# 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_d8v19607
_audit_block_doi                 10.5517/ccdc.csd.cc23j6pk
_database_code_depnum_ccdc_archive 'CCDC 1951998'
loop_
_audit_author_name
_audit_author_address
'guangyi zhang'
;shanghai normal university
China
;
_audit_update_record             
;
2019-09-06 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 N2 O2'
_chemical_formula_weight         282.33

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'

_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                   16.9108(15)
_cell_length_b                   7.6555(6)
_cell_length_c                   11.6950(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.615(3)
_cell_angle_gamma                90
_cell_volume                     1458.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    6222
_cell_measurement_theta_min      6.435
_cell_measurement_theta_max      54.780

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6041
_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            14661
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.940
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2857
_reflns_number_gt                2299
_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)+(0.0459P)²+0.5996P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.027(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2857
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.23054(8) 0.80441(16) 0.15677(12) 0.0472(4) Uani 1 1 d . . . . .
O2 O 0.05629(9) -0.05390(19) 0.39977(13) 0.0611(4) Uani 1 1 d . . . . .
N1 N 0.27109(9) 0.52254(19) 0.11093(12) 0.0390(4) Uani 1 1 d . . . . .
H1 H 0.2546 0.5175 0.0329 0.047 Uiso 1 1 calc R U . . .
N2 N 0.24312(10) 0.5472(2) 0.40093(14) 0.0432(4) Uani 1 1 d . . . . .
C1 C 0.33935(10) 0.4347(2) 0.18096(14) 0.0335(4) Uani 1 1 d . . . . .
C2 C 0.39052(12) 0.3194(2) 0.14416(18) 0.0488(5) Uani 1 1 d . . . . .
H2A H 0.3818 0.2922 0.0624 0.059 Uiso 1 1 calc R U . . .
C3 C 0.45442(12) 0.2449(3) 0.2290(2) 0.0571(6) Uani 1 1 d . . . . .
H3 H 0.4896 0.1641 0.2053 0.069 Uiso 1 1 calc R U . . .
C4 C 0.46822(12) 0.2856(3) 0.3481(2) 0.0539(5) Uani 1 1 d . . . . .
H4 H 0.5128 0.2335 0.4052 0.065 Uiso 1 1 calc R U . . .
C5 C 0.41688(10) 0.4028(2) 0.38409(16) 0.0402(4) Uani 1 1 d . . . . .
H5 H 0.4265 0.4324 0.4656 0.048 Uiso 1 1 calc R U . . .
C6 C 0.35192(9) 0.4756(2) 0.30024(14) 0.0302(4) Uani 1 1 d . . . . .
C7 C 0.28637(10) 0.6012(2) 0.31527(14) 0.0323(4) Uani 1 1 d . . . . .
C8 C 0.23121(10) 0.6228(2) 0.18387(15) 0.0359(4) Uani 1 1 d . . . . .
H8 H 0.1743 0.5789 0.1759 0.043 Uiso 1 1 calc R U . . .
C9 C 0.30836(12) 0.8715(2) 0.22449(17) 0.0450(5) Uani 1 1 d . . . . .
H9A H 0.3069 1.0004 0.2303 0.054 Uiso 1 1 calc R U . . .
H9B H 0.3527 0.8379 0.1882 0.054 Uiso 1 1 calc R U . . .
C10 C 0.32094(12) 0.7877(2) 0.34543(16) 0.0412(4) Uani 1 1 d . . . . .
H10A H 0.2903 0.8513 0.3937 0.049 Uiso 1 1 calc R U . . .
H10B H 0.3799 0.7844 0.3890 0.049 Uiso 1 1 calc R U . . .
C11 C 0.19716(10) 0.3945(2) 0.39459(14) 0.0317(4) Uani 1 1 d . . . . .
C12 C 0.15061(10) 0.3708(2) 0.47625(14) 0.0365(4) Uani 1 1 d . . . . .
H12 H 0.1507 0.4590 0.5334 0.044 Uiso 1 1 calc R U . . .
C13 C 0.10466(11) 0.2216(2) 0.47491(15) 0.0408(4) Uani 1 1 d . . . . .
H13 H 0.0736 0.2086 0.5311 0.049 Uiso 1 1 calc R U . . .
C14 C 0.10313(10) 0.0902(2) 0.39246(15) 0.0368(4) Uani 1 1 d . . . . .
C15 C 0.14807(10) 0.1120(2) 0.31042(14) 0.0337(4) Uani 1 1 d . . . . .
H15 H 0.1474 0.0236 0.2531 0.040 Uiso 1 1 calc R U . . .
C16 C 0.19413(10) 0.2629(2) 0.31168(14) 0.0350(4) Uani 1 1 d . . . . .
H16 H 0.2243 0.2763 0.2544 0.042 Uiso 1 1 calc R U . . .
C17 C 0.05130(13) -0.1873(3) 0.3148(2) 0.0578(6) Uani 1 1 d . . . . .
H17A H 0.0268 -0.1403 0.2351 0.087 Uiso 1 1 calc R U . . .
H17B H 0.0171 -0.2828 0.3306 0.087 Uiso 1 1 calc R U . . .
H17C H 0.1065 -0.2314 0.3196 0.087 Uiso 1 1 calc R U . . .
H2 H 0.2392(12) 0.621(3) 0.4550(19) 0.051(6) Uiso 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
