#------------------------------------------------------------------------------
#$Date: 2024-08-05 19:58:36 +0200 (Mon 05 de Aug de 2024) $
#$Revision: 293745 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/18/1571895.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_1571895
loop_
_publ_author_name
'Hua, Yong'
'Zou, Zhi'
'Prescimone, Alessandro'
'Ward, Thomas R.'
'Mayor, Marcel'
'Köhler, Valentin'
_publ_section_title
;
 NSPs: chromogenic linkers for fast, selective, and irreversible cysteine
 modification.
;
_journal_issue                   28
_journal_name_full               'Chemical science'
_journal_page_first              10997
_journal_page_last               11004
_journal_paper_doi               10.1039/d4sc01710b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C16 H16 N2 O4 S2, H2 O'
_chemical_formula_sum            'C16 H18 N2 O5 S2'
_chemical_formula_weight         382.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-17
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-06-30 deposited with the CCDC.	2024-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                113.735(2)
_cell_angle_beta                 92.388(2)
_cell_angle_gamma                99.774(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2197(2)
_cell_length_b                   9.7011(2)
_cell_length_c                   11.5746(2)
_cell_measurement_reflns_used    54727
_cell_measurement_temperature    150
_cell_measurement_theta_max      73.32
_cell_measurement_theta_min      4.20
_cell_volume                     826.42(3)
_computing_cell_refinement       'X-Area Recipe 1.37.0.0 (STOE, 2021)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)'
_computing_data_reduction
;
X-Area Integrate 2.5.1.0 (STOE, 2021)
X-Area LANA 2.6.2.0 (STOE, 2021)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'EIGER2 1M'
_diffrn_detector_area_resol_mean 13.33
_diffrn_detector_type            'DECTRIS EIGER2 1M'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
 5740 frames, detector distance = 40 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_unetI/netI     0.0073
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22220
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         72.830
_diffrn_reflns_theta_min         5.076
_diffrn_source                   'Axo Cu'
_diffrn_source_current           1.00
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    3.208
_exptl_absorpt_correction_T_max  0.1331
_exptl_absorpt_correction_T_min  0.1022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens in: F. R. Ahmed (Editor), "Crystallographic Computing", Munksgaard,
Copenhagen (1970), 255 - 270. Afterwards scaling of reflection intensities was
performed within STOE LANA. J. Koziskova, F. Hahn, J. Richter, J. Kozisek, Acta
Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Finally a spherical absorption correction was done within STOE LANA.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of water and acetone  by solvent layering'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.1
_exptl_crystal_size_rad          0.170
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0111(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0379
_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)+(0.0555P)²+0.6655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1010
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3191
_reflns_number_total             3201
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc01710b2.cif
_cod_data_source_block           yh20220106-1_150k
_cod_depositor_comments          'Adding full bibliography for 1571895.cif.'
_cod_database_code               1571895
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.740
_shelx_estimated_absorpt_t_min   0.566
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C7(H7), C10(H10), C6(H6), C8(H8), C13(H13), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_date_sample_data_collection 2022-01-15
_olex2_date_sample_submission    2022-01-10
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop in perfluoroether oil'
_olex2_submission_original_sample_id YH20220106_1_150K
