#------------------------------------------------------------------------------
#$Date: 2023-05-05 04:19:16 +0300 (Fri, 05 May 2023) $
#$Revision: 283200 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/64/7246432.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_7246432
loop_
_publ_author_name
'Arul, Anand'
'Ramaclus, Jerald Vijay'
_publ_section_title
;
 4-[4-(4-Methoxyphenyl)-1,3-butadienyl]-1-methylpyridinium 4-chlorobenzene
 sulphonate (MBMPCBS) -- an efficient nonlinear optical crystal with
 superior thermal stability
;
_journal_issue                   17
_journal_name_full               CrystEngComm
_journal_page_first              2534
_journal_page_last               2545
_journal_paper_doi               10.1039/D3CE00090G
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C17 H18 N O, C6 H4 Cl O3 S '
_chemical_formula_sum            'C23 H22 Cl N O4 S'
_chemical_formula_weight         443.92
_chemical_name_systematic
'4-[4-(4-Methoxyphenyl)-1,3-butadienyl]-1-methylpyridinium 4-chlorobenzene sulfonate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-12-09 deposited with the CCDC.	2023-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.552(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.8216(2)
_cell_length_b                   9.2134(2)
_cell_length_c                   12.6540(4)
_cell_measurement_reflns_used    9353
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30.94
_cell_measurement_theta_min      2.86
_cell_volume                     2163.92(10)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1054
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            36832
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.116
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (bruker, 2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             928
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile-Millipore water'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 2659 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     602
_refine_ls_number_reflns         36832
_refine_ls_number_restraints     176
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0583
_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)+(0.0166P)²+1.1786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1582
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_full    0.912
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                30935
_reflns_number_total             36832
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00090g2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7246432--7246433.cif.'
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               7246432
_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_min   0.915
_shelx_estimated_absorpt_t_max   0.928
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
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
C1 C 0.0734(5) 0.3484(10) 0.4600(7) 0.042(2) Uani 1 1 d . . . . .
C2 C 0.1156(6) 0.4685(10) 0.4473(8) 0.042(2) Uani 1 1 d . . . . .
H2 H 0.112850 0.552465 0.489935 0.050 Uiso 1 1 calc R U . . .
C3 C 0.1616(6) 0.4665(11) 0.3727(9) 0.046(2) Uani 1 1 d . . . . .
H3 H 0.190533 0.549308 0.365577 0.055 Uiso 1 1 calc R U . . .
C4 C 0.1665(4) 0.3461(9) 0.3078(6) 0.0377(19) Uani 1 1 d . . . . .
C5 C 0.1234(5) 0.2260(10) 0.3220(7) 0.044(2) Uani 1 1 d . . . . .
H5 H 0.126308 0.141191 0.280181 0.053 Uiso 1 1 calc R U . . .
C6 C 0.0780(5) 0.2283(10) 0.3939(8) 0.052(2) Uani 1 1 d . . . . .
H6 H 0.048288 0.146239 0.399711 0.062 Uiso 1 1 calc R U . . .
C7 C 0.2134(5) 0.3398(10) 0.2265(7) 0.045(2) Uani 1 1 d . . . . .
H7 H 0.220470 0.246316 0.198267 0.054 Uiso 1 1 calc R U . . .
C8 C 0.2477(5) 0.4495(11) 0.1871(7) 0.045(2) Uani 1 1 d . . . . .
H8 H 0.243324 0.544292 0.214858 0.054 Uiso 1 1 calc R U . . .
C9 C 0.2911(5) 0.4295(12) 0.1036(7) 0.048(2) Uani 1 1 d . . . . .
H9 H 0.298639 0.333269 0.080964 0.057 Uiso 1 1 calc R U . . .
C10 C 0.3211(6) 0.5380(13) 0.0567(9) 0.050(3) Uani 1 1 d . . . . .
H10 H 0.314441 0.633442 0.081883 0.060 Uiso 1 1 calc R U . . .
C11 C 0.3632(7) 0.5231(12) -0.0300(9) 0.048(3) Uani 1 1 d . . . . .
C12 C 0.3852(7) 0.6444(16) -0.0812(9) 0.058(3) Uani 1 1 d . . . . .
H12 H 0.373177 0.738475 -0.058987 0.070 Uiso 1 1 calc R U . . .
C13 C 0.4235(7) 0.6308(18) -0.1618(9) 0.069(4) Uani 1 1 d . . . . .
