#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/97/2229743.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_2229743
loop_
_publ_author_name
'Rida, Mohamed'
'Essassi, El Mokhtar'
'Massip, Stéphane'
'Lazar, Saïd'
'Zouihri, Hafid'
_publ_section_title
;
 rac-(3S,4S)-3-Hydroxy-4-phenyl-1-[(S)-(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)methyl]-4,5-dihydro-1H-1,5-benzodiazepin-2(3H)-one
;
_journal_coeditor_code           LD2003
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o945
_journal_page_last               o946
_journal_paper_doi               10.1107/S1600536811010129
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C25 H23 N3 O3'
_chemical_formula_moiety         'C25 H23 N3 O3'
_chemical_formula_sum            'C25 H23 N3 O3'
_chemical_formula_weight         413.46
_chemical_name_systematic
;
rac-(3S,4S)-3-Hydroxy-4-phenyl-1-[(S)-(3-phenyl-
4,5-dihydro-1,2-oxazol-5-yl)methyl]-4,5-dihydro-1H-1,5-benzodiazepin-
2(3H)-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.373(10)
_cell_angle_beta                 102.433(10)
_cell_angle_gamma                100.03(2)
_cell_formula_units_Z            2
_cell_length_a                   8.981(2)
_cell_length_b                   9.044(2)
_cell_length_c                   13.6850(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35
_cell_measurement_theta_min      25
_cell_volume                     1058.9(4)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0099
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3584
_diffrn_reflns_theta_full        64.92
_diffrn_reflns_theta_max         64.92
_diffrn_reflns_theta_min         5.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  90
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  0.9463
_exptl_absorpt_correction_T_min  0.9026
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.172
_refine_ls_extinction_coef       0.086(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3584
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0902P)²+0.3630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1573
_reflns_number_gt                3232
_reflns_number_total             3584
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ld2003.cif
_cod_data_source_block           I
_cod_original_cell_volume        1058.9(3)
_cod_database_code               2229743
_cod_database_fobs_code          2229743
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
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
O O14 -0.14283(18) 0.8107(2) 0.54940(13) 0.0717(5) Uani d . 1 . .
O O15 0.1367(2) 0.8258(3) 0.51556(12) 0.0931(7) Uani d . 1 . .
O O22 0.45964(14) 1.08367(16) 0.74426(11) 0.0562(4) Uani d . 1 . .
N N10 0.25123(17) 0.78999(18) 0.67247(11) 0.0479(4) Uani d . 1 . .
N N13 0.0378(2) 0.52139(19) 0.67025(15) 0.0621(5) Uani d D 1 . .
N N23 0.61410(18) 1.11628(19) 0.80393(13) 0.0534(4) Uani d . 1 . .
C C1 -0.2338(2) 0.5566(2) 0.66492(17) 0.0546(5) Uani d . 1 . .
C C2 -0.2327(3) 0.6165(3) 0.76241(19) 0.0742(7) Uani d . 1 . .
C C3 -0.3594(3) 0.5798(4) 0.8033(2) 0.0860(8) Uani d . 1 . .
C C4 -0.4916(3) 0.4842(3) 0.7485(3) 0.0888(9) Uani d . 1 . .
C C5 -0.4981(3) 0.4269(3) 0.6516(3) 0.0944(10) Uani d . 1 . .
C C6 -0.3691(3) 0.4630(3) 0.6095(2) 0.0768(7) Uani d . 1 . .
C C7 -0.0924(2) 0.5884(2) 0.62070(16) 0.0550(5) Uani d . 1 . .
C C8 -0.0343(2) 0.7579(2) 0.62179(15) 0.0521(5) Uani d . 1 . .
C C9 0.1256(2) 0.7912(2) 0.59864(14) 0.0560(5) Uani d . 1 . .
C C11 0.2384(2) 0.7330(2) 0.76507(14) 0.0478(5) Uani d . 1 . .
