# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2207290'
loop_
_audit_author_name
_audit_author_address
'Maxime Siegler'
;Johns Hopkins University
United States of America
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'tert-butyl (4-azido-5-oxotetrahydrofuran-3-yl)carbamate'
_chemical_name_common            '2S-azido 3S-Boc-amino butyrolactone'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H14 N4 O4'
_chemical_formula_sum            'C9 H14 N4 O4'
_chemical_formula_weight         242.24

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                   5.17882(11)
_cell_length_b                   9.5846(2)
_cell_length_c                   23.5161(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1167.27(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3373
_cell_measurement_theta_min      5.90
_cell_measurement_theta_max      72.01

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.664
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.058
_exptl_absorpt_coefficient_mu    0.934
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.264
_oxdiff_exptl_absorpt_empirical_full_max 1.951
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         .
_diffrn_standards_interval_time  .
_diffrn_reflns_number            9129
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.759
_diffrn_reflns_theta_max         71.781
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2299
_reflns_number_gt                2240
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+0.0595P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 888 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2299
_refine_ls_number_parameters     192
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0782
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_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 0.1112(3) 0.59516(18) 0.51304(7) 0.0404(4) Uani 1 1 d . . . . .
C2 C 0.0984(3) 0.76803(16) 0.58081(7) 0.0369(3) Uani 1 1 d . . . . .
H2A H -0.048691 0.768750 0.607694 0.044 Uiso 1 1 calc R U . . .
H2B H 0.170342 0.863542 0.578399 0.044 Uiso 1 1 calc R U . . .
C3 C 0.3070(3) 0.66449(15) 0.60079(6) 0.0334(3) Uani 1 1 d . . . . .
H3 H 0.481087 0.703804 0.591765 0.040 Uiso 1 1 calc R U . . .
C4 C 0.2598(3) 0.53683(16) 0.56347(7) 0.0383(3) Uani 1 1 d . . . . .
H4 H 0.150050 0.467925 0.584353 0.046 Uiso 1 1 calc R U . . .
C5 C 0.4974(3) 0.64374(15) 0.69591(6) 0.0325(3) Uani 1 1 d . . . . .
C6 C 0.6107(3) 0.6393(2) 0.79753(7) 0.0438(4) Uani 0.515(17) 1 d D U P A 1
C7 C 0.794(2) 0.7689(9) 0.7916(6) 0.0441(18) Uani 0.515(17) 1 d D U P A 1
H7A H 0.924184 0.750249 0.762272 0.066 Uiso 0.515(17) 1 calc R U P A 1
H7B H 0.880829 0.786219 0.828037 0.066 Uiso 0.515(17) 1 calc R U P A 1
H7C H 0.692945 0.851111 0.780925 0.066 Uiso 0.515(17) 1 calc R U P A 1
C8 C 0.4387(10) 0.6756(13) 0.8497(2) 0.0612(19) Uani 0.515(17) 1 d D U P A 1
H8A H 0.363425 0.768531 0.844607 0.092 Uiso 0.515(17) 1 calc R U P A 1
H8B H 0.544210 0.674516 0.884328 0.092 Uiso 0.515(17) 1 calc R U P A 1
H8C H 0.300069 0.606464 0.853166 0.092 Uiso 0.515(17) 1 calc R U P A 1
C9 C 0.748(3) 0.5080(11) 0.8008(6) 0.059(3) Uani 0.515(17) 1 d D U P A 1
H9A H 0.625640 0.432525 0.808621 0.088 Uiso 0.515(17) 1 calc R U P A 1
H9B H 0.876186 0.512596 0.831462 0.088 Uiso 0.515(17) 1 calc R U P A 1
H9C H 0.835823 0.490170 0.764614 0.088 Uiso 0.515(17) 1 calc R U P A 1
C6' C 0.6107(3) 0.6393(2) 0.79753(7) 0.0438(4) Uani 0.485(17) 1 d D U P A 2
C7' C 0.734(3) 0.7730(12) 0.8017(7) 0.057(3) Uani 0.485(17) 1 d D U P A 2
H7'1 H 0.832719 0.791078 0.766858 0.086 Uiso 0.485(17) 1 calc R U P A 2
H7'2 H 0.851228 0.773517 0.834410 0.086 Uiso 0.485(17) 1 calc R U P A 2
H7'3 H 0.602949 0.845688 0.806548 0.086 Uiso 0.485(17) 1 calc R U P A 2
C8' C 0.4422(11) 0.5945(14) 0.8479(2) 0.059(2) Uani 0.485(17) 1 d D U P A 2
H8'1 H 0.298255 0.659983 0.852224 0.089 Uiso 0.485(17) 1 calc R U P A 2
H8'2 H 0.546239 0.594184 0.882711 0.089 Uiso 0.485(17) 1 calc R U P A 2
H8'3 H 0.374391 0.500532 0.840974 0.089 Uiso 0.485(17) 1 calc R U P A 2
C9' C 0.803(2) 0.5133(11) 0.7880(5) 0.0431(17) Uani 0.485(17) 1 d D U P A 2
H9'1 H 0.705060 0.429140 0.778476 0.065 Uiso 0.485(17) 1 calc R U P A 2
H9'2 H 0.902552 0.497111 0.822884 0.065 Uiso 0.485(17) 1 calc R U P A 2
H9'3 H 0.921682 0.535686 0.756806 0.065 Uiso 0.485(17) 1 calc R U P A 2
N1 N 0.5323(4) 0.3164(2) 0.46978(9) 0.0690(5) Uani 1 1 d . . . . .
N2 N 0.5011(3) 0.39072(15) 0.50624(7) 0.0496(4) Uani 1 1 d . . . . .
N3 N 0.5069(3) 0.47149(17) 0.54743(7) 0.0522(4) Uani 1 1 d . . . . .
N4 N 0.2886(3) 0.64216(15) 0.66127(5) 0.0350(3) Uani 1 1 d . . . . .
H4N H 0.147(4) 0.639(2) 0.6756(8) 0.036(5) Uiso 1 1 d . . . . .
O1 O 0.0767(3) 0.53997(15) 0.46794(6) 0.0560(4) Uani 1 1 d . . . . .
O2 O 0.0153(2) 0.72093(12) 0.52537(5) 0.0407(3) Uani 1 1 d . . . . .
O3 O 0.7188(2) 0.64971(16) 0.67951(5) 0.0485(3) Uani 1 1 d . . . . .
O4 O 0.4211(2) 0.63792(15) 0.75022(4) 0.0431(3) 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 O1 1.198(2) . ?
C1 O2 1.335(2) . ?
C1 C4 1.520(2) . ?
C2 O2 1.4450(19) . ?
C2 C3 1.540(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N4 1.4415(19) . ?
C3 C4 1.525(2) . ?
C3 H3 1.0000 . ?
C4 N3 1.474(2) . ?
C4 H4 1.0000 . ?
C5 O3 1.211(2) . ?
C5 O4 1.3380(18) . ?
C5 N4 1.354(2) . ?
C6 C9 1.448(10) . ?
C6 O4 1.4837(18) . ?
C6 C8 1.556(6) . ?
C6 C7 1.571(9) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C6' C7' 1.435(12) . ?
C6' O4 1.4837(18) . ?
C6' C8' 1.533(6) . ?
C6' C9' 1.583(9) . ?
C7' H7'1 0.9800 . ?
C7' H7'2 0.9800 . ?
C7' H7'3 0.9800 . ?
C8' H8'1 0.9800 . ?
C8' H8'2 0.9800 . ?
C8' H8'3 0.9800 . ?
C9' H9'1 0.9800 . ?
C9' H9'2 0.9800 . ?
C9' H9'3 0.9800 . ?
N1 N2 1.126(2) . ?
N2 N3 1.240(2) . ?
N4 H4N 0.81(2) . ?