H13 H 0.438624 0.715929 -0.194121 0.082 Uiso 1 1 calc R U . . .
N1 N 0.4408(6) 0.5005(12) -0.1979(9) 0.063(4) Uani 1 1 d . . . . .
C15 C 0.4217(6) 0.3773(15) -0.1507(9) 0.059(3) Uani 1 1 d . . . . .
H15 H 0.434603 0.284806 -0.174718 0.071 Uiso 1 1 calc R U . . .
C16 C 0.3831(7) 0.3890(15) -0.0672(9) 0.055(3) Uani 1 1 d . . . . .
H16 H 0.369686 0.302945 -0.034094 0.066 Uiso 1 1 calc R U . . .
C17 C 0.0262(7) 0.4545(13) 0.6069(10) 0.065(3) Uani 1 1 d . . . . .
H17A H 0.074536 0.467896 0.648303 0.097 Uiso 1 1 calc R U . . .
H17B H -0.007636 0.431370 0.655592 0.097 Uiso 1 1 calc R U . . .
H17C H 0.010857 0.543978 0.567765 0.097 Uiso 1 1 calc R U . . .
C18 C 0.7006(4) 0.5636(8) -0.4353(6) 0.0313(18) Uani 1 1 d . . . . .
C19 C 0.7031(5) 0.5607(9) -0.3254(7) 0.0399(19) Uani 1 1 d . . . . .
H19 H 0.661522 0.532434 -0.296970 0.048 Uiso 1 1 calc R U . . .
C20 C 0.7660(5) 0.5990(10) -0.2558(8) 0.049(2) Uani 1 1 d . . . . .
H20 H 0.767281 0.600224 -0.180418 0.059 Uiso 1 1 calc R U . . .
C21 C 0.8262(5) 0.6351(10) -0.2998(9) 0.050(2) Uani 1 1 d . . . . .
C22 C 0.8255(5) 0.6398(10) -0.4090(9) 0.055(3) Uani 1 1 d . . . . .
H22 H 0.867478 0.666348 -0.437092 0.065 Uiso 1 1 calc R U . . .
C23 C 0.7619(5) 0.6048(10) -0.4770(7) 0.043(2) Uani 1 1 d . . . . .
H23 H 0.760029 0.608817 -0.552448 0.052 Uiso 1 1 calc R U . . .
C14 C 0.4835(9) 0.4911(15) -0.2854(12) 0.081(5) Uani 1 1 d . . . . .
H1A H 0.466511 0.408998 -0.332067 0.122 Uiso 1 1 calc R U . . .
H1B H 0.534419 0.476997 -0.255126 0.122 Uiso 1 1 calc R U . . .
H1C H 0.477963 0.581134 -0.327268 0.122 Uiso 1 1 calc R U . . .
O1 O 0.0273(4) 0.3378(7) 0.5322(5) 0.0583(18) Uani 1 1 d . . . . .
Cl1 Cl 0.90745(18) 0.6711(3) -0.2145(3) 0.0807(11) Uani 1 1 d . . . . .
S1 S 0.61943(14) 0.5192(2) -0.52357(18) 0.0306(6) Uani 1 1 d D U . . .
O2 O 0.6343(12) 0.391(3) -0.5833(19) 0.059(6) Uani 0.55(4) 1 d D U P A 1
O3 O 0.5653(10) 0.493(3) -0.4584(13) 0.048(7) Uani 0.55(4) 1 d D U P A 1
O4 O 0.6015(12) 0.643(2) -0.595(2) 0.066(8) Uani 0.55(4) 1 d D U P A 1
O2' O 0.6446(13) 0.469(4) -0.6158(19) 0.059(8) Uani 0.45(4) 1 d D U P A 2
O3' O 0.5857(15) 0.409(3) -0.4675(19) 0.059(8) Uani 0.45(4) 1 d D U P A 2
O4' O 0.5807(11) 0.653(2) -0.532(3) 0.053(8) Uani 0.45(4) 1 d D U P A 2
C24 C 0.2372(5) 0.8956(10) 0.1418(7) 0.043(2) Uani 1 1 d . . . . .
H24 H 0.239143 0.891150 0.067332 0.052 Uiso 1 1 calc R U . . .
C25 C 0.1738(5) 0.8615(10) 0.1789(9) 0.052(2) Uani 1 1 d . . . . .
H25 H 0.131872 0.835539 0.129861 0.063 Uiso 1 1 calc R U . . .
