# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_d8v21340_0m
_database_code_depnum_ccdc_archive 'CCDC 2082928'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2022-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 N O'
_chemical_formula_weight         289.36

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                   9.2952(3)
_cell_length_b                   15.1908(6)
_cell_length_c                   21.6017(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3050.19(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    7108
_cell_measurement_theta_min      5.473
_cell_measurement_theta_max      54.855

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6646
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(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            14282
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.737
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2976
_reflns_number_gt                2569
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0431P)²+0.9952P] 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
_refine_ls_extinction_coef       0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2976
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 0.11787(11) 0.87455(6) 0.65600(5) 0.0410(3) Uani 1 1 d . . . . .
N1 N 0.15642(11) 0.74975(7) 0.60113(5) 0.0305(3) Uani 1 1 d . . . . .
C1 C 0.19490(14) 0.83181(8) 0.62120(6) 0.0294(3) Uani 1 1 d . . . . .
C2 C 0.34098(14) 0.86457(8) 0.59922(6) 0.0293(3) Uani 1 1 d . . . . .
H2 H 0.3502 0.8498 0.5548 0.035 Uiso 1 1 calc R U . . .
C3 C 0.45077(13) 0.80992(8) 0.63455(5) 0.0251(3) Uani 1 1 d . . . . .
C4 C 0.53241(14) 0.84867(8) 0.68825(6) 0.0313(3) Uani 1 1 d . . . . .
H4A H 0.4758 0.8417 0.7262 0.038 Uiso 1 1 calc R U . . .
H4B H 0.5467 0.9118 0.6812 0.038 Uiso 1 1 calc R U . . .
C5 C 0.67786(14) 0.80433(8) 0.69655(6) 0.0316(3) Uani 1 1 d . . . . .
H5A H 0.7421 0.8224 0.6629 0.038 Uiso 1 1 calc R U . . .
H5B H 0.7207 0.8237 0.7357 0.038 Uiso 1 1 calc R U . . .
C6 C 0.66474(13) 0.70557(8) 0.69670(5) 0.0264(3) Uani 1 1 d . . . . .
C7 C 0.75225(14) 0.65243(9) 0.73297(6) 0.0333(3) Uani 1 1 d . . . . .
H7 H 0.8217 0.6785 0.7587 0.040 Uiso 1 1 calc R U . . .
C8 C 0.73900(15) 0.56151(9) 0.73184(6) 0.0361(3) Uani 1 1 d . . . . .
H8 H 0.8005 0.5263 0.7559 0.043 Uiso 1 1 calc R U . . .
C9 C 0.63456(14) 0.52305(9) 0.69508(6) 0.0330(3) Uani 1 1 d . . . . .
H9 H 0.6234 0.4615 0.6948 0.040 Uiso 1 1 calc R U . . .
C10 C 0.54635(13) 0.57521(8) 0.65862(6) 0.0266(3) Uani 1 1 d . . . . .
H10 H 0.4751 0.5486 0.6340 0.032 Uiso 1 1 calc R U . . .
C11 C 0.56170(12) 0.66675(8) 0.65788(5) 0.0232(3) Uani 1 1 d . . . . .
C12 C 0.46700(12) 0.72400(7) 0.62017(5) 0.0229(3) Uani 1 1 d . . . . .
C13 C 0.38735(13) 0.68504(7) 0.56750(5) 0.0239(3) Uani 1 1 d . . . . .
C14 C 0.46043(14) 0.63324(8) 0.52410(6) 0.0290(3) Uani 1 1 d . . . . .
H14 H 0.5596 0.6236 0.5292 0.035 Uiso 1 1 calc R U . . .
C15 C 0.39085(16) 0.59590(8) 0.47401(6) 0.0353(3) Uani 1 1 d . . . . .
H15 H 0.4422 0.5615 0.4454 0.042 Uiso 1 1 calc R U . . .
C16 C 0.24435(17) 0.60973(9) 0.46640(6) 0.0383(3) Uani 1 1 d . . . . .
H16 H 0.1957 0.5837 0.4329 0.046 Uiso 1 1 calc R U . . .
C17 C 0.17013(15) 0.66150(9) 0.50780(6) 0.0356(3) Uani 1 1 d . . . . .
H17 H 0.0713 0.6715 0.5019 0.043 Uiso 1 1 calc R U . . .
C18 C 0.23971(14) 0.69937(8) 0.55846(5) 0.0268(3) Uani 1 1 d . . . . .
C19 C 0.01881(15) 0.71373(10) 0.62258(8) 0.0444(4) Uani 1 1 d . . . . .
H19A H -0.0576 0.7330 0.5952 0.067 Uiso 1 1 calc R U . . .
H19B H -0.0004 0.7344 0.6642 0.067 Uiso 1 1 calc R U . . .
H19C H 0.0235 0.6499 0.6225 0.067 Uiso 1 1 calc R U . . .
C20 C 0.35312(17) 0.96414(8) 0.60553(7) 0.0420(4) Uani 1 1 d . . . . .
H20A H 0.3403 0.9806 0.6486 0.063 Uiso 1 1 calc R U . . .
H20B H 0.2795 0.9921 0.5805 0.063 Uiso 1 1 calc R U . . .
H20C H 0.4473 0.9831 0.5915 0.063 Uiso 1 1 calc R U . . .


