# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1902886'
loop_
_audit_author_name
_audit_author_address
'Jianbo Wang'
;Peking University
China
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 N2 O3'
_chemical_formula_weight         324.37

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                   6.5666(3)
_cell_length_b                   16.4713(6)
_cell_length_c                   8.0376(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.405(5)
_cell_angle_gamma                90
_cell_volume                     809.39(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    180.00(10)
_cell_measurement_reflns_used    3032
_cell_measurement_theta_min      2.7190
_cell_measurement_theta_max      28.8470

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.94243
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5239
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.473
_diffrn_reflns_theta_max         29.261
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.636
_diffrn_reflns_point_group_measured_fraction_full 0.739
_reflns_number_total             2802
_reflns_number_gt                2586
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.353
_reflns_Friedel_fraction_max     0.343
_reflns_Friedel_fraction_full    0.459

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0513P)²+0.0107P] 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 663 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2802
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0880
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.4899(4) 0.76430(11) 0.5195(3) 0.0535(5) Uani 1 1 d . . . . .
O2 O 0.0787(2) 0.31161(9) 0.1023(2) 0.0354(4) Uani 1 1 d . . . . .
O3 O 0.3647(3) 0.28090(9) 0.0254(2) 0.0342(4) Uani 1 1 d . . . . .
N1 N 0.3178(2) 0.52794(9) 0.2886(2) 0.0204(3) Uani 1 1 d . . . . .
N2 N 0.2364(2) 0.45304(9) 0.2121(2) 0.0208(3) Uani 1 1 d . . . . .
C1 C 0.3418(3) 0.63596(12) 0.4556(3) 0.0245(4) Uani 1 1 d . . . . .
C2 C 0.4405(3) 0.65325(12) 0.3323(3) 0.0255(4) Uani 1 1 d . . . . .
C3 C 0.4217(3) 0.58712(12) 0.2230(3) 0.0227(4) Uani 1 1 d . . . . .
C4 C 0.2611(3) 0.55812(11) 0.4281(2) 0.0208(4) Uani 1 1 d . . . . .
C5 C 0.3628(4) 0.70712(13) 0.5752(3) 0.0364(5) Uani 1 1 d . . . . .
H5A H 0.2204 0.7293 0.5600 0.044 Uiso 1 1 calc R U . . .
H5B H 0.4371 0.6921 0.6994 0.044 Uiso 1 1 calc R U . . .
C6 C 0.5339(4) 0.73704(14) 0.3664(3) 0.0353(5) Uani 1 1 d . . . . .
H6A H 0.6899 0.7362 0.3912 0.042 Uiso 1 1 calc R U . . .
H6B H 0.4635 0.7720 0.2644 0.042 Uiso 1 1 calc R U . . .
C7 C 0.1416(3) 0.51300(12) 0.5203(2) 0.0218(4) Uani 1 1 d . . . . .
C8 C -0.0084(3) 0.55508(13) 0.5731(3) 0.0280(4) Uani 1 1 d . . . . .
H8 H -0.0304 0.6102 0.5479 0.034 Uiso 1 1 calc R U . . .
C9 C -0.1255(4) 0.51633(15) 0.6623(3) 0.0345(5) Uani 1 1 d . . . . .
H9 H -0.2261 0.5453 0.6956 0.041 Uiso 1 1 calc R U . . .
C10 C -0.0933(4) 0.43544(16) 0.7018(3) 0.0365(5) Uani 1 1 d . . . . .
H10 H -0.1711 0.4096 0.7627 0.044 Uiso 1 1 calc R U . . .
C11 C 0.0546(4) 0.39208(14) 0.6510(3) 0.0337(5) Uani 1 1 d . . . . .
H11 H 0.0755 0.3370 0.6775 0.040 Uiso 1 1 calc R U . . .
C12 C 0.1724(3) 0.43028(13) 0.5606(3) 0.0271(4) Uani 1 1 d . . . . .
H12 H 0.2718 0.4008 0.5269 0.032 Uiso 1 1 calc R U . . .
C13 C 0.4586(4) 0.58110(13) 0.0509(3) 0.0278(4) Uani 1 1 d . . . . .
H13A H 0.4535 0.6355 0.0034 0.033 Uiso 1 1 calc R U . . .
H13B H 0.3376 0.5510 -0.0330 0.033 Uiso 1 1 calc R U . . .
