#------------------------------------------------------------------------------
#$Date: 2023-07-05 13:12:18 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284924 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/67/7246784.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_7246784
loop_
_publ_author_name
'Hu, Xingchen'
'Xiao, Yuntian'
'Qi, Luguang'
'Bai, Yunhe'
'Sun, Ying'
'Ye, Yang'
'Xie, Chuang'
_publ_section_title
;
 Enhancing the dissolution and bacteriostatic activity of trimethoprim
 through salt formation
;
_journal_issue                   23
_journal_name_full               CrystEngComm
_journal_page_first              3445
_journal_page_last               3459
_journal_paper_doi               10.1039/D3CE00128H
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C14 H19 N4 O3, C7 H5 O4'
_chemical_formula_sum            'C21 H24 N4 O7'
_chemical_formula_weight         444.44
_chemical_name_systematic        TMP-26HBA
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-02
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-22 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.922(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.4626(13)
_cell_length_b                   9.2831(4)
_cell_length_c                   19.5540(11)
_cell_measurement_reflns_used    7323
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      31.9390
_cell_measurement_theta_min      2.2610
_cell_volume                     4287.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.923
_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   1.00    1.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  30.00   1.00    1.00    --  -30.00  45.00  90.00  150
  3  ω   -120.00  30.00   1.00    1.00    --  -30.00  45.00 180.00  150
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0245209000
_diffrn_orient_matrix_UB_12      0.0425244000
_diffrn_orient_matrix_UB_13      0.0063614000
_diffrn_orient_matrix_UB_21      0.0169500000
_diffrn_orient_matrix_UB_22      -0.0630752000
_diffrn_orient_matrix_UB_23      0.0084627000
_diffrn_orient_matrix_UB_31      -0.0037056000
_diffrn_orient_matrix_UB_32      -0.0069969000
_diffrn_orient_matrix_UB_33      -0.0376406000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            23814
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.258
_diffrn_reflns_theta_min         2.264
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0023(3)
_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   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         7029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0603
_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)+(0.0549P)²+1.5795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1585
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4306
_reflns_number_total             7029
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00128h2.cif
_cod_data_source_block           r20220722b
_cod_depositor_comments
'Adding full bibliography for 7246781--7246785.cif.'
_cod_database_code               7246784
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C9(H9), C14(H14), C16(H16), C17(H17), C18(H18)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N4(H4A,H4B)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2C,H2D,H2E), C3(H3A,H3B,H3C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.822
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.61315(5) 0.87024(13) 0.66582(6) 0.0363(3) Uani 1 1 d . . . . .
O2 O 0.52323(5) 0.72074(13) 0.66569(6) 0.0338(3) Uani 1 1 d . . . . .
O3 O 0.44378(5) 0.62598(13) 0.53978(6) 0.0352(3) Uani 1 1 d . . . . .
N1 N 0.61960(6) 0.63978(15) 0.34941(8) 0.0353(3) Uani 1 1 d . . . . .
H1 H 0.633393 0.553414 0.364272 0.042 Uiso 1 1 calc R U . . .
N2 N 0.66417(7) 0.63847(16) 0.26652(9) 0.0457(4) Uani 1 1 d . . . . .
H2A H 0.672996 0.679300 0.231621 0.055 Uiso 1 1 calc R U . . .
H2B H 0.676603 0.551371 0.282041 0.055 Uiso 1 1 calc R U . . .
N3 N 0.61302(6) 0.84042(15) 0.27254(8) 0.0322(3) Uani 1 1 d . . . . .
N4 N 0.56806(6) 1.04471(15) 0.28506(8) 0.0333(3) Uani 1 1 d . . . . .
H4A H 0.578622 1.084902 0.251486 0.040 Uiso 1 1 calc R U . . .
H4B H 0.548008 1.094238 0.305076 0.040 Uiso 1 1 calc R U . . .
C1 C 0.66145(8) 0.9520(2) 0.66704(12) 0.0457(5) Uani 1 1 d . . . . .
H1A H 0.681651 0.898323 0.641249 0.069 Uiso 1 1 calc R U . . .
H1B H 0.686818 0.968575 0.718237 0.069 Uiso 1 1 calc R U . . .
H1C H 0.648819 1.044717 0.642455 0.069 Uiso 1 1 calc R U . . .
