# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_11
_database_code_depnum_ccdc_archive 'CCDC 2098712'
loop_
_audit_author_name
_audit_author_address
'Shaojun Liu'
;Shi He Zi University
China
;
_audit_update_record             
;
2021-07-23 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_audit_creation_date             2020-11-02
_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 H22 N2 O'
_chemical_formula_sum            'C23 H22 N2 O'
_chemical_formula_weight         342.42
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   9.8383(3)
_cell_length_b                   9.8397(3)
_cell_length_c                   10.3983(3)
_cell_angle_alpha                96.2480(10)
_cell_angle_beta                 115.9080(10)
_cell_angle_gamma                94.5980(10)
_cell_volume                     890.84(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6672
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      77.15
_cell_measurement_theta_min      4.79
_shelx_estimated_absorpt_T_max   0.877
_shelx_estimated_absorpt_T_min   0.862
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  0.7541
_exptl_absorpt_correction_T_min  0.5836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13254
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.508
_diffrn_reflns_theta_min         4.790
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3031
_reflns_number_total             3684
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3684
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0540
_refine_ls_restrained_S_all      1.080
_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)+(0.0901P)²+0.1948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1547
_refine_ls_wR_factor_ref         0.1663
_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
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), N1(H1)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
C1 C 0.37505(18) 0.52403(16) 0.11218(16) 0.0323(3) Uani 1 1 d . . . . .
C2 C 0.26079(17) 0.52286(16) 0.16764(16) 0.0319(3) Uani 1 1 d . . . . .
C3 C 0.16259(18) 0.62029(17) 0.13369(17) 0.0345(4) Uani 1 1 d . . . . .
H3 H 0.173555 0.688308 0.079379 0.041 Uiso 1 1 calc R . . . .
C4 C 0.04657(18) 0.62079(17) 0.17799(17) 0.0346(4) Uani 1 1 d . . . . .
C5 C -0.0571(2) 0.71906(19) 0.14355(19) 0.0410(4) Uani 1 1 d . . . . .
H5 H -0.048224 0.788320 0.089659 0.049 Uiso 1 1 calc R . . . .
C6 C -0.1696(2) 0.71488(19) 0.1872(2) 0.0432(4) Uani 1 1 d . . . . .
H6 H -0.237825 0.781554 0.164297 0.052 Uiso 1 1 calc R . . . .
C7 C -0.18466(19) 0.61173(19) 0.26635(19) 0.0429(4) Uani 1 1 d . . . . .
H7 H -0.263445 0.609651 0.295894 0.051 Uiso 1 1 calc R . . . .
C8 C -0.08803(19) 0.51505(18) 0.30108(18) 0.0395(4) Uani 1 1 d . . . . .
H8 H -0.100101 0.446476 0.354376 0.047 Uiso 1 1 calc R . . . .
C9 C 0.03119(18) 0.51628(17) 0.25780(17) 0.0350(4) Uani 1 1 d . . . . .
C10 C 0.13257(19) 0.41814(17) 0.29187(17) 0.0350(4) Uani 1 1 d . . . . .
H10 H 0.121462 0.349231 0.345224 0.042 Uiso 1 1 calc R . . . .
C11 C 0.24893(18) 0.41891(16) 0.24970(16) 0.0319(3) Uani 1 1 d . . . . .
C12 C 0.35850(18) 0.32043(16) 0.28581(16) 0.0317(3) Uani 1 1 d . . . . .
C13 C 0.46606(18) 0.32885(16) 0.23727(16) 0.0319(3) Uani 1 1 d . . . . .
C14 C 0.59241(18) 0.24393(16) 0.27374(17) 0.0323(3) Uani 1 1 d . . . . .
C15 C 0.69502(19) 0.24467(17) 0.41823(17) 0.0360(4) Uani 1 1 d . . . . .
H15 H 0.679724 0.294713 0.493129 0.043 Uiso 1 1 calc R . . . .
C16 C 0.8185(2) 0.17347(19) 0.45341(18) 0.0405(4) Uani 1 1 d . . . . .
H16 H 0.887795 0.175161 0.552168 0.049 Uiso 1 1 calc R . . . .
C17 C 0.8418(2) 0.0994(2) 0.3451(2) 0.0457(4) Uani 1 1 d . . . . .
H17 H 0.926096 0.049471 0.369380 0.055 Uiso 1 1 calc R . . . .
C18 C 0.7411(2) 0.0987(2) 0.2013(2) 0.0470(4) Uani 1 1 d . . . . .
H18 H 0.756979 0.048386 0.126841 0.056 Uiso 1 1 calc R . . . .
C19 C 0.6178(2) 0.17075(18) 0.16522(18) 0.0400(4) Uani 1 1 d . . . . .
H19 H 0.550019 0.170455 0.066280 0.048 Uiso 1 1 calc R . . . .
