# 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_20191119LI_CZDX_QSS_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2011121'
loop_
_audit_author_name
_audit_author_address
'Song Sun'
;Changzhou University
China
;
_audit_update_record             
;
2020-06-21 deposited with the CCDC.	2020-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 N O3'
_chemical_formula_weight         335.39

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.3648(3)
_cell_length_b                   24.4988(11)
_cell_length_c                   8.6463(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.405(2)
_cell_angle_gamma                90
_cell_volume                     1699.73(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4519
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.992
_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      296(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            12666
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.593
_diffrn_reflns_theta_max         25.003
_diffrn_reflns_theta_full        25.003
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2976
_reflns_number_gt                2382
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0552P)²+0.5725P] 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_number_reflns         2976
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.2243(3) 0.49299(10) -0.1152(2) 0.0638(6) Uani 1 1 d . . . . .
H1A H 0.195005 0.460859 -0.180623 0.096 Uiso 1 1 calc R U . . .
H1B H 0.277913 0.518695 -0.167922 0.096 Uiso 1 1 calc R U . . .
H1C H 0.125327 0.509117 -0.099685 0.096 Uiso 1 1 calc R U . . .
C2 C 0.2815(2) 0.44135(7) 0.1220(2) 0.0363(4) Uani 1 1 d . . . . .
C3 C 0.4068(2) 0.43334(7) 0.2828(2) 0.0378(4) Uani 1 1 d . . . . .
H3A H 0.417118 0.467361 0.342233 0.045 Uiso 1 1 calc R U . . .
H3B H 0.514059 0.425845 0.265010 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3689(2) 0.38762(6) 0.3889(2) 0.0326(4) Uani 1 1 d . . . . .
C5 C 0.2005(2) 0.39290(7) 0.4328(2) 0.0343(4) Uani 1 1 d . . . . .
C6 C 0.1583(2) 0.45225(7) 0.4578(2) 0.0423(4) Uani 1 1 d . . . . .
H6A H 0.134081 0.471344 0.356917 0.063 Uiso 1 1 calc R U . . .
H6B H 0.251426 0.469194 0.533813 0.063 Uiso 1 1 calc R U . . .
H6C H 0.062807 0.453541 0.498545 0.063 Uiso 1 1 calc R U . . .
C7 C 0.2390(2) 0.36219(8) 0.5972(2) 0.0434(5) Uani 1 1 d . . . . .
H7A H 0.170527 0.375868 0.662426 0.052 Uiso 1 1 calc R U . . .
H7B H 0.220410 0.323268 0.581049 0.052 Uiso 1 1 calc R U . . .
C8 C 0.4186(3) 0.37423(7) 0.6740(2) 0.0448(5) Uani 1 1 d . . . . .
C9 C 0.5086(3) 0.37258(9) 0.8352(2) 0.0612(6) Uani 1 1 d . . . . .
H9 H 0.457965 0.361754 0.913144 0.073 Uiso 1 1 calc R U . . .
C10 C 0.6748(4) 0.38729(10) 0.8784(3) 0.0747(8) Uani 1 1 d . . . . .
H10 H 0.736381 0.386323 0.986270 0.090 Uiso 1 1 calc R U . . .
C11 C 0.7508(3) 0.40347(9) 0.7628(3) 0.0684(7) Uani 1 1 d . . . . .
H11 H 0.862534 0.413534 0.794090 0.082 Uiso 1 1 calc R U . . .
C12 C 0.6618(2) 0.40483(7) 0.6004(3) 0.0499(5) Uani 1 1 d . . . . .
H12 H 0.712887 0.415466 0.522661 0.060 Uiso 1 1 calc R U . . .
C13 C 0.4947(2) 0.38992(7) 0.5571(2) 0.0389(4) Uani 1 1 d . . . . .
C14 C 0.0503(2) 0.36528(7) 0.3194(2) 0.0369(4) Uani 1 1 d . . . . .
C15 C -0.0667(2) 0.28791(9) 0.1510(3) 0.0565(6) Uani 1 1 d . . . . .
H15A H -0.166974 0.307129 0.150042 0.085 Uiso 1 1 calc R U . . .
H15B H -0.068034 0.252439 0.197800 0.085 Uiso 1 1 calc R U . . .
H15C H -0.059815 0.284036 0.042565 0.085 Uiso 1 1 calc R U . . .
C16 C 0.2545(2) 0.24862(8) 0.1858(3) 0.0519(5) Uani 1 1 d . . . . .
H16 H 0.160789 0.226875 0.145730 0.062 Uiso 1 1 calc R U . . .
C17 C 0.4077(3) 0.22990(9) 0.1814(3) 0.0619(6) Uani 1 1 d . . . . .
H17 H 0.417115 0.195845 0.137236 0.074 Uiso 1 1 calc R U . . .
C18 C 0.5470(3) 0.26133(9) 0.2420(3) 0.0607(6) Uani 1 1 d . . . . .
H18 H 0.651095 0.248608 0.239699 0.073 Uiso 1 1 calc R U . . .
C19 C 0.5320(2) 0.31181(8) 0.3064(3) 0.0456(5) Uani 1 1 d . . . . .
H19 H 0.626985 0.332975 0.346420 0.055 Uiso 1 1 calc R U . . .
C20 C 0.3794(2) 0.33205(7) 0.3132(2) 0.0335(4) Uani 1 1 d . . . . .
C21 C 0.2376(2) 0.29982(7) 0.2495(2) 0.0374(4) Uani 1 1 d . . . . .
N1 N 0.07750(17) 0.31853(6) 0.24619(18) 0.0380(4) Uani 1 1 d . . . . .
O1 O 0.33598(17) 0.47845(6) 0.03874(15) 0.0502(4) Uani 1 1 d . . . . .
O2 O 0.14895(19) 0.41960(7) 0.07481(17) 0.0689(5) Uani 1 1 d . . . . .
O3 O -0.09085(15) 0.38226(5) 0.30622(17) 0.0503(4) 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 1.438(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O2 1.193(2) . ?
C2 O1 1.318(2) . ?
C2 C3 1.499(2) . ?
C3 C4 1.536(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C20 1.524(2) . ?
C4 C13 1.536(2) . ?
C4 C5 1.564(2) . ?
C5 C14 1.517(2) . ?
C5 C6 1.526(2) . ?
C5 C7 1.559(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.490(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.385(3) . ?
C8 C13 1.392(3) . ?
C9 C10 1.382(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9300 . ?
C14 O3 1.227(2) . ?
C14 N1 1.359(2) . ?
C15 N1 1.461(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.372(3) . ?
C16 C21 1.393(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.376(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.386(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.401(2) . ?
C21 N1 1.408(2) . ?

