#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/23/2222314.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_2222314
loop_
_publ_author_name
'Lough, Alan J.'
'Machin, Ben P.'
'Tam, William'
_publ_section_title
;tert-Butyl
 N-hydroxy-N-[(1S*,2R*)-2-(1-naphthyl)cyclopent-3-en-1-yl]carbamate
;
_journal_coeditor_code           HB2980
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1481
_journal_paper_doi               10.1107/S1600536809020315
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H23 N O3'
_chemical_formula_moiety         'C20 H23 N O3'
_chemical_formula_sum            'C20 H23 N O3'
_chemical_formula_weight         325.39
_chemical_name_systematic
;
tert-Butyl N-hydroxy-N-[(1S*,2R*)-
2-(1-naphthyl)cyclopent-3-en-1-yl]carbamate
;
_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
_cell_angle_alpha                95.980(3)
_cell_angle_beta                 95.419(2)
_cell_angle_gamma                111.960(2)
_cell_formula_units_Z            4
_cell_length_a                   8.4710(5)
_cell_length_b                   8.4880(4)
_cell_length_c                   26.1836(12)
_cell_measurement_reflns_used    10769
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      26.3
_cell_measurement_theta_min      2.6
_cell_volume                     1718.30(15)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0765
_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       30
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            10769
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.31
_diffrn_reflns_theta_min         2.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.245
_refine_ls_extinction_coef       0.0086(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Version 6.1; Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         6622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0652P)²+0.4209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1666
_reflns_number_gt                4089
_reflns_number_total             6622
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2980.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1718.32(15)
_cod_database_code               2222314
_cod_database_fobs_code          2222314
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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 O1A 0.6043(2) 0.4234(3) 0.45322(7) 0.0357(5) Uani d . 1 . .
H H1OA 0.632(5) 0.537(5) 0.4709(13) 0.077(12) Uiso d . 1 . .
O O2A 0.1728(2) 0.2277(2) 0.39933(6) 0.0282(4) Uani d . 1 . .
O O3A 0.2995(2) 0.2761(2) 0.48346(7) 0.0330(5) Uani d . 1 . .
N N1A 0.4517(3) 0.3873(3) 0.41951(8) 0.0286(5) Uani d . 1 . .
C C1A 0.4750(3) 0.3877(3) 0.36519(10) 0.0284(6) Uani d . 1 . .
H H2 0.3603 0.3618 0.3446 0.034 Uiso calc R 1 . .
C C2A 0.5993(4) 0.5614(4) 0.35413(11) 0.0401(7) Uani d . 1 . .
H H3 0.5380 0.6363 0.3455 0.048 Uiso calc R 1 . .
H H4 0.6908 0.6217 0.3840 0.048 Uiso calc R 1 . .
C C3A 0.6710(4) 0.5081(4) 0.30832(11) 0.0417(7) Uani d . 1 . .
H H3A 0.7319 0.5847 0.2864 0.050 Uiso calc R 1 . .
C C4A 0.6395(4) 0.3422(4) 0.30201(11) 0.0396(7) Uani d . 1 . .
H H4A 0.6735 0.2855 0.2745 0.047 Uiso calc R 1 . .
C C5A 0.5439(3) 0.2528(3) 0.34302(10) 0.0297(6) Uani d . 1 . .
H H5 0.6280 0.2422 0.3705 0.036 Uiso calc R 1 . .
C C6A 0.4023(3) 0.0765(3) 0.32410(9) 0.0286(6) Uani d . 1 . .
C C7A 0.3103(4) 0.0433(4) 0.27530(10) 0.0326(7) Uani d . 1 . .
H H6 0.3390 0.1303 0.2537 0.039 Uiso calc R 1 . .
C C8A 0.1752(4) -0.1155(4) 0.25649(10) 0.0363(7) Uani d . 1 . .
H H7 0.1135 -0.1342 0.2227 0.044 Uiso calc R 1 . .
C C9A 0.1323(4) -0.2427(4) 0.28649(11) 0.0367(7) Uani d . 1 . .
H H8 0.0412 -0.3500 0.2733 0.044 Uiso calc R 1 . .