_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 C1 1.2245(15) . ?
N1 C1 1.3673(17) . ?
N1 C18 1.4265(16) . ?
N1 C19 1.4664(17) . ?
C1 C2 1.5220(18) . ?
C2 C3 1.5208(17) . ?
C2 C20 1.5229(17) . ?
C2 H2 0.9900 . ?
C3 C12 1.3501(16) . ?
C3 C4 1.5061(17) . ?
C4 C5 1.5210(18) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C6 1.5052(17) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 C7 1.3882(17) . ?
C6 C11 1.4030(16) . ?
C7 C8 1.3868(19) . ?
C7 H7 0.9400 . ?
C8 C9 1.3836(19) . ?
C8 H8 0.9400 . ?
C9 C10 1.3857(17) . ?
C9 H9 0.9400 . ?
C10 C11 1.3981(16) . ?
C10 H10 0.9400 . ?
C11 C12 1.4815(16) . ?
C12 C13 1.4809(16) . ?
C13 C14 1.3999(17) . ?
C13 C18 1.4032(17) . ?
C14 C15 1.3823(18) . ?
C14 H14 0.9400 . ?
C15 C16 1.388(2) . ?
C15 H15 0.9400 . ?
C16 C17 1.376(2) . ?
C16 H16 0.9400 . ?
C17 C18 1.3953(18) . ?
C17 H17 0.9400 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?

