#------------------------------------------------------------------------------
#$Date: 2024-07-10 04:50:55 +0300 (Wed, 10 Jul 2024) $
#$Revision: 293349 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/31/2023190.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_2023190
loop_
_publ_author_name
'Isobe, Mami'
'Kashiwagi, Yukiyasu'
'Kubono, Koji'
_publ_section_title
;
 Crystal structure of the 1:1 co-crystal 4-(dimethylamino)pyridin-1-ium
 8-hydroxyquinoline-5-sulfonate--N,N-dimethylpyridin-4-amine
;
_journal_coeditor_code           OX2006
_journal_issue                   8
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S205698902400642X
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C7 H11 N2 +, C9 H6 N O4 S -, C7 H10 N2'
_chemical_formula_moiety         'C7 H11 N2 +, C9 H6 N O4 S -, C7 H10 N2'
_chemical_formula_sum            'C23 H27 N5 O4 S'
_chemical_formula_weight         469.55
_chemical_name_systematic
;
4-(Dimethylamino)pyridin-1-ium 8-hydroxyquinoline-5-sulfonate;
N,N-dimethylpyridin-4-amine
;
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.6050(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.00032(10)
_cell_length_b                   15.14469(18)
_cell_length_c                   18.9141(2)
_cell_measurement_reflns_used    11719
_cell_measurement_temperature    100
_cell_measurement_theta_max      76.8410
_cell_measurement_theta_min      3.7490
_cell_volume                     2252.53(5)
_computing_cell_refinement
;
CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)
;
_computing_data_collection
;
CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)
;
_computing_data_reduction
;
CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)
;
_computing_molecular_graphics
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16358
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.159
_diffrn_reflns_theta_min         3.765
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.622
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2023)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.302
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.393
_refine_ls_abs_structure_details
;
 Refined as an inversion twin
;
_refine_ls_abs_structure_Flack   0.478(18)
_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     620
_refine_ls_number_reflns         6813
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0325
_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)+(0.0463P)²+0.5548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0848
_reflns_number_gt                6608
_reflns_number_total             6813
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ox2006.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               2023190
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
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_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.17772(8) 0.49921(4) 0.37557(4) 0.01431(15) Uani d 1 . .
S S2 0.88938(8) 0.99725(4) 0.36763(4) 0.01686(16) Uani d 1 . .
O O5 0.0868(3) 0.46728(13) 0.43037(11) 0.0198(4) Uani d 1 . .
O O10 0.3080(3) 0.75413(13) 0.36853(12) 0.0189(4) Uani d 1 . .
O O4 0.2618(3) 0.58342(12) 0.39552(12) 0.0222(4) Uani d 1 . .
O O7 1.0147(3) 0.97468(16) 0.43079(12) 0.0274(5) Uani d 1 . .
O O6 0.7498(3) 0.25632(14) 0.35776(12) 0.0191(4) Uani d 1 . .
N N11 0.4365(3) 0.18427(15) 0.35601(13) 0.0168(5) Uani d 1 . .
O O3 0.0728(3) 0.49865(13) 0.30454(12) 0.0251(5) Uani d 1 . .
N N14 0.0994(3) 0.57921(17) 0.61872(14) 0.0228(5) Uani d 1 . .
O O9 0.9547(3) 0.98318(15) 0.30206(12) 0.0253(5) Uani d 1 . .
N N18 1.0806(4) 1.06837(18) 0.62048(15) 0.0283(6) Uani d 1 . .
N N12 0.6186(3) 0.68257(14) 0.36322(13) 0.0153(5) Uani d 1 . .
N N17 1.3114(3) 1.31360(18) 0.63022(14) 0.0268(6) Uani d 1 . .
N N13 0.3275(3) 0.82252(17) 0.60874(14) 0.0248(6) Uani d 1 . .
C C25 0.3141(4) 0.33136(18) 0.36637(15) 0.0132(5) Uani d 1 . .
N N16 -0.3146(4) 0.16966(18) 0.60144(14) 0.0300(6) Uani d 1 . .
N N15 -0.0827(3) 0.41978(17) 0.61461(14) 0.0258(6) Uani d 1 . .
C C30 0.4422(3) 0.80852(18) 0.36639(15) 0.0152(6) Uani d 1 . .
N N20 0.6851(4) 0.65381(18) 0.61189(15) 0.0297(6) Uani d 1 . .
C C29 0.4524(4) 0.27401(18) 0.36172(15) 0.0141(5) Uani d 1 . .
N N19 0.9083(4) 0.90581(18) 0.61654(15) 0.0271(6) Uani d 1 . .
C C35 0.9054(4) 0.79031(19) 0.36300(15) 0.0157(5) Uani d 1 . .
H H35 1.003375 0.825760 0.363038 0.019 Uiso calc 1 . .
O O8 0.8170(3) 1.08342(14) 0.37345(18) 0.0427(7) Uani d 1 . .
