# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3a-JG-SArN3-Mo-123K
_database_code_depnum_ccdc_archive 'CCDC 2225278'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-12-09 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
2R,3S,4S,6S)-4-azido-3-(benzyloxy)-2-((benzyloxy)methyl)-6-(p-tolyl)tetrahydro-2H-pyran
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H29 N3 O3'
_chemical_formula_sum            'C27 H29 N3 O3'
_chemical_formula_weight         443.53

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.8747(2)
_cell_length_b                   10.5771(4)
_cell_length_c                   44.7202(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2305.78(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9625
_cell_measurement_theta_min      2.1430
_cell_measurement_theta_max      27.9290

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.027
_exptl_absorpt_coefficient_mu    0.084
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 2 -1 0.0234
-2 0 5 0.0761
0 -5 3 0.0308
2 0 -5 0.0592
0 0 -1 0.0183
0 0 1 0.0083
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.75a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      123(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            25032
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         2.130
_diffrn_reflns_theta_max         25.341
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4183
_reflns_number_gt                3483
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.992

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²+0.2843P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.7(6)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4181
_refine_ls_number_parameters     336
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.0948
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.5741(5) 0.3823(2) 0.35229(5) 0.0303(6) Uani 1 1 d . . . . .
H1 H 0.436667 0.416148 0.366844 0.036 Uiso 1 1 calc R U . . .
C2 C 0.6742(5) 0.2575(2) 0.36537(5) 0.0294(6) Uani 1 1 d . . . . .
H2 H 0.798204 0.274491 0.382717 0.035 Uiso 1 1 calc R U . . .
C3 C 0.8272(5) 0.1798(2) 0.34190(5) 0.0318(6) Uani 1 1 d . . . . .
H3 H 0.996695 0.227805 0.336460 0.038 Uiso 1 1 calc R U . . .
C4 C 0.6558(5) 0.1668(2) 0.31363(6) 0.0333(6) Uani 1 1 d . . . . .
H4A H 0.761827 0.120798 0.298196 0.040 Uiso 1 1 calc R U . . .
H4B H 0.487784 0.117577 0.318020 0.040 Uiso 1 1 calc R U . . .
C5 C 0.5778(5) 0.2966(2) 0.30201(5) 0.0287(6) Uani 1 1 d . . . . .
H5 H 0.749515 0.344045 0.297125 0.034 Uiso 1 1 calc R U . . .
O6 O 0.4289(3) 0.36568(16) 0.32461(3) 0.0307(4) Uani 1 1 d . . . . .
C7 C 0.7948(6) 0.4833(2) 0.34959(5) 0.0324(6) Uani 1 1 d . . . . .
H7A H 0.945180 0.453844 0.336448 0.039 Uiso 1 1 calc R U . . .
H7B H 0.717054 0.561970 0.341091 0.039 Uiso 1 1 calc R U . . .
O8 O 0.4477(3) 0.18288(17) 0.37497(4) 0.0362(4) Uani 1 1 d . . . . .
N9 N 0.9155(5) 0.0562(2) 0.35403(5) 0.0420(6) Uani 1 1 d . . . . .
C10 C 0.3947(5) 0.2955(2) 0.27457(5) 0.0305(6) Uani 1 1 d . . . . .
C11 C 0.3761(6) 0.1901(3) 0.25601(6) 0.0402(7) Uani 1 1 d . . . . .
H11 H 0.479340 0.116379 0.260587 0.048 Uiso 1 1 calc R U . . .
C12 C 0.2076(6) 0.1914(3) 0.23079(6) 0.0456(7) Uani 1 1 d . . . . .
H12 H 0.199370 0.118606 0.218395 0.055 Uiso 1 1 calc R U . . .
C13 C 0.0534(6) 0.2957(3) 0.22346(5) 0.0379(7) Uani 1 1 d . . . . .
C14 C 0.0755(6) 0.4009(3) 0.24169(6) 0.0386(7) Uani 1 1 d . . . . .
H14 H -0.026102 0.474834 0.236938 0.046 Uiso 1 1 calc R U . . .
C15 C 0.2434(6) 0.4006(3) 0.26683(6) 0.0353(6) Uani 1 1 d . . . . .
H15 H 0.253957 0.474309 0.278910 0.042 Uiso 1 1 calc R U . . .
C16 C -0.1365(6) 0.2959(3) 0.19651(6) 0.0525(8) Uani 1 1 d . . . . .
H16A H -0.128295 0.213455 0.186570 0.079 Uiso 1 1 calc R U . . .
H16B H -0.078800 0.362038 0.182507 0.079 Uiso 1 1 calc R U . . .
H16C H -0.324888 0.312475 0.203089 0.079 Uiso 1 1 calc R U . . .
O17 O 0.8937(4) 0.50499(16) 0.37910(4) 0.0371(4) Uani 1 1 d . . . . .
C18 C 1.0445(6) 0.6195(3) 0.38227(6) 0.0397(7) Uani 1 1 d . . . . .
H18A H 0.928406 0.692300 0.376463 0.048 Uiso 1 1 calc R U . . .
