# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_cww1
_database_code_depnum_ccdc_archive 'CCDC 2092223'
loop_
_audit_author_name
_audit_author_address
li
;tyut
China
;
_audit_update_record             
;
2021-06-24 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;
_audit_creation_date             2018-06-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H21 N3 O3'
_chemical_formula_sum            'C24 H21 N3 O3'
_chemical_formula_weight         399.44
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.1633(9)
_cell_length_b                   16.9191(14)
_cell_length_c                   20.7850(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4277.4(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9867
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.572
_cell_measurement_theta_min      2.283
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1052 before and 0.0562 after correction. The Ratio of minimum to maximum transmission is 0.9453. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            73985
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_min         2.845
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3383
_reflns_number_total             5330
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.291
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.045
_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)+(0.0617P)²+1.2521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1476
_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:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7), C20(H20), C11(H11), C24(H24), C14(H14), C8(H8), C18(H18),
 C21(H21), C9(H9), C10(H10), C15(H15), C23(H23), C22(H22), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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
O2 O 0.37725(11) 0.31439(8) 0.52189(6) 0.0599(4) Uani 1 1 d . . . . .
N1 N 0.30359(11) 0.36422(8) 0.38504(6) 0.0385(3) Uani 1 1 d . . . . .
O1 O 0.54971(12) 0.35367(9) 0.54038(7) 0.0694(4) Uani 1 1 d . . . . .
N2 N 0.36099(11) 0.45766(8) 0.45543(7) 0.0405(3) Uani 1 1 d . . . . .
N3 N 0.55583(11) 0.43730(9) 0.43177(7) 0.0466(4) Uani 1 1 d . . . . .
H3 H 0.6092 0.4300 0.4583 0.056 Uiso 1 1 calc R . . . .
C6 C 0.23440(13) 0.32309(9) 0.34016(8) 0.0379(4) Uani 1 1 d . . . . .
C12 C 0.28110(13) 0.43320(9) 0.42058(8) 0.0367(4) Uani 1 1 d . . . . .
C5 C 0.41080(13) 0.34246(9) 0.39631(8) 0.0390(4) Uani 1 1 d . . . . .
C19 C 0.57602(14) 0.48288(10) 0.37734(8) 0.0419(4) Uani 1 1 d . . . . .
C13 C 0.17578(14) 0.47544(10) 0.41708(8) 0.0397(4) Uani 1 1 d . . . . .
C1 C 0.45282(13) 0.40196(10) 0.44653(8) 0.0399(4) Uani 1 1 d . . . . .
C7 C 0.19665(15) 0.24951(10) 0.35650(9) 0.0478(4) Uani 1 1 d . . . . .
H7 H 0.2158 0.2272 0.3958 0.057 Uiso 1 1 calc R . . . .
C2 C 0.46778(15) 0.35441(10) 0.50925(9) 0.0462(4) Uani 1 1 d . . . . .
C20 C 0.50527(16) 0.48944(11) 0.32541(9) 0.0497(4) Uani 1 1 d . . . . .
H20 H 0.4372 0.4644 0.3267 0.060 Uiso 1 1 calc R . . . .
C11 C 0.20784(16) 0.35651(11) 0.28198(9) 0.0536(5) Uani 1 1 d . . . . .
H11 H 0.2346 0.4061 0.2707 0.064 Uiso 1 1 calc R . . . .
C24 C 0.67599(16) 0.52238(13) 0.37396(10) 0.0582(5) Uani 1 1 d . . . . .
H24 H 0.7247 0.5196 0.4084 0.070 Uiso 1 1 calc R . . . .
C14 C 0.07553(15) 0.43787(12) 0.41184(10) 0.0552(5) Uani 1 1 d . . . . .
H14 H 0.0728 0.3831 0.4087 0.066 Uiso 1 1 calc R . . . .
C8 C 0.13018(18) 0.20861(12) 0.31437(10) 0.0595(5) Uani 1 1 d . . . . .
H8 H 0.1045 0.1586 0.3252 0.071 Uiso 1 1 calc R . . . .
C18 C 0.17815(16) 0.55688(11) 0.42186(10) 0.0556(5) Uani 1 1 d . . . . .
H18 H 0.2451 0.5830 0.4259 0.067 Uiso 1 1 calc R . . . .
C21 C 0.53442(19) 0.53269(12) 0.27160(10) 0.0599(5) Uani 1 1 d . . . . .
H21 H 0.4862 0.5358 0.2370 0.072 Uiso 1 1 calc R . . . .
C9 C 0.10210(18) 0.24152(12) 0.25670(10) 0.0615(5) Uani 1 1 d . . . . .
H9 H 0.0568 0.2141 0.2284 0.074 Uiso 1 1 calc R . . . .
C10 C 0.14082(19) 0.31508(13) 0.24065(10) 0.0644(6) Uani 1 1 d . . . . .
H10 H 0.1215 0.3372 0.2013 0.077 Uiso 1 1 calc R . . . .
C15 C -0.02045(17) 0.48080(14) 0.41127(12) 0.0696(6) Uani 1 1 d . . . . .
H15 H -0.0877 0.4550 0.4080 0.084 Uiso 1 1 calc R . . . .
C23 C 0.7038(2) 0.56554(14) 0.32031(11) 0.0719(7) Uani 1 1 d . . . . .
