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#$Date: 2022-12-07 04:26:09 +0200 (Wed, 07 Dec 2022) $
#$Revision: 279758 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/59/7245976.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_7245976
loop_
_publ_author_name
'Hua, Xiu-Ni'
'Pan, Xia'
'Zhu, Yang'
'Cai, Zhuoer'
'Song, Qi'
'Li, Yaozhenhui'
'Feng, Wenbin'
'Chen, Xin'
'Zhang, Hui'
'Sun, Baiwang'
_publ_section_title
;
 Novel pharmaceutical salts of cephalexin with organic counterions:
 structural analysis and properties
;
_journal_issue                   54
_journal_name_full               'RSC Advances'
_journal_page_first              34843
_journal_page_last               34850
_journal_paper_doi               10.1039/D2RA05565A
_journal_volume                  12
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H18 N3 O4 S, C7 H5 O4, H2 O'
_chemical_formula_sum            'C23 H25 N3 O9 S'
_chemical_formula_weight         519.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-10-29 deposited with the CCDC.	2022-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.858(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3188(13)
_cell_length_b                   7.2613(9)
_cell_length_c                   14.983(2)
_cell_measurement_reflns_used    2530
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4020
_cell_measurement_theta_min      2.1830
_cell_volume                     1225.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8395
_diffrn_reflns_point_group_measured_fraction_full 0.917
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.153
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       strip
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1134 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         3942
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0598P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1080
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_full    0.819
_reflns_Friedel_fraction_max     0.819
_reflns_number_gt                3182
_reflns_number_total             3942
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra05565a2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7245976
_shelx_shelxl_version_number     2014/7
_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_min   0.963
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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 0.52150(10) 0.69583(17) 0.20317(7) 0.0546(3) Uani 1 1 d . . . . .
O1 O 0.9656(2) 0.5555(5) 0.37447(18) 0.0480(8) Uani 1 1 d . . . . .
H1 H 1.0118 0.5174 0.4161 0.072 Uiso 1 1 calc R U . . .
O2 O 0.8315(2) 0.4852(5) 0.46843(18) 0.0508(8) Uani 1 1 d . . . . .
O3 O 0.6490(2) 0.7911(5) 0.48653(18) 0.0533(9) Uani 1 1 d . . . . .
O4 O 0.2356(2) 0.6545(4) 0.3501(2) 0.0538(8) Uani 1 1 d . . . . .
O5 O 0.2078(3) 0.5978(5) 0.6545(2) 0.0628(9) Uani 1 1 d . . . . .
O6 O 0.0827(2) 0.5720(5) 0.7588(2) 0.0655(10) Uani 1 1 d . . . . .
O7 O 0.4283(2) 0.6269(4) 0.69638(18) 0.0505(8) Uani 1 1 d . . . . .
H7 H 0.3662 0.6322 0.6631 0.076 Uiso 1 1 calc R U . . .
O8 O 0.1572(3) 0.6014(6) 0.9251(2) 0.0666(10) Uani 1 1 d . . . . .
H8 H 0.1091 0.5776 0.8820 0.100 Uiso 1 1 calc R U . . .
O9 O 0.1114(2) 0.4383(5) 0.50425(19) 0.0562(9) Uani 1 1 d . . . . .
H9A H 0.1227 0.5334 0.5467 0.067 Uiso 1 1 d R U . . .
H9B H 0.1823 0.4048 0.4953 0.067 Uiso 1 1 d R U . . .
N1 N 0.0876(2) 0.9292(5) 0.3573(2) 0.0402(8) Uani 1 1 d . . . . .
H1A H 0.0344 0.9979 0.3244 0.060 Uiso 1 1 calc R U . . .
H1B H 0.0812 0.9487 0.4152 0.060 Uiso 1 1 calc R U . . .
H1C H 0.0743 0.8108 0.3446 0.060 Uiso 1 1 calc R U . . .
