# 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_210830c
_database_code_depnum_ccdc_archive 'CCDC 2107239'
loop_
_audit_author_name
_audit_author_address
'XiaoLong. Zhu'
;Qingdao University of science and technology
China
;
_audit_update_record             
;
2021-09-03 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 N2 O3'
_chemical_formula_weight         298.33

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.5217(9)
_cell_length_b                   16.1081(16)
_cell_length_c                   9.6233(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.665(4)
_cell_angle_gamma                90.00
_cell_volume                     1427.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2454
_cell_measurement_theta_min      2.527
_cell_measurement_theta_max      28.053

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9717
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus 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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7006
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2519
_reflns_number_gt                1831
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0531P)²+0.1618P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2519
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1080
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.58476(14) 0.08846(9) 0.36055(14) 0.0309(3) Uani 1 1 d . . .
N2 N 0.51941(14) 0.18126(9) 0.57812(14) 0.0311(3) Uani 1 1 d . . .
O1 O 0.80592(13) 0.14731(8) 0.41622(14) 0.0450(4) Uani 1 1 d . . .
O2 O 0.46822(14) 0.10048(10) 0.04742(15) 0.0562(4) Uani 1 1 d . . .
H2 H 0.4616 0.1387 -0.0102 0.084 Uiso 1 1 calc R . .
O3 O 0.96908(15) 0.27835(9) 0.35296(15) 0.0614(4) Uani 1 1 d . . .
H3C H 0.9168 0.2363 0.3581 0.074 Uiso 1 1 d R . .
H3D H 0.9754 0.2834 0.2668 0.074 Uiso 1 1 d R . .
C1 C 0.68604(17) 0.14072(11) 0.43946(18) 0.0322(4) Uani 1 1 d . . .
C2 C 0.64537(17) 0.18620(10) 0.55480(17) 0.0301(4) Uani 1 1 d . . .
C3 C 0.41634(17) 0.13097(10) 0.49112(17) 0.0303(4) Uani 1 1 d . . .
C4 C 0.44659(17) 0.08270(10) 0.38289(17) 0.0296(4) Uani 1 1 d . . .
C5 C 0.33891(18) 0.03191(11) 0.30309(19) 0.0374(4) Uani 1 1 d . . .
H5 H 0.3580 -0.0014 0.2311 0.045 Uiso 1 1 calc R . .
C6 C 0.20496(19) 0.03052(12) 0.3295(2) 0.0434(5) Uani 1 1 d . . .
H6 H 0.1338 -0.0045 0.2762 0.052 Uiso 1 1 calc R . .
C7 C 0.17347(19) 0.08009(12) 0.4336(2) 0.0445(5) Uani 1 1 d . . .
H7 H 0.0810 0.0797 0.4493 0.053 Uiso 1 1 calc R . .
C8 C 0.27841(18) 0.12962(12) 0.51339(19) 0.0393(4) Uani 1 1 d . . .
H8 H 0.2574 0.1632 0.5841 0.047 Uiso 1 1 calc R . .
C9 C 0.75770(18) 0.24032(11) 0.64912(19) 0.0352(4) Uani 1 1 d . . .
H9A H 0.7103 0.2782 0.7012 0.042 Uiso 1 1 calc R . .
H9B H 0.8044 0.2733 0.5894 0.042 Uiso 1 1 calc R . .
C10 C 0.87146(17) 0.19213(10) 0.75492(18) 0.0315(4) Uani 1 1 d . . .
C11 C 0.84213(19) 0.16038(11) 0.87704(19) 0.0381(4) Uani 1 1 d . . .
H11 H 0.7512 0.1688 0.8937 0.046 Uiso 1 1 calc R . .
C12 C 0.9453(2) 0.11640(12) 0.9747(2) 0.0440(5) Uani 1 1 d . . .
H12 H 0.9242 0.0955 1.0572 0.053 Uiso 1 1 calc R . .
C13 C 1.0790(2) 0.10326(12) 0.9507(2) 0.0436(5) Uani 1 1 d . . .
H13 H 1.1486 0.0728 1.0161 0.052 Uiso 1 1 calc R . .
C14 C 1.10937(19) 0.13477(12) 0.8315(2) 0.0457(5) Uani 1 1 d . . .
H14 H 1.2006 0.1262 0.8155 0.055 Uiso 1 1 calc R . .
C15 C 1.00696(18) 0.17934(12) 0.7337(2) 0.0399(4) Uani 1 1 d . . .
H15 H 1.0297 0.2010 0.6524 0.048 Uiso 1 1 calc R . .
C16 C 0.62865(19) 0.03980(11) 0.25072(18) 0.0379(4) Uani 1 1 d . . .
H16A H 0.5699 -0.0101 0.2316 0.045 Uiso 1 1 calc R . .
H16B H 0.7290 0.0229 0.2872 0.045 Uiso 1 1 calc R . .
C17 C 0.6138(2) 0.08595(12) 0.11367(19) 0.0434(5) Uani 1 1 d . . .
H17A H 0.6649 0.1384 0.1330 0.052 Uiso 1 1 calc R . .
H17B H 0.6572 0.0540 0.0500 0.052 Uiso 1 1 calc R . .