H18B H 1.207282 0.617984 0.369041 0.048 Uiso 1 1 calc R U . . .
C20 C 0.3602(5) 0.2101(3) 0.40502(6) 0.0430(7) Uani 1 1 d . . . . .
H20A H 0.187331 0.164072 0.409097 0.052 Uiso 1 1 calc R U . . .
H20B H 0.321744 0.301702 0.406777 0.052 Uiso 1 1 calc R U . . .
C21 C 0.5704(6) 0.1735(3) 0.42818(6) 0.0404(7) Uani 1 1 d . . . . .
C19 C 1.1328(5) 0.6329(2) 0.41422(6) 0.0336(6) Uani 1 1 d D . . . .
C22 C 1.2446(12) 0.7479(5) 0.42345(11) 0.0421(16) Uani 0.543(5) 1 d D . P A 1
H22 H 1.267212 0.814734 0.409468 0.051 Uiso 0.543(5) 1 calc R U P A 1
C23 C 1.3229(13) 0.7650(6) 0.45310(11) 0.0468(17) Uani 0.543(5) 1 d D . P A 1
H23 H 1.391932 0.844168 0.459705 0.056 Uiso 0.543(5) 1 calc R U P A 1
C22B C 1.3881(14) 0.6716(7) 0.42136(14) 0.0407(17) Uani 0.457(5) 1 d D . P A 2
H22B H 1.512071 0.691976 0.405691 0.049 Uiso 0.457(5) 1 calc R U P A 2
C23B C 1.4756(15) 0.6826(7) 0.45046(15) 0.049(2) Uani 0.457(5) 1 d D . P A 2
H23B H 1.660810 0.704515 0.454577 0.059 Uiso 0.457(5) 1 calc R U P A 2
C24 C 1.2980(6) 0.6621(3) 0.47333(7) 0.0473(8) Uani 1 1 d D . . . .
H24 H 1.357356 0.670683 0.493463 0.057 Uiso 0.543(5) 1 calc R U P A 1
H24A H 1.352503 0.678909 0.493337 0.057 Uiso 0.457(5) 1 calc R U P A 2
C25 C 1.1907(15) 0.5539(5) 0.46383(13) 0.0472(17) Uani 0.543(5) 1 d D . P A 1
H25 H 1.166534 0.486442 0.477609 0.057 Uiso 0.543(5) 1 calc R U P A 1
C26 C 1.1138(15) 0.5371(5) 0.43442(12) 0.0473(17) Uani 0.543(5) 1 d D . P A 1
H26 H 1.046167 0.457198 0.428143 0.057 Uiso 0.543(5) 1 calc R U P A 1
C25B C 1.0360(18) 0.6166(8) 0.46741(14) 0.048(2) Uani 0.457(5) 1 d . . P A 2
H25B H 0.917768 0.593834 0.483410 0.058 Uiso 0.457(5) 1 calc R U P A 2
C26B C 0.9476(14) 0.6046(7) 0.43794(13) 0.0408(18) Uani 0.457(5) 1 d . . P A 2
H26B H 0.765777 0.577785 0.433691 0.049 Uiso 0.457(5) 1 calc R U P A 2
C27 C 0.6783(6) 0.2608(3) 0.44781(6) 0.0490(8) Uani 1 1 d . . . . .
H27 H 0.618568 0.346229 0.446959 0.059 Uiso 1 1 calc R U . . .
C28 C 0.8734(6) 0.2252(4) 0.46882(7) 0.0548(9) Uani 1 1 d . . . . .
H28 H 0.945977 0.286447 0.482185 0.066 Uiso 1 1 calc R U . . .
C29 C 0.9613(7) 0.1036(4) 0.47043(7) 0.0561(9) Uani 1 1 d . . . . .
H29 H 1.094366 0.079777 0.484893 0.067 Uiso 1 1 calc R U . . .
C30 C 0.8565(8) 0.0149(3) 0.45099(7) 0.0638(10) Uani 1 1 d . . . . .
H30 H 0.918024 -0.070232 0.451856 0.077 Uiso 1 1 calc R U . . .
C31 C 0.6607(7) 0.0506(3) 0.43014(7) 0.0555(9) Uani 1 1 d . . . . .
H31 H 0.587369 -0.011154 0.416934 0.067 Uiso 1 1 calc R U . . .
N32 N 0.7375(5) -0.0266(2) 0.35562(5) 0.0432(6) Uani 1 1 d . . . . .
N33 N 0.6004(6) -0.1132(2) 0.35813(6) 0.0560(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 O6 1.437(3) . ?
C1 C7 1.521(4) . ?
C1 C2 1.525(3) . ?
C1 H1 1.0000 . ?
C2 O8 1.423(3) . ?
C2 C3 1.527(3) . ?
C2 H2 1.0000 . ?
C3 N9 1.479(3) . ?
C3 C4 1.522(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.516(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O6 1.443(3) . ?
C5 C10 1.517(3) . ?
C5 H5 1.0000 . ?
C7 O17 1.424(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O8 C20 1.439(3) . ?
N9 N32 1.236(3) . ?