N2 N 0.4016(3) 0.8265(5) 0.3676(2) 0.0426(8) Uani 1 1 d . . . . .
H2A H 0.4324 0.9348 0.3679 0.051 Uiso 1 1 calc R U . . .
N3 N 0.6475(2) 0.6017(5) 0.3577(2) 0.0371(8) Uani 1 1 d . . . . .
C1 C 0.5322(3) 0.5703(6) 0.3066(3) 0.0413(10) Uani 1 1 d . . . . .
H1D H 0.5112 0.4398 0.2994 0.050 Uiso 1 1 calc R U . . .
C2 C 0.7602(3) 0.5834(5) 0.3239(2) 0.0342(9) Uani 1 1 d . . . . .
C3 C 0.7671(4) 0.5877(6) 0.2348(2) 0.0392(9) Uani 1 1 d . . . . .
C4 C 0.6605(4) 0.6161(6) 0.1670(3) 0.0481(11) Uani 1 1 d . . . . .
H4A H 0.6447 0.4999 0.1361 0.058 Uiso 1 1 calc R U . . .
H4B H 0.6834 0.7032 0.1228 0.058 Uiso 1 1 calc R U . . .
C5 C 0.8796(4) 0.5583(7) 0.1907(3) 0.0548(12) Uani 1 1 d . . . . .
H5A H 0.9155 0.6752 0.1806 0.082 Uiso 1 1 calc R U . . .
H5B H 0.8611 0.4963 0.1344 0.082 Uiso 1 1 calc R U . . .
H5C H 0.9339 0.4846 0.2291 0.082 Uiso 1 1 calc R U . . .
C6 C 0.8549(3) 0.5373(6) 0.3951(3) 0.0358(9) Uani 1 1 d . . . . .
C7 C 0.6041(3) 0.7033(6) 0.4238(2) 0.0388(9) Uani 1 1 d . . . . .
C8 C 0.4760(3) 0.6662(6) 0.3849(3) 0.0431(10) Uani 1 1 d . . . . .
H8A H 0.4380 0.5760 0.4213 0.052 Uiso 1 1 calc R U . . .
C9 C 0.2828(3) 0.8041(6) 0.3511(2) 0.0359(9) Uani 1 1 d . . . . .
C10 C 0.2096(3) 0.9799(5) 0.3364(2) 0.0326(9) Uani 1 1 d . . . . .
H10 H 0.2420 1.0743 0.3788 0.039 Uiso 1 1 calc R U . . .
C11 C 0.2034(3) 1.0565(6) 0.2412(3) 0.0364(9) Uani 1 1 d . . . . .
C12 C 0.2008(4) 1.2444(6) 0.2282(3) 0.0548(13) Uani 1 1 d . . . . .
H12 H 0.2103 1.3230 0.2774 0.066 Uiso 1 1 calc R U . . .
C13 C 0.1842(5) 1.3170(8) 0.1424(4) 0.0732(17) Uani 1 1 d . . . . .
H13 H 0.1835 1.4438 0.1337 0.088 Uiso 1 1 calc R U . . .
C14 C 0.1687(5) 1.2001(10) 0.0707(3) 0.0777(17) Uani 1 1 d . . . . .
H14 H 0.1552 1.2486 0.0131 0.093 Uiso 1 1 calc R U . . .
C15 C 0.1728(5) 1.0135(9) 0.0819(3) 0.0753(16) Uani 1 1 d . . . . .
H15 H 0.1644 0.9359 0.0322 0.090 Uiso 1 1 calc R U . . .
C16 C 0.1894(4) 0.9404(7) 0.1677(3) 0.0535(12) Uani 1 1 d . . . . .
H16 H 0.1912 0.8135 0.1759 0.064 Uiso 1 1 calc R U . . .
C17 C 0.2862(3) 0.6159(6) 0.8059(3) 0.0395(9) Uani 1 1 d . . . . .