C2 C 0.55191(11) 0.5917(2) 0.69938(12) 0.0559(6) Uani 1 1 d . . . . .
H2C H 0.531946 0.508168 0.670787 0.084 Uiso 1 1 calc R U . . .
H2D H 0.552692 0.584812 0.749765 0.084 Uiso 1 1 calc R U . . .
H2E H 0.590757 0.593706 0.700699 0.084 Uiso 1 1 calc R U . . .
C3 C 0.39919(8) 0.5824(2) 0.47332(10) 0.0420(4) Uani 1 1 d . . . . .
H3A H 0.381098 0.667874 0.444820 0.063 Uiso 1 1 calc R U . . .
H3B H 0.371099 0.526804 0.485422 0.063 Uiso 1 1 calc R U . . .
H3C H 0.414765 0.522664 0.444107 0.063 Uiso 1 1 calc R U . . .
C4 C 0.57307(7) 0.83722(17) 0.59794(9) 0.0275(3) Uani 1 1 d . . . . .
C5 C 0.52790(7) 0.75283(16) 0.59896(8) 0.0267(3) Uani 1 1 d . . . . .
C6 C 0.48524(6) 0.71140(16) 0.53284(9) 0.0268(3) Uani 1 1 d . . . . .
C7 C 0.48626(7) 0.76223(17) 0.46591(9) 0.0295(3) Uani 1 1 d . . . . .
H7 H 0.457199 0.735269 0.420741 0.035 Uiso 1 1 calc R U . . .
C8 C 0.52985(7) 0.85219(17) 0.46562(9) 0.0292(3) Uani 1 1 d . . . . .
C9 C 0.57405(7) 0.88734(17) 0.53119(9) 0.0304(3) Uani 1 1 d . . . . .
H9 H 0.604650 0.945041 0.530456 0.036 Uiso 1 1 calc R U . . .
C10 C 0.52916(8) 0.91815(19) 0.39441(9) 0.0342(4) Uani 1 1 d . . . . .
H10A H 0.489650 0.919319 0.358309 0.041 Uiso 1 1 calc R U . . .
H10B H 0.542078 1.019354 0.404034 0.041 Uiso 1 1 calc R U . . .
C11 C 0.56566(7) 0.84068(17) 0.36044(9) 0.0292(3) Uani 1 1 d . . . . .
C12 C 0.58246(7) 0.90848(17) 0.30564(9) 0.0289(3) Uani 1 1 d . . . . .
C13 C 0.63197(7) 0.70851(18) 0.29584(10) 0.0333(4) Uani 1 1 d . . . . .
C14 C 0.58563(7) 0.70570(18) 0.38000(10) 0.0330(4) Uani 1 1 d . . . . .
H14 H 0.575796 0.655525 0.415864 0.040 Uiso 1 1 calc R U . . .
O4 O 0.77562(6) 0.18705(16) 0.32980(8) 0.0527(4) Uani 1 1 d . . . . .
H4 H 0.762165 0.270737 0.324894 0.079 Uiso 1 1 calc R U . . .
O5 O 0.65305(6) 0.13453(14) 0.46466(8) 0.0472(4) Uani 1 1 d . . . . .
H5 H 0.644200 0.219060 0.449380 0.071 Uiso 1 1 calc R U . . .
O6 O 0.71851(7) 0.39432(15) 0.34240(9) 0.0577(4) Uani 1 1 d . . . . .
O7 O 0.65806(6) 0.37171(13) 0.39990(8) 0.0463(4) Uani 1 1 d . . . . .
C15 C 0.75222(7) 0.1056(2) 0.36869(10) 0.0375(4) Uani 1 1 d . . . . .
C16 C 0.76641(8) -0.0389(2) 0.38031(11) 0.0453(5) Uani 1 1 d . . . . .
H16 H 0.791523 -0.081219 0.360311 0.054 Uiso 1 1 calc R U . . .
C17 C 0.74352(8) -0.1206(2) 0.42140(12) 0.0486(5) Uani 1 1 d . . . . .
H17 H 0.753324 -0.219636 0.429567 0.058 Uiso 1 1 calc R U . . .
C18 C 0.70669(8) -0.0619(2) 0.45093(11) 0.0453(5) Uani 1 1 d . . . . .
