#------------------------------------------------------------------------------
#$Date: 2019-12-25 20:49:56 +0200 (Wed, 25 Dec 2019) $
#$Revision: 245693 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/12/2311220.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_2311220
loop_
_publ_author_name
'Akkurt, Mehmet'
'Mague, Joel T.'
'Mohamed, Shaaban K.'
'Younes, Sabry H. H.'
'Albayati, Mustafa R.'
_publ_section_title
;
 Bis(2-amino-5-benzyl-3-eth-oxy-carbonyl-4,5,6,7-tetra-hydro-thieno[3,2-c]pyridin-5-ium)
 bis-(4-meth-oxy-phen-yl)di-phos-phon-ate.
;
_journal_coeditor_code           RZ5105
_journal_issue                   'Pt 3'
_journal_name_full
'Acta crystallographica. Section E, Structure reports online'
_journal_page_first              o348
_journal_page_last               9
_journal_paper_doi               10.1107/S1600536814003766
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          '2C17 H21 N2 O2 S +, C14 H14 O7 P2 2-'
_chemical_formula_moiety         '2(C17 H21 N2 O2 S +), C14 H14 O7 P2 2-'
_chemical_formula_sum            'C48 H56 N4 O11 P2 S2'
_chemical_formula_weight         991.05
_chemical_name_systematic
'Bis(2-amino-5-benzyl-3-ethoxycarbonyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-ium) bis(4-methoxyphenyl)diphosphonate'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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   mixed
_cell_angle_alpha                90
_cell_angle_beta                 114.3270(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.9420(9)
_cell_length_b                   10.8718(7)
_cell_length_c                   16.0773(10)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.3391
_cell_measurement_theta_min      2.3328
_cell_volume                     2379.8(3)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3660
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            41576
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2013)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.771
_refine_diff_density_min         -0.620
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5955
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0486
_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)+(0.0554P)²+1.6086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                4481
_reflns_number_total             5955
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz5105sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2311220
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.57869(4) 1.03372(5) 0.46675(4) 0.0305(2) Uani d . 1.000 . .
O O3 0.86773(11) 0.62642(14) 0.61933(12) 0.0427(5) Uani d . 1.000 . .
O O4A 0.5173(2) 1.0157(3) 0.3725(2) 0.0309(5) Uani d UP 0.500 B 1
O O4B 0.5512(2) 1.0296(3) 0.3642(2) 0.0309(5) Uani d UP 0.500 B 2
O O5A 0.5998(2) 1.1419(3) 0.5154(2) 0.0309(5) Uani d UP 0.500 B 1
O O5B 0.6358(2) 1.1646(3) 0.4900(2) 0.0309(5) Uani d UP 0.500 B 2
O O6 0.52418(18) 1.0374(2) 0.53284(18) 0.0274(8) Uani d P 0.500 B .
C C18 0.96967(18) 0.6470(3) 0.6554(2) 0.0581(10) Uani d . 1.000 . .
C C19 0.80643(15) 0.72531(19) 0.58665(14) 0.0316(6) Uani d . 1.000 . .
C C20 0.83752(15) 0.8459(2) 0.59149(16) 0.0361(6) Uani d . 1.000 . .
C C21 0.76781(15) 0.93886(19) 0.55603(15) 0.0346(6) Uani d . 1.000 . .
C C22 0.66850(14) 0.91441(18) 0.51714(13) 0.0272(5) Uani d . 1.000 . .
C C23 0.63917(15) 0.7916(2) 0.51452(15) 0.0344(6) Uani d . 1.000 . .
C C24 0.70699(16) 0.69865(19) 0.54824(16) 0.0370(7) Uani d . 1.000 . .
S S1 0.58537(4) 1.08926(4) 0.08978(3) 0.02890(10) Uani d . 1.000 . .
O O1 0.91131(13) 1.09586(18) 0.27696(13) 0.0560(7) Uani d . 1.000 . .
O O2 0.87989(13) 0.92245(18) 0.33537(13) 0.0570(6) Uani d . 1.000 . .
N N1 0.49957(14) 0.85683(15) 0.23756(12) 0.0331(5) Uani d . 1.000 . .
N N2 0.75816(16) 1.19991(18) 0.13051(15) 0.0400(6) Uani d . 1.000 . .
C C1 0.31772(17) 0.8669(2) 0.18867(15) 0.0381(7) Uani d . 1.000 . .