C C12 0.1330(2) 0.5989(2) 0.76299(17) 0.0543(5) Uani d . 1 . .
C C16 0.3373(3) 0.8063(3) 0.85519(15) 0.0599(5) Uani d . 1 . .
C C17 0.3345(3) 0.7461(4) 0.94383(18) 0.0787(8) Uani d . 1 . .
C C18 0.2311(4) 0.6129(4) 0.9423(2) 0.0884(9) Uani d . 1 . .
C C19 0.1311(3) 0.5418(3) 0.8540(2) 0.0733(7) Uani d . 1 . .
C C20 0.4057(2) 0.8317(2) 0.65084(14) 0.0497(5) Uani d . 1 . .
C C21 0.4573(2) 0.9998(2) 0.64844(14) 0.0492(5) Uani d . 1 . .
C C24 0.7062(2) 1.0913(2) 0.74752(14) 0.0455(4) Uani d . 1 . .
C C25 0.6252(2) 1.0381(2) 0.63910(14) 0.0505(5) Uani d . 1 . .
C C26 0.8751(2) 1.1172(2) 0.78925(14) 0.0460(4) Uani d . 1 . .
C C27 0.9750(2) 1.1281(2) 0.72391(16) 0.0529(5) Uani d . 1 . .
C C28 1.1338(2) 1.1536(3) 0.76154(19) 0.0634(6) Uani d . 1 . .
C C29 1.1953(3) 1.1658(3) 0.8629(2) 0.0721(7) Uani d . 1 . .
C C30 1.0978(3) 1.1550(3) 0.92885(19) 0.0741(7) Uani d . 1 . .
C C31 0.9385(3) 1.1308(3) 0.89236(16) 0.0611(5) Uani d . 1 . .
H H2 -0.1443 0.6829 0.8010 0.089 Uiso calc R 1 . .
H H3 -0.3548 0.6208 0.8691 0.103 Uiso calc R 1 . .
H H4 -0.5762 0.4584 0.7768 0.107 Uiso calc R 1 . .
H H5 -0.5886 0.3635 0.6131 0.113 Uiso calc R 1 . .
H H6 -0.3752 0.4230 0.5433 0.092 Uiso calc R 1 . .
H H7 -0.1244 0.5420 0.5498 0.066 Uiso calc R 1 . .
H H8 -0.0283 0.8109 0.6888 0.062 Uiso calc R 1 . .
H H13 0.001(3) 0.421(2) 0.677(2) 0.090(8) Uiso d D 1 . .
H H14 -0.1016 0.8399 0.5048 0.108 Uiso calc R 1 . .
H H16 0.4058 0.8964 0.8559 0.072 Uiso calc R 1 . .
H H17 0.4016 0.7947 1.0042 0.094 Uiso calc R 1 . .
H H18 0.2296 0.5714 1.0018 0.106 Uiso calc R 1 . .
H H19 0.0603 0.4538 0.8546 0.088 Uiso calc R 1 . .
H H20a 0.4042 0.7770 0.5861 0.060 Uiso calc R 1 . .
H H20b 0.4817 0.7994 0.7018 0.060 Uiso calc R 1 . .
H H21 0.3879 1.0336 0.5932 0.059 Uiso calc R 1 . .
H H25a 0.6590 0.9496 0.6126 0.061 Uiso calc R 1 . .
H H25b 0.6403 1.1174 0.5971 0.061 Uiso calc R 1 . .
H H27 0.9342 1.1181 0.6546 0.064 Uiso calc R 1 . .
H H28 1.1996 1.1626 0.7175 0.076 Uiso calc R 1 . .
H H29 1.3025 1.1813 0.8877 0.086 Uiso calc R 1 . .
H H30 1.1397 1.1641 0.9980 0.089 Uiso calc R 1 . .
