# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_d8v20635
_database_code_depnum_ccdc_archive 'CCDC 2062592'
loop_
_audit_author_name
_audit_author_address
'Hao Li'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2021-02-11 deposited with the CCDC.	2021-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H21 N O3'
_chemical_formula_weight         275.34

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.3280(6)
_cell_length_b                   5.5386(2)
_cell_length_c                   17.0245(6)
_cell_angle_alpha                90
_cell_angle_beta                 115.7840(10)
_cell_angle_gamma                90
_cell_volume                     1471.22(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    4111
_cell_measurement_theta_min      5.601
_cell_measurement_theta_max      55.017

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6747
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6846
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.801
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2873
_reflns_number_gt                2484
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0390P)²+0.4600P] 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     SHELXL
_refine_ls_extinction_coef       0.034(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2873
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
O1 O 0.24851(6) 1.01649(15) 0.16900(6) 0.0329(2) Uani 1 1 d . . . . .
O2 O 0.24094(5) 0.44513(15) 0.26193(6) 0.0291(2) Uani 1 1 d . . . . .
H2 H 0.2183 0.3317 0.2266 0.044 Uiso 1 1 calc R U . . .
O3 O 0.09883(6) 0.40232(17) 0.12283(7) 0.0394(3) Uani 1 1 d . . . . .
N1 N 0.32306(6) 0.66545(18) 0.18667(7) 0.0254(2) Uani 1 1 d . . . . .
H1 H 0.3252 0.5157 0.2048 0.031 Uiso 1 1 calc R U . . .
C1 C 0.45148(8) 0.5641(2) 0.17523(8) 0.0314(3) Uani 1 1 d . . . . .
H1A H 0.4526 0.4179 0.2049 0.038 Uiso 1 1 calc R U . . .
C2 C 0.51551(9) 0.6128(3) 0.14973(9) 0.0413(4) Uani 1 1 d . . . . .
H2A H 0.5605 0.4997 0.1620 0.050 Uiso 1 1 calc R U . . .
C3 C 0.51448(9) 0.8250(3) 0.10654(9) 0.0431(4) Uani 1 1 d . . . . .
H3 H 0.5591 0.8597 0.0900 0.052 Uiso 1 1 calc R U . . .
C4 C 0.44784(9) 0.9858(3) 0.08769(9) 0.0389(3) Uani 1 1 d . . . . .
H4 H 0.4464 1.1304 0.0571 0.047 Uiso 1 1 calc R U . . .
C5 C 0.38285(8) 0.9402(2) 0.11267(8) 0.0314(3) Uani 1 1 d . . . . .
H5 H 0.3373 1.0520 0.0993 0.038 Uiso 1 1 calc R U . . .
C6 C 0.38544(7) 0.7286(2) 0.15752(7) 0.0251(3) Uani 1 1 d . . . . .
C7 C 0.26081(7) 0.8039(2) 0.19041(7) 0.0237(3) Uani 1 1 d . . . . .
C8 C 0.20245(7) 0.6657(2) 0.22309(8) 0.0239(3) Uani 1 1 d . . . . .
C9 C 0.11720(8) 0.6114(2) 0.14202(8) 0.0269(3) Uani 1 1 d . . . . .
C10 C 0.06141(9) 0.8137(3) 0.09069(9) 0.0367(3) Uani 1 1 d . . . . .
H10A H 0.0150 0.7499 0.0374 0.055 Uiso 1 1 calc R U . . .
H10B H 0.0955 0.9288 0.0753 0.055 Uiso 1 1 calc R U . . .
H10C H 0.0369 0.8956 0.1257 0.055 Uiso 1 1 calc R U . . .
C11 C 0.18724(7) 0.8228(2) 0.28987(8) 0.0245(3) Uani 1 1 d . . . . .
H11 H 0.1652 0.9830 0.2620 0.029 Uiso 1 1 calc R U . . .
C12 C 0.12029(8) 0.7141(3) 0.31582(9) 0.0329(3) Uani 1 1 d . . . . .
H12A H 0.0657 0.6903 0.2630 0.040 Uiso 1 1 calc R U . . .
H12B H 0.1403 0.5545 0.3434 0.040 Uiso 1 1 calc R U . . .
C13 C 0.10546(9) 0.8802(3) 0.37939(9) 0.0419(4) Uani 1 1 d . . . . .
H13A H 0.0813 1.0354 0.3501 0.050 Uiso 1 1 calc R U . . .
H13B H 0.0633 0.8052 0.3966 0.050 Uiso 1 1 calc R U . . .
C14 C 0.18848(10) 0.9280(3) 0.46060(9) 0.0444(4) Uani 1 1 d . . . . .
H14A H 0.1774 1.0444 0.4987 0.053 Uiso 1 1 calc R U . . .
H14B H 0.2091 0.7757 0.4935 0.053 Uiso 1 1 calc R U . . .
C15 C 0.25708(9) 1.0288(3) 0.43686(9) 0.0385(3) Uani 1 1 d . . . . .
H15A H 0.3116 1.0441 0.4904 0.046 Uiso 1 1 calc R U . . .
H15B H 0.2399 1.1920 0.4115 0.046 Uiso 1 1 calc R U . . .
C16 C 0.27110(8) 0.8674(3) 0.37162(8) 0.0318(3) Uani 1 1 d . . . . .
H16A H 0.2952 0.7108 0.3996 0.038 Uiso 1 1 calc R U . . .
H16B H 0.3131 0.9445 0.3546 0.038 Uiso 1 1 calc R U . . .


