# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2115545'
loop_
_audit_author_name
_audit_author_address
'Meng Sun'
;Northwest University (China)
China
;
_audit_update_record             
;
2021-10-14 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H19 N O2'
_chemical_formula_weight         413.45

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'
O O 0.0106 0.0060 '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'

_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                   10.336(3)
_cell_length_b                   10.907(3)
_cell_length_c                   11.626(3)
_cell_angle_alpha                117.746(12)
_cell_angle_beta                 101.702(16)
_cell_angle_gamma                100.621(16)
_cell_volume                     1075.5(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7150
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      25.33

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   0.4070
_exptl_transmission_factor_max   0.7052
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_reflns_number            15122
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.441
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3888
_reflns_number_gt                2967
_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 SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0400P)²+0.3642P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3888
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
O1 O 0.36402(11) 0.32651(12) -0.03351(13) 0.0285(3) Uani 1 1 d . . . . .
O2 O 1.13042(12) 0.62389(14) 0.42039(13) 0.0377(3) Uani 1 1 d . . . . .
N1 N 0.60171(13) 0.43361(14) 0.07349(14) 0.0217(3) Uani 1 1 d . . . . .
H1 H 0.613065 0.493577 0.042823 0.026 Uiso 1 1 calc R U . . .
C7 C 0.64266(17) 0.30135(17) 0.17631(17) 0.0204(4) Uani 1 1 d . . . . .
C24 C 0.94378(16) 0.74898(17) 0.54064(17) 0.0217(4) Uani 1 1 d . . . . .
C10 C 0.97233(16) 0.46815(17) 0.19274(17) 0.0215(4) Uani 1 1 d . . . . .
C2 C 0.50243(17) 0.24898(17) 0.10023(17) 0.0218(4) Uani 1 1 d . . . . .
C9 C 0.83305(16) 0.40169(17) 0.10802(17) 0.0200(4) Uani 1 1 d . . . . .
C12 C 0.89973(16) 0.62979(17) 0.39388(17) 0.0208(4) Uani 1 1 d . . . . .
C18 C 0.65518(16) 0.63332(17) 0.35383(17) 0.0208(4) Uani 1 1 d . . . . .
C14 C 0.80120(18) 0.30479(18) -0.03252(18) 0.0249(4) Uani 1 1 d . . . . .
H14 H 0.706647 0.259189 -0.091210 0.030 Uiso 1 1 calc R U . . .
C6 C 0.69653(18) 0.24247(18) 0.25031(18) 0.0246(4) Uani 1 1 d . . . . .
H6 H 0.792943 0.277776 0.301947 0.029 Uiso 1 1 calc R U . . .
C1 C 0.47630(16) 0.33651(17) 0.03683(17) 0.0219(4) Uani 1 1 d . . . . .
C11 C 1.01014(17) 0.57622(18) 0.34212(18) 0.0237(4) Uani 1 1 d . . . . .
C13 C 0.76530(16) 0.56909(17) 0.31111(17) 0.0195(4) Uani 1 1 d . . . . .
C8 C 0.71668(16) 0.43089(17) 0.16803(17) 0.0197(4) Uani 1 1 d . . . . .
C25 C 0.89055(18) 0.72412(19) 0.63087(18) 0.0283(4) Uani 1 1 d . . . . .
H25 H 0.825679 0.631394 0.597592 0.034 Uiso 1 1 calc R U . . .
C29 C 1.04112(18) 0.88536(18) 0.59277(19) 0.0283(4) Uani 1 1 d . . . . .
H29 H 1.080522 0.904299 0.533315 0.034 Uiso 1 1 calc R U . . .
C17 C 1.07785(18) 0.43706(18) 0.13642(19) 0.0255(4) Uani 1 1 d . . . . .
H17 H 1.172681 0.482542 0.194373 0.031 Uiso 1 1 calc R U . . .
C3 C 0.40947(18) 0.13592(19) 0.09542(19) 0.0290(4) Uani 1 1 d . . . . .
