#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:36:25 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257134 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/87/4038773.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_4038773
loop_
_publ_author_name
'Richaud, Alexis D.'
'Roche, Stéphane P'
_publ_section_title
;
 Structure-Property Relationship Study of N-(Hydroxy)Peptides for
 the Design of Self-Assembled Parallel β-Sheets.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12329
_journal_page_last               12342
_journal_paper_doi               10.1021/acs.joc.0c01441
_journal_volume                  85
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C14 H25 N3 O7'
_chemical_formula_sum            'C14 H25 N3 O7'
_chemical_formula_weight         347.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90.242(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5051(18)
_cell_length_b                   8.8409(18)
_cell_length_c                   20.790(4)
_cell_measurement_reflns_used    2811
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      11.82
_cell_measurement_theta_min      2.17
_cell_volume                     1747.0(6)
_computing_cell_refinement       'APEX II v2014.11-0 (Bruker, 2014)'
_computing_data_collection       '15IDD, ChemMatCARS, 2019'
_computing_data_reduction        'APEX II v2014.11-0 (Bruker, 2014)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2016)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2016)'
_computing_structure_solution    'SHELX (Bruker, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Pilatus1M pixel array detector'
_diffrn_detector_area_resol_mean 5.8
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details
'0.5 degree frames measured for 1 seconds each'
_diffrn_measurement_device       'three-circle goniometer with fixed chi'
_diffrn_measurement_device_type  'huber three-circle diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'silicon  1 1 1 and 3 1 1'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.41328
_diffrn_reflns_av_R_equivalents  0.1178
_diffrn_reflns_av_unetI/netI     0.1065
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            39900
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        14.357
_diffrn_reflns_theta_max         14.614
_diffrn_reflns_theta_min         1.139
_exptl_absorpt_coefficient_mu    0.041
_exptl_absorpt_correction_T_max  0.7438
_exptl_absorpt_correction_T_min  0.6130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Sheldrick; 2018'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.015
_exptl_crystal_size_mid          0.004
_exptl_crystal_size_min          0.002
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details
;
 Flack x determined using 1650 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -4.0(10)
_refine_ls_extinction_coef       0.23(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6458
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0689
_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)+(0.0986P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.1873
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                4346
_reflns_number_total             6458
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01441_si_002.cif
_cod_data_source_block           s19031
_cod_depositor_comments          'Adding full bibliography for 4038773.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038773
_shelx_shelxl_version_number     2017/1
_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_min   0.999
_shelx_estimated_absorpt_t_max   1.000
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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_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
O1A O 0.5359(5) 0.2882(4) 0.9817(2) 0.0478(11) Uani 1 1 d . . . . .
O2A O 0.6988(5) 0.6360(4) 1.0128(2) 0.0462(11) Uani 1 1 d . . . . .
H2OA H 0.635586 0.701345 1.007615 0.05(2) Uiso 1 1 calc R . . . .
O3A O 0.5585(4) 0.5949(4) 0.8616(2) 0.0443(10) Uani 1 1 d . . . . .
O4A O 0.8737(5) 0.4169(5) 0.7151(2) 0.0475(11) Uani 1 1 d . . . . .
O5A O 0.6025(5) 0.6187(5) 0.6402(3) 0.0562(12) Uani 1 1 d . . . . .
H5OA H 0.524298 0.596682 0.656375 0.084 Uiso 1 1 calc R U . . .
O6A O 0.7983(7) 0.4319(7) 0.4901(3) 0.0801(17) Uani 1 1 d . . . . .
O7A O 0.8711(6) 0.6147(7) 0.5576(3) 0.0792(17) Uani 1 1 d . . . . .
N1A N 0.6587(5) 0.5021(5) 0.9826(3) 0.0417(12) Uani 1 1 d . . . . .
N2A N 0.7773(5) 0.5681(5) 0.8196(2) 0.0410(12) Uani 1 1 d . . . . .
H2NA H 0.864909 0.541412 0.827487 0.06(2) Uiso 1 1 calc R . . . .
N3A N 0.6989(6) 0.5029(6) 0.6531(3) 0.0480(13) Uani 1 1 d . . . . .
C1A C 0.5112(7) 0.4499(7) 1.0745(3) 0.0469(15) Uani 1 1 d . . . . .