C18 C 0.4036(3) 0.6335(5) 0.7838(3) 0.0406(10) Uani 1 1 d . . . . .
C19 C 0.4966(4) 0.6593(7) 0.8489(3) 0.0530(12) Uani 1 1 d . . . . .
H19 H 0.5735 0.6733 0.8332 0.064 Uiso 1 1 calc R U . . .
C20 C 0.4750(4) 0.6642(8) 0.9378(3) 0.0636(14) Uani 1 1 d . . . . .
H20 H 0.5378 0.6830 0.9819 0.076 Uiso 1 1 calc R U . . .
C21 C 0.3610(4) 0.6415(7) 0.9625(3) 0.0586(13) Uani 1 1 d . . . . .
H21 H 0.3481 0.6418 1.0228 0.070 Uiso 1 1 calc R U . . .
C22 C 0.2670(4) 0.6187(6) 0.8974(3) 0.0448(10) Uani 1 1 d . . . . .
C23 C 0.1860(4) 0.5933(6) 0.7351(3) 0.0449(10) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C4 96.45(19) . . ?
C6 O1 H1 109.5 . . ?
C18 O7 H7 109.5 . . ?
C22 O8 H8 109.5 . . ?
H9A O9 H9B 104.3 . . ?
C10 N1 H1A 109.5 . . ?
C10 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C10 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C9 N2 C8 119.1(3) . . ?
C9 N2 H2A 120.4 . . ?
C8 N2 H2A 120.4 . . ?
C7 N3 C2 135.2(3) . . ?
C7 N3 C1 95.5(3) . . ?
C2 N3 C1 125.6(3) . . ?
N3 C1 C8 87.0(3) . . ?
N3 C1 S1 110.6(3) . . ?
C8 C1 S1 115.3(3) . . ?
N3 C1 H1D 113.7 . . ?
C8 C1 H1D 113.7 . . ?
S1 C1 H1D 113.7 . . ?
C3 C2 N3 119.7(3) . . ?
C3 C2 C6 127.8(4) . . ?
N3 C2 C6 112.1(3) . . ?
C2 C3 C5 124.7(4) . . ?
C2 C3 C4 123.2(4) . . ?
C5 C3 C4 112.1(3) . . ?
C3 C4 S1 120.1(3) . . ?
C3 C4 H4A 107.3 . . ?
S1 C4 H4A 107.3 . . ?
C3 C4 H4B 107.3 . . ?
S1 C4 H4B 107.3 . . ?
H4A C4 H4B 106.9 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O2 C6 O1 122.6(4) . . ?
O2 C6 C2 121.1(3) . . ?
O1 C6 C2 116.4(3) . . ?
O3 C7 N3 134.2(3) . . ?
O3 C7 C8 134.3(4) . . ?
N3 C7 C8 91.5(3) . . ?
N2 C8 C7 116.0(4) . . ?
N2 C8 C1 120.1(3) . . ?
C7 C8 C1 85.5(3) . . ?
N2 C8 H8A 111.0 . . ?
C7 C8 H8A 111.0 . . ?
C1 C8 H8A 111.0 . . ?
O4 C9 N2 122.7(4) . . ?
O4 C9 C10 121.1(3) . . ?
N2 C9 C10 116.2(4) . . ?
N1 C10 C11 109.3(3) . . ?
N1 C10 C9 105.3(3) . . ?
C11 C10 C9 114.3(3) . . ?
N1 C10 H10 109.3 . . ?
C11 C10 H10 109.3 . . ?
C9 C10 H10 109.3 . . ?
C12 C11 C16 119.4(4) . . ?
C12 C11 C10 119.4(4) . . ?
C16 C11 C10 120.9(4) . . ?
C11 C12 C13 120.5(5) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.2(5) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C15 C14 C13 121.3(5) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 119.6(5) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C11 C16 C15 120.0(5) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C22 118.0(4) . . ?
