#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/32/4023256.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_4023256
loop_
_publ_author_name
'Christopher J. MacNevin'
'Rhonda L. Moore'
'Dennis C. Liotta'
_publ_section_title
;
 Stereoselective Synthesis of Quaternary Center Bearing Azetines
 and Their β-Amino Acid Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1264
_journal_page_last               1269
_journal_paper_doi               10.1021/jo7018202
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C33.5 H40.5 N3.5 O3.5'
_chemical_formula_weight         548.19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 102.648(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5010(4)
_cell_length_b                   21.4606(9)
_cell_length_c                   12.8318(5)
_cell_measurement_reflns_used    5645
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      65.84
_cell_measurement_theta_min      3.53
_cell_volume                     3090.3(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.881
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15046
_diffrn_reflns_theta_full        66.14
_diffrn_reflns_theta_max         66.14
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  0.8626
_exptl_absorpt_correction_T_min  0.8196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10, Sheldrick 2003'
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(13)
_refine_ls_extinction_coef       0.00220(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1024
_refine_ls_number_reflns         7842
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0517P)²+0.4898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0815
_reflns_number_gt                7687
_reflns_number_total             7842
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7018202-File003.cif
_cod_data_source_block           A2304
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C33.50 H40.50 N3.50 O3.50'
_cod_database_code               4023256
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.01908(16) 1.05043(9) 0.83151(15) 0.0430(4) Uani 1 1 d . . .
N2A N 0.12394(13) 0.99047(8) 0.95948(12) 0.0283(3) Uani 1 1 d . . .
N3A N 0.19397(13) 0.83693(8) 0.96377(13) 0.0259(3) Uani 1 1 d . . .
N1B N 0.60508(15) 0.73482(9) 0.29582(13) 0.0396(4) Uani 1 1 d . . .
N2B N 0.69424(13) 0.76874(8) 0.45767(12) 0.0293(3) Uani 1 1 d . . .
N3B N 0.98633(13) 0.78703(7) 0.56931(13) 0.0279(3) Uani 1 1 d . A .
O1A O 0.16372(12) 0.98946(7) 0.78685(11) 0.0371(3) Uani 1 1 d . . .
O2A O 0.20756(12) 0.95546(7) 1.12253(10) 0.0384(3) Uani 1 1 d . . .
O3A O 0.07263(12) 0.81602(7) 0.80508(11) 0.0382(3) Uani 1 1 d . . .
O1B O 0.72898(13) 0.81841(8) 0.30296(10) 0.0421(4) Uani 1 1 d . . .
O2B O 0.68606(14) 0.80572(7) 0.61882(11) 0.0404(3) Uani 1 1 d . . .
O3B O 0.97045(14) 0.71740(7) 0.43373(12) 0.0435(4) Uani 1 1 d . A .
C1A C 0.10910(16) 1.00867(9) 0.85149(16) 0.0319(4) Uani 1 1 d . . .
C2A C -0.0068(3) 1.08475(16) 0.7312(3) 0.0630(8) Uani 1 1 d . . .
C3A C -0.0141(2) 1.07230(11) 0.9291(2) 0.0465(6) Uani 1 1 d . . .
C4A C -0.1441(3) 1.09110(15) 0.9149(3) 0.0640(8) Uani 1 1 d . . .
C5A C 0.02681(17) 1.01745(10) 1.00514(18) 0.0345(4) Uani 1 1 d . . .
C6A C -0.06928(16) 0.96980(9) 1.01102(15) 0.0305(4) Uani 1 1 d . . .
C7A C -0.11646(18) 0.93133(10) 0.92557(17) 0.0363(4) Uani 1 1 d . . .
C8A C -0.20983(19) 0.89132(11) 0.9296(2) 0.0439(5) Uani 1 1 d . . .
C9A C -0.25620(19) 0.88848(11) 1.0203(2) 0.0476(6) Uani 1 1 d . . .
C10A C -0.2085(2) 0.92578(13) 1.1064(2) 0.0512(6) Uani 1 1 d . . .
