# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_wcs-nn
_database_code_depnum_ccdc_archive 'CCDC 2279386'
loop_
_audit_author_name
_audit_author_address
'Cong-Shuai Wang'
;Wuhan University
China
;
_audit_update_record             
;
2023-07-05 deposited with the CCDC.	2023-10-05 downloaded from the CCDC.
;
_audit_creation_date             2023-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C30 H25 N3 O2'
_chemical_formula_sum            'C30 H25 N3 O2'
_chemical_formula_weight         459.53
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.3836(2)
_cell_length_b                   17.6933(6)
_cell_length_c                   18.4913(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2415.71(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.0670
_cell_measurement_theta_min      3.4140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12507
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.487
_diffrn_reflns_theta_min         3.457
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3854
_reflns_number_total             4262
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 
;
 Flack x determined using 1517 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.04(10)
_refine_ls_extinction_coef       0.0048(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.086
_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)+(0.0570P)²+0.0400P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0924
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C18(H18),
 C20(H20), C21(H21), C23(H23), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C24(H24A,H24B,H24C)
;
_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
O1 O -0.6280(3) -0.13134(9) -0.00060(8) 0.0691(5) Uani 1 1 d . . . . .
O2 O -0.8760(2) -0.18212(9) 0.04991(8) 0.0644(4) Uani 1 1 d . . . . .
N1 N -0.4534(2) -0.15519(9) 0.21950(8) 0.0441(4) Uani 1 1 d . . . . .
N2 N -0.3037(2) -0.13822(9) 0.26172(8) 0.0469(4) Uani 1 1 d . . . . .
N3 N -0.1537(3) -0.35954(12) 0.17111(11) 0.0754(6) Uani 1 1 d . . . . .
H3 H -0.1483 -0.3821 0.1300 0.091 Uiso 1 1 calc R . . . .
C1 C -0.5954(3) -0.20244(11) 0.24091(10) 0.0452(4) Uani 1 1 d . . . . .
C2 C -0.7038(3) -0.20869(12) 0.18170(11) 0.0489(5) Uani 1 1 d . . . . .
H2 H -0.8109 -0.2363 0.1793 0.059 Uiso 1 1 calc R . . . .
C3 C -0.6272(3) -0.16633(11) 0.12417(10) 0.0469(5) Uani 1 1 d . . . . .
C4 C -0.4696(3) -0.13408(11) 0.14877(10) 0.0470(5) Uani 1 1 d . . . . .
C5 C -0.7037(3) -0.15724(12) 0.05196(11) 0.0518(5) Uani 1 1 d . . . . .
C6 C -0.9681(4) -0.17491(17) -0.01794(13) 0.0789(8) Uani 1 1 d . . . . .
H6A H -0.9187 -0.2105 -0.0518 0.118 Uiso 1 1 calc GR . . . .
H6B H -0.9524 -0.1245 -0.0362 0.118 Uiso 1 1 calc GR . . . .
H6C H -1.0948 -0.1849 -0.0113 0.118 Uiso 1 1 calc GR . . . .
C7 C -0.3350(4) -0.08270(15) 0.11412(13) 0.0694(7) Uani 1 1 d . . . . .
H7A H -0.3455 -0.0331 0.1347 0.104 Uiso 1 1 calc GR . . . .
H7B H -0.3579 -0.0802 0.0631 0.104 Uiso 1 1 calc GR . . . .
H7C H -0.2150 -0.1018 0.1223 0.104 Uiso 1 1 calc GR . . . .
C8 C -0.2913(3) -0.07345(12) 0.30402(10) 0.0483(5) Uani 1 1 d . . . . .
C9 C -0.3878(3) -0.00659(12) 0.29902(11) 0.0581(5) Uani 1 1 d . . . . .
H9 H -0.4785 0.0002 0.2647 0.070 Uiso 1 1 calc R . . . .
C10 C -0.3424(4) 0.04947(14) 0.34751(13) 0.0679(7) Uani 1 1 d . . . . .
H10 H -0.4036 0.0954 0.3461 0.081 Uiso 1 1 calc R . . . .
C11 C -0.2056(4) 0.03836(15) 0.39887(13) 0.0708(7) Uani 1 1 d . . . . .
H11 H -0.1781 0.0771 0.4310 0.085 Uiso 1 1 calc R . . . .