C10 C15 1.378(4) . ?
C10 C11 1.393(4) . ?
C11 C12 1.395(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(4) . ?
C13 C16 1.519(4) . ?
C14 C15 1.390(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O17 C18 1.424(3) . ?
C18 C19 1.499(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C20 C21 1.508(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C31 1.375(4) . ?
C21 C27 1.379(4) . ?
C19 C22B 1.348(7) . ?
C19 C26 1.361(6) . ?
C19 C22 1.395(6) . ?
C19 C26B 1.425(7) . ?
C22 C23 1.391(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.420(6) . ?
C23 H23 0.9500 . ?
C22B C23B 1.375(8) . ?
C22B H22B 0.9500 . ?
C23B C24 1.358(8) . ?
C23B H23B 0.9500 . ?
C24 C25 1.329(6) . ?
C24 C25B 1.390(8) . ?
C24 H24 0.9500 . ?
C24 H24A 0.9500 . ?
C25 C26 1.379(7) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C25B C26B 1.393(9) . ?
C25B H25B 0.9500 . ?
C26B H26B 0.9500 . ?
C27 C28 1.389(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.358(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.377(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.387(4) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
N32 N33 1.139(3) . ?

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
O6 C1 C7 111.47(19) . . ?
O6 C1 C2 112.4(2) . . ?
C7 C1 C2 114.4(2) . . ?
O6 C1 H1 105.9 . . ?
C7 C1 H1 105.9 . . ?
C2 C1 H1 105.9 . . ?
O8 C2 C1 110.3(2) . . ?
O8 C2 C3 106.7(2) . . ?
C1 C2 C3 111.0(2) . . ?
O8 C2 H2 109.6 . . ?
C1 C2 H2 109.6 . . ?
C3 C2 H2 109.6 . . ?
N9 C3 C4 112.6(2) . . ?
N9 C3 C2 111.4(2) . . ?
C4 C3 C2 110.6(2) . . ?
N9 C3 H3 107.3 . . ?
C4 C3 H3 107.3 . . ?
C2 C3 H3 107.3 . . ?
C5 C4 C3 109.9(2) . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
O6 C5 C4 110.15(19) . . ?
O6 C5 C10 105.90(19) . . ?
C4 C5 C10 114.7(2) . . ?
O6 C5 H5 108.6 . . ?
C4 C5 H5 108.6 . . ?
C10 C5 H5 108.6 . . ?
C1 O6 C5 114.70(17) . . ?
O17 C7 C1 106.2(2) . . ?
O17 C7 H7A 110.5 . . ?
C1 C7 H7A 110.5 . . ?
O17 C7 H7B 110.5 . . ?
C1 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C2 O8 C20 113.6(2) . . ?
N32 N9 C3 116.3(2) . . ?
C15 C10 C11 117.5(2) . . ?
C15 C10 C5 120.8(2) . . ?
C11 C10 C5 121.7(2) . . ?
C10 C11 C12 120.8(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 121.6(3) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 117.5(2) . . ?
C12 C13 C16 121.6(3) . . ?
C14 C13 C16 120.9(3) . . ?
C13 C14 C15 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C10 C15 C14 121.3(2) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 O17 C18 113.83(19) . . ?
O17 C18 C19 108.9(2) . . ?
O17 C18 H18A 109.9 . . ?
C19 C18 H18A 109.9 . . ?
O17 C18 H18B 109.9 . . ?
C19 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
O8 C20 C21 112.9(2) . . ?
O8 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
O8 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C31 C21 C27 118.1(3) . . ?
C31 C21 C20 120.3(3) . . ?
C27 C21 C20 121.6(3) . . ?
C26 C19 C22 118.6(4) . . ?
C22B C19 C26B 118.2(4) . . ?
C22B C19 C18 121.3(4) . . ?
C26 C19 C18 122.9(3) . . ?
C22 C19 C18 118.5(3) . . ?
C26B C19 C18 120.5(3) . . ?
C23 C22 C19 120.1(4) . . ?
C23 C22 H22 119.9 . . ?
C19 C22 H22 119.9 . . ?
C22 C23 C24 119.0(5) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C19 C22B C23B 122.4(6) . . ?
C19 C22B H22B 118.8 . . ?
C23B C22B H22B 118.8 . . ?
C24 C23B C22B 120.1(6) . . ?
C24 C23B H23B 119.9 . . ?
C22B C23B H23B 119.9 . . ?
C23B C24 C25B 119.8(4) . . ?
C25 C24 C23 119.3(4) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C23B C24 H24A 120.1 . . ?
C25B C24 H24A 120.1 . . ?
C24 C25 C26 121.5(5) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C19 C26 C25 121.3(5) . . ?
C19 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C24 C25B C26B 119.8(6) . . ?
C24 C25B H25B 120.1 . . ?
C26B C25B H25B 120.1 . . ?
C25B C26B C19 119.3(6) . . ?
C25B C26B H26B 120.3 . . ?
C19 C26B H26B 120.3 . . ?
C21 C27 C28 120.7(3) . . ?