C11A C -0.11617(19) 0.96675(12) 1.10174(18) 0.0407(5) Uani 1 1 d . . .
C12A C 0.21652(15) 0.95965(9) 1.02964(15) 0.0279(4) Uani 1 1 d . . .
C13A C 0.32383(15) 0.92972(9) 0.99394(14) 0.0256(4) Uani 1 1 d . . .
C14A C 0.39957(16) 0.97500(9) 0.94101(16) 0.0283(4) Uani 1 1 d . . .
C15A C 0.45318(19) 1.03234(10) 1.00480(19) 0.0393(5) Uani 1 1 d . . .
C16A C 0.5576(2) 1.05620(13) 0.9608(3) 0.0594(7) Uani 1 1 d . . .
C17A C 0.3622(3) 1.08463(12) 0.9991(3) 0.0565(7) Uani 1 1 d . . .
C18A C 0.40711(17) 0.90336(10) 1.09495(16) 0.0312(4) Uani 1 1 d . . .
C19A C 0.27119(15) 0.87617(9) 0.91489(14) 0.0251(4) Uani 1 1 d . . .
C20A C 0.09553(15) 0.81123(9) 0.90343(15) 0.0279(4) Uani 1 1 d . . .
C21A C 0.01215(16) 0.77830(9) 0.96021(16) 0.0313(4) Uani 1 1 d . . .
C22A C 0.01227(18) 0.78920(11) 1.06700(18) 0.0391(5) Uani 1 1 d . . .
C23A C -0.0710(2) 0.75992(12) 1.1139(2) 0.0490(6) Uani 1 1 d . . .
C24A C -0.1551(2) 0.72070(11) 1.0534(2) 0.0532(7) Uani 1 1 d . . .
C25A C -0.1564(2) 0.71027(11) 0.9470(2) 0.0506(6) Uani 1 1 d . . .
C26A C -0.07288(18) 0.73903(10) 0.9002(2) 0.0420(5) Uani 1 1 d . . .
C27A C 0.36507(15) 0.83906(9) 0.87504(14) 0.0260(4) Uani 1 1 d . . .
C28A C 0.39769(18) 0.85734(10) 0.78132(16) 0.0336(4) Uani 1 1 d . . .
C29A C 0.48670(18) 0.82650(11) 0.74518(16) 0.0383(5) Uani 1 1 d . . .
C30A C 0.54461(18) 0.77649(11) 0.80101(17) 0.0401(5) Uani 1 1 d . . .
C31A C 0.51063(19) 0.75698(11) 0.89245(19) 0.0412(5) Uani 1 1 d . . .
C32A C 0.42140(17) 0.78778(10) 0.92947(16) 0.0338(4) Uani 1 1 d . . .
C1B C 0.68220(16) 0.77826(10) 0.34605(15) 0.0329(4) Uani 1 1 d . . .
C2B C 0.5737(2) 0.72928(15) 0.18077(19) 0.0482(6) Uani 1 1 d . . .
C3B C 0.58130(19) 0.68600(11) 0.36694(17) 0.0411(5) Uani 1 1 d . . .
C4B C 0.6584(3) 0.62866(13) 0.3615(2) 0.0612(7) Uani 1 1 d . . .
C5B C 0.60687(17) 0.72091(10) 0.47418(16) 0.0336(4) Uani 1 1 d . . .
C6B C 0.64508(18) 0.67846(9) 0.56966(16) 0.0328(4) Uani 1 1 d . . .
C7B C 0.5584(2) 0.65110(11) 0.61382(19) 0.0419(5) Uani 1 1 d . . .
C8B C 0.5885(3) 0.60714(12) 0.6939(2) 0.0514(6) Uani 1 1 d . . .
C9B C 0.7064(2) 0.58975(12) 0.7313(2) 0.0497(6) Uani 1 1 d . . .
C10B C 0.7938(2) 0.61851(12) 0.6900(2) 0.0465(5) Uani 1 1 d . . .
C11B C 0.7634(2) 0.66210(11) 0.60968(18) 0.0398(5) Uani 1 1 d . . .