C C48 -0.2420(4) 0.25088(19) 0.60531(16) 0.0222(6) Uani d 1 . .
C C23 0.5063(4) 0.45581(18) 0.37350(16) 0.0165(6) Uani d 1 . .
H H23 0.525964 0.517580 0.378068 0.020 Uiso calc 1 . .
C C24 0.3458(4) 0.42408(18) 0.37218(15) 0.0156(6) Uani d 1 . .
C C27 0.1385(4) 0.20164(19) 0.35746(16) 0.0195(6) Uani d 1 . .
H H27 0.031056 0.173969 0.355266 0.023 Uiso calc 1 . .
C C26 0.1533(4) 0.29119(19) 0.36372(15) 0.0162(6) Uani d 1 . .
H H26 0.056312 0.326366 0.366290 0.019 Uiso calc 1 . .
C C34 0.7451(3) 0.82997(18) 0.36388(15) 0.0137(5) Uani d 1 . .
C C49 -0.2102(4) 0.29987(19) 0.66961(16) 0.0224(6) Uani d 1 . .
H H49 -0.243039 0.277078 0.711817 0.027 Uiso calc 1 . .
C C31 0.4187(4) 0.89824(19) 0.36710(17) 0.0192(6) Uani d 1 . .
H H31 0.309000 0.921934 0.367659 0.023 Uiso calc 1 . .
C C38 0.6054(4) 0.77244(17) 0.36430(15) 0.0130(5) Uani d 1 . .
C C28 0.2840(4) 0.15080(18) 0.35428(16) 0.0197(6) Uani d 1 . .
H H28 0.271473 0.088498 0.350666 0.024 Uiso calc 1 . .
C C33 0.7176(4) 0.92240(18) 0.36554(15) 0.0152(5) Uani d 1 . .
C C61 0.8018(4) 0.7746(2) 0.55202(16) 0.0215(6) Uani d 1 . .
H H61 0.781003 0.744043 0.507393 0.026 Uiso calc 1 . .
C C54 1.1908(4) 1.1940(2) 0.68862(16) 0.0220(6) Uani d 1 . .
H H54 1.212304 1.223795 0.733567 0.026 Uiso calc 1 . .
C C36 0.9166(4) 0.70039(19) 0.36211(16) 0.0184(6) Uani d 1 . .
H H36 1.022730 0.672608 0.361413 0.022 Uiso calc 1 . .
C C62 0.7562(4) 0.7356(2) 0.61344(17) 0.0237(6) Uani d 1 . .
C C60 0.8763(4) 0.8566(2) 0.55657(17) 0.0257(7) Uani d 1 . .
H H60 0.907308 0.880142 0.514258 0.031 Uiso calc 1 . .
C C50 -0.1315(4) 0.3809(2) 0.67126(17) 0.0247(6) Uani d 1 . .
H H50 -0.110204 0.411581 0.715822 0.030 Uiso calc 1 . .
C C22 0.6432(4) 0.39925(19) 0.36825(17) 0.0193(6) Uani d 1 . .
H H22 0.753237 0.423009 0.368649 0.023 Uiso calc 1 . .
C C40 0.2142(4) 0.7096(2) 0.67653(16) 0.0209(6) Uani d 1 . .
H H40 0.240263 0.743534 0.719363 0.025 Uiso calc 1 . .
C C53 1.1159(4) 1.1131(2) 0.68335(18) 0.0257(7) Uani d 1 . .
H H53 1.087382 1.087116 0.725275 0.031 Uiso calc 1 . .
C C37 0.7696(4) 0.64896(18) 0.36221(17) 0.0183(6) Uani d 1 . .
H H37 0.780438 0.586507 0.361522 0.022 Uiso calc 1 . .
C C42 0.2165(4) 0.6872(2) 0.55097(16) 0.0229(6) Uani d 1 . .
H H42 0.243782 0.705189 0.506333 0.027 Uiso calc 1 . .
C C41 0.2560(4) 0.74334(19) 0.61167(16) 0.0200(6) Uani d 1 . .
C C21 0.6173(4) 0.30979(18) 0.36257(15) 0.0145(5) Uani d 1 . .
C C47 -0.1930(4) 0.2920(2) 0.54526(16) 0.0237(6) Uani d 1 . .
H H47 -0.212812 0.263269 0.499838 0.028 Uiso calc 1 . .
C C64 0.8639(4) 0.8686(2) 0.67528(18) 0.0296(7) Uani d 1 . .
H H64 0.885457 0.901387 0.718843 0.036 Uiso calc 1 . .
C C55 1.2371(4) 1.23419(19) 0.62685(16) 0.0218(6) Uani d 1 . .
C C52 -0.3516(5) 0.1263(2) 0.66566(19) 0.0318(7) Uani d 1 . .
H H52A -0.246320 0.120190 0.701170 0.048 Uiso calc 1 . .
