#------------------------------------------------------------------------------
#$Date: 2024-08-05 21:25:00 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293785 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/87/7248799.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_7248799
loop_
_publ_author_name
'Zhang, Liang'
'Wu, Di'
'Zhang, Menglong'
'Yu, Fuhai'
'Bao, Ying'
'Xie, Chuang'
'Hou, Baohong'
'Jing, Dingding'
'Zhang, Chuntao'
'Chen, Wei'
_publ_section_title
;
 Theoretical and experimental study of pharmaceutical salts: a case of
 trimethoprim
;
_journal_issue                   28
_journal_name_full               CrystEngComm
_journal_page_first              3808
_journal_page_last               3822
_journal_paper_doi               10.1039/D4CE00345D
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C14 H19 N4 O3, C7 H5 O4, C2 H3 N'
_chemical_formula_sum            'C23 H27 N5 O7'
_chemical_formula_weight         485.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-05-17
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-19 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.150(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0964(3)
_cell_length_b                   9.7449(2)
_cell_length_c                   20.4019(6)
_cell_measurement_reflns_used    9347
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35.2820
_cell_measurement_theta_min      2.0330
_cell_volume                     2359.54(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   0.50    0.50    --  -30.00   0.00 180.00  360
  2  ω    -62.00  60.00   0.50    0.50    --  -30.00  70.00 180.00  244
  3  ω    -62.00  60.00   0.50    0.50    --  -30.00  70.00  90.00  244
  4  ω   -120.00  20.00   0.50    0.50    --  -30.00   0.00  90.00  280
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0094468000
_diffrn_orient_matrix_UB_12      0.0717674000
_diffrn_orient_matrix_UB_13      -0.0028261000
_diffrn_orient_matrix_UB_21      0.0112648000
_diffrn_orient_matrix_UB_22      0.0058140000
_diffrn_orient_matrix_UB_23      0.0353258000
_diffrn_orient_matrix_UB_31      0.0579237000
_diffrn_orient_matrix_UB_32      0.0105792000
_diffrn_orient_matrix_UB_33      -0.0002819000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0862
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            50758
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.454
_diffrn_reflns_theta_min         1.716
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         11282
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1613
_refine_ls_R_factor_gt           0.0944
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0644P)²+1.3740P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1802
_refine_ls_wR_factor_ref         0.2138
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6581
_reflns_number_total             11282
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00345d2.cif
_cod_data_source_block           r20230402b_autored
_cod_depositor_comments
'Adding full bibliography for 7248797--7248804.cif.'
_cod_database_code               7248799
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C11 H10 N O'
_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.
;
_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
2.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C11(H11), C15(H15), C16(H16), C18(H18)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C5(H5A,H5B,H5C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.275
_oxdiff_exptl_absorpt_empirical_full_min 0.605
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
O1 O -0.09539(11) 0.71492(14) 0.45957(7) 0.0352(3) Uani 1 1 d . . . . .
O2 O -0.06715(10) 0.81720(13) 0.58369(7) 0.0317(3) Uani 1 1 d . . . . .
O3 O 0.11769(11) 0.96268(14) 0.63661(7) 0.0314(3) Uani 1 1 d . . . . .
N1 N 0.49875(12) 0.70323(15) 0.51374(8) 0.0268(3) Uani 1 1 d . . . . .
N2 N 0.57297(12) 0.84714(16) 0.44029(8) 0.0290(3) Uani 1 1 d . . . . .
N3 N 0.68575(14) 0.69141(19) 0.50755(9) 0.0357(4) Uani 1 1 d . . . . .
N4 N 0.46040(15) 1.00108(18) 0.37501(9) 0.0335(4) Uani 1 1 d . . . . .
C1 C 0.58549(14) 0.74809(18) 0.48641(9) 0.0270(3) Uani 1 1 d . . . . .
C2 C 0.47027(14) 0.90256(18) 0.42133(9) 0.0263(3) Uani 1 1 d . . . . .
C3 C 0.37521(14) 0.86225(17) 0.44916(9) 0.0253(3) Uani 1 1 d . . . . .
C4 C 0.39510(14) 0.76087(18) 0.49515(9) 0.0266(3) Uani 1 1 d . . . . .
H4 H 0.3363 0.7297 0.5146 0.032 Uiso 1 1 calc R U . . .
C24 C 0.26155(14) 0.92882(19) 0.42683(9) 0.0284(3) Uani 1 1 d . . . . .
H24A H 0.2318 0.9019 0.3810 0.034 Uiso 1 1 calc R U . . .
H24B H 0.2714 1.0276 0.4274 0.034 Uiso 1 1 calc R U . . .
