#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/62/2226293.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226293
loop_
_publ_author_name
'Huang, Gang'
'Xu, Xing Yan'
'Zeng, Xiang Chao'
'Zheng, Le'
'Li, Kai Ping'
_publ_section_title
;
 Methyl 3-(1H-indole-3-carboxamido)propionate hemihydrate
;
_journal_coeditor_code           SJ2794
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1472
_journal_paper_doi               10.1107/S1600536810018015
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H14 N2 O3, 0.5H2 O'
_chemical_formula_moiety         'C13 H14 N2 O3, 0.5(H2 O)'
_chemical_formula_sum            'C13 H15 N2 O3.5'
_chemical_formula_weight         255.27
_chemical_melting_point          409
_chemical_name_systematic
;
Methyl 3-(1H-indole-3-carboxamido)propionate hemihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.422(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.8220(13)
_cell_length_b                   9.7668(12)
_cell_length_c                   23.623(3)
_cell_measurement_reflns_used    7482
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.26
_cell_volume                     2494.6(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            13021
_diffrn_reflns_theta_full        27.12
_diffrn_reflns_theta_max         27.12
_diffrn_reflns_theta_min         1.73
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9620
_exptl_absorpt_correction_T_min  0.9554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.235
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0626P)²+0.3718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1259
_reflns_number_gt                4349
_reflns_number_total             5484
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2794.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226293
_cod_database_fobs_code          2226293
loop_
_symmetry_equiv_pos_as_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.80813(13) -0.08599(15) 0.03833(6) 0.0318(3) Uani d . 1 . .
H H1 0.8269 -0.0666 0.0002 0.038 Uiso calc R 1 . .
C C2 0.71838(12) -0.02181(14) 0.06810(6) 0.0272(3) Uani d . 1 . .
C C3 0.72133(12) -0.08192(14) 0.12390(6) 0.0275(3) Uani d . 1 . .
C C4 0.65431(14) -0.06387(16) 0.17297(6) 0.0341(3) Uani d . 1 . .
H H4 0.5917 0.0041 0.1743 0.041 Uiso calc R 1 . .
C C5 0.68093(15) -0.14651(17) 0.21922(6) 0.0398(4) Uani d . 1 . .
H H5 0.6352 -0.1356 0.2524 0.048 Uiso calc R 1 . .
C C6 0.77349(16) -0.24579(17) 0.21840(7) 0.0421(4) Uani d . 1 . .
H H6 0.7892 -0.3012 0.2510 0.051 Uiso calc R 1 . .
C C7 0.84253(14) -0.26528(16) 0.17145(7) 0.0373(3) Uani d . 1 . .
H H7 0.9061 -0.3323 0.1710 0.045 Uiso calc R 1 . .
C C8 0.81497(12) -0.18210(14) 0.12439(6) 0.0297(3) Uani d . 1 . .
C C9 0.62911(13) 0.08453(15) 0.04984(6) 0.0305(3) Uani d . 1 . .
C C10 0.53881(13) 0.24140(15) -0.01892(6) 0.0311(3) Uani d . 1 . .
H H10A 0.5536 0.3226 0.0055 0.037 Uiso calc R 1 . .
H H10B 0.4544 0.2074 -0.0125 0.037 Uiso calc R 1 . .
C C11 0.54663(13) 0.28339(15) -0.08026(6) 0.0321(3) Uani d . 1 . .
H H11A 0.6316 0.3150 -0.0872 0.039 Uiso calc R 1 . .
H H11B 0.5286 0.2034 -0.1050 0.039 Uiso calc R 1 . .
C C12 0.45597(13) 0.39641(15) -0.09478(6) 0.0308(3) Uani d . 1 . .
C C13 0.39062(16) 0.55673(18) -0.16381(7) 0.0433(4) Uani d . 1 . .
H H13A 0.3959 0.6307 -0.1358 0.065 Uiso calc R 1 . .
H H13B 0.3056 0.5222 -0.1670 0.065 Uiso calc R 1 . .