C21 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C29 C28 C27 120.6(3) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 119.6(3) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C29 C30 C31 119.6(3) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C21 C31 C30 121.3(3) . . ?
C21 C31 H31 119.3 . . ?
C30 C31 H31 119.3 . . ?
N33 N32 N9 171.1(3) . . ?

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
O6 C1 C2 O8 -68.1(3) . . . . ?
C7 C1 C2 O8 163.4(2) . . . . ?
O6 C1 C2 C3 50.0(3) . . . . ?
C7 C1 C2 C3 -78.4(3) . . . . ?
O8 C2 C3 N9 -57.4(2) . . . . ?
C1 C2 C3 N9 -177.7(2) . . . . ?
O8 C2 C3 C4 68.6(2) . . . . ?
C1 C2 C3 C4 -51.7(3) . . . . ?
N9 C3 C4 C5 -178.7(2) . . . . ?
C2 C3 C4 C5 55.9(3) . . . . ?
C3 C4 C5 O6 -57.9(3) . . . . ?
C3 C4 C5 C10 -177.27(19) . . . . ?
C7 C1 O6 C5 75.7(2) . . . . ?
C2 C1 O6 C5 -54.2(3) . . . . ?
C4 C5 O6 C1 58.0(2) . . . . ?
C10 C5 O6 C1 -177.40(18) . . . . ?
O6 C1 C7 O17 171.22(19) . . . . ?
C2 C1 C7 O17 -59.8(3) . . . . ?
C1 C2 O8 C20 -86.7(2) . . . . ?
C3 C2 O8 C20 152.6(2) . . . . ?
C4 C3 N9 N32 -46.2(3) . . . . ?
C2 C3 N9 N32 78.7(3) . . . . ?
O6 C5 C10 C15 39.0(3) . . . . ?
C4 C5 C10 C15 160.7(2) . . . . ?
O6 C5 C10 C11 -142.1(2) . . . . ?
C4 C5 C10 C11 -20.4(3) . . . . ?
C15 C10 C11 C12 -0.7(4) . . . . ?
C5 C10 C11 C12 -179.6(2) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C11 C12 C13 C14 1.4(4) . . . . ?
C11 C12 C13 C16 -178.2(2) . . . . ?
C12 C13 C14 C15 -1.2(4) . . . . ?
C16 C13 C14 C15 178.4(2) . . . . ?
C11 C10 C15 C14 0.9(4) . . . . ?
C5 C10 C15 C14 179.8(2) . . . . ?
C13 C14 C15 C10 0.1(4) . . . . ?
C1 C7 O17 C18 -163.4(2) . . . . ?
C7 O17 C18 C19 179.0(2) . . . . ?
C2 O8 C20 C21 -66.7(3) . . . . ?
O8 C20 C21 C31 -58.1(4) . . . . ?
O8 C20 C21 C27 121.7(3) . . . . ?
O17 C18 C19 C22B 136.9(4) . . . . ?
O17 C18 C19 C26 11.6(5) . . . . ?
O17 C18 C19 C22 -169.7(4) . . . . ?
O17 C18 C19 C26B -43.0(5) . . . . ?
C26 C19 C22 C23 -2.8(8) . . . . ?
C18 C19 C22 C23 178.5(5) . . . . ?
C19 C22 C23 C24 2.6(9) . . . . ?
C26B C19 C22B C23B 1.0(9) . . . . ?
C18 C19 C22B C23B -178.9(5) . . . . ?
C19 C22B C23B C24 -4.3(11) . . . . ?
C22B C23B C24 C25B 7.1(10) . . . . ?
C22 C23 C24 C25 -2.6(9) . . . . ?
C23 C24 C25 C26 2.8(10) . . . . ?
C22 C19 C26 C25 3.0(9) . . . . ?
C18 C19 C26 C25 -178.4(5) . . . . ?
C24 C25 C26 C19 -3.1(11) . . . . ?
C23B C24 C25B C26B -6.6(10) . . . . ?
C24 C25B C26B C19 3.3(11) . . . . ?
C22B C19 C26B C25B -0.5(9) . . . . ?
C18 C19 C26B C25B 179.3(6) . . . . ?
C31 C21 C27 C28 0.3(4) . . . . ?
C20 C21 C27 C28 -179.5(2) . . . . ?
C21 C27 C28 C29 -0.1(4) . . . . ?
C27 C28 C29 C30 0.2(5) . . . . ?
C28 C29 C30 C31 -0.5(5) . . . . ?
C27 C21 C31 C30 -0.6(5) . . . . ?
C20 C21 C31 C30 179.1(3) . . . . ?
C29 C30 C31 C21 0.8(5) . . . . ?