_olex2_submission_special_instructions 'No special instructions were received'
_stoe_detector_distance          '40.0 mm'
_stoe_detector_pixelsize_x       '0.075 mm'
_stoe_detector_pixelsize_y       '0.075 mm'
_stoe_detector_size_x            '8.0 cm'
_stoe_detector_size_y            '7.7 cm'
_stoe_evaluation_integration_a   7.2
_stoe_evaluation_integration_b   0.1
_stoe_evaluation_integration_ems 0.016
_stoe_evaluation_lana_bis_l_even_max -
_stoe_evaluation_lana_bis_l_odd_max -
_stoe_evaluation_lana_bos_l_even_max 4
_stoe_evaluation_lana_bos_l_odd_max 1
_stoe_evaluation_lana_completeness 97.4
_stoe_evaluation_lana_dxs_max_order 1
_stoe_evaluation_lana_dys_max_order 1
_stoe_evaluation_lana_fs_max_order 3
_stoe_evaluation_lana_max_2theta_available 145.7
_stoe_evaluation_lana_max_2theta_desired 145.7
_stoe_evaluation_lana_mean_redundancy 6.9
_stoe_evaluation_lana_number_refls_after_or 22220
_stoe_evaluation_lana_number_refls_outliers 7089
_stoe_evaluation_lana_number_refls_total 29309
_stoe_evaluation_lana_number_refls_unique 3201
_stoe_evaluation_lana_number_refls_written 22220
_stoe_evaluation_lana_or_c1      0.035
_stoe_evaluation_lana_or_c2      0
_stoe_evaluation_lana_or_c3      0
_stoe_evaluation_lana_or_c4      0.7
_stoe_evaluation_lana_point_group -1
_stoe_evaluation_lana_table
;
#--------------------------------------
2Theta          15.5   30.9   46.3   61.7   77.1   92.5  107.9  123.3  138.7
#--------------------------------------
<Resolution>    4.47   2.77   1.94   1.49   1.23   1.07   0.95   0.88   0.83
N(total)         119   1089   2408   4210   6733   6576   3936   2931   1307
<Redundancy>     3.3    8.2    8.7    9.3   11.2    9.1    5.1    3.8    2.6
Complet. [perc] 90.3  100.0  100.0  100.0  100.0   99.6   99.1   98.4   84.2
<I/sigma>     1335.6  698.7  381.0  234.1  190.6  151.3  118.0  121.0  118.2
R(int)         0.009  0.011  0.013  0.015  0.015  0.015  0.019  0.020  0.053
#--------------------------------------
;
_stoe_measurement_identifier     YH20220106-1_150K
_stoe_measurement_max_exposure_per_frame '15.0 s'
_stoe_measurement_mean_exposure_per_frame '15.0 s'
_stoe_measurement_min_exposure_per_frame '4.0 s'
_stoe_measurement_total_exposure_time '23.9 h'
_stoe_measurement_total_frame_number 5740
_stoe_measurement_total_run_number 99
_stoe_measurement_tube_power     '50.0 W'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.68134(5) -0.14334(5) 0.08109(4) 0.02088(15) Uani 1 1 d . . . . .
S2 S 0.51116(5) 0.15197(5) 0.43471(4) 0.02271(15) Uani 1 1 d . . . . .
O3 O 0.56095(17) -0.27502(15) 0.07356(13) 0.0293(3) Uani 1 1 d . . . . .
O4 O 0.85100(16) -0.14765(15) 0.12169(13) 0.0272(3) Uani 1 1 d . . . . .
O2 O 0.67273(18) -0.11748(16) -0.03493(12) 0.0297(3) Uani 1 1 d . . . . .
O1 O 0.97376(18) 0.63751(16) 0.67020(14) 0.0328(3) Uani 1 1 d . . . . .
H1 H 0.957430 0.723640 0.720057 0.049 Uiso 1 1 calc R U . . .
O5 O 0.9088(2) 0.89391(18) 0.81618(15) 0.0422(4) Uani 1 1 d G . . . .
H5A H 0.851375 0.896109 0.876074 0.063 Uiso 1 1 d G U . . .
H5B H 0.986085 0.973508 0.850107 0.063 Uiso 1 1 d G U . . .
N2 N 0.80414(19) 0.30532(18) 0.90850(14) 0.0225(3) Uani 1 1 d . . . . .
N1 N 0.8272(2) 0.55033(17) 0.59300(15) 0.0237(3) Uani 1 1 d . . . . .
C4 C 0.7544(2) 0.4094(2) 0.58933(17) 0.0221(4) Uani 1 1 d . . . . .
C5 C 0.7759(2) 0.3742(2) 0.69914(17) 0.0224(4) Uani 1 1 d . . . . .
C2 C 0.6590(2) 0.4255(2) 0.40904(17) 0.0222(4) Uani 1 1 d . . . . .
C9 C 0.7969(2) 0.4499(2) 0.92520(18) 0.0249(4) Uani 1 1 d . . . . .
H9 H 0.799939 0.526879 1.008668 0.030 Uiso 1 1 calc R U . . .
C16 C 0.6288(2) 0.0231(2) 0.19951(17) 0.0236(4) Uani 1 1 d . . . . .
H16A H 0.710701 0.115183 0.208130 0.028 Uiso 1 1 calc R U . . .
H16B H 0.518071 0.033976 0.171464 0.028 Uiso 1 1 calc R U . . .
C3 C 0.6481(2) 0.3290(2) 0.47650(17) 0.0216(4) Uani 1 1 d . . . . .
C7 C 0.7967(2) 0.1940(2) 0.79040(18) 0.0245(4) Uani 1 1 d . . . . .
H7 H 0.801583 0.092524 0.779838 0.029 Uiso 1 1 calc R U . . .
C15 C 0.6254(2) 0.0167(2) 0.32853(17) 0.0228(4) Uani 1 1 d . . . . .
H15A H 0.741007 0.039609 0.369041 0.027 Uiso 1 1 calc R U . . .
H15B H 0.573382 -0.088879 0.316136 0.027 Uiso 1 1 calc R U . . .
