#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/14/1551405.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_1551405
loop_
_publ_author_name
'Meghan B. Ward'
'Andreas Scheitler'
'Meng Yu'
'Laura Senft'
'Annika S. Zillmann'
'John D. Gorden'
'Dean D. Schwartz'
'Ivana Ivanovic-Burmazovic'
'Christian R. Goldsmith'
_publ_section_title
;
 Superoxide dismutase activity enabled by a redox-active ligand rather
 than metal
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              1207
_journal_page_last               1212
_journal_paper_doi               10.1038/s41557-018-0137-1
_journal_volume                  10
_journal_year                    2018
_chemical_formula_moiety         'C27 H29 N5 O2, C H4 O'
_chemical_formula_sum            'C28 H33 N5 O3'
_chemical_formula_weight         487.61
_chemical_name_systematic
'2-({(2-{bis{(pyridin-2-yl)methyl}amino}ethyl){(pyridin-2-yl)methyl]amino]methyl)benzene-1,4-diol methanol solvate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_cell_angle_alpha                93.769(2)
_cell_angle_beta                 113.6270(10)
_cell_angle_gamma                103.020(2)
_cell_formula_units_Z            2
_cell_length_a                   10.2291(6)
_cell_length_b                   11.3937(6)
_cell_length_c                   12.5182(7)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    180
_cell_measurement_theta_max      25.77
_cell_measurement_theta_min      2.21
_cell_volume                     1282.25(13)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.9760
_diffrn_measured_fraction_theta_max 0.9760
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26957
_diffrn_reflns_theta_full        25.7719
_diffrn_reflns_theta_max         25.77
_diffrn_reflns_theta_min         1.80
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1027 before and 0.0575 after correction. The Ratio of minimum to maximum transmission is 0.8546. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear yellowish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.2628
_exptl_crystal_description       Block
_exptl_crystal_F_000             520.2235
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.3529
_refine_diff_density_min         -0.3264
_refine_diff_density_rms         0.0741
_refine_ls_d_res_high            0.8173
_refine_ls_d_res_low             11.2923
_refine_ls_goodness_of_fit_ref   1.0795
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    56
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0795
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0588
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0000P)²+2.5140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1294
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                4169
_reflns_number_total             4802
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            41557_2018_137_MOESM27_ESM.cif
_cod_data_source_block           Goldsmith051616_0m_a
_cod_database_code               1551405
_cod_database_fobs_code          1551405
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6a,H6b), C7(H7a,H7b), C21(H21a,H21b), C15(H15a,H15b), C14(H14a,H14b),
 C13(H13a,H13b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2a), C1(H1a), C3(H3), C4(H4), C9(H9), C20(H20), C24(H24), C25(H25),
 C27(H27), C19(H19), C18(H18), C17(H17), C12(H12), C11(H11), C10(H10)
2.c Idealised Me refined as rotating group:
 C010(H01a,H01b,H01c)
2.d Idealised tetrahedral OH refined as rotating group with stretchable bonds:
 O1(H1), O3(H3a)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -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_refinement_flags_posn
O2 O 0.4204(2) 0.36012(17) 0.80588(18) 0.0357(5) Uani 1.000000 .
C2 C 0.9370(3) 0.2101(3) 0.8399(3) 0.0394(7) Uani 1.000000 .
H2a H 1.0410(3) 0.2465(3) 0.8812(3) 0.0473(8) Uiso 1.000000 R
O1 O 0.0726(2) 0.68290(19) 0.71425(19) 0.0417(5) Uani 1.000000 .
H1 H 0.124(3) 0.758(3) 0.766(3) 0.0625(8) Uiso 1.000000 GR
N1 N 0.7350(2) 0.0572(2) 0.6862(2) 0.0300(5) Uani 1.000000 .
H2 H 0.386(4) 0.306(3) 0.735(3) 0.054(10) Uiso 1.000000 .
C1 C 0.8807(3) 0.1112(3) 0.7497(3) 0.0373(7) Uani 1.000000 .
H1a H 0.9488(3) 0.0793(3) 0.7314(3) 0.0448(8) Uiso 1.000000 R
N2 N 0.3779(2) 0.06086(18) 0.68668(18) 0.0219(4) Uani 1.000000 .
N3 N 0.2057(2) -0.08780(19) 0.85337(19) 0.0267(5) Uani 1.000000 .
O3 O 0.1758(3) 0.30195(19) 0.1411(2) 0.0471(6) Uani 1.000000 .
H3a H 0.233(4) 0.2952(4) 0.218(3) 0.0707(8) Uiso 1.000000 GR
C3 C 0.8386(3) 0.2551(3) 0.8689(3) 0.0366(7) Uani 1.000000 .
