -39.2(14)
C12 C13 C16 F2' 140.6(12)
C14 C13 C16 F1 128.1(14)
C12 C13 C16 F1 -52.1(15)
C14 C13 C16 F3 -112.3(13)
C12 C13 C16 F3 67.5(13)
C14 C13 C16 F1' 84.0(10)
C12 C13 C16 F1' -96.2(10)
C14 C13 C16 F2 6.6(13)
C12 C13 C16 F2 -173.6(10)
C14 C13 C16 F3' -159.2(9)
C12 C13 C16 F3' 20.6(12)
O1 P1 O2 C17 11.1(8)
O3 P1 O2 C17 -116.3(8)
C9 P1 O2 C17 135.2(8)
O1 P1 O2 C17' 61.0(9)
O3 P1 O2 C17' -66.4(9)
C9 P1 O2 C17' -174.9(9)
C17' O2 C17 C19 25.8(16)
P1 O2 C17 C19 122.5(11)
C17' O2 C17 C18 147(2)
P1 O2 C17 C18 -116.5(10)
C17 O2 C17' C19' -126(2)
P1 O2 C17' C19' 125.5(16)
C17 O2 C17' C18' -10.3(15)
P1 O2 C17' C18' -119.2(15)
P1 O3 C20 C22 -94.3(6)
P1 O3 C20 C21 140.2(5)
C29 N3 C23 C24 -178.9(4)
C29 N3 C23 C28 -0.7(6)
C28 C23 C24 C25 1.6(7)
N3 C23 C24 C25 179.7(4)
C28 C23 C24 C30 -178.8(4)
N3 C23 C24 C30 -0.7(7)
C23 C24 C25 C26 -2.0(9)
C30 C24 C25 C26 178.4(6)
C24 C25 C26 C27 2.3(11)
C25 C26 C27 C28 -2.1(11)
C26 C27 C28 C23 1.8(10)
C26 C27 C28 S2 -178.9(5)
C24 C23 C28 C27 -1.6(8)
N3 C23 C28 C27 -179.9(5)
C24 C23 C28 S2 178.9(4)
N3 C23 C28 S2 0.7(5)
C29 S2 C28 C27 -179.7(6)
C29 S2 C28 C23 -0.3(4)
C23 N3 C29 N4 179.8(4)
C23 N3 C29 S2 0.5(5)
C31 N4 C29 N3 -1.6(7)
C31 N4 C29 S2 177.7(3)
C28 S2 C29 N3 -0.1(4)
C28 S2 C29 N4 -179.4(4)
C29 N4 C31 C32 -96.5(5)
C29 N4 C31 P2 137.4(4)
O4 P2 C31 N4 70.0(4)
O6 P2 C31 N4 -49.6(4)
O5 P2 C31 N4 -165.3(3)
O4 P2 C31 C32 -56.7(4)
O6 P2 C31 C32 -176.2(3)
O5 P2 C31 C32 68.0(4)
N4 C31 C32 C33 -51.7(6)
P2 C31 C32 C33 72.8(5)
N4 C31 C32 C37 125.9(5)
P2 C31 C32 C37 -109.7(4)
C37 C32 C33 C34 -1.2(8)
C31 C32 C33 C34 176.4(5)
C32 C33 C34 C35 0.7(10)
C33 C34 C35 C36 0.7(10)
C33 C34 C35 C38 -180.0(6)
C34 C35 C36 C37 -1.6(9)
C38 C35 C36 C37 179.1(5)
C33 C32 C37 C36 0.3(7)
C31 C32 C37 C36 -177.3(4)
C35 C36 C37 C32 1.1(8)
C34 C35 C38 F6 -75.5(12)
C36 C35 C38 F6 103.8(11)
C34 C35 C38 F4' 124.3(17)
C36 C35 C38 F4' -56.4(18)
C34 C35 C38 F4 47.1(11)
C36 C35 C38 F4 -133.6(9)
C34 C35 C38 F6' 0.0(15)
C36 C35 C38 F6' 179.3(14)
C34 C35 C38 F5' -112.4(14)
C36 C35 C38 F5' 66.9(14)
C34 C35 C38 F5 164.0(8)
C36 C35 C38 F5 -16.7(11)
P2 O5 C39 C40 -104.5(6)
P2 O5 C39 C41 130.1(5)
P2 O6 C42 C43 -101.6(7)
P2 O6 C42 C44 140.5(5)