C10 C 0.5802(2) 0.4104(2) 0.29303(17) 0.0255(4) Uani 1 1 d . . . . .
H10 H 0.496088 0.323013 0.243372 0.031 Uiso 1 1 calc R U . . .
C6 C 0.7821(2) 0.2253(2) 0.68543(17) 0.0234(4) Uani 1 1 d . . . . .
H6 H 0.776146 0.145374 0.602931 0.028 Uiso 1 1 calc R U . . .
C8 C 0.7852(2) 0.4871(2) 0.82324(17) 0.0240(4) Uani 1 1 d . . . . .
H8 H 0.783409 0.590070 0.836751 0.029 Uiso 1 1 calc R U . . .
C1 C 0.7785(2) 0.5598(2) 0.48190(17) 0.0236(4) Uani 1 1 d . . . . .
C13 C 0.8303(3) 0.6753(2) 0.44111(19) 0.0282(4) Uani 1 1 d . . . . .
H13 H 0.914005 0.763187 0.490365 0.034 Uiso 1 1 calc R U . . .
C11 C 0.6286(3) 0.5262(2) 0.25341(18) 0.0287(4) Uani 1 1 d . . . . .
H11 H 0.575916 0.518205 0.175696 0.034 Uiso 1 1 calc R U . . .
C12 C 0.7536(3) 0.6553(2) 0.3250(2) 0.0309(4) Uani 1 1 d . . . . .
H12 H 0.786343 0.730809 0.293214 0.037 Uiso 1 1 calc R U . . .
C14 C 0.8148(3) 0.2654(2) 1.01855(18) 0.0289(4) Uani 1 1 d . . . . .
H14A H 0.826310 0.358804 1.097386 0.043 Uiso 1 1 calc R U . . .
H14B H 0.911701 0.218604 1.017738 0.043 Uiso 1 1 calc R U . . .
H14C H 0.713618 0.192431 1.013591 0.043 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -2 30 0.0660
28 25 -30 0.0658
7 -15 9 0.0635
-15 2 -6 0.0622
9 30 -8 0.0829
-1 2 -10 0.0684
30 3 20 0.0815
-11 30 -29 0.0564
-2 -2 3 0.0599
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
O3 S1 O4 112.38(8) . . ?
O3 S1 O2 113.50(8) . . ?
O3 S1 C16 107.15(8) . . ?
O4 S1 C16 107.02(8) . . ?
O2 S1 O4 111.64(8) . . ?
O2 S1 C16 104.51(8) . . ?
C3 S2 C15 102.09(8) . . ?
N1 O1 H1 109.5 . . ?
H5A O5 H5B 104.5 . . ?
C9 N2 C7 120.32(16) . . ?
C9 N2 C14 120.59(16) . . ?
C7 N2 C14 119.06(16) . . ?
C4 N1 O1 122.22(15) . . ?
C1 N1 O1 122.76(15) . . ?
C1 N1 C4 110.19(15) . . ?
N1 C4 C5 121.21(16) . . ?
N1 C4 C3 108.16(16) . . ?
C3 C4 C5 130.01(16) . . ?
C6 C5 C4 121.51(16) . . ?
C6 C5 C8 117.13(17) . . ?
C8 C5 C4 121.31(16) . . ?
C10 C2 C3 133.96(18) . . ?
C10 C2 C1 118.94(17) . . ?
C1 C2 C3 107.10(16) . . ?
N2 C9 H9 119.6 . . ?
N2 C9 C8 120.79(17) . . ?
C8 C9 H9 119.6 . . ?
S1 C16 H16A 109.0 . . ?
S1 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C15 C16 S1 112.89(13) . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C4 C3 S2 125.55(14) . . ?
C4 C3 C2 107.05(16) . . ?
C2 C3 S2 127.08(14) . . ?
N2 C7 H7 119.5 . . ?
N2 C7 C6 120.91(17) . . ?
C6 C7 H7 119.5 . . ?
S2 C15 H15A 109.0 . . ?
S2 C15 H15B 109.0 . . ?
C16 C15 S2 112.87(13) . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C2 C10 H10 120.9 . . ?
C11 C10 C2 118.13(18) . . ?
C11 C10 H10 120.9 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.36(17) . . ?
C7 C6 H6 119.8 . . ?
C5 C8 H8 119.8 . . ?
C9 C8 C5 120.46(17) . . ?
C9 C8 H8 119.8 . . ?
N1 C1 C2 107.24(16) . . ?
N1 C1 C13 129.69(18) . . ?
C13 C1 C2 123.07(18) . . ?