H H52B -0.399916 0.067773 0.652889 0.048 Uiso calc 1 . .
H H52C -0.433271 0.161935 0.686096 0.048 Uiso calc 1 . .
C C63 0.7900(4) 0.7873(2) 0.67674(17) 0.0282(7) Uani d 1 . .
H H63 0.761539 0.765609 0.720146 0.034 Uiso calc 1 . .
C C44 0.3650(5) 0.8790(2) 0.67269(19) 0.0302(7) Uani d 1 . .
H H44A 0.258673 0.894730 0.688314 0.045 Uiso calc 1 . .
H H44B 0.422323 0.932840 0.661072 0.045 Uiso calc 1 . .
H H44C 0.439097 0.847174 0.711421 0.045 Uiso calc 1 . .
C C46 -0.1165(4) 0.3737(2) 0.55256(17) 0.0250(6) Uani d 1 . .
H H46 -0.085302 0.399369 0.511048 0.030 Uiso calc 1 . .
C C43 0.1398(4) 0.6079(2) 0.55592(17) 0.0238(6) Uani d 1 . .
H H43 0.113795 0.571602 0.514381 0.029 Uiso calc 1 . .
C C39 0.1381(4) 0.6302(2) 0.67832(17) 0.0230(6) Uani d 1 . .
H H39 0.111083 0.609654 0.722336 0.028 Uiso calc 1 . .
C C32 0.5578(4) 0.95491(19) 0.36698(17) 0.0202(6) Uani d 1 . .
H H32 0.541065 1.016967 0.367926 0.024 Uiso calc 1 . .
C C56 1.2007(4) 1.1840(2) 0.56237(17) 0.0252(6) Uani d 1 . .
H H56 1.230849 1.206924 0.519661 0.030 Uiso calc 1 . .
C C58 1.3420(5) 1.3650(2) 0.69703(19) 0.0322(7) Uani d 1 . .
H H58A 1.233475 1.377047 0.712141 0.048 Uiso calc 1 . .
H H58B 1.397149 1.420969 0.688945 0.048 Uiso calc 1 . .
H H58C 1.415965 1.331447 0.734677 0.048 Uiso calc 1 . .
C C57 1.1241(4) 1.1046(2) 0.56067(18) 0.0292(7) Uani d 1 . .
H H57 1.100001 1.073059 0.516531 0.035 Uiso calc 1 . .
C C66 0.6549(5) 0.6125(2) 0.6777(2) 0.0355(8) Uani d 1 . .
H H66A 0.761279 0.610761 0.712932 0.053 Uiso calc 1 . .
H H66B 0.613111 0.552185 0.667276 0.053 Uiso calc 1 . .
H H66C 0.569870 0.646643 0.697307 0.053 Uiso calc 1 . .
C C51 -0.3476(5) 0.1193(2) 0.53443(18) 0.0345(8) Uani d 1 . .
H H51A -0.429289 0.151412 0.498551 0.052 Uiso calc 1 . .
H H51B -0.394504 0.061445 0.543216 0.052 Uiso calc 1 . .
H H51C -0.241090 0.111422 0.516567 0.052 Uiso calc 1 . .
C C45 0.3605(5) 0.8585(2) 0.54079(18) 0.0316(7) Uani d 1 . .
H H45A 0.434078 0.817948 0.520221 0.047 Uiso calc 1 . .
H H45B 0.416725 0.916003 0.549571 0.047 Uiso calc 1 . .
H H45C 0.252586 0.865738 0.507093 0.047 Uiso calc 1 . .
C C65 0.6452(5) 0.6043(2) 0.54515(19) 0.0320(7) Uani d 1 . .
H H65A 0.569908 0.639435 0.509079 0.048 Uiso calc 1 . .
H H65B 0.588361 0.549017 0.553627 0.048 Uiso calc 1 . .
H H65C 0.750475 0.591031 0.527717 0.048 Uiso calc 1 . .
C C59 1.3515(5) 1.3552(2) 0.5656(2) 0.0355(8) Uani d 1 . .
H H59A 1.429459 1.317305 0.545016 0.053 Uiso calc 1 . .
H H59B 1.405242 1.412637 0.578214 0.053 Uiso calc 1 . .
H H59C 1.246532 1.363609 0.530309 0.053 Uiso calc 1 . .
H H14 0.047(5) 0.5262(17) 0.616(2) 0.029(9) Uiso d 1 . .
H H10 0.336(6) 0.697(3) 0.372(2) 0.037(11) Uiso d 1 . .
H H18 1.027(6) 1.016(2) 0.618(3) 0.057(15) Uiso d 1 . .
H H6 0.714(6) 0.204(3) 0.357(2) 0.039(12) Uiso d 1 . .