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
C3 H3 O6 1.00 2.62 3.615(3) 176.1 1_655 yes
C7 H7A O6 0.99 2.59 3.515(3) 155.4 1_655 yes

_refine_diff_density_max         0.152
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.033





_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: deuterated chloroform'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_JG-SArN3
_database_code_depnum_ccdc_archive 'CCDC 2225279'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-12-08 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
2R,3S,4S,6S)-4-azido-3-(benzyloxy)-2-((benzyloxy)methyl)-6-(p-tolyl)tetrahydro-2H-pyran
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H29 N3 O3'
_chemical_formula_sum            'C27 H29 N3 O3'
_chemical_formula_weight         443.53

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.9654(3)
_cell_length_b                   10.7233(8)
_cell_length_c                   44.847(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2387.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9925
_cell_measurement_theta_min      6.9
_cell_measurement_theta_max      68.0

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.649
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.592
_exptl_absorpt_process_details   'Abscor (Rigaku,1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku micromax 007 1.2kW'
_diffrn_radiation_monochromator  'Confocal Osmic mirrors'
_diffrn_measurement_device       
'four-circle partial χ goniometer diffractometer'
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_type            
'RAPID II large area curved imaging plate detector '
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            21847
_diffrn_reflns_av_unetI/netI     0.0858
_diffrn_reflns_av_R_equivalents  0.1014
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_theta_min         7.223
_diffrn_reflns_theta_max         65.083
_diffrn_reflns_theta_full        65.083
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4045
_reflns_number_gt                1855
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.1(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4045
_refine_ls_number_parameters     337
_refine_ls_number_restraints     183
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   0.810
_refine_ls_restrained_S_all      0.810
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.5714(8) 0.3814(4) 0.35229(7) 0.0867(10) Uani 1 1 d . . . . .
H1 H 0.440677 0.413869 0.366698 0.104 Uiso 1 1 calc R U . . .
C2 C 0.6705(7) 0.2580(4) 0.36491(8) 0.0852(10) Uani 1 1 d . . . . .
H2 H 0.790891 0.273854 0.381806 0.102 Uiso 1 1 calc R U . . .
C3 C 0.8175(8) 0.1826(4) 0.34156(8) 0.0896(11) Uani 1 1 d . . . . .
H3 H 0.978326 0.230231 0.336049 0.108 Uiso 1 1 calc R U . . .
C4 C 0.6476(7) 0.1700(3) 0.31346(8) 0.0940(11) Uani 1 1 d . . . . .
H4A H 0.749098 0.126034 0.298273 0.113 Uiso 1 1 calc R U . . .
H4B H 0.486689 0.122099 0.317824 0.113 Uiso 1 1 calc R U . . .
C5 C 0.5698(7) 0.2969(3) 0.30212(7) 0.0854(10) Uani 1 1 d . . . . .
H5 H 0.734772 0.342583 0.297154 0.102 Uiso 1 1 calc R U . . .
O6 O 0.4270(5) 0.3661(2) 0.32466(5) 0.0887(7) Uani 1 1 d . . . . .
C7 C 0.7883(9) 0.4810(3) 0.34927(8) 0.0967(12) Uani 1 1 d . . . . .
H7A H 0.932120 0.451887 0.336394 0.116 Uiso 1 1 calc R U . . .
H7B H 0.713027 0.556546 0.340803 0.116 Uiso 1 1 calc R U . . .
O8 O 0.4477(5) 0.1850(2) 0.37457(5) 0.0992(8) Uani 1 1 d . . . . .
N9 N 0.9120(8) 0.0619(4) 0.35344(9) 0.1178(13) Uani 1 1 d . . . . .
C10 C 0.3880(7) 0.2961(4) 0.27468(8) 0.0849(10) Uani 1 1 d . . . . .
C11 C 0.3641(8) 0.1935(4) 0.25664(9) 0.1182(14) Uani 1 1 d . . . . .
H11 H 0.459570 0.121401 0.261256 0.142 Uiso 1 1 calc R U . . .
C12 C 0.1990(10) 0.1954(5) 0.23150(10) 0.1289(16) Uani 1 1 d . . . . .
H12 H 0.191092 0.124906 0.219441 0.155 Uiso 1 1 calc R U . . .
C13 C 0.0487(9) 0.2972(5) 0.22398(8) 0.1052(13) Uani 1 1 d . . . . .
C14 C 0.0780(9) 0.4000(5) 0.24170(9) 0.1123(13) Uani 1 1 d . . . . .
H14 H -0.015997 0.472254 0.236853 0.135 Uiso 1 1 calc R U . . .
C15 C 0.2453(9) 0.4003(4) 0.26700(9) 0.1051(13) Uani 1 1 d . . . . .
H15 H 0.259004 0.471970 0.278595 0.126 Uiso 1 1 calc R U . . .
C16 C -0.1354(8) 0.2990(4) 0.19746(8) 0.1399(16) Uani 1 1 d . . . . .
H16A H -0.255985 0.229178 0.198431 0.210 Uiso 1 1 calc R U . . .
H16B H -0.030569 0.294111 0.179511 0.210 Uiso 1 1 calc R U . . .
H16C H -0.237555 0.375065 0.197456 0.210 Uiso 1 1 calc R U . . .
O17 O 0.8877(6) 0.5041(3) 0.37839(6) 0.1114(9) Uani 1 1 d . . . . .
C18 C 1.0224(11) 0.6172(4) 0.38192(9) 0.1248(15) Uani 1 1 d . . . . .
