#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:09:31 +0100 (Sat 04 de Mar de 2023) $
#$Revision: 281412 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/61/7246190.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_7246190
loop_
_publ_author_name
'Surampudi, Anuja Venkata Sai Durga'
'Ramakrishna, Sistla'
'Pallavi, Alegete'
'Balasubramanian, Sridhar'
_publ_section_title
;
 Novel salts and cocrystals of the antifolate drug trimethoprim and their
 role in the enhancement of solubility and dissolution
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              1220
_journal_page_last               1231
_journal_paper_doi               10.1039/D2CE01436J
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C14 H19 N4 O3, C9 H9 N4 O4'
_chemical_formula_sum            'C23 H28 N8 O7'
_chemical_formula_weight         528.53
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-06-20 deposited with the CCDC.	2023-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                104.2296(6)
_cell_angle_beta                 95.4410(7)
_cell_angle_gamma                97.9255(7)
_cell_formula_units_Z            2
_cell_length_a                   7.9637(2)
_cell_length_b                   9.4953(2)
_cell_length_c                   17.6571(4)
_cell_measurement_reflns_used    9639
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      30.4005
_cell_measurement_theta_min      2.2445
_cell_volume                     1270.29(5)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23764
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.244
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         4441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0450
_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)+(0.0620P)²+0.3449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3757
_reflns_number_total             4441
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01436j2.cif
_cod_data_source_block           KB194_0m
_cod_depositor_comments
'Adding full bibliography for 7246190--7246193.cif.'
_cod_database_code               7246190
_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   0.972
_shelx_estimated_absorpt_t_max   0.983
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
C1 C 0.5069(2) 0.51323(17) 0.38199(9) 0.0337(3) Uani 1 1 d . . . . .
C2 C 0.3629(2) 0.39482(17) 0.35843(9) 0.0353(4) Uani 1 1 d . . . . .
C3 C 0.5030(2) 0.24886(17) 0.41964(9) 0.0348(4) Uani 1 1 d . . . . .
C4 C 0.6449(2) 0.48479(17) 0.42330(9) 0.0364(4) Uani 1 1 d . . . . .
H4 H 0.741585 0.557283 0.439966 0.044 Uiso 1 1 calc R U . . .
C5 C 0.5010(2) 0.65985(17) 0.36435(9) 0.0360(4) Uani 1 1 d . . . . .
H5A H 0.576673 0.734763 0.405446 0.043 Uiso 1 1 calc R U . . .
H5B H 0.385851 0.681143 0.367728 0.043 Uiso 1 1 calc R U . . .
C6 C 0.54957(19) 0.67529(17) 0.28496(9) 0.0336(3) Uani 1 1 d . . . . .
C7 C 0.5327(2) 0.80667(18) 0.26581(10) 0.0385(4) Uani 1 1 d . . . . .
H7 H 0.485703 0.878066 0.299348 0.046 Uiso 1 1 calc R U . . .
C8 C 0.5857(2) 0.83190(18) 0.19681(10) 0.0403(4) Uani 1 1 d . . . . .
C9 C 0.6575(2) 0.72515(19) 0.14665(10) 0.0407(4) Uani 1 1 d . . . . .
C10 C 0.6712(2) 0.59329(18) 0.16528(9) 0.0385(4) Uani 1 1 d . . . . .
C11 C 0.6178(2) 0.56812(18) 0.23459(9) 0.0369(4) Uani 1 1 d . . . . .
H11 H 0.627934 0.479652 0.246911 0.044 Uiso 1 1 calc R U . . .
C12 C 0.5186(3) 1.0745(2) 0.22528(14) 0.0631(6) Uani 1 1 d . . . . .
H12A H 0.502999 1.150628 0.199440 0.095 Uiso 1 1 calc R U . . .
H12B H 0.602840 1.113644 0.271021 0.095 Uiso 1 1 calc R U . . .
H12C H 0.412090 1.038913 0.240949 0.095 Uiso 1 1 calc R U . . .
C13 C 0.6071(3) 0.7334(4) 0.01394(13) 0.0910(9) Uani 1 1 d . . . . .
H13A H 0.666586 0.754638 -0.027803 0.137 Uiso 1 1 calc R U . . .