C12B C 0.72902(16) 0.81234(9) 0.54124(15) 0.0291(4) Uani 1 1 d . . .
C13B C 0.82039(16) 0.86517(9) 0.53915(14) 0.0285(4) Uani 1 1 d . A .
C14B C 0.76326(19) 0.91989(10) 0.46679(18) 0.0368(5) Uani 1 1 d . . .
C18B C 0.85715(18) 0.88957(10) 0.65417(16) 0.0333(4) Uani 1 1 d . . .
C19B C 0.92850(15) 0.83755(9) 0.49902(15) 0.0274(4) Uani 1 1 d . . .
C20B C 1.00902(16) 0.73147(9) 0.52761(16) 0.0308(4) Uani 1 1 d . . .
C21B C 1.08355(17) 0.68573(9) 0.60349(16) 0.0328(4) Uani 1 1 d . A .
C22B C 1.06194(19) 0.62265(10) 0.5842(2) 0.0414(5) Uani 1 1 d . . .
C23B C 1.1278(2) 0.57837(12) 0.6515(2) 0.0519(6) Uani 1 1 d . A .
C24B C 1.2180(2) 0.59689(12) 0.7354(2) 0.0569(7) Uani 1 1 d . . .
C25B C 1.2411(2) 0.65963(13) 0.7529(2) 0.0566(7) Uani 1 1 d . A .
C26B C 1.17401(19) 0.70449(11) 0.68794(19) 0.0410(5) Uani 1 1 d . . .
C27B C 1.02025(16) 0.88574(9) 0.48189(15) 0.0298(4) Uani 1 1 d . A .
C28B C 1.02667(18) 0.90077(11) 0.37729(16) 0.0366(5) Uani 1 1 d . . .
C29B C 1.1113(2) 0.94252(12) 0.35774(18) 0.0448(5) Uani 1 1 d . A .
C30B C 1.19066(19) 0.97045(11) 0.44243(19) 0.0449(5) Uani 1 1 d . . .
C31B C 1.18514(19) 0.95577(11) 0.54616(19) 0.0404(5) Uani 1 1 d . A .
C32B C 1.10134(18) 0.91328(10) 0.56602(17) 0.0339(4) Uani 1 1 d . . .
C16C C 0.6416(2) 0.94241(13) 0.4829(2) 0.0596(7) Uani 0.50 1 d P A 1
H16C H 0.6347 0.9159 0.5454 0.072 Uiso 0.50 1 d PR A 1
C17C C 0.6493(7) 1.0083(4) 0.5374(6) 0.0764(13) Uiso 0.50 1 d P A 1
H17A H 0.6839 1.0381 0.4949 0.115 Uiso 0.50 1 d PR A 1
H17B H 0.6996 1.0059 0.6096 0.115 Uiso 0.50 1 d PR A 1
H17C H 0.5692 1.0220 0.5414 0.115 Uiso 0.50 1 d PR A 1
C18C C 0.5414(6) 0.9212(4) 0.4088(6) 0.0755(12) Uiso 0.50 1 d P A 1
H18A H 0.5441 0.9377 0.3381 0.113 Uiso 0.50 1 d PR A 1
H18B H 0.4689 0.9359 0.4293 0.113 Uiso 0.50 1 d PR A 1
H18C H 0.5413 0.8756 0.4065 0.113 Uiso 0.50 1 d PR A 1
C16D C 0.6416(2) 0.94241(13) 0.4829(2) 0.0596(7) Uani 0.50 1 d P A 2
H16D H 0.6096 0.9194 0.5386 0.072 Uiso 0.50 1 d PR A 2
C17D C 0.6443(7) 1.0173(4) 0.4941(6) 0.0764(13) Uiso 0.50 1 d P A 2
H17D H 0.7097 1.0294 0.5533 0.115 Uiso 0.50 1 d PR A 2
H17E H 0.5685 1.0319 0.5083 0.115 Uiso 0.50 1 d PR A 2
H17F H 0.6564 1.0361 0.4277 0.115 Uiso 0.50 1 d PR A 2
C18D C 0.5548(6) 0.9479(4) 0.3705(5) 0.0755(12) Uiso 0.50 1 d P A 2
H18D H 0.5828 0.9805 0.3286 0.113 Uiso 0.50 1 d PR A 2
H18E H 0.4746 0.9582 0.3794 0.113 Uiso 0.50 1 d PR A 2
H18F H 0.5527 0.9079 0.3332 0.113 Uiso 0.50 1 d PR A 2
H1 H -0.085(3) 1.0892(17) 0.704(3) 0.081(10) Uiso 1 1 d . . .