H1A H 0.441469 0.530647 1.069304 0.070 Uiso 1 1 calc R U . . .
H1B H 0.588107 0.485417 1.102157 0.070 Uiso 1 1 calc R U . . .
H1C H 0.466641 0.361414 1.094128 0.070 Uiso 1 1 calc R U . . .
C2A C 0.5686(6) 0.4074(6) 1.0099(3) 0.0397(14) Uani 1 1 d . . . . .
C3A C 0.7372(6) 0.4687(7) 0.9249(3) 0.0419(14) Uani 1 1 d . . . . .
H3A H 0.733132 0.358521 0.916536 0.050 Uiso 1 1 calc R U . . .
H3B H 0.837048 0.496407 0.931776 0.050 Uiso 1 1 calc R U . . .
C4A C 0.6819(6) 0.5520(6) 0.8665(3) 0.0385(14) Uani 1 1 d . . . . .
C5A C 0.7427(7) 0.6273(7) 0.7567(3) 0.0426(14) Uani 1 1 d . . . . .
H5A H 0.639074 0.646614 0.755049 0.051 Uiso 1 1 calc R U . . .
C6A C 0.7781(6) 0.5080(6) 0.7065(3) 0.0432(14) Uani 1 1 d . . . . .
C7A C 0.7306(7) 0.4116(8) 0.5975(3) 0.0520(16) Uani 1 1 d . . . . .
H7A H 0.641785 0.372490 0.578780 0.062 Uiso 1 1 calc R U . . .
H7B H 0.788321 0.323844 0.610899 0.062 Uiso 1 1 calc R U . . .
C8A C 0.8086(8) 0.4999(9) 0.5470(4) 0.0609(19) Uani 1 1 d . . . . .
C9A C 0.8561(12) 0.5106(13) 0.4334(5) 0.101(4) Uani 1 1 d . . . . .
H9A H 0.801719 0.479740 0.394894 0.121 Uiso 1 1 calc R U . . .
H9B H 0.843181 0.620864 0.439141 0.121 Uiso 1 1 calc R U . . .
C10A C 0.9947(12) 0.4821(13) 0.4230(6) 0.111(4) Uani 1 1 d . . . . .
H10A H 1.050702 0.523496 0.458537 0.167 Uiso 1 1 calc R U . . .
H10B H 1.023653 0.529555 0.382552 0.167 Uiso 1 1 calc R U . . .
H10C H 1.009727 0.372566 0.420314 0.167 Uiso 1 1 calc R U . . .
C11A C 0.8202(7) 0.7773(7) 0.7411(4) 0.0483(16) Uani 1 1 d . . . . .
H11A H 0.791843 0.807665 0.696577 0.058 Uiso 1 1 calc R U . . .
C12A C 0.7736(7) 0.9009(7) 0.7857(4) 0.0504(16) Uani 1 1 d . . . . .
H12A H 0.804932 0.875403 0.829866 0.061 Uiso 1 1 calc R U . . .
H12B H 0.669436 0.903901 0.785805 0.061 Uiso 1 1 calc R U . . .
C13A C 0.8284(8) 1.0581(7) 0.7688(4) 0.0547(17) Uani 1 1 d . . . . .
H13A H 0.931343 1.058803 0.771843 0.082 Uiso 1 1 calc R U . . .
H13B H 0.789597 1.132336 0.798916 0.082 Uiso 1 1 calc R U . . .
H13C H 0.799580 1.084061 0.724887 0.082 Uiso 1 1 calc R U . . .
C14A C 0.9795(7) 0.7564(8) 0.7412(4) 0.063(2) Uani 1 1 d . . . . .
H14A H 1.024750 0.851130 0.728285 0.095 Uiso 1 1 calc R U . . .
H14B H 1.004793 0.676061 0.710937 0.095 Uiso 1 1 calc R U . . .
H14C H 1.011168 0.728556 0.784559 0.095 Uiso 1 1 calc R U . . .
O1B O 0.0254(5) 0.7943(4) 0.9812(2) 0.0465(11) Uani 1 1 d . . . . .
O2B O 0.2052(4) 0.4546(4) 1.0096(2) 0.0457(10) Uani 1 1 d . . . . .
H2OB H 0.138580 0.392336 1.010934 0.038(17) Uiso 1 1 calc R . . . .
