# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_180530j
_database_code_depnum_ccdc_archive 'CCDC 1938560'
loop_
_audit_author_name
_audit_author_address
'Rao jiarui'
;Guizhou University
China
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-12-18 downloaded from the CCDC.
;
_audit_creation_date             2019-07-05
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.03.18 svn.r3573 for OlexSys, GUI svn.r5794)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H22 N2 O3'
_chemical_formula_sum            'C19 H22 N2 O3'
_chemical_formula_weight         326.38
_chemical_melting_point          ?
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'

_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.
;
_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'
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                   7.2797(5)
_cell_length_b                   14.3957(12)
_cell_length_c                   32.249(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3379.5(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2321
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.436
_cell_measurement_theta_min      2.527
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9659
_exptl_absorpt_correction_T_min  0.9618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.4
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15106
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.017
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_min         2.526
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1701
_reflns_number_total             2987
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2987
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0231P)²+3.0480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1557
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C9(H9A,H9B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
N1 N 0.1619(3) 0.34995(16) 0.15090(7) 0.0395(6) Uani 1 1 d . . . . .
N2 N 0.5962(4) 0.17457(19) 0.19110(9) 0.0616(8) Uani 1 1 d . . . . .
H2 H 0.6640 0.1631 0.2123 0.074 Uiso 1 1 calc R . . . .
O1 O 0.3635(3) 0.43517(15) 0.08960(7) 0.0558(6) Uani 1 1 d . . . . .
O2 O 0.2391(3) 0.46843(14) 0.19368(7) 0.0603(7) Uani 1 1 d . . . . .
O3 O 0.2080(4) 0.14921(15) 0.21968(7) 0.0668(8) Uani 1 1 d . . . . .
H3 H 0.2287 0.0953 0.2129 0.100 Uiso 1 1 calc GR . . . .
C1 C 0.2273(4) 0.4363(2) 0.15847(10) 0.0427(8) Uani 1 1 d . . . . .
C2 C 0.2864(5) 0.4909(2) 0.12155(10) 0.0483(8) Uani 1 1 d . . . . .
H2A H 0.1812 0.5241 0.1105 0.058 Uiso 1 1 calc R . . . .
H2B H 0.3765 0.5367 0.1302 0.058 Uiso 1 1 calc R . . . .
C3 C 0.2572(4) 0.3601(2) 0.07941(9) 0.0434(7) Uani 1 1 d . . . . .
C4 C 0.1519(4) 0.31705(19) 0.10941(9) 0.0373(7) Uani 1 1 d . . . . .
C5 C 0.0480(4) 0.2403(2) 0.09838(10) 0.0500(8) Uani 1 1 d . . . . .
H5 H -0.0282 0.2121 0.1178 0.060 Uiso 1 1 calc R . . . .
C6 C 0.0578(5) 0.2057(2) 0.05847(11) 0.0625(10) Uani 1 1 d . . . . .
H6 H -0.0107 0.1536 0.0512 0.075 Uiso 1 1 calc R . . . .
C7 C 0.1677(5) 0.2476(3) 0.02949(11) 0.0663(11) Uani 1 1 d . . . . .
H7 H 0.1764 0.2231 0.0029 0.080 Uiso 1 1 calc R . . . .
C8 C 0.2644(5) 0.3254(2) 0.03985(10) 0.0574(9) Uani 1 1 d . . . . .
H8 H 0.3357 0.3552 0.0199 0.069 Uiso 1 1 calc R . . . .
C9 C 0.1218(4) 0.2874(2) 0.18550(9) 0.0450(8) Uani 1 1 d . . . . .
H9A H 0.0001 0.2611 0.1820 0.054 Uiso 1 1 calc R . . . .
H9B H 0.1236 0.3220 0.2113 0.054 Uiso 1 1 calc R . . . .
C10 C 0.2630(4) 0.2096(2) 0.18739(9) 0.0435(8) Uani 1 1 d . . . . .
H10 H 0.2600 0.1753 0.1611 0.052 Uiso 1 1 calc R . . . .
C11 C 0.4566(5) 0.2459(2) 0.19429(10) 0.0529(9) Uani 1 1 d . . . . .