H13B H 0.525122 0.798296 0.025281 0.137 Uiso 1 1 calc R U . . .
H13C H 0.549041 0.633083 -0.001996 0.137 Uiso 1 1 calc R U . . .
C14 C 0.7670(3) 0.3613(2) 0.12968(12) 0.0643(6) Uani 1 1 d . . . . .
H14A H 0.658338 0.306800 0.133080 0.097 Uiso 1 1 calc R U . . .
H14B H 0.839565 0.381644 0.179015 0.097 Uiso 1 1 calc R U . . .
H14C H 0.819563 0.304436 0.088562 0.097 Uiso 1 1 calc R U . . .
O1 O 0.57435(19) 0.95716(14) 0.17280(8) 0.0596(4) Uani 1 1 d . . . . .
O2 O 0.72551(16) 0.75399(16) 0.08207(7) 0.0570(4) Uani 1 1 d . . . . .
O3 O 0.74255(17) 0.49539(15) 0.11256(7) 0.0526(3) Uani 1 1 d . . . . .
N1 N 0.36346(17) 0.26777(14) 0.37866(8) 0.0392(3) Uani 1 1 d . . . . .
N2 N 0.64602(17) 0.35330(15) 0.44111(8) 0.0370(3) Uani 1 1 d . . . . .
H2N H 0.739(3) 0.332(2) 0.4724(12) 0.060(6) Uiso 1 1 d . . . . .
N3 N 0.2213(2) 0.40564(19) 0.31560(10) 0.0499(4) Uani 1 1 d . . . . .
H3NA H 0.140(3) 0.325(3) 0.3052(13) 0.070(7) Uiso 1 1 d . . . . .
H3NB H 0.205(2) 0.488(2) 0.3001(11) 0.051(5) Uiso 1 1 d . . . . .
N4 N 0.5049(2) 0.12245(16) 0.43917(9) 0.0453(4) Uani 1 1 d . . . . .
H4NA H 0.404(3) 0.062(2) 0.4316(12) 0.055(6) Uiso 1 1 d . . . . .
H4NB H 0.594(3) 0.114(2) 0.4724(12) 0.053(5) Uiso 1 1 d . . . . .
C15 C 0.8863(2) 0.1569(2) 0.88748(10) 0.0460(4) Uani 1 1 d . . . . .
C16 C 0.91699(19) 0.26441(18) 0.77262(9) 0.0358(4) Uani 1 1 d . . . . .
C17 C 0.96507(19) 0.12848(17) 0.73552(9) 0.0329(3) Uani 1 1 d . . . . .
C18 C 0.96932(19) 0.01495(17) 0.77037(9) 0.0351(4) Uani 1 1 d . . . . .
C19 C 0.9486(4) -0.0897(3) 0.88401(13) 0.0738(7) Uani 1 1 d . . . . .
H19A H 0.923173 -0.183667 0.845703 0.111 Uiso 1 1 calc R U . . .
H19B H 0.872274 -0.087543 0.923070 0.111 Uiso 1 1 calc R U . . .
H19C H 1.064538 -0.074617 0.908922 0.111 Uiso 1 1 calc R U . . .
C20 C 0.8273(3) 0.4048(2) 0.89391(12) 0.0570(5) Uani 1 1 d . . . . .
H20A H 0.750539 0.439826 0.860252 0.085 Uiso 1 1 calc R U . . .
H20B H 0.927726 0.478161 0.913952 0.085 Uiso 1 1 calc R U . . .
H20C H 0.771553 0.385580 0.937076 0.085 Uiso 1 1 calc R U . . .
C21 C 1.0492(2) -0.05821(18) 0.65903(9) 0.0398(4) Uani 1 1 d . . . . .
H21 H 1.086589 -0.116498 0.615533 0.048 Uiso 1 1 calc R U . . .
C22 C 1.0554(2) 0.16583(19) 0.60712(9) 0.0375(4) Uani 1 1 d . . . . .
H22A H 1.132175 0.119857 0.573014 0.045 Uiso 1 1 calc R U . . .
H22B H 1.115030 0.263002 0.636270 0.045 Uiso 1 1 calc R U . . .
