# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1946779'
loop_
_audit_author_name
_audit_author_address
'Yingchao Zhang'
;Jilin University
China
;
_audit_update_record             
;
2019-08-13 deposited with the CCDC.	2020-07-07 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            'C21 H19 N3 O2'
_chemical_formula_weight         345.39

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   12.4892(11)
_cell_length_b                   7.3635(6)
_cell_length_c                   18.9497(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1742.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5625
_cell_measurement_theta_min      2
_cell_measurement_theta_max      26

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             728
_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   multi-scan
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  0.8
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean graphite
_diffrn_reflns_number            9497
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.631
_diffrn_reflns_theta_max         26.375
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3459
_reflns_number_gt                2929
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.939
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.0648P] 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 1150 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3459
_refine_ls_number_parameters     239
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_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 0.95630(14) 0.3558(2) 0.46382(10) 0.0314(5) Uani 1 1 d . . . . .
O2 O 0.60018(17) -0.0547(3) 0.26339(12) 0.0408(5) Uani 1 1 d . . . . .
N1 N 0.60643(18) 0.5426(3) 0.37788(13) 0.0322(5) Uani 1 1 d . . . . .
N2 N 0.58212(18) 0.2299(3) 0.30854(12) 0.0298(5) Uani 1 1 d . . . . .
H2 H 0.5386 0.3238 0.3090 0.036 Uiso 1 1 calc R U . . .
N3 N 0.9520(2) -0.0672(4) 0.54023(16) 0.0525(7) Uani 1 1 d . . . . .
C1 C 0.6762(2) 0.2494(4) 0.34820(14) 0.0267(6) Uani 1 1 d . . . . .
C2 C 0.6877(2) 0.4187(3) 0.38455(14) 0.0260(6) Uani 1 1 d . . . . .
C3 C 0.7810(2) 0.4530(4) 0.42481(14) 0.0270(6) Uani 1 1 d . . . . .
C4 C 0.7557(2) 0.1222(4) 0.35310(14) 0.0287(6) Uani 1 1 d . . . . .
H4 H 0.7488 0.0101 0.3288 0.034 Uiso 1 1 calc R U . . .
C5 C 0.3314(3) 0.3106(5) 0.1611(2) 0.0512(9) Uani 1 1 d . . . . .
H5 H 0.3213 0.4198 0.1353 0.061 Uiso 1 1 calc R U . . .
C6 C 0.4432(2) 0.1175(4) 0.23272(15) 0.0325(6) Uani 1 1 d . . . . .
C7 C 0.3638(2) -0.0154(4) 0.23419(16) 0.0375(7) Uani 1 1 d . . . . .
C8 C 0.5489(2) 0.0855(4) 0.26943(15) 0.0301(6) Uani 1 1 d . . . . .
C9 C 0.2520(3) 0.1833(5) 0.16315(19) 0.0488(9) Uani 1 1 d . . . . .
H9 H 0.1862 0.2052 0.1395 0.059 Uiso 1 1 calc R U . . .
C10 C 0.8606(2) 0.3161(4) 0.42903(14) 0.0265(6) Uani 1 1 d . . . . .
C11 C 0.8479(2) 0.1561(4) 0.39395(14) 0.0290(6) Uani 1 1 d . . . . .
H11 H 0.9020 0.0658 0.3971 0.035 Uiso 1 1 calc R U . . .
C12 C 0.7893(2) 0.6248(4) 0.45742(16) 0.0333(6) Uani 1 1 d . . . . .
H12 H 0.8512 0.6555 0.4840 0.040 Uiso 1 1 calc R U . . .
C13 C 0.4269(3) 0.2807(5) 0.19666(17) 0.0404(7) Uani 1 1 d . . . . .
H13 H 0.4811 0.3711 0.1965 0.049 Uiso 1 1 calc R U . . .
C14 C 0.2670(2) 0.0234(5) 0.19941(17) 0.0447(8) Uani 1 1 d . . . . .
H14 H 0.2105 -0.0630 0.2010 0.054 Uiso 1 1 calc R U . . .
C15 C 0.6181(2) 0.6997(4) 0.41058(16) 0.0379(7) Uani 1 1 d . . . . .
H15 H 0.5619 0.7860 0.4067 0.046 Uiso 1 1 calc R U . . .
C16 C 0.7075(2) 0.7467(4) 0.45041(16) 0.0372(7) Uani 1 1 d . . . . .