H2 H 0.034(3) 1.0634(17) 0.678(3) 0.080(10) Uiso 1 1 d . . .
H3 H 0.024(3) 1.1269(19) 0.743(3) 0.090(11) Uiso 1 1 d . . .
H4 H 0.042(3) 1.1075(14) 0.955(2) 0.055(7) Uiso 1 1 d . . .
H5 H -0.194(2) 1.0563(13) 0.8729(19) 0.048(7) Uiso 1 1 d . . .
H6 H -0.160(3) 1.133(2) 0.864(3) 0.102(12) Uiso 1 1 d . . .
H7 H -0.160(3) 1.0995(15) 0.995(3) 0.074(9) Uiso 1 1 d . . .
H8 H 0.060(2) 1.0321(14) 1.075(2) 0.052(7) Uiso 1 1 d . . .
H9 H -0.0842(19) 0.9297(10) 0.8624(17) 0.032(5) Uiso 1 1 d . . .
H10 H -0.252(3) 0.8607(15) 0.867(2) 0.064(8) Uiso 1 1 d . . .
H11 H -0.325(3) 0.8586(14) 1.031(2) 0.059(8) Uiso 1 1 d . . .
H12 H -0.242(2) 0.9261(13) 1.168(2) 0.056(7) Uiso 1 1 d . . .
H13 H -0.083(2) 0.9919(12) 1.162(2) 0.040(6) Uiso 1 1 d . . .
H14 H 0.355(2) 0.9877(11) 0.8705(19) 0.034(6) Uiso 1 1 d . . .
H15 H 0.4630(19) 0.9508(10) 0.9244(15) 0.028(5) Uiso 1 1 d . . .
H16 H 0.488(3) 1.0181(18) 1.073(3) 0.088(11) Uiso 1 1 d . . .
H17 H 0.297(3) 1.0687(14) 1.037(2) 0.061(8) Uiso 1 1 d . . .
H18 H 0.399(3) 1.1199(19) 1.033(3) 0.086(11) Uiso 1 1 d . . .
H19 H 0.328(3) 1.0987(19) 0.913(3) 0.097(12) Uiso 1 1 d . . .
H20 H 0.597(3) 1.0937(17) 1.000(3) 0.075(10) Uiso 1 1 d . . .
H21 H 0.526(3) 1.0627(19) 0.877(3) 0.098(12) Uiso 1 1 d . . .
H22 H 0.616(3) 1.0266(14) 0.968(2) 0.058(8) Uiso 1 1 d . . .
H23 H 0.366(2) 0.8716(12) 1.1253(18) 0.042(6) Uiso 1 1 d . . .
H24 H 0.432(2) 0.9366(13) 1.1488(19) 0.044(6) Uiso 1 1 d . . .
H25 H 0.477(2) 0.8895(11) 1.0713(17) 0.032(5) Uiso 1 1 d . . .
H26 H 0.2183(19) 0.8951(10) 0.8563(17) 0.029(5) Uiso 1 1 d . . .
H27 H 0.2128(18) 0.8259(11) 1.0314(19) 0.030(6) Uiso 1 1 d . . .
H28 H 0.073(2) 0.8171(11) 1.1088(17) 0.034(6) Uiso 1 1 d . . .
H29 H -0.068(2) 0.7657(13) 1.188(2) 0.051(7) Uiso 1 1 d . . .
H30 H -0.207(3) 0.7017(16) 1.095(2) 0.073(9) Uiso 1 1 d . . .