C C2 0.29320(18) 0.9500(2) 0.24134(16) 0.0423(7) Uani d . 1.000 . .
C C3 0.2121(2) 1.0252(3) 0.2017(2) 0.0544(10) Uani d . 1.000 . .
C C4 0.1555(2) 1.0191(3) 0.1092(2) 0.0628(11) Uani d . 1.000 . .
C C5 0.1785(2) 0.9363(3) 0.0564(2) 0.0629(10) Uani d . 1.000 . .
C C6 0.25792(19) 0.8596(3) 0.09563(17) 0.0501(8) Uani d . 1.000 . .
C C7 0.40835(18) 0.7891(2) 0.23008(16) 0.0412(7) Uani d . 1.000 . .
C C8 0.48723(16) 0.91160(19) 0.14823(14) 0.0331(6) Uani d . 1.000 . .
C C9 0.58213(16) 0.96802(17) 0.15942(14) 0.0304(6) Uani d . 1.000 . .
C C10 0.67162(16) 0.94260(18) 0.22578(14) 0.0323(6) Uani d . 1.000 . .
C C11 0.68191(17) 0.8442(2) 0.29481(15) 0.0386(7) Uani d . 1.000 . .
C C12 0.58719(18) 0.77301(19) 0.27059(15) 0.0399(7) Uani d . 1.000 . .
C C13 0.71049(16) 1.11013(18) 0.15399(14) 0.0317(6) Uani d . 1.000 . .
C C14 0.74755(16) 1.02343(19) 0.22349(14) 0.0330(6) Uani d . 1.000 . .
C C15 0.85221(18) 1.0206(2) 0.27950(16) 0.0423(7) Uani d . 1.000 . .
C C16A 0.9874(3) 0.9227(4) 0.3882(4) 0.0673(10) Uani d P 0.753(5) A 1
C C17A 1.0074(3) 0.8018(4) 0.4371(3) 0.0673(10) Uani d P 0.753(5) A 1
C C17B 1.0233(8) 0.8259(10) 0.3766(6) 0.0673(10) Uani d P 0.247(5) A 2
C C16B 0.9693(9) 0.8858(11) 0.4036(11) 0.0673(10) Uani d P 0.247(5) A 2
H H18A 1.00440 0.56880 0.67590 0.0870 Uiso c RU 1.000 . .
H H18B 0.98850 0.70380 0.70710 0.0870 Uiso c RU 1.000 . .
H H18C 0.98720 0.68280 0.60810 0.0870 Uiso c RU 1.000 . .
H H20 0.90560 0.86510 0.61870 0.0430 Uiso c RU 1.000 . .
H H21 0.78940 1.02150 0.55880 0.0420 Uiso c RU 1.000 . .
H H23 0.57110 0.77220 0.48900 0.0410 Uiso c RU 1.000 . .
H H24 0.68560 0.61580 0.54520 0.0440 Uiso c RU 1.000 . .
H H2 0.33250 0.95530 0.30510 0.0510 Uiso c RU 1.000 . .
H H2N 0.7183(19) 1.261(3) 0.0898(18) 0.0480 Uiso d U 1.000 . .
H H3N 0.816(2) 1.207(3) 0.1698(18) 0.0480 Uiso d U 1.000 . .
H H4 0.10050 1.07210 0.08190 0.0750 Uiso c RU 1.000 . .
H H3 0.19530 1.08130 0.23830 0.0650 Uiso c RU 1.000 . .
H H1N 0.5116(18) 0.919(2) 0.2803(17) 0.0400 Uiso d U 1.000 . .
H H7A 0.40010 0.71460 0.19220 0.0490 Uiso c RU 1.000 . .
H H7B 0.41660 0.76230 0.29170 0.0490 Uiso c RU 1.000 . .
H H8A 0.46820 0.84700 0.10060 0.0400 Uiso c RU 1.000 . .
H H8B 0.43500 0.97490 0.12920 0.0400 Uiso c RU 1.000 . .
H H11A 0.70120 0.88250 0.35560 0.0460 Uiso c RU 1.000 . .
H H11B 0.73470 0.78670 0.29840 0.0460 Uiso c RU 1.000 . .
H H12A 0.58000 0.71220 0.22240 0.0480 Uiso c RU 1.000 . .
H H12B 0.59020 0.72750 0.32500 0.0480 Uiso c RU 1.000 . .