O3B O 0.0549(4) 0.4731(4) 0.8642(2) 0.0450(10) Uani 1 1 d . . . . .
O4B O 0.3883(5) 0.5438(5) 0.7100(2) 0.0534(12) Uani 1 1 d . . . . .
O5B O 0.1012(5) 0.3338(5) 0.6550(2) 0.0533(12) Uani 1 1 d . . . . .
H5OB H 0.024538 0.360814 0.671294 0.05(2) Uiso 1 1 calc R . . . .
O6B O 0.3341(5) 0.4965(5) 0.4998(2) 0.0585(13) Uani 1 1 d . . . . .
O7B O 0.3801(5) 0.3179(6) 0.5737(3) 0.0630(13) Uani 1 1 d . . . . .
N1B N 0.1593(5) 0.5878(5) 0.9803(3) 0.0409(12) Uani 1 1 d . . . . .
N2B N 0.2775(5) 0.4743(6) 0.8257(3) 0.0446(12) Uani 1 1 d . . . . .
H2NB H 0.363269 0.510003 0.830696 0.035(16) Uiso 1 1 calc R . . . .
N3B N 0.1982(5) 0.4516(6) 0.6598(3) 0.0491(13) Uani 1 1 d . . . . .
C1B C 0.0109(7) 0.6315(7) 1.0731(3) 0.0456(15) Uani 1 1 d . . . . .
H1D H -0.021122 0.721734 1.096137 0.068 Uiso 1 1 calc R U . . .
H1E H 0.086920 0.582928 1.097443 0.068 Uiso 1 1 calc R U . . .
H1F H -0.067654 0.560619 1.068143 0.068 Uiso 1 1 calc R U . . .
C2B C 0.0637(6) 0.6761(6) 1.0082(3) 0.0398(14) Uani 1 1 d . . . . .
C3B C 0.2280(6) 0.6202(6) 0.9208(3) 0.0402(14) Uani 1 1 d . . . . .
H3C H 0.330976 0.609070 0.926472 0.048 Uiso 1 1 calc R U . . .
H3D H 0.208516 0.726127 0.908200 0.048 Uiso 1 1 calc R U . . .
C4B C 0.1776(6) 0.5139(6) 0.8675(3) 0.0387(14) Uani 1 1 d . . . . .
C5B C 0.2469(7) 0.3728(7) 0.7718(3) 0.0461(15) Uani 1 1 d . . . . .
H5B H 0.143463 0.352071 0.770888 0.055 Uiso 1 1 calc R U . . .
C6B C 0.2855(7) 0.4585(7) 0.7116(3) 0.0480(15) Uani 1 1 d . . . . .
C7B C 0.2270(7) 0.5254(8) 0.6000(3) 0.0536(17) Uani 1 1 d . . . . .
H7C H 0.271877 0.624453 0.608657 0.064 Uiso 1 1 calc R U . . .
H7D H 0.137266 0.544489 0.577024 0.064 Uiso 1 1 calc R U . . .
C8B C 0.3228(7) 0.4321(8) 0.5573(3) 0.0492(16) Uani 1 1 d . . . . .
C9B C 0.4172(10) 0.4122(9) 0.4529(4) 0.072(2) Uani 1 1 d . . . . .
H9C H 0.375582 0.310860 0.445854 0.086 Uiso 1 1 calc R U . . .
H9D H 0.514689 0.399130 0.468832 0.086 Uiso 1 1 calc R U . . .
C10B C 0.4171(9) 0.4992(10) 0.3918(4) 0.069(2) Uani 1 1 d . . . . .
H10D H 0.320709 0.506795 0.375188 0.104 Uiso 1 1 calc R U . . .
H10E H 0.476189 0.447412 0.360169 0.104 Uiso 1 1 calc R U . . .
H10F H 0.454396 0.600940 0.399669 0.104 Uiso 1 1 calc R U . . .
C11B C 0.3254(7) 0.2215(7) 0.7808(4) 0.0480(16) Uani 1 1 d . . . . .
H11B H 0.298322 0.182684 0.824245 0.058 Uiso 1 1 calc R U . . .
C12B C 0.2773(7) 0.1016(7) 0.7321(4) 0.0478(15) Uani 1 1 d . . . . .
H12C H 0.315449 0.127359 0.689256 0.057 Uiso 1 1 calc R U . . .
