#------------------------------------------------------------------------------
#$Date: 2023-07-05 13:12:18 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284924 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/67/7246783.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_7246783
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
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-03-14
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-03-17 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.469(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0172(3)
_cell_length_b                   28.2186(13)
_cell_length_c                   10.7877(5)
_cell_measurement_reflns_used    7215
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      31.3890
_cell_measurement_theta_min      2.0640
_cell_volume                     2077.38(17)
_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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      113.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.947
_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  60.00   1.00    1.00    --  -30.00  45.00  90.00  180
  3  ω   -120.00  60.00   1.00    1.00    --  -30.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_unetI/netI     0.0772
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26572
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.257
_diffrn_reflns_theta_min         2.071
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0115(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         6989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0659
_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)+(0.0548P)²+0.7520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1671
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4341
_reflns_number_total             6989
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00128h2.cif
_cod_data_source_block           r20210921c
_cod_depositor_comments
'Adding full bibliography for 7246781--7246785.cif.'
_cod_database_code               7246783
_shelx_shelxl_version_number     2019/3
_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_max   0.983
_shelx_estimated_absorpt_t_min   0.976
_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:
 N3(H3), C5(H5), C7(H7), C14(H14), C16(H16), C19(H19), C20(H20)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N4(H4A,H4B)
2.d Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5A)
;
_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
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 -0.1161(2) 0.20960(5) 0.13265(13) 0.0323(3) Uani 1 1 d . . . . .
O2 O 0.2286(2) 0.18729(5) 0.28361(12) 0.0280(3) Uani 1 1 d . . . . .
O3 O 0.53642(19) 0.24670(5) 0.31870(13) 0.0290(3) Uani 1 1 d . . . . .
N1 N 0.3453(3) 0.34326(6) -0.13254(17) 0.0341(4) Uani 1 1 d . . . . .
H1A H 0.412433 0.334181 -0.187826 0.041 Uiso 1 1 calc R U . . .
H1B H 0.236850 0.328304 -0.128464 0.041 Uiso 1 1 calc R U . . .
N2 N 0.5747(2) 0.40080(5) -0.06665(16) 0.0265(3) Uani 1 1 d . . . . .
N3 N 0.5428(2) 0.45415(5) 0.09588(15) 0.0243(3) Uani 1 1 d . . . . .
H3 H 0.589780 0.478441 0.144638 0.029 Uiso 1 1 calc R U . . .
N4 N 0.7988(2) 0.46144(6) -0.00303(16) 0.0295(4) Uani 1 1 d . . . . .
H4A H 0.864603 0.452191 -0.058926 0.035 Uiso 1 1 calc R U . . .
H4B H 0.839277 0.486053 0.046143 0.035 Uiso 1 1 calc R U . . .
C1 C -0.3005(3) 0.21862(8) 0.04669(19) 0.0337(5) Uani 1 1 d . . . . .
H1C H -0.361358 0.246512 0.075469 0.050 Uiso 1 1 calc R U . . .
H1D H -0.386323 0.191086 0.044523 0.050 Uiso 1 1 calc R U . . .
H1E H -0.280246 0.224431 -0.038885 0.050 Uiso 1 1 calc R U . . .
C2 C 0.0252(3) 0.24398(7) 0.14641(17) 0.0238(4) Uani 1 1 d . . . . .
C3 C 0.2068(3) 0.23085(6) 0.22343(17) 0.0239(4) Uani 1 1 d . . . . .
C4 C 0.3625(3) 0.26295(7) 0.24417(16) 0.0225(4) Uani 1 1 d . . . . .
C5 C 0.3349(3) 0.30817(6) 0.18935(17) 0.0233(4) Uani 1 1 d . . . . .
H5 H 0.439908 0.330268 0.204565 0.028 Uiso 1 1 calc R U . . .
C6 C 0.1543(3) 0.32071(6) 0.11286(17) 0.0225(4) Uani 1 1 d . . . . .
C7 C -0.0015(3) 0.28867(7) 0.09062(17) 0.0237(4) Uani 1 1 d . . . . .
H7 H -0.124773 0.297308 0.037837 0.028 Uiso 1 1 calc R U . . .
C8 C 0.2716(3) 0.14960(7) 0.20460(19) 0.0310(4) Uani 1 1 d . . . . .
H8A H 0.279593 0.119516 0.250916 0.046 Uiso 1 1 calc R U . . .
H8B H 0.397033 0.155918 0.182566 0.046 Uiso 1 1 calc R U . . .
H8C H 0.167473 0.147680 0.126463 0.046 Uiso 1 1 calc R U . . .
C9 C 0.6863(3) 0.28125(8) 0.3623(2) 0.0336(5) Uani 1 1 d . . . . .
H9A H 0.791985 0.267091 0.427390 0.050 Uiso 1 1 calc R U . . .
H9B H 0.631036 0.308306 0.398809 0.050 Uiso 1 1 calc R U . . .
H9C H 0.738612 0.292001 0.290380 0.050 Uiso 1 1 calc R U . . .
C10 C 0.1182(3) 0.36989(6) 0.05303(18) 0.0240(4) Uani 1 1 d . . . . .