H H16A 1.00820 0.99200 0.43200 0.0810 Uiso c RUP 0.753(5) A 1
H H16B 1.02190 0.92850 0.34740 0.0810 Uiso c RUP 0.753(5) A 1
H H17A 1.07800 0.79360 0.47450 0.1010 Uiso c RUP 0.753(5) A 1
H H17B 0.98540 0.73480 0.39240 0.1010 Uiso c RUP 0.753(5) A 1
H H17C 0.97190 0.79790 0.47650 0.1010 Uiso c RUP 0.753(5) A 1
H H5 0.13940 0.93220 -0.00740 0.0750 Uiso c RU 1.000 . .
H H6 0.27220 0.80100 0.05900 0.0600 Uiso c RU 1.000 . .
H H16C 1.00540 0.96010 0.43580 0.0810 Uiso c RUP 0.247(5) A 2
H H16D 0.95610 0.83530 0.44850 0.0810 Uiso c RUP 0.247(5) A 2
H H17D 1.08390 0.80320 0.42890 0.1010 Uiso c RUP 0.247(5) A 2
H H17E 1.03950 0.87620 0.33410 0.1010 Uiso c RUP 0.247(5) A 2
H H17F 0.98900 0.75130 0.34540 0.1010 Uiso c RUP 0.247(5) A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 S1 C13 . . 91.43(11) no
O4A P1 O5B . . 114.38(17) no
O4A P1 O6 . . 115.68(17) no
O4A P1 O5A . . 128.22(19) no
O4A P1 O6 . 3_676 75.99(16) no
O4B P1 O5A . . 122.41(18) no
O4B P1 O5B . . 99.01(16) no
O4B P1 O6 . . 137.86(16) no
O4B P1 C22 . . 106.48(14) no
O4B P1 O6 . 3_676 98.48(15) no
O5A P1 O6 . . 69.98(16) no
O5A P1 C22 . . 113.97(15) no
O5A P1 O6 . 3_676 112.18(16) no
O5B P1 O6 . . 100.98(14) no
O5B P1 C22 . . 107.72(13) no
O5B P1 O6 . 3_676 141.12(14) no
O6 P1 C22 . . 102.14(11) no
O4A P1 C22 . . 114.41(15) no
O6 P1 C22 3_676 . 100.12(11) no
O6 P1 O6 . 3_676 45.77(13) no
C18 O3 C19 . . 118.2(2) no
P1 O5A O6 . . 60.75(15) no
P1 O6 O5A . . 49.27(13) no
P1 O6 P1 . 3_676 134.23(16) no
P1 O6 O5A 3_676 . 162.2(2) no
C15 O2 C16A . . 110.2(3) no
C15 O2 C16B . . 133.2(6) no
C8 N1 C12 . . 109.04(19) no
C7 N1 C8 . . 111.58(18) no
C7 N1 C12 . . 111.06(17) no
C8 N1 H1N . . 109.4(15) no
C12 N1 H1N . . 107.8(17) no
C7 N1 H1N . . 107.9(18) no
C13 N2 H2N . . 116.4(19) no
C13 N2 H3N . . 111(2) no
H2N N2 H3N . . 128(3) no
O3 C19 C20 . . 124.5(2) no
O3 C19 C24 . . 115.60(19) no
C20 C19 C24 . . 119.8(2) no
C19 C20 C21 . . 119.2(2) no
C20 C21 C22 . . 122.0(2) no
P1 C22 C23 . . 120.47(17) no
P1 C22 C21 . . 121.92(16) no
C21 C22 C23 . . 117.56(19) no
C22 C23 C24 . . 121.2(2) no
C19 C24 C23 . . 120.2(2) no
O3 C18 H18B . . 110.00 no
O3 C18 H18C . . 109.00 no
H18A C18 H18B . . 110.00 no
O3 C18 H18A . . 110.00 no
H18A C18 H18C . . 109.00 no
H18B C18 H18C . . 109.00 no
C21 C20 H20 . . 120.00 no
C19 C20 H20 . . 120.00 no
C20 C21 H21 . . 119.00 no
C22 C21 H21 . . 119.00 no
C24 C23 H23 . . 119.00 no
C22 C23 H23 . . 119.00 no
C23 C24 H24 . . 120.00 no
C19 C24 H24 . . 120.00 no
C2 C1 C6 . . 118.6(2) no