H3 H 0.313333 0.099924 0.042673 0.035 Uiso 1 1 calc R U . . .
C16 C 1.04521(18) 0.34096(19) -0.00247(19) 0.0282(4) Uani 1 1 d . . . . .
H16 H 1.117192 0.320013 -0.040436 0.034 Uiso 1 1 calc R U . . .
C19 C 0.54805(17) 0.56529(18) 0.38134(18) 0.0249(4) Uani 1 1 d . . . . .
H19 H 0.546139 0.476631 0.378802 0.030 Uiso 1 1 calc R U . . .
C20 C 0.44442(18) 0.6262(2) 0.41234(19) 0.0300(4) Uani 1 1 d . . . . .
H20 H 0.372096 0.579074 0.431323 0.036 Uiso 1 1 calc R U . . .
C15 C 0.90634(19) 0.27468(19) -0.08697(19) 0.0283(4) Uani 1 1 d . . . . .
H15 H 0.883594 0.208171 -0.182876 0.034 Uiso 1 1 calc R U . . .
C27 C 1.0253(2) 0.9666(2) 0.8181(2) 0.0334(5) Uani 1 1 d . . . . .
H27 H 1.052671 1.040937 0.912437 0.040 Uiso 1 1 calc R U . . .
C5 C 0.60323(19) 0.12923(19) 0.2458(2) 0.0311(4) Uani 1 1 d . . . . .
H5 H 0.636846 0.086312 0.295389 0.037 Uiso 1 1 calc R U . . .
C26 C 0.9301(2) 0.8320(2) 0.76874(19) 0.0334(5) Uani 1 1 d . . . . .
H26 H 0.892012 0.813361 0.829006 0.040 Uiso 1 1 calc R U . . .
C28 C 1.08051(19) 0.99303(19) 0.7305(2) 0.0343(5) Uani 1 1 d . . . . .
H28 H 1.146021 1.085710 0.764709 0.041 Uiso 1 1 calc R U . . .
C23 C 0.65603(19) 0.76392(19) 0.3603(2) 0.0314(4) Uani 1 1 d . . . . .
H23 H 0.729503 0.813011 0.344018 0.038 Uiso 1 1 calc R U . . .
C4 C 0.4623(2) 0.0775(2) 0.1706(2) 0.0338(5) Uani 1 1 d . . . . .
H4 H 0.401195 0.000980 0.170616 0.041 Uiso 1 1 calc R U . . .
C21 C 0.44489(19) 0.7540(2) 0.4160(2) 0.0350(5) Uani 1 1 d . . . . .
H21 H 0.372590 0.794350 0.436061 0.042 Uiso 1 1 calc R U . . .
C22 C 0.5513(2) 0.8236(2) 0.3903(2) 0.0385(5) Uani 1 1 d . . . . .
H22 H 0.552506 0.912322 0.393085 0.046 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 1.2300(19) . ?
O2 C11 1.227(2) . ?
N1 C1 1.354(2) . ?
N1 C8 1.4611(19) . ?
N1 H1 0.8800 . ?
C7 C2 1.383(2) . ?
C7 C6 1.384(2) . ?
C7 C8 1.533(2) . ?
C24 C25 1.386(2) . ?
C24 C29 1.398(2) . ?
C24 C12 1.487(2) . ?
C10 C9 1.394(2) . ?
C10 C17 1.397(2) . ?
C10 C11 1.486(2) . ?
C2 C3 1.387(2) . ?
C2 C1 1.482(2) . ?
C9 C14 1.393(2) . ?
C9 C8 1.520(2) . ?
C12 C13 1.349(2) . ?
C12 C11 1.484(2) . ?
C18 C23 1.389(2) . ?
C18 C19 1.393(2) . ?
C18 C13 1.494(2) . ?
C14 C15 1.381(2) . ?
C14 H14 0.9500 . ?
C6 C5 1.392(2) . ?
C6 H6 0.9500 . ?