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
0 0 -1 0.0333
0 0 1 0.0788
1 1 0 0.1185
1 1 2 0.1009
0 -1 -1 0.1244
-2 1 2 0.0858
0 2 -1 0.1767
0 -10 0 0.1691
4 -4 -8 0.1589
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
O5 S1 O4 . . 111.94(13) ?
O5 S1 C24 . . 107.15(12) ?
O4 S1 C24 . . 104.71(13) ?
O3 S1 O5 . . 112.26(14) ?
O3 S1 O4 . . 113.97(13) ?
O3 S1 C24 . . 106.09(13) ?
O7 S2 C33 . . 106.42(13) ?
O9 S2 O7 . . 111.50(14) ?
O9 S2 C33 . . 106.67(13) ?
O8 S2 O7 . . 112.15(17) ?
O8 S2 O9 . . 114.36(16) ?
O8 S2 C33 . . 105.04(14) ?
C30 O10 H10 . . 114(3) ?
C21 O6 H6 . . 107(3) ?
C28 N11 C29 . . 117.2(2) ?
C43 N14 H14 . . 115(2) ?
C39 N14 C43 . . 119.4(3) ?
C39 N14 H14 . . 125(2) ?
C53 N18 C57 . . 119.1(3) ?
C53 N18 H18 . . 121(3) ?
C57 N18 H18 . . 120(3) ?
C37 N12 C38 . . 117.4(2) ?
C55 N17 C58 . . 121.4(3) ?
C55 N17 C59 . . 120.8(3) ?
C59 N17 C58 . . 117.6(3) ?
C41 N13 C44 . . 120.9(3) ?
C41 N13 C45 . . 121.3(3) ?
C45 N13 C44 . . 117.7(3) ?
C29 C25 C24 . . 118.4(2) ?
C26 C25 C29 . . 116.6(2) ?
C26 C25 C24 . . 125.0(2) ?
C48 N16 C52 . . 120.9(3) ?
C48 N16 C51 . . 121.8(3) ?
C52 N16 C51 . . 117.1(3) ?
C50 N15 C46 . . 115.2(3) ?
O10 C30 C31 . . 119.3(2) ?
O10 C30 C38 . . 120.1(2) ?
C31 C30 C38 . . 120.6(2) ?
C62 N20 C66 . . 120.6(3) ?
C62 N20 C65 . . 120.8(3) ?
C65 N20 C66 . . 118.5(3) ?
N11 C29 C25 . . 123.4(3) ?
N11 C29 C21 . . 116.8(2) ?
C25 C29 C21 . . 119.8(2) ?
C60 N19 C64 . . 115.2(3) ?
C34 C35 H35 . . 120.5 ?
C36 C35 H35 . . 120.5 ?
C36 C35 C34 . . 118.9(3) ?
N16 C48 C49 . . 122.2(3) ?
N16 C48 C47 . . 122.4(3) ?
C49 C48 C47 . . 115.4(3) ?
C24 C23 H23 . . 119.2 ?
C24 C23 C22 . . 121.7(2) ?
C22 C23 H23 . . 119.2 ?
C25 C24 S1 . . 120.6(2) ?
C23 C24 S1 . . 119.4(2) ?
C23 C24 C25 . . 120.0(2) ?
C26 C27 H27 . . 120.4 ?
C26 C27 C28 . . 119.2(3) ?
C28 C27 H27 . . 120.4 ?
C25 C26 H26 . . 120.2 ?
C27 C26 C25 . . 119.6(3) ?
C27 C26 H26 . . 120.2 ?
C35 C34 C38 . . 117.1(2) ?
C33 C34 C35 . . 124.2(2) ?
C33 C34 C38 . . 118.7(2) ?
C48 C49 H49 . . 120.0 ?
C50 C49 C48 . . 119.9(3) ?
C50 C49 H49 . . 120.0 ?
C30 C31 H31 . . 120.2 ?
C30 C31 C32 . . 119.7(3) ?
C32 C31 H31 . . 120.2 ?
N12 C38 C30 . . 117.2(2) ?
N12 C38 C34 . . 123.3(3) ?
C34 C38 C30 . . 119.5(2) ?
N11 C28 C27 . . 124.0(3) ?
N11 C28 H28 . . 118.0 ?
C27 C28 H28 . . 118.0 ?
C34 C33 S2 . . 120.5(2) ?
C32 C33 S2 . . 119.3(2) ?
C32 C33 C34 . . 120.2(3) ?
C62 C61 H61 . . 119.9 ?
C60 C61 H61 . . 119.9 ?
C60 C61 C62 . . 120.1(3) ?
C53 C54 H54 . . 119.9 ?
C53 C54 C55 . . 120.2(3) ?
C55 C54 H54 . . 119.9 ?
C35 C36 H36 . . 120.2 ?
C35 C36 C37 . . 119.6(3) ?
C37 C36 H36 . . 120.2 ?
N20 C62 C61 . . 122.2(3) ?
N20 C62 C63 . . 122.4(3) ?