H18A H 0.903273 0.685483 0.376714 0.150 Uiso 1 1 calc R U . . .
H18B H 1.176961 0.619948 0.368721 0.150 Uiso 1 1 calc R U . . .
C20 C 0.3578(8) 0.2104(4) 0.40444(8) 0.1119(13) Uani 1 1 d . . . . .
H20A H 0.191325 0.165562 0.408059 0.134 Uiso 1 1 calc R U . . .
H20B H 0.320368 0.298799 0.406353 0.134 Uiso 1 1 calc R U . . .
C21 C 0.5620(9) 0.1732(6) 0.42767(9) 0.1001(12) Uani 1 1 d . . . . .
C19 C 1.1133(11) 0.6311(4) 0.41357(10) 0.1008(13) Uani 1 1 d D . . . .
C22 C 1.234(3) 0.7409(11) 0.4216(3) 0.120(4) Uani 0.577(16) 1 d D . P A 1
H22 H 1.263695 0.803183 0.407570 0.145 Uiso 0.577(16) 1 calc R U P A 1
C23 C 1.311(3) 0.7577(12) 0.4512(2) 0.134(5) Uani 0.577(16) 1 d D . P A 1
H23 H 1.377449 0.834585 0.457379 0.161 Uiso 0.577(16) 1 calc R U P A 1
C22B C 1.363(3) 0.676(2) 0.4194(4) 0.139(6) Uani 0.423(16) 1 d D . P A 2
H22B H 1.473153 0.699591 0.403632 0.167 Uiso 0.423(16) 1 calc R U P A 2
C23B C 1.456(3) 0.687(2) 0.4480(3) 0.148(6) Uani 0.423(16) 1 d D . P A 2
H23B H 1.632403 0.712606 0.451399 0.178 Uiso 0.423(16) 1 calc R U P A 2
C24 C 1.2903(13) 0.6610(6) 0.47142(12) 0.1358(18) Uani 1 1 d D . . . .
H24 H 1.355193 0.670487 0.490738 0.163 Uiso 0.577(16) 1 calc R U P A 1
H24A H 1.346169 0.678224 0.490778 0.163 Uiso 0.423(16) 1 calc R U P A 2
C25 C 1.178(3) 0.5551(11) 0.4632(3) 0.125(5) Uani 0.577(16) 1 d D . P A 1
H25 H 1.151742 0.491523 0.476962 0.149 Uiso 0.577(16) 1 calc R U P A 1
C26 C 1.099(3) 0.5393(11) 0.4341(3) 0.131(4) Uani 0.577(16) 1 d D . P A 1
H26 H 1.033607 0.461799 0.428308 0.157 Uiso 0.577(16) 1 calc R U P A 1
C25B C 1.047(4) 0.610(2) 0.4666(4) 0.142(7) Uani 0.423(16) 1 d D . P A 2
H25B H 0.942892 0.582181 0.482459 0.170 Uiso 0.423(16) 1 calc R U P A 2
C26B C 0.956(4) 0.601(2) 0.4379(3) 0.128(6) Uani 0.423(16) 1 d D . P A 2
H26B H 0.780510 0.574218 0.434694 0.154 Uiso 0.423(16) 1 calc R U P A 2
C27 C 0.6701(10) 0.2581(5) 0.44727(11) 0.1199(15) Uani 1 1 d . . . . .
H27 H 0.614941 0.340898 0.446451 0.144 Uiso 1 1 calc R U . . .
C28 C 0.8607(11) 0.2221(7) 0.46831(11) 0.1354(18) Uani 1 1 d . . . . .
H28 H 0.929645 0.280598 0.481576 0.162 Uiso 1 1 calc R U . . .
C29 C 0.9463(12) 0.1028(8) 0.46959(12) 0.1358(19) Uani 1 1 d . . . . .
H29 H 1.074504 0.079448 0.483646 0.163 Uiso 1 1 calc R U . . .
C30 C 0.8449(13) 0.0163(5) 0.45030(15) 0.146(2) Uani 1 1 d . . . . .
H30 H 0.903258 -0.066026 0.450917 0.175 Uiso 1 1 calc R U . . .
C31 C 0.6535(12) 0.0540(6) 0.42981(10) 0.1242(16) Uani 1 1 d . . . . .
H31 H 0.583572 -0.005254 0.416810 0.149 Uiso 1 1 calc R U . . .
N32 N 0.7418(11) -0.0200(5) 0.35475(9) 0.1185(14) Uani 1 1 d . . . . .
N33 N 0.6067(10) -0.1070(4) 0.35743(10) 0.1454(17) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 O6 1.441(3) . ?
C1 C2 1.521(4) . ?
C1 C7 1.522(5) . ?
C1 H1 0.9800 . ?
C2 O8 1.423(3) . ?
C2 C3 1.511(4) . ?
C2 H2 0.9800 . ?
C3 N9 1.476(5) . ?
C3 C4 1.522(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.503(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O6 1.440(3) . ?
C5 C10 1.526(4) . ?
C5 H5 0.9800 . ?
C7 O17 1.418(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
O8 C20 1.438(4) . ?