H31 H -0.214(3) 0.6844(14) 0.905(2) 0.055(7) Uiso 1 1 d . . .
H32 H -0.074(2) 0.7362(12) 0.819(2) 0.046(7) Uiso 1 1 d . . .
H33 H 0.359(2) 0.8913(12) 0.7417(18) 0.037(6) Uiso 1 1 d . . .
H34 H 0.507(2) 0.8390(11) 0.6770(19) 0.040(6) Uiso 1 1 d . . .
H35 H 0.613(2) 0.7552(11) 0.7797(17) 0.036(6) Uiso 1 1 d . . .
H36 H 0.548(2) 0.7213(13) 0.9321(19) 0.045(6) Uiso 1 1 d . . .
H37 H 0.395(2) 0.7713(12) 0.9939(19) 0.041(6) Uiso 1 1 d . . .
H38 H 0.622(3) 0.6926(15) 0.158(2) 0.065(8) Uiso 1 1 d . . .
H39 H 0.592(3) 0.7652(16) 0.154(2) 0.064(9) Uiso 1 1 d . . .
H40 H 0.484(3) 0.7221(14) 0.154(2) 0.062(8) Uiso 1 1 d . . .
H41 H 0.492(2) 0.6751(12) 0.3490(19) 0.046(7) Uiso 1 1 d . . .
H42 H 0.643(3) 0.6105(15) 0.283(3) 0.070(9) Uiso 1 1 d . . .
H43 H 0.632(3) 0.5967(17) 0.418(3) 0.083(10) Uiso 1 1 d . . .
H44 H 0.750(4) 0.647(2) 0.378(3) 0.107(13) Uiso 1 1 d . . .
H45 H 0.534(2) 0.7450(13) 0.4813(19) 0.048(7) Uiso 1 1 d . . .
H46 H 0.478(3) 0.6658(14) 0.591(2) 0.055(7) Uiso 1 1 d . . .
H47 H 0.531(2) 0.5902(13) 0.724(2) 0.048(7) Uiso 1 1 d . . .
H48 H 0.729(3) 0.5585(15) 0.790(2) 0.062(8) Uiso 1 1 d . . .
H49 H 0.875(3) 0.6098(13) 0.718(2) 0.056(8) Uiso 1 1 d . . .
H50 H 0.832(3) 0.6791(14) 0.583(2) 0.059(8) Uiso 1 1 d . . .
H51 H 0.761(2) 0.9099(12) 0.391(2) 0.044(6) Uiso 1 1 d . . .
H52 H 0.820(2) 0.9568(12) 0.4843(17) 0.042(6) Uiso 1 1 d . . .
H53 H 0.790(2) 0.9040(12) 0.6750(18) 0.040(6) Uiso 1 1 d . . .
H54 H 0.915(2) 0.9224(12) 0.6519(18) 0.041(6) Uiso 1 1 d . . .
H55 H 0.893(2) 0.8586(12) 0.7085(18) 0.038(6) Uiso 1 1 d . . .
H56 H 0.8983(17) 0.8189(10) 0.4284(16) 0.023(5) Uiso 1 1 d . . .
H57 H 1.006(2) 0.7938(11) 0.637(2) 0.034(6) Uiso 1 1 d . . .
H58 H 1.004(2) 0.6093(11) 0.5236(19) 0.036(6) Uiso 1 1 d . . .
H59 H 1.104(3) 0.5360(16) 0.635(2) 0.069(9) Uiso 1 1 d . . .
H60 H 1.266(3) 0.5654(16) 0.777(2) 0.070(9) Uiso 1 1 d . . .
H61 H 1.310(3) 0.6711(16) 0.811(3) 0.078(10) Uiso 1 1 d . . .
H62 H 1.190(2) 0.7481(15) 0.702(2) 0.057(7) Uiso 1 1 d . . .
H63 H 0.966(2) 0.8855(11) 0.3213(19) 0.039(6) Uiso 1 1 d . . .
H64 H 1.119(2) 0.9512(13) 0.284(2) 0.048(7) Uiso 1 1 d . . .
