# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_20191008_mdl_wc_7_89_0m
_database_code_depnum_ccdc_archive 'CCDC 1974919'
loop_
_audit_author_name
_audit_author_address
'Dong-Liang Mo'
;Guangxi Normal University
China
;
_audit_update_record             
;
2019-12-31 deposited with the CCDC.	2020-05-08 downloaded from the CCDC.
;
_audit_creation_date             2019-12-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H23 N O3'
_chemical_formula_sum            'C23 H23 N O3'
_chemical_formula_weight         361.42
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1065(19)
_cell_length_b                   9.212(2)
_cell_length_c                   13.496(3)
_cell_angle_alpha                83.868(3)
_cell_angle_beta                 70.305(3)
_cell_angle_gamma                66.759(3)
_cell_volume                     979.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3836
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.32
_exptl_absorpt_correction_T_min  0.24
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10350
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         1.603
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2637
_reflns_number_total             3363
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0540
_refine_ls_restrained_S_all      1.056
_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)+(0.0843P)²+0.3205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1660
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0(10)
 1(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C14(H14), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C22(H22A,H22B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C11(H11), C5(H5), C8(H8), C9(H9), C4(H4), C10(H10), C3(H3)
3.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.9007(2) 0.94378(19) 0.26980(12) 0.0462(4) Uani 1 1 d . . . . .
C13 C 0.8305(2) 1.1189(2) 0.27745(14) 0.0405(4) Uani 1 1 d . . . . .
C12 C 0.9248(2) 1.1858(2) 0.18140(15) 0.0433(5) Uani 1 1 d . . . . .
C7 C 1.0115(2) 1.2627(2) 0.20782(17) 0.0481(5) Uani 1 1 d . . . . .
C1 C 0.8701(2) 1.1734(2) 0.36460(15) 0.0452(5) Uani 1 1 d . . . . .
C16 C 0.7809(3) 0.8936(2) 0.29567(15) 0.0495(5) Uani 1 1 d . . . . .
O3 O 0.4482(2) 1.6536(2) 0.19077(16) 0.0762(5) Uani 1 1 d . . . . .
C6 C 0.9759(3) 1.2564(2) 0.32227(18) 0.0505(5) Uani 1 1 d . . . . .
C14 C 0.6383(2) 1.1685(2) 0.29281(15) 0.0447(5) Uani 1 1 d . . . . .
H14 H 0.624639 1.191793 0.223148 0.054 Uiso 1 1 calc R . . . .
C2 C 0.8187(3) 1.1468(3) 0.47122(17) 0.0598(6) Uani 1 1 d . . . . .
H2 H 0.749400 1.090504 0.499084 0.072 Uiso 1 1 calc R . . . .
C11 C 0.9349(3) 1.1749(3) 0.07774(16) 0.0567(6) Uani 1 1 d . . . . .
H11 H 0.876522 1.123902 0.060195 0.068 Uiso 1 1 calc R . . . .
C19 C 0.5241(3) 1.3154(3) 0.36231(19) 0.0573(6) Uani 1 1 d . . . . .
C21 C 0.4324(3) 1.5269(3) 0.2400(2) 0.0654(7) Uani 1 1 d . . . . .
O1 O 0.4336(3) 1.3092(2) 0.45009(16) 0.0956(7) Uani 1 1 d . . . . .
C15 C 0.6042(3) 1.0198(3) 0.32848(19) 0.0590(6) Uani 1 1 d . . . . .
H15 H 0.557941 1.024172 0.405515 0.071 Uiso 1 1 calc R . . . .
C5 C 1.0300(3) 1.3158(3) 0.3876(2) 0.0705(7) Uani 1 1 d . . . . .
H5 H 1.100411 1.371176 0.360354 0.085 Uiso 1 1 calc R . . . .
C8 C 1.1102(3) 1.3279(3) 0.1288(2) 0.0665(7) Uani 1 1 d . . . . .
H8 H 1.169006 1.379383 0.145334 0.080 Uiso 1 1 calc R . . . .
C20 C 0.5292(3) 1.4705(3) 0.3163(2) 0.0610(6) Uani 1 1 d . . . . .
H20A H 0.481742 1.549224 0.372706 0.073 Uiso 1 1 calc R . . . .
H20B H 0.645673 1.457921 0.280635 0.073 Uiso 1 1 calc R . . . .
C17 C 0.8141(4) 0.7217(3) 0.29771(19) 0.0677(7) Uani 1 1 d . . . . .
H17A H 0.768139 0.697871 0.250039 0.102 Uiso 1 1 calc GR . . . .
H17B H 0.762000 0.694496 0.367717 0.102 Uiso 1 1 calc GR . . . .
H17C H 0.933709 0.661774 0.276688 0.102 Uiso 1 1 calc GR . . . .