C23 C 0.8995(2) 0.18366(17) 0.55585(9) 0.0350(4) Uani 1 1 d . . . . .
N5 N 0.92718(18) 0.02657(16) 0.84506(8) 0.0421(3) Uani 1 1 d . . . . .
N6 N 0.87640(18) 0.26824(16) 0.84862(8) 0.0415(3) Uani 1 1 d . . . . .
N7 N 1.01945(16) 0.07908(14) 0.66305(7) 0.0343(3) Uani 1 1 d . . . . .
N8 N 1.02012(18) -0.10326(15) 0.72303(8) 0.0410(3) Uani 1 1 d . . . . .
O4 O 0.8565(2) 0.17328(18) 0.95508(8) 0.0709(4) Uani 1 1 d . . . . .
O5 O 0.90779(16) 0.36908(13) 0.74401(7) 0.0480(3) Uani 1 1 d . . . . .
O6 O 0.76588(16) 0.09423(15) 0.54810(8) 0.0593(4) Uani 1 1 d . . . . .
O7 O 0.92195(15) 0.28516(14) 0.52246(7) 0.0495(3) 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'
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
C4 C1 C2 115.33(14) . . ?
C4 C1 C5 122.69(14) . . ?
C2 C1 C5 121.94(13) . . ?
N3 C2 N1 116.08(15) . . ?
N3 C2 C1 121.82(15) . . ?
N1 C2 C1 122.10(14) . . ?
N1 C3 N4 119.10(15) . . ?
N1 C3 N2 122.23(14) . . ?
N4 C3 N2 118.66(14) . . ?
C1 C4 N2 121.97(15) . . ?
C1 C4 H4 119.0 . . ?
N2 C4 H4 119.0 . . ?
C1 C5 C6 117.09(13) . . ?
C1 C5 H5A 108.0 . . ?
C6 C5 H5A 108.0 . . ?
C1 C5 H5B 108.0 . . ?
C6 C5 H5B 108.0 . . ?
H5A C5 H5B 107.3 . . ?
C11 C6 C7 119.87(14) . . ?
C11 C6 C5 122.57(14) . . ?
C7 C6 C5 117.46(13) . . ?
C8 C7 C6 120.36(15) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
O1 C8 C7 124.75(16) . . ?
O1 C8 C9 115.38(15) . . ?
C7 C8 C9 119.87(15) . . ?
O2 C9 C10 119.74(15) . . ?
O2 C9 C8 120.55(15) . . ?
C10 C9 C8 119.54(15) . . ?
O3 C10 C9 115.36(14) . . ?
O3 C10 C11 124.14(15) . . ?
C9 C10 C11 120.49(15) . . ?
C6 C11 C10 119.85(14) . . ?
C6 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 O1 C12 117.51(14) . . ?
C9 O2 C13 115.69(15) . . ?
C10 O3 C14 118.27(14) . . ?
C3 N1 C2 118.87(14) . . ?
C3 N2 C4 119.40(13) . . ?
C3 N2 H2N 116.8(13) . . ?
C4 N2 H2N 123.6(13) . . ?
C2 N3 H3NA 113.6(15) . . ?
C2 N3 H3NB 123.6(12) . . ?
H3NA N3 H3NB 122.7(19) . . ?
C3 N4 H4NA 116.3(13) . . ?
C3 N4 H4NB 118.9(13) . . ?
H4NA N4 H4NB 121.6(18) . . ?
O4 C15 N5 121.43(17) . . ?
O4 C15 N6 121.48(17) . . ?
N5 C15 N6 117.07(14) . . ?
O5 C16 N6 121.60(15) . . ?
O5 C16 C17 126.34(15) . . ?
N6 C16 C17 112.05(13) . . ?
C18 C17 N7 105.00(13) . . ?
C18 C17 C16 123.29(14) . . ?
N7 C17 C16 131.68(14) . . ?
N8 C18 C17 112.14(14) . . ?
N8 C18 N5 126.48(14) . . ?
C17 C18 N5 121.38(14) . . ?
N5 C19 H19A 109.5 . . ?
N5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N6 C20 H20A 109.5 . . ?
N6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N8 C21 N7 113.84(14) . . ?
N8 C21 H21 123.1 . . ?