C61 C62 C63 . . 115.4(3) ?
N19 C60 C61 . . 124.6(3) ?
N19 C60 H60 . . 117.7 ?
C61 C60 H60 . . 117.7 ?
N15 C50 C49 . . 124.9(3) ?
N15 C50 H50 . . 117.6 ?
C49 C50 H50 . . 117.6 ?
C23 C22 H22 . . 120.1 ?
C21 C22 C23 . . 119.9(3) ?
C21 C22 H22 . . 120.1 ?
C41 C40 H40 . . 119.3 ?
C39 C40 H40 . . 119.3 ?
C39 C40 C41 . . 121.3(3) ?
N18 C53 C54 . . 122.3(3) ?
N18 C53 H53 . . 118.9 ?
C54 C53 H53 . . 118.9 ?
N12 C37 C36 . . 123.7(2) ?
N12 C37 H37 . . 118.2 ?
C36 C37 H37 . . 118.2 ?
C41 C42 H42 . . 119.6 ?
C43 C42 H42 . . 119.6 ?
C43 C42 C41 . . 120.7(3) ?
N13 C41 C40 . . 121.9(3) ?
N13 C41 C42 . . 122.6(3) ?
C42 C41 C40 . . 115.4(3) ?
O6 C21 C29 . . 120.6(2) ?
O6 C21 C22 . . 119.3(3) ?
C22 C21 C29 . . 120.2(3) ?
C48 C47 H47 . . 120.0 ?
C46 C47 C48 . . 120.0(3) ?
C46 C47 H47 . . 120.0 ?
N19 C64 H64 . . 117.6 ?
N19 C64 C63 . . 124.9(3) ?
C63 C64 H64 . . 117.6 ?
N17 C55 C54 . . 121.7(3) ?
N17 C55 C56 . . 122.7(3) ?
C56 C55 C54 . . 115.6(3) ?
N16 C52 H52A . . 109.5 ?
N16 C52 H52B . . 109.5 ?
N16 C52 H52C . . 109.5 ?
H52A C52 H52B . . 109.5 ?
H52A C52 H52C . . 109.5 ?
H52B C52 H52C . . 109.5 ?
C62 C63 H63 . . 120.1 ?
C64 C63 C62 . . 119.8(3) ?
C64 C63 H63 . . 120.1 ?
N13 C44 H44A . . 109.5 ?
N13 C44 H44B . . 109.5 ?
N13 C44 H44C . . 109.5 ?
H44A C44 H44B . . 109.5 ?
H44A C44 H44C . . 109.5 ?
H44B C44 H44C . . 109.5 ?
N15 C46 C47 . . 124.5(3) ?
N15 C46 H46 . . 117.7 ?
C47 C46 H46 . . 117.7 ?
N14 C43 C42 . . 121.7(3) ?
N14 C43 H43 . . 119.1 ?
C42 C43 H43 . . 119.1 ?
N14 C39 H39 . . 119.3 ?
C40 C39 N14 . . 121.4(3) ?
C40 C39 H39 . . 119.3 ?
C31 C32 H32 . . 119.3 ?
C33 C32 C31 . . 121.4(2) ?
C33 C32 H32 . . 119.3 ?
C55 C56 H56 . . 119.4 ?
C57 C56 C55 . . 121.2(3) ?
C57 C56 H56 . . 119.4 ?
N17 C58 H58A . . 109.5 ?
N17 C58 H58B . . 109.5 ?
N17 C58 H58C . . 109.5 ?
H58A C58 H58B . . 109.5 ?
H58A C58 H58C . . 109.5 ?
H58B C58 H58C . . 109.5 ?
N18 C57 H57 . . 119.2 ?
C56 C57 N18 . . 121.7(3) ?
C56 C57 H57 . . 119.2 ?
N20 C66 H66A . . 109.5 ?
N20 C66 H66B . . 109.5 ?
N20 C66 H66C . . 109.5 ?
H66A C66 H66B . . 109.5 ?
H66A C66 H66C . . 109.5 ?
H66B C66 H66C . . 109.5 ?
N16 C51 H51A . . 109.5 ?
N16 C51 H51B . . 109.5 ?
N16 C51 H51C . . 109.5 ?
H51A C51 H51B . . 109.5 ?
H51A C51 H51C . . 109.5 ?
H51B C51 H51C . . 109.5 ?
N13 C45 H45A . . 109.5 ?
N13 C45 H45B . . 109.5 ?
N13 C45 H45C . . 109.5 ?
H45A C45 H45B . . 109.5 ?
H45A C45 H45C . . 109.5 ?
H45B C45 H45C . . 109.5 ?
N20 C65 H65A . . 109.5 ?
N20 C65 H65B . . 109.5 ?
N20 C65 H65C . . 109.5 ?
H65A C65 H65B . . 109.5 ?
H65A C65 H65C . . 109.5 ?
