# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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. 
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data_cu_cxy0113_0m
_database_code_depnum_ccdc_archive 'CCDC 1946036'
loop_
_audit_author_name
_audit_author_address
'Jun WANG'
;Southern University of Science and Technology 
China
;
_audit_update_record             
;
2019-08-08 deposited with the CCDC.	2020-05-25 downloaded from the CCDC.
;
_audit_creation_date             2017-08-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2016/6
_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_absolute_configuration ad
_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.9107(3)
_cell_length_b                   12.0632(3)
_cell_length_c                   14.3759(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1718.71(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9771
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.43
_cell_measurement_theta_min      3.66
_shelx_estimated_absorpt_T_max   0.809
_shelx_estimated_absorpt_T_min   0.015
_exptl_absorpt_coefficient_mu    0.616
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0821 before and 0.0532 after correction. The Ratio of minimum to maximum transmission is 0.9264. 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    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.36
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23392
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.426
_diffrn_reflns_theta_min         4.785
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 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'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3096
_reflns_number_total             3150
_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         0.191
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1310 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_coef       0.0133(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0249
_refine_ls_restrained_S_all      1.065
_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)+(0.0273P)²+0.4048P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0610
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
  C15(H15), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
O1 O 0.82483(11) 0.72363(9) 0.57171(8) 0.0179(3) Uani 1 1 d . . . . .
H1 H 0.873902 0.713865 0.524775 0.027 Uiso 1 1 calc GR . . . .
N1 N 0.87226(14) 0.48576(11) 0.59573(9) 0.0148(3) Uani 1 1 d . . . . .
C1 C 0.56970(17) 0.81220(14) 0.60485(11) 0.0176(3) Uani 1 1 d . . . . .
H1A H 0.640406 0.859674 0.584754 0.021 Uiso 1 1 calc R . . . .
C2 C 0.44694(18) 0.85728(14) 0.63402(11) 0.0202(4) Uani 1 1 d . . . . .
H2 H 0.435437 0.935441 0.635667 0.024 Uiso 1 1 calc R . . . .
C3 C 0.34185(17) 0.78832(15) 0.66057(12) 0.0208(4) Uani 1 1 d . . . . .
H3 H 0.257644 0.819108 0.678718 0.025 Uiso 1 1 calc R . . . .
C4 C 0.35995(17) 0.67400(15) 0.66059(11) 0.0192(4) Uani 1 1 d . . . . .
H4 H 0.287739 0.626818 0.678512 0.023 Uiso 1 1 calc R . . . .
C5 C 0.48329(17) 0.62826(13) 0.63450(11) 0.0163(3) Uani 1 1 d . . . . .
C6 C 0.58864(16) 0.69786(13) 0.60515(11) 0.0155(3) Uani 1 1 d . . . . .
C7 C 0.50863(17) 0.50856(13) 0.64191(11) 0.0175(3) Uani 1 1 d . . . . .
H7 H 0.434407 0.459203 0.647660 0.021 Uiso 1 1 calc R . . . .
C8 C 0.63332(17) 0.46792(13) 0.64074(11) 0.0170(3) Uani 1 1 d . . . . .
H8 H 0.646754 0.390175 0.645740 0.020 Uiso 1 1 calc R . . . .
C9 C 0.75402(15) 0.54377(13) 0.63155(11) 0.0147(3) Uani 1 1 d . . . . .
H9 H 0.776834 0.571595 0.695158 0.018 Uiso 1 1 calc R . . . .
C10 C 0.71793(15) 0.64484(13) 0.57122(11) 0.0147(3) Uani 1 1 d . . . . .
H10 H 0.703832 0.619074 0.505819 0.018 Uiso 1 1 calc R . . . .
C11 C 0.87555(16) 0.42471(13) 0.51381(10) 0.0137(3) Uani 1 1 d . . . . .
C12 C 0.77050(17) 0.39399(13) 0.45392(12) 0.0169(3) Uani 1 1 d . . . . .
H12 H 0.680184 0.416856 0.464980 0.020 Uiso 1 1 calc R . . . .
C13 C 0.80375(17) 0.32883(13) 0.37783(11) 0.0169(3) Uani 1 1 d . . . . .
H13 H 0.734552 0.305986 0.336307 0.020 Uiso 1 1 calc R . . . .
C14 C 0.93751(17) 0.29578(13) 0.36070(11) 0.0180(3) Uani 1 1 d . . . . .
H14 H 0.957299 0.251789 0.307615 0.022 Uiso 1 1 calc R . . . .
C15 C 1.04059(16) 0.32650(13) 0.42013(11) 0.0174(3) Uani 1 1 d . . . . .
H15 H 1.130831 0.304193 0.408034 0.021 Uiso 1 1 calc R . . . .
C16 C 1.01020(16) 0.39100(12) 0.49845(11) 0.0149(3) Uani 1 1 d . . . . .