C C10A 0.2221(3) -0.2172(3) 0.33715(10) 0.0306(6) Uani d . 1 . .
C C11A 0.1782(4) -0.3471(4) 0.36895(11) 0.0372(7) Uani d . 1 . .
H H11A 0.0884 -0.4553 0.3558 0.045 Uiso calc R 1 . .
C C12A 0.2619(4) -0.3208(4) 0.41804(12) 0.0406(7) Uani d . 1 . .
H H12A 0.2302 -0.4096 0.4389 0.049 Uiso calc R 1 . .
C C13A 0.3959(4) -0.1609(4) 0.43766(11) 0.0374(7) Uani d . 1 . .
H H13A 0.4550 -0.1427 0.4718 0.045 Uiso calc R 1 . .
C C14A 0.4416(4) -0.0323(3) 0.40817(10) 0.0312(6) Uani d . 1 . .
H H14A 0.5312 0.0750 0.4223 0.037 Uiso calc R 1 . .
C C15A 0.3582(3) -0.0552(3) 0.35665(9) 0.0280(6) Uani d . 1 . .
C C16A 0.3056(3) 0.2920(3) 0.43773(10) 0.0268(6) Uani d . 1 . .
C C17A -0.0021(3) 0.1253(3) 0.40984(9) 0.0295(6) Uani d . 1 . .
C C18A -0.1061(4) 0.0807(4) 0.35615(10) 0.0396(7) Uani d . 1 . .
H H18A -0.0993 0.1866 0.3429 0.059 Uiso calc R 1 . .
H H18B -0.2264 0.0099 0.3581 0.059 Uiso calc R 1 . .
H H18C -0.0597 0.0167 0.3327 0.059 Uiso calc R 1 . .
C C19A -0.0044(4) -0.0364(3) 0.42982(11) 0.0375(7) Uani d . 1 . .
H H19A 0.0770 -0.0054 0.4619 0.056 Uiso calc R 1 . .
H H19B 0.0289 -0.1049 0.4037 0.056 Uiso calc R 1 . .
H H19C -0.1204 -0.1036 0.4367 0.056 Uiso calc R 1 . .
C C20A -0.0614(4) 0.2358(4) 0.44690(11) 0.0369(7) Uani d . 1 . .
H H20A 0.0147 0.2710 0.4802 0.055 Uiso calc R 1 . .
H H20B -0.1794 0.1694 0.4524 0.055 Uiso calc R 1 . .
H H20C -0.0576 0.3381 0.4319 0.055 Uiso calc R 1 . .
O O1B 0.4907(3) 0.6687(2) 0.05737(8) 0.0385(5) Uani d . 1 . .
H H1OB 0.557(5) 0.667(5) 0.0335(13) 0.071(12) Uiso d . 1 . .
O O2B 0.3481(2) 0.2662(2) 0.09741(6) 0.0301(4) Uani d . 1 . .
O O3B 0.3099(2) 0.3398(2) 0.01728(7) 0.0352(5) Uani d . 1 . .
N N1B 0.4828(3) 0.5352(3) 0.08597(8) 0.0306(5) Uani d . 1 . .
C C1B 0.5343(3) 0.5915(3) 0.14138(10) 0.0296(6) Uani d . 1 . .
H H10 0.5293 0.4885 0.1576 0.036 Uiso calc R 1 . .
C C2B 0.7184(4) 0.7273(4) 0.15626(11) 0.0381(7) Uani d . 1 . .
H H11 0.8036 0.6735 0.1596 0.046 Uiso calc R 1 . .
H H12 0.7483 0.8080 0.1307 0.046 Uiso calc R 1 . .
C C3B 0.7070(4) 0.8157(3) 0.20804(11) 0.0380(7) Uani d . 1 . .
H H3B 0.8040 0.8856 0.2328 0.046 Uiso calc R 1 . .
C C4B 0.5462(4) 0.7841(3) 0.21470(11) 0.0369(7) Uani d . 1 . .
H H13 0.5138 0.8284 0.2450 0.044 Uiso calc R 1 . .