H65B C65 H65C . . 109.5 ?
N17 C59 H59A . . 109.5 ?
N17 C59 H59B . . 109.5 ?
N17 C59 H59C . . 109.5 ?
H59A C59 H59B . . 109.5 ?
H59A C59 H59C . . 109.5 ?
H59B C59 H59C . . 109.5 ?
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 O5 . 1.455(2) ?
S1 O4 . 1.459(2) ?
S1 O3 . 1.447(2) ?
S1 C24 . 1.772(3) ?
S2 O7 . 1.452(2) ?
S2 O9 . 1.448(2) ?
S2 O8 . 1.440(2) ?
S2 C33 . 1.776(3) ?
O10 C30 . 1.359(3) ?
O10 H10 . 0.90(4) ?
O6 C21 . 1.350(3) ?
O6 H6 . 0.84(4) ?
N11 C29 . 1.367(4) ?
N11 C28 . 1.316(4) ?
N14 C43 . 1.358(4) ?
N14 C39 . 1.354(4) ?
N14 H14 . 0.90(2) ?
N18 C53 . 1.353(4) ?
N18 C57 . 1.359(5) ?
N18 H18 . 0.90(2) ?
N12 C38 . 1.366(3) ?
N12 C37 . 1.315(4) ?
N17 C55 . 1.338(4) ?
N17 C58 . 1.466(4) ?
N17 C59 . 1.462(4) ?
N13 C41 . 1.334(4) ?
N13 C44 . 1.467(4) ?
N13 C45 . 1.464(4) ?
C25 C29 . 1.422(4) ?
C25 C24 . 1.428(4) ?
C25 C26 . 1.415(4) ?
N16 C48 . 1.356(4) ?
N16 C52 . 1.458(4) ?
N16 C51 . 1.461(4) ?
N15 C50 . 1.342(4) ?
N15 C46 . 1.350(4) ?
C30 C31 . 1.372(4) ?
C30 C38 . 1.423(4) ?
N20 C62 . 1.362(4) ?
N20 C66 . 1.453(4) ?
N20 C65 . 1.452(4) ?
C29 C21 . 1.424(4) ?
N19 C60 . 1.342(4) ?
N19 C64 . 1.350(4) ?
C35 H35 . 0.9500 ?
C35 C34 . 1.419(4) ?
C35 C36 . 1.365(4) ?
C48 C49 . 1.407(4) ?
C48 C47 . 1.413(4) ?
C23 H23 . 0.9500 ?
C23 C24 . 1.367(4) ?
C23 C22 . 1.408(4) ?
C27 H27 . 0.9500 ?
C27 C26 . 1.365(4) ?
C27 C28 . 1.407(4) ?
C26 H26 . 0.9500 ?
C34 C38 . 1.419(4) ?
C34 C33 . 1.418(4) ?
C49 H49 . 0.9500 ?
C49 C50 . 1.377(4) ?
C31 H31 . 0.9500 ?
C31 C32 . 1.406(4) ?
C28 H28 . 0.9500 ?
C33 C32 . 1.375(4) ?
C61 H61 . 0.9500 ?
C61 C62 . 1.409(4) ?
C61 C60 . 1.373(4) ?
C54 H54 . 0.9500 ?
C54 C53 . 1.359(4) ?
C54 C55 . 1.426(4) ?
C36 H36 . 0.9500 ?
C36 C37 . 1.410(4) ?
C62 C63 . 1.414(4) ?
C60 H60 . 0.9500 ?
C50 H50 . 0.9500 ?
C22 H22 . 0.9500 ?
C22 C21 . 1.372(4) ?
C40 H40 . 0.9500 ?
C40 C41 . 1.425(4) ?
C40 C39 . 1.351(4) ?
C53 H53 . 0.9500 ?
C37 H37 . 0.9500 ?
C42 H42 . 0.9500 ?
C42 C41 . 1.417(4) ?
C42 C43 . 1.360(4) ?
C47 H47 . 0.9500 ?
C47 C46 . 1.375(4) ?
C64 H64 . 0.9500 ?
C64 C63 . 1.369(5) ?
C55 C56 . 1.421(4) ?
C52 H52A . 0.9800 ?
C52 H52B . 0.9800 ?
C52 H52C . 0.9800 ?
C63 H63 . 0.9500 ?
C44 H44A . 0.9800 ?
C44 H44B . 0.9800 ?
C44 H44C . 0.9800 ?
C46 H46 . 0.9500 ?
C43 H43 . 0.9500 ?
C39 H39 . 0.9500 ?
C32 H32 . 0.9500 ?
C56 H56 . 0.9500 ?
C56 C57 . 1.348(5) ?
C58 H58A . 0.9800 ?
C58 H58B . 0.9800 ?
C58 H58C . 0.9800 ?
C57 H57 . 0.9500 ?
C66 H66A . 0.9800 ?