H H13C 0.4145 0.5917 -0.2007 0.065 Uiso calc R 1 . .
C C14 0.29377(13) 0.36840(16) 0.06182(6) 0.0341(3) Uani d . 1 . .
H H14 0.3102 0.3692 0.0226 0.041 Uiso calc R 1 . .
C C15 0.21024(12) 0.45232(14) 0.08725(6) 0.0290(3) Uani d . 1 . .
C C16 0.21441(12) 0.41712(14) 0.14649(6) 0.0284(3) Uani d . 1 . .
C C17 0.15418(14) 0.46235(16) 0.19450(6) 0.0354(3) Uani d . 1 . .
H H17 0.0928 0.5317 0.1913 0.042 Uiso calc R 1 . .
C C18 0.18574(16) 0.40417(17) 0.24654(7) 0.0432(4) Uani d . 1 . .
H H18 0.1446 0.4335 0.2791 0.052 Uiso calc R 1 . .
C C19 0.27677(16) 0.30334(18) 0.25209(7) 0.0441(4) Uani d . 1 . .
H H19 0.2977 0.2669 0.2885 0.053 Uiso calc R 1 . .
C C20 0.33663(15) 0.25580(17) 0.20592(7) 0.0399(4) Uani d . 1 . .
H H20 0.3981 0.1866 0.2097 0.048 Uiso calc R 1 . .
C C21 0.30395(13) 0.31267(15) 0.15322(6) 0.0319(3) Uani d . 1 . .
C C22 0.13786(12) 0.56060(14) 0.05926(6) 0.0290(3) Uani d . 1 . .
C C23 0.08226(13) 0.69102(15) -0.02576(6) 0.0301(3) Uani d . 1 . .
H H23A 0.1048 0.7807 -0.0088 0.036 Uiso calc R 1 . .
H H23B -0.0072 0.6763 -0.0211 0.036 Uiso calc R 1 . .
C C24 0.10799(13) 0.69297(15) -0.08814(6) 0.0328(3) Uani d . 1 . .
H H24A 0.1972 0.7095 -0.0929 0.039 Uiso calc R 1 . .
H H24B 0.0866 0.6029 -0.1051 0.039 Uiso calc R 1 . .
C C25 0.03353(13) 0.80346(15) -0.11816(6) 0.0310(3) Uani d . 1 . .
C C26 -0.01206(18) 0.91058(19) -0.20573(7) 0.0497(4) Uani d . 1 . .
H H26A -0.1005 0.8992 -0.1997 0.075 Uiso calc R 1 . .
H H26B 0.0033 0.8978 -0.2460 0.075 Uiso calc R 1 . .
H H26C 0.0139 1.0028 -0.1940 0.075 Uiso calc R 1 . .
N N1 0.86589(11) -0.18166(13) 0.07191(5) 0.0333(3) Uani d . 1 . .
H H1A 0.9265 -0.2351 0.0617 0.040 Uiso calc R 1 . .
N N2 0.62849(11) 0.13484(13) -0.00271(5) 0.0317(3) Uani d . 1 . .
H H2 0.6811 0.1044 -0.0272 0.038 Uiso calc R 1 . .
N N3 0.34897(12) 0.28454(14) 0.10095(5) 0.0375(3) Uani d . 1 . .
H H3 0.4048 0.2220 0.0940 0.045 Uiso calc R 1 . .
N N4 0.15203(11) 0.58337(12) 0.00368(5) 0.0320(3) Uani d . 1 . .
H H4A 0.2039 0.5327 -0.0150 0.038 Uiso calc R 1 . .
O O1 0.55464(11) 0.12826(13) 0.08443(5) 0.0466(3) Uani d . 1 . .
O O2 0.37724(10) 0.43840(12) -0.06434(4) 0.0405(3) Uani d . 1 . .
O O3 0.47321(10) 0.44687(12) -0.14607(4) 0.0393(3) Uani d . 1 . .
O O4 0.06489(10) 0.63299(11) 0.08581(4) 0.0396(3) Uani d . 1 . .
