# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_190507a_a
_database_code_depnum_ccdc_archive 'CCDC 1965912'
loop_
_audit_author_name
_audit_author_address
'Manyi Wu'
;Anhui Normal University
China
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H21 N O2'
_chemical_formula_weight         379.44

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   9.5932(14)
_cell_length_b                   9.5959(14)
_cell_length_c                   12.0259(18)
_cell_angle_alpha                89.867(2)
_cell_angle_beta                 77.432(2)
_cell_angle_gamma                67.972(2)
_cell_volume                     997.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4346
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.984
_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      293(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            8800
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.742
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4499
_reflns_number_gt                3394
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0716P)²+0.1825P] 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         4499
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1462
_refine_ls_wR_factor_gt          0.1311
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.54785(17) 0.28013(15) 0.52845(13) 0.0463(3) Uani 1 1 d . . . . .
C2 C 0.6577(2) 0.32321(18) 0.56088(16) 0.0601(4) Uani 1 1 d . . . . .
H2 H 0.720408 0.359931 0.509421 0.072 Uiso 1 1 calc R U . . .
C3 C 0.6689(3) 0.3088(2) 0.67260(18) 0.0706(5) Uani 1 1 d . . . . .
H3 H 0.742200 0.334234 0.697478 0.085 Uiso 1 1 calc R U . . .
C4 C 0.5720(3) 0.2566(2) 0.74906(17) 0.0720(6) Uani 1 1 d . . . . .
H4 H 0.581813 0.249112 0.824313 0.086 Uiso 1 1 calc R U . . .
C5 C 0.4613(2) 0.21522(17) 0.71746(14) 0.0595(4) Uani 1 1 d . . . . .
H5 H 0.396471 0.182391 0.770404 0.071 Uiso 1 1 calc R U . . .
C6 C 0.45013(17) 0.22450(15) 0.60268(13) 0.0467(3) Uani 1 1 d . . . . .
C7 C 0.35880(16) 0.18431(15) 0.53650(12) 0.0435(3) Uani 1 1 d . . . . .
C8 C 0.40553(15) 0.21865(14) 0.42608(12) 0.0401(3) Uani 1 1 d . . . . .
C9 C 0.38507(15) 0.20102(15) 0.30710(12) 0.0408(3) Uani 1 1 d . . . . .
H9 H 0.425716 0.093139 0.282358 0.049 Uiso 1 1 calc R U . . .
C10 C 0.49203(16) 0.27250(16) 0.23443(12) 0.0440(3) Uani 1 1 d . . . . .
H10 H 0.426669 0.372031 0.216515 0.053 Uiso 1 1 calc R U . . .
C11 C 0.59438(17) 0.29507(18) 0.30980(13) 0.0485(3) Uani 1 1 d . . . . .
H11A H 0.698916 0.219540 0.288058 0.058 Uiso 1 1 calc R U . . .
H11B H 0.597735 0.394762 0.305604 0.058 Uiso 1 1 calc R U . . .
C12 C 0.25271(17) 0.11070(17) 0.58076(15) 0.0529(4) Uani 1 1 d . . . . .
C13 C 0.1573(2) 0.0808(2) 0.50803(18) 0.0683(5) Uani 1 1 d . . . . .
H13A H 0.106943 0.018154 0.545788 0.102 Uiso 1 1 calc R U . . .
H13B H 0.222785 0.030335 0.435708 0.102 Uiso 1 1 calc R U . . .
H13C H 0.080782 0.174657 0.495857 0.102 Uiso 1 1 calc R U . . .
C14 C 0.22179(15) 0.27327(15) 0.29021(13) 0.0430(3) Uani 1 1 d . . . . .
C15 C 0.11744(17) 0.40652(16) 0.35124(13) 0.0492(4) Uani 1 1 d . . . . .
H15 H 0.146249 0.451817 0.405732 0.059 Uiso 1 1 calc R U . . .
C16 C -0.02978(18) 0.47373(18) 0.33236(16) 0.0594(4) Uani 1 1 d . . . . .
H16 H -0.099457 0.562956 0.374829 0.071 Uiso 1 1 calc R U . . .
C17 C -0.0730(2) 0.4096(2) 0.25175(19) 0.0694(5) Uani 1 1 d . . . . .
H17 H -0.171686 0.455149 0.238864 0.083 Uiso 1 1 calc R U . . .
C18 C 0.0291(2) 0.2785(2) 0.1902(2) 0.0850(7) Uani 1 1 d . . . . .
H18 H -0.000246 0.234992 0.135099 0.102 Uiso 1 1 calc R U . . .
C19 C 0.1767(2) 0.2092(2) 0.20891(18) 0.0699(5) Uani 1 1 d . . . . .
H19 H 0.245271 0.119436 0.166592 0.084 Uiso 1 1 calc R U . . .
C20 C 0.58872(18) 0.17942(19) 0.12242(14) 0.0535(4) Uani 1 1 d . . . . .
C21 C 0.69675(18) 0.2373(2) 0.04624(13) 0.0570(4) Uani 1 1 d . . . . .
C22 C 0.6767(2) 0.3869(3) 0.05014(17) 0.0733(5) Uani 1 1 d . . . . .
H22 H 0.593757 0.457312 0.102357 0.088 Uiso 1 1 calc R U . . .
C23 C 0.7812(3) 0.4323(4) -0.0245(2) 0.1038(9) Uani 1 1 d . . . . .
H23 H 0.767441 0.533582 -0.023611 0.125 Uiso 1 1 calc R U . . .
C24 C 0.9056(4) 0.3261(5) -0.1001(2) 0.1182(12) Uani 1 1 d . . . . .
H24 H 0.976550 0.356010 -0.149088 0.142 Uiso 1 1 calc R U . . .
C25 C 0.9250(3) 0.1788(5) -0.10339(19) 0.1090(10) Uani 1 1 d . . . . .
H25 H 1.009086 0.108266 -0.154666 0.131 Uiso 1 1 calc R U . . .
C26 C 0.8220(2) 0.1337(3) -0.03198(15) 0.0771(6) Uani 1 1 d . . . . .
H26 H 0.835589 0.032474 -0.035525 0.093 Uiso 1 1 calc R U . . .
N1 N 0.51539(13) 0.27705(13) 0.42246(10) 0.0439(3) Uani 1 1 d . . . . .
O1 O 0.24198(16) 0.07117(17) 0.67854(12) 0.0792(4) Uani 1 1 d . . . . .
O2 O 0.58121(18) 0.06151(16) 0.09618(12) 0.0829(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 N1 1.3793(18) . ?
C1 C2 1.393(2) . ?
C1 C6 1.403(2) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.408(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.452(2) . ?
C7 C8 1.387(2) . ?
C7 C12 1.456(2) . ?
C8 N1 1.3600(18) . ?
C8 C9 1.504(2) . ?
C9 C14 1.5161(18) . ?
C9 C10 1.556(2) . ?
C9 H9 0.9800 . ?
C10 C20 1.521(2) . ?
C10 C11 1.543(2) . ?
C10 H10 0.9800 . ?
C11 N1 1.4458(19) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O1 1.230(2) . ?
C12 C13 1.494(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.378(2) . ?
C14 C19 1.381(2) . ?
C15 C16 1.385(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.363(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.361(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.388(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 O2 1.207(2) . ?
C20 C21 1.496(2) . ?
C21 C22 1.375(3) . ?
C21 C26 1.391(3) . ?
C22 C23 1.392(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.381(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.354(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.361(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