_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
N1 C1 1.358(2) . ?
N1 C4 1.389(2) . ?
N1 C16 1.459(2) . ?
N2 C2 1.2773(19) . ?
N2 C3 1.380(2) . ?
O1 C1 1.2220(19) . ?
O2 C17 1.391(2) . ?
O2 H2 0.8200 . ?
O3 H3C 0.8501 . ?
O3 H3D 0.8500 . ?
C1 C2 1.462(2) . ?
C2 C9 1.495(2) . ?
C3 C8 1.383(2) . ?
C3 C4 1.387(2) . ?
C4 C5 1.383(2) . ?
C5 C6 1.362(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.355(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.501(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.372(2) . ?
C10 C11 1.374(2) . ?
C11 C12 1.372(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.351(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.489(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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
C1 N1 C4 121.41(14) . . ?
C1 N1 C16 116.42(14) . . ?
C4 N1 C16 122.17(14) . . ?
C2 N2 C3 119.02(14) . . ?
C17 O2 H2 109.5 . . ?
H3C O3 H3D 108.7 . . ?
O1 C1 N1 121.02(16) . . ?
O1 C1 C2 122.33(15) . . ?
N1 C1 C2 116.62(14) . . ?
N2 C2 C1 122.91(15) . . ?
N2 C2 C9 119.26(15) . . ?
C1 C2 C9 117.83(14) . . ?
N2 C3 C8 118.19(16) . . ?
N2 C3 C4 122.25(15) . . ?
C8 C3 C4 119.55(15) . . ?
C5 C4 C3 118.88(15) . . ?
C5 C4 N1 123.50(15) . . ?
C3 C4 N1 117.62(14) . . ?
C6 C5 C4 120.25(17) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.97(17) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 119.35(17) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C3 120.96(18) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
C2 C9 C10 113.11(14) . . ?
C2 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C2 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C15 C10 C11 118.31(16) . . ?
C15 C10 C9 121.38(16) . . ?
C11 C10 C9 120.31(15) . . ?
C12 C11 C10 120.86(17) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.03(18) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 119.60(17) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.72(18) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C10 C15 C14 120.47(18) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
N1 C16 C17 113.13(15) . . ?
N1 C16 H16A 109.0 . . ?
C17 C16 H16A 109.0 . . ?
N1 C16 H16B 109.0 . . ?
C17 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
O2 C17 C16 110.52(15) . . ?
O2 C17 H17A 109.5 . . ?
C16 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?

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
C4 N1 C1 O1 -177.74(15) . . . . ?
C16 N1 C1 O1 1.6(2) . . . . ?
C4 N1 C1 C2 3.9(2) . . . . ?
C16 N1 C1 C2 -176.74(14) . . . . ?
C3 N2 C2 C1 0.0(2) . . . . ?
C3 N2 C2 C9 -179.74(14) . . . . ?
O1 C1 C2 N2 178.39(16) . . . . ?
N1 C1 C2 N2 -3.3(2) . . . . ?
O1 C1 C2 C9 -1.9(2) . . . . ?
N1 C1 C2 C9 176.41(14) . . . . ?
C2 N2 C3 C8 -176.81(15) . . . . ?
C2 N2 C3 C4 2.8(2) . . . . ?
N2 C3 C4 C5 178.00(15) . . . . ?
C8 C3 C4 C5 -2.3(2) . . . . ?
N2 C3 C4 N1 -2.2(2) . . . . ?
C8 C3 C4 N1 177.49(15) . . . . ?
C1 N1 C4 C5 178.42(15) . . . . ?
C16 N1 C4 C5 -0.9(2) . . . . ?
C1 N1 C4 C3 -1.4(2) . . . . ?
C16 N1 C4 C3 179.31(15) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
N1 C4 C5 C6 -178.88(16) . . . . ?
C4 C5 C6 C7 1.0(3) . . . . ?
C5 C6 C7 C8 -1.5(3) . . . . ?
C6 C7 C8 C3 0.1(3) . . . . ?
N2 C3 C8 C7 -178.49(16) . . . . ?
C4 C3 C8 C7 1.8(3) . . . . ?
N2 C2 C9 C10 104.81(18) . . . . ?
C1 C2 C9 C10 -74.91(19) . . . . ?
C2 C9 C10 C15 102.70(19) . . . . ?
C2 C9 C10 C11 -78.0(2) . . . . ?
C15 C10 C11 C12 -0.5(3) . . . . ?
C9 C10 C11 C12 -179.85(16) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C11 C10 C15 C14 1.0(3) . . . . ?
C9 C10 C15 C14 -179.74(17) . . . . ?
C13 C14 C15 C10 -0.5(3) . . . . ?
C1 N1 C16 C17 -83.44(18) . . . . ?
C4 N1 C16 C17 95.88(18) . . . . ?
N1 C16 C17 O2 -67.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.038