C6 C 0.17623(14) 0.89252(17) 0.46918(9) 0.0261(3) Uani 1 1 d . . . . .
C7 C 0.19089(14) 0.94277(18) 0.53388(9) 0.0266(3) Uani 1 1 d . . . . .
H7 H 0.2541 0.9951 0.5512 0.032 Uiso 1 1 calc R U . . .
C8 C 0.11118(14) 0.91496(17) 0.57289(9) 0.0259(3) Uani 1 1 d . . . . .
C9 C 0.01559(14) 0.83744(17) 0.54651(9) 0.0269(3) Uani 1 1 d . . . . .
C10 C 0.00243(14) 0.78716(17) 0.48175(10) 0.0279(4) Uani 1 1 d . . . . .
C11 C 0.08252(14) 0.81306(18) 0.44281(10) 0.0287(4) Uani 1 1 d . . . . .
H11 H 0.0737 0.7778 0.3997 0.034 Uiso 1 1 calc R U . . .
C12 C -0.10362(19) 0.6414(3) 0.39838(14) 0.0535(7) Uani 1 1 d . . . . .
H12A H -0.1058 0.7051 0.3623 0.080 Uiso 1 1 calc R U . . .
H12B H -0.1712 0.5872 0.3906 0.080 Uiso 1 1 calc R U . . .
H12C H -0.0394 0.5822 0.4010 0.080 Uiso 1 1 calc R U . . .
C13 C -0.06419(18) 0.6830(2) 0.61256(12) 0.0420(5) Uani 1 1 d . . . . .
H13A H -0.0738 0.6153 0.5777 0.063 Uiso 1 1 calc R U . . .
H13B H -0.1238 0.6744 0.6372 0.063 Uiso 1 1 calc R U . . .
H13C H 0.0070 0.6692 0.6421 0.063 Uiso 1 1 calc R U . . .
C14 C 0.21886(17) 1.0330(2) 0.66607(10) 0.0359(4) Uani 1 1 d . . . . .
H14A H 0.2288 1.1114 0.6393 0.054 Uiso 1 1 calc R U . . .
H14B H 0.2820 0.9722 0.6684 0.054 Uiso 1 1 calc R U . . .
H14C H 0.2138 1.0625 0.7103 0.054 Uiso 1 1 calc R U . . .
O4 O 0.66745(13) 0.08235(16) 0.84696(9) 0.0445(4) Uani 1 1 d . . . . .
O5 O 0.82092(11) 0.33407(16) 0.68980(8) 0.0392(3) Uani 1 1 d . . . . .
O6 O 0.69704(12) 0.48701(15) 0.60882(8) 0.0372(3) Uani 1 1 d . . . . .
O7 O 0.51507(11) 0.51123(14) 0.61014(7) 0.0334(3) Uani 1 1 d . . . . .
C15 C 0.53179(15) 0.32058(18) 0.71784(9) 0.0285(4) Uani 1 1 d . . . . .
H15 H 0.4612 0.3580 0.7013 0.034 Uiso 1 1 calc R U . . .
C16 C 0.54320(15) 0.22923(19) 0.77025(10) 0.0298(4) Uani 1 1 d . . . . .
H16 H 0.4813 0.2054 0.7887 0.036 Uiso 1 1 calc R U . . .
C17 C 0.64958(16) 0.17261(19) 0.79546(10) 0.0320(4) Uani 1 1 d . . . . .
C18 C 0.74082(15) 0.2095(2) 0.76796(11) 0.0356(4) Uani 1 1 d . . . . .
H18 H 0.8113 0.1724 0.7850 0.043 Uiso 1 1 calc R U . . .
C19 C 0.72873(15) 0.30151(19) 0.71507(10) 0.0304(4) Uani 1 1 d . . . . .
C20 C 0.62283(14) 0.35907(17) 0.68866(9) 0.0265(3) Uani 1 1 d . . . . .
C21 C 0.61035(15) 0.45885(18) 0.63290(9) 0.0287(4) Uani 1 1 d . . . . .
N22 N 0.26525(17) 1.1542(2) 0.28304(12) 0.0552(6) Uani 1 1 d . . . . .
C23 C 0.1771(2) 1.1132(3) 0.27811(13) 0.0575(7) Uani 1 1 d . . . . .
C5 C 0.0591(2) 1.0543(3) 0.27059(13) 0.0552(7) Uani 1 1 d . . . . .
H5A H 0.0071 1.1115 0.2411 0.083 Uiso 1 1 calc R U . . .
H5B H 0.0379 1.0507 0.3135 0.083 Uiso 1 1 calc R U . . .