C17 C 1.08794(16) 0.43255(13) 0.57454(11) 0.0162(3) Uani 1 1 d . . . . .
H17 H 1.182191 0.422784 0.583342 0.019 Uiso 1 1 calc R . . . .
C18 C 1.00261(16) 0.48888(12) 0.63245(11) 0.0148(3) Uani 1 1 d . . . . .
C19 C 1.03349(15) 0.53611(13) 0.72518(11) 0.0154(3) Uani 1 1 d . . . . .
C20 C 1.07580(18) 0.46549(14) 0.79649(12) 0.0210(4) Uani 1 1 d . . . . .
H20 H 1.083647 0.388225 0.784888 0.025 Uiso 1 1 calc R . . . .
C21 C 1.10654(18) 0.50692(15) 0.88418(12) 0.0227(4) Uani 1 1 d . . . . .
H21 H 1.133555 0.457902 0.932434 0.027 Uiso 1 1 calc R . . . .
C22 C 1.09775(16) 0.61985(15) 0.90119(12) 0.0205(4) Uani 1 1 d . . . . .
H22 H 1.118175 0.648400 0.961150 0.025 Uiso 1 1 calc R . . . .
C23 C 1.05907(16) 0.69072(14) 0.83035(12) 0.0200(4) Uani 1 1 d . . . . .
H23 H 1.055046 0.768261 0.841563 0.024 Uiso 1 1 calc R . . . .
C24 C 1.02609(16) 0.64963(13) 0.74303(12) 0.0180(3) Uani 1 1 d . . . . .
H24 H 0.998367 0.699022 0.695246 0.022 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 H1 0.8400 . ?
O1 C10 1.4233(18) . ?
N1 C9 1.459(2) . ?
N1 C11 1.389(2) . ?
N1 C18 1.396(2) . ?
C1 H1A 0.9500 . ?
C1 C2 1.397(2) . ?
C1 C6 1.392(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(2) . ?
C5 C6 1.405(2) . ?
C5 C7 1.469(2) . ?
C6 C10 1.513(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.330(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.512(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.538(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.401(2) . ?
C11 C16 1.412(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.406(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.401(2) . ?
C16 C17 1.429(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.367(2) . ?
C18 C19 1.482(2) . ?
C19 C20 1.397(2) . ?
C19 C24 1.395(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.390(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.389(2) . ?
C24 H24 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
C10 O1 H1 109.5 . . ?
C11 N1 C9 124.91(13) . . ?
C11 N1 C18 108.25(13) . . ?
C18 N1 C9 126.65(13) . . ?
C2 C1 H1A 119.9 . . ?
C6 C1 H1A 119.9 . . ?
C6 C1 C2 120.15(16) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.21(15) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.88(16) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.40(16) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.77(15) . . ?
C4 C5 C7 121.32(15) . . ?
C6 C5 C7 118.82(15) . . ?
C1 C6 C5 119.54(15) . . ?
C1 C6 C10 122.15(15) . . ?
C5 C6 C10 118.27(14) . . ?
C5 C7 H7 119.3 . . ?
C8 C7 C5 121.35(15) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.89(14) . . ?
C9 C8 H8 119.6 . . ?
N1 C9 C8 112.09(12) . . ?
N1 C9 H9 107.6 . . ?
N1 C9 C10 111.59(13) . . ?
C8 C9 H9 107.6 . . ?
C8 C9 C10 110.18(13) . . ?
C10 C9 H9 107.6 . . ?
O1 C10 C6 110.27(12) . . ?
O1 C10 C9 110.69(12) . . ?
O1 C10 H10 108.4 . . ?
C6 C10 C9 110.49(13) . . ?
C6 C10 H10 108.4 . . ?
C9 C10 H10 108.4 . . ?
N1 C11 C12 130.07(15) . . ?
N1 C11 C16 107.90(14) . . ?
C12 C11 C16 122.00(14) . . ?
C11 C12 H12 121.4 . . ?
C13 C12 C11 117.26(15) . . ?
C13 C12 H12 121.4 . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.53(15) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.84(15) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.12(15) . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C17 106.79(14) . . ?
C15 C16 C11 119.24(15) . . ?
C15 C16 C17 133.95(15) . . ?
C16 C17 H17 126.1 . . ?
C18 C17 C16 107.88(14) . . ?
C18 C17 H17 126.1 . . ?
N1 C18 C19 122.80(14) . . ?
C17 C18 N1 109.18(14) . . ?
C17 C18 C19 127.67(15) . . ?
C20 C19 C18 119.18(14) . . ?
C24 C19 C18 122.15(15) . . ?
C24 C19 C20 118.64(15) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.79(16) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 119.96(16) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.63(16) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.66(16) . . ?
C24 C23 H23 119.7 . . ?
C19 C24 H24 119.9 . . ?
C23 C24 C19 120.29(16) . . ?
C23 C24 H24 119.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