N7 C21 H21 123.1 . . ?
N7 C22 C23 115.25(13) . . ?
N7 C22 H22A 108.5 . . ?
C23 C22 H22A 108.5 . . ?
N7 C22 H22B 108.5 . . ?
C23 C22 H22B 108.5 . . ?
H22A C22 H22B 107.5 . . ?
O6 C23 O7 126.12(15) . . ?
O6 C23 C22 118.18(14) . . ?
O7 C23 C22 115.63(14) . . ?
C18 N5 C15 119.74(14) . . ?
C18 N5 C19 120.43(15) . . ?
C15 N5 C19 119.26(15) . . ?
C15 N6 C16 126.26(14) . . ?
C15 N6 C20 116.38(15) . . ?
C16 N6 C20 117.28(14) . . ?
C21 N7 C17 105.99(13) . . ?
C21 N7 C22 127.42(14) . . ?
C17 N7 C22 126.24(13) . . ?
C21 N8 C18 103.01(13) . . ?
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 C4 1.356(2) . ?
C1 C2 1.441(2) . ?
C1 C5 1.505(2) . ?
C2 N3 1.327(2) . ?
C2 N1 1.340(2) . ?
C3 N1 1.326(2) . ?
C3 N4 1.329(2) . ?
C3 N2 1.359(2) . ?
C4 N2 1.362(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.524(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C11 1.386(2) . ?
C6 C7 1.391(2) . ?
C7 C8 1.390(2) . ?
C7 H7 0.9300 . ?
C8 O1 1.3685(19) . ?
C8 C9 1.397(2) . ?
C9 O2 1.3780(19) . ?
C9 C10 1.386(2) . ?
C10 O3 1.369(2) . ?
C10 C11 1.397(2) . ?
C11 H11 0.9300 . ?
C12 O1 1.416(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O2 1.412(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O3 1.413(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N2 H2N 0.95(2) . ?
N3 H3NA 0.90(2) . ?
N3 H3NB 0.91(2) . ?
N4 H4NA 0.90(2) . ?
N4 H4NB 0.90(2) . ?
C15 O4 1.216(2) . ?
C15 N5 1.378(2) . ?
C15 N6 1.402(2) . ?
C16 O5 1.2281(19) . ?
C16 N6 1.403(2) . ?
C16 C17 1.418(2) . ?
C17 C18 1.369(2) . ?
C17 N7 1.382(2) . ?
C18 N8 1.360(2) . ?
C18 N5 1.373(2) . ?
C19 N5 1.458(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N6 1.471(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N8 1.332(2) . ?
C21 N7 1.343(2) . ?
C21 H21 0.9300 . ?
C22 N7 1.4574(19) . ?
C22 C23 1.520(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 O6 1.240(2) . ?
C23 O7 1.2491(19) . ?
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
C13 H13B O1 0.96 2.63 3.133(3) 112.9 . yes
C14 H14C O4 0.96 2.45 3.356(2) 158.2 1_554 yes
N2 H2N O7 0.95(2) 1.80(2) 2.7497(17) 174.3(19) . yes
N3 H3NA N8 0.90(2) 2.22(3) 3.110(2) 169(2) 2_656 yes
N3 H3NB O5 0.91(2) 2.00(2) 2.8722(19) 161.1(17) 2_666 yes
N4 H4NA O6 0.90(2) 1.99(2) 2.833(2) 155.6(18) 2_656 yes
N4 H4NB O6 0.90(2) 1.88(2) 2.7823(19) 174.9(18) . yes
C21 H21 O7 0.93 2.55 3.442(2) 159.7 2_756 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
C4 C1 C2 N3 -177.86(15) . . . . ?
C5 C1 C2 N3 4.4(2) . . . . ?
C4 C1 C2 N1 2.4(2) . . . . ?
C5 C1 C2 N1 -175.36(14) . . . . ?
C2 C1 C4 N2 -0.1(2) . . . . ?
C5 C1 C4 N2 177.68(14) . . . . ?
C4 C1 C5 C6 95.06(18) . . . . ?
C2 C1 C5 C6 -87.32(18) . . . . ?
C1 C5 C6 C11 -8.2(2) . . . . ?
C1 C5 C6 C7 175.52(14) . . . . ?