C C5B 0.4195(3) 0.6695(3) 0.16871(10) 0.0310(6) Uani d . 1 . .
H H14 0.3883 0.7435 0.1457 0.037 Uiso calc R 1 . .
C C6B 0.2554(3) 0.5356(3) 0.18060(10) 0.0276(6) Uani d . 1 . .
C C7B 0.2584(4) 0.4624(4) 0.22474(10) 0.0351(7) Uani d . 1 . .
H H15 0.3642 0.4970 0.2472 0.042 Uiso calc R 1 . .
C C8B 0.1108(4) 0.3382(4) 0.23788(11) 0.0394(7) Uani d . 1 . .
H H16 0.1174 0.2898 0.2687 0.047 Uiso calc R 1 . .
C C9B -0.0427(4) 0.2871(4) 0.20617(11) 0.0404(7) Uani d . 1 . .
H H17 -0.1429 0.2046 0.2155 0.049 Uiso calc R 1 . .
C C10B -0.0543(4) 0.3553(3) 0.15974(11) 0.0349(7) Uani d . 1 . .
C C11B -0.2113(4) 0.2982(4) 0.12554(12) 0.0440(8) Uani d . 1 . .
H H11B -0.3122 0.2162 0.1348 0.053 Uiso calc R 1 . .
C C12B -0.2198(4) 0.3590(4) 0.07978(12) 0.0459(8) Uani d . 1 . .
H H12B -0.3258 0.3179 0.0571 0.055 Uiso calc R 1 . .
C C13B -0.0730(4) 0.4820(4) 0.06591(11) 0.0422(8) Uani d . 1 . .
H H13B -0.0803 0.5254 0.0341 0.051 Uiso calc R 1 . .
C C14B 0.0808(4) 0.5398(4) 0.09798(10) 0.0330(7) Uani d . 1 . .
H H14B 0.1796 0.6218 0.0877 0.040 Uiso calc R 1 . .
C C15B 0.0967(3) 0.4806(3) 0.14624(10) 0.0292(6) Uani d . 1 . .
C C16B 0.3713(3) 0.3763(3) 0.06313(10) 0.0286(6) Uani d . 1 . .
C C17B 0.2321(4) 0.0831(3) 0.08300(10) 0.0312(6) Uani d . 1 . .
C C18B 0.2446(4) 0.0185(4) 0.13454(10) 0.0426(8) Uani d . 1 . .
H H18D 0.3636 0.0327 0.1454 0.064 Uiso calc R 1 . .
H H18E 0.1692 -0.1034 0.1307 0.064 Uiso calc R 1 . .
H H18F 0.2091 0.0845 0.1608 0.064 Uiso calc R 1 . .
C C19B 0.0503(4) 0.0681(4) 0.06712(11) 0.0376(7) Uani d . 1 . .
H H19D 0.0130 0.1225 0.0958 0.056 Uiso calc R 1 . .
H H19E -0.0263 -0.0535 0.0585 0.056 Uiso calc R 1 . .
H H19F 0.0463 0.1255 0.0367 0.056 Uiso calc R 1 . .
C C20B 0.2987(4) -0.0052(4) 0.04207(11) 0.0381(7) Uani d . 1 . .
H H20D 0.4169 0.0097 0.0546 0.057 Uiso calc R 1 . .
H H20E 0.2969 0.0455 0.0102 0.057 Uiso calc R 1 . .
H H20F 0.2255 -0.1280 0.0349 0.057 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 0.0033 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
N1A O1A H1OA . . 104(2) ?
C16A O2A C17A . . 120.66(19) ?
C16A N1A O1A . . 114.3(2) ?
C16A N1A C1A . . 125.8(2) ?
O1A N1A C1A . . 113.7(2) ?
N1A C1A C2A . . 113.2(2) ?
N1A C1A C5A . . 114.6(2) ?
C2A C1A C5A . . 105.8(2) ?
N1A C1A H2 . . 107.7 ?
C2A C1A H2 . . 107.7 ?
C5A C1A H2 . . 107.7 ?
C3A C2A C1A . . 101.8(2) ?
C3A C2A H3 . . 111.4 ?