H65 H 1.250(2) 1.0021(13) 0.426(2) 0.052(7) Uiso 1 1 d . . .
H66 H 1.238(2) 0.9763(12) 0.601(2) 0.043(6) Uiso 1 1 d . . .
H67 H 1.1010(19) 0.9034(11) 0.6408(18) 0.034(6) Uiso 1 1 d . . .
C1S C 0.2927(2) 0.79975(14) 0.4683(2) 0.0516(6) Uani 1 1 d . . .
C2S C 0.2398(3) 0.70452(14) 0.3593(3) 0.0574(7) Uani 1 1 d . . .
C3S C 0.3011(2) 0.79804(12) 0.28028(19) 0.0459(5) Uani 1 1 d . . .
N1S N 0.28347(15) 0.76834(9) 0.36699(14) 0.0414(4) Uani 1 1 d . . .
O1S O 0.28932(15) 0.77514(9) 0.19062(13) 0.0523(4) Uani 1 1 d . . .
H1S H 0.210(3) 0.8045(15) 0.480(2) 0.071(9) Uiso 1 1 d . . .
H2S H 0.332(3) 0.8402(19) 0.458(3) 0.093(11) Uiso 1 1 d . . .
H3S H 0.364(3) 0.7798(17) 0.534(3) 0.091(11) Uiso 1 1 d . . .
H4S H 0.279(4) 0.684(2) 0.425(3) 0.104(14) Uiso 1 1 d . . .
H5S H 0.157(4) 0.7084(19) 0.359(3) 0.107(13) Uiso 1 1 d . . .
H6S H 0.250(3) 0.6897(15) 0.285(3) 0.073(9) Uiso 1 1 d . . .
H7S H 0.329(3) 0.8428(16) 0.299(2) 0.068(9) Uiso 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A N1A C2A 120.2(2) . . ?
C1A N1A C3A 112.51(18) . . ?
C2A N1A C3A 123.5(2) . . ?
C12A N2A C1A 132.23(15) . . ?
C12A N2A C5A 117.48(16) . . ?
C1A N2A C5A 109.80(15) . . ?
C20A N3A C19A 120.29(16) . . ?
C1B N1B C2B 122.4(2) . . ?
C1B N1B C3B 113.10(16) . . ?
C2B N1B C3B 122.9(2) . . ?
C12B N2B C1B 128.12(17) . . ?
C12B N2B C5B 115.96(15) . . ?
C1B N2B C5B 108.87(15) . . ?
C20B N3B C19B 120.40(16) . . ?
O1A C1A N1A 125.74(19) . . ?
O1A C1A N2A 127.23(17) . . ?
N1A C1A N2A 107.00(17) . . ?
N1A C3A C4A 114.6(2) . . ?
N1A C3A C5A 101.35(17) . . ?
C4A C3A C5A 115.9(2) . . ?
N2A C5A C6A 112.01(17) . . ?
N2A C5A C3A 101.54(16) . . ?
C6A C5A C3A 114.99(16) . . ?
C7A C6A C11A 118.64(19) . . ?
C7A C6A C5A 121.66(17) . . ?
C11A C6A C5A 119.60(19) . . ?
C6A C7A C8A 120.86(19) . . ?
C9A C8A C7A 120.2(2) . . ?
C10A C9A C8A 119.3(2) . . ?
C9A C10A C11A 120.5(2) . . ?
C6A C11A C10A 120.4(2) . . ?
O2A C12A N2A 116.55(17) . . ?
O2A C12A C13A 120.10(17) . . ?
N2A C12A C13A 123.32(16) . . ?
C18A C13A C12A 107.01(15) . . ?
C18A C13A C14A 106.98(15) . . ?
C12A C13A C14A 115.39(15) . . ?
C18A C13A C19A 110.91(15) . . ?
C12A C13A C19A 106.05(13) . . ?
C14A C13A C19A 110.48(14) . . ?
C15A C14A C13A 117.83(17) . . ?
C16A C15A C17A 108.8(2) . . ?
C16A C15A C14A 109.3(2) . . ?