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 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 123.53(17) . . ?
O2 C2 C3 126.67(16) . . ?
O1 C2 C3 109.75(15) . . ?
C2 C3 C4 116.19(14) . . ?
C2 C3 H3A 108.2 . . ?
C4 C3 H3A 108.2 . . ?
C2 C3 H3B 108.2 . . ?
C4 C3 H3B 108.2 . . ?
H3A C3 H3B 107.4 . . ?
C20 C4 C3 110.37(14) . . ?
C20 C4 C13 109.41(13) . . ?
C3 C4 C13 109.68(13) . . ?
C20 C4 C5 110.06(13) . . ?
C3 C4 C5 115.87(14) . . ?
C13 C4 C5 100.97(13) . . ?
C14 C5 C6 109.50(14) . . ?
C14 C5 C7 107.11(14) . . ?
C6 C5 C7 109.08(14) . . ?
C14 C5 C4 116.38(14) . . ?
C6 C5 C4 111.93(14) . . ?
C7 C5 C4 102.30(13) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C5 103.49(15) . . ?
C8 C7 H7A 111.1 . . ?
C5 C7 H7A 111.1 . . ?
C8 C7 H7B 111.1 . . ?
C5 C7 H7B 111.1 . . ?
H7A C7 H7B 109.0 . . ?
C9 C8 C13 120.6(2) . . ?
C9 C8 C7 129.5(2) . . ?
C13 C8 C7 109.96(16) . . ?
C8 C9 C10 118.9(2) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 118.5(2) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C12 C13 C8 120.54(18) . . ?
C12 C13 C4 129.24(18) . . ?
C8 C13 C4 110.21(16) . . ?
O3 C14 N1 121.73(16) . . ?
O3 C14 C5 120.57(16) . . ?
N1 C14 C5 117.40(14) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 120.78(18) . . ?
C17 C16 H16 119.6 . . ?
C21 C16 H16 119.6 . . ?
C16 C17 C18 120.09(19) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 119.60(18) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C20 121.95(17) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C19 C20 C21 117.97(16) . . ?
C19 C20 C4 120.21(15) . . ?
C21 C20 C4 121.82(15) . . ?
C16 C21 C20 119.58(16) . . ?
C16 C21 N1 119.15(16) . . ?
C20 C21 N1 121.26(15) . . ?
C14 N1 C21 123.24(14) . . ?
C14 N1 C15 118.38(15) . . ?
C21 N1 C15 118.26(15) . . ?
C2 O1 C1 116.20(15) . . ?

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.034