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 129.32(15) . . ?
N1 C1 C6 106.71(12) . . ?
C2 C1 C6 123.94(15) . . ?
C3 C2 C1 116.71(18) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C2 C3 C4 120.89(18) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 122.57(17) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C4 C5 C6 117.88(18) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C1 C6 C5 117.98(15) . . ?
C1 C6 C7 107.72(13) . . ?
C5 C6 C7 134.28(16) . . ?
C8 C7 C6 105.56(13) . . ?
C8 C7 C12 129.78(14) . . ?
C6 C7 C12 124.44(14) . . ?
N1 C8 C7 109.48(12) . . ?
N1 C8 C9 109.29(12) . . ?
C7 C8 C9 140.96(13) . . ?
C8 C9 C14 116.66(11) . . ?
C8 C9 C10 103.17(11) . . ?
C14 C9 C10 110.84(11) . . ?
C8 C9 H9 108.6 . . ?
C14 C9 H9 108.6 . . ?
C10 C9 H9 108.6 . . ?
C20 C10 C11 111.62(12) . . ?
C20 C10 C9 113.24(12) . . ?
C11 C10 C9 107.37(11) . . ?
C20 C10 H10 108.2 . . ?
C11 C10 H10 108.2 . . ?
C9 C10 H10 108.2 . . ?
N1 C11 C10 101.94(11) . . ?
N1 C11 H11A 111.4 . . ?
C10 C11 H11A 111.4 . . ?
N1 C11 H11B 111.4 . . ?
C10 C11 H11B 111.4 . . ?
H11A C11 H11B 109.2 . . ?
O1 C12 C7 120.03(16) . . ?
O1 C12 C13 119.29(16) . . ?
C7 C12 C13 120.68(15) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 118.47(14) . . ?
C15 C14 C9 121.39(13) . . ?
C19 C14 C9 120.09(13) . . ?
C14 C15 C16 120.77(15) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 120.26(16) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 119.66(16) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.73(18) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C14 C19 C18 120.11(16) . . ?
C14 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
O2 C20 C21 120.74(15) . . ?
O2 C20 C10 121.56(15) . . ?
C21 C20 C10 117.68(14) . . ?
C22 C21 C26 119.30(18) . . ?
C22 C21 C20 122.95(16) . . ?
C26 C21 C20 117.75(18) . . ?
C21 C22 C23 119.6(2) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C22 119.6(3) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C25 C24 C23 120.6(2) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 120.2(3) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 120.7(3) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
C8 N1 C1 110.52(12) . . ?
C8 N1 C11 116.02(12) . . ?
C1 N1 C11 132.16(12) . . ?

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.038