C1 C13 H13 121.7 . . ?
C12 C13 C1 116.60(19) . . ?
C12 C13 H13 121.7 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.67(18) . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C11 121.48(18) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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 O3 1.4467(13) . ?
S1 O4 1.4657(14) . ?
S1 O2 1.4630(13) . ?
S1 C16 1.7824(18) . ?
S2 C3 1.7550(18) . ?
S2 C15 1.8248(18) . ?
O1 H1 0.8400 . ?
O1 N1 1.386(2) . ?
O5 H5A 0.8502 . ?
O5 H5B 0.8499 . ?
N2 C9 1.349(2) . ?
N2 C7 1.349(2) . ?
N2 C14 1.476(2) . ?
N1 C4 1.379(2) . ?
N1 C1 1.374(2) . ?
C4 C5 1.454(2) . ?
C4 C3 1.390(3) . ?
C5 C6 1.399(3) . ?
C5 C8 1.402(3) . ?
C2 C3 1.435(2) . ?
C2 C10 1.408(3) . ?
C2 C1 1.409(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.370(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.521(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.371(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C10 H10 0.9500 . ?
C10 C11 1.382(3) . ?
C6 H6 0.9500 . ?
C8 H8 0.9500 . ?
C1 C13 1.392(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.403(3) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
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
_geom_hbond_publ_flag
O1 H1 O5 0.84 1.71 2.544(2) 175.6 . yes
O5 H5A O2 0.85 1.85 2.666(2) 161.8 1_566 yes
O5 H5B O4 0.85 1.87 2.698(2) 163.6 2_766 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C16 C15 S2 -161.88(10) . . . . ?
O3 S1 C16 C15 57.52(15) . . . . ?
O4 S1 C16 C15 -63.23(15) . . . . ?
O2 S1 C16 C15 178.24(13) . . . . ?
O1 N1 C4 C5 28.6(3) . . . . ?
O1 N1 C4 C3 -159.60(16) . . . . ?
O1 N1 C1 C2 161.00(16) . . . . ?
O1 N1 C1 C13 -19.0(3) . . . . ?
N2 C9 C8 C5 1.8(3) . . . . ?
N2 C7 C6 C5 0.5(3) . . . . ?
N1 C4 C5 C6 -146.88(18) . . . . ?
N1 C4 C5 C8 35.5(3) . . . . ?
N1 C4 C3 S2 -173.24(13) . . . . ?
N1 C4 C3 C2 0.6(2) . . . . ?
N1 C1 C13 C12 -177.65(18) . . . . ?
C4 N1 C1 C2 5.2(2) . . . . ?
C4 N1 C1 C13 -174.83(19) . . . . ?
C4 C5 C6 C7 -177.74(17) . . . . ?
C4 C5 C8 C9 176.64(17) . . . . ?
C5 C4 C3 S2 -2.4(3) . . . . ?
C5 C4 C3 C2 171.43(18) . . . . ?
C2 C10 C11 C12 0.6(3) . . . . ?
C2 C1 C13 C12 2.3(3) . . . . ?
C9 N2 C7 C6 0.2(3) . . . . ?
C3 S2 C15 C16 -73.00(14) . . . . ?
C3 C4 C5 C6 43.3(3) . . . . ?
C3 C4 C5 C8 -134.3(2) . . . . ?
C3 C2 C10 C11 -176.72(19) . . . . ?
C3 C2 C1 N1 -4.7(2) . . . . ?
C3 C2 C1 C13 175.35(17) . . . . ?
C7 N2 C9 C8 -1.3(3) . . . . ?
C15 S2 C3 C4 -100.29(17) . . . . ?
C15 S2 C3 C2 87.10(17) . . . . ?
C10 C2 C3 S2 -4.5(3) . . . . ?
C10 C2 C3 C4 -178.2(2) . . . . ?
C10 C2 C1 N1 175.96(16) . . . . ?
C10 C2 C1 C13 -4.0(3) . . . . ?
C10 C11 C12 C13 -2.3(3) . . . . ?
C6 C5 C8 C9 -1.1(3) . . . . ?
C8 C5 C6 C7 0.0(3) . . . . ?
C1 N1 C4 C5 -175.43(16) . . . . ?
C1 N1 C4 C3 -3.6(2) . . . . ?
C1 C2 C3 S2 176.23(14) . . . . ?
C1 C2 C3 C4 2.5(2) . . . . ?
C1 C2 C10 C11 2.4(3) . . . . ?
C1 C13 C12 C11 0.8(3) . . . . ?
C14 N2 C9 C8 -179.32(17) . . . . ?
C14 N2 C7 C6 178.21(17) . . . . ?