C6 C1 C7 . . 120.5(2) no
C2 C1 C7 . . 120.9(2) no
C1 C2 C3 . . 120.4(2) no
C2 C3 C4 . . 120.1(3) no
C3 C4 C5 . . 120.0(3) no
C4 C5 C6 . . 120.2(3) no
C1 C6 C5 . . 120.6(3) no
N1 C7 C1 . . 112.38(18) no
N1 C8 C9 . . 108.32(18) no
C8 C9 C10 . . 126.54(19) no
S1 C9 C8 . . 120.79(16) no
S1 C9 C10 . . 112.42(18) no
C9 C10 C11 . . 119.7(2) no
C11 C10 C14 . . 127.5(2) no
C9 C10 C14 . . 112.75(19) no
C10 C11 C12 . . 111.89(19) no
N1 C12 C11 . . 111.51(17) no
N2 C13 C14 . . 129.3(2) no
S1 C13 C14 . . 111.32(17) no
S1 C13 N2 . . 119.36(17) no
C10 C14 C13 . . 112.0(2) no
C10 C14 C15 . . 128.92(19) no
C13 C14 C15 . . 119.0(2) no
O1 C15 O2 . . 121.9(2) no
O1 C15 C14 . . 125.3(2) no
O2 C15 C14 . . 112.8(2) no
O2 C16A C17A . . 103.6(4) no
O2 C16B C17B . . 115.1(12) no
C1 C2 H2 . . 120.00 no
C3 C2 H2 . . 120.00 no
C2 C3 H3 . . 120.00 no
C4 C3 H3 . . 120.00 no
C3 C4 H4 . . 120.00 no
C5 C4 H4 . . 120.00 no
C4 C5 H5 . . 120.00 no
C6 C5 H5 . . 120.00 no
C1 C6 H6 . . 120.00 no
C5 C6 H6 . . 120.00 no
N1 C7 H7A . . 109.00 no
N1 C7 H7B . . 109.00 no
C1 C7 H7A . . 109.00 no
C1 C7 H7B . . 109.00 no
H7A C7 H7B . . 108.00 no
N1 C8 H8A . . 110.00 no
N1 C8 H8B . . 110.00 no
C9 C8 H8A . . 110.00 no
C9 C8 H8B . . 110.00 no
H8A C8 H8B . . 108.00 no
C10 C11 H11A . . 109.00 no
C10 C11 H11B . . 109.00 no
C12 C11 H11A . . 109.00 no
C12 C11 H11B . . 109.00 no
H11A C11 H11B . . 108.00 no
N1 C12 H12A . . 109.00 no
N1 C12 H12B . . 109.00 no
C11 C12 H12A . . 109.00 no
C11 C12 H12B . . 109.00 no
H12A C12 H12B . . 108.00 no
O2 C16A H16A . . 111.00 no
O2 C16A H16B . . 111.00 no
C17A C16A H16A . . 111.00 no
C17A C16A H16B . . 111.00 no
H16A C16A H16B . . 109.00 no
O2 C16B H16D . . 109.00 no
C17B C16B H16C . . 108.00 no
C17B C16B H16D . . 108.00 no
H16C C16B H16D . . 107.00 no
O2 C16B H16C . . 109.00 no
H17A C17A H17C . . 109.00 no
H17B C17A H17C . . 110.00 no
C16A C17A H17A . . 109.00 no
C16A C17A H17B . . 109.00 no
C16A C17A H17C . . 109.00 no
H17A C17A H17B . . 109.00 no
C16B C17B H17D . . 110.00 no
C16B C17B H17E . . 109.00 no
C16B C17B H17F . . 109.00 no
H17D C17B H17E . . 109.00 no
H17D C17B H17F . . 110.00 no
H17E C17B H17F . . 109.00 no
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
S1 C9 . 1.743(2) no
S1 C13 . 1.739(2) no
P1 O4A . 1.425(3) no
P1 O5B . 1.622(3) no
P1 O6 . 1.583(3) no
P1 C22 . 1.801(2) no
P1 O6 3_676 1.723(3) no
P1 O4B . 1.527(3) no
P1 O5A . 1.375(3) no
O3 C18 . 1.407(4) no
O3 C19 . 1.369(3) no
O5A O6 . 1.705(4) no
O1 C15 . 1.217(3) no