H12D H 0.173401 0.103401 0.728984 0.057 Uiso 1 1 calc R U . . .
C13B C 0.3253(8) -0.0589(7) 0.7504(4) 0.0571(18) Uani 1 1 d . . . . .
H13D H 0.427569 -0.059969 0.756378 0.086 Uiso 1 1 calc R U . . .
H13E H 0.299262 -0.129418 0.715981 0.086 Uiso 1 1 calc R U . . .
H13F H 0.279468 -0.089535 0.790480 0.086 Uiso 1 1 calc R U . . .
C14B C 0.4832(7) 0.2402(8) 0.7821(4) 0.0592(19) Uani 1 1 d . . . . .
H14D H 0.527510 0.142560 0.791437 0.089 Uiso 1 1 calc R U . . .
H14E H 0.509308 0.313397 0.815450 0.089 Uiso 1 1 calc R U . . .
H14F H 0.515161 0.276868 0.740117 0.089 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0001 0.0005 '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 0.0005 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0017 0.0018 '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
N1A O2A H2OA 109.5 . . ?
N3A O5A H5OA 109.5 . . ?
C8A O6A C9A 118.1(8) . . ?
C2A N1A O2A 121.3(5) . . ?
C2A N1A C3A 124.2(5) . . ?
O2A N1A C3A 114.0(5) . . ?
C4A N2A C5A 122.9(5) . . ?
C4A N2A H2NA 118.5 . . ?
C5A N2A H2NA 118.5 . . ?
C6A N3A O5A 120.0(5) . . ?
C6A N3A C7A 124.4(5) . . ?
O5A N3A C7A 113.2(5) . . ?
C2A C1A H1A 109.5 . . ?
C2A C1A H1B 109.5 . . ?
H1A C1A H1B 109.5 . . ?
C2A C1A H1C 109.5 . . ?
H1A C1A H1C 109.5 . . ?
H1B C1A H1C 109.5 . . ?
O1A C2A N1A 119.6(6) . . ?
O1A C2A C1A 122.9(5) . . ?
N1A C2A C1A 117.6(5) . . ?
N1A C3A C4A 112.8(5) . . ?
N1A C3A H3A 109.0 . . ?
C4A C3A H3A 109.0 . . ?
N1A C3A H3B 109.0 . . ?
C4A C3A H3B 109.0 . . ?
H3A C3A H3B 107.8 . . ?
O3A C4A N2A 123.5(6) . . ?
O3A C4A C3A 122.8(6) . . ?
N2A C4A C3A 113.6(5) . . ?
N2A C5A C6A 108.6(5) . . ?
N2A C5A C11A 113.1(5) . . ?
C6A C5A C11A 110.0(5) . . ?
N2A C5A H5A 108.3 . . ?
C6A C5A H5A 108.3 . . ?
C11A C5A H5A 108.3 . . ?
O4A C6A N3A 120.7(6) . . ?
O4A C6A C5A 121.4(6) . . ?
N3A C6A C5A 117.8(5) . . ?
N3A C7A C8A 112.0(6) . . ?
N3A C7A H7A 109.2 . . ?
C8A C7A H7A 109.2 . . ?
N3A C7A H7B 109.2 . . ?
C8A C7A H7B 109.2 . . ?
H7A C7A H7B 107.9 . . ?
O7A C8A O6A 125.7(7) . . ?
O7A C8A C7A 123.8(8) . . ?
O6A C8A C7A 110.5(7) . . ?
C10A C9A O6A 113.9(9) . . ?
C10A C9A H9A 108.8 . . ?
O6A C9A H9A 108.8 . . ?
C10A C9A H9B 108.8 . . ?
O6A C9A H9B 108.8 . . ?
H9A C9A H9B 107.7 . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C9A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C12A C11A C14A 112.5(6) . . ?
C12A C11A C5A 110.6(5) . . ?
C14A C11A C5A 111.6(5) . . ?
C12A C11A H11A 107.3 . . ?
C14A C11A H11A 107.3 . . ?
C5A C11A H11A 107.3 . . ?
C11A C12A C13A 114.8(6) . . ?
C11A C12A H12A 108.6 . . ?
C13A C12A H12A 108.6 . . ?
C11A C12A H12B 108.6 . . ?
C13A C12A H12B 108.6 . . ?