H3 H 0.8738(3) 0.3223(3) 0.9316(3) 0.0439(8) Uiso 1.000000 R
N4 N 0.2487(2) 0.25737(18) 0.57187(18) 0.0224(4) Uani 1.000000 .
C4 C 0.6880(3) 0.2007(2) 0.8050(2) 0.0283(6) Uani 1.000000 .
H4 H 0.6181(3) 0.2298(2) 0.8234(2) 0.0340(7) Uiso 1.000000 R
N5 N 0.4036(3) 0.3097(2) 0.36940(19) 0.0302(5) Uani 1.000000 .
C5 C 0.6405(3) 0.1029(2) 0.7137(2) 0.0235(5) Uani 1.000000 .
C6 C 0.4782(3) 0.0455(2) 0.6330(2) 0.0245(5) Uani 1.000000 .
H6a H 0.4626(3) -0.0430(2) 0.6095(2) 0.0294(6) Uiso 1.000000 R
H6b H 0.4520(3) 0.0821(2) 0.5603(2) 0.0294(6) Uiso 1.000000 R
C9 C 0.3619(3) 0.1171(2) 0.9231(2) 0.0295(6) Uani 1.000000 .
H9 H 0.4372(3) 0.1806(2) 0.9192(2) 0.0354(7) Uiso 1.000000 R
C8 C 0.3142(3) 0.0037(2) 0.8519(2) 0.0239(5) Uani 1.000000 .
C7 C 0.3841(3) -0.0244(2) 0.7711(2) 0.0280(6) Uani 1.000000 .
H7a H 0.3325(3) -0.1087(2) 0.7263(2) 0.0336(7) Uiso 1.000000 R
H7b H 0.4891(3) -0.0209(2) 0.8198(2) 0.0336(7) Uiso 1.000000 R
C010 C 0.1866(5) 0.4255(3) 0.1332(4) 0.0716(12) Uani 1.000000 .
H01a H 0.141(3) 0.4339(5) 0.0498(4) 0.1074(19) Uiso 1.000000 GR
H01b H 0.135(3) 0.4565(8) 0.175(2) 0.1074(19) Uiso 1.000000 GR
H01c H 0.2914(5) 0.4724(5) 0.169(2) 0.1074(19) Uiso 1.000000 GR
C20 C 0.5258(3) 0.3023(3) 0.3558(3) 0.0355(7) Uani 1.000000 .
H20 H 0.5173(3) 0.2858(3) 0.2775(3) 0.0427(8) Uiso 1.000000 R
C21 C 0.1346(3) 0.2863(2) 0.6052(2) 0.0258(5) Uani 1.000000 .
H21a H 0.0474(3) 0.2878(2) 0.5327(2) 0.0310(7) Uiso 1.000000 R
H21b H 0.1017(3) 0.2210(2) 0.6447(2) 0.0310(7) Uiso 1.000000 R
C22 C 0.1917(3) 0.4080(2) 0.6871(2) 0.0233(5) Uani 1.000000 .
C23 C 0.3307(3) 0.4380(2) 0.7846(2) 0.0250(5) Uani 1.000000 .
C24 C 0.3792(3) 0.5475(2) 0.8622(2) 0.0308(6) Uani 1.000000 .
H24 H 0.4719(3) 0.5668(2) 0.9298(2) 0.0369(7) Uiso 1.000000 R
C25 C 0.2931(3) 0.6293(2) 0.8420(2) 0.0304(6) Uani 1.000000 .
H25 H 0.3271(3) 0.7037(2) 0.8961(2) 0.0365(7) Uiso 1.000000 R
C26 C 0.1580(3) 0.6029(2) 0.7433(2) 0.0275(6) Uani 1.000000 .
C27 C 0.1082(3) 0.4915(2) 0.6672(2) 0.0256(5) Uani 1.000000 .
H27 H 0.0149(3) 0.4722(2) 0.6002(2) 0.0307(7) Uiso 1.000000 R
C19 C 0.6623(3) 0.3173(2) 0.4485(3) 0.0336(6) Uani 1.000000 .
H19 H 0.7450(3) 0.3096(2) 0.4346(3) 0.0404(8) Uiso 1.000000 R
C18 C 0.6759(3) 0.3438(2) 0.5620(3) 0.0328(6) Uani 1.000000 .
H18 H 0.7686(3) 0.3554(2) 0.6282(3) 0.0394(7) Uiso 1.000000 R
C17 C 0.5524(3) 0.3531(2) 0.5779(2) 0.0289(6) Uani 1.000000 .
H17 H 0.5597(3) 0.3723(2) 0.6554(2) 0.0347(7) Uiso 1.000000 R
C16 C 0.4176(3) 0.3345(2) 0.4801(2) 0.0235(5) Uani 1.000000 .
C15 C 0.2800(3) 0.3419(2) 0.4944(2) 0.0273(6) Uani 1.000000 .