H23 H 0.7712 0.5914 0.3189 0.086 Uiso 1 1 calc R . . . .
C22 C 0.6335(2) 0.57100(13) 0.26869(11) 0.0694(6) Uani 1 1 d . . . . .
H22 H 0.6528 0.6002 0.2325 0.083 Uiso 1 1 calc R . . . .
C16 C -0.01721(18) 0.56129(14) 0.41553(11) 0.0702(6) Uani 1 1 d . . . . .
H16 H -0.0822 0.5902 0.4150 0.084 Uiso 1 1 calc R . . . .
C17 C 0.08183(18) 0.59943(13) 0.42063(12) 0.0706(6) Uani 1 1 d . . . . .
H17 H 0.0839 0.6543 0.4233 0.085 Uiso 1 1 calc R . . . .
C3 C 0.3783(2) 0.26361(14) 0.57824(12) 0.0745(7) Uani 1 1 d . . . . .
H3A H 0.3852 0.2951 0.6170 0.089 Uiso 1 1 calc R . . . .
H3B H 0.4399 0.2273 0.5762 0.089 Uiso 1 1 calc R . . . .
C4 C 0.2741(3) 0.2197(2) 0.57882(15) 0.1133(11) Uani 1 1 d . . . . .
H4A H 0.2661 0.1913 0.5391 0.170 Uiso 1 1 calc GR . . . .
H4B H 0.2140 0.2560 0.5837 0.170 Uiso 1 1 calc GR . . . .
H4C H 0.2741 0.1830 0.6141 0.170 Uiso 1 1 calc GR . . . .
O3 O 0.45957(10) 0.28730(7) 0.37333(6) 0.0512(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
O2 C2 1.319(2) . ?
O2 C3 1.452(2) . ?
N1 C6 1.436(2) . ?
N1 C12 1.408(2) . ?
N1 C5 1.375(2) . ?
O1 C2 1.188(2) . ?
N2 C12 1.281(2) . ?
N2 C1 1.473(2) . ?
N3 C19 1.391(2) . ?
N3 C1 1.422(2) . ?
C6 C7 1.370(2) . ?
C6 C11 1.373(2) . ?
C12 C13 1.469(2) . ?
C5 C1 1.538(2) . ?
C5 O3 1.2045(19) . ?
C19 C20 1.385(3) . ?
C19 C24 1.389(3) . ?
C13 C14 1.379(2) . ?
C13 C18 1.382(2) . ?
C1 C2 1.543(2) . ?
C7 C8 1.378(3) . ?
C20 C21 1.383(3) . ?
C11 C10 1.376(3) . ?
C24 C23 1.375(3) . ?
C14 C15 1.375(3) . ?
C8 C9 1.365(3) . ?
C18 C17 1.375(3) . ?
C21 C22 1.369(3) . ?
C9 C10 1.372(3) . ?
C15 C16 1.365(3) . ?
C23 C22 1.375(3) . ?
C16 C17 1.371(3) . ?
C3 C4 1.470(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
C2 O2 C3 117.19(16) . . ?
C12 N1 C6 128.94(13) . . ?
C5 N1 C6 122.45(13) . . ?
C5 N1 C12 108.47(13) . . ?
C12 N2 C1 107.32(13) . . ?
C19 N3 C1 124.35(14) . . ?
C7 C6 N1 118.41(15) . . ?
C7 C6 C11 120.90(16) . . ?
C11 C6 N1 120.68(15) . . ?
N1 C12 C13 123.15(14) . . ?
N2 C12 N1 114.65(14) . . ?
N2 C12 C13 122.18(14) . . ?
N1 C5 C1 104.80(13) . . ?
O3 C5 N1 127.36(16) . . ?
O3 C5 C1 127.79(15) . . ?
C20 C19 N3 124.66(16) . . ?
C20 C19 C24 117.76(17) . . ?
C24 C19 N3 117.54(16) . . ?
C14 C13 C12 123.41(15) . . ?
C14 C13 C18 118.93(16) . . ?
C18 C13 C12 117.61(15) . . ?
N2 C1 C5 104.60(13) . . ?
N2 C1 C2 108.48(13) . . ?
N3 C1 N2 115.23(13) . . ?
N3 C1 C5 114.95(14) . . ?
N3 C1 C2 107.32(13) . . ?
C5 C1 C2 105.75(13) . . ?
C6 C7 C8 119.71(17) . . ?
O2 C2 C1 109.73(15) . . ?
O1 C2 O2 125.89(17) . . ?
O1 C2 C1 124.37(16) . . ?
C21 C20 C19 120.90(18) . . ?
C6 C11 C10 118.63(17) . . ?
C23 C24 C19 120.8(2) . . ?
C15 C14 C13 120.51(18) . . ?
C9 C8 C7 119.99(18) . . ?
C17 C18 C13 120.19(18) . . ?
C22 C21 C20 120.8(2) . . ?
C8 C9 C10 119.85(18) . . ?
C9 C10 C11 120.91(18) . . ?
C16 C15 C14 120.1(2) . . ?
C24 C23 C22 121.0(2) . . ?
C21 C22 C23 118.8(2) . . ?
C15 C16 C17 120.00(19) . . ?
C16 C17 C18 120.2(2) . . ?
O2 C3 C4 107.4(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