H12A C12A H12B 107.6 . . ?
C12A C13A H13A 109.5 . . ?
C12A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C12A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C11A C14A H14A 109.5 . . ?
C11A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C11A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
N1B O2B H2OB 109.5 . . ?
N3B O5B H5OB 109.5 . . ?
C8B O6B C9B 115.3(5) . . ?
C2B N1B O2B 121.1(5) . . ?
C2B N1B C3B 125.1(5) . . ?
O2B N1B C3B 113.8(5) . . ?
C4B N2B C5B 121.3(5) . . ?
C4B N2B H2NB 119.4 . . ?
C5B N2B H2NB 119.4 . . ?
C6B N3B O5B 119.4(5) . . ?
C6B N3B C7B 123.4(6) . . ?
O5B N3B C7B 114.1(5) . . ?
C2B C1B H1D 109.5 . . ?
C2B C1B H1E 109.5 . . ?
H1D C1B H1E 109.5 . . ?
C2B C1B H1F 109.5 . . ?
H1D C1B H1F 109.5 . . ?
H1E C1B H1F 109.5 . . ?
O1B C2B N1B 119.7(6) . . ?
O1B C2B C1B 122.2(6) . . ?
N1B C2B C1B 118.1(5) . . ?
N1B C3B C4B 111.1(5) . . ?
N1B C3B H3C 109.4 . . ?
C4B C3B H3C 109.4 . . ?
N1B C3B H3D 109.4 . . ?
C4B C3B H3D 109.4 . . ?
H3C C3B H3D 108.0 . . ?
O3B C4B N2B 124.4(6) . . ?
O3B C4B C3B 121.3(5) . . ?
N2B C4B C3B 114.3(5) . . ?
N2B C5B C6B 106.2(5) . . ?
N2B C5B C11B 110.1(5) . . ?
C6B C5B C11B 114.7(5) . . ?
N2B C5B H5B 108.6 . . ?
C6B C5B H5B 108.6 . . ?
C11B C5B H5B 108.6 . . ?
O4B C6B N3B 119.1(6) . . ?
O4B C6B C5B 121.7(6) . . ?
N3B C6B C5B 119.0(6) . . ?
N3B C7B C8B 112.1(6) . . ?
N3B C7B H7C 109.2 . . ?
C8B C7B H7C 109.2 . . ?
N3B C7B H7D 109.2 . . ?
C8B C7B H7D 109.2 . . ?
H7C C7B H7D 107.9 . . ?
O7B C8B O6B 125.3(6) . . ?
O7B C8B C7B 124.5(7) . . ?
O6B C8B C7B 110.1(6) . . ?
O6B C9B C10B 107.9(7) . . ?
O6B C9B H9C 110.1 . . ?
C10B C9B H9C 110.1 . . ?
O6B C9B H9D 110.1 . . ?
C10B C9B H9D 110.1 . . ?
H9C C9B H9D 108.4 . . ?
C9B C10B H10D 109.5 . . ?
C9B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C9B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C14B C11B C12B 112.3(6) . . ?
C14B C11B C5B 112.8(5) . . ?
C12B C11B C5B 112.1(5) . . ?
C14B C11B H11B 106.4 . . ?
C12B C11B H11B 106.4 . . ?
C5B C11B H11B 106.4 . . ?
C11B C12B C13B 112.8(6) . . ?
C11B C12B H12C 109.0 . . ?
C13B C12B H12C 109.0 . . ?
C11B C12B H12D 109.0 . . ?
C13B C12B H12D 109.0 . . ?
H12C C12B H12D 107.8 . . ?
C12B C13B H13D 109.5 . . ?
C12B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C12B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C11B C14B H14D 109.5 . . ?
C11B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C11B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
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
O1A C2A 1.245(7) . ?
O2A N1A 1.392(6) . ?
O2A H2OA 0.8400 . ?
O3A C4A 1.237(7) . ?
O4A C6A 1.227(7) . ?
O5A N3A 1.399(7) . ?
O5A H5OA 0.8400 . ?
O6A C8A 1.329(10) . ?
O6A C9A 1.476(11) . ?
O7A C8A 1.197(10) . ?
N1A C2A 1.327(7) . ?
N1A C3A 1.447(8) . ?
N2A C4A 1.342(8) . ?