H18 H 0.692206 -0.119513 0.480037 0.054 Uiso 1 1 calc R U . . .
C19 C 0.69103(7) 0.08207(19) 0.43771(10) 0.0360(4) Uani 1 1 d . . . . .
C20 C 0.71371(7) 0.16858(19) 0.39641(9) 0.0325(4) Uani 1 1 d . . . . .
C21 C 0.69577(8) 0.3206(2) 0.37888(11) 0.0388(4) 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 O1 C1 117.14(13) . . ?
C5 O2 C2 113.91(13) . . ?
C6 O3 C3 117.06(13) . . ?
C13 N1 H1 120.2 . . ?
C13 N1 C14 119.57(14) . . ?
C14 N1 H1 120.2 . . ?
H2A N2 H2B 120.0 . . ?
C13 N2 H2A 120.0 . . ?
C13 N2 H2B 120.0 . . ?
C13 N3 C12 117.96(13) . . ?
H4A N4 H4B 120.0 . . ?
C12 N4 H4A 120.0 . . ?
C12 N4 H4B 120.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 H2C 109.5 . . ?
O2 C2 H2D 109.5 . . ?
O2 C2 H2E 109.5 . . ?
H2C C2 H2D 109.5 . . ?
H2C C2 H2E 109.5 . . ?
H2D C2 H2E 109.5 . . ?
O3 C3 H3A 109.5 . . ?
O3 C3 H3B 109.5 . . ?
O3 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 C5 115.45(14) . . ?
O1 C4 C9 124.31(15) . . ?
C9 C4 C5 120.17(15) . . ?
O2 C5 C4 119.60(14) . . ?
O2 C5 C6 120.12(14) . . ?
C6 C5 C4 120.06(14) . . ?
O3 C6 C5 115.49(13) . . ?
O3 C6 C7 124.94(14) . . ?
C5 C6 C7 119.52(14) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 119.97(15) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 120.58(15) . . ?
C7 C8 C10 120.73(15) . . ?
C9 C8 C10 118.65(15) . . ?
C4 C9 H9 120.2 . . ?
C8 C9 C4 119.52(15) . . ?
C8 C9 H9 120.2 . . ?
C8 C10 H10A 108.7 . . ?
C8 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C8 114.43(13) . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C12 C11 C10 121.46(14) . . ?
C14 C11 C10 122.99(14) . . ?
C14 C11 C12 115.53(14) . . ?
N3 C12 C11 122.73(14) . . ?
N4 C12 N3 116.34(14) . . ?
N4 C12 C11 120.93(14) . . ?
N2 C13 N1 117.33(15) . . ?
N2 C13 N3 120.24(15) . . ?
N3 C13 N1 122.42(14) . . ?
N1 C14 H14 119.2 . . ?
C11 C14 N1 121.58(14) . . ?
C11 C14 H14 119.2 . . ?
C15 O4 H4 109.5 . . ?
C19 O5 H5 109.5 . . ?
O4 C15 C16 119.25(16) . . ?
O4 C15 C20 119.84(16) . . ?
C16 C15 C20 120.91(17) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.07(18) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.67(18) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.53(19) . . ?
C19 C18 H18 120.2 . . ?
O5 C19 C18 118.05(17) . . ?
O5 C19 C20 121.63(15) . . ?
C18 C19 C20 120.31(17) . . ?
C15 C20 C21 120.20(15) . . ?
C19 C20 C15 118.48(16) . . ?
C19 C20 C21 121.25(15) . . ?
O6 C21 C20 118.40(15) . . ?
O7 C21 O6 122.56(17) . . ?
O7 C21 C20 119.04(15) . . ?
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 C1 1.438(2) . ?
O1 C4 1.373(2) . ?
O2 C2 1.429(2) . ?
O2 C5 1.3861(18) . ?
O3 C3 1.428(2) . ?
O3 C6 1.3669(18) . ?
N1 H1 0.8800 . ?
N1 C13 1.360(2) . ?
N1 C14 1.3664(19) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C13 1.332(2) . ?
N3 C12 1.342(2) . ?
N3 C13 1.333(2) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C12 1.336(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2C 0.9800 . ?
C2 H2D 0.9800 . ?
C2 H2E 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.398(2) . ?