O2 C16A . 1.476(6) no
O2 C15 . 1.346(3) no
O2 C16B . 1.393(16) no
N1 C8 . 1.494(3) no
N1 C7 . 1.510(3) no
N1 C12 . 1.501(3) no
N2 C13 . 1.351(3) no
N1 H1N . 0.93(2) no
N2 H2N . 0.95(3) no
N2 H3N . 0.84(3) no
C19 C20 . 1.382(3) no
C19 C24 . 1.385(3) no
C20 C21 . 1.394(3) no
C21 C22 . 1.378(3) no
C22 C23 . 1.401(3) no
C23 C24 . 1.375(3) no
C18 H18A . 0.9800 no
C18 H18B . 0.9800 no
C18 H18C . 0.9800 no
C20 H20 . 0.9500 no
C21 H21 . 0.9500 no
C23 H23 . 0.9500 no
C24 H24 . 0.9500 no
C1 C2 . 1.387(3) no
C1 C7 . 1.500(4) no
C1 C6 . 1.393(3) no
C2 C3 . 1.381(4) no
C3 C4 . 1.377(4) no
C4 C5 . 1.375(4) no
C5 C6 . 1.373(4) no
C8 C9 . 1.486(3) no
C9 C10 . 1.352(3) no
C10 C11 . 1.503(3) no
C10 C14 . 1.448(3) no
C11 C12 . 1.517(4) no
C13 C14 . 1.391(3) no
C14 C15 . 1.448(4) no
C16A C17A . 1.497(6) no
C16B C17B . 1.246(19) no
C2 H2 . 0.9500 no
C3 H3 . 0.9500 no
C4 H4 . 0.9500 no
C5 H5 . 0.9500 no
C6 H6 . 0.9500 no
C7 H7A . 0.9900 no
C7 H7B . 0.9900 no
C8 H8A . 0.9900 no
C8 H8B . 0.9900 no
C11 H11A . 0.9900 no
C11 H11B . 0.9900 no
C12 H12A . 0.9900 no
C12 H12B . 0.9900 no
C16A H16A . 0.9900 no
C16A H16B . 0.9900 no
C16B H16C . 0.9900 no
C16B H16D . 0.9900 no
C17A H17C . 0.9800 no
C17A H17A . 0.9800 no
C17A H17B . 0.9800 no
C17B H17D . 0.9800 no
C17B H17E . 0.9800 no
C17B H17F . 0.9800 no
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
_geom_hbond_publ_flag
N1 H1N O4A . 0.93(2) 1.79(3) 2.699(4) 165(2) yes
N1 H1N O4B . 0.93(2) 1.72(2) 2.641(4) 171(2) yes
N2 H2N O5A 4_574 0.95(3) 1.98(3) 2.894(4) 160(3) yes
N2 H2N O5B 4_574 0.95(3) 1.77(3) 2.686(4) 162(3) yes
N2 H3N O1 . 0.84(3) 2.11(3) 2.761(3) 135(3) yes
C6 H6 O5B 2_645 0.95 2.37 3.273(4) 159 yes
C7 H7A O4B 2_645 0.99 2.44 3.373(4) 157 yes
C7 H7B S1 2_645 0.99 2.69 3.591(2) 152 yes
C8 H8A O5B 2_645 0.99 2.57 3.488(4) 154 yes
C18 H18B O1 3_776 0.98 2.60 3.251(4) 124 yes
C20 H20 O1 3_776 0.95 2.59 3.524(3) 168 yes
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_4
_geom_torsion
_geom_torsion_publ_flag
C13 S1 C9 C10 . . . -1.85(18) no
C13 S1 C9 C8 . . . 172.78(18) no
C9 S1 C13 C14 . . . 2.30(17) no
C9 S1 C13 N2 . . . -179.77(19) no
C22 P1 O5A O6 . . . -94.76(15) no
O5B P1 O5A O6 . . . -179.4(4) no
O4B P1 O6 O5A . . . -116.6(2) no
O6 P1 O5A O6 3_676 . . 18.13(17) no
O4A P1 O6 O5A . . . -123.7(2) no
O6 P1 O6 O5A 3_676 . . -156.3(2) no
O4A P1 O6 P1 . . 3_676 32.6(3) no
O4B P1 O6 P1 . . 3_676 39.7(3) no
O5A P1 O6 P1 . . 3_676 156.3(3) no
O5B P1 O6 P1 . . 3_676 156.6(2) no
O5B P1 O6 O5A . . . 0.31(19) no