C12 C -0.1111(4) -0.02817(15) 0.40293(12) 0.0666(7) Uani 1 1 d . . . . .
H12 H -0.0199 -0.0344 0.4371 0.080 Uiso 1 1 calc R . . . .
C13 C -0.1537(3) -0.08681(13) 0.35476(11) 0.0532(5) Uani 1 1 d . . . . .
C14 C -0.0878(3) -0.16146(13) 0.34294(11) 0.0573(5) Uani 1 1 d . . . . .
H14 H 0.0039 -0.1849 0.3691 0.069 Uiso 1 1 calc R . . . .
C15 C -0.1820(3) -0.19296(12) 0.28670(11) 0.0492(5) Uani 1 1 d . . . . .
C16 C -0.1726(3) -0.26712(13) 0.25316(11) 0.0526(5) Uani 1 1 d . . . . .
C17 C -0.1633(3) -0.33792(12) 0.29038(12) 0.0549(5) Uani 1 1 d . . . . .
C18 C -0.1675(3) -0.35834(14) 0.36337(14) 0.0655(6) Uani 1 1 d . . . . .
H18 H -0.1795 -0.3213 0.3988 0.079 Uiso 1 1 calc R . . . .
C19 C -0.1538(4) -0.43291(16) 0.38282(18) 0.0808(8) Uani 1 1 d . . . . .
C20 C -0.1369(4) -0.48823(16) 0.3276(2) 0.0880(9) Uani 1 1 d . . . . .
H20 H -0.1265 -0.5388 0.3408 0.106 Uiso 1 1 calc R . . . .
C21 C -0.1354(4) -0.47017(16) 0.2562(2) 0.0830(8) Uani 1 1 d . . . . .
H21 H -0.1247 -0.5075 0.2210 0.100 Uiso 1 1 calc R . . . .
C22 C -0.1504(3) -0.39410(14) 0.23698(15) 0.0653(6) Uani 1 1 d . . . . .
C23 C -0.1670(3) -0.28325(15) 0.18091(13) 0.0632(6) Uani 1 1 d . . . . .
H23 H -0.1716 -0.2476 0.1440 0.076 Uiso 1 1 calc R . . . .
C24 C -0.1531(7) -0.4554(2) 0.4619(2) 0.1270(15) Uani 1 1 d . . . . .
H24A H -0.0310 -0.4649 0.4772 0.190 Uiso 1 1 calc GR . . . .
H24B H -0.2243 -0.5003 0.4683 0.190 Uiso 1 1 calc GR . . . .
H24C H -0.2037 -0.4152 0.4904 0.190 Uiso 1 1 calc GR . . . .
C25 C -0.6096(3) -0.23893(12) 0.31214(10) 0.0483(5) Uani 1 1 d . . . . .
C26 C -0.5615(3) -0.20428(16) 0.37661(12) 0.0644(6) Uani 1 1 d . . . . .
H26 H -0.5163 -0.1552 0.3760 0.077 Uiso 1 1 calc R . . . .
C27 C -0.5800(4) -0.24166(18) 0.44149(13) 0.0809(8) Uani 1 1 d . . . . .
H27 H -0.5453 -0.2178 0.4841 0.097 Uiso 1 1 calc R . . . .
C28 C -0.6488(4) -0.31358(18) 0.44416(16) 0.0810(8) Uani 1 1 d . . . . .
H28 H -0.6609 -0.3386 0.4881 0.097 Uiso 1 1 calc R . . . .
C29 C -0.6991(4) -0.34789(16) 0.38110(16) 0.0785(8) Uani 1 1 d . . . . .
H29 H -0.7472 -0.3965 0.3826 0.094 Uiso 1 1 calc R . . . .
C30 C -0.6801(3) -0.31190(13) 0.31519(14) 0.0623(6) Uani 1 1 d . . . . .
H30 H -0.7143 -0.3364 0.2729 0.075 Uiso 1 1 calc R . . . .


_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 C5 1.211(3) . ?
O2 C5 1.347(3) . ?
O2 C6 1.433(3) . ?
N1 N2 1.386(2) . ?
N1 C1 1.399(3) . ?
N1 C4 1.365(2) . ?
N2 C8 1.391(2) . ?
N2 C15 1.400(3) . ?