C4 C9 1.395(2) . ?
C5 C6 1.397(2) . ?
C6 C7 1.401(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.391(2) . ?
C8 C9 1.393(2) . ?
C8 C10 1.515(2) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.511(2) . ?
C11 C12 1.439(2) . ?
C11 C14 1.353(2) . ?
C14 H14 0.9500 . ?
O4 H4 0.8400 . ?
O4 C15 1.357(2) . ?
O5 H5 0.8400 . ?
O5 C19 1.353(2) . ?
O6 C21 1.273(2) . ?
O7 C21 1.2691(19) . ?
C15 C16 1.386(3) . ?
C15 C20 1.412(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(2) . ?
C19 C20 1.407(2) . ?
C20 C21 1.484(2) . ?
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 C4 C5 O2 6.3(2) . . . . ?
O1 C4 C5 C6 -179.07(13) . . . . ?
O1 C4 C9 C8 -177.20(14) . . . . ?
O2 C5 C6 O3 -7.0(2) . . . . ?
O2 C5 C6 C7 170.72(13) . . . . ?
O3 C6 C7 C8 178.10(14) . . . . ?
C1 O1 C4 C5 177.55(14) . . . . ?
C1 O1 C4 C9 -5.4(2) . . . . ?
C2 O2 C5 C4 -89.60(19) . . . . ?
C2 O2 C5 C6 95.77(19) . . . . ?
C3 O3 C6 C5 179.52(14) . . . . ?
C3 O3 C6 C7 1.9(2) . . . . ?
C4 C5 C6 O3 178.38(13) . . . . ?
C4 C5 C6 C7 -3.9(2) . . . . ?
C5 C4 C9 C8 -0.3(2) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C6 C7 C8 C9 2.9(2) . . . . ?
C6 C7 C8 C10 -174.92(14) . . . . ?
C7 C8 C9 C4 -3.0(2) . . . . ?
C7 C8 C10 C11 -99.38(18) . . . . ?
C8 C10 C11 C12 -162.53(16) . . . . ?
C8 C10 C11 C14 16.1(2) . . . . ?
C9 C4 C5 O2 -170.90(14) . . . . ?
C9 C4 C5 C6 3.7(2) . . . . ?
C9 C8 C10 C11 82.77(19) . . . . ?
C10 C8 C9 C4 174.81(14) . . . . ?
C10 C11 C12 N3 -177.39(15) . . . . ?
C10 C11 C12 N4 2.6(3) . . . . ?
C10 C11 C14 N1 -178.52(16) . . . . ?
C12 N3 C13 N1 2.5(3) . . . . ?
C12 N3 C13 N2 -177.64(16) . . . . ?
C12 C11 C14 N1 0.2(2) . . . . ?
C13 N1 C14 C11 -2.7(3) . . . . ?
C13 N3 C12 N4 174.76(15) . . . . ?
C13 N3 C12 C11 -5.2(2) . . . . ?
C14 N1 C13 N2 -178.46(16) . . . . ?
C14 N1 C13 N3 1.4(3) . . . . ?
C14 C11 C12 N3 3.9(2) . . . . ?
C14 C11 C12 N4 -176.11(16) . . . . ?
O4 C15 C16 C17 178.50(18) . . . . ?
O4 C15 C20 C19 -178.79(16) . . . . ?
O4 C15 C20 C21 4.2(3) . . . . ?
O5 C19 C20 C15 -178.64(16) . . . . ?
O5 C19 C20 C21 -1.6(3) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C15 C20 C21 O6 -4.2(3) . . . . ?
C15 C20 C21 O7 174.93(17) . . . . ?
C16 C15 C20 C19 1.5(3) . . . . ?
C16 C15 C20 C21 -175.54(17) . . . . ?
C16 C17 C18 C19 1.6(3) . . . . ?
C17 C18 C19 O5 177.16(17) . . . . ?
C17 C18 C19 C20 -1.8(3) . . . . ?
C18 C19 C20 C15 0.3(3) . . . . ?
C18 C19 C20 C21 177.33(18) . . . . ?
C19 C20 C21 O6 178.80(18) . . . . ?
C19 C20 C21 O7 -2.0(3) . . . . ?
C20 C15 C16 C17 -1.8(3) . . . . ?