H10A H 0.026231 0.366890 -0.031424 0.029 Uiso 1 1 calc R U . . .
H10B H 0.054075 0.389779 0.107102 0.029 Uiso 1 1 calc R U . . .
C11 C 0.3006(3) 0.39493(6) 0.03634(17) 0.0226(4) Uani 1 1 d . . . . .
C12 C 0.4077(3) 0.37964(6) -0.05500(18) 0.0242(4) Uani 1 1 d . . . . .
C13 C 0.6375(3) 0.43810(6) 0.00716(18) 0.0231(4) Uani 1 1 d . . . . .
C14 C 0.3750(2) 0.43239(6) 0.10871(17) 0.0218(3) Uani 1 1 d . . . . .
H14 H 0.309052 0.443949 0.170156 0.026 Uiso 1 1 calc R U . . .
O4 O 1.4366(2) 0.58523(7) 0.61568(15) 0.0499(5) Uani 1 1 d . . . . .
H4 H 1.496964 0.577543 0.559995 0.075 Uiso 1 1 calc R U . . .
O5 O 0.6365(2) 0.57047(7) 0.43382(16) 0.0451(4) Uani 1 1 d . . . . .
H5A H 0.608428 0.555716 0.364312 0.068 Uiso 1 1 calc R U . . .
O6 O 0.69224(19) 0.52716(5) 0.24398(14) 0.0332(3) Uani 1 1 d . . . . .
O7 O 0.9898(2) 0.52341(5) 0.20311(14) 0.0359(4) Uani 1 1 d . . . . .
C15 C 1.2389(3) 0.57993(8) 0.56729(19) 0.0331(5) Uani 1 1 d . . . . .
C16 C 1.1619(3) 0.55846(7) 0.45067(18) 0.0279(4) Uani 1 1 d . . . . .
H16 H 1.247792 0.545730 0.402928 0.033 Uiso 1 1 calc R U . . .
C17 C 0.9598(3) 0.55535(6) 0.40276(18) 0.0238(4) Uani 1 1 d . . . . .
C18 C 0.8354(3) 0.57315(7) 0.47596(19) 0.0302(4) Uani 1 1 d . . . . .
C19 C 0.9131(3) 0.59448(8) 0.5930(2) 0.0345(5) Uani 1 1 d . . . . .
H19 H 0.827846 0.606840 0.641768 0.041 Uiso 1 1 calc R U . . .
C20 C 1.1140(3) 0.59779(8) 0.6388(2) 0.0334(5) Uani 1 1 d . . . . .
H20 H 1.166513 0.612254 0.718981 0.040 Uiso 1 1 calc R U . . .
C21 C 0.8788(3) 0.53371(7) 0.27392(19) 0.0274(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
C2 O1 C1 117.87(15) . . ?
C3 O2 C8 113.26(14) . . ?
C4 O3 C9 116.72(15) . . ?
H1A N1 H1B 120.0 . . ?
C12 N1 H1A 120.0 . . ?
C12 N1 H1B 120.0 . . ?
C13 N2 C12 117.97(15) . . ?
C13 N3 H3 120.1 . . ?
C14 N3 H3 120.1 . . ?
C14 N3 C13 119.70(15) . . ?
H4A N4 H4B 120.0 . . ?
C13 N4 H4A 120.0 . . ?
C13 N4 H4B 120.0 . . ?
O1 C1 H1C 109.5 . . ?
O1 C1 H1D 109.5 . . ?
O1 C1 H1E 109.5 . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
O1 C2 C3 114.37(16) . . ?
O1 C2 C7 125.01(17) . . ?
C7 C2 C3 120.62(16) . . ?
O2 C3 C2 120.03(16) . . ?
O2 C3 C4 120.32(16) . . ?
C4 C3 C2 119.57(17) . . ?
O3 C4 C3 115.62(16) . . ?
O3 C4 C5 124.57(16) . . ?
C3 C4 C5 119.82(16) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.05(16) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 120.49(17) . . ?
C5 C6 C10 121.46(16) . . ?
C7 C6 C10 118.03(16) . . ?
C2 C7 C6 119.44(17) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 108.6 . . ?
C6 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C6 114.48(15) . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C12 C11 C10 122.31(16) . . ?
C14 C11 C10 121.58(16) . . ?
C14 C11 C12 116.08(16) . . ?
N1 C12 N2 116.69(16) . . ?
N1 C12 C11 120.90(17) . . ?
N2 C12 C11 122.41(16) . . ?
N2 C13 N3 122.31(16) . . ?
N2 C13 N4 120.63(16) . . ?
N4 C13 N3 117.06(16) . . ?
N3 C14 H14 119.3 . . ?
C11 C14 N3 121.49(16) . . ?
C11 C14 H14 119.3 . . ?
C15 O4 H4 109.5 . . ?
C18 O5 H5A 109.5 . . ?
O4 C15 C16 122.56(18) . . ?
O4 C15 C20 117.50(19) . . ?
C16 C15 C20 119.93(18) . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.75(17) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C18 118.84(17) . . ?
C16 C17 C21 120.08(16) . . ?