C18 C17 C23 121.0(4) . . ?
C22 C17 C23 121.0(4) . . ?
O7 C18 C19 117.9(4) . . ?
O7 C18 C17 120.8(4) . . ?
C19 C18 C17 121.3(4) . . ?
C18 C19 C20 119.4(4) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C19 C20 C21 121.0(4) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 119.8(4) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
O8 C22 C21 117.4(4) . . ?
O8 C22 C17 122.3(4) . . ?
C21 C22 C17 120.4(4) . . ?
O5 C23 O6 123.3(4) . . ?
O5 C23 C17 118.3(4) . . ?
O6 C23 C17 118.4(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 C1 1.792(4) . ?
S1 C4 1.811(4) . ?
O1 C6 1.328(4) . ?
O1 H1 0.8200 . ?
O2 C6 1.217(4) . ?
O3 C7 1.205(5) . ?
O4 C9 1.210(5) . ?
O5 C23 1.257(5) . ?
O6 C23 1.265(5) . ?
O7 C18 1.367(5) . ?
O7 H7 0.8200 . ?
O8 C22 1.355(4) . ?
O8 H8 0.8200 . ?
O9 H9A 0.9391 . ?
O9 H9B 0.8623 . ?
N1 C10 1.493(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 C9 1.352(5) . ?
N2 C8 1.444(5) . ?
N2 H2A 0.8600 . ?
N3 C7 1.366(5) . ?
N3 C2 1.426(4) . ?
N3 C1 1.462(5) . ?
C1 C8 1.555(5) . ?
C1 H1D 0.9800 . ?
C2 C3 1.345(5) . ?
C2 C6 1.472(5) . ?
C3 C5 1.509(5) . ?
C3 C4 1.511(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C7 C8 1.531(5) . ?
C8 H8A 0.9800 . ?
C9 C10 1.526(6) . ?
C10 C11 1.525(5) . ?
C10 H10 0.9800 . ?
C11 C12 1.378(6) . ?
C11 C16 1.383(6) . ?
C12 C13 1.385(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.366(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.366(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.407(5) . ?
C17 C22 1.410(5) . ?
C17 C23 1.480(5) . ?
C18 C19 1.374(6) . ?
C19 C20 1.379(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.388(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(6) . ?
C21 H21 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1D O7 0.98 2.37 3.252(5) 148.9 2_646
N2 H2A O7 0.86 2.38 3.125(4) 145.0 2_656
N1 H1C O4 0.89 2.14 2.614(4) 112.3 .
N1 H1C O1 0.89 2.29 3.067(5) 145.2 1_455
N1 H1B O9 0.89 2.60 3.215(4) 127.1 2_556
N1 H1B O2 0.89 1.93 2.708(4) 144.8 2_656
N1 H1A O6 0.89 1.81 2.670(4) 162.8 2_556
O9 H9B O3 0.86 2.07 2.905(4) 162.2 2_646
O9 H9A O5 0.94 1.85 2.665(4) 143.0 .
O8 H8 O6 0.82 1.84 2.557(4) 145.3 .
O7 H7 O5 0.82 1.80 2.519(4) 145.3 .
O1 H1 O9 0.82 1.74 2.564(4) 179.3 1_655
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
C7 N3 C1 C8 -5.8(3) . . . . ?
C2 N3 C1 C8 -166.8(4) . . . . ?
C7 N3 C1 S1 110.2(3) . . . . ?
C2 N3 C1 S1 -50.8(5) . . . . ?
C4 S1 C1 N3 50.7(3) . . . . ?
C4 S1 C1 C8 147.3(3) . . . . ?
C7 N3 C2 C3 -133.0(5) . . . . ?
C1 N3 C2 C3 19.7(6) . . . . ?
C7 N3 C2 C6 54.4(6) . . . . ?
C1 N3 C2 C6 -152.9(4) . . . . ?