N9 N32 1.220(5) . ?
C10 C15 1.367(4) . ?
C10 C11 1.371(4) . ?
C11 C12 1.394(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.365(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(5) . ?
C13 C16 1.500(5) . ?
C14 C15 1.406(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O17 C18 1.393(4) . ?
C18 C19 1.497(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 C21 1.507(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C31 1.359(6) . ?
C21 C27 1.375(5) . ?
C19 C26 1.351(9) . ?
C19 C22B 1.355(13) . ?
C19 C22 1.370(10) . ?
C19 C26B 1.380(13) . ?
C22 C23 1.392(10) . ?
C22 H22 0.9300 . ?
C23 C24 1.382(10) . ?
C23 H23 0.9300 . ?
C22B C23B 1.367(14) . ?
C22B H22B 0.9300 . ?
C23B C24 1.365(13) . ?
C23B H23B 0.9300 . ?
C24 C25 1.319(10) . ?
C24 C25B 1.340(14) . ?
C24 H24 0.9300 . ?
C24 H24A 0.9300 . ?
C25 C26 1.369(11) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C25B C26B 1.368(14) . ?
C25B H25B 0.9300 . ?
C26B H26B 0.9300 . ?
C27 C28 1.391(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.349(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.364(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.383(6) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
N32 N33 1.155(5) . ?

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
O6 C1 C2 112.4(3) . . ?
O6 C1 C7 110.8(3) . . ?
C2 C1 C7 114.5(3) . . ?
O6 C1 H1 106.1 . . ?
C2 C1 H1 106.1 . . ?
C7 C1 H1 106.1 . . ?
O8 C2 C3 107.0(3) . . ?
O8 C2 C1 109.9(3) . . ?
C3 C2 C1 111.3(3) . . ?
O8 C2 H2 109.5 . . ?
C3 C2 H2 109.5 . . ?
C1 C2 H2 109.5 . . ?
N9 C3 C2 111.9(3) . . ?
N9 C3 C4 113.4(3) . . ?
C2 C3 C4 110.7(3) . . ?
N9 C3 H3 106.8 . . ?
C2 C3 H3 106.8 . . ?
C4 C3 H3 106.8 . . ?
C5 C4 C3 110.0(3) . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
O6 C5 C4 110.8(3) . . ?
O6 C5 C10 106.1(3) . . ?
C4 C5 C10 114.8(3) . . ?
O6 C5 H5 108.3 . . ?
C4 C5 H5 108.3 . . ?
C10 C5 H5 108.3 . . ?
C5 O6 C1 114.7(3) . . ?
O17 C7 C1 106.7(3) . . ?
O17 C7 H7A 110.4 . . ?
C1 C7 H7A 110.4 . . ?
O17 C7 H7B 110.4 . . ?
C1 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
C2 O8 C20 114.9(3) . . ?
N32 N9 C3 115.3(4) . . ?
C15 C10 C11 117.6(4) . . ?
C15 C10 C5 120.3(4) . . ?
C11 C10 C5 122.1(4) . . ?
C10 C11 C12 121.1(4) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 122.2(4) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C14 116.3(4) . . ?
C12 C13 C16 122.7(4) . . ?
C14 C13 C16 121.0(5) . . ?
C13 C14 C15 122.3(4) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C10 C15 C14 120.5(4) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 O17 C7 115.1(3) . . ?
O17 C18 C19 109.8(4) . . ?
O17 C18 H18A 109.7 . . ?
C19 C18 H18A 109.7 . . ?
O17 C18 H18B 109.7 . . ?
C19 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
O8 C20 C21 112.7(3) . . ?
O8 C20 H20A 109.1 . . ?
C21 C20 H20A 109.1 . . ?
O8 C20 H20B 109.1 . . ?
C21 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
C31 C21 C27 116.5(5) . . ?
C31 C21 C20 121.5(5) . . ?
C27 C21 C20 122.0(5) . . ?
C26 C19 C22 118.0(8) . . ?
C22B C19 C26B 116.5(11) . . ?
C26 C19 C18 124.0(6) . . ?
C22B C19 C18 119.6(9) . . ?
C22 C19 C18 117.9(6) . . ?
C26B C19 C18 123.8(8) . . ?
C19 C22 C23 118.9(9) . . ?
C19 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C24 C23 C22 120.5(9) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C19 C22B C23B 121.5(15) . . ?
C19 C22B H22B 119.3 . . ?
C23B C22B H22B 119.3 . . ?
C24 C23B C22B 120.0(14) . . ?
C24 C23B H23B 120.0 . . ?
C22B C23B H23B 120.0 . . ?
C25B C24 C23B 120.2(12) . . ?
C25 C24 C23 119.6(9) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C25B C24 H24A 119.9 . . ?
C23B C24 H24A 119.9 . . ?
C24 C25 C26 119.6(12) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C19 C26 C25 123.0(11) . . ?
C19 C26 H26 118.5 . . ?
C25 C26 H26 118.5 . . ?
C24 C25B C26B 118.6(15) . . ?
C24 C25B H25B 120.7 . . ?