H15a H 0.1942(3) 0.3211(2) 0.4157(2) 0.0327(7) Uiso 1.000000 R
H15b H 0.2933(3) 0.4268(2) 0.5291(2) 0.0327(7) Uiso 1.000000 R
C14 C 0.2014(3) 0.1292(2) 0.5122(2) 0.0244(5) Uani 1.000000 .
H14a H 0.0949(3) 0.1081(2) 0.4570(2) 0.0293(6) Uiso 1.000000 R
H14b H 0.2575(3) 0.1213(2) 0.4647(2) 0.0293(6) Uiso 1.000000 R
C13 C 0.2247(3) 0.0383(2) 0.5972(2) 0.0253(5) Uani 1.000000 .
H13a H 0.1927(3) -0.0449(2) 0.5506(2) 0.0303(7) Uiso 1.000000 R
H13b H 0.1599(3) 0.0399(2) 0.6382(2) 0.0303(7) Uiso 1.000000 R
C12 C 0.1463(3) -0.0665(2) 0.9286(2) 0.0301(6) Uani 1.000000 .
H12 H 0.0698(3) -0.1306(2) 0.9303(2) 0.0361(7) Uiso 1.000000 R
C11 C 0.1903(3) 0.0429(3) 1.0031(2) 0.0320(6) Uani 1.000000 .
H11 H 0.1466(3) 0.0535(3) 1.0560(2) 0.0384(7) Uiso 1.000000 R
C10 C 0.2996(3) 0.1374(2) 0.9996(2) 0.0321(6) Uani 1.000000 .
H10 H 0.3311(3) 0.2147(2) 1.0489(2) 0.0385(7) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C23 O2 H2 106(2) . .
C1 C2 H2a 120.83(17) . .
C3 C2 H2a 120.83(17) . .
C3 C2 C1 118.3(3) . .
C26 O1 H1 109.5 . .
C5 N1 C1 117.3(2) . .
N1 C1 C2 123.9(3) . .
H1a C1 C2 118.06(17) . .
H1a C1 N1 118.06(16) . .
C7 N2 C6 108.77(19) . .
C13 N2 C6 111.79(19) . .
C13 N2 C7 109.83(19) . .
C12 N3 C8 117.7(2) . .
C010 O3 H3a 109.5 . .
H3 C3 C2 120.57(17) . .
C4 C3 C2 118.9(3) . .
C4 C3 H3 120.57(17) . .
C15 N4 C21 109.78(19) . .
C14 N4 C21 111.19(18) . .
C14 N4 C15 110.49(19) . .
H4 C4 C3 120.48(17) . .
C5 C4 C3 119.0(2) . .
C5 C4 H4 120.48(15) . .
C16 N5 C20 117.5(2) . .
C4 C5 N1 122.6(2) . .
C6 C5 N1 115.0(2) . .
C6 C5 C4 122.3(2) . .
C5 C6 N2 113.9(2) . .
H6a C6 N2 108.78(12) . .
H6a C6 C5 108.78(13) . .
H6b C6 N2 108.78(13) . .
H6b C6 C5 108.78(13) . .
H6b C6 H6a 107.7 . .
C8 C9 H9 120.17(15) . .
C10 C9 H9 120.17(16) . .
C10 C9 C8 119.7(2) . .
C9 C8 N3 121.8(2) . .
C7 C8 N3 116.7(2) . .
C7 C8 C9 121.4(2) . .
C8 C7 N2 113.1(2) . .
H7a C7 N2 108.96(13) . .
H7a C7 C8 108.96(14) . .
H7b C7 N2 108.96(13) . .
H7b C7 C8 108.96(14) . .
H7b C7 H7a 107.8 . .
H01a C010 O3 109.5 . .
H01b C010 O3 109.5 . .
H01b C010 H01a 109.5 . .
H01c C010 O3 109.5 . .
H01c C010 H01a 109.5 . .
H01c C010 H01b 109.5 . .
H20 C20 N5 118.06(16) . .
C19 C20 N5 123.9(3) . .
C19 C20 H20 118.06(16) . .
H21a C21 N4 109.16(13) . .
H21b C21 N4 109.16(13) . .
H21b C21 H21a 107.9 . .
C22 C21 N4 112.22(19) . .
C22 C21 H21a 109.16(14) . .
C22 C21 H21b 109.16(13) . .
C23 C22 C21 120.1(2) . .
C27 C22 C21 120.9(2) . .
C27 C22 C23 119.0(2) . .
C22 C23 O2 121.3(2) . .
C24 C23 O2 119.0(2) . .
C24 C23 C22 119.7(2) . .
H24 C24 C23 119.73(15) . .
C25 C24 C23 120.5(2) . .
C25 C24 H24 119.73(15) . .
H25 C25 C24 119.80(15) . .
C26 C25 C24 120.4(2) . .