O O5 -0.03955(10) 0.87601(12) -0.09532(4) 0.0402(3) Uani d . 1 . .
O O6 0.05767(10) 0.80986(12) -0.17246(4) 0.0413(3) Uani d . 1 . .
O O1W 0.20002(11) 0.89955(13) 0.09463(5) 0.0507(3) Uani d . 1 . .
H H1B 0.1537 0.8301 0.0994 0.076 Uiso d R 1 . .
H H1C 0.1592 0.9704 0.1031 0.076 Uiso d R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 109.39(12) ?
N1 C1 H1 . . 125.3 ?
C2 C1 H1 . . 125.3 ?
C1 C2 C3 . . 107.05(12) ?
C1 C2 C9 . . 129.92(13) ?
C3 C2 C9 . . 122.99(12) ?
C4 C3 C8 . . 118.49(13) ?
C4 C3 C2 . . 135.33(13) ?
C8 C3 C2 . . 106.17(12) ?
C5 C4 C3 . . 118.86(14) ?
C5 C4 H4 . . 120.6 ?
C3 C4 H4 . . 120.6 ?
C4 C5 C6 . . 121.47(15) ?
C4 C5 H5 . . 119.3 ?
C6 C5 H5 . . 119.3 ?
C7 C6 C5 . . 121.46(15) ?
C7 C6 H6 . . 119.3 ?
C5 C6 H6 . . 119.3 ?
C6 C7 C8 . . 117.08(14) ?
C6 C7 H7 . . 121.5 ?
C8 C7 H7 . . 121.5 ?
N1 C8 C7 . . 129.56(13) ?
N1 C8 C3 . . 107.79(12) ?
C7 C8 C3 . . 122.63(14) ?
O1 C9 N2 . . 120.34(13) ?
O1 C9 C2 . . 118.97(13) ?
N2 C9 C2 . . 120.68(12) ?
N2 C10 C11 . . 112.37(11) ?
N2 C10 H10A . . 109.1 ?
C11 C10 H10A . . 109.1 ?
N2 C10 H10B . . 109.1 ?
C11 C10 H10B . . 109.1 ?
H10A C10 H10B . . 107.9 ?
C12 C11 C10 . . 110.78(12) ?
C12 C11 H11A . . 109.5 ?
C10 C11 H11A . . 109.5 ?
C12 C11 H11B . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 108.1 ?
O2 C12 O3 . . 123.10(13) ?
O2 C12 C11 . . 125.54(13) ?
O3 C12 C11 . . 111.36(12) ?
O3 C13 H13A . . 109.5 ?
O3 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
O3 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N3 C14 C15 . . 109.93(13) ?
N3 C14 H14 . . 125.0 ?
C15 C14 H14 . . 125.0 ?
C14 C15 C16 . . 106.73(12) ?
C14 C15 C22 . . 125.74(13) ?
C16 C15 C22 . . 127.45(12) ?
C17 C16 C21 . . 118.46(13) ?
C17 C16 C15 . . 135.56(13) ?
C21 C16 C15 . . 105.98(12) ?
C18 C17 C16 . . 118.89(14) ?
C18 C17 H17 . . 120.6 ?
C16 C17 H17 . . 120.6 ?
C17 C18 C19 . . 121.33(15) ?
C17 C18 H18 . . 119.3 ?
C19 C18 H18 . . 119.3 ?
C20 C19 C18 . . 121.28(15) ?
C20 C19 H19 . . 119.4 ?
C18 C19 H19 . . 119.4 ?
C19 C20 C21 . . 117.64(14) ?
C19 C20 H20 . . 121.2 ?
C21 C20 H20 . . 121.2 ?
N3 C21 C20 . . 129.50(13) ?
N3 C21 C16 . . 108.12(12) ?
C20 C21 C16 . . 122.37(14) ?
O4 C22 N4 . . 119.79(12) ?
O4 C22 C15 . . 121.47(13) ?
N4 C22 C15 . . 118.73(12) ?
