# 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 2132074'
loop_
_audit_author_name
_audit_author_address
'Shaojun Liu'
;Shi He Zi University
China
;
_audit_update_record             
;
2022-01-03 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_audit_creation_date             2021-11-25
_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 0.0033 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                   9.4001(5)
_cell_length_b                   9.5785(5)
_cell_length_c                   10.6816(5)
_cell_angle_alpha                94.508(2)
_cell_angle_beta                 94.426(2)
_cell_angle_gamma                110.611(2)
_cell_volume                     891.73(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4719
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1197 before and 0.0455 after correction. The Ratio of minimum to maximum transmission is 0.8997. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11292
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.741
_diffrn_reflns_theta_min         2.286
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_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                3051
_reflns_number_total             3783
_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       ?
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3783
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.032
_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)+(0.0605P)²+0.2915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1324
_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:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), 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     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
C1 C 0.13942(17) 0.87689(16) 0.99368(13) 0.0270(3) Uani 1 1 d . . . . .
C2 C 0.25240(16) 0.80482(15) 1.00151(12) 0.0250(3) Uani 1 1 d . . . . .
C3 C 0.37175(16) 0.83408(16) 0.91828(13) 0.0262(3) Uani 1 1 d . . . . .
C4 C 0.38132(17) 0.92102(17) 0.81569(14) 0.0305(3) Uani 1 1 d . . . . .
H4 H 0.305727 0.963700 0.798325 0.037 Uiso 1 1 calc R . . . .
C5 C 0.49827(18) 0.94442(18) 0.74105(15) 0.0348(4) Uani 1 1 d . . . . .
H5 H 0.502081 1.002816 0.672626 0.042 Uiso 1 1 calc R . . . .
C6 C 0.61222(18) 0.88370(18) 0.76399(15) 0.0366(4) Uani 1 1 d . . . . .
H6 H 0.692275 0.900473 0.711355 0.044 Uiso 1 1 calc R . . . .
C7 C 0.60715(18) 0.80035(17) 0.86249(15) 0.0339(3) Uani 1 1 d . . . . .
H7 H 0.685077 0.760343 0.878888 0.041 Uiso 1 1 calc R . . . .
C8 C 0.48763(17) 0.77266(16) 0.94051(13) 0.0288(3) Uani 1 1 d . . . . .
C9 C 0.48273(18) 0.68346(17) 1.04155(14) 0.0320(3) Uani 1 1 d . . . . .
H9 H 0.562216 0.645379 1.057555 0.038 Uiso 1 1 calc R . . . .
C10 C 0.36729(17) 0.65173(17) 1.11531(14) 0.0302(3) Uani 1 1 d . . . . .
H10 H 0.365295 0.589089 1.180343 0.036 Uiso 1 1 calc R . . . .
C11 C 0.24829(16) 0.71089(15) 1.09703(13) 0.0260(3) Uani 1 1 d . . . . .
C12 C 0.12898(16) 0.67650(15) 1.18057(13) 0.0260(3) Uani 1 1 d . . . . .
C13 C 0.02245(16) 0.74243(16) 1.16764(13) 0.0263(3) Uani 1 1 d . . . . .
C14 C -0.10966(17) 0.71883(16) 1.24260(13) 0.0280(3) Uani 1 1 d . . . . .
C15 C -0.1253(2) 0.83843(18) 1.31544(15) 0.0360(4) Uani 1 1 d . . . . .
H15 H -0.052091 0.936789 1.316294 0.043 Uiso 1 1 calc R . . . .
C16 C -0.2474(2) 0.8149(2) 1.38695(16) 0.0433(4) Uani 1 1 d . . . . .
H16 H -0.257377 0.897279 1.436157 0.052 Uiso 1 1 calc R . . . .
C17 C -0.3544(2) 0.6721(2) 1.38685(16) 0.0439(4) Uani 1 1 d . . . . .
H17 H -0.436398 0.655876 1.437344 0.053 Uiso 1 1 calc R . . . .
C18 C -0.34138(19) 0.5535(2) 1.31317(16) 0.0411(4) Uani 1 1 d . . . . .
H18 H -0.415574 0.455572 1.311959 0.049 Uiso 1 1 calc R . . . .
C19 C -0.22061(17) 0.57619(18) 1.24071(15) 0.0333(3) Uani 1 1 d . . . . .
H19 H -0.213409 0.493863 1.189368 0.040 Uiso 1 1 calc R . . . .
C20 C 0.12244(18) 0.62777(18) 1.40600(14) 0.0341(4) Uani 1 1 d . . . . .
H20A H 0.144208 0.557625 1.461100 0.041 Uiso 1 1 calc R . . . .
H20B H 0.015752 0.620792 1.412735 0.041 Uiso 1 1 calc R . . . .