C20 C 0.3738(2) 0.25077(19) 0.51231(18) 0.0413(4) Uani 1 1 d . . . . .
H20A H 0.272438 0.246928 0.511142 0.050 Uiso 1 1 calc R . . . .
H20B H 0.425569 0.347289 0.548656 0.050 Uiso 1 1 calc R . . . .
C21 C 0.4670(2) 0.1579(2) 0.61461(18) 0.0445(4) Uani 1 1 d . . . . .
H21A H 0.414425 0.062730 0.581124 0.067 Uiso 1 1 calc GR . . . .
H21B H 0.479155 0.189362 0.712232 0.067 Uiso 1 1 calc GR . . . .
H21C H 0.567792 0.161695 0.616573 0.067 Uiso 1 1 calc GR . . . .
C22 C 0.2291(2) 0.09661(18) 0.2796(2) 0.0410(4) Uani 1 1 d . . . . .
H22A H 0.130036 0.131737 0.250527 0.049 Uiso 1 1 calc R . . . .
H22B H 0.233420 0.025820 0.341551 0.049 Uiso 1 1 calc R . . . .
C23 C 0.2374(2) 0.03007(18) 0.14539(18) 0.0421(4) Uani 1 1 d . . . . .
H23A H 0.230368 0.099062 0.082341 0.063 Uiso 1 1 calc GR . . . .
H23B H 0.152619 -0.045562 0.093375 0.063 Uiso 1 1 calc GR . . . .
H23C H 0.334486 -0.006376 0.173576 0.063 Uiso 1 1 calc GR . . . .
N1 N 0.46807(15) 0.42556(14) 0.14883(14) 0.0323(3) Uani 1 1 d . . . . .
H1 H 0.535092 0.422271 0.114162 0.039 Uiso 1 1 calc R . . . .
N2 N 0.35319(16) 0.21080(14) 0.36392(14) 0.0337(3) Uani 1 1 d . . . . .
O1 O 0.38847(14) 0.60881(12) 0.03738(13) 0.0397(3) 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 C2 1.470(2) . ?
C1 N1 1.356(2) . ?
C1 O1 1.238(2) . ?
C2 C3 1.379(2) . ?
C2 C11 1.430(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.405(2) . ?
C4 C5 1.421(2) . ?
C4 C9 1.428(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.367(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.412(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.363(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.428(2) . ?
C9 C10 1.405(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.393(2) . ?
C11 C12 1.461(2) . ?
C12 C13 1.358(2) . ?
C12 N2 1.430(2) . ?
C13 C14 1.487(2) . ?
C13 N1 1.398(2) . ?
C14 C15 1.396(2) . ?
C14 C19 1.397(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.380(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.384(2) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.517(3) . ?
C20 N2 1.469(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.514(2) . ?
C22 N2 1.467(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
N1 H1 0.8800 . ?

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
N1 C1 C2 115.75(14) . . ?
O1 C1 C2 123.33(14) . . ?
O1 C1 N1 120.92(14) . . ?
C3 C2 C1 118.47(15) . . ?
C3 C2 C11 121.33(15) . . ?
C11 C2 C1 120.16(14) . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.19(16) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 122.46(16) . . ?
C3 C4 C9 118.29(15) . . ?
C5 C4 C9 119.23(16) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.60(18) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.17(16) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.12(16) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.37(17) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C4 118.50(15) . . ?
C10 C9 C4 119.75(15) . . ?
C10 C9 C8 121.75(16) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 C9 121.92(16) . . ?
C11 C10 H10 119.0 . . ?
C2 C11 C12 119.03(14) . . ?
C10 C11 C2 117.50(15) . . ?
C10 C11 C12 123.47(15) . . ?
C13 C12 C11 118.73(15) . . ?
C13 C12 N2 118.17(14) . . ?
N2 C12 C11 123.03(14) . . ?
C12 C13 C14 125.32(14) . . ?
C12 C13 N1 120.84(14) . . ?
N1 C13 C14 113.82(13) . . ?
C15 C14 C13 120.03(13) . . ?
C15 C14 C19 118.76(15) . . ?
C19 C14 C13 121.03(14) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.67(15) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.27(15) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.53(16) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.49(16) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.27(16) . . ?
C18 C19 H19 119.9 . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
N2 C20 H20A 109.1 . . ?
N2 C20 H20B 109.1 . . ?
N2 C20 C21 112.41(14) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
N2 C22 H22A 109.1 . . ?
N2 C22 H22B 109.1 . . ?
N2 C22 C23 112.69(14) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 C13 125.26(13) . . ?
C1 N1 H1 117.4 . . ?
C13 N1 H1 117.4 . . ?
C12 N2 C20 116.80(13) . . ?
C12 N2 C22 114.30(13) . . ?
C22 N2 C20 113.48(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