N3 C2 C3 C5 -176.1(4) . . . . ?
C6 C2 C3 C5 -4.8(7) . . . . ?
N3 C2 C3 C4 1.6(6) . . . . ?
C6 C2 C3 C4 172.9(4) . . . . ?
C2 C3 C4 S1 13.5(6) . . . . ?
C5 C3 C4 S1 -168.6(3) . . . . ?
C1 S1 C4 C3 -37.0(4) . . . . ?
C3 C2 C6 O2 -157.9(4) . . . . ?
N3 C2 C6 O2 13.9(5) . . . . ?
C3 C2 C6 O1 22.0(6) . . . . ?
N3 C2 C6 O1 -166.2(3) . . . . ?
C2 N3 C7 O3 -14.5(8) . . . . ?
C1 N3 C7 O3 -172.5(5) . . . . ?
C2 N3 C7 C8 163.9(4) . . . . ?
C1 N3 C7 C8 5.9(3) . . . . ?
C9 N2 C8 C7 -166.5(3) . . . . ?
C9 N2 C8 C1 93.0(4) . . . . ?
O3 C7 C8 N2 51.4(7) . . . . ?
N3 C7 C8 N2 -127.0(4) . . . . ?
O3 C7 C8 C1 172.8(5) . . . . ?
N3 C7 C8 C1 -5.5(3) . . . . ?
N3 C1 C8 N2 122.7(4) . . . . ?
S1 C1 C8 N2 11.4(5) . . . . ?
N3 C1 C8 C7 5.1(3) . . . . ?
S1 C1 C8 C7 -106.2(3) . . . . ?
C8 N2 C9 O4 0.1(6) . . . . ?
C8 N2 C9 C10 178.1(3) . . . . ?
O4 C9 C10 N1 20.8(5) . . . . ?
N2 C9 C10 N1 -157.3(3) . . . . ?
O4 C9 C10 C11 -99.2(4) . . . . ?
N2 C9 C10 C11 82.7(4) . . . . ?
N1 C10 C11 C12 97.3(4) . . . . ?
C9 C10 C11 C12 -145.0(4) . . . . ?
N1 C10 C11 C16 -76.7(4) . . . . ?
C9 C10 C11 C16 41.0(5) . . . . ?
C16 C11 C12 C13 0.1(7) . . . . ?
C10 C11 C12 C13 -174.0(4) . . . . ?
C11 C12 C13 C14 0.9(8) . . . . ?
C12 C13 C14 C15 -1.9(9) . . . . ?
C13 C14 C15 C16 1.9(9) . . . . ?
C12 C11 C16 C15 -0.1(7) . . . . ?
C10 C11 C16 C15 173.9(4) . . . . ?
C14 C15 C16 C11 -0.9(8) . . . . ?
C22 C17 C18 O7 178.2(4) . . . . ?
C23 C17 C18 O7 -1.1(6) . . . . ?
C22 C17 C18 C19 -2.3(6) . . . . ?
C23 C17 C18 C19 178.3(4) . . . . ?
O7 C18 C19 C20 -179.1(4) . . . . ?
C17 C18 C19 C20 1.4(7) . . . . ?
C18 C19 C20 C21 0.7(8) . . . . ?
C19 C20 C21 C22 -1.8(8) . . . . ?
C20 C21 C22 O8 -178.5(5) . . . . ?
C20 C21 C22 C17 0.7(7) . . . . ?
C18 C17 C22 O8 -179.6(4) . . . . ?
C23 C17 C22 O8 -0.2(6) . . . . ?
C18 C17 C22 C21 1.2(6) . . . . ?
C23 C17 C22 C21 -179.4(4) . . . . ?
C18 C17 C23 O5 -2.9(6) . . . . ?
C22 C17 C23 O5 177.7(4) . . . . ?
C18 C17 C23 O6 177.7(4) . . . . ?
C22 C17 C23 O6 -1.6(6) . . . . ?