C9 C 1.1192(3) 1.3148(3) 0.0263(2) 0.0752(8) Uani 1 1 d . . . . .
H9 H 1.185437 1.357306 -0.026746 0.090 Uiso 1 1 calc R . . . .
O2 O 0.3479(4) 1.4658(3) 0.2266(3) 0.1278(11) Uani 1 1 d . . . . .
C4 C 0.9767(4) 1.2905(3) 0.4937(3) 0.0836(9) Uani 1 1 d . . . . .
H4 H 1.010899 1.330774 0.538475 0.100 Uiso 1 1 calc R . . . .
C10 C 1.0325(3) 1.2405(3) 0.0006(2) 0.0712(7) Uani 1 1 d . . . . .
H10 H 1.039412 1.234109 -0.069263 0.085 Uiso 1 1 calc R . . . .
C3 C 0.8744(4) 1.2075(3) 0.5357(2) 0.0787(9) Uani 1 1 d . . . . .
H3 H 0.841837 1.191543 0.607716 0.094 Uiso 1 1 calc R . . . .
C18 C 0.4828(4) 0.9948(4) 0.2846(3) 0.1003(11) Uani 1 1 d . . . . .
H18A H 0.527288 0.988535 0.209078 0.150 Uiso 1 1 calc GR . . . .
H18B H 0.375550 1.081752 0.306573 0.150 Uiso 1 1 calc GR . . . .
H18C H 0.468683 0.898272 0.310265 0.150 Uiso 1 1 calc GR . . . .
C22 C 0.3499(5) 1.7246(4) 0.1184(3) 0.1025(11) Uani 1 1 d . . . . .
H22A H 0.379965 1.646962 0.064384 0.123 Uiso 1 1 calc R . . . .
H22B H 0.230490 1.755667 0.157083 0.123 Uiso 1 1 calc R . . . .
C23 C 0.3815(6) 1.8581(5) 0.0708(4) 0.1271(15) Uani 1 1 d . . . . .
H23A H 0.326529 1.895173 0.018256 0.191 Uiso 1 1 calc GR . . . .
H23B H 0.500897 1.829586 0.038325 0.191 Uiso 1 1 calc GR . . . .
H23C H 0.338460 1.940179 0.123276 0.191 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 C13 1.483(2) . ?
N1 C16 1.277(3) . ?
C13 C12 1.515(3) . ?
C13 C1 1.523(3) . ?
C13 C14 1.568(3) . ?
C12 C7 1.392(3) . ?
C12 C11 1.383(3) . ?
C7 C6 1.467(3) . ?
C7 C8 1.396(3) . ?
C1 C6 1.399(3) . ?
C1 C2 1.382(3) . ?
C16 C15 1.513(3) . ?
C16 C17 1.490(3) . ?
O3 C21 1.314(3) . ?
O3 C22 1.474(4) . ?
C6 C5 1.389(3) . ?
C14 C19 1.516(3) . ?
C14 C15 1.516(3) . ?
C2 C3 1.397(4) . ?
C11 C10 1.380(3) . ?
C19 O1 1.204(3) . ?
C19 C20 1.507(3) . ?
C21 C20 1.498(4) . ?
C21 O2 1.183(3) . ?
C15 C18 1.515(4) . ?
C5 C4 1.375(4) . ?
C8 C9 1.374(4) . ?
C9 C10 1.369(4) . ?
C4 C3 1.374(5) . ?
C22 C23 1.412(5) . ?

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
C16 N1 C13 109.99(16) . . ?
N1 C13 C12 110.75(14) . . ?
N1 C13 C1 109.97(15) . . ?
N1 C13 C14 104.52(15) . . ?
C12 C13 C1 101.42(15) . . ?
C12 C13 C14 114.52(15) . . ?
C1 C13 C14 115.79(15) . . ?
C7 C12 C13 111.38(17) . . ?
C11 C12 C13 128.20(18) . . ?
C11 C12 C7 120.40(19) . . ?
C12 C7 C6 108.02(18) . . ?
C12 C7 C8 119.6(2) . . ?
C8 C7 C6 132.4(2) . . ?
C6 C1 C13 110.24(17) . . ?
C2 C1 C13 128.4(2) . . ?
C2 C1 C6 121.3(2) . . ?
N1 C16 C15 115.63(18) . . ?
N1 C16 C17 121.8(2) . . ?
C17 C16 C15 122.5(2) . . ?
C21 O3 C22 117.5(2) . . ?
C1 C6 C7 108.91(17) . . ?
C5 C6 C7 130.9(2) . . ?
C5 C6 C1 120.2(2) . . ?
C19 C14 C13 113.85(17) . . ?
C19 C14 C15 116.28(18) . . ?
C15 C14 C13 104.51(16) . . ?
C1 C2 C3 117.7(3) . . ?
C10 C11 C12 119.3(2) . . ?
O1 C19 C14 121.9(2) . . ?