N4 C23 C24 . . 111.22(11) ?
N4 C23 H23A . . 109.4 ?
C24 C23 H23A . . 109.4 ?
N4 C23 H23B . . 109.4 ?
C24 C23 H23B . . 109.4 ?
H23A C23 H23B . . 108.0 ?
C25 C24 C23 . . 110.56(11) ?
C25 C24 H24A . . 109.5 ?
C23 C24 H24A . . 109.5 ?
C25 C24 H24B . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 108.1 ?
O5 C25 O6 . . 124.53(13) ?
O5 C25 C24 . . 123.92(13) ?
O6 C25 C24 . . 111.54(12) ?
O6 C26 H26A . . 109.5 ?
O6 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
O6 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C1 N1 C8 . . 109.60(11) ?
C1 N1 H1A . . 125.2 ?
C8 N1 H1A . . 125.2 ?
C9 N2 C10 . . 118.86(11) ?
C9 N2 H2 . . 120.6 ?
C10 N2 H2 . . 120.6 ?
C14 N3 C21 . . 109.23(12) ?
C14 N3 H3 . . 125.4 ?
C21 N3 H3 . . 125.4 ?
C22 N4 C23 . . 120.49(11) ?
C22 N4 H4A . . 119.8 ?
C23 N4 H4A . . 119.8 ?
C12 O3 C13 . . 115.49(12) ?
C25 O6 C26 . . 116.00(12) ?
H1B O1W H1C . . 107.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.3606(18) ?
C1 C2 . 1.3744(19) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.4421(19) ?
C2 C9 . 1.4706(19) ?
C3 C4 . 1.404(2) ?
C3 C8 . 1.4083(19) ?
C4 C5 . 1.379(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.395(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.376(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.399(2) ?
C7 H7 . 0.9500 ?
C8 N1 . 1.3779(19) ?
C9 O1 . 1.2470(17) ?
C9 N2 . 1.3348(18) ?
C10 N2 . 1.4630(17) ?
C10 C11 . 1.512(2) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.507(2) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 O2 . 1.2095(17) ?
C12 O3 . 1.3285(17) ?
C13 O3 . 1.4470(19) ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 N3 . 1.3548(19) ?
C14 C15 . 1.377(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.4399(19) ?
C15 C22 . 1.4579(19) ?
C16 C17 . 1.403(2) ?
C16 C21 . 1.4114(19) ?
C17 C18 . 1.384(2) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.395(2) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.373(2) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.395(2) ?
C20 H20 . 0.9500 ?
C21 N3 . 1.3743(19) ?
C22 O4 . 1.2485(17) ?
C22 N4 . 1.3467(18) ?
C23 N4 . 1.4543(17) ?
C23 C24 . 1.511(2) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C24 C25 . 1.506(2) ?
C24 H24A . 0.9900 ?
C24 H24B . 0.9900 ?
C25 O5 . 1.2062(18) ?
C25 O6 . 1.3212(17) ?
C26 O6 . 1.451(2) ?
C26 H26A . 0.9800 ?
C26 H26B . 0.9800 ?
C26 H26C . 0.9800 ?
N1 H1A . 0.8800 ?
N2 H2 . 0.8800 ?
N3 H3 . 0.8800 ?
N4 H4A . 0.8800 ?
O1W H1B . 0.8533 ?
O1W H1C . 0.8497 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O4 1_645 0.88 2.04 2.8219(15) 147.7
N2 H2 O1W 3_665 0.88 2.09 2.9348(17) 160.6
N3 H3 O1 . 0.88 1.88 2.7404(16) 164.0
N4 H4A O2 . 0.88 2.43 3.2952(15) 167.0
O1W H1B O4 . 0.85 2.17 2.9890(18) 160.9
O1W H1C O5 3_575 0.85 1.98 2.7970(16) 159.6
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . 0.15(16) ?
N1 C1 C2 C9 . . . . -177.67(14) ?
C1 C2 C3 C4 . . . . -179.04(15) ?
C9 C2 C3 C4 . . . . -1.0(2) ?