C17A C15A C14A 111.97(19) . . ?
N3A C19A C27A 112.74(15) . . ?
N3A C19A C13A 109.29(14) . . ?
C27A C19A C13A 113.64(14) . . ?
O3A C20A N3A 121.27(17) . . ?
O3A C20A C21A 121.25(16) . . ?
N3A C20A C21A 117.45(16) . . ?
C26A C21A C22A 119.8(2) . . ?
C26A C21A C20A 117.57(19) . . ?
C22A C21A C20A 122.44(17) . . ?
C23A C22A C21A 120.0(2) . . ?
C24A C23A C22A 119.7(2) . . ?
C25A C24A C23A 120.6(2) . . ?
C24A C25A C26A 119.9(2) . . ?
C25A C26A C21A 120.0(2) . . ?
C32A C27A C28A 118.32(17) . . ?
C32A C27A C19A 122.37(16) . . ?
C28A C27A C19A 119.31(17) . . ?
C29A C28A C27A 120.97(19) . . ?
C30A C29A C28A 120.51(19) . . ?
C29A C30A C31A 118.91(19) . . ?
C30A C31A C32A 121.0(2) . . ?
C27A C32A C31A 120.29(19) . . ?
O1B C1B N1B 125.77(19) . . ?
O1B C1B N2B 127.33(19) . . ?
N1B C1B N2B 106.87(17) . . ?
N1B C3B C4B 111.2(2) . . ?
N1B C3B C5B 100.67(18) . . ?
C4B C3B C5B 115.7(2) . . ?
N2B C5B C6B 116.52(15) . . ?
N2B C5B C3B 102.25(15) . . ?
C6B C5B C3B 113.33(18) . . ?
C7B C6B C11B 118.5(2) . . ?
C7B C6B C5B 118.72(19) . . ?
C11B C6B C5B 122.59(17) . . ?
C6B C7B C8B 120.6(2) . . ?
C7B C8B C9B 120.5(2) . . ?
C10B C9B C8B 119.1(2) . . ?
C11B C10B C9B 120.2(2) . . ?
C10B C11B C6B 121.0(2) . . ?
O2B C12B N2B 116.53(17) . . ?
O2B C12B C13B 119.97(17) . . ?
N2B C12B C13B 123.47(15) . . ?
C18B C13B C12B 106.13(15) . . ?
C18B C13B C14B 107.96(17) . . ?
C12B C13B C14B 111.36(15) . . ?
C18B C13B C19B 112.00(15) . . ?
C12B C13B C19B 108.64(15) . . ?
C14B C13B C19B 110.68(15) . . ?
C16C C14B C13B 115.87(17) . . ?
N3B C19B C27B 110.67(14) . . ?
N3B C19B C13B 111.26(14) . . ?
C27B C19B C13B 114.53(16) . . ?
O3B C20B N3B 123.00(19) . . ?
O3B C20B C21B 120.34(18) . . ?
N3B C20B C21B 116.64(17) . . ?
C26B C21B C22B 119.7(2) . . ?
C26B C21B C20B 122.51(19) . . ?
C22B C21B C20B 117.70(19) . . ?
C21B C22B C23B 120.2(2) . . ?
C24B C23B C22B 120.1(2) . . ?
C23B C24B C25B 119.5(2) . . ?
C24B C25B C26B 121.0(2) . . ?
C21B C26B C25B 119.3(2) . . ?
C32B C27B C28B 118.60(19) . . ?
C32B C27B C19B 122.80(17) . . ?
C28B C27B C19B 118.54(18) . . ?
C29B C28B C27B 120.7(2) . . ?
C28B C29B C30B 120.2(2) . . ?
C31B C30B C29B 119.5(2) . . ?
C30B C31B C32B 120.4(2) . . ?
C31B C32B C27B 120.61(19) . . ?
C18C C16C C14B 116.4(4) . . ?
C18C C16C C17C 123.6(5) . . ?
C14B C16C C17C 112.2(3) . . ?
O1S C3S N1S 125.6(2) . . ?