C1A C2A H3 . . 111.4 ?
C3A C2A H4 . . 111.4 ?
C1A C2A H4 . . 111.4 ?
H3 C2A H4 . . 109.3 ?
C4A C3A C2A . . 112.1(3) ?
C4A C3A H3A . . 124.0 ?
C2A C3A H3A . . 124.0 ?
C3A C4A C5A . . 112.6(2) ?
C3A C4A H4A . . 123.7 ?
C5A C4A H4A . . 123.7 ?
C4A C5A C6A . . 115.7(2) ?
C4A C5A C1A . . 100.6(2) ?
C6A C5A C1A . . 113.1(2) ?
C4A C5A H5 . . 109.0 ?
C6A C5A H5 . . 109.0 ?
C1A C5A H5 . . 109.0 ?
C7A C6A C15A . . 118.9(2) ?
C7A C6A C5A . . 119.6(2) ?
C15A C6A C5A . . 121.5(2) ?
C6A C7A C8A . . 121.9(3) ?
C6A C7A H6 . . 119.1 ?
C8A C7A H6 . . 119.1 ?
C9A C8A C7A . . 120.2(3) ?
C9A C8A H7 . . 119.9 ?
C7A C8A H7 . . 119.9 ?
C8A C9A C10A . . 120.8(3) ?
C8A C9A H8 . . 119.6 ?
C10A C9A H8 . . 119.6 ?
C11A C10A C9A . . 121.6(3) ?
C11A C10A C15A . . 119.3(2) ?
C9A C10A C15A . . 119.1(2) ?
C12A C11A C10A . . 121.4(3) ?
C12A C11A H11A . . 119.3 ?
C10A C11A H11A . . 119.3 ?
C11A C12A C13A . . 119.6(3) ?
C11A C12A H12A . . 120.2 ?
C13A C12A H12A . . 120.2 ?
C14A C13A C12A . . 120.7(3) ?
C14A C13A H13A . . 119.7 ?
C12A C13A H13A . . 119.7 ?
C13A C14A C15A . . 121.4(3) ?
C13A C14A H14A . . 119.3 ?
C15A C14A H14A . . 119.3 ?
C14A C15A C10A . . 117.6(2) ?
C14A C15A C6A . . 123.3(2) ?
C10A C15A C6A . . 119.1(2) ?
O3A C16A O2A . . 126.1(2) ?
O3A C16A N1A . . 123.3(2) ?
O2A C16A N1A . . 110.4(2) ?
O2A C17A C19A . . 109.8(2) ?
O2A C17A C18A . . 101.86(19) ?
C19A C17A C18A . . 110.2(2) ?
O2A C17A C20A . . 109.7(2) ?
C19A C17A C20A . . 113.1(2) ?
C18A C17A C20A . . 111.5(2) ?
C17A C18A H18A . . 109.5 ?
C17A C18A H18B . . 109.5 ?
H18A C18A H18B . . 109.5 ?
C17A C18A H18C . . 109.5 ?
H18A C18A H18C . . 109.5 ?
H18B C18A H18C . . 109.5 ?
C17A C19A H19A . . 109.5 ?
C17A C19A H19B . . 109.5 ?
H19A C19A H19B . . 109.5 ?
C17A C19A H19C . . 109.5 ?
H19A C19A H19C . . 109.5 ?
H19B C19A H19C . . 109.5 ?
C17A C20A H20A . . 109.5 ?
C17A C20A H20B . . 109.5 ?
H20A C20A H20B . . 109.5 ?
C17A C20A H20C . . 109.5 ?
H20A C20A H20C . . 109.5 ?
H20B C20A H20C . . 109.5 ?
N1B O1B H1OB . . 107(2) ?
C16B O2B C17B . . 121.51(19) ?
C16B N1B O1B . . 115.0(2) ?
C16B N1B C1B . . 125.7(2) ?
O1B N1B C1B . . 113.83(19) ?
N1B C1B C2B . . 114.0(2) ?
N1B C1B C5B . . 115.4(2) ?
C2B C1B C5B . . 105.2(2) ?