C14 C 0.6711(3) 0.54125(13) 0.0571(3) 0.0313(5) Uani 1 1 d . . . . .
H14A H 0.7015 0.5583 -0.0470 0.038 Uiso 1 1 calc R U . . .
H14B H 0.7897 0.5606 0.1621 0.038 Uiso 1 1 calc R U . . .
C15 C 0.6676(3) 0.44904(14) 0.0618(3) 0.0294(5) Uani 1 1 d . . . . .
H15A H 0.8102 0.4287 0.0720 0.035 Uiso 1 1 calc R U . . .
H15B H 0.5617 0.4292 -0.0500 0.035 Uiso 1 1 calc R U . . .
C16 C 0.6095(3) 0.41548(12) 0.2169(3) 0.0243(4) Uani 1 1 d . . . . .
H16A H 0.6792 0.3630 0.2509 0.029 Uiso 1 1 calc R U . . .
H16B H 0.6699 0.4515 0.3186 0.029 Uiso 1 1 calc R U . . .
C17 C 0.3708(3) 0.40603(11) 0.1772(2) 0.0194(4) Uani 1 1 d . . . . .
C18 C 0.2728(3) 0.32612(12) 0.0930(2) 0.0243(4) Uani 1 1 d . . . . .
C19 C -0.0170(5) 0.23449(16) 0.0331(4) 0.0553(8) Uani 1 1 d . . . . .
H19A H -0.0323 0.2300 -0.0900 0.083 Uiso 1 1 calc R U . . .
H19B H -0.1584 0.2303 0.0423 0.083 Uiso 1 1 calc R U . . .
H19C H 0.0755 0.1917 0.1007 0.083 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 C5 1.434(3) . ?
O1 C6 1.435(3) . ?
O2 C18 1.325(2) . ?
O2 C19 1.436(3) . ?
O3 C18 1.206(2) . ?
N1 N2 1.395(2) . ?
N1 C4 1.395(2) . ?
N1 C3 1.399(2) . ?
N2 C17 1.280(2) . ?
C1 C4 1.374(3) . ?
C1 C2 1.398(3) . ?
C1 C5 1.490(3) . ?
C2 C3 1.376(3) . ?
C2 C6 1.494(3) . ?
C3 C13 1.492(3) . ?
C4 C7 1.464(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.391(3) . ?
C7 C12 1.398(3) . ?
C8 C9 1.384(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.368(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.526(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.520(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.533(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.490(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.512(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
C5 O1 C6 112.59(16) . . ?
C18 O2 C19 115.59(19) . . ?
N2 N1 C4 119.85(15) . . ?
N2 N1 C3 127.69(15) . . ?
C4 N1 C3 111.37(15) . . ?
C17 N2 N1 116.61(15) . . ?
C4 C1 C2 109.11(17) . . ?
C4 C1 C5 141.03(19) . . ?
C2 C1 C5 109.84(18) . . ?
C3 C2 C1 109.54(17) . . ?
C3 C2 C6 141.6(2) . . ?
C1 C2 C6 108.87(19) . . ?
C2 C3 N1 104.70(17) . . ?
C2 C3 C13 129.57(18) . . ?
N1 C3 C13 124.72(17) . . ?
C1 C4 N1 105.16(16) . . ?
C1 C4 C7 129.71(17) . . ?
N1 C4 C7 125.13(16) . . ?
O1 C5 C1 104.08(18) . . ?
O1 C5 H5A 110.9 . . ?
C1 C5 H5A 110.9 . . ?
O1 C5 H5B 110.9 . . ?
C1 C5 H5B 110.9 . . ?
H5A C5 H5B 109.0 . . ?
O1 C6 C2 104.41(19) . . ?
O1 C6 H6A 110.9 . . ?
C2 C6 H6A 110.9 . . ?
O1 C6 H6B 110.9 . . ?
C2 C6 H6B 110.9 . . ?
H6A C6 H6B 108.9 . . ?
C8 C7 C12 118.26(18) . . ?
C8 C7 C4 118.14(17) . . ?
C12 C7 C4 123.60(18) . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.1(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 120.1(2) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
C3 C13 C14 117.01(17) . . ?
C3 C13 H13A 108.0 . . ?
C14 C13 H13A 108.0 . . ?
C3 C13 H13B 108.0 . . ?
C14 C13 H13B 108.0 . . ?
H13A C13 H13B 107.3 . . ?
C15 C14 C13 114.11(17) . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 C16 113.02(16) . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 114.71(15) . . ?
C17 C16 H16A 108.6 . . ?
C15 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
C15 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
N2 C17 C16 130.22(16) . . ?
N2 C17 C18 114.21(16) . . ?
C16 C17 C18 115.44(16) . . ?
O3 C18 O2 124.32(19) . . ?
O3 C18 C17 122.56(19) . . ?
O2 C18 C17 113.12(16) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.142
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041



