# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_aaaa
_database_code_depnum_ccdc_archive 'CCDC 1903603'
loop_
_audit_author_name
_audit_author_address
'Dong-Liang Mo'
;Guangxi Normal University
China
;
_audit_update_record             
;
2019-03-16 deposited with the CCDC.	2019-05-05 downloaded from the CCDC.
;
_audit_creation_date             2018-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H19 N O'
_chemical_formula_sum            'C24 H19 N O'
_chemical_formula_weight         337.40
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   10.273(4)
_cell_length_b                   10.178(4)
_cell_length_c                   16.954(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.610(6)
_cell_angle_gamma                90.00
_cell_volume                     1747.7(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8738
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.51
_cell_measurement_theta_min      2.34
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_correction_T_min  0.9740
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20541
_diffrn_reflns_theta_full        26.51
_diffrn_reflns_theta_max         26.51
_diffrn_reflns_theta_min         2.01
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2972
_reflns_number_total             3606
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3606
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0590P)²+0.4400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1202
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18),
 C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.66809(10) 0.02494(10) 0.07115(6) 0.0348(3) Uani 1 d . . .
C2 C 0.60472(12) 0.13405(12) 0.06944(7) 0.0324(3) Uani 1 d . . .
O1 O 0.43759(11) 0.36320(10) 0.06509(7) 0.0502(3) Uani 1 d . . .
C4 C 0.52357(12) 0.16171(12) 0.13161(8) 0.0346(3) Uani 1 d . . .
C5 C 0.74501(12) 0.00002(13) 0.01039(8) 0.0348(3) Uani 1 d . . .
C6 C 0.73197(13) 0.07449(13) -0.06005(8) 0.0364(3) Uani 1 d . . .
C7 C 0.91284(13) 0.42507(13) 0.13414(8) 0.0363(3) Uani 1 d . . .
C8 C 0.60935(12) 0.24300(12) 0.00833(8) 0.0340(3) Uani 1 d . . .
C9 C 0.52540(14) 0.07908(14) 0.19782(8) 0.0398(3) Uani 1 d . . .
H9 H 0.5787 0.0047 0.2027 0.048 Uiso 1 calc . . R
C10 C 0.44344(14) 0.27320(13) 0.12624(9) 0.0405(3) Uani 1 d . . .
C11 C 0.71705(13) 0.34161(12) 0.03884(8) 0.0373(3) Uani 1 d . . .
H11 H 0.7209 0.4166 0.0080 0.045 Uiso 1 calc . . R
C12 C 1.12186(14) 0.59240(14) 0.19444(9) 0.0446(3) Uani 1 d . . .
H12 H 1.1917 0.6478 0.2143 0.054 Uiso 1 calc . . R
C13 C 0.83025(14) -0.10725(14) 0.02068(9) 0.0414(3) Uani 1 d . . .
H13 H 0.8389 -0.1563 0.0676 0.050 Uiso 1 calc . . R
C14 C 0.80529(13) 0.33191(13) 0.10425(8) 0.0395(3) Uani 1 d . . .
H14 H 0.7995 0.2577 0.1355 0.047 Uiso 1 calc . . R
C15 C 0.80500(15) 0.03886(15) -0.11860(9) 0.0450(3) Uani 1 d . . .
H15 H 0.7972 0.0875 -0.1656 0.054 Uiso 1 calc . . R
C16 C 0.36594(15) 0.29954(16) 0.18411(10) 0.0501(4) Uani 1 d . . .
H16 H 0.3116 0.3732 0.1793 0.060 Uiso 1 calc . . R
C17 C 0.63148(14) 0.18234(13) -0.07176(8) 0.0403(3) Uani 1 d . . .
H17A H 0.5485 0.1477 -0.0997 0.048 Uiso 1 calc . . R
H17B H 0.6605 0.2504 -0.1049 0.048 Uiso 1 calc . . R
C18 C 0.99385(14) 0.39953(15) 0.20675(8) 0.0421(3) Uani 1 d . . .
H18 H 0.9785 0.3251 0.2357 0.050 Uiso 1 calc . . R
C19 C 0.88942(15) -0.06834(16) -0.10790(10) 0.0507(4) Uani 1 d . . .
H19 H 0.9377 -0.0911 -0.1476 0.061 Uiso 1 calc . . R
C20 C 1.09691(14) 0.48272(16) 0.23681(9) 0.0448(3) Uani 1 d . . .
H20 H 1.1493 0.4643 0.2858 0.054 Uiso 1 calc . . R
C21 C 0.36965(17) 0.21662(18) 0.24849(10) 0.0551(4) Uani 1 d . . .