C13 C8 1.529(2) . ?
C25 C26 1.386(3) . ?
C25 H25 0.9500 . ?
C29 C28 1.384(3) . ?
C29 H29 0.9500 . ?
C17 C16 1.376(3) . ?
C17 H17 0.9500 . ?
C3 C4 1.386(2) . ?
C3 H3 0.9500 . ?
C16 C15 1.390(3) . ?
C16 H16 0.9500 . ?
C19 C20 1.384(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.374(3) . ?
C20 H20 0.9500 . ?
C15 H15 0.9500 . ?
C27 C28 1.376(3) . ?
C27 C26 1.381(3) . ?
C27 H27 0.9500 . ?
C5 C4 1.387(3) . ?
C5 H5 0.9500 . ?
C26 H26 0.9500 . ?
C28 H28 0.9500 . ?
C23 C22 1.386(3) . ?
C23 H23 0.9500 . ?
C4 H4 0.9500 . ?
C21 C22 1.383(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

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 C8 114.64(13) . . ?
C1 N1 H1 122.7 . . ?
C8 N1 H1 122.7 . . ?
C2 C7 C6 121.38(15) . . ?
C2 C7 C8 109.50(13) . . ?
C6 C7 C8 129.05(15) . . ?
C25 C24 C29 118.23(16) . . ?
C25 C24 C12 119.53(15) . . ?
C29 C24 C12 122.21(16) . . ?
C9 C10 C17 119.98(16) . . ?
C9 C10 C11 120.49(15) . . ?
C17 C10 C11 119.50(15) . . ?
C7 C2 C3 121.57(15) . . ?
C7 C2 C1 108.67(14) . . ?
C3 C2 C1 129.72(15) . . ?
C14 C9 C10 119.15(16) . . ?
C14 C9 C8 120.11(14) . . ?
C10 C9 C8 120.72(15) . . ?
C13 C12 C11 120.76(16) . . ?
C13 C12 C24 122.20(15) . . ?
C11 C12 C24 117.01(14) . . ?
C23 C18 C19 118.39(16) . . ?
C23 C18 C13 118.35(15) . . ?
C19 C18 C13 123.19(14) . . ?
C15 C14 C9 120.35(16) . . ?
C15 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
C7 C6 C5 117.08(16) . . ?
C7 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
O1 C1 N1 125.86(15) . . ?
O1 C1 C2 127.85(15) . . ?
N1 C1 C2 106.28(13) . . ?
O2 C11 C12 120.56(16) . . ?
O2 C11 C10 121.09(16) . . ?
C12 C11 C10 118.30(14) . . ?
C12 C13 C18 121.89(15) . . ?
C12 C13 C8 122.05(15) . . ?
C18 C13 C8 116.06(13) . . ?
N1 C8 C9 111.17(14) . . ?
N1 C8 C13 110.77(13) . . ?
C9 C8 C13 113.84(13) . . ?
N1 C8 C7 100.69(12) . . ?
C9 C8 C7 111.28(13) . . ?
C13 C8 C7 108.29(13) . . ?
C26 C25 C24 121.25(16) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C28 C29 C24 120.44(17) . . ?
C28 C29 H29 119.8 . . ?
C24 C29 H29 119.8 . . ?
C16 C17 C10 120.39(16) . . ?
C16 C17 H17 119.8 . . ?
C10 C17 H17 119.8 . . ?
C4 C3 C2 117.39(16) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C17 C16 C15 119.64(17) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C20 C19 C18 120.34(16) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 120.77(17) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C14 C15 C16 120.49(17) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C28 C27 C26 119.98(18) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C4 C5 C6 121.59(16) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C27 C26 C25 119.68(18) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C27 C28 C29 120.39(17) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C22 C23 C18 120.96(17) . . ?
C22 C23 H23 119.5 . . ?
C18 C23 H23 119.5 . . ?
C3 C4 C5 120.98(16) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C20 C21 C22 119.58(17) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C23 119.95(17) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.046