C26B C25B H25B 120.7 . . ?
C25B C26B C19 122.7(14) . . ?
C25B C26B H26B 118.6 . . ?
C19 C26B H26B 118.6 . . ?
C21 C27 C28 121.0(5) . . ?
C21 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
C29 C28 C27 120.4(6) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 120.1(6) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C30 C31 118.5(6) . . ?
C29 C30 H30 120.8 . . ?
C31 C30 H30 120.8 . . ?
C21 C31 C30 123.5(5) . . ?
C21 C31 H31 118.3 . . ?
C30 C31 H31 118.3 . . ?
N33 N32 N9 171.2(5) . . ?

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
O6 C1 C2 O8 -68.6(4) . . . . ?
C7 C1 C2 O8 163.8(3) . . . . ?
O6 C1 C2 C3 49.8(4) . . . . ?
C7 C1 C2 C3 -77.8(4) . . . . ?
O8 C2 C3 N9 -59.3(4) . . . . ?
C1 C2 C3 N9 -179.4(3) . . . . ?
O8 C2 C3 C4 68.3(4) . . . . ?
C1 C2 C3 C4 -51.8(4) . . . . ?
N9 C3 C4 C5 -177.6(3) . . . . ?
C2 C3 C4 C5 55.7(4) . . . . ?
C3 C4 C5 O6 -57.2(4) . . . . ?
C3 C4 C5 C10 -177.4(3) . . . . ?
C4 C5 O6 C1 56.9(4) . . . . ?
C10 C5 O6 C1 -177.8(3) . . . . ?
C2 C1 O6 C5 -53.0(4) . . . . ?
C7 C1 O6 C5 76.5(3) . . . . ?
O6 C1 C7 O17 170.5(3) . . . . ?
C2 C1 C7 O17 -61.0(4) . . . . ?
C3 C2 O8 C20 153.1(3) . . . . ?
C1 C2 O8 C20 -85.9(3) . . . . ?
C2 C3 N9 N32 80.2(5) . . . . ?
C4 C3 N9 N32 -45.9(5) . . . . ?
O6 C5 C10 C15 39.6(4) . . . . ?
C4 C5 C10 C15 162.3(3) . . . . ?
O6 C5 C10 C11 -141.5(4) . . . . ?
C4 C5 C10 C11 -18.8(5) . . . . ?
C15 C10 C11 C12 -0.3(6) . . . . ?
C5 C10 C11 C12 -179.3(3) . . . . ?
C10 C11 C12 C13 -1.7(7) . . . . ?
C11 C12 C13 C14 3.0(7) . . . . ?
C11 C12 C13 C16 -178.3(4) . . . . ?
C12 C13 C14 C15 -2.4(6) . . . . ?
C16 C13 C14 C15 178.8(3) . . . . ?
C11 C10 C15 C14 0.9(6) . . . . ?
C5 C10 C15 C14 179.9(3) . . . . ?
C13 C14 C15 C10 0.5(6) . . . . ?
C1 C7 O17 C18 -160.5(3) . . . . ?
C7 O17 C18 C19 179.2(4) . . . . ?
C2 O8 C20 C21 -66.8(4) . . . . ?
O8 C20 C21 C31 -58.0(5) . . . . ?
O8 C20 C21 C27 120.4(4) . . . . ?
O17 C18 C19 C26 8.7(12) . . . . ?
O17 C18 C19 C22B 137.4(12) . . . . ?
O17 C18 C19 C22 -175.7(8) . . . . ?
O17 C18 C19 C26B -43.1(14) . . . . ?
C26 C19 C22 C23 -6.5(14) . . . . ?
C18 C19 C22 C23 177.7(7) . . . . ?
C19 C22 C23 C24 6.1(15) . . . . ?
C26B C19 C22B C23B 2(2) . . . . ?
C18 C19 C22B C23B -178.4(11) . . . . ?
C19 C22B C23B C24 -5(2) . . . . ?
C22B C23B C24 C25B 8(2) . . . . ?
C22 C23 C24 C25 -5.1(16) . . . . ?
C23 C24 C25 C26 4.4(16) . . . . ?
C22 C19 C26 C25 6.1(17) . . . . ?
C18 C19 C26 C25 -178.4(9) . . . . ?
C24 C25 C26 C19 -5.1(18) . . . . ?
C23B C24 C25B C26B -9(2) . . . . ?
C24 C25B C26B C19 6(2) . . . . ?
C22B C19 C26B C25B -3(2) . . . . ?
C18 C19 C26B C25B 177.4(11) . . . . ?
C31 C21 C27 C28 -0.7(6) . . . . ?
C20 C21 C27 C28 -179.2(3) . . . . ?
C21 C27 C28 C29 0.9(7) . . . . ?
C27 C28 C29 C30 -0.4(8) . . . . ?
C28 C29 C30 C31 -0.4(8) . . . . ?
C27 C21 C31 C30 0.0(7) . . . . ?
C20 C21 C31 C30 178.5(4) . . . . ?
C29 C30 C31 C21 0.6(8) . . . . ?

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.064




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: deuterated chloroform'