C21 C 0.2281(2) 0.7842(2) 1.45240(16) 0.0474(4) Uani 1 1 d . . . . .
H21A H 0.200247 0.855379 1.403981 0.071 Uiso 1 1 calc GR . . . .
H21B H 0.333537 0.793666 1.441503 0.071 Uiso 1 1 calc GR . . . .
H21C H 0.219759 0.806211 1.542123 0.071 Uiso 1 1 calc GR . . . .
C22 C 0.0650(2) 0.42030(17) 1.23330(16) 0.0371(4) Uani 1 1 d . . . . .
H22A H 0.076680 0.402675 1.142727 0.044 Uiso 1 1 calc R . . . .
H22B H -0.045791 0.388183 1.241455 0.044 Uiso 1 1 calc R . . . .
C23 C 0.1311(2) 0.3241(2) 1.30659(17) 0.0431(4) Uani 1 1 d . . . . .
H23A H 0.090903 0.220923 1.264898 0.065 Uiso 1 1 calc GR . . . .
H23B H 0.102270 0.325032 1.392815 0.065 Uiso 1 1 calc GR . . . .
H23C H 0.242779 0.364157 1.309557 0.065 Uiso 1 1 calc GR . . . .
N1 N 0.03452(14) 0.84246(14) 1.07907(11) 0.0276(3) Uani 1 1 d . . . . .
H1 H -0.031689 0.888470 1.077441 0.033 Uiso 1 1 calc R . . . .
N2 N 0.13649(14) 0.58121(13) 1.27484(11) 0.0279(3) Uani 1 1 d . . . . .
O1 O 0.13137(13) 0.96634(13) 0.91714(10) 0.0355(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 1.4570(19) . ?
C1 N1 1.3676(18) . ?
C1 O1 1.2467(17) . ?
C2 C3 1.449(2) . ?
C2 C11 1.4063(19) . ?
C3 C4 1.417(2) . ?
C3 C8 1.422(2) . ?
C4 C5 1.373(2) . ?
C5 C6 1.402(2) . ?
C6 C7 1.364(2) . ?
C7 C8 1.413(2) . ?
C8 C9 1.422(2) . ?
C9 C10 1.352(2) . ?
C10 C11 1.4284(19) . ?
C11 C12 1.450(2) . ?
C12 C13 1.363(2) . ?
C12 N2 1.4251(17) . ?
C13 C14 1.490(2) . ?
C13 N1 1.3815(17) . ?
C14 C15 1.391(2) . ?
C14 C19 1.394(2) . ?
C15 C16 1.390(2) . ?
C16 C17 1.384(3) . ?
C17 C18 1.377(3) . ?
C18 C19 1.387(2) . ?
C20 C21 1.496(2) . ?
C20 N2 1.4666(19) . ?
C22 C23 1.512(2) . ?
C22 N2 1.4633(19) . ?

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 116.09(12) . . ?
O1 C1 C2 125.75(13) . . ?
O1 C1 N1 118.15(13) . . ?
C3 C2 C1 121.62(12) . . ?
C11 C2 C1 118.26(13) . . ?
C11 C2 C3 120.03(12) . . ?
C4 C3 C2 124.20(13) . . ?
C4 C3 C8 117.44(13) . . ?
C8 C3 C2 118.36(13) . . ?
C5 C4 C3 120.93(14) . . ?
C4 C5 C6 121.19(15) . . ?
C7 C6 C5 119.44(14) . . ?
C6 C7 C8 120.93(14) . . ?
C7 C8 C3 120.07(14) . . ?
C7 C8 C9 120.20(14) . . ?
C9 C8 C3 119.73(13) . . ?
C10 C9 C8 121.36(14) . . ?
C9 C10 C11 121.06(14) . . ?
C2 C11 C10 119.34(13) . . ?
C2 C11 C12 121.67(12) . . ?
C10 C11 C12 118.96(13) . . ?
C13 C12 C11 118.20(12) . . ?
C13 C12 N2 124.66(13) . . ?
N2 C12 C11 117.06(12) . . ?
C12 C13 C14 125.99(13) . . ?
C12 C13 N1 119.25(13) . . ?
N1 C13 C14 114.76(12) . . ?
C15 C14 C13 120.80(14) . . ?
C15 C14 C19 118.65(14) . . ?
C19 C14 C13 120.55(13) . . ?
C16 C15 C14 120.40(16) . . ?
C17 C16 C15 120.32(16) . . ?
C18 C17 C16 119.65(16) . . ?
C17 C18 C19 120.39(16) . . ?
C18 C19 C14 120.55(15) . . ?
N2 C20 C21 113.10(13) . . ?
N2 C22 C23 113.96(14) . . ?
C1 N1 C13 126.29(12) . . ?
C12 N2 C20 118.86(11) . . ?
C12 N2 C22 114.96(11) . . ?
C22 N2 C20 115.77(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