C66 H66B . 0.9800 ?
C66 H66C . 0.9800 ?
C51 H51A . 0.9800 ?
C51 H51B . 0.9800 ?
C51 H51C . 0.9800 ?
C45 H45A . 0.9800 ?
C45 H45B . 0.9800 ?
C45 H45C . 0.9800 ?
C65 H65A . 0.9800 ?
C65 H65B . 0.9800 ?
C65 H65C . 0.9800 ?
C59 H59A . 0.9800 ?
C59 H59B . 0.9800 ?
C59 H59C . 0.9800 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
N14 H14 0.84 1_555 ? no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_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
O6 H6 O8 . . 1_545 0.84(5) 2.00(5) 2.679(3) 137(4) yes
O6 H6 N11 . . . 0.84(5) 2.24(5) 2.728(3) 117(4) yes
O10 H10 O4 . . 1_555 0.89(5) 1.90(5) 2.674(3) 144(4) yes
O10 H10 N12 . . . 0.89(5) 2.31(5) 2.730(3) 109(4) yes
N14 H14 N15 . . 1_555 0.90(3) 1.91(3) 2.814(4) 174(3) yes
N18 H18 N19 . . 1_555 0.90(3) 1.92(4) 2.816(4) 177(7) yes
C27 H27 O6 . . 1_455 0.95 2.58 3.219(4) 125 yes
C27 H27 O8 . . 1_445 0.95 2.27 3.194(4) 164 yes
C36 H36 O4 . . 1_655 0.95 2.33 3.244(4) 160 yes
C36 H36 O10 . . 1_655 0.95 2.58 3.216(4) 125 yes
C39 H39 O3 . . 2_565 0.95 2.32 3.200(4) 154 yes
C43 H43 O5 . . . 0.95 2.22 3.160(4) 169 yes
C46 H46 O5 . . . 0.95 2.46 3.373(4) 161 yes
C50 H50 O3 . . 2_565 0.95 2.43 3.292(4) 151 yes
C53 H53 O9 . . 2_575 0.95 2.22 3.146(4) 164 yes
C54 H54 O10 . . 2_675 0.95 2.55 3.450(4) 158 yes
C57 H57 O7 . . . 0.95 2.22 3.143(4) 165 yes
C60 H60 O7 . . . 0.95 2.40 3.325(4) 163 yes
C64 H64 O9 . . 2_575 0.95 2.35 3.267(4) 162 yes
C40 H40 Cg1 . . 2_565 0.95 2.63 3.498(3) 153 yes
C49 H49 Cg2 . . 2_465 0.95 2.87 3.754(3) 156 yes
C61 H61 Cg2 . . 1_555 0.95 2.70 3.571(3) 152 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_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
S2 C33 C32 C31 . . . . -178.5(2) ?
O5 S1 C24 C25 . . . . 50.1(3) ?
O5 S1 C24 C23 . . . . -131.4(2) ?
O10 C30 C31 C32 . . . . 178.2(3) ?
O10 C30 C38 N12 . . . . 1.2(4) ?
O10 C30 C38 C34 . . . . -178.4(2) ?
O4 S1 C24 C25 . . . . 169.1(2) ?
O4 S1 C24 C23 . . . . -12.4(3) ?
O7 S2 C33 C34 . . . . -57.5(3) ?
O7 S2 C33 C32 . . . . 121.2(3) ?
N11 C29 C21 O6 . . . . 0.1(4) ?
N11 C29 C21 C22 . . . . -179.9(3) ?
O3 S1 C24 C25 . . . . -70.0(3) ?
O3 S1 C24 C23 . . . . 108.5(2) ?
O9 S2 C33 C34 . . . . 61.6(3) ?
O9 S2 C33 C32 . . . . -119.6(3) ?
N17 C55 C56 C57 . . . . -179.3(3) ?
C25 C29 C21 O6 . . . . -179.6(3) ?
C25 C29 C21 C22 . . . . 0.4(4) ?
N16 C48 C49 C50 . . . . 178.0(3) ?
N16 C48 C47 C46 . . . . -178.6(3) ?
C30 C31 C32 C33 . . . . 0.6(5) ?
N20 C62 C63 C64 . . . . 179.1(3) ?
C29 N11 C28 C27 . . . . 0.4(4) ?
C29 C25 C24 S1 . . . . 178.2(2) ?
C29 C25 C24 C23 . . . . -0.3(4) ?
C29 C25 C26 C27 . . . . 0.4(4) ?
N19 C64 C63 C62 . . . . 0.4(5) ?
C35 C34 C38 N12 . . . . -0.7(4) ?
C35 C34 C38 C30 . . . . 179.0(3) ?
C35 C34 C33 S2 . . . . -0.7(4) ?
C35 C34 C33 C32 . . . . -179.4(3) ?
C35 C36 C37 N12 . . . . -0.1(5) ?