H11A H 0.4820 0.2940 0.1740 0.064 Uiso 1 1 calc R . . . .
H11B H 0.4634 0.2740 0.2216 0.064 Uiso 1 1 calc R . . . .
C12 C 0.6241(4) 0.1244(2) 0.15517(10) 0.0457(8) Uani 1 1 d . . . . .
C13 C 0.6989(4) 0.0346(2) 0.15752(10) 0.0474(8) Uani 1 1 d . . . . .
C14 C 0.7251(4) -0.0138(2) 0.12082(11) 0.0548(9) Uani 1 1 d . . . . .
H14 H 0.7748 -0.0732 0.1224 0.066 Uiso 1 1 calc R . . . .
C15 C 0.6817(4) 0.0207(3) 0.08218(11) 0.0584(9) Uani 1 1 d . . . . .
C16 C 0.6094(4) 0.1089(3) 0.08078(11) 0.0581(9) Uani 1 1 d . . . . .
H16 H 0.5790 0.1346 0.0552 0.070 Uiso 1 1 calc R . . . .
C17 C 0.5808(4) 0.1601(2) 0.11632(10) 0.0525(9) Uani 1 1 d . . . . .
H17 H 0.5317 0.2196 0.1143 0.063 Uiso 1 1 calc R . . . .
C18 C 0.7460(5) -0.0075(3) 0.19855(10) 0.0661(10) Uani 1 1 d . . . . .
H18A H 0.7862 -0.0704 0.1946 0.099 Uiso 1 1 calc GR . . . .
H18B H 0.6396 -0.0069 0.2161 0.099 Uiso 1 1 calc GR . . . .
H18C H 0.8426 0.0278 0.2113 0.099 Uiso 1 1 calc GR . . . .
C19 C 0.7113(6) -0.0362(3) 0.04335(12) 0.0834(13) Uani 1 1 d . . . . .
H19A H 0.8389 -0.0346 0.0358 0.125 Uiso 1 1 calc GR . . . .
H19B H 0.6389 -0.0109 0.0212 0.125 Uiso 1 1 calc GR . . . .
H19C H 0.6749 -0.0993 0.0484 0.125 Uiso 1 1 calc GR . . . .


_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 1.354(4) . ?
N1 C4 1.422(3) . ?
N1 C9 1.463(3) . ?
N2 H2 0.8600 . ?
N2 C11 1.449(4) . ?
N2 C12 1.380(4) . ?
O1 C2 1.422(4) . ?
O1 C3 1.370(3) . ?
O2 C1 1.229(3) . ?
O3 H3 0.8200 . ?
O3 C10 1.414(3) . ?
C1 C2 1.490(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.381(4) . ?
C3 C8 1.371(4) . ?
C4 C5 1.385(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.370(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.365(5) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.521(4) . ?
C10 H10 0.9800 . ?
C10 C11 1.520(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.405(4) . ?
C12 C17 1.391(4) . ?
C13 C14 1.387(4) . ?
C13 C18 1.495(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(5) . ?
C15 C16 1.375(5) . ?
C15 C19 1.512(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(5) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
C1 N1 C4 119.6(2) . . ?
C1 N1 C9 119.9(2) . . ?
C4 N1 C9 120.2(2) . . ?
C11 N2 H2 118.9 . . ?
C12 N2 H2 118.9 . . ?
C12 N2 C11 122.3(3) . . ?
C3 O1 C2 113.4(2) . . ?
C10 O3 H3 109.5 . . ?
N1 C1 C2 116.2(3) . . ?
O2 C1 N1 122.4(3) . . ?
O2 C1 C2 121.3(3) . . ?
O1 C2 C1 113.3(2) . . ?
O1 C2 H2A 108.9 . . ?
O1 C2 H2B 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
O1 C3 C4 120.0(3) . . ?
O1 C3 C8 119.3(3) . . ?
C8 C3 C4 120.7(3) . . ?
C3 C4 N1 118.8(3) . . ?
C3 C4 C5 118.7(3) . . ?
C5 C4 N1 122.4(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.7(3) . . ?
C8 C7 H7 120.2 . . ?
C3 C8 H8 119.8 . . ?
C7 C8 C3 120.5(3) . . ?
C7 C8 H8 119.8 . . ?