C3S N1S C1S 122.1(2) . . ?
C3S N1S C2S 120.4(2) . . ?
C1S N1S C2S 117.1(2) . . ?
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
N1A C1A 1.351(3) . ?
N1A C2A 1.456(3) . ?
N1A C3A 1.464(3) . ?
N2A C12A 1.401(2) . ?
N2A C1A 1.414(3) . ?
N2A C5A 1.488(2) . ?
N3A C20A 1.342(2) . ?
N3A C19A 1.461(2) . ?
N1B C1B 1.350(3) . ?
N1B C2B 1.446(3) . ?
N1B C3B 1.454(3) . ?
N2B C12B 1.413(3) . ?
N2B C1B 1.423(3) . ?
N2B C5B 1.484(2) . ?
N3B C20B 1.356(3) . ?
N3B C19B 1.473(2) . ?
O1A C1A 1.217(2) . ?
O2A C12A 1.222(2) . ?
O3A C20A 1.236(2) . ?
O1B C1B 1.211(3) . ?
O2B C12B 1.213(2) . ?
O3B C20B 1.227(2) . ?
C3A C4A 1.520(3) . ?
C3A C5A 1.536(3) . ?
C5A C6A 1.520(3) . ?
C6A C7A 1.385(3) . ?
C6A C11A 1.388(3) . ?
C7A C8A 1.385(3) . ?
C8A C9A 1.384(3) . ?
C9A C10A 1.377(4) . ?
C10A C11A 1.390(4) . ?
C12A C13A 1.547(2) . ?
C13A C18A 1.541(3) . ?
C13A C14A 1.557(2) . ?
C13A C19A 1.564(3) . ?
C14A C15A 1.531(3) . ?
C15A C16A 1.524(3) . ?
C15A C17A 1.525(3) . ?
C19A C27A 1.518(2) . ?
C20A C21A 1.502(3) . ?
C21A C26A 1.389(3) . ?
C21A C22A 1.390(3) . ?
C22A C23A 1.388(3) . ?
C23A C24A 1.384(4) . ?
C24A C25A 1.380(4) . ?
C25A C26A 1.385(3) . ?
C27A C32A 1.386(3) . ?
C27A C28A 1.392(3) . ?
C28A C29A 1.382(3) . ?
C29A C30A 1.378(3) . ?
C30A C31A 1.380(3) . ?
C31A C32A 1.389(3) . ?
C3B C4B 1.527(4) . ?
C3B C5B 1.538(3) . ?
C5B C6B 1.513(3) . ?
C6B C7B 1.381(3) . ?
C6B C11B 1.390(3) . ?
C7B C8B 1.382(4) . ?
C8B C9B 1.387(4) . ?
C9B C10B 1.381(4) . ?
C10B C11B 1.379(3) . ?
C12B C13B 1.550(3) . ?
C13B C18B 1.536(3) . ?
C13B C14B 1.551(3) . ?
C13B C19B 1.563(2) . ?
C14B C16C 1.537(3) . ?
C19B C27B 1.527(3) . ?
C20B C21B 1.510(3) . ?
C21B C26B 1.387(3) . ?
C21B C22B 1.389(3) . ?
C22B C23B 1.391(3) . ?
C23B C24B 1.380(4) . ?
C24B C25B 1.381(4) . ?
C25B C26B 1.391(3) . ?
C27B C32B 1.394(3) . ?
C27B C28B 1.398(3) . ?
C28B C29B 1.386(3) . ?
C29B C30B 1.392(3) . ?
C30B C31B 1.383(3) . ?
C31B C32B 1.390(3) . ?
C16C C18C 1.400(8) . ?
C16C C17C 1.571(8) . ?
C1S N1S 1.448(3) . ?
C2S N1S 1.455(3) . ?
C3S O1S 1.231(3) . ?
C3S N1S 1.335(3) . ?
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
N3A H27 O1S 0.88(2) 2.31(2) 3.168(2) 164(2) 1_556
N3B H57 O3A 0.86(2) 2.18(3) 3.035(2) 174(2) 1_655