C1 C2 C3 C8 . . . . -0.29(15) ?
C9 C2 C3 C8 . . . . 177.72(12) ?
C8 C3 C4 C5 . . . . -1.3(2) ?
C2 C3 C4 C5 . . . . 177.35(15) ?
C3 C4 C5 C6 . . . . 0.8(2) ?
C4 C5 C6 C7 . . . . 0.2(2) ?
C5 C6 C7 C8 . . . . -0.6(2) ?
C6 C7 C8 N1 . . . . -177.99(14) ?
C6 C7 C8 C3 . . . . 0.1(2) ?
C4 C3 C8 N1 . . . . 179.32(12) ?
C2 C3 C8 N1 . . . . 0.31(15) ?
C4 C3 C8 C7 . . . . 0.9(2) ?
C2 C3 C8 C7 . . . . -178.12(13) ?
C1 C2 C9 O1 . . . . 179.73(15) ?
C3 C2 C9 O1 . . . . 2.2(2) ?
C1 C2 C9 N2 . . . . -1.0(2) ?
C3 C2 C9 N2 . . . . -178.56(12) ?
N2 C10 C11 C12 . . . . -178.09(12) ?
C10 C11 C12 O2 . . . . -8.0(2) ?
C10 C11 C12 O3 . . . . 171.58(12) ?
N3 C14 C15 C16 . . . . -0.08(17) ?
N3 C14 C15 C22 . . . . 176.72(13) ?
C14 C15 C16 C17 . . . . -179.97(16) ?
C22 C15 C16 C17 . . . . 3.3(3) ?
C14 C15 C16 C21 . . . . 0.82(16) ?
C22 C15 C16 C21 . . . . -175.91(14) ?
C21 C16 C17 C18 . . . . 0.7(2) ?
C15 C16 C17 C18 . . . . -178.40(16) ?
C16 C17 C18 C19 . . . . 0.8(3) ?
C17 C18 C19 C20 . . . . -1.5(3) ?
C18 C19 C20 C21 . . . . 0.5(3) ?
C19 C20 C21 N3 . . . . 179.75(16) ?
C19 C20 C21 C16 . . . . 1.1(2) ?
C17 C16 C21 N3 . . . . 179.37(13) ?
C15 C16 C21 N3 . . . . -1.26(16) ?
C17 C16 C21 C20 . . . . -1.7(2) ?
C15 C16 C21 C20 . . . . 177.67(14) ?
C14 C15 C22 O4 . . . . -179.26(14) ?
C16 C15 C22 O4 . . . . -3.1(2) ?
C14 C15 C22 N4 . . . . -0.2(2) ?
C16 C15 C22 N4 . . . . 175.97(13) ?
N4 C23 C24 C25 . . . . 179.09(12) ?
C23 C24 C25 O5 . . . . -2.6(2) ?
C23 C24 C25 O6 . . . . 177.96(12) ?
C2 C1 N1 C8 . . . . 0.05(16) ?
C7 C8 N1 C1 . . . . 178.05(15) ?
C3 C8 N1 C1 . . . . -0.23(16) ?
O1 C9 N2 C10 . . . . -0.2(2) ?
C2 C9 N2 C10 . . . . -179.46(12) ?
C11 C10 N2 C9 . . . . -177.74(12) ?
C15 C14 N3 C21 . . . . -0.72(18) ?
C20 C21 N3 C14 . . . . -177.58(16) ?
C16 C21 N3 C14 . . . . 1.25(17) ?
O4 C22 N4 C23 . . . . -0.5(2) ?
C15 C22 N4 C23 . . . . -179.56(13) ?
C24 C23 N4 C22 . . . . -177.04(12) ?
O2 C12 O3 C13 . . . . -0.2(2) ?
C11 C12 O3 C13 . . . . -179.74(13) ?
O5 C25 O6 C26 . . . . -1.2(2) ?
C24 C25 O6 C26 . . . . 178.26(13) ?
loop_
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1 PubChem 139079010