H21 H 0.3181 0.2349 0.2873 0.066 Uiso 1 calc . . R
C22 C 0.47505(14) 0.31166(14) -0.00649(9) 0.0424(3) Uani 1 d . . .
H22A H 0.4778 0.3829 -0.0442 0.051 Uiso 1 calc . . R
H22B H 0.4084 0.2496 -0.0306 0.051 Uiso 1 calc . . R
C23 C 0.90205(15) -0.14145(16) -0.03828(9) 0.0485(4) Uani 1 d . . .
H23 H 0.9586 -0.2134 -0.0312 0.058 Uiso 1 calc . . R
C24 C 0.93857(15) 0.53745(15) 0.09249(9) 0.0502(4) Uani 1 d . . .
H24 H 0.8853 0.5575 0.0441 0.060 Uiso 1 calc . . R
C25 C 0.44973(16) 0.10570(16) 0.25601(9) 0.0497(4) Uani 1 d . . .
H25 H 0.4523 0.0500 0.2997 0.060 Uiso 1 calc . . R
C26 C 1.04272(16) 0.61969(15) 0.12235(10) 0.0540(4) Uani 1 d . . .
H26 H 1.0593 0.6938 0.0935 0.065 Uiso 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
N1 C2 1.2852(17) . ?
N1 C5 1.4219(17) . ?
C2 C4 1.4760(19) . ?
C2 C8 1.5238(18) . ?
O1 C10 1.3772(18) . ?
O1 C22 1.4324(18) . ?
C4 C9 1.4001(19) . ?
C4 C10 1.3959(19) . ?
C5 C6 1.4018(19) . ?
C5 C13 1.3922(19) . ?
C6 C15 1.389(2) . ?
C6 C17 1.497(2) . ?
C7 C14 1.4797(18) . ?
C7 C18 1.3904(19) . ?
C7 C24 1.393(2) . ?
C8 C11 1.5192(17) . ?
C8 C17 1.5426(19) . ?
C8 C22 1.5295(19) . ?
C9 C25 1.381(2) . ?
C10 C16 1.389(2) . ?
C11 C14 1.3137(19) . ?
C12 C20 1.375(2) . ?
C12 C26 1.379(2) . ?
C13 C23 1.382(2) . ?
C15 C19 1.387(2) . ?
C16 C21 1.375(2) . ?
C18 C20 1.385(2) . ?
C19 C23 1.383(2) . ?
C21 C25 1.390(2) . ?
C24 C26 1.386(2) . ?

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 N1 C5 118.59(11) . . ?
N1 C2 C4 119.54(11) . . ?
N1 C2 C8 124.82(12) . . ?
C4 C2 C8 115.61(11) . . ?
C10 O1 C22 114.21(11) . . ?
C9 C4 C2 121.62(12) . . ?
C10 C4 C2 120.37(12) . . ?
C10 C4 C9 118.00(12) . . ?
C6 C5 N1 122.35(12) . . ?
C13 C5 N1 117.58(12) . . ?
C13 C5 C6 119.96(12) . . ?
C5 C6 C17 118.36(12) . . ?
C15 C6 C5 118.79(13) . . ?
C15 C6 C17 122.65(13) . . ?
C18 C7 C14 119.06(12) . . ?
C18 C7 C24 117.79(12) . . ?
C24 C7 C14 123.15(12) . . ?
C2 C8 C17 109.46(11) . . ?
C2 C8 C22 108.33(11) . . ?
C11 C8 C2 110.66(10) . . ?
C11 C8 C17 110.99(11) . . ?
C11 C8 C22 109.86(11) . . ?
C22 C8 C17 107.44(11) . . ?
C25 C9 C4 121.40(14) . . ?
O1 C10 C4 122.75(12) . . ?
O1 C10 C16 116.44(13) . . ?
C16 C10 C4 120.81(14) . . ?
C14 C11 C8 126.76(12) . . ?
C20 C12 C26 119.55(13) . . ?
C23 C13 C5 120.48(14) . . ?
C11 C14 C7 127.70(13) . . ?
C19 C15 C6 120.84(14) . . ?
C21 C16 C10 119.93(14) . . ?
C6 C17 C8 112.11(11) . . ?
C20 C18 C7 121.29(13) . . ?
C23 C19 C15 120.17(14) . . ?
C12 C20 C18 120.14(13) . . ?
C16 C21 C25 120.58(14) . . ?
O1 C22 C8 113.00(11) . . ?
C13 C23 C19 119.76(14) . . ?
C26 C24 C7 120.75(14) . . ?
C9 C25 C21 119.27(15) . . ?
C12 C26 C24 120.48(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
