# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_v900
_database_code_depnum_ccdc_archive 'CCDC 1588294'
loop_
_audit_author_name
_audit_author_address
'E. Rusanov' 'Institute of Organic Chemistry NAS Ukraine'
_audit_update_record             
;
2017-11-29 deposited with the CCDC.	2019-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        
'Benzyl 8-azaspiro[bicyclo[3.2.1]octane-(exo)-3,2?-oxirane]-8-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          376-377.5
_chemical_formula_moiety         'C16 H19 N O3'
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         273.32

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   7.9218(11)
_cell_length_b                   6.5193(8)
_cell_length_c                   13.4340(16)
_cell_angle_alpha                90
_cell_angle_beta                 101.580(4)
_cell_angle_gamma                90
_cell_volume                     679.67(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(1)
_cell_measurement_reflns_used    1347
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      24.92

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9802
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.547
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_full        25.242
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2956
_reflns_number_gt                2672
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_max     0.997
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0408P)²+0.0310P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1104 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2956
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0772
_refine_ls_wR_factor_gt          0.0751
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 0.7722(2) -0.0273(3) 0.67391(14) 0.0238(4) Uani 1 1 d . . . . .
H1 H 0.773333 -0.163930 0.704440 0.029 Uiso 1 1 calc R U . . .
C2 C 0.8522(2) 0.1336(3) 0.75195(14) 0.0253(4) Uani 1 1 d . . . . .
H2A H 0.786212 0.142753 0.805325 0.030 Uiso 1 1 calc R U . . .
H2B H 0.969161 0.094317 0.782575 0.030 Uiso 1 1 calc R U . . .
C3 C 0.8527(2) 0.3388(3) 0.70000(15) 0.0240(4) Uani 1 1 d . . . . .
C4 C 0.6835(2) 0.3963(3) 0.63139(15) 0.0252(4) Uani 1 1 d . . . . .
H4A H 0.700298 0.513196 0.589780 0.030 Uiso 1 1 calc R U . . .
H4B H 0.600234 0.434051 0.672142 0.030 Uiso 1 1 calc R U . . .
C5 C 0.6162(2) 0.2142(3) 0.56352(14) 0.0241(4) Uani 1 1 d . . . . .
H5 H 0.507885 0.247407 0.516790 0.029 Uiso 1 1 calc R U . . .
C6 C 0.8551(3) -0.0288(3) 0.57960(15) 0.0282(4) Uani 1 1 d . . . . .
H6A H 0.846526 -0.163786 0.548656 0.034 Uiso 1 1 calc R U . . .
H6B H 0.975595 0.009809 0.597623 0.034 Uiso 1 1 calc R U . . .
C7 C 0.7516(2) 0.1304(3) 0.50641(15) 0.0277(4) Uani 1 1 d . . . . .
H7A H 0.826218 0.239526 0.491714 0.033 Uiso 1 1 calc R U . . .
H7B H 0.696616 0.066080 0.443078 0.033 Uiso 1 1 calc R U . . .
C8 C 1.0144(3) 0.4217(3) 0.68020(16) 0.0319(5) Uani 1 1 d . . . . .