C22 P1 O6 O5A . . . 111.34(16) no
O4B P1 O5A O6 . . . 134.7(2) no
O4B P1 O6 P1 3_676 3_676 . 154.3(2) no
O5A P1 O6 P1 3_676 3_676 . 24.1(3) no
O5B P1 O6 P1 3_676 3_676 . 38.4(3) no
O6 P1 O6 P1 3_676 3_676 . 0.02(18) no
C22 P1 O6 P1 3_676 3_676 . -97.2(2) no
O4A P1 C22 C23 . . . -56.9(2) no
O4B P1 C22 C23 . . . -79.8(2) no
O5A P1 C22 C23 . . . 142.2(2) no
O5B P1 C22 C23 . . . 174.75(19) no
O6 P1 C22 C23 . . . 68.9(2) no
O6 P1 C22 C23 3_676 . . 22.2(2) no
O6 P1 C22 C21 . . . -113.8(2) no
O6 P1 C22 C21 3_676 . . -160.46(19) no
O5A P1 C22 C21 . . . -40.5(2) no
O4A P1 O6 P1 3_676 3_676 . 150.0(3) no
O4B P1 C22 C21 . . . 97.5(2) no
C22 P1 O6 P1 . . 3_676 -92.4(2) no
O5B P1 C22 C21 . . . -7.9(2) no
O4A P1 O5A O6 . . . 107.5(2) no
O4A P1 C22 C21 . . . 120.4(2) no
O6 P1 O6 P1 3_676 . 3_676 0.00(16) no
C18 O3 C19 C24 . . . 177.2(2) no
C18 O3 C19 C20 . . . -4.1(3) no
C16A O2 C15 O1 . . . -0.6(4) no
C16A O2 C15 C14 . . . 178.1(3) no
C15 O2 C16A C17A . . . -173.1(3) no
C7 N1 C12 C11 . . . -169.64(18) no
C12 N1 C8 C9 . . . -52.7(2) no
C7 N1 C8 C9 . . . -175.70(17) no
C8 N1 C12 C11 . . . 67.0(2) no
C12 N1 C7 C1 . . . -174.44(18) no
C8 N1 C7 C1 . . . -52.6(2) no
O3 C19 C24 C23 . . . 179.1(2) no
C24 C19 C20 C21 . . . -1.1(3) no
C20 C19 C24 C23 . . . 0.3(3) no
O3 C19 C20 C21 . . . -179.7(2) no
C19 C20 C21 C22 . . . 0.8(3) no
C20 C21 C22 P1 . . . -177.16(18) no
C20 C21 C22 C23 . . . 0.2(3) no
C21 C22 C23 C24 . . . -1.0(3) no
P1 C22 C23 C24 . . . 176.45(18) no
C22 C23 C24 C19 . . . 0.7(3) no
C7 C1 C6 C5 . . . -175.7(3) no
C2 C1 C7 N1 . . . -82.4(3) no
C7 C1 C2 C3 . . . 177.0(3) no
C6 C1 C7 N1 . . . 95.7(3) no
C2 C1 C6 C5 . . . 2.4(4) no
C6 C1 C2 C3 . . . -1.1(4) no
C1 C2 C3 C4 . . . -0.7(4) no
C2 C3 C4 C5 . . . 1.3(5) no
C3 C4 C5 C6 . . . -0.1(5) no
C4 C5 C6 C1 . . . -1.8(5) no
N1 C8 C9 S1 . . . -153.96(15) no
N1 C8 C9 C10 . . . 19.9(3) no
S1 C9 C10 C11 . . . 177.33(16) no
S1 C9 C10 C14 . . . 0.9(2) no
C8 C9 C10 C11 . . . 3.1(3) no
C8 C9 C10 C14 . . . -173.3(2) no
C9 C10 C11 C12 . . . 8.0(3) no
C14 C10 C11 C12 . . . -176.1(2) no
C9 C10 C14 C13 . . . 0.8(3) no
C9 C10 C14 C15 . . . -176.2(2) no
C11 C10 C14 C13 . . . -175.2(2) no
C11 C10 C14 C15 . . . 7.8(4) no
C10 C11 C12 N1 . . . -42.3(3) no
S1 C13 C14 C10 . . . -2.2(2) no
N2 C13 C14 C15 . . . -2.5(4) no
S1 C13 C14 C15 . . . 175.15(17) no
N2 C13 C14 C10 . . . -179.9(2) no
C10 C14 C15 O1 . . . -175.9(2) no
C10 C14 C15 O2 . . . 5.5(3) no
C13 C14 C15 O1 . . . 7.3(4) no
C13 C14 C15 O2 . . . -171.4(2) no