H5C H 0.0578 0.9633 0.2523 0.083 Uiso 1 1 calc R U . . .
H4A H 0.396(2) 1.036(3) 0.3562(12) 0.040(6) Uiso 1 1 d . . . . .
H4B H 0.519(2) 1.021(2) 0.3569(12) 0.041(6) Uiso 1 1 d . . . . .
H3A H 0.692(2) 0.625(3) 0.5404(13) 0.052(7) Uiso 1 1 d . . . . .
H3B H 0.746(2) 0.727(3) 0.4933(13) 0.049(7) Uiso 1 1 d . . . . .
H1 H 0.510(2) 0.633(3) 0.5481(14) 0.056(8) Uiso 1 1 d . . . . .
H4C H 0.603(3) 0.054(4) 0.8561(16) 0.080(10) Uiso 1 1 d . . . . .
H5 H 0.792(3) 0.393(4) 0.6537(16) 0.075(10) Uiso 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
C10 O1 C12 117.06(16) . . ?
C9 O2 C13 113.14(15) . . ?
C8 O3 C14 116.71(14) . . ?
C1 N1 C4 119.91(16) . . ?
C1 N1 H1 120.9(16) . . ?
C4 N1 H1 119.2(16) . . ?
C1 N2 C2 117.81(15) . . ?
C1 N3 H3A 117.8(16) . . ?
C1 N3 H3B 118.8(17) . . ?
H3A N3 H3B 123(2) . . ?
C2 N4 H4A 122.9(16) . . ?
C2 N4 H4B 119.1(16) . . ?
H4A N4 H4B 117(2) . . ?
N2 C1 N1 122.18(16) . . ?
N3 C1 N1 117.70(17) . . ?
N3 C1 N2 120.11(17) . . ?
N2 C2 C3 123.03(16) . . ?
N4 C2 N2 116.38(16) . . ?
N4 C2 C3 120.58(16) . . ?
C2 C3 C24 121.12(16) . . ?
C4 C3 C2 115.27(16) . . ?
C4 C3 C24 123.60(16) . . ?
N1 C4 H4 119.1 . . ?
C3 C4 N1 121.77(16) . . ?
C3 C4 H4 119.1 . . ?
C3 C24 H24A 108.7 . . ?
C3 C24 H24B 108.7 . . ?
C3 C24 C6 114.20(15) . . ?
H24A C24 H24B 107.6 . . ?
C6 C24 H24A 108.7 . . ?
C6 C24 H24B 108.7 . . ?
C7 C6 C24 119.08(15) . . ?
C7 C6 C11 120.60(17) . . ?
C11 C6 C24 120.29(16) . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.06(16) . . ?
C8 C7 H7 120.0 . . ?
O3 C8 C7 123.96(15) . . ?
O3 C8 C9 116.13(16) . . ?
C7 C8 C9 119.88(16) . . ?
O2 C9 C8 119.90(16) . . ?
O2 C9 C10 120.65(15) . . ?
C10 C9 C8 119.38(16) . . ?
O1 C10 C9 115.24(16) . . ?
O1 C10 C11 123.72(17) . . ?
C9 C10 C11 121.02(16) . . ?
C6 C11 H11 120.5 . . ?
C10 C11 C6 119.05(17) . . ?
C10 C11 H11 120.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C17 O4 H4C 111(2) . . ?
C19 O5 H5 103.3(19) . . ?
C16 C15 H15 118.9 . . ?
C16 C15 C20 122.27(16) . . ?
C20 C15 H15 118.9 . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 119.07(18) . . ?
C17 C16 H16 120.5 . . ?
O4 C17 C16 122.48(18) . . ?
O4 C17 C18 117.68(17) . . ?
C18 C17 C16 119.84(18) . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.82(17) . . ?
C19 C18 H18 119.6 . . ?
O5 C19 C18 118.46(17) . . ?
O5 C19 C20 121.13(18) . . ?
C18 C19 C20 120.41(17) . . ?
C15 C20 C19 117.59(17) . . ?
C15 C20 C21 122.03(16) . . ?
C19 C20 C21 120.37(16) . . ?
O6 C21 C20 117.98(16) . . ?
O7 C21 O6 122.18(18) . . ?
O7 C21 C20 119.83(16) . . ?
N22 C23 C5 178.4(3) . . ?
C23 C5 H5A 109.5 . . ?
C23 C5 H5B 109.5 . . ?
C23 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 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
O1 C10 1.376(2) . ?
O1 C12 1.426(3) . ?
O2 C9 1.382(2) . ?
O2 C13 1.432(2) . ?
O3 C8 1.369(2) . ?