C26 C 0.1720(5) 0.8655(10) 0.2860(9) 0.049(2) Uani 1 1 d . . . . .
C27 C 0.2323(5) 0.9020(10) 0.3602(8) 0.050(2) Uani 1 1 d . . . . .
H27 H 0.230376 0.901280 0.434759 0.060 Uiso 1 1 calc R U . . .
C28 C 0.2962(5) 0.9399(10) 0.3232(7) 0.0396(19) Uani 1 1 d . . . . .
H28 H 0.337628 0.967603 0.372637 0.048 Uiso 1 1 calc R U . . .
C29 C 0.2985(4) 0.9369(8) 0.2151(6) 0.0313(18) Uani 1 1 d . . . . .
N2 N 0.5582(7) 0.9970(13) 0.5843(9) 0.073(4) Uani 1 1 d . . . . .
C31 C 0.5777(7) 0.8781(17) 0.6412(10) 0.069(4) Uani 1 1 d . . . . .
H31 H 0.564890 0.785816 0.610322 0.083 Uiso 1 1 calc R U . . .
C32 C 0.6158(7) 0.8853(16) 0.7432(9) 0.062(4) Uani 1 1 d . . . . .
H32 H 0.628349 0.798222 0.782136 0.074 Uiso 1 1 calc R U . . .
C33 C 0.6366(7) 1.0196(12) 0.7910(10) 0.053(3) Uani 1 1 d . . . . .
C34 C 0.6147(8) 1.1413(17) 0.7300(10) 0.065(4) Uani 1 1 d . . . . .
H34 H 0.626393 1.235233 0.758621 0.077 Uiso 1 1 calc R U . . .
C35 C 0.5764(7) 1.1273(19) 0.6290(11) 0.075(5) Uani 1 1 d . . . . .
H35 H 0.562105 1.212547 0.588729 0.090 Uiso 1 1 calc R U . . .
C36 C 0.6784(6) 1.0340(13) 0.8976(9) 0.050(3) Uani 1 1 d . . . . .
H36 H 0.685082 1.129818 0.925133 0.059 Uiso 1 1 calc R U . . .
C37 C 0.7081(5) 0.9285(11) 0.9609(7) 0.046(2) Uani 1 1 d . . . . .
H37 H 0.699739 0.831881 0.935767 0.055 Uiso 1 1 calc R U . . .
C38 C 0.7520(5) 0.9470(11) 1.0641(8) 0.046(2) Uani 1 1 d . . . . .
H38 H 0.757248 1.042040 1.093412 0.056 Uiso 1 1 calc R U . . .
C39 C 0.7859(5) 0.8380(10) 1.1214(7) 0.046(2) Uani 1 1 d . . . . .
H39 H 0.778317 0.744151 1.090546 0.055 Uiso 1 1 calc R U . . .
C40 C 0.8331(5) 0.8446(9) 1.2258(7) 0.0381(19) Uani 1 1 d . . . . .
C41 C 0.8384(6) 0.9667(10) 1.2917(8) 0.043(2) Uani 1 1 d . . . . .
H41 H 0.810136 1.049729 1.268647 0.052 Uiso 1 1 calc R U . . .
C42 C 0.8838(6) 0.9705(10) 1.3901(8) 0.044(2) Uani 1 1 d . . . . .
H42 H 0.886205 1.054475 1.434112 0.052 Uiso 1 1 calc R U . . .
C43 C 0.9258(5) 0.8489(10) 1.4232(7) 0.042(2) Uani 1 1 d . . . . .
C44 C 0.9223(5) 0.7285(11) 1.3564(8) 0.052(2) Uani 1 1 d . . . . .
H44 H 0.952152 0.646849 1.377512 0.063 Uiso 1 1 calc R U . . .
C45 C 0.8767(5) 0.7262(10) 1.2612(7) 0.041(2) Uani 1 1 d . . . . .
H45 H 0.874443 0.641789 1.217630 0.050 Uiso 1 1 calc R U . . .
C46 C 0.9733(8) 0.9577(13) 1.5935(10) 0.066(3) Uani 1 1 d . . . . .
H46A H 0.987027 1.047207 1.560294 0.099 Uiso 1 1 calc R U . . .
H46B H 1.008161 0.937104 1.658283 0.099 Uiso 1 1 calc R U . . .
H46C H 0.925206 0.969328 1.612535 0.099 Uiso 1 1 calc R U . . .
C30 C 0.5161(9) 0.9885(16) 0.4752(12) 0.092(6) Uani 1 1 d . . . . .