H H31 0.8735 1.1235 0.9370 0.073 Uiso calc 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 O14 H14 . . . 109.00 no
N23 O22 C21 . . . 108.51(14) no
C9 N10 C11 . . . 122.14(16) no
C9 N10 C20 . . . 117.82(15) no
C11 N10 C20 . . . 119.62(15) no
C7 N13 C12 . . . 117.66(16) no
C7 N13 H13 . . . 109.8(17) no
C12 N13 H13 . . . 110.1(16) no
O22 N23 C24 . . . 108.88(16) no
C2 C1 C6 . . . 117.1(2) no
C2 C1 C7 . . . 122.4(2) no
C6 C1 C7 . . . 120.5(2) no
C1 C2 C3 . . . 121.6(2) no
C1 C2 H2 . . . 119.00 no
C3 C2 H2 . . . 119.00 no
C2 C3 C4 . . . 120.8(3) no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C3 C4 C5 . . . 119.1(3) no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C4 C5 C6 . . . 120.5(3) no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C1 C6 C5 . . . 120.9(3) no
C1 C6 H6 . . . 120.00 no
C5 C6 H6 . . . 120.00 no
N13 C7 C1 . . . 113.45(17) no
N13 C7 C8 . . . 109.22(16) no
N13 C7 H7 . . . 107.00 no
C1 C7 C8 . . . 112.31(15) no
C1 C7 H7 . . . 107.00 no
C8 C7 H7 . . . 107.00 no
O14 C8 C7 . . . 108.40(16) no
O14 C8 C9 . . . 109.81(16) no
O14 C8 H8 . . . 109.00 no
C7 C8 C9 . . . 112.00(15) no
C7 C8 H8 . . . 109.00 no
C9 C8 H8 . . . 109.00 no
O15 C9 N10 . . . 122.11(18) no
O15 C9 C8 . . . 119.30(18) no
N10 C9 C8 . . . 118.48(16) no
N10 C11 C12 . . . 119.65(17) no
N10 C11 C16 . . . 119.64(18) no
C12 C11 C16 . . . 120.59(19) no
N13 C12 C11 . . . 120.15(19) no
N13 C12 C19 . . . 121.85(19) no
C11 C12 C19 . . . 117.9(2) no
C11 C16 C17 . . . 120.3(2) no
C11 C16 H16 . . . 120.00 no
C17 C16 H16 . . . 120.00 no
C16 C17 C18 . . . 119.5(2) no
C16 C17 H17 . . . 120.00 no
C18 C17 H17 . . . 120.00 no
C17 C18 C19 . . . 120.5(3) no
C17 C18 H18 . . . 120.00 no
C19 C18 H18 . . . 120.00 no
C12 C19 C18 . . . 121.2(3) no
C12 C19 H19 . . . 119.00 no
C18 C19 H19 . . . 119.00 no
N10 C20 C21 . . . 114.08(15) no
N10 C20 H20a . . . 109.00 no
N10 C20 H20b . . . 109.00 no
C21 C20 H20a . . . 109.00 no
C21 C20 H20b . . . 109.00 no
H20a C20 H20b . . . 108.00 no
O22 C21 C20 . . . 109.67(15) no
O22 C21 C25 . . . 103.98(14) no
O22 C21 H21 . . . 110.00 no
C20 C21 C25 . . . 111.47(15) no
C20 C21 H21 . . . 111.00 no
C25 C21 H21 . . . 111.00 no
N23 C24 C25 . . . 113.70(17) no
N23 C24 C26 . . . 120.91(17) no
C25 C24 C26 . . . 125.39(16) no
C21 C25 C24 . . . 100.10(15) no
C21 C25 H25a . . . 112.00 no
C21 C25 H25b . . . 112.00 no
C24 C25 H25a . . . 112.00 no