O1 C19 C20 121.4(2) . . ?
C20 C19 C14 116.72(19) . . ?
O3 C21 C20 113.0(2) . . ?
O2 C21 O3 123.3(3) . . ?
O2 C21 C20 123.7(2) . . ?
C16 C15 C14 101.64(17) . . ?
C16 C15 C18 114.8(2) . . ?
C18 C15 C14 114.6(2) . . ?
C4 C5 C6 118.2(3) . . ?
C9 C8 C7 119.0(2) . . ?
C21 C20 C19 111.6(2) . . ?
C10 C9 C8 121.3(2) . . ?
C3 C4 C5 122.0(2) . . ?
C9 C10 C11 120.4(3) . . ?
C4 C3 C2 120.7(3) . . ?
C23 C22 O3 110.9(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
N1 C13 C12 C7 -114.73(18) . . . . ?
N1 C13 C12 C11 63.7(3) . . . . ?
N1 C13 C1 C6 115.97(17) . . . . ?
N1 C13 C1 C2 -62.4(2) . . . . ?
N1 C13 C14 C19 146.15(17) . . . . ?
N1 C13 C14 C15 18.23(19) . . . . ?
N1 C16 C15 C14 12.9(2) . . . . ?
N1 C16 C15 C18 137.2(2) . . . . ?
C13 N1 C16 C15 -1.1(2) . . . . ?
C13 N1 C16 C17 -178.54(18) . . . . ?
C13 C12 C7 C6 -1.9(2) . . . . ?
C13 C12 C7 C8 178.03(18) . . . . ?
C13 C12 C11 C10 -178.0(2) . . . . ?
C13 C1 C6 C7 0.2(2) . . . . ?
C13 C1 C6 C5 -179.25(18) . . . . ?
C13 C1 C2 C3 178.97(19) . . . . ?
C13 C14 C19 O1 -107.8(3) . . . . ?
C13 C14 C19 C20 72.1(2) . . . . ?
C13 C14 C15 C16 -18.0(2) . . . . ?
C13 C14 C15 C18 -142.3(2) . . . . ?
C12 C13 C1 C6 -1.28(19) . . . . ?
C12 C13 C1 C2 -179.64(19) . . . . ?
C12 C13 C14 C19 -92.5(2) . . . . ?
C12 C13 C14 C15 139.58(17) . . . . ?
C12 C7 C6 C1 1.0(2) . . . . ?
C12 C7 C6 C5 -179.5(2) . . . . ?
C12 C7 C8 C9 0.1(3) . . . . ?
C12 C11 C10 C9 0.4(4) . . . . ?
C7 C12 C11 C10 0.3(3) . . . . ?
C7 C6 C5 C4 -179.4(2) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
C1 C13 C12 C7 1.95(19) . . . . ?
C1 C13 C12 C11 -179.7(2) . . . . ?
C1 C13 C14 C19 25.0(2) . . . . ?
C1 C13 C14 C15 -102.90(19) . . . . ?
C1 C6 C5 C4 0.0(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C16 N1 C13 C12 -134.75(17) . . . . ?
C16 N1 C13 C1 113.97(18) . . . . ?
C16 N1 C13 C14 -10.9(2) . . . . ?
O3 C21 C20 C19 -173.7(2) . . . . ?
C6 C7 C8 C9 -179.9(2) . . . . ?
C6 C1 C2 C3 0.8(3) . . . . ?
C6 C5 C4 C3 0.8(4) . . . . ?
C14 C13 C12 C7 127.40(17) . . . . ?
C14 C13 C12 C11 -54.2(3) . . . . ?
C14 C13 C1 C6 -125.88(17) . . . . ?
C14 C13 C1 C2 55.8(3) . . . . ?
C14 C19 C20 C21 77.2(3) . . . . ?
C2 C1 C6 C7 178.74(18) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C11 C12 C7 C6 179.55(18) . . . . ?
C11 C12 C7 C8 -0.5(3) . . . . ?
C19 C14 C15 C16 -144.40(19) . . . . ?
C19 C14 C15 C18 91.2(3) . . . . ?
C21 O3 C22 C23 -179.3(3) . . . . ?
O1 C19 C20 C21 -103.0(3) . . . . ?
C15 C14 C19 O1 13.8(3) . . . . ?
C15 C14 C19 C20 -166.3(2) . . . . ?
C5 C4 C3 C2 -0.8(4) . . . . ?
C8 C7 C6 C1 -178.9(2) . . . . ?
C8 C7 C6 C5 0.5(4) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C17 C16 C15 C14 -169.67(19) . . . . ?
C17 C16 C15 C18 -45.4(3) . . . . ?
O2 C21 C20 C19 7.6(4) . . . . ?
C22 O3 C21 C20 -176.5(3) . . . . ?
C22 O3 C21 O2 2.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0(10)
2 1(10)