H2A H 0.525601 1.074682 0.434361 0.138 Uiso 1 1 calc R U . . .
H2B H 0.464611 0.983871 0.479471 0.138 Uiso 1 1 calc R U . . .
H2C H 0.530042 0.901298 0.439328 0.138 Uiso 1 1 calc R U . . .
O5 O 0.9724(4) 0.8384(8) 1.5187(5) 0.0573(18) Uani 1 1 d . . . . .
Cl2 Cl 0.09147(18) 0.8290(3) 0.3320(3) 0.0811(11) Uani 1 1 d . . . . .
S2 S 0.37970(14) 0.9814(2) 0.16671(19) 0.0313(6) Uani 1 1 d D U . . .
O6 O 0.3970(13) 0.858(2) 0.105(3) 0.067(8) Uani 0.64(6) 1 d D U P B 3
O7 O 0.3646(13) 1.108(3) 0.098(3) 0.067(7) Uani 0.64(6) 1 d D U P B 3
O8 O 0.4322(11) 1.009(4) 0.2597(14) 0.062(8) Uani 0.64(6) 1 d D U P B 3
O6' O 0.4168(16) 0.844(3) 0.170(4) 0.050(10) Uani 0.36(6) 1 d D U P B 4
O7' O 0.355(2) 1.033(8) 0.061(3) 0.071(13) Uani 0.36(6) 1 d D U P B 4
O8' O 0.416(2) 1.085(5) 0.240(4) 0.065(11) Uani 0.36(6) 1 d D U P B 4
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'
Cl Cl 0.1484 0.1585 '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
O1 C1 C2 125.2(8) . . ?
O1 C1 C6 117.0(8) . . ?
C2 C1 C6 117.9(9) . . ?
C3 C2 C1 120.3(9) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.5(9) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 117.2(8) . . ?
C3 C4 C7 123.6(8) . . ?
C5 C4 C7 119.2(8) . . ?
C6 C5 C4 121.3(9) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 121.7(9) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
C8 C7 C4 128.0(9) . . ?
C8 C7 H7 116.0 . . ?
C4 C7 H7 116.0 . . ?
C7 C8 C9 122.7(9) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
C10 C9 C8 124.0(11) . . ?
C10 C9 H9 118.0 . . ?
C8 C9 H9 118.0 . . ?
C9 C10 C11 125.8(11) . . ?
C9 C10 H10 117.1 . . ?
C11 C10 H10 117.1 . . ?
C12 C11 C16 116.0(13) . . ?
C12 C11 C10 121.0(11) . . ?
C16 C11 C10 123.1(10) . . ?
C13 C12 C11 121.1(14) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
N1 C13 C12 122.0(13) . . ?
N1 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 N1 C15 120.1(12) . . ?
C13 N1 C14 120.0(10) . . ?
C15 N1 C14 119.8(11) . . ?
N1 C15 C16 118.8(13) . . ?
N1 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C11 122.1(12) . . ?
C15 C16 H16 119.0 . . ?
C11 C16 H16 119.0 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 119.6(8) . . ?
C19 C18 S1 120.5(6) . . ?
C23 C18 S1 120.0(6) . . ?
C18 C19 C20 120.8(9) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C21 C20 C19 118.1(9) . . ?
C21 C20 H20 120.9 . . ?
C19 C20 H20 120.9 . . ?
C22 C21 C20 122.5(9) . . ?
C22 C21 Cl1 118.3(8) . . ?
C20 C21 Cl1 119.2(8) . . ?
C21 C22 C23 118.4(9) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 H22 120.8 . . ?
C22 C23 C18 120.6(9) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
N1 C14 H1A 109.5 . . ?
N1 C14 H1B 109.5 . . ?
H1A C14 H1B 109.5 . . ?
N1 C14 H1C 109.5 . . ?
H1A C14 H1C 109.5 . . ?
H1B C14 H1C 109.5 . . ?
C1 O1 C17 117.9(8) . . ?
O2' S1 O4' 117.3(13) . . ?
O2' S1 O3' 114.4(15) . . ?
O4' S1 O3' 112.5(13) . . ?
O3 S1 O2 112.3(10) . . ?
O3 S1 O4 112.1(11) . . ?
O2 S1 O4 110.7(13) . . ?
O2' S1 C18 102.9(10) . . ?
O4' S1 C18 102.9(7) . . ?
O3 S1 C18 107.1(7) . . ?
O3' S1 C18 104.7(8) . . ?