N2A C5A 1.444(8) . ?
N2A H2NA 0.8800 . ?
N3A C6A 1.340(9) . ?
N3A C7A 1.444(9) . ?
C1A C2A 1.499(9) . ?
C1A H1A 0.9800 . ?
C1A H1B 0.9800 . ?
C1A H1C 0.9800 . ?
C3A C4A 1.512(9) . ?
C3A H3A 0.9900 . ?
C3A H3B 0.9900 . ?
C5A C6A 1.522(9) . ?
C5A C11A 1.552(9) . ?
C5A H5A 1.0000 . ?
C7A C8A 1.506(10) . ?
C7A H7A 0.9900 . ?
C7A H7B 0.9900 . ?
C9A C10A 1.360(13) . ?
C9A H9A 0.9900 . ?
C9A H9B 0.9900 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C11A C12A 1.501(9) . ?
C11A C14A 1.525(9) . ?
C11A H11A 1.0000 . ?
C12A C13A 1.526(9) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
O1B C2B 1.240(7) . ?
O2B N1B 1.395(6) . ?
O2B H2OB 0.8400 . ?
O3B C4B 1.223(7) . ?
O4B C6B 1.235(8) . ?
O5B N3B 1.394(7) . ?
O5B H5OB 0.8400 . ?
O6B C8B 1.330(8) . ?
O6B C9B 1.461(9) . ?
O7B C8B 1.196(8) . ?
N1B C2B 1.333(8) . ?
N1B C3B 1.430(8) . ?
N2B C4B 1.336(8) . ?
N2B C5B 1.465(8) . ?
N2B H2NB 0.8800 . ?
N3B C6B 1.359(9) . ?
N3B C7B 1.432(9) . ?
C1B C2B 1.494(9) . ?
C1B H1D 0.9800 . ?
C1B H1E 0.9800 . ?
C1B H1F 0.9800 . ?
C3B C4B 1.528(9) . ?
C3B H3C 0.9900 . ?
C3B H3D 0.9900 . ?
C5B C6B 1.509(10) . ?
C5B C11B 1.542(9) . ?
C5B H5B 1.0000 . ?
C7B C8B 1.517(9) . ?
C7B H7C 0.9900 . ?
C7B H7D 0.9900 . ?
C9B C10B 1.485(12) . ?
C9B H9C 0.9900 . ?
C9B H9D 0.9900 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11B C14B 1.509(9) . ?
C11B C12B 1.535(9) . ?
C11B H11B 1.0000 . ?
C12B C13B 1.537(9) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
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
_geom_hbond_publ_flag
O2A H2OA O1A 0.84 1.82 2.608(6) 156.4 2_657 yes
O5A H5OA O4B 0.84 1.77 2.591(7) 164.1 . yes
N2A H2NA O3B 0.88 2.05 2.916(6) 168.6 1_655 yes
C1A H1A O1A 0.98 2.52 3.241(8) 130.2 2_657 yes
C1A H1A O2B 0.98 2.65 3.201(8) 116.0 . yes
C1A H1C O3A 0.98 2.54 3.473(8) 158.9 2_647 yes
C3A H3B O3B 0.99 2.52 3.277(7) 133.6 1_655 yes
C7A H7A O7B 0.99 2.54 3.466(9) 156.6 . yes
C10A H10C O7A 0.98 2.59 3.511(12) 157.6 2_746 yes
O2B H2OB O1B 0.84 1.79 2.618(6) 167.6 2_547 yes
O5B H5OB O4A 0.84 1.77 2.608(6) 172.8 1_455 yes
N2B H2NB O3A 0.88 2.10 2.968(7) 168.9 . yes
C1B H1D O3B 0.98 2.39 3.350(7) 165.3 2_557 yes
C1B H1F O2A 0.98 2.58 3.216(8) 122.3 1_455 yes
C1B H1F O1B 0.98 2.60 3.206(7) 120.1 2_547 yes
C3B H3C O3A 0.99 2.56 3.386(7) 141.3 . yes
C7B H7D O7A 0.99 2.63 3.580(9) 159.8 1_455 yes
C9B H9C O5A 0.99 2.48 3.242(10) 133.9 2_646 yes
C10B H10F O7B 0.98 2.54 3.487(9) 162.3 2_656 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2A N1A C2A O1A -179.5(5) . . . . ?