C26 C25 H25 119.80(15) . .
C25 C26 O1 123.2(2) . .
C27 C26 O1 117.9(2) . .
C27 C26 C25 118.8(2) . .
C26 C27 C22 121.5(2) . .
H27 C27 C22 119.26(14) . .
H27 C27 C26 119.26(15) . .
H19 C19 C20 120.89(16) . .
C18 C19 C20 118.2(3) . .
C18 C19 H19 120.89(16) . .
H18 C18 C19 120.59(16) . .
C17 C18 C19 118.8(3) . .
C17 C18 H18 120.59(16) . .
H17 C17 C18 120.12(16) . .
C16 C17 C18 119.8(2) . .
C16 C17 H17 120.12(15) . .
C17 C16 N5 121.8(2) . .
C15 C16 N5 117.1(2) . .
C15 C16 C17 121.1(2) . .
C16 C15 N4 111.43(19) . .
H15a C15 N4 109.34(13) . .
H15a C15 C16 109.34(14) . .
H15b C15 N4 109.34(13) . .
H15b C15 C16 109.34(13) . .
H15b C15 H15a 108.0 . .
H14a C14 N4 108.85(12) . .
H14b C14 N4 108.85(12) . .
H14b C14 H14a 107.7 . .
C13 C14 N4 113.6(2) . .
C13 C14 H14a 108.85(13) . .
C13 C14 H14b 108.85(13) . .
C14 C13 N2 114.72(19) . .
H13a C13 N2 108.59(12) . .
H13a C13 C14 108.59(13) . .
H13b C13 N2 108.59(12) . .
H13b C13 C14 108.59(13) . .
H13b C13 H13a 107.6 . .
H12 C12 N3 118.27(15) . .
C11 C12 N3 123.5(2) . .
C11 C12 H12 118.27(15) . .
H11 C11 C12 120.71(15) . .
C10 C11 C12 118.6(2) . .
C10 C11 H11 120.71(16) . .
C11 C10 C9 118.7(2) . .
H10 C10 C9 120.64(16) . .
H10 C10 C11 120.64(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 H2 0.93(4) .
O2 C23 1.379(3) .
C2 H2a 0.9500 .
C2 C1 1.376(4) .
C2 C3 1.381(4) .
O1 H1 0.94(4) .
O1 C26 1.368(3) .
N1 C1 1.343(3) .
N1 C5 1.340(3) .
C1 H1a 0.9500 .
N2 C6 1.467(3) .
N2 C7 1.474(3) .
N2 C13 1.467(3) .
N3 C8 1.347(3) .
N3 C12 1.346(3) .
O3 H3a 0.92(4) .
O3 C010 1.400(4) .
C3 H3 0.9500 .
C3 C4 1.384(4) .
N4 C21 1.481(3) .
N4 C15 1.484(3) .
N4 C14 1.474(3) .
C4 H4 0.9500 .
C4 C5 1.388(4) .
N5 C20 1.347(4) .
N5 C16 1.339(3) .
C5 C6 1.511(3) .
C6 H6a 0.9900 .
C6 H6b 0.9900 .
C9 H9 0.9500 .
C9 C8 1.385(4) .
C9 C10 1.380(4) .
C8 C7 1.510(3) .
C7 H7a 0.9900 .
C7 H7b 0.9900 .
C010 H01a 0.9800 .
C010 H01b 0.9800 .
C010 H01c 0.9800 .
C20 H20 0.9500 .
C20 C19 1.376(4) .
C21 H21a 0.9900 .
C21 H21b 0.9900 .
C21 C22 1.511(3) .
C22 C23 1.401(3) .
C22 C27 1.387(4) .
C23 C24 1.386(4) .
C24 H24 0.9500 .
C24 C25 1.388(4) .
C25 H25 0.9500 .
C25 C26 1.387(4) .
C26 C27 1.392(3) .
C27 H27 0.9500 .
C19 H19 0.9500 .
C19 C18 1.377(4) .
C18 H18 0.9500 .
C18 C17 1.380(4) .
C17 H17 0.9500 .
C17 C16 1.388(4) .
C16 C15 1.508(3) .
C15 H15a 0.9900 .
C15 H15b 0.9900 .
C14 H14a 0.9900 .
C14 H14b 0.9900 .
C14 C13 1.521(4) .
C13 H13a 0.9900 .
C13 H13b 0.9900 .
C12 H12 0.9500 .
C12 C11 1.372(4) .
C11 H11 0.9500 .
C11 C10 1.384(4) .
C10 H10 0.9500 .
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
O1 H1 N3 0.94(4) 1.82(4) 2.759(3) 172.4(7) 1_565
O2 H2 N4 0.93(4) 1.91(4) 2.745(3) 148(3) .
O3 H3a N5 0.92(4) 1.96(4) 2.854(3) 162(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168302890