H16 H 0.7116 0.8623 0.4725 0.045 Uiso 1 1 calc R U . . .
C17 C 0.9600(2) 0.0867(4) 0.53577(17) 0.0361(7) Uani 1 1 d . . . . .
C18 C 0.3766(3) -0.1931(5) 0.27067(19) 0.0519(9) Uani 1 1 d . . . . .
H18A H 0.4298 -0.2666 0.2456 0.078 Uiso 1 1 calc R U . . .
H18B H 0.3079 -0.2572 0.2712 0.078 Uiso 1 1 calc R U . . .
H18C H 0.4006 -0.1725 0.3193 0.078 Uiso 1 1 calc R U . . .
C19 C 0.8918(3) 0.3689(5) 0.58663(16) 0.0439(8) Uani 1 1 d . . . . .
H19A H 0.9006 0.5011 0.5881 0.066 Uiso 1 1 calc R U . . .
H19B H 0.9048 0.3183 0.6337 0.066 Uiso 1 1 calc R U . . .
H19C H 0.8187 0.3394 0.5716 0.066 Uiso 1 1 calc R U . . .
C20 C 1.0861(2) 0.3375(5) 0.55304(18) 0.0446(8) Uani 1 1 d . . . . .
H20A H 1.1341 0.2926 0.5161 0.067 Uiso 1 1 calc R U . . .
H20B H 1.1054 0.2818 0.5983 0.067 Uiso 1 1 calc R U . . .
H20C H 1.0927 0.4697 0.5567 0.067 Uiso 1 1 calc R U . . .
C21 C 0.9713(2) 0.2881(4) 0.53464(16) 0.0326(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
O1 C10 1.396(3) . ?
O1 C21 1.444(4) . ?
O2 C8 1.220(3) . ?
N1 C15 1.320(4) . ?
N1 C2 1.370(3) . ?
N2 C8 1.360(4) . ?
N2 C1 1.403(3) . ?
N2 H2 0.8800 . ?
N3 C17 1.141(4) . ?
C1 C4 1.368(4) . ?
C1 C2 1.431(4) . ?
C2 C3 1.416(4) . ?
C3 C12 1.412(4) . ?
C3 C10 1.418(4) . ?
C4 C11 1.409(4) . ?
C4 H4 0.9500 . ?
C5 C9 1.365(5) . ?
C5 C13 1.386(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(4) . ?
C6 C13 1.397(4) . ?
C6 C8 1.511(4) . ?
C7 C14 1.406(4) . ?
C7 C18 1.489(5) . ?
C9 C14 1.376(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.362(4) . ?
C11 H11 0.9500 . ?
C12 C16 1.366(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.391(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C21 1.490(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C21 1.520(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.519(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C10 O1 C21 118.5(2) . . ?
C15 N1 C2 117.3(2) . . ?
C8 N2 C1 128.9(2) . . ?
C8 N2 H2 115.6 . . ?
C1 N2 H2 115.6 . . ?
C4 C1 N2 125.0(2) . . ?
C4 C1 C2 119.4(2) . . ?
N2 C1 C2 115.5(2) . . ?
N1 C2 C3 122.7(2) . . ?
N1 C2 C1 117.5(2) . . ?
C3 C2 C1 119.8(2) . . ?
C12 C3 C2 117.1(2) . . ?
C12 C3 C10 124.1(2) . . ?
C2 C3 C10 118.7(2) . . ?
C1 C4 C11 120.6(2) . . ?
C1 C4 H4 119.7 . . ?
C11 C4 H4 119.7 . . ?
C9 C5 C13 120.1(3) . . ?
C9 C5 H5 119.9 . . ?
C13 C5 H5 119.9 . . ?
C7 C6 C13 120.6(3) . . ?
C7 C6 C8 120.2(3) . . ?
C13 C6 C8 119.2(3) . . ?
C6 C7 C14 117.4(3) . . ?
C6 C7 C18 123.3(3) . . ?
C14 C7 C18 119.3(3) . . ?
O2 C8 N2 123.5(3) . . ?
O2 C8 C6 123.2(2) . . ?
N2 C8 C6 113.3(2) . . ?
C5 C9 C14 120.2(3) . . ?
C5 C9 H9 119.9 . . ?
C14 C9 H9 119.9 . . ?
C11 C10 O1 120.8(2) . . ?
C11 C10 C3 120.4(2) . . ?