H8A H 1.117015 0.337586 0.698174 0.038 Uiso 1 1 calc R U . . .
H8B H 1.009055 0.505990 0.620143 0.038 Uiso 1 1 calc R U . . .
C9 C 0.4510(2) 0.0041(3) 0.66261(14) 0.0234(4) Uani 1 1 d . . . . .
C10 C 0.3269(3) -0.1982(3) 0.77611(16) 0.0323(5) Uani 1 1 d . . . . .
H10A H 0.338685 -0.340411 0.797563 0.039 Uiso 1 1 calc R U . . .
H10B H 0.225532 -0.187676 0.722193 0.039 Uiso 1 1 calc R U . . .
C11 C 0.3009(2) -0.0682(3) 0.86431(15) 0.0273(5) Uani 1 1 d . . . . .
C12 C 0.3699(3) 0.1258(4) 0.88202(16) 0.0331(5) Uani 1 1 d . . . . .
H12 H 0.436740 0.180069 0.838862 0.040 Uiso 1 1 calc R U . . .
C13 C 0.3403(3) 0.2405(4) 0.96379(17) 0.0437(6) Uani 1 1 d . . . . .
H13 H 0.387463 0.370971 0.975644 0.052 Uiso 1 1 calc R U . . .
C14 C 0.2401(3) 0.1598(5) 1.02767(18) 0.0497(7) Uani 1 1 d . . . . .
H14 H 0.220446 0.235715 1.082849 0.060 Uiso 1 1 calc R U . . .
C15 C 0.1696(3) -0.0327(5) 1.00954(17) 0.0454(7) Uani 1 1 d . . . . .
H15 H 0.101403 -0.086062 1.052172 0.055 Uiso 1 1 calc R U . . .
C16 C 0.1996(3) -0.1473(4) 0.92809(15) 0.0340(5) Uani 1 1 d . . . . .
H16 H 0.151755 -0.277437 0.916169 0.041 Uiso 1 1 calc R U . . .
N1 N 0.59596(19) 0.0392(2) 0.62848(12) 0.0230(4) Uani 1 1 d . . . . .
O1 O 0.94036(19) 0.5030(2) 0.76171(10) 0.0340(4) Uani 1 1 d . . . . .
O2 O 0.31283(16) 0.0863(2) 0.62991(10) 0.0323(4) Uani 1 1 d . . . . .
O3 O 0.47664(17) -0.1396(2) 0.73660(10) 0.0300(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 N1 1.472(2) . ?
C1 C2 1.528(3) . ?
C1 C6 1.539(3) . ?
C2 C3 1.510(3) . ?
C3 O1 1.443(2) . ?
C3 C8 1.463(3) . ?
C3 C4 1.513(3) . ?
C4 C5 1.526(3) . ?
C5 N1 1.465(2) . ?
C5 C7 1.539(3) . ?
C6 C7 1.546(3) . ?
C8 O1 1.443(3) . ?
C9 O2 1.218(2) . ?
C9 N1 1.339(2) . ?
C9 O3 1.351(2) . ?
C10 O3 1.445(2) . ?
C10 C11 1.504(3) . ?
C11 C12 1.379(3) . ?
C11 C16 1.386(3) . ?
C12 C13 1.387(3) . ?
C13 C14 1.384(4) . ?
C14 C15 1.375(4) . ?
C15 C16 1.385(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
N1 C1 C2 108.09(15) . . ?
N1 C1 C6 100.73(15) . . ?
C2 C1 C6 112.50(16) . . ?
C3 C2 C1 109.30(14) . . ?
O1 C3 C8 59.52(13) . . ?
O1 C3 C2 115.92(15) . . ?
C8 C3 C2 119.67(17) . . ?
O1 C3 C4 115.58(16) . . ?
C8 C3 C4 119.91(18) . . ?
C2 C3 C4 114.63(16) . . ?
C3 C4 C5 109.41(16) . . ?
N1 C5 C4 108.47(14) . . ?
N1 C5 C7 101.00(16) . . ?
C4 C5 C7 112.25(16) . . ?
C1 C6 C7 105.08(15) . . ?
C5 C7 C6 104.76(16) . . ?
O1 C8 C3 59.56(13) . . ?
O2 C9 N1 124.85(18) . . ?
O2 C9 O3 124.17(17) . . ?
N1 C9 O3 110.95(16) . . ?
O3 C10 C11 113.14(16) . . ?
C12 C11 C16 119.5(2) . . ?
C12 C11 C10 122.70(18) . . ?
C16 C11 C10 117.73(19) . . ?
C11 C12 C13 120.4(2) . . ?
C14 C13 C12 119.7(3) . . ?
C15 C14 C13 120.0(2) . . ?
C14 C15 C16 120.3(2) . . ?
C15 C16 C11 120.0(2) . . ?
C9 N1 C5 122.74(16) . . ?
C9 N1 C1 127.95(16) . . ?
C5 N1 C1 105.57(14) . . ?
C8 O1 C3 60.92(12) . . ?
C9 O3 C10 116.11(16) . . ?

_refine_diff_density_max         0.150
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.036



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