C18 C17 C21 121.07(16) . . ?
O5 C18 C17 121.05(17) . . ?
O5 C18 C19 118.70(17) . . ?
C19 C18 C17 120.24(17) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.28(18) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 119.93(19) . . ?
C19 C20 H20 120.0 . . ?
O6 C21 C17 115.72(16) . . ?
O7 C21 O6 123.89(18) . . ?
O7 C21 C17 120.39(17) . . ?
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 1.428(2) . ?
O1 C2 1.370(2) . ?
O2 C3 1.382(2) . ?
O2 C8 1.438(2) . ?
O3 C4 1.374(2) . ?
O3 C9 1.431(2) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C12 1.332(2) . ?
N2 C12 1.346(2) . ?
N2 C13 1.332(2) . ?
N3 H3 0.8800 . ?
N3 C13 1.364(2) . ?
N3 C14 1.364(2) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C13 1.336(2) . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C2 C3 1.399(3) . ?
C2 C7 1.391(3) . ?
C3 C4 1.396(2) . ?
C4 C5 1.401(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(2) . ?
C6 C7 1.396(2) . ?
C6 C10 1.527(2) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.509(2) . ?
C11 C12 1.438(2) . ?
C11 C14 1.345(3) . ?
C14 H14 0.9500 . ?
O4 H4 0.8400 . ?
O4 C15 1.372(2) . ?
O5 H5A 0.8400 . ?
O5 C18 1.366(2) . ?
O6 C21 1.287(2) . ?
O7 C21 1.246(2) . ?
C15 C16 1.387(3) . ?
C15 C20 1.390(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.394(2) . ?
C17 C18 1.400(3) . ?
C17 C21 1.503(3) . ?
C18 C19 1.390(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(3) . ?
C20 H20 0.9500 . ?
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 C2 C3 O2 -3.4(2) . . . . ?
O1 C2 C3 C4 179.82(15) . . . . ?
O1 C2 C7 C6 179.56(16) . . . . ?
O2 C3 C4 O3 4.6(2) . . . . ?
O2 C3 C4 C5 -175.80(15) . . . . ?
O3 C4 C5 C6 178.39(16) . . . . ?
C1 O1 C2 C3 -174.66(16) . . . . ?
C1 O1 C2 C7 5.3(3) . . . . ?
C2 C3 C4 O3 -178.63(15) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C2 C7 C6 -0.5(3) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C4 C5 C6 C10 179.17(16) . . . . ?
C5 C6 C7 C2 0.3(3) . . . . ?
C5 C6 C10 C11 24.2(2) . . . . ?
C6 C10 C11 C12 69.7(2) . . . . ?
C6 C10 C11 C14 -108.7(2) . . . . ?
C7 C2 C3 O2 176.64(15) . . . . ?
C7 C2 C3 C4 -0.1(3) . . . . ?
C7 C6 C10 C11 -157.14(16) . . . . ?
C8 O2 C3 C2 85.2(2) . . . . ?
C8 O2 C3 C4 -98.05(19) . . . . ?
C9 O3 C4 C3 -168.06(16) . . . . ?
C9 O3 C4 C5 12.4(2) . . . . ?
C10 C6 C7 C2 -178.39(15) . . . . ?
C10 C11 C12 N1 2.4(3) . . . . ?
C10 C11 C12 N2 -177.37(17) . . . . ?
C10 C11 C14 N3 178.16(16) . . . . ?
C12 N2 C13 N3 2.3(3) . . . . ?
C12 N2 C13 N4 -177.87(17) . . . . ?
C12 C11 C14 N3 -0.4(3) . . . . ?
C13 N2 C12 N1 178.14(17) . . . . ?
C13 N2 C12 C11 -2.1(3) . . . . ?
C13 N3 C14 C11 0.6(3) . . . . ?
C14 N3 C13 N2 -1.6(3) . . . . ?
C14 N3 C13 N4 178.57(16) . . . . ?
C14 C11 C12 N1 -179.12(18) . . . . ?
C14 C11 C12 N2 1.1(3) . . . . ?
O4 C15 C16 C17 -177.6(2) . . . . ?
O4 C15 C20 C19 178.4(2) . . . . ?
O5 C18 C19 C20 179.9(2) . . . . ?
C15 C16 C17 C18 -1.7(3) . . . . ?
C15 C16 C17 C21 177.57(18) . . . . ?
C16 C15 C20 C19 -0.5(3) . . . . ?
C16 C17 C18 O5 -179.27(19) . . . . ?
C16 C17 C18 C19 1.4(3) . . . . ?
C16 C17 C21 O6 172.02(17) . . . . ?
C16 C17 C21 O7 -8.2(3) . . . . ?
C17 C18 C19 C20 -0.8(3) . . . . ?
C18 C17 C21 O6 -8.7(3) . . . . ?
C18 C17 C21 O7 171.03(19) . . . . ?
C18 C19 C20 C15 0.3(3) . . . . ?
C20 C15 C16 C17 1.3(3) . . . . ?
C21 C17 C18 O5 1.5(3) . . . . ?
C21 C17 C18 C19 -177.82(19) . . . . ?