O3 C14 1.429(2) . ?
N1 C1 1.352(2) . ?
N1 C4 1.359(2) . ?
N1 H1 0.97(3) . ?
N2 C1 1.336(2) . ?
N2 C2 1.341(2) . ?
N3 C1 1.327(2) . ?
N3 H3A 0.93(3) . ?
N3 H3B 0.91(3) . ?
N4 C2 1.336(2) . ?
N4 H4A 0.87(3) . ?
N4 H4B 0.88(3) . ?
C2 C3 1.432(2) . ?
C3 C4 1.352(2) . ?
C3 C24 1.509(2) . ?
C4 H4 0.9300 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C6 1.511(2) . ?
C6 C7 1.387(3) . ?
C6 C11 1.392(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.390(2) . ?
C8 C9 1.399(2) . ?
C9 C10 1.389(3) . ?
C10 C11 1.390(3) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O4 C17 1.355(2) . ?
O4 H4C 0.88(3) . ?
O5 C19 1.354(2) . ?
O5 H5 0.95(3) . ?
O6 C21 1.271(2) . ?
O7 C21 1.264(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(3) . ?
C15 C20 1.400(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.403(2) . ?
C17 C18 1.379(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.389(3) . ?
C19 C20 1.407(2) . ?
C20 C21 1.482(3) . ?
N22 C23 1.125(3) . ?
C23 C5 1.518(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
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
O1 C10 C11 C6 177.16(16) . . . . ?
O2 C9 C10 O1 -1.6(2) . . . . ?
O2 C9 C10 C11 176.68(15) . . . . ?
O3 C8 C9 O2 2.2(2) . . . . ?
O3 C8 C9 C10 179.12(15) . . . . ?
N2 C2 C3 C4 -1.7(3) . . . . ?
N2 C2 C3 C24 179.24(16) . . . . ?
N4 C2 C3 C4 179.48(16) . . . . ?
N4 C2 C3 C24 0.4(3) . . . . ?
C1 N1 C4 C3 0.6(3) . . . . ?
C1 N2 C2 N4 -179.83(16) . . . . ?
C1 N2 C2 C3 1.3(3) . . . . ?
C2 N2 C1 N1 0.1(3) . . . . ?
C2 N2 C1 N3 -179.01(17) . . . . ?
C2 C3 C4 N1 0.7(2) . . . . ?
C2 C3 C24 C6 -169.93(15) . . . . ?
C3 C24 C6 C7 69.7(2) . . . . ?
C3 C24 C6 C11 -112.16(18) . . . . ?
C4 N1 C1 N2 -1.1(3) . . . . ?
C4 N1 C1 N3 178.10(17) . . . . ?
C4 C3 C24 C6 11.1(2) . . . . ?
C24 C3 C4 N1 179.76(16) . . . . ?
C24 C6 C7 C8 177.57(15) . . . . ?
C24 C6 C11 C10 -176.71(16) . . . . ?
C6 C7 C8 O3 -178.59(15) . . . . ?
C6 C7 C8 C9 -0.7(2) . . . . ?
C7 C6 C11 C10 1.4(3) . . . . ?
C7 C8 C9 O2 -175.85(15) . . . . ?
C7 C8 C9 C10 1.0(2) . . . . ?
C8 C9 C10 O1 -178.51(15) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C6 -1.0(3) . . . . ?
C11 C6 C7 C8 -0.5(3) . . . . ?
C12 O1 C10 C9 -169.33(19) . . . . ?
C12 O1 C10 C11 12.4(3) . . . . ?
C13 O2 C9 C8 -103.50(19) . . . . ?
C13 O2 C9 C10 79.6(2) . . . . ?
C14 O3 C8 C7 -6.7(2) . . . . ?
C14 O3 C8 C9 175.32(15) . . . . ?
O4 C17 C18 C19 179.99(18) . . . . ?
O5 C19 C20 C15 -179.69(16) . . . . ?
O5 C19 C20 C21 -0.9(3) . . . . ?
C15 C16 C17 O4 179.87(18) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C15 C20 C21 O6 -179.26(17) . . . . ?
C15 C20 C21 O7 -0.4(3) . . . . ?
C16 C15 C20 C19 -0.4(3) . . . . ?
C16 C15 C20 C21 -179.15(17) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C17 C18 C19 O5 -179.84(18) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C19 C20 C15 0.3(3) . . . . ?
C18 C19 C20 C21 179.06(17) . . . . ?
C19 C20 C21 O6 2.0(2) . . . . ?
C19 C20 C21 O7 -179.10(16) . . . . ?
C20 C15 C16 C17 0.1(3) . . . . ?