C24 C25 H25b . . . 112.00 no
H25a C25 H25b . . . 109.00 no
C24 C26 C27 . . . 119.42(17) no
C24 C26 C31 . . . 121.77(19) no
C27 C26 C31 . . . 118.82(19) no
C26 C27 C28 . . . 120.3(2) no
C26 C27 H27 . . . 120.00 no
C28 C27 H27 . . . 120.00 no
C27 C28 C29 . . . 120.5(2) no
C27 C28 H28 . . . 120.00 no
C29 C28 H28 . . . 120.00 no
C28 C29 C30 . . . 119.9(2) no
C28 C29 H29 . . . 120.00 no
C30 C29 H29 . . . 120.00 no
C29 C30 C31 . . . 120.3(2) no
C29 C30 H30 . . . 120.00 no
C31 C30 H30 . . . 120.00 no
C26 C31 C30 . . . 120.2(2) no
C26 C31 H31 . . . 120.00 no
C30 C31 H31 . . . 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O14 C8 . . 1.412(3) no
O14 H14 . . 0.8200 no
O15 C9 . . 1.227(3) no
O22 N23 . . 1.415(2) no
O22 C21 . . 1.446(2) no
N10 C9 . . 1.345(2) no
N10 C11 . . 1.432(2) no
N10 C20 . . 1.473(2) no
N13 C7 . . 1.475(3) no
N13 C12 . . 1.411(3) no
N13 H13 . . 0.931(19) no
N23 C24 . . 1.280(3) no
C1 C2 . . 1.390(3) no
C1 C6 . . 1.376(3) no
C1 C7 . . 1.516(3) no
C2 C3 . . 1.377(4) no
C2 H2 . . 0.9300 no
C3 C4 . . 1.363(4) no
C3 H3 . . 0.9300 no
C4 C5 . . 1.363(5) no
C4 H4 . . 0.9300 no
C5 C6 . . 1.404(4) no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C7 C8 . . 1.529(3) no
C7 H7 . . 0.9800 no
C8 C9 . . 1.522(3) no
C8 H8 . . 0.9800 no
C11 C12 . . 1.396(3) no
C11 C16 . . 1.386(3) no
C12 C19 . . 1.395(3) no
C16 C17 . . 1.379(4) no
C16 H16 . . 0.9300 no
C17 C18 . . 1.383(5) no
C17 H17 . . 0.9300 no
C18 C19 . . 1.366(4) no
C18 H18 . . 0.9300 no
C19 H19 . . 0.9300 no
C20 C21 . . 1.516(3) no
C20 H20a . . 0.9700 no
C20 H20b . . 0.9700 no
C21 C25 . . 1.523(3) no
C21 H21 . . 0.9800 no
C24 C25 . . 1.497(3) no
C24 C26 . . 1.470(3) no
C25 H25a . . 0.9700 no
C25 H25b . . 0.9700 no
C26 C27 . . 1.395(3) no
C26 C31 . . 1.388(3) no
C27 C28 . . 1.378(3) no
C27 H27 . . 0.9300 no
C28 C29 . . 1.364(4) no
C28 H28 . . 0.9300 no
C29 C30 . . 1.385(4) no
C29 H29 . . 0.9300 no
C30 C31 . . 1.381(4) no
C30 H30 . . 0.9300 no
C31 H31 . . 0.9300 no
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
_geom_hbond_publ_flag
O14 H14 O15 . 0.82 2.14 2.632(3) 118 yes
C16 H16 O22 . 0.93 2.44 3.206(3) 140 yes
C25 H25a O14 1_655 0.97 2.59 3.493(3) 154 yes
C27 H27 O15 2_676 0.93 2.40 3.302(3) 162 yes
C28 H28 O22 1_655 0.93 2.52 3.152(2) 125 yes
C19 H19 Cg4 1_445 0.93 2.78 3.534(3) 139 yes
N13 H13 Cg4 1_445 0.931(19) 2.766(19) 3.671(3) 164 yes
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