N1B C1B H10 . . 107.3 ?
C2B C1B H10 . . 107.3 ?
C5B C1B H10 . . 107.3 ?
C3B C2B C1B . . 101.4(2) ?
C3B C2B H11 . . 111.5 ?
C1B C2B H11 . . 111.5 ?
C3B C2B H12 . . 111.5 ?
C1B C2B H12 . . 111.5 ?
H11 C2B H12 . . 109.3 ?
C4B C3B C2B . . 111.8(3) ?
C4B C3B H3B . . 124.1 ?
C2B C3B H3B . . 124.1 ?
C3B C4B C5B . . 112.3(2) ?
C3B C4B H13 . . 123.8 ?
C5B C4B H13 . . 123.8 ?
C4B C5B C6B . . 116.6(2) ?
C4B C5B C1B . . 100.6(2) ?
C6B C5B C1B . . 113.5(2) ?
C4B C5B H14 . . 108.6 ?
C6B C5B H14 . . 108.6 ?
C1B C5B H14 . . 108.6 ?
C7B C6B C15B . . 118.8(3) ?
C7B C6B C5B . . 119.6(2) ?
C15B C6B C5B . . 121.6(2) ?
C6B C7B C8B . . 122.3(3) ?
C6B C7B H15 . . 118.9 ?
C8B C7B H15 . . 118.9 ?
C9B C8B C7B . . 119.8(3) ?
C9B C8B H16 . . 120.1 ?
C7B C8B H16 . . 120.1 ?
C8B C9B C10B . . 120.9(3) ?
C8B C9B H17 . . 119.5 ?
C10B C9B H17 . . 119.5 ?
C9B C10B C11B . . 121.4(3) ?
C9B C10B C15B . . 119.2(3) ?
C11B C10B C15B . . 119.4(3) ?
C12B C11B C10B . . 121.0(3) ?
C12B C11B H11B . . 119.5 ?
C10B C11B H11B . . 119.5 ?
C11B C12B C13B . . 120.3(3) ?
C11B C12B H12B . . 119.8 ?
C13B C12B H12B . . 119.8 ?
C14B C13B C12B . . 120.2(3) ?
C14B C13B H13B . . 119.9 ?
C12B C13B H13B . . 119.9 ?
C13B C14B C15B . . 121.8(3) ?
C13B C14B H14B . . 119.1 ?
C15B C14B H14B . . 119.1 ?
C14B C15B C10B . . 117.2(3) ?
C14B C15B C6B . . 123.6(3) ?
C10B C15B C6B . . 119.1(2) ?
O3B C16B O2B . . 125.9(2) ?
O3B C16B N1B . . 124.1(2) ?
O2B C16B N1B . . 109.9(2) ?
O2B C17B C19B . . 109.9(2) ?
O2B C17B C20B . . 110.5(2) ?
C19B C17B C20B . . 113.5(2) ?
O2B C17B C18B . . 100.9(2) ?
C19B C17B C18B . . 109.6(2) ?
C20B C17B C18B . . 111.6(2) ?
C17B C18B H18D . . 109.5 ?
C17B C18B H18E . . 109.5 ?
H18D C18B H18E . . 109.5 ?
C17B C18B H18F . . 109.5 ?
H18D C18B H18F . . 109.5 ?
H18E C18B H18F . . 109.5 ?
C17B C19B H19D . . 109.5 ?
C17B C19B H19E . . 109.5 ?
H19D C19B H19E . . 109.5 ?
C17B C19B H19F . . 109.5 ?
H19D C19B H19F . . 109.5 ?
H19E C19B H19F . . 109.5 ?
C17B C20B H20D . . 109.5 ?
C17B C20B H20E . . 109.5 ?
H20D C20B H20E . . 109.5 ?
C17B C20B H20F . . 109.5 ?
H20D C20B H20F . . 109.5 ?
H20E C20B H20F . . 109.5 ?
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
O1A N1A . 1.405(3) ?
O1A H1OA . 0.96(4) ?
O2A C16A . 1.337(3) ?
O2A C17A . 1.480(3) ?
O3A C16A . 1.223(3) ?