O2 S1 C18 107.1(8) . . ?
O4 S1 C18 107.2(7) . . ?
C25 C24 C29 119.6(8) . . ?
C25 C24 H24 120.2 . . ?
C29 C24 H24 120.2 . . ?
C26 C25 C24 119.7(9) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C27 121.8(9) . . ?
C25 C26 Cl2 119.6(8) . . ?
C27 C26 Cl2 118.6(8) . . ?
C26 C27 C28 118.9(9) . . ?
C26 C27 H27 120.5 . . ?
C28 C27 H27 120.5 . . ?
C29 C28 C27 119.7(8) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C28 C29 C24 120.2(8) . . ?
C28 C29 S2 120.4(6) . . ?
C24 C29 S2 119.4(6) . . ?
C31 N2 C35 118.7(13) . . ?
C31 N2 C30 121.3(13) . . ?
C35 N2 C30 120.0(11) . . ?
N2 C31 C32 121.6(14) . . ?
N2 C31 H31 119.2 . . ?
C32 C31 H31 119.2 . . ?
C31 C32 C33 120.8(13) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C34 C33 C32 116.0(14) . . ?
C34 C33 C36 120.7(12) . . ?
C32 C33 C36 123.3(11) . . ?
C35 C34 C33 120.5(15) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
N2 C35 C34 122.3(13) . . ?
N2 C35 H35 118.8 . . ?
C34 C35 H35 118.8 . . ?
C37 C36 C33 127.3(12) . . ?
C37 C36 H36 116.3 . . ?
C33 C36 H36 116.3 . . ?
C36 C37 C38 125.9(11) . . ?
C36 C37 H37 117.1 . . ?
C38 C37 H37 117.1 . . ?
C39 C38 C37 123.8(10) . . ?
C39 C38 H38 118.1 . . ?
C37 C38 H38 118.1 . . ?
C38 C39 C40 128.4(9) . . ?
C38 C39 H39 115.8 . . ?
C40 C39 H39 115.8 . . ?
C45 C40 C41 117.3(8) . . ?
C45 C40 C39 119.6(8) . . ?
C41 C40 C39 123.0(8) . . ?
C42 C41 C40 122.0(9) . . ?
C42 C41 H41 119.0 . . ?
C40 C41 H41 119.0 . . ?
C41 C42 C43 118.9(9) . . ?
C41 C42 H42 120.6 . . ?
C43 C42 H42 120.6 . . ?
O5 C43 C44 116.0(8) . . ?
O5 C43 C42 124.6(8) . . ?
C44 C43 C42 119.4(9) . . ?
C45 C44 C43 120.7(9) . . ?
C45 C44 H44 119.6 . . ?
C43 C44 H44 119.6 . . ?
C44 C45 C40 121.7(9) . . ?
C44 C45 H45 119.2 . . ?
C40 C45 H45 119.2 . . ?
O5 C46 H46A 109.5 . . ?
O5 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
O5 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
N2 C30 H2A 109.5 . . ?
N2 C30 H2B 109.5 . . ?
H2A C30 H2B 109.5 . . ?
N2 C30 H2C 109.5 . . ?
H2A C30 H2C 109.5 . . ?
H2B C30 H2C 109.5 . . ?
C43 O5 C46 117.2(8) . . ?
O8' S2 O7' 116(2) . . ?
O8' S2 O6' 113.1(17) . . ?
O7' S2 O6' 113.9(18) . . ?
O8 S2 O6 113.5(11) . . ?
O8 S2 O7 113.0(11) . . ?
O6 S2 O7 110.2(12) . . ?
O8' S2 C29 106.1(15) . . ?
O7' S2 C29 103.1(15) . . ?
O8 S2 C29 105.8(8) . . ?
O6' S2 C29 103.1(10) . . ?
O6 S2 C29 106.7(7) . . ?
O7 S2 C29 107.2(9) . . ?
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
C1 O1 1.364(10) . ?
C1 C2 1.387(12) . ?
C1 C6 1.399(12) . ?
C2 C3 1.383(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(12) . ?
C4 C7 1.464(12) . ?
C5 C6 1.348(13) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.339(13) . ?
C7 H7 0.9500 . ?
C8 C9 1.450(13) . ?
C8 H8 0.9500 . ?
C9 C10 1.335(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.464(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(16) . ?
C11 C16 1.395(17) . ?
C12 C13 1.349(18) . ?
C12 H12 0.9500 . ?