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
O1 C1 O2 122.35(17) . . ?
O1 C1 C4 127.12(17) . . ?
O2 C1 C4 110.52(14) . . ?
O2 C2 C3 106.42(12) . . ?
O2 C2 H2A 110.4 . . ?
C3 C2 H2A 110.4 . . ?
O2 C2 H2B 110.4 . . ?
C3 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
N4 C3 C4 115.97(13) . . ?
N4 C3 C2 110.51(12) . . ?
C4 C3 C2 103.23(12) . . ?
N4 C3 H3 109.0 . . ?
C4 C3 H3 109.0 . . ?
C2 C3 H3 109.0 . . ?
N3 C4 C1 113.33(14) . . ?
N3 C4 C3 110.42(13) . . ?
C1 C4 C3 103.59(13) . . ?
N3 C4 H4 109.8 . . ?
C1 C4 H4 109.8 . . ?
C3 C4 H4 109.8 . . ?
O3 C5 O4 125.83(13) . . ?
O3 C5 N4 124.41(14) . . ?
O4 C5 N4 109.76(13) . . ?
C9 C6 O4 110.9(6) . . ?
C9 C6 C8 115.7(5) . . ?
O4 C6 C8 102.4(2) . . ?
C9 C6 C7 113.2(7) . . ?
O4 C6 C7 110.0(5) . . ?
C8 C6 C7 103.9(5) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7' C6' O4 110.7(7) . . ?
C7' C6' C8' 116.9(6) . . ?
O4 C6' C8' 101.6(3) . . ?
C7' C6' C9' 114.2(7) . . ?
O4 C6' C9' 107.7(5) . . ?
C8' C6' C9' 104.7(5) . . ?
C6' C7' H7'1 109.5 . . ?
C6' C7' H7'2 109.5 . . ?
H7'1 C7' H7'2 109.5 . . ?
C6' C7' H7'3 109.5 . . ?
H7'1 C7' H7'3 109.5 . . ?
H7'2 C7' H7'3 109.5 . . ?
C6' C8' H8'1 109.5 . . ?
C6' C8' H8'2 109.5 . . ?
H8'1 C8' H8'2 109.5 . . ?
C6' C8' H8'3 109.5 . . ?
H8'1 C8' H8'3 109.5 . . ?
H8'2 C8' H8'3 109.5 . . ?
C6' C9' H9'1 109.5 . . ?
C6' C9' H9'2 109.5 . . ?
H9'1 C9' H9'2 109.5 . . ?
C6' C9' H9'3 109.5 . . ?
H9'1 C9' H9'3 109.5 . . ?
H9'2 C9' H9'3 109.5 . . ?
N1 N2 N3 170.3(2) . . ?
N2 N3 C4 116.37(16) . . ?
C5 N4 C3 122.64(13) . . ?
C5 N4 H4N 118.3(14) . . ?
C3 N4 H4N 118.5(14) . . ?
C1 O2 C2 111.55(13) . . ?
C5 O4 C6' 121.34(12) . . ?
C5 O4 C6 121.34(12) . . ?