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 C18 123.51(11) . . ?
C1 N1 C19 117.92(11) . . ?
C18 N1 C19 118.51(11) . . ?
O1 C1 N1 121.67(12) . . ?
O1 C1 C2 122.67(12) . . ?
N1 C1 C2 115.63(10) . . ?
C3 C2 C1 105.29(10) . . ?
C3 C2 C20 116.58(11) . . ?
C1 C2 C20 111.28(11) . . ?
C3 C2 H2 107.8 . . ?
C1 C2 H2 107.8 . . ?
C20 C2 H2 107.8 . . ?
C12 C3 C4 119.91(11) . . ?
C12 C3 C2 119.16(11) . . ?
C4 C3 C2 120.76(10) . . ?
C3 C4 C5 111.45(10) . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 111.69(10) . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C11 119.53(12) . . ?
C7 C6 C5 122.24(11) . . ?
C11 C6 C5 118.22(11) . . ?
C8 C7 C6 121.15(12) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C7 119.53(12) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 119.99(12) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 120.99(12) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C6 118.74(11) . . ?
C10 C11 C12 121.98(11) . . ?
C6 C11 C12 119.18(10) . . ?
C3 C12 C13 120.48(11) . . ?
C3 C12 C11 120.50(11) . . ?
C13 C12 C11 119.00(10) . . ?
C14 C13 C18 117.94(11) . . ?
C14 C13 C12 119.78(11) . . ?
C18 C13 C12 122.26(11) . . ?
C15 C14 C13 121.86(12) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 119.33(13) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 120.09(12) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.86(13) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C13 119.90(12) . . ?
C17 C18 N1 118.46(12) . . ?
C13 C18 N1 121.61(11) . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 C20 H20A 109.5 . . ?
C2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C18 N1 C1 O1 177.10(11) . . . . ?
C19 N1 C1 O1 0.02(18) . . . . ?
C18 N1 C1 C2 -4.89(16) . . . . ?
C19 N1 C1 C2 178.03(11) . . . . ?
O1 C1 C2 C3 106.56(13) . . . . ?
N1 C1 C2 C3 -71.43(13) . . . . ?
O1 C1 C2 C20 -20.61(17) . . . . ?
N1 C1 C2 C20 161.40(11) . . . . ?
C1 C2 C3 C12 71.08(13) . . . . ?
C20 C2 C3 C12 -165.04(12) . . . . ?
C1 C2 C3 C4 -104.11(12) . . . . ?
C20 C2 C3 C4 19.76(17) . . . . ?
C12 C3 C4 C5 32.21(16) . . . . ?
C2 C3 C4 C5 -152.62(11) . . . . ?
C3 C4 C5 C6 -49.32(14) . . . . ?
C4 C5 C6 C7 -145.49(12) . . . . ?
C4 C5 C6 C11 35.58(15) . . . . ?
C11 C6 C7 C8 -0.44(19) . . . . ?
C5 C6 C7 C8 -179.36(12) . . . . ?
C6 C7 C8 C9 -1.6(2) . . . . ?
C7 C8 C9 C10 1.5(2) . . . . ?
C8 C9 C10 C11 0.51(19) . . . . ?
C9 C10 C11 C6 -2.48(17) . . . . ?
C9 C10 C11 C12 -178.87(11) . . . . ?
C7 C6 C11 C10 2.42(17) . . . . ?
C5 C6 C11 C10 -178.62(11) . . . . ?
C7 C6 C11 C12 178.92(11) . . . . ?
C5 C6 C11 C12 -2.12(16) . . . . ?
C4 C3 C12 C13 179.98(11) . . . . ?
C2 C3 C12 C13 4.74(17) . . . . ?
C4 C3 C12 C11 1.63(17) . . . . ?
C2 C3 C12 C11 -173.61(10) . . . . ?
C10 C11 C12 C3 158.24(11) . . . . ?
C6 C11 C12 C3 -18.13(16) . . . . ?
C10 C11 C12 C13 -20.13(16) . . . . ?
C6 C11 C12 C13 163.50(10) . . . . ?
C3 C12 C13 C14 131.92(12) . . . . ?
C11 C12 C13 C14 -49.71(15) . . . . ?
C3 C12 C13 C18 -46.89(16) . . . . ?
C11 C12 C13 C18 131.48(12) . . . . ?
C18 C13 C14 C15 -0.78(18) . . . . ?
C12 C13 C14 C15 -179.64(11) . . . . ?
C13 C14 C15 C16 -0.19(19) . . . . ?
C14 C15 C16 C17 1.2(2) . . . . ?
C15 C16 C17 C18 -1.2(2) . . . . ?
C16 C17 C18 C13 0.23(19) . . . . ?
C16 C17 C18 N1 -177.73(12) . . . . ?
C14 C13 C18 C17 0.76(17) . . . . ?
C12 C13 C18 C17 179.59(11) . . . . ?
C14 C13 C18 N1 178.65(11) . . . . ?
C12 C13 C18 N1 -2.52(17) . . . . ?
C1 N1 C18 C17 -131.18(13) . . . . ?
C19 N1 C18 C17 45.88(16) . . . . ?
C1 N1 C18 C13 50.89(17) . . . . ?
C19 N1 C18 C13 -132.04(13) . . . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.032

_shelxl_version_number           2013-4

