# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 2005596'
loop_
_audit_author_name
_audit_author_address
'hengwei wei'
;Shaanxi Normal University
China
;
_audit_update_record             
;
2020-05-25 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H19 N O3'
_chemical_formula_sum            'C27 H19 N O3'
_chemical_formula_weight         405.44

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'
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'
H H 0.0000 0.0000 '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 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.73920(10)
_cell_length_b                   11.05470(10)
_cell_length_c                   19.1794(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.8760(10)
_cell_angle_gamma                90
_cell_volume                     2020.73(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    180
_cell_measurement_reflns_used    12815
_cell_measurement_theta_min      2.3820
_cell_measurement_theta_max      75.5890

_exptl_crystal_description       transparent
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             773
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.695
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16576
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         6.186
_diffrn_reflns_theta_max         75.753
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4027
_reflns_number_gt                3748
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0631P)²+0.6596P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4027
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1190
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
O001 O 0.59409(11) 0.06871(8) 0.60105(6) 0.0434(3) Uani 1 1 d . . . . .
O002 O 0.48718(11) 0.47475(8) 0.65471(5) 0.0426(3) Uani 1 1 d . . . . .
O003 O 0.44579(11) 0.65641(9) 0.68905(5) 0.0451(3) Uani 1 1 d . . . . .
N004 N 0.18287(14) 1.14249(11) 0.80824(7) 0.0458(3) Uani 1 1 d . . . . .
C00A C 0.19990(14) 1.06708(12) 0.77022(7) 0.0354(3) Uani 1 1 d . . . . .
C00B C 0.18814(14) 0.50877(11) 0.46398(7) 0.0317(3) Uani 1 1 d . . . . .
H00B H 0.1794 0.4486 0.4294 0.038 Uiso 1 1 calc R U . . .
C00C C 0.21174(13) 0.97083(11) 0.72111(7) 0.0313(3) Uani 1 1 d . . . . .
C00D C 0.09386(13) 0.60656(12) 0.45366(7) 0.0315(3) Uani 1 1 d . . . . .
C00E C 0.30995(14) 0.88838(12) 0.62667(7) 0.0341(3) Uani 1 1 d . . . . .
H00E H 0.3719 0.8942 0.5958 0.041 Uiso 1 1 calc R U . . .
C00F C 0.45080(14) 0.18819(12) 0.51467(7) 0.0347(3) Uani 1 1 d . . . . .
H00F H 0.4455 0.1234 0.4833 0.042 Uiso 1 1 calc R U . . .
C00G C 0.10784(13) 0.69980(11) 0.50577(7) 0.0316(3) Uani 1 1 d . . . . .
C00H C 0.30625(14) 0.97898(12) 0.67582(7) 0.0343(3) Uani 1 1 d . . . . .
H00H H 0.3664 1.0449 0.6786 0.041 Uiso 1 1 calc R U . . .
C00I C 0.12858(15) 0.78101(12) 0.66859(8) 0.0373(3) Uani 1 1 d . . . . .
H00I H 0.0691 0.7146 0.6661 0.045 Uiso 1 1 calc R U . . .
C00J C 0.21718(13) 0.69226(11) 0.56764(7) 0.0299(3) Uani 1 1 d . . . . .
C00K C 0.37716(14) 0.29273(12) 0.49327(7) 0.0337(3) Uani 1 1 d . . . . .
H00K H 0.3226 0.2973 0.4475 0.040 Uiso 1 1 calc R U . . .
C00L C 0.41608(14) 0.58198(11) 0.64295(7) 0.0334(3) Uani 1 1 d . . . . .
C00M C 0.12333(15) 0.87153(12) 0.71785(7) 0.0370(3) Uani 1 1 d . . . . .
H00M H 0.0611 0.8659 0.7485 0.044 Uiso 1 1 calc R U . . .
C00N C 0.47037(14) 0.38163(11) 0.60544(7) 0.0335(3) Uani 1 1 d . . . . .
C00O C 0.00841(15) 0.79627(13) 0.49455(8) 0.0385(3) Uani 1 1 d . . . . .
H00O H 0.0163 0.8586 0.5277 0.046 Uiso 1 1 calc R U . . .
C00P C -0.11197(15) 0.70593(14) 0.38462(8) 0.0419(3) Uani 1 1 d . . . . .
H00P H -0.1848 0.7088 0.3448 0.050 Uiso 1 1 calc R U . . .
C00Q C 0.54559(15) 0.27738(12) 0.62926(8) 0.0390(3) Uani 1 1 d . . . . .
H00Q H 0.6022 0.2738 0.6746 0.047 Uiso 1 1 calc R U . . .
C00R C -0.01885(14) 0.61184(13) 0.39309(7) 0.0370(3) Uani 1 1 d . . . . .
H00R H -0.0291 0.5508 0.3591 0.044 Uiso 1 1 calc R U . . .
C00S C -0.09786(15) 0.79842(14) 0.43599(8) 0.0429(3) Uani 1 1 d . . . . .
H00S H -0.1619 0.8619 0.4299 0.052 Uiso 1 1 calc R U . . .
C00T C 0.69769(15) 0.05617(12) 0.66732(8) 0.0395(3) Uani 1 1 d . . . . .
H00T H 0.6651 0.0988 0.7057 0.047 Uiso 1 1 calc R U . . .
C00U C 0.83391(17) 0.10923(16) 0.65774(11) 0.0550(4) Uani 1 1 d . . . . .
H00A H 0.8684 0.0642 0.6221 0.082 Uiso 1 1 calc R U . . .
H00C H 0.9010 0.1055 0.7020 0.082 Uiso 1 1 calc R U . . .
H00D H 0.8198 0.1920 0.6429 0.082 Uiso 1 1 calc R U . . .
C00V C 0.70786(19) -0.07726(15) 0.68335(11) 0.0584(5) Uani 1 1 d . . . . .
H00G H 0.6180 -0.1069 0.6887 0.088 Uiso 1 1 calc R U . . .
H00J H 0.7756 -0.0907 0.7267 0.088 Uiso 1 1 calc R U . . .
H00L H 0.7365 -0.1192 0.6449 0.088 Uiso 1 1 calc R U . . .
C005 C 0.29331(13) 0.49984(11) 0.52411(6) 0.0288(3) Uani 1 1 d . . . . .
C006 C 0.22188(13) 0.78851(11) 0.62288(7) 0.0305(3) Uani 1 1 d . . . . .
C007 C 0.30788(13) 0.59349(11) 0.57652(6) 0.0293(3) Uani 1 1 d . . . . .
C008 C 0.53376(14) 0.17899(11) 0.58353(7) 0.0349(3) Uani 1 1 d . . . . .
C009 C 0.38253(13) 0.39267(11) 0.53907(7) 0.0300(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
O001 C008 1.3649(15) . ?
O001 C00T 1.4578(17) . ?
O002 C00L 1.3679(15) . ?
O002 C00N 1.3840(15) . ?
O003 C00L 1.1988(16) . ?
N004 C00A 1.1419(18) . ?
C00A C00C 1.4413(18) . ?
C00B C005 1.3794(18) . ?
C00B C00D 1.4058(18) . ?
C00C C00M 1.3885(19) . ?
C00C C00H 1.3925(18) . ?
C00D C00G 1.4226(18) . ?
C00D C00R 1.4258(18) . ?
C00E C00H 1.3809(18) . ?
C00E C006 1.3907(18) . ?
C00F C00K 1.3773(18) . ?
C00F C008 1.4029(19) . ?
C00G C00J 1.4244(18) . ?
C00G C00O 1.4267(18) . ?
C00I C00M 1.3844(19) . ?
C00I C006 1.3889(18) . ?
C00J C007 1.3927(17) . ?
C00J C006 1.4955(17) . ?
C00K C009 1.4057(18) . ?
C00L C007 1.4823(18) . ?
C00N C009 1.3853(18) . ?
C00N C00Q 1.3914(18) . ?
C00O C00S 1.362(2) . ?
C00P C00R 1.368(2) . ?
C00P C00S 1.407(2) . ?
C00Q C008 1.3871(19) . ?
C00T C00U 1.496(2) . ?
C00T C00V 1.506(2) . ?
C005 C007 1.4296(17) . ?
C005 C009 1.4623(17) . ?