O14 C8 C9 O15 . . . . -15.0(3) no
O14 C8 C9 N10 . . . . 161.30(17) no
O22 N23 C24 C25 . . . . 0.4(2) no
O22 N23 C24 C26 . . . . 179.36(16) no
O22 C21 C25 C24 . . . . 20.06(17) no
N10 C11 C12 N13 . . . . -1.1(3) no
N10 C11 C12 C19 . . . . 175.89(19) no
N10 C11 C16 C17 . . . . -174.9(2) no
N10 C20 C21 O22 . . . . 58.2(2) no
N10 C20 C21 C25 . . . . 172.78(15) no
N13 C7 C8 O14 . . . . 162.39(16) no
N13 C7 C8 C9 . . . . 41.1(2) no
N13 C12 C19 C18 . . . . 175.7(3) no
N23 O22 C21 C20 . . . . 97.71(17) no
N23 O22 C21 C25 . . . . -21.61(18) no
N23 C24 C25 C21 . . . . -13.3(2) no
N23 C24 C26 C27 . . . . -163.20(18) no
N23 C24 C26 C31 . . . . 17.0(3) no
C1 C2 C3 C4 . . . . -0.8(5) no
C1 C7 C8 O14 . . . . -70.8(2) no
C1 C7 C8 C9 . . . . 167.85(17) no
C2 C1 C6 C5 . . . . -1.8(4) no
C2 C1 C7 N13 . . . . 67.0(3) no
C2 C1 C7 C8 . . . . -57.4(3) no
C2 C3 C4 C5 . . . . -1.1(5) no
C3 C4 C5 C6 . . . . 1.5(4) no
C4 C5 C6 C1 . . . . 0.0(4) no
C6 C1 C2 C3 . . . . 2.2(4) no
C6 C1 C7 N13 . . . . -111.5(2) no
C6 C1 C7 C8 . . . . 124.0(2) no
C7 N13 C12 C11 . . . . -73.2(2) no
C7 N13 C12 C19 . . . . 110.0(2) no
C7 C1 C2 C3 . . . . -176.4(2) no
C7 C1 C6 C5 . . . . 176.8(2) no
C7 C8 C9 O15 . . . . 105.5(2) no
C7 C8 C9 N10 . . . . -78.2(2) no
C9 N10 C11 C12 . . . . 42.8(3) no
C9 N10 C11 C16 . . . . -141.1(2) no
C9 N10 C20 C21 . . . . 74.2(2) no
C11 N10 C9 O15 . . . . -172.6(2) no
C11 N10 C9 C8 . . . . 11.3(3) no
C11 N10 C20 C21 . . . . -113.19(18) no
C11 C12 C19 C18 . . . . -1.2(4) no
C11 C16 C17 C18 . . . . -0.7(4) no
C12 N13 C7 C1 . . . . -79.9(2) no
C12 N13 C7 C8 . . . . 46.2(2) no
C12 C11 C16 C17 . . . . 1.1(4) no
C16 C11 C12 N13 . . . . -177.1(2) no
C16 C11 C12 C19 . . . . -0.1(3) no
C16 C17 C18 C19 . . . . -0.7(5) no
C17 C18 C19 C12 . . . . 1.7(5) no
C20 N10 C9 O15 . . . . -0.1(3) no
C20 N10 C9 C8 . . . . -176.28(15) no
C20 N10 C11 C12 . . . . -129.51(19) no
C20 N10 C11 C16 . . . . 46.5(3) no
C20 C21 C25 C24 . . . . -98.02(17) no
C21 O22 N23 C24 . . . . 13.9(2) no
C24 C26 C27 C28 . . . . 179.47(19) no
C24 C26 C31 C30 . . . . 180.0(2) no
C25 C24 C26 C27 . . . . 15.6(3) no
C25 C24 C26 C31 . . . . -164.2(2) no
C26 C24 C25 C21 . . . . 167.78(17) no
C26 C27 C28 C29 . . . . 1.2(4) no
C27 C26 C31 C30 . . . . 0.1(3) no
C27 C28 C29 C30 . . . . -1.1(4) no
C28 C29 C30 C31 . . . . 0.5(4) no
C29 C30 C31 C26 . . . . 0.0(4) no
C31 C26 C27 C28 . . . . -0.7(3) no