N1 C9 H9A 109.6 . . ?
N1 C9 H9B 109.6 . . ?
N1 C9 C10 110.4(2) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
O3 C10 C9 106.9(2) . . ?
O3 C10 H10 108.7 . . ?
O3 C10 C11 111.5(3) . . ?
C9 C10 H10 108.7 . . ?
C11 C10 C9 112.2(2) . . ?
C11 C10 H10 108.7 . . ?
N2 C11 C10 113.3(3) . . ?
N2 C11 H11A 108.9 . . ?
N2 C11 H11B 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
N2 C12 C13 119.6(3) . . ?
N2 C12 C17 121.9(3) . . ?
C17 C12 C13 118.5(3) . . ?
C12 C13 C18 120.6(3) . . ?
C14 C13 C12 118.0(3) . . ?
C14 C13 C18 121.3(3) . . ?
C13 C14 H14 118.0 . . ?
C15 C14 C13 124.0(3) . . ?
C15 C14 H14 118.0 . . ?
C14 C15 C19 121.4(4) . . ?
C16 C15 C14 116.8(3) . . ?
C16 C15 C19 121.8(4) . . ?
C15 C16 H16 119.2 . . ?
C15 C16 C17 121.6(3) . . ?
C17 C16 H16 119.2 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.1(3) . . ?
C16 C17 H17 119.4 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
N1 C1 C2 O1 -33.7(4) . . . . ?
N1 C4 C5 C6 -173.5(3) . . . . ?
N1 C9 C10 O3 -176.2(2) . . . . ?
N1 C9 C10 C11 61.2(3) . . . . ?
N2 C12 C13 C14 180.0(3) . . . . ?
N2 C12 C13 C18 0.8(5) . . . . ?
N2 C12 C17 C16 -179.9(3) . . . . ?
O1 C3 C4 N1 -2.4(4) . . . . ?
O1 C3 C4 C5 -179.0(3) . . . . ?
O1 C3 C8 C7 176.4(3) . . . . ?
O2 C1 C2 O1 145.8(3) . . . . ?
O3 C10 C11 N2 67.3(3) . . . . ?
C1 N1 C4 C3 19.4(4) . . . . ?
C1 N1 C4 C5 -164.1(3) . . . . ?
C1 N1 C9 C10 -108.5(3) . . . . ?
C2 O1 C3 C4 -32.4(4) . . . . ?
C2 O1 C3 C8 151.1(3) . . . . ?
C3 O1 C2 C1 49.8(4) . . . . ?
C3 C4 C5 C6 3.0(5) . . . . ?
C4 N1 C1 O2 180.0(3) . . . . ?
C4 N1 C1 C2 -0.5(4) . . . . ?
C4 N1 C9 C10 64.5(3) . . . . ?
C4 C3 C8 C7 -0.1(5) . . . . ?
C4 C5 C6 C7 -0.9(5) . . . . ?
C5 C6 C7 C8 -1.7(6) . . . . ?
C6 C7 C8 C3 2.2(5) . . . . ?
C8 C3 C4 N1 174.1(3) . . . . ?
C8 C3 C4 C5 -2.5(5) . . . . ?
C9 N1 C1 O2 -6.9(4) . . . . ?
C9 N1 C1 C2 172.6(3) . . . . ?
C9 N1 C4 C3 -153.6(3) . . . . ?
C9 N1 C4 C5 22.8(4) . . . . ?
C9 C10 C11 N2 -172.8(3) . . . . ?
C11 N2 C12 C13 -153.3(3) . . . . ?
C11 N2 C12 C17 26.8(5) . . . . ?
C12 N2 C11 C10 60.9(4) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
C13 C12 C17 C16 0.3(5) . . . . ?
C13 C14 C15 C16 0.4(5) . . . . ?
C13 C14 C15 C19 -179.2(3) . . . . ?
C14 C15 C16 C17 -0.3(5) . . . . ?
C15 C16 C17 C12 0.0(5) . . . . ?
C17 C12 C13 C14 -0.2(5) . . . . ?
C17 C12 C13 C18 -179.3(3) . . . . ?
C18 C13 C14 C15 179.0(3) . . . . ?
C19 C15 C16 C17 179.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