C13 N1 1.343(17) . ?
C13 H13 0.9500 . ?
N1 C15 1.358(15) . ?
N1 C14 1.476(19) . ?
C15 C16 1.382(16) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O1 1.434(12) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.383(11) . ?
C18 C23 1.398(11) . ?
C18 S1 1.785(8) . ?
C19 C20 1.399(12) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(13) . ?
C20 H20 0.9500 . ?
C21 C22 1.380(14) . ?
C21 Cl1 1.750(9) . ?
C22 C23 1.392(13) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C14 H1A 0.9800 . ?
C14 H1B 0.9800 . ?
C14 H1C 0.9800 . ?
S1 O2' 1.408(18) . ?
S1 O4' 1.425(16) . ?
S1 O3 1.433(15) . ?
S1 O3' 1.443(16) . ?
S1 O2 1.453(16) . ?
S1 O4 1.461(14) . ?
C24 C25 1.389(12) . ?
C24 C29 1.407(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.362(14) . ?
C25 H25 0.9500 . ?
C26 C27 1.389(14) . ?
C26 Cl2 1.743(9) . ?
C27 C28 1.405(12) . ?
C27 H27 0.9500 . ?
C28 C29 1.376(11) . ?
C28 H28 0.9500 . ?
C29 S2 1.786(8) . ?
N2 C31 1.328(16) . ?
N2 C35 1.346(19) . ?
N2 C30 1.476(19) . ?
C31 C32 1.371(17) . ?
C31 H31 0.9500 . ?
C32 C33 1.404(18) . ?
C32 H32 0.9500 . ?
C33 C34 1.384(16) . ?
C33 C36 1.451(17) . ?
C34 C35 1.37(2) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 C37 1.323(14) . ?
C36 H36 0.9500 . ?
C37 C38 1.434(13) . ?
C37 H37 0.9500 . ?
C38 C39 1.337(13) . ?
C38 H38 0.9500 . ?
C39 C40 1.466(12) . ?
C39 H39 0.9500 . ?
C40 C45 1.393(12) . ?
C40 C41 1.394(12) . ?
C41 C42 1.389(15) . ?
C41 H41 0.9500 . ?
C42 C43 1.395(13) . ?
C42 H42 0.9500 . ?
C43 O5 1.373(11) . ?
C43 C44 1.390(12) . ?
C44 C45 1.359(13) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 O5 1.449(12) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C30 H2A 0.9800 . ?
C30 H2B 0.9800 . ?
C30 H2C 0.9800 . ?
S2 O8' 1.42(3) . ?
S2 O7' 1.42(3) . ?
S2 O8 1.429(17) . ?
S2 O6' 1.44(2) . ?
S2 O6 1.450(14) . ?
S2 O7 1.452(16) . ?
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
C12 H12 O6^c 0.95 2.32 3.05(3) 132.4 . yes
C13 H13 O8^c 0.95 2.60 3.48(4) 153.6 2_574 yes
C13 H13 O8'^d 0.95 2.03 2.89(4) 149.9 2_574 yes
C15 H15 O6'^d 0.95 2.27 3.04(4) 137.4 2_564 yes
C16 H16 O7^c 0.95 2.47 3.38(2) 161.8 1_545 yes
C19 H19 O2'^b 0.95 2.37 3.05(2) 128.3 2_565 yes
C20 H20 O2'^b 0.95 2.65 3.18(2) 115.3 2_565 yes
C14 H1A O6'^d 0.98 2.51 3.35(3) 142.6 2_564 yes
C14 H1B O4^a 0.98 2.46 3.24(3) 135.8 2_565 yes
C14 H1B O2'^b 0.98 2.54 3.43(3) 151.5 2_565 yes
C28 H28 O7'^d 0.95 2.35 3.04(3) 128.7 2_575 yes
C31 H31 O4'^b 0.95 2.24 3.03(3) 139.6 1_556 yes
C32 H32 O2^a 0.95 2.43 3.34(2) 161.6 2_566 yes
C34 H34 O4^a 0.95 2.28 3.01(2) 133.9 2_576 yes
C35 H35 O3'^b 0.95 2.02 2.89(3) 150.4 1_566 yes
C30 H2B O6^c 0.98 2.63 3.31(3) 126.1 2_575 yes
C30 H2B O7'^d 0.98 2.47 3.40(4) 158.7 2_575 yes
C30 H2C O4'^b 0.98 2.48 3.33(2) 144.6 1_556 yes