O8 S2 C33 C34 . . . . -176.6(2) ?
O8 S2 C33 C32 . . . . 2.1(3) ?
C48 C49 C50 N15 . . . . 1.2(5) ?
C48 C47 C46 N15 . . . . 0.1(5) ?
C23 C22 C21 O6 . . . . -179.8(3) ?
C23 C22 C21 C29 . . . . 0.2(4) ?
C24 C25 C29 N11 . . . . 180.0(3) ?
C24 C25 C29 C21 . . . . -0.3(4) ?
C24 C25 C26 C27 . . . . 179.4(3) ?
C24 C23 C22 C21 . . . . -0.8(4) ?
C26 C25 C29 N11 . . . . -0.9(4) ?
C26 C25 C29 C21 . . . . 178.7(3) ?
C26 C25 C24 S1 . . . . -0.8(4) ?
C26 C25 C24 C23 . . . . -179.3(3) ?
C26 C27 C28 N11 . . . . -0.9(5) ?
C34 C35 C36 C37 . . . . -0.1(4) ?
C34 C33 C32 C31 . . . . 0.2(5) ?
C49 C48 C47 C46 . . . . 1.3(4) ?
C31 C30 C38 N12 . . . . -179.6(3) ?
C31 C30 C38 C34 . . . . 0.8(4) ?
C38 N12 C37 C36 . . . . -0.1(4) ?
C38 C30 C31 C32 . . . . -1.1(4) ?
C38 C34 C33 S2 . . . . 178.2(2) ?
C38 C34 C33 C32 . . . . -0.5(4) ?
C28 N11 C29 C25 . . . . 0.5(4) ?
C28 N11 C29 C21 . . . . -179.2(3) ?
C28 C27 C26 C25 . . . . 0.5(4) ?
C33 C34 C38 N12 . . . . -179.6(3) ?
C33 C34 C38 C30 . . . . 0.0(4) ?
C61 C62 C63 C64 . . . . -0.7(5) ?
C54 C55 C56 C57 . . . . 1.3(4) ?
C36 C35 C34 C38 . . . . 0.5(4) ?
C36 C35 C34 C33 . . . . 179.4(3) ?
C62 C61 C60 N19 . . . . -1.2(5) ?
C60 N19 C64 C63 . . . . -0.5(5) ?
C60 C61 C62 N20 . . . . -178.7(3) ?
C60 C61 C62 C63 . . . . 1.1(5) ?
C50 N15 C46 C47 . . . . -0.9(5) ?
C22 C23 C24 S1 . . . . -177.6(2) ?
C22 C23 C24 C25 . . . . 0.9(4) ?
C53 N18 C57 C56 . . . . -0.4(5) ?
C53 C54 C55 N17 . . . . -179.8(3) ?
C53 C54 C55 C56 . . . . -0.4(4) ?
C37 N12 C38 C30 . . . . -179.2(3) ?
C37 N12 C38 C34 . . . . 0.5(4) ?
C41 C40 C39 N14 . . . . 0.4(5) ?
C41 C42 C43 N14 . . . . -0.4(5) ?
C47 C48 C49 C50 . . . . -1.9(4) ?
C64 N19 C60 C61 . . . . 0.9(5) ?
C55 C54 C53 N18 . . . . -0.8(5) ?
C55 C56 C57 N18 . . . . -0.9(5) ?
C52 N16 C48 C49 . . . . -4.7(5) ?
C52 N16 C48 C47 . . . . 175.2(3) ?
C44 N13 C41 C40 . . . . -0.5(5) ?
C44 N13 C41 C42 . . . . 179.4(3) ?
C46 N15 C50 C49 . . . . 0.3(5) ?
C43 N14 C39 C40 . . . . 0.8(5) ?
C43 C42 C41 N13 . . . . -178.4(3) ?
C43 C42 C41 C40 . . . . 1.6(4) ?
C39 N14 C43 C42 . . . . -0.8(5) ?
C39 C40 C41 N13 . . . . 178.4(3) ?
C39 C40 C41 C42 . . . . -1.6(4) ?
C58 N17 C55 C54 . . . . -2.7(4) ?
C58 N17 C55 C56 . . . . 177.9(3) ?
C57 N18 C53 C54 . . . . 1.2(5) ?
C66 N20 C62 C61 . . . . 174.1(3) ?
C66 N20 C62 C63 . . . . -5.7(5) ?
C51 N16 C48 C49 . . . . 179.8(3) ?
C51 N16 C48 C47 . . . . -0.3(5) ?
C45 N13 C41 C40 . . . . -176.3(3) ?
C45 N13 C41 C42 . . . . 3.7(5) ?
C65 N20 C62 C61 . . . . -3.0(5) ?
C65 N20 C62 C63 . . . . 177.2(3) ?
C59 N17 C55 C54 . . . . -177.4(3) ?
C59 N17 C55 C56 . . . . 3.2(5) ?
