# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_mo_20180522A_0m
_database_code_depnum_ccdc_archive 'CCDC 1937084'
loop_
_audit_author_name
_audit_author_address
ZR
;XIBEISHIFANDAXUE
China
;
_audit_update_record             
;
2019-06-28 deposited with the CCDC.	2020-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.33

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   9.0158(2)
_cell_length_b                   10.7244(3)
_cell_length_c                   32.8321(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3174.50(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53238
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.1390
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.481
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3116
_reflns_number_gt                2454
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1102P)²+0.3715P] 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-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3116
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1810
_refine_ls_wR_factor_gt          0.1723
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
C1 C 0.8899(2) 0.91012(14) 0.03987(5) 0.0516(4) Uani 1 1 d . . . . .
C2 C 0.77231(18) 0.97826(13) 0.06175(4) 0.0476(4) Uani 1 1 d . . . . .
C3 C 0.6275(2) 0.96971(18) 0.04711(6) 0.0631(5) Uani 1 1 d . . . . .
H3 H 0.606840 0.920331 0.024520 0.076 Uiso 1 1 calc R U . . .
C4 C 0.5154(2) 1.0340(2) 0.06597(7) 0.0745(6) Uani 1 1 d . . . . .
H4 H 0.418588 1.027754 0.056439 0.089 Uiso 1 1 calc R U . . .
C5 C 0.5473(3) 1.1081(2) 0.09919(7) 0.0769(6) Uani 1 1 d . . . . .
H5 H 0.471765 1.152493 0.111888 0.092 Uiso 1 1 calc R U . . .
C6 C 0.6894(2) 1.11674(18) 0.11358(6) 0.0661(5) Uani 1 1 d . . . . .
H6 H 0.709160 1.167519 0.135888 0.079 Uiso 1 1 calc R U . . .
C7 C 0.80433(19) 1.05134(13) 0.09556(4) 0.0480(4) Uani 1 1 d . . . . .
C8 C 0.9620(2) 1.06505(16) 0.11024(5) 0.0532(4) Uani 1 1 d . . . . .
C9 C 1.0651(2) 0.96497(19) 0.09371(5) 0.0613(5) Uani 1 1 d . . . . .
C10 C 1.1444(2) 0.83366(19) 0.03691(6) 0.0671(5) Uani 1 1 d . . . . .
H10A H 1.200866 0.887388 0.019392 0.101 Uiso 1 1 calc R U . . .
H10B H 1.098890 0.769087 0.020979 0.101 Uiso 1 1 calc R U . . .
H10C H 1.208954 0.796850 0.056814 0.101 Uiso 1 1 calc R U . . .
C11 C 1.0248(3) 1.1898(2) 0.09420(6) 0.0826(7) Uani 1 1 d . . . . .
H11A H 1.024186 1.189267 0.064958 0.124 Uiso 1 1 calc R U . . .
H11B H 1.124668 1.200277 0.103760 0.124 Uiso 1 1 calc R U . . .
H11C H 0.964614 1.257401 0.103907 0.124 Uiso 1 1 calc R U . . .
C12 C 0.9752(2) 1.06785(16) 0.15696(5) 0.0587(5) Uani 1 1 d . . . . .
H12A H 1.078981 1.077287 0.164099 0.070 Uiso 1 1 calc R U . . .
H12B H 0.923075 1.140752 0.167011 0.070 Uiso 1 1 calc R U . . .
C13 C 0.9156(2) 0.95527(15) 0.17829(5) 0.0585(5) Uani 1 1 d . . . . .
C14 C 0.9029(2) 0.95705(16) 0.22365(5) 0.0575(5) Uani 1 1 d . . . . .
C15 C 0.9669(3) 1.0499(2) 0.24688(6) 0.0800(6) Uani 1 1 d . . . . .
H15 H 1.016480 1.115094 0.234083 0.096 Uiso 1 1 calc R U . . .
C16 C 0.9584(3) 1.0472(3) 0.28902(7) 0.1009(9) Uani 1 1 d . . . . .
H16 H 1.002877 1.109846 0.304350 0.121 Uiso 1 1 calc R U . . .
C17 C 0.8841(3) 0.9520(3) 0.30806(7) 0.0971(8) Uani 1 1 d . . . . .
H17 H 0.879499 0.949286 0.336340 0.117 Uiso 1 1 calc R U . . .
C18 C 0.8173(3) 0.8617(3) 0.28555(8) 0.0963(8) Uani 1 1 d . . . . .
H18 H 0.765268 0.798357 0.298590 0.116 Uiso 1 1 calc R U . . .
C19 C 0.8259(3) 0.8629(2) 0.24307(7) 0.0780(6) Uani 1 1 d . . . . .
H19 H 0.779980 0.800538 0.227939 0.094 Uiso 1 1 calc R U . . .
N1 N 1.02903(15) 0.90657(13) 0.05761(4) 0.0515(4) Uani 1 1 d . . . . .
O1 O 0.86831(17) 0.85764(15) 0.00777(4) 0.0804(5) Uani 1 1 d . . . . .
O2 O 1.18305(18) 0.9436(2) 0.10950(5) 0.1110(7) Uani 1 1 d . . . . .
O3 O 0.8807(2) 0.86377(12) 0.15912(4) 0.0964(6) 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 O1 1.2104(19) . ?
C1 N1 1.384(2) . ?
C1 C2 1.474(2) . ?
C2 C7 1.389(2) . ?
C2 C3 1.395(3) . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.508(2) . ?
C8 C9 1.520(3) . ?
C8 C12 1.539(2) . ?
C8 C11 1.545(3) . ?
C9 O2 1.205(2) . ?
C9 N1 1.380(2) . ?
C10 N1 1.468(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.496(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O3 1.208(2) . ?
C13 C14 1.494(2) . ?
C14 C15 1.381(3) . ?
C14 C19 1.382(3) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.359(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.397(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

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
O1 C1 N1 119.95(16) . . ?
O1 C1 C2 122.62(16) . . ?
N1 C1 C2 117.42(13) . . ?
C7 C2 C3 120.47(16) . . ?
C7 C2 C1 121.30(15) . . ?
C3 C2 C1 118.22(14) . . ?
C4 C3 C2 120.07(18) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.47(19) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 121.26(18) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C2 118.17(16) . . ?
C6 C7 C8 121.30(15) . . ?
C2 C7 C8 120.41(14) . . ?
C7 C8 C9 113.16(13) . . ?
C7 C8 C12 113.16(14) . . ?
C9 C8 C12 108.81(15) . . ?
C7 C8 C11 108.72(16) . . ?
C9 C8 C11 105.41(16) . . ?
C12 C8 C11 107.13(13) . . ?
O2 C9 N1 119.41(18) . . ?
O2 C9 C8 121.37(17) . . ?
N1 C9 C8 118.90(16) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C8 115.05(13) . . ?
C13 C12 H12A 108.5 . . ?
C8 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C8 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
O3 C13 C14 120.66(16) . . ?
O3 C13 C12 120.37(16) . . ?
C14 C13 C12 118.96(14) . . ?
C15 C14 C19 118.84(18) . . ?
C15 C14 C13 121.86(17) . . ?
C19 C14 C13 119.30(17) . . ?
C14 C15 C16 120.9(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 119.9(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.8(2) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C14 C19 C18 119.7(2) . . ?
C14 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C9 N1 C1 124.25(14) . . ?
C9 N1 C10 118.20(15) . . ?
C1 N1 C10 117.54(13) . . ?

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.072