O1 C10 C3 118.6(2) . . ?
C10 C11 C4 121.1(2) . . ?
C10 C11 H11 119.4 . . ?
C4 C11 H11 119.4 . . ?
C16 C12 C3 119.4(3) . . ?
C16 C12 H12 120.3 . . ?
C3 C12 H12 120.3 . . ?
C5 C13 C6 120.0(3) . . ?
C5 C13 H13 120.0 . . ?
C6 C13 H13 120.0 . . ?
C9 C14 C7 121.6(3) . . ?
C9 C14 H14 119.2 . . ?
C7 C14 H14 119.2 . . ?
N1 C15 C16 124.1(3) . . ?
N1 C15 H15 117.9 . . ?
C16 C15 H15 117.9 . . ?
C12 C16 C15 119.3(3) . . ?
C12 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
N3 C17 C21 176.6(3) . . ?
C7 C18 H18A 109.5 . . ?
C7 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C7 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C19 H19A 109.5 . . ?
C21 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C21 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C21 C17 110.1(2) . . ?
O1 C21 C20 104.7(2) . . ?
C17 C21 C20 108.9(2) . . ?
O1 C21 C19 112.5(2) . . ?
C17 C21 C19 108.6(3) . . ?
C20 C21 C19 112.0(3) . . ?

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 N2 C1 C4 1.8(4) . . . . ?
C8 N2 C1 C2 -179.3(3) . . . . ?
C15 N1 C2 C3 0.4(4) . . . . ?
C15 N1 C2 C1 -179.0(3) . . . . ?
C4 C1 C2 N1 179.6(2) . . . . ?
N2 C1 C2 N1 0.7(3) . . . . ?
C4 C1 C2 C3 0.3(4) . . . . ?
N2 C1 C2 C3 -178.7(2) . . . . ?
N1 C2 C3 C12 -1.5(4) . . . . ?
C1 C2 C3 C12 177.9(2) . . . . ?
N1 C2 C3 C10 179.6(2) . . . . ?
C1 C2 C3 C10 -1.1(4) . . . . ?
N2 C1 C4 C11 179.4(2) . . . . ?
C2 C1 C4 C11 0.5(4) . . . . ?
C13 C6 C7 C14 -1.2(4) . . . . ?
C8 C6 C7 C14 179.6(3) . . . . ?
C13 C6 C7 C18 179.0(3) . . . . ?
C8 C6 C7 C18 -0.1(4) . . . . ?
C1 N2 C8 O2 -0.1(5) . . . . ?
C1 N2 C8 C6 -178.7(2) . . . . ?
C7 C6 C8 O2 46.9(4) . . . . ?
C13 C6 C8 O2 -132.3(3) . . . . ?
C7 C6 C8 N2 -134.4(3) . . . . ?
C13 C6 C8 N2 46.4(4) . . . . ?
C13 C5 C9 C14 -1.2(5) . . . . ?
C21 O1 C10 C11 -84.4(3) . . . . ?
C21 O1 C10 C3 102.0(3) . . . . ?
C12 C3 C10 C11 -177.8(3) . . . . ?
C2 C3 C10 C11 1.1(4) . . . . ?
C12 C3 C10 O1 -4.1(4) . . . . ?
C2 C3 C10 O1 174.7(2) . . . . ?
O1 C10 C11 C4 -173.8(2) . . . . ?
C3 C10 C11 C4 -0.3(4) . . . . ?
C1 C4 C11 C10 -0.5(4) . . . . ?
C2 C3 C12 C16 1.6(4) . . . . ?
C10 C3 C12 C16 -179.5(3) . . . . ?
C9 C5 C13 C6 2.1(5) . . . . ?
C7 C6 C13 C5 -0.9(5) . . . . ?
C8 C6 C13 C5 178.3(3) . . . . ?
C5 C9 C14 C7 -1.0(5) . . . . ?
C6 C7 C14 C9 2.2(4) . . . . ?
C18 C7 C14 C9 -178.1(3) . . . . ?
C2 N1 C15 C16 0.6(4) . . . . ?
C3 C12 C16 C15 -0.7(4) . . . . ?
N1 C15 C16 C12 -0.4(5) . . . . ?
C10 O1 C21 C17 57.2(3) . . . . ?
C10 O1 C21 C20 174.1(2) . . . . ?
C10 O1 C21 C19 -64.1(3) . . . . ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.035