_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
O1 C7 1.2233(15) . ?
O2 C8 1.4112(14) . ?
O2 H2 0.8400 . ?
O3 C9 1.2078(15) . ?
N1 C7 1.3475(15) . ?
N1 C6 1.4156(15) . ?
N1 H1 0.8800 . ?
C1 C2 1.3825(19) . ?
C1 C6 1.3892(17) . ?
C1 H1A 0.9500 . ?
C2 C3 1.382(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.381(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3891(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3886(18) . ?
C5 H5 0.9500 . ?
C7 C8 1.5516(16) . ?
C8 C11 1.5426(16) . ?
C8 C9 1.5505(17) . ?
C9 C10 1.4895(18) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.5329(16) . ?
C11 C16 1.5330(17) . ?
C11 H11 1.0000 . ?
C12 C13 1.5252(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.523(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.518(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5251(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

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
C8 O2 H2 109.5 . . ?
C7 N1 C6 128.69(10) . . ?
C7 N1 H1 115.7 . . ?
C6 N1 H1 115.7 . . ?
C2 C1 C6 120.11(13) . . ?
C2 C1 H1A 119.9 . . ?
C6 C1 H1A 119.9 . . ?
C3 C2 C1 120.44(13) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C4 C3 C2 119.21(13) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.24(13) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 119.03(12) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 119.95(11) . . ?
C5 C6 N1 123.66(11) . . ?
C1 C6 N1 116.39(11) . . ?
O1 C7 N1 124.96(11) . . ?
O1 C7 C8 121.69(10) . . ?
N1 C7 C8 113.34(10) . . ?
O2 C8 C11 109.91(9) . . ?
O2 C8 C9 108.80(9) . . ?
C11 C8 C9 111.31(9) . . ?
O2 C8 C7 110.26(9) . . ?
C11 C8 C7 109.45(9) . . ?
C9 C8 C7 107.08(9) . . ?
O3 C9 C10 122.36(12) . . ?
O3 C9 C8 117.63(11) . . ?
C10 C9 C8 120.01(10) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 109.81(10) . . ?
C12 C11 C8 112.58(10) . . ?
C16 C11 C8 111.19(10) . . ?
C12 C11 H11 107.7 . . ?
C16 C11 H11 107.7 . . ?
C8 C11 H11 107.7 . . ?
C13 C12 C11 110.46(11) . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 111.40(11) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C13 111.21(11) . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 111.69(12) . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 C11 111.54(10) . . ?
C15 C16 H16A 109.3 . . ?
C11 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C11 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?

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
C6 C1 C2 C3 0.0(2) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 C1 -1.28(18) . . . . ?
C4 C5 C6 N1 179.40(11) . . . . ?
C2 C1 C6 C5 1.23(18) . . . . ?
C2 C1 C6 N1 -179.40(12) . . . . ?
C7 N1 C6 C5 -11.86(19) . . . . ?
C7 N1 C6 C1 168.79(11) . . . . ?
C6 N1 C7 O1 -0.80(19) . . . . ?
C6 N1 C7 C8 177.73(10) . . . . ?
O1 C7 C8 O2 -166.60(11) . . . . ?
N1 C7 C8 O2 14.81(13) . . . . ?
O1 C7 C8 C11 -45.59(15) . . . . ?
N1 C7 C8 C11 135.82(10) . . . . ?
O1 C7 C8 C9 75.19(13) . . . . ?
N1 C7 C8 C9 -103.40(11) . . . . ?
O2 C8 C9 O3 -2.80(15) . . . . ?
C11 C8 C9 O3 -124.06(12) . . . . ?
C7 C8 C9 O3 116.36(12) . . . . ?
O2 C8 C9 C10 177.43(11) . . . . ?
C11 C8 C9 C10 56.17(15) . . . . ?
C7 C8 C9 C10 -63.42(14) . . . . ?
O2 C8 C11 C12 -66.70(12) . . . . ?
C9 C8 C11 C12 53.90(13) . . . . ?
C7 C8 C11 C12 172.08(9) . . . . ?
O2 C8 C11 C16 57.01(13) . . . . ?
C9 C8 C11 C16 177.62(10) . . . . ?
C7 C8 C11 C16 -64.21(12) . . . . ?
C16 C11 C12 C13 57.46(14) . . . . ?
C8 C11 C12 C13 -178.07(10) . . . . ?
C11 C12 C13 C14 -57.51(16) . . . . ?
C12 C13 C14 C15 55.45(17) . . . . ?
C13 C14 C15 C16 -53.94(17) . . . . ?
C14 C15 C16 C11 55.00(15) . . . . ?
C12 C11 C16 C15 -56.41(14) . . . . ?
C8 C11 C16 C15 178.31(11) . . . . ?

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.032

_shelxl_version_number           2013-4