O1 C8 1.425(2) . ?
O1 C9 1.436(2) . ?
O2 C14 1.374(2) . ?
O2 C17 1.412(2) . ?
N1 C1 1.395(2) . ?
N1 C8 1.443(2) . ?
N1 H1 0.8800 . ?
N2 C11 1.394(2) . ?
N2 C7 1.451(2) . ?
N2 H2 0.87(2) . ?
C1 C2 1.383(2) . ?
C1 C6 1.389(2) . ?
C2 C3 1.378(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.513(2) . ?
C7 C10 1.547(2) . ?
C7 C8 1.577(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.515(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.390(2) . ?
C11 C12 1.403(2) . ?
C12 C13 1.379(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(2) . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 O1 C9 105.97(13) . . ?
C14 O2 C17 117.59(14) . . ?
C1 N1 C8 110.74(13) . . ?
C1 N1 H1 124.6 . . ?
C8 N1 H1 124.6 . . ?
C11 N2 C7 125.43(14) . . ?
C11 N2 H2 115.9(13) . . ?
C7 N2 H2 118.1(13) . . ?
C2 C1 C6 121.12(17) . . ?
C2 C1 N1 127.81(16) . . ?
C6 C1 N1 111.08(14) . . ?
C3 C2 C1 118.37(18) . . ?
C3 C2 H2A 120.8 . . ?
C1 C2 H2A 120.8 . . ?
C2 C3 C4 121.19(18) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 120.01(18) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.25(17) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 120.05(16) . . ?
C5 C6 C7 130.01(15) . . ?
C1 C6 C7 109.94(14) . . ?
N2 C7 C6 114.85(14) . . ?
N2 C7 C10 109.60(13) . . ?
C6 C7 C10 111.68(14) . . ?
N2 C7 C8 115.28(14) . . ?
C6 C7 C8 102.31(12) . . ?
C10 C7 C8 102.31(13) . . ?
O1 C8 N1 111.38(13) . . ?
O1 C8 C7 106.64(13) . . ?
N1 C8 C7 105.79(13) . . ?
O1 C8 H8 110.9 . . ?
N1 C8 H8 110.9 . . ?
C7 C8 H8 110.9 . . ?
O1 C9 C10 103.93(14) . . ?
O1 C9 H9A 111.0 . . ?
C10 C9 H9A 111.0 . . ?
O1 C9 H9B 111.0 . . ?
C10 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
C9 C10 C7 103.22(14) . . ?
C9 C10 H10A 111.1 . . ?
C7 C10 H10A 111.1 . . ?
C9 C10 H10B 111.1 . . ?
C7 C10 H10B 111.1 . . ?
H10A C10 H10B 109.1 . . ?
C16 C11 N2 124.06(14) . . ?
C16 C11 C12 117.33(15) . . ?
N2 C11 C12 118.61(14) . . ?
C13 C12 C11 121.12(15) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.87(15) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
O2 C14 C15 124.94(16) . . ?
O2 C14 C13 116.22(15) . . ?
C15 C14 C13 118.84(15) . . ?
C14 C15 C16 120.18(15) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 121.66(15) . . ?
C11 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C8 N1 C1 C2 176.51(17) . . . . ?
C8 N1 C1 C6 -3.02(19) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
N1 C1 C2 C3 -179.20(17) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 -1.4(2) . . . . ?
C4 C5 C6 C7 178.30(16) . . . . ?
C2 C1 C6 C5 0.9(2) . . . . ?
N1 C1 C6 C5 -179.55(14) . . . . ?
C2 C1 C6 C7 -178.88(15) . . . . ?
N1 C1 C6 C7 0.68(18) . . . . ?
C11 N2 C7 C6 -60.2(2) . . . . ?
C11 N2 C7 C10 173.12(16) . . . . ?
C11 N2 C7 C8 58.4(2) . . . . ?
C5 C6 C7 N2 -52.5(2) . . . . ?
C1 C6 C7 N2 127.28(15) . . . . ?
C5 C6 C7 C10 73.1(2) . . . . ?
C1 C6 C7 C10 -107.12(15) . . . . ?
C5 C6 C7 C8 -178.10(16) . . . . ?
C1 C6 C7 C8 1.64(17) . . . . ?
C9 O1 C8 N1 -84.32(16) . . . . ?
C9 O1 C8 C7 30.65(17) . . . . ?
C1 N1 C8 O1 119.40(15) . . . . ?
C1 N1 C8 C7 3.91(17) . . . . ?
N2 C7 C8 O1 112.69(15) . . . . ?
C6 C7 C8 O1 -121.95(13) . . . . ?
C10 C7 C8 O1 -6.19(16) . . . . ?
N2 C7 C8 N1 -128.63(15) . . . . ?
C6 C7 C8 N1 -3.26(16) . . . . ?
C10 C7 C8 N1 112.50(14) . . . . ?
C8 O1 C9 C10 -43.42(17) . . . . ?
O1 C9 C10 C7 37.96(17) . . . . ?
N2 C7 C10 C9 -141.59(15) . . . . ?
C6 C7 C10 C9 89.97(16) . . . . ?
C8 C7 C10 C9 -18.79(17) . . . . ?
C7 N2 C11 C16 7.6(3) . . . . ?
C7 N2 C11 C12 -172.21(16) . . . . ?
C16 C11 C12 C13 0.8(3) . . . . ?
N2 C11 C12 C13 -179.33(16) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C17 O2 C14 C15 -2.3(3) . . . . ?
C17 O2 C14 C13 177.97(18) . . . . ?
C12 C13 C14 O2 179.17(16) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
O2 C14 C15 C16 -179.40(17) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
N2 C11 C16 C15 179.10(16) . . . . ?
C12 C11 C16 C15 -1.1(2) . . . . ?
C14 C15 C16 C11 0.5(3) . . . . ?

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4