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
C008 O001 C00T 119.03(10) . . ?
C00L O002 C00N 123.18(10) . . ?
N004 C00A C00C 176.32(15) . . ?
C005 C00B C00D 121.59(12) . . ?
C00M C00C C00H 120.43(12) . . ?
C00M C00C C00A 118.73(12) . . ?
C00H C00C C00A 120.79(12) . . ?
C00B C00D C00G 119.54(12) . . ?
C00B C00D C00R 121.15(12) . . ?
C00G C00D C00R 119.28(12) . . ?
C00H C00E C006 120.60(12) . . ?
C00K C00F C008 120.33(12) . . ?
C00D C00G C00J 119.34(11) . . ?
C00D C00G C00O 118.15(12) . . ?
C00J C00G C00O 122.49(12) . . ?
C00E C00H C00C 119.49(12) . . ?
C00M C00I C006 120.56(12) . . ?
C007 C00J C00G 119.63(11) . . ?
C007 C00J C006 123.02(11) . . ?
C00G C00J C006 117.21(11) . . ?
C00F C00K C009 121.54(12) . . ?
O003 C00L O002 115.85(12) . . ?
O003 C00L C007 126.58(12) . . ?
O002 C00L C007 117.53(11) . . ?
C00I C00M C00C 119.51(12) . . ?
O002 C00N C009 121.72(11) . . ?
O002 C00N C00Q 114.31(11) . . ?
C009 C00N C00Q 123.95(12) . . ?
C00S C00O C00G 120.96(13) . . ?
C00R C00P C00S 120.18(13) . . ?
C008 C00Q C00N 118.18(12) . . ?
C00P C00R C00D 120.56(13) . . ?
C00O C00S C00P 120.86(13) . . ?
O001 C00T C00U 109.13(13) . . ?
O001 C00T C00V 106.01(12) . . ?
C00U C00T C00V 112.73(13) . . ?
C00B C005 C007 119.03(11) . . ?
C00B C005 C009 122.07(11) . . ?
C007 C005 C009 118.67(11) . . ?
C00I C006 C00E 119.40(12) . . ?
C00I C006 C00J 118.42(11) . . ?
C00E C006 C00J 122.04(11) . . ?
C00J C007 C005 120.87(11) . . ?
C00J C007 C00L 119.55(11) . . ?
C005 C007 C00L 119.49(11) . . ?
O001 C008 C00Q 124.69(12) . . ?
O001 C008 C00F 115.58(11) . . ?
C00Q C008 C00F 119.68(12) . . ?
C00N C009 C00K 116.20(11) . . ?
C00N C009 C005 118.77(11) . . ?
C00K C009 C005 124.75(12) . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.043