C3A N1A C2A O1A -8.1(9) . . . . ?
O2A N1A C2A C1A 0.1(8) . . . . ?
C3A N1A C2A C1A 171.5(5) . . . . ?
C2A N1A C3A C4A 106.0(6) . . . . ?
O2A N1A C3A C4A -82.0(6) . . . . ?
C5A N2A C4A O3A -4.7(9) . . . . ?
C5A N2A C4A C3A 172.2(5) . . . . ?
N1A C3A C4A O3A -25.9(8) . . . . ?
N1A C3A C4A N2A 157.2(5) . . . . ?
C4A N2A C5A C6A -120.5(6) . . . . ?
C4A N2A C5A C11A 117.1(6) . . . . ?
O5A N3A C6A O4A -171.8(5) . . . . ?
C7A N3A C6A O4A -10.7(9) . . . . ?
O5A N3A C6A C5A 9.8(8) . . . . ?
C7A N3A C6A C5A 170.9(5) . . . . ?
N2A C5A C6A O4A -29.9(8) . . . . ?
C11A C5A C6A O4A 94.4(7) . . . . ?
N2A C5A C6A N3A 148.4(5) . . . . ?
C11A C5A C6A N3A -87.3(7) . . . . ?
C6A N3A C7A C8A -95.5(8) . . . . ?
O5A N3A C7A C8A 66.8(7) . . . . ?
C9A O6A C8A O7A -6.5(12) . . . . ?
C9A O6A C8A C7A 173.8(7) . . . . ?
N3A C7A C8A O7A 19.7(11) . . . . ?
N3A C7A C8A O6A -160.7(6) . . . . ?
C8A O6A C9A C10A 87.7(11) . . . . ?
N2A C5A C11A C12A -64.8(7) . . . . ?
C6A C5A C11A C12A 173.5(6) . . . . ?
N2A C5A C11A C14A 61.2(7) . . . . ?
C6A C5A C11A C14A -60.5(8) . . . . ?
C14A C11A C12A C13A 62.3(8) . . . . ?
C5A C11A C12A C13A -172.2(6) . . . . ?
O2B N1B C2B O1B 179.6(5) . . . . ?
C3B N1B C2B O1B 2.2(9) . . . . ?
O2B N1B C2B C1B 2.3(8) . . . . ?
C3B N1B C2B C1B -175.0(5) . . . . ?
C2B N1B C3B C4B -109.6(6) . . . . ?
O2B N1B C3B C4B 72.9(6) . . . . ?
C5B N2B C4B O3B -1.5(9) . . . . ?
C5B N2B C4B C3B 179.9(5) . . . . ?
N1B C3B C4B O3B 37.0(7) . . . . ?
N1B C3B C4B N2B -144.3(5) . . . . ?
C4B N2B C5B C6B 122.3(6) . . . . ?
C4B N2B C5B C11B -113.0(6) . . . . ?
O5B N3B C6B O4B 165.9(5) . . . . ?
C7B N3B C6B O4B 7.2(9) . . . . ?
O5B N3B C6B C5B -19.5(8) . . . . ?
C7B N3B C6B C5B -178.3(5) . . . . ?
N2B C5B C6B O4B 36.9(8) . . . . ?
C11B C5B C6B O4B -84.9(7) . . . . ?
N2B C5B C6B N3B -137.4(6) . . . . ?
C11B C5B C6B N3B 100.8(7) . . . . ?
C6B N3B C7B C8B 83.7(8) . . . . ?
O5B N3B C7B C8B -76.1(7) . . . . ?
C9B O6B C8B O7B 4.1(10) . . . . ?
C9B O6B C8B C7B -176.5(7) . . . . ?
N3B C7B C8B O7B -7.4(10) . . . . ?
N3B C7B C8B O6B 173.1(5) . . . . ?
C8B O6B C9B C10B 179.3(6) . . . . ?
N2B C5B C11B C14B -61.9(8) . . . . ?
C6B C5B C11B C14B 57.7(8) . . . . ?
N2B C5B C11B C12B 170.1(5) . . . . ?
C6B C5B C11B C12B -70.3(7) . . . . ?
C14B C11B C12B C13B 66.2(8) . . . . ?
C5B C11B C12B C13B -165.6(6) . . . . ?