N1A C16A . 1.363(3) ?
N1A C1A . 1.454(3) ?
C1A C2A . 1.534(4) ?
C1A C5A . 1.554(3) ?
C1A H2 . 1.0000 ?
C2A C3A . 1.497(4) ?
C2A H3 . 0.9900 ?
C2A H4 . 0.9900 ?
C3A C4A . 1.321(4) ?
C3A H3A . 0.9500 ?
C4A C5A . 1.503(4) ?
C4A H4A . 0.9500 ?
C5A C6A . 1.521(4) ?
C5A H5 . 1.0000 ?
C6A C7A . 1.375(4) ?
C6A C15A . 1.436(4) ?
C7A C8A . 1.404(4) ?
C7A H6 . 0.9500 ?
C8A C9A . 1.361(4) ?
C8A H7 . 0.9500 ?
C9A C10A . 1.418(4) ?
C9A H8 . 0.9500 ?
C10A C11A . 1.411(4) ?
C10A C15A . 1.427(4) ?
C11A C12A . 1.362(4) ?
C11A H11A . 0.9500 ?
C12A C13A . 1.409(4) ?
C12A H12A . 0.9500 ?
C13A C14A . 1.362(4) ?
C13A H13A . 0.9500 ?
C14A C15A . 1.421(4) ?
C14A H14A . 0.9500 ?
C17A C19A . 1.513(4) ?
C17A C18A . 1.517(4) ?
C17A C20A . 1.526(3) ?
C18A H18A . 0.9800 ?
C18A H18B . 0.9800 ?
C18A H18C . 0.9800 ?
C19A H19A . 0.9800 ?
C19A H19B . 0.9800 ?
C19A H19C . 0.9800 ?
C20A H20A . 0.9800 ?
C20A H20B . 0.9800 ?
C20A H20C . 0.9800 ?
O1B N1B . 1.407(3) ?
O1B H1OB . 0.88(3) ?
O2B C16B . 1.337(3) ?
O2B C17B . 1.479(3) ?
O3B C16B . 1.222(3) ?
N1B C16B . 1.357(3) ?
N1B C1B . 1.450(3) ?
C1B C2B . 1.536(4) ?
C1B C5B . 1.553(3) ?
C1B H10 . 1.0000 ?
C2B C3B . 1.509(4) ?
C2B H11 . 0.9900 ?
C2B H12 . 0.9900 ?
C3B C4B . 1.319(4) ?
C3B H3B . 0.9500 ?
C4B C5B . 1.510(4) ?
C4B H13 . 0.9500 ?
C5B C6B . 1.515(4) ?
C5B H14 . 1.0000 ?
C6B C7B . 1.371(4) ?
C6B C15B . 1.431(4) ?
C7B C8B . 1.402(4) ?
C7B H15 . 0.9500 ?
C8B C9B . 1.366(4) ?
C8B H16 . 0.9500 ?
C9B C10B . 1.410(4) ?
C9B H17 . 0.9500 ?
C10B C11B . 1.417(4) ?
C10B C15B . 1.428(4) ?
C11B C12B . 1.359(4) ?
C11B H11B . 0.9500 ?
C12B C13B . 1.400(4) ?
C12B H12B . 0.9500 ?
C13B C14B . 1.369(4) ?
C13B H13B . 0.9500 ?
C14B C15B . 1.421(4) ?
C14B H14B . 0.9500 ?
C17B C19B . 1.511(4) ?
C17B C20B . 1.514(3) ?
C17B C18B . 1.518(4) ?
C18B H18D . 0.9800 ?
C18B H18E . 0.9800 ?
C18B H18F . 0.9800 ?
C19B H19D . 0.9800 ?
C19B H19E . 0.9800 ?
C19B H19F . 0.9800 ?
C20B H20D . 0.9800 ?
C20B H20E . 0.9800 ?
C20B H20F . 0.9800 ?
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
O1A H1OA O3A 2_666 0.96(4) 1.75(4) 2.689(3) 165(3)
O1B H1OB O3B 2_665 0.88(3) 1.84(4) 2.714(3) 179(4)