C11 C6 C7 C8 -0.7(2) . . . . ?
C5 C6 C7 C8 175.60(14) . . . . ?
C6 C7 C8 O1 179.91(15) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
O1 C8 C9 O2 5.9(2) . . . . ?
C7 C8 C9 O2 -173.76(14) . . . . ?
O1 C8 C9 C10 -178.73(14) . . . . ?
C7 C8 C9 C10 1.6(2) . . . . ?
O2 C9 C10 O3 -4.8(2) . . . . ?
C8 C9 C10 O3 179.81(14) . . . . ?
O2 C9 C10 C11 173.83(14) . . . . ?
C8 C9 C10 C11 -1.6(2) . . . . ?
C7 C6 C11 C10 0.8(2) . . . . ?
C5 C6 C11 C10 -175.37(14) . . . . ?
O3 C10 C11 C6 178.89(15) . . . . ?
C9 C10 C11 C6 0.4(2) . . . . ?
C7 C8 O1 C12 5.8(3) . . . . ?
C9 C8 O1 C12 -173.83(16) . . . . ?
C10 C9 O2 C13 101.5(2) . . . . ?
C8 C9 O2 C13 -83.2(2) . . . . ?
C9 C10 O3 C14 177.37(16) . . . . ?
C11 C10 O3 C14 -1.2(2) . . . . ?
N4 C3 N1 C2 -179.33(15) . . . . ?
N2 C3 N1 C2 -0.7(2) . . . . ?
N3 C2 N1 C3 178.20(15) . . . . ?
C1 C2 N1 C3 -2.1(2) . . . . ?
N1 C3 N2 C4 3.0(2) . . . . ?
N4 C3 N2 C4 -178.37(14) . . . . ?
C1 C4 N2 C3 -2.5(2) . . . . ?
O5 C16 C17 C18 -178.64(15) . . . . ?
N6 C16 C17 C18 0.5(2) . . . . ?
O5 C16 C17 N7 3.2(3) . . . . ?
N6 C16 C17 N7 -177.65(15) . . . . ?
N7 C17 C18 N8 -1.18(18) . . . . ?
C16 C17 C18 N8 -179.76(14) . . . . ?
N7 C17 C18 N5 178.25(13) . . . . ?
C16 C17 C18 N5 -0.3(2) . . . . ?
N7 C22 C23 O6 -20.1(2) . . . . ?
N7 C22 C23 O7 162.91(14) . . . . ?
N8 C18 N5 C15 176.68(15) . . . . ?
C17 C18 N5 C15 -2.7(2) . . . . ?
N8 C18 N5 C19 5.4(3) . . . . ?
C17 C18 N5 C19 -173.96(18) . . . . ?
O4 C15 N5 C18 -176.36(17) . . . . ?
N6 C15 N5 C18 5.1(2) . . . . ?
O4 C15 N5 C19 -5.0(3) . . . . ?
N6 C15 N5 C19 176.54(18) . . . . ?
O4 C15 N6 C16 176.23(17) . . . . ?
N5 C15 N6 C16 -5.3(3) . . . . ?
O4 C15 N6 C20 -0.4(3) . . . . ?
N5 C15 N6 C20 178.13(15) . . . . ?
O5 C16 N6 C15 -178.42(15) . . . . ?
C17 C16 N6 C15 2.4(2) . . . . ?
O5 C16 N6 C20 -1.8(2) . . . . ?
C17 C16 N6 C20 178.96(14) . . . . ?
N8 C21 N7 C17 -0.45(18) . . . . ?
N8 C21 N7 C22 173.07(14) . . . . ?
C18 C17 N7 C21 0.95(16) . . . . ?
C16 C17 N7 C21 179.36(16) . . . . ?
C18 C17 N7 C22 -172.67(13) . . . . ?
C16 C17 N7 C22 5.7(3) . . . . ?
C23 C22 N7 C21 106.86(18) . . . . ?
C23 C22 N7 C17 -80.87(19) . . . . ?
N7 C21 N8 C18 -0.25(18) . . . . ?
C17 C18 N8 C21 0.90(18) . . . . ?
N5 C18 N8 C21 -178.49(15) . . . . ?