N3 C22 1.363(3) . ?
N3 C23 1.365(3) . ?
C1 C2 1.361(3) . ?
C1 C25 1.471(3) . ?
C2 C3 1.419(3) . ?
C3 C4 1.373(3) . ?
C3 C5 1.459(3) . ?
C4 C7 1.492(3) . ?
C8 C9 1.384(3) . ?
C8 C13 1.403(3) . ?
C9 C10 1.378(3) . ?
C10 C11 1.400(4) . ?
C11 C12 1.371(4) . ?
C12 C13 1.403(3) . ?
C13 C14 1.424(3) . ?
C14 C15 1.369(3) . ?
C15 C16 1.453(3) . ?
C16 C17 1.431(3) . ?
C16 C23 1.367(3) . ?
C17 C18 1.398(3) . ?
C17 C22 1.404(3) . ?
C18 C19 1.371(4) . ?
C19 C20 1.420(4) . ?
C19 C24 1.516(5) . ?
C20 C21 1.358(5) . ?
C21 C22 1.396(4) . ?
C25 C26 1.387(3) . ?
C25 C30 1.393(3) . ?
C26 C27 1.377(3) . ?
C27 C28 1.371(4) . ?
C28 C29 1.366(4) . ?
C29 C30 1.382(4) . ?

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
C5 O2 C6 116.33(19) . . ?
N2 N1 C1 124.61(16) . . ?
C4 N1 N2 123.38(16) . . ?
C4 N1 C1 111.65(16) . . ?
N1 N2 C8 123.22(17) . . ?
N1 N2 C15 123.23(16) . . ?
C8 N2 C15 110.02(16) . . ?
C22 N3 C23 109.0(2) . . ?
N1 C1 C25 124.70(17) . . ?
C2 C1 N1 105.19(17) . . ?
C2 C1 C25 130.03(18) . . ?
C1 C2 C3 109.00(18) . . ?
C2 C3 C5 126.15(19) . . ?
C4 C3 C2 108.00(17) . . ?
C4 C3 C5 125.84(19) . . ?
N1 C4 C3 106.13(17) . . ?
N1 C4 C7 121.32(19) . . ?
C3 C4 C7 132.5(2) . . ?
O1 C5 O2 122.5(2) . . ?
O1 C5 C3 126.7(2) . . ?
O2 C5 C3 110.82(19) . . ?
N2 C8 C13 106.55(18) . . ?
C9 C8 N2 129.28(19) . . ?
C9 C8 C13 124.15(19) . . ?
C10 C9 C8 116.5(2) . . ?
C9 C10 C11 121.0(2) . . ?
C12 C11 C10 121.7(2) . . ?
C11 C12 C13 119.1(2) . . ?
C8 C13 C12 117.5(2) . . ?
C8 C13 C14 107.50(18) . . ?
C12 C13 C14 134.9(2) . . ?
C15 C14 C13 108.70(19) . . ?
N2 C15 C16 120.98(17) . . ?
C14 C15 N2 107.16(18) . . ?
C14 C15 C16 131.9(2) . . ?
C17 C16 C15 125.99(19) . . ?
C23 C16 C15 127.4(2) . . ?
C23 C16 C17 106.6(2) . . ?
C18 C17 C16 133.6(2) . . ?
C18 C17 C22 119.8(2) . . ?
C22 C17 C16 106.5(2) . . ?
C19 C18 C17 120.0(3) . . ?
C18 C19 C20 118.7(3) . . ?
C18 C19 C24 120.4(3) . . ?
C20 C19 C24 120.9(3) . . ?
C21 C20 C19 122.5(3) . . ?
C20 C21 C22 118.3(3) . . ?
N3 C22 C17 108.0(2) . . ?
N3 C22 C21 131.4(3) . . ?
C21 C22 C17 120.6(3) . . ?
N3 C23 C16 109.8(2) . . ?
C26 C25 C1 123.90(19) . . ?
C26 C25 C30 118.1(2) . . ?
C30 C25 C1 118.01(19) . . ?
C27 C26 C25 120.8(2) . . ?
C28 C27 C26 120.9(3) . . ?
C29 C28 C27 118.9(2) . . ?
C28 C29 C30 121.3(3) . . ?
C29 C30 C25 120.0(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