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
O2 C2 C3 N4 -143.81(13) . . . . ?
O2 C2 C3 C4 -19.18(15) . . . . ?
O1 C1 C4 N3 44.4(3) . . . . ?
O2 C1 C4 N3 -136.42(15) . . . . ?
O1 C1 C4 C3 164.04(18) . . . . ?
O2 C1 C4 C3 -16.75(17) . . . . ?
N4 C3 C4 N3 -96.41(16) . . . . ?
C2 C3 C4 N3 142.60(14) . . . . ?
N4 C3 C4 C1 141.94(14) . . . . ?
C2 C3 C4 C1 20.96(15) . . . . ?
C1 C4 N3 N2 -46.4(2) . . . . ?
C3 C4 N3 N2 -162.05(15) . . . . ?
O3 C5 N4 C3 -7.7(2) . . . . ?
O4 C5 N4 C3 172.20(14) . . . . ?
C4 C3 N4 C5 109.04(17) . . . . ?
C2 C3 N4 C5 -133.96(15) . . . . ?
O1 C1 O2 C2 -176.16(17) . . . . ?
C4 C1 O2 C2 4.58(18) . . . . ?
C3 C2 O2 C1 9.58(17) . . . . ?
O3 C5 O4 C6' 0.5(3) . . . . ?
N4 C5 O4 C6' -179.47(14) . . . . ?
O3 C5 O4 C6 0.5(3) . . . . ?
N4 C5 O4 C6 -179.47(14) . . . . ?
C7' C6' O4 C5 68.9(6) . . . . ?
C8' C6' O4 C5 -166.4(5) . . . . ?
C9' C6' O4 C5 -56.6(4) . . . . ?
C9 C6 O4 C5 -72.2(6) . . . . ?
C8 C6 O4 C5 163.8(5) . . . . ?
C7 C6 O4 C5 53.8(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
N4 H4N O3 0.81(2) 2.22(2) 2.9828(17) 157.2(18) 1_455 yes

_refine_diff_density_max         0.125
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.034

